Hexamethylenetetramine-benzoic acid (1/2) (HBA) and hexamethylenetetramine-4-methylbenzoic acid (1/2) (HMBA) co-crystals undergo order–disorder structural phase transition from a low-temperature monoclinic crystal structure to a high-temperature orthorhombic crystal structure at the transition temperatures of 257.5 (5) K (
Pn ↔
Fmm2) and 265.5 (5) K (
P2
1/
n ↔
Cmcm), respectively, using variable-temperature single-crystal X-ray diffraction analysis. The observed phase transitions were confirmed to be reversible first-order transitions as indicated by the sharp endothermic and exothermic peaks in the differential scanning calorimetry measurement. The three-molecule aggregate of HBA and HMBA consists of a hexamethylenetetramine molecule and two benzoic acid or two 4-methylbenzoic acid molecules, respectively. The acid molecules are ordered at the low-temperature phase and are equally disordered over two positions, which are related by a mirror symmetry, at the high-temperature phase. The two-dimensional supramolecular constructs common to both co-crystals are formed by three-molecule aggregates
via weak intermolecular C—H
O and C—H
π interactions into molecular trilayers parallel to the
ac plane with small
XPac dissimilarity indices and parameters. The
PIXEL interaction energies of all corresponding molecular contacts were calculated and the results are comparable between HBA and HMBA co-crystals, resulting in similar lattice energies and transition temperatures despite their two-dimensional isostructural relationship. The observed phase transitions of these two energetically similar co-crystals are triggered by similar mechanisms,
i.e. the molecular rotator ordering and structural order–disorder transformation, which induced non-merohedral twinning with similar twin matrices in the low-temperature crystal form of both co-crystals.
Supporting information
| Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520617009520/gw5053sup1.cif Contains datablocks 1533065, 1533066, 1533067, 1533068, 1533069, 1533070, 1533071, 1533072, 1533073, 1533074, 1533075, 1533076 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617009520/gw50531533065sup2.hkl Contains datablock 1533065 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617009520/gw50531533066sup3.hkl Contains datablock 1533066 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617009520/gw50531533067sup4.hkl Contains datablock 1533067 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617009520/gw50531533068sup5.hkl Contains datablock 1533068 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617009520/gw50531533069sup6.hkl Contains datablock 1533069 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617009520/gw50531533070sup7.hkl Contains datablock 1533070 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617009520/gw50531533071sup8.hkl Contains datablock 1533071 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617009520/gw50531533072sup9.hkl Contains datablock 1533072 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617009520/gw50531533073sup10.hkl Contains datablock 1533073 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617009520/gw50531533074sup11.hkl Contains datablock 1533074 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617009520/gw50531533075sup12.hkl Contains datablock 1533075 |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617009520/gw50531533076sup13.hkl Contains datablock 1533076 |
CCDC references: 1533065; 1533066; 1533067; 1533068; 1533069; 1533070; 1533071; 1533072; 1533073; 1533074; 1533075; 1533076
For all structures, data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015). Molecular graphics: SHELXTL (Sheldrick, 2008), Mercury (Macrae et al., 2008) for 1533065, 1533066, 1533067, 1533068, 1533069, 1533070, 1533071, 1533072, 1533073, 1533075, 1533076; SHELXTL (Sheldrick, 2008), (Macrae et al., 2008) for 1533074. For all structures, software used to prepare material for publication: PLATON (Spek, 2009).
Hexamethylenetetramine bis(benzoic acid) (1533065)
top
Crystal data top
C6H12N4·2(C7H6O2) | F(000) = 816 |
Mr = 384.43 | Dx = 1.343 Mg m−3 |
Monoclinic, Pn | Mo Kα radiation, λ = 0.71073 Å |
a = 6.0925 (5) Å | Cell parameters from 9986 reflections |
b = 26.145 (2) Å | θ = 2.9–28.4° |
c = 12.1017 (10) Å | µ = 0.10 mm−1 |
β = 99.3633 (17)° | T = 100 K |
V = 1902.0 (3) Å3 | Block, colourless |
Z = 4 | 0.76 × 0.39 × 0.21 mm |
Data collection top
Bruker APEX Duo CCD area detector diffractometer | 4725 independent reflections |
Radiation source: fine-focus sealed tube | 3719 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
φ and ω scans | θmax = 28.4°, θmin = 1.9° |
Absorption correction: multi-scan (TWINABS; Sheldrick, 2012) | h = −8→8 |
Tmin = 0.810, Tmax = 0.929 | k = 0→34 |
5967 measured reflections | l = 0→16 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.0424P)2 + 0.5679P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.113 | (Δ/σ)max = 0.001 |
S = 1.11 | Δρmax = 0.29 e Å−3 |
4725 reflections | Δρmin = −0.21 e Å−3 |
522 parameters | Absolute structure: No quotients, so Flack parameter determined by classical intensity fit |
6 restraints | Absolute structure parameter: −0.3 (8) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1A | 0.6880 (5) | 0.37873 (10) | 0.4653 (2) | 0.0286 (6) | |
H1O1 | 0.625 (7) | 0.4020 (13) | 0.496 (4) | 0.044 (13)* | |
O2A | 0.4041 (4) | 0.39828 (10) | 0.3314 (2) | 0.0331 (7) | |
O3A | 0.4289 (4) | 0.61070 (9) | 0.3987 (2) | 0.0210 (5) | |
H1O3 | 0.429 (7) | 0.5901 (13) | 0.452 (3) | 0.031 (11)* | |
O4A | 0.7923 (4) | 0.60567 (10) | 0.4617 (2) | 0.0283 (6) | |
N1A | 0.4883 (4) | 0.44883 (10) | 0.5718 (2) | 0.0165 (6) | |
N2A | 0.4013 (4) | 0.53955 (10) | 0.5446 (2) | 0.0171 (6) | |
N3A | 0.1385 (5) | 0.48222 (10) | 0.6143 (2) | 0.0183 (6) | |
N4A | 0.4892 (5) | 0.50519 (10) | 0.7329 (2) | 0.0198 (6) | |
C1A | 0.5090 (6) | 0.49429 (12) | 0.5019 (3) | 0.0181 (7) | |
H1AA | 0.4385 | 0.4872 | 0.4238 | 0.022* | |
H1AB | 0.6684 | 0.5017 | 0.5019 | 0.022* | |
C2A | 0.1653 (5) | 0.52706 (12) | 0.5449 (3) | 0.0191 (7) | |
H2AA | 0.0909 | 0.5568 | 0.5735 | 0.023* | |
H2AB | 0.0915 | 0.5204 | 0.4672 | 0.023* | |
C3A | 0.2498 (5) | 0.43883 (11) | 0.5704 (3) | 0.0179 (6) | |
H3AA | 0.1774 | 0.4317 | 0.4926 | 0.022* | |
H3AB | 0.2329 | 0.4081 | 0.6161 | 0.022* | |
C4A | 0.5941 (6) | 0.46104 (12) | 0.6883 (3) | 0.0204 (7) | |
H4AA | 0.5825 | 0.4310 | 0.7368 | 0.024* | |
H4AB | 0.7540 | 0.4683 | 0.6896 | 0.024* | |
C5A | 0.5108 (6) | 0.54930 (12) | 0.6618 (3) | 0.0190 (7) | |
H5AA | 0.6704 | 0.5568 | 0.6628 | 0.023* | |
H5AB | 0.4420 | 0.5796 | 0.6915 | 0.023* | |
C6A | 0.2525 (6) | 0.49358 (14) | 0.7285 (3) | 0.0221 (7) | |
H6AA | 0.1788 | 0.5231 | 0.7582 | 0.027* | |
H6AB | 0.2375 | 0.4638 | 0.7773 | 0.027* | |
C7A | 0.6943 (6) | 0.34656 (12) | 0.2835 (3) | 0.0190 (7) | |
C8A | 0.9124 (6) | 0.32952 (12) | 0.3149 (3) | 0.0232 (7) | |
H8AA | 0.9891 | 0.3352 | 0.3887 | 0.028* | |
C9A | 1.0160 (7) | 0.30396 (13) | 0.2365 (3) | 0.0299 (9) | |
H9AA | 1.1655 | 0.2927 | 0.2564 | 0.036* | |
C10A | 0.9035 (7) | 0.29491 (14) | 0.1308 (4) | 0.0342 (10) | |
H10A | 0.9750 | 0.2771 | 0.0782 | 0.041* | |
C11A | 0.6868 (7) | 0.31141 (13) | 0.1002 (3) | 0.0311 (9) | |
H11A | 0.6102 | 0.3051 | 0.0266 | 0.037* | |
C12A | 0.5808 (6) | 0.33718 (13) | 0.1768 (3) | 0.0243 (7) | |
H12A | 0.4313 | 0.3483 | 0.1562 | 0.029* | |
C13A | 0.5807 (6) | 0.37694 (12) | 0.3619 (3) | 0.0208 (7) | |
C14A | 0.6695 (5) | 0.65438 (12) | 0.2975 (3) | 0.0167 (6) | |
C15A | 0.4914 (5) | 0.66774 (12) | 0.2163 (3) | 0.0183 (7) | |
H15A | 0.3459 | 0.6565 | 0.2230 | 0.022* | |
C16A | 0.5237 (6) | 0.69748 (12) | 0.1252 (3) | 0.0229 (7) | |
H16A | 0.4014 | 0.7059 | 0.0690 | 0.027* | |
C17A | 0.7349 (6) | 0.71474 (12) | 0.1169 (3) | 0.0241 (7) | |
H17A | 0.7569 | 0.7361 | 0.0561 | 0.029* | |
C18A | 0.9143 (6) | 0.70103 (11) | 0.1969 (3) | 0.0204 (7) | |
H18A | 1.0595 | 0.7123 | 0.1896 | 0.024* | |
C19A | 0.8836 (6) | 0.67096 (11) | 0.2877 (3) | 0.0186 (7) | |
H19A | 1.0070 | 0.6617 | 0.3427 | 0.022* | |
C20A | 0.6370 (6) | 0.62169 (11) | 0.3944 (3) | 0.0170 (7) | |
O1B | 1.4421 (5) | 0.88191 (10) | 0.7182 (2) | 0.0268 (6) | |
H2O1 | 1.368 (9) | 0.9007 (19) | 0.753 (5) | 0.08 (2)* | |
O2B | 1.1677 (4) | 0.90082 (10) | 0.5798 (2) | 0.0316 (6) | |
O3B | 1.1732 (4) | 1.11186 (9) | 0.6510 (2) | 0.0229 (5) | |
H2O3 | 1.161 (10) | 1.0899 (17) | 0.701 (4) | 0.08 (2)* | |
O4B | 1.5356 (4) | 1.10986 (10) | 0.7191 (2) | 0.0294 (6) | |
N1B | 1.2365 (5) | 0.95068 (9) | 0.8223 (2) | 0.0153 (6) | |
N2B | 1.1441 (4) | 1.04133 (9) | 0.7986 (2) | 0.0138 (5) | |
N3B | 0.8855 (5) | 0.98287 (11) | 0.8657 (2) | 0.0204 (6) | |
N4B | 1.2341 (5) | 1.00494 (10) | 0.9860 (2) | 0.0179 (6) | |
C1B | 1.2541 (6) | 0.99711 (10) | 0.7548 (3) | 0.0143 (7) | |
H1BA | 1.1846 | 0.9906 | 0.6763 | 0.017* | |
H1BB | 1.4130 | 1.0052 | 0.7554 | 0.017* | |
C2B | 0.9072 (5) | 1.02839 (12) | 0.7976 (3) | 0.0200 (7) | |
H2BA | 0.8313 | 1.0576 | 0.8271 | 0.024* | |
H2BB | 0.8342 | 1.0221 | 0.7195 | 0.024* | |
C3B | 0.9972 (5) | 0.94012 (12) | 0.8203 (3) | 0.0203 (7) | |
H3BA | 0.9252 | 0.9335 | 0.7422 | 0.024* | |
H3BB | 0.9810 | 0.9090 | 0.8648 | 0.024* | |
C4B | 1.3405 (6) | 0.96169 (12) | 0.9401 (3) | 0.0190 (7) | |
H4BA | 1.3284 | 0.9311 | 0.9868 | 0.023* | |
H4BB | 1.5005 | 0.9692 | 0.9426 | 0.023* | |
C5B | 1.2528 (6) | 1.05016 (11) | 0.9157 (3) | 0.0180 (7) | |
H5BA | 1.4118 | 1.0583 | 0.9168 | 0.022* | |
H5BB | 1.1824 | 1.0799 | 0.9467 | 0.022* | |
C6B | 0.9972 (6) | 0.99309 (13) | 0.9804 (3) | 0.0210 (7) | |
H6BA | 0.9229 | 1.0222 | 1.0113 | 0.025* | |
H6BB | 0.9818 | 0.9628 | 1.0276 | 0.025* | |
C7B | 1.4563 (6) | 0.84617 (11) | 0.5417 (3) | 0.0175 (7) | |
C8B | 1.6752 (6) | 0.83103 (11) | 0.5744 (3) | 0.0194 (7) | |
H8BA | 1.7519 | 0.8400 | 0.6465 | 0.023* | |
C9B | 1.7832 (7) | 0.80270 (13) | 0.5018 (3) | 0.0291 (8) | |
H9BA | 1.9331 | 0.7923 | 0.5245 | 0.035* | |
C10B | 1.6713 (7) | 0.78974 (13) | 0.3966 (3) | 0.0323 (9) | |
H10B | 1.7443 | 0.7701 | 0.3474 | 0.039* | |
C11B | 1.4553 (8) | 0.80517 (14) | 0.3631 (3) | 0.0329 (9) | |
H11B | 1.3797 | 0.7961 | 0.2908 | 0.039* | |
C12B | 1.3464 (6) | 0.83402 (12) | 0.4343 (3) | 0.0236 (7) | |
H12B | 1.1983 | 0.8454 | 0.4100 | 0.028* | |
C13B | 1.3402 (6) | 0.87835 (11) | 0.6138 (3) | 0.0182 (7) | |
C14B | 1.4158 (5) | 1.15522 (11) | 0.5505 (3) | 0.0139 (6) | |
C15B | 1.2410 (5) | 1.16483 (11) | 0.4641 (3) | 0.0162 (6) | |
H15B | 1.0977 | 1.1513 | 0.4680 | 0.019* | |
C16B | 1.2732 (6) | 1.19398 (11) | 0.3723 (3) | 0.0192 (7) | |
H16B | 1.1522 | 1.2010 | 0.3142 | 0.023* | |
C17B | 1.4838 (6) | 1.21281 (12) | 0.3661 (3) | 0.0213 (7) | |
H17B | 1.5072 | 1.2324 | 0.3030 | 0.026* | |
C18B | 1.6600 (6) | 1.20328 (13) | 0.4512 (3) | 0.0236 (7) | |
H18B | 1.8032 | 1.2167 | 0.4467 | 0.028* | |
C19B | 1.6275 (6) | 1.17396 (12) | 0.5435 (3) | 0.0207 (7) | |
H19B | 1.7488 | 1.1668 | 0.6013 | 0.025* | |
C20B | 1.3810 (6) | 1.12393 (11) | 0.6485 (3) | 0.0177 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0296 (15) | 0.0353 (14) | 0.0200 (13) | 0.0159 (12) | 0.0018 (11) | −0.0055 (11) |
O2A | 0.0238 (14) | 0.0419 (15) | 0.0309 (15) | 0.0135 (12) | −0.0037 (12) | −0.0084 (12) |
O3A | 0.0189 (12) | 0.0247 (12) | 0.0197 (12) | 0.0005 (10) | 0.0037 (10) | 0.0109 (10) |
O4A | 0.0207 (13) | 0.0373 (14) | 0.0248 (13) | 0.0011 (11) | −0.0025 (11) | 0.0113 (11) |
N1A | 0.0120 (14) | 0.0218 (13) | 0.0165 (13) | 0.0012 (10) | 0.0047 (11) | 0.0034 (10) |
N2A | 0.0158 (15) | 0.0230 (13) | 0.0131 (13) | 0.0006 (11) | 0.0041 (11) | −0.0005 (10) |
N3A | 0.0142 (14) | 0.0185 (13) | 0.0233 (14) | −0.0001 (11) | 0.0066 (12) | 0.0028 (11) |
N4A | 0.0207 (16) | 0.0235 (13) | 0.0151 (15) | −0.0013 (11) | 0.0026 (13) | 0.0009 (10) |
C1A | 0.0133 (17) | 0.0268 (16) | 0.0159 (17) | 0.0021 (12) | 0.0071 (14) | 0.0007 (12) |
C2A | 0.0147 (16) | 0.0202 (14) | 0.0224 (16) | 0.0024 (12) | 0.0025 (14) | 0.0006 (12) |
C3A | 0.0167 (16) | 0.0142 (13) | 0.0234 (16) | −0.0028 (12) | 0.0051 (13) | −0.0001 (12) |
C4A | 0.0193 (18) | 0.0213 (15) | 0.0199 (16) | 0.0021 (13) | 0.0015 (14) | 0.0048 (12) |
C5A | 0.0206 (17) | 0.0220 (15) | 0.0147 (15) | −0.0041 (13) | 0.0039 (13) | 0.0002 (12) |
C6A | 0.0215 (19) | 0.0284 (16) | 0.0191 (17) | −0.0011 (14) | 0.0106 (15) | 0.0016 (13) |
C7A | 0.0185 (16) | 0.0189 (14) | 0.0208 (17) | 0.0034 (13) | 0.0065 (14) | 0.0023 (12) |
C8A | 0.0239 (18) | 0.0193 (15) | 0.0282 (18) | 0.0051 (13) | 0.0098 (15) | 0.0041 (13) |
C9A | 0.032 (2) | 0.0209 (16) | 0.042 (2) | 0.0125 (15) | 0.0225 (19) | 0.0130 (15) |
C10A | 0.047 (3) | 0.0246 (17) | 0.037 (2) | 0.0112 (17) | 0.025 (2) | 0.0055 (16) |
C11A | 0.048 (3) | 0.0217 (17) | 0.0239 (19) | 0.0019 (17) | 0.0082 (18) | −0.0002 (14) |
C12A | 0.0269 (19) | 0.0250 (16) | 0.0212 (17) | 0.0013 (14) | 0.0044 (15) | 0.0022 (13) |
C13A | 0.0195 (18) | 0.0222 (15) | 0.0211 (17) | 0.0015 (13) | 0.0045 (15) | −0.0015 (13) |
C14A | 0.0156 (16) | 0.0175 (14) | 0.0175 (15) | −0.0001 (12) | 0.0040 (13) | −0.0009 (12) |
C15A | 0.0164 (16) | 0.0184 (14) | 0.0206 (15) | 0.0027 (12) | 0.0045 (13) | 0.0006 (12) |
C16A | 0.0219 (17) | 0.0240 (16) | 0.0222 (17) | 0.0024 (13) | 0.0016 (15) | 0.0031 (13) |
C17A | 0.0301 (19) | 0.0194 (15) | 0.0250 (18) | 0.0019 (14) | 0.0114 (15) | 0.0047 (13) |
C18A | 0.0209 (17) | 0.0153 (14) | 0.0274 (18) | −0.0010 (13) | 0.0109 (15) | 0.0037 (13) |
C19A | 0.0151 (15) | 0.0195 (14) | 0.0215 (16) | 0.0029 (12) | 0.0037 (13) | 0.0027 (12) |
C20A | 0.0179 (17) | 0.0169 (13) | 0.0159 (15) | 0.0018 (12) | 0.0017 (13) | 0.0010 (12) |
O1B | 0.0321 (15) | 0.0292 (13) | 0.0185 (12) | 0.0177 (11) | 0.0021 (11) | −0.0039 (10) |
O2B | 0.0256 (14) | 0.0373 (14) | 0.0285 (14) | 0.0148 (12) | −0.0057 (12) | −0.0073 (12) |
O3B | 0.0218 (13) | 0.0245 (12) | 0.0211 (13) | −0.0012 (10) | 0.0000 (11) | 0.0087 (10) |
O4B | 0.0267 (15) | 0.0341 (13) | 0.0243 (13) | 0.0020 (11) | −0.0053 (12) | 0.0125 (11) |
N1B | 0.0199 (15) | 0.0130 (11) | 0.0128 (12) | −0.0006 (10) | 0.0020 (11) | −0.0012 (10) |
N2B | 0.0188 (15) | 0.0091 (10) | 0.0130 (12) | −0.0010 (10) | 0.0012 (11) | 0.0007 (9) |
N3B | 0.0151 (14) | 0.0246 (14) | 0.0226 (15) | 0.0002 (11) | 0.0061 (12) | −0.0032 (11) |
N4B | 0.0247 (17) | 0.0173 (12) | 0.0114 (14) | −0.0016 (11) | 0.0024 (12) | −0.0011 (9) |
C1B | 0.0200 (18) | 0.0083 (13) | 0.0152 (16) | −0.0010 (10) | 0.0040 (14) | 0.0011 (9) |
C2B | 0.0145 (16) | 0.0238 (15) | 0.0210 (16) | 0.0035 (13) | 0.0011 (14) | 0.0043 (13) |
C3B | 0.0208 (17) | 0.0198 (14) | 0.0208 (16) | −0.0031 (13) | 0.0047 (14) | −0.0021 (12) |
C4B | 0.0210 (18) | 0.0218 (15) | 0.0127 (15) | 0.0031 (13) | −0.0014 (13) | 0.0035 (12) |
C5B | 0.0218 (18) | 0.0157 (13) | 0.0161 (15) | −0.0015 (12) | 0.0019 (14) | −0.0037 (11) |
C6B | 0.027 (2) | 0.0203 (14) | 0.0177 (17) | 0.0009 (14) | 0.0103 (15) | 0.0016 (12) |
C7B | 0.0272 (18) | 0.0079 (12) | 0.0173 (15) | −0.0006 (12) | 0.0034 (14) | −0.0001 (11) |
C8B | 0.0235 (18) | 0.0145 (14) | 0.0205 (16) | −0.0009 (13) | 0.0044 (14) | −0.0008 (12) |
C9B | 0.033 (2) | 0.0241 (17) | 0.033 (2) | 0.0045 (15) | 0.0145 (17) | 0.0029 (14) |
C10B | 0.051 (3) | 0.0181 (15) | 0.033 (2) | 0.0030 (17) | 0.022 (2) | −0.0070 (15) |
C11B | 0.053 (3) | 0.0260 (18) | 0.0198 (17) | −0.0006 (18) | 0.0073 (18) | −0.0065 (14) |
C12B | 0.031 (2) | 0.0188 (15) | 0.0204 (17) | −0.0020 (14) | 0.0008 (15) | −0.0005 (13) |
C13B | 0.0230 (17) | 0.0133 (13) | 0.0175 (16) | 0.0023 (12) | 0.0006 (14) | −0.0029 (12) |
C14B | 0.0196 (16) | 0.0085 (12) | 0.0139 (14) | 0.0016 (11) | 0.0031 (13) | −0.0011 (10) |
C15B | 0.0173 (16) | 0.0114 (12) | 0.0192 (15) | −0.0006 (11) | 0.0011 (13) | 0.0016 (11) |
C16B | 0.0231 (17) | 0.0176 (14) | 0.0156 (15) | 0.0005 (13) | −0.0005 (13) | 0.0007 (12) |
C17B | 0.0281 (18) | 0.0168 (14) | 0.0197 (16) | 0.0010 (14) | 0.0055 (14) | 0.0039 (13) |
C18B | 0.0171 (17) | 0.0245 (16) | 0.0298 (19) | −0.0006 (13) | 0.0052 (15) | −0.0053 (14) |
C19B | 0.0181 (16) | 0.0210 (14) | 0.0216 (16) | 0.0033 (13) | −0.0005 (14) | −0.0042 (12) |
C20B | 0.0237 (18) | 0.0123 (13) | 0.0161 (16) | 0.0017 (12) | −0.0003 (14) | −0.0008 (11) |
Geometric parameters (Å, º) top
O1A—C13A | 1.316 (4) | O1B—C13B | 1.316 (4) |
O1A—H1O1 | 0.840 (19) | O1B—H2O1 | 0.83 (2) |
O2A—C13A | 1.214 (4) | O2B—C13B | 1.216 (4) |
O3A—C20A | 1.309 (4) | O3B—C20B | 1.310 (4) |
O3A—H1O3 | 0.837 (19) | O3B—H2O3 | 0.84 (2) |
O4A—C20A | 1.218 (4) | O4B—C20B | 1.221 (4) |
N1A—C3A | 1.474 (4) | N1B—C1B | 1.477 (4) |
N1A—C1A | 1.476 (4) | N1B—C3B | 1.480 (4) |
N1A—C4A | 1.487 (4) | N1B—C4B | 1.491 (4) |
N2A—C2A | 1.476 (4) | N2B—C1B | 1.477 (4) |
N2A—C1A | 1.486 (4) | N2B—C2B | 1.480 (4) |
N2A—C5A | 1.487 (4) | N2B—C5B | 1.481 (4) |
N3A—C3A | 1.465 (4) | N3B—C3B | 1.462 (4) |
N3A—C2A | 1.466 (4) | N3B—C2B | 1.466 (4) |
N3A—C6A | 1.472 (4) | N3B—C6B | 1.468 (4) |
N4A—C5A | 1.458 (4) | N4B—C4B | 1.458 (4) |
N4A—C4A | 1.465 (4) | N4B—C6B | 1.467 (5) |
N4A—C6A | 1.466 (5) | N4B—C5B | 1.472 (4) |
C1A—H1AA | 0.9900 | C1B—H1BA | 0.9900 |
C1A—H1AB | 0.9900 | C1B—H1BB | 0.9900 |
C2A—H2AA | 0.9900 | C2B—H2BA | 0.9900 |
C2A—H2AB | 0.9900 | C2B—H2BB | 0.9900 |
C3A—H3AA | 0.9900 | C3B—H3BA | 0.9900 |
C3A—H3AB | 0.9900 | C3B—H3BB | 0.9900 |
C4A—H4AA | 0.9900 | C4B—H4BA | 0.9900 |
C4A—H4AB | 0.9900 | C4B—H4BB | 0.9900 |
C5A—H5AA | 0.9900 | C5B—H5BA | 0.9900 |
C5A—H5AB | 0.9900 | C5B—H5BB | 0.9900 |
C6A—H6AA | 0.9900 | C6B—H6BA | 0.9900 |
C6A—H6AB | 0.9900 | C6B—H6BB | 0.9900 |
C7A—C12A | 1.383 (5) | C7B—C8B | 1.386 (5) |
C7A—C8A | 1.394 (5) | C7B—C12B | 1.399 (5) |
C7A—C13A | 1.492 (5) | C7B—C13B | 1.473 (5) |
C8A—C9A | 1.394 (5) | C8B—C9B | 1.393 (5) |
C8A—H8AA | 0.9500 | C8B—H8BA | 0.9500 |
C9A—C10A | 1.369 (6) | C9B—C10B | 1.385 (6) |
C9A—H9AA | 0.9500 | C9B—H9BA | 0.9500 |
C10A—C11A | 1.381 (6) | C10B—C11B | 1.373 (6) |
C10A—H10A | 0.9500 | C10B—H10B | 0.9500 |
C11A—C12A | 1.388 (5) | C11B—C12B | 1.392 (5) |
C11A—H11A | 0.9500 | C11B—H11B | 0.9500 |
C12A—H12A | 0.9500 | C12B—H12B | 0.9500 |
C14A—C15A | 1.385 (4) | C14B—C15B | 1.388 (4) |
C14A—C19A | 1.398 (5) | C14B—C19B | 1.395 (5) |
C14A—C20A | 1.490 (5) | C14B—C20B | 1.484 (4) |
C15A—C16A | 1.389 (5) | C15B—C16B | 1.388 (4) |
C15A—H15A | 0.9500 | C15B—H15B | 0.9500 |
C16A—C17A | 1.382 (5) | C16B—C17B | 1.388 (5) |
C16A—H16A | 0.9500 | C16B—H16B | 0.9500 |
C17A—C18A | 1.384 (5) | C17B—C18B | 1.383 (5) |
C17A—H17A | 0.9500 | C17B—H17B | 0.9500 |
C18A—C19A | 1.388 (4) | C18B—C19B | 1.396 (5) |
C18A—H18A | 0.9500 | C18B—H18B | 0.9500 |
C19A—H19A | 0.9500 | C19B—H19B | 0.9500 |
| | | |
C13A—O1A—H1O1 | 105 (3) | C13B—O1B—H2O1 | 109 (4) |
C20A—O3A—H1O3 | 107 (3) | C20B—O3B—H2O3 | 112 (4) |
C3A—N1A—C1A | 108.2 (2) | C1B—N1B—C3B | 107.7 (3) |
C3A—N1A—C4A | 108.8 (3) | C1B—N1B—C4B | 108.2 (2) |
C1A—N1A—C4A | 107.8 (2) | C3B—N1B—C4B | 108.4 (2) |
C2A—N2A—C1A | 108.1 (2) | C1B—N2B—C2B | 108.5 (2) |
C2A—N2A—C5A | 108.8 (2) | C1B—N2B—C5B | 107.9 (2) |
C1A—N2A—C5A | 108.2 (2) | C2B—N2B—C5B | 109.1 (2) |
C3A—N3A—C2A | 108.1 (3) | C3B—N3B—C2B | 108.6 (3) |
C3A—N3A—C6A | 108.7 (3) | C3B—N3B—C6B | 108.8 (3) |
C2A—N3A—C6A | 107.3 (3) | C2B—N3B—C6B | 108.3 (3) |
C5A—N4A—C4A | 108.6 (3) | C4B—N4B—C6B | 108.3 (3) |
C5A—N4A—C6A | 109.0 (3) | C4B—N4B—C5B | 108.8 (3) |
C4A—N4A—C6A | 108.0 (3) | C6B—N4B—C5B | 108.1 (3) |
N1A—C1A—N2A | 111.0 (3) | N1B—C1B—N2B | 111.5 (3) |
N1A—C1A—H1AA | 109.4 | N1B—C1B—H1BA | 109.3 |
N2A—C1A—H1AA | 109.4 | N2B—C1B—H1BA | 109.3 |
N1A—C1A—H1AB | 109.4 | N1B—C1B—H1BB | 109.3 |
N2A—C1A—H1AB | 109.4 | N2B—C1B—H1BB | 109.3 |
H1AA—C1A—H1AB | 108.0 | H1BA—C1B—H1BB | 108.0 |
N3A—C2A—N2A | 112.2 (2) | N3B—C2B—N2B | 111.0 (2) |
N3A—C2A—H2AA | 109.2 | N3B—C2B—H2BA | 109.4 |
N2A—C2A—H2AA | 109.2 | N2B—C2B—H2BA | 109.4 |
N3A—C2A—H2AB | 109.2 | N3B—C2B—H2BB | 109.4 |
N2A—C2A—H2AB | 109.2 | N2B—C2B—H2BB | 109.4 |
H2AA—C2A—H2AB | 107.9 | H2BA—C2B—H2BB | 108.0 |
N3A—C3A—N1A | 111.8 (2) | N3B—C3B—N1B | 111.7 (2) |
N3A—C3A—H3AA | 109.3 | N3B—C3B—H3BA | 109.3 |
N1A—C3A—H3AA | 109.3 | N1B—C3B—H3BA | 109.3 |
N3A—C3A—H3AB | 109.3 | N3B—C3B—H3BB | 109.3 |
N1A—C3A—H3AB | 109.3 | N1B—C3B—H3BB | 109.3 |
H3AA—C3A—H3AB | 107.9 | H3BA—C3B—H3BB | 107.9 |
N4A—C4A—N1A | 111.8 (3) | N4B—C4B—N1B | 111.6 (2) |
N4A—C4A—H4AA | 109.3 | N4B—C4B—H4BA | 109.3 |
N1A—C4A—H4AA | 109.3 | N1B—C4B—H4BA | 109.3 |
N4A—C4A—H4AB | 109.3 | N4B—C4B—H4BB | 109.3 |
N1A—C4A—H4AB | 109.3 | N1B—C4B—H4BB | 109.3 |
H4AA—C4A—H4AB | 107.9 | H4BA—C4B—H4BB | 108.0 |
N4A—C5A—N2A | 111.0 (3) | N4B—C5B—N2B | 111.3 (2) |
N4A—C5A—H5AA | 109.4 | N4B—C5B—H5BA | 109.4 |
N2A—C5A—H5AA | 109.4 | N2B—C5B—H5BA | 109.4 |
N4A—C5A—H5AB | 109.4 | N4B—C5B—H5BB | 109.4 |
N2A—C5A—H5AB | 109.4 | N2B—C5B—H5BB | 109.4 |
H5AA—C5A—H5AB | 108.0 | H5BA—C5B—H5BB | 108.0 |
N4A—C6A—N3A | 112.8 (3) | N4B—C6B—N3B | 112.5 (3) |
N4A—C6A—H6AA | 109.0 | N4B—C6B—H6BA | 109.1 |
N3A—C6A—H6AA | 109.0 | N3B—C6B—H6BA | 109.1 |
N4A—C6A—H6AB | 109.0 | N4B—C6B—H6BB | 109.1 |
N3A—C6A—H6AB | 109.0 | N3B—C6B—H6BB | 109.1 |
H6AA—C6A—H6AB | 107.8 | H6BA—C6B—H6BB | 107.8 |
C12A—C7A—C8A | 120.5 (3) | C8B—C7B—C12B | 119.5 (3) |
C12A—C7A—C13A | 118.3 (3) | C8B—C7B—C13B | 121.8 (3) |
C8A—C7A—C13A | 121.1 (3) | C12B—C7B—C13B | 118.5 (3) |
C9A—C8A—C7A | 119.0 (3) | C7B—C8B—C9B | 120.2 (3) |
C9A—C8A—H8AA | 120.5 | C7B—C8B—H8BA | 119.9 |
C7A—C8A—H8AA | 120.5 | C9B—C8B—H8BA | 119.9 |
C10A—C9A—C8A | 120.4 (4) | C10B—C9B—C8B | 119.8 (4) |
C10A—C9A—H9AA | 119.8 | C10B—C9B—H9BA | 120.1 |
C8A—C9A—H9AA | 119.8 | C8B—C9B—H9BA | 120.1 |
C9A—C10A—C11A | 120.5 (4) | C11B—C10B—C9B | 120.3 (3) |
C9A—C10A—H10A | 119.7 | C11B—C10B—H10B | 119.9 |
C11A—C10A—H10A | 119.7 | C9B—C10B—H10B | 119.9 |
C10A—C11A—C12A | 120.1 (4) | C10B—C11B—C12B | 120.5 (3) |
C10A—C11A—H11A | 120.0 | C10B—C11B—H11B | 119.8 |
C12A—C11A—H11A | 120.0 | C12B—C11B—H11B | 119.8 |
C7A—C12A—C11A | 119.5 (3) | C11B—C12B—C7B | 119.6 (3) |
C7A—C12A—H12A | 120.2 | C11B—C12B—H12B | 120.2 |
C11A—C12A—H12A | 120.2 | C7B—C12B—H12B | 120.2 |
O2A—C13A—O1A | 123.4 (3) | O2B—C13B—O1B | 122.5 (3) |
O2A—C13A—C7A | 122.1 (3) | O2B—C13B—C7B | 123.2 (3) |
O1A—C13A—C7A | 114.4 (3) | O1B—C13B—C7B | 114.3 (3) |
C15A—C14A—C19A | 119.7 (3) | C15B—C14B—C19B | 119.6 (3) |
C15A—C14A—C20A | 120.9 (3) | C15B—C14B—C20B | 120.7 (3) |
C19A—C14A—C20A | 119.3 (3) | C19B—C14B—C20B | 119.7 (3) |
C14A—C15A—C16A | 120.5 (3) | C16B—C15B—C14B | 120.8 (3) |
C14A—C15A—H15A | 119.7 | C16B—C15B—H15B | 119.6 |
C16A—C15A—H15A | 119.7 | C14B—C15B—H15B | 119.6 |
C17A—C16A—C15A | 119.6 (3) | C15B—C16B—C17B | 119.4 (3) |
C17A—C16A—H16A | 120.2 | C15B—C16B—H16B | 120.3 |
C15A—C16A—H16A | 120.2 | C17B—C16B—H16B | 120.3 |
C16A—C17A—C18A | 120.2 (3) | C18B—C17B—C16B | 120.5 (3) |
C16A—C17A—H17A | 119.9 | C18B—C17B—H17B | 119.7 |
C18A—C17A—H17A | 119.9 | C16B—C17B—H17B | 119.7 |
C17A—C18A—C19A | 120.5 (3) | C17B—C18B—C19B | 120.0 (3) |
C17A—C18A—H18A | 119.7 | C17B—C18B—H18B | 120.0 |
C19A—C18A—H18A | 119.7 | C19B—C18B—H18B | 120.0 |
C18A—C19A—C14A | 119.4 (3) | C14B—C19B—C18B | 119.7 (3) |
C18A—C19A—H19A | 120.3 | C14B—C19B—H19B | 120.2 |
C14A—C19A—H19A | 120.3 | C18B—C19B—H19B | 120.2 |
O4A—C20A—O3A | 123.4 (3) | O4B—C20B—O3B | 123.4 (3) |
O4A—C20A—C14A | 122.3 (3) | O4B—C20B—C14B | 122.1 (3) |
O3A—C20A—C14A | 114.2 (3) | O3B—C20B—C14B | 114.5 (3) |
| | | |
C3A—N1A—C1A—N2A | 59.0 (3) | C3B—N1B—C1B—N2B | 58.5 (3) |
C4A—N1A—C1A—N2A | −58.6 (3) | C4B—N1B—C1B—N2B | −58.5 (3) |
C2A—N2A—C1A—N1A | −58.4 (3) | C2B—N2B—C1B—N1B | −58.7 (3) |
C5A—N2A—C1A—N1A | 59.3 (3) | C5B—N2B—C1B—N1B | 59.3 (3) |
C3A—N3A—C2A—N2A | −58.9 (3) | C3B—N3B—C2B—N2B | −59.5 (3) |
C6A—N3A—C2A—N2A | 58.2 (3) | C6B—N3B—C2B—N2B | 58.5 (3) |
C1A—N2A—C2A—N3A | 58.6 (3) | C1B—N2B—C2B—N3B | 58.8 (3) |
C5A—N2A—C2A—N3A | −58.7 (3) | C5B—N2B—C2B—N3B | −58.5 (3) |
C2A—N3A—C3A—N1A | 59.2 (3) | C2B—N3B—C3B—N1B | 60.1 (3) |
C6A—N3A—C3A—N1A | −57.0 (3) | C6B—N3B—C3B—N1B | −57.6 (3) |
C1A—N1A—C3A—N3A | −59.7 (3) | C1B—N1B—C3B—N3B | −59.2 (3) |
C4A—N1A—C3A—N3A | 57.2 (3) | C4B—N1B—C3B—N3B | 57.6 (3) |
C5A—N4A—C4A—N1A | −59.9 (3) | C6B—N4B—C4B—N1B | 58.4 (3) |
C6A—N4A—C4A—N1A | 58.2 (3) | C5B—N4B—C4B—N1B | −58.8 (3) |
C3A—N1A—C4A—N4A | −58.1 (3) | C1B—N1B—C4B—N4B | 58.2 (3) |
C1A—N1A—C4A—N4A | 59.1 (3) | C3B—N1B—C4B—N4B | −58.3 (3) |
C4A—N4A—C5A—N2A | 59.8 (3) | C4B—N4B—C5B—N2B | 59.7 (3) |
C6A—N4A—C5A—N2A | −57.6 (3) | C6B—N4B—C5B—N2B | −57.7 (3) |
C2A—N2A—C5A—N4A | 57.6 (3) | C1B—N2B—C5B—N4B | −59.5 (3) |
C1A—N2A—C5A—N4A | −59.6 (3) | C2B—N2B—C5B—N4B | 58.2 (3) |
C5A—N4A—C6A—N3A | 59.2 (4) | C4B—N4B—C6B—N3B | −58.7 (3) |
C4A—N4A—C6A—N3A | −58.6 (3) | C5B—N4B—C6B—N3B | 59.0 (3) |
C3A—N3A—C6A—N4A | 58.1 (3) | C3B—N3B—C6B—N4B | 58.3 (3) |
C2A—N3A—C6A—N4A | −58.5 (3) | C2B—N3B—C6B—N4B | −59.6 (3) |
C12A—C7A—C8A—C9A | 1.5 (5) | C12B—C7B—C8B—C9B | −1.8 (5) |
C13A—C7A—C8A—C9A | −176.1 (3) | C13B—C7B—C8B—C9B | −176.9 (3) |
C7A—C8A—C9A—C10A | −1.3 (5) | C7B—C8B—C9B—C10B | 0.2 (5) |
C8A—C9A—C10A—C11A | 0.7 (6) | C8B—C9B—C10B—C11B | 0.7 (5) |
C9A—C10A—C11A—C12A | −0.3 (6) | C9B—C10B—C11B—C12B | 0.1 (6) |
C8A—C7A—C12A—C11A | −1.2 (5) | C10B—C11B—C12B—C7B | −1.7 (5) |
C13A—C7A—C12A—C11A | 176.5 (3) | C8B—C7B—C12B—C11B | 2.5 (5) |
C10A—C11A—C12A—C7A | 0.6 (5) | C13B—C7B—C12B—C11B | 177.8 (3) |
C12A—C7A—C13A—O2A | −8.4 (5) | C8B—C7B—C13B—O2B | 164.4 (3) |
C8A—C7A—C13A—O2A | 169.3 (3) | C12B—C7B—C13B—O2B | −10.8 (5) |
C12A—C7A—C13A—O1A | 171.9 (3) | C8B—C7B—C13B—O1B | −13.9 (5) |
C8A—C7A—C13A—O1A | −10.4 (5) | C12B—C7B—C13B—O1B | 170.9 (3) |
C19A—C14A—C15A—C16A | 0.0 (5) | C19B—C14B—C15B—C16B | −1.7 (4) |
C20A—C14A—C15A—C16A | −178.9 (3) | C20B—C14B—C15B—C16B | −179.9 (3) |
C14A—C15A—C16A—C17A | −1.3 (5) | C14B—C15B—C16B—C17B | 1.3 (5) |
C15A—C16A—C17A—C18A | 2.2 (5) | C15B—C16B—C17B—C18B | −0.8 (5) |
C16A—C17A—C18A—C19A | −1.7 (5) | C16B—C17B—C18B—C19B | 0.8 (5) |
C17A—C18A—C19A—C14A | 0.3 (5) | C15B—C14B—C19B—C18B | 1.7 (5) |
C15A—C14A—C19A—C18A | 0.5 (5) | C20B—C14B—C19B—C18B | 179.9 (3) |
C20A—C14A—C19A—C18A | 179.4 (3) | C17B—C18B—C19B—C14B | −1.3 (5) |
C15A—C14A—C20A—O4A | 173.5 (3) | C15B—C14B—C20B—O4B | 171.3 (3) |
C19A—C14A—C20A—O4A | −5.4 (5) | C19B—C14B—C20B—O4B | −6.9 (5) |
C15A—C14A—C20A—O3A | −4.7 (4) | C15B—C14B—C20B—O3B | −7.1 (4) |
C19A—C14A—C20A—O3A | 176.4 (3) | C19B—C14B—C20B—O3B | 174.7 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1O1···N1A | 0.84 (4) | 1.81 (4) | 2.648 (4) | 175 (4) |
O3A—H1O3···N2A | 0.84 (4) | 1.76 (4) | 2.589 (3) | 169 (4) |
O1B—H2O1···N1B | 0.83 (6) | 1.81 (5) | 2.627 (4) | 170 (5) |
O3B—H2O3···N2B | 0.85 (5) | 1.75 (5) | 2.593 (3) | 176 (4) |
C1A—H1AA···O2A | 0.99 | 2.57 | 3.246 (4) | 125 |
C2A—H2AA···O4Ai | 0.99 | 2.44 | 3.108 (4) | 124 |
C5A—H5AA···O2Aii | 0.99 | 2.57 | 3.199 (4) | 121 |
C2B—H2BA···O4Bi | 0.99 | 2.46 | 3.141 (4) | 126 |
C5B—H5BA···O2Biii | 0.99 | 2.54 | 3.216 (4) | 125 |
C3A—H3AB···Cg17iv | 0.99 | 2.67 | 3.652 (3) | 169 |
C10A—H10A···Cg16v | 0.95 | 2.91 | 3.765 (4) | 150 |
C10B—H10B···Cg17vi | 0.95 | 2.80 | 3.612 (4) | 144 |
C5A—H5AB···Cg15iv | 0.99 | 2.77 | 3.711 (4) | 159 |
C17A—H17A···Cg18vii | 0.95 | 2.76 | 3.640 (4) | 154 |
C3B—H3BB···Cg18viii | 0.99 | 2.70 | 3.680 (3) | 171 |
C5B—H5BB···Cg16viii | 0.99 | 2.78 | 3.718 (3) | 157 |
Symmetry codes: (i) x−1, y, z; (ii) x+1/2, −y+1, z+1/2; (iii) x+1/2, −y+2, z+1/2; (iv) x−1/2, −y+1, z+1/2; (v) x−1/2, −y+1, z−1/2; (vi) x+1, y, z; (vii) x−1/2, −y+2, z−1/2; (viii) x−1/2, −y+2, z+1/2. |
Hexamethylenetetramine bis(benzoic acid) (1533066)
top
Crystal data top
C6H12N4·2(C7H6O2) | F(000) = 816 |
Mr = 384.43 | Dx = 1.317 Mg m−3 |
Monoclinic, Pn | Mo Kα radiation, λ = 0.71073 Å |
a = 6.1262 (6) Å | Cell parameters from 9928 reflections |
b = 26.531 (2) Å | θ = 2.3–28.3° |
c = 12.0982 (11) Å | µ = 0.09 mm−1 |
β = 99.5055 (16)° | T = 200 K |
V = 1939.4 (3) Å3 | Block, colourless |
Z = 4 | 0.76 × 0.39 × 0.21 mm |
Data collection top
Bruker APEX Duo CCD area detector diffractometer | 4805 independent reflections |
Radiation source: fine-focus sealed tube | 3599 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
φ and ω scans | θmax = 28.3°, θmin = 1.9° |
Absorption correction: multi-scan (TWINABS; Sheldrick, 2012) | h = −8→8 |
Tmin = 0.606, Tmax = 0.937 | k = 0→35 |
6280 measured reflections | l = 0→16 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.046 | w = 1/[σ2(Fo2) + (0.0326P)2 + 0.4932P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.109 | (Δ/σ)max = 0.001 |
S = 1.09 | Δρmax = 0.17 e Å−3 |
4805 reflections | Δρmin = −0.18 e Å−3 |
522 parameters | Absolute structure: No quotients, so Flack parameter determined by classical intensity fit |
6 restraints | Absolute structure parameter: −1.0 (10) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1A | 0.6811 (5) | 0.38031 (11) | 0.4634 (2) | 0.0551 (8) | |
O2A | 0.4058 (5) | 0.39921 (12) | 0.3279 (3) | 0.0685 (10) | |
O3A | 0.4250 (4) | 0.61015 (10) | 0.3981 (2) | 0.0423 (6) | |
O4A | 0.7860 (4) | 0.60515 (10) | 0.4608 (2) | 0.0544 (7) | |
N1A | 0.4818 (4) | 0.44969 (10) | 0.5697 (2) | 0.0316 (6) | |
N2A | 0.3965 (4) | 0.53913 (10) | 0.5442 (2) | 0.0303 (6) | |
N3A | 0.1351 (4) | 0.48288 (11) | 0.6133 (2) | 0.0378 (7) | |
N4A | 0.4850 (5) | 0.50457 (11) | 0.7321 (2) | 0.0387 (7) | |
C1A | 0.5005 (5) | 0.49476 (12) | 0.5005 (3) | 0.0328 (8) | |
H1AA | 0.4281 | 0.4881 | 0.4225 | 0.039* | |
H1AB | 0.6588 | 0.5020 | 0.4995 | 0.039* | |
C2A | 0.1603 (5) | 0.52740 (12) | 0.5444 (3) | 0.0373 (8) | |
H2AA | 0.0880 | 0.5567 | 0.5739 | 0.045* | |
H2AB | 0.0857 | 0.5212 | 0.4666 | 0.045* | |
C3A | 0.2426 (5) | 0.44020 (12) | 0.5692 (3) | 0.0362 (7) | |
H3AA | 0.1689 | 0.4333 | 0.4915 | 0.043* | |
H3AB | 0.2256 | 0.4100 | 0.6150 | 0.043* | |
C4A | 0.5871 (5) | 0.46114 (13) | 0.6853 (3) | 0.0392 (8) | |
H4AA | 0.5757 | 0.4313 | 0.7331 | 0.047* | |
H4AB | 0.7461 | 0.4682 | 0.6864 | 0.047* | |
C5A | 0.5058 (6) | 0.54840 (13) | 0.6608 (3) | 0.0361 (8) | |
H5AA | 0.6644 | 0.5559 | 0.6617 | 0.043* | |
H5AB | 0.4377 | 0.5781 | 0.6909 | 0.043* | |
C6A | 0.2492 (6) | 0.49343 (14) | 0.7275 (3) | 0.0439 (9) | |
H6AA | 0.1771 | 0.5225 | 0.7579 | 0.053* | |
H6AB | 0.2338 | 0.4639 | 0.7756 | 0.053* | |
C7A | 0.6923 (6) | 0.34692 (12) | 0.2835 (3) | 0.0355 (8) | |
C8A | 0.9082 (6) | 0.33028 (13) | 0.3165 (3) | 0.0437 (9) | |
H8AA | 0.9838 | 0.3367 | 0.3902 | 0.052* | |
C9A | 1.0119 (8) | 0.30431 (15) | 0.2405 (4) | 0.0595 (12) | |
H9AA | 1.1607 | 0.2934 | 0.2617 | 0.071* | |
C10A | 0.9015 (10) | 0.29420 (16) | 0.1353 (4) | 0.0696 (14) | |
H10A | 0.9735 | 0.2760 | 0.0841 | 0.083* | |
C11A | 0.6875 (9) | 0.31015 (16) | 0.1032 (4) | 0.0634 (12) | |
H11A | 0.6116 | 0.3030 | 0.0299 | 0.076* | |
C12A | 0.5824 (7) | 0.33663 (13) | 0.1776 (3) | 0.0467 (9) | |
H12A | 0.4342 | 0.3477 | 0.1555 | 0.056* | |
C13A | 0.5775 (5) | 0.37778 (13) | 0.3597 (3) | 0.0383 (8) | |
C14A | 0.6644 (5) | 0.65404 (12) | 0.2981 (3) | 0.0300 (7) | |
C15A | 0.4878 (5) | 0.66744 (12) | 0.2171 (3) | 0.0354 (7) | |
H15A | 0.3433 | 0.6560 | 0.2230 | 0.043* | |
C16A | 0.5192 (6) | 0.69744 (14) | 0.1275 (3) | 0.0465 (9) | |
H16A | 0.3969 | 0.7064 | 0.0720 | 0.056* | |
C17A | 0.7283 (7) | 0.71424 (13) | 0.1191 (3) | 0.0466 (9) | |
H17A | 0.7502 | 0.7351 | 0.0581 | 0.056* | |
C18A | 0.9051 (6) | 0.70085 (13) | 0.1988 (3) | 0.0441 (9) | |
H18A | 1.0493 | 0.7124 | 0.1924 | 0.053* | |
C19A | 0.8752 (6) | 0.67062 (12) | 0.2886 (3) | 0.0372 (8) | |
H19A | 0.9983 | 0.6613 | 0.3433 | 0.045* | |
C20A | 0.6317 (5) | 0.62094 (11) | 0.3945 (3) | 0.0318 (7) | |
O1B | 1.4441 (5) | 0.88285 (10) | 0.7172 (2) | 0.0524 (8) | |
O2B | 1.1756 (5) | 0.90136 (11) | 0.5778 (2) | 0.0643 (9) | |
O3B | 1.1805 (4) | 1.11090 (9) | 0.6509 (2) | 0.0437 (6) | |
O4B | 1.5399 (4) | 1.10890 (11) | 0.7184 (2) | 0.0571 (8) | |
N1B | 1.2385 (4) | 0.95116 (9) | 0.8214 (2) | 0.0292 (6) | |
N2B | 1.1504 (4) | 1.04067 (9) | 0.7987 (2) | 0.0291 (6) | |
N3B | 0.8914 (4) | 0.98348 (11) | 0.8659 (2) | 0.0381 (7) | |
N4B | 1.2404 (5) | 1.00429 (9) | 0.9854 (2) | 0.0349 (7) | |
C1B | 1.2569 (6) | 0.99692 (10) | 0.7543 (3) | 0.0299 (7) | |
H1BA | 1.1864 | 0.9907 | 0.6758 | 0.036* | |
H1BB | 1.4152 | 1.0045 | 0.7545 | 0.036* | |
C2B | 0.9147 (5) | 1.02809 (12) | 0.7984 (3) | 0.0378 (8) | |
H2BA | 0.8404 | 1.0570 | 0.8282 | 0.045* | |
H2BB | 0.8408 | 1.0220 | 0.7203 | 0.045* | |
C3B | 1.0005 (5) | 0.94129 (11) | 0.8198 (3) | 0.0356 (7) | |
H3BA | 0.9278 | 0.9351 | 0.7417 | 0.043* | |
H3BB | 0.9836 | 0.9105 | 0.8640 | 0.043* | |
C4B | 1.3436 (5) | 0.96148 (11) | 0.9383 (3) | 0.0348 (7) | |
H4BA | 1.3312 | 0.9312 | 0.9848 | 0.042* | |
H4BB | 1.5029 | 0.9686 | 0.9403 | 0.042* | |
C5B | 1.2593 (6) | 1.04872 (11) | 0.9159 (3) | 0.0342 (7) | |
H5BA | 1.4177 | 1.0565 | 0.9171 | 0.041* | |
H5BB | 1.1905 | 1.0780 | 0.9475 | 0.041* | |
C6B | 1.0039 (6) | 0.99324 (13) | 0.9805 (3) | 0.0393 (8) | |
H6BA | 0.9878 | 0.9634 | 1.0277 | 0.047* | |
H6BB | 0.9320 | 1.0222 | 1.0117 | 0.047* | |
C7B | 1.4619 (6) | 0.84718 (10) | 0.5417 (3) | 0.0342 (8) | |
C8B | 1.6789 (6) | 0.83186 (12) | 0.5768 (3) | 0.0400 (8) | |
H8BA | 1.7540 | 0.8407 | 0.6493 | 0.048* | |
C9B | 1.7858 (8) | 0.80343 (14) | 0.5050 (4) | 0.0591 (12) | |
H9BA | 1.9354 | 0.7934 | 0.5278 | 0.071* | |
C10B | 1.6747 (10) | 0.78983 (16) | 0.4010 (4) | 0.0719 (15) | |
H10B | 1.7459 | 0.7694 | 0.3532 | 0.086* | |
C11B | 1.4610 (10) | 0.80578 (16) | 0.3661 (4) | 0.0706 (15) | |
H11B | 1.3864 | 0.7970 | 0.2935 | 0.085* | |
C12B | 1.3550 (7) | 0.83431 (14) | 0.4356 (3) | 0.0511 (10) | |
H12B | 1.2075 | 0.8453 | 0.4107 | 0.061* | |
C13B | 1.3445 (6) | 0.87889 (11) | 0.6135 (3) | 0.0356 (7) | |
C14B | 1.4200 (5) | 1.15473 (10) | 0.5517 (3) | 0.0272 (6) | |
C15B | 1.2457 (5) | 1.16471 (10) | 0.4658 (3) | 0.0312 (7) | |
H15B | 1.1027 | 1.1516 | 0.4694 | 0.037* | |
C16B | 1.2794 (6) | 1.19375 (11) | 0.3746 (3) | 0.0366 (7) | |
H16B | 1.1596 | 1.2005 | 0.3159 | 0.044* | |
C17B | 1.4870 (6) | 1.21281 (13) | 0.3693 (3) | 0.0431 (8) | |
H17B | 1.5096 | 1.2329 | 0.3072 | 0.052* | |
C18B | 1.6617 (6) | 1.20269 (12) | 0.4539 (3) | 0.0451 (9) | |
H18B | 1.8045 | 1.2158 | 0.4499 | 0.054* | |
C19B | 1.6293 (6) | 1.17350 (12) | 0.5447 (3) | 0.0399 (8) | |
H19B | 1.7503 | 1.1663 | 0.6024 | 0.048* | |
C20B | 1.3858 (6) | 1.12314 (11) | 0.6491 (3) | 0.0341 (7) | |
H1O1 | 0.617 (6) | 0.4006 (13) | 0.500 (3) | 0.063 (13)* | |
H1O3 | 0.425 (9) | 0.5875 (13) | 0.446 (3) | 0.082 (16)* | |
H2O1 | 1.367 (7) | 0.9023 (15) | 0.749 (4) | 0.085 (17)* | |
H2O3 | 1.173 (9) | 1.0893 (16) | 0.701 (3) | 0.10 (2)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.0583 (18) | 0.0661 (18) | 0.0402 (16) | 0.0321 (15) | 0.0061 (14) | −0.0067 (13) |
O2A | 0.0473 (16) | 0.090 (2) | 0.063 (2) | 0.0328 (16) | −0.0077 (15) | −0.0202 (17) |
O3A | 0.0348 (13) | 0.0524 (15) | 0.0405 (15) | −0.0005 (11) | 0.0087 (11) | 0.0204 (12) |
O4A | 0.0389 (14) | 0.0680 (17) | 0.0525 (17) | 0.0040 (13) | −0.0035 (12) | 0.0279 (14) |
N1A | 0.0276 (14) | 0.0391 (14) | 0.0303 (14) | 0.0030 (11) | 0.0108 (11) | 0.0045 (11) |
N2A | 0.0279 (14) | 0.0414 (15) | 0.0234 (14) | −0.0003 (11) | 0.0092 (11) | 0.0044 (11) |
N3A | 0.0261 (13) | 0.0474 (16) | 0.0438 (17) | −0.0013 (12) | 0.0174 (12) | 0.0054 (14) |
N4A | 0.0416 (17) | 0.0518 (18) | 0.0235 (16) | −0.0005 (12) | 0.0076 (13) | 0.0022 (11) |
C1A | 0.0288 (16) | 0.0483 (19) | 0.0254 (18) | 0.0000 (13) | 0.0163 (14) | 0.0013 (12) |
C2A | 0.0266 (16) | 0.0415 (18) | 0.045 (2) | 0.0056 (13) | 0.0078 (14) | 0.0051 (15) |
C3A | 0.0301 (16) | 0.0399 (18) | 0.0397 (18) | −0.0057 (13) | 0.0086 (14) | 0.0026 (14) |
C4A | 0.0306 (17) | 0.052 (2) | 0.0338 (18) | 0.0038 (15) | 0.0028 (14) | 0.0095 (15) |
C5A | 0.0389 (18) | 0.0435 (18) | 0.0262 (17) | −0.0088 (14) | 0.0058 (14) | 0.0004 (13) |
C6A | 0.048 (2) | 0.049 (2) | 0.041 (2) | −0.0008 (16) | 0.0242 (18) | 0.0039 (16) |
C7A | 0.0401 (18) | 0.0328 (16) | 0.0357 (19) | 0.0032 (14) | 0.0121 (15) | 0.0033 (13) |
C8A | 0.0427 (19) | 0.0374 (18) | 0.053 (2) | 0.0092 (15) | 0.0153 (17) | 0.0094 (16) |
C9A | 0.060 (3) | 0.051 (2) | 0.077 (3) | 0.022 (2) | 0.040 (2) | 0.017 (2) |
C10A | 0.102 (4) | 0.052 (2) | 0.066 (3) | 0.020 (3) | 0.048 (3) | 0.006 (2) |
C11A | 0.093 (4) | 0.057 (3) | 0.043 (2) | 0.002 (2) | 0.017 (2) | −0.0052 (19) |
C12A | 0.056 (2) | 0.0396 (18) | 0.045 (2) | 0.0040 (17) | 0.0099 (18) | 0.0013 (16) |
C13A | 0.0349 (18) | 0.0386 (17) | 0.042 (2) | 0.0061 (14) | 0.0084 (16) | −0.0023 (15) |
C14A | 0.0294 (15) | 0.0311 (15) | 0.0312 (16) | 0.0041 (12) | 0.0101 (13) | 0.0008 (12) |
C15A | 0.0333 (17) | 0.0378 (17) | 0.0363 (18) | 0.0026 (13) | 0.0090 (14) | 0.0038 (14) |
C16A | 0.050 (2) | 0.052 (2) | 0.038 (2) | 0.0076 (17) | 0.0084 (17) | 0.0138 (16) |
C17A | 0.062 (2) | 0.0389 (19) | 0.044 (2) | 0.0022 (17) | 0.0254 (19) | 0.0135 (16) |
C18A | 0.0370 (18) | 0.0434 (19) | 0.058 (2) | −0.0020 (15) | 0.0254 (17) | 0.0067 (17) |
C19A | 0.0326 (17) | 0.0365 (17) | 0.0440 (19) | 0.0052 (14) | 0.0108 (15) | 0.0019 (14) |
C20A | 0.0335 (16) | 0.0296 (14) | 0.0323 (17) | 0.0053 (13) | 0.0054 (14) | 0.0047 (13) |
O1B | 0.0646 (19) | 0.0537 (16) | 0.0358 (15) | 0.0328 (14) | −0.0006 (13) | −0.0081 (12) |
O2B | 0.0567 (19) | 0.0695 (18) | 0.0585 (18) | 0.0313 (15) | −0.0150 (15) | −0.0201 (15) |
O3B | 0.0441 (14) | 0.0429 (14) | 0.0417 (16) | −0.0010 (11) | 0.0004 (12) | 0.0177 (11) |
O4B | 0.0477 (16) | 0.0676 (18) | 0.0498 (17) | 0.0063 (13) | −0.0104 (13) | 0.0272 (14) |
N1B | 0.0356 (15) | 0.0220 (11) | 0.0298 (14) | 0.0041 (10) | 0.0047 (11) | 0.0003 (10) |
N2B | 0.0382 (15) | 0.0212 (11) | 0.0267 (14) | 0.0009 (10) | 0.0013 (12) | 0.0035 (9) |
N3B | 0.0327 (14) | 0.0393 (15) | 0.0441 (17) | −0.0012 (12) | 0.0110 (13) | −0.0006 (13) |
N4B | 0.0506 (18) | 0.0292 (13) | 0.0231 (15) | −0.0031 (11) | 0.0012 (13) | 0.0004 (10) |
C1B | 0.0398 (18) | 0.0229 (14) | 0.0275 (18) | 0.0005 (11) | 0.0075 (15) | 0.0026 (10) |
C2B | 0.0330 (17) | 0.0392 (17) | 0.0402 (19) | 0.0097 (13) | 0.0027 (15) | 0.0051 (14) |
C3B | 0.0408 (18) | 0.0244 (14) | 0.0412 (19) | −0.0075 (13) | 0.0055 (15) | −0.0017 (13) |
C4B | 0.0409 (19) | 0.0319 (15) | 0.0292 (17) | 0.0069 (14) | −0.0007 (14) | 0.0072 (13) |
C5B | 0.0452 (19) | 0.0251 (14) | 0.0310 (17) | −0.0047 (13) | 0.0024 (15) | −0.0070 (12) |
C6B | 0.054 (2) | 0.0399 (17) | 0.0292 (19) | −0.0004 (15) | 0.0221 (17) | 0.0019 (14) |
C7B | 0.054 (2) | 0.0170 (13) | 0.0316 (17) | −0.0004 (13) | 0.0078 (15) | 0.0011 (11) |
C8B | 0.051 (2) | 0.0290 (16) | 0.0411 (19) | 0.0040 (15) | 0.0126 (16) | −0.0011 (14) |
C9B | 0.072 (3) | 0.041 (2) | 0.071 (3) | 0.015 (2) | 0.031 (2) | 0.0038 (19) |
C10B | 0.123 (5) | 0.046 (2) | 0.058 (3) | 0.017 (3) | 0.045 (3) | −0.008 (2) |
C11B | 0.124 (5) | 0.050 (2) | 0.038 (2) | 0.003 (3) | 0.014 (3) | −0.0147 (19) |
C12B | 0.071 (3) | 0.0425 (19) | 0.038 (2) | −0.0018 (19) | 0.0031 (19) | −0.0021 (16) |
C13B | 0.0422 (19) | 0.0283 (15) | 0.0351 (18) | 0.0056 (14) | 0.0026 (15) | −0.0010 (13) |
C14B | 0.0354 (16) | 0.0177 (12) | 0.0270 (15) | 0.0028 (11) | 0.0008 (13) | −0.0029 (11) |
C15B | 0.0349 (17) | 0.0242 (13) | 0.0323 (16) | 0.0005 (12) | −0.0009 (13) | 0.0025 (12) |
C16B | 0.0447 (19) | 0.0274 (15) | 0.0347 (17) | 0.0011 (14) | −0.0020 (14) | 0.0049 (13) |
C17B | 0.055 (2) | 0.0312 (17) | 0.043 (2) | −0.0001 (16) | 0.0093 (17) | 0.0074 (15) |
C18B | 0.0397 (19) | 0.0348 (17) | 0.061 (2) | −0.0053 (15) | 0.0086 (17) | −0.0035 (17) |
C19B | 0.0346 (17) | 0.0347 (16) | 0.048 (2) | −0.0001 (14) | −0.0008 (15) | −0.0043 (15) |
C20B | 0.046 (2) | 0.0256 (14) | 0.0281 (17) | 0.0031 (14) | −0.0005 (15) | 0.0019 (12) |
Geometric parameters (Å, º) top
O1A—C13A | 1.311 (4) | O1B—C13B | 1.305 (4) |
O1A—H1O1 | 0.833 (19) | O1B—H2O1 | 0.84 (2) |
O2A—C13A | 1.202 (4) | O2B—C13B | 1.211 (4) |
O3A—C20A | 1.306 (4) | O3B—C20B | 1.303 (4) |
O3A—H1O3 | 0.84 (2) | O3B—H2O3 | 0.84 (2) |
O4A—C20A | 1.209 (4) | O4B—C20B | 1.215 (4) |
N1A—C4A | 1.472 (4) | N1B—C1B | 1.475 (4) |
N1A—C1A | 1.475 (4) | N1B—C3B | 1.478 (4) |
N1A—C3A | 1.486 (4) | N1B—C4B | 1.479 (4) |
N2A—C1A | 1.477 (4) | N2B—C1B | 1.475 (4) |
N2A—C5A | 1.479 (4) | N2B—C5B | 1.479 (4) |
N2A—C2A | 1.481 (4) | N2B—C2B | 1.482 (4) |
N3A—C3A | 1.455 (4) | N3B—C2B | 1.458 (4) |
N3A—C6A | 1.468 (5) | N3B—C3B | 1.461 (4) |
N3A—C2A | 1.469 (4) | N3B—C6B | 1.466 (4) |
N4A—C5A | 1.466 (4) | N4B—C4B | 1.460 (4) |
N4A—C6A | 1.467 (5) | N4B—C5B | 1.464 (4) |
N4A—C4A | 1.468 (5) | N4B—C6B | 1.470 (5) |
C1A—H1AA | 0.9900 | C1B—H1BA | 0.9900 |
C1A—H1AB | 0.9900 | C1B—H1BB | 0.9900 |
C2A—H2AA | 0.9900 | C2B—H2BA | 0.9900 |
C2A—H2AB | 0.9900 | C2B—H2BB | 0.9900 |
C3A—H3AA | 0.9900 | C3B—H3BA | 0.9900 |
C3A—H3AB | 0.9900 | C3B—H3BB | 0.9900 |
C4A—H4AA | 0.9900 | C4B—H4BA | 0.9900 |
C4A—H4AB | 0.9900 | C4B—H4BB | 0.9900 |
C5A—H5AA | 0.9900 | C5B—H5BA | 0.9900 |
C5A—H5AB | 0.9900 | C5B—H5BB | 0.9900 |
C6A—H6AA | 0.9900 | C6B—H6BA | 0.9900 |
C6A—H6AB | 0.9900 | C6B—H6BB | 0.9900 |
C7A—C12A | 1.372 (5) | C7B—C12B | 1.385 (5) |
C7A—C8A | 1.389 (5) | C7B—C8B | 1.388 (5) |
C7A—C13A | 1.493 (5) | C7B—C13B | 1.479 (5) |
C8A—C9A | 1.384 (5) | C8B—C9B | 1.393 (5) |
C8A—H8AA | 0.9500 | C8B—H8BA | 0.9500 |
C9A—C10A | 1.366 (7) | C9B—C10B | 1.376 (7) |
C9A—H9AA | 0.9500 | C9B—H9BA | 0.9500 |
C10A—C11A | 1.371 (7) | C10B—C11B | 1.374 (7) |
C10A—H10A | 0.9500 | C10B—H10B | 0.9500 |
C11A—C12A | 1.382 (6) | C11B—C12B | 1.372 (6) |
C11A—H11A | 0.9500 | C11B—H11B | 0.9500 |
C12A—H12A | 0.9500 | C12B—H12B | 0.9500 |
C14A—C15A | 1.381 (4) | C14B—C15B | 1.387 (4) |
C14A—C19A | 1.387 (4) | C14B—C19B | 1.391 (5) |
C14A—C20A | 1.500 (4) | C14B—C20B | 1.488 (4) |
C15A—C16A | 1.383 (5) | C15B—C16B | 1.389 (4) |
C15A—H15A | 0.9500 | C15B—H15B | 0.9500 |
C16A—C17A | 1.376 (5) | C16B—C17B | 1.380 (5) |
C16A—H16A | 0.9500 | C16B—H16B | 0.9500 |
C17A—C18A | 1.373 (5) | C17B—C18B | 1.380 (5) |
C17A—H17A | 0.9500 | C17B—H17B | 0.9500 |
C18A—C19A | 1.387 (5) | C18B—C19B | 1.385 (5) |
C18A—H18A | 0.9500 | C18B—H18B | 0.9500 |
C19A—H19A | 0.9500 | C19B—H19B | 0.9500 |
| | | |
C13A—O1A—H1O1 | 110 (3) | C13B—O1B—H2O1 | 107 (4) |
C20A—O3A—H1O3 | 107 (4) | C20B—O3B—H2O3 | 110 (4) |
C4A—N1A—C1A | 108.0 (2) | C1B—N1B—C3B | 107.7 (2) |
C4A—N1A—C3A | 108.4 (2) | C1B—N1B—C4B | 108.2 (2) |
C1A—N1A—C3A | 107.7 (2) | C3B—N1B—C4B | 108.6 (2) |
C1A—N2A—C5A | 108.6 (2) | C1B—N2B—C5B | 107.8 (2) |
C1A—N2A—C2A | 108.2 (3) | C1B—N2B—C2B | 108.1 (2) |
C5A—N2A—C2A | 108.8 (2) | C5B—N2B—C2B | 108.7 (2) |
C3A—N3A—C6A | 108.6 (3) | C2B—N3B—C3B | 108.4 (3) |
C3A—N3A—C2A | 108.7 (3) | C2B—N3B—C6B | 108.2 (3) |
C6A—N3A—C2A | 107.6 (3) | C3B—N3B—C6B | 108.8 (3) |
C5A—N4A—C6A | 108.5 (3) | C4B—N4B—C5B | 108.8 (3) |
C5A—N4A—C4A | 108.2 (3) | C4B—N4B—C6B | 108.4 (3) |
C6A—N4A—C4A | 107.8 (3) | C5B—N4B—C6B | 108.0 (3) |
N1A—C1A—N2A | 111.4 (2) | N1B—C1B—N2B | 111.6 (3) |
N1A—C1A—H1AA | 109.4 | N1B—C1B—H1BA | 109.3 |
N2A—C1A—H1AA | 109.4 | N2B—C1B—H1BA | 109.3 |
N1A—C1A—H1AB | 109.4 | N1B—C1B—H1BB | 109.3 |
N2A—C1A—H1AB | 109.4 | N2B—C1B—H1BB | 109.3 |
H1AA—C1A—H1AB | 108.0 | H1BA—C1B—H1BB | 108.0 |
N3A—C2A—N2A | 111.4 (2) | N3B—C2B—N2B | 111.5 (2) |
N3A—C2A—H2AA | 109.4 | N3B—C2B—H2BA | 109.3 |
N2A—C2A—H2AA | 109.4 | N2B—C2B—H2BA | 109.3 |
N3A—C2A—H2AB | 109.4 | N3B—C2B—H2BB | 109.3 |
N2A—C2A—H2AB | 109.4 | N2B—C2B—H2BB | 109.3 |
H2AA—C2A—H2AB | 108.0 | H2BA—C2B—H2BB | 108.0 |
N3A—C3A—N1A | 111.9 (3) | N3B—C3B—N1B | 111.8 (2) |
N3A—C3A—H3AA | 109.2 | N3B—C3B—H3BA | 109.3 |
N1A—C3A—H3AA | 109.2 | N1B—C3B—H3BA | 109.3 |
N3A—C3A—H3AB | 109.2 | N3B—C3B—H3BB | 109.3 |
N1A—C3A—H3AB | 109.2 | N1B—C3B—H3BB | 109.3 |
H3AA—C3A—H3AB | 107.9 | H3BA—C3B—H3BB | 107.9 |
N4A—C4A—N1A | 112.4 (3) | N4B—C4B—N1B | 111.6 (2) |
N4A—C4A—H4AA | 109.1 | N4B—C4B—H4BA | 109.3 |
N1A—C4A—H4AA | 109.1 | N1B—C4B—H4BA | 109.3 |
N4A—C4A—H4AB | 109.1 | N4B—C4B—H4BB | 109.3 |
N1A—C4A—H4AB | 109.1 | N1B—C4B—H4BB | 109.3 |
H4AA—C4A—H4AB | 107.9 | H4BA—C4B—H4BB | 108.0 |
N4A—C5A—N2A | 111.1 (3) | N4B—C5B—N2B | 111.6 (2) |
N4A—C5A—H5AA | 109.4 | N4B—C5B—H5BA | 109.3 |
N2A—C5A—H5AA | 109.4 | N2B—C5B—H5BA | 109.3 |
N4A—C5A—H5AB | 109.4 | N4B—C5B—H5BB | 109.3 |
N2A—C5A—H5AB | 109.4 | N2B—C5B—H5BB | 109.3 |
H5AA—C5A—H5AB | 108.0 | H5BA—C5B—H5BB | 108.0 |
N4A—C6A—N3A | 112.8 (3) | N3B—C6B—N4B | 112.3 (3) |
N4A—C6A—H6AA | 109.0 | N3B—C6B—H6BA | 109.1 |
N3A—C6A—H6AA | 109.0 | N4B—C6B—H6BA | 109.1 |
N4A—C6A—H6AB | 109.0 | N3B—C6B—H6BB | 109.1 |
N3A—C6A—H6AB | 109.0 | N4B—C6B—H6BB | 109.1 |
H6AA—C6A—H6AB | 107.8 | H6BA—C6B—H6BB | 107.9 |
C12A—C7A—C8A | 120.1 (3) | C12B—C7B—C8B | 119.6 (3) |
C12A—C7A—C13A | 118.5 (3) | C12B—C7B—C13B | 118.9 (3) |
C8A—C7A—C13A | 121.4 (3) | C8B—C7B—C13B | 121.4 (3) |
C9A—C8A—C7A | 119.2 (4) | C7B—C8B—C9B | 119.5 (4) |
C9A—C8A—H8AA | 120.4 | C7B—C8B—H8BA | 120.2 |
C7A—C8A—H8AA | 120.4 | C9B—C8B—H8BA | 120.2 |
C10A—C9A—C8A | 120.4 (4) | C10B—C9B—C8B | 120.0 (4) |
C10A—C9A—H9AA | 119.8 | C10B—C9B—H9BA | 120.0 |
C8A—C9A—H9AA | 119.8 | C8B—C9B—H9BA | 120.0 |
C9A—C10A—C11A | 120.4 (4) | C11B—C10B—C9B | 120.2 (4) |
C9A—C10A—H10A | 119.8 | C11B—C10B—H10B | 119.9 |
C11A—C10A—H10A | 119.8 | C9B—C10B—H10B | 119.9 |
C10A—C11A—C12A | 119.9 (4) | C12B—C11B—C10B | 120.3 (4) |
C10A—C11A—H11A | 120.1 | C12B—C11B—H11B | 119.8 |
C12A—C11A—H11A | 120.1 | C10B—C11B—H11B | 119.8 |
C7A—C12A—C11A | 120.0 (4) | C11B—C12B—C7B | 120.3 (4) |
C7A—C12A—H12A | 120.0 | C11B—C12B—H12B | 119.8 |
C11A—C12A—H12A | 120.0 | C7B—C12B—H12B | 119.8 |
O2A—C13A—O1A | 122.9 (3) | O2B—C13B—O1B | 122.7 (3) |
O2A—C13A—C7A | 122.5 (3) | O2B—C13B—C7B | 122.7 (3) |
O1A—C13A—C7A | 114.6 (3) | O1B—C13B—C7B | 114.5 (3) |
C15A—C14A—C19A | 119.4 (3) | C15B—C14B—C19B | 119.3 (3) |
C15A—C14A—C20A | 120.9 (3) | C15B—C14B—C20B | 120.6 (3) |
C19A—C14A—C20A | 119.7 (3) | C19B—C14B—C20B | 120.1 (3) |
C14A—C15A—C16A | 120.7 (3) | C14B—C15B—C16B | 120.3 (3) |
C14A—C15A—H15A | 119.7 | C14B—C15B—H15B | 119.9 |
C16A—C15A—H15A | 119.7 | C16B—C15B—H15B | 119.9 |
C17A—C16A—C15A | 119.7 (3) | C17B—C16B—C15B | 120.0 (3) |
C17A—C16A—H16A | 120.1 | C17B—C16B—H16B | 120.0 |
C15A—C16A—H16A | 120.1 | C15B—C16B—H16B | 120.0 |
C18A—C17A—C16A | 120.0 (3) | C16B—C17B—C18B | 120.1 (3) |
C18A—C17A—H17A | 120.0 | C16B—C17B—H17B | 119.9 |
C16A—C17A—H17A | 120.0 | C18B—C17B—H17B | 119.9 |
C17A—C18A—C19A | 120.6 (3) | C17B—C18B—C19B | 120.2 (3) |
C17A—C18A—H18A | 119.7 | C17B—C18B—H18B | 119.9 |
C19A—C18A—H18A | 119.7 | C19B—C18B—H18B | 119.9 |
C14A—C19A—C18A | 119.6 (3) | C18B—C19B—C14B | 120.2 (3) |
C14A—C19A—H19A | 120.2 | C18B—C19B—H19B | 119.9 |
C18A—C19A—H19A | 120.2 | C14B—C19B—H19B | 119.9 |
O4A—C20A—O3A | 123.9 (3) | O4B—C20B—O3B | 123.6 (3) |
O4A—C20A—C14A | 121.9 (3) | O4B—C20B—C14B | 121.8 (3) |
O3A—C20A—C14A | 114.2 (3) | O3B—C20B—C14B | 114.6 (3) |
| | | |
C4A—N1A—C1A—N2A | −58.0 (3) | C3B—N1B—C1B—N2B | 58.6 (3) |
C3A—N1A—C1A—N2A | 58.9 (3) | C4B—N1B—C1B—N2B | −58.6 (3) |
C5A—N2A—C1A—N1A | 58.7 (3) | C5B—N2B—C1B—N1B | 58.8 (3) |
C2A—N2A—C1A—N1A | −59.2 (3) | C2B—N2B—C1B—N1B | −58.5 (3) |
C3A—N3A—C2A—N2A | −58.9 (3) | C3B—N3B—C2B—N2B | −59.4 (3) |
C6A—N3A—C2A—N2A | 58.6 (3) | C6B—N3B—C2B—N2B | 58.4 (4) |
C1A—N2A—C2A—N3A | 58.7 (3) | C1B—N2B—C2B—N3B | 58.7 (3) |
C5A—N2A—C2A—N3A | −59.2 (3) | C5B—N2B—C2B—N3B | −58.0 (3) |
C6A—N3A—C3A—N1A | −57.6 (3) | C2B—N3B—C3B—N1B | 60.0 (3) |
C2A—N3A—C3A—N1A | 59.2 (3) | C6B—N3B—C3B—N1B | −57.5 (3) |
C4A—N1A—C3A—N3A | 57.5 (3) | C1B—N1B—C3B—N3B | −59.3 (3) |
C1A—N1A—C3A—N3A | −59.1 (3) | C4B—N1B—C3B—N3B | 57.7 (3) |
C5A—N4A—C4A—N1A | −59.4 (3) | C5B—N4B—C4B—N1B | −58.8 (3) |
C6A—N4A—C4A—N1A | 57.8 (4) | C6B—N4B—C4B—N1B | 58.4 (3) |
C1A—N1A—C4A—N4A | 58.7 (3) | C1B—N1B—C4B—N4B | 58.3 (3) |
C3A—N1A—C4A—N4A | −57.8 (3) | C3B—N1B—C4B—N4B | −58.3 (3) |
C6A—N4A—C5A—N2A | −57.7 (4) | C4B—N4B—C5B—N2B | 59.3 (3) |
C4A—N4A—C5A—N2A | 59.0 (3) | C6B—N4B—C5B—N2B | −58.2 (3) |
C1A—N2A—C5A—N4A | −59.2 (3) | C1B—N2B—C5B—N4B | −59.0 (3) |
C2A—N2A—C5A—N4A | 58.4 (3) | C2B—N2B—C5B—N4B | 58.0 (3) |
C5A—N4A—C6A—N3A | 58.9 (4) | C2B—N3B—C6B—N4B | −59.6 (4) |
C4A—N4A—C6A—N3A | −58.1 (4) | C3B—N3B—C6B—N4B | 57.9 (3) |
C3A—N3A—C6A—N4A | 58.6 (4) | C4B—N4B—C6B—N3B | −58.4 (3) |
C2A—N3A—C6A—N4A | −59.0 (4) | C5B—N4B—C6B—N3B | 59.3 (3) |
C12A—C7A—C8A—C9A | 1.4 (5) | C12B—C7B—C8B—C9B | −0.4 (5) |
C13A—C7A—C8A—C9A | −176.3 (3) | C13B—C7B—C8B—C9B | −177.8 (3) |
C7A—C8A—C9A—C10A | −1.4 (6) | C7B—C8B—C9B—C10B | −1.4 (6) |
C8A—C9A—C10A—C11A | 0.7 (7) | C8B—C9B—C10B—C11B | 2.4 (7) |
C9A—C10A—C11A—C12A | 0.0 (7) | C9B—C10B—C11B—C12B | −1.6 (7) |
C8A—C7A—C12A—C11A | −0.7 (5) | C10B—C11B—C12B—C7B | −0.2 (7) |
C13A—C7A—C12A—C11A | 177.0 (3) | C8B—C7B—C12B—C11B | 1.2 (5) |
C10A—C11A—C12A—C7A | 0.0 (6) | C13B—C7B—C12B—C11B | 178.7 (4) |
C12A—C7A—C13A—O2A | −9.8 (5) | C12B—C7B—C13B—O2B | −13.2 (5) |
C8A—C7A—C13A—O2A | 168.0 (4) | C8B—C7B—C13B—O2B | 164.2 (4) |
C12A—C7A—C13A—O1A | 171.5 (3) | C12B—C7B—C13B—O1B | 170.3 (3) |
C8A—C7A—C13A—O1A | −10.8 (5) | C8B—C7B—C13B—O1B | −12.3 (5) |
C19A—C14A—C15A—C16A | −0.5 (5) | C19B—C14B—C15B—C16B | −0.9 (4) |
C20A—C14A—C15A—C16A | −179.1 (3) | C20B—C14B—C15B—C16B | −179.3 (3) |
C14A—C15A—C16A—C17A | −0.2 (5) | C14B—C15B—C16B—C17B | 0.0 (5) |
C15A—C16A—C17A—C18A | 0.6 (6) | C15B—C16B—C17B—C18B | 0.6 (5) |
C16A—C17A—C18A—C19A | −0.4 (6) | C16B—C17B—C18B—C19B | −0.2 (5) |
C15A—C14A—C19A—C18A | 0.8 (5) | C17B—C18B—C19B—C14B | −0.8 (5) |
C20A—C14A—C19A—C18A | 179.4 (3) | C15B—C14B—C19B—C18B | 1.3 (5) |
C17A—C18A—C19A—C14A | −0.3 (5) | C20B—C14B—C19B—C18B | 179.7 (3) |
C15A—C14A—C20A—O4A | 173.4 (3) | C15B—C14B—C20B—O4B | 171.1 (3) |
C19A—C14A—C20A—O4A | −5.2 (5) | C19B—C14B—C20B—O4B | −7.2 (5) |
C15A—C14A—C20A—O3A | −5.1 (4) | C15B—C14B—C20B—O3B | −6.6 (4) |
C19A—C14A—C20A—O3A | 176.2 (3) | C19B—C14B—C20B—O3B | 175.1 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1O1···N1A | 0.84 (4) | 1.82 (4) | 2.656 (4) | 174 (3) |
O3A—H1O3···N2A | 0.84 (4) | 1.78 (4) | 2.609 (4) | 174 (6) |
O1B—H2O1···N1B | 0.84 (4) | 1.82 (4) | 2.643 (4) | 171 (4) |
O3B—H2O3···N2B | 0.84 (4) | 1.77 (4) | 2.610 (3) | 176 (5) |
C2A—H2AA···O4Ai | 0.99 | 2.47 | 3.126 (4) | 123 |
C5A—H5AA···O2Aii | 0.99 | 2.58 | 3.223 (5) | 122 |
C2B—H2BA···O4Bi | 0.99 | 2.50 | 3.174 (4) | 125 |
C5B—H5BA···O2Biii | 0.99 | 2.55 | 3.232 (5) | 126 |
C3A—H3AB···Cg17iv | 0.99 | 2.76 | 3.734 (4) | 169 |
C5A—H5AB···Cg15iv | 0.99 | 2.85 | 3.787 (4) | 159 |
C10A—H10A···Cg16v | 0.95 | 2.97 | 3.829 (5) | 152 |
C10B—H10B···Cg17vi | 0.95 | 2.85 | 3.665 (5) | 145 |
C17A—H17A···Cg18vii | 0.95 | 2.85 | 3.718 (4) | 153 |
C3B—H3BB···Cg18viii | 0.99 | 2.77 | 3.757 (3) | 171 |
C5B—H5BB···Cg16viii | 0.99 | 2.86 | 3.797 (3) | 157 |
Symmetry codes: (i) x−1, y, z; (ii) x+1/2, −y+1, z+1/2; (iii) x+1/2, −y+2, z+1/2; (iv) x−1/2, −y+1, z+1/2; (v) x−1/2, −y+1, z−1/2; (vi) x+1, y, z; (vii) x−1/2, −y+2, z−1/2; (viii) x−1/2, −y+2, z+1/2. |
Hexamethylenetetramine bis(benzoic acid) (1533067)
top
Crystal data top
C6H12N4·2(C7H6O2) | F(000) = 816 |
Mr = 384.43 | Dx = 1.311 Mg m−3 |
Monoclinic, Pn | Mo Kα radiation, λ = 0.71073 Å |
a = 6.1343 (9) Å | Cell parameters from 4974 reflections |
b = 26.629 (4) Å | θ = 2.9–28.3° |
c = 12.0933 (18) Å | µ = 0.09 mm−1 |
β = 99.514 (3)° | T = 220 K |
V = 1948.3 (5) Å3 | Block, colourless |
Z = 4 | 0.76 × 0.39 × 0.21 mm |
Data collection top
Bruker APEX Duo CCD area detector diffractometer | 4871 independent reflections |
Radiation source: fine-focus sealed tube | 2951 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.065 |
φ and ω scans | θmax = 28.4°, θmin = 1.5° |
Absorption correction: multi-scan (TWINABS; Sheldrick, 2012) | h = −8→8 |
Tmin = 0.701, Tmax = 0.937 | k = 0→35 |
6362 measured reflections | l = 0→16 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.063 | w = 1/[σ2(Fo2) + (0.086P)2 + 0.3083P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.190 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.23 e Å−3 |
4871 reflections | Δρmin = −0.23 e Å−3 |
522 parameters | Absolute structure: No quotients, so Flack parameter determined by classical intensity fit |
6 restraints | Absolute structure parameter: −0.9 (14) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1A | 0.3220 (8) | 0.61940 (18) | 0.5375 (4) | 0.0626 (14) | |
H1O1 | 0.371 (12) | 0.599 (2) | 0.497 (6) | 0.09 (3)* | |
O2A | 0.5941 (8) | 0.60048 (19) | 0.6733 (4) | 0.0765 (17) | |
O3A | 0.5763 (6) | 0.38972 (16) | 0.6023 (3) | 0.0490 (11) | |
H1O3 | 0.589 (13) | 0.412 (2) | 0.556 (5) | 0.09 (2)* | |
O4A | 0.2146 (7) | 0.39497 (16) | 0.5394 (4) | 0.0625 (13) | |
N1A | 0.5209 (7) | 0.55005 (15) | 0.4300 (4) | 0.0353 (10) | |
N2A | 0.6064 (6) | 0.46071 (15) | 0.4553 (3) | 0.0347 (10) | |
N3A | 0.8661 (7) | 0.51701 (18) | 0.3870 (4) | 0.0421 (11) | |
N4A | 0.5148 (9) | 0.49569 (17) | 0.2678 (4) | 0.0449 (13) | |
C1A | 0.5017 (9) | 0.50516 (18) | 0.4994 (5) | 0.0366 (13) | |
H1AA | 0.3453 | 0.4981 | 0.5003 | 0.044* | |
H1AB | 0.5733 | 0.5117 | 0.5767 | 0.044* | |
C2A | 0.8416 (8) | 0.47322 (19) | 0.4553 (5) | 0.0429 (13) | |
H2AA | 0.9144 | 0.4796 | 0.5324 | 0.052* | |
H2AB | 0.9151 | 0.4445 | 0.4266 | 0.052* | |
C3A | 0.7584 (9) | 0.55963 (18) | 0.4316 (5) | 0.0424 (13) | |
H3AA | 0.7758 | 0.5896 | 0.3868 | 0.051* | |
H3AB | 0.8303 | 0.5662 | 0.5088 | 0.051* | |
C4A | 0.4163 (8) | 0.5389 (2) | 0.3147 (5) | 0.0423 (13) | |
H4AA | 0.2586 | 0.5325 | 0.3133 | 0.051* | |
H4AB | 0.4294 | 0.5684 | 0.2676 | 0.051* | |
C5A | 0.4949 (9) | 0.45239 (19) | 0.3401 (4) | 0.0412 (13) | |
H5AA | 0.3381 | 0.4455 | 0.3404 | 0.049* | |
H5AB | 0.5590 | 0.4228 | 0.3094 | 0.049* | |
C6A | 0.7505 (11) | 0.5065 (2) | 0.2721 (5) | 0.0502 (16) | |
H6AA | 0.7663 | 0.5355 | 0.2243 | 0.060* | |
H6AB | 0.8209 | 0.4776 | 0.2419 | 0.060* | |
C7A | 0.3083 (10) | 0.6532 (2) | 0.7148 (5) | 0.0429 (14) | |
C8A | 0.0923 (10) | 0.6696 (2) | 0.6838 (6) | 0.0502 (16) | |
H8AA | 0.0160 | 0.6630 | 0.6113 | 0.060* | |
C9A | −0.0098 (13) | 0.6955 (2) | 0.7589 (7) | 0.066 (2) | |
H9AA | −0.1564 | 0.7064 | 0.7377 | 0.080* | |
C10A | 0.0981 (16) | 0.7054 (3) | 0.8628 (7) | 0.081 (3) | |
H10A | 0.0258 | 0.7230 | 0.9136 | 0.098* | |
C11A | 0.3165 (15) | 0.6898 (3) | 0.8961 (7) | 0.073 (2) | |
H11A | 0.3921 | 0.6971 | 0.9683 | 0.087* | |
C12A | 0.4190 (11) | 0.6635 (2) | 0.8216 (5) | 0.0525 (15) | |
H12A | 0.5654 | 0.6525 | 0.8432 | 0.063* | |
C13A | 0.4242 (9) | 0.6221 (2) | 0.6414 (5) | 0.0427 (14) | |
C14A | 0.3383 (9) | 0.34606 (18) | 0.7015 (5) | 0.0359 (12) | |
C15A | 0.5132 (9) | 0.33283 (19) | 0.7834 (4) | 0.0397 (13) | |
H15A | 0.6558 | 0.3446 | 0.7787 | 0.048* | |
C16A | 0.4820 (10) | 0.3024 (2) | 0.8725 (5) | 0.0522 (15) | |
H16A | 0.6022 | 0.2932 | 0.9275 | 0.063* | |
C17A | 0.2725 (12) | 0.2858 (2) | 0.8790 (5) | 0.0554 (17) | |
H17A | 0.2504 | 0.2647 | 0.9386 | 0.067* | |
C18A | 0.0957 (10) | 0.2993 (2) | 0.8005 (6) | 0.0490 (15) | |
H18A | −0.0469 | 0.2880 | 0.8072 | 0.059* | |
C19A | 0.1264 (9) | 0.32930 (19) | 0.7116 (5) | 0.0398 (13) | |
H19A | 0.0046 | 0.3386 | 0.6576 | 0.048* | |
C20A | 0.3699 (9) | 0.37923 (18) | 0.6061 (5) | 0.0378 (12) | |
O1B | −0.4438 (8) | 0.11695 (17) | 0.2823 (4) | 0.0610 (14) | |
H2O1 | −0.351 (12) | 0.098 (3) | 0.262 (8) | 0.12 (4)* | |
O2B | −0.1755 (8) | 0.09856 (17) | 0.4222 (4) | 0.0743 (17) | |
O3B | −0.1816 (7) | −0.11056 (15) | 0.3494 (4) | 0.0506 (11) | |
H2O3 | −0.166 (18) | −0.089 (3) | 0.302 (7) | 0.16 (5)* | |
O4B | −0.5399 (7) | −0.10897 (18) | 0.2810 (4) | 0.0696 (15) | |
N1B | −0.2361 (7) | 0.04854 (14) | 0.1793 (4) | 0.0367 (10) | |
N2B | −0.1514 (7) | −0.04063 (14) | 0.2017 (4) | 0.0337 (10) | |
N3B | 0.1077 (7) | 0.01580 (18) | 0.1350 (4) | 0.0427 (11) | |
N4B | −0.2397 (8) | −0.00403 (14) | 0.0154 (4) | 0.0401 (12) | |
C1B | −0.2575 (10) | 0.00291 (15) | 0.2464 (5) | 0.0338 (13) | |
H1BA | −0.1886 | 0.0088 | 0.3244 | 0.041* | |
H1BB | −0.4144 | −0.0044 | 0.2455 | 0.041* | |
C2B | 0.0847 (9) | −0.02831 (19) | 0.2023 (5) | 0.0439 (14) | |
H2BA | 0.1576 | −0.0223 | 0.2795 | 0.053* | |
H2BB | 0.1578 | −0.0569 | 0.1728 | 0.053* | |
C3B | −0.0011 (9) | 0.05823 (18) | 0.1814 (5) | 0.0422 (13) | |
H3BA | 0.0706 | 0.0643 | 0.2588 | 0.051* | |
H3BB | 0.0163 | 0.0885 | 0.1377 | 0.051* | |
C4B | −0.3428 (9) | 0.03858 (18) | 0.0629 (5) | 0.0426 (13) | |
H4BA | −0.5000 | 0.0315 | 0.0615 | 0.051* | |
H4BB | −0.3313 | 0.0685 | 0.0170 | 0.051* | |
C5B | −0.2601 (10) | −0.04884 (17) | 0.0850 (4) | 0.0399 (13) | |
H5BA | −0.4168 | −0.0564 | 0.0837 | 0.048* | |
H5BB | −0.1924 | −0.0777 | 0.0537 | 0.048* | |
C6B | −0.0063 (11) | 0.0068 (2) | 0.0204 (5) | 0.0470 (15) | |
H6BA | 0.0097 | 0.0364 | −0.0255 | 0.056* | |
H6BB | 0.0641 | −0.0216 | −0.0115 | 0.056* | |
C7B | −0.4616 (10) | 0.15290 (16) | 0.4588 (5) | 0.0394 (13) | |
C8B | −0.6795 (10) | 0.1683 (2) | 0.4236 (5) | 0.0468 (14) | |
H8BA | −0.7538 | 0.1596 | 0.3519 | 0.056* | |
C9B | −0.7845 (14) | 0.1963 (2) | 0.4940 (7) | 0.069 (2) | |
H9BA | −0.9320 | 0.2062 | 0.4708 | 0.083* | |
C10B | −0.6758 (17) | 0.2099 (3) | 0.5979 (7) | 0.084 (3) | |
H10B | −0.7484 | 0.2297 | 0.6451 | 0.101* | |
C11B | −0.4601 (17) | 0.1948 (3) | 0.6339 (7) | 0.076 (2) | |
H11B | −0.3862 | 0.2041 | 0.7053 | 0.092* | |
C12B | −0.3531 (12) | 0.1657 (2) | 0.5637 (6) | 0.0588 (17) | |
H12B | −0.2072 | 0.1548 | 0.5879 | 0.071* | |
C13B | −0.3466 (10) | 0.12076 (18) | 0.3868 (5) | 0.0411 (13) | |
C14B | −0.4202 (8) | −0.15433 (16) | 0.4486 (4) | 0.0326 (11) | |
C15B | −0.2465 (8) | −0.16474 (17) | 0.5346 (4) | 0.0364 (12) | |
H15B | −0.1050 | −0.1519 | 0.5313 | 0.044* | |
C16B | −0.2797 (10) | −0.19391 (18) | 0.6252 (5) | 0.0447 (14) | |
H16B | −0.1613 | −0.2008 | 0.6832 | 0.054* | |
C17B | −0.4859 (11) | −0.2127 (2) | 0.6300 (6) | 0.0513 (16) | |
H17B | −0.5087 | −0.2326 | 0.6913 | 0.062* | |
C18B | −0.6610 (11) | −0.2025 (2) | 0.5451 (6) | 0.0545 (17) | |
H18B | −0.8019 | −0.2155 | 0.5492 | 0.065* | |
C19B | −0.6304 (10) | −0.1737 (2) | 0.4556 (5) | 0.0460 (14) | |
H19B | −0.7503 | −0.1668 | 0.3985 | 0.055* | |
C20B | −0.3863 (9) | −0.12296 (18) | 0.3524 (5) | 0.0399 (13) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.067 (3) | 0.071 (3) | 0.049 (3) | 0.036 (2) | 0.007 (3) | −0.008 (2) |
O2A | 0.057 (3) | 0.102 (4) | 0.065 (3) | 0.038 (3) | −0.008 (3) | −0.025 (3) |
O3A | 0.040 (2) | 0.064 (3) | 0.043 (3) | −0.0016 (18) | 0.010 (2) | 0.023 (2) |
O4A | 0.043 (2) | 0.076 (3) | 0.065 (3) | 0.007 (2) | −0.002 (2) | 0.028 (2) |
N1A | 0.031 (2) | 0.046 (2) | 0.031 (2) | 0.0050 (18) | 0.0123 (19) | 0.0092 (18) |
N2A | 0.028 (2) | 0.047 (2) | 0.032 (3) | −0.0019 (18) | 0.013 (2) | 0.0042 (19) |
N3A | 0.027 (2) | 0.051 (3) | 0.052 (3) | −0.008 (2) | 0.020 (2) | 0.005 (2) |
N4A | 0.048 (3) | 0.058 (3) | 0.031 (3) | −0.003 (2) | 0.011 (2) | 0.0058 (19) |
C1A | 0.029 (3) | 0.055 (3) | 0.030 (3) | −0.001 (2) | 0.016 (2) | 0.001 (2) |
C2A | 0.028 (3) | 0.048 (3) | 0.055 (4) | 0.001 (2) | 0.013 (3) | 0.004 (3) |
C3A | 0.037 (3) | 0.039 (3) | 0.053 (4) | −0.005 (2) | 0.011 (3) | 0.001 (2) |
C4A | 0.030 (3) | 0.058 (3) | 0.042 (3) | 0.009 (2) | 0.015 (2) | 0.012 (3) |
C5A | 0.047 (3) | 0.047 (3) | 0.033 (3) | −0.010 (2) | 0.018 (3) | 0.001 (2) |
C6A | 0.058 (4) | 0.058 (3) | 0.043 (4) | 0.000 (3) | 0.033 (3) | 0.009 (3) |
C7A | 0.048 (3) | 0.038 (3) | 0.046 (4) | 0.008 (2) | 0.014 (3) | 0.001 (2) |
C8A | 0.047 (3) | 0.043 (3) | 0.067 (4) | 0.012 (3) | 0.026 (3) | 0.012 (3) |
C9A | 0.067 (5) | 0.058 (4) | 0.083 (6) | 0.029 (3) | 0.038 (4) | 0.016 (4) |
C10A | 0.123 (8) | 0.057 (4) | 0.081 (6) | 0.024 (4) | 0.065 (5) | 0.008 (4) |
C11A | 0.099 (6) | 0.062 (4) | 0.058 (5) | −0.002 (4) | 0.018 (4) | −0.005 (4) |
C12A | 0.068 (4) | 0.047 (3) | 0.042 (4) | 0.007 (3) | 0.011 (3) | 0.005 (3) |
C13A | 0.040 (3) | 0.042 (3) | 0.046 (4) | 0.008 (2) | 0.007 (3) | −0.005 (2) |
C14A | 0.038 (3) | 0.036 (2) | 0.037 (3) | 0.000 (2) | 0.016 (2) | 0.001 (2) |
C15A | 0.041 (3) | 0.044 (3) | 0.038 (3) | −0.001 (2) | 0.016 (3) | 0.004 (2) |
C16A | 0.055 (4) | 0.059 (3) | 0.043 (4) | 0.004 (3) | 0.008 (3) | 0.016 (3) |
C17A | 0.077 (5) | 0.048 (3) | 0.049 (4) | −0.001 (3) | 0.030 (3) | 0.014 (3) |
C18A | 0.041 (3) | 0.047 (3) | 0.066 (4) | −0.004 (2) | 0.028 (3) | 0.008 (3) |
C19A | 0.031 (3) | 0.042 (3) | 0.050 (3) | 0.003 (2) | 0.017 (2) | 0.001 (2) |
C20A | 0.039 (3) | 0.033 (2) | 0.042 (3) | 0.004 (2) | 0.008 (3) | 0.004 (2) |
O1B | 0.073 (3) | 0.065 (3) | 0.040 (3) | 0.036 (2) | −0.006 (2) | −0.008 (2) |
O2B | 0.064 (3) | 0.080 (3) | 0.068 (3) | 0.036 (3) | −0.020 (3) | −0.020 (3) |
O3B | 0.044 (2) | 0.050 (2) | 0.055 (3) | −0.0019 (18) | 0.001 (2) | 0.021 (2) |
O4B | 0.052 (3) | 0.078 (3) | 0.070 (3) | 0.005 (2) | −0.017 (2) | 0.035 (3) |
N1B | 0.042 (3) | 0.0254 (18) | 0.043 (3) | 0.0027 (17) | 0.007 (2) | −0.0019 (17) |
N2B | 0.042 (3) | 0.0253 (18) | 0.033 (2) | 0.0017 (16) | 0.002 (2) | 0.0027 (16) |
N3B | 0.035 (3) | 0.048 (2) | 0.048 (3) | 0.005 (2) | 0.014 (2) | 0.003 (2) |
N4B | 0.056 (3) | 0.039 (2) | 0.024 (3) | −0.0011 (19) | −0.001 (2) | 0.0011 (16) |
C1B | 0.041 (3) | 0.027 (2) | 0.033 (3) | 0.0027 (17) | 0.006 (3) | 0.0002 (17) |
C2B | 0.035 (3) | 0.048 (3) | 0.046 (3) | 0.012 (2) | 0.000 (3) | 0.000 (2) |
C3B | 0.044 (3) | 0.038 (3) | 0.044 (3) | −0.006 (2) | 0.005 (3) | −0.003 (2) |
C4B | 0.041 (3) | 0.044 (3) | 0.040 (3) | 0.009 (2) | 0.000 (3) | 0.008 (2) |
C5B | 0.052 (3) | 0.034 (2) | 0.032 (3) | −0.005 (2) | 0.002 (3) | −0.007 (2) |
C6B | 0.062 (4) | 0.049 (3) | 0.034 (4) | 0.004 (3) | 0.020 (3) | 0.001 (2) |
C7B | 0.059 (4) | 0.021 (2) | 0.038 (3) | −0.001 (2) | 0.008 (3) | 0.000 (2) |
C8B | 0.053 (4) | 0.039 (3) | 0.050 (4) | 0.007 (2) | 0.012 (3) | 0.000 (2) |
C9B | 0.084 (5) | 0.053 (4) | 0.076 (5) | 0.019 (3) | 0.032 (4) | 0.003 (3) |
C10B | 0.138 (9) | 0.059 (4) | 0.067 (5) | 0.017 (5) | 0.049 (6) | −0.014 (4) |
C11B | 0.120 (8) | 0.064 (4) | 0.046 (4) | 0.003 (5) | 0.017 (4) | −0.017 (4) |
C12B | 0.075 (5) | 0.049 (3) | 0.047 (4) | 0.000 (3) | −0.005 (3) | −0.004 (3) |
C13B | 0.047 (3) | 0.036 (2) | 0.039 (3) | 0.005 (2) | 0.004 (3) | −0.004 (2) |
C14B | 0.034 (3) | 0.024 (2) | 0.036 (3) | 0.0059 (18) | −0.003 (2) | −0.003 (2) |
C15B | 0.039 (3) | 0.036 (2) | 0.034 (3) | 0.005 (2) | 0.002 (2) | 0.006 (2) |
C16B | 0.052 (4) | 0.038 (3) | 0.041 (3) | 0.004 (2) | −0.001 (3) | 0.007 (2) |
C17B | 0.059 (4) | 0.038 (3) | 0.059 (4) | 0.004 (3) | 0.016 (3) | 0.007 (3) |
C18B | 0.047 (4) | 0.039 (3) | 0.074 (5) | −0.003 (3) | 0.002 (3) | −0.007 (3) |
C19B | 0.039 (3) | 0.045 (3) | 0.052 (4) | 0.000 (2) | 0.000 (3) | −0.001 (3) |
C20B | 0.046 (3) | 0.034 (2) | 0.036 (3) | 0.006 (2) | −0.005 (3) | 0.000 (2) |
Geometric parameters (Å, º) top
O1A—C13A | 1.310 (7) | O1B—C13B | 1.309 (7) |
O1A—H1O1 | 0.82 (2) | O1B—H2O1 | 0.83 (2) |
O2A—C13A | 1.197 (7) | O2B—C13B | 1.219 (7) |
O3A—C20A | 1.305 (7) | O3B—C20B | 1.305 (7) |
O3A—H1O3 | 0.82 (2) | O3B—H2O3 | 0.84 (2) |
O4A—C20A | 1.216 (7) | O4B—C20B | 1.226 (6) |
N1A—C4A | 1.466 (7) | N1B—C3B | 1.461 (7) |
N1A—C3A | 1.476 (7) | N1B—C4B | 1.475 (7) |
N1A—C1A | 1.476 (6) | N1B—C1B | 1.479 (6) |
N2A—C5A | 1.463 (7) | N2B—C5B | 1.475 (6) |
N2A—C2A | 1.481 (6) | N2B—C1B | 1.475 (6) |
N2A—C1A | 1.487 (6) | N2B—C2B | 1.484 (7) |
N3A—C2A | 1.451 (7) | N3B—C2B | 1.449 (7) |
N3A—C3A | 1.461 (7) | N3B—C6B | 1.464 (7) |
N3A—C6A | 1.479 (8) | N3B—C3B | 1.470 (7) |
N4A—C4A | 1.458 (7) | N4B—C6B | 1.452 (8) |
N4A—C5A | 1.464 (6) | N4B—C4B | 1.462 (7) |
N4A—C6A | 1.467 (8) | N4B—C5B | 1.477 (6) |
C1A—H1AA | 0.9800 | C1B—H1BA | 0.9800 |
C1A—H1AB | 0.9800 | C1B—H1BB | 0.9800 |
C2A—H2AA | 0.9800 | C2B—H2BA | 0.9800 |
C2A—H2AB | 0.9800 | C2B—H2BB | 0.9800 |
C3A—H3AA | 0.9800 | C3B—H3BA | 0.9800 |
C3A—H3AB | 0.9800 | C3B—H3BB | 0.9800 |
C4A—H4AA | 0.9800 | C4B—H4BA | 0.9800 |
C4A—H4AB | 0.9800 | C4B—H4BB | 0.9800 |
C5A—H5AA | 0.9800 | C5B—H5BA | 0.9800 |
C5A—H5AB | 0.9800 | C5B—H5BB | 0.9800 |
C6A—H6AA | 0.9800 | C6B—H6BA | 0.9800 |
C6A—H6AB | 0.9800 | C6B—H6BB | 0.9800 |
C7A—C12A | 1.383 (8) | C7B—C12B | 1.375 (8) |
C7A—C8A | 1.387 (8) | C7B—C8B | 1.396 (8) |
C7A—C13A | 1.480 (8) | C7B—C13B | 1.480 (8) |
C8A—C9A | 1.372 (9) | C8B—C9B | 1.369 (8) |
C8A—H8AA | 0.9400 | C8B—H8BA | 0.9400 |
C9A—C10A | 1.346 (11) | C9B—C10B | 1.371 (12) |
C9A—H9AA | 0.9400 | C9B—H9BA | 0.9400 |
C10A—C11A | 1.397 (12) | C10B—C11B | 1.383 (12) |
C10A—H10A | 0.9400 | C10B—H10B | 0.9400 |
C11A—C12A | 1.372 (10) | C11B—C12B | 1.391 (10) |
C11A—H11A | 0.9400 | C11B—H11B | 0.9400 |
C12A—H12A | 0.9400 | C12B—H12B | 0.9400 |
C14A—C15A | 1.380 (8) | C14B—C15B | 1.389 (6) |
C14A—C19A | 1.399 (7) | C14B—C19B | 1.405 (8) |
C14A—C20A | 1.490 (7) | C14B—C20B | 1.475 (8) |
C15A—C16A | 1.387 (7) | C15B—C16B | 1.385 (7) |
C15A—H15A | 0.9400 | C15B—H15B | 0.9400 |
C16A—C17A | 1.373 (9) | C16B—C17B | 1.370 (9) |
C16A—H16A | 0.9400 | C16B—H16B | 0.9400 |
C17A—C18A | 1.366 (9) | C17B—C18B | 1.385 (9) |
C17A—H17A | 0.9400 | C17B—H17B | 0.9400 |
C18A—C19A | 1.378 (7) | C18B—C19B | 1.364 (9) |
C18A—H18A | 0.9400 | C18B—H18B | 0.9400 |
C19A—H19A | 0.9400 | C19B—H19B | 0.9400 |
| | | |
C13A—O1A—H1O1 | 116 (6) | C13B—O1B—H2O1 | 96 (7) |
C20A—O3A—H1O3 | 112 (6) | C20B—O3B—H2O3 | 115 (8) |
C4A—N1A—C3A | 108.8 (4) | C3B—N1B—C4B | 109.2 (4) |
C4A—N1A—C1A | 108.3 (4) | C3B—N1B—C1B | 108.2 (4) |
C3A—N1A—C1A | 107.7 (4) | C4B—N1B—C1B | 108.1 (4) |
C5A—N2A—C2A | 109.6 (4) | C5B—N2B—C1B | 108.1 (4) |
C5A—N2A—C1A | 107.5 (4) | C5B—N2B—C2B | 108.9 (4) |
C2A—N2A—C1A | 107.4 (4) | C1B—N2B—C2B | 108.3 (4) |
C2A—N3A—C3A | 108.6 (4) | C2B—N3B—C6B | 108.8 (5) |
C2A—N3A—C6A | 107.7 (4) | C2B—N3B—C3B | 108.4 (4) |
C3A—N3A—C6A | 108.6 (4) | C6B—N3B—C3B | 108.2 (4) |
C4A—N4A—C5A | 108.0 (5) | C6B—N4B—C4B | 108.5 (4) |
C4A—N4A—C6A | 107.6 (4) | C6B—N4B—C5B | 108.2 (4) |
C5A—N4A—C6A | 108.2 (4) | C4B—N4B—C5B | 108.7 (5) |
N1A—C1A—N2A | 111.1 (4) | N2B—C1B—N1B | 111.1 (4) |
N1A—C1A—H1AA | 109.4 | N2B—C1B—H1BA | 109.4 |
N2A—C1A—H1AA | 109.4 | N1B—C1B—H1BA | 109.4 |
N1A—C1A—H1AB | 109.4 | N2B—C1B—H1BB | 109.4 |
N2A—C1A—H1AB | 109.4 | N1B—C1B—H1BB | 109.4 |
H1AA—C1A—H1AB | 108.0 | H1BA—C1B—H1BB | 108.0 |
N3A—C2A—N2A | 111.9 (4) | N3B—C2B—N2B | 111.2 (4) |
N3A—C2A—H2AA | 109.2 | N3B—C2B—H2BA | 109.4 |
N2A—C2A—H2AA | 109.2 | N2B—C2B—H2BA | 109.4 |
N3A—C2A—H2AB | 109.2 | N3B—C2B—H2BB | 109.4 |
N2A—C2A—H2AB | 109.2 | N2B—C2B—H2BB | 109.4 |
H2AA—C2A—H2AB | 107.9 | H2BA—C2B—H2BB | 108.0 |
N3A—C3A—N1A | 111.5 (4) | N1B—C3B—N3B | 111.5 (4) |
N3A—C3A—H3AA | 109.3 | N1B—C3B—H3BA | 109.3 |
N1A—C3A—H3AA | 109.3 | N3B—C3B—H3BA | 109.3 |
N3A—C3A—H3AB | 109.3 | N1B—C3B—H3BB | 109.3 |
N1A—C3A—H3AB | 109.3 | N3B—C3B—H3BB | 109.3 |
H3AA—C3A—H3AB | 108.0 | H3BA—C3B—H3BB | 108.0 |
N4A—C4A—N1A | 112.6 (4) | N4B—C4B—N1B | 111.2 (4) |
N4A—C4A—H4AA | 109.1 | N4B—C4B—H4BA | 109.4 |
N1A—C4A—H4AA | 109.1 | N1B—C4B—H4BA | 109.4 |
N4A—C4A—H4AB | 109.1 | N4B—C4B—H4BB | 109.4 |
N1A—C4A—H4AB | 109.1 | N1B—C4B—H4BB | 109.4 |
H4AA—C4A—H4AB | 107.8 | H4BA—C4B—H4BB | 108.0 |
N2A—C5A—N4A | 112.1 (4) | N2B—C5B—N4B | 111.0 (4) |
N2A—C5A—H5AA | 109.2 | N2B—C5B—H5BA | 109.4 |
N4A—C5A—H5AA | 109.2 | N4B—C5B—H5BA | 109.4 |
N2A—C5A—H5AB | 109.2 | N2B—C5B—H5BB | 109.4 |
N4A—C5A—H5AB | 109.2 | N4B—C5B—H5BB | 109.4 |
H5AA—C5A—H5AB | 107.9 | H5BA—C5B—H5BB | 108.0 |
N4A—C6A—N3A | 112.8 (5) | N4B—C6B—N3B | 112.7 (5) |
N4A—C6A—H6AA | 109.0 | N4B—C6B—H6BA | 109.1 |
N3A—C6A—H6AA | 109.0 | N3B—C6B—H6BA | 109.1 |
N4A—C6A—H6AB | 109.0 | N4B—C6B—H6BB | 109.1 |
N3A—C6A—H6AB | 109.0 | N3B—C6B—H6BB | 109.1 |
H6AA—C6A—H6AB | 107.8 | H6BA—C6B—H6BB | 107.8 |
C12A—C7A—C8A | 119.3 (5) | C12B—C7B—C8B | 120.1 (5) |
C12A—C7A—C13A | 117.5 (5) | C12B—C7B—C13B | 118.7 (5) |
C8A—C7A—C13A | 123.1 (6) | C8B—C7B—C13B | 121.1 (5) |
C9A—C8A—C7A | 120.0 (7) | C9B—C8B—C7B | 119.7 (6) |
C9A—C8A—H8AA | 120.0 | C9B—C8B—H8BA | 120.2 |
C7A—C8A—H8AA | 120.0 | C7B—C8B—H8BA | 120.2 |
C10A—C9A—C8A | 120.6 (7) | C8B—C9B—C10B | 120.5 (7) |
C10A—C9A—H9AA | 119.7 | C8B—C9B—H9BA | 119.8 |
C8A—C9A—H9AA | 119.7 | C10B—C9B—H9BA | 119.8 |
C9A—C10A—C11A | 120.7 (7) | C9B—C10B—C11B | 120.4 (7) |
C9A—C10A—H10A | 119.7 | C9B—C10B—H10B | 119.8 |
C11A—C10A—H10A | 119.7 | C11B—C10B—H10B | 119.8 |
C12A—C11A—C10A | 119.0 (8) | C10B—C11B—C12B | 119.6 (7) |
C12A—C11A—H11A | 120.5 | C10B—C11B—H11B | 120.2 |
C10A—C11A—H11A | 120.5 | C12B—C11B—H11B | 120.2 |
C11A—C12A—C7A | 120.4 (7) | C7B—C12B—C11B | 119.7 (7) |
C11A—C12A—H12A | 119.8 | C7B—C12B—H12B | 120.1 |
C7A—C12A—H12A | 119.8 | C11B—C12B—H12B | 120.1 |
O2A—C13A—O1A | 122.4 (5) | O2B—C13B—O1B | 122.0 (5) |
O2A—C13A—C7A | 123.7 (6) | O2B—C13B—C7B | 122.7 (5) |
O1A—C13A—C7A | 113.9 (5) | O1B—C13B—C7B | 115.3 (5) |
C15A—C14A—C19A | 118.6 (5) | C15B—C14B—C19B | 118.7 (5) |
C15A—C14A—C20A | 121.5 (5) | C15B—C14B—C20B | 120.9 (5) |
C19A—C14A—C20A | 119.9 (5) | C19B—C14B—C20B | 120.4 (5) |
C14A—C15A—C16A | 121.1 (5) | C16B—C15B—C14B | 120.6 (5) |
C14A—C15A—H15A | 119.5 | C16B—C15B—H15B | 119.7 |
C16A—C15A—H15A | 119.5 | C14B—C15B—H15B | 119.7 |
C17A—C16A—C15A | 118.9 (5) | C17B—C16B—C15B | 119.7 (6) |
C17A—C16A—H16A | 120.5 | C17B—C16B—H16B | 120.1 |
C15A—C16A—H16A | 120.5 | C15B—C16B—H16B | 120.1 |
C18A—C17A—C16A | 121.2 (5) | C16B—C17B—C18B | 120.3 (6) |
C18A—C17A—H17A | 119.4 | C16B—C17B—H17B | 119.8 |
C16A—C17A—H17A | 119.4 | C18B—C17B—H17B | 119.8 |
C17A—C18A—C19A | 120.0 (5) | C19B—C18B—C17B | 120.5 (6) |
C17A—C18A—H18A | 120.0 | C19B—C18B—H18B | 119.8 |
C19A—C18A—H18A | 120.0 | C17B—C18B—H18B | 119.8 |
C18A—C19A—C14A | 120.2 (5) | C18B—C19B—C14B | 120.1 (5) |
C18A—C19A—H19A | 119.9 | C18B—C19B—H19B | 119.9 |
C14A—C19A—H19A | 119.9 | C14B—C19B—H19B | 119.9 |
O4A—C20A—O3A | 124.1 (5) | O4B—C20B—O3B | 122.4 (5) |
O4A—C20A—C14A | 122.0 (5) | O4B—C20B—C14B | 122.4 (6) |
O3A—C20A—C14A | 113.9 (5) | O3B—C20B—C14B | 115.3 (5) |
| | | |
C4A—N1A—C1A—N2A | 58.0 (5) | C5B—N2B—C1B—N1B | −59.7 (5) |
C3A—N1A—C1A—N2A | −59.5 (5) | C2B—N2B—C1B—N1B | 58.2 (5) |
C5A—N2A—C1A—N1A | −59.0 (5) | C3B—N1B—C1B—N2B | −58.6 (5) |
C2A—N2A—C1A—N1A | 58.9 (5) | C4B—N1B—C1B—N2B | 59.6 (5) |
C3A—N3A—C2A—N2A | 59.6 (6) | C6B—N3B—C2B—N2B | −57.8 (6) |
C6A—N3A—C2A—N2A | −57.8 (6) | C3B—N3B—C2B—N2B | 59.6 (6) |
C5A—N2A—C2A—N3A | 57.5 (6) | C5B—N2B—C2B—N3B | 58.2 (5) |
C1A—N2A—C2A—N3A | −59.0 (6) | C1B—N2B—C2B—N3B | −59.1 (6) |
C2A—N3A—C3A—N1A | −59.8 (6) | C4B—N1B—C3B—N3B | −58.0 (5) |
C6A—N3A—C3A—N1A | 57.0 (5) | C1B—N1B—C3B—N3B | 59.4 (5) |
C4A—N1A—C3A—N3A | −57.5 (6) | C2B—N3B—C3B—N1B | −60.3 (6) |
C1A—N1A—C3A—N3A | 59.7 (5) | C6B—N3B—C3B—N1B | 57.5 (6) |
C5A—N4A—C4A—N1A | 58.3 (6) | C6B—N4B—C4B—N1B | −57.9 (5) |
C6A—N4A—C4A—N1A | −58.3 (5) | C5B—N4B—C4B—N1B | 59.5 (5) |
C3A—N1A—C4A—N4A | 58.7 (5) | C3B—N1B—C4B—N4B | 58.1 (5) |
C1A—N1A—C4A—N4A | −58.1 (5) | C1B—N1B—C4B—N4B | −59.4 (5) |
C2A—N2A—C5A—N4A | −56.5 (6) | C1B—N2B—C5B—N4B | 59.3 (5) |
C1A—N2A—C5A—N4A | 59.9 (5) | C2B—N2B—C5B—N4B | −58.1 (5) |
C4A—N4A—C5A—N2A | −59.5 (6) | C6B—N4B—C5B—N2B | 58.2 (6) |
C6A—N4A—C5A—N2A | 56.7 (6) | C4B—N4B—C5B—N2B | −59.5 (6) |
C4A—N4A—C6A—N3A | 57.9 (6) | C4B—N4B—C6B—N3B | 58.9 (6) |
C5A—N4A—C6A—N3A | −58.5 (6) | C5B—N4B—C6B—N3B | −58.8 (6) |
C2A—N3A—C6A—N4A | 59.3 (6) | C2B—N3B—C6B—N4B | 59.1 (6) |
C3A—N3A—C6A—N4A | −58.1 (6) | C3B—N3B—C6B—N4B | −58.5 (6) |
C12A—C7A—C8A—C9A | −0.4 (9) | C12B—C7B—C8B—C9B | 0.0 (8) |
C13A—C7A—C8A—C9A | 175.6 (5) | C13B—C7B—C8B—C9B | 177.3 (5) |
C7A—C8A—C9A—C10A | 0.3 (10) | C7B—C8B—C9B—C10B | 1.1 (10) |
C8A—C9A—C10A—C11A | 0.3 (11) | C8B—C9B—C10B—C11B | −1.3 (12) |
C9A—C10A—C11A—C12A | −0.8 (11) | C9B—C10B—C11B—C12B | 0.2 (12) |
C10A—C11A—C12A—C7A | 0.7 (10) | C8B—C7B—C12B—C11B | −1.1 (9) |
C8A—C7A—C12A—C11A | −0.1 (9) | C13B—C7B—C12B—C11B | −178.3 (6) |
C13A—C7A—C12A—C11A | −176.3 (6) | C10B—C11B—C12B—C7B | 0.9 (11) |
C12A—C7A—C13A—O2A | 9.6 (9) | C12B—C7B—C13B—O2B | 12.1 (9) |
C8A—C7A—C13A—O2A | −166.5 (6) | C8B—C7B—C13B—O2B | −165.1 (6) |
C12A—C7A—C13A—O1A | −171.5 (5) | C12B—C7B—C13B—O1B | −169.1 (5) |
C8A—C7A—C13A—O1A | 12.4 (8) | C8B—C7B—C13B—O1B | 13.6 (8) |
C19A—C14A—C15A—C16A | 1.8 (8) | C19B—C14B—C15B—C16B | 0.4 (7) |
C20A—C14A—C15A—C16A | 179.3 (5) | C20B—C14B—C15B—C16B | 179.5 (5) |
C14A—C15A—C16A—C17A | −0.7 (9) | C14B—C15B—C16B—C17B | 0.0 (8) |
C15A—C16A—C17A—C18A | −0.9 (10) | C15B—C16B—C17B—C18B | −0.3 (9) |
C16A—C17A—C18A—C19A | 1.2 (10) | C16B—C17B—C18B—C19B | 0.1 (9) |
C17A—C18A—C19A—C14A | 0.0 (9) | C17B—C18B—C19B—C14B | 0.3 (9) |
C15A—C14A—C19A—C18A | −1.5 (8) | C15B—C14B—C19B—C18B | −0.5 (8) |
C20A—C14A—C19A—C18A | −179.0 (5) | C20B—C14B—C19B—C18B | −179.6 (5) |
C15A—C14A—C20A—O4A | −172.9 (6) | C15B—C14B—C20B—O4B | −172.5 (5) |
C19A—C14A—C20A—O4A | 4.5 (8) | C19B—C14B—C20B—O4B | 6.6 (8) |
C15A—C14A—C20A—O3A | 6.5 (7) | C15B—C14B—C20B—O3B | 6.5 (7) |
C19A—C14A—C20A—O3A | −176.1 (5) | C19B—C14B—C20B—O3B | −174.4 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1O1···N1A | 0.82 (6) | 1.86 (6) | 2.667 (6) | 169 (6) |
O3A—H1O3···N2A | 0.83 (6) | 1.79 (6) | 2.622 (6) | 178 (9) |
O1B—H2O1···N1B | 0.83 (8) | 1.86 (8) | 2.649 (6) | 159 (9) |
O3B—H2O3···N2B | 0.83 (9) | 1.78 (8) | 2.608 (6) | 176 (11) |
C2A—H2AB···O4Ai | 0.98 | 2.48 | 3.137 (7) | 124 |
C5A—H5AA···O2Aii | 0.98 | 2.61 | 3.234 (7) | 121 |
C2B—H2BB···O4Bi | 0.98 | 2.50 | 3.178 (7) | 126 |
C5B—H5BA···O2Biii | 0.98 | 2.56 | 3.235 (7) | 126 |
C3A—H3AA···Cg17iv | 0.98 | 2.78 | 3.754 (6) | 170 |
C10A—H10A···Cg16v | 0.94 | 3.01 | 3.854 (9) | 151 |
C10B—H10B···Cg17vi | 0.94 | 2.88 | 3.682 (9) | 143 |
C5A—H5AB···Cg15iv | 0.98 | 2.89 | 3.823 (6) | 160 |
C17A—H17A···Cg18vii | 0.94 | 2.87 | 3.743 (6) | 155 |
C3B—H3BA···Cg18viii | 0.98 | 2.81 | 3.785 (6) | 171 |
C5B—H5BB···Cg16viii | 0.98 | 2.89 | 3.814 (5) | 158 |
Symmetry codes: (i) x+1, y, z; (ii) x−1/2, −y+1, z−1/2; (iii) x−1/2, −y, z−1/2; (iv) x+1/2, −y+1, z−1/2; (v) x+1/2, −y+1, z+1/2; (vi) x−1, y, z; (vii) x+1/2, −y, z+1/2; (viii) x+1/2, −y, z−1/2. |
Hexamethylenetetramine bis(benzoic acid) (1533068)
top
Crystal data top
C6H12N4·2(C7H6O2) | F(000) = 816 |
Mr = 384.43 | Dx = 1.307 Mg m−3 |
Monoclinic, Pn | Mo Kα radiation, λ = 0.71073 Å |
a = 6.1398 (8) Å | Cell parameters from 6036 reflections |
b = 26.721 (4) Å | θ = 2.9–28.2° |
c = 12.0772 (17) Å | µ = 0.09 mm−1 |
β = 99.554 (2)° | T = 240 K |
V = 1953.9 (5) Å3 | Block, colourless |
Z = 4 | 0.76 × 0.39 × 0.21 mm |
Data collection top
Bruker APEX Duo CCD area detector diffractometer | 4889 independent reflections |
Radiation source: fine-focus sealed tube | 2934 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
φ and ω scans | θmax = 28.5°, θmin = 1.9° |
Absorption correction: multi-scan (TWINABS; Sheldrick, 2012) | h = −8→8 |
Tmin = 0.789, Tmax = 0.937 | k = 0→35 |
6401 measured reflections | l = 0→16 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.057 | w = 1/[σ2(Fo2) + (0.0706P)2 + 0.2054P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.168 | (Δ/σ)max < 0.001 |
S = 1.10 | Δρmax = 0.23 e Å−3 |
4889 reflections | Δρmin = −0.20 e Å−3 |
522 parameters | Absolute structure: No quotients, so Flack parameter determined by classical intensity fit |
6 restraints | Absolute structure parameter: −1.3 (13) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1A | 0.6799 (7) | 0.38149 (16) | 0.4618 (4) | 0.0671 (13) | |
H1O1 | 0.624 (7) | 0.4009 (15) | 0.501 (4) | 0.051 (15)* | |
O2A | 0.4065 (7) | 0.39955 (17) | 0.3264 (4) | 0.0864 (16) | |
O3A | 0.4242 (6) | 0.60996 (13) | 0.3973 (3) | 0.0528 (10) | |
H1O3 | 0.419 (11) | 0.5920 (19) | 0.452 (3) | 0.08 (2)* | |
O4A | 0.7823 (6) | 0.60495 (15) | 0.4611 (4) | 0.0691 (12) | |
N1A | 0.4776 (6) | 0.45021 (13) | 0.5685 (3) | 0.0402 (9) | |
N2A | 0.3959 (6) | 0.53964 (13) | 0.5440 (3) | 0.0385 (9) | |
N3A | 0.1345 (6) | 0.48337 (16) | 0.6127 (4) | 0.0465 (10) | |
N4A | 0.4854 (7) | 0.50406 (14) | 0.7318 (4) | 0.0460 (11) | |
C1A | 0.4984 (8) | 0.49542 (14) | 0.5004 (5) | 0.0409 (12) | |
H1AA | 0.6552 | 0.5022 | 0.5001 | 0.049* | |
H1AB | 0.4277 | 0.4892 | 0.4227 | 0.049* | |
C2A | 0.1595 (7) | 0.52738 (17) | 0.5439 (5) | 0.0479 (12) | |
H2AA | 0.0867 | 0.5561 | 0.5728 | 0.057* | |
H2AB | 0.0865 | 0.5212 | 0.4667 | 0.057* | |
C3A | 0.2431 (8) | 0.44083 (16) | 0.5684 (5) | 0.0461 (12) | |
H3AA | 0.2271 | 0.4111 | 0.6140 | 0.055* | |
H3AB | 0.1701 | 0.4339 | 0.4914 | 0.055* | |
C4A | 0.5841 (8) | 0.46123 (19) | 0.6846 (4) | 0.0497 (13) | |
H4AA | 0.5721 | 0.4318 | 0.7317 | 0.060* | |
H4AB | 0.7414 | 0.4678 | 0.6856 | 0.060* | |
C5A | 0.5055 (8) | 0.54787 (17) | 0.6605 (4) | 0.0464 (12) | |
H5AA | 0.6622 | 0.5551 | 0.6612 | 0.056* | |
H5AB | 0.4394 | 0.5770 | 0.6913 | 0.056* | |
C6A | 0.2499 (9) | 0.4932 (2) | 0.7281 (5) | 0.0518 (14) | |
H6AA | 0.1799 | 0.5218 | 0.7592 | 0.062* | |
H6AB | 0.2346 | 0.4640 | 0.7752 | 0.062* | |
C7A | 0.6928 (8) | 0.34711 (16) | 0.2844 (5) | 0.0436 (12) | |
C8A | 0.9068 (9) | 0.33143 (18) | 0.3188 (5) | 0.0527 (14) | |
H8AA | 0.9802 | 0.3385 | 0.3917 | 0.063* | |
C9A | 1.0135 (12) | 0.3049 (2) | 0.2439 (7) | 0.077 (2) | |
H9AA | 1.1613 | 0.2950 | 0.2655 | 0.092* | |
C10A | 0.9040 (14) | 0.2934 (2) | 0.1395 (7) | 0.089 (2) | |
H10A | 0.9752 | 0.2748 | 0.0899 | 0.107* | |
C11A | 0.6891 (14) | 0.3089 (2) | 0.1064 (6) | 0.084 (2) | |
H11A | 0.6136 | 0.3010 | 0.0344 | 0.101* | |
C12A | 0.5854 (11) | 0.33600 (19) | 0.1789 (6) | 0.0652 (16) | |
H12A | 0.4395 | 0.3470 | 0.1559 | 0.078* | |
C13A | 0.5776 (8) | 0.37846 (18) | 0.3596 (5) | 0.0503 (14) | |
C14A | 0.6649 (7) | 0.65408 (15) | 0.2984 (4) | 0.0358 (10) | |
C15A | 0.4872 (8) | 0.66713 (17) | 0.2181 (4) | 0.0459 (12) | |
H15A | 0.3449 | 0.6557 | 0.2239 | 0.055* | |
C16A | 0.5191 (10) | 0.69709 (19) | 0.1290 (5) | 0.0610 (15) | |
H16A | 0.3991 | 0.7059 | 0.0735 | 0.073* | |
C17A | 0.7261 (11) | 0.71381 (19) | 0.1225 (5) | 0.0626 (16) | |
H17A | 0.7463 | 0.7349 | 0.0628 | 0.075* | |
C18A | 0.9043 (9) | 0.70088 (19) | 0.1996 (6) | 0.0604 (16) | |
H18A | 1.0462 | 0.7123 | 0.1927 | 0.073* | |
C19A | 0.8724 (8) | 0.66998 (18) | 0.2902 (5) | 0.0511 (13) | |
H19A | 0.9933 | 0.6605 | 0.3445 | 0.061* | |
C20A | 0.6303 (8) | 0.62042 (16) | 0.3945 (4) | 0.0389 (11) | |
O1B | 1.4453 (7) | 0.88345 (17) | 0.7161 (3) | 0.0679 (13) | |
H2O1 | 1.388 (10) | 0.9048 (18) | 0.752 (5) | 0.09 (2)* | |
O2B | 1.1785 (7) | 0.90126 (18) | 0.5778 (4) | 0.0830 (16) | |
O3B | 1.1830 (6) | 1.11072 (15) | 0.6502 (3) | 0.0569 (11) | |
H2O3 | 1.156 (12) | 1.0867 (19) | 0.691 (5) | 0.12 (3)* | |
O4B | 1.5410 (6) | 1.10827 (17) | 0.7177 (3) | 0.0735 (13) | |
N1B | 1.2388 (6) | 0.95182 (14) | 0.8208 (3) | 0.0381 (9) | |
N2B | 1.1530 (6) | 1.04018 (15) | 0.7985 (3) | 0.0381 (9) | |
N3B | 0.8956 (6) | 0.98407 (18) | 0.8659 (4) | 0.0490 (11) | |
N4B | 1.2440 (7) | 1.00420 (15) | 0.9855 (4) | 0.0475 (12) | |
C1B | 1.2577 (8) | 0.99715 (15) | 0.7538 (4) | 0.0369 (11) | |
H1BA | 1.4141 | 1.0045 | 0.7539 | 0.044* | |
H1BB | 1.1876 | 0.9912 | 0.6759 | 0.044* | |
C2B | 0.9196 (7) | 1.02835 (19) | 0.7987 (4) | 0.0474 (12) | |
H2BA | 0.8481 | 1.0569 | 0.8290 | 0.057* | |
H2BB | 0.8454 | 1.0227 | 0.7214 | 0.057* | |
C3B | 1.0015 (7) | 0.94231 (19) | 0.8194 (4) | 0.0479 (12) | |
H3BA | 0.9289 | 0.9364 | 0.7419 | 0.057* | |
H3BB | 0.9842 | 0.9121 | 0.8630 | 0.057* | |
C4B | 1.3452 (7) | 0.96191 (18) | 0.9376 (4) | 0.0456 (12) | |
H4BA | 1.3336 | 0.9321 | 0.9835 | 0.055* | |
H4BB | 1.5024 | 0.9689 | 0.9390 | 0.055* | |
C5B | 1.2625 (8) | 1.04795 (18) | 0.9162 (4) | 0.0465 (12) | |
H5BA | 1.4190 | 1.0555 | 0.9173 | 0.056* | |
H5BB | 1.1952 | 1.0767 | 0.9477 | 0.056* | |
C6B | 1.0088 (9) | 0.99318 (19) | 0.9805 (4) | 0.0483 (13) | |
H6BA | 0.9933 | 0.9636 | 1.0265 | 0.058* | |
H6BB | 0.9381 | 1.0214 | 1.0123 | 0.058* | |
C7B | 1.4648 (8) | 0.84750 (18) | 0.5415 (4) | 0.0439 (12) | |
C8B | 1.6785 (9) | 0.8318 (2) | 0.5775 (5) | 0.0536 (13) | |
H8BA | 1.7510 | 0.8401 | 0.6500 | 0.064* | |
C9B | 1.7872 (12) | 0.8036 (2) | 0.5061 (6) | 0.079 (2) | |
H9BA | 1.9348 | 0.7937 | 0.5287 | 0.094* | |
C10B | 1.6728 (16) | 0.7903 (3) | 0.4007 (7) | 0.097 (3) | |
H10B | 1.7422 | 0.7703 | 0.3528 | 0.116* | |
C11B | 1.4649 (15) | 0.8059 (3) | 0.3670 (6) | 0.089 (2) | |
H11B | 1.3918 | 0.7973 | 0.2949 | 0.107* | |
C12B | 1.3562 (12) | 0.8341 (2) | 0.4358 (5) | 0.0692 (17) | |
H12B | 1.2095 | 0.8442 | 0.4113 | 0.083* | |
C13B | 1.3469 (8) | 0.87924 (19) | 0.6129 (4) | 0.0460 (12) | |
C14B | 1.4236 (7) | 1.15407 (17) | 0.5516 (4) | 0.0371 (10) | |
C15B | 1.2487 (7) | 1.16472 (17) | 0.4669 (4) | 0.0420 (11) | |
H15B | 1.1071 | 1.1524 | 0.4714 | 0.050* | |
C16B | 1.2808 (9) | 1.19339 (19) | 0.3757 (4) | 0.0509 (12) | |
H16B | 1.1624 | 1.1999 | 0.3174 | 0.061* | |
C17B | 1.4887 (9) | 1.2125 (2) | 0.3708 (5) | 0.0573 (14) | |
H17B | 1.5108 | 1.2325 | 0.3097 | 0.069* | |
C18B | 1.6612 (9) | 1.2024 (2) | 0.4541 (5) | 0.0557 (14) | |
H18B | 1.8024 | 1.2149 | 0.4495 | 0.067* | |
C19B | 1.6297 (8) | 1.17383 (19) | 0.5450 (5) | 0.0505 (13) | |
H19B | 1.7490 | 1.1677 | 0.6030 | 0.061* | |
C20B | 1.3884 (8) | 1.12333 (18) | 0.6482 (4) | 0.0432 (12) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.073 (3) | 0.067 (3) | 0.059 (3) | 0.037 (2) | 0.003 (2) | −0.008 (2) |
O2A | 0.065 (3) | 0.095 (3) | 0.091 (4) | 0.040 (2) | −0.013 (2) | −0.028 (3) |
O3A | 0.051 (2) | 0.048 (2) | 0.059 (3) | −0.0044 (16) | 0.0088 (18) | 0.0247 (19) |
O4A | 0.056 (2) | 0.076 (3) | 0.069 (3) | 0.004 (2) | −0.008 (2) | 0.031 (2) |
N1A | 0.041 (2) | 0.0291 (18) | 0.051 (2) | 0.0041 (15) | 0.0093 (18) | 0.0038 (18) |
N2A | 0.043 (2) | 0.0300 (18) | 0.043 (2) | 0.0000 (16) | 0.0099 (18) | 0.0033 (17) |
N3A | 0.038 (2) | 0.042 (2) | 0.063 (3) | −0.0022 (18) | 0.0180 (19) | 0.005 (2) |
N4A | 0.060 (3) | 0.042 (2) | 0.036 (3) | −0.0030 (17) | 0.007 (2) | 0.0026 (17) |
C1A | 0.043 (3) | 0.036 (2) | 0.046 (3) | 0.0002 (18) | 0.013 (2) | 0.0032 (19) |
C2A | 0.039 (2) | 0.041 (3) | 0.064 (3) | 0.0065 (19) | 0.010 (2) | 0.004 (2) |
C3A | 0.046 (2) | 0.032 (2) | 0.061 (3) | −0.008 (2) | 0.010 (2) | 0.005 (2) |
C4A | 0.046 (3) | 0.049 (3) | 0.051 (3) | 0.010 (2) | 0.000 (2) | 0.015 (3) |
C5A | 0.053 (3) | 0.034 (2) | 0.053 (3) | −0.008 (2) | 0.009 (2) | −0.001 (2) |
C6A | 0.058 (3) | 0.054 (3) | 0.049 (4) | −0.004 (2) | 0.026 (3) | 0.006 (3) |
C7A | 0.054 (3) | 0.020 (2) | 0.057 (3) | 0.0067 (19) | 0.011 (2) | 0.001 (2) |
C8A | 0.057 (3) | 0.034 (2) | 0.069 (4) | 0.011 (2) | 0.014 (3) | 0.003 (3) |
C9A | 0.083 (4) | 0.058 (4) | 0.096 (5) | 0.030 (3) | 0.034 (4) | 0.013 (4) |
C10A | 0.130 (7) | 0.049 (3) | 0.104 (6) | 0.018 (4) | 0.071 (5) | −0.001 (4) |
C11A | 0.133 (7) | 0.059 (4) | 0.064 (5) | 0.003 (4) | 0.026 (4) | −0.019 (4) |
C12A | 0.084 (4) | 0.037 (3) | 0.074 (4) | 0.001 (3) | 0.010 (3) | 0.000 (3) |
C13A | 0.049 (3) | 0.035 (2) | 0.066 (4) | 0.012 (2) | 0.006 (3) | −0.002 (3) |
C14A | 0.044 (2) | 0.0183 (19) | 0.046 (3) | 0.0033 (17) | 0.011 (2) | 0.0020 (19) |
C15A | 0.052 (3) | 0.033 (2) | 0.053 (3) | 0.001 (2) | 0.009 (2) | 0.005 (2) |
C16A | 0.078 (4) | 0.045 (3) | 0.058 (4) | 0.008 (3) | 0.006 (3) | 0.017 (3) |
C17A | 0.089 (4) | 0.040 (3) | 0.064 (4) | 0.001 (3) | 0.026 (3) | 0.013 (3) |
C18A | 0.056 (3) | 0.041 (3) | 0.090 (5) | −0.002 (2) | 0.029 (3) | 0.005 (3) |
C19A | 0.047 (3) | 0.031 (2) | 0.077 (4) | 0.006 (2) | 0.014 (3) | 0.001 (3) |
C20A | 0.046 (3) | 0.024 (2) | 0.046 (3) | 0.0010 (19) | 0.006 (2) | 0.005 (2) |
O1B | 0.076 (3) | 0.089 (3) | 0.037 (2) | 0.046 (2) | 0.0033 (19) | −0.011 (2) |
O2B | 0.066 (3) | 0.106 (3) | 0.066 (3) | 0.038 (2) | −0.018 (2) | −0.025 (3) |
O3B | 0.050 (2) | 0.070 (3) | 0.049 (2) | −0.0013 (18) | 0.0046 (18) | 0.023 (2) |
O4B | 0.054 (2) | 0.102 (3) | 0.058 (3) | 0.008 (2) | −0.010 (2) | 0.035 (2) |
N1B | 0.041 (2) | 0.050 (2) | 0.0261 (19) | 0.0065 (17) | 0.0119 (15) | −0.0007 (17) |
N2B | 0.042 (2) | 0.051 (2) | 0.0225 (19) | −0.0003 (17) | 0.0075 (15) | 0.0030 (17) |
N3B | 0.035 (2) | 0.067 (3) | 0.049 (3) | 0.002 (2) | 0.0186 (18) | 0.000 (2) |
N4B | 0.060 (3) | 0.058 (3) | 0.023 (2) | −0.0022 (19) | 0.0011 (19) | −0.0015 (17) |
C1B | 0.039 (2) | 0.050 (3) | 0.026 (3) | 0.0040 (17) | 0.018 (2) | 0.0017 (17) |
C2B | 0.038 (2) | 0.060 (3) | 0.044 (3) | 0.012 (2) | 0.007 (2) | 0.006 (2) |
C3B | 0.043 (3) | 0.060 (3) | 0.042 (3) | −0.010 (2) | 0.009 (2) | −0.002 (2) |
C4B | 0.045 (3) | 0.059 (3) | 0.031 (3) | 0.006 (2) | 0.001 (2) | 0.010 (2) |
C5B | 0.055 (3) | 0.052 (3) | 0.031 (3) | −0.009 (2) | 0.003 (2) | −0.005 (2) |
C6B | 0.061 (3) | 0.058 (3) | 0.031 (3) | 0.001 (2) | 0.023 (2) | 0.002 (2) |
C7B | 0.060 (3) | 0.042 (3) | 0.032 (3) | −0.005 (2) | 0.013 (2) | 0.004 (2) |
C8B | 0.060 (3) | 0.056 (3) | 0.049 (3) | 0.007 (3) | 0.021 (3) | 0.005 (3) |
C9B | 0.081 (4) | 0.072 (4) | 0.094 (5) | 0.016 (3) | 0.048 (4) | 0.007 (4) |
C10B | 0.156 (8) | 0.078 (5) | 0.069 (5) | 0.021 (5) | 0.058 (5) | −0.013 (4) |
C11B | 0.137 (7) | 0.084 (5) | 0.048 (4) | 0.015 (5) | 0.023 (4) | −0.009 (4) |
C12B | 0.095 (4) | 0.077 (4) | 0.035 (3) | 0.001 (4) | 0.010 (3) | −0.005 (3) |
C13B | 0.054 (3) | 0.048 (3) | 0.035 (3) | 0.004 (2) | 0.006 (2) | −0.006 (2) |
C14B | 0.041 (2) | 0.040 (2) | 0.029 (2) | 0.0048 (19) | 0.0040 (19) | −0.007 (2) |
C15B | 0.037 (2) | 0.048 (3) | 0.040 (3) | −0.001 (2) | 0.0039 (19) | 0.002 (2) |
C16B | 0.056 (3) | 0.053 (3) | 0.043 (3) | 0.001 (2) | 0.004 (2) | 0.010 (3) |
C17B | 0.064 (3) | 0.060 (3) | 0.051 (3) | 0.000 (3) | 0.018 (3) | 0.018 (3) |
C18B | 0.050 (3) | 0.059 (3) | 0.061 (4) | −0.005 (2) | 0.018 (2) | −0.003 (3) |
C19B | 0.037 (2) | 0.057 (3) | 0.056 (3) | 0.005 (2) | 0.005 (2) | −0.004 (3) |
C20B | 0.049 (3) | 0.045 (3) | 0.033 (3) | 0.003 (2) | −0.002 (2) | 0.003 (2) |
Geometric parameters (Å, º) top
O1A—C13A | 1.291 (7) | O1B—C13B | 1.298 (6) |
O1A—H1O1 | 0.82 (2) | O1B—H2O1 | 0.83 (2) |
O2A—C13A | 1.201 (6) | O2B—C13B | 1.204 (6) |
O3A—C20A | 1.301 (6) | O3B—C20B | 1.309 (6) |
O3A—H1O3 | 0.82 (2) | O3B—H2O3 | 0.84 (2) |
O4A—C20A | 1.200 (6) | O4B—C20B | 1.218 (5) |
N1A—C3A | 1.461 (6) | N1B—C1B | 1.472 (6) |
N1A—C4A | 1.475 (6) | N1B—C3B | 1.476 (6) |
N1A—C1A | 1.479 (5) | N1B—C4B | 1.477 (5) |
N2A—C5A | 1.471 (6) | N2B—C1B | 1.464 (5) |
N2A—C1A | 1.476 (6) | N2B—C2B | 1.468 (6) |
N2A—C2A | 1.488 (5) | N2B—C5B | 1.483 (6) |
N3A—C2A | 1.463 (6) | N3B—C3B | 1.451 (6) |
N3A—C3A | 1.464 (6) | N3B—C2B | 1.456 (7) |
N3A—C6A | 1.478 (7) | N3B—C6B | 1.463 (6) |
N4A—C4A | 1.454 (6) | N4B—C5B | 1.453 (6) |
N4A—C6A | 1.468 (7) | N4B—C4B | 1.455 (6) |
N4A—C5A | 1.470 (6) | N4B—C6B | 1.465 (7) |
C1A—H1AA | 0.9800 | C1B—H1BA | 0.9800 |
C1A—H1AB | 0.9800 | C1B—H1BB | 0.9800 |
C2A—H2AA | 0.9800 | C2B—H2BA | 0.9800 |
C2A—H2AB | 0.9800 | C2B—H2BB | 0.9800 |
C3A—H3AA | 0.9800 | C3B—H3BA | 0.9800 |
C3A—H3AB | 0.9800 | C3B—H3BB | 0.9800 |
C4A—H4AA | 0.9800 | C4B—H4BA | 0.9800 |
C4A—H4AB | 0.9800 | C4B—H4BB | 0.9800 |
C5A—H5AA | 0.9800 | C5B—H5BA | 0.9800 |
C5A—H5AB | 0.9800 | C5B—H5BB | 0.9800 |
C6A—H6AA | 0.9800 | C6B—H6BA | 0.9800 |
C6A—H6AB | 0.9800 | C6B—H6BB | 0.9800 |
C7A—C12A | 1.367 (8) | C7B—C8B | 1.377 (7) |
C7A—C8A | 1.376 (7) | C7B—C12B | 1.386 (7) |
C7A—C13A | 1.496 (7) | C7B—C13B | 1.481 (7) |
C8A—C9A | 1.395 (8) | C8B—C9B | 1.396 (7) |
C8A—H8AA | 0.9400 | C8B—H8BA | 0.9400 |
C9A—C10A | 1.362 (10) | C9B—C10B | 1.394 (11) |
C9A—H9AA | 0.9400 | C9B—H9BA | 0.9400 |
C10A—C11A | 1.378 (11) | C10B—C11B | 1.340 (11) |
C10A—H10A | 0.9400 | C10B—H10B | 0.9400 |
C11A—C12A | 1.371 (9) | C11B—C12B | 1.374 (9) |
C11A—H11A | 0.9400 | C11B—H11B | 0.9400 |
C12A—H12A | 0.9400 | C12B—H12B | 0.9400 |
C14A—C19A | 1.362 (7) | C14B—C15B | 1.385 (6) |
C14A—C15A | 1.379 (6) | C14B—C19B | 1.386 (7) |
C14A—C20A | 1.511 (6) | C14B—C20B | 1.472 (7) |
C15A—C16A | 1.380 (7) | C15B—C16B | 1.382 (7) |
C15A—H15A | 0.9400 | C15B—H15B | 0.9400 |
C16A—C17A | 1.362 (8) | C16B—C17B | 1.385 (7) |
C16A—H16A | 0.9400 | C16B—H16B | 0.9400 |
C17A—C18A | 1.359 (8) | C17B—C18B | 1.361 (7) |
C17A—H17A | 0.9400 | C17B—H17B | 0.9400 |
C18A—C19A | 1.411 (8) | C18B—C19B | 1.376 (8) |
C18A—H18A | 0.9400 | C18B—H18B | 0.9400 |
C19A—H19A | 0.9400 | C19B—H19B | 0.9400 |
| | | |
C13A—O1A—H1O1 | 114 (4) | C13B—O1B—H2O1 | 113 (5) |
C20A—O3A—H1O3 | 108 (5) | C20B—O3B—H2O3 | 119 (5) |
C3A—N1A—C4A | 108.4 (4) | C1B—N1B—C3B | 107.7 (4) |
C3A—N1A—C1A | 108.4 (4) | C1B—N1B—C4B | 108.2 (4) |
C4A—N1A—C1A | 107.5 (4) | C3B—N1B—C4B | 108.8 (3) |
C5A—N2A—C1A | 107.9 (4) | C1B—N2B—C2B | 108.7 (4) |
C5A—N2A—C2A | 108.9 (4) | C1B—N2B—C5B | 107.8 (4) |
C1A—N2A—C2A | 107.3 (4) | C2B—N2B—C5B | 108.4 (3) |
C2A—N3A—C3A | 108.6 (4) | C3B—N3B—C2B | 108.4 (4) |
C2A—N3A—C6A | 108.2 (4) | C3B—N3B—C6B | 108.7 (4) |
C3A—N3A—C6A | 107.9 (4) | C2B—N3B—C6B | 108.4 (4) |
C4A—N4A—C6A | 107.8 (4) | C5B—N4B—C4B | 108.4 (4) |
C4A—N4A—C5A | 108.4 (4) | C5B—N4B—C6B | 108.0 (4) |
C6A—N4A—C5A | 108.5 (4) | C4B—N4B—C6B | 108.1 (4) |
N2A—C1A—N1A | 112.0 (4) | N2B—C1B—N1B | 111.3 (4) |
N2A—C1A—H1AA | 109.2 | N2B—C1B—H1BA | 109.4 |
N1A—C1A—H1AA | 109.2 | N1B—C1B—H1BA | 109.4 |
N2A—C1A—H1AB | 109.2 | N2B—C1B—H1BB | 109.4 |
N1A—C1A—H1AB | 109.2 | N1B—C1B—H1BB | 109.4 |
H1AA—C1A—H1AB | 107.9 | H1BA—C1B—H1BB | 108.0 |
N3A—C2A—N2A | 111.8 (3) | N3B—C2B—N2B | 111.4 (4) |
N3A—C2A—H2AA | 109.3 | N3B—C2B—H2BA | 109.3 |
N2A—C2A—H2AA | 109.3 | N2B—C2B—H2BA | 109.3 |
N3A—C2A—H2AB | 109.3 | N3B—C2B—H2BB | 109.3 |
N2A—C2A—H2AB | 109.3 | N2B—C2B—H2BB | 109.3 |
H2AA—C2A—H2AB | 107.9 | H2BA—C2B—H2BB | 108.0 |
N1A—C3A—N3A | 112.0 (3) | N3B—C3B—N1B | 111.6 (4) |
N1A—C3A—H3AA | 109.2 | N3B—C3B—H3BA | 109.3 |
N3A—C3A—H3AA | 109.2 | N1B—C3B—H3BA | 109.3 |
N1A—C3A—H3AB | 109.2 | N3B—C3B—H3BB | 109.3 |
N3A—C3A—H3AB | 109.2 | N1B—C3B—H3BB | 109.3 |
H3AA—C3A—H3AB | 107.9 | H3BA—C3B—H3BB | 108.0 |
N4A—C4A—N1A | 112.4 (4) | N4B—C4B—N1B | 111.8 (4) |
N4A—C4A—H4AA | 109.1 | N4B—C4B—H4BA | 109.3 |
N1A—C4A—H4AA | 109.1 | N1B—C4B—H4BA | 109.3 |
N4A—C4A—H4AB | 109.1 | N4B—C4B—H4BB | 109.3 |
N1A—C4A—H4AB | 109.1 | N1B—C4B—H4BB | 109.3 |
H4AA—C4A—H4AB | 107.8 | H4BA—C4B—H4BB | 107.9 |
N4A—C5A—N2A | 111.8 (4) | N4B—C5B—N2B | 111.9 (4) |
N4A—C5A—H5AA | 109.3 | N4B—C5B—H5BA | 109.2 |
N2A—C5A—H5AA | 109.3 | N2B—C5B—H5BA | 109.2 |
N4A—C5A—H5AB | 109.3 | N4B—C5B—H5BB | 109.2 |
N2A—C5A—H5AB | 109.3 | N2B—C5B—H5BB | 109.2 |
H5AA—C5A—H5AB | 107.9 | H5BA—C5B—H5BB | 107.9 |
N4A—C6A—N3A | 112.3 (4) | N3B—C6B—N4B | 112.5 (4) |
N4A—C6A—H6AA | 109.1 | N3B—C6B—H6BA | 109.1 |
N3A—C6A—H6AA | 109.1 | N4B—C6B—H6BA | 109.1 |
N4A—C6A—H6AB | 109.1 | N3B—C6B—H6BB | 109.1 |
N3A—C6A—H6AB | 109.1 | N4B—C6B—H6BB | 109.1 |
H6AA—C6A—H6AB | 107.9 | H6BA—C6B—H6BB | 107.8 |
C12A—C7A—C8A | 120.2 (5) | C8B—C7B—C12B | 120.0 (5) |
C12A—C7A—C13A | 118.9 (5) | C8B—C7B—C13B | 121.5 (5) |
C8A—C7A—C13A | 120.8 (5) | C12B—C7B—C13B | 118.5 (5) |
C7A—C8A—C9A | 119.1 (6) | C7B—C8B—C9B | 119.8 (6) |
C7A—C8A—H8AA | 120.4 | C7B—C8B—H8BA | 120.1 |
C9A—C8A—H8AA | 120.4 | C9B—C8B—H8BA | 120.1 |
C10A—C9A—C8A | 120.2 (6) | C10B—C9B—C8B | 118.8 (7) |
C10A—C9A—H9AA | 119.9 | C10B—C9B—H9BA | 120.6 |
C8A—C9A—H9AA | 119.9 | C8B—C9B—H9BA | 120.6 |
C9A—C10A—C11A | 120.1 (6) | C11B—C10B—C9B | 120.6 (6) |
C9A—C10A—H10A | 120.0 | C11B—C10B—H10B | 119.7 |
C11A—C10A—H10A | 120.0 | C9B—C10B—H10B | 119.7 |
C12A—C11A—C10A | 119.9 (7) | C10B—C11B—C12B | 121.4 (7) |
C12A—C11A—H11A | 120.1 | C10B—C11B—H11B | 119.3 |
C10A—C11A—H11A | 120.1 | C12B—C11B—H11B | 119.3 |
C7A—C12A—C11A | 120.4 (6) | C11B—C12B—C7B | 119.4 (7) |
C7A—C12A—H12A | 119.8 | C11B—C12B—H12B | 120.3 |
C11A—C12A—H12A | 119.8 | C7B—C12B—H12B | 120.3 |
O2A—C13A—O1A | 123.3 (5) | O2B—C13B—O1B | 122.1 (5) |
O2A—C13A—C7A | 122.4 (5) | O2B—C13B—C7B | 123.3 (5) |
O1A—C13A—C7A | 114.3 (4) | O1B—C13B—C7B | 114.5 (4) |
C19A—C14A—C15A | 120.7 (5) | C15B—C14B—C19B | 118.8 (5) |
C19A—C14A—C20A | 119.6 (4) | C15B—C14B—C20B | 120.2 (4) |
C15A—C14A—C20A | 119.7 (4) | C19B—C14B—C20B | 121.0 (4) |
C14A—C15A—C16A | 119.8 (5) | C16B—C15B—C14B | 120.5 (5) |
C14A—C15A—H15A | 120.1 | C16B—C15B—H15B | 119.7 |
C16A—C15A—H15A | 120.1 | C14B—C15B—H15B | 119.7 |
C17A—C16A—C15A | 119.3 (5) | C15B—C16B—C17B | 119.5 (5) |
C17A—C16A—H16A | 120.3 | C15B—C16B—H16B | 120.3 |
C15A—C16A—H16A | 120.3 | C17B—C16B—H16B | 120.3 |
C18A—C17A—C16A | 122.0 (5) | C18B—C17B—C16B | 120.4 (5) |
C18A—C17A—H17A | 119.0 | C18B—C17B—H17B | 119.8 |
C16A—C17A—H17A | 119.0 | C16B—C17B—H17B | 119.8 |
C17A—C18A—C19A | 118.8 (5) | C17B—C18B—C19B | 120.3 (5) |
C17A—C18A—H18A | 120.6 | C17B—C18B—H18B | 119.9 |
C19A—C18A—H18A | 120.6 | C19B—C18B—H18B | 119.9 |
C14A—C19A—C18A | 119.4 (5) | C18B—C19B—C14B | 120.5 (5) |
C14A—C19A—H19A | 120.3 | C18B—C19B—H19B | 119.7 |
C18A—C19A—H19A | 120.3 | C14B—C19B—H19B | 119.7 |
O4A—C20A—O3A | 124.0 (5) | O4B—C20B—O3B | 122.4 (5) |
O4A—C20A—C14A | 121.8 (4) | O4B—C20B—C14B | 122.2 (5) |
O3A—C20A—C14A | 114.2 (4) | O3B—C20B—C14B | 115.2 (4) |
| | | |
C5A—N2A—C1A—N1A | 58.9 (5) | C2B—N2B—C1B—N1B | −58.5 (5) |
C2A—N2A—C1A—N1A | −58.3 (5) | C5B—N2B—C1B—N1B | 58.8 (5) |
C3A—N1A—C1A—N2A | 58.6 (5) | C3B—N1B—C1B—N2B | 58.5 (5) |
C4A—N1A—C1A—N2A | −58.4 (5) | C4B—N1B—C1B—N2B | −58.9 (5) |
C3A—N3A—C2A—N2A | −59.2 (5) | C3B—N3B—C2B—N2B | −59.3 (5) |
C6A—N3A—C2A—N2A | 57.7 (5) | C6B—N3B—C2B—N2B | 58.6 (5) |
C5A—N2A—C2A—N3A | −57.7 (5) | C1B—N2B—C2B—N3B | 58.6 (5) |
C1A—N2A—C2A—N3A | 58.8 (5) | C5B—N2B—C2B—N3B | −58.3 (5) |
C4A—N1A—C3A—N3A | 58.1 (5) | C2B—N3B—C3B—N1B | 60.0 (5) |
C1A—N1A—C3A—N3A | −58.3 (5) | C6B—N3B—C3B—N1B | −57.7 (5) |
C2A—N3A—C3A—N1A | 58.9 (5) | C1B—N1B—C3B—N3B | −59.5 (5) |
C6A—N3A—C3A—N1A | −58.2 (5) | C4B—N1B—C3B—N3B | 57.5 (5) |
C6A—N4A—C4A—N1A | 58.2 (5) | C5B—N4B—C4B—N1B | −58.9 (5) |
C5A—N4A—C4A—N1A | −59.0 (5) | C6B—N4B—C4B—N1B | 58.0 (5) |
C3A—N1A—C4A—N4A | −58.4 (5) | C1B—N1B—C4B—N4B | 58.7 (5) |
C1A—N1A—C4A—N4A | 58.6 (5) | C3B—N1B—C4B—N4B | −57.9 (5) |
C4A—N4A—C5A—N2A | 58.9 (5) | C4B—N4B—C5B—N2B | 59.1 (5) |
C6A—N4A—C5A—N2A | −57.9 (5) | C6B—N4B—C5B—N2B | −57.8 (5) |
C1A—N2A—C5A—N4A | −58.6 (5) | C1B—N2B—C5B—N4B | −59.2 (5) |
C2A—N2A—C5A—N4A | 57.5 (5) | C2B—N2B—C5B—N4B | 58.3 (5) |
C4A—N4A—C6A—N3A | −58.5 (5) | C3B—N3B—C6B—N4B | 58.7 (6) |
C5A—N4A—C6A—N3A | 58.7 (5) | C2B—N3B—C6B—N4B | −59.0 (5) |
C2A—N3A—C6A—N4A | −58.8 (5) | C5B—N4B—C6B—N3B | 58.5 (6) |
C3A—N3A—C6A—N4A | 58.6 (5) | C4B—N4B—C6B—N3B | −58.6 (5) |
C12A—C7A—C8A—C9A | 1.1 (8) | C12B—C7B—C8B—C9B | 1.8 (8) |
C13A—C7A—C8A—C9A | −176.0 (5) | C13B—C7B—C8B—C9B | −177.5 (5) |
C7A—C8A—C9A—C10A | −2.1 (9) | C7B—C8B—C9B—C10B | −2.3 (9) |
C8A—C9A—C10A—C11A | 1.6 (10) | C8B—C9B—C10B—C11B | 2.3 (11) |
C9A—C10A—C11A—C12A | −0.1 (11) | C9B—C10B—C11B—C12B | −1.7 (13) |
C8A—C7A—C12A—C11A | 0.4 (8) | C10B—C11B—C12B—C7B | 1.0 (11) |
C13A—C7A—C12A—C11A | 177.6 (5) | C8B—C7B—C12B—C11B | −1.1 (9) |
C10A—C11A—C12A—C7A | −0.9 (10) | C13B—C7B—C12B—C11B | 178.2 (5) |
C12A—C7A—C13A—O2A | −9.8 (8) | C8B—C7B—C13B—O2B | 165.7 (6) |
C8A—C7A—C13A—O2A | 167.4 (6) | C12B—C7B—C13B—O2B | −13.5 (8) |
C12A—C7A—C13A—O1A | 171.4 (5) | C8B—C7B—C13B—O1B | −11.2 (7) |
C8A—C7A—C13A—O1A | −11.4 (7) | C12B—C7B—C13B—O1B | 169.5 (5) |
C19A—C14A—C15A—C16A | −0.8 (7) | C19B—C14B—C15B—C16B | 1.8 (7) |
C20A—C14A—C15A—C16A | −178.7 (4) | C20B—C14B—C15B—C16B | −179.7 (4) |
C14A—C15A—C16A—C17A | −0.7 (8) | C14B—C15B—C16B—C17B | −1.5 (8) |
C15A—C16A—C17A—C18A | 1.7 (9) | C15B—C16B—C17B—C18B | 1.2 (9) |
C16A—C17A—C18A—C19A | −1.2 (9) | C16B—C17B—C18B—C19B | −1.2 (9) |
C15A—C14A—C19A—C18A | 1.2 (7) | C17B—C18B—C19B—C14B | 1.5 (8) |
C20A—C14A—C19A—C18A | 179.2 (4) | C15B—C14B—C19B—C18B | −1.8 (7) |
C17A—C18A—C19A—C14A | −0.2 (8) | C20B—C14B—C19B—C18B | 179.7 (4) |
C19A—C14A—C20A—O4A | −4.0 (7) | C15B—C14B—C20B—O4B | 171.3 (5) |
C15A—C14A—C20A—O4A | 174.0 (5) | C19B—C14B—C20B—O4B | −10.3 (7) |
C19A—C14A—C20A—O3A | 176.3 (4) | C15B—C14B—C20B—O3B | −4.5 (7) |
C15A—C14A—C20A—O3A | −5.7 (6) | C19B—C14B—C20B—O3B | 173.9 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1O1···N1A | 0.82 (4) | 1.86 (4) | 2.666 (6) | 171 (5) |
O3A—H1O3···N2A | 0.82 (4) | 1.81 (5) | 2.608 (5) | 165 (5) |
O1B—H2O1···N1B | 0.83 (6) | 1.83 (6) | 2.660 (6) | 175 (7) |
O3B—H2O3···N2B | 0.84 (6) | 1.80 (6) | 2.628 (5) | 167 (5) |
C2A—H2AA···O4Ai | 0.98 | 2.49 | 3.145 (6) | 124 |
C5A—H5AA···O2Aii | 0.98 | 2.59 | 3.227 (7) | 123 |
C2B—H2BA···O4Bi | 0.98 | 2.53 | 3.188 (6) | 124 |
C5B—H5BA···O2Biii | 0.98 | 2.57 | 3.243 (7) | 126 |
C3A—H3AB···Cg17iv | 0.98 | 2.81 | 3.775 (5) | 169 |
C10A—H10A···Cg16v | 0.94 | 2.99 | 3.855 (7) | 154 |
C10B—H10B···Cg17vi | 0.94 | 2.87 | 3.681 (8) | 145 |
C5A—H5AB···Cg15iv | 0.98 | 2.90 | 3.831 (5) | 159 |
C17A—H17A···Cg18vii | 0.94 | 2.91 | 3.775 (6) | 154 |
C3B—H3BB···Cg18viii | 0.98 | 2.83 | 3.801 (5) | 171 |
C5B—H5BB···Cg16viii | 0.98 | 2.92 | 3.841 (6) | 157 |
Symmetry codes: (i) x−1, y, z; (ii) x+1/2, −y+1, z+1/2; (iii) x+1/2, −y+2, z+1/2; (iv) x−1/2, −y+1, z+1/2; (v) x−1/2, −y+1, z−1/2; (vi) x+1, y, z; (vii) x−1/2, −y+2, z−1/2; (viii) x−1/2, −y+2, z+1/2. |
Hexamethylenetetramine bis(benzoic acid) (1533069)
top
Crystal data top
C6H12N4·2(C7H6O2) | F(000) = 816 |
Mr = 384.43 | Dx = 1.304 Mg m−3 |
Monoclinic, Pn | Mo Kα radiation, λ = 0.71073 Å |
a = 6.1457 (8) Å | Cell parameters from 7036 reflections |
b = 26.765 (3) Å | θ = 2.9–28.1° |
c = 12.0716 (16) Å | µ = 0.09 mm−1 |
β = 99.654 (2)° | T = 250 K |
V = 1957.6 (4) Å3 | Block, colourless |
Z = 4 | 0.76 × 0.39 × 0.21 mm |
Data collection top
Bruker APEX Duo CCD area detector diffractometer | 4828 independent reflections |
Radiation source: fine-focus sealed tube | 3264 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
φ and ω scans | θmax = 28.3°, θmin = 1.9° |
Absorption correction: multi-scan (TWINABS; Sheldrick, 2012) | h = −8→8 |
Tmin = 0.755, Tmax = 0.937 | k = 0→35 |
6406 measured reflections | l = 0→16 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.051 | w = 1/[σ2(Fo2) + (0.0476P)2 + 0.380P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.128 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.18 e Å−3 |
4828 reflections | Δρmin = −0.15 e Å−3 |
522 parameters | Absolute structure: No quotients, so Flack parameter determined by classical intensity fit |
6 restraints | Absolute structure parameter: −1.6 (11) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1A | 0.6788 (5) | 0.38153 (13) | 0.4623 (3) | 0.0726 (10) | |
O2A | 0.4072 (5) | 0.39984 (14) | 0.3254 (3) | 0.0924 (13) | |
O3A | 0.4235 (4) | 0.60988 (11) | 0.3977 (2) | 0.0565 (8) | |
O4A | 0.7820 (5) | 0.60473 (12) | 0.4601 (3) | 0.0727 (9) | |
N1A | 0.4764 (4) | 0.45020 (11) | 0.5681 (2) | 0.0414 (7) | |
N2A | 0.3942 (4) | 0.53901 (10) | 0.5439 (2) | 0.0384 (7) | |
N3A | 0.1336 (5) | 0.48355 (13) | 0.6123 (3) | 0.0488 (8) | |
N4A | 0.4832 (6) | 0.50426 (13) | 0.7311 (3) | 0.0515 (9) | |
C1A | 0.4953 (6) | 0.49486 (13) | 0.4992 (3) | 0.0435 (9) | |
H1AA | 0.4222 | 0.4886 | 0.4219 | 0.052* | |
H1AB | 0.6515 | 0.5016 | 0.4977 | 0.052* | |
C2A | 0.1599 (5) | 0.52745 (14) | 0.5442 (4) | 0.0493 (10) | |
H2AA | 0.0891 | 0.5562 | 0.5737 | 0.059* | |
H2AB | 0.0857 | 0.5216 | 0.4669 | 0.059* | |
C3A | 0.2393 (6) | 0.44142 (14) | 0.5681 (3) | 0.0481 (9) | |
H3AA | 0.1656 | 0.4348 | 0.4910 | 0.058* | |
H3AB | 0.2221 | 0.4118 | 0.6134 | 0.058* | |
C4A | 0.5828 (6) | 0.46128 (16) | 0.6839 (3) | 0.0511 (10) | |
H4AA | 0.5713 | 0.4319 | 0.7312 | 0.061* | |
H4AB | 0.7398 | 0.4680 | 0.6848 | 0.061* | |
C5A | 0.5050 (6) | 0.54757 (14) | 0.6607 (3) | 0.0473 (9) | |
H5AA | 0.6618 | 0.5545 | 0.6614 | 0.057* | |
H5AB | 0.4398 | 0.5768 | 0.6914 | 0.057* | |
C6A | 0.2490 (7) | 0.49339 (17) | 0.7265 (4) | 0.0558 (11) | |
H6AA | 0.1787 | 0.5218 | 0.7577 | 0.067* | |
H6AB | 0.2339 | 0.4642 | 0.7737 | 0.067* | |
C7A | 0.6919 (6) | 0.34695 (14) | 0.2839 (3) | 0.0465 (9) | |
C8A | 0.9077 (7) | 0.33086 (15) | 0.3186 (4) | 0.0596 (11) | |
H8AA | 0.9820 | 0.3379 | 0.3916 | 0.072* | |
C9A | 1.0108 (9) | 0.30435 (19) | 0.2440 (5) | 0.0827 (17) | |
H9AA | 1.1574 | 0.2937 | 0.2662 | 0.099* | |
C10A | 0.9038 (12) | 0.2935 (2) | 0.1394 (6) | 0.099 (2) | |
H10A | 0.9761 | 0.2754 | 0.0896 | 0.118* | |
C11A | 0.6868 (11) | 0.3091 (2) | 0.1057 (5) | 0.0875 (17) | |
H11A | 0.6111 | 0.3011 | 0.0336 | 0.105* | |
C12A | 0.5844 (8) | 0.33605 (15) | 0.1784 (4) | 0.0631 (11) | |
H12A | 0.4388 | 0.3472 | 0.1555 | 0.076* | |
C13A | 0.5781 (6) | 0.37862 (15) | 0.3590 (4) | 0.0518 (10) | |
C14A | 0.6618 (5) | 0.65384 (13) | 0.2985 (3) | 0.0383 (8) | |
C15A | 0.4874 (6) | 0.66734 (14) | 0.2175 (3) | 0.0469 (9) | |
H15A | 0.3447 | 0.6560 | 0.2226 | 0.056* | |
C16A | 0.5190 (7) | 0.69728 (16) | 0.1287 (4) | 0.0619 (11) | |
H16A | 0.3985 | 0.7060 | 0.0733 | 0.074* | |
C17A | 0.7243 (8) | 0.71422 (16) | 0.1213 (4) | 0.0663 (13) | |
H17A | 0.7450 | 0.7351 | 0.0612 | 0.080* | |
C18A | 0.9023 (7) | 0.70114 (16) | 0.2010 (4) | 0.0628 (12) | |
H18A | 1.0440 | 0.7130 | 0.1952 | 0.075* | |
C19A | 0.8725 (6) | 0.67045 (14) | 0.2900 (4) | 0.0528 (10) | |
H19A | 0.9939 | 0.6610 | 0.3441 | 0.063* | |
C20A | 0.6294 (6) | 0.62049 (13) | 0.3948 (3) | 0.0417 (8) | |
O1B | 1.4442 (6) | 0.88365 (12) | 0.7162 (3) | 0.0717 (10) | |
O2B | 1.1789 (6) | 0.90126 (13) | 0.5775 (3) | 0.0881 (13) | |
O3B | 1.1836 (5) | 1.11033 (11) | 0.6504 (3) | 0.0585 (8) | |
O4B | 1.5397 (5) | 1.10825 (13) | 0.7183 (3) | 0.0780 (10) | |
N1B | 1.2381 (5) | 0.95177 (10) | 0.8205 (3) | 0.0408 (7) | |
N2B | 1.1537 (5) | 1.04034 (10) | 0.7986 (2) | 0.0402 (7) | |
N3B | 0.8947 (5) | 0.98443 (13) | 0.8663 (3) | 0.0504 (8) | |
N4B | 1.2443 (6) | 1.00401 (10) | 0.9848 (3) | 0.0467 (8) | |
C1B | 1.2573 (6) | 0.99707 (11) | 0.7535 (3) | 0.0382 (9) | |
H1BA | 1.4137 | 1.0043 | 0.7534 | 0.046* | |
H1BB | 1.1865 | 0.9912 | 0.6756 | 0.046* | |
C2B | 0.9188 (6) | 1.02840 (14) | 0.7991 (3) | 0.0504 (10) | |
H2BA | 0.8475 | 1.0569 | 0.8291 | 0.060* | |
H2BB | 0.8443 | 1.0227 | 0.7218 | 0.060* | |
C3B | 1.0008 (6) | 0.94246 (13) | 0.8194 (3) | 0.0501 (10) | |
H3BA | 0.9276 | 0.9366 | 0.7420 | 0.060* | |
H3BB | 0.9837 | 0.9123 | 0.8632 | 0.060* | |
C4B | 1.3429 (6) | 0.96158 (13) | 0.9371 (3) | 0.0491 (10) | |
H4BA | 1.3287 | 0.9319 | 0.9829 | 0.059* | |
H4BB | 1.5006 | 0.9680 | 0.9393 | 0.059* | |
C5B | 1.2634 (7) | 1.04821 (13) | 0.9162 (3) | 0.0472 (9) | |
H5BA | 1.4197 | 1.0559 | 0.9174 | 0.057* | |
H5BB | 1.1958 | 1.0768 | 0.9480 | 0.057* | |
C6B | 1.0084 (7) | 0.99315 (15) | 0.9809 (3) | 0.0543 (11) | |
H6BA | 0.9931 | 0.9635 | 1.0267 | 0.065* | |
H6BB | 0.9387 | 1.0213 | 1.0132 | 0.065* | |
C7B | 1.4633 (7) | 0.84761 (11) | 0.5422 (3) | 0.0444 (9) | |
C8B | 1.6777 (7) | 0.83275 (14) | 0.5771 (4) | 0.0562 (11) | |
H8BA | 1.7519 | 0.8420 | 0.6487 | 0.067* | |
C9B | 1.7858 (10) | 0.80394 (17) | 0.5069 (5) | 0.0819 (16) | |
H9BA | 1.9328 | 0.7939 | 0.5303 | 0.098* | |
C10B | 1.6753 (13) | 0.7907 (2) | 0.4043 (6) | 0.100 (2) | |
H10B | 1.7463 | 0.7708 | 0.3569 | 0.120* | |
C11B | 1.4627 (13) | 0.8057 (2) | 0.3687 (5) | 0.097 (2) | |
H11B | 1.3892 | 0.7963 | 0.2971 | 0.117* | |
C12B | 1.3556 (9) | 0.83441 (16) | 0.4368 (4) | 0.0711 (13) | |
H12B | 1.2099 | 0.8450 | 0.4118 | 0.085* | |
C13B | 1.3477 (7) | 0.87933 (13) | 0.6132 (3) | 0.0487 (9) | |
C14B | 1.4232 (6) | 1.15406 (11) | 0.5521 (3) | 0.0367 (8) | |
C15B | 1.2495 (6) | 1.16462 (12) | 0.4663 (3) | 0.0432 (9) | |
H15B | 1.1082 | 1.1519 | 0.4697 | 0.052* | |
C16B | 1.2823 (7) | 1.19361 (13) | 0.3760 (3) | 0.0533 (10) | |
H16B | 1.1641 | 1.2003 | 0.3177 | 0.064* | |
C17B | 1.4882 (8) | 1.21261 (15) | 0.3716 (4) | 0.0612 (11) | |
H17B | 1.5096 | 1.2330 | 0.3109 | 0.073* | |
C18B | 1.6619 (7) | 1.20223 (14) | 0.4544 (4) | 0.0610 (11) | |
H18B | 1.8029 | 1.2149 | 0.4500 | 0.073* | |
C19B | 1.6305 (7) | 1.17284 (15) | 0.5458 (4) | 0.0544 (10) | |
H19B | 1.7501 | 1.1658 | 0.6030 | 0.065* | |
C20B | 1.3884 (7) | 1.12257 (12) | 0.6487 (3) | 0.0455 (9) | |
H1O1 | 0.609 (7) | 0.4031 (14) | 0.495 (4) | 0.086 (17)* | |
H1O3 | 0.416 (10) | 0.5865 (15) | 0.443 (4) | 0.11 (2)* | |
H2O1 | 1.383 (9) | 0.9045 (16) | 0.753 (4) | 0.10 (2)* | |
H2O3 | 1.177 (14) | 1.090 (2) | 0.702 (5) | 0.18 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1A | 0.072 (2) | 0.086 (2) | 0.058 (2) | 0.0413 (18) | 0.0070 (17) | −0.0091 (17) |
O2A | 0.061 (2) | 0.122 (3) | 0.086 (3) | 0.046 (2) | −0.0142 (18) | −0.026 (2) |
O3A | 0.0454 (15) | 0.0682 (19) | 0.0562 (18) | −0.0020 (13) | 0.0093 (13) | 0.0258 (15) |
O4A | 0.0519 (17) | 0.087 (2) | 0.074 (2) | 0.0020 (16) | −0.0055 (15) | 0.0365 (18) |
N1A | 0.0355 (16) | 0.0503 (16) | 0.0413 (17) | 0.0048 (13) | 0.0144 (13) | 0.0053 (13) |
N2A | 0.0339 (15) | 0.0471 (16) | 0.0370 (17) | −0.0007 (12) | 0.0137 (12) | 0.0048 (13) |
N3A | 0.0300 (15) | 0.062 (2) | 0.060 (2) | −0.0062 (14) | 0.0218 (14) | 0.0028 (17) |
N4A | 0.054 (2) | 0.069 (2) | 0.0312 (19) | −0.0023 (15) | 0.0073 (15) | 0.0036 (14) |
C1A | 0.0365 (19) | 0.065 (2) | 0.034 (2) | −0.0020 (15) | 0.0205 (16) | 0.0024 (15) |
C2A | 0.0318 (18) | 0.056 (2) | 0.061 (3) | 0.0073 (15) | 0.0093 (17) | 0.0049 (19) |
C3A | 0.0391 (19) | 0.051 (2) | 0.056 (2) | −0.0089 (16) | 0.0122 (16) | 0.0018 (18) |
C4A | 0.0357 (19) | 0.070 (3) | 0.046 (2) | 0.0071 (17) | 0.0035 (16) | 0.0163 (19) |
C5A | 0.046 (2) | 0.058 (2) | 0.039 (2) | −0.0103 (17) | 0.0071 (16) | −0.0027 (17) |
C6A | 0.056 (2) | 0.069 (3) | 0.050 (3) | −0.003 (2) | 0.034 (2) | 0.0024 (19) |
C7A | 0.051 (2) | 0.0411 (19) | 0.049 (2) | 0.0052 (16) | 0.0139 (17) | 0.0025 (16) |
C8A | 0.052 (2) | 0.055 (2) | 0.075 (3) | 0.014 (2) | 0.019 (2) | 0.009 (2) |
C9A | 0.082 (4) | 0.071 (3) | 0.106 (5) | 0.031 (3) | 0.050 (3) | 0.020 (3) |
C10A | 0.142 (6) | 0.074 (3) | 0.098 (5) | 0.021 (4) | 0.074 (4) | −0.002 (3) |
C11A | 0.126 (5) | 0.081 (4) | 0.058 (3) | −0.002 (3) | 0.023 (3) | −0.011 (3) |
C12A | 0.076 (3) | 0.050 (2) | 0.064 (3) | 0.005 (2) | 0.013 (2) | 0.002 (2) |
C13A | 0.046 (2) | 0.050 (2) | 0.059 (3) | 0.0082 (17) | 0.0085 (19) | −0.0057 (19) |
C14A | 0.0324 (17) | 0.0404 (18) | 0.044 (2) | 0.0008 (13) | 0.0111 (15) | −0.0028 (15) |
C15A | 0.041 (2) | 0.050 (2) | 0.050 (2) | 0.0014 (16) | 0.0104 (17) | 0.0067 (17) |
C16A | 0.063 (3) | 0.071 (3) | 0.051 (3) | 0.006 (2) | 0.009 (2) | 0.016 (2) |
C17A | 0.082 (3) | 0.056 (3) | 0.068 (3) | 0.007 (2) | 0.032 (3) | 0.020 (2) |
C18A | 0.051 (2) | 0.060 (2) | 0.086 (3) | −0.007 (2) | 0.036 (2) | 0.004 (2) |
C19A | 0.041 (2) | 0.048 (2) | 0.072 (3) | 0.0078 (17) | 0.0180 (19) | 0.0070 (19) |
C20A | 0.0400 (19) | 0.0402 (18) | 0.045 (2) | 0.0051 (15) | 0.0071 (16) | 0.0070 (16) |
O1B | 0.090 (3) | 0.072 (2) | 0.0488 (19) | 0.0457 (18) | 0.0010 (17) | −0.0095 (15) |
O2B | 0.077 (2) | 0.091 (2) | 0.084 (3) | 0.0405 (19) | −0.019 (2) | −0.028 (2) |
O3B | 0.0592 (19) | 0.0572 (17) | 0.0562 (19) | −0.0005 (13) | 0.0009 (15) | 0.0245 (14) |
O4B | 0.066 (2) | 0.090 (2) | 0.069 (2) | 0.0078 (17) | −0.0135 (17) | 0.0353 (18) |
N1B | 0.0494 (19) | 0.0302 (14) | 0.0431 (17) | 0.0047 (12) | 0.0091 (14) | −0.0011 (12) |
N2B | 0.0537 (19) | 0.0300 (14) | 0.0355 (16) | 0.0014 (12) | 0.0035 (13) | 0.0032 (12) |
N3B | 0.0411 (17) | 0.0561 (19) | 0.056 (2) | −0.0010 (15) | 0.0128 (15) | 0.0016 (17) |
N4B | 0.062 (2) | 0.0464 (18) | 0.0298 (18) | −0.0021 (14) | 0.0013 (15) | 0.0010 (12) |
C1B | 0.046 (2) | 0.0282 (17) | 0.041 (2) | 0.0020 (12) | 0.0070 (17) | 0.0026 (12) |
C2B | 0.041 (2) | 0.055 (2) | 0.054 (2) | 0.0125 (16) | 0.0027 (17) | 0.0076 (18) |
C3B | 0.056 (2) | 0.0381 (19) | 0.057 (2) | −0.0138 (16) | 0.0101 (18) | −0.0027 (17) |
C4B | 0.056 (2) | 0.046 (2) | 0.042 (2) | 0.0116 (17) | −0.0019 (17) | 0.0125 (17) |
C5B | 0.060 (2) | 0.0339 (17) | 0.046 (2) | −0.0060 (16) | 0.0033 (18) | −0.0076 (15) |
C6B | 0.077 (3) | 0.052 (2) | 0.040 (2) | 0.000 (2) | 0.029 (2) | 0.0019 (17) |
C7B | 0.066 (3) | 0.0228 (15) | 0.045 (2) | −0.0010 (16) | 0.0110 (18) | 0.0024 (14) |
C8B | 0.073 (3) | 0.038 (2) | 0.061 (3) | 0.0059 (19) | 0.021 (2) | −0.0021 (18) |
C9B | 0.099 (4) | 0.059 (3) | 0.097 (4) | 0.018 (3) | 0.045 (3) | −0.002 (3) |
C10B | 0.168 (7) | 0.064 (3) | 0.083 (4) | 0.025 (4) | 0.066 (4) | −0.008 (3) |
C11B | 0.170 (7) | 0.071 (4) | 0.052 (3) | 0.010 (4) | 0.020 (4) | −0.016 (3) |
C12B | 0.100 (4) | 0.059 (3) | 0.050 (3) | 0.003 (3) | 0.003 (2) | −0.005 (2) |
C13B | 0.059 (2) | 0.0381 (19) | 0.048 (2) | 0.0068 (17) | 0.0057 (19) | −0.0033 (17) |
C14B | 0.047 (2) | 0.0217 (14) | 0.0400 (19) | 0.0031 (13) | 0.0027 (15) | −0.0016 (13) |
C15B | 0.050 (2) | 0.0332 (17) | 0.044 (2) | 0.0002 (15) | −0.0006 (16) | 0.0052 (15) |
C16B | 0.066 (3) | 0.041 (2) | 0.049 (2) | −0.0010 (18) | −0.0010 (18) | 0.0087 (18) |
C17B | 0.079 (3) | 0.045 (2) | 0.062 (3) | −0.002 (2) | 0.018 (2) | 0.010 (2) |
C18B | 0.057 (3) | 0.046 (2) | 0.081 (3) | −0.0085 (19) | 0.013 (2) | −0.001 (2) |
C19B | 0.044 (2) | 0.051 (2) | 0.065 (3) | 0.0004 (18) | 0.0012 (18) | −0.003 (2) |
C20B | 0.057 (2) | 0.0333 (17) | 0.043 (2) | 0.0061 (16) | 0.0002 (18) | 0.0018 (15) |
Geometric parameters (Å, º) top
O1A—C13A | 1.297 (5) | O1B—C13B | 1.289 (5) |
O1A—H1O1 | 0.85 (2) | O1B—H2O1 | 0.84 (2) |
O2A—C13A | 1.203 (5) | O2B—C13B | 1.207 (5) |
O3A—C20A | 1.303 (4) | O3B—C20B | 1.304 (5) |
O3A—H1O3 | 0.84 (2) | O3B—H2O3 | 0.84 (2) |
O4A—C20A | 1.197 (4) | O4B—C20B | 1.207 (4) |
N1A—C4A | 1.471 (5) | N1B—C4B | 1.471 (4) |
N1A—C1A | 1.472 (4) | N1B—C1B | 1.473 (4) |
N1A—C3A | 1.476 (4) | N1B—C3B | 1.477 (5) |
N2A—C2A | 1.474 (4) | N2B—C1B | 1.470 (4) |
N2A—C5A | 1.477 (4) | N2B—C2B | 1.479 (5) |
N2A—C1A | 1.479 (4) | N2B—C5B | 1.481 (5) |
N3A—C3A | 1.447 (5) | N3B—C2B | 1.452 (5) |
N3A—C2A | 1.459 (5) | N3B—C6B | 1.459 (5) |
N3A—C6A | 1.465 (5) | N3B—C3B | 1.460 (5) |
N4A—C5A | 1.456 (5) | N4B—C4B | 1.451 (5) |
N4A—C6A | 1.461 (5) | N4B—C5B | 1.460 (5) |
N4A—C4A | 1.463 (5) | N4B—C6B | 1.472 (5) |
C1A—H1AA | 0.9800 | C1B—H1BA | 0.9800 |
C1A—H1AB | 0.9800 | C1B—H1BB | 0.9800 |
C2A—H2AA | 0.9800 | C2B—H2BA | 0.9800 |
C2A—H2AB | 0.9800 | C2B—H2BB | 0.9800 |
C3A—H3AA | 0.9800 | C3B—H3BA | 0.9800 |
C3A—H3AB | 0.9800 | C3B—H3BB | 0.9800 |
C4A—H4AA | 0.9800 | C4B—H4BA | 0.9800 |
C4A—H4AB | 0.9800 | C4B—H4BB | 0.9800 |
C5A—H5AA | 0.9800 | C5B—H5BA | 0.9800 |
C5A—H5AB | 0.9800 | C5B—H5BB | 0.9800 |
C6A—H6AA | 0.9800 | C6B—H6BA | 0.9800 |
C6A—H6AB | 0.9800 | C6B—H6BB | 0.9800 |
C7A—C12A | 1.364 (6) | C7B—C8B | 1.373 (6) |
C7A—C8A | 1.391 (6) | C7B—C12B | 1.378 (6) |
C7A—C13A | 1.498 (5) | C7B—C13B | 1.471 (5) |
C8A—C9A | 1.381 (6) | C8B—C9B | 1.394 (6) |
C8A—H8AA | 0.9400 | C8B—H8BA | 0.9400 |
C9A—C10A | 1.355 (8) | C9B—C10B | 1.356 (9) |
C9A—H9AA | 0.9400 | C9B—H9BA | 0.9400 |
C10A—C11A | 1.392 (9) | C10B—C11B | 1.366 (9) |
C10A—H10A | 0.9400 | C10B—H10B | 0.9400 |
C11A—C12A | 1.369 (7) | C11B—C12B | 1.372 (7) |
C11A—H11A | 0.9400 | C11B—H11B | 0.9400 |
C12A—H12A | 0.9400 | C12B—H12B | 0.9400 |
C14A—C15A | 1.373 (5) | C14B—C19B | 1.383 (5) |
C14A—C19A | 1.389 (5) | C14B—C15B | 1.386 (5) |
C14A—C20A | 1.505 (5) | C14B—C20B | 1.483 (5) |
C15A—C16A | 1.378 (5) | C15B—C16B | 1.380 (5) |
C15A—H15A | 0.9400 | C15B—H15B | 0.9400 |
C16A—C17A | 1.358 (6) | C16B—C17B | 1.373 (6) |
C16A—H16A | 0.9400 | C16B—H16B | 0.9400 |
C17A—C18A | 1.375 (7) | C17B—C18B | 1.363 (6) |
C17A—H17A | 0.9400 | C17B—H17B | 0.9400 |
C18A—C19A | 1.389 (6) | C18B—C19B | 1.394 (6) |
C18A—H18A | 0.9400 | C18B—H18B | 0.9400 |
C19A—H19A | 0.9400 | C19B—H19B | 0.9400 |
| | | |
C13A—O1A—H1O1 | 107 (4) | C13B—O1B—H2O1 | 113 (4) |
C20A—O3A—H1O3 | 110 (4) | C20B—O3B—H2O3 | 110 (6) |
C4A—N1A—C1A | 108.0 (3) | C4B—N1B—C1B | 108.4 (3) |
C4A—N1A—C3A | 108.3 (3) | C4B—N1B—C3B | 108.1 (3) |
C1A—N1A—C3A | 107.5 (3) | C1B—N1B—C3B | 107.7 (3) |
C2A—N2A—C5A | 108.9 (3) | C1B—N2B—C2B | 108.4 (3) |
C2A—N2A—C1A | 107.7 (3) | C1B—N2B—C5B | 108.2 (3) |
C5A—N2A—C1A | 108.5 (3) | C2B—N2B—C5B | 108.3 (3) |
C3A—N3A—C2A | 108.7 (3) | C2B—N3B—C6B | 108.8 (3) |
C3A—N3A—C6A | 108.1 (3) | C2B—N3B—C3B | 108.2 (3) |
C2A—N3A—C6A | 107.7 (3) | C6B—N3B—C3B | 108.4 (3) |
C5A—N4A—C6A | 108.8 (3) | C4B—N4B—C5B | 109.3 (3) |
C5A—N4A—C4A | 108.3 (3) | C4B—N4B—C6B | 107.9 (3) |
C6A—N4A—C4A | 107.6 (3) | C5B—N4B—C6B | 108.3 (3) |
N1A—C1A—N2A | 111.4 (3) | N2B—C1B—N1B | 111.4 (3) |
N1A—C1A—H1AA | 109.4 | N2B—C1B—H1BA | 109.3 |
N2A—C1A—H1AA | 109.4 | N1B—C1B—H1BA | 109.3 |
N1A—C1A—H1AB | 109.4 | N2B—C1B—H1BB | 109.3 |
N2A—C1A—H1AB | 109.4 | N1B—C1B—H1BB | 109.3 |
H1AA—C1A—H1AB | 108.0 | H1BA—C1B—H1BB | 108.0 |
N3A—C2A—N2A | 111.8 (3) | N3B—C2B—N2B | 111.6 (3) |
N3A—C2A—H2AA | 109.3 | N3B—C2B—H2BA | 109.3 |
N2A—C2A—H2AA | 109.3 | N2B—C2B—H2BA | 109.3 |
N3A—C2A—H2AB | 109.3 | N3B—C2B—H2BB | 109.3 |
N2A—C2A—H2AB | 109.3 | N2B—C2B—H2BB | 109.3 |
H2AA—C2A—H2AB | 107.9 | H2BA—C2B—H2BB | 108.0 |
N3A—C3A—N1A | 112.3 (3) | N3B—C3B—N1B | 111.8 (3) |
N3A—C3A—H3AA | 109.1 | N3B—C3B—H3BA | 109.3 |
N1A—C3A—H3AA | 109.1 | N1B—C3B—H3BA | 109.3 |
N3A—C3A—H3AB | 109.1 | N3B—C3B—H3BB | 109.3 |
N1A—C3A—H3AB | 109.1 | N1B—C3B—H3BB | 109.3 |
H3AA—C3A—H3AB | 107.9 | H3BA—C3B—H3BB | 107.9 |
N4A—C4A—N1A | 112.4 (3) | N4B—C4B—N1B | 112.0 (3) |
N4A—C4A—H4AA | 109.1 | N4B—C4B—H4BA | 109.2 |
N1A—C4A—H4AA | 109.1 | N1B—C4B—H4BA | 109.2 |
N4A—C4A—H4AB | 109.1 | N4B—C4B—H4BB | 109.2 |
N1A—C4A—H4AB | 109.1 | N1B—C4B—H4BB | 109.2 |
H4AA—C4A—H4AB | 107.9 | H4BA—C4B—H4BB | 107.9 |
N4A—C5A—N2A | 111.1 (3) | N4B—C5B—N2B | 111.2 (3) |
N4A—C5A—H5AA | 109.4 | N4B—C5B—H5BA | 109.4 |
N2A—C5A—H5AA | 109.4 | N2B—C5B—H5BA | 109.4 |
N4A—C5A—H5AB | 109.4 | N4B—C5B—H5BB | 109.4 |
N2A—C5A—H5AB | 109.4 | N2B—C5B—H5BB | 109.4 |
H5AA—C5A—H5AB | 108.0 | H5BA—C5B—H5BB | 108.0 |
N4A—C6A—N3A | 112.9 (3) | N3B—C6B—N4B | 112.0 (3) |
N4A—C6A—H6AA | 109.0 | N3B—C6B—H6BA | 109.2 |
N3A—C6A—H6AA | 109.0 | N4B—C6B—H6BA | 109.2 |
N4A—C6A—H6AB | 109.0 | N3B—C6B—H6BB | 109.2 |
N3A—C6A—H6AB | 109.0 | N4B—C6B—H6BB | 109.2 |
H6AA—C6A—H6AB | 107.8 | H6BA—C6B—H6BB | 107.9 |
C12A—C7A—C8A | 120.2 (4) | C8B—C7B—C12B | 119.8 (4) |
C12A—C7A—C13A | 119.0 (4) | C8B—C7B—C13B | 121.4 (4) |
C8A—C7A—C13A | 120.7 (4) | C12B—C7B—C13B | 118.8 (4) |
C9A—C8A—C7A | 118.7 (5) | C7B—C8B—C9B | 120.3 (5) |
C9A—C8A—H8AA | 120.6 | C7B—C8B—H8BA | 119.9 |
C7A—C8A—H8AA | 120.6 | C9B—C8B—H8BA | 119.9 |
C10A—C9A—C8A | 121.0 (5) | C10B—C9B—C8B | 118.9 (6) |
C10A—C9A—H9AA | 119.5 | C10B—C9B—H9BA | 120.5 |
C8A—C9A—H9AA | 119.5 | C8B—C9B—H9BA | 120.5 |
C9A—C10A—C11A | 120.0 (5) | C9B—C10B—C11B | 121.1 (5) |
C9A—C10A—H10A | 120.0 | C9B—C10B—H10B | 119.5 |
C11A—C10A—H10A | 120.0 | C11B—C10B—H10B | 119.5 |
C12A—C11A—C10A | 119.5 (5) | C10B—C11B—C12B | 120.4 (5) |
C12A—C11A—H11A | 120.3 | C10B—C11B—H11B | 119.8 |
C10A—C11A—H11A | 120.3 | C12B—C11B—H11B | 119.8 |
C7A—C12A—C11A | 120.6 (5) | C11B—C12B—C7B | 119.5 (5) |
C7A—C12A—H12A | 119.7 | C11B—C12B—H12B | 120.2 |
C11A—C12A—H12A | 119.7 | C7B—C12B—H12B | 120.2 |
O2A—C13A—O1A | 123.0 (4) | O2B—C13B—O1B | 122.0 (4) |
O2A—C13A—C7A | 122.2 (4) | O2B—C13B—C7B | 122.8 (4) |
O1A—C13A—C7A | 114.8 (3) | O1B—C13B—C7B | 115.1 (3) |
C15A—C14A—C19A | 119.3 (3) | C19B—C14B—C15B | 119.0 (3) |
C15A—C14A—C20A | 121.2 (3) | C19B—C14B—C20B | 120.4 (3) |
C19A—C14A—C20A | 119.5 (3) | C15B—C14B—C20B | 120.6 (3) |
C14A—C15A—C16A | 120.8 (4) | C16B—C15B—C14B | 120.6 (4) |
C14A—C15A—H15A | 119.6 | C16B—C15B—H15B | 119.7 |
C16A—C15A—H15A | 119.6 | C14B—C15B—H15B | 119.7 |
C17A—C16A—C15A | 119.9 (4) | C17B—C16B—C15B | 119.8 (4) |
C17A—C16A—H16A | 120.0 | C17B—C16B—H16B | 120.1 |
C15A—C16A—H16A | 120.0 | C15B—C16B—H16B | 120.1 |
C16A—C17A—C18A | 120.5 (4) | C18B—C17B—C16B | 120.6 (4) |
C16A—C17A—H17A | 119.7 | C18B—C17B—H17B | 119.7 |
C18A—C17A—H17A | 119.7 | C16B—C17B—H17B | 119.7 |
C17A—C18A—C19A | 119.9 (4) | C17B—C18B—C19B | 120.0 (4) |
C17A—C18A—H18A | 120.0 | C17B—C18B—H18B | 120.0 |
C19A—C18A—H18A | 120.0 | C19B—C18B—H18B | 120.0 |
C14A—C19A—C18A | 119.5 (4) | C14B—C19B—C18B | 120.0 (4) |
C14A—C19A—H19A | 120.3 | C14B—C19B—H19B | 120.0 |
C18A—C19A—H19A | 120.3 | C18B—C19B—H19B | 120.0 |
O4A—C20A—O3A | 124.3 (4) | O4B—C20B—O3B | 122.8 (4) |
O4A—C20A—C14A | 121.8 (3) | O4B—C20B—C14B | 122.2 (4) |
O3A—C20A—C14A | 113.9 (3) | O3B—C20B—C14B | 114.9 (3) |
| | | |
C4A—N1A—C1A—N2A | −57.7 (4) | C2B—N2B—C1B—N1B | −58.4 (4) |
C3A—N1A—C1A—N2A | 59.0 (4) | C5B—N2B—C1B—N1B | 58.9 (4) |
C2A—N2A—C1A—N1A | −59.3 (4) | C4B—N1B—C1B—N2B | −58.3 (4) |
C5A—N2A—C1A—N1A | 58.4 (4) | C3B—N1B—C1B—N2B | 58.5 (4) |
C3A—N3A—C2A—N2A | −58.8 (4) | C6B—N3B—C2B—N2B | 58.3 (4) |
C6A—N3A—C2A—N2A | 58.1 (4) | C3B—N3B—C2B—N2B | −59.4 (4) |
C5A—N2A—C2A—N3A | −58.7 (4) | C1B—N2B—C2B—N3B | 58.8 (4) |
C1A—N2A—C2A—N3A | 58.8 (4) | C5B—N2B—C2B—N3B | −58.3 (4) |
C2A—N3A—C3A—N1A | 58.9 (4) | C2B—N3B—C3B—N1B | 60.0 (4) |
C6A—N3A—C3A—N1A | −57.8 (4) | C6B—N3B—C3B—N1B | −58.0 (4) |
C4A—N1A—C3A—N3A | 57.5 (4) | C4B—N1B—C3B—N3B | 57.7 (4) |
C1A—N1A—C3A—N3A | −58.9 (4) | C1B—N1B—C3B—N3B | −59.3 (4) |
C5A—N4A—C4A—N1A | −59.7 (4) | C5B—N4B—C4B—N1B | −58.4 (4) |
C6A—N4A—C4A—N1A | 57.8 (4) | C6B—N4B—C4B—N1B | 59.2 (4) |
C1A—N1A—C4A—N4A | 58.6 (4) | C1B—N1B—C4B—N4B | 57.9 (4) |
C3A—N1A—C4A—N4A | −57.5 (4) | C3B—N1B—C4B—N4B | −58.7 (4) |
C6A—N4A—C5A—N2A | −57.3 (4) | C4B—N4B—C5B—N2B | 58.6 (4) |
C4A—N4A—C5A—N2A | 59.4 (4) | C6B—N4B—C5B—N2B | −58.7 (4) |
C2A—N2A—C5A—N4A | 57.7 (4) | C1B—N2B—C5B—N4B | −58.7 (4) |
C1A—N2A—C5A—N4A | −59.2 (4) | C2B—N2B—C5B—N4B | 58.5 (4) |
C5A—N4A—C6A—N3A | 58.6 (4) | C2B—N3B—C6B—N4B | −58.7 (4) |
C4A—N4A—C6A—N3A | −58.6 (4) | C3B—N3B—C6B—N4B | 58.8 (4) |
C3A—N3A—C6A—N4A | 58.9 (4) | C4B—N4B—C6B—N3B | −59.3 (4) |
C2A—N3A—C6A—N4A | −58.4 (4) | C5B—N4B—C6B—N3B | 58.9 (4) |
C12A—C7A—C8A—C9A | 0.8 (6) | C12B—C7B—C8B—C9B | −0.7 (6) |
C13A—C7A—C8A—C9A | −176.0 (4) | C13B—C7B—C8B—C9B | −178.1 (4) |
C7A—C8A—C9A—C10A | −0.9 (7) | C7B—C8B—C9B—C10B | −0.4 (7) |
C8A—C9A—C10A—C11A | 0.0 (9) | C8B—C9B—C10B—C11B | 1.0 (9) |
C9A—C10A—C11A—C12A | 1.0 (9) | C9B—C10B—C11B—C12B | −0.4 (10) |
C8A—C7A—C12A—C11A | 0.2 (7) | C10B—C11B—C12B—C7B | −0.8 (8) |
C13A—C7A—C12A—C11A | 177.1 (4) | C8B—C7B—C12B—C11B | 1.3 (7) |
C10A—C11A—C12A—C7A | −1.1 (8) | C13B—C7B—C12B—C11B | 178.7 (4) |
C12A—C7A—C13A—O2A | −9.4 (6) | C8B—C7B—C13B—O2B | 164.5 (4) |
C8A—C7A—C13A—O2A | 167.5 (5) | C12B—C7B—C13B—O2B | −12.9 (6) |
C12A—C7A—C13A—O1A | 171.0 (4) | C8B—C7B—C13B—O1B | −13.0 (6) |
C8A—C7A—C13A—O1A | −12.1 (6) | C12B—C7B—C13B—O1B | 169.6 (4) |
C19A—C14A—C15A—C16A | −0.4 (6) | C19B—C14B—C15B—C16B | −0.3 (5) |
C20A—C14A—C15A—C16A | −179.0 (4) | C20B—C14B—C15B—C16B | −179.5 (3) |
C14A—C15A—C16A—C17A | −0.7 (6) | C14B—C15B—C16B—C17B | −0.7 (6) |
C15A—C16A—C17A—C18A | 0.9 (7) | C15B—C16B—C17B—C18B | 1.4 (7) |
C16A—C17A—C18A—C19A | −0.1 (7) | C16B—C17B—C18B—C19B | −1.2 (7) |
C15A—C14A—C19A—C18A | 1.2 (6) | C15B—C14B—C19B—C18B | 0.5 (6) |
C20A—C14A—C19A—C18A | 179.9 (3) | C20B—C14B—C19B—C18B | 179.7 (3) |
C17A—C18A—C19A—C14A | −0.9 (6) | C17B—C18B—C19B—C14B | 0.2 (6) |
C15A—C14A—C20A—O4A | 173.0 (4) | C19B—C14B—C20B—O4B | −7.4 (6) |
C19A—C14A—C20A—O4A | −5.6 (6) | C15B—C14B—C20B—O4B | 171.8 (4) |
C15A—C14A—C20A—O3A | −5.4 (5) | C19B—C14B—C20B—O3B | 174.7 (3) |
C19A—C14A—C20A—O3A | 176.0 (3) | C15B—C14B—C20B—O3B | −6.0 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1O1···N1A | 0.85 (4) | 1.81 (4) | 2.663 (4) | 177 (4) |
O3A—H1O3···N2A | 0.84 (4) | 1.78 (4) | 2.618 (4) | 177 (6) |
O1B—H2O1···N1B | 0.84 (5) | 1.82 (5) | 2.655 (5) | 175 (5) |
O3B—H2O3···N2B | 0.83 (6) | 1.79 (6) | 2.618 (4) | 173 (7) |
C2A—H2AA···O4Ai | 0.98 | 2.50 | 3.148 (5) | 123 |
C5A—H5AA···O2Aii | 0.98 | 2.59 | 3.224 (5) | 123 |
C2B—H2BA···O4Bi | 0.98 | 2.53 | 3.191 (5) | 125 |
C5B—H5BA···O2Biii | 0.98 | 2.56 | 3.236 (5) | 126 |
C3A—H3AB···Cg17iv | 0.98 | 2.83 | 3.798 (4) | 169 |
C5A—H5AB···Cg15iv | 0.98 | 2.92 | 3.848 (4) | 159 |
C10A—H10A···Cg16v | 0.94 | 3.00 | 3.856 (7) | 152 |
C10B—H10B···Cg17vi | 0.94 | 2.91 | 3.713 (6) | 144 |
C17A—H17A···Cg18vii | 0.94 | 2.90 | 3.770 (5) | 153 |
C3B—H3BB···Cg18viii | 0.98 | 2.84 | 3.807 (4) | 171 |
C5B—H5BB···Cg16viii | 0.98 | 2.92 | 3.840 (4) | 157 |
Symmetry codes: (i) x−1, y, z; (ii) x+1/2, −y+1, z+1/2; (iii) x+1/2, −y+2, z+1/2; (iv) x−1/2, −y+1, z+1/2; (v) x−1/2, −y+1, z−1/2; (vi) x+1, y, z; (vii) x−1/2, −y+2, z−1/2; (viii) x−1/2, −y+2, z+1/2. |
Hexamethylenetetramine bis(benzoic acid) (1533070)
top
Crystal data top
C6H12N4·2(C7H6O2) | Dx = 1.303 Mg m−3 |
Mr = 384.43 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Fmm2 | Cell parameters from 1844 reflections |
a = 10.1183 (18) Å | θ = 3.0–23.8° |
b = 27.015 (5) Å | µ = 0.09 mm−1 |
c = 7.1684 (13) Å | T = 260 K |
V = 1959.5 (6) Å3 | Block, colourless |
Z = 4 | 0.76 × 0.39 × 0.21 mm |
F(000) = 816 | |
Data collection top
Bruker APEX Duo CCD area detector diffractometer | 1191 independent reflections |
Radiation source: fine-focus sealed tube | 1004 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
φ and ω scans | θmax = 27.5°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −11→13 |
Tmin = 0.860, Tmax = 0.937 | k = −34→34 |
4726 measured reflections | l = −9→9 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.049 | w = 1/[σ2(Fo2) + (0.0559P)2 + 1.217P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.137 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.11 e Å−3 |
1191 reflections | Δρmin = −0.14 e Å−3 |
103 parameters | Absolute structure: Flack x determined using 382 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
2 restraints | Absolute structure parameter: 0.1 (6) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.5820 (7) | 0.6126 (2) | 0.6928 (8) | 0.0835 (17) | 0.5 |
H1O1 | 0.557 (7) | 0.597 (3) | 0.600 (8) | 0.12 (3)* | 0.5 |
O2 | 0.3726 (6) | 0.6044 (3) | 0.7737 (12) | 0.121 (3) | 0.5 |
C4 | 0.4757 (6) | 0.62132 (19) | 0.7979 (8) | 0.056 (2) | 0.5 |
C5 | 0.5051 (10) | 0.65328 (12) | 0.9615 (5) | 0.0605 (12) | 0.5 |
C6 | 0.6342 (9) | 0.6662 (2) | 1.0067 (9) | 0.081 (3) | 0.5 |
H6A | 0.7039 | 0.6553 | 0.9328 | 0.097* | 0.5 |
C7 | 0.6590 (7) | 0.6955 (3) | 1.1623 (10) | 0.104 (3) | 0.5 |
H7A | 0.7453 | 0.7042 | 1.1925 | 0.124* | 0.5 |
C8 | 0.5547 (8) | 0.71181 (17) | 1.2727 (6) | 0.118 (5) | 0.5 |
H8A | 0.5713 | 0.7314 | 1.3768 | 0.142* | 0.5 |
C9 | 0.4257 (7) | 0.6988 (3) | 1.2274 (8) | 0.097 (3) | 0.5 |
H9A | 0.3560 | 0.7098 | 1.3013 | 0.116* | 0.5 |
C10 | 0.4009 (8) | 0.6696 (3) | 1.0719 (9) | 0.081 (2) | 0.5 |
H10A | 0.3146 | 0.6609 | 1.0416 | 0.097* | 0.5 |
N1 | 0.5000 | 0.54393 (12) | 0.4453 (4) | 0.0794 (11) | |
N2 | 0.3816 (3) | 0.5000 | 0.2092 (5) | 0.0939 (14) | |
C1 | 0.3838 (5) | 0.54284 (17) | 0.3256 (5) | 0.1231 (19) | |
H1A | 0.3050 | 0.5433 | 0.4025 | 0.148* | |
H1B | 0.3829 | 0.5723 | 0.2481 | 0.148* | |
C2 | 0.5000 | 0.5000 | 0.5611 (6) | 0.0559 (12) | |
H2A | 0.4198 | 0.5000 | 0.6352 | 0.067* | |
C3 | 0.5000 | 0.5000 | 0.0949 (8) | 0.0813 (19) | |
H3A | 0.5000 | 0.5294 | 0.0175 | 0.098* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.072 (4) | 0.100 (4) | 0.079 (4) | −0.024 (3) | 0.010 (3) | −0.034 (3) |
O2 | 0.080 (4) | 0.160 (6) | 0.123 (6) | −0.041 (4) | 0.010 (4) | −0.065 (5) |
C4 | 0.034 (6) | 0.059 (2) | 0.075 (3) | −0.006 (2) | −0.001 (2) | −0.004 (2) |
C5 | 0.068 (3) | 0.0469 (17) | 0.066 (2) | −0.018 (6) | 0.008 (9) | 0.0013 (17) |
C6 | 0.087 (6) | 0.064 (4) | 0.092 (7) | −0.007 (3) | −0.014 (5) | −0.016 (4) |
C7 | 0.111 (6) | 0.084 (4) | 0.116 (8) | −0.019 (5) | −0.013 (5) | −0.031 (5) |
C8 | 0.173 (13) | 0.090 (5) | 0.092 (6) | 0.003 (6) | −0.006 (6) | −0.034 (5) |
C9 | 0.118 (8) | 0.096 (6) | 0.076 (5) | 0.012 (6) | 0.016 (5) | −0.018 (5) |
C10 | 0.082 (5) | 0.071 (4) | 0.089 (6) | −0.005 (4) | 0.007 (5) | −0.003 (4) |
N1 | 0.134 (3) | 0.0583 (17) | 0.0463 (17) | 0.000 | 0.000 | −0.0016 (15) |
N2 | 0.0586 (19) | 0.170 (4) | 0.0532 (18) | 0.000 | −0.0194 (17) | 0.000 |
C1 | 0.145 (4) | 0.163 (4) | 0.0612 (18) | 0.097 (3) | −0.010 (2) | 0.005 (2) |
C2 | 0.064 (3) | 0.066 (3) | 0.037 (2) | 0.000 | 0.000 | 0.000 |
C3 | 0.109 (5) | 0.098 (5) | 0.036 (2) | 0.000 | 0.000 | 0.000 |
Geometric parameters (Å, º) top
O1—C4 | 1.334 (8) | C10—H10A | 0.9300 |
O1—H1O1 | 0.83 (3) | N1—C2 | 1.448 (4) |
O2—C4 | 1.153 (9) | N1—C1 | 1.456 (4) |
C4—C5 | 1.486 (7) | N1—C1i | 1.456 (4) |
C5—C6 | 1.3900 | N2—C1ii | 1.427 (5) |
C5—C10 | 1.3900 | N2—C1 | 1.427 (5) |
C6—C7 | 1.3900 | N2—C3 | 1.452 (5) |
C6—H6A | 0.9300 | C1—H1A | 0.9700 |
C7—C8 | 1.3900 | C1—H1B | 0.9700 |
C7—H7A | 0.9300 | C2—N1iii | 1.448 (4) |
C8—C9 | 1.3900 | C2—H2A | 0.9700 |
C8—H8A | 0.9300 | C3—N2iii | 1.452 (5) |
C9—C10 | 1.3900 | C3—H3A | 0.9700 |
C9—H9A | 0.9300 | | |
| | | |
C4—O1—H1O1 | 107 (6) | C9—C10—H10A | 120.0 |
O2—C4—O1 | 125.1 (7) | C5—C10—H10A | 120.0 |
O2—C4—C5 | 122.1 (7) | C2—N1—C1 | 108.7 (3) |
O1—C4—C5 | 112.7 (6) | C2—N1—C1i | 108.7 (3) |
C6—C5—C10 | 120.0 | C1—N1—C1i | 107.7 (4) |
C6—C5—C4 | 121.2 (6) | C1ii—N2—C1 | 108.4 (4) |
C10—C5—C4 | 118.8 (6) | C1ii—N2—C3 | 108.5 (3) |
C7—C6—C5 | 120.0 | C1—N2—C3 | 108.5 (3) |
C7—C6—H6A | 120.0 | N2—C1—N1 | 112.0 (3) |
C5—C6—H6A | 120.0 | N2—C1—H1A | 109.2 |
C6—C7—C8 | 120.0 | N1—C1—H1A | 109.2 |
C6—C7—H7A | 120.0 | N2—C1—H1B | 109.2 |
C8—C7—H7A | 120.0 | N1—C1—H1B | 109.2 |
C9—C8—C7 | 120.0 | H1A—C1—H1B | 107.9 |
C9—C8—H8A | 120.0 | N1—C2—N1iii | 110.1 (4) |
C7—C8—H8A | 120.0 | N1—C2—H2A | 108.3 |
C8—C9—C10 | 120.0 | N1iii—C2—H2A | 108.3 |
C8—C9—H9A | 120.0 | N2iii—C3—N2 | 111.3 (4) |
C10—C9—H9A | 120.0 | N2iii—C3—H3A | 108.9 |
C9—C10—C5 | 120.0 | N2—C3—H3A | 108.9 |
| | | |
O2—C4—C5—C6 | 168.5 (8) | C6—C5—C10—C9 | 0.0 |
O1—C4—C5—C6 | −7.8 (7) | C4—C5—C10—C9 | 179.0 (3) |
O2—C4—C5—C10 | −10.4 (10) | C1ii—N2—C1—N1 | 58.5 (6) |
O1—C4—C5—C10 | 173.3 (6) | C3—N2—C1—N1 | −59.1 (4) |
C10—C5—C6—C7 | 0.0 | C2—N1—C1—N2 | −59.2 (4) |
C4—C5—C6—C7 | −178.9 (4) | C1i—N1—C1—N2 | 58.5 (6) |
C5—C6—C7—C8 | 0.0 | C1—N1—C2—N1iii | 58.5 (2) |
C6—C7—C8—C9 | 0.0 | C1i—N1—C2—N1iii | −58.5 (2) |
C7—C8—C9—C10 | 0.0 | C1ii—N2—C3—N2iii | −58.8 (2) |
C8—C9—C10—C5 | 0.0 | C1—N2—C3—N2iii | 58.8 (2) |
Symmetry codes: (i) −x+1, y, z; (ii) x, −y+1, z; (iii) −x+1, −y+1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···N1 | 0.83 (6) | 1.90 (7) | 2.698 (6) | 161 (7) |
Hexamethylenetetramine bis(benzoic acid) (1533071)
top
Crystal data top
C6H12N4·2(C7H6O2) | Dx = 1.288 Mg m−3 |
Mr = 384.43 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Fmm2 | Cell parameters from 1825 reflections |
a = 10.1464 (11) Å | θ = 3.0–23.4° |
b = 27.166 (3) Å | µ = 0.09 mm−1 |
c = 7.1898 (8) Å | T = 280 K |
V = 1981.8 (4) Å3 | Block, colourless |
Z = 4 | 0.76 × 0.39 × 0.21 mm |
F(000) = 816 | |
Data collection top
Bruker APEX Duo CCD area detector diffractometer | 1044 independent reflections |
Radiation source: fine-focus sealed tube | 837 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
φ and ω scans | θmax = 27.5°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −11→13 |
Tmin = 0.819, Tmax = 0.937 | k = −34→34 |
4852 measured reflections | l = −9→7 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.044 | w = 1/[σ2(Fo2) + (0.0557P)2 + 1.006P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.128 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.10 e Å−3 |
1044 reflections | Δρmin = −0.11 e Å−3 |
103 parameters | Absolute structure: Flack x determined using 263 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
2 restraints | Absolute structure parameter: −0.8 (7) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.4182 (7) | 0.3876 (3) | 0.8081 (9) | 0.0930 (19) | 0.5 |
H1O1 | 0.450 (14) | 0.401 (4) | 0.902 (11) | 0.24 (8)* | 0.5 |
O2 | 0.6266 (7) | 0.3959 (3) | 0.7257 (13) | 0.135 (3) | 0.5 |
C4 | 0.5241 (7) | 0.37906 (19) | 0.7022 (9) | 0.063 (2) | 0.5 |
C5 | 0.4939 (10) | 0.34680 (11) | 0.5389 (5) | 0.0648 (12) | 0.5 |
C6 | 0.3655 (9) | 0.3335 (2) | 0.4940 (9) | 0.088 (3) | 0.5 |
H6A | 0.2958 | 0.3442 | 0.5677 | 0.106* | 0.5 |
C7 | 0.3414 (7) | 0.3042 (3) | 0.3392 (10) | 0.115 (3) | 0.5 |
H7A | 0.2555 | 0.2953 | 0.3093 | 0.138* | 0.5 |
C8 | 0.4456 (8) | 0.28822 (16) | 0.2292 (6) | 0.121 (4) | 0.5 |
H8A | 0.4294 | 0.2686 | 0.1257 | 0.145* | 0.5 |
C9 | 0.5740 (7) | 0.3015 (3) | 0.2740 (9) | 0.108 (3) | 0.5 |
H9A | 0.6437 | 0.2909 | 0.2004 | 0.129* | 0.5 |
C10 | 0.5982 (8) | 0.3308 (3) | 0.4288 (9) | 0.088 (3) | 0.5 |
H10A | 0.6841 | 0.3398 | 0.4588 | 0.106* | 0.5 |
N1 | 0.5000 | 0.45617 (11) | 1.0543 (4) | 0.0836 (11) | |
N2 | 0.6185 (3) | 0.5000 | 1.2901 (5) | 0.0974 (13) | |
C1 | 0.6164 (4) | 0.45733 (16) | 1.1739 (5) | 0.1245 (17) | |
H1A | 0.6175 | 0.4281 | 1.2513 | 0.149* | |
H1B | 0.6950 | 0.4569 | 1.0972 | 0.149* | |
C2 | 0.5000 | 0.5000 | 0.9387 (7) | 0.0632 (12) | |
H2A | 0.4211 | 0.5000 | 0.8626 | 0.076* | |
C3 | 0.5000 | 0.5000 | 1.4046 (8) | 0.0878 (18) | |
H3A | 0.5000 | 0.5301 | 1.4770 | 0.105* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.083 (4) | 0.111 (4) | 0.085 (4) | −0.028 (3) | 0.014 (3) | −0.035 (3) |
O2 | 0.090 (4) | 0.176 (6) | 0.138 (7) | −0.048 (4) | 0.011 (4) | −0.075 (5) |
C4 | 0.046 (8) | 0.064 (2) | 0.079 (3) | −0.003 (2) | 0.001 (3) | −0.003 (2) |
C5 | 0.074 (3) | 0.0510 (16) | 0.069 (2) | −0.013 (6) | 0.009 (9) | 0.0015 (17) |
C6 | 0.095 (6) | 0.072 (4) | 0.098 (7) | −0.010 (3) | −0.014 (5) | −0.016 (4) |
C7 | 0.125 (6) | 0.097 (4) | 0.123 (8) | −0.024 (5) | −0.008 (6) | −0.035 (5) |
C8 | 0.169 (12) | 0.098 (5) | 0.095 (6) | −0.001 (5) | −0.008 (6) | −0.036 (5) |
C9 | 0.137 (8) | 0.106 (6) | 0.080 (5) | 0.013 (6) | 0.018 (6) | −0.022 (5) |
C10 | 0.088 (6) | 0.081 (5) | 0.096 (7) | −0.005 (3) | 0.005 (5) | 0.002 (4) |
N1 | 0.138 (3) | 0.0635 (17) | 0.0496 (18) | 0.000 | 0.000 | −0.0011 (15) |
N2 | 0.0637 (19) | 0.171 (4) | 0.0572 (18) | 0.000 | −0.0203 (18) | 0.000 |
C1 | 0.140 (3) | 0.165 (4) | 0.069 (2) | 0.089 (3) | −0.012 (2) | 0.007 (2) |
C2 | 0.072 (3) | 0.076 (3) | 0.042 (2) | 0.000 | 0.000 | 0.000 |
C3 | 0.119 (5) | 0.104 (4) | 0.040 (3) | 0.000 | 0.000 | 0.000 |
Geometric parameters (Å, º) top
O1—C4 | 1.337 (10) | C10—H10A | 0.9300 |
O1—H1O1 | 0.83 (3) | N1—C2 | 1.452 (4) |
O2—C4 | 1.148 (11) | N1—C1i | 1.461 (4) |
C4—C5 | 1.497 (7) | N1—C1 | 1.461 (4) |
C5—C6 | 1.3900 | N2—C1ii | 1.429 (4) |
C5—C10 | 1.3900 | N2—C1 | 1.429 (4) |
C6—C7 | 1.3900 | N2—C3 | 1.457 (5) |
C6—H6A | 0.9300 | C1—H1A | 0.9700 |
C7—C8 | 1.3900 | C1—H1B | 0.9700 |
C7—H7A | 0.9300 | C2—N1iii | 1.452 (4) |
C8—C9 | 1.3900 | C2—H2A | 0.9700 |
C8—H8A | 0.9300 | C3—N2iii | 1.457 (5) |
C9—C10 | 1.3900 | C3—H3A | 0.9700 |
C9—H9A | 0.9300 | | |
| | | |
C4—O1—H1O1 | 103 (10) | C9—C10—H10A | 120.0 |
O2—C4—O1 | 125.1 (7) | C5—C10—H10A | 120.0 |
O2—C4—C5 | 122.2 (7) | C2—N1—C1i | 108.6 (3) |
O1—C4—C5 | 112.6 (7) | C2—N1—C1 | 108.6 (3) |
C6—C5—C10 | 120.0 | C1i—N1—C1 | 107.8 (3) |
C6—C5—C4 | 121.7 (6) | C1ii—N2—C1 | 108.4 (4) |
C10—C5—C4 | 118.3 (6) | C1ii—N2—C3 | 108.5 (3) |
C7—C6—C5 | 120.0 | C1—N2—C3 | 108.5 (3) |
C7—C6—H6A | 120.0 | N2—C1—N1 | 112.0 (3) |
C5—C6—H6A | 120.0 | N2—C1—H1A | 109.2 |
C6—C7—C8 | 120.0 | N1—C1—H1A | 109.2 |
C6—C7—H7A | 120.0 | N2—C1—H1B | 109.2 |
C8—C7—H7A | 120.0 | N1—C1—H1B | 109.2 |
C9—C8—C7 | 120.0 | H1A—C1—H1B | 107.9 |
C9—C8—H8A | 120.0 | N1—C2—N1iii | 110.2 (4) |
C7—C8—H8A | 120.0 | N1—C2—H2A | 108.8 |
C8—C9—C10 | 120.0 | N1iii—C2—H2A | 108.8 |
C8—C9—H9A | 120.0 | N2—C3—N2iii | 111.2 (4) |
C10—C9—H9A | 120.0 | N2—C3—H3A | 107.6 |
C9—C10—C5 | 120.0 | N2iii—C3—H3A | 107.6 |
| | | |
O2—C4—C5—C6 | −168.9 (9) | C6—C5—C10—C9 | 0.0 |
O1—C4—C5—C6 | 7.8 (8) | C4—C5—C10—C9 | −178.9 (3) |
O2—C4—C5—C10 | 9.9 (10) | C1ii—N2—C1—N1 | −58.7 (6) |
O1—C4—C5—C10 | −173.3 (6) | C3—N2—C1—N1 | 59.0 (4) |
C10—C5—C6—C7 | 0.0 | C2—N1—C1—N2 | 59.2 (4) |
C4—C5—C6—C7 | 178.8 (4) | C1i—N1—C1—N2 | −58.3 (5) |
C5—C6—C7—C8 | 0.0 | C1i—N1—C2—N1iii | 58.49 (19) |
C6—C7—C8—C9 | 0.0 | C1—N1—C2—N1iii | −58.50 (19) |
C7—C8—C9—C10 | 0.0 | C1ii—N2—C3—N2iii | 58.8 (2) |
C8—C9—C10—C5 | 0.0 | C1—N2—C3—N2iii | −58.8 (2) |
Symmetry codes: (i) −x+1, y, z; (ii) x, −y+1, z; (iii) −x+1, −y+1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···N1 | 0.83 (11) | 1.92 (10) | 2.700 (8) | 155 (11) |
Hexamethylenetetramine bis(benzoic acid) (1533072)
top
Crystal data top
C6H12N4·2(C7H6O2) | Dx = 1.276 Mg m−3 |
Mr = 384.43 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Fmm2 | Cell parameters from 1750 reflections |
a = 10.1732 (13) Å | θ = 3.0–23.3° |
b = 27.291 (4) Å | µ = 0.09 mm−1 |
c = 7.2049 (9) Å | T = 300 K |
V = 2000.4 (4) Å3 | Block, colourless |
Z = 4 | 0.76 × 0.39 × 0.21 mm |
F(000) = 816 | |
Data collection top
Bruker APEX Duo CCD area detector diffractometer | 1100 independent reflections |
Radiation source: fine-focus sealed tube | 874 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 27.5°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −7→13 |
Tmin = 0.827, Tmax = 0.937 | k = −35→35 |
4853 measured reflections | l = −7→9 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.0578P)2 + 0.7615P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.132 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.07 e Å−3 |
1100 reflections | Δρmin = −0.11 e Å−3 |
103 parameters | Absolute structure: Flack x determined using 288 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
2 restraints | Absolute structure parameter: 0.0 (6) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.4192 (7) | 0.3877 (3) | 0.8077 (9) | 0.0999 (19) | 0.5 |
H1O1 | 0.453 (17) | 0.398 (5) | 0.904 (13) | 0.27 (9)* | 0.5 |
O2 | 0.6267 (6) | 0.3959 (4) | 0.7254 (13) | 0.146 (3) | 0.5 |
C4 | 0.5244 (6) | 0.37915 (19) | 0.7021 (8) | 0.069 (2) | 0.5 |
C5 | 0.4943 (10) | 0.34679 (12) | 0.5396 (5) | 0.0698 (12) | 0.5 |
C6 | 0.3660 (9) | 0.3337 (3) | 0.4954 (9) | 0.094 (3) | 0.5 |
H6A | 0.2967 | 0.3445 | 0.5689 | 0.113* | 0.5 |
C7 | 0.3414 (7) | 0.3044 (3) | 0.3413 (11) | 0.125 (3) | 0.5 |
H7A | 0.2556 | 0.2957 | 0.3118 | 0.150* | 0.5 |
C8 | 0.4450 (8) | 0.28830 (16) | 0.2315 (6) | 0.132 (5) | 0.5 |
H8A | 0.4285 | 0.2687 | 0.1284 | 0.158* | 0.5 |
C9 | 0.5733 (7) | 0.3014 (3) | 0.2756 (9) | 0.118 (3) | 0.5 |
H9A | 0.6426 | 0.2906 | 0.2021 | 0.142* | 0.5 |
C10 | 0.5979 (8) | 0.3306 (3) | 0.4297 (10) | 0.096 (3) | 0.5 |
H10A | 0.6838 | 0.3394 | 0.4592 | 0.115* | 0.5 |
N1 | 0.5000 | 0.45628 (11) | 1.0541 (4) | 0.0878 (11) | |
N2 | 0.6184 (3) | 0.5000 | 1.2889 (5) | 0.1020 (12) | |
C1 | 0.6162 (4) | 0.45742 (15) | 1.1737 (5) | 0.1260 (16) | |
H1A | 0.6170 | 0.4284 | 1.2514 | 0.151* | |
H1B | 0.6946 | 0.4569 | 1.0972 | 0.151* | |
C2 | 0.5000 | 0.5000 | 0.9386 (6) | 0.0686 (13) | |
H2A | 0.4207 | 0.5000 | 0.8639 | 0.082* | |
C3 | 0.5000 | 0.5000 | 1.4038 (8) | 0.0958 (19) | |
H3A | 0.5000 | 0.5298 | 1.4774 | 0.115* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.090 (4) | 0.117 (4) | 0.092 (5) | −0.031 (3) | 0.016 (3) | −0.038 (4) |
O2 | 0.095 (4) | 0.187 (7) | 0.155 (8) | −0.048 (4) | 0.015 (4) | −0.083 (5) |
C4 | 0.053 (7) | 0.070 (2) | 0.086 (3) | −0.005 (2) | −0.001 (3) | −0.003 (2) |
C5 | 0.081 (3) | 0.0554 (17) | 0.073 (2) | −0.013 (7) | 0.007 (9) | 0.0012 (18) |
C6 | 0.100 (6) | 0.080 (4) | 0.102 (7) | −0.008 (3) | −0.013 (5) | −0.021 (4) |
C7 | 0.134 (7) | 0.108 (5) | 0.134 (9) | −0.021 (5) | −0.008 (6) | −0.042 (6) |
C8 | 0.189 (13) | 0.102 (5) | 0.104 (6) | −0.009 (5) | −0.007 (6) | −0.038 (5) |
C9 | 0.149 (8) | 0.117 (7) | 0.089 (6) | 0.009 (6) | 0.021 (6) | −0.029 (6) |
C10 | 0.097 (6) | 0.087 (5) | 0.102 (7) | −0.007 (4) | 0.007 (5) | 0.000 (5) |
N1 | 0.141 (3) | 0.0691 (18) | 0.0535 (18) | 0.000 | 0.000 | −0.0011 (16) |
N2 | 0.0726 (18) | 0.170 (4) | 0.0637 (19) | 0.000 | −0.0234 (17) | 0.000 |
C1 | 0.139 (3) | 0.162 (4) | 0.077 (2) | 0.083 (3) | −0.013 (2) | 0.006 (2) |
C2 | 0.079 (3) | 0.082 (3) | 0.045 (3) | 0.000 | 0.000 | 0.000 |
C3 | 0.131 (5) | 0.114 (5) | 0.043 (3) | 0.000 | 0.000 | 0.000 |
Geometric parameters (Å, º) top
O1—C4 | 1.334 (9) | C10—H10A | 0.9300 |
O1—H1O1 | 0.83 (3) | N1—C2 | 1.455 (4) |
O2—C4 | 1.149 (10) | N1—C1 | 1.463 (4) |
C4—C5 | 1.498 (7) | N1—C1i | 1.463 (4) |
C5—C6 | 1.3900 | N2—C1ii | 1.428 (4) |
C5—C10 | 1.3900 | N2—C1 | 1.428 (4) |
C6—C7 | 1.3900 | N2—C3 | 1.462 (5) |
C6—H6A | 0.9300 | C1—H1A | 0.9700 |
C7—C8 | 1.3900 | C1—H1B | 0.9700 |
C7—H7A | 0.9300 | C2—N1iii | 1.455 (4) |
C8—C9 | 1.3900 | C2—H2A | 0.9700 |
C8—H8A | 0.9300 | C3—N2iii | 1.462 (5) |
C9—C10 | 1.3900 | C3—H3A | 0.9700 |
C9—H9A | 0.9300 | | |
| | | |
C4—O1—H1O1 | 102 (10) | C9—C10—H10A | 120.0 |
O2—C4—O1 | 125.0 (7) | C5—C10—H10A | 120.0 |
O2—C4—C5 | 122.3 (7) | C2—N1—C1 | 108.6 (3) |
O1—C4—C5 | 112.7 (6) | C2—N1—C1i | 108.6 (2) |
C6—C5—C10 | 120.0 | C1—N1—C1i | 107.8 (3) |
C6—C5—C4 | 121.5 (6) | C1ii—N2—C1 | 108.9 (4) |
C10—C5—C4 | 118.5 (6) | C1ii—N2—C3 | 108.4 (3) |
C5—C6—C7 | 120.0 | C1—N2—C3 | 108.4 (3) |
C5—C6—H6A | 120.0 | N2—C1—N1 | 111.9 (3) |
C7—C6—H6A | 120.0 | N2—C1—H1A | 109.2 |
C8—C7—C6 | 120.0 | N1—C1—H1A | 109.2 |
C8—C7—H7A | 120.0 | N2—C1—H1B | 109.2 |
C6—C7—H7A | 120.0 | N1—C1—H1B | 109.2 |
C9—C8—C7 | 120.0 | H1A—C1—H1B | 107.9 |
C9—C8—H8A | 120.0 | N1iii—C2—N1 | 110.2 (4) |
C7—C8—H8A | 120.0 | N1iii—C2—H2A | 108.5 |
C10—C9—C8 | 120.0 | N1—C2—H2A | 108.5 |
C10—C9—H9A | 120.0 | N2—C3—N2iii | 111.0 (4) |
C8—C9—H9A | 120.0 | N2—C3—H3A | 108.0 |
C9—C10—C5 | 120.0 | N2iii—C3—H3A | 108.0 |
| | | |
O2—C4—C5—C6 | −168.7 (9) | C6—C5—C10—C9 | 0.0 |
O1—C4—C5—C6 | 8.2 (8) | C4—C5—C10—C9 | −178.7 (3) |
O2—C4—C5—C10 | 9.9 (10) | C1ii—N2—C1—N1 | −58.5 (6) |
O1—C4—C5—C10 | −173.1 (6) | C3—N2—C1—N1 | 59.3 (4) |
C10—C5—C6—C7 | 0.0 | C2—N1—C1—N2 | 58.9 (4) |
C4—C5—C6—C7 | 178.7 (4) | C1i—N1—C1—N2 | −58.6 (5) |
C5—C6—C7—C8 | 0.0 | C1—N1—C2—N1iii | −58.48 (19) |
C6—C7—C8—C9 | 0.0 | C1i—N1—C2—N1iii | 58.48 (19) |
C7—C8—C9—C10 | 0.0 | C1ii—N2—C3—N2iii | 59.0 (2) |
C8—C9—C10—C5 | 0.0 | C1—N2—C3—N2iii | −59.0 (2) |
Symmetry codes: (i) −x+1, y, z; (ii) x, −y+1, z; (iii) −x+1, −y+1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···N1 | 0.82 (13) | 1.98 (12) | 2.707 (8) | 147 (13) |
Hexamethylenetetramine bis(4-methylbenzoic acid) (1533073)
top
Crystal data top
2(C8H8O2)·C6H12N4 | F(000) = 880 |
Mr = 412.48 | Dx = 1.323 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.1425 (4) Å | Cell parameters from 9593 reflections |
b = 28.0850 (18) Å | θ = 2.9–28.3° |
c = 12.1822 (8) Å | µ = 0.09 mm−1 |
β = 99.6957 (12)° | T = 100 K |
V = 2071.6 (2) Å3 | Block, colourless |
Z = 4 | 0.38 × 0.18 × 0.13 mm |
Data collection top
Bruker APEX Duo CCD area detector diffractometer | 4998 independent reflections |
Radiation source: fine-focus sealed tube | 4100 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
φ and ω scans | θmax = 28.3°, θmin = 1.5° |
Absorption correction: multi-scan (TWINABS; Sheldrick, 2012) | h = −8→8 |
Tmin = 0.885, Tmax = 0.967 | k = 0→36 |
6265 measured reflections | l = 0→16 |
Refinement top
Refinement on F2 | 2 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.121 | w = 1/[σ2(Fo2) + (0.0557P)2 + 0.7009P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
4998 reflections | Δρmax = 0.36 e Å−3 |
282 parameters | Δρmin = −0.22 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.86258 (18) | 0.64597 (4) | 0.28594 (10) | 0.0223 (3) | |
O2 | 0.50255 (19) | 0.65158 (4) | 0.21784 (10) | 0.0285 (3) | |
O3 | 0.59938 (19) | 0.86065 (4) | 0.21667 (10) | 0.0262 (3) | |
O4 | 0.8878 (2) | 0.84366 (5) | 0.34800 (10) | 0.0320 (3) | |
N1 | 0.8917 (2) | 0.71160 (4) | 0.13904 (10) | 0.0173 (3) | |
N2 | 0.7975 (2) | 0.79569 (4) | 0.11100 (10) | 0.0174 (3) | |
N3 | 0.7985 (2) | 0.74354 (5) | −0.04924 (11) | 0.0211 (3) | |
N4 | 1.1472 (2) | 0.76568 (5) | 0.06872 (11) | 0.0211 (3) | |
C1 | 0.7830 (2) | 0.75317 (5) | 0.18076 (12) | 0.0173 (3) | |
H1A | 0.8540 | 0.7601 | 0.2583 | 0.021* | |
H1B | 0.6258 | 0.7456 | 0.1814 | 0.021* | |
C2 | 0.6917 (3) | 0.78430 (6) | −0.00492 (13) | 0.0205 (3) | |
H2A | 0.5336 | 0.7770 | −0.0063 | 0.025* | |
H2B | 0.7009 | 0.8124 | −0.0530 | 0.025* | |
C3 | 0.7823 (3) | 0.70224 (5) | 0.02226 (12) | 0.0200 (3) | |
H3A | 0.8527 | 0.6744 | −0.0073 | 0.024* | |
H3B | 0.6247 | 0.6945 | 0.0214 | 0.024* | |
C4 | 1.1271 (2) | 0.72397 (6) | 0.13865 (14) | 0.0210 (3) | |
H4A | 1.2010 | 0.7306 | 0.2158 | 0.025* | |
H4B | 1.2026 | 0.6965 | 0.1105 | 0.025* | |
C5 | 1.0355 (2) | 0.80590 (5) | 0.11195 (13) | 0.0193 (3) | |
H5A | 1.0496 | 0.8344 | 0.0660 | 0.023* | |
H5B | 1.1082 | 0.8129 | 0.1891 | 0.023* | |
C6 | 1.0337 (3) | 0.75493 (6) | −0.04482 (13) | 0.0226 (3) | |
H6A | 1.1078 | 0.7276 | −0.0743 | 0.027* | |
H6B | 1.0467 | 0.7827 | −0.0933 | 0.027* | |
C7 | 0.6120 (2) | 0.60799 (5) | 0.38500 (12) | 0.0170 (3) | |
C8 | 0.7831 (2) | 0.59586 (5) | 0.47010 (13) | 0.0186 (3) | |
H8A | 0.9296 | 0.6057 | 0.4663 | 0.022* | |
C9 | 0.7414 (3) | 0.56935 (5) | 0.56097 (13) | 0.0197 (3) | |
H9A | 0.8598 | 0.5611 | 0.6186 | 0.024* | |
C10 | 0.5280 (3) | 0.55483 (5) | 0.56803 (13) | 0.0200 (3) | |
C11 | 0.3576 (3) | 0.56703 (5) | 0.48201 (14) | 0.0213 (3) | |
H11A | 0.2112 | 0.5570 | 0.4855 | 0.026* | |
C12 | 0.3973 (2) | 0.59358 (5) | 0.39145 (13) | 0.0194 (3) | |
H12A | 0.2787 | 0.6019 | 0.3341 | 0.023* | |
C13 | 0.6531 (2) | 0.63711 (5) | 0.28769 (12) | 0.0177 (3) | |
C14 | 0.6023 (2) | 0.89207 (5) | 0.39676 (12) | 0.0183 (3) | |
C15 | 0.3851 (3) | 0.90790 (5) | 0.36796 (13) | 0.0208 (3) | |
H15A | 0.3038 | 0.9013 | 0.2961 | 0.025* | |
C16 | 0.2879 (3) | 0.93339 (6) | 0.44493 (14) | 0.0234 (3) | |
H16A | 0.1400 | 0.9442 | 0.4248 | 0.028* | |
C17 | 0.4031 (3) | 0.94328 (5) | 0.55042 (13) | 0.0238 (3) | |
C18 | 0.6204 (3) | 0.92707 (6) | 0.57832 (14) | 0.0252 (4) | |
H18A | 0.7018 | 0.9337 | 0.6501 | 0.030* | |
C19 | 0.7185 (3) | 0.90150 (6) | 0.50256 (13) | 0.0222 (3) | |
H19A | 0.8658 | 0.8904 | 0.5230 | 0.027* | |
C20 | 0.7115 (2) | 0.86323 (5) | 0.31887 (13) | 0.0191 (3) | |
C21 | 0.4771 (3) | 0.52763 (6) | 0.66749 (14) | 0.0257 (4) | |
H21A | 0.6147 | 0.5155 | 0.7110 | 0.038* | |
H21B | 0.3791 | 0.5009 | 0.6420 | 0.038* | |
H21C | 0.4043 | 0.5488 | 0.7140 | 0.038* | |
C22 | 0.2970 (3) | 0.97108 (6) | 0.63318 (15) | 0.0306 (4) | |
H22A | 0.3566 | 0.9603 | 0.7088 | 0.046* | |
H22B | 0.1369 | 0.9660 | 0.6183 | 0.046* | |
H22C | 0.3286 | 1.0051 | 0.6263 | 0.046* | |
H1O3 | 0.674 (4) | 0.8423 (8) | 0.179 (2) | 0.064 (8)* | |
H1O1 | 0.869 (4) | 0.6654 (8) | 0.2281 (17) | 0.065 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0212 (5) | 0.0238 (6) | 0.0222 (6) | 0.0000 (4) | 0.0041 (4) | 0.0079 (5) |
O2 | 0.0241 (6) | 0.0314 (6) | 0.0277 (6) | 0.0006 (5) | −0.0018 (5) | 0.0109 (5) |
O3 | 0.0299 (6) | 0.0284 (6) | 0.0200 (6) | 0.0127 (5) | 0.0035 (5) | −0.0037 (5) |
O4 | 0.0266 (6) | 0.0383 (7) | 0.0291 (7) | 0.0129 (5) | −0.0011 (5) | −0.0099 (5) |
N1 | 0.0195 (6) | 0.0158 (6) | 0.0169 (6) | 0.0009 (5) | 0.0041 (5) | 0.0009 (5) |
N2 | 0.0190 (6) | 0.0159 (6) | 0.0181 (6) | 0.0011 (5) | 0.0051 (5) | 0.0007 (5) |
N3 | 0.0268 (7) | 0.0208 (7) | 0.0159 (6) | −0.0022 (5) | 0.0044 (5) | −0.0001 (5) |
N4 | 0.0203 (6) | 0.0197 (6) | 0.0250 (7) | −0.0003 (5) | 0.0084 (5) | 0.0002 (5) |
C1 | 0.0204 (7) | 0.0164 (7) | 0.0165 (7) | 0.0003 (5) | 0.0066 (5) | 0.0012 (5) |
C2 | 0.0216 (7) | 0.0212 (8) | 0.0181 (7) | 0.0023 (6) | 0.0019 (6) | 0.0034 (6) |
C3 | 0.0253 (7) | 0.0171 (7) | 0.0175 (7) | −0.0030 (6) | 0.0034 (6) | −0.0019 (6) |
C4 | 0.0177 (7) | 0.0192 (7) | 0.0262 (8) | 0.0028 (6) | 0.0043 (6) | 0.0020 (6) |
C5 | 0.0193 (7) | 0.0166 (7) | 0.0225 (8) | −0.0019 (6) | 0.0051 (6) | −0.0010 (6) |
C6 | 0.0279 (8) | 0.0215 (8) | 0.0211 (8) | −0.0003 (6) | 0.0122 (6) | 0.0004 (6) |
C7 | 0.0207 (7) | 0.0130 (6) | 0.0176 (7) | 0.0011 (5) | 0.0043 (5) | −0.0015 (5) |
C8 | 0.0183 (7) | 0.0176 (7) | 0.0200 (8) | 0.0004 (5) | 0.0038 (6) | 0.0009 (6) |
C9 | 0.0222 (7) | 0.0175 (7) | 0.0188 (7) | 0.0018 (6) | 0.0014 (6) | −0.0002 (6) |
C10 | 0.0271 (8) | 0.0140 (7) | 0.0210 (8) | 0.0003 (6) | 0.0097 (6) | −0.0024 (6) |
C11 | 0.0189 (7) | 0.0180 (7) | 0.0282 (9) | −0.0002 (6) | 0.0076 (6) | −0.0015 (6) |
C12 | 0.0177 (7) | 0.0173 (7) | 0.0225 (8) | 0.0021 (6) | 0.0017 (6) | −0.0022 (6) |
C13 | 0.0211 (7) | 0.0137 (6) | 0.0177 (7) | 0.0014 (5) | 0.0018 (6) | −0.0014 (5) |
C14 | 0.0239 (7) | 0.0130 (6) | 0.0193 (7) | 0.0004 (6) | 0.0077 (6) | 0.0017 (5) |
C15 | 0.0251 (8) | 0.0184 (7) | 0.0196 (8) | 0.0014 (6) | 0.0055 (6) | 0.0020 (6) |
C16 | 0.0249 (8) | 0.0206 (8) | 0.0267 (8) | 0.0047 (6) | 0.0097 (6) | 0.0028 (6) |
C17 | 0.0339 (8) | 0.0170 (7) | 0.0234 (8) | 0.0001 (6) | 0.0135 (7) | 0.0016 (6) |
C18 | 0.0343 (9) | 0.0234 (8) | 0.0184 (8) | −0.0003 (7) | 0.0058 (6) | −0.0009 (6) |
C19 | 0.0257 (8) | 0.0199 (8) | 0.0213 (8) | 0.0014 (6) | 0.0043 (6) | 0.0012 (6) |
C20 | 0.0221 (7) | 0.0153 (7) | 0.0204 (7) | 0.0013 (6) | 0.0050 (6) | 0.0003 (6) |
C21 | 0.0339 (9) | 0.0215 (8) | 0.0242 (8) | −0.0023 (6) | 0.0125 (7) | 0.0007 (6) |
C22 | 0.0423 (10) | 0.0249 (9) | 0.0286 (9) | 0.0025 (7) | 0.0174 (8) | −0.0034 (7) |
Geometric parameters (Å, º) top
O1—C13 | 1.3145 (18) | C7—C8 | 1.389 (2) |
O1—H1O1 | 0.898 (16) | C7—C12 | 1.394 (2) |
O2—C13 | 1.2161 (18) | C7—C13 | 1.496 (2) |
O3—C20 | 1.3193 (19) | C8—C9 | 1.393 (2) |
O3—H1O3 | 0.869 (17) | C8—H8A | 0.9500 |
O4—C20 | 1.2132 (19) | C9—C10 | 1.389 (2) |
N1—C1 | 1.4768 (18) | C9—H9A | 0.9500 |
N1—C4 | 1.4879 (19) | C10—C11 | 1.393 (2) |
N1—C3 | 1.4909 (19) | C10—C21 | 1.509 (2) |
N2—C1 | 1.4770 (18) | C11—C12 | 1.387 (2) |
N2—C2 | 1.4865 (19) | C11—H11A | 0.9500 |
N2—C5 | 1.4879 (18) | C12—H12A | 0.9500 |
N3—C3 | 1.464 (2) | C14—C19 | 1.390 (2) |
N3—C2 | 1.466 (2) | C14—C15 | 1.394 (2) |
N3—C6 | 1.472 (2) | C14—C20 | 1.490 (2) |
N4—C5 | 1.465 (2) | C15—C16 | 1.392 (2) |
N4—C4 | 1.466 (2) | C15—H15A | 0.9500 |
N4—C6 | 1.471 (2) | C16—C17 | 1.387 (2) |
C1—H1A | 0.9900 | C16—H16A | 0.9500 |
C1—H1B | 0.9900 | C17—C18 | 1.397 (2) |
C2—H2A | 0.9900 | C17—C22 | 1.507 (2) |
C2—H2B | 0.9900 | C18—C19 | 1.385 (2) |
C3—H3A | 0.9900 | C18—H18A | 0.9500 |
C3—H3B | 0.9900 | C19—H19A | 0.9500 |
C4—H4A | 0.9900 | C21—H21A | 0.9800 |
C4—H4B | 0.9900 | C21—H21B | 0.9800 |
C5—H5A | 0.9900 | C21—H21C | 0.9800 |
C5—H5B | 0.9900 | C22—H22A | 0.9800 |
C6—H6A | 0.9900 | C22—H22B | 0.9800 |
C6—H6B | 0.9900 | C22—H22C | 0.9800 |
| | | |
C13—O1—H1O1 | 107.5 (17) | C12—C7—C13 | 119.38 (13) |
C20—O3—H1O3 | 107.0 (18) | C7—C8—C9 | 120.45 (14) |
C1—N1—C4 | 108.19 (11) | C7—C8—H8A | 119.8 |
C1—N1—C3 | 108.09 (11) | C9—C8—H8A | 119.8 |
C4—N1—C3 | 108.68 (11) | C10—C9—C8 | 120.53 (14) |
C1—N2—C2 | 108.27 (11) | C10—C9—H9A | 119.7 |
C1—N2—C5 | 107.79 (11) | C8—C9—H9A | 119.7 |
C2—N2—C5 | 108.69 (11) | C9—C10—C11 | 118.57 (14) |
C3—N3—C2 | 108.65 (12) | C9—C10—C21 | 121.57 (14) |
C3—N3—C6 | 108.36 (12) | C11—C10—C21 | 119.83 (14) |
C2—N3—C6 | 108.30 (12) | C12—C11—C10 | 121.32 (14) |
C5—N4—C4 | 108.48 (12) | C12—C11—H11A | 119.3 |
C5—N4—C6 | 108.66 (12) | C10—C11—H11A | 119.3 |
C4—N4—C6 | 108.03 (12) | C11—C12—C7 | 119.72 (14) |
N1—C1—N2 | 111.51 (11) | C11—C12—H12A | 120.1 |
N1—C1—H1A | 109.3 | C7—C12—H12A | 120.1 |
N2—C1—H1A | 109.3 | O2—C13—O1 | 123.81 (14) |
N1—C1—H1B | 109.3 | O2—C13—C7 | 121.82 (14) |
N2—C1—H1B | 109.3 | O1—C13—C7 | 114.36 (12) |
H1A—C1—H1B | 108.0 | C19—C14—C15 | 119.54 (14) |
N3—C2—N2 | 111.52 (12) | C19—C14—C20 | 118.57 (14) |
N3—C2—H2A | 109.3 | C15—C14—C20 | 121.83 (14) |
N2—C2—H2A | 109.3 | C16—C15—C14 | 119.71 (15) |
N3—C2—H2B | 109.3 | C16—C15—H15A | 120.1 |
N2—C2—H2B | 109.3 | C14—C15—H15A | 120.1 |
H2A—C2—H2B | 108.0 | C17—C16—C15 | 121.17 (15) |
N3—C3—N1 | 111.30 (12) | C17—C16—H16A | 119.4 |
N3—C3—H3A | 109.4 | C15—C16—H16A | 119.4 |
N1—C3—H3A | 109.4 | C16—C17—C18 | 118.53 (14) |
N3—C3—H3B | 109.4 | C16—C17—C22 | 120.88 (15) |
N1—C3—H3B | 109.4 | C18—C17—C22 | 120.59 (15) |
H3A—C3—H3B | 108.0 | C19—C18—C17 | 120.80 (15) |
N4—C4—N1 | 111.44 (12) | C19—C18—H18A | 119.6 |
N4—C4—H4A | 109.3 | C17—C18—H18A | 119.6 |
N1—C4—H4A | 109.3 | C18—C19—C14 | 120.25 (15) |
N4—C4—H4B | 109.3 | C18—C19—H19A | 119.9 |
N1—C4—H4B | 109.3 | C14—C19—H19A | 119.9 |
H4A—C4—H4B | 108.0 | O4—C20—O3 | 123.33 (14) |
N4—C5—N2 | 111.56 (12) | O4—C20—C14 | 122.37 (14) |
N4—C5—H5A | 109.3 | O3—C20—C14 | 114.30 (13) |
N2—C5—H5A | 109.3 | C10—C21—H21A | 109.5 |
N4—C5—H5B | 109.3 | C10—C21—H21B | 109.5 |
N2—C5—H5B | 109.3 | H21A—C21—H21B | 109.5 |
H5A—C5—H5B | 108.0 | C10—C21—H21C | 109.5 |
N4—C6—N3 | 112.68 (12) | H21A—C21—H21C | 109.5 |
N4—C6—H6A | 109.1 | H21B—C21—H21C | 109.5 |
N3—C6—H6A | 109.1 | C17—C22—H22A | 109.5 |
N4—C6—H6B | 109.1 | C17—C22—H22B | 109.5 |
N3—C6—H6B | 109.1 | H22A—C22—H22B | 109.5 |
H6A—C6—H6B | 107.8 | C17—C22—H22C | 109.5 |
C8—C7—C12 | 119.40 (14) | H22A—C22—H22C | 109.5 |
C8—C7—C13 | 121.21 (13) | H22B—C22—H22C | 109.5 |
| | | |
C4—N1—C1—N2 | 58.80 (15) | C7—C8—C9—C10 | −0.2 (2) |
C3—N1—C1—N2 | −58.72 (15) | C8—C9—C10—C11 | 0.5 (2) |
C2—N2—C1—N1 | 58.51 (15) | C8—C9—C10—C21 | −177.76 (14) |
C5—N2—C1—N1 | −58.91 (15) | C9—C10—C11—C12 | −0.8 (2) |
C3—N3—C2—N2 | 59.35 (15) | C21—C10—C11—C12 | 177.50 (14) |
C6—N3—C2—N2 | −58.16 (16) | C10—C11—C12—C7 | 0.8 (2) |
C1—N2—C2—N3 | −58.60 (15) | C8—C7—C12—C11 | −0.5 (2) |
C5—N2—C2—N3 | 58.23 (15) | C13—C7—C12—C11 | −179.28 (13) |
C2—N3—C3—N1 | −59.55 (15) | C8—C7—C13—O2 | −173.28 (14) |
C6—N3—C3—N1 | 57.92 (16) | C12—C7—C13—O2 | 5.4 (2) |
C1—N1—C3—N3 | 59.13 (15) | C8—C7—C13—O1 | 5.7 (2) |
C4—N1—C3—N3 | −58.07 (15) | C12—C7—C13—O1 | −175.54 (13) |
C5—N4—C4—N1 | 59.28 (16) | C19—C14—C15—C16 | 0.7 (2) |
C6—N4—C4—N1 | −58.34 (16) | C20—C14—C15—C16 | 177.87 (14) |
C1—N1—C4—N4 | −58.75 (15) | C14—C15—C16—C17 | −0.2 (2) |
C3—N1—C4—N4 | 58.38 (16) | C15—C16—C17—C18 | 0.0 (2) |
C4—N4—C5—N2 | −59.72 (15) | C15—C16—C17—C22 | 179.73 (15) |
C6—N4—C5—N2 | 57.49 (16) | C16—C17—C18—C19 | −0.3 (2) |
C1—N2—C5—N4 | 59.32 (15) | C22—C17—C18—C19 | 179.99 (15) |
C2—N2—C5—N4 | −57.82 (16) | C17—C18—C19—C14 | 0.8 (2) |
C5—N4—C6—N3 | −58.34 (16) | C15—C14—C19—C18 | −1.0 (2) |
C4—N4—C6—N3 | 59.16 (16) | C20—C14—C19—C18 | −178.24 (14) |
C3—N3—C6—N4 | −59.13 (16) | C19—C14—C20—O4 | 7.8 (2) |
C2—N3—C6—N4 | 58.56 (16) | C15—C14—C20—O4 | −169.39 (15) |
C12—C7—C8—C9 | 0.3 (2) | C19—C14—C20—O3 | −172.65 (13) |
C13—C7—C8—C9 | 178.98 (13) | C15—C14—C20—O3 | 10.1 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H1O3···N2 | 0.87 (2) | 1.79 (2) | 2.6447 (17) | 169 (2) |
O1—H1O1···N1 | 0.90 (2) | 1.71 (2) | 2.5961 (17) | 168 (2) |
C1—H1A···O4 | 0.99 | 2.58 | 3.253 (2) | 125 |
C3—H3B···O4i | 0.99 | 2.59 | 3.211 (2) | 121 |
C4—H4B···O2ii | 0.99 | 2.43 | 3.1037 (19) | 125 |
C3—H3A···Cg2iii | 0.99 | 2.77 | 3.7117 (16) | 160 |
C5—H5A···Cg1iii | 0.99 | 2.62 | 3.5925 (16) | 169 |
C21—H21B···Cg1iv | 0.98 | 2.77 | 3.5161 (18) | 133 |
C22—H22C···Cg2v | 0.98 | 2.77 | 3.6773 (19) | 153 |
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x+1, y, z; (iii) x+1/2, −y+3/2, z−1/2; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y+2, −z+1. |
Hexamethylenetetramine bis(4-methylbenzoic acid) (1533074)
top
Crystal data top
2(C8H8O2)·C6H12N4 | F(000) = 880 |
Mr = 412.48 | Dx = 1.289 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.202 (2) Å | Cell parameters from 9903 reflections |
b = 28.482 (10) Å | θ = 2.7–27.9° |
c = 12.225 (4) Å | µ = 0.09 mm−1 |
β = 100.276 (7)° | T = 250 K |
V = 2124.9 (13) Å3 | Block, colourless |
Z = 4 | 0.38 × 0.18 × 0.13 mm |
Data collection top
Bruker APEX Duo CCD area detector diffractometer | 5101 independent reflections |
Radiation source: fine-focus sealed tube | 3518 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
φ and ω scans | θmax = 28.3°, θmin = 1.4° |
Absorption correction: multi-scan (TWINABS; Sheldrick, 2012) | h = −8→8 |
Tmin = 0.869, Tmax = 0.967 | k = 0→37 |
7003 measured reflections | l = 0→16 |
Refinement top
Refinement on F2 | 2 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.065 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.151 | w = 1/[σ2(Fo2) + (0.0446P)2 + 0.8061P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
5101 reflections | Δρmax = 0.20 e Å−3 |
282 parameters | Δρmin = −0.19 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.8535 (3) | 0.64682 (6) | 0.29434 (15) | 0.0547 (5) | |
O2 | 0.5008 (3) | 0.65279 (7) | 0.22439 (16) | 0.0713 (6) | |
O3 | 0.5970 (3) | 0.85896 (7) | 0.22531 (15) | 0.0635 (5) | |
O4 | 0.8831 (3) | 0.84455 (8) | 0.35495 (18) | 0.0858 (7) | |
N1 | 0.8856 (3) | 0.71191 (6) | 0.14667 (14) | 0.0403 (4) | |
N2 | 0.7959 (3) | 0.79484 (6) | 0.12000 (15) | 0.0402 (4) | |
N3 | 0.7899 (4) | 0.74382 (7) | −0.04001 (17) | 0.0503 (5) | |
N4 | 1.1379 (3) | 0.76474 (7) | 0.07661 (18) | 0.0503 (5) | |
C1 | 0.7821 (4) | 0.75295 (7) | 0.18887 (18) | 0.0402 (5) | |
H1A | 0.8543 | 0.7594 | 0.2654 | 0.048* | |
H1B | 0.6278 | 0.7459 | 0.1899 | 0.048* | |
C2 | 0.6882 (4) | 0.78391 (9) | 0.00511 (19) | 0.0495 (6) | |
H2A | 0.5330 | 0.7771 | 0.0042 | 0.059* | |
H2B | 0.6967 | 0.8114 | −0.0422 | 0.059* | |
C3 | 0.7750 (4) | 0.70318 (8) | 0.03073 (19) | 0.0486 (6) | |
H3A | 0.8426 | 0.6760 | 0.0011 | 0.058* | |
H3B | 0.6205 | 0.6958 | 0.0299 | 0.058* | |
C4 | 1.1172 (4) | 0.72388 (9) | 0.1460 (2) | 0.0510 (6) | |
H4A | 1.1913 | 0.7303 | 0.2223 | 0.061* | |
H4B | 1.1899 | 0.6970 | 0.1183 | 0.061* | |
C5 | 1.0296 (4) | 0.80430 (8) | 0.1202 (2) | 0.0474 (6) | |
H5A | 1.0429 | 0.8322 | 0.0750 | 0.057* | |
H5B | 1.1033 | 0.8110 | 0.1964 | 0.057* | |
C6 | 1.0217 (5) | 0.75462 (8) | −0.0361 (2) | 0.0560 (7) | |
H6A | 1.0338 | 0.7818 | −0.0837 | 0.067* | |
H6B | 1.0922 | 0.7279 | −0.0660 | 0.067* | |
C7 | 0.6035 (4) | 0.60892 (7) | 0.38948 (17) | 0.0381 (4) | |
C8 | 0.7700 (4) | 0.59660 (8) | 0.47546 (19) | 0.0447 (5) | |
H8A | 0.9145 | 0.6062 | 0.4740 | 0.054* | |
C9 | 0.7250 (4) | 0.57022 (8) | 0.5637 (2) | 0.0512 (6) | |
H9A | 0.8399 | 0.5621 | 0.6217 | 0.061* | |
C10 | 0.5152 (4) | 0.55568 (8) | 0.5682 (2) | 0.0510 (6) | |
C11 | 0.3501 (4) | 0.56802 (9) | 0.4817 (2) | 0.0548 (6) | |
H11A | 0.2060 | 0.5580 | 0.4829 | 0.066* | |
C12 | 0.3917 (4) | 0.59470 (8) | 0.3935 (2) | 0.0482 (6) | |
H12A | 0.2762 | 0.6032 | 0.3363 | 0.058* | |
C13 | 0.6465 (4) | 0.63802 (7) | 0.29467 (18) | 0.0425 (5) | |
C14 | 0.6007 (4) | 0.89171 (7) | 0.40248 (18) | 0.0429 (5) | |
C15 | 0.3863 (4) | 0.90673 (8) | 0.3743 (2) | 0.0508 (6) | |
H15A | 0.3044 | 0.8995 | 0.3040 | 0.061* | |
C16 | 0.2920 (5) | 0.93230 (9) | 0.4494 (2) | 0.0593 (7) | |
H16A | 0.1459 | 0.9423 | 0.4292 | 0.071* | |
C17 | 0.4067 (5) | 0.94347 (8) | 0.5532 (2) | 0.0582 (7) | |
C18 | 0.6207 (5) | 0.92797 (9) | 0.5805 (2) | 0.0630 (7) | |
H18A | 0.7026 | 0.9352 | 0.6508 | 0.076* | |
C19 | 0.7167 (5) | 0.90208 (9) | 0.5064 (2) | 0.0561 (6) | |
H19A | 0.8619 | 0.8915 | 0.5272 | 0.067* | |
C20 | 0.7084 (4) | 0.86300 (8) | 0.32595 (19) | 0.0468 (5) | |
C21 | 0.4626 (5) | 0.52812 (10) | 0.6657 (2) | 0.0714 (9) | |
H21A | 0.5943 | 0.5128 | 0.7040 | 0.107* | |
H21B | 0.3523 | 0.5046 | 0.6392 | 0.107* | |
H21C | 0.4075 | 0.5493 | 0.7165 | 0.107* | |
C22 | 0.3035 (6) | 0.97145 (10) | 0.6347 (3) | 0.0823 (10) | |
H22A | 0.3780 | 0.9647 | 0.7097 | 0.123* | |
H22B | 0.1500 | 0.9630 | 0.6273 | 0.123* | |
H22C | 0.3160 | 1.0047 | 0.6197 | 0.123* | |
H1O3 | 0.672 (5) | 0.8402 (10) | 0.190 (2) | 0.097 (12)* | |
H1O1 | 0.860 (5) | 0.6662 (9) | 0.239 (2) | 0.094 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0519 (10) | 0.0556 (10) | 0.0561 (11) | −0.0001 (8) | 0.0082 (8) | 0.0214 (9) |
O2 | 0.0584 (11) | 0.0794 (14) | 0.0687 (12) | −0.0011 (9) | −0.0085 (9) | 0.0327 (10) |
O3 | 0.0736 (12) | 0.0687 (12) | 0.0469 (10) | 0.0313 (10) | 0.0070 (9) | −0.0097 (9) |
O4 | 0.0682 (12) | 0.1073 (17) | 0.0739 (14) | 0.0397 (12) | −0.0089 (10) | −0.0343 (12) |
N1 | 0.0470 (10) | 0.0349 (9) | 0.0397 (10) | 0.0018 (8) | 0.0097 (8) | 0.0024 (7) |
N2 | 0.0466 (10) | 0.0346 (9) | 0.0408 (10) | 0.0028 (8) | 0.0116 (8) | 0.0013 (7) |
N3 | 0.0664 (14) | 0.0500 (12) | 0.0347 (11) | −0.0049 (10) | 0.0099 (9) | 0.0008 (8) |
N4 | 0.0431 (11) | 0.0508 (11) | 0.0612 (13) | −0.0021 (9) | 0.0206 (9) | 0.0018 (10) |
C1 | 0.0443 (13) | 0.0402 (11) | 0.0387 (12) | −0.0001 (9) | 0.0143 (9) | 0.0016 (8) |
C2 | 0.0514 (13) | 0.0501 (14) | 0.0457 (13) | 0.0058 (11) | 0.0048 (10) | 0.0105 (11) |
C3 | 0.0631 (15) | 0.0404 (12) | 0.0428 (13) | −0.0077 (11) | 0.0105 (11) | −0.0045 (10) |
C4 | 0.0436 (12) | 0.0511 (14) | 0.0586 (15) | 0.0100 (11) | 0.0096 (11) | 0.0039 (12) |
C5 | 0.0515 (13) | 0.0395 (12) | 0.0524 (14) | −0.0076 (10) | 0.0127 (11) | −0.0019 (10) |
C6 | 0.0762 (19) | 0.0518 (14) | 0.0480 (16) | −0.0011 (12) | 0.0327 (13) | −0.0004 (11) |
C7 | 0.0448 (12) | 0.0296 (9) | 0.0403 (11) | 0.0035 (9) | 0.0084 (9) | −0.0021 (9) |
C8 | 0.0443 (12) | 0.0438 (12) | 0.0461 (13) | 0.0026 (10) | 0.0082 (10) | 0.0068 (10) |
C9 | 0.0616 (15) | 0.0470 (13) | 0.0442 (13) | 0.0024 (11) | 0.0074 (11) | 0.0061 (11) |
C10 | 0.0702 (16) | 0.0366 (12) | 0.0513 (14) | 0.0003 (11) | 0.0249 (12) | −0.0013 (10) |
C11 | 0.0493 (14) | 0.0452 (13) | 0.0754 (18) | −0.0030 (11) | 0.0256 (13) | −0.0019 (13) |
C12 | 0.0429 (12) | 0.0426 (12) | 0.0583 (15) | 0.0040 (10) | 0.0072 (11) | −0.0006 (11) |
C13 | 0.0481 (13) | 0.0334 (11) | 0.0445 (12) | 0.0023 (9) | 0.0038 (10) | 0.0015 (9) |
C14 | 0.0572 (14) | 0.0304 (10) | 0.0430 (13) | 0.0037 (10) | 0.0144 (10) | 0.0034 (9) |
C15 | 0.0599 (15) | 0.0464 (13) | 0.0476 (14) | 0.0067 (11) | 0.0140 (11) | −0.0020 (11) |
C16 | 0.0653 (16) | 0.0558 (15) | 0.0620 (17) | 0.0145 (13) | 0.0256 (13) | 0.0028 (13) |
C17 | 0.088 (2) | 0.0417 (13) | 0.0522 (16) | 0.0060 (13) | 0.0322 (14) | 0.0024 (11) |
C18 | 0.090 (2) | 0.0569 (16) | 0.0422 (14) | 0.0037 (15) | 0.0121 (13) | −0.0052 (12) |
C19 | 0.0665 (16) | 0.0513 (14) | 0.0492 (14) | 0.0069 (12) | 0.0067 (12) | −0.0018 (12) |
C20 | 0.0559 (14) | 0.0382 (11) | 0.0462 (13) | 0.0066 (10) | 0.0085 (11) | −0.0024 (10) |
C21 | 0.105 (2) | 0.0540 (15) | 0.0654 (18) | −0.0085 (15) | 0.0425 (17) | 0.0038 (13) |
C22 | 0.120 (3) | 0.0669 (18) | 0.073 (2) | 0.0083 (18) | 0.0516 (19) | −0.0089 (15) |
Geometric parameters (Å, º) top
O1—C13 | 1.309 (3) | C7—C8 | 1.381 (3) |
O1—H1O1 | 0.882 (17) | C7—C12 | 1.384 (3) |
O2—C13 | 1.206 (3) | C7—C13 | 1.487 (3) |
O3—C20 | 1.304 (3) | C8—C9 | 1.384 (3) |
O3—H1O3 | 0.871 (18) | C8—H8A | 0.9400 |
O4—C20 | 1.199 (3) | C9—C10 | 1.376 (3) |
N1—C1 | 1.471 (3) | C9—H9A | 0.9400 |
N1—C4 | 1.477 (3) | C10—C11 | 1.379 (4) |
N1—C3 | 1.481 (3) | C10—C21 | 1.511 (3) |
N2—C1 | 1.472 (3) | C11—C12 | 1.381 (4) |
N2—C5 | 1.474 (3) | C11—H11A | 0.9400 |
N2—C2 | 1.477 (3) | C12—H12A | 0.9400 |
N3—C3 | 1.458 (3) | C14—C19 | 1.376 (3) |
N3—C2 | 1.459 (3) | C14—C15 | 1.381 (3) |
N3—C6 | 1.463 (3) | C14—C20 | 1.488 (3) |
N4—C4 | 1.459 (3) | C15—C16 | 1.381 (3) |
N4—C5 | 1.460 (3) | C15—H15A | 0.9400 |
N4—C6 | 1.466 (3) | C16—C17 | 1.376 (4) |
C1—H1A | 0.9800 | C16—H16A | 0.9400 |
C1—H1B | 0.9800 | C17—C18 | 1.382 (4) |
C2—H2A | 0.9800 | C17—C22 | 1.505 (3) |
C2—H2B | 0.9800 | C18—C19 | 1.382 (4) |
C3—H3A | 0.9800 | C18—H18A | 0.9400 |
C3—H3B | 0.9800 | C19—H19A | 0.9400 |
C4—H4A | 0.9800 | C21—H21A | 0.9700 |
C4—H4B | 0.9800 | C21—H21B | 0.9700 |
C5—H5A | 0.9800 | C21—H21C | 0.9700 |
C5—H5B | 0.9800 | C22—H22A | 0.9700 |
C6—H6A | 0.9800 | C22—H22B | 0.9700 |
C6—H6B | 0.9800 | C22—H22C | 0.9700 |
| | | |
C13—O1—H1O1 | 108 (2) | C12—C7—C13 | 119.6 (2) |
C20—O3—H1O3 | 106 (2) | C7—C8—C9 | 120.3 (2) |
C1—N1—C4 | 107.72 (17) | C7—C8—H8A | 119.9 |
C1—N1—C3 | 108.19 (17) | C9—C8—H8A | 119.9 |
C4—N1—C3 | 108.56 (17) | C10—C9—C8 | 121.2 (2) |
C1—N2—C5 | 107.76 (17) | C10—C9—H9A | 119.4 |
C1—N2—C2 | 108.09 (17) | C8—C9—H9A | 119.4 |
C5—N2—C2 | 108.55 (17) | C9—C10—C11 | 118.1 (2) |
C3—N3—C2 | 108.6 (2) | C9—C10—C21 | 121.7 (2) |
C3—N3—C6 | 108.3 (2) | C11—C10—C21 | 120.1 (2) |
C2—N3—C6 | 108.17 (19) | C10—C11—C12 | 121.5 (2) |
C4—N4—C5 | 108.00 (19) | C10—C11—H11A | 119.3 |
C4—N4—C6 | 108.08 (19) | C12—C11—H11A | 119.3 |
C5—N4—C6 | 108.29 (19) | C11—C12—C7 | 120.0 (2) |
N1—C1—N2 | 111.71 (16) | C11—C12—H12A | 120.0 |
N1—C1—H1A | 109.3 | C7—C12—H12A | 120.0 |
N2—C1—H1A | 109.3 | O2—C13—O1 | 122.8 (2) |
N1—C1—H1B | 109.3 | O2—C13—C7 | 122.3 (2) |
N2—C1—H1B | 109.3 | O1—C13—C7 | 114.93 (19) |
H1A—C1—H1B | 107.9 | C19—C14—C15 | 119.0 (2) |
N3—C2—N2 | 111.82 (18) | C19—C14—C20 | 118.6 (2) |
N3—C2—H2A | 109.3 | C15—C14—C20 | 122.3 (2) |
N2—C2—H2A | 109.3 | C14—C15—C16 | 120.1 (2) |
N3—C2—H2B | 109.3 | C14—C15—H15A | 120.0 |
N2—C2—H2B | 109.3 | C16—C15—H15A | 120.0 |
H2A—C2—H2B | 107.9 | C17—C16—C15 | 121.6 (3) |
N3—C3—N1 | 111.52 (18) | C17—C16—H16A | 119.2 |
N3—C3—H3A | 109.3 | C15—C16—H16A | 119.2 |
N1—C3—H3A | 109.3 | C16—C17—C18 | 117.7 (2) |
N3—C3—H3B | 109.3 | C16—C17—C22 | 121.4 (3) |
N1—C3—H3B | 109.3 | C18—C17—C22 | 120.8 (3) |
H3A—C3—H3B | 108.0 | C17—C18—C19 | 121.3 (3) |
N4—C4—N1 | 111.95 (18) | C17—C18—H18A | 119.3 |
N4—C4—H4A | 109.2 | C19—C18—H18A | 119.3 |
N1—C4—H4A | 109.2 | C14—C19—C18 | 120.3 (3) |
N4—C4—H4B | 109.2 | C14—C19—H19A | 119.9 |
N1—C4—H4B | 109.2 | C18—C19—H19A | 119.9 |
H4A—C4—H4B | 107.9 | O4—C20—O3 | 122.6 (2) |
N4—C5—N2 | 112.01 (17) | O4—C20—C14 | 122.6 (2) |
N4—C5—H5A | 109.2 | O3—C20—C14 | 114.8 (2) |
N2—C5—H5A | 109.2 | C10—C21—H21A | 109.5 |
N4—C5—H5B | 109.2 | C10—C21—H21B | 109.5 |
N2—C5—H5B | 109.2 | H21A—C21—H21B | 109.5 |
H5A—C5—H5B | 107.9 | C10—C21—H21C | 109.5 |
N3—C6—N4 | 112.80 (17) | H21A—C21—H21C | 109.5 |
N3—C6—H6A | 109.0 | H21B—C21—H21C | 109.5 |
N4—C6—H6A | 109.0 | C17—C22—H22A | 109.5 |
N3—C6—H6B | 109.0 | C17—C22—H22B | 109.5 |
N4—C6—H6B | 109.0 | H22A—C22—H22B | 109.5 |
H6A—C6—H6B | 107.8 | C17—C22—H22C | 109.5 |
C8—C7—C12 | 118.9 (2) | H22A—C22—H22C | 109.5 |
C8—C7—C13 | 121.4 (2) | H22B—C22—H22C | 109.5 |
| | | |
C4—N1—C1—N2 | 58.8 (2) | C7—C8—C9—C10 | 0.0 (4) |
C3—N1—C1—N2 | −58.4 (2) | C8—C9—C10—C11 | 0.2 (4) |
C5—N2—C1—N1 | −58.8 (2) | C8—C9—C10—C21 | −178.1 (2) |
C2—N2—C1—N1 | 58.3 (2) | C9—C10—C11—C12 | −0.8 (4) |
C3—N3—C2—N2 | 59.2 (2) | C21—C10—C11—C12 | 177.5 (2) |
C6—N3—C2—N2 | −58.1 (2) | C10—C11—C12—C7 | 1.2 (4) |
C1—N2—C2—N3 | −58.6 (2) | C8—C7—C12—C11 | −1.0 (3) |
C5—N2—C2—N3 | 58.0 (2) | C13—C7—C12—C11 | −179.5 (2) |
C2—N3—C3—N1 | −59.1 (3) | C8—C7—C13—O2 | −172.9 (2) |
C6—N3—C3—N1 | 58.2 (2) | C12—C7—C13—O2 | 5.6 (3) |
C1—N1—C3—N3 | 58.7 (2) | C8—C7—C13—O1 | 6.2 (3) |
C4—N1—C3—N3 | −58.0 (2) | C12—C7—C13—O1 | −175.4 (2) |
C5—N4—C4—N1 | 59.3 (2) | C19—C14—C15—C16 | 0.9 (4) |
C6—N4—C4—N1 | −57.6 (2) | C20—C14—C15—C16 | 178.3 (2) |
C1—N1—C4—N4 | −59.1 (2) | C14—C15—C16—C17 | 0.0 (4) |
C3—N1—C4—N4 | 57.9 (2) | C15—C16—C17—C18 | −0.4 (4) |
C4—N4—C5—N2 | −59.4 (2) | C15—C16—C17—C22 | 179.9 (2) |
C6—N4—C5—N2 | 57.4 (2) | C16—C17—C18—C19 | −0.1 (4) |
C1—N2—C5—N4 | 59.1 (2) | C22—C17—C18—C19 | 179.7 (2) |
C2—N2—C5—N4 | −57.7 (2) | C15—C14—C19—C18 | −1.3 (4) |
C3—N3—C6—N4 | −59.0 (3) | C20—C14—C19—C18 | −178.9 (2) |
C2—N3—C6—N4 | 58.6 (3) | C17—C18—C19—C14 | 0.9 (4) |
C4—N4—C6—N3 | 58.6 (3) | C19—C14—C20—O4 | 7.8 (4) |
C5—N4—C6—N3 | −58.2 (3) | C15—C14—C20—O4 | −169.7 (3) |
C12—C7—C8—C9 | 0.4 (3) | C19—C14—C20—O3 | −173.0 (2) |
C13—C7—C8—C9 | 178.8 (2) | C15—C14—C20—O3 | 9.5 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H1O3···N2 | 0.87 (3) | 1.80 (3) | 2.661 (3) | 171 (3) |
O1—H1O1···N1 | 0.88 (3) | 1.75 (3) | 2.620 (3) | 170 (2) |
C3—H3B···O4i | 0.98 | 2.63 | 3.242 (3) | 120 |
C4—H4B···O2ii | 0.98 | 2.47 | 3.141 (3) | 126 |
C3—H3A···Cg2iii | 0.98 | 2.87 | 3.815 (3) | 161 |
C5—H5A···Cg1iii | 0.98 | 2.71 | 3.683 (3) | 170 |
C21—H21B···Cg1iv | 0.97 | 2.97 | 3.599 (3) | 124 |
C22—H22C···Cg2v | 0.97 | 2.84 | 3.732 (4) | 153 |
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x+1, y, z; (iii) x−1/2, −y+1/2, z−3/2; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y+2, −z+1. |
Hexamethylenetetramine bis(4-methylbenzoic acid) (1533075)
top
Crystal data top
2(C8H8O2)·C6H12N4 | Dx = 1.274 Mg m−3 |
Mr = 412.48 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Cmcm | Cell parameters from 2689 reflections |
a = 10.1948 (13) Å | θ = 2.8–25.9° |
b = 7.3566 (9) Å | µ = 0.09 mm−1 |
c = 28.679 (4) Å | T = 280 K |
V = 2150.9 (5) Å3 | Block, colourless |
Z = 4 | 0.38 × 0.18 × 0.13 mm |
F(000) = 880 | |
Data collection top
Bruker APEX Duo CCD area detector diffractometer | 1403 independent reflections |
Radiation source: fine-focus sealed tube | 960 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
φ and ω scans | θmax = 28.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −13→13 |
Tmin = 0.919, Tmax = 0.967 | k = −9→9 |
10210 measured reflections | l = −37→33 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.080 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.243 | w = 1/[σ2(Fo2) + (0.090P)2 + 2.2465P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max < 0.001 |
1403 reflections | Δρmax = 0.32 e Å−3 |
112 parameters | Δρmin = −0.32 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.0866 (8) | −0.0326 (10) | 0.6450 (3) | 0.0781 (18) | 0.5 |
H1O1 | 0.066 (6) | 0.063 (12) | 0.663 (3) | 0.12 (3)* | 0.5 |
O2 | −0.1241 (8) | −0.0868 (14) | 0.6518 (4) | 0.115 (4) | 0.5 |
C4 | −0.0227 (10) | −0.1280 (7) | 0.63717 (15) | 0.057 (3) | 0.5 |
C5 | 0.0024 (12) | −0.2955 (3) | 0.60850 (8) | 0.0576 (11) | 0.5 |
C6 | 0.1273 (10) | −0.3573 (11) | 0.5973 (3) | 0.0671 (19) | 0.5 |
H6A | 0.2007 | −0.2929 | 0.6073 | 0.080* | 0.5 |
C7 | 0.1426 (4) | −0.5153 (11) | 0.5713 (3) | 0.074 (2) | 0.5 |
H7A | 0.2262 | −0.5567 | 0.5639 | 0.089* | 0.5 |
C8 | 0.0330 (3) | −0.6115 (4) | 0.55647 (10) | 0.061 (2) | 0.5 |
C9 | −0.0920 (3) | −0.5497 (10) | 0.5676 (3) | 0.072 (2) | 0.5 |
H9A | −0.1653 | −0.6141 | 0.5577 | 0.086* | 0.5 |
C10 | −0.1073 (8) | −0.3917 (11) | 0.5936 (3) | 0.072 (2) | 0.5 |
H10A | −0.1909 | −0.3504 | 0.6011 | 0.087* | 0.5 |
C11 | 0.0466 (7) | −0.7869 (7) | 0.5286 (2) | 0.100 (3) | 0.5 |
H11A | 0.1355 | −0.8224 | 0.5223 | 0.150* | 0.5 |
H11B | 0.0058 | −0.8814 | 0.5465 | 0.150* | 0.5 |
H11C | 0.0011 | −0.7773 | 0.4993 | 0.150* | 0.5 |
N1 | 0.0000 | 0.2162 (4) | 0.70891 (10) | 0.0933 (13) | |
N2 | 0.1172 (3) | 0.4485 (4) | 0.7500 | 0.1049 (15) | |
C1 | 0.1143 (4) | 0.3332 (4) | 0.70966 (17) | 0.150 (2) | |
H1A | 0.1928 | 0.2587 | 0.7092 | 0.180* | |
H1B | 0.1146 | 0.4081 | 0.6818 | 0.180* | |
C2 | 0.0000 | 0.1040 (5) | 0.7500 | 0.0550 (10) | |
H2A | 0.0763 | 0.0253 | 0.7500 | 0.066* | |
C3 | 0.0000 | 0.5583 (6) | 0.7500 | 0.0769 (16) | |
H3A | 0.0000 | 0.6342 | 0.7224 | 0.092* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.083 (4) | 0.067 (4) | 0.084 (3) | −0.011 (3) | 0.019 (3) | −0.026 (3) |
O2 | 0.086 (5) | 0.115 (7) | 0.144 (6) | −0.010 (4) | 0.030 (4) | −0.065 (5) |
C4 | 0.058 (8) | 0.063 (2) | 0.051 (2) | −0.001 (3) | 0.002 (2) | −0.0019 (17) |
C5 | 0.073 (2) | 0.0550 (18) | 0.0446 (17) | −0.008 (10) | −0.016 (7) | 0.0021 (15) |
C6 | 0.080 (5) | 0.067 (4) | 0.054 (4) | 0.001 (3) | 0.004 (3) | −0.013 (3) |
C7 | 0.084 (5) | 0.069 (4) | 0.069 (4) | 0.003 (4) | −0.003 (5) | −0.015 (3) |
C8 | 0.074 (6) | 0.057 (2) | 0.053 (2) | 0.000 (2) | 0.0013 (19) | 0.0003 (18) |
C9 | 0.068 (5) | 0.071 (5) | 0.076 (4) | −0.010 (4) | 0.007 (4) | −0.013 (4) |
C10 | 0.063 (4) | 0.077 (5) | 0.076 (5) | 0.000 (4) | 0.013 (3) | −0.006 (4) |
C11 | 0.160 (9) | 0.064 (3) | 0.076 (3) | 0.002 (3) | 0.002 (3) | −0.013 (3) |
N1 | 0.186 (4) | 0.0462 (15) | 0.0478 (16) | 0.000 | 0.000 | −0.0029 (13) |
N2 | 0.069 (2) | 0.0540 (18) | 0.192 (5) | −0.0159 (16) | 0.000 | 0.000 |
C1 | 0.198 (4) | 0.0579 (17) | 0.193 (4) | −0.008 (2) | 0.138 (4) | 0.002 (2) |
C2 | 0.072 (3) | 0.039 (2) | 0.054 (2) | 0.000 | 0.000 | 0.000 |
C3 | 0.114 (4) | 0.038 (2) | 0.078 (3) | 0.000 | 0.000 | 0.000 |
Geometric parameters (Å, º) top
O1—C4 | 1.337 (12) | C11—H11A | 0.9600 |
O1—H1O1 | 0.90 (9) | C11—H11B | 0.9600 |
O2—C4 | 1.155 (14) | C11—H11C | 0.9600 |
C4—C5 | 1.503 (6) | N1—C2 | 1.439 (4) |
C5—C6 | 1.3900 | N1—C1 | 1.449 (4) |
C5—C10 | 1.3900 | N1—C1i | 1.449 (4) |
C6—C7 | 1.3900 | N2—C1 | 1.435 (4) |
C6—H6A | 0.9300 | N2—C1ii | 1.435 (4) |
C7—C8 | 1.3900 | N2—C3 | 1.442 (4) |
C7—H7A | 0.9300 | C1—H1A | 0.9700 |
C8—C9 | 1.3900 | C1—H1B | 0.9700 |
C8—C11 | 1.525 (6) | C2—N1ii | 1.439 (4) |
C9—C10 | 1.3900 | C2—H2A | 0.9700 |
C9—H9A | 0.9300 | C3—N2iii | 1.442 (4) |
C10—H10A | 0.9300 | C3—H3A | 0.9700 |
| | | |
C4—O1—H1O1 | 108 (4) | C8—C11—H11B | 107.0 |
O2—C4—O1 | 123.2 (6) | H11A—C11—H11B | 108.2 |
O2—C4—C5 | 124.4 (8) | C8—C11—H11C | 110.6 |
O1—C4—C5 | 112.4 (9) | H11A—C11—H11C | 108.2 |
C6—C5—C10 | 120.0 | H11B—C11—H11C | 108.2 |
C6—C5—C4 | 123.4 (8) | C2—N1—C1 | 109.2 (3) |
C10—C5—C4 | 116.6 (8) | C2—N1—C1i | 109.2 (3) |
C5—C6—C7 | 120.0 | C1—N1—C1i | 107.1 (3) |
C5—C6—H6A | 120.0 | C1—N2—C1ii | 107.5 (4) |
C7—C6—H6A | 120.0 | C1—N2—C3 | 108.3 (3) |
C8—C7—C6 | 120.0 | C1ii—N2—C3 | 108.3 (3) |
C8—C7—H7A | 120.0 | N2—C1—N1 | 112.3 (3) |
C6—C7—H7A | 120.0 | N2—C1—H1A | 109.1 |
C9—C8—C7 | 120.0 | N1—C1—H1A | 109.1 |
C9—C8—C11 | 118.7 (4) | N2—C1—H1B | 109.1 |
C7—C8—C11 | 121.2 (4) | N1—C1—H1B | 109.1 |
C8—C9—C10 | 120.0 | H1A—C1—H1B | 107.9 |
C8—C9—H9A | 120.0 | N1ii—C2—N1 | 110.0 (3) |
C10—C9—H9A | 120.0 | N1ii—C2—H2A | 110.0 |
C9—C10—C5 | 120.0 | N1—C2—H2A | 110.0 |
C9—C10—H10A | 120.0 | N2—C3—N2iii | 111.9 (4) |
C5—C10—H10A | 120.0 | N2—C3—H3A | 108.8 |
C8—C11—H11A | 114.5 | N2iii—C3—H3A | 108.8 |
| | | |
O2—C4—C5—C6 | −169.8 (9) | C8—C9—C10—C5 | 0.0 |
O1—C4—C5—C6 | 8.7 (8) | C6—C5—C10—C9 | 0.0 |
O2—C4—C5—C10 | 9.1 (10) | C4—C5—C10—C9 | −178.9 (3) |
O1—C4—C5—C10 | −172.4 (7) | C1ii—N2—C1—N1 | 57.8 (6) |
C10—C5—C6—C7 | 0.0 | C3—N2—C1—N1 | −59.0 (4) |
C4—C5—C6—C7 | 178.9 (3) | C2—N1—C1—N2 | −59.3 (4) |
C5—C6—C7—C8 | 0.0 | C1i—N1—C1—N2 | 58.8 (6) |
C6—C7—C8—C9 | 0.0 | C1—N1—C2—N1ii | 58.38 (19) |
C6—C7—C8—C11 | −179.0 (3) | C1i—N1—C2—N1ii | −58.38 (19) |
C7—C8—C9—C10 | 0.0 | C1—N2—C3—N2iii | 58.12 (19) |
C11—C8—C9—C10 | 179.0 (3) | C1ii—N2—C3—N2iii | −58.12 (19) |
Symmetry codes: (i) −x, y, z; (ii) x, y, −z+3/2; (iii) −x, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···N1 | 0.90 (9) | 1.86 (8) | 2.737 (8) | 165 (7) |
C11—H11C···Cg7iv | 0.96 | 2.90 | 3.655 (6) | 136 |
C11—H11C···Cg7v | 0.96 | 2.90 | 3.702 (6) | 141 |
Symmetry codes: (iv) x, −y−1, −z+1; (v) −x, −y−1, −z+1. |
Hexamethylenetetramine bis(4-methylbenzoic acid) (1533076)
top
Crystal data top
2(C8H8O2)·C6H12N4 | Dx = 1.271 Mg m−3 |
Mr = 412.48 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Cmcm | Cell parameters from 2577 reflections |
a = 10.1958 (13) Å | θ = 2.8–23.4° |
b = 7.3592 (9) Å | µ = 0.09 mm−1 |
c = 28.718 (4) Å | T = 290 K |
V = 2154.8 (5) Å3 | Block, colourless |
Z = 4 | 0.38 × 0.18 × 0.13 mm |
F(000) = 880 | |
Data collection top
Bruker APEX Duo CCD area detector diffractometer | 1537 independent reflections |
Radiation source: fine-focus sealed tube | 1010 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 29.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −13→13 |
Tmin = 0.906, Tmax = 0.967 | k = −10→9 |
10890 measured reflections | l = −39→38 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.079 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.242 | w = 1/[σ2(Fo2) + (0.0875P)2 + 1.9708P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
1537 reflections | Δρmax = 0.29 e Å−3 |
112 parameters | Δρmin = −0.27 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.0854 (7) | −0.0348 (10) | 0.6449 (3) | 0.0806 (16) | 0.5 |
H1O1 | 0.067 (5) | 0.065 (10) | 0.661 (2) | 0.11 (2)* | 0.5 |
O2 | −0.1254 (7) | −0.0883 (13) | 0.6522 (4) | 0.120 (3) | 0.5 |
C4 | −0.0239 (8) | −0.1290 (7) | 0.63718 (14) | 0.060 (2) | 0.5 |
C5 | 0.0015 (12) | −0.2965 (3) | 0.60865 (8) | 0.0604 (10) | 0.5 |
C6 | 0.1264 (9) | −0.3572 (10) | 0.5971 (3) | 0.0710 (18) | 0.5 |
H6A | 0.1997 | −0.2924 | 0.6069 | 0.085* | 0.5 |
C7 | 0.1418 (4) | −0.5149 (10) | 0.5711 (3) | 0.076 (2) | 0.5 |
H7A | 0.2254 | −0.5555 | 0.5634 | 0.092* | 0.5 |
C8 | 0.0323 (3) | −0.6119 (3) | 0.55649 (9) | 0.064 (2) | 0.5 |
C9 | −0.0927 (4) | −0.5512 (10) | 0.5680 (3) | 0.0751 (19) | 0.5 |
H9A | −0.1660 | −0.6161 | 0.5583 | 0.090* | 0.5 |
C10 | −0.1081 (8) | −0.3935 (10) | 0.5941 (3) | 0.0745 (19) | 0.5 |
H10A | −0.1917 | −0.3529 | 0.6018 | 0.089* | 0.5 |
C11 | 0.0450 (8) | −0.7872 (7) | 0.52848 (19) | 0.109 (4) | 0.5 |
H11A | 0.1320 | −0.8291 | 0.5216 | 0.163* | 0.5 |
H11B | 0.0026 | −0.8823 | 0.5457 | 0.163* | 0.5 |
H11C | −0.0003 | −0.7771 | 0.4993 | 0.163* | 0.5 |
N1 | 0.0000 | 0.2148 (4) | 0.70895 (9) | 0.0944 (12) | |
N2 | 0.1173 (3) | 0.4461 (4) | 0.7500 | 0.1074 (14) | |
C1 | 0.1143 (4) | 0.3310 (4) | 0.70970 (16) | 0.1499 (19) | |
H1A | 0.1927 | 0.2562 | 0.7093 | 0.180* | |
H1B | 0.1149 | 0.4059 | 0.6819 | 0.180* | |
C2 | 0.0000 | 0.1026 (5) | 0.7500 | 0.0574 (10) | |
H2A | 0.0748 | 0.0211 | 0.7500 | 0.069* | |
C3 | 0.0000 | 0.5568 (6) | 0.7500 | 0.0817 (16) | |
H3A | 0.0000 | 0.6279 | 0.7216 | 0.098* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.084 (4) | 0.071 (3) | 0.086 (3) | −0.011 (3) | 0.016 (3) | −0.028 (3) |
O2 | 0.089 (4) | 0.123 (7) | 0.147 (6) | −0.012 (3) | 0.033 (3) | −0.069 (5) |
C4 | 0.061 (7) | 0.065 (2) | 0.0532 (19) | −0.003 (2) | 0.004 (2) | −0.0031 (16) |
C5 | 0.078 (2) | 0.0566 (16) | 0.0461 (16) | −0.004 (11) | −0.018 (7) | 0.0027 (15) |
C6 | 0.086 (5) | 0.070 (4) | 0.057 (4) | −0.003 (3) | 0.006 (3) | −0.011 (3) |
C7 | 0.089 (5) | 0.070 (4) | 0.070 (3) | −0.001 (4) | 0.000 (4) | −0.013 (3) |
C8 | 0.077 (6) | 0.058 (2) | 0.056 (2) | −0.0010 (19) | 0.0029 (19) | −0.0001 (16) |
C9 | 0.071 (5) | 0.070 (4) | 0.085 (4) | −0.009 (4) | 0.005 (4) | −0.012 (4) |
C10 | 0.067 (4) | 0.075 (4) | 0.082 (5) | −0.003 (3) | 0.012 (3) | −0.008 (4) |
C11 | 0.179 (11) | 0.065 (3) | 0.081 (3) | 0.004 (3) | 0.002 (4) | −0.015 (2) |
N1 | 0.186 (4) | 0.0476 (14) | 0.0497 (14) | 0.000 | 0.000 | −0.0028 (11) |
N2 | 0.073 (2) | 0.0569 (17) | 0.192 (4) | −0.0156 (15) | 0.000 | 0.000 |
C1 | 0.199 (4) | 0.0613 (16) | 0.190 (4) | −0.008 (2) | 0.135 (3) | 0.003 (2) |
C2 | 0.075 (3) | 0.0399 (18) | 0.057 (2) | 0.000 | 0.000 | 0.000 |
C3 | 0.123 (4) | 0.040 (2) | 0.082 (3) | 0.000 | 0.000 | 0.000 |
Geometric parameters (Å, º) top
O1—C4 | 1.331 (10) | C11—H11A | 0.9600 |
O1—H1O1 | 0.89 (8) | C11—H11B | 0.9600 |
O2—C4 | 1.161 (11) | C11—H11C | 0.9600 |
C4—C5 | 1.503 (6) | N1—C2 | 1.439 (3) |
C5—C6 | 1.3900 | N1—C1 | 1.446 (4) |
C5—C10 | 1.3900 | N1—C1i | 1.446 (4) |
C6—C7 | 1.3900 | N2—C1ii | 1.434 (4) |
C6—H6A | 0.9300 | N2—C1 | 1.434 (4) |
C7—C8 | 1.3900 | N2—C3 | 1.447 (4) |
C7—H7A | 0.9300 | C1—H1A | 0.9700 |
C8—C9 | 1.3900 | C1—H1B | 0.9700 |
C8—C11 | 1.526 (5) | C2—N1ii | 1.439 (3) |
C9—C10 | 1.3900 | C2—H2A | 0.9700 |
C9—H9A | 0.9300 | C3—N2iii | 1.447 (4) |
C10—H10A | 0.9300 | C3—H3A | 0.9700 |
| | | |
C4—O1—H1O1 | 110 (4) | C8—C11—H11B | 107.9 |
O2—C4—O1 | 123.4 (6) | H11A—C11—H11B | 106.8 |
O2—C4—C5 | 124.6 (8) | C8—C11—H11C | 110.7 |
O1—C4—C5 | 112.0 (8) | H11A—C11—H11C | 106.8 |
C6—C5—C10 | 120.0 | H11B—C11—H11C | 106.8 |
C6—C5—C4 | 123.4 (8) | C2—N1—C1 | 109.1 (2) |
C10—C5—C4 | 116.5 (8) | C2—N1—C1i | 109.1 (2) |
C5—C6—C7 | 120.0 | C1—N1—C1i | 107.5 (3) |
C5—C6—H6A | 120.0 | C1ii—N2—C1 | 107.6 (3) |
C7—C6—H6A | 120.0 | C1ii—N2—C3 | 108.4 (3) |
C8—C7—C6 | 120.0 | C1—N2—C3 | 108.4 (3) |
C8—C7—H7A | 120.0 | N2—C1—N1 | 112.2 (3) |
C6—C7—H7A | 120.0 | N2—C1—H1A | 109.2 |
C7—C8—C9 | 120.0 | N1—C1—H1A | 109.2 |
C7—C8—C11 | 121.6 (4) | N2—C1—H1B | 109.2 |
C9—C8—C11 | 118.4 (4) | N1—C1—H1B | 109.2 |
C8—C9—C10 | 120.0 | H1A—C1—H1B | 107.9 |
C8—C9—H9A | 120.0 | N1ii—C2—N1 | 110.0 (3) |
C10—C9—H9A | 120.0 | N1ii—C2—H2A | 110.8 |
C9—C10—C5 | 120.0 | N1—C2—H2A | 110.8 |
C9—C10—H10A | 120.0 | N2iii—C3—N2 | 111.5 (3) |
C5—C10—H10A | 120.0 | N2iii—C3—H3A | 107.7 |
C8—C11—H11A | 117.3 | N2—C3—H3A | 107.7 |
| | | |
O2—C4—C5—C6 | −169.7 (9) | C8—C9—C10—C5 | 0.0 |
O1—C4—C5—C6 | 7.9 (8) | C6—C5—C10—C9 | 0.0 |
O2—C4—C5—C10 | 9.5 (10) | C4—C5—C10—C9 | −179.3 (2) |
O1—C4—C5—C10 | −172.9 (6) | C1ii—N2—C1—N1 | 58.0 (5) |
C10—C5—C6—C7 | 0.0 | C3—N2—C1—N1 | −59.0 (4) |
C4—C5—C6—C7 | 179.2 (3) | C2—N1—C1—N2 | −59.4 (4) |
C5—C6—C7—C8 | 0.0 | C1i—N1—C1—N2 | 58.8 (5) |
C6—C7—C8—C9 | 0.0 | C1—N1—C2—N1ii | 58.55 (18) |
C6—C7—C8—C11 | −179.0 (3) | C1i—N1—C2—N1ii | −58.55 (18) |
C7—C8—C9—C10 | 0.0 | C1ii—N2—C3—N2iii | −58.22 (18) |
C11—C8—C9—C10 | 179.0 (3) | C1—N2—C3—N2iii | 58.22 (18) |
Symmetry codes: (i) −x, y, z; (ii) x, y, −z+3/2; (iii) −x, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O1···N1 | 0.89 (7) | 1.89 (6) | 2.742 (8) | 160 (6) |
C11—H11C···Cg1iv | 0.96 | 2.91 | 3.662 (6) | 136 |
C11—H11C···Cg1v | 0.96 | 2.91 | 3.705 (6) | 141 |
Symmetry codes: (iv) x, −y−1, −z+1; (v) −x, −y−1, −z+1. |