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Compounds with more than one molecule in the crystallographic asymmetric unit (Z′ > 1) display a noticeably stronger propensity to form cocrystals. Deferiprone is an anti-thalassemia drug known to exhibit polymorphic behaviour. Previously, three polymorphs were reported out of which one of them exhibited Z′ > 1. In the present manuscript, a fourth polymorph of deferiprone was identified and it also possessed Z′ > 1. All the four polymorphs showed similar hydrogen bonding features and differed in crystal packing. The ability of deferiprone to crystallize as Z′ > 1 prompted us to investigate the hydrogen bonding and synthon variation upon cocrystallization of deferiprone with hydroxyl-group-containing coformers such as catechol, hydroquinone, phloroglucinol, resorcinol and pyrogallol. Crystallization attempts along with PXRD analysis aided in obtaining 11 new cocrystal structures which involve different stoichiometric cocrystals and some polymorphs. Synthon analysis, crystal packing as well as thermal behaviour were assessed and compared. The presence of multiple phases in each cocrystal system in its respective bulk powders was identified and quantified using PXRD and Rietveld analysis. Homosynthons were observed in three co-crystal systems, while a heterosynthon was observed in five systems. The combination of both homo- and heterosynthon was observed in three cocrystal systems. The phase transformation events were observed in most of the systems. In nine co-crystal systems, the melting points were observed intermediate between those of the API and the coformers.
Supporting information
| Crystallographic Information File (CIF) https://doi.org/10.1107/S205252062100980X/lo5093sup1.cif Contains datablocks global, Id, Def-cat_1_2, KA1036_0m_Def-cat_2_3, KA955_0m_def-cat_1_1_form1, KA1027_0m_4def-cat_1_1_form2, KA254_0M_def-hq_1_0.5, KA951_0mdef-res_2_1, KA1018_0m_def-res_1_1, KA773_0m_def-phg_2_1, KA1017_0m_def-phghyd_2_1_2, KA803_0m_def-pyro_1_2, KA1032_0m_def-pyro_2_4 |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252062100980X/lo5093Idsup2.hkl Contains datablock Id |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252062100980X/lo5093Def-cat_1_2sup3.hkl Contains datablock Def-cat_1_2 |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252062100980X/lo5093KA1036_0m_Def-cat_2_3sup4.hkl Contains datablock KA1036_0m_Def-cat_2_3 |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252062100980X/lo5093KA955_0m_def-cat_1_1_form1sup5.hkl Contains datablock KA955_0m_def-cat_1_1_form1 |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252062100980X/lo5093KA1027_0m_4def-cat_1_1_form2sup6.hkl Contains datablock KA1027_0m_4def-cat_1_1_form2 |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252062100980X/lo5093KA254_0M_def-hq_1_0.5sup7.hkl Contains datablock KA254_0M_def-hq_1_0.5 |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252062100980X/lo5093KA951_0mdef-res_2_1sup8.hkl Contains datablock KA951_0mdef-res_2_1 |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252062100980X/lo5093KA1018_0m_def-res_1_1sup9.hkl Contains datablock KA1018_0m_def-res_1_1 |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252062100980X/lo5093KA773_0m_def-phg_2_1sup10.hkl Contains datablock KA773_0m_def-phg_2_1 |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252062100980X/lo5093KA1017_0m_def-phghyd_2_1_2sup11.hkl Contains datablock KA1017_0m_def-phghyd_2_1_2 |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252062100980X/lo5093KA803_0m_def-pyro_1_2sup12.hkl Contains datablock KA803_0m_def-pyro_1_2 |
| Structure factor file (CIF format) https://doi.org/10.1107/S205252062100980X/lo5093KA1032_0m_def-pyro_2_4sup13.hkl Contains datablock KA1032_0m_def-pyro_2_4 |
CCDC references: 2110909; 2110910; 2110911; 2110912; 2110913; 2110914; 2110915; 2110916; 2110917; 2110918; 2110919; 2110920
For all structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: Bruker SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015). Program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2018) for (Id), KA1036_0m_Def-cat_2_3, KA955_0m_def-cat_1_1_form1, KA1027_0m_4def-cat_1_1_form2, KA951_0mdef-res_2_1, KA1018_0m_def-res_1_1, KA773_0m_def-phg_2_1, KA1017_0m_def-phghyd_2_1_2, KA803_0m_def-pyro_1_2, KA1032_0m_def-pyro_2_4; SHELXL2014 (Sheldrick, 2015) for Def-cat_1_2, KA254_0M_def-hq_1_0.5. For all structures, molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: Bruker SHELXTL.
Crystal data top
C7H9NO2 | Dx = 1.456 Mg m−3 |
Mr = 139.15 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 9953 reflections |
a = 13.70079 (19) Å | θ = 2.2–30.6° |
b = 7.16238 (10) Å | µ = 0.11 mm−1 |
c = 25.8688 (4) Å | T = 100 K |
V = 2538.51 (6) Å3 | Block, colorless |
Z = 16 | 0.32 × 0.28 × 0.16 mm |
F(000) = 1184 | |
Data collection top
Bruker D8 QUEST PHOTON-100 diffractometer | 3243 reflections with I > 2σ(I) |
Radiation source: microfocus | Rint = 0.033 |
ω and φ scans | θmax = 30.6°, θmin = 2.2° |
Absorption correction: multi-scan SADABS, Bruker, 2016 | h = −19→13 |
Tmin = 0.686, Tmax = 0.746 | k = −10→8 |
18090 measured reflections | l = −36→36 |
3892 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.0572P)2 + 1.1028P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3892 reflections | Δρmax = 0.47 e Å−3 |
193 parameters | Δρmin = −0.29 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 | |
C1A | 0.21728 (7) | 0.62677 (14) | 0.40135 (3) | 0.00954 (18) | |
C2A | 0.31652 (7) | 0.61778 (14) | 0.39406 (3) | 0.00989 (19) | |
C3A | 0.38516 (7) | 0.66671 (14) | 0.43395 (4) | 0.01034 (19) | |
C4A | 0.34209 (8) | 0.71939 (16) | 0.48193 (4) | 0.0125 (2) | |
H4A | 0.383001 | 0.748526 | 0.510465 | 0.015* | |
C5A | 0.24323 (8) | 0.72877 (15) | 0.48765 (4) | 0.0120 (2) | |
H5A | 0.216874 | 0.767039 | 0.519925 | 0.014* | |
C6A | 0.07595 (7) | 0.69611 (16) | 0.45748 (4) | 0.0143 (2) | |
H6AA | 0.046317 | 0.778195 | 0.431553 | 0.021* | |
H6AB | 0.063665 | 0.746489 | 0.492097 | 0.021* | |
H6AC | 0.047350 | 0.571088 | 0.454761 | 0.021* | |
C7A | 0.14580 (8) | 0.57642 (15) | 0.35975 (4) | 0.0126 (2) | |
H7AA | 0.107538 | 0.686930 | 0.350352 | 0.019* | |
H7AB | 0.101953 | 0.478425 | 0.372389 | 0.019* | |
H7AC | 0.181177 | 0.531003 | 0.329324 | 0.019* | |
O1A | 0.35166 (6) | 0.56375 (11) | 0.34700 (3) | 0.01343 (17) | |
H1O | 0.4160 (13) | 0.541 (3) | 0.3497 (7) | 0.036 (5)* | |
O2A | 0.47635 (5) | 0.66402 (12) | 0.42541 (3) | 0.01489 (17) | |
N1A | 0.18170 (6) | 0.68496 (12) | 0.44853 (3) | 0.01016 (17) | |
C1B | 0.78598 (7) | 0.46177 (14) | 0.34963 (4) | 0.00977 (19) | |
C2B | 0.68662 (7) | 0.47054 (14) | 0.35668 (3) | 0.00965 (19) | |
C3B | 0.61827 (7) | 0.41306 (14) | 0.31736 (4) | 0.01006 (19) | |
C4B | 0.66177 (8) | 0.35314 (15) | 0.27017 (4) | 0.01127 (19) | |
H4B | 0.621243 | 0.313886 | 0.242421 | 0.014* | |
C5B | 0.76071 (8) | 0.35123 (15) | 0.26419 (4) | 0.01177 (19) | |
H5B | 0.787378 | 0.312561 | 0.232023 | 0.014* | |
C6B | 0.92792 (8) | 0.39829 (16) | 0.29339 (4) | 0.0149 (2) | |
H6BA | 0.940519 | 0.364649 | 0.257286 | 0.022* | |
H6BB | 0.958114 | 0.305606 | 0.316218 | 0.022* | |
H6BC | 0.955687 | 0.521705 | 0.300548 | 0.022* | |
C7B | 0.85682 (8) | 0.51145 (15) | 0.39161 (4) | 0.0127 (2) | |
H7BA | 0.898474 | 0.403569 | 0.399113 | 0.019* | |
H7BB | 0.820857 | 0.546837 | 0.422856 | 0.019* | |
H7BC | 0.897432 | 0.616411 | 0.380298 | 0.019* | |
O1B | 0.65159 (6) | 0.52954 (12) | 0.40310 (3) | 0.01335 (16) | |
H2O | 0.5858 (14) | 0.547 (3) | 0.4017 (7) | 0.043 (5)* | |
O2B | 0.52702 (5) | 0.41437 (11) | 0.32617 (3) | 0.01374 (17) | |
N1B | 0.82201 (6) | 0.40264 (12) | 0.30260 (3) | 0.01037 (18) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.0101 (4) | 0.0093 (4) | 0.0092 (4) | 0.0002 (4) | 0.0003 (3) | 0.0000 (3) |
C2A | 0.0104 (4) | 0.0110 (4) | 0.0083 (4) | 0.0002 (4) | 0.0009 (3) | −0.0004 (3) |
C3A | 0.0097 (5) | 0.0108 (4) | 0.0105 (4) | −0.0005 (3) | 0.0004 (3) | −0.0012 (3) |
C4A | 0.0113 (5) | 0.0167 (5) | 0.0095 (4) | −0.0010 (4) | −0.0001 (3) | −0.0029 (3) |
C5A | 0.0119 (5) | 0.0147 (5) | 0.0095 (4) | −0.0012 (4) | 0.0015 (3) | −0.0022 (3) |
C6A | 0.0072 (4) | 0.0193 (5) | 0.0163 (4) | 0.0005 (4) | 0.0025 (3) | −0.0013 (4) |
C7A | 0.0115 (5) | 0.0147 (5) | 0.0115 (4) | 0.0003 (4) | −0.0028 (3) | −0.0007 (3) |
O1A | 0.0100 (4) | 0.0208 (4) | 0.0095 (3) | 0.0018 (3) | 0.0015 (2) | −0.0044 (3) |
O2A | 0.0076 (4) | 0.0212 (4) | 0.0159 (3) | −0.0002 (3) | 0.0019 (3) | −0.0049 (3) |
N1A | 0.0077 (4) | 0.0125 (4) | 0.0103 (3) | −0.0002 (3) | 0.0016 (3) | −0.0011 (3) |
C1B | 0.0104 (4) | 0.0094 (4) | 0.0095 (4) | 0.0008 (4) | −0.0002 (3) | −0.0002 (3) |
C2B | 0.0102 (4) | 0.0105 (4) | 0.0082 (4) | 0.0002 (3) | 0.0007 (3) | −0.0010 (3) |
C3B | 0.0098 (4) | 0.0107 (4) | 0.0097 (4) | 0.0003 (3) | −0.0001 (3) | 0.0005 (3) |
C4B | 0.0117 (5) | 0.0134 (5) | 0.0087 (4) | 0.0004 (4) | −0.0004 (3) | −0.0012 (3) |
C5B | 0.0128 (5) | 0.0133 (5) | 0.0092 (4) | 0.0010 (4) | 0.0009 (3) | −0.0001 (3) |
C6B | 0.0082 (4) | 0.0203 (5) | 0.0163 (4) | 0.0016 (4) | 0.0032 (3) | −0.0001 (4) |
C7B | 0.0099 (4) | 0.0153 (5) | 0.0127 (4) | 0.0005 (4) | −0.0026 (3) | −0.0013 (4) |
O1B | 0.0092 (3) | 0.0211 (4) | 0.0097 (3) | 0.0018 (3) | 0.0012 (2) | −0.0045 (3) |
O2B | 0.0078 (3) | 0.0192 (4) | 0.0142 (3) | −0.0004 (3) | 0.0005 (3) | −0.0029 (3) |
N1B | 0.0080 (4) | 0.0128 (4) | 0.0103 (3) | 0.0003 (3) | 0.0013 (3) | 0.0006 (3) |
Geometric parameters (Å, º) top
C1A—C2A | 1.3742 (14) | C1B—C2B | 1.3749 (14) |
C1A—N1A | 1.3788 (12) | C1B—N1B | 1.3796 (12) |
C1A—C7A | 1.4991 (13) | C1B—C7B | 1.4992 (13) |
C2A—O1A | 1.3652 (11) | C2B—O1B | 1.3605 (11) |
C2A—C3A | 1.4393 (13) | C2B—C3B | 1.4425 (13) |
C3A—O2A | 1.2689 (12) | C3B—O2B | 1.2708 (12) |
C3A—C4A | 1.4253 (13) | C3B—C4B | 1.4248 (13) |
C4A—C5A | 1.3642 (15) | C4B—C5B | 1.3645 (15) |
C4A—H4A | 0.9500 | C4B—H4B | 0.9500 |
C5A—N1A | 1.3540 (13) | C5B—N1B | 1.3521 (13) |
C5A—H5A | 0.9500 | C5B—H5B | 0.9500 |
C6A—N1A | 1.4693 (13) | C6B—N1B | 1.4708 (13) |
C6A—H6AA | 0.9800 | C6B—H6BA | 0.9800 |
C6A—H6AB | 0.9800 | C6B—H6BB | 0.9800 |
C6A—H6AC | 0.9800 | C6B—H6BC | 0.9800 |
C7A—H7AA | 0.9800 | C7B—H7BA | 0.9800 |
C7A—H7AB | 0.9800 | C7B—H7BB | 0.9800 |
C7A—H7AC | 0.9800 | C7B—H7BC | 0.9800 |
O1A—H1O | 0.899 (18) | O1B—H2O | 0.911 (19) |
| | | |
C2A—C1A—N1A | 119.05 (9) | C2B—C1B—N1B | 119.02 (9) |
C2A—C1A—C7A | 122.45 (9) | C2B—C1B—C7B | 122.28 (9) |
N1A—C1A—C7A | 118.50 (9) | N1B—C1B—C7B | 118.69 (9) |
O1A—C2A—C1A | 118.98 (9) | O1B—C2B—C1B | 118.72 (9) |
O1A—C2A—C3A | 118.55 (9) | O1B—C2B—C3B | 118.81 (9) |
C1A—C2A—C3A | 122.46 (9) | C1B—C2B—C3B | 122.43 (9) |
O2A—C3A—C4A | 124.28 (9) | O2B—C3B—C4B | 124.56 (9) |
O2A—C3A—C2A | 120.99 (9) | O2B—C3B—C2B | 120.68 (9) |
C4A—C3A—C2A | 114.73 (9) | C4B—C3B—C2B | 114.75 (9) |
C5A—C4A—C3A | 121.23 (9) | C5B—C4B—C3B | 121.04 (9) |
C5A—C4A—H4A | 119.4 | C5B—C4B—H4B | 119.5 |
C3A—C4A—H4A | 119.4 | C3B—C4B—H4B | 119.5 |
N1A—C5A—C4A | 121.72 (9) | N1B—C5B—C4B | 122.08 (9) |
N1A—C5A—H5A | 119.1 | N1B—C5B—H5B | 119.0 |
C4A—C5A—H5A | 119.1 | C4B—C5B—H5B | 119.0 |
N1A—C6A—H6AA | 109.5 | N1B—C6B—H6BA | 109.5 |
N1A—C6A—H6AB | 109.5 | N1B—C6B—H6BB | 109.5 |
H6AA—C6A—H6AB | 109.5 | H6BA—C6B—H6BB | 109.5 |
N1A—C6A—H6AC | 109.5 | N1B—C6B—H6BC | 109.5 |
H6AA—C6A—H6AC | 109.5 | H6BA—C6B—H6BC | 109.5 |
H6AB—C6A—H6AC | 109.5 | H6BB—C6B—H6BC | 109.5 |
C1A—C7A—H7AA | 109.5 | C1B—C7B—H7BA | 109.5 |
C1A—C7A—H7AB | 109.5 | C1B—C7B—H7BB | 109.5 |
H7AA—C7A—H7AB | 109.5 | H7BA—C7B—H7BB | 109.5 |
C1A—C7A—H7AC | 109.5 | C1B—C7B—H7BC | 109.5 |
H7AA—C7A—H7AC | 109.5 | H7BA—C7B—H7BC | 109.5 |
H7AB—C7A—H7AC | 109.5 | H7BB—C7B—H7BC | 109.5 |
C2A—O1A—H1O | 109.0 (11) | C2B—O1B—H2O | 110.8 (11) |
C5A—N1A—C1A | 120.76 (9) | C5B—N1B—C1B | 120.63 (9) |
C5A—N1A—C6A | 118.92 (8) | C5B—N1B—C6B | 119.21 (8) |
C1A—N1A—C6A | 120.30 (8) | C1B—N1B—C6B | 120.15 (8) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1O···O2B | 0.899 (18) | 1.874 (18) | 2.6847 (11) | 149 (2) |
O1B—H2O···O2A | 0.911 (19) | 1.825 (19) | 2.6504 (11) | 150 (2) |
C6A—H6AB···O2Ai | 0.98 | 2.53 | 3.4705 (12) | 161 |
C7A—H7AA···O2Bii | 0.98 | 2.54 | 3.4957 (13) | 165 |
C6B—H6BA···O2Biii | 0.98 | 2.49 | 3.3798 (12) | 151 |
C7B—H7BA···O2Aiv | 0.98 | 2.52 | 3.4901 (13) | 171 |
Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) −x+1/2, y+1/2, z; (iii) x+1/2, y, −z+1/2; (iv) −x+3/2, y−1/2, z. |
Crystal data top
C7H9NO2·2(C6H6O2) | Dx = 1.375 Mg m−3 |
Mr = 359.37 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P42/n | Cell parameters from 9989 reflections |
a = 22.550 (4) Å | θ = 2.4–30.1° |
c = 6.8267 (1) Å | µ = 0.10 mm−1 |
V = 3471.42 (5) Å3 | T = 100 K |
Z = 8 | Needle, colorless |
F(000) = 1520 | 0.28 × 0.12 × 0.09 mm |
Data collection top
Bruker D8 QUEST PHOTON-100 diffractometer | 4017 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.073 |
Absorption correction: multi-scan SADABS, Bruker, 2016 | θmax = 30.6°, θmin = 2.6° |
Tmin = 0.706, Tmax = 0.746 | h = −32→26 |
47912 measured reflections | k = −32→32 |
5309 independent reflections | l = −9→9 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.058 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.131 | w = 1/[σ2(Fo2) + (0.0519P)2 + 2.1309P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
5309 reflections | Δρmax = 0.41 e Å−3 |
257 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 | |
C1 | 0.47835 (6) | 0.66438 (6) | 0.6865 (2) | 0.0122 (3) | |
C2 | 0.49546 (6) | 0.60852 (6) | 0.6266 (2) | 0.0113 (3) | |
C3 | 0.52343 (6) | 0.56812 (6) | 0.7564 (2) | 0.0117 (3) | |
C4 | 0.52834 (7) | 0.58639 (7) | 0.9529 (2) | 0.0150 (3) | |
H4 | 0.544184 | 0.560063 | 1.048095 | 0.018* | |
C5 | 0.51042 (7) | 0.64178 (7) | 1.0070 (2) | 0.0154 (3) | |
H5 | 0.514663 | 0.653586 | 1.139891 | 0.018* | |
C6 | 0.46925 (7) | 0.73987 (7) | 0.9457 (2) | 0.0192 (3) | |
H6A | 0.489125 | 0.770035 | 0.865921 | 0.029* | |
H6B | 0.480744 | 0.744772 | 1.083231 | 0.029* | |
H6C | 0.426185 | 0.744369 | 0.933321 | 0.029* | |
C7 | 0.45202 (7) | 0.70840 (7) | 0.5480 (2) | 0.0171 (3) | |
H7A | 0.442144 | 0.688644 | 0.424357 | 0.026* | |
H7B | 0.480697 | 0.740182 | 0.523120 | 0.026* | |
H7C | 0.415963 | 0.725263 | 0.605587 | 0.026* | |
N1 | 0.48687 (5) | 0.68024 (5) | 0.87751 (18) | 0.0129 (2) | |
O1 | 0.48697 (5) | 0.59372 (5) | 0.43606 (15) | 0.0151 (2) | |
H1O | 0.4866 (9) | 0.5564 (10) | 0.422 (3) | 0.025 (5)* | |
O2 | 0.54424 (5) | 0.51789 (4) | 0.68932 (15) | 0.0145 (2) | |
C8A | 0.70093 (7) | 0.59102 (7) | 0.2529 (2) | 0.0189 (3) | |
C9A | 0.66270 (7) | 0.58040 (7) | 0.4104 (2) | 0.0173 (3) | |
C10A | 0.67482 (8) | 0.60455 (8) | 0.5928 (2) | 0.0228 (3) | |
H10A | 0.648727 | 0.597654 | 0.699700 | 0.027* | |
C11A | 0.72541 (9) | 0.63892 (9) | 0.6184 (3) | 0.0331 (4) | |
H11A | 0.733905 | 0.655371 | 0.743351 | 0.040* | |
C12A | 0.76343 (9) | 0.64936 (10) | 0.4634 (3) | 0.0343 (5) | |
H12A | 0.798036 | 0.672711 | 0.482156 | 0.041* | |
C13A | 0.75091 (8) | 0.62555 (8) | 0.2797 (3) | 0.0266 (4) | |
H13A | 0.776764 | 0.633070 | 0.172717 | 0.032* | |
O3A | 0.69064 (6) | 0.56766 (6) | 0.07146 (17) | 0.0246 (3) | |
H2O | 0.6607 (11) | 0.5439 (11) | 0.071 (3) | 0.041 (7)* | |
O4A | 0.61484 (5) | 0.54393 (5) | 0.37399 (17) | 0.0201 (2) | |
H3O | 0.5940 (10) | 0.5356 (10) | 0.481 (3) | 0.037 (6)* | |
C8B | 0.65264 (6) | 0.39669 (7) | 0.1487 (2) | 0.0137 (3) | |
C9B | 0.63404 (6) | 0.42066 (6) | −0.0309 (2) | 0.0124 (3) | |
C10B | 0.64106 (6) | 0.38840 (7) | −0.2019 (2) | 0.0147 (3) | |
H10B | 0.628714 | 0.404702 | −0.323601 | 0.018* | |
C11B | 0.66622 (7) | 0.33209 (7) | −0.1954 (2) | 0.0186 (3) | |
H11B | 0.670998 | 0.309949 | −0.312766 | 0.022* | |
C12B | 0.68432 (7) | 0.30827 (7) | −0.0182 (3) | 0.0221 (3) | |
H12B | 0.701553 | 0.269843 | −0.014162 | 0.026* | |
C13B | 0.67729 (7) | 0.34046 (7) | 0.1531 (2) | 0.0190 (3) | |
H13B | 0.689476 | 0.323842 | 0.274487 | 0.023* | |
O3B | 0.64716 (5) | 0.42727 (6) | 0.31959 (16) | 0.0201 (3) | |
H4O | 0.6321 (11) | 0.4639 (12) | 0.297 (4) | 0.048 (7)* | |
O4B | 0.61048 (5) | 0.47649 (5) | −0.02346 (16) | 0.0186 (2) | |
H5O | 0.5903 (10) | 0.4857 (10) | −0.129 (4) | 0.036 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0117 (6) | 0.0131 (6) | 0.0117 (6) | −0.0015 (5) | −0.0006 (5) | 0.0005 (5) |
C2 | 0.0117 (6) | 0.0141 (6) | 0.0082 (6) | −0.0015 (5) | −0.0006 (5) | −0.0002 (5) |
C3 | 0.0123 (6) | 0.0115 (6) | 0.0111 (6) | 0.0002 (5) | −0.0004 (5) | −0.0011 (5) |
C4 | 0.0195 (7) | 0.0165 (7) | 0.0092 (7) | 0.0029 (6) | −0.0021 (5) | 0.0009 (5) |
C5 | 0.0180 (7) | 0.0191 (7) | 0.0091 (6) | 0.0010 (6) | −0.0011 (5) | −0.0025 (5) |
C6 | 0.0234 (8) | 0.0141 (7) | 0.0201 (8) | 0.0022 (6) | −0.0033 (6) | −0.0077 (6) |
C7 | 0.0229 (8) | 0.0128 (7) | 0.0155 (7) | 0.0021 (6) | −0.0025 (6) | 0.0005 (5) |
N1 | 0.0143 (6) | 0.0120 (6) | 0.0123 (6) | 0.0001 (5) | −0.0003 (5) | −0.0029 (5) |
O1 | 0.0235 (6) | 0.0135 (5) | 0.0082 (5) | 0.0020 (4) | −0.0034 (4) | −0.0017 (4) |
O2 | 0.0183 (5) | 0.0135 (5) | 0.0118 (5) | 0.0037 (4) | −0.0024 (4) | −0.0020 (4) |
C8A | 0.0228 (8) | 0.0214 (8) | 0.0125 (7) | 0.0051 (6) | −0.0009 (6) | −0.0005 (6) |
C9A | 0.0173 (7) | 0.0205 (7) | 0.0140 (7) | 0.0035 (6) | −0.0003 (6) | −0.0014 (6) |
C10A | 0.0239 (8) | 0.0291 (9) | 0.0154 (7) | 0.0003 (7) | 0.0021 (6) | −0.0034 (6) |
C11A | 0.0356 (10) | 0.0429 (11) | 0.0207 (9) | −0.0115 (9) | 0.0003 (8) | −0.0100 (8) |
C12A | 0.0324 (10) | 0.0434 (11) | 0.0270 (10) | −0.0161 (9) | 0.0025 (8) | −0.0079 (8) |
C13A | 0.0262 (9) | 0.0339 (10) | 0.0198 (8) | −0.0036 (7) | 0.0046 (7) | −0.0003 (7) |
O3A | 0.0254 (6) | 0.0357 (7) | 0.0126 (5) | −0.0032 (6) | 0.0022 (5) | −0.0039 (5) |
O4A | 0.0178 (5) | 0.0296 (6) | 0.0130 (5) | −0.0013 (5) | 0.0025 (4) | −0.0050 (5) |
C8B | 0.0099 (6) | 0.0209 (7) | 0.0101 (6) | −0.0026 (5) | −0.0022 (5) | 0.0015 (5) |
C9B | 0.0099 (6) | 0.0154 (7) | 0.0118 (7) | −0.0002 (5) | −0.0019 (5) | 0.0017 (5) |
C10B | 0.0128 (6) | 0.0201 (7) | 0.0111 (7) | −0.0005 (5) | −0.0012 (5) | 0.0004 (6) |
C11B | 0.0157 (7) | 0.0202 (7) | 0.0199 (7) | 0.0009 (6) | −0.0004 (6) | −0.0053 (6) |
C12B | 0.0188 (8) | 0.0158 (7) | 0.0316 (9) | 0.0022 (6) | −0.0068 (7) | 0.0001 (7) |
C13B | 0.0169 (7) | 0.0207 (8) | 0.0193 (8) | −0.0018 (6) | −0.0072 (6) | 0.0067 (6) |
O3B | 0.0220 (6) | 0.0287 (6) | 0.0095 (5) | 0.0004 (5) | −0.0035 (4) | −0.0011 (4) |
O4B | 0.0256 (6) | 0.0169 (5) | 0.0135 (5) | 0.0071 (4) | −0.0093 (4) | −0.0023 (4) |
Geometric parameters (Å, º) top
C1—N1 | 1.3655 (18) | C10A—C11A | 1.390 (3) |
C1—C2 | 1.380 (2) | C10A—H10A | 0.9500 |
C1—C7 | 1.494 (2) | C11A—C12A | 1.382 (3) |
C2—O1 | 1.3567 (17) | C11A—H11A | 0.9500 |
C2—C3 | 1.419 (2) | C12A—C13A | 1.393 (3) |
C3—O2 | 1.3089 (17) | C12A—H12A | 0.9500 |
C3—C4 | 1.407 (2) | C13A—H13A | 0.9500 |
C4—C5 | 1.364 (2) | O3A—H2O | 0.86 (3) |
C4—H4 | 0.9500 | O4A—H3O | 0.89 (2) |
C5—N1 | 1.3477 (19) | C8B—O3B | 1.3611 (18) |
C5—H5 | 0.9500 | C8B—C13B | 1.385 (2) |
C6—N1 | 1.4776 (19) | C8B—C9B | 1.404 (2) |
C6—H6A | 0.9800 | C9B—O4B | 1.3674 (18) |
C6—H6B | 0.9800 | C9B—C10B | 1.385 (2) |
C6—H6C | 0.9800 | C10B—C11B | 1.391 (2) |
C7—H7A | 0.9800 | C10B—H10B | 0.9500 |
C7—H7B | 0.9800 | C11B—C12B | 1.385 (2) |
C7—H7C | 0.9800 | C11B—H11B | 0.9500 |
O1—H1O | 0.85 (2) | C12B—C13B | 1.386 (2) |
C8A—O3A | 1.3658 (19) | C12B—H12B | 0.9500 |
C8A—C13A | 1.382 (2) | C13B—H13B | 0.9500 |
C8A—C9A | 1.399 (2) | O3B—H4O | 0.91 (3) |
C9A—O4A | 1.3794 (19) | O4B—H5O | 0.88 (2) |
C9A—C10A | 1.387 (2) | | |
| | | |
N1—C1—C2 | 118.87 (13) | C10A—C9A—C8A | 120.11 (15) |
N1—C1—C7 | 119.10 (13) | C9A—C10A—C11A | 119.56 (16) |
C2—C1—C7 | 122.02 (13) | C9A—C10A—H10A | 120.2 |
O1—C2—C1 | 118.00 (13) | C11A—C10A—H10A | 120.2 |
O1—C2—C3 | 120.25 (13) | C12A—C11A—C10A | 120.56 (17) |
C1—C2—C3 | 121.70 (13) | C12A—C11A—H11A | 119.7 |
O2—C3—C4 | 123.97 (13) | C10A—C11A—H11A | 119.7 |
O2—C3—C2 | 119.76 (13) | C11A—C12A—C13A | 119.84 (17) |
C4—C3—C2 | 116.24 (13) | C11A—C12A—H12A | 120.1 |
C5—C4—C3 | 120.21 (13) | C13A—C12A—H12A | 120.1 |
C5—C4—H4 | 119.9 | C8A—C13A—C12A | 120.12 (16) |
C3—C4—H4 | 119.9 | C8A—C13A—H13A | 119.9 |
N1—C5—C4 | 121.89 (14) | C12A—C13A—H13A | 119.9 |
N1—C5—H5 | 119.1 | C8A—O3A—H2O | 112.0 (16) |
C4—C5—H5 | 119.1 | C9A—O4A—H3O | 113.0 (15) |
N1—C6—H6A | 109.5 | O3B—C8B—C13B | 118.78 (13) |
N1—C6—H6B | 109.5 | O3B—C8B—C9B | 121.76 (13) |
H6A—C6—H6B | 109.5 | C13B—C8B—C9B | 119.46 (14) |
N1—C6—H6C | 109.5 | O4B—C9B—C10B | 124.00 (13) |
H6A—C6—H6C | 109.5 | O4B—C9B—C8B | 116.01 (13) |
H6B—C6—H6C | 109.5 | C10B—C9B—C8B | 119.98 (13) |
C1—C7—H7A | 109.5 | C9B—C10B—C11B | 119.94 (14) |
C1—C7—H7B | 109.5 | C9B—C10B—H10B | 120.0 |
H7A—C7—H7B | 109.5 | C11B—C10B—H10B | 120.0 |
C1—C7—H7C | 109.5 | C12B—C11B—C10B | 120.13 (15) |
H7A—C7—H7C | 109.5 | C12B—C11B—H11B | 119.9 |
H7B—C7—H7C | 109.5 | C10B—C11B—H11B | 119.9 |
C5—N1—C1 | 120.89 (12) | C11B—C12B—C13B | 120.02 (15) |
C5—N1—C6 | 119.00 (12) | C11B—C12B—H12B | 120.0 |
C1—N1—C6 | 120.10 (12) | C13B—C12B—H12B | 120.0 |
C2—O1—H1O | 110.6 (14) | C8B—C13B—C12B | 120.47 (14) |
O3A—C8A—C13A | 118.43 (15) | C8B—C13B—H13B | 119.8 |
O3A—C8A—C9A | 121.76 (15) | C12B—C13B—H13B | 119.8 |
C13A—C8A—C9A | 119.81 (15) | C8B—O3B—H4O | 110.4 (17) |
O4A—C9A—C10A | 123.38 (14) | C9B—O4B—H5O | 112.8 (15) |
O4A—C9A—C8A | 116.47 (13) | | |
| | | |
N1—C1—C2—O1 | −179.60 (12) | C13A—C8A—C9A—C10A | 0.2 (2) |
C7—C1—C2—O1 | −0.9 (2) | O4A—C9A—C10A—C11A | 177.38 (16) |
N1—C1—C2—C3 | −2.2 (2) | C8A—C9A—C10A—C11A | −0.5 (3) |
C7—C1—C2—C3 | 176.45 (13) | C9A—C10A—C11A—C12A | 0.3 (3) |
O1—C2—C3—O2 | 4.1 (2) | C10A—C11A—C12A—C13A | 0.3 (3) |
C1—C2—C3—O2 | −173.26 (13) | O3A—C8A—C13A—C12A | −178.94 (17) |
O1—C2—C3—C4 | −177.70 (13) | C9A—C8A—C13A—C12A | 0.5 (3) |
C1—C2—C3—C4 | 5.0 (2) | C11A—C12A—C13A—C8A | −0.7 (3) |
O2—C3—C4—C5 | 173.81 (14) | O3B—C8B—C9B—O4B | 0.3 (2) |
C2—C3—C4—C5 | −4.3 (2) | C13B—C8B—C9B—O4B | −179.63 (13) |
C3—C4—C5—N1 | 1.0 (2) | O3B—C8B—C9B—C10B | 179.19 (13) |
C4—C5—N1—C1 | 2.0 (2) | C13B—C8B—C9B—C10B | −0.8 (2) |
C4—C5—N1—C6 | −179.08 (14) | O4B—C9B—C10B—C11B | 179.17 (14) |
C2—C1—N1—C5 | −1.4 (2) | C8B—C9B—C10B—C11B | 0.4 (2) |
C7—C1—N1—C5 | 179.92 (14) | C9B—C10B—C11B—C12B | −0.1 (2) |
C2—C1—N1—C6 | 179.70 (13) | C10B—C11B—C12B—C13B | 0.1 (2) |
C7—C1—N1—C6 | 1.0 (2) | O3B—C8B—C13B—C12B | −179.14 (14) |
O3A—C8A—C9A—O4A | 1.5 (2) | C9B—C8B—C13B—C12B | 0.8 (2) |
C13A—C8A—C9A—O4A | −177.90 (15) | C11B—C12B—C13B—C8B | −0.5 (2) |
O3A—C8A—C9A—C10A | 179.55 (15) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O2i | 0.85 (2) | 1.97 (2) | 2.7499 (15) | 153.2 (19) |
O4A—H3O···O2 | 0.89 (2) | 1.86 (2) | 2.7410 (16) | 175 (2) |
O3B—H4O···O4A | 0.91 (3) | 1.92 (3) | 2.7550 (18) | 152 (2) |
O3B—H4O···O4B | 0.91 (3) | 2.26 (3) | 2.7205 (16) | 111 (2) |
O4B—H5O···O2ii | 0.88 (2) | 1.77 (2) | 2.6358 (15) | 167 (2) |
C5—H5···O1iii | 0.95 | 2.51 | 3.1673 (18) | 126 |
C10B—H10B···O3Bii | 0.95 | 2.52 | 3.3847 (18) | 151 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z−1; (iii) x, y, z+1. |
Deferiprone-Catechol (2:3) cocrystal (KA1036_0m_Def-cat_2_3)
top
Crystal data top
2(C7H9NO2)·3(C6H6O2) | F(000) = 644 |
Mr = 608.63 | Dx = 1.396 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.9488 (17) Å | Cell parameters from 9899 reflections |
b = 9.982 (2) Å | θ = 2.8–30.6° |
c = 20.881 (5) Å | µ = 0.10 mm−1 |
β = 90.927 (7)° | T = 100 K |
V = 1448.3 (6) Å3 | Block, colorless |
Z = 2 | 0.32 × 0.28 × 0.21 mm |
Data collection top
Bruker D8 QUEST PHOTON-100 diffractometer | 8447 reflections with I > 2σ(I) |
Radiation source: microfocus | Rint = 0.049 |
ω and φ scans | θmax = 30.6°, θmin = 2.3° |
Absorption correction: multi-scan SADABS, Bruker, 2016 | h = −9→9 |
Tmin = 0.649, Tmax = 0.746 | k = −14→14 |
34096 measured reflections | l = −29→29 |
8799 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.062 | w = 1/[σ2(Fo2) + (0.0525P)2 + 2.4574P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.168 | (Δ/σ)max < 0.001 |
S = 1.11 | Δρmax = 0.41 e Å−3 |
8799 reflections | Δρmin = −0.41 e Å−3 |
458 parameters | Absolute structure: Flack x determined using 3652 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
1 restraint | Absolute structure parameter: 0.3 (2) |
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) |
C1A | 0.2719 (5) | 0.6492 (4) | 0.13991 (16) | 0.0161 (6) | |
C2A | 0.3566 (5) | 0.5416 (4) | 0.16957 (16) | 0.0146 (6) | |
C3A | 0.2540 (5) | 0.4203 (4) | 0.18182 (16) | 0.0156 (6) | |
C4A | 0.0574 (6) | 0.4202 (5) | 0.16367 (19) | 0.0225 (8) | |
H4A | −0.018600 | 0.342786 | 0.170995 | 0.027* | |
C5A | −0.0237 (6) | 0.5296 (5) | 0.13590 (19) | 0.0245 (8) | |
H5A | −0.157042 | 0.528008 | 0.125068 | 0.029* | |
C6A | −0.0145 (7) | 0.7561 (5) | 0.0917 (2) | 0.0307 (10) | |
H6AA | 0.057348 | 0.781428 | 0.053522 | 0.046* | |
H6AB | −0.017871 | 0.831972 | 0.121405 | 0.046* | |
H6AC | −0.146191 | 0.731242 | 0.079099 | 0.046* | |
C7A | 0.3843 (6) | 0.7723 (4) | 0.12293 (18) | 0.0207 (7) | |
H7AA | 0.398524 | 0.776876 | 0.076360 | 0.031* | |
H7AB | 0.511831 | 0.768415 | 0.143572 | 0.031* | |
H7AC | 0.315875 | 0.852083 | 0.137759 | 0.031* | |
N1A | 0.0803 (5) | 0.6417 (4) | 0.12308 (15) | 0.0206 (6) | |
O1A | 0.5481 (4) | 0.5482 (3) | 0.18441 (13) | 0.0168 (5) | |
H1A | 0.575399 | 0.490481 | 0.212363 | 0.025* | |
O2A | 0.3434 (4) | 0.3174 (3) | 0.20574 (13) | 0.0196 (5) | |
C1B | 0.7093 (5) | 0.1151 (3) | 0.36593 (15) | 0.0109 (5) | |
C2B | 0.6458 (5) | 0.2298 (3) | 0.33367 (16) | 0.0108 (6) | |
C3B | 0.7742 (4) | 0.3371 (3) | 0.31883 (15) | 0.0098 (5) | |
C4B | 0.9709 (5) | 0.3156 (3) | 0.33511 (16) | 0.0124 (6) | |
H4B | 1.064066 | 0.381066 | 0.324301 | 0.015* | |
C5B | 1.0272 (5) | 0.2012 (3) | 0.36626 (17) | 0.0125 (6) | |
H5B | 1.159657 | 0.188761 | 0.376540 | 0.015* | |
C6B | 0.9695 (5) | −0.0134 (4) | 0.41889 (18) | 0.0166 (7) | |
H6BA | 0.939460 | −0.094763 | 0.394401 | 0.025* | |
H6BB | 0.905816 | −0.017344 | 0.460390 | 0.025* | |
H6BC | 1.108990 | −0.006843 | 0.425731 | 0.025* | |
C7B | 0.5733 (5) | 0.0055 (3) | 0.38372 (17) | 0.0137 (6) | |
H7BA | 0.449223 | 0.019581 | 0.361799 | 0.021* | |
H7BB | 0.554977 | 0.006148 | 0.430148 | 0.021* | |
H7BC | 0.626807 | −0.081103 | 0.370848 | 0.021* | |
N1B | 0.9001 (4) | 0.1054 (3) | 0.38284 (14) | 0.0113 (5) | |
O1B | 0.4544 (3) | 0.2388 (3) | 0.32002 (12) | 0.0138 (5) | |
H1B | 0.437990 | 0.277578 | 0.284660 | 0.021* | |
O2B | 0.7103 (3) | 0.4468 (2) | 0.29240 (12) | 0.0111 (4) | |
C8A | 0.1347 (5) | 0.8348 (4) | 0.26655 (15) | 0.0129 (6) | |
C9A | −0.0287 (5) | 0.7535 (3) | 0.27123 (15) | 0.0114 (6) | |
C10A | −0.2105 (5) | 0.8043 (4) | 0.25475 (17) | 0.0145 (6) | |
H10A | −0.321524 | 0.749479 | 0.258468 | 0.017* | |
C11A | −0.2280 (5) | 0.9356 (4) | 0.23287 (18) | 0.0174 (7) | |
H11A | −0.350870 | 0.969958 | 0.220901 | 0.021* | |
C12A | −0.0659 (6) | 1.0165 (4) | 0.22850 (18) | 0.0185 (7) | |
H12A | −0.079036 | 1.106277 | 0.213931 | 0.022* | |
C13A | 0.1167 (5) | 0.9669 (4) | 0.24540 (17) | 0.0156 (6) | |
H13A | 0.227117 | 1.022576 | 0.242472 | 0.019* | |
O3A | 0.3152 (4) | 0.7880 (3) | 0.28248 (13) | 0.0173 (5) | |
H3A | 0.305761 | 0.712549 | 0.299998 | 0.026* | |
O4A | 0.0018 (3) | 0.6260 (2) | 0.29408 (12) | 0.0133 (4) | |
H4A1 | −0.102005 | 0.582892 | 0.292445 | 0.020* | |
C8B | 0.3178 (5) | 0.6869 (3) | 0.44165 (16) | 0.0124 (6) | |
C9B | 0.4664 (5) | 0.6240 (3) | 0.40733 (15) | 0.0116 (6) | |
C10B | 0.6558 (5) | 0.6363 (4) | 0.42883 (16) | 0.0138 (6) | |
H10B | 0.756010 | 0.593042 | 0.406365 | 0.017* | |
C11B | 0.6995 (5) | 0.7125 (4) | 0.48363 (16) | 0.0141 (6) | |
H11B | 0.829099 | 0.720224 | 0.498365 | 0.017* | |
C12B | 0.5536 (5) | 0.7765 (4) | 0.51627 (16) | 0.0156 (6) | |
H12B | 0.583573 | 0.829442 | 0.552886 | 0.019* | |
C13B | 0.3626 (5) | 0.7631 (4) | 0.49536 (17) | 0.0147 (6) | |
H13B | 0.262921 | 0.806361 | 0.518072 | 0.018* | |
O3B | 0.1290 (4) | 0.6730 (3) | 0.42250 (13) | 0.0171 (5) | |
H3B | 0.123517 | 0.631489 | 0.387518 | 0.026* | |
O4B | 0.4100 (3) | 0.5544 (3) | 0.35333 (12) | 0.0144 (5) | |
H4B1 | 0.507579 | 0.524566 | 0.334864 | 0.022* | |
C8C | 0.5575 (8) | 0.1394 (6) | 0.0863 (3) | 0.0158 (17) | 0.578 (7) |
C9C | 0.3632 (8) | 0.1287 (7) | 0.0702 (3) | 0.0193 (19) | 0.578 (7) |
H9C | 0.270146 | 0.175277 | 0.094530 | 0.023* | 0.578 (7) |
C10C | 0.3050 (8) | 0.0501 (6) | 0.0185 (2) | 0.0226 (16) | 0.578 (7) |
H10C | 0.172198 | 0.042817 | 0.007483 | 0.027* | 0.578 (7) |
C11C | 0.4411 (10) | −0.0180 (5) | −0.0171 (2) | 0.0217 (15) | 0.578 (7) |
H11C | 0.401318 | −0.071790 | −0.052472 | 0.026* | 0.578 (7) |
C12C | 0.6354 (10) | −0.0074 (6) | −0.0010 (2) | 0.0229 (16) | 0.578 (7) |
H12C | 0.728388 | −0.053938 | −0.025380 | 0.028* | 0.578 (7) |
C13C | 0.6936 (7) | 0.0713 (6) | 0.0507 (3) | 0.0206 (15) | 0.578 (7) |
O3C | 0.6313 (7) | 0.2146 (5) | 0.1371 (2) | 0.0194 (11) | 0.578 (7) |
H3C | 0.567557 | 0.285703 | 0.140539 | 0.029* | 0.578 (7) |
O4C | 0.8821 (10) | 0.0792 (8) | 0.0632 (4) | 0.0418 (18) | 0.578 (7) |
H4C | 0.911084 | 0.026615 | 0.093299 | 0.063* | 0.578 (7) |
C8' | 0.4207 (10) | 0.1138 (10) | 0.0776 (4) | 0.017 (3) | 0.422 (7) |
C9' | 0.3890 (10) | 0.0332 (8) | 0.0242 (3) | 0.018 (2) | 0.422 (7) |
C10' | 0.5441 (13) | −0.0140 (7) | −0.0104 (3) | 0.019 (2) | 0.422 (7) |
H10' | 0.522448 | −0.069134 | −0.046929 | 0.023* | 0.422 (7) |
C11' | 0.7308 (11) | 0.0194 (8) | 0.0083 (3) | 0.025 (2) | 0.422 (7) |
H11' | 0.836817 | −0.012902 | −0.015340 | 0.030* | 0.422 (7) |
C12' | 0.7625 (10) | 0.1000 (9) | 0.0617 (4) | 0.022 (2) | 0.422 (7) |
H12' | 0.890119 | 0.122834 | 0.074571 | 0.027* | 0.422 (7) |
C13' | 0.6074 (12) | 0.1472 (10) | 0.0964 (4) | 0.022 (3) | 0.422 (7) |
H13' | 0.629050 | 0.202340 | 0.132894 | 0.027* | 0.422 (7) |
O3' | 0.2566 (9) | 0.1517 (7) | 0.1107 (3) | 0.0198 (15) | 0.422 (7) |
H3' | 0.288568 | 0.200047 | 0.142011 | 0.030* | 0.422 (7) |
O4' | 0.2137 (13) | −0.0044 (9) | 0.0049 (4) | 0.033 (2) | 0.422 (7) |
H4' | 0.131371 | 0.046055 | 0.021380 | 0.049* | 0.422 (7) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.0151 (15) | 0.0208 (17) | 0.0123 (14) | 0.0005 (13) | −0.0009 (11) | −0.0011 (13) |
C2A | 0.0134 (15) | 0.0190 (16) | 0.0112 (13) | −0.0018 (12) | −0.0013 (11) | −0.0009 (12) |
C3A | 0.0175 (15) | 0.0209 (17) | 0.0085 (13) | −0.0051 (13) | −0.0002 (11) | −0.0001 (12) |
C4A | 0.0164 (16) | 0.032 (2) | 0.0186 (17) | −0.0121 (15) | −0.0005 (13) | 0.0004 (15) |
C5A | 0.0114 (15) | 0.043 (2) | 0.0195 (17) | −0.0036 (15) | −0.0014 (13) | −0.0004 (16) |
C6A | 0.028 (2) | 0.039 (2) | 0.0247 (19) | 0.0151 (19) | −0.0063 (16) | 0.0051 (18) |
C7A | 0.0240 (18) | 0.0203 (17) | 0.0177 (16) | 0.0004 (14) | −0.0020 (13) | 0.0034 (14) |
N1A | 0.0143 (14) | 0.0321 (18) | 0.0152 (13) | 0.0059 (13) | −0.0020 (11) | 0.0035 (13) |
O1A | 0.0130 (11) | 0.0200 (12) | 0.0173 (12) | −0.0045 (10) | −0.0053 (9) | 0.0062 (10) |
O2A | 0.0253 (13) | 0.0184 (13) | 0.0150 (11) | −0.0048 (10) | −0.0040 (10) | 0.0017 (10) |
C1B | 0.0116 (13) | 0.0100 (13) | 0.0111 (13) | −0.0007 (11) | −0.0007 (10) | 0.0010 (11) |
C2B | 0.0097 (13) | 0.0094 (13) | 0.0135 (13) | −0.0010 (10) | −0.0005 (10) | −0.0002 (11) |
C3B | 0.0091 (13) | 0.0100 (13) | 0.0102 (13) | −0.0005 (11) | −0.0023 (10) | −0.0007 (11) |
C4B | 0.0098 (13) | 0.0114 (14) | 0.0158 (14) | −0.0012 (11) | −0.0012 (11) | −0.0002 (11) |
C5B | 0.0074 (13) | 0.0132 (14) | 0.0170 (14) | 0.0000 (11) | −0.0010 (10) | 0.0003 (11) |
C6B | 0.0166 (16) | 0.0121 (14) | 0.0209 (16) | 0.0036 (12) | −0.0037 (13) | 0.0062 (12) |
C7B | 0.0147 (15) | 0.0089 (13) | 0.0175 (15) | −0.0026 (11) | 0.0015 (12) | 0.0029 (11) |
N1B | 0.0107 (12) | 0.0082 (12) | 0.0150 (12) | 0.0012 (9) | −0.0016 (10) | 0.0006 (10) |
O1B | 0.0089 (10) | 0.0155 (11) | 0.0170 (11) | −0.0019 (8) | −0.0025 (8) | 0.0054 (9) |
O2B | 0.0102 (10) | 0.0090 (10) | 0.0141 (10) | 0.0006 (8) | −0.0012 (8) | 0.0018 (8) |
C8A | 0.0126 (14) | 0.0152 (15) | 0.0106 (13) | −0.0032 (12) | −0.0029 (11) | −0.0009 (11) |
C9A | 0.0146 (14) | 0.0093 (13) | 0.0103 (13) | −0.0017 (11) | −0.0028 (11) | 0.0009 (10) |
C10A | 0.0127 (14) | 0.0145 (15) | 0.0162 (14) | −0.0012 (12) | −0.0014 (11) | −0.0030 (12) |
C11A | 0.0165 (15) | 0.0174 (16) | 0.0183 (15) | 0.0042 (13) | −0.0038 (12) | −0.0001 (13) |
C12A | 0.0244 (18) | 0.0112 (14) | 0.0199 (16) | 0.0006 (13) | −0.0032 (14) | 0.0026 (12) |
C13A | 0.0180 (15) | 0.0144 (15) | 0.0144 (14) | −0.0044 (12) | 0.0000 (12) | −0.0007 (12) |
O3A | 0.0096 (11) | 0.0167 (12) | 0.0256 (13) | −0.0027 (9) | −0.0018 (9) | 0.0011 (10) |
O4A | 0.0122 (10) | 0.0102 (10) | 0.0174 (11) | −0.0031 (8) | −0.0040 (8) | 0.0031 (9) |
C8B | 0.0111 (14) | 0.0125 (14) | 0.0136 (14) | 0.0005 (11) | 0.0002 (11) | 0.0030 (11) |
C9B | 0.0116 (13) | 0.0103 (13) | 0.0128 (13) | −0.0008 (11) | −0.0017 (11) | −0.0001 (11) |
C10B | 0.0114 (14) | 0.0145 (14) | 0.0154 (14) | 0.0019 (11) | −0.0012 (11) | 0.0021 (12) |
C11B | 0.0135 (14) | 0.0156 (15) | 0.0130 (14) | −0.0011 (12) | −0.0022 (11) | 0.0037 (12) |
C12B | 0.0191 (16) | 0.0171 (16) | 0.0106 (13) | 0.0007 (13) | −0.0006 (11) | 0.0026 (12) |
C13B | 0.0144 (15) | 0.0150 (15) | 0.0146 (14) | 0.0031 (12) | 0.0017 (11) | 0.0009 (12) |
O3B | 0.0096 (11) | 0.0249 (14) | 0.0166 (12) | 0.0027 (9) | −0.0014 (9) | −0.0023 (10) |
O4B | 0.0101 (10) | 0.0158 (11) | 0.0174 (11) | 0.0029 (9) | −0.0017 (8) | −0.0061 (9) |
C8C | 0.019 (4) | 0.015 (3) | 0.012 (3) | 0.003 (3) | −0.002 (3) | 0.003 (2) |
C9C | 0.021 (4) | 0.015 (4) | 0.023 (4) | 0.001 (3) | −0.001 (3) | −0.003 (3) |
C10C | 0.024 (4) | 0.026 (4) | 0.017 (3) | −0.010 (4) | −0.006 (3) | −0.001 (3) |
C11C | 0.038 (5) | 0.016 (3) | 0.011 (3) | −0.002 (3) | −0.002 (3) | 0.002 (2) |
C12C | 0.030 (5) | 0.023 (4) | 0.015 (3) | 0.005 (4) | 0.000 (4) | 0.004 (3) |
C13C | 0.016 (4) | 0.026 (4) | 0.020 (3) | 0.006 (3) | 0.000 (3) | 0.008 (3) |
O3C | 0.013 (2) | 0.021 (2) | 0.024 (2) | 0.0017 (17) | −0.0078 (17) | −0.0045 (19) |
O4C | 0.027 (3) | 0.050 (4) | 0.048 (4) | 0.003 (3) | −0.011 (3) | −0.005 (3) |
C8' | 0.029 (7) | 0.012 (4) | 0.012 (4) | 0.006 (5) | 0.002 (4) | −0.002 (3) |
C9' | 0.020 (5) | 0.016 (4) | 0.018 (4) | −0.003 (4) | −0.003 (4) | 0.007 (3) |
C10' | 0.025 (6) | 0.019 (4) | 0.014 (4) | −0.005 (5) | −0.001 (5) | −0.001 (3) |
C11' | 0.021 (5) | 0.029 (5) | 0.024 (5) | 0.002 (4) | 0.002 (4) | 0.007 (4) |
C12' | 0.005 (5) | 0.036 (6) | 0.026 (5) | 0.001 (4) | −0.002 (4) | 0.001 (4) |
C13' | 0.022 (6) | 0.025 (5) | 0.020 (5) | 0.001 (4) | −0.003 (4) | 0.007 (4) |
O3' | 0.016 (3) | 0.025 (3) | 0.019 (3) | −0.003 (2) | 0.005 (2) | −0.009 (2) |
O4' | 0.032 (4) | 0.040 (5) | 0.026 (4) | 0.001 (4) | −0.001 (3) | −0.004 (3) |
Geometric parameters (Å, º) top
C1A—C2A | 1.369 (5) | C12A—C13A | 1.403 (5) |
C1A—N1A | 1.374 (4) | C12A—H12A | 0.9500 |
C1A—C7A | 1.501 (5) | C13A—H13A | 0.9500 |
C2A—O1A | 1.363 (4) | O3A—H3A | 0.8400 |
C2A—C3A | 1.430 (5) | O4A—H4A1 | 0.8400 |
C3A—O2A | 1.296 (5) | C8B—O3B | 1.372 (4) |
C3A—C4A | 1.411 (5) | C8B—C13B | 1.386 (5) |
C4A—C5A | 1.355 (6) | C8B—C9B | 1.414 (5) |
C4A—H4A | 0.9500 | C9B—O4B | 1.376 (4) |
C5A—N1A | 1.362 (6) | C9B—C10B | 1.389 (4) |
C5A—H5A | 0.9500 | C10B—C11B | 1.403 (5) |
C6A—N1A | 1.467 (6) | C10B—H10B | 0.9500 |
C6A—H6AA | 0.9800 | C11B—C12B | 1.387 (5) |
C6A—H6AB | 0.9800 | C11B—H11B | 0.9500 |
C6A—H6AC | 0.9800 | C12B—C13B | 1.397 (5) |
C7A—H7AA | 0.9800 | C12B—H12B | 0.9500 |
C7A—H7AB | 0.9800 | C13B—H13B | 0.9500 |
C7A—H7AC | 0.9800 | O3B—H3B | 0.8400 |
O1A—H1A | 0.8400 | O4B—H4B1 | 0.8400 |
C1B—N1B | 1.370 (4) | C8C—C9C | 1.3900 |
C1B—C2B | 1.397 (4) | C8C—C13C | 1.3900 |
C1B—C7B | 1.496 (5) | C8C—O3C | 1.391 (6) |
C2B—O1B | 1.358 (4) | C9C—C10C | 1.3900 |
C2B—C3B | 1.431 (4) | C9C—H9C | 0.9500 |
C3B—O2B | 1.301 (4) | C10C—C11C | 1.3900 |
C3B—C4B | 1.419 (4) | C10C—H10C | 0.9500 |
C4B—C5B | 1.368 (5) | C11C—C12C | 1.3900 |
C4B—H4B | 0.9500 | C11C—H11C | 0.9500 |
C5B—N1B | 1.351 (4) | C12C—C13C | 1.3900 |
C5B—H5B | 0.9500 | C12C—H12C | 0.9500 |
C6B—N1B | 1.481 (4) | C13C—O4C | 1.334 (8) |
C6B—H6BA | 0.9800 | O3C—H3C | 0.8400 |
C6B—H6BB | 0.9800 | O4C—H4C | 0.8400 |
C6B—H6BC | 0.9800 | C8'—C9' | 1.3900 |
C7B—H7BA | 0.9800 | C8'—C13' | 1.3900 |
C7B—H7BB | 0.9800 | C8'—O3' | 1.394 (8) |
C7B—H7BC | 0.9800 | C9'—O4' | 1.331 (11) |
O1B—H1B | 0.8400 | C9'—C10' | 1.3900 |
C8A—O3A | 1.375 (4) | C10'—C11' | 1.3900 |
C8A—C13A | 1.395 (5) | C10'—H10' | 0.9500 |
C8A—C9A | 1.400 (4) | C11'—C12' | 1.3900 |
C9A—O4A | 1.375 (4) | C11'—H11' | 0.9500 |
C9A—C10A | 1.399 (5) | C12'—C13' | 1.3900 |
C10A—C11A | 1.393 (5) | C12'—H12' | 0.9500 |
C10A—H10A | 0.9500 | C13'—H13' | 0.9500 |
C11A—C12A | 1.390 (5) | O3'—H3' | 0.8400 |
C11A—H11A | 0.9500 | O4'—H4' | 0.8400 |
| | | |
C2A—C1A—N1A | 118.7 (3) | C12A—C11A—C10A | 120.1 (3) |
C2A—C1A—C7A | 121.9 (3) | C12A—C11A—H11A | 119.9 |
N1A—C1A—C7A | 119.3 (3) | C10A—C11A—H11A | 119.9 |
O1A—C2A—C1A | 118.4 (3) | C11A—C12A—C13A | 120.6 (3) |
O1A—C2A—C3A | 119.2 (3) | C11A—C12A—H12A | 119.7 |
C1A—C2A—C3A | 122.3 (3) | C13A—C12A—H12A | 119.7 |
O2A—C3A—C4A | 124.0 (3) | C8A—C13A—C12A | 119.3 (3) |
O2A—C3A—C2A | 120.1 (3) | C8A—C13A—H13A | 120.4 |
C4A—C3A—C2A | 115.8 (3) | C12A—C13A—H13A | 120.4 |
C5A—C4A—C3A | 120.6 (4) | C8A—O3A—H3A | 109.5 |
C5A—C4A—H4A | 119.7 | C9A—O4A—H4A1 | 109.5 |
C3A—C4A—H4A | 119.7 | O3B—C8B—C13B | 119.5 (3) |
C4A—C5A—N1A | 121.9 (3) | O3B—C8B—C9B | 120.7 (3) |
C4A—C5A—H5A | 119.1 | C13B—C8B—C9B | 119.8 (3) |
N1A—C5A—H5A | 119.1 | O4B—C9B—C10B | 124.5 (3) |
N1A—C6A—H6AA | 109.5 | O4B—C9B—C8B | 116.0 (3) |
N1A—C6A—H6AB | 109.5 | C10B—C9B—C8B | 119.5 (3) |
H6AA—C6A—H6AB | 109.5 | C9B—C10B—C11B | 120.2 (3) |
N1A—C6A—H6AC | 109.5 | C9B—C10B—H10B | 119.9 |
H6AA—C6A—H6AC | 109.5 | C11B—C10B—H10B | 119.9 |
H6AB—C6A—H6AC | 109.5 | C12B—C11B—C10B | 120.0 (3) |
C1A—C7A—H7AA | 109.5 | C12B—C11B—H11B | 120.0 |
C1A—C7A—H7AB | 109.5 | C10B—C11B—H11B | 120.0 |
H7AA—C7A—H7AB | 109.5 | C11B—C12B—C13B | 120.1 (3) |
C1A—C7A—H7AC | 109.5 | C11B—C12B—H12B | 120.0 |
H7AA—C7A—H7AC | 109.5 | C13B—C12B—H12B | 120.0 |
H7AB—C7A—H7AC | 109.5 | C8B—C13B—C12B | 120.4 (3) |
C5A—N1A—C1A | 120.7 (3) | C8B—C13B—H13B | 119.8 |
C5A—N1A—C6A | 119.4 (3) | C12B—C13B—H13B | 119.8 |
C1A—N1A—C6A | 119.9 (4) | C8B—O3B—H3B | 109.5 |
C2A—O1A—H1A | 109.5 | C9B—O4B—H4B1 | 109.5 |
N1B—C1B—C2B | 118.6 (3) | C9C—C8C—C13C | 120.0 |
N1B—C1B—C7B | 119.8 (3) | C9C—C8C—O3C | 124.8 (4) |
C2B—C1B—C7B | 121.6 (3) | C13C—C8C—O3C | 115.2 (4) |
O1B—C2B—C1B | 117.1 (3) | C10C—C9C—C8C | 120.0 |
O1B—C2B—C3B | 121.1 (3) | C10C—C9C—H9C | 120.0 |
C1B—C2B—C3B | 121.7 (3) | C8C—C9C—H9C | 120.0 |
O2B—C3B—C4B | 123.3 (3) | C9C—C10C—C11C | 120.0 |
O2B—C3B—C2B | 120.8 (3) | C9C—C10C—H10C | 120.0 |
C4B—C3B—C2B | 115.9 (3) | C11C—C10C—H10C | 120.0 |
C5B—C4B—C3B | 120.5 (3) | C12C—C11C—C10C | 120.0 |
C5B—C4B—H4B | 119.8 | C12C—C11C—H11C | 120.0 |
C3B—C4B—H4B | 119.8 | C10C—C11C—H11C | 120.0 |
N1B—C5B—C4B | 122.0 (3) | C13C—C12C—C11C | 120.0 |
N1B—C5B—H5B | 119.0 | C13C—C12C—H12C | 120.0 |
C4B—C5B—H5B | 119.0 | C11C—C12C—H12C | 120.0 |
N1B—C6B—H6BA | 109.5 | O4C—C13C—C12C | 117.3 (5) |
N1B—C6B—H6BB | 109.5 | O4C—C13C—C8C | 122.7 (5) |
H6BA—C6B—H6BB | 109.5 | C12C—C13C—C8C | 120.0 |
N1B—C6B—H6BC | 109.5 | C8C—O3C—H3C | 109.5 |
H6BA—C6B—H6BC | 109.5 | C13C—O4C—H4C | 109.5 |
H6BB—C6B—H6BC | 109.5 | C9'—C8'—C13' | 120.0 |
C1B—C7B—H7BA | 109.5 | C9'—C8'—O3' | 115.7 (6) |
C1B—C7B—H7BB | 109.5 | C13'—C8'—O3' | 124.2 (6) |
H7BA—C7B—H7BB | 109.5 | O4'—C9'—C10' | 117.4 (6) |
C1B—C7B—H7BC | 109.5 | O4'—C9'—C8' | 122.6 (6) |
H7BA—C7B—H7BC | 109.5 | C10'—C9'—C8' | 120.0 |
H7BB—C7B—H7BC | 109.5 | C9'—C10'—C11' | 120.0 |
C5B—N1B—C1B | 121.2 (3) | C9'—C10'—H10' | 120.0 |
C5B—N1B—C6B | 119.2 (3) | C11'—C10'—H10' | 120.0 |
C1B—N1B—C6B | 119.6 (3) | C10'—C11'—C12' | 120.0 |
C2B—O1B—H1B | 109.5 | C10'—C11'—H11' | 120.0 |
O3A—C8A—C13A | 118.3 (3) | C12'—C11'—H11' | 120.0 |
O3A—C8A—C9A | 121.6 (3) | C13'—C12'—C11' | 120.0 |
C13A—C8A—C9A | 120.1 (3) | C13'—C12'—H12' | 120.0 |
O4A—C9A—C10A | 123.7 (3) | C11'—C12'—H12' | 120.0 |
O4A—C9A—C8A | 116.1 (3) | C12'—C13'—C8' | 120.0 |
C10A—C9A—C8A | 120.2 (3) | C12'—C13'—H13' | 120.0 |
C11A—C10A—C9A | 119.7 (3) | C8'—C13'—H13' | 120.0 |
C11A—C10A—H10A | 120.2 | C8'—O3'—H3' | 109.5 |
C9A—C10A—H10A | 120.2 | C9'—O4'—H4' | 109.5 |
| | | |
N1A—C1A—C2A—O1A | 178.1 (3) | C8A—C9A—C10A—C11A | 0.8 (5) |
C7A—C1A—C2A—O1A | 0.7 (5) | C9A—C10A—C11A—C12A | −1.1 (5) |
N1A—C1A—C2A—C3A | 2.0 (5) | C10A—C11A—C12A—C13A | 0.6 (6) |
C7A—C1A—C2A—C3A | −175.4 (3) | O3A—C8A—C13A—C12A | 179.6 (3) |
O1A—C2A—C3A—O2A | −1.2 (5) | C9A—C8A—C13A—C12A | −0.5 (5) |
C1A—C2A—C3A—O2A | 174.9 (3) | C11A—C12A—C13A—C8A | 0.2 (5) |
O1A—C2A—C3A—C4A | −178.5 (3) | O3B—C8B—C9B—O4B | 2.6 (5) |
C1A—C2A—C3A—C4A | −2.4 (5) | C13B—C8B—C9B—O4B | −177.7 (3) |
O2A—C3A—C4A—C5A | −176.6 (4) | O3B—C8B—C9B—C10B | −178.0 (3) |
C2A—C3A—C4A—C5A | 0.6 (5) | C13B—C8B—C9B—C10B | 1.6 (5) |
C3A—C4A—C5A—N1A | 1.6 (6) | O4B—C9B—C10B—C11B | 178.3 (3) |
C4A—C5A—N1A—C1A | −2.1 (6) | C8B—C9B—C10B—C11B | −1.0 (5) |
C4A—C5A—N1A—C6A | 178.7 (4) | C9B—C10B—C11B—C12B | −0.4 (5) |
C2A—C1A—N1A—C5A | 0.3 (5) | C10B—C11B—C12B—C13B | 1.2 (5) |
C7A—C1A—N1A—C5A | 177.8 (4) | O3B—C8B—C13B—C12B | 178.8 (3) |
C2A—C1A—N1A—C6A | 179.5 (4) | C9B—C8B—C13B—C12B | −0.9 (5) |
C7A—C1A—N1A—C6A | −3.0 (5) | C11B—C12B—C13B—C8B | −0.6 (5) |
N1B—C1B—C2B—O1B | −177.3 (3) | C13C—C8C—C9C—C10C | 0.0 |
C7B—C1B—C2B—O1B | 1.1 (5) | O3C—C8C—C9C—C10C | −179.7 (7) |
N1B—C1B—C2B—C3B | −0.8 (5) | C8C—C9C—C10C—C11C | 0.0 |
C7B—C1B—C2B—C3B | 177.5 (3) | C9C—C10C—C11C—C12C | 0.0 |
O1B—C2B—C3B—O2B | 0.7 (5) | C10C—C11C—C12C—C13C | 0.0 |
C1B—C2B—C3B—O2B | −175.6 (3) | C11C—C12C—C13C—O4C | −179.1 (6) |
O1B—C2B—C3B—C4B | −179.7 (3) | C11C—C12C—C13C—C8C | 0.0 |
C1B—C2B—C3B—C4B | 4.0 (5) | C9C—C8C—C13C—O4C | 179.0 (7) |
O2B—C3B—C4B—C5B | 176.1 (3) | O3C—C8C—C13C—O4C | −1.3 (7) |
C2B—C3B—C4B—C5B | −3.5 (5) | C9C—C8C—C13C—C12C | 0.0 |
C3B—C4B—C5B—N1B | −0.2 (5) | O3C—C8C—C13C—C12C | 179.7 (6) |
C4B—C5B—N1B—C1B | 3.7 (5) | C13'—C8'—C9'—O4' | 178.4 (8) |
C4B—C5B—N1B—C6B | −177.5 (3) | O3'—C8'—C9'—O4' | 0.9 (9) |
C2B—C1B—N1B—C5B | −3.1 (5) | C13'—C8'—C9'—C10' | 0.0 |
C7B—C1B—N1B—C5B | 178.5 (3) | O3'—C8'—C9'—C10' | −177.5 (8) |
C2B—C1B—N1B—C6B | 178.1 (3) | O4'—C9'—C10'—C11' | −178.5 (8) |
C7B—C1B—N1B—C6B | −0.3 (5) | C8'—C9'—C10'—C11' | 0.0 |
O3A—C8A—C9A—O4A | 1.6 (5) | C9'—C10'—C11'—C12' | 0.0 |
C13A—C8A—C9A—O4A | −178.4 (3) | C10'—C11'—C12'—C13' | 0.0 |
O3A—C8A—C9A—C10A | 179.9 (3) | C11'—C12'—C13'—C8' | 0.0 |
C13A—C8A—C9A—C10A | 0.0 (5) | C9'—C8'—C13'—C12' | 0.0 |
O4A—C9A—C10A—C11A | 179.0 (3) | O3'—C8'—C13'—C12' | 177.3 (9) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O2B | 0.84 | 1.95 | 2.702 (3) | 148 |
O1B—H1B···O2A | 0.84 | 1.81 | 2.617 (4) | 161 |
O3A—H3A···O4A | 0.84 | 2.28 | 2.726 (3) | 113 |
O3A—H3A···O4B | 0.84 | 2.06 | 2.833 (4) | 153 |
O4A—H4A1···O2Bi | 0.84 | 1.88 | 2.702 (3) | 165 |
O3B—H3B···O4A | 0.84 | 2.11 | 2.849 (4) | 146 |
O3B—H3B···O4B | 0.84 | 2.26 | 2.719 (4) | 115 |
O4B—H4B1···O2B | 0.84 | 1.85 | 2.686 (3) | 175 |
O3Ca—H3Ca···O2A | 0.84 | 2.11 | 2.684 (6) | 125 |
O3′b—H3′b···O2A | 0.84 | 1.81 | 2.646 (7) | 174 |
O4′b—H4′b···O3′b | 0.84 | 2.30 | 2.715 (11) | 111 |
C5A—H5A···O1Ai | 0.95 | 2.42 | 3.164 (5) | 135 |
C4B—H4B···O4Aii | 0.95 | 2.56 | 3.223 (4) | 127 |
C5B—H5B···O1Bii | 0.95 | 2.43 | 3.159 (4) | 133 |
C10Ca—H10Ca···O4Cai | 0.95 | 2.37 | 3.112 (9) | 134 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |
(KA955_0m_def-cat_1_1_form1)
top
Crystal data top
C7H9NO2·C6H6O2 | Dx = 1.368 Mg m−3 |
Mr = 249.26 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 9084 reflections |
a = 9.4231 (1) Å | θ = 2.7–30.5° |
b = 10.3938 (1) Å | µ = 0.10 mm−1 |
c = 24.7171 (3) Å | T = 100 K |
V = 2420.84 (5) Å3 | Needle, colorless |
Z = 8 | 0.32 × 0.16 × 0.14 mm |
F(000) = 1056 | |
Data collection top
Bruker D8 QUEST PHOTON-100 diffractometer | 2970 reflections with I > 2σ(I) |
Radiation source: microfocus | Rint = 0.033 |
ω and φ scans | θmax = 30.6°, θmin = 2.7° |
Absorption correction: multi-scan SADABS, Bruker, 2016 | h = −10→13 |
Tmin = 0.695, Tmax = 0.746 | k = −11→14 |
16449 measured reflections | l = −35→34 |
3709 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.107 | w = 1/[σ2(Fo2) + (0.042P)2 + 1.3237P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
3709 reflections | Δρmax = 0.44 e Å−3 |
177 parameters | Δρmin = −0.26 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 | |
C1 | 0.66723 (13) | 0.96080 (10) | 0.55761 (4) | 0.0126 (2) | |
C2 | 0.70159 (12) | 0.94328 (10) | 0.50386 (4) | 0.0121 (2) | |
C3 | 0.62955 (13) | 0.85230 (10) | 0.47042 (4) | 0.0117 (2) | |
C4 | 0.52122 (13) | 0.78110 (10) | 0.49606 (5) | 0.0139 (2) | |
H4 | 0.469658 | 0.718666 | 0.476022 | 0.017* | |
C5 | 0.48954 (13) | 0.80096 (10) | 0.54951 (4) | 0.0139 (2) | |
H5 | 0.415861 | 0.752016 | 0.565773 | 0.017* | |
C6 | 0.51967 (14) | 0.90743 (12) | 0.63704 (4) | 0.0173 (2) | |
H6A | 0.483873 | 0.995152 | 0.642042 | 0.026* | |
H6B | 0.602676 | 0.894006 | 0.660251 | 0.026* | |
H6C | 0.445398 | 0.845602 | 0.646743 | 0.026* | |
C7 | 0.74235 (15) | 1.05827 (12) | 0.59171 (5) | 0.0195 (3) | |
H7A | 0.819646 | 1.097080 | 0.570794 | 0.029* | |
H7B | 0.781373 | 1.016220 | 0.623926 | 0.029* | |
H7C | 0.675255 | 1.125362 | 0.602738 | 0.029* | |
N1 | 0.56054 (11) | 0.88862 (9) | 0.57980 (4) | 0.0127 (2) | |
O1 | 0.80951 (10) | 1.01425 (8) | 0.48340 (3) | 0.0184 (2) | |
H1O | 0.8060 (19) | 1.0123 (17) | 0.4482 (7) | 0.031 (5)* | |
C8 | 0.93540 (13) | 1.08553 (10) | 0.34185 (4) | 0.0124 (2) | |
C9 | 0.94223 (13) | 0.96060 (10) | 0.32084 (4) | 0.0132 (2) | |
C10 | 1.04269 (14) | 0.93083 (12) | 0.28180 (5) | 0.0174 (2) | |
H10 | 1.048064 | 0.845799 | 0.267849 | 0.021* | |
C11 | 1.13542 (15) | 1.02439 (13) | 0.26296 (5) | 0.0209 (3) | |
H11 | 1.204309 | 1.003196 | 0.236352 | 0.025* | |
C12 | 1.12751 (15) | 1.14887 (13) | 0.28299 (5) | 0.0211 (3) | |
H12 | 1.190219 | 1.213222 | 0.269816 | 0.025* | |
C13 | 1.02741 (14) | 1.17936 (11) | 0.32246 (5) | 0.0175 (2) | |
H13 | 1.022025 | 1.264603 | 0.336171 | 0.021* | |
O2 | 0.66500 (10) | 0.83992 (7) | 0.42014 (3) | 0.01465 (18) | |
O3 | 0.83552 (10) | 1.10809 (8) | 0.38077 (3) | 0.01516 (18) | |
H3O | 0.843 (2) | 1.189 (2) | 0.3932 (8) | 0.051 (6)* | |
O4 | 0.85051 (10) | 0.86689 (8) | 0.33754 (3) | 0.01696 (19) | |
H4O | 0.797 (2) | 0.8911 (17) | 0.3634 (7) | 0.033 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0116 (6) | 0.0116 (5) | 0.0148 (5) | −0.0001 (4) | −0.0011 (4) | 0.0009 (4) |
C2 | 0.0106 (6) | 0.0104 (4) | 0.0154 (5) | −0.0012 (4) | −0.0009 (4) | 0.0017 (3) |
C3 | 0.0118 (6) | 0.0085 (4) | 0.0147 (5) | 0.0023 (4) | −0.0011 (4) | 0.0001 (3) |
C4 | 0.0125 (6) | 0.0114 (5) | 0.0177 (5) | −0.0013 (4) | −0.0011 (4) | −0.0004 (4) |
C5 | 0.0112 (6) | 0.0113 (5) | 0.0191 (5) | −0.0007 (4) | 0.0010 (4) | 0.0020 (4) |
C6 | 0.0185 (6) | 0.0196 (5) | 0.0137 (5) | −0.0015 (5) | 0.0039 (4) | 0.0014 (4) |
C7 | 0.0216 (7) | 0.0217 (6) | 0.0151 (5) | −0.0084 (5) | −0.0003 (5) | −0.0024 (4) |
N1 | 0.0125 (5) | 0.0119 (4) | 0.0137 (4) | 0.0008 (4) | 0.0007 (4) | 0.0022 (3) |
O1 | 0.0192 (5) | 0.0212 (4) | 0.0147 (4) | −0.0103 (4) | 0.0022 (3) | 0.0000 (3) |
C8 | 0.0126 (6) | 0.0135 (5) | 0.0112 (4) | 0.0017 (4) | 0.0000 (4) | 0.0008 (4) |
C9 | 0.0138 (6) | 0.0133 (5) | 0.0123 (4) | 0.0006 (4) | −0.0022 (4) | 0.0000 (4) |
C10 | 0.0176 (7) | 0.0206 (5) | 0.0140 (5) | 0.0044 (5) | −0.0014 (4) | −0.0042 (4) |
C11 | 0.0171 (7) | 0.0307 (7) | 0.0149 (5) | 0.0027 (5) | 0.0034 (5) | 0.0000 (4) |
C12 | 0.0180 (7) | 0.0250 (6) | 0.0204 (5) | −0.0025 (5) | 0.0023 (5) | 0.0053 (4) |
C13 | 0.0186 (7) | 0.0148 (5) | 0.0192 (5) | −0.0016 (5) | 0.0015 (5) | 0.0020 (4) |
O2 | 0.0188 (5) | 0.0115 (3) | 0.0137 (4) | −0.0017 (3) | 0.0014 (3) | −0.0012 (3) |
O3 | 0.0191 (5) | 0.0100 (4) | 0.0164 (4) | 0.0004 (3) | 0.0056 (3) | −0.0015 (3) |
O4 | 0.0206 (5) | 0.0115 (4) | 0.0188 (4) | −0.0015 (3) | 0.0046 (3) | −0.0025 (3) |
Geometric parameters (Å, º) top
C1—N1 | 1.3691 (15) | C7—H7C | 0.9800 |
C1—C2 | 1.3797 (15) | O1—H1O | 0.870 (17) |
C1—C7 | 1.4959 (16) | C8—O3 | 1.3660 (14) |
C2—O1 | 1.3542 (14) | C8—C13 | 1.3902 (16) |
C2—C3 | 1.4276 (15) | C8—C9 | 1.3999 (15) |
C3—O2 | 1.2933 (13) | C9—O4 | 1.3660 (14) |
C3—C4 | 1.4110 (16) | C9—C10 | 1.3868 (17) |
C4—C5 | 1.3700 (16) | C10—C11 | 1.3878 (18) |
C4—H4 | 0.9500 | C10—H10 | 0.9500 |
C5—N1 | 1.3559 (14) | C11—C12 | 1.3873 (19) |
C5—H5 | 0.9500 | C11—H11 | 0.9500 |
C6—N1 | 1.4792 (14) | C12—C13 | 1.3935 (18) |
C6—H6A | 0.9800 | C12—H12 | 0.9500 |
C6—H6B | 0.9800 | C13—H13 | 0.9500 |
C6—H6C | 0.9800 | O3—H3O | 0.90 (2) |
C7—H7A | 0.9800 | O4—H4O | 0.851 (19) |
C7—H7B | 0.9800 | | |
| | | |
N1—C1—C2 | 119.07 (10) | H7B—C7—H7C | 109.5 |
N1—C1—C7 | 119.53 (10) | C5—N1—C1 | 120.62 (9) |
C2—C1—C7 | 121.39 (10) | C5—N1—C6 | 119.25 (10) |
O1—C2—C1 | 117.64 (10) | C1—N1—C6 | 120.13 (10) |
O1—C2—C3 | 120.12 (10) | C2—O1—H1O | 109.3 (12) |
C1—C2—C3 | 122.23 (10) | O3—C8—C13 | 123.51 (10) |
O2—C3—C4 | 124.49 (10) | O3—C8—C9 | 116.88 (10) |
O2—C3—C2 | 119.96 (10) | C13—C8—C9 | 119.61 (11) |
C4—C3—C2 | 115.56 (10) | O4—C9—C10 | 118.88 (10) |
C5—C4—C3 | 120.77 (10) | O4—C9—C8 | 121.35 (10) |
C5—C4—H4 | 119.6 | C10—C9—C8 | 119.77 (11) |
C3—C4—H4 | 119.6 | C9—C10—C11 | 120.46 (11) |
N1—C5—C4 | 121.75 (11) | C9—C10—H10 | 119.8 |
N1—C5—H5 | 119.1 | C11—C10—H10 | 119.8 |
C4—C5—H5 | 119.1 | C12—C11—C10 | 120.00 (12) |
N1—C6—H6A | 109.5 | C12—C11—H11 | 120.0 |
N1—C6—H6B | 109.5 | C10—C11—H11 | 120.0 |
H6A—C6—H6B | 109.5 | C11—C12—C13 | 119.88 (12) |
N1—C6—H6C | 109.5 | C11—C12—H12 | 120.1 |
H6A—C6—H6C | 109.5 | C13—C12—H12 | 120.1 |
H6B—C6—H6C | 109.5 | C8—C13—C12 | 120.27 (11) |
C1—C7—H7A | 109.5 | C8—C13—H13 | 119.9 |
C1—C7—H7B | 109.5 | C12—C13—H13 | 119.9 |
H7A—C7—H7B | 109.5 | C8—O3—H3O | 110.2 (13) |
C1—C7—H7C | 109.5 | C9—O4—H4O | 112.9 (12) |
H7A—C7—H7C | 109.5 | | |
| | | |
N1—C1—C2—O1 | −178.68 (10) | C7—C1—N1—C5 | 179.06 (11) |
C7—C1—C2—O1 | 2.35 (16) | C2—C1—N1—C6 | −178.75 (10) |
N1—C1—C2—C3 | 0.04 (17) | C7—C1—N1—C6 | 0.24 (16) |
C7—C1—C2—C3 | −178.93 (11) | O3—C8—C9—O4 | 1.74 (16) |
O1—C2—C3—O2 | −1.74 (16) | C13—C8—C9—O4 | −177.78 (10) |
C1—C2—C3—O2 | 179.57 (10) | O3—C8—C9—C10 | −179.04 (10) |
O1—C2—C3—C4 | 178.45 (10) | C13—C8—C9—C10 | 1.44 (17) |
C1—C2—C3—C4 | −0.24 (16) | O4—C9—C10—C11 | 178.50 (11) |
O2—C3—C4—C5 | −179.45 (11) | C8—C9—C10—C11 | −0.74 (18) |
C2—C3—C4—C5 | 0.34 (16) | C9—C10—C11—C12 | −0.35 (19) |
C3—C4—C5—N1 | −0.26 (18) | C10—C11—C12—C13 | 0.7 (2) |
C4—C5—N1—C1 | 0.04 (17) | O3—C8—C13—C12 | 179.45 (11) |
C4—C5—N1—C6 | 178.86 (11) | C9—C8—C13—C12 | −1.06 (18) |
C2—C1—N1—C5 | 0.07 (16) | C11—C12—C13—C8 | −0.01 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O3 | 0.870 (17) | 1.963 (17) | 2.7289 (11) | 146.3 (16) |
O3—H3O···O2i | 0.90 (2) | 1.70 (2) | 2.5987 (11) | 172 (2) |
O4—H4O···O2 | 0.851 (19) | 1.950 (19) | 2.7024 (12) | 146.8 (17) |
C5—H5···O2ii | 0.95 | 2.57 | 3.4726 (15) | 158 |
C6—H6C···O4ii | 0.98 | 2.41 | 3.3264 (15) | 155 |
Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) x−1/2, −y+3/2, −z+1. |
(KA1027_0m_4def-cat_1_1_form2)
top
Crystal data top
C7H9NO2·C6H6O2 | F(000) = 528 |
Mr = 249.26 | Dx = 1.374 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.867 (3) Å | Cell parameters from 6762 reflections |
b = 9.550 (2) Å | θ = 2.7–30.7° |
c = 10.487 (2) Å | µ = 0.10 mm−1 |
β = 110.761 (7)° | T = 100 K |
V = 1205.1 (5) Å3 | Block, colorless |
Z = 4 | 0.26 × 0.24 × 0.18 mm |
Data collection top
Bruker D8 QUEST PHOTON-100 diffractometer | 2125 measured reflections |
Radiation source: microfocus | 2125 independent reflections |
ω and φ scans | 1755 reflections with I > 2σ(I) |
Absorption correction: multi-scan SADABS, Bruker, 2016 | Rint = 0.071 |
Tmin = 0.686, Tmax = 0.746 | θmax = 25.0°, θmin = 2.7° |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.086 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.203 | w = 1/[σ2(Fo2) + (0.041P)2 + 5.1435P] where P = (Fo2 + 2Fc2)/3 |
S = 1.25 | (Δ/σ)max < 0.001 |
2125 reflections | Δρmax = 0.38 e Å−3 |
177 parameters | Δρmin = −0.38 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 | |
C1 | 0.6092 (3) | 0.1664 (4) | 1.0866 (4) | 0.0153 (9) | |
C2 | 0.4997 (3) | 0.2036 (4) | 1.0566 (4) | 0.0146 (9) | |
C3 | 0.4313 (3) | 0.1361 (4) | 1.1195 (4) | 0.0149 (9) | |
C4 | 0.4823 (3) | 0.0299 (4) | 1.2123 (4) | 0.0172 (9) | |
H4 | 0.440667 | −0.018518 | 1.257328 | 0.021* | |
C5 | 0.5908 (3) | −0.0053 (4) | 1.2395 (4) | 0.0160 (9) | |
H5 | 0.623165 | −0.078582 | 1.302291 | 0.019* | |
C6 | 0.7707 (3) | 0.0197 (5) | 1.2108 (4) | 0.0196 (10) | |
H6A | 0.779711 | −0.020463 | 1.129388 | 0.029* | |
H6B | 0.790890 | −0.050254 | 1.283867 | 0.029* | |
H6C | 0.818976 | 0.101786 | 1.240608 | 0.029* | |
C7 | 0.6800 (4) | 0.2378 (5) | 1.0204 (5) | 0.0259 (11) | |
H7A | 0.635731 | 0.308211 | 0.955960 | 0.039* | |
H7B | 0.707886 | 0.168534 | 0.971404 | 0.039* | |
H7C | 0.742808 | 0.283428 | 1.090196 | 0.039* | |
O1 | 0.4587 (3) | 0.3097 (3) | 0.9670 (3) | 0.0241 (8) | |
H1O | 0.391 (7) | 0.310 (8) | 0.945 (8) | 0.08 (3)* | |
O2 | 0.3284 (2) | 0.1748 (3) | 1.0879 (3) | 0.0179 (7) | |
N1 | 0.6534 (3) | 0.0623 (4) | 1.1784 (3) | 0.0160 (8) | |
C8 | 0.1729 (3) | 0.4424 (4) | 0.7692 (4) | 0.0143 (9) | |
C9 | 0.1345 (3) | 0.4598 (4) | 0.8763 (4) | 0.0155 (9) | |
C10 | 0.0592 (4) | 0.5661 (5) | 0.8703 (5) | 0.0207 (10) | |
H10 | 0.033708 | 0.579797 | 0.943963 | 0.025* | |
C11 | 0.0218 (4) | 0.6513 (5) | 0.7578 (5) | 0.0229 (10) | |
H11 | −0.029763 | 0.723678 | 0.754502 | 0.027* | |
C12 | 0.0577 (4) | 0.6336 (5) | 0.6491 (5) | 0.0241 (10) | |
H12 | 0.030612 | 0.692229 | 0.571093 | 0.029* | |
C13 | 0.1347 (4) | 0.5276 (5) | 0.6565 (4) | 0.0214 (10) | |
H13 | 0.160714 | 0.514500 | 0.583096 | 0.026* | |
O3 | 0.2485 (2) | 0.3362 (3) | 0.7826 (3) | 0.0172 (7) | |
H3O | 0.268 (4) | 0.343 (5) | 0.704 (5) | 0.017 (12)* | |
O4 | 0.1675 (3) | 0.3741 (3) | 0.9884 (3) | 0.0216 (7) | |
H4O | 0.211 (6) | 0.305 (7) | 0.975 (7) | 0.06 (2)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.016 (2) | 0.014 (2) | 0.011 (2) | −0.0016 (16) | −0.0002 (16) | 0.0009 (16) |
C2 | 0.014 (2) | 0.014 (2) | 0.012 (2) | −0.0004 (16) | 0.0005 (16) | 0.0005 (16) |
C3 | 0.019 (2) | 0.015 (2) | 0.0070 (19) | 0.0001 (16) | 0.0000 (16) | −0.0030 (16) |
C4 | 0.022 (2) | 0.017 (2) | 0.014 (2) | −0.0007 (17) | 0.0073 (18) | 0.0004 (16) |
C5 | 0.023 (2) | 0.014 (2) | 0.0073 (19) | 0.0030 (17) | 0.0003 (17) | 0.0020 (16) |
C6 | 0.011 (2) | 0.024 (2) | 0.019 (2) | 0.0043 (17) | −0.0002 (17) | 0.0017 (18) |
C7 | 0.016 (2) | 0.026 (2) | 0.030 (3) | 0.0024 (19) | 0.0015 (19) | 0.013 (2) |
O1 | 0.0136 (16) | 0.0263 (18) | 0.0299 (18) | 0.0051 (13) | 0.0045 (14) | 0.0164 (14) |
O2 | 0.0145 (15) | 0.0213 (16) | 0.0161 (15) | 0.0038 (12) | 0.0033 (12) | 0.0035 (12) |
N1 | 0.0134 (18) | 0.0158 (18) | 0.0147 (18) | 0.0017 (14) | −0.0002 (14) | −0.0002 (14) |
C8 | 0.0069 (19) | 0.017 (2) | 0.015 (2) | −0.0021 (15) | −0.0008 (16) | −0.0020 (16) |
C9 | 0.014 (2) | 0.015 (2) | 0.013 (2) | −0.0053 (16) | −0.0004 (16) | −0.0028 (16) |
C10 | 0.018 (2) | 0.019 (2) | 0.026 (2) | −0.0004 (17) | 0.0094 (19) | −0.0025 (19) |
C11 | 0.017 (2) | 0.018 (2) | 0.031 (3) | 0.0035 (17) | 0.0053 (19) | 0.0012 (19) |
C12 | 0.021 (2) | 0.019 (2) | 0.026 (2) | 0.0024 (18) | 0.0006 (19) | 0.0070 (19) |
C13 | 0.020 (2) | 0.024 (2) | 0.019 (2) | −0.0009 (18) | 0.0048 (18) | 0.0010 (18) |
O3 | 0.0180 (15) | 0.0191 (16) | 0.0134 (15) | 0.0055 (12) | 0.0042 (12) | 0.0022 (12) |
O4 | 0.0244 (17) | 0.0248 (17) | 0.0153 (16) | 0.0075 (14) | 0.0064 (13) | 0.0041 (13) |
Geometric parameters (Å, º) top
C1—N1 | 1.361 (5) | C7—H7C | 0.9800 |
C1—C2 | 1.378 (6) | O1—H1O | 0.82 (8) |
C1—C7 | 1.491 (6) | C8—C13 | 1.375 (6) |
C2—O1 | 1.355 (5) | C8—O3 | 1.377 (5) |
C2—C3 | 1.427 (6) | C8—C9 | 1.388 (6) |
C3—O2 | 1.299 (5) | C9—O4 | 1.370 (5) |
C3—C4 | 1.398 (6) | C9—C10 | 1.389 (6) |
C4—C5 | 1.365 (6) | C10—C11 | 1.372 (6) |
C4—H4 | 0.9500 | C10—H10 | 0.9500 |
C5—N1 | 1.357 (5) | C11—C12 | 1.384 (7) |
C5—H5 | 0.9500 | C11—H11 | 0.9500 |
C6—N1 | 1.481 (5) | C12—C13 | 1.399 (6) |
C6—H6A | 0.9800 | C12—H12 | 0.9500 |
C6—H6B | 0.9800 | C13—H13 | 0.9500 |
C6—H6C | 0.9800 | O3—H3O | 0.95 (5) |
C7—H7A | 0.9800 | O4—H4O | 0.91 (7) |
C7—H7B | 0.9800 | | |
| | | |
N1—C1—C2 | 119.2 (4) | H7B—C7—H7C | 109.5 |
N1—C1—C7 | 119.5 (4) | C2—O1—H1O | 108 (6) |
C2—C1—C7 | 121.3 (4) | C5—N1—C1 | 120.8 (3) |
O1—C2—C1 | 117.8 (4) | C5—N1—C6 | 119.2 (3) |
O1—C2—C3 | 120.4 (4) | C1—N1—C6 | 120.0 (4) |
C1—C2—C3 | 121.8 (4) | C13—C8—O3 | 123.2 (4) |
O2—C3—C4 | 124.6 (4) | C13—C8—C9 | 120.2 (4) |
O2—C3—C2 | 119.6 (4) | O3—C8—C9 | 116.5 (4) |
C4—C3—C2 | 115.8 (4) | O4—C9—C8 | 122.1 (4) |
C5—C4—C3 | 121.1 (4) | O4—C9—C10 | 118.4 (4) |
C5—C4—H4 | 119.4 | C8—C9—C10 | 119.5 (4) |
C3—C4—H4 | 119.4 | C11—C10—C9 | 120.0 (4) |
N1—C5—C4 | 121.3 (4) | C11—C10—H10 | 120.0 |
N1—C5—H5 | 119.4 | C9—C10—H10 | 120.0 |
C4—C5—H5 | 119.4 | C10—C11—C12 | 121.2 (4) |
N1—C6—H6A | 109.5 | C10—C11—H11 | 119.4 |
N1—C6—H6B | 109.5 | C12—C11—H11 | 119.4 |
H6A—C6—H6B | 109.5 | C11—C12—C13 | 118.7 (4) |
N1—C6—H6C | 109.5 | C11—C12—H12 | 120.7 |
H6A—C6—H6C | 109.5 | C13—C12—H12 | 120.7 |
H6B—C6—H6C | 109.5 | C8—C13—C12 | 120.4 (4) |
C1—C7—H7A | 109.5 | C8—C13—H13 | 119.8 |
C1—C7—H7B | 109.5 | C12—C13—H13 | 119.8 |
H7A—C7—H7B | 109.5 | C8—O3—H3O | 105 (3) |
C1—C7—H7C | 109.5 | C9—O4—H4O | 109 (4) |
H7A—C7—H7C | 109.5 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O2 | 0.82 (8) | 2.33 (8) | 2.754 (4) | 113 (6) |
O1—H1O···O3 | 0.82 (8) | 2.03 (8) | 2.723 (4) | 142 (7) |
O3—H3O···O2i | 0.95 (5) | 1.67 (5) | 2.594 (4) | 165 (4) |
O4—H4O···O2 | 0.91 (7) | 1.99 (7) | 2.732 (4) | 138 (6) |
O4—H4O···O3 | 0.91 (7) | 2.26 (7) | 2.733 (4) | 112 (5) |
C5—H5···O2ii | 0.95 | 2.60 | 3.516 (5) | 162 |
C6—H6B···O4ii | 0.98 | 2.37 | 3.277 (5) | 154 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, y−1/2, −z+5/2. |
(KA254_0M_def-hq_1_0.5)
top
Crystal data top
C7H9NO2·0.5(C6H6O2) | Z = 2 |
Mr = 194.21 | F(000) = 206 |
Triclinic, P1 | Dx = 1.450 Mg m−3 |
a = 6.83171 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.09634 (10) Å | Cell parameters from 8964 reflections |
c = 10.01294 (14) Å | θ = 3.1–30.5° |
α = 72.4243 (4)° | µ = 0.11 mm−1 |
β = 85.7351 (4)° | T = 100 K |
γ = 73.9285 (4)° | Block, colorless |
V = 444.66 (1) Å3 | 0.41 × 0.38 × 0.22 mm |
Data collection top
Bruker D8 QUEST PHOTON-100 diffractometer | 2471 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.024 |
Absorption correction: multi-scan SADABS, Bruker,2016 | θmax = 30.5°, θmin = 2.1° |
Tmin = 0.719, Tmax = 0.746 | h = −8→9 |
11173 measured reflections | k = −9→10 |
2708 independent reflections | l = −14→14 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.0512P)2 + 0.1917P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
2708 reflections | Δρmax = 0.45 e Å−3 |
137 parameters | Δρmin = −0.26 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 | |
C1 | 1.06764 (12) | 0.64378 (13) | 0.60013 (8) | 0.00925 (16) | |
C2 | 0.86615 (13) | 0.75480 (13) | 0.57949 (8) | 0.00904 (16) | |
C3 | 0.71807 (12) | 0.73275 (13) | 0.68833 (9) | 0.00915 (16) | |
C4 | 0.79096 (13) | 0.58247 (13) | 0.81665 (9) | 0.01072 (16) | |
H4 | 0.6997 | 0.5572 | 0.8922 | 0.013* | |
C5 | 0.99177 (13) | 0.47335 (13) | 0.83276 (9) | 0.01053 (16) | |
H5 | 1.0366 | 0.3727 | 0.9195 | 0.013* | |
C6 | 1.34255 (13) | 0.38421 (14) | 0.75540 (10) | 0.01397 (18) | |
H6A | 1.3790 | 0.2921 | 0.6963 | 0.021* | |
H6B | 1.3606 | 0.3031 | 0.8542 | 0.021* | |
H6C | 1.4306 | 0.4774 | 0.7333 | 0.021* | |
C7 | 1.22236 (13) | 0.66929 (14) | 0.48694 (9) | 0.01321 (17) | |
H7A | 1.1544 | 0.7622 | 0.3994 | 0.020* | |
H7B | 1.2910 | 0.5355 | 0.4736 | 0.020* | |
H7C | 1.3229 | 0.7270 | 0.5137 | 0.020* | |
N1 | 1.12814 (11) | 0.50447 (11) | 0.72884 (8) | 0.00952 (15) | |
O1 | 0.80721 (10) | 0.88597 (10) | 0.45067 (7) | 0.01354 (15) | |
H1O | 0.677 (3) | 0.949 (3) | 0.452 (2) | 0.052 (6)* | |
O2 | 0.53234 (10) | 0.84161 (10) | 0.66573 (7) | 0.01308 (15) | |
C8 | 0.20047 (12) | 0.92636 (13) | 0.95892 (8) | 0.00975 (16) | |
C9 | 0.03678 (13) | 0.95351 (13) | 0.87318 (8) | 0.01011 (16) | |
H9 | 0.0612 | 0.9223 | 0.7866 | 0.012* | |
C10 | −0.16245 (13) | 1.02634 (13) | 0.91429 (9) | 0.01028 (16) | |
H10 | −0.2732 | 1.0439 | 0.8556 | 0.012* | |
O3 | 0.39904 (10) | 0.85127 (11) | 0.92593 (7) | 0.01518 (15) | |
H2O | 0.412 (3) | 0.851 (3) | 0.840 (2) | 0.041 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0085 (3) | 0.0101 (3) | 0.0085 (3) | −0.0019 (3) | 0.0000 (3) | −0.0023 (3) |
C2 | 0.0091 (3) | 0.0099 (3) | 0.0071 (3) | −0.0017 (3) | −0.0001 (3) | −0.0017 (3) |
C3 | 0.0080 (3) | 0.0105 (3) | 0.0086 (3) | −0.0018 (3) | 0.0002 (3) | −0.0030 (3) |
C4 | 0.0095 (4) | 0.0124 (4) | 0.0086 (3) | −0.0021 (3) | 0.0011 (3) | −0.0016 (3) |
C5 | 0.0109 (4) | 0.0102 (3) | 0.0085 (3) | −0.0017 (3) | 0.0000 (3) | −0.0009 (3) |
C6 | 0.0075 (4) | 0.0154 (4) | 0.0147 (4) | 0.0010 (3) | −0.0016 (3) | −0.0015 (3) |
C7 | 0.0094 (4) | 0.0164 (4) | 0.0116 (4) | −0.0024 (3) | 0.0028 (3) | −0.0026 (3) |
N1 | 0.0073 (3) | 0.0101 (3) | 0.0094 (3) | −0.0006 (2) | −0.0007 (2) | −0.0018 (2) |
O1 | 0.0097 (3) | 0.0168 (3) | 0.0077 (3) | 0.0014 (2) | −0.0002 (2) | 0.0013 (2) |
O2 | 0.0074 (3) | 0.0167 (3) | 0.0104 (3) | 0.0012 (2) | −0.0004 (2) | −0.0011 (2) |
C8 | 0.0077 (3) | 0.0102 (3) | 0.0091 (3) | −0.0008 (3) | 0.0020 (3) | −0.0014 (3) |
C9 | 0.0108 (4) | 0.0109 (4) | 0.0076 (3) | −0.0021 (3) | 0.0011 (3) | −0.0021 (3) |
C10 | 0.0092 (4) | 0.0117 (4) | 0.0085 (3) | −0.0018 (3) | −0.0002 (3) | −0.0018 (3) |
O3 | 0.0075 (3) | 0.0232 (3) | 0.0116 (3) | 0.0012 (2) | 0.0023 (2) | −0.0057 (3) |
Geometric parameters (Å, º) top
C1—N1 | 1.3757 (10) | C6—H6C | 0.9800 |
C1—C2 | 1.3790 (11) | C7—H7A | 0.9800 |
C1—C7 | 1.4961 (12) | C7—H7B | 0.9800 |
C2—O1 | 1.3554 (10) | C7—H7C | 0.9800 |
C2—C3 | 1.4339 (11) | O1—H1O | 0.88 (2) |
C3—O2 | 1.2855 (10) | C8—O3 | 1.3685 (10) |
C3—C4 | 1.4177 (11) | C8—C9 | 1.3959 (12) |
C4—C5 | 1.3700 (11) | C8—C10i | 1.3971 (12) |
C4—H4 | 0.9500 | C9—C10 | 1.3946 (11) |
C5—N1 | 1.3529 (11) | C9—H9 | 0.9500 |
C5—H5 | 0.9500 | C10—C8i | 1.3970 (12) |
C6—N1 | 1.4742 (11) | C10—H10 | 0.9500 |
C6—H6A | 0.9800 | O3—H2O | 0.86 (2) |
C6—H6B | 0.9800 | | |
| | | |
N1—C1—C2 | 118.91 (8) | C1—C7—H7A | 109.5 |
N1—C1—C7 | 118.94 (7) | C1—C7—H7B | 109.5 |
C2—C1—C7 | 122.15 (7) | H7A—C7—H7B | 109.5 |
O1—C2—C1 | 118.26 (7) | C1—C7—H7C | 109.5 |
O1—C2—C3 | 119.45 (7) | H7A—C7—H7C | 109.5 |
C1—C2—C3 | 122.28 (8) | H7B—C7—H7C | 109.5 |
O2—C3—C4 | 124.12 (8) | C5—N1—C1 | 120.70 (7) |
O2—C3—C2 | 120.44 (8) | C5—N1—C6 | 118.77 (7) |
C4—C3—C2 | 115.42 (7) | C1—N1—C6 | 120.53 (7) |
C5—C4—C3 | 120.61 (8) | C2—O1—H1O | 109.2 (13) |
C5—C4—H4 | 119.7 | O3—C8—C9 | 122.95 (8) |
C3—C4—H4 | 119.7 | O3—C8—C10i | 117.73 (8) |
N1—C5—C4 | 122.01 (8) | C9—C8—C10i | 119.31 (7) |
N1—C5—H5 | 119.0 | C10—C9—C8 | 120.17 (7) |
C4—C5—H5 | 119.0 | C10—C9—H9 | 119.9 |
N1—C6—H6A | 109.5 | C8—C9—H9 | 119.9 |
N1—C6—H6B | 109.5 | C9—C10—C8i | 120.52 (8) |
H6A—C6—H6B | 109.5 | C9—C10—H10 | 119.7 |
N1—C6—H6C | 109.5 | C8i—C10—H10 | 119.7 |
H6A—C6—H6C | 109.5 | C8—O3—H2O | 112.1 (12) |
H6B—C6—H6C | 109.5 | | |
| | | |
N1—C1—C2—O1 | −177.62 (7) | C3—C4—C5—N1 | 0.48 (14) |
C7—C1—C2—O1 | 2.13 (13) | C4—C5—N1—C1 | −2.23 (13) |
N1—C1—C2—C3 | 1.13 (13) | C4—C5—N1—C6 | 178.60 (8) |
C7—C1—C2—C3 | −179.13 (8) | C2—C1—N1—C5 | 1.40 (12) |
O1—C2—C3—O2 | −2.48 (13) | C7—C1—N1—C5 | −178.35 (8) |
C1—C2—C3—O2 | 178.79 (8) | C2—C1—N1—C6 | −179.45 (8) |
O1—C2—C3—C4 | 176.02 (7) | C7—C1—N1—C6 | 0.80 (12) |
C1—C2—C3—C4 | −2.71 (12) | O3—C8—C9—C10 | 178.52 (8) |
O2—C3—C4—C5 | −179.66 (8) | C10i—C8—C9—C10 | −0.26 (14) |
C2—C3—C4—C5 | 1.90 (12) | C8—C9—C10—C8i | 0.26 (14) |
Symmetry code: (i) −x, −y+2, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O2ii | 0.88 (2) | 1.91 (2) | 2.6523 (9) | 140.7 (18) |
O3—H2O···O2 | 0.86 (2) | 1.88 (2) | 2.7097 (9) | 160.6 (18) |
C4—H4···O3 | 0.95 | 2.58 | 3.1625 (11) | 120 |
C7—H7C···O2iii | 0.98 | 2.60 | 3.5361 (12) | 161 |
C9—H9···O1ii | 0.95 | 2.59 | 3.2978 (10) | 132 |
Symmetry codes: (ii) −x+1, −y+2, −z+1; (iii) x+1, y, z. |
(KA951_0mdef-res_2_1)
top
Crystal data top
2(C7H9NO2)·C6H6O2 | F(000) = 824 |
Mr = 388.41 | Dx = 1.385 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.71471 (15) Å | Cell parameters from 7177 reflections |
b = 7.32566 (10) Å | θ = 2.6–30.5° |
c = 22.0867 (3) Å | µ = 0.10 mm−1 |
β = 100.6076 (7)° | T = 100 K |
V = 1863.04 (4) Å3 | Block, colorless |
Z = 4 | 0.36 × 0.28 × 0.18 mm |
Data collection top
Bruker D8 QUEST PHOTON-100 diffractometer | 4023 reflections with I > 2σ(I) |
Radiation source: microfocus | Rint = 0.051 |
ω and φ scans | θmax = 30.5°, θmin = 2.2° |
Absorption correction: multi-scan SADABS, Bruker, 2016 | h = −15→16 |
Tmin = 0.570, Tmax = 0.746 | k = −10→10 |
16659 measured reflections | l = −31→31 |
5665 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.054 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.0401P)2 + 1.3362P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
5665 reflections | Δρmax = 0.35 e Å−3 |
273 parameters | Δρmin = −0.40 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 | |
C1A | 0.00048 (13) | 0.7409 (2) | 0.79773 (7) | 0.0136 (3) | |
C2A | 0.02881 (12) | 0.7559 (2) | 0.74009 (7) | 0.0125 (3) | |
C3A | 0.13876 (13) | 0.6954 (2) | 0.72806 (7) | 0.0126 (3) | |
C4A | 0.21768 (13) | 0.6298 (2) | 0.77945 (7) | 0.0149 (3) | |
H4A | 0.292429 | 0.589378 | 0.774412 | 0.018* | |
C5A | 0.18797 (13) | 0.6235 (2) | 0.83641 (7) | 0.0162 (3) | |
H5A | 0.242986 | 0.579842 | 0.870381 | 0.019* | |
C6A | 0.05466 (15) | 0.6591 (2) | 0.90774 (7) | 0.0196 (3) | |
H6A | 0.000468 | 0.557440 | 0.908146 | 0.029* | |
H6B | 0.018974 | 0.772256 | 0.918922 | 0.029* | |
H6C | 0.126136 | 0.635299 | 0.937474 | 0.029* | |
C7A | −0.11812 (14) | 0.7897 (2) | 0.80881 (7) | 0.0186 (3) | |
H7A | −0.169401 | 0.814112 | 0.769332 | 0.028* | |
H7B | −0.113139 | 0.898787 | 0.834833 | 0.028* | |
H7C | −0.149443 | 0.687982 | 0.829518 | 0.028* | |
N1A | 0.08235 (11) | 0.67786 (18) | 0.84561 (6) | 0.0138 (3) | |
O1A | −0.05101 (10) | 0.82944 (17) | 0.69425 (5) | 0.0186 (3) | |
H1O | −0.039 (2) | 0.801 (3) | 0.6575 (12) | 0.046 (7)* | |
O2A | 0.16024 (9) | 0.70137 (16) | 0.67308 (5) | 0.0153 (2) | |
C1B | 0.10296 (13) | 0.7833 (2) | 0.46944 (7) | 0.0132 (3) | |
C2B | 0.05680 (13) | 0.8045 (2) | 0.52196 (7) | 0.0118 (3) | |
C3B | −0.05645 (12) | 0.7385 (2) | 0.52614 (7) | 0.0116 (3) | |
C4B | −0.11969 (13) | 0.6579 (2) | 0.47199 (7) | 0.0130 (3) | |
H4B | −0.195888 | 0.612945 | 0.471623 | 0.016* | |
C5B | −0.07202 (13) | 0.6442 (2) | 0.42039 (7) | 0.0138 (3) | |
H5B | −0.116342 | 0.590157 | 0.384528 | 0.017* | |
C6B | 0.08152 (16) | 0.6835 (2) | 0.36112 (8) | 0.0210 (4) | |
H6D | 0.023032 | 0.623332 | 0.330086 | 0.032* | |
H6E | 0.152148 | 0.608886 | 0.369076 | 0.032* | |
H6F | 0.099681 | 0.803789 | 0.345985 | 0.032* | |
C7B | 0.22516 (14) | 0.8381 (2) | 0.46654 (8) | 0.0200 (3) | |
H7D | 0.224097 | 0.937097 | 0.436599 | 0.030* | |
H7E | 0.266981 | 0.733083 | 0.453876 | 0.030* | |
H7F | 0.264275 | 0.879915 | 0.507242 | 0.030* | |
N1B | 0.03605 (11) | 0.70498 (18) | 0.41845 (6) | 0.0135 (3) | |
O1B | 0.12117 (9) | 0.89164 (16) | 0.57104 (5) | 0.0160 (2) | |
H2O | 0.118 (2) | 0.837 (3) | 0.6070 (12) | 0.044 (7)* | |
O2B | −0.09658 (9) | 0.75194 (16) | 0.57650 (5) | 0.0148 (2) | |
C8 | 0.43028 (13) | 0.6596 (2) | 0.62482 (7) | 0.0132 (3) | |
C9 | 0.49976 (13) | 0.6426 (2) | 0.58025 (7) | 0.0140 (3) | |
H9 | 0.468191 | 0.593785 | 0.540871 | 0.017* | |
C10 | 0.61549 (13) | 0.6972 (2) | 0.59351 (7) | 0.0132 (3) | |
C11 | 0.66151 (13) | 0.7753 (2) | 0.65022 (7) | 0.0145 (3) | |
H11 | 0.740060 | 0.814780 | 0.659066 | 0.017* | |
C12 | 0.59007 (13) | 0.7942 (2) | 0.69370 (7) | 0.0150 (3) | |
H12 | 0.620756 | 0.847754 | 0.732450 | 0.018* | |
C13 | 0.47511 (13) | 0.7369 (2) | 0.68191 (7) | 0.0144 (3) | |
H13 | 0.427811 | 0.750170 | 0.712255 | 0.017* | |
O3 | 0.31994 (9) | 0.59454 (17) | 0.61019 (5) | 0.0184 (3) | |
H3O | 0.278 (2) | 0.631 (4) | 0.6371 (12) | 0.049 (7)* | |
O4 | 0.68062 (10) | 0.66889 (17) | 0.54920 (5) | 0.0192 (3) | |
H4O | 0.754 (2) | 0.702 (3) | 0.5626 (10) | 0.030 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.0123 (7) | 0.0151 (7) | 0.0130 (7) | 0.0002 (6) | 0.0012 (5) | −0.0021 (6) |
C2A | 0.0099 (7) | 0.0144 (7) | 0.0125 (7) | 0.0011 (5) | 0.0003 (5) | −0.0015 (5) |
C3A | 0.0114 (7) | 0.0117 (7) | 0.0146 (7) | −0.0019 (5) | 0.0020 (5) | −0.0009 (5) |
C4A | 0.0101 (7) | 0.0160 (7) | 0.0183 (8) | 0.0013 (6) | 0.0014 (5) | 0.0015 (6) |
C5A | 0.0148 (7) | 0.0152 (7) | 0.0167 (7) | 0.0007 (6) | −0.0022 (6) | 0.0027 (6) |
C6A | 0.0268 (9) | 0.0219 (8) | 0.0106 (7) | 0.0001 (7) | 0.0049 (6) | 0.0016 (6) |
C7A | 0.0156 (7) | 0.0270 (9) | 0.0140 (7) | 0.0018 (7) | 0.0050 (6) | −0.0032 (6) |
N1A | 0.0151 (6) | 0.0150 (6) | 0.0110 (6) | −0.0012 (5) | 0.0019 (5) | 0.0005 (5) |
O1A | 0.0138 (5) | 0.0311 (7) | 0.0103 (5) | 0.0092 (5) | 0.0006 (4) | −0.0012 (5) |
O2A | 0.0128 (5) | 0.0211 (6) | 0.0126 (5) | 0.0013 (4) | 0.0045 (4) | −0.0001 (4) |
C1B | 0.0118 (7) | 0.0124 (7) | 0.0158 (7) | −0.0003 (5) | 0.0037 (5) | 0.0028 (6) |
C2B | 0.0118 (7) | 0.0103 (7) | 0.0129 (7) | −0.0002 (5) | 0.0011 (5) | 0.0000 (5) |
C3B | 0.0102 (6) | 0.0120 (7) | 0.0128 (7) | 0.0021 (5) | 0.0024 (5) | 0.0011 (5) |
C4B | 0.0113 (7) | 0.0136 (7) | 0.0140 (7) | −0.0014 (5) | 0.0024 (5) | −0.0002 (6) |
C5B | 0.0145 (7) | 0.0137 (7) | 0.0132 (7) | −0.0007 (6) | 0.0024 (5) | −0.0005 (6) |
C6B | 0.0253 (9) | 0.0252 (9) | 0.0158 (8) | −0.0027 (7) | 0.0123 (6) | −0.0024 (6) |
C7B | 0.0138 (7) | 0.0244 (9) | 0.0235 (8) | −0.0026 (6) | 0.0081 (6) | 0.0023 (7) |
N1B | 0.0156 (6) | 0.0136 (6) | 0.0130 (6) | −0.0004 (5) | 0.0069 (5) | −0.0004 (5) |
O1B | 0.0153 (5) | 0.0186 (6) | 0.0128 (5) | −0.0054 (4) | −0.0005 (4) | −0.0003 (4) |
O2B | 0.0128 (5) | 0.0226 (6) | 0.0097 (5) | 0.0000 (4) | 0.0035 (4) | −0.0014 (4) |
C8 | 0.0095 (7) | 0.0135 (7) | 0.0171 (7) | −0.0002 (5) | 0.0033 (5) | −0.0004 (6) |
C9 | 0.0125 (7) | 0.0168 (7) | 0.0126 (7) | 0.0003 (6) | 0.0023 (5) | −0.0023 (6) |
C10 | 0.0132 (7) | 0.0159 (7) | 0.0119 (7) | 0.0009 (6) | 0.0059 (5) | 0.0008 (6) |
C11 | 0.0104 (7) | 0.0178 (8) | 0.0156 (7) | −0.0019 (6) | 0.0035 (5) | −0.0001 (6) |
C12 | 0.0140 (7) | 0.0190 (8) | 0.0120 (7) | −0.0015 (6) | 0.0026 (5) | −0.0031 (6) |
C13 | 0.0133 (7) | 0.0179 (8) | 0.0135 (7) | −0.0003 (6) | 0.0066 (5) | −0.0019 (6) |
O3 | 0.0089 (5) | 0.0253 (6) | 0.0221 (6) | −0.0032 (5) | 0.0059 (4) | −0.0083 (5) |
O4 | 0.0110 (5) | 0.0328 (7) | 0.0156 (5) | −0.0026 (5) | 0.0072 (4) | −0.0048 (5) |
Geometric parameters (Å, º) top
C1A—N1A | 1.3705 (19) | C4B—C5B | 1.362 (2) |
C1A—C2A | 1.378 (2) | C4B—H4B | 0.9500 |
C1A—C7A | 1.498 (2) | C5B—N1B | 1.3500 (19) |
C2A—O1A | 1.3570 (18) | C5B—H5B | 0.9500 |
C2A—C3A | 1.433 (2) | C6B—N1B | 1.4697 (19) |
C3A—O2A | 1.2852 (18) | C6B—H6D | 0.9800 |
C3A—C4A | 1.410 (2) | C6B—H6E | 0.9800 |
C4A—C5A | 1.367 (2) | C6B—H6F | 0.9800 |
C4A—H4A | 0.9500 | C7B—H7D | 0.9800 |
C5A—N1A | 1.350 (2) | C7B—H7E | 0.9800 |
C5A—H5A | 0.9500 | C7B—H7F | 0.9800 |
C6A—N1A | 1.4734 (19) | O1B—H2O | 0.90 (2) |
C6A—H6A | 0.9800 | C8—O3 | 1.3596 (18) |
C6A—H6B | 0.9800 | C8—C9 | 1.394 (2) |
C6A—H6C | 0.9800 | C8—C13 | 1.394 (2) |
C7A—H7A | 0.9800 | C9—C10 | 1.392 (2) |
C7A—H7B | 0.9800 | C9—H9 | 0.9500 |
C7A—H7C | 0.9800 | C10—O4 | 1.3630 (17) |
O1A—H1O | 0.87 (3) | C10—C11 | 1.392 (2) |
C1B—N1B | 1.374 (2) | C11—C12 | 1.392 (2) |
C1B—C2B | 1.376 (2) | C11—H11 | 0.9500 |
C1B—C7B | 1.499 (2) | C12—C13 | 1.389 (2) |
C2B—O1B | 1.3603 (18) | C12—H12 | 0.9500 |
C2B—C3B | 1.431 (2) | C13—H13 | 0.9500 |
C3B—O2B | 1.2886 (17) | O3—H3O | 0.88 (3) |
C3B—C4B | 1.415 (2) | O4—H4O | 0.89 (2) |
| | | |
N1A—C1A—C2A | 119.10 (13) | C5B—C4B—H4B | 119.8 |
N1A—C1A—C7A | 119.53 (13) | C3B—C4B—H4B | 119.8 |
C2A—C1A—C7A | 121.37 (14) | N1B—C5B—C4B | 122.25 (14) |
O1A—C2A—C1A | 118.08 (13) | N1B—C5B—H5B | 118.9 |
O1A—C2A—C3A | 120.27 (13) | C4B—C5B—H5B | 118.9 |
C1A—C2A—C3A | 121.64 (14) | N1B—C6B—H6D | 109.5 |
O2A—C3A—C4A | 123.97 (14) | N1B—C6B—H6E | 109.5 |
O2A—C3A—C2A | 120.25 (13) | H6D—C6B—H6E | 109.5 |
C4A—C3A—C2A | 115.77 (13) | N1B—C6B—H6F | 109.5 |
C5A—C4A—C3A | 120.82 (14) | H6D—C6B—H6F | 109.5 |
C5A—C4A—H4A | 119.6 | H6E—C6B—H6F | 109.5 |
C3A—C4A—H4A | 119.6 | C1B—C7B—H7D | 109.5 |
N1A—C5A—C4A | 121.63 (14) | C1B—C7B—H7E | 109.5 |
N1A—C5A—H5A | 119.2 | H7D—C7B—H7E | 109.5 |
C4A—C5A—H5A | 119.2 | C1B—C7B—H7F | 109.5 |
N1A—C6A—H6A | 109.5 | H7D—C7B—H7F | 109.5 |
N1A—C6A—H6B | 109.5 | H7E—C7B—H7F | 109.5 |
H6A—C6A—H6B | 109.5 | C5B—N1B—C1B | 120.57 (13) |
N1A—C6A—H6C | 109.5 | C5B—N1B—C6B | 118.85 (13) |
H6A—C6A—H6C | 109.5 | C1B—N1B—C6B | 120.57 (13) |
H6B—C6A—H6C | 109.5 | C2B—O1B—H2O | 112.9 (16) |
C1A—C7A—H7A | 109.5 | O3—C8—C9 | 117.01 (14) |
C1A—C7A—H7B | 109.5 | O3—C8—C13 | 122.74 (13) |
H7A—C7A—H7B | 109.5 | C9—C8—C13 | 120.24 (14) |
C1A—C7A—H7C | 109.5 | C10—C9—C8 | 119.90 (14) |
H7A—C7A—H7C | 109.5 | C10—C9—H9 | 120.0 |
H7B—C7A—H7C | 109.5 | C8—C9—H9 | 120.0 |
C5A—N1A—C1A | 120.92 (13) | O4—C10—C9 | 117.22 (13) |
C5A—N1A—C6A | 118.53 (13) | O4—C10—C11 | 122.23 (14) |
C1A—N1A—C6A | 120.48 (13) | C9—C10—C11 | 120.55 (13) |
C2A—O1A—H1O | 113.2 (16) | C12—C11—C10 | 118.63 (14) |
N1B—C1B—C2B | 119.00 (13) | C12—C11—H11 | 120.7 |
N1B—C1B—C7B | 118.82 (13) | C10—C11—H11 | 120.7 |
C2B—C1B—C7B | 122.16 (14) | C13—C12—C11 | 121.73 (14) |
O1B—C2B—C1B | 118.59 (13) | C13—C12—H12 | 119.1 |
O1B—C2B—C3B | 119.45 (13) | C11—C12—H12 | 119.1 |
C1B—C2B—C3B | 121.96 (14) | C12—C13—C8 | 118.91 (13) |
O2B—C3B—C4B | 122.97 (13) | C12—C13—H13 | 120.5 |
O2B—C3B—C2B | 121.32 (13) | C8—C13—H13 | 120.5 |
C4B—C3B—C2B | 115.71 (13) | C8—O3—H3O | 111.2 (17) |
C5B—C4B—C3B | 120.43 (14) | C10—O4—H4O | 110.7 (13) |
| | | |
N1A—C1A—C2A—O1A | −175.89 (14) | C1B—C2B—C3B—O2B | 176.85 (14) |
C7A—C1A—C2A—O1A | 5.0 (2) | O1B—C2B—C3B—C4B | 176.90 (13) |
N1A—C1A—C2A—C3A | 4.4 (2) | C1B—C2B—C3B—C4B | −2.8 (2) |
C7A—C1A—C2A—C3A | −174.76 (15) | O2B—C3B—C4B—C5B | −178.76 (14) |
O1A—C2A—C3A—O2A | −3.7 (2) | C2B—C3B—C4B—C5B | 0.9 (2) |
C1A—C2A—C3A—O2A | 176.01 (14) | C3B—C4B—C5B—N1B | 0.3 (2) |
O1A—C2A—C3A—C4A | 176.86 (14) | C4B—C5B—N1B—C1B | 0.3 (2) |
C1A—C2A—C3A—C4A | −3.4 (2) | C4B—C5B—N1B—C6B | 179.39 (15) |
O2A—C3A—C4A—C5A | −178.50 (15) | C2B—C1B—N1B—C5B | −2.1 (2) |
C2A—C3A—C4A—C5A | 0.9 (2) | C7B—C1B—N1B—C5B | 176.18 (14) |
C3A—C4A—C5A—N1A | 0.6 (2) | C2B—C1B—N1B—C6B | 178.76 (14) |
C4A—C5A—N1A—C1A | 0.3 (2) | C7B—C1B—N1B—C6B | −2.9 (2) |
C4A—C5A—N1A—C6A | 177.19 (15) | O3—C8—C9—C10 | −176.45 (14) |
C2A—C1A—N1A—C5A | −2.8 (2) | C13—C8—C9—C10 | 2.2 (2) |
C7A—C1A—N1A—C5A | 176.39 (15) | C8—C9—C10—O4 | 176.84 (14) |
C2A—C1A—N1A—C6A | −179.61 (14) | C8—C9—C10—C11 | −2.4 (2) |
C7A—C1A—N1A—C6A | −0.5 (2) | O4—C10—C11—C12 | −178.02 (15) |
N1B—C1B—C2B—O1B | −176.25 (13) | C9—C10—C11—C12 | 1.2 (2) |
C7B—C1B—C2B—O1B | 5.5 (2) | C10—C11—C12—C13 | 0.2 (2) |
N1B—C1B—C2B—C3B | 3.5 (2) | C11—C12—C13—C8 | −0.4 (2) |
C7B—C1B—C2B—C3B | −174.80 (14) | O3—C8—C13—C12 | 177.80 (15) |
O1B—C2B—C3B—O2B | −3.5 (2) | C9—C8—C13—C12 | −0.8 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1O···O2B | 0.87 (3) | 1.83 (3) | 2.6191 (15) | 150 (2) |
O1B—H2O···O2A | 0.90 (2) | 1.76 (3) | 2.6177 (16) | 160 (2) |
O3—H3O···O2A | 0.88 (3) | 1.79 (3) | 2.6457 (15) | 164 (2) |
O4—H4O···O2Bi | 0.89 (2) | 1.76 (2) | 2.6394 (16) | 170 (2) |
C5A—H5A···O1Bii | 0.95 | 2.31 | 3.2218 (19) | 160 |
C4B—H4B···O3iii | 0.95 | 2.59 | 3.2632 (19) | 128 |
C4B—H4B···O4iv | 0.95 | 2.47 | 3.1393 (18) | 127 |
C5B—H5B···O2Aiii | 0.95 | 2.49 | 3.3098 (19) | 144 |
C11—H11···O1Ai | 0.95 | 2.43 | 3.3524 (19) | 164 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1/2, y−1/2, −z+3/2; (iii) −x, −y+1, −z+1; (iv) x−1, y, z. |
(KA1018_0m_def-res_1_1)
top
Crystal data top
C7H9NO2·C6H6O2 | F(000) = 528 |
Mr = 249.26 | Dx = 1.398 Mg m−3 Dm = colorless Mg m−3 Dm measured by ? |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.13393 (8) Å | Cell parameters from 9916 reflections |
b = 18.2199 (2) Å | θ = 2.2–30.6° |
c = 9.1517 (1) Å | µ = 0.10 mm−1 |
β = 95.4213 (4)° | T = 100 K |
V = 1184.21 (2) Å3 | Block |
Z = 4 | 0.28 × 0.24 × 0.17 mm |
Data collection top
Bruker D8 QUEST PHOTON-100 diffractometer | 2528 reflections with I > 2σ(I) |
Radiation source: microfocus | Rint = 0.022 |
ω and φ scans | θmax = 27.5°, θmin = 2.2° |
Absorption correction: multi-scan SADABS, Bruker, 2016 | h = −9→9 |
Tmin = 0.686, Tmax = 0.746 | k = −20→23 |
12941 measured reflections | l = −11→11 |
2715 independent reflections | |
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)] = 0.035 | w = 1/[σ2(Fo2) + (0.0591P)2 + 0.4132P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.105 | (Δ/σ)max = 0.001 |
S = 1.09 | Δρmax = 0.38 e Å−3 |
2715 reflections | Δρmin = −0.20 e Å−3 |
178 parameters | Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.026 (5) |
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 | |
C1 | 0.34797 (14) | 0.42574 (6) | 0.36771 (11) | 0.0132 (2) | |
C2 | 0.40005 (14) | 0.46620 (5) | 0.25087 (11) | 0.0124 (2) | |
C3 | 0.26616 (14) | 0.50666 (5) | 0.15610 (11) | 0.0121 (2) | |
C4 | 0.07844 (14) | 0.50428 (6) | 0.19399 (11) | 0.0143 (2) | |
H4 | −0.016728 | 0.530970 | 0.136996 | 0.017* | |
C5 | 0.03237 (14) | 0.46415 (6) | 0.31138 (11) | 0.0149 (2) | |
H5 | −0.095060 | 0.463082 | 0.333482 | 0.018* | |
C6 | 0.10146 (16) | 0.37912 (6) | 0.51535 (12) | 0.0179 (2) | |
H6A | −0.031352 | 0.388862 | 0.527197 | 0.027* | |
H6B | 0.177913 | 0.390082 | 0.607417 | 0.027* | |
H6C | 0.117091 | 0.327365 | 0.489976 | 0.027* | |
C7 | 0.48703 (15) | 0.38159 (6) | 0.46339 (12) | 0.0182 (2) | |
H7A | 0.506876 | 0.404483 | 0.560518 | 0.027* | |
H7B | 0.606772 | 0.379661 | 0.419124 | 0.027* | |
H7C | 0.438629 | 0.331674 | 0.473263 | 0.027* | |
O1 | 0.58549 (10) | 0.46813 (5) | 0.22767 (9) | 0.0177 (2) | |
H1O | 0.598 (3) | 0.4771 (10) | 0.137 (2) | 0.041 (5)* | |
O2 | 0.31733 (10) | 0.54248 (4) | 0.04550 (8) | 0.01461 (19) | |
N1 | 0.16275 (12) | 0.42583 (5) | 0.39720 (9) | 0.0132 (2) | |
C8 | 0.52644 (14) | 0.69772 (6) | 0.17439 (11) | 0.0134 (2) | |
C9 | 0.34253 (14) | 0.70504 (6) | 0.21173 (11) | 0.0131 (2) | |
H9 | 0.246363 | 0.673007 | 0.170895 | 0.016* | |
C10 | 0.30140 (14) | 0.76005 (6) | 0.30990 (11) | 0.0134 (2) | |
C11 | 0.44171 (15) | 0.80734 (6) | 0.36981 (11) | 0.0156 (2) | |
H11 | 0.413759 | 0.844168 | 0.437960 | 0.019* | |
C12 | 0.62358 (15) | 0.79981 (6) | 0.32826 (12) | 0.0171 (2) | |
H12 | 0.719158 | 0.832580 | 0.367217 | 0.021* | |
C13 | 0.66813 (15) | 0.74534 (6) | 0.23098 (11) | 0.0160 (2) | |
H13 | 0.792730 | 0.740654 | 0.203580 | 0.019* | |
O3 | 0.57473 (11) | 0.64441 (4) | 0.07833 (8) | 0.01707 (19) | |
H3O | 0.481 (3) | 0.6080 (10) | 0.070 (2) | 0.043 (5)* | |
O4 | 0.11893 (11) | 0.76519 (4) | 0.34212 (9) | 0.0182 (2) | |
H4O | 0.111 (3) | 0.8001 (10) | 0.410 (2) | 0.043 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0143 (5) | 0.0126 (5) | 0.0125 (5) | 0.0004 (4) | 0.0003 (4) | −0.0019 (4) |
C2 | 0.0113 (5) | 0.0131 (5) | 0.0126 (5) | 0.0001 (3) | 0.0003 (4) | −0.0018 (4) |
C3 | 0.0143 (5) | 0.0099 (5) | 0.0119 (4) | −0.0006 (3) | 0.0002 (4) | −0.0017 (3) |
C4 | 0.0136 (5) | 0.0135 (5) | 0.0155 (5) | 0.0024 (4) | −0.0008 (4) | −0.0009 (4) |
C5 | 0.0131 (5) | 0.0146 (5) | 0.0172 (5) | 0.0006 (4) | 0.0021 (4) | −0.0021 (4) |
C6 | 0.0216 (5) | 0.0165 (5) | 0.0167 (5) | −0.0011 (4) | 0.0066 (4) | 0.0025 (4) |
C7 | 0.0182 (5) | 0.0196 (5) | 0.0163 (5) | 0.0025 (4) | −0.0006 (4) | 0.0046 (4) |
O1 | 0.0109 (4) | 0.0276 (5) | 0.0145 (4) | 0.0017 (3) | 0.0014 (3) | 0.0051 (3) |
O2 | 0.0168 (4) | 0.0141 (4) | 0.0129 (4) | −0.0004 (3) | 0.0014 (3) | 0.0015 (3) |
N1 | 0.0150 (4) | 0.0121 (4) | 0.0128 (4) | −0.0009 (3) | 0.0026 (3) | −0.0003 (3) |
C8 | 0.0161 (5) | 0.0127 (5) | 0.0115 (5) | 0.0004 (4) | 0.0015 (4) | 0.0029 (3) |
C9 | 0.0137 (5) | 0.0134 (5) | 0.0120 (4) | −0.0022 (4) | −0.0006 (4) | 0.0015 (4) |
C10 | 0.0138 (5) | 0.0143 (5) | 0.0121 (5) | 0.0008 (4) | 0.0010 (4) | 0.0037 (4) |
C11 | 0.0202 (5) | 0.0130 (5) | 0.0134 (5) | −0.0007 (4) | 0.0001 (4) | 0.0003 (4) |
C12 | 0.0181 (5) | 0.0165 (5) | 0.0159 (5) | −0.0053 (4) | −0.0026 (4) | 0.0021 (4) |
C13 | 0.0131 (5) | 0.0181 (5) | 0.0166 (5) | −0.0019 (4) | 0.0009 (4) | 0.0039 (4) |
O3 | 0.0179 (4) | 0.0149 (4) | 0.0194 (4) | −0.0019 (3) | 0.0066 (3) | −0.0018 (3) |
O4 | 0.0146 (4) | 0.0212 (4) | 0.0195 (4) | 0.0003 (3) | 0.0047 (3) | −0.0037 (3) |
Geometric parameters (Å, º) top
C1—N1 | 1.3734 (13) | C7—H7C | 0.9800 |
C1—C2 | 1.3783 (14) | O1—H1O | 0.85 (2) |
C1—C7 | 1.4946 (14) | C8—O3 | 1.3756 (12) |
C2—O1 | 1.3600 (12) | C8—C9 | 1.3931 (14) |
C2—C3 | 1.4323 (14) | C8—C13 | 1.3942 (15) |
C3—O2 | 1.2859 (12) | C9—C10 | 1.3956 (14) |
C3—C4 | 1.4153 (14) | C9—H9 | 0.9500 |
C4—C5 | 1.3652 (15) | C10—O4 | 1.3648 (12) |
C4—H4 | 0.9500 | C10—C11 | 1.3933 (15) |
C5—N1 | 1.3533 (14) | C11—C12 | 1.3928 (15) |
C5—H5 | 0.9500 | C11—H11 | 0.9500 |
C6—N1 | 1.4744 (13) | C12—C13 | 1.3899 (15) |
C6—H6A | 0.9800 | C12—H12 | 0.9500 |
C6—H6B | 0.9800 | C13—H13 | 0.9500 |
C6—H6C | 0.9800 | O3—H3O | 0.937 (19) |
C7—H7A | 0.9800 | O4—H4O | 0.893 (19) |
C7—H7B | 0.9800 | | |
| | | |
N1—C1—C2 | 119.12 (9) | H7B—C7—H7C | 109.5 |
N1—C1—C7 | 118.89 (9) | C2—O1—H1O | 110.2 (13) |
C2—C1—C7 | 121.99 (9) | C5—N1—C1 | 120.52 (9) |
O1—C2—C1 | 118.19 (9) | C5—N1—C6 | 119.23 (9) |
O1—C2—C3 | 119.68 (9) | C1—N1—C6 | 120.06 (8) |
C1—C2—C3 | 122.13 (9) | O3—C8—C9 | 121.53 (9) |
O2—C3—C4 | 123.64 (9) | O3—C8—C13 | 117.41 (9) |
O2—C3—C2 | 121.01 (9) | C9—C8—C13 | 121.06 (10) |
C4—C3—C2 | 115.35 (9) | C8—C9—C10 | 119.13 (9) |
C5—C4—C3 | 120.86 (9) | C8—C9—H9 | 120.4 |
C5—C4—H4 | 119.6 | C10—C9—H9 | 120.4 |
C3—C4—H4 | 119.6 | O4—C10—C11 | 122.48 (9) |
N1—C5—C4 | 121.99 (9) | O4—C10—C9 | 116.82 (9) |
N1—C5—H5 | 119.0 | C11—C10—C9 | 120.70 (10) |
C4—C5—H5 | 119.0 | C12—C11—C10 | 119.00 (10) |
N1—C6—H6A | 109.5 | C12—C11—H11 | 120.5 |
N1—C6—H6B | 109.5 | C10—C11—H11 | 120.5 |
H6A—C6—H6B | 109.5 | C13—C12—C11 | 121.36 (10) |
N1—C6—H6C | 109.5 | C13—C12—H12 | 119.3 |
H6A—C6—H6C | 109.5 | C11—C12—H12 | 119.3 |
H6B—C6—H6C | 109.5 | C12—C13—C8 | 118.73 (10) |
C1—C7—H7A | 109.5 | C12—C13—H13 | 120.6 |
C1—C7—H7B | 109.5 | C8—C13—H13 | 120.6 |
H7A—C7—H7B | 109.5 | C8—O3—H3O | 109.4 (11) |
C1—C7—H7C | 109.5 | C10—O4—H4O | 109.0 (12) |
H7A—C7—H7C | 109.5 | | |
| | | |
N1—C1—C2—O1 | 176.99 (9) | C7—C1—N1—C5 | −178.85 (9) |
C7—C1—C2—O1 | −3.10 (15) | C2—C1—N1—C6 | 175.92 (9) |
N1—C1—C2—C3 | −1.98 (15) | C7—C1—N1—C6 | −4.00 (14) |
C7—C1—C2—C3 | 177.93 (9) | O3—C8—C9—C10 | 179.92 (9) |
O1—C2—C3—O2 | 2.86 (15) | C13—C8—C9—C10 | −1.40 (15) |
C1—C2—C3—O2 | −178.18 (9) | C8—C9—C10—O4 | 179.60 (9) |
O1—C2—C3—C4 | −176.77 (9) | C8—C9—C10—C11 | 0.19 (15) |
C1—C2—C3—C4 | 2.19 (14) | O4—C10—C11—C12 | −178.23 (9) |
O2—C3—C4—C5 | 178.83 (10) | C9—C10—C11—C12 | 1.14 (15) |
C2—C3—C4—C5 | −1.56 (14) | C10—C11—C12—C13 | −1.31 (15) |
C3—C4—C5—N1 | 0.78 (16) | C11—C12—C13—C8 | 0.14 (15) |
C4—C5—N1—C1 | −0.48 (15) | O3—C8—C13—C12 | 179.97 (9) |
C4—C5—N1—C6 | −175.38 (9) | C9—C8—C13—C12 | 1.24 (15) |
C2—C1—N1—C5 | 1.07 (14) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O2i | 0.85 (2) | 1.87 (2) | 2.6638 (11) | 154 (2) |
O3—H3O···O2 | 0.937 (19) | 1.673 (19) | 2.6090 (11) | 177 (2) |
O4—H4O···O3ii | 0.893 (19) | 1.88 (2) | 2.7594 (11) | 167 (2) |
C5—H5···O1iii | 0.95 | 2.39 | 3.2084 (13) | 144 |
C13—H13···O4iv | 0.95 | 2.58 | 3.2999 (13) | 133 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1/2, −y+3/2, z+1/2; (iii) x−1, y, z; (iv) x+1, y, z. |
(KA773_0m_def-phg_2_1)
top
Crystal data top
2(C7H9NO2)·C6H6O3 | Dx = 1.441 Mg m−3 |
Mr = 404.41 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 4198 reflections |
a = 6.9983 (2) Å | θ = 2.3–30.3° |
b = 18.4416 (6) Å | µ = 0.11 mm−1 |
c = 28.8960 (8) Å | T = 100 K |
V = 3729.31 (19) Å3 | Block, colorless |
Z = 8 | 0.28 × 0.24 × 0.12 mm |
F(000) = 1712 | |
Data collection top
Bruker D8 QUEST PHOTON-100 diffractometer | 2498 reflections with I > 2σ(I) |
Radiation source: microfocus | Rint = 0.106 |
ω and φ scans | θmax = 26.3°, θmin = 2.6° |
Absorption correction: multi-scan SADABS, Bruker, 2016 | h = −6→8 |
Tmin = 0.656, Tmax = 0.746 | k = −21→22 |
18441 measured reflections | l = −35→35 |
3759 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.057 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.0352P)2 + 3.1236P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
3759 reflections | Δρmax = 0.27 e Å−3 |
286 parameters | Δρmin = −0.30 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 | |
C1A | 1.0878 (4) | 0.94502 (14) | 0.54403 (8) | 0.0124 (6) | |
C2A | 0.9194 (4) | 0.93700 (13) | 0.56781 (7) | 0.0105 (6) | |
C3A | 0.7833 (4) | 0.88173 (14) | 0.55713 (7) | 0.0114 (6) | |
C4A | 0.8308 (4) | 0.83800 (14) | 0.51865 (8) | 0.0140 (6) | |
H4A | 0.746161 | 0.800564 | 0.509190 | 0.017* | |
C5A | 0.9964 (4) | 0.84889 (14) | 0.49502 (8) | 0.0155 (6) | |
H5A | 1.024005 | 0.818670 | 0.469244 | 0.019* | |
C6A | 1.3027 (4) | 0.90659 (15) | 0.48078 (8) | 0.0186 (6) | |
H6A | 1.409387 | 0.892534 | 0.500833 | 0.028* | |
H6B | 1.320344 | 0.956772 | 0.470478 | 0.028* | |
H6C | 1.298486 | 0.874442 | 0.453796 | 0.028* | |
C7A | 1.2351 (4) | 0.99952 (14) | 0.55728 (8) | 0.0166 (6) | |
H7A | 1.185485 | 1.030147 | 0.582258 | 0.025* | |
H7B | 1.265969 | 1.029772 | 0.530420 | 0.025* | |
H7C | 1.350594 | 0.974499 | 0.567874 | 0.025* | |
O1A | 0.8851 (3) | 0.98286 (9) | 0.60349 (6) | 0.0144 (4) | |
H1O | 0.766 (5) | 0.9750 (16) | 0.6178 (9) | 0.031 (9)* | |
O2A | 0.6314 (2) | 0.87464 (9) | 0.58151 (5) | 0.0145 (4) | |
N1A | 1.1224 (3) | 0.90061 (11) | 0.50665 (6) | 0.0129 (5) | |
C1B | 0.6777 (4) | 0.85960 (13) | 0.75243 (8) | 0.0119 (6) | |
C2B | 0.6565 (3) | 0.88916 (14) | 0.70906 (8) | 0.0109 (6) | |
C3B | 0.6000 (4) | 0.96222 (13) | 0.70218 (8) | 0.0110 (6) | |
C4B | 0.5589 (3) | 1.00161 (14) | 0.74259 (8) | 0.0116 (5) | |
H4B | 0.516178 | 1.050365 | 0.740205 | 0.014* | |
C5B | 0.5795 (4) | 0.97086 (14) | 0.78508 (8) | 0.0125 (6) | |
H5B | 0.549349 | 0.998507 | 0.811841 | 0.015* | |
C6B | 0.6726 (4) | 0.87373 (15) | 0.83712 (8) | 0.0167 (6) | |
H6D | 0.576882 | 0.836388 | 0.843823 | 0.025* | |
H6E | 0.660788 | 0.913218 | 0.859635 | 0.025* | |
H6F | 0.800729 | 0.852548 | 0.839157 | 0.025* | |
C7B | 0.7337 (4) | 0.78253 (14) | 0.76013 (8) | 0.0163 (6) | |
H7D | 0.634968 | 0.758113 | 0.778441 | 0.024* | |
H7E | 0.855593 | 0.780788 | 0.776789 | 0.024* | |
H7F | 0.747372 | 0.758041 | 0.730211 | 0.024* | |
O1B | 0.6944 (3) | 0.84620 (10) | 0.67188 (6) | 0.0154 (4) | |
H2O | 0.668 (4) | 0.8684 (17) | 0.6466 (10) | 0.036 (10)* | |
O2B | 0.5862 (2) | 0.98766 (9) | 0.66070 (5) | 0.0131 (4) | |
N1B | 0.6416 (3) | 0.90233 (11) | 0.79018 (6) | 0.0122 (5) | |
C8 | 0.4243 (4) | 0.65664 (14) | 0.65454 (8) | 0.0113 (5) | |
C9 | 0.2434 (4) | 0.62709 (14) | 0.66009 (7) | 0.0117 (5) | |
H9 | 0.221819 | 0.589960 | 0.682274 | 0.014* | |
C10 | 0.0945 (4) | 0.65236 (13) | 0.63289 (8) | 0.0107 (5) | |
C11 | 0.1226 (4) | 0.70806 (13) | 0.60133 (8) | 0.0115 (6) | |
H11 | 0.019877 | 0.725611 | 0.583000 | 0.014* | |
C12 | 0.3043 (4) | 0.73755 (13) | 0.59715 (8) | 0.0107 (6) | |
C13 | 0.4575 (4) | 0.71206 (14) | 0.62323 (7) | 0.0109 (6) | |
H13 | 0.581578 | 0.732169 | 0.619639 | 0.013* | |
O3 | 0.5680 (3) | 0.63034 (10) | 0.68217 (6) | 0.0160 (4) | |
H3O | 0.686 (5) | 0.6420 (18) | 0.6707 (10) | 0.044 (10)* | |
O4 | −0.0849 (3) | 0.62285 (11) | 0.63639 (6) | 0.0161 (4) | |
H4O | −0.080 (5) | 0.5765 (18) | 0.6457 (10) | 0.044 (10)* | |
O5 | 0.3282 (3) | 0.79285 (10) | 0.56613 (6) | 0.0153 (4) | |
H5O | 0.447 (5) | 0.8191 (19) | 0.5724 (11) | 0.061 (12)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.0123 (14) | 0.0138 (14) | 0.0112 (12) | 0.0037 (12) | −0.0017 (11) | 0.0029 (10) |
C2A | 0.0132 (15) | 0.0112 (14) | 0.0070 (11) | 0.0018 (11) | −0.0022 (10) | 0.0017 (10) |
C3A | 0.0139 (15) | 0.0099 (14) | 0.0104 (11) | 0.0012 (11) | −0.0025 (10) | 0.0041 (10) |
C4A | 0.0165 (16) | 0.0114 (14) | 0.0139 (12) | −0.0019 (12) | −0.0054 (11) | 0.0015 (10) |
C5A | 0.0207 (15) | 0.0167 (15) | 0.0091 (11) | 0.0044 (13) | 0.0004 (11) | −0.0012 (11) |
C6A | 0.0156 (15) | 0.0256 (16) | 0.0147 (13) | 0.0030 (13) | 0.0060 (11) | 0.0027 (11) |
C7A | 0.0151 (15) | 0.0175 (15) | 0.0172 (13) | −0.0015 (12) | 0.0022 (11) | 0.0031 (11) |
O1A | 0.0136 (11) | 0.0148 (10) | 0.0149 (9) | −0.0027 (8) | 0.0041 (8) | −0.0046 (7) |
O2A | 0.0122 (10) | 0.0177 (10) | 0.0137 (8) | −0.0046 (8) | 0.0013 (7) | −0.0010 (7) |
N1A | 0.0129 (12) | 0.0159 (12) | 0.0098 (10) | 0.0019 (10) | 0.0028 (9) | 0.0016 (9) |
C1B | 0.0059 (13) | 0.0122 (14) | 0.0178 (12) | −0.0018 (11) | −0.0002 (10) | 0.0007 (11) |
C2B | 0.0073 (14) | 0.0119 (15) | 0.0136 (12) | −0.0040 (11) | −0.0005 (10) | −0.0028 (10) |
C3B | 0.0047 (14) | 0.0135 (14) | 0.0149 (12) | −0.0029 (11) | 0.0006 (10) | −0.0004 (10) |
C4B | 0.0057 (13) | 0.0094 (13) | 0.0197 (13) | −0.0006 (11) | 0.0001 (10) | 0.0012 (10) |
C5B | 0.0079 (14) | 0.0154 (15) | 0.0142 (12) | −0.0013 (12) | 0.0028 (10) | −0.0038 (10) |
C6B | 0.0154 (15) | 0.0214 (16) | 0.0133 (12) | 0.0041 (12) | 0.0001 (11) | 0.0047 (11) |
C7B | 0.0157 (15) | 0.0135 (14) | 0.0197 (13) | 0.0018 (12) | −0.0039 (11) | 0.0020 (11) |
O1B | 0.0232 (12) | 0.0112 (10) | 0.0118 (9) | 0.0034 (8) | −0.0010 (8) | −0.0026 (8) |
O2B | 0.0158 (10) | 0.0142 (10) | 0.0093 (8) | 0.0030 (8) | 0.0004 (7) | 0.0027 (7) |
N1B | 0.0121 (12) | 0.0135 (12) | 0.0110 (10) | −0.0006 (10) | −0.0003 (9) | 0.0018 (9) |
C8 | 0.0123 (14) | 0.0109 (13) | 0.0108 (11) | 0.0017 (12) | −0.0018 (10) | −0.0013 (10) |
C9 | 0.0147 (14) | 0.0094 (13) | 0.0109 (11) | −0.0002 (12) | 0.0032 (11) | 0.0026 (10) |
C10 | 0.0082 (14) | 0.0088 (13) | 0.0151 (12) | 0.0001 (11) | 0.0029 (10) | −0.0027 (10) |
C11 | 0.0137 (15) | 0.0093 (13) | 0.0117 (11) | 0.0007 (11) | −0.0045 (10) | 0.0003 (10) |
C12 | 0.0153 (15) | 0.0060 (13) | 0.0108 (11) | −0.0006 (11) | −0.0004 (10) | −0.0003 (10) |
C13 | 0.0079 (14) | 0.0119 (14) | 0.0129 (12) | −0.0018 (11) | 0.0032 (10) | −0.0036 (10) |
O3 | 0.0087 (11) | 0.0214 (11) | 0.0177 (9) | −0.0005 (9) | −0.0027 (8) | 0.0064 (8) |
O4 | 0.0111 (10) | 0.0126 (11) | 0.0247 (9) | −0.0029 (9) | −0.0002 (8) | 0.0043 (8) |
O5 | 0.0158 (11) | 0.0138 (10) | 0.0163 (9) | −0.0039 (9) | −0.0034 (8) | 0.0065 (8) |
Geometric parameters (Å, º) top
C1A—C2A | 1.373 (3) | C4B—H4B | 0.9500 |
C1A—N1A | 1.377 (3) | C5B—N1B | 1.344 (3) |
C1A—C7A | 1.490 (4) | C5B—H5B | 0.9500 |
C2A—O1A | 1.355 (3) | C6B—N1B | 1.471 (3) |
C2A—C3A | 1.429 (4) | C6B—H6D | 0.9800 |
C3A—O2A | 1.282 (3) | C6B—H6E | 0.9800 |
C3A—C4A | 1.413 (3) | C6B—H6F | 0.9800 |
C4A—C5A | 1.360 (4) | C7B—H7D | 0.9800 |
C4A—H4A | 0.9500 | C7B—H7E | 0.9800 |
C5A—N1A | 1.342 (3) | C7B—H7F | 0.9800 |
C5A—H5A | 0.9500 | O1B—H2O | 0.86 (3) |
C6A—N1A | 1.470 (3) | C8—O3 | 1.372 (3) |
C6A—H6A | 0.9800 | C8—C13 | 1.385 (3) |
C6A—H6B | 0.9800 | C8—C9 | 1.388 (4) |
C6A—H6C | 0.9800 | C9—C10 | 1.386 (3) |
C7A—H7A | 0.9800 | C9—H9 | 0.9500 |
C7A—H7B | 0.9800 | C10—O4 | 1.372 (3) |
C7A—H7C | 0.9800 | C10—C11 | 1.388 (3) |
O1A—H1O | 0.94 (3) | C11—C12 | 1.388 (4) |
C1B—N1B | 1.369 (3) | C11—H11 | 0.9500 |
C1B—C2B | 1.375 (3) | C12—O5 | 1.368 (3) |
C1B—C7B | 1.491 (3) | C12—C13 | 1.392 (3) |
C2B—O1B | 1.361 (3) | C13—H13 | 0.9500 |
C2B—C3B | 1.418 (4) | O3—H3O | 0.92 (3) |
C3B—O2B | 1.291 (3) | O4—H4O | 0.90 (3) |
C3B—C4B | 1.405 (3) | O5—H5O | 0.98 (4) |
C4B—C5B | 1.360 (3) | | |
| | | |
C2A—C1A—N1A | 118.7 (2) | C3B—C4B—H4B | 119.6 |
C2A—C1A—C7A | 122.6 (2) | N1B—C5B—C4B | 121.7 (2) |
N1A—C1A—C7A | 118.8 (2) | N1B—C5B—H5B | 119.2 |
O1A—C2A—C1A | 117.8 (2) | C4B—C5B—H5B | 119.2 |
O1A—C2A—C3A | 119.5 (2) | N1B—C6B—H6D | 109.5 |
C1A—C2A—C3A | 122.8 (2) | N1B—C6B—H6E | 109.5 |
O2A—C3A—C4A | 124.7 (2) | H6D—C6B—H6E | 109.5 |
O2A—C3A—C2A | 120.4 (2) | N1B—C6B—H6F | 109.5 |
C4A—C3A—C2A | 114.8 (2) | H6D—C6B—H6F | 109.5 |
C5A—C4A—C3A | 120.8 (2) | H6E—C6B—H6F | 109.5 |
C5A—C4A—H4A | 119.6 | C1B—C7B—H7D | 109.5 |
C3A—C4A—H4A | 119.6 | C1B—C7B—H7E | 109.5 |
N1A—C5A—C4A | 122.6 (2) | H7D—C7B—H7E | 109.5 |
N1A—C5A—H5A | 118.7 | C1B—C7B—H7F | 109.5 |
C4A—C5A—H5A | 118.7 | H7D—C7B—H7F | 109.5 |
N1A—C6A—H6A | 109.5 | H7E—C7B—H7F | 109.5 |
N1A—C6A—H6B | 109.5 | C2B—O1B—H2O | 111 (2) |
H6A—C6A—H6B | 109.5 | C5B—N1B—C1B | 120.9 (2) |
N1A—C6A—H6C | 109.5 | C5B—N1B—C6B | 119.0 (2) |
H6A—C6A—H6C | 109.5 | C1B—N1B—C6B | 120.1 (2) |
H6B—C6A—H6C | 109.5 | O3—C8—C13 | 121.2 (2) |
C1A—C7A—H7A | 109.5 | O3—C8—C9 | 117.5 (2) |
C1A—C7A—H7B | 109.5 | C13—C8—C9 | 121.2 (2) |
H7A—C7A—H7B | 109.5 | C10—C9—C8 | 119.2 (2) |
C1A—C7A—H7C | 109.5 | C10—C9—H9 | 120.4 |
H7A—C7A—H7C | 109.5 | C8—C9—H9 | 120.4 |
H7B—C7A—H7C | 109.5 | O4—C10—C9 | 120.8 (2) |
C2A—O1A—H1O | 113.3 (17) | O4—C10—C11 | 118.2 (2) |
C5A—N1A—C1A | 120.2 (2) | C9—C10—C11 | 121.0 (2) |
C5A—N1A—C6A | 119.3 (2) | C10—C11—C12 | 118.5 (2) |
C1A—N1A—C6A | 120.3 (2) | C10—C11—H11 | 120.7 |
N1B—C1B—C2B | 118.6 (2) | C12—C11—H11 | 120.7 |
N1B—C1B—C7B | 118.6 (2) | O5—C12—C11 | 117.5 (2) |
C2B—C1B—C7B | 122.9 (2) | O5—C12—C13 | 120.8 (2) |
O1B—C2B—C1B | 117.9 (2) | C11—C12—C13 | 121.7 (2) |
O1B—C2B—C3B | 119.8 (2) | C8—C13—C12 | 118.3 (2) |
C1B—C2B—C3B | 122.3 (2) | C8—C13—H13 | 120.9 |
O2B—C3B—C4B | 124.6 (2) | C12—C13—H13 | 120.9 |
O2B—C3B—C2B | 119.8 (2) | C8—O3—H3O | 112 (2) |
C4B—C3B—C2B | 115.6 (2) | C10—O4—H4O | 111 (2) |
C5B—C4B—C3B | 120.9 (2) | C12—O5—H5O | 110 (2) |
C5B—C4B—H4B | 119.6 | | |
| | | |
N1A—C1A—C2A—O1A | −177.8 (2) | O1B—C2B—C3B—C4B | 178.3 (2) |
C7A—C1A—C2A—O1A | 2.6 (3) | C1B—C2B—C3B—C4B | −2.7 (4) |
N1A—C1A—C2A—C3A | 3.8 (4) | O2B—C3B—C4B—C5B | −179.2 (2) |
C7A—C1A—C2A—C3A | −175.8 (2) | C2B—C3B—C4B—C5B | 2.1 (4) |
O1A—C2A—C3A—O2A | −1.2 (3) | C3B—C4B—C5B—N1B | 0.7 (4) |
C1A—C2A—C3A—O2A | 177.2 (2) | C4B—C5B—N1B—C1B | −3.2 (4) |
O1A—C2A—C3A—C4A | 178.6 (2) | C4B—C5B—N1B—C6B | 176.1 (2) |
C1A—C2A—C3A—C4A | −3.0 (3) | C2B—C1B—N1B—C5B | 2.5 (4) |
O2A—C3A—C4A—C5A | −179.3 (2) | C7B—C1B—N1B—C5B | −176.0 (2) |
C2A—C3A—C4A—C5A | 0.9 (3) | C2B—C1B—N1B—C6B | −176.8 (2) |
C3A—C4A—C5A—N1A | 0.2 (4) | C7B—C1B—N1B—C6B | 4.7 (3) |
C4A—C5A—N1A—C1A | 0.5 (4) | O3—C8—C9—C10 | 179.9 (2) |
C4A—C5A—N1A—C6A | 177.0 (2) | C13—C8—C9—C10 | 1.7 (4) |
C2A—C1A—N1A—C5A | −2.5 (3) | C8—C9—C10—O4 | 177.9 (2) |
C7A—C1A—N1A—C5A | 177.1 (2) | C8—C9—C10—C11 | −1.9 (4) |
C2A—C1A—N1A—C6A | −178.9 (2) | O4—C10—C11—C12 | −179.2 (2) |
C7A—C1A—N1A—C6A | 0.7 (3) | C9—C10—C11—C12 | 0.7 (4) |
N1B—C1B—C2B—O1B | 179.5 (2) | C10—C11—C12—O5 | −179.4 (2) |
C7B—C1B—C2B—O1B | −2.1 (4) | C10—C11—C12—C13 | 0.8 (4) |
N1B—C1B—C2B—C3B | 0.4 (4) | O3—C8—C13—C12 | −178.3 (2) |
C7B—C1B—C2B—C3B | 178.9 (2) | C9—C8—C13—C12 | −0.2 (4) |
O1B—C2B—C3B—O2B | −0.5 (4) | O5—C12—C13—C8 | 179.1 (2) |
C1B—C2B—C3B—O2B | 178.5 (2) | C11—C12—C13—C8 | −1.1 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1O···O2B | 0.94 (3) | 1.78 (3) | 2.668 (2) | 156 (3) |
O1B—H2O···O2A | 0.86 (3) | 1.90 (3) | 2.700 (2) | 154 (3) |
O1B—H2O···O2B | 0.86 (3) | 2.31 (3) | 2.736 (2) | 111 (2) |
O3—H3O···O4i | 0.92 (3) | 1.92 (3) | 2.769 (3) | 154 (3) |
O4—H4O···O2Bii | 0.90 (3) | 1.69 (3) | 2.590 (2) | 175 (3) |
O5—H5O···O2A | 0.98 (4) | 1.67 (4) | 2.641 (3) | 172 (3) |
C5B—H5B···O3iii | 0.95 | 2.57 | 3.258 (3) | 129 |
C6B—H6E···O1Aiv | 0.98 | 2.55 | 3.323 (3) | 136 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1/2, y−1/2, z; (iii) −x+1, y+1/2, −z+3/2; (iv) x−1/2, y, −z+3/2. |
(KA1017_0m_def-phghyd_2_1_2)
top
Crystal data top
2(C7H9NO2)·C6H6O3·2(H2O) | Z = 2 |
Mr = 440.44 | F(000) = 468 |
Triclinic, P1 | Dx = 1.398 Mg m−3 |
a = 7.9892 (19) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.197 (3) Å | Cell parameters from 9849 reflections |
c = 12.876 (4) Å | θ = 2.5–30.5° |
α = 91.088 (8)° | µ = 0.11 mm−1 |
β = 93.874 (7)° | T = 100 K |
γ = 90.209 (7)° | Block, colorless |
V = 1046.4 (5) Å3 | 0.32 × 0.26 × 0.17 mm |
Data collection top
Bruker D8 QUEST PHOTON-100 diffractometer | 4349 reflections with I > 2σ(I) |
Radiation source: microfocus | Rint = 0.057 |
ω and φ scans | θmax = 27.0°, θmin = 2.5° |
Absorption correction: multi-scan SADABS, Bruker, 2016 | h = −9→10 |
Tmin = 0.538, Tmax = 0.746 | k = −13→13 |
20542 measured reflections | l = −16→16 |
4542 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.084 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.205 | w = 1/[σ2(Fo2) + 4.4439P] where P = (Fo2 + 2Fc2)/3 |
S = 1.25 | (Δ/σ)max < 0.001 |
4542 reflections | Δρmax = 0.48 e Å−3 |
300 parameters | Δρmin = −0.56 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) |
C1A | 0.7653 (4) | 0.5446 (3) | 1.2756 (2) | 0.0103 (6) | |
C2A | 0.6792 (4) | 0.5415 (3) | 1.1793 (2) | 0.0106 (6) | |
C3A | 0.6705 (4) | 0.6539 (3) | 1.1136 (3) | 0.0118 (6) | |
C4A | 0.7611 (4) | 0.7654 (3) | 1.1533 (3) | 0.0159 (7) | |
H4A | 0.762921 | 0.842147 | 1.112628 | 0.019* | |
C5A | 0.8460 (4) | 0.7648 (3) | 1.2490 (3) | 0.0158 (7) | |
H5A | 0.905462 | 0.841341 | 1.273594 | 0.019* | |
C6A | 0.9337 (4) | 0.6654 (4) | 1.4150 (3) | 0.0175 (7) | |
H6A | 1.013010 | 0.592687 | 1.423615 | 0.026* | |
H6B | 0.850697 | 0.659934 | 1.467449 | 0.026* | |
H6C | 0.994574 | 0.748908 | 1.423700 | 0.026* | |
C7A | 0.7710 (5) | 0.4277 (3) | 1.3451 (3) | 0.0163 (7) | |
H7A | 0.697749 | 0.358410 | 1.313651 | 0.024* | |
H7B | 0.732598 | 0.453297 | 1.413248 | 0.024* | |
H7C | 0.886330 | 0.395327 | 1.353705 | 0.024* | |
N1A | 0.8474 (3) | 0.6573 (3) | 1.3097 (2) | 0.0129 (6) | |
O1A | 0.5992 (3) | 0.4286 (2) | 1.14639 (19) | 0.0139 (5) | |
O2A | 0.5843 (3) | 0.6491 (2) | 1.02570 (18) | 0.0149 (5) | |
H1OA | 0.551 (7) | 0.439 (5) | 1.084 (4) | 0.044 (15)* | |
C1B | 0.2381 (4) | 0.5294 (3) | 0.2286 (3) | 0.0153 (7) | |
C2B | 0.3228 (5) | 0.5350 (3) | 0.3240 (3) | 0.0167 (7) | |
C3B | 0.4026 (4) | 0.6531 (3) | 0.3660 (3) | 0.0154 (7) | |
C4B | 0.3821 (4) | 0.7644 (3) | 0.3016 (3) | 0.0164 (7) | |
H4B | 0.428248 | 0.846557 | 0.325218 | 0.020* | |
C5B | 0.2969 (5) | 0.7547 (3) | 0.2065 (3) | 0.0168 (7) | |
H5B | 0.286583 | 0.830421 | 0.164751 | 0.020* | |
C6B | 0.1424 (5) | 0.6351 (4) | 0.0642 (3) | 0.0204 (7) | |
H6D | 0.144101 | 0.722251 | 0.033457 | 0.031* | |
H6E | 0.026000 | 0.606206 | 0.068303 | 0.031* | |
H6F | 0.201202 | 0.572865 | 0.020752 | 0.031* | |
C7B | 0.1576 (5) | 0.4051 (3) | 0.1844 (3) | 0.0205 (7) | |
H7D | 0.038753 | 0.421044 | 0.164962 | 0.031* | |
H7E | 0.167422 | 0.336550 | 0.236714 | 0.031* | |
H7F | 0.214041 | 0.376744 | 0.122612 | 0.031* | |
N1B | 0.2267 (4) | 0.6412 (3) | 0.1696 (2) | 0.0149 (6) | |
O1B | 0.3299 (4) | 0.4240 (2) | 0.3812 (2) | 0.0216 (6) | |
H1OB | 0.402 (6) | 0.433 (4) | 0.434 (3) | 0.015 (10)* | |
O2B | 0.4837 (3) | 0.6542 (2) | 0.45484 (19) | 0.0194 (5) | |
C8 | 0.0720 (4) | 0.8999 (3) | 0.6541 (2) | 0.0101 (6) | |
C9 | −0.1014 (4) | 0.9102 (3) | 0.6534 (2) | 0.0111 (6) | |
H9 | −0.168462 | 0.911490 | 0.589668 | 0.013* | |
C10 | −0.1745 (4) | 0.9187 (3) | 0.7484 (2) | 0.0075 (6) | |
C11 | −0.0789 (4) | 0.9219 (3) | 0.8429 (2) | 0.0100 (6) | |
H11 | −0.130662 | 0.931263 | 0.906883 | 0.012* | |
C12 | 0.0949 (4) | 0.9109 (3) | 0.8411 (2) | 0.0094 (6) | |
C13 | 0.1722 (4) | 0.8992 (3) | 0.7472 (2) | 0.0099 (6) | |
H13 | 0.290568 | 0.890981 | 0.746785 | 0.012* | |
O3 | 0.1396 (3) | 0.8906 (3) | 0.56004 (18) | 0.0190 (6) | |
H3O | 0.249 (7) | 0.890 (5) | 0.569 (4) | 0.035 (14)* | |
O4 | −0.3468 (3) | 0.9221 (2) | 0.74928 (17) | 0.0112 (5) | |
H4O | −0.383223 | 0.933341 | 0.687952 | 0.017* | |
O5 | 0.1849 (3) | 0.9122 (2) | 0.93497 (18) | 0.0136 (5) | |
H5O | 0.283 (8) | 0.911 (6) | 0.930 (5) | 0.056 (19)* | |
O1W | 0.4799 (3) | 0.8860 (2) | 0.55806 (18) | 0.0127 (5) | |
H1W | 0.491418 | 0.813132 | 0.524821 | 0.019* | |
H2W | 0.535172 | 0.877486 | 0.625250 | 0.019* | 0.5 |
H2WD | 0.492888 | 0.952574 | 0.520027 | 0.019* | 0.5 |
O2W | 0.5173 (3) | 0.8819 (2) | 0.93695 (17) | 0.0136 (5) | |
H3W | 0.541136 | 0.810013 | 0.966539 | 0.020* | |
H4W | 0.558828 | 0.894838 | 0.873059 | 0.020* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.0099 (14) | 0.0059 (14) | 0.0152 (15) | −0.0021 (11) | 0.0001 (11) | −0.0002 (11) |
C2A | 0.0071 (14) | 0.0098 (14) | 0.0148 (15) | −0.0014 (11) | 0.0004 (11) | −0.0014 (11) |
C3A | 0.0102 (14) | 0.0099 (15) | 0.0155 (15) | 0.0007 (11) | 0.0019 (12) | 0.0005 (12) |
C4A | 0.0151 (16) | 0.0096 (15) | 0.0230 (17) | −0.0018 (12) | −0.0011 (13) | 0.0046 (13) |
C5A | 0.0121 (15) | 0.0107 (15) | 0.0242 (17) | −0.0028 (12) | −0.0010 (13) | 0.0010 (13) |
C6A | 0.0140 (16) | 0.0190 (17) | 0.0181 (17) | −0.0020 (13) | −0.0080 (13) | −0.0029 (13) |
C7A | 0.0216 (17) | 0.0122 (15) | 0.0147 (15) | 0.0002 (13) | −0.0026 (13) | 0.0022 (12) |
N1A | 0.0107 (13) | 0.0114 (13) | 0.0159 (13) | −0.0008 (10) | −0.0030 (10) | −0.0016 (10) |
O1A | 0.0184 (12) | 0.0080 (11) | 0.0145 (11) | −0.0041 (9) | −0.0046 (9) | 0.0003 (9) |
O2A | 0.0169 (12) | 0.0123 (11) | 0.0148 (11) | −0.0003 (9) | −0.0040 (9) | 0.0025 (9) |
C1B | 0.0192 (17) | 0.0098 (15) | 0.0181 (16) | 0.0060 (12) | 0.0087 (13) | 0.0044 (12) |
C2B | 0.0231 (18) | 0.0132 (16) | 0.0149 (15) | 0.0084 (13) | 0.0075 (13) | 0.0059 (12) |
C3B | 0.0204 (17) | 0.0123 (16) | 0.0141 (15) | 0.0078 (13) | 0.0052 (13) | 0.0019 (12) |
C4B | 0.0223 (17) | 0.0102 (15) | 0.0173 (16) | 0.0030 (13) | 0.0036 (13) | 0.0036 (12) |
C5B | 0.0234 (18) | 0.0086 (15) | 0.0192 (16) | 0.0047 (13) | 0.0052 (14) | 0.0051 (12) |
C6B | 0.0283 (19) | 0.0182 (17) | 0.0155 (16) | 0.0072 (14) | 0.0046 (14) | 0.0062 (13) |
C7B | 0.0289 (19) | 0.0145 (17) | 0.0184 (17) | 0.0027 (14) | 0.0036 (14) | 0.0026 (13) |
N1B | 0.0192 (14) | 0.0140 (14) | 0.0119 (13) | 0.0058 (11) | 0.0026 (11) | 0.0045 (11) |
O1B | 0.0349 (16) | 0.0105 (12) | 0.0191 (13) | −0.0005 (10) | −0.0033 (11) | 0.0063 (10) |
O2B | 0.0287 (14) | 0.0146 (12) | 0.0147 (12) | 0.0082 (10) | −0.0014 (10) | 0.0026 (9) |
C8 | 0.0135 (15) | 0.0088 (14) | 0.0081 (14) | −0.0015 (11) | 0.0011 (11) | −0.0019 (11) |
C9 | 0.0097 (14) | 0.0122 (15) | 0.0110 (14) | 0.0006 (11) | −0.0016 (11) | 0.0018 (11) |
C10 | 0.0062 (13) | 0.0024 (12) | 0.0137 (14) | −0.0023 (10) | 0.0005 (11) | 0.0002 (10) |
C11 | 0.0117 (15) | 0.0078 (14) | 0.0108 (14) | −0.0016 (11) | 0.0023 (11) | 0.0000 (11) |
C12 | 0.0116 (14) | 0.0057 (13) | 0.0108 (14) | −0.0013 (11) | −0.0007 (11) | 0.0019 (11) |
C13 | 0.0074 (14) | 0.0103 (14) | 0.0119 (14) | 0.0010 (11) | −0.0009 (11) | −0.0008 (11) |
O3 | 0.0092 (12) | 0.0377 (15) | 0.0102 (11) | −0.0008 (10) | 0.0017 (9) | −0.0033 (10) |
O4 | 0.0064 (10) | 0.0152 (11) | 0.0118 (10) | 0.0001 (8) | −0.0013 (8) | 0.0013 (8) |
O5 | 0.0102 (12) | 0.0183 (12) | 0.0118 (11) | −0.0017 (9) | −0.0025 (9) | 0.0009 (9) |
O1W | 0.0121 (11) | 0.0101 (11) | 0.0159 (11) | 0.0001 (8) | 0.0003 (9) | 0.0017 (8) |
O2W | 0.0177 (12) | 0.0099 (11) | 0.0125 (11) | 0.0008 (9) | −0.0038 (9) | 0.0029 (8) |
Geometric parameters (Å, º) top
C1A—N1A | 1.371 (4) | C5B—H5B | 0.9500 |
C1A—C2A | 1.377 (4) | C6B—N1B | 1.474 (4) |
C1A—C7A | 1.503 (4) | C6B—H6D | 0.9800 |
C2A—O1A | 1.361 (4) | C6B—H6E | 0.9800 |
C2A—C3A | 1.437 (4) | C6B—H6F | 0.9800 |
C3A—O2A | 1.285 (4) | C7B—H7D | 0.9800 |
C3A—C4A | 1.414 (5) | C7B—H7E | 0.9800 |
C4A—C5A | 1.366 (5) | C7B—H7F | 0.9800 |
C4A—H4A | 0.9500 | O1B—H1OB | 0.86 (4) |
C5A—N1A | 1.359 (4) | C8—O3 | 1.362 (4) |
C5A—H5A | 0.9500 | C8—C9 | 1.389 (4) |
C6A—N1A | 1.480 (4) | C8—C13 | 1.396 (4) |
C6A—H6A | 0.9800 | C9—C10 | 1.392 (4) |
C6A—H6B | 0.9800 | C9—H9 | 0.9500 |
C6A—H6C | 0.9800 | C10—O4 | 1.379 (4) |
C7A—H7A | 0.9800 | C10—C11 | 1.391 (4) |
C7A—H7B | 0.9800 | C11—C12 | 1.395 (4) |
C7A—H7C | 0.9800 | C11—H11 | 0.9500 |
O1A—H1OA | 0.87 (6) | C12—O5 | 1.364 (4) |
C1B—C2B | 1.362 (5) | C12—C13 | 1.397 (4) |
C1B—N1B | 1.381 (4) | C13—H13 | 0.9500 |
C1B—C7B | 1.504 (5) | O3—H3O | 0.87 (6) |
C2B—O1B | 1.362 (4) | O4—H4O | 0.8330 |
C2B—C3B | 1.439 (5) | O5—H5O | 0.79 (7) |
C3B—O2B | 1.276 (4) | O1W—H1W | 0.8584 |
C3B—C4B | 1.422 (4) | O1W—H2W | 0.9500 |
C4B—C5B | 1.362 (5) | O1W—H2WD | 0.8550 |
C4B—H4B | 0.9500 | O2W—H3W | 0.8487 |
C5B—N1B | 1.349 (5) | O2W—H4W | 0.9192 |
| | | |
N1A—C1A—C2A | 119.4 (3) | N1B—C5B—H5B | 118.9 |
N1A—C1A—C7A | 118.9 (3) | C4B—C5B—H5B | 118.9 |
C2A—C1A—C7A | 121.7 (3) | N1B—C6B—H6D | 109.5 |
O1A—C2A—C1A | 118.7 (3) | N1B—C6B—H6E | 109.5 |
O1A—C2A—C3A | 119.5 (3) | H6D—C6B—H6E | 109.5 |
C1A—C2A—C3A | 121.8 (3) | N1B—C6B—H6F | 109.5 |
O2A—C3A—C4A | 124.3 (3) | H6D—C6B—H6F | 109.5 |
O2A—C3A—C2A | 120.3 (3) | H6E—C6B—H6F | 109.5 |
C4A—C3A—C2A | 115.4 (3) | C1B—C7B—H7D | 109.5 |
C5A—C4A—C3A | 121.2 (3) | C1B—C7B—H7E | 109.5 |
C5A—C4A—H4A | 119.4 | H7D—C7B—H7E | 109.5 |
C3A—C4A—H4A | 119.4 | C1B—C7B—H7F | 109.5 |
N1A—C5A—C4A | 121.5 (3) | H7D—C7B—H7F | 109.5 |
N1A—C5A—H5A | 119.3 | H7E—C7B—H7F | 109.5 |
C4A—C5A—H5A | 119.3 | C5B—N1B—C1B | 120.4 (3) |
N1A—C6A—H6A | 109.5 | C5B—N1B—C6B | 119.8 (3) |
N1A—C6A—H6B | 109.5 | C1B—N1B—C6B | 119.8 (3) |
H6A—C6A—H6B | 109.5 | C2B—O1B—H1OB | 110 (3) |
N1A—C6A—H6C | 109.5 | O3—C8—C9 | 117.0 (3) |
H6A—C6A—H6C | 109.5 | O3—C8—C13 | 121.6 (3) |
H6B—C6A—H6C | 109.5 | C9—C8—C13 | 121.4 (3) |
C1A—C7A—H7A | 109.5 | C8—C9—C10 | 118.4 (3) |
C1A—C7A—H7B | 109.5 | C8—C9—H9 | 120.8 |
H7A—C7A—H7B | 109.5 | C10—C9—H9 | 120.8 |
C1A—C7A—H7C | 109.5 | O4—C10—C11 | 118.8 (3) |
H7A—C7A—H7C | 109.5 | O4—C10—C9 | 119.1 (3) |
H7B—C7A—H7C | 109.5 | C11—C10—C9 | 122.0 (3) |
C5A—N1A—C1A | 120.6 (3) | C10—C11—C12 | 118.2 (3) |
C5A—N1A—C6A | 118.8 (3) | C10—C11—H11 | 120.9 |
C1A—N1A—C6A | 120.5 (3) | C12—C11—H11 | 120.9 |
C2A—O1A—H1OA | 109 (4) | O5—C12—C11 | 116.9 (3) |
C2B—C1B—N1B | 119.2 (3) | O5—C12—C13 | 121.9 (3) |
C2B—C1B—C7B | 122.3 (3) | C11—C12—C13 | 121.3 (3) |
N1B—C1B—C7B | 118.6 (3) | C8—C13—C12 | 118.6 (3) |
O1B—C2B—C1B | 117.9 (3) | C8—C13—H13 | 120.7 |
O1B—C2B—C3B | 119.5 (3) | C12—C13—H13 | 120.7 |
C1B—C2B—C3B | 122.5 (3) | C8—O3—H3O | 110 (3) |
O2B—C3B—C4B | 124.2 (3) | C10—O4—H4O | 106.4 |
O2B—C3B—C2B | 120.9 (3) | C12—O5—H5O | 113 (4) |
C4B—C3B—C2B | 114.9 (3) | H1W—O1W—H2W | 107.5 |
C5B—C4B—C3B | 120.7 (3) | H1W—O1W—H2WD | 112.5 |
C5B—C4B—H4B | 119.6 | H2W—O1W—H2WD | 122.9 |
C3B—C4B—H4B | 119.6 | H3W—O2W—H4W | 117.2 |
N1B—C5B—C4B | 122.2 (3) | | |
| | | |
N1A—C1A—C2A—O1A | 179.7 (3) | O1B—C2B—C3B—C4B | −177.7 (3) |
C7A—C1A—C2A—O1A | −0.8 (5) | C1B—C2B—C3B—C4B | 1.8 (5) |
N1A—C1A—C2A—C3A | −0.9 (5) | O2B—C3B—C4B—C5B | 178.4 (3) |
C7A—C1A—C2A—C3A | 178.6 (3) | C2B—C3B—C4B—C5B | −2.0 (5) |
O1A—C2A—C3A—O2A | 1.8 (5) | C3B—C4B—C5B—N1B | 0.9 (5) |
C1A—C2A—C3A—O2A | −177.6 (3) | C4B—C5B—N1B—C1B | 0.6 (5) |
O1A—C2A—C3A—C4A | −178.4 (3) | C4B—C5B—N1B—C6B | −177.3 (3) |
C1A—C2A—C3A—C4A | 2.1 (5) | C2B—C1B—N1B—C5B | −0.8 (5) |
O2A—C3A—C4A—C5A | 178.0 (3) | C7B—C1B—N1B—C5B | 179.9 (3) |
C2A—C3A—C4A—C5A | −1.8 (5) | C2B—C1B—N1B—C6B | 177.1 (3) |
C3A—C4A—C5A—N1A | 0.2 (5) | C7B—C1B—N1B—C6B | −2.3 (5) |
C4A—C5A—N1A—C1A | 1.2 (5) | O3—C8—C9—C10 | 179.4 (3) |
C4A—C5A—N1A—C6A | −176.6 (3) | C13—C8—C9—C10 | −0.6 (5) |
C2A—C1A—N1A—C5A | −0.8 (5) | C8—C9—C10—O4 | −176.7 (3) |
C7A—C1A—N1A—C5A | 179.6 (3) | C8—C9—C10—C11 | 2.4 (5) |
C2A—C1A—N1A—C6A | 176.9 (3) | O4—C10—C11—C12 | 176.4 (3) |
C7A—C1A—N1A—C6A | −2.6 (4) | C9—C10—C11—C12 | −2.6 (4) |
N1B—C1B—C2B—O1B | 179.1 (3) | C10—C11—C12—O5 | −179.0 (3) |
C7B—C1B—C2B—O1B | −1.6 (5) | C10—C11—C12—C13 | 1.1 (4) |
N1B—C1B—C2B—C3B | −0.5 (5) | O3—C8—C13—C12 | 179.2 (3) |
C7B—C1B—C2B—C3B | 178.9 (3) | C9—C8—C13—C12 | −0.8 (5) |
O1B—C2B—C3B—O2B | 1.9 (5) | O5—C12—C13—C8 | −179.3 (3) |
C1B—C2B—C3B—O2B | −178.6 (3) | C11—C12—C13—C8 | 0.6 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1OA···O2A | 0.87 (6) | 2.30 (6) | 2.756 (3) | 113 (4) |
O1A—H1OA···O2Ai | 0.87 (6) | 1.93 (6) | 2.678 (3) | 143 (5) |
O1B—H1OB···O2Bii | 0.86 (4) | 1.89 (4) | 2.638 (4) | 145 (4) |
O3—H3O···O1W | 0.87 (6) | 1.86 (6) | 2.721 (3) | 168 (5) |
O4—H4O···O1Wiii | 0.83 | 1.99 | 2.760 (3) | 154 |
O5—H5O···O2W | 0.79 (7) | 1.90 (7) | 2.673 (3) | 168 (6) |
O1W—H1W···O2B | 0.86 | 1.84 | 2.690 (3) | 172 |
O1W—H2W···O4iv | 0.95 | 1.85 | 2.760 (3) | 160 |
O1W—H2WD···O1Wv | 0.85 | 1.96 | 2.818 (5) | 176 |
O2W—H3W···O2A | 0.85 | 1.85 | 2.693 (3) | 177 |
O2W—H4W···O4iv | 0.92 | 1.83 | 2.752 (3) | 177 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y+1, −z+1; (iii) x−1, y, z; (iv) x+1, y, z; (v) −x+1, −y+2, −z+1. |
(KA803_0m_def-pyro_1_2)
top
Crystal data top
C7H9NO2·2(C6H6O3) | F(000) = 1648 |
Mr = 391.37 | Dx = 1.431 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 28.0626 (4) Å | Cell parameters from 9898 reflections |
b = 9.2719 (1) Å | θ = 2.6–30.6° |
c = 14.6075 (2) Å | µ = 0.11 mm−1 |
β = 107.0808 (5)° | T = 100 K |
V = 3633.13 (8) Å3 | Needle, colorless |
Z = 8 | 0.32 × 0.18 × 0.16 mm |
Data collection top
Bruker D8 QUEST PHOTON-100 diffractometer | 3357 reflections with I > 2σ(I) |
Radiation source: microfocus | Rint = 0.027 |
ω and φ scans | θmax = 26.3°, θmin = 2.3° |
Absorption correction: multi-scan SADABS, Bruker, 2016 | h = −34→34 |
Tmin = 0.693, Tmax = 0.746 | k = −11→11 |
23872 measured reflections | l = −18→18 |
3664 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.035 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.0563P)2 + 2.7534P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
3664 reflections | Δρmax = 0.43 e Å−3 |
283 parameters | Δρmin = −0.30 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 | |
C1 | 0.43916 (4) | −0.07673 (12) | 1.02071 (8) | 0.0132 (2) | |
C2 | 0.44400 (4) | 0.07094 (12) | 1.02368 (7) | 0.0117 (2) | |
C3 | 0.44137 (4) | 0.15283 (12) | 0.93988 (7) | 0.0113 (2) | |
C4 | 0.43261 (4) | 0.07434 (13) | 0.85397 (8) | 0.0145 (2) | |
H4 | 0.429760 | 0.123952 | 0.795703 | 0.017* | |
C5 | 0.42819 (4) | −0.07221 (13) | 0.85358 (8) | 0.0158 (2) | |
H5 | 0.422651 | −0.123025 | 0.794902 | 0.019* | |
C6 | 0.42792 (4) | −0.30550 (13) | 0.93044 (9) | 0.0205 (3) | |
H6A | 0.418201 | −0.336831 | 0.863421 | 0.031* | |
H6B | 0.402856 | −0.337643 | 0.960631 | 0.031* | |
H6C | 0.460343 | −0.347465 | 0.964452 | 0.031* | |
C7 | 0.44205 (5) | −0.16221 (13) | 1.10874 (9) | 0.0193 (2) | |
H7A | 0.453893 | −0.100239 | 1.165233 | 0.029* | |
H7B | 0.465237 | −0.242826 | 1.113520 | 0.029* | |
H7C | 0.408913 | −0.199693 | 1.105288 | 0.029* | |
O1 | 0.45241 (3) | 0.13873 (9) | 1.10948 (5) | 0.01534 (18) | |
H1O | 0.4552 (6) | 0.230 (2) | 1.0988 (12) | 0.034 (4)* | |
O2 | 0.44709 (3) | 0.29148 (8) | 0.94658 (5) | 0.01268 (18) | |
N1 | 0.43149 (3) | −0.14677 (10) | 0.93469 (7) | 0.0144 (2) | |
C8A | 0.41139 (4) | 0.45227 (11) | 0.73380 (7) | 0.0107 (2) | |
C9A | 0.41208 (4) | 0.52017 (11) | 0.64935 (7) | 0.0107 (2) | |
C10A | 0.36733 (4) | 0.55132 (12) | 0.57936 (7) | 0.0126 (2) | |
C11A | 0.32198 (4) | 0.51724 (13) | 0.59421 (8) | 0.0159 (2) | |
H11A | 0.291544 | 0.539665 | 0.546996 | 0.019* | |
C12A | 0.32171 (4) | 0.44987 (13) | 0.67907 (8) | 0.0168 (2) | |
H12A | 0.290803 | 0.426236 | 0.689604 | 0.020* | |
C13A | 0.36601 (4) | 0.41654 (12) | 0.74881 (8) | 0.0142 (2) | |
H13A | 0.365352 | 0.369731 | 0.806273 | 0.017* | |
O3A | 0.45640 (3) | 0.42227 (8) | 0.79924 (5) | 0.01282 (18) | |
H2O | 0.4516 (7) | 0.374 (2) | 0.8531 (13) | 0.043 (5)* | |
O4A | 0.45549 (3) | 0.56065 (9) | 0.63061 (6) | 0.01373 (18) | |
H3O | 0.4815 (7) | 0.5131 (19) | 0.6648 (13) | 0.037 (5)* | |
O5A | 0.36726 (3) | 0.61355 (9) | 0.49454 (5) | 0.01565 (18) | |
H40 | 0.3971 (7) | 0.629 (2) | 0.4928 (13) | 0.039 (5)* | |
C8B | 0.30615 (4) | 1.02767 (13) | 0.28780 (8) | 0.0172 (2) | |
C9B | 0.30945 (4) | 0.94795 (13) | 0.37025 (8) | 0.0148 (2) | |
C10B | 0.30958 (4) | 1.01835 (13) | 0.45470 (8) | 0.0171 (2) | |
C11B | 0.30578 (4) | 1.16756 (14) | 0.45566 (9) | 0.0213 (3) | |
H11B | 0.305663 | 1.216281 | 0.512810 | 0.026* | |
C12B | 0.30212 (4) | 1.24557 (14) | 0.37222 (10) | 0.0234 (3) | |
H12B | 0.299365 | 1.347647 | 0.373056 | 0.028* | |
C13B | 0.30244 (4) | 1.17663 (14) | 0.28774 (9) | 0.0217 (3) | |
H13B | 0.300172 | 1.230551 | 0.231318 | 0.026* | |
O3B | 0.30700 (3) | 0.95430 (11) | 0.20586 (6) | 0.0233 (2) | |
H5O | 0.3088 (7) | 0.861 (2) | 0.2211 (14) | 0.047 (5)* | |
O4B | 0.31178 (3) | 0.80175 (9) | 0.36250 (6) | 0.01821 (19) | |
H6O | 0.3236 (7) | 0.760 (2) | 0.4197 (15) | 0.048 (5)* | |
O5B | 0.31351 (3) | 0.92959 (10) | 0.53142 (6) | 0.0233 (2) | |
H7O | 0.3116 (7) | 0.978 (2) | 0.5838 (15) | 0.049 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0099 (5) | 0.0151 (5) | 0.0152 (5) | 0.0009 (4) | 0.0047 (4) | 0.0005 (4) |
C2 | 0.0098 (5) | 0.0148 (5) | 0.0111 (5) | 0.0011 (4) | 0.0040 (4) | −0.0007 (4) |
C3 | 0.0079 (5) | 0.0137 (5) | 0.0127 (5) | 0.0014 (4) | 0.0038 (4) | 0.0006 (4) |
C4 | 0.0144 (5) | 0.0186 (6) | 0.0110 (5) | 0.0010 (4) | 0.0046 (4) | 0.0007 (4) |
C5 | 0.0138 (5) | 0.0199 (6) | 0.0136 (5) | 0.0007 (4) | 0.0037 (4) | −0.0043 (4) |
C6 | 0.0202 (6) | 0.0124 (6) | 0.0279 (6) | 0.0003 (4) | 0.0052 (5) | −0.0038 (5) |
C7 | 0.0232 (6) | 0.0159 (6) | 0.0209 (6) | 0.0015 (5) | 0.0099 (5) | 0.0050 (4) |
O1 | 0.0226 (4) | 0.0143 (4) | 0.0099 (4) | 0.0006 (3) | 0.0059 (3) | −0.0003 (3) |
O2 | 0.0149 (4) | 0.0119 (4) | 0.0120 (4) | −0.0004 (3) | 0.0051 (3) | 0.0008 (3) |
N1 | 0.0131 (4) | 0.0126 (5) | 0.0179 (5) | 0.0002 (3) | 0.0049 (4) | −0.0021 (4) |
C8A | 0.0105 (5) | 0.0097 (5) | 0.0112 (5) | 0.0005 (4) | 0.0020 (4) | −0.0017 (4) |
C9A | 0.0099 (5) | 0.0102 (5) | 0.0130 (5) | −0.0002 (4) | 0.0049 (4) | −0.0012 (4) |
C10A | 0.0142 (5) | 0.0119 (5) | 0.0116 (5) | 0.0008 (4) | 0.0036 (4) | 0.0009 (4) |
C11A | 0.0107 (5) | 0.0201 (6) | 0.0155 (5) | 0.0007 (4) | 0.0015 (4) | 0.0014 (4) |
C12A | 0.0115 (5) | 0.0204 (6) | 0.0196 (6) | −0.0023 (4) | 0.0062 (4) | 0.0007 (4) |
C13A | 0.0148 (5) | 0.0162 (5) | 0.0129 (5) | −0.0016 (4) | 0.0061 (4) | 0.0018 (4) |
O3A | 0.0101 (4) | 0.0170 (4) | 0.0108 (4) | −0.0002 (3) | 0.0020 (3) | 0.0035 (3) |
O4A | 0.0097 (4) | 0.0170 (4) | 0.0153 (4) | 0.0013 (3) | 0.0049 (3) | 0.0066 (3) |
O5A | 0.0125 (4) | 0.0218 (4) | 0.0124 (4) | 0.0016 (3) | 0.0033 (3) | 0.0062 (3) |
C8B | 0.0105 (5) | 0.0247 (6) | 0.0159 (5) | 0.0009 (4) | 0.0032 (4) | 0.0021 (5) |
C9B | 0.0095 (5) | 0.0177 (6) | 0.0165 (5) | 0.0024 (4) | 0.0026 (4) | 0.0013 (4) |
C10B | 0.0112 (5) | 0.0231 (6) | 0.0166 (5) | 0.0020 (4) | 0.0036 (4) | 0.0005 (5) |
C11B | 0.0138 (5) | 0.0235 (6) | 0.0260 (6) | 0.0006 (5) | 0.0050 (5) | −0.0058 (5) |
C12B | 0.0144 (5) | 0.0174 (6) | 0.0368 (7) | 0.0005 (5) | 0.0049 (5) | 0.0003 (5) |
C13B | 0.0138 (5) | 0.0235 (6) | 0.0261 (6) | 0.0005 (5) | 0.0034 (5) | 0.0085 (5) |
O3B | 0.0299 (5) | 0.0261 (5) | 0.0146 (4) | 0.0000 (4) | 0.0078 (3) | 0.0040 (4) |
O4B | 0.0239 (4) | 0.0180 (4) | 0.0124 (4) | 0.0056 (3) | 0.0049 (3) | 0.0018 (3) |
O5B | 0.0325 (5) | 0.0255 (5) | 0.0134 (4) | 0.0049 (4) | 0.0091 (4) | −0.0002 (3) |
Geometric parameters (Å, º) top
C1—N1 | 1.3741 (14) | C10A—C11A | 1.3888 (15) |
C1—C2 | 1.3753 (16) | C11A—C12A | 1.3901 (16) |
C1—C7 | 1.4924 (15) | C11A—H11A | 0.9500 |
C2—O1 | 1.3593 (13) | C12A—C13A | 1.3909 (16) |
C2—C3 | 1.4238 (15) | C12A—H12A | 0.9500 |
C3—O2 | 1.2957 (14) | C13A—H13A | 0.9500 |
C3—C4 | 1.4084 (15) | O3A—H2O | 0.95 (2) |
C4—C5 | 1.3643 (17) | O4A—H3O | 0.872 (19) |
C4—H4 | 0.9500 | O5A—H40 | 0.858 (19) |
C5—N1 | 1.3513 (15) | C8B—O3B | 1.3831 (15) |
C5—H5 | 0.9500 | C8B—C13B | 1.3850 (18) |
C6—N1 | 1.4752 (15) | C8B—C9B | 1.3928 (16) |
C6—H6A | 0.9800 | C9B—O4B | 1.3634 (14) |
C6—H6B | 0.9800 | C9B—C10B | 1.3947 (16) |
C6—H6C | 0.9800 | C10B—O5B | 1.3684 (15) |
C7—H7A | 0.9800 | C10B—C11B | 1.3880 (18) |
C7—H7B | 0.9800 | C11B—C12B | 1.3950 (19) |
C7—H7C | 0.9800 | C11B—H11B | 0.9500 |
O1—H1O | 0.872 (19) | C12B—C13B | 1.3920 (19) |
C8A—O3A | 1.3701 (12) | C12B—H12B | 0.9500 |
C8A—C9A | 1.3901 (15) | C13B—H13B | 0.9500 |
C8A—C13A | 1.3940 (15) | O3B—H5O | 0.89 (2) |
C9A—O4A | 1.3769 (12) | O4B—H6O | 0.89 (2) |
C9A—C10A | 1.3969 (15) | O5B—H7O | 0.91 (2) |
C10A—O5A | 1.3662 (13) | | |
| | | |
N1—C1—C2 | 119.14 (10) | O5A—C10A—C11A | 118.71 (9) |
N1—C1—C7 | 119.42 (10) | O5A—C10A—C9A | 120.84 (9) |
C2—C1—C7 | 121.44 (10) | C11A—C10A—C9A | 120.44 (10) |
O1—C2—C1 | 118.57 (9) | C10A—C11A—C12A | 119.13 (10) |
O1—C2—C3 | 119.82 (10) | C10A—C11A—H11A | 120.4 |
C1—C2—C3 | 121.60 (10) | C12A—C11A—H11A | 120.4 |
O2—C3—C4 | 124.42 (10) | C11A—C12A—C13A | 121.01 (10) |
O2—C3—C2 | 119.35 (9) | C11A—C12A—H12A | 119.5 |
C4—C3—C2 | 116.23 (10) | C13A—C12A—H12A | 119.5 |
C5—C4—C3 | 120.68 (10) | C12A—C13A—C8A | 119.55 (10) |
C5—C4—H4 | 119.7 | C12A—C13A—H13A | 120.2 |
C3—C4—H4 | 119.7 | C8A—C13A—H13A | 120.2 |
N1—C5—C4 | 121.54 (10) | C8A—O3A—H2O | 110.4 (11) |
N1—C5—H5 | 119.2 | C9A—O4A—H3O | 112.8 (12) |
C4—C5—H5 | 119.2 | C10A—O5A—H40 | 110.9 (12) |
N1—C6—H6A | 109.5 | O3B—C8B—C13B | 120.69 (11) |
N1—C6—H6B | 109.5 | O3B—C8B—C9B | 118.27 (11) |
H6A—C6—H6B | 109.5 | C13B—C8B—C9B | 121.04 (11) |
N1—C6—H6C | 109.5 | O4B—C9B—C8B | 116.64 (10) |
H6A—C6—H6C | 109.5 | O4B—C9B—C10B | 123.44 (10) |
H6B—C6—H6C | 109.5 | C8B—C9B—C10B | 119.91 (11) |
C1—C7—H7A | 109.5 | O5B—C10B—C11B | 125.39 (11) |
C1—C7—H7B | 109.5 | O5B—C10B—C9B | 114.93 (10) |
H7A—C7—H7B | 109.5 | C11B—C10B—C9B | 119.68 (11) |
C1—C7—H7C | 109.5 | C10B—C11B—C12B | 119.61 (11) |
H7A—C7—H7C | 109.5 | C10B—C11B—H11B | 120.2 |
H7B—C7—H7C | 109.5 | C12B—C11B—H11B | 120.2 |
C2—O1—H1O | 106.6 (11) | C13B—C12B—C11B | 121.23 (12) |
C5—N1—C1 | 120.80 (10) | C13B—C12B—H12B | 119.4 |
C5—N1—C6 | 119.15 (10) | C11B—C12B—H12B | 119.4 |
C1—N1—C6 | 120.03 (10) | C8B—C13B—C12B | 118.51 (11) |
O3A—C8A—C9A | 117.44 (9) | C8B—C13B—H13B | 120.7 |
O3A—C8A—C13A | 122.65 (9) | C12B—C13B—H13B | 120.7 |
C9A—C8A—C13A | 119.92 (9) | C8B—O3B—H5O | 106.0 (12) |
O4A—C9A—C8A | 122.93 (9) | C9B—O4B—H6O | 111.4 (13) |
O4A—C9A—C10A | 117.11 (9) | C10B—O5B—H7O | 112.4 (13) |
C8A—C9A—C10A | 119.95 (9) | | |
| | | |
N1—C1—C2—O1 | −178.89 (9) | O4A—C9A—C10A—C11A | −178.29 (10) |
C7—C1—C2—O1 | 1.11 (15) | C8A—C9A—C10A—C11A | 1.16 (16) |
N1—C1—C2—C3 | −0.14 (15) | O5A—C10A—C11A—C12A | 178.05 (10) |
C7—C1—C2—C3 | 179.86 (9) | C9A—C10A—C11A—C12A | −0.90 (17) |
O1—C2—C3—O2 | 0.05 (14) | C10A—C11A—C12A—C13A | 0.05 (17) |
C1—C2—C3—O2 | −178.69 (9) | C11A—C12A—C13A—C8A | 0.55 (17) |
O1—C2—C3—C4 | 179.91 (9) | O3A—C8A—C13A—C12A | −179.79 (10) |
C1—C2—C3—C4 | 1.17 (15) | C9A—C8A—C13A—C12A | −0.29 (16) |
O2—C3—C4—C5 | 178.42 (10) | O3B—C8B—C9B—O4B | −1.93 (15) |
C2—C3—C4—C5 | −1.43 (15) | C13B—C8B—C9B—O4B | 178.50 (10) |
C3—C4—C5—N1 | 0.69 (17) | O3B—C8B—C9B—C10B | 178.90 (10) |
C4—C5—N1—C1 | 0.43 (16) | C13B—C8B—C9B—C10B | −0.67 (16) |
C4—C5—N1—C6 | −178.18 (10) | O4B—C9B—C10B—O5B | 1.57 (15) |
C2—C1—N1—C5 | −0.69 (15) | C8B—C9B—C10B—O5B | −179.32 (9) |
C7—C1—N1—C5 | 179.31 (9) | O4B—C9B—C10B—C11B | −178.31 (10) |
C2—C1—N1—C6 | 177.90 (9) | C8B—C9B—C10B—C11B | 0.81 (16) |
C7—C1—N1—C6 | −2.10 (15) | O5B—C10B—C11B—C12B | 179.81 (10) |
O3A—C8A—C9A—O4A | −1.61 (15) | C9B—C10B—C11B—C12B | −0.33 (17) |
C13A—C8A—C9A—O4A | 178.86 (10) | C10B—C11B—C12B—C13B | −0.30 (17) |
O3A—C8A—C9A—C10A | 178.97 (9) | O3B—C8B—C13B—C12B | −179.51 (10) |
C13A—C8A—C9A—C10A | −0.56 (15) | C9B—C8B—C13B—C12B | 0.05 (17) |
O4A—C9A—C10A—O5A | 2.79 (15) | C11B—C12B—C13B—C8B | 0.44 (17) |
C8A—C9A—C10A—O5A | −177.76 (9) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O4Ai | 0.872 (19) | 1.992 (19) | 2.8029 (12) | 154 (2) |
O3A—H2O···O2 | 0.95 (2) | 1.60 (2) | 2.5498 (10) | 177 (2) |
O4A—H3O···O3Aii | 0.872 (19) | 1.868 (19) | 2.7059 (11) | 161 (2) |
O5A—H40···O2iii | 0.858 (19) | 1.877 (19) | 2.6846 (11) | 156 (2) |
O3B—H5O···O4B | 0.89 (2) | 2.11 (2) | 2.6595 (12) | 119 (2) |
O4B—H6O···O5A | 0.89 (2) | 1.94 (2) | 2.7249 (11) | 146 (2) |
O5B—H7O···O3Biv | 0.91 (2) | 1.93 (2) | 2.8213 (12) | 169 (2) |
C6—H6C···O2v | 0.98 | 2.59 | 3.4416 (14) | 145 |
C13A—H13A···O4Bi | 0.95 | 2.49 | 3.2642 (13) | 139 |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) −x+1, y, −z+3/2; (iii) x, −y+1, z−1/2; (iv) x, −y+2, z+1/2; (v) −x+1, −y, −z+2. |
(KA1032_0m_def-pyro_2_4)
top
Crystal data top
C7H9NO2·2(C6H6O3) | Dx = 1.428 Mg m−3 |
Mr = 391.37 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pna21 | Cell parameters from 7479 reflections |
a = 14.592 (2) Å | θ = 2.3–30.5° |
b = 9.3121 (11) Å | µ = 0.11 mm−1 |
c = 26.795 (4) Å | T = 100 K |
V = 3640.9 (8) Å3 | Block, colorless |
Z = 8 | 0.32 × 0.28 × 0.18 mm |
F(000) = 1648 | |
Data collection top
Bruker D8 QUEST PHOTON-100 diffractometer | 3817 reflections with I > 2σ(I) |
Radiation source: microfocus | Rint = 0.120 |
ω and φ scans | θmax = 27.5°, θmin = 2.3° |
Absorption correction: multi-scan SADABS, Bruker, 2016 | h = −18→18 |
Tmin = 0.545, Tmax = 0.746 | k = −12→12 |
16757 measured reflections | l = −34→30 |
6362 independent reflections | |
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)] = 0.073 | w = 1/[σ2(Fo2) + (0.0646P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.156 | (Δ/σ)max = 0.027 |
S = 1.05 | Δρmax = 0.45 e Å−3 |
6362 reflections | Δρmin = −0.40 e Å−3 |
565 parameters | Absolute structure: Flack x determined using 732 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
6 restraints | Absolute structure parameter: 0.4 (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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1A | 0.3562 (4) | 0.1729 (7) | 0.4402 (2) | 0.0175 (14) | |
C2A | 0.3562 (4) | 0.3219 (7) | 0.4453 (2) | 0.0139 (13) | |
C3A | 0.4381 (4) | 0.4023 (6) | 0.44335 (18) | 0.0135 (12) | |
C4A | 0.5198 (4) | 0.3246 (6) | 0.43433 (19) | 0.0167 (13) | |
H4A | 0.576537 | 0.373994 | 0.431810 | 0.020* | |
C5A | 0.5171 (4) | 0.1782 (7) | 0.4292 (2) | 0.0197 (13) | |
H5A | 0.572644 | 0.127773 | 0.423365 | 0.024* | |
C6A | 0.4414 (4) | −0.0549 (6) | 0.4277 (2) | 0.0238 (14) | |
H6A | 0.394029 | −0.087117 | 0.404292 | 0.036* | |
H6B | 0.430649 | −0.098587 | 0.460449 | 0.036* | |
H6C | 0.501808 | −0.083940 | 0.415288 | 0.036* | |
C7A | 0.2707 (4) | 0.0865 (7) | 0.4426 (2) | 0.0238 (16) | |
H7A | 0.254302 | 0.053989 | 0.408928 | 0.036* | |
H7B | 0.220969 | 0.145466 | 0.456118 | 0.036* | |
H7C | 0.280410 | 0.002903 | 0.464153 | 0.036* | |
O1A | 0.2748 (3) | 0.3879 (5) | 0.45389 (15) | 0.0175 (9) | |
H1O | 0.281 (5) | 0.477 (3) | 0.453 (3) | 0.06 (3)* | |
O2A | 0.4347 (2) | 0.5415 (4) | 0.44946 (13) | 0.0150 (9) | |
N1A | 0.4379 (3) | 0.1035 (5) | 0.43227 (16) | 0.0181 (11) | |
C1B | 0.9657 (4) | 0.1746 (6) | 0.5630 (2) | 0.0167 (13) | |
C2B | 0.9659 (4) | 0.3197 (6) | 0.55825 (19) | 0.0148 (12) | |
C3B | 0.8835 (4) | 0.4031 (7) | 0.55999 (19) | 0.0137 (13) | |
C4B | 0.8033 (4) | 0.3242 (6) | 0.5682 (2) | 0.0171 (14) | |
H4B | 0.746618 | 0.373940 | 0.570732 | 0.021* | |
C5B | 0.8036 (4) | 0.1810 (6) | 0.5725 (2) | 0.0176 (14) | |
H5B | 0.747149 | 0.132030 | 0.577152 | 0.021* | |
C6B | 0.8796 (5) | −0.0545 (6) | 0.5736 (2) | 0.0256 (15) | |
H6D | 0.816281 | −0.086581 | 0.578407 | 0.038* | |
H6E | 0.917147 | −0.086234 | 0.601857 | 0.038* | |
H6F | 0.903942 | −0.095843 | 0.542660 | 0.038* | |
C7B | 1.0513 (4) | 0.0890 (6) | 0.5606 (2) | 0.0220 (14) | |
H7D | 1.042701 | 0.008030 | 0.537725 | 0.033* | |
H7E | 1.066167 | 0.052628 | 0.593971 | 0.033* | |
H7F | 1.101460 | 0.149728 | 0.548595 | 0.033* | |
O1B | 1.0472 (3) | 0.3880 (4) | 0.54975 (14) | 0.0189 (9) | |
H2O | 1.040 (5) | 0.475 (3) | 0.542 (3) | 0.05 (2)* | |
O2B | 0.8875 (2) | 0.5416 (4) | 0.55430 (14) | 0.0165 (9) | |
N1B | 0.8820 (3) | 0.1045 (5) | 0.57032 (16) | 0.0165 (11) | |
C8A | 0.6274 (4) | 0.7024 (6) | 0.41384 (19) | 0.0139 (12) | |
C9A | 0.7118 (4) | 0.7707 (6) | 0.41431 (19) | 0.0135 (12) | |
C10A | 0.7569 (4) | 0.7999 (6) | 0.3698 (2) | 0.0156 (12) | |
C11A | 0.7175 (4) | 0.7654 (6) | 0.3249 (2) | 0.0198 (13) | |
H11A | 0.748141 | 0.787077 | 0.294542 | 0.024* | |
C12A | 0.6330 (5) | 0.6987 (7) | 0.3242 (2) | 0.0230 (14) | |
H12A | 0.605602 | 0.675173 | 0.293132 | 0.028* | |
C13A | 0.5869 (4) | 0.6653 (6) | 0.3686 (2) | 0.0171 (14) | |
H13A | 0.529222 | 0.618127 | 0.367821 | 0.021* | |
O3A | 0.5863 (3) | 0.6726 (4) | 0.45876 (13) | 0.0160 (10) | |
H3O | 0.528 (5) | 0.637 (6) | 0.453 (2) | 0.034 (19)* | |
O4A | 0.7547 (3) | 0.8129 (4) | 0.45811 (14) | 0.0192 (9) | |
H4O | 0.734 (4) | 0.757 (6) | 0.479 (2) | 0.008 (14)* | |
O5A | 0.8423 (3) | 0.8623 (4) | 0.36995 (15) | 0.0193 (9) | |
H5O | 0.862 (8) | 0.857 (11) | 0.3984 (18) | 0.12 (4)* | |
C8B | 0.8484 (4) | 1.2642 (7) | 0.3106 (2) | 0.0215 (15) | |
C9B | 0.9321 (4) | 1.1931 (6) | 0.3108 (2) | 0.0156 (13) | |
C10B | 1.0125 (4) | 1.2732 (7) | 0.30622 (19) | 0.0207 (14) | |
C11B | 1.0107 (4) | 1.4222 (7) | 0.3010 (2) | 0.0248 (14) | |
H11B | 1.065798 | 1.475824 | 0.297616 | 0.030* | |
C12B | 0.9240 (5) | 1.4912 (7) | 0.3009 (2) | 0.0274 (15) | |
H12B | 0.920408 | 1.592532 | 0.297330 | 0.033* | |
C13B | 0.8448 (4) | 1.4116 (7) | 0.3058 (2) | 0.0234 (14) | |
H13B | 0.787149 | 1.458846 | 0.305987 | 0.028* | |
O3B | 0.7728 (3) | 1.1758 (5) | 0.31597 (16) | 0.0253 (10) | |
H6O | 0.728 (5) | 1.227 (7) | 0.312 (2) | 0.018 (19)* | |
O4B | 0.9422 (3) | 1.0483 (5) | 0.31351 (15) | 0.0216 (9) | |
H7O | 0.893 (4) | 1.009 (6) | 0.326 (2) | 0.015 (15)* | |
O5B | 1.0959 (3) | 1.2018 (6) | 0.30738 (16) | 0.0264 (11) | |
H8O | 1.086 (6) | 1.111 (9) | 0.304 (3) | 0.07 (3)* | |
C8C | 0.2995 (4) | 1.2728 (7) | 0.6946 (2) | 0.0210 (14) | |
C9C | 0.3809 (5) | 1.1979 (7) | 0.6920 (2) | 0.0228 (14) | |
C10C | 0.4649 (4) | 1.2718 (7) | 0.6921 (2) | 0.0230 (15) | |
C11C | 0.4649 (5) | 1.4215 (7) | 0.6961 (2) | 0.0298 (16) | |
H11C | 0.520792 | 1.473729 | 0.696490 | 0.036* | |
C12C | 0.3810 (5) | 1.4923 (7) | 0.6995 (2) | 0.0309 (17) | |
H12C | 0.380472 | 1.593854 | 0.702884 | 0.037* | |
C13C | 0.2990 (5) | 1.4202 (7) | 0.6980 (2) | 0.0301 (16) | |
H13C | 0.242728 | 1.471279 | 0.699365 | 0.036* | |
O3C | 0.2189 (3) | 1.1958 (6) | 0.69358 (16) | 0.0300 (11) | |
H9O | 0.227 (5) | 1.108 (7) | 0.689 (2) | 0.03 (2)* | |
O4C | 0.3759 (3) | 1.0515 (5) | 0.68998 (15) | 0.0232 (10) | |
H10O | 0.419 (7) | 0.996 (13) | 0.687 (6) | 0.21 (7)* | |
O5C | 0.5409 (3) | 1.1870 (6) | 0.68822 (18) | 0.0305 (11) | |
H11O | 0.591 (4) | 1.226 (10) | 0.694 (5) | 0.10 (5)* | |
C8D | 0.5652 (4) | 0.8007 (6) | 0.6347 (2) | 0.0146 (12) | |
C9D | 0.6100 (4) | 0.7699 (6) | 0.58971 (19) | 0.0149 (12) | |
C10D | 0.6950 (4) | 0.7030 (6) | 0.59073 (18) | 0.0150 (12) | |
C11D | 0.7356 (4) | 0.6676 (6) | 0.6363 (2) | 0.0185 (13) | |
H11D | 0.793727 | 0.621581 | 0.636940 | 0.022* | |
C12D | 0.6909 (4) | 0.7000 (7) | 0.6805 (2) | 0.0223 (14) | |
H12D | 0.718888 | 0.676015 | 0.711409 | 0.027* | |
C13D | 0.6061 (4) | 0.7666 (6) | 0.6803 (2) | 0.0208 (14) | |
H13D | 0.576139 | 0.788913 | 0.710814 | 0.025* | |
O3D | 0.4804 (3) | 0.8635 (4) | 0.63489 (15) | 0.0203 (9) | |
H12O | 0.460 (5) | 0.874 (7) | 0.607 (3) | 0.04 (2)* | |
O4D | 0.5667 (3) | 0.8107 (4) | 0.54649 (14) | 0.0166 (10) | |
H13O | 0.578 (6) | 0.773 (9) | 0.516 (4) | 0.08 (3)* | |
O5D | 0.7342 (3) | 0.6738 (4) | 0.54591 (13) | 0.0159 (9) | |
H14O | 0.777 (4) | 0.618 (6) | 0.552 (2) | 0.021 (17)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.011 (3) | 0.029 (4) | 0.013 (3) | −0.002 (3) | −0.003 (2) | 0.002 (2) |
C2A | 0.008 (3) | 0.018 (3) | 0.016 (3) | 0.000 (2) | −0.003 (2) | −0.002 (2) |
C3A | 0.008 (3) | 0.021 (4) | 0.011 (3) | −0.003 (2) | −0.002 (2) | 0.003 (2) |
C4A | 0.004 (3) | 0.027 (4) | 0.019 (3) | 0.000 (2) | 0.000 (2) | 0.000 (2) |
C5A | 0.010 (3) | 0.027 (4) | 0.022 (3) | 0.007 (3) | 0.001 (2) | −0.001 (2) |
C6A | 0.018 (3) | 0.021 (4) | 0.032 (3) | 0.002 (3) | −0.001 (3) | 0.003 (3) |
C7A | 0.024 (4) | 0.020 (4) | 0.028 (3) | −0.003 (3) | −0.006 (3) | −0.001 (2) |
O1A | 0.005 (2) | 0.021 (3) | 0.026 (2) | 0.0038 (17) | 0.0013 (17) | 0.0012 (18) |
O2A | 0.007 (2) | 0.019 (2) | 0.0188 (19) | −0.0025 (16) | 0.0010 (16) | −0.0015 (16) |
N1A | 0.014 (3) | 0.022 (3) | 0.018 (2) | 0.003 (2) | −0.004 (2) | −0.001 (2) |
C1B | 0.017 (3) | 0.019 (3) | 0.014 (2) | −0.002 (3) | −0.001 (2) | 0.002 (2) |
C2B | 0.008 (3) | 0.021 (3) | 0.016 (3) | −0.004 (2) | 0.003 (2) | −0.002 (2) |
C3B | 0.011 (3) | 0.023 (4) | 0.006 (2) | 0.000 (2) | −0.001 (2) | −0.001 (2) |
C4B | 0.014 (3) | 0.020 (3) | 0.017 (3) | 0.000 (3) | 0.000 (2) | 0.001 (2) |
C5B | 0.005 (3) | 0.030 (4) | 0.018 (3) | −0.004 (3) | 0.000 (2) | −0.002 (2) |
C6B | 0.032 (4) | 0.023 (4) | 0.022 (3) | −0.004 (3) | 0.003 (3) | 0.006 (2) |
C7B | 0.018 (3) | 0.020 (3) | 0.028 (3) | 0.007 (3) | −0.004 (3) | −0.001 (2) |
O1B | 0.010 (2) | 0.019 (3) | 0.028 (2) | 0.0020 (18) | 0.0010 (18) | 0.0034 (18) |
O2B | 0.011 (2) | 0.020 (2) | 0.0190 (19) | 0.0001 (16) | 0.0005 (16) | 0.0024 (16) |
N1B | 0.019 (3) | 0.014 (3) | 0.016 (2) | −0.003 (2) | 0.003 (2) | −0.0003 (19) |
C8A | 0.014 (3) | 0.016 (3) | 0.012 (2) | 0.007 (2) | 0.001 (2) | −0.001 (2) |
C9A | 0.011 (3) | 0.016 (3) | 0.014 (2) | 0.005 (2) | −0.003 (2) | −0.001 (2) |
C10A | 0.013 (3) | 0.016 (3) | 0.018 (2) | 0.000 (2) | 0.001 (2) | 0.000 (2) |
C11A | 0.013 (3) | 0.030 (4) | 0.016 (3) | 0.004 (3) | 0.002 (2) | 0.000 (2) |
C12A | 0.024 (4) | 0.032 (4) | 0.013 (2) | −0.001 (3) | −0.003 (3) | −0.002 (2) |
C13A | 0.014 (3) | 0.021 (4) | 0.016 (3) | −0.005 (2) | −0.005 (2) | 0.003 (2) |
O3A | 0.008 (2) | 0.028 (3) | 0.0119 (19) | −0.0073 (18) | 0.0001 (16) | 0.0002 (16) |
O4A | 0.023 (2) | 0.022 (2) | 0.0135 (18) | −0.0093 (19) | −0.0016 (17) | 0.0030 (16) |
O5A | 0.011 (2) | 0.028 (3) | 0.0185 (19) | −0.0055 (17) | −0.0016 (18) | 0.0036 (17) |
C8B | 0.016 (4) | 0.035 (4) | 0.014 (3) | −0.003 (3) | 0.000 (3) | 0.002 (3) |
C9B | 0.009 (3) | 0.022 (4) | 0.016 (3) | −0.003 (2) | −0.002 (2) | 0.003 (2) |
C10B | 0.017 (3) | 0.033 (4) | 0.012 (3) | 0.003 (3) | 0.001 (2) | 0.002 (2) |
C11B | 0.021 (4) | 0.033 (4) | 0.021 (3) | −0.012 (3) | 0.003 (3) | 0.001 (2) |
C12B | 0.039 (4) | 0.025 (4) | 0.018 (3) | 0.004 (3) | 0.000 (3) | 0.002 (2) |
C13B | 0.016 (4) | 0.033 (4) | 0.021 (3) | 0.007 (3) | −0.001 (3) | 0.000 (3) |
O3B | 0.010 (2) | 0.033 (3) | 0.033 (2) | 0.004 (2) | −0.002 (2) | 0.0063 (19) |
O4B | 0.013 (2) | 0.024 (3) | 0.027 (2) | −0.0012 (19) | 0.0041 (19) | 0.0032 (19) |
O5B | 0.011 (3) | 0.035 (3) | 0.033 (3) | −0.003 (2) | 0.001 (2) | 0.000 (2) |
C8C | 0.020 (4) | 0.027 (4) | 0.016 (3) | 0.002 (3) | 0.001 (3) | −0.004 (2) |
C9C | 0.029 (4) | 0.026 (4) | 0.013 (3) | 0.000 (3) | 0.002 (3) | −0.004 (2) |
C10C | 0.019 (4) | 0.032 (4) | 0.018 (3) | −0.003 (3) | 0.001 (3) | −0.002 (3) |
C11C | 0.043 (5) | 0.030 (4) | 0.017 (3) | −0.013 (3) | 0.004 (3) | −0.004 (3) |
C12C | 0.050 (5) | 0.023 (4) | 0.019 (3) | 0.004 (3) | 0.002 (3) | 0.002 (2) |
C13C | 0.029 (4) | 0.044 (5) | 0.018 (3) | 0.010 (3) | 0.005 (3) | −0.003 (3) |
O3C | 0.018 (3) | 0.040 (3) | 0.032 (2) | 0.010 (2) | 0.001 (2) | −0.005 (2) |
O4C | 0.015 (2) | 0.029 (3) | 0.026 (2) | −0.002 (2) | −0.0021 (19) | −0.0085 (19) |
O5C | 0.010 (3) | 0.042 (3) | 0.039 (3) | −0.001 (2) | 0.000 (2) | 0.002 (2) |
C8D | 0.012 (3) | 0.017 (3) | 0.015 (2) | −0.001 (3) | 0.004 (2) | 0.000 (2) |
C9D | 0.013 (3) | 0.015 (3) | 0.017 (3) | −0.003 (2) | −0.002 (2) | 0.002 (2) |
C10D | 0.012 (3) | 0.019 (3) | 0.014 (2) | −0.006 (2) | 0.003 (2) | −0.002 (2) |
C11D | 0.011 (3) | 0.027 (4) | 0.018 (3) | 0.001 (2) | 0.004 (2) | 0.002 (2) |
C12D | 0.018 (3) | 0.036 (4) | 0.013 (2) | 0.004 (3) | −0.001 (2) | 0.001 (2) |
C13D | 0.021 (4) | 0.030 (4) | 0.011 (2) | −0.002 (3) | 0.004 (2) | −0.001 (2) |
O3D | 0.009 (2) | 0.035 (3) | 0.0162 (18) | 0.0058 (18) | −0.0005 (18) | −0.0007 (17) |
O4D | 0.012 (2) | 0.024 (2) | 0.0137 (19) | 0.0073 (18) | −0.0024 (17) | −0.0018 (16) |
O5D | 0.010 (2) | 0.024 (3) | 0.0144 (18) | 0.0050 (18) | 0.0027 (17) | 0.0015 (16) |
Geometric parameters (Å, º) top
C1A—N1A | 1.373 (8) | C13A—H13A | 0.9500 |
C1A—C2A | 1.395 (9) | O3A—H3O | 0.93 (7) |
C1A—C7A | 1.486 (8) | O4A—H4O | 0.82 (5) |
C2A—O1A | 1.357 (7) | O5A—H5O | 0.82 (3) |
C2A—C3A | 1.411 (8) | C8B—C13B | 1.379 (9) |
C3A—O2A | 1.308 (7) | C8B—O3B | 1.383 (7) |
C3A—C4A | 1.414 (8) | C8B—C9B | 1.389 (9) |
C4A—C5A | 1.370 (9) | C9B—O4B | 1.358 (7) |
C4A—H4A | 0.9500 | C9B—C10B | 1.396 (9) |
C5A—N1A | 1.352 (8) | C10B—O5B | 1.388 (8) |
C5A—H5A | 0.9500 | C10B—C11B | 1.395 (8) |
C6A—N1A | 1.481 (8) | C11B—C12B | 1.420 (9) |
C6A—H6A | 0.9800 | C11B—H11B | 0.9500 |
C6A—H6B | 0.9800 | C12B—C13B | 1.378 (9) |
C6A—H6C | 0.9800 | C12B—H12B | 0.9500 |
C7A—H7A | 0.9800 | C13B—H13B | 0.9500 |
C7A—H7B | 0.9800 | O3B—H6O | 0.82 (7) |
C7A—H7C | 0.9800 | O4B—H7O | 0.87 (6) |
O1A—H1O | 0.84 (3) | O5B—H8O | 0.86 (9) |
C1B—C2B | 1.357 (8) | C8C—C13C | 1.375 (9) |
C1B—N1B | 1.399 (8) | C8C—O3C | 1.377 (8) |
C1B—C7B | 1.483 (8) | C8C—C9C | 1.379 (10) |
C2B—O1B | 1.365 (7) | C9C—O4C | 1.366 (8) |
C2B—C3B | 1.432 (8) | C9C—C10C | 1.406 (9) |
C3B—O2B | 1.300 (7) | C10C—O5C | 1.366 (8) |
C3B—C4B | 1.400 (9) | C10C—C11C | 1.398 (9) |
C4B—C5B | 1.338 (8) | C11C—C12C | 1.394 (10) |
C4B—H4B | 0.9500 | C11C—H11C | 0.9500 |
C5B—N1B | 1.349 (8) | C12C—C13C | 1.372 (10) |
C5B—H5B | 0.9500 | C12C—H12C | 0.9500 |
C6B—N1B | 1.484 (8) | C13C—H13C | 0.9500 |
C6B—H6D | 0.9800 | O3C—H9O | 0.83 (7) |
C6B—H6E | 0.9800 | O4C—H10O | 0.82 (3) |
C6B—H6F | 0.9800 | O5C—H11O | 0.84 (3) |
C7B—H7D | 0.9800 | C8D—O3D | 1.369 (7) |
C7B—H7E | 0.9800 | C8D—C13D | 1.397 (8) |
C7B—H7F | 0.9800 | C8D—C9D | 1.401 (8) |
O1B—H2O | 0.84 (3) | C9D—O4D | 1.373 (6) |
C8A—O3A | 1.373 (6) | C9D—C10D | 1.388 (8) |
C8A—C9A | 1.386 (8) | C10D—O5D | 1.358 (6) |
C8A—C13A | 1.392 (8) | C10D—C11D | 1.396 (8) |
C9A—O4A | 1.387 (6) | C11D—C12D | 1.386 (8) |
C9A—C10A | 1.390 (8) | C11D—H11D | 0.9500 |
C10A—C11A | 1.371 (8) | C12D—C13D | 1.384 (9) |
C10A—O5A | 1.375 (7) | C12D—H12D | 0.9500 |
C11A—C12A | 1.381 (9) | C13D—H13D | 0.9500 |
C11A—H11A | 0.9500 | O3D—H12O | 0.82 (7) |
C12A—C13A | 1.400 (8) | O4D—H13O | 0.91 (9) |
C12A—H12A | 0.9500 | O5D—H14O | 0.83 (6) |
| | | |
N1A—C1A—C2A | 118.9 (6) | C12A—C11A—H11A | 120.3 |
N1A—C1A—C7A | 118.7 (6) | C11A—C12A—C13A | 121.2 (5) |
C2A—C1A—C7A | 122.4 (6) | C11A—C12A—H12A | 119.4 |
O1A—C2A—C1A | 117.8 (5) | C13A—C12A—H12A | 119.4 |
O1A—C2A—C3A | 120.5 (5) | C8A—C13A—C12A | 118.7 (5) |
C1A—C2A—C3A | 121.6 (6) | C8A—C13A—H13A | 120.7 |
O2A—C3A—C2A | 119.2 (5) | C12A—C13A—H13A | 120.7 |
O2A—C3A—C4A | 124.1 (5) | C8A—O3A—H3O | 110 (4) |
C2A—C3A—C4A | 116.7 (6) | C9A—O4A—H4O | 103 (4) |
C5A—C4A—C3A | 120.1 (5) | C10A—O5A—H5O | 107 (8) |
C5A—C4A—H4A | 119.9 | C13B—C8B—O3B | 124.9 (6) |
C3A—C4A—H4A | 119.9 | C13B—C8B—C9B | 120.5 (6) |
N1A—C5A—C4A | 122.1 (6) | O3B—C8B—C9B | 114.6 (6) |
N1A—C5A—H5A | 119.0 | O4B—C9B—C8B | 124.7 (6) |
C4A—C5A—H5A | 119.0 | O4B—C9B—C10B | 116.4 (5) |
N1A—C6A—H6A | 109.5 | C8B—C9B—C10B | 118.9 (6) |
N1A—C6A—H6B | 109.5 | O5B—C10B—C9B | 118.7 (6) |
H6A—C6A—H6B | 109.5 | O5B—C10B—C11B | 119.6 (6) |
N1A—C6A—H6C | 109.5 | C9B—C10B—C11B | 121.7 (6) |
H6A—C6A—H6C | 109.5 | C10B—C11B—C12B | 117.8 (6) |
H6B—C6A—H6C | 109.5 | C10B—C11B—H11B | 121.1 |
C1A—C7A—H7A | 109.5 | C12B—C11B—H11B | 121.1 |
C1A—C7A—H7B | 109.5 | C13B—C12B—C11B | 120.2 (6) |
H7A—C7A—H7B | 109.5 | C13B—C12B—H12B | 119.9 |
C1A—C7A—H7C | 109.5 | C11B—C12B—H12B | 119.9 |
H7A—C7A—H7C | 109.5 | C12B—C13B—C8B | 120.9 (6) |
H7B—C7A—H7C | 109.5 | C12B—C13B—H13B | 119.6 |
C2A—O1A—H1O | 111 (6) | C8B—C13B—H13B | 119.6 |
C5A—N1A—C1A | 120.6 (5) | C8B—O3B—H6O | 106 (5) |
C5A—N1A—C6A | 118.6 (5) | C9B—O4B—H7O | 110 (4) |
C1A—N1A—C6A | 120.8 (5) | C10B—O5B—H8O | 108 (6) |
C2B—C1B—N1B | 118.7 (5) | C13C—C8C—O3C | 121.1 (6) |
C2B—C1B—C7B | 121.9 (6) | C13C—C8C—C9C | 120.8 (6) |
N1B—C1B—C7B | 119.3 (5) | O3C—C8C—C9C | 118.1 (6) |
C1B—C2B—O1B | 118.8 (5) | O4C—C9C—C8C | 117.4 (6) |
C1B—C2B—C3B | 122.3 (6) | O4C—C9C—C10C | 122.4 (6) |
O1B—C2B—C3B | 118.8 (5) | C8C—C9C—C10C | 120.2 (6) |
O2B—C3B—C4B | 125.2 (6) | O5C—C10C—C11C | 125.6 (6) |
O2B—C3B—C2B | 119.8 (5) | O5C—C10C—C9C | 115.1 (6) |
C4B—C3B—C2B | 115.0 (6) | C11C—C10C—C9C | 119.2 (6) |
C5B—C4B—C3B | 122.2 (6) | C12C—C11C—C10C | 118.5 (6) |
C5B—C4B—H4B | 118.9 | C12C—C11C—H11C | 120.8 |
C3B—C4B—H4B | 118.9 | C10C—C11C—H11C | 120.8 |
C4B—C5B—N1B | 121.7 (6) | C13C—C12C—C11C | 122.1 (6) |
C4B—C5B—H5B | 119.1 | C13C—C12C—H12C | 118.9 |
N1B—C5B—H5B | 119.1 | C11C—C12C—H12C | 118.9 |
N1B—C6B—H6D | 109.5 | C12C—C13C—C8C | 119.1 (6) |
N1B—C6B—H6E | 109.5 | C12C—C13C—H13C | 120.5 |
H6D—C6B—H6E | 109.5 | C8C—C13C—H13C | 120.5 |
N1B—C6B—H6F | 109.5 | C8C—O3C—H9O | 113 (5) |
H6D—C6B—H6F | 109.5 | C9C—O4C—H10O | 127 (10) |
H6E—C6B—H6F | 109.5 | C10C—O5C—H11O | 117 (7) |
C1B—C7B—H7D | 109.5 | O3D—C8D—C13D | 118.7 (5) |
C1B—C7B—H7E | 109.5 | O3D—C8D—C9D | 120.8 (5) |
H7D—C7B—H7E | 109.5 | C13D—C8D—C9D | 120.5 (5) |
C1B—C7B—H7F | 109.5 | O4D—C9D—C10D | 123.5 (5) |
H7D—C7B—H7F | 109.5 | O4D—C9D—C8D | 117.0 (5) |
H7E—C7B—H7F | 109.5 | C10D—C9D—C8D | 119.5 (5) |
C2B—O1B—H2O | 112 (5) | O5D—C10D—C9D | 116.7 (5) |
C5B—N1B—C1B | 120.0 (5) | O5D—C10D—C11D | 123.1 (5) |
C5B—N1B—C6B | 120.4 (5) | C9D—C10D—C11D | 120.2 (5) |
C1B—N1B—C6B | 119.6 (5) | C12D—C11D—C10D | 119.7 (5) |
O3A—C8A—C9A | 118.2 (5) | C12D—C11D—H11D | 120.1 |
O3A—C8A—C13A | 121.9 (5) | C10D—C11D—H11D | 120.1 |
C9A—C8A—C13A | 119.9 (5) | C13D—C12D—C11D | 121.0 (5) |
C8A—C9A—O4A | 122.6 (5) | C13D—C12D—H12D | 119.5 |
C8A—C9A—C10A | 120.2 (5) | C11D—C12D—H12D | 119.5 |
O4A—C9A—C10A | 117.3 (5) | C12D—C13D—C8D | 119.1 (5) |
C11A—C10A—O5A | 118.8 (5) | C12D—C13D—H13D | 120.4 |
C11A—C10A—C9A | 120.6 (5) | C8D—C13D—H13D | 120.4 |
O5A—C10A—C9A | 120.6 (5) | C8D—O3D—H12O | 112 (5) |
C10A—C11A—C12A | 119.4 (5) | C9D—O4D—H13O | 125 (6) |
C10A—C11A—H11A | 120.3 | C10D—O5D—H14O | 106 (4) |
| | | |
N1A—C1A—C2A—O1A | −179.1 (5) | O3A—C8A—C13A—C12A | −179.8 (5) |
C7A—C1A—C2A—O1A | 1.6 (8) | C9A—C8A—C13A—C12A | −0.2 (8) |
N1A—C1A—C2A—C3A | −1.0 (8) | C11A—C12A—C13A—C8A | 0.9 (9) |
C7A—C1A—C2A—C3A | 179.6 (5) | C13B—C8B—C9B—O4B | −177.5 (5) |
O1A—C2A—C3A—O2A | −0.5 (8) | O3B—C8B—C9B—O4B | 3.2 (8) |
C1A—C2A—C3A—O2A | −178.5 (5) | C13B—C8B—C9B—C10B | 0.1 (9) |
O1A—C2A—C3A—C4A | 179.9 (5) | O3B—C8B—C9B—C10B | −179.2 (5) |
C1A—C2A—C3A—C4A | 1.9 (7) | O4B—C9B—C10B—O5B | −3.4 (7) |
O2A—C3A—C4A—C5A | 178.9 (5) | C8B—C9B—C10B—O5B | 178.9 (5) |
C2A—C3A—C4A—C5A | −1.6 (7) | O4B—C9B—C10B—C11B | 177.2 (5) |
C3A—C4A—C5A—N1A | 0.3 (8) | C8B—C9B—C10B—C11B | −0.6 (9) |
C4A—C5A—N1A—C1A | 0.6 (8) | O5B—C10B—C11B—C12B | −178.9 (5) |
C4A—C5A—N1A—C6A | −178.4 (5) | C9B—C10B—C11B—C12B | 0.5 (8) |
C2A—C1A—N1A—C5A | −0.3 (8) | C10B—C11B—C12B—C13B | 0.1 (9) |
C7A—C1A—N1A—C5A | 179.1 (5) | C11B—C12B—C13B—C8B | −0.5 (9) |
C2A—C1A—N1A—C6A | 178.7 (5) | O3B—C8B—C13B—C12B | 179.7 (5) |
C7A—C1A—N1A—C6A | −1.9 (7) | C9B—C8B—C13B—C12B | 0.5 (9) |
N1B—C1B—C2B—O1B | −178.2 (4) | C13C—C8C—C9C—O4C | 178.4 (5) |
C7B—C1B—C2B—O1B | 1.7 (8) | O3C—C8C—C9C—O4C | −1.7 (8) |
N1B—C1B—C2B—C3B | −0.6 (8) | C13C—C8C—C9C—C10C | −0.9 (9) |
C7B—C1B—C2B—C3B | 179.3 (5) | O3C—C8C—C9C—C10C | 179.0 (5) |
C1B—C2B—C3B—O2B | −178.7 (5) | O4C—C9C—C10C—O5C | 2.3 (9) |
O1B—C2B—C3B—O2B | −1.1 (7) | C8C—C9C—C10C—O5C | −178.5 (5) |
C1B—C2B—C3B—C4B | 1.5 (8) | O4C—C9C—C10C—C11C | −177.7 (5) |
O1B—C2B—C3B—C4B | 179.1 (4) | C8C—C9C—C10C—C11C | 1.5 (9) |
O2B—C3B—C4B—C5B | 178.3 (5) | O5C—C10C—C11C—C12C | 179.6 (6) |
C2B—C3B—C4B—C5B | −2.0 (8) | C9C—C10C—C11C—C12C | −0.4 (9) |
C3B—C4B—C5B—N1B | 1.6 (9) | C10C—C11C—C12C—C13C | −1.3 (9) |
C4B—C5B—N1B—C1B | −0.5 (8) | C11C—C12C—C13C—C8C | 1.9 (9) |
C4B—C5B—N1B—C6B | −178.0 (5) | O3C—C8C—C13C—C12C | 179.3 (5) |
C2B—C1B—N1B—C5B | 0.1 (8) | C9C—C8C—C13C—C12C | −0.8 (9) |
C7B—C1B—N1B—C5B | −179.9 (5) | O3D—C8D—C9D—O4D | 2.6 (8) |
C2B—C1B—N1B—C6B | 177.6 (5) | C13D—C8D—C9D—O4D | −178.0 (5) |
C7B—C1B—N1B—C6B | −2.4 (7) | O3D—C8D—C9D—C10D | −178.4 (5) |
O3A—C8A—C9A—O4A | −1.7 (8) | C13D—C8D—C9D—C10D | 1.0 (8) |
C13A—C8A—C9A—O4A | 178.7 (5) | O4D—C9D—C10D—O5D | −2.1 (8) |
O3A—C8A—C9A—C10A | 178.5 (5) | C8D—C9D—C10D—O5D | 178.9 (5) |
C13A—C8A—C9A—C10A | −1.1 (9) | O4D—C9D—C10D—C11D | 178.5 (5) |
C8A—C9A—C10A—C11A | 1.8 (8) | C8D—C9D—C10D—C11D | −0.5 (8) |
O4A—C9A—C10A—C11A | −178.0 (5) | O5D—C10D—C11D—C12D | −179.5 (6) |
C8A—C9A—C10A—O5A | −177.3 (5) | C9D—C10D—C11D—C12D | −0.2 (8) |
O4A—C9A—C10A—O5A | 2.9 (8) | C10D—C11D—C12D—C13D | 0.2 (9) |
O5A—C10A—C11A—C12A | 178.0 (5) | C11D—C12D—C13D—C8D | 0.4 (10) |
C9A—C10A—C11A—C12A | −1.1 (9) | O3D—C8D—C13D—C12D | 178.4 (6) |
C10A—C11A—C12A—C13A | −0.3 (9) | C9D—C8D—C13D—C12D | −1.0 (9) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1O···O4Ai | 0.84 (3) | 2.00 (4) | 2.804 (6) | 162 (8) |
O1B—H2O···O4Dii | 0.84 (3) | 2.04 (4) | 2.821 (6) | 155 (7) |
O3A—H3O···O2A | 0.93 (7) | 1.63 (7) | 2.539 (5) | 167 (6) |
O4A—H4O···O3A | 0.82 (5) | 2.35 (6) | 2.782 (6) | 114 (4) |
O4A—H4O···O5D | 0.82 (5) | 1.96 (5) | 2.702 (5) | 151 (5) |
O5A—H5O···O2Aii | 0.82 (3) | 1.97 (7) | 2.676 (5) | 144 (10) |
O5A—H5O···O4A | 0.82 (3) | 2.28 (11) | 2.726 (6) | 115 (10) |
O3B—H6O···O5Biii | 0.82 (7) | 2.04 (7) | 2.831 (7) | 163 (6) |
O4B—H7O···O5A | 0.87 (6) | 1.95 (6) | 2.722 (6) | 146 (5) |
O5B—H8O···O4B | 0.86 (9) | 2.19 (9) | 2.666 (6) | 114 (7) |
O3C—H9O···O4C | 0.83 (7) | 2.24 (7) | 2.657 (7) | 111 (6) |
O4C—H10O···O3D | 0.82 (3) | 2.06 (11) | 2.752 (6) | 142 (15) |
O5C—H11O···O3Civ | 0.84 (3) | 2.00 (4) | 2.821 (7) | 169 (12) |
O3D—H12O···O2Bi | 0.82 (7) | 1.92 (7) | 2.698 (6) | 157 (7) |
O3D—H12O···O4D | 0.82 (7) | 2.32 (7) | 2.727 (6) | 112 (6) |
O4D—H13O···O3A | 0.91 (9) | 1.80 (9) | 2.695 (5) | 170 (9) |
O5D—H14O···O2B | 0.83 (6) | 1.76 (6) | 2.564 (5) | 163 (6) |
C13A—H13A···O4Bi | 0.95 | 2.48 | 3.255 (7) | 139 |
C6B—H6F···O2Av | 0.98 | 2.59 | 3.424 (7) | 143 |
C11D—H11D···O4Cii | 0.95 | 2.46 | 3.228 (7) | 138 |
Symmetry codes: (i) x−1/2, −y+3/2, z; (ii) x+1/2, −y+3/2, z; (iii) x−1/2, −y+5/2, z; (iv) x+1/2, −y+5/2, z; (v) x+1/2, −y+1/2, z. |
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