Temperature-induced order–disorder structural phase transitions of two-dimensional isostructural hexa­methyl­enetetramine co-crystals

Hexamethylenetetramine-benzoic acid (1/2) (HBA) and hexamethylenetetramine-4-methylbenzoic acid (1/2) (HMBA) co-crystals undergo order–disorder structural phase transition from a low-temperature monoclinic crystal structure to a high-temperature orthorhombic crystal structure at the transition temperatures of 257.5 (5) K (Pn ↔ Fmm2) and 265.5 (5) K (P2₁/n ↔ Cmcm), respectively, using variable-temperature single-crystal X-ray diffraction analysis. The observed phase transitions were confirmed to be reversible first-order transitions as indicated by the sharp endothermic and exothermic peaks in the differential scanning calorimetry measurement. The three-molecule aggregate of HBA and HMBA consists of a hexamethylenetetramine molecule and two benzoic acid or two 4-methylbenzoic acid molecules, respectively. The acid molecules are ordered at the low-temperature phase and are equally disordered over two positions, which are related by a mirror symmetry, at the high-temperature phase. The two-dimensional supramolecular constructs common to both co-crystals are formed by three-molecule aggregates via weak intermolecular C—H...O and C—H...π interactions into molecular trilayers parallel to the ac plane with small XPac dissimilarity indices and parameters. The PIXEL interaction energies of all corresponding molecular contacts were calculated and the results are comparable between HBA and HMBA co-crystals, resulting in similar lattice energies and transition temperatures despite their two-dimensional isostructural relationship. The observed phase transitions of these two energetically similar co-crystals are triggered by similar mechanisms, i.e. the molecular rotator ordering and structural order–disorder transformation, which induced non-merohedral twinning with similar twin matrices in the low-temperature crystal form of both co-crystals.

Computing details

For all structures, data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015). Molecular graphics: SHELXTL (Sheldrick, 2008), Mercury (Macrae et al., 2008) for 1533065, 1533066, 1533067, 1533068, 1533069, 1533070, 1533071, 1533072, 1533073, 1533075, 1533076; SHELXTL (Sheldrick, 2008), (Macrae et al., 2008) for 1533074. For all structures, software used to prepare material for publication: PLATON (Spek, 2009).

Hexamethylenetetramine bis(benzoic acid) (1533065)

Crystal data

C6H12N4·2(C7H6O2)	F(000) = 816
Mr = 384.43	Dx = 1.343 Mg m^−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
a = 6.0925 (5) Å	Cell parameters from 9986 reflections
b = 26.145 (2) Å	θ = 2.9–28.4°
c = 12.1017 (10) Å	µ = 0.10 mm^−1
β = 99.3633 (17)°	T = 100 K
V = 1902.0 (3) Å^3	Block, colourless
Z = 4	0.76 × 0.39 × 0.21 mm

Data collection

Bruker APEX Duo CCD area detector diffractometer	4725 independent reflections
Radiation source: fine-focus sealed tube	3719 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
φ and ω scans	θmax = 28.4°, θmin = 1.9°
Absorption correction: multi-scan (TWINABS; Sheldrick, 2012)	h = −8→8
Tmin = 0.810, Tmax = 0.929	k = 0→34
5967 measured reflections	l = 0→16

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.0424P)^2 + 0.5679P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.113	(Δ/σ)max = 0.001
S = 1.11	Δρmax = 0.29 e Å^−3
4725 reflections	Δρmin = −0.21 e Å^−3
522 parameters	Absolute structure: No quotients, so Flack parameter determined by classical intensity fit
6 restraints	Absolute structure parameter: −0.3 (8)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1A	0.6880 (5)	0.37873 (10)	0.4653 (2)	0.0286 (6)
H1O1	0.625 (7)	0.4020 (13)	0.496 (4)	0.044 (13)*
O2A	0.4041 (4)	0.39828 (10)	0.3314 (2)	0.0331 (7)
O3A	0.4289 (4)	0.61070 (9)	0.3987 (2)	0.0210 (5)
H1O3	0.429 (7)	0.5901 (13)	0.452 (3)	0.031 (11)*
O4A	0.7923 (4)	0.60567 (10)	0.4617 (2)	0.0283 (6)
N1A	0.4883 (4)	0.44883 (10)	0.5718 (2)	0.0165 (6)
N2A	0.4013 (4)	0.53955 (10)	0.5446 (2)	0.0171 (6)
N3A	0.1385 (5)	0.48222 (10)	0.6143 (2)	0.0183 (6)
N4A	0.4892 (5)	0.50519 (10)	0.7329 (2)	0.0198 (6)
C1A	0.5090 (6)	0.49429 (12)	0.5019 (3)	0.0181 (7)
H1AA	0.4385	0.4872	0.4238	0.022*
H1AB	0.6684	0.5017	0.5019	0.022*
C2A	0.1653 (5)	0.52706 (12)	0.5449 (3)	0.0191 (7)
H2AA	0.0909	0.5568	0.5735	0.023*
H2AB	0.0915	0.5204	0.4672	0.023*
C3A	0.2498 (5)	0.43883 (11)	0.5704 (3)	0.0179 (6)
H3AA	0.1774	0.4317	0.4926	0.022*
H3AB	0.2329	0.4081	0.6161	0.022*
C4A	0.5941 (6)	0.46104 (12)	0.6883 (3)	0.0204 (7)
H4AA	0.5825	0.4310	0.7368	0.024*
H4AB	0.7540	0.4683	0.6896	0.024*
C5A	0.5108 (6)	0.54930 (12)	0.6618 (3)	0.0190 (7)
H5AA	0.6704	0.5568	0.6628	0.023*
H5AB	0.4420	0.5796	0.6915	0.023*
C6A	0.2525 (6)	0.49358 (14)	0.7285 (3)	0.0221 (7)
H6AA	0.1788	0.5231	0.7582	0.027*
H6AB	0.2375	0.4638	0.7773	0.027*
C7A	0.6943 (6)	0.34656 (12)	0.2835 (3)	0.0190 (7)
C8A	0.9124 (6)	0.32952 (12)	0.3149 (3)	0.0232 (7)
H8AA	0.9891	0.3352	0.3887	0.028*
C9A	1.0160 (7)	0.30396 (13)	0.2365 (3)	0.0299 (9)
H9AA	1.1655	0.2927	0.2564	0.036*
C10A	0.9035 (7)	0.29491 (14)	0.1308 (4)	0.0342 (10)
H10A	0.9750	0.2771	0.0782	0.041*
C11A	0.6868 (7)	0.31141 (13)	0.1002 (3)	0.0311 (9)
H11A	0.6102	0.3051	0.0266	0.037*
C12A	0.5808 (6)	0.33718 (13)	0.1768 (3)	0.0243 (7)
H12A	0.4313	0.3483	0.1562	0.029*
C13A	0.5807 (6)	0.37694 (12)	0.3619 (3)	0.0208 (7)
C14A	0.6695 (5)	0.65438 (12)	0.2975 (3)	0.0167 (6)
C15A	0.4914 (5)	0.66774 (12)	0.2163 (3)	0.0183 (7)
H15A	0.3459	0.6565	0.2230	0.022*
C16A	0.5237 (6)	0.69748 (12)	0.1252 (3)	0.0229 (7)
H16A	0.4014	0.7059	0.0690	0.027*
C17A	0.7349 (6)	0.71474 (12)	0.1169 (3)	0.0241 (7)
H17A	0.7569	0.7361	0.0561	0.029*
C18A	0.9143 (6)	0.70103 (11)	0.1969 (3)	0.0204 (7)
H18A	1.0595	0.7123	0.1896	0.024*
C19A	0.8836 (6)	0.67096 (11)	0.2877 (3)	0.0186 (7)
H19A	1.0070	0.6617	0.3427	0.022*
C20A	0.6370 (6)	0.62169 (11)	0.3944 (3)	0.0170 (7)
O1B	1.4421 (5)	0.88191 (10)	0.7182 (2)	0.0268 (6)
H2O1	1.368 (9)	0.9007 (19)	0.753 (5)	0.08 (2)*
O2B	1.1677 (4)	0.90082 (10)	0.5798 (2)	0.0316 (6)
O3B	1.1732 (4)	1.11186 (9)	0.6510 (2)	0.0229 (5)
H2O3	1.161 (10)	1.0899 (17)	0.701 (4)	0.08 (2)*
O4B	1.5356 (4)	1.10986 (10)	0.7191 (2)	0.0294 (6)
N1B	1.2365 (5)	0.95068 (9)	0.8223 (2)	0.0153 (6)
N2B	1.1441 (4)	1.04133 (9)	0.7986 (2)	0.0138 (5)
N3B	0.8855 (5)	0.98287 (11)	0.8657 (2)	0.0204 (6)
N4B	1.2341 (5)	1.00494 (10)	0.9860 (2)	0.0179 (6)
C1B	1.2541 (6)	0.99711 (10)	0.7548 (3)	0.0143 (7)
H1BA	1.1846	0.9906	0.6763	0.017*
H1BB	1.4130	1.0052	0.7554	0.017*
C2B	0.9072 (5)	1.02839 (12)	0.7976 (3)	0.0200 (7)
H2BA	0.8313	1.0576	0.8271	0.024*
H2BB	0.8342	1.0221	0.7195	0.024*
C3B	0.9972 (5)	0.94012 (12)	0.8203 (3)	0.0203 (7)
H3BA	0.9252	0.9335	0.7422	0.024*
H3BB	0.9810	0.9090	0.8648	0.024*
C4B	1.3405 (6)	0.96169 (12)	0.9401 (3)	0.0190 (7)
H4BA	1.3284	0.9311	0.9868	0.023*
H4BB	1.5005	0.9692	0.9426	0.023*
C5B	1.2528 (6)	1.05016 (11)	0.9157 (3)	0.0180 (7)
H5BA	1.4118	1.0583	0.9168	0.022*
H5BB	1.1824	1.0799	0.9467	0.022*
C6B	0.9972 (6)	0.99309 (13)	0.9804 (3)	0.0210 (7)
H6BA	0.9229	1.0222	1.0113	0.025*
H6BB	0.9818	0.9628	1.0276	0.025*
C7B	1.4563 (6)	0.84617 (11)	0.5417 (3)	0.0175 (7)
C8B	1.6752 (6)	0.83103 (11)	0.5744 (3)	0.0194 (7)
H8BA	1.7519	0.8400	0.6465	0.023*
C9B	1.7832 (7)	0.80270 (13)	0.5018 (3)	0.0291 (8)
H9BA	1.9331	0.7923	0.5245	0.035*
C10B	1.6713 (7)	0.78974 (13)	0.3966 (3)	0.0323 (9)
H10B	1.7443	0.7701	0.3474	0.039*
C11B	1.4553 (8)	0.80517 (14)	0.3631 (3)	0.0329 (9)
H11B	1.3797	0.7961	0.2908	0.039*
C12B	1.3464 (6)	0.83402 (12)	0.4343 (3)	0.0236 (7)
H12B	1.1983	0.8454	0.4100	0.028*
C13B	1.3402 (6)	0.87835 (11)	0.6138 (3)	0.0182 (7)
C14B	1.4158 (5)	1.15522 (11)	0.5505 (3)	0.0139 (6)
C15B	1.2410 (5)	1.16483 (11)	0.4641 (3)	0.0162 (6)
H15B	1.0977	1.1513	0.4680	0.019*
C16B	1.2732 (6)	1.19398 (11)	0.3723 (3)	0.0192 (7)
H16B	1.1522	1.2010	0.3142	0.023*
C17B	1.4838 (6)	1.21281 (12)	0.3661 (3)	0.0213 (7)
H17B	1.5072	1.2324	0.3030	0.026*
C18B	1.6600 (6)	1.20328 (13)	0.4512 (3)	0.0236 (7)
H18B	1.8032	1.2167	0.4467	0.028*
C19B	1.6275 (6)	1.17396 (12)	0.5435 (3)	0.0207 (7)
H19B	1.7488	1.1668	0.6013	0.025*
C20B	1.3810 (6)	1.12393 (11)	0.6485 (3)	0.0177 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0296 (15)	0.0353 (14)	0.0200 (13)	0.0159 (12)	0.0018 (11)	−0.0055 (11)
O2A	0.0238 (14)	0.0419 (15)	0.0309 (15)	0.0135 (12)	−0.0037 (12)	−0.0084 (12)
O3A	0.0189 (12)	0.0247 (12)	0.0197 (12)	0.0005 (10)	0.0037 (10)	0.0109 (10)
O4A	0.0207 (13)	0.0373 (14)	0.0248 (13)	0.0011 (11)	−0.0025 (11)	0.0113 (11)
N1A	0.0120 (14)	0.0218 (13)	0.0165 (13)	0.0012 (10)	0.0047 (11)	0.0034 (10)
N2A	0.0158 (15)	0.0230 (13)	0.0131 (13)	0.0006 (11)	0.0041 (11)	−0.0005 (10)
N3A	0.0142 (14)	0.0185 (13)	0.0233 (14)	−0.0001 (11)	0.0066 (12)	0.0028 (11)
N4A	0.0207 (16)	0.0235 (13)	0.0151 (15)	−0.0013 (11)	0.0026 (13)	0.0009 (10)
C1A	0.0133 (17)	0.0268 (16)	0.0159 (17)	0.0021 (12)	0.0071 (14)	0.0007 (12)
C2A	0.0147 (16)	0.0202 (14)	0.0224 (16)	0.0024 (12)	0.0025 (14)	0.0006 (12)
C3A	0.0167 (16)	0.0142 (13)	0.0234 (16)	−0.0028 (12)	0.0051 (13)	−0.0001 (12)
C4A	0.0193 (18)	0.0213 (15)	0.0199 (16)	0.0021 (13)	0.0015 (14)	0.0048 (12)
C5A	0.0206 (17)	0.0220 (15)	0.0147 (15)	−0.0041 (13)	0.0039 (13)	0.0002 (12)
C6A	0.0215 (19)	0.0284 (16)	0.0191 (17)	−0.0011 (14)	0.0106 (15)	0.0016 (13)
C7A	0.0185 (16)	0.0189 (14)	0.0208 (17)	0.0034 (13)	0.0065 (14)	0.0023 (12)
C8A	0.0239 (18)	0.0193 (15)	0.0282 (18)	0.0051 (13)	0.0098 (15)	0.0041 (13)
C9A	0.032 (2)	0.0209 (16)	0.042 (2)	0.0125 (15)	0.0225 (19)	0.0130 (15)
C10A	0.047 (3)	0.0246 (17)	0.037 (2)	0.0112 (17)	0.025 (2)	0.0055 (16)
C11A	0.048 (3)	0.0217 (17)	0.0239 (19)	0.0019 (17)	0.0082 (18)	−0.0002 (14)
C12A	0.0269 (19)	0.0250 (16)	0.0212 (17)	0.0013 (14)	0.0044 (15)	0.0022 (13)
C13A	0.0195 (18)	0.0222 (15)	0.0211 (17)	0.0015 (13)	0.0045 (15)	−0.0015 (13)
C14A	0.0156 (16)	0.0175 (14)	0.0175 (15)	−0.0001 (12)	0.0040 (13)	−0.0009 (12)
C15A	0.0164 (16)	0.0184 (14)	0.0206 (15)	0.0027 (12)	0.0045 (13)	0.0006 (12)
C16A	0.0219 (17)	0.0240 (16)	0.0222 (17)	0.0024 (13)	0.0016 (15)	0.0031 (13)
C17A	0.0301 (19)	0.0194 (15)	0.0250 (18)	0.0019 (14)	0.0114 (15)	0.0047 (13)
C18A	0.0209 (17)	0.0153 (14)	0.0274 (18)	−0.0010 (13)	0.0109 (15)	0.0037 (13)
C19A	0.0151 (15)	0.0195 (14)	0.0215 (16)	0.0029 (12)	0.0037 (13)	0.0027 (12)
C20A	0.0179 (17)	0.0169 (13)	0.0159 (15)	0.0018 (12)	0.0017 (13)	0.0010 (12)
O1B	0.0321 (15)	0.0292 (13)	0.0185 (12)	0.0177 (11)	0.0021 (11)	−0.0039 (10)
O2B	0.0256 (14)	0.0373 (14)	0.0285 (14)	0.0148 (12)	−0.0057 (12)	−0.0073 (12)
O3B	0.0218 (13)	0.0245 (12)	0.0211 (13)	−0.0012 (10)	0.0000 (11)	0.0087 (10)
O4B	0.0267 (15)	0.0341 (13)	0.0243 (13)	0.0020 (11)	−0.0053 (12)	0.0125 (11)
N1B	0.0199 (15)	0.0130 (11)	0.0128 (12)	−0.0006 (10)	0.0020 (11)	−0.0012 (10)
N2B	0.0188 (15)	0.0091 (10)	0.0130 (12)	−0.0010 (10)	0.0012 (11)	0.0007 (9)
N3B	0.0151 (14)	0.0246 (14)	0.0226 (15)	0.0002 (11)	0.0061 (12)	−0.0032 (11)
N4B	0.0247 (17)	0.0173 (12)	0.0114 (14)	−0.0016 (11)	0.0024 (12)	−0.0011 (9)
C1B	0.0200 (18)	0.0083 (13)	0.0152 (16)	−0.0010 (10)	0.0040 (14)	0.0011 (9)
C2B	0.0145 (16)	0.0238 (15)	0.0210 (16)	0.0035 (13)	0.0011 (14)	0.0043 (13)
C3B	0.0208 (17)	0.0198 (14)	0.0208 (16)	−0.0031 (13)	0.0047 (14)	−0.0021 (12)
C4B	0.0210 (18)	0.0218 (15)	0.0127 (15)	0.0031 (13)	−0.0014 (13)	0.0035 (12)
C5B	0.0218 (18)	0.0157 (13)	0.0161 (15)	−0.0015 (12)	0.0019 (14)	−0.0037 (11)
C6B	0.027 (2)	0.0203 (14)	0.0177 (17)	0.0009 (14)	0.0103 (15)	0.0016 (12)
C7B	0.0272 (18)	0.0079 (12)	0.0173 (15)	−0.0006 (12)	0.0034 (14)	−0.0001 (11)
C8B	0.0235 (18)	0.0145 (14)	0.0205 (16)	−0.0009 (13)	0.0044 (14)	−0.0008 (12)
C9B	0.033 (2)	0.0241 (17)	0.033 (2)	0.0045 (15)	0.0145 (17)	0.0029 (14)
C10B	0.051 (3)	0.0181 (15)	0.033 (2)	0.0030 (17)	0.022 (2)	−0.0070 (15)
C11B	0.053 (3)	0.0260 (18)	0.0198 (17)	−0.0006 (18)	0.0073 (18)	−0.0065 (14)
C12B	0.031 (2)	0.0188 (15)	0.0204 (17)	−0.0020 (14)	0.0008 (15)	−0.0005 (13)
C13B	0.0230 (17)	0.0133 (13)	0.0175 (16)	0.0023 (12)	0.0006 (14)	−0.0029 (12)
C14B	0.0196 (16)	0.0085 (12)	0.0139 (14)	0.0016 (11)	0.0031 (13)	−0.0011 (10)
C15B	0.0173 (16)	0.0114 (12)	0.0192 (15)	−0.0006 (11)	0.0011 (13)	0.0016 (11)
C16B	0.0231 (17)	0.0176 (14)	0.0156 (15)	0.0005 (13)	−0.0005 (13)	0.0007 (12)
C17B	0.0281 (18)	0.0168 (14)	0.0197 (16)	0.0010 (14)	0.0055 (14)	0.0039 (13)
C18B	0.0171 (17)	0.0245 (16)	0.0298 (19)	−0.0006 (13)	0.0052 (15)	−0.0053 (14)
C19B	0.0181 (16)	0.0210 (14)	0.0216 (16)	0.0033 (13)	−0.0005 (14)	−0.0042 (12)
C20B	0.0237 (18)	0.0123 (13)	0.0161 (16)	0.0017 (12)	−0.0003 (14)	−0.0008 (11)

Geometric parameters (Å, º)

O1A—C13A	1.316 (4)	O1B—C13B	1.316 (4)
O1A—H1O1	0.840 (19)	O1B—H2O1	0.83 (2)
O2A—C13A	1.214 (4)	O2B—C13B	1.216 (4)
O3A—C20A	1.309 (4)	O3B—C20B	1.310 (4)
O3A—H1O3	0.837 (19)	O3B—H2O3	0.84 (2)
O4A—C20A	1.218 (4)	O4B—C20B	1.221 (4)
N1A—C3A	1.474 (4)	N1B—C1B	1.477 (4)
N1A—C1A	1.476 (4)	N1B—C3B	1.480 (4)
N1A—C4A	1.487 (4)	N1B—C4B	1.491 (4)
N2A—C2A	1.476 (4)	N2B—C1B	1.477 (4)
N2A—C1A	1.486 (4)	N2B—C2B	1.480 (4)
N2A—C5A	1.487 (4)	N2B—C5B	1.481 (4)
N3A—C3A	1.465 (4)	N3B—C3B	1.462 (4)
N3A—C2A	1.466 (4)	N3B—C2B	1.466 (4)
N3A—C6A	1.472 (4)	N3B—C6B	1.468 (4)
N4A—C5A	1.458 (4)	N4B—C4B	1.458 (4)
N4A—C4A	1.465 (4)	N4B—C6B	1.467 (5)
N4A—C6A	1.466 (5)	N4B—C5B	1.472 (4)
C1A—H1AA	0.9900	C1B—H1BA	0.9900
C1A—H1AB	0.9900	C1B—H1BB	0.9900
C2A—H2AA	0.9900	C2B—H2BA	0.9900
C2A—H2AB	0.9900	C2B—H2BB	0.9900
C3A—H3AA	0.9900	C3B—H3BA	0.9900
C3A—H3AB	0.9900	C3B—H3BB	0.9900
C4A—H4AA	0.9900	C4B—H4BA	0.9900
C4A—H4AB	0.9900	C4B—H4BB	0.9900
C5A—H5AA	0.9900	C5B—H5BA	0.9900
C5A—H5AB	0.9900	C5B—H5BB	0.9900
C6A—H6AA	0.9900	C6B—H6BA	0.9900
C6A—H6AB	0.9900	C6B—H6BB	0.9900
C7A—C12A	1.383 (5)	C7B—C8B	1.386 (5)
C7A—C8A	1.394 (5)	C7B—C12B	1.399 (5)
C7A—C13A	1.492 (5)	C7B—C13B	1.473 (5)
C8A—C9A	1.394 (5)	C8B—C9B	1.393 (5)
C8A—H8AA	0.9500	C8B—H8BA	0.9500
C9A—C10A	1.369 (6)	C9B—C10B	1.385 (6)
C9A—H9AA	0.9500	C9B—H9BA	0.9500
C10A—C11A	1.381 (6)	C10B—C11B	1.373 (6)
C10A—H10A	0.9500	C10B—H10B	0.9500
C11A—C12A	1.388 (5)	C11B—C12B	1.392 (5)
C11A—H11A	0.9500	C11B—H11B	0.9500
C12A—H12A	0.9500	C12B—H12B	0.9500
C14A—C15A	1.385 (4)	C14B—C15B	1.388 (4)
C14A—C19A	1.398 (5)	C14B—C19B	1.395 (5)
C14A—C20A	1.490 (5)	C14B—C20B	1.484 (4)
C15A—C16A	1.389 (5)	C15B—C16B	1.388 (4)
C15A—H15A	0.9500	C15B—H15B	0.9500
C16A—C17A	1.382 (5)	C16B—C17B	1.388 (5)
C16A—H16A	0.9500	C16B—H16B	0.9500
C17A—C18A	1.384 (5)	C17B—C18B	1.383 (5)
C17A—H17A	0.9500	C17B—H17B	0.9500
C18A—C19A	1.388 (4)	C18B—C19B	1.396 (5)
C18A—H18A	0.9500	C18B—H18B	0.9500
C19A—H19A	0.9500	C19B—H19B	0.9500
C13A—O1A—H1O1	105 (3)	C13B—O1B—H2O1	109 (4)
C20A—O3A—H1O3	107 (3)	C20B—O3B—H2O3	112 (4)
C3A—N1A—C1A	108.2 (2)	C1B—N1B—C3B	107.7 (3)
C3A—N1A—C4A	108.8 (3)	C1B—N1B—C4B	108.2 (2)
C1A—N1A—C4A	107.8 (2)	C3B—N1B—C4B	108.4 (2)
C2A—N2A—C1A	108.1 (2)	C1B—N2B—C2B	108.5 (2)
C2A—N2A—C5A	108.8 (2)	C1B—N2B—C5B	107.9 (2)
C1A—N2A—C5A	108.2 (2)	C2B—N2B—C5B	109.1 (2)
C3A—N3A—C2A	108.1 (3)	C3B—N3B—C2B	108.6 (3)
C3A—N3A—C6A	108.7 (3)	C3B—N3B—C6B	108.8 (3)
C2A—N3A—C6A	107.3 (3)	C2B—N3B—C6B	108.3 (3)
C5A—N4A—C4A	108.6 (3)	C4B—N4B—C6B	108.3 (3)
C5A—N4A—C6A	109.0 (3)	C4B—N4B—C5B	108.8 (3)
C4A—N4A—C6A	108.0 (3)	C6B—N4B—C5B	108.1 (3)
N1A—C1A—N2A	111.0 (3)	N1B—C1B—N2B	111.5 (3)
N1A—C1A—H1AA	109.4	N1B—C1B—H1BA	109.3
N2A—C1A—H1AA	109.4	N2B—C1B—H1BA	109.3
N1A—C1A—H1AB	109.4	N1B—C1B—H1BB	109.3
N2A—C1A—H1AB	109.4	N2B—C1B—H1BB	109.3
H1AA—C1A—H1AB	108.0	H1BA—C1B—H1BB	108.0
N3A—C2A—N2A	112.2 (2)	N3B—C2B—N2B	111.0 (2)
N3A—C2A—H2AA	109.2	N3B—C2B—H2BA	109.4
N2A—C2A—H2AA	109.2	N2B—C2B—H2BA	109.4
N3A—C2A—H2AB	109.2	N3B—C2B—H2BB	109.4
N2A—C2A—H2AB	109.2	N2B—C2B—H2BB	109.4
H2AA—C2A—H2AB	107.9	H2BA—C2B—H2BB	108.0
N3A—C3A—N1A	111.8 (2)	N3B—C3B—N1B	111.7 (2)
N3A—C3A—H3AA	109.3	N3B—C3B—H3BA	109.3
N1A—C3A—H3AA	109.3	N1B—C3B—H3BA	109.3
N3A—C3A—H3AB	109.3	N3B—C3B—H3BB	109.3
N1A—C3A—H3AB	109.3	N1B—C3B—H3BB	109.3
H3AA—C3A—H3AB	107.9	H3BA—C3B—H3BB	107.9
N4A—C4A—N1A	111.8 (3)	N4B—C4B—N1B	111.6 (2)
N4A—C4A—H4AA	109.3	N4B—C4B—H4BA	109.3
N1A—C4A—H4AA	109.3	N1B—C4B—H4BA	109.3
N4A—C4A—H4AB	109.3	N4B—C4B—H4BB	109.3
N1A—C4A—H4AB	109.3	N1B—C4B—H4BB	109.3
H4AA—C4A—H4AB	107.9	H4BA—C4B—H4BB	108.0
N4A—C5A—N2A	111.0 (3)	N4B—C5B—N2B	111.3 (2)
N4A—C5A—H5AA	109.4	N4B—C5B—H5BA	109.4
N2A—C5A—H5AA	109.4	N2B—C5B—H5BA	109.4
N4A—C5A—H5AB	109.4	N4B—C5B—H5BB	109.4
N2A—C5A—H5AB	109.4	N2B—C5B—H5BB	109.4
H5AA—C5A—H5AB	108.0	H5BA—C5B—H5BB	108.0
N4A—C6A—N3A	112.8 (3)	N4B—C6B—N3B	112.5 (3)
N4A—C6A—H6AA	109.0	N4B—C6B—H6BA	109.1
N3A—C6A—H6AA	109.0	N3B—C6B—H6BA	109.1
N4A—C6A—H6AB	109.0	N4B—C6B—H6BB	109.1
N3A—C6A—H6AB	109.0	N3B—C6B—H6BB	109.1
H6AA—C6A—H6AB	107.8	H6BA—C6B—H6BB	107.8
C12A—C7A—C8A	120.5 (3)	C8B—C7B—C12B	119.5 (3)
C12A—C7A—C13A	118.3 (3)	C8B—C7B—C13B	121.8 (3)
C8A—C7A—C13A	121.1 (3)	C12B—C7B—C13B	118.5 (3)
C9A—C8A—C7A	119.0 (3)	C7B—C8B—C9B	120.2 (3)
C9A—C8A—H8AA	120.5	C7B—C8B—H8BA	119.9
C7A—C8A—H8AA	120.5	C9B—C8B—H8BA	119.9
C10A—C9A—C8A	120.4 (4)	C10B—C9B—C8B	119.8 (4)
C10A—C9A—H9AA	119.8	C10B—C9B—H9BA	120.1
C8A—C9A—H9AA	119.8	C8B—C9B—H9BA	120.1
C9A—C10A—C11A	120.5 (4)	C11B—C10B—C9B	120.3 (3)
C9A—C10A—H10A	119.7	C11B—C10B—H10B	119.9
C11A—C10A—H10A	119.7	C9B—C10B—H10B	119.9
C10A—C11A—C12A	120.1 (4)	C10B—C11B—C12B	120.5 (3)
C10A—C11A—H11A	120.0	C10B—C11B—H11B	119.8
C12A—C11A—H11A	120.0	C12B—C11B—H11B	119.8
C7A—C12A—C11A	119.5 (3)	C11B—C12B—C7B	119.6 (3)
C7A—C12A—H12A	120.2	C11B—C12B—H12B	120.2
C11A—C12A—H12A	120.2	C7B—C12B—H12B	120.2
O2A—C13A—O1A	123.4 (3)	O2B—C13B—O1B	122.5 (3)
O2A—C13A—C7A	122.1 (3)	O2B—C13B—C7B	123.2 (3)
O1A—C13A—C7A	114.4 (3)	O1B—C13B—C7B	114.3 (3)
C15A—C14A—C19A	119.7 (3)	C15B—C14B—C19B	119.6 (3)
C15A—C14A—C20A	120.9 (3)	C15B—C14B—C20B	120.7 (3)
C19A—C14A—C20A	119.3 (3)	C19B—C14B—C20B	119.7 (3)
C14A—C15A—C16A	120.5 (3)	C16B—C15B—C14B	120.8 (3)
C14A—C15A—H15A	119.7	C16B—C15B—H15B	119.6
C16A—C15A—H15A	119.7	C14B—C15B—H15B	119.6
C17A—C16A—C15A	119.6 (3)	C15B—C16B—C17B	119.4 (3)
C17A—C16A—H16A	120.2	C15B—C16B—H16B	120.3
C15A—C16A—H16A	120.2	C17B—C16B—H16B	120.3
C16A—C17A—C18A	120.2 (3)	C18B—C17B—C16B	120.5 (3)
C16A—C17A—H17A	119.9	C18B—C17B—H17B	119.7
C18A—C17A—H17A	119.9	C16B—C17B—H17B	119.7
C17A—C18A—C19A	120.5 (3)	C17B—C18B—C19B	120.0 (3)
C17A—C18A—H18A	119.7	C17B—C18B—H18B	120.0
C19A—C18A—H18A	119.7	C19B—C18B—H18B	120.0
C18A—C19A—C14A	119.4 (3)	C14B—C19B—C18B	119.7 (3)
C18A—C19A—H19A	120.3	C14B—C19B—H19B	120.2
C14A—C19A—H19A	120.3	C18B—C19B—H19B	120.2
O4A—C20A—O3A	123.4 (3)	O4B—C20B—O3B	123.4 (3)
O4A—C20A—C14A	122.3 (3)	O4B—C20B—C14B	122.1 (3)
O3A—C20A—C14A	114.2 (3)	O3B—C20B—C14B	114.5 (3)
C3A—N1A—C1A—N2A	59.0 (3)	C3B—N1B—C1B—N2B	58.5 (3)
C4A—N1A—C1A—N2A	−58.6 (3)	C4B—N1B—C1B—N2B	−58.5 (3)
C2A—N2A—C1A—N1A	−58.4 (3)	C2B—N2B—C1B—N1B	−58.7 (3)
C5A—N2A—C1A—N1A	59.3 (3)	C5B—N2B—C1B—N1B	59.3 (3)
C3A—N3A—C2A—N2A	−58.9 (3)	C3B—N3B—C2B—N2B	−59.5 (3)
C6A—N3A—C2A—N2A	58.2 (3)	C6B—N3B—C2B—N2B	58.5 (3)
C1A—N2A—C2A—N3A	58.6 (3)	C1B—N2B—C2B—N3B	58.8 (3)
C5A—N2A—C2A—N3A	−58.7 (3)	C5B—N2B—C2B—N3B	−58.5 (3)
C2A—N3A—C3A—N1A	59.2 (3)	C2B—N3B—C3B—N1B	60.1 (3)
C6A—N3A—C3A—N1A	−57.0 (3)	C6B—N3B—C3B—N1B	−57.6 (3)
C1A—N1A—C3A—N3A	−59.7 (3)	C1B—N1B—C3B—N3B	−59.2 (3)
C4A—N1A—C3A—N3A	57.2 (3)	C4B—N1B—C3B—N3B	57.6 (3)
C5A—N4A—C4A—N1A	−59.9 (3)	C6B—N4B—C4B—N1B	58.4 (3)
C6A—N4A—C4A—N1A	58.2 (3)	C5B—N4B—C4B—N1B	−58.8 (3)
C3A—N1A—C4A—N4A	−58.1 (3)	C1B—N1B—C4B—N4B	58.2 (3)
C1A—N1A—C4A—N4A	59.1 (3)	C3B—N1B—C4B—N4B	−58.3 (3)
C4A—N4A—C5A—N2A	59.8 (3)	C4B—N4B—C5B—N2B	59.7 (3)
C6A—N4A—C5A—N2A	−57.6 (3)	C6B—N4B—C5B—N2B	−57.7 (3)
C2A—N2A—C5A—N4A	57.6 (3)	C1B—N2B—C5B—N4B	−59.5 (3)
C1A—N2A—C5A—N4A	−59.6 (3)	C2B—N2B—C5B—N4B	58.2 (3)
C5A—N4A—C6A—N3A	59.2 (4)	C4B—N4B—C6B—N3B	−58.7 (3)
C4A—N4A—C6A—N3A	−58.6 (3)	C5B—N4B—C6B—N3B	59.0 (3)
C3A—N3A—C6A—N4A	58.1 (3)	C3B—N3B—C6B—N4B	58.3 (3)
C2A—N3A—C6A—N4A	−58.5 (3)	C2B—N3B—C6B—N4B	−59.6 (3)
C12A—C7A—C8A—C9A	1.5 (5)	C12B—C7B—C8B—C9B	−1.8 (5)
C13A—C7A—C8A—C9A	−176.1 (3)	C13B—C7B—C8B—C9B	−176.9 (3)
C7A—C8A—C9A—C10A	−1.3 (5)	C7B—C8B—C9B—C10B	0.2 (5)
C8A—C9A—C10A—C11A	0.7 (6)	C8B—C9B—C10B—C11B	0.7 (5)
C9A—C10A—C11A—C12A	−0.3 (6)	C9B—C10B—C11B—C12B	0.1 (6)
C8A—C7A—C12A—C11A	−1.2 (5)	C10B—C11B—C12B—C7B	−1.7 (5)
C13A—C7A—C12A—C11A	176.5 (3)	C8B—C7B—C12B—C11B	2.5 (5)
C10A—C11A—C12A—C7A	0.6 (5)	C13B—C7B—C12B—C11B	177.8 (3)
C12A—C7A—C13A—O2A	−8.4 (5)	C8B—C7B—C13B—O2B	164.4 (3)
C8A—C7A—C13A—O2A	169.3 (3)	C12B—C7B—C13B—O2B	−10.8 (5)
C12A—C7A—C13A—O1A	171.9 (3)	C8B—C7B—C13B—O1B	−13.9 (5)
C8A—C7A—C13A—O1A	−10.4 (5)	C12B—C7B—C13B—O1B	170.9 (3)
C19A—C14A—C15A—C16A	0.0 (5)	C19B—C14B—C15B—C16B	−1.7 (4)
C20A—C14A—C15A—C16A	−178.9 (3)	C20B—C14B—C15B—C16B	−179.9 (3)
C14A—C15A—C16A—C17A	−1.3 (5)	C14B—C15B—C16B—C17B	1.3 (5)
C15A—C16A—C17A—C18A	2.2 (5)	C15B—C16B—C17B—C18B	−0.8 (5)
C16A—C17A—C18A—C19A	−1.7 (5)	C16B—C17B—C18B—C19B	0.8 (5)
C17A—C18A—C19A—C14A	0.3 (5)	C15B—C14B—C19B—C18B	1.7 (5)
C15A—C14A—C19A—C18A	0.5 (5)	C20B—C14B—C19B—C18B	179.9 (3)
C20A—C14A—C19A—C18A	179.4 (3)	C17B—C18B—C19B—C14B	−1.3 (5)
C15A—C14A—C20A—O4A	173.5 (3)	C15B—C14B—C20B—O4B	171.3 (3)
C19A—C14A—C20A—O4A	−5.4 (5)	C19B—C14B—C20B—O4B	−6.9 (5)
C15A—C14A—C20A—O3A	−4.7 (4)	C15B—C14B—C20B—O3B	−7.1 (4)
C19A—C14A—C20A—O3A	176.4 (3)	C19B—C14B—C20B—O3B	174.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1O1···N1A	0.84 (4)	1.81 (4)	2.648 (4)	175 (4)
O3A—H1O3···N2A	0.84 (4)	1.76 (4)	2.589 (3)	169 (4)
O1B—H2O1···N1B	0.83 (6)	1.81 (5)	2.627 (4)	170 (5)
O3B—H2O3···N2B	0.85 (5)	1.75 (5)	2.593 (3)	176 (4)
C1A—H1AA···O2A	0.99	2.57	3.246 (4)	125
C2A—H2AA···O4A^i	0.99	2.44	3.108 (4)	124
C5A—H5AA···O2A^ii	0.99	2.57	3.199 (4)	121
C2B—H2BA···O4B^i	0.99	2.46	3.141 (4)	126
C5B—H5BA···O2B^iii	0.99	2.54	3.216 (4)	125
C3A—H3AB···Cg17^iv	0.99	2.67	3.652 (3)	169
C10A—H10A···Cg16^v	0.95	2.91	3.765 (4)	150
C10B—H10B···Cg17^vi	0.95	2.80	3.612 (4)	144
C5A—H5AB···Cg15^iv	0.99	2.77	3.711 (4)	159
C17A—H17A···Cg18^vii	0.95	2.76	3.640 (4)	154
C3B—H3BB···Cg18^viii	0.99	2.70	3.680 (3)	171
C5B—H5BB···Cg16^viii	0.99	2.78	3.718 (3)	157

Symmetry codes: (i) x−1, y, z; (ii) x+1/2, −y+1, z+1/2; (iii) x+1/2, −y+2, z+1/2; (iv) x−1/2, −y+1, z+1/2; (v) x−1/2, −y+1, z−1/2; (vi) x+1, y, z; (vii) x−1/2, −y+2, z−1/2; (viii) x−1/2, −y+2, z+1/2.

Hexamethylenetetramine bis(benzoic acid) (1533066)

Crystal data

C6H12N4·2(C7H6O2)	F(000) = 816
Mr = 384.43	Dx = 1.317 Mg m^−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
a = 6.1262 (6) Å	Cell parameters from 9928 reflections
b = 26.531 (2) Å	θ = 2.3–28.3°
c = 12.0982 (11) Å	µ = 0.09 mm^−1
β = 99.5055 (16)°	T = 200 K
V = 1939.4 (3) Å^3	Block, colourless
Z = 4	0.76 × 0.39 × 0.21 mm

Data collection

Bruker APEX Duo CCD area detector diffractometer	4805 independent reflections
Radiation source: fine-focus sealed tube	3599 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
φ and ω scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (TWINABS; Sheldrick, 2012)	h = −8→8
Tmin = 0.606, Tmax = 0.937	k = 0→35
6280 measured reflections	l = 0→16

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.046	w = 1/[σ^2(Fo^2) + (0.0326P)^2 + 0.4932P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.109	(Δ/σ)max = 0.001
S = 1.09	Δρmax = 0.17 e Å^−3
4805 reflections	Δρmin = −0.18 e Å^−3
522 parameters	Absolute structure: No quotients, so Flack parameter determined by classical intensity fit
6 restraints	Absolute structure parameter: −1.0 (10)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1A	0.6811 (5)	0.38031 (11)	0.4634 (2)	0.0551 (8)
O2A	0.4058 (5)	0.39921 (12)	0.3279 (3)	0.0685 (10)
O3A	0.4250 (4)	0.61015 (10)	0.3981 (2)	0.0423 (6)
O4A	0.7860 (4)	0.60515 (10)	0.4608 (2)	0.0544 (7)
N1A	0.4818 (4)	0.44969 (10)	0.5697 (2)	0.0316 (6)
N2A	0.3965 (4)	0.53913 (10)	0.5442 (2)	0.0303 (6)
N3A	0.1351 (4)	0.48288 (11)	0.6133 (2)	0.0378 (7)
N4A	0.4850 (5)	0.50457 (11)	0.7321 (2)	0.0387 (7)
C1A	0.5005 (5)	0.49476 (12)	0.5005 (3)	0.0328 (8)
H1AA	0.4281	0.4881	0.4225	0.039*
H1AB	0.6588	0.5020	0.4995	0.039*
C2A	0.1603 (5)	0.52740 (12)	0.5444 (3)	0.0373 (8)
H2AA	0.0880	0.5567	0.5739	0.045*
H2AB	0.0857	0.5212	0.4666	0.045*
C3A	0.2426 (5)	0.44020 (12)	0.5692 (3)	0.0362 (7)
H3AA	0.1689	0.4333	0.4915	0.043*
H3AB	0.2256	0.4100	0.6150	0.043*
C4A	0.5871 (5)	0.46114 (13)	0.6853 (3)	0.0392 (8)
H4AA	0.5757	0.4313	0.7331	0.047*
H4AB	0.7461	0.4682	0.6864	0.047*
C5A	0.5058 (6)	0.54840 (13)	0.6608 (3)	0.0361 (8)
H5AA	0.6644	0.5559	0.6617	0.043*
H5AB	0.4377	0.5781	0.6909	0.043*
C6A	0.2492 (6)	0.49343 (14)	0.7275 (3)	0.0439 (9)
H6AA	0.1771	0.5225	0.7579	0.053*
H6AB	0.2338	0.4639	0.7756	0.053*
C7A	0.6923 (6)	0.34692 (12)	0.2835 (3)	0.0355 (8)
C8A	0.9082 (6)	0.33028 (13)	0.3165 (3)	0.0437 (9)
H8AA	0.9838	0.3367	0.3902	0.052*
C9A	1.0119 (8)	0.30431 (15)	0.2405 (4)	0.0595 (12)
H9AA	1.1607	0.2934	0.2617	0.071*
C10A	0.9015 (10)	0.29420 (16)	0.1353 (4)	0.0696 (14)
H10A	0.9735	0.2760	0.0841	0.083*
C11A	0.6875 (9)	0.31015 (16)	0.1032 (4)	0.0634 (12)
H11A	0.6116	0.3030	0.0299	0.076*
C12A	0.5824 (7)	0.33663 (13)	0.1776 (3)	0.0467 (9)
H12A	0.4342	0.3477	0.1555	0.056*
C13A	0.5775 (5)	0.37778 (13)	0.3597 (3)	0.0383 (8)
C14A	0.6644 (5)	0.65404 (12)	0.2981 (3)	0.0300 (7)
C15A	0.4878 (5)	0.66744 (12)	0.2171 (3)	0.0354 (7)
H15A	0.3433	0.6560	0.2230	0.043*
C16A	0.5192 (6)	0.69744 (14)	0.1275 (3)	0.0465 (9)
H16A	0.3969	0.7064	0.0720	0.056*
C17A	0.7283 (7)	0.71424 (13)	0.1191 (3)	0.0466 (9)
H17A	0.7502	0.7351	0.0581	0.056*
C18A	0.9051 (6)	0.70085 (13)	0.1988 (3)	0.0441 (9)
H18A	1.0493	0.7124	0.1924	0.053*
C19A	0.8752 (6)	0.67062 (12)	0.2886 (3)	0.0372 (8)
H19A	0.9983	0.6613	0.3433	0.045*
C20A	0.6317 (5)	0.62094 (11)	0.3945 (3)	0.0318 (7)
O1B	1.4441 (5)	0.88285 (10)	0.7172 (2)	0.0524 (8)
O2B	1.1756 (5)	0.90136 (11)	0.5778 (2)	0.0643 (9)
O3B	1.1805 (4)	1.11090 (9)	0.6509 (2)	0.0437 (6)
O4B	1.5399 (4)	1.10890 (11)	0.7184 (2)	0.0571 (8)
N1B	1.2385 (4)	0.95116 (9)	0.8214 (2)	0.0292 (6)
N2B	1.1504 (4)	1.04067 (9)	0.7987 (2)	0.0291 (6)
N3B	0.8914 (4)	0.98348 (11)	0.8659 (2)	0.0381 (7)
N4B	1.2404 (5)	1.00429 (9)	0.9854 (2)	0.0349 (7)
C1B	1.2569 (6)	0.99692 (10)	0.7543 (3)	0.0299 (7)
H1BA	1.1864	0.9907	0.6758	0.036*
H1BB	1.4152	1.0045	0.7545	0.036*
C2B	0.9147 (5)	1.02809 (12)	0.7984 (3)	0.0378 (8)
H2BA	0.8404	1.0570	0.8282	0.045*
H2BB	0.8408	1.0220	0.7203	0.045*
C3B	1.0005 (5)	0.94129 (11)	0.8198 (3)	0.0356 (7)
H3BA	0.9278	0.9351	0.7417	0.043*
H3BB	0.9836	0.9105	0.8640	0.043*
C4B	1.3436 (5)	0.96148 (11)	0.9383 (3)	0.0348 (7)
H4BA	1.3312	0.9312	0.9848	0.042*
H4BB	1.5029	0.9686	0.9403	0.042*
C5B	1.2593 (6)	1.04872 (11)	0.9159 (3)	0.0342 (7)
H5BA	1.4177	1.0565	0.9171	0.041*
H5BB	1.1905	1.0780	0.9475	0.041*
C6B	1.0039 (6)	0.99324 (13)	0.9805 (3)	0.0393 (8)
H6BA	0.9878	0.9634	1.0277	0.047*
H6BB	0.9320	1.0222	1.0117	0.047*
C7B	1.4619 (6)	0.84718 (10)	0.5417 (3)	0.0342 (8)
C8B	1.6789 (6)	0.83186 (12)	0.5768 (3)	0.0400 (8)
H8BA	1.7540	0.8407	0.6493	0.048*
C9B	1.7858 (8)	0.80343 (14)	0.5050 (4)	0.0591 (12)
H9BA	1.9354	0.7934	0.5278	0.071*
C10B	1.6747 (10)	0.78983 (16)	0.4010 (4)	0.0719 (15)
H10B	1.7459	0.7694	0.3532	0.086*
C11B	1.4610 (10)	0.80578 (16)	0.3661 (4)	0.0706 (15)
H11B	1.3864	0.7970	0.2935	0.085*
C12B	1.3550 (7)	0.83431 (14)	0.4356 (3)	0.0511 (10)
H12B	1.2075	0.8453	0.4107	0.061*
C13B	1.3445 (6)	0.87889 (11)	0.6135 (3)	0.0356 (7)
C14B	1.4200 (5)	1.15473 (10)	0.5517 (3)	0.0272 (6)
C15B	1.2457 (5)	1.16471 (10)	0.4658 (3)	0.0312 (7)
H15B	1.1027	1.1516	0.4694	0.037*
C16B	1.2794 (6)	1.19375 (11)	0.3746 (3)	0.0366 (7)
H16B	1.1596	1.2005	0.3159	0.044*
C17B	1.4870 (6)	1.21281 (13)	0.3693 (3)	0.0431 (8)
H17B	1.5096	1.2329	0.3072	0.052*
C18B	1.6617 (6)	1.20269 (12)	0.4539 (3)	0.0451 (9)
H18B	1.8045	1.2158	0.4499	0.054*
C19B	1.6293 (6)	1.17350 (12)	0.5447 (3)	0.0399 (8)
H19B	1.7503	1.1663	0.6024	0.048*
C20B	1.3858 (6)	1.12314 (11)	0.6491 (3)	0.0341 (7)
H1O1	0.617 (6)	0.4006 (13)	0.500 (3)	0.063 (13)*
H1O3	0.425 (9)	0.5875 (13)	0.446 (3)	0.082 (16)*
H2O1	1.367 (7)	0.9023 (15)	0.749 (4)	0.085 (17)*
H2O3	1.173 (9)	1.0893 (16)	0.701 (3)	0.10 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0583 (18)	0.0661 (18)	0.0402 (16)	0.0321 (15)	0.0061 (14)	−0.0067 (13)
O2A	0.0473 (16)	0.090 (2)	0.063 (2)	0.0328 (16)	−0.0077 (15)	−0.0202 (17)
O3A	0.0348 (13)	0.0524 (15)	0.0405 (15)	−0.0005 (11)	0.0087 (11)	0.0204 (12)
O4A	0.0389 (14)	0.0680 (17)	0.0525 (17)	0.0040 (13)	−0.0035 (12)	0.0279 (14)
N1A	0.0276 (14)	0.0391 (14)	0.0303 (14)	0.0030 (11)	0.0108 (11)	0.0045 (11)
N2A	0.0279 (14)	0.0414 (15)	0.0234 (14)	−0.0003 (11)	0.0092 (11)	0.0044 (11)
N3A	0.0261 (13)	0.0474 (16)	0.0438 (17)	−0.0013 (12)	0.0174 (12)	0.0054 (14)
N4A	0.0416 (17)	0.0518 (18)	0.0235 (16)	−0.0005 (12)	0.0076 (13)	0.0022 (11)
C1A	0.0288 (16)	0.0483 (19)	0.0254 (18)	0.0000 (13)	0.0163 (14)	0.0013 (12)
C2A	0.0266 (16)	0.0415 (18)	0.045 (2)	0.0056 (13)	0.0078 (14)	0.0051 (15)
C3A	0.0301 (16)	0.0399 (18)	0.0397 (18)	−0.0057 (13)	0.0086 (14)	0.0026 (14)
C4A	0.0306 (17)	0.052 (2)	0.0338 (18)	0.0038 (15)	0.0028 (14)	0.0095 (15)
C5A	0.0389 (18)	0.0435 (18)	0.0262 (17)	−0.0088 (14)	0.0058 (14)	0.0004 (13)
C6A	0.048 (2)	0.049 (2)	0.041 (2)	−0.0008 (16)	0.0242 (18)	0.0039 (16)
C7A	0.0401 (18)	0.0328 (16)	0.0357 (19)	0.0032 (14)	0.0121 (15)	0.0033 (13)
C8A	0.0427 (19)	0.0374 (18)	0.053 (2)	0.0092 (15)	0.0153 (17)	0.0094 (16)
C9A	0.060 (3)	0.051 (2)	0.077 (3)	0.022 (2)	0.040 (2)	0.017 (2)
C10A	0.102 (4)	0.052 (2)	0.066 (3)	0.020 (3)	0.048 (3)	0.006 (2)
C11A	0.093 (4)	0.057 (3)	0.043 (2)	0.002 (2)	0.017 (2)	−0.0052 (19)
C12A	0.056 (2)	0.0396 (18)	0.045 (2)	0.0040 (17)	0.0099 (18)	0.0013 (16)
C13A	0.0349 (18)	0.0386 (17)	0.042 (2)	0.0061 (14)	0.0084 (16)	−0.0023 (15)
C14A	0.0294 (15)	0.0311 (15)	0.0312 (16)	0.0041 (12)	0.0101 (13)	0.0008 (12)
C15A	0.0333 (17)	0.0378 (17)	0.0363 (18)	0.0026 (13)	0.0090 (14)	0.0038 (14)
C16A	0.050 (2)	0.052 (2)	0.038 (2)	0.0076 (17)	0.0084 (17)	0.0138 (16)
C17A	0.062 (2)	0.0389 (19)	0.044 (2)	0.0022 (17)	0.0254 (19)	0.0135 (16)
C18A	0.0370 (18)	0.0434 (19)	0.058 (2)	−0.0020 (15)	0.0254 (17)	0.0067 (17)
C19A	0.0326 (17)	0.0365 (17)	0.0440 (19)	0.0052 (14)	0.0108 (15)	0.0019 (14)
C20A	0.0335 (16)	0.0296 (14)	0.0323 (17)	0.0053 (13)	0.0054 (14)	0.0047 (13)
O1B	0.0646 (19)	0.0537 (16)	0.0358 (15)	0.0328 (14)	−0.0006 (13)	−0.0081 (12)
O2B	0.0567 (19)	0.0695 (18)	0.0585 (18)	0.0313 (15)	−0.0150 (15)	−0.0201 (15)
O3B	0.0441 (14)	0.0429 (14)	0.0417 (16)	−0.0010 (11)	0.0004 (12)	0.0177 (11)
O4B	0.0477 (16)	0.0676 (18)	0.0498 (17)	0.0063 (13)	−0.0104 (13)	0.0272 (14)
N1B	0.0356 (15)	0.0220 (11)	0.0298 (14)	0.0041 (10)	0.0047 (11)	0.0003 (10)
N2B	0.0382 (15)	0.0212 (11)	0.0267 (14)	0.0009 (10)	0.0013 (12)	0.0035 (9)
N3B	0.0327 (14)	0.0393 (15)	0.0441 (17)	−0.0012 (12)	0.0110 (13)	−0.0006 (13)
N4B	0.0506 (18)	0.0292 (13)	0.0231 (15)	−0.0031 (11)	0.0012 (13)	0.0004 (10)
C1B	0.0398 (18)	0.0229 (14)	0.0275 (18)	0.0005 (11)	0.0075 (15)	0.0026 (10)
C2B	0.0330 (17)	0.0392 (17)	0.0402 (19)	0.0097 (13)	0.0027 (15)	0.0051 (14)
C3B	0.0408 (18)	0.0244 (14)	0.0412 (19)	−0.0075 (13)	0.0055 (15)	−0.0017 (13)
C4B	0.0409 (19)	0.0319 (15)	0.0292 (17)	0.0069 (14)	−0.0007 (14)	0.0072 (13)
C5B	0.0452 (19)	0.0251 (14)	0.0310 (17)	−0.0047 (13)	0.0024 (15)	−0.0070 (12)
C6B	0.054 (2)	0.0399 (17)	0.0292 (19)	−0.0004 (15)	0.0221 (17)	0.0019 (14)
C7B	0.054 (2)	0.0170 (13)	0.0316 (17)	−0.0004 (13)	0.0078 (15)	0.0011 (11)
C8B	0.051 (2)	0.0290 (16)	0.0411 (19)	0.0040 (15)	0.0126 (16)	−0.0011 (14)
C9B	0.072 (3)	0.041 (2)	0.071 (3)	0.015 (2)	0.031 (2)	0.0038 (19)
C10B	0.123 (5)	0.046 (2)	0.058 (3)	0.017 (3)	0.045 (3)	−0.008 (2)
C11B	0.124 (5)	0.050 (2)	0.038 (2)	0.003 (3)	0.014 (3)	−0.0147 (19)
C12B	0.071 (3)	0.0425 (19)	0.038 (2)	−0.0018 (19)	0.0031 (19)	−0.0021 (16)
C13B	0.0422 (19)	0.0283 (15)	0.0351 (18)	0.0056 (14)	0.0026 (15)	−0.0010 (13)
C14B	0.0354 (16)	0.0177 (12)	0.0270 (15)	0.0028 (11)	0.0008 (13)	−0.0029 (11)
C15B	0.0349 (17)	0.0242 (13)	0.0323 (16)	0.0005 (12)	−0.0009 (13)	0.0025 (12)
C16B	0.0447 (19)	0.0274 (15)	0.0347 (17)	0.0011 (14)	−0.0020 (14)	0.0049 (13)
C17B	0.055 (2)	0.0312 (17)	0.043 (2)	−0.0001 (16)	0.0093 (17)	0.0074 (15)
C18B	0.0397 (19)	0.0348 (17)	0.061 (2)	−0.0053 (15)	0.0086 (17)	−0.0035 (17)
C19B	0.0346 (17)	0.0347 (16)	0.048 (2)	−0.0001 (14)	−0.0008 (15)	−0.0043 (15)
C20B	0.046 (2)	0.0256 (14)	0.0281 (17)	0.0031 (14)	−0.0005 (15)	0.0019 (12)

Geometric parameters (Å, º)

O1A—C13A	1.311 (4)	O1B—C13B	1.305 (4)
O1A—H1O1	0.833 (19)	O1B—H2O1	0.84 (2)
O2A—C13A	1.202 (4)	O2B—C13B	1.211 (4)
O3A—C20A	1.306 (4)	O3B—C20B	1.303 (4)
O3A—H1O3	0.84 (2)	O3B—H2O3	0.84 (2)
O4A—C20A	1.209 (4)	O4B—C20B	1.215 (4)
N1A—C4A	1.472 (4)	N1B—C1B	1.475 (4)
N1A—C1A	1.475 (4)	N1B—C3B	1.478 (4)
N1A—C3A	1.486 (4)	N1B—C4B	1.479 (4)
N2A—C1A	1.477 (4)	N2B—C1B	1.475 (4)
N2A—C5A	1.479 (4)	N2B—C5B	1.479 (4)
N2A—C2A	1.481 (4)	N2B—C2B	1.482 (4)
N3A—C3A	1.455 (4)	N3B—C2B	1.458 (4)
N3A—C6A	1.468 (5)	N3B—C3B	1.461 (4)
N3A—C2A	1.469 (4)	N3B—C6B	1.466 (4)
N4A—C5A	1.466 (4)	N4B—C4B	1.460 (4)
N4A—C6A	1.467 (5)	N4B—C5B	1.464 (4)
N4A—C4A	1.468 (5)	N4B—C6B	1.470 (5)
C1A—H1AA	0.9900	C1B—H1BA	0.9900
C1A—H1AB	0.9900	C1B—H1BB	0.9900
C2A—H2AA	0.9900	C2B—H2BA	0.9900
C2A—H2AB	0.9900	C2B—H2BB	0.9900
C3A—H3AA	0.9900	C3B—H3BA	0.9900
C3A—H3AB	0.9900	C3B—H3BB	0.9900
C4A—H4AA	0.9900	C4B—H4BA	0.9900
C4A—H4AB	0.9900	C4B—H4BB	0.9900
C5A—H5AA	0.9900	C5B—H5BA	0.9900
C5A—H5AB	0.9900	C5B—H5BB	0.9900
C6A—H6AA	0.9900	C6B—H6BA	0.9900
C6A—H6AB	0.9900	C6B—H6BB	0.9900
C7A—C12A	1.372 (5)	C7B—C12B	1.385 (5)
C7A—C8A	1.389 (5)	C7B—C8B	1.388 (5)
C7A—C13A	1.493 (5)	C7B—C13B	1.479 (5)
C8A—C9A	1.384 (5)	C8B—C9B	1.393 (5)
C8A—H8AA	0.9500	C8B—H8BA	0.9500
C9A—C10A	1.366 (7)	C9B—C10B	1.376 (7)
C9A—H9AA	0.9500	C9B—H9BA	0.9500
C10A—C11A	1.371 (7)	C10B—C11B	1.374 (7)
C10A—H10A	0.9500	C10B—H10B	0.9500
C11A—C12A	1.382 (6)	C11B—C12B	1.372 (6)
C11A—H11A	0.9500	C11B—H11B	0.9500
C12A—H12A	0.9500	C12B—H12B	0.9500
C14A—C15A	1.381 (4)	C14B—C15B	1.387 (4)
C14A—C19A	1.387 (4)	C14B—C19B	1.391 (5)
C14A—C20A	1.500 (4)	C14B—C20B	1.488 (4)
C15A—C16A	1.383 (5)	C15B—C16B	1.389 (4)
C15A—H15A	0.9500	C15B—H15B	0.9500
C16A—C17A	1.376 (5)	C16B—C17B	1.380 (5)
C16A—H16A	0.9500	C16B—H16B	0.9500
C17A—C18A	1.373 (5)	C17B—C18B	1.380 (5)
C17A—H17A	0.9500	C17B—H17B	0.9500
C18A—C19A	1.387 (5)	C18B—C19B	1.385 (5)
C18A—H18A	0.9500	C18B—H18B	0.9500
C19A—H19A	0.9500	C19B—H19B	0.9500
C13A—O1A—H1O1	110 (3)	C13B—O1B—H2O1	107 (4)
C20A—O3A—H1O3	107 (4)	C20B—O3B—H2O3	110 (4)
C4A—N1A—C1A	108.0 (2)	C1B—N1B—C3B	107.7 (2)
C4A—N1A—C3A	108.4 (2)	C1B—N1B—C4B	108.2 (2)
C1A—N1A—C3A	107.7 (2)	C3B—N1B—C4B	108.6 (2)
C1A—N2A—C5A	108.6 (2)	C1B—N2B—C5B	107.8 (2)
C1A—N2A—C2A	108.2 (3)	C1B—N2B—C2B	108.1 (2)
C5A—N2A—C2A	108.8 (2)	C5B—N2B—C2B	108.7 (2)
C3A—N3A—C6A	108.6 (3)	C2B—N3B—C3B	108.4 (3)
C3A—N3A—C2A	108.7 (3)	C2B—N3B—C6B	108.2 (3)
C6A—N3A—C2A	107.6 (3)	C3B—N3B—C6B	108.8 (3)
C5A—N4A—C6A	108.5 (3)	C4B—N4B—C5B	108.8 (3)
C5A—N4A—C4A	108.2 (3)	C4B—N4B—C6B	108.4 (3)
C6A—N4A—C4A	107.8 (3)	C5B—N4B—C6B	108.0 (3)
N1A—C1A—N2A	111.4 (2)	N1B—C1B—N2B	111.6 (3)
N1A—C1A—H1AA	109.4	N1B—C1B—H1BA	109.3
N2A—C1A—H1AA	109.4	N2B—C1B—H1BA	109.3
N1A—C1A—H1AB	109.4	N1B—C1B—H1BB	109.3
N2A—C1A—H1AB	109.4	N2B—C1B—H1BB	109.3
H1AA—C1A—H1AB	108.0	H1BA—C1B—H1BB	108.0
N3A—C2A—N2A	111.4 (2)	N3B—C2B—N2B	111.5 (2)
N3A—C2A—H2AA	109.4	N3B—C2B—H2BA	109.3
N2A—C2A—H2AA	109.4	N2B—C2B—H2BA	109.3
N3A—C2A—H2AB	109.4	N3B—C2B—H2BB	109.3
N2A—C2A—H2AB	109.4	N2B—C2B—H2BB	109.3
H2AA—C2A—H2AB	108.0	H2BA—C2B—H2BB	108.0
N3A—C3A—N1A	111.9 (3)	N3B—C3B—N1B	111.8 (2)
N3A—C3A—H3AA	109.2	N3B—C3B—H3BA	109.3
N1A—C3A—H3AA	109.2	N1B—C3B—H3BA	109.3
N3A—C3A—H3AB	109.2	N3B—C3B—H3BB	109.3
N1A—C3A—H3AB	109.2	N1B—C3B—H3BB	109.3
H3AA—C3A—H3AB	107.9	H3BA—C3B—H3BB	107.9
N4A—C4A—N1A	112.4 (3)	N4B—C4B—N1B	111.6 (2)
N4A—C4A—H4AA	109.1	N4B—C4B—H4BA	109.3
N1A—C4A—H4AA	109.1	N1B—C4B—H4BA	109.3
N4A—C4A—H4AB	109.1	N4B—C4B—H4BB	109.3
N1A—C4A—H4AB	109.1	N1B—C4B—H4BB	109.3
H4AA—C4A—H4AB	107.9	H4BA—C4B—H4BB	108.0
N4A—C5A—N2A	111.1 (3)	N4B—C5B—N2B	111.6 (2)
N4A—C5A—H5AA	109.4	N4B—C5B—H5BA	109.3
N2A—C5A—H5AA	109.4	N2B—C5B—H5BA	109.3
N4A—C5A—H5AB	109.4	N4B—C5B—H5BB	109.3
N2A—C5A—H5AB	109.4	N2B—C5B—H5BB	109.3
H5AA—C5A—H5AB	108.0	H5BA—C5B—H5BB	108.0
N4A—C6A—N3A	112.8 (3)	N3B—C6B—N4B	112.3 (3)
N4A—C6A—H6AA	109.0	N3B—C6B—H6BA	109.1
N3A—C6A—H6AA	109.0	N4B—C6B—H6BA	109.1
N4A—C6A—H6AB	109.0	N3B—C6B—H6BB	109.1
N3A—C6A—H6AB	109.0	N4B—C6B—H6BB	109.1
H6AA—C6A—H6AB	107.8	H6BA—C6B—H6BB	107.9
C12A—C7A—C8A	120.1 (3)	C12B—C7B—C8B	119.6 (3)
C12A—C7A—C13A	118.5 (3)	C12B—C7B—C13B	118.9 (3)
C8A—C7A—C13A	121.4 (3)	C8B—C7B—C13B	121.4 (3)
C9A—C8A—C7A	119.2 (4)	C7B—C8B—C9B	119.5 (4)
C9A—C8A—H8AA	120.4	C7B—C8B—H8BA	120.2
C7A—C8A—H8AA	120.4	C9B—C8B—H8BA	120.2
C10A—C9A—C8A	120.4 (4)	C10B—C9B—C8B	120.0 (4)
C10A—C9A—H9AA	119.8	C10B—C9B—H9BA	120.0
C8A—C9A—H9AA	119.8	C8B—C9B—H9BA	120.0
C9A—C10A—C11A	120.4 (4)	C11B—C10B—C9B	120.2 (4)
C9A—C10A—H10A	119.8	C11B—C10B—H10B	119.9
C11A—C10A—H10A	119.8	C9B—C10B—H10B	119.9
C10A—C11A—C12A	119.9 (4)	C12B—C11B—C10B	120.3 (4)
C10A—C11A—H11A	120.1	C12B—C11B—H11B	119.8
C12A—C11A—H11A	120.1	C10B—C11B—H11B	119.8
C7A—C12A—C11A	120.0 (4)	C11B—C12B—C7B	120.3 (4)
C7A—C12A—H12A	120.0	C11B—C12B—H12B	119.8
C11A—C12A—H12A	120.0	C7B—C12B—H12B	119.8
O2A—C13A—O1A	122.9 (3)	O2B—C13B—O1B	122.7 (3)
O2A—C13A—C7A	122.5 (3)	O2B—C13B—C7B	122.7 (3)
O1A—C13A—C7A	114.6 (3)	O1B—C13B—C7B	114.5 (3)
C15A—C14A—C19A	119.4 (3)	C15B—C14B—C19B	119.3 (3)
C15A—C14A—C20A	120.9 (3)	C15B—C14B—C20B	120.6 (3)
C19A—C14A—C20A	119.7 (3)	C19B—C14B—C20B	120.1 (3)
C14A—C15A—C16A	120.7 (3)	C14B—C15B—C16B	120.3 (3)
C14A—C15A—H15A	119.7	C14B—C15B—H15B	119.9
C16A—C15A—H15A	119.7	C16B—C15B—H15B	119.9
C17A—C16A—C15A	119.7 (3)	C17B—C16B—C15B	120.0 (3)
C17A—C16A—H16A	120.1	C17B—C16B—H16B	120.0
C15A—C16A—H16A	120.1	C15B—C16B—H16B	120.0
C18A—C17A—C16A	120.0 (3)	C16B—C17B—C18B	120.1 (3)
C18A—C17A—H17A	120.0	C16B—C17B—H17B	119.9
C16A—C17A—H17A	120.0	C18B—C17B—H17B	119.9
C17A—C18A—C19A	120.6 (3)	C17B—C18B—C19B	120.2 (3)
C17A—C18A—H18A	119.7	C17B—C18B—H18B	119.9
C19A—C18A—H18A	119.7	C19B—C18B—H18B	119.9
C14A—C19A—C18A	119.6 (3)	C18B—C19B—C14B	120.2 (3)
C14A—C19A—H19A	120.2	C18B—C19B—H19B	119.9
C18A—C19A—H19A	120.2	C14B—C19B—H19B	119.9
O4A—C20A—O3A	123.9 (3)	O4B—C20B—O3B	123.6 (3)
O4A—C20A—C14A	121.9 (3)	O4B—C20B—C14B	121.8 (3)
O3A—C20A—C14A	114.2 (3)	O3B—C20B—C14B	114.6 (3)
C4A—N1A—C1A—N2A	−58.0 (3)	C3B—N1B—C1B—N2B	58.6 (3)
C3A—N1A—C1A—N2A	58.9 (3)	C4B—N1B—C1B—N2B	−58.6 (3)
C5A—N2A—C1A—N1A	58.7 (3)	C5B—N2B—C1B—N1B	58.8 (3)
C2A—N2A—C1A—N1A	−59.2 (3)	C2B—N2B—C1B—N1B	−58.5 (3)
C3A—N3A—C2A—N2A	−58.9 (3)	C3B—N3B—C2B—N2B	−59.4 (3)
C6A—N3A—C2A—N2A	58.6 (3)	C6B—N3B—C2B—N2B	58.4 (4)
C1A—N2A—C2A—N3A	58.7 (3)	C1B—N2B—C2B—N3B	58.7 (3)
C5A—N2A—C2A—N3A	−59.2 (3)	C5B—N2B—C2B—N3B	−58.0 (3)
C6A—N3A—C3A—N1A	−57.6 (3)	C2B—N3B—C3B—N1B	60.0 (3)
C2A—N3A—C3A—N1A	59.2 (3)	C6B—N3B—C3B—N1B	−57.5 (3)
C4A—N1A—C3A—N3A	57.5 (3)	C1B—N1B—C3B—N3B	−59.3 (3)
C1A—N1A—C3A—N3A	−59.1 (3)	C4B—N1B—C3B—N3B	57.7 (3)
C5A—N4A—C4A—N1A	−59.4 (3)	C5B—N4B—C4B—N1B	−58.8 (3)
C6A—N4A—C4A—N1A	57.8 (4)	C6B—N4B—C4B—N1B	58.4 (3)
C1A—N1A—C4A—N4A	58.7 (3)	C1B—N1B—C4B—N4B	58.3 (3)
C3A—N1A—C4A—N4A	−57.8 (3)	C3B—N1B—C4B—N4B	−58.3 (3)
C6A—N4A—C5A—N2A	−57.7 (4)	C4B—N4B—C5B—N2B	59.3 (3)
C4A—N4A—C5A—N2A	59.0 (3)	C6B—N4B—C5B—N2B	−58.2 (3)
C1A—N2A—C5A—N4A	−59.2 (3)	C1B—N2B—C5B—N4B	−59.0 (3)
C2A—N2A—C5A—N4A	58.4 (3)	C2B—N2B—C5B—N4B	58.0 (3)
C5A—N4A—C6A—N3A	58.9 (4)	C2B—N3B—C6B—N4B	−59.6 (4)
C4A—N4A—C6A—N3A	−58.1 (4)	C3B—N3B—C6B—N4B	57.9 (3)
C3A—N3A—C6A—N4A	58.6 (4)	C4B—N4B—C6B—N3B	−58.4 (3)
C2A—N3A—C6A—N4A	−59.0 (4)	C5B—N4B—C6B—N3B	59.3 (3)
C12A—C7A—C8A—C9A	1.4 (5)	C12B—C7B—C8B—C9B	−0.4 (5)
C13A—C7A—C8A—C9A	−176.3 (3)	C13B—C7B—C8B—C9B	−177.8 (3)
C7A—C8A—C9A—C10A	−1.4 (6)	C7B—C8B—C9B—C10B	−1.4 (6)
C8A—C9A—C10A—C11A	0.7 (7)	C8B—C9B—C10B—C11B	2.4 (7)
C9A—C10A—C11A—C12A	0.0 (7)	C9B—C10B—C11B—C12B	−1.6 (7)
C8A—C7A—C12A—C11A	−0.7 (5)	C10B—C11B—C12B—C7B	−0.2 (7)
C13A—C7A—C12A—C11A	177.0 (3)	C8B—C7B—C12B—C11B	1.2 (5)
C10A—C11A—C12A—C7A	0.0 (6)	C13B—C7B—C12B—C11B	178.7 (4)
C12A—C7A—C13A—O2A	−9.8 (5)	C12B—C7B—C13B—O2B	−13.2 (5)
C8A—C7A—C13A—O2A	168.0 (4)	C8B—C7B—C13B—O2B	164.2 (4)
C12A—C7A—C13A—O1A	171.5 (3)	C12B—C7B—C13B—O1B	170.3 (3)
C8A—C7A—C13A—O1A	−10.8 (5)	C8B—C7B—C13B—O1B	−12.3 (5)
C19A—C14A—C15A—C16A	−0.5 (5)	C19B—C14B—C15B—C16B	−0.9 (4)
C20A—C14A—C15A—C16A	−179.1 (3)	C20B—C14B—C15B—C16B	−179.3 (3)
C14A—C15A—C16A—C17A	−0.2 (5)	C14B—C15B—C16B—C17B	0.0 (5)
C15A—C16A—C17A—C18A	0.6 (6)	C15B—C16B—C17B—C18B	0.6 (5)
C16A—C17A—C18A—C19A	−0.4 (6)	C16B—C17B—C18B—C19B	−0.2 (5)
C15A—C14A—C19A—C18A	0.8 (5)	C17B—C18B—C19B—C14B	−0.8 (5)
C20A—C14A—C19A—C18A	179.4 (3)	C15B—C14B—C19B—C18B	1.3 (5)
C17A—C18A—C19A—C14A	−0.3 (5)	C20B—C14B—C19B—C18B	179.7 (3)
C15A—C14A—C20A—O4A	173.4 (3)	C15B—C14B—C20B—O4B	171.1 (3)
C19A—C14A—C20A—O4A	−5.2 (5)	C19B—C14B—C20B—O4B	−7.2 (5)
C15A—C14A—C20A—O3A	−5.1 (4)	C15B—C14B—C20B—O3B	−6.6 (4)
C19A—C14A—C20A—O3A	176.2 (3)	C19B—C14B—C20B—O3B	175.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1O1···N1A	0.84 (4)	1.82 (4)	2.656 (4)	174 (3)
O3A—H1O3···N2A	0.84 (4)	1.78 (4)	2.609 (4)	174 (6)
O1B—H2O1···N1B	0.84 (4)	1.82 (4)	2.643 (4)	171 (4)
O3B—H2O3···N2B	0.84 (4)	1.77 (4)	2.610 (3)	176 (5)
C2A—H2AA···O4A^i	0.99	2.47	3.126 (4)	123
C5A—H5AA···O2A^ii	0.99	2.58	3.223 (5)	122
C2B—H2BA···O4B^i	0.99	2.50	3.174 (4)	125
C5B—H5BA···O2B^iii	0.99	2.55	3.232 (5)	126
C3A—H3AB···Cg17^iv	0.99	2.76	3.734 (4)	169
C5A—H5AB···Cg15^iv	0.99	2.85	3.787 (4)	159
C10A—H10A···Cg16^v	0.95	2.97	3.829 (5)	152
C10B—H10B···Cg17^vi	0.95	2.85	3.665 (5)	145
C17A—H17A···Cg18^vii	0.95	2.85	3.718 (4)	153
C3B—H3BB···Cg18^viii	0.99	2.77	3.757 (3)	171
C5B—H5BB···Cg16^viii	0.99	2.86	3.797 (3)	157

Symmetry codes: (i) x−1, y, z; (ii) x+1/2, −y+1, z+1/2; (iii) x+1/2, −y+2, z+1/2; (iv) x−1/2, −y+1, z+1/2; (v) x−1/2, −y+1, z−1/2; (vi) x+1, y, z; (vii) x−1/2, −y+2, z−1/2; (viii) x−1/2, −y+2, z+1/2.

Hexamethylenetetramine bis(benzoic acid) (1533067)

Crystal data

C6H12N4·2(C7H6O2)	F(000) = 816
Mr = 384.43	Dx = 1.311 Mg m^−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
a = 6.1343 (9) Å	Cell parameters from 4974 reflections
b = 26.629 (4) Å	θ = 2.9–28.3°
c = 12.0933 (18) Å	µ = 0.09 mm^−1
β = 99.514 (3)°	T = 220 K
V = 1948.3 (5) Å^3	Block, colourless
Z = 4	0.76 × 0.39 × 0.21 mm

Data collection

Bruker APEX Duo CCD area detector diffractometer	4871 independent reflections
Radiation source: fine-focus sealed tube	2951 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
φ and ω scans	θmax = 28.4°, θmin = 1.5°
Absorption correction: multi-scan (TWINABS; Sheldrick, 2012)	h = −8→8
Tmin = 0.701, Tmax = 0.937	k = 0→35
6362 measured reflections	l = 0→16

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.063	w = 1/[σ^2(Fo^2) + (0.086P)^2 + 0.3083P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.190	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.23 e Å^−3
4871 reflections	Δρmin = −0.23 e Å^−3
522 parameters	Absolute structure: No quotients, so Flack parameter determined by classical intensity fit
6 restraints	Absolute structure parameter: −0.9 (14)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1A	0.3220 (8)	0.61940 (18)	0.5375 (4)	0.0626 (14)
H1O1	0.371 (12)	0.599 (2)	0.497 (6)	0.09 (3)*
O2A	0.5941 (8)	0.60048 (19)	0.6733 (4)	0.0765 (17)
O3A	0.5763 (6)	0.38972 (16)	0.6023 (3)	0.0490 (11)
H1O3	0.589 (13)	0.412 (2)	0.556 (5)	0.09 (2)*
O4A	0.2146 (7)	0.39497 (16)	0.5394 (4)	0.0625 (13)
N1A	0.5209 (7)	0.55005 (15)	0.4300 (4)	0.0353 (10)
N2A	0.6064 (6)	0.46071 (15)	0.4553 (3)	0.0347 (10)
N3A	0.8661 (7)	0.51701 (18)	0.3870 (4)	0.0421 (11)
N4A	0.5148 (9)	0.49569 (17)	0.2678 (4)	0.0449 (13)
C1A	0.5017 (9)	0.50516 (18)	0.4994 (5)	0.0366 (13)
H1AA	0.3453	0.4981	0.5003	0.044*
H1AB	0.5733	0.5117	0.5767	0.044*
C2A	0.8416 (8)	0.47322 (19)	0.4553 (5)	0.0429 (13)
H2AA	0.9144	0.4796	0.5324	0.052*
H2AB	0.9151	0.4445	0.4266	0.052*
C3A	0.7584 (9)	0.55963 (18)	0.4316 (5)	0.0424 (13)
H3AA	0.7758	0.5896	0.3868	0.051*
H3AB	0.8303	0.5662	0.5088	0.051*
C4A	0.4163 (8)	0.5389 (2)	0.3147 (5)	0.0423 (13)
H4AA	0.2586	0.5325	0.3133	0.051*
H4AB	0.4294	0.5684	0.2676	0.051*
C5A	0.4949 (9)	0.45239 (19)	0.3401 (4)	0.0412 (13)
H5AA	0.3381	0.4455	0.3404	0.049*
H5AB	0.5590	0.4228	0.3094	0.049*
C6A	0.7505 (11)	0.5065 (2)	0.2721 (5)	0.0502 (16)
H6AA	0.7663	0.5355	0.2243	0.060*
H6AB	0.8209	0.4776	0.2419	0.060*
C7A	0.3083 (10)	0.6532 (2)	0.7148 (5)	0.0429 (14)
C8A	0.0923 (10)	0.6696 (2)	0.6838 (6)	0.0502 (16)
H8AA	0.0160	0.6630	0.6113	0.060*
C9A	−0.0098 (13)	0.6955 (2)	0.7589 (7)	0.066 (2)
H9AA	−0.1564	0.7064	0.7377	0.080*
C10A	0.0981 (16)	0.7054 (3)	0.8628 (7)	0.081 (3)
H10A	0.0258	0.7230	0.9136	0.098*
C11A	0.3165 (15)	0.6898 (3)	0.8961 (7)	0.073 (2)
H11A	0.3921	0.6971	0.9683	0.087*
C12A	0.4190 (11)	0.6635 (2)	0.8216 (5)	0.0525 (15)
H12A	0.5654	0.6525	0.8432	0.063*
C13A	0.4242 (9)	0.6221 (2)	0.6414 (5)	0.0427 (14)
C14A	0.3383 (9)	0.34606 (18)	0.7015 (5)	0.0359 (12)
C15A	0.5132 (9)	0.33283 (19)	0.7834 (4)	0.0397 (13)
H15A	0.6558	0.3446	0.7787	0.048*
C16A	0.4820 (10)	0.3024 (2)	0.8725 (5)	0.0522 (15)
H16A	0.6022	0.2932	0.9275	0.063*
C17A	0.2725 (12)	0.2858 (2)	0.8790 (5)	0.0554 (17)
H17A	0.2504	0.2647	0.9386	0.067*
C18A	0.0957 (10)	0.2993 (2)	0.8005 (6)	0.0490 (15)
H18A	−0.0469	0.2880	0.8072	0.059*
C19A	0.1264 (9)	0.32930 (19)	0.7116 (5)	0.0398 (13)
H19A	0.0046	0.3386	0.6576	0.048*
C20A	0.3699 (9)	0.37923 (18)	0.6061 (5)	0.0378 (12)
O1B	−0.4438 (8)	0.11695 (17)	0.2823 (4)	0.0610 (14)
H2O1	−0.351 (12)	0.098 (3)	0.262 (8)	0.12 (4)*
O2B	−0.1755 (8)	0.09856 (17)	0.4222 (4)	0.0743 (17)
O3B	−0.1816 (7)	−0.11056 (15)	0.3494 (4)	0.0506 (11)
H2O3	−0.166 (18)	−0.089 (3)	0.302 (7)	0.16 (5)*
O4B	−0.5399 (7)	−0.10897 (18)	0.2810 (4)	0.0696 (15)
N1B	−0.2361 (7)	0.04854 (14)	0.1793 (4)	0.0367 (10)
N2B	−0.1514 (7)	−0.04063 (14)	0.2017 (4)	0.0337 (10)
N3B	0.1077 (7)	0.01580 (18)	0.1350 (4)	0.0427 (11)
N4B	−0.2397 (8)	−0.00403 (14)	0.0154 (4)	0.0401 (12)
C1B	−0.2575 (10)	0.00291 (15)	0.2464 (5)	0.0338 (13)
H1BA	−0.1886	0.0088	0.3244	0.041*
H1BB	−0.4144	−0.0044	0.2455	0.041*
C2B	0.0847 (9)	−0.02831 (19)	0.2023 (5)	0.0439 (14)
H2BA	0.1576	−0.0223	0.2795	0.053*
H2BB	0.1578	−0.0569	0.1728	0.053*
C3B	−0.0011 (9)	0.05823 (18)	0.1814 (5)	0.0422 (13)
H3BA	0.0706	0.0643	0.2588	0.051*
H3BB	0.0163	0.0885	0.1377	0.051*
C4B	−0.3428 (9)	0.03858 (18)	0.0629 (5)	0.0426 (13)
H4BA	−0.5000	0.0315	0.0615	0.051*
H4BB	−0.3313	0.0685	0.0170	0.051*
C5B	−0.2601 (10)	−0.04884 (17)	0.0850 (4)	0.0399 (13)
H5BA	−0.4168	−0.0564	0.0837	0.048*
H5BB	−0.1924	−0.0777	0.0537	0.048*
C6B	−0.0063 (11)	0.0068 (2)	0.0204 (5)	0.0470 (15)
H6BA	0.0097	0.0364	−0.0255	0.056*
H6BB	0.0641	−0.0216	−0.0115	0.056*
C7B	−0.4616 (10)	0.15290 (16)	0.4588 (5)	0.0394 (13)
C8B	−0.6795 (10)	0.1683 (2)	0.4236 (5)	0.0468 (14)
H8BA	−0.7538	0.1596	0.3519	0.056*
C9B	−0.7845 (14)	0.1963 (2)	0.4940 (7)	0.069 (2)
H9BA	−0.9320	0.2062	0.4708	0.083*
C10B	−0.6758 (17)	0.2099 (3)	0.5979 (7)	0.084 (3)
H10B	−0.7484	0.2297	0.6451	0.101*
C11B	−0.4601 (17)	0.1948 (3)	0.6339 (7)	0.076 (2)
H11B	−0.3862	0.2041	0.7053	0.092*
C12B	−0.3531 (12)	0.1657 (2)	0.5637 (6)	0.0588 (17)
H12B	−0.2072	0.1548	0.5879	0.071*
C13B	−0.3466 (10)	0.12076 (18)	0.3868 (5)	0.0411 (13)
C14B	−0.4202 (8)	−0.15433 (16)	0.4486 (4)	0.0326 (11)
C15B	−0.2465 (8)	−0.16474 (17)	0.5346 (4)	0.0364 (12)
H15B	−0.1050	−0.1519	0.5313	0.044*
C16B	−0.2797 (10)	−0.19391 (18)	0.6252 (5)	0.0447 (14)
H16B	−0.1613	−0.2008	0.6832	0.054*
C17B	−0.4859 (11)	−0.2127 (2)	0.6300 (6)	0.0513 (16)
H17B	−0.5087	−0.2326	0.6913	0.062*
C18B	−0.6610 (11)	−0.2025 (2)	0.5451 (6)	0.0545 (17)
H18B	−0.8019	−0.2155	0.5492	0.065*
C19B	−0.6304 (10)	−0.1737 (2)	0.4556 (5)	0.0460 (14)
H19B	−0.7503	−0.1668	0.3985	0.055*
C20B	−0.3863 (9)	−0.12296 (18)	0.3524 (5)	0.0399 (13)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.067 (3)	0.071 (3)	0.049 (3)	0.036 (2)	0.007 (3)	−0.008 (2)
O2A	0.057 (3)	0.102 (4)	0.065 (3)	0.038 (3)	−0.008 (3)	−0.025 (3)
O3A	0.040 (2)	0.064 (3)	0.043 (3)	−0.0016 (18)	0.010 (2)	0.023 (2)
O4A	0.043 (2)	0.076 (3)	0.065 (3)	0.007 (2)	−0.002 (2)	0.028 (2)
N1A	0.031 (2)	0.046 (2)	0.031 (2)	0.0050 (18)	0.0123 (19)	0.0092 (18)
N2A	0.028 (2)	0.047 (2)	0.032 (3)	−0.0019 (18)	0.013 (2)	0.0042 (19)
N3A	0.027 (2)	0.051 (3)	0.052 (3)	−0.008 (2)	0.020 (2)	0.005 (2)
N4A	0.048 (3)	0.058 (3)	0.031 (3)	−0.003 (2)	0.011 (2)	0.0058 (19)
C1A	0.029 (3)	0.055 (3)	0.030 (3)	−0.001 (2)	0.016 (2)	0.001 (2)
C2A	0.028 (3)	0.048 (3)	0.055 (4)	0.001 (2)	0.013 (3)	0.004 (3)
C3A	0.037 (3)	0.039 (3)	0.053 (4)	−0.005 (2)	0.011 (3)	0.001 (2)
C4A	0.030 (3)	0.058 (3)	0.042 (3)	0.009 (2)	0.015 (2)	0.012 (3)
C5A	0.047 (3)	0.047 (3)	0.033 (3)	−0.010 (2)	0.018 (3)	0.001 (2)
C6A	0.058 (4)	0.058 (3)	0.043 (4)	0.000 (3)	0.033 (3)	0.009 (3)
C7A	0.048 (3)	0.038 (3)	0.046 (4)	0.008 (2)	0.014 (3)	0.001 (2)
C8A	0.047 (3)	0.043 (3)	0.067 (4)	0.012 (3)	0.026 (3)	0.012 (3)
C9A	0.067 (5)	0.058 (4)	0.083 (6)	0.029 (3)	0.038 (4)	0.016 (4)
C10A	0.123 (8)	0.057 (4)	0.081 (6)	0.024 (4)	0.065 (5)	0.008 (4)
C11A	0.099 (6)	0.062 (4)	0.058 (5)	−0.002 (4)	0.018 (4)	−0.005 (4)
C12A	0.068 (4)	0.047 (3)	0.042 (4)	0.007 (3)	0.011 (3)	0.005 (3)
C13A	0.040 (3)	0.042 (3)	0.046 (4)	0.008 (2)	0.007 (3)	−0.005 (2)
C14A	0.038 (3)	0.036 (2)	0.037 (3)	0.000 (2)	0.016 (2)	0.001 (2)
C15A	0.041 (3)	0.044 (3)	0.038 (3)	−0.001 (2)	0.016 (3)	0.004 (2)
C16A	0.055 (4)	0.059 (3)	0.043 (4)	0.004 (3)	0.008 (3)	0.016 (3)
C17A	0.077 (5)	0.048 (3)	0.049 (4)	−0.001 (3)	0.030 (3)	0.014 (3)
C18A	0.041 (3)	0.047 (3)	0.066 (4)	−0.004 (2)	0.028 (3)	0.008 (3)
C19A	0.031 (3)	0.042 (3)	0.050 (3)	0.003 (2)	0.017 (2)	0.001 (2)
C20A	0.039 (3)	0.033 (2)	0.042 (3)	0.004 (2)	0.008 (3)	0.004 (2)
O1B	0.073 (3)	0.065 (3)	0.040 (3)	0.036 (2)	−0.006 (2)	−0.008 (2)
O2B	0.064 (3)	0.080 (3)	0.068 (3)	0.036 (3)	−0.020 (3)	−0.020 (3)
O3B	0.044 (2)	0.050 (2)	0.055 (3)	−0.0019 (18)	0.001 (2)	0.021 (2)
O4B	0.052 (3)	0.078 (3)	0.070 (3)	0.005 (2)	−0.017 (2)	0.035 (3)
N1B	0.042 (3)	0.0254 (18)	0.043 (3)	0.0027 (17)	0.007 (2)	−0.0019 (17)
N2B	0.042 (3)	0.0253 (18)	0.033 (2)	0.0017 (16)	0.002 (2)	0.0027 (16)
N3B	0.035 (3)	0.048 (2)	0.048 (3)	0.005 (2)	0.014 (2)	0.003 (2)
N4B	0.056 (3)	0.039 (2)	0.024 (3)	−0.0011 (19)	−0.001 (2)	0.0011 (16)
C1B	0.041 (3)	0.027 (2)	0.033 (3)	0.0027 (17)	0.006 (3)	0.0002 (17)
C2B	0.035 (3)	0.048 (3)	0.046 (3)	0.012 (2)	0.000 (3)	0.000 (2)
C3B	0.044 (3)	0.038 (3)	0.044 (3)	−0.006 (2)	0.005 (3)	−0.003 (2)
C4B	0.041 (3)	0.044 (3)	0.040 (3)	0.009 (2)	0.000 (3)	0.008 (2)
C5B	0.052 (3)	0.034 (2)	0.032 (3)	−0.005 (2)	0.002 (3)	−0.007 (2)
C6B	0.062 (4)	0.049 (3)	0.034 (4)	0.004 (3)	0.020 (3)	0.001 (2)
C7B	0.059 (4)	0.021 (2)	0.038 (3)	−0.001 (2)	0.008 (3)	0.000 (2)
C8B	0.053 (4)	0.039 (3)	0.050 (4)	0.007 (2)	0.012 (3)	0.000 (2)
C9B	0.084 (5)	0.053 (4)	0.076 (5)	0.019 (3)	0.032 (4)	0.003 (3)
C10B	0.138 (9)	0.059 (4)	0.067 (5)	0.017 (5)	0.049 (6)	−0.014 (4)
C11B	0.120 (8)	0.064 (4)	0.046 (4)	0.003 (5)	0.017 (4)	−0.017 (4)
C12B	0.075 (5)	0.049 (3)	0.047 (4)	0.000 (3)	−0.005 (3)	−0.004 (3)
C13B	0.047 (3)	0.036 (2)	0.039 (3)	0.005 (2)	0.004 (3)	−0.004 (2)
C14B	0.034 (3)	0.024 (2)	0.036 (3)	0.0059 (18)	−0.003 (2)	−0.003 (2)
C15B	0.039 (3)	0.036 (2)	0.034 (3)	0.005 (2)	0.002 (2)	0.006 (2)
C16B	0.052 (4)	0.038 (3)	0.041 (3)	0.004 (2)	−0.001 (3)	0.007 (2)
C17B	0.059 (4)	0.038 (3)	0.059 (4)	0.004 (3)	0.016 (3)	0.007 (3)
C18B	0.047 (4)	0.039 (3)	0.074 (5)	−0.003 (3)	0.002 (3)	−0.007 (3)
C19B	0.039 (3)	0.045 (3)	0.052 (4)	0.000 (2)	0.000 (3)	−0.001 (3)
C20B	0.046 (3)	0.034 (2)	0.036 (3)	0.006 (2)	−0.005 (3)	0.000 (2)

Geometric parameters (Å, º)

O1A—C13A	1.310 (7)	O1B—C13B	1.309 (7)
O1A—H1O1	0.82 (2)	O1B—H2O1	0.83 (2)
O2A—C13A	1.197 (7)	O2B—C13B	1.219 (7)
O3A—C20A	1.305 (7)	O3B—C20B	1.305 (7)
O3A—H1O3	0.82 (2)	O3B—H2O3	0.84 (2)
O4A—C20A	1.216 (7)	O4B—C20B	1.226 (6)
N1A—C4A	1.466 (7)	N1B—C3B	1.461 (7)
N1A—C3A	1.476 (7)	N1B—C4B	1.475 (7)
N1A—C1A	1.476 (6)	N1B—C1B	1.479 (6)
N2A—C5A	1.463 (7)	N2B—C5B	1.475 (6)
N2A—C2A	1.481 (6)	N2B—C1B	1.475 (6)
N2A—C1A	1.487 (6)	N2B—C2B	1.484 (7)
N3A—C2A	1.451 (7)	N3B—C2B	1.449 (7)
N3A—C3A	1.461 (7)	N3B—C6B	1.464 (7)
N3A—C6A	1.479 (8)	N3B—C3B	1.470 (7)
N4A—C4A	1.458 (7)	N4B—C6B	1.452 (8)
N4A—C5A	1.464 (6)	N4B—C4B	1.462 (7)
N4A—C6A	1.467 (8)	N4B—C5B	1.477 (6)
C1A—H1AA	0.9800	C1B—H1BA	0.9800
C1A—H1AB	0.9800	C1B—H1BB	0.9800
C2A—H2AA	0.9800	C2B—H2BA	0.9800
C2A—H2AB	0.9800	C2B—H2BB	0.9800
C3A—H3AA	0.9800	C3B—H3BA	0.9800
C3A—H3AB	0.9800	C3B—H3BB	0.9800
C4A—H4AA	0.9800	C4B—H4BA	0.9800
C4A—H4AB	0.9800	C4B—H4BB	0.9800
C5A—H5AA	0.9800	C5B—H5BA	0.9800
C5A—H5AB	0.9800	C5B—H5BB	0.9800
C6A—H6AA	0.9800	C6B—H6BA	0.9800
C6A—H6AB	0.9800	C6B—H6BB	0.9800
C7A—C12A	1.383 (8)	C7B—C12B	1.375 (8)
C7A—C8A	1.387 (8)	C7B—C8B	1.396 (8)
C7A—C13A	1.480 (8)	C7B—C13B	1.480 (8)
C8A—C9A	1.372 (9)	C8B—C9B	1.369 (8)
C8A—H8AA	0.9400	C8B—H8BA	0.9400
C9A—C10A	1.346 (11)	C9B—C10B	1.371 (12)
C9A—H9AA	0.9400	C9B—H9BA	0.9400
C10A—C11A	1.397 (12)	C10B—C11B	1.383 (12)
C10A—H10A	0.9400	C10B—H10B	0.9400
C11A—C12A	1.372 (10)	C11B—C12B	1.391 (10)
C11A—H11A	0.9400	C11B—H11B	0.9400
C12A—H12A	0.9400	C12B—H12B	0.9400
C14A—C15A	1.380 (8)	C14B—C15B	1.389 (6)
C14A—C19A	1.399 (7)	C14B—C19B	1.405 (8)
C14A—C20A	1.490 (7)	C14B—C20B	1.475 (8)
C15A—C16A	1.387 (7)	C15B—C16B	1.385 (7)
C15A—H15A	0.9400	C15B—H15B	0.9400
C16A—C17A	1.373 (9)	C16B—C17B	1.370 (9)
C16A—H16A	0.9400	C16B—H16B	0.9400
C17A—C18A	1.366 (9)	C17B—C18B	1.385 (9)
C17A—H17A	0.9400	C17B—H17B	0.9400
C18A—C19A	1.378 (7)	C18B—C19B	1.364 (9)
C18A—H18A	0.9400	C18B—H18B	0.9400
C19A—H19A	0.9400	C19B—H19B	0.9400
C13A—O1A—H1O1	116 (6)	C13B—O1B—H2O1	96 (7)
C20A—O3A—H1O3	112 (6)	C20B—O3B—H2O3	115 (8)
C4A—N1A—C3A	108.8 (4)	C3B—N1B—C4B	109.2 (4)
C4A—N1A—C1A	108.3 (4)	C3B—N1B—C1B	108.2 (4)
C3A—N1A—C1A	107.7 (4)	C4B—N1B—C1B	108.1 (4)
C5A—N2A—C2A	109.6 (4)	C5B—N2B—C1B	108.1 (4)
C5A—N2A—C1A	107.5 (4)	C5B—N2B—C2B	108.9 (4)
C2A—N2A—C1A	107.4 (4)	C1B—N2B—C2B	108.3 (4)
C2A—N3A—C3A	108.6 (4)	C2B—N3B—C6B	108.8 (5)
C2A—N3A—C6A	107.7 (4)	C2B—N3B—C3B	108.4 (4)
C3A—N3A—C6A	108.6 (4)	C6B—N3B—C3B	108.2 (4)
C4A—N4A—C5A	108.0 (5)	C6B—N4B—C4B	108.5 (4)
C4A—N4A—C6A	107.6 (4)	C6B—N4B—C5B	108.2 (4)
C5A—N4A—C6A	108.2 (4)	C4B—N4B—C5B	108.7 (5)
N1A—C1A—N2A	111.1 (4)	N2B—C1B—N1B	111.1 (4)
N1A—C1A—H1AA	109.4	N2B—C1B—H1BA	109.4
N2A—C1A—H1AA	109.4	N1B—C1B—H1BA	109.4
N1A—C1A—H1AB	109.4	N2B—C1B—H1BB	109.4
N2A—C1A—H1AB	109.4	N1B—C1B—H1BB	109.4
H1AA—C1A—H1AB	108.0	H1BA—C1B—H1BB	108.0
N3A—C2A—N2A	111.9 (4)	N3B—C2B—N2B	111.2 (4)
N3A—C2A—H2AA	109.2	N3B—C2B—H2BA	109.4
N2A—C2A—H2AA	109.2	N2B—C2B—H2BA	109.4
N3A—C2A—H2AB	109.2	N3B—C2B—H2BB	109.4
N2A—C2A—H2AB	109.2	N2B—C2B—H2BB	109.4
H2AA—C2A—H2AB	107.9	H2BA—C2B—H2BB	108.0
N3A—C3A—N1A	111.5 (4)	N1B—C3B—N3B	111.5 (4)
N3A—C3A—H3AA	109.3	N1B—C3B—H3BA	109.3
N1A—C3A—H3AA	109.3	N3B—C3B—H3BA	109.3
N3A—C3A—H3AB	109.3	N1B—C3B—H3BB	109.3
N1A—C3A—H3AB	109.3	N3B—C3B—H3BB	109.3
H3AA—C3A—H3AB	108.0	H3BA—C3B—H3BB	108.0
N4A—C4A—N1A	112.6 (4)	N4B—C4B—N1B	111.2 (4)
N4A—C4A—H4AA	109.1	N4B—C4B—H4BA	109.4
N1A—C4A—H4AA	109.1	N1B—C4B—H4BA	109.4
N4A—C4A—H4AB	109.1	N4B—C4B—H4BB	109.4
N1A—C4A—H4AB	109.1	N1B—C4B—H4BB	109.4
H4AA—C4A—H4AB	107.8	H4BA—C4B—H4BB	108.0
N2A—C5A—N4A	112.1 (4)	N2B—C5B—N4B	111.0 (4)
N2A—C5A—H5AA	109.2	N2B—C5B—H5BA	109.4
N4A—C5A—H5AA	109.2	N4B—C5B—H5BA	109.4
N2A—C5A—H5AB	109.2	N2B—C5B—H5BB	109.4
N4A—C5A—H5AB	109.2	N4B—C5B—H5BB	109.4
H5AA—C5A—H5AB	107.9	H5BA—C5B—H5BB	108.0
N4A—C6A—N3A	112.8 (5)	N4B—C6B—N3B	112.7 (5)
N4A—C6A—H6AA	109.0	N4B—C6B—H6BA	109.1
N3A—C6A—H6AA	109.0	N3B—C6B—H6BA	109.1
N4A—C6A—H6AB	109.0	N4B—C6B—H6BB	109.1
N3A—C6A—H6AB	109.0	N3B—C6B—H6BB	109.1
H6AA—C6A—H6AB	107.8	H6BA—C6B—H6BB	107.8
C12A—C7A—C8A	119.3 (5)	C12B—C7B—C8B	120.1 (5)
C12A—C7A—C13A	117.5 (5)	C12B—C7B—C13B	118.7 (5)
C8A—C7A—C13A	123.1 (6)	C8B—C7B—C13B	121.1 (5)
C9A—C8A—C7A	120.0 (7)	C9B—C8B—C7B	119.7 (6)
C9A—C8A—H8AA	120.0	C9B—C8B—H8BA	120.2
C7A—C8A—H8AA	120.0	C7B—C8B—H8BA	120.2
C10A—C9A—C8A	120.6 (7)	C8B—C9B—C10B	120.5 (7)
C10A—C9A—H9AA	119.7	C8B—C9B—H9BA	119.8
C8A—C9A—H9AA	119.7	C10B—C9B—H9BA	119.8
C9A—C10A—C11A	120.7 (7)	C9B—C10B—C11B	120.4 (7)
C9A—C10A—H10A	119.7	C9B—C10B—H10B	119.8
C11A—C10A—H10A	119.7	C11B—C10B—H10B	119.8
C12A—C11A—C10A	119.0 (8)	C10B—C11B—C12B	119.6 (7)
C12A—C11A—H11A	120.5	C10B—C11B—H11B	120.2
C10A—C11A—H11A	120.5	C12B—C11B—H11B	120.2
C11A—C12A—C7A	120.4 (7)	C7B—C12B—C11B	119.7 (7)
C11A—C12A—H12A	119.8	C7B—C12B—H12B	120.1
C7A—C12A—H12A	119.8	C11B—C12B—H12B	120.1
O2A—C13A—O1A	122.4 (5)	O2B—C13B—O1B	122.0 (5)
O2A—C13A—C7A	123.7 (6)	O2B—C13B—C7B	122.7 (5)
O1A—C13A—C7A	113.9 (5)	O1B—C13B—C7B	115.3 (5)
C15A—C14A—C19A	118.6 (5)	C15B—C14B—C19B	118.7 (5)
C15A—C14A—C20A	121.5 (5)	C15B—C14B—C20B	120.9 (5)
C19A—C14A—C20A	119.9 (5)	C19B—C14B—C20B	120.4 (5)
C14A—C15A—C16A	121.1 (5)	C16B—C15B—C14B	120.6 (5)
C14A—C15A—H15A	119.5	C16B—C15B—H15B	119.7
C16A—C15A—H15A	119.5	C14B—C15B—H15B	119.7
C17A—C16A—C15A	118.9 (5)	C17B—C16B—C15B	119.7 (6)
C17A—C16A—H16A	120.5	C17B—C16B—H16B	120.1
C15A—C16A—H16A	120.5	C15B—C16B—H16B	120.1
C18A—C17A—C16A	121.2 (5)	C16B—C17B—C18B	120.3 (6)
C18A—C17A—H17A	119.4	C16B—C17B—H17B	119.8
C16A—C17A—H17A	119.4	C18B—C17B—H17B	119.8
C17A—C18A—C19A	120.0 (5)	C19B—C18B—C17B	120.5 (6)
C17A—C18A—H18A	120.0	C19B—C18B—H18B	119.8
C19A—C18A—H18A	120.0	C17B—C18B—H18B	119.8
C18A—C19A—C14A	120.2 (5)	C18B—C19B—C14B	120.1 (5)
C18A—C19A—H19A	119.9	C18B—C19B—H19B	119.9
C14A—C19A—H19A	119.9	C14B—C19B—H19B	119.9
O4A—C20A—O3A	124.1 (5)	O4B—C20B—O3B	122.4 (5)
O4A—C20A—C14A	122.0 (5)	O4B—C20B—C14B	122.4 (6)
O3A—C20A—C14A	113.9 (5)	O3B—C20B—C14B	115.3 (5)
C4A—N1A—C1A—N2A	58.0 (5)	C5B—N2B—C1B—N1B	−59.7 (5)
C3A—N1A—C1A—N2A	−59.5 (5)	C2B—N2B—C1B—N1B	58.2 (5)
C5A—N2A—C1A—N1A	−59.0 (5)	C3B—N1B—C1B—N2B	−58.6 (5)
C2A—N2A—C1A—N1A	58.9 (5)	C4B—N1B—C1B—N2B	59.6 (5)
C3A—N3A—C2A—N2A	59.6 (6)	C6B—N3B—C2B—N2B	−57.8 (6)
C6A—N3A—C2A—N2A	−57.8 (6)	C3B—N3B—C2B—N2B	59.6 (6)
C5A—N2A—C2A—N3A	57.5 (6)	C5B—N2B—C2B—N3B	58.2 (5)
C1A—N2A—C2A—N3A	−59.0 (6)	C1B—N2B—C2B—N3B	−59.1 (6)
C2A—N3A—C3A—N1A	−59.8 (6)	C4B—N1B—C3B—N3B	−58.0 (5)
C6A—N3A—C3A—N1A	57.0 (5)	C1B—N1B—C3B—N3B	59.4 (5)
C4A—N1A—C3A—N3A	−57.5 (6)	C2B—N3B—C3B—N1B	−60.3 (6)
C1A—N1A—C3A—N3A	59.7 (5)	C6B—N3B—C3B—N1B	57.5 (6)
C5A—N4A—C4A—N1A	58.3 (6)	C6B—N4B—C4B—N1B	−57.9 (5)
C6A—N4A—C4A—N1A	−58.3 (5)	C5B—N4B—C4B—N1B	59.5 (5)
C3A—N1A—C4A—N4A	58.7 (5)	C3B—N1B—C4B—N4B	58.1 (5)
C1A—N1A—C4A—N4A	−58.1 (5)	C1B—N1B—C4B—N4B	−59.4 (5)
C2A—N2A—C5A—N4A	−56.5 (6)	C1B—N2B—C5B—N4B	59.3 (5)
C1A—N2A—C5A—N4A	59.9 (5)	C2B—N2B—C5B—N4B	−58.1 (5)
C4A—N4A—C5A—N2A	−59.5 (6)	C6B—N4B—C5B—N2B	58.2 (6)
C6A—N4A—C5A—N2A	56.7 (6)	C4B—N4B—C5B—N2B	−59.5 (6)
C4A—N4A—C6A—N3A	57.9 (6)	C4B—N4B—C6B—N3B	58.9 (6)
C5A—N4A—C6A—N3A	−58.5 (6)	C5B—N4B—C6B—N3B	−58.8 (6)
C2A—N3A—C6A—N4A	59.3 (6)	C2B—N3B—C6B—N4B	59.1 (6)
C3A—N3A—C6A—N4A	−58.1 (6)	C3B—N3B—C6B—N4B	−58.5 (6)
C12A—C7A—C8A—C9A	−0.4 (9)	C12B—C7B—C8B—C9B	0.0 (8)
C13A—C7A—C8A—C9A	175.6 (5)	C13B—C7B—C8B—C9B	177.3 (5)
C7A—C8A—C9A—C10A	0.3 (10)	C7B—C8B—C9B—C10B	1.1 (10)
C8A—C9A—C10A—C11A	0.3 (11)	C8B—C9B—C10B—C11B	−1.3 (12)
C9A—C10A—C11A—C12A	−0.8 (11)	C9B—C10B—C11B—C12B	0.2 (12)
C10A—C11A—C12A—C7A	0.7 (10)	C8B—C7B—C12B—C11B	−1.1 (9)
C8A—C7A—C12A—C11A	−0.1 (9)	C13B—C7B—C12B—C11B	−178.3 (6)
C13A—C7A—C12A—C11A	−176.3 (6)	C10B—C11B—C12B—C7B	0.9 (11)
C12A—C7A—C13A—O2A	9.6 (9)	C12B—C7B—C13B—O2B	12.1 (9)
C8A—C7A—C13A—O2A	−166.5 (6)	C8B—C7B—C13B—O2B	−165.1 (6)
C12A—C7A—C13A—O1A	−171.5 (5)	C12B—C7B—C13B—O1B	−169.1 (5)
C8A—C7A—C13A—O1A	12.4 (8)	C8B—C7B—C13B—O1B	13.6 (8)
C19A—C14A—C15A—C16A	1.8 (8)	C19B—C14B—C15B—C16B	0.4 (7)
C20A—C14A—C15A—C16A	179.3 (5)	C20B—C14B—C15B—C16B	179.5 (5)
C14A—C15A—C16A—C17A	−0.7 (9)	C14B—C15B—C16B—C17B	0.0 (8)
C15A—C16A—C17A—C18A	−0.9 (10)	C15B—C16B—C17B—C18B	−0.3 (9)
C16A—C17A—C18A—C19A	1.2 (10)	C16B—C17B—C18B—C19B	0.1 (9)
C17A—C18A—C19A—C14A	0.0 (9)	C17B—C18B—C19B—C14B	0.3 (9)
C15A—C14A—C19A—C18A	−1.5 (8)	C15B—C14B—C19B—C18B	−0.5 (8)
C20A—C14A—C19A—C18A	−179.0 (5)	C20B—C14B—C19B—C18B	−179.6 (5)
C15A—C14A—C20A—O4A	−172.9 (6)	C15B—C14B—C20B—O4B	−172.5 (5)
C19A—C14A—C20A—O4A	4.5 (8)	C19B—C14B—C20B—O4B	6.6 (8)
C15A—C14A—C20A—O3A	6.5 (7)	C15B—C14B—C20B—O3B	6.5 (7)
C19A—C14A—C20A—O3A	−176.1 (5)	C19B—C14B—C20B—O3B	−174.4 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1O1···N1A	0.82 (6)	1.86 (6)	2.667 (6)	169 (6)
O3A—H1O3···N2A	0.83 (6)	1.79 (6)	2.622 (6)	178 (9)
O1B—H2O1···N1B	0.83 (8)	1.86 (8)	2.649 (6)	159 (9)
O3B—H2O3···N2B	0.83 (9)	1.78 (8)	2.608 (6)	176 (11)
C2A—H2AB···O4A^i	0.98	2.48	3.137 (7)	124
C5A—H5AA···O2A^ii	0.98	2.61	3.234 (7)	121
C2B—H2BB···O4B^i	0.98	2.50	3.178 (7)	126
C5B—H5BA···O2B^iii	0.98	2.56	3.235 (7)	126
C3A—H3AA···Cg17^iv	0.98	2.78	3.754 (6)	170
C10A—H10A···Cg16^v	0.94	3.01	3.854 (9)	151
C10B—H10B···Cg17^vi	0.94	2.88	3.682 (9)	143
C5A—H5AB···Cg15^iv	0.98	2.89	3.823 (6)	160
C17A—H17A···Cg18^vii	0.94	2.87	3.743 (6)	155
C3B—H3BA···Cg18^viii	0.98	2.81	3.785 (6)	171
C5B—H5BB···Cg16^viii	0.98	2.89	3.814 (5)	158

Symmetry codes: (i) x+1, y, z; (ii) x−1/2, −y+1, z−1/2; (iii) x−1/2, −y, z−1/2; (iv) x+1/2, −y+1, z−1/2; (v) x+1/2, −y+1, z+1/2; (vi) x−1, y, z; (vii) x+1/2, −y, z+1/2; (viii) x+1/2, −y, z−1/2.

Hexamethylenetetramine bis(benzoic acid) (1533068)

Crystal data

C6H12N4·2(C7H6O2)	F(000) = 816
Mr = 384.43	Dx = 1.307 Mg m^−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
a = 6.1398 (8) Å	Cell parameters from 6036 reflections
b = 26.721 (4) Å	θ = 2.9–28.2°
c = 12.0772 (17) Å	µ = 0.09 mm^−1
β = 99.554 (2)°	T = 240 K
V = 1953.9 (5) Å^3	Block, colourless
Z = 4	0.76 × 0.39 × 0.21 mm

Data collection

Bruker APEX Duo CCD area detector diffractometer	4889 independent reflections
Radiation source: fine-focus sealed tube	2934 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
φ and ω scans	θmax = 28.5°, θmin = 1.9°
Absorption correction: multi-scan (TWINABS; Sheldrick, 2012)	h = −8→8
Tmin = 0.789, Tmax = 0.937	k = 0→35
6401 measured reflections	l = 0→16

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.057	w = 1/[σ^2(Fo^2) + (0.0706P)^2 + 0.2054P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.168	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.23 e Å^−3
4889 reflections	Δρmin = −0.20 e Å^−3
522 parameters	Absolute structure: No quotients, so Flack parameter determined by classical intensity fit
6 restraints	Absolute structure parameter: −1.3 (13)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1A	0.6799 (7)	0.38149 (16)	0.4618 (4)	0.0671 (13)
H1O1	0.624 (7)	0.4009 (15)	0.501 (4)	0.051 (15)*
O2A	0.4065 (7)	0.39955 (17)	0.3264 (4)	0.0864 (16)
O3A	0.4242 (6)	0.60996 (13)	0.3973 (3)	0.0528 (10)
H1O3	0.419 (11)	0.5920 (19)	0.452 (3)	0.08 (2)*
O4A	0.7823 (6)	0.60495 (15)	0.4611 (4)	0.0691 (12)
N1A	0.4776 (6)	0.45021 (13)	0.5685 (3)	0.0402 (9)
N2A	0.3959 (6)	0.53964 (13)	0.5440 (3)	0.0385 (9)
N3A	0.1345 (6)	0.48337 (16)	0.6127 (4)	0.0465 (10)
N4A	0.4854 (7)	0.50406 (14)	0.7318 (4)	0.0460 (11)
C1A	0.4984 (8)	0.49542 (14)	0.5004 (5)	0.0409 (12)
H1AA	0.6552	0.5022	0.5001	0.049*
H1AB	0.4277	0.4892	0.4227	0.049*
C2A	0.1595 (7)	0.52738 (17)	0.5439 (5)	0.0479 (12)
H2AA	0.0867	0.5561	0.5728	0.057*
H2AB	0.0865	0.5212	0.4667	0.057*
C3A	0.2431 (8)	0.44083 (16)	0.5684 (5)	0.0461 (12)
H3AA	0.2271	0.4111	0.6140	0.055*
H3AB	0.1701	0.4339	0.4914	0.055*
C4A	0.5841 (8)	0.46123 (19)	0.6846 (4)	0.0497 (13)
H4AA	0.5721	0.4318	0.7317	0.060*
H4AB	0.7414	0.4678	0.6856	0.060*
C5A	0.5055 (8)	0.54787 (17)	0.6605 (4)	0.0464 (12)
H5AA	0.6622	0.5551	0.6612	0.056*
H5AB	0.4394	0.5770	0.6913	0.056*
C6A	0.2499 (9)	0.4932 (2)	0.7281 (5)	0.0518 (14)
H6AA	0.1799	0.5218	0.7592	0.062*
H6AB	0.2346	0.4640	0.7752	0.062*
C7A	0.6928 (8)	0.34711 (16)	0.2844 (5)	0.0436 (12)
C8A	0.9068 (9)	0.33143 (18)	0.3188 (5)	0.0527 (14)
H8AA	0.9802	0.3385	0.3917	0.063*
C9A	1.0135 (12)	0.3049 (2)	0.2439 (7)	0.077 (2)
H9AA	1.1613	0.2950	0.2655	0.092*
C10A	0.9040 (14)	0.2934 (2)	0.1395 (7)	0.089 (2)
H10A	0.9752	0.2748	0.0899	0.107*
C11A	0.6891 (14)	0.3089 (2)	0.1064 (6)	0.084 (2)
H11A	0.6136	0.3010	0.0344	0.101*
C12A	0.5854 (11)	0.33600 (19)	0.1789 (6)	0.0652 (16)
H12A	0.4395	0.3470	0.1559	0.078*
C13A	0.5776 (8)	0.37846 (18)	0.3596 (5)	0.0503 (14)
C14A	0.6649 (7)	0.65408 (15)	0.2984 (4)	0.0358 (10)
C15A	0.4872 (8)	0.66713 (17)	0.2181 (4)	0.0459 (12)
H15A	0.3449	0.6557	0.2239	0.055*
C16A	0.5191 (10)	0.69709 (19)	0.1290 (5)	0.0610 (15)
H16A	0.3991	0.7059	0.0735	0.073*
C17A	0.7261 (11)	0.71381 (19)	0.1225 (5)	0.0626 (16)
H17A	0.7463	0.7349	0.0628	0.075*
C18A	0.9043 (9)	0.70088 (19)	0.1996 (6)	0.0604 (16)
H18A	1.0462	0.7123	0.1927	0.073*
C19A	0.8724 (8)	0.66998 (18)	0.2902 (5)	0.0511 (13)
H19A	0.9933	0.6605	0.3445	0.061*
C20A	0.6303 (8)	0.62042 (16)	0.3945 (4)	0.0389 (11)
O1B	1.4453 (7)	0.88345 (17)	0.7161 (3)	0.0679 (13)
H2O1	1.388 (10)	0.9048 (18)	0.752 (5)	0.09 (2)*
O2B	1.1785 (7)	0.90126 (18)	0.5778 (4)	0.0830 (16)
O3B	1.1830 (6)	1.11072 (15)	0.6502 (3)	0.0569 (11)
H2O3	1.156 (12)	1.0867 (19)	0.691 (5)	0.12 (3)*
O4B	1.5410 (6)	1.10827 (17)	0.7177 (3)	0.0735 (13)
N1B	1.2388 (6)	0.95182 (14)	0.8208 (3)	0.0381 (9)
N2B	1.1530 (6)	1.04018 (15)	0.7985 (3)	0.0381 (9)
N3B	0.8956 (6)	0.98407 (18)	0.8659 (4)	0.0490 (11)
N4B	1.2440 (7)	1.00420 (15)	0.9855 (4)	0.0475 (12)
C1B	1.2577 (8)	0.99715 (15)	0.7538 (4)	0.0369 (11)
H1BA	1.4141	1.0045	0.7539	0.044*
H1BB	1.1876	0.9912	0.6759	0.044*
C2B	0.9196 (7)	1.02835 (19)	0.7987 (4)	0.0474 (12)
H2BA	0.8481	1.0569	0.8290	0.057*
H2BB	0.8454	1.0227	0.7214	0.057*
C3B	1.0015 (7)	0.94231 (19)	0.8194 (4)	0.0479 (12)
H3BA	0.9289	0.9364	0.7419	0.057*
H3BB	0.9842	0.9121	0.8630	0.057*
C4B	1.3452 (7)	0.96191 (18)	0.9376 (4)	0.0456 (12)
H4BA	1.3336	0.9321	0.9835	0.055*
H4BB	1.5024	0.9689	0.9390	0.055*
C5B	1.2625 (8)	1.04795 (18)	0.9162 (4)	0.0465 (12)
H5BA	1.4190	1.0555	0.9173	0.056*
H5BB	1.1952	1.0767	0.9477	0.056*
C6B	1.0088 (9)	0.99318 (19)	0.9805 (4)	0.0483 (13)
H6BA	0.9933	0.9636	1.0265	0.058*
H6BB	0.9381	1.0214	1.0123	0.058*
C7B	1.4648 (8)	0.84750 (18)	0.5415 (4)	0.0439 (12)
C8B	1.6785 (9)	0.8318 (2)	0.5775 (5)	0.0536 (13)
H8BA	1.7510	0.8401	0.6500	0.064*
C9B	1.7872 (12)	0.8036 (2)	0.5061 (6)	0.079 (2)
H9BA	1.9348	0.7937	0.5287	0.094*
C10B	1.6728 (16)	0.7903 (3)	0.4007 (7)	0.097 (3)
H10B	1.7422	0.7703	0.3528	0.116*
C11B	1.4649 (15)	0.8059 (3)	0.3670 (6)	0.089 (2)
H11B	1.3918	0.7973	0.2949	0.107*
C12B	1.3562 (12)	0.8341 (2)	0.4358 (5)	0.0692 (17)
H12B	1.2095	0.8442	0.4113	0.083*
C13B	1.3469 (8)	0.87924 (19)	0.6129 (4)	0.0460 (12)
C14B	1.4236 (7)	1.15407 (17)	0.5516 (4)	0.0371 (10)
C15B	1.2487 (7)	1.16472 (17)	0.4669 (4)	0.0420 (11)
H15B	1.1071	1.1524	0.4714	0.050*
C16B	1.2808 (9)	1.19339 (19)	0.3757 (4)	0.0509 (12)
H16B	1.1624	1.1999	0.3174	0.061*
C17B	1.4887 (9)	1.2125 (2)	0.3708 (5)	0.0573 (14)
H17B	1.5108	1.2325	0.3097	0.069*
C18B	1.6612 (9)	1.2024 (2)	0.4541 (5)	0.0557 (14)
H18B	1.8024	1.2149	0.4495	0.067*
C19B	1.6297 (8)	1.17383 (19)	0.5450 (5)	0.0505 (13)
H19B	1.7490	1.1677	0.6030	0.061*
C20B	1.3884 (8)	1.12333 (18)	0.6482 (4)	0.0432 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.073 (3)	0.067 (3)	0.059 (3)	0.037 (2)	0.003 (2)	−0.008 (2)
O2A	0.065 (3)	0.095 (3)	0.091 (4)	0.040 (2)	−0.013 (2)	−0.028 (3)
O3A	0.051 (2)	0.048 (2)	0.059 (3)	−0.0044 (16)	0.0088 (18)	0.0247 (19)
O4A	0.056 (2)	0.076 (3)	0.069 (3)	0.004 (2)	−0.008 (2)	0.031 (2)
N1A	0.041 (2)	0.0291 (18)	0.051 (2)	0.0041 (15)	0.0093 (18)	0.0038 (18)
N2A	0.043 (2)	0.0300 (18)	0.043 (2)	0.0000 (16)	0.0099 (18)	0.0033 (17)
N3A	0.038 (2)	0.042 (2)	0.063 (3)	−0.0022 (18)	0.0180 (19)	0.005 (2)
N4A	0.060 (3)	0.042 (2)	0.036 (3)	−0.0030 (17)	0.007 (2)	0.0026 (17)
C1A	0.043 (3)	0.036 (2)	0.046 (3)	0.0002 (18)	0.013 (2)	0.0032 (19)
C2A	0.039 (2)	0.041 (3)	0.064 (3)	0.0065 (19)	0.010 (2)	0.004 (2)
C3A	0.046 (2)	0.032 (2)	0.061 (3)	−0.008 (2)	0.010 (2)	0.005 (2)
C4A	0.046 (3)	0.049 (3)	0.051 (3)	0.010 (2)	0.000 (2)	0.015 (3)
C5A	0.053 (3)	0.034 (2)	0.053 (3)	−0.008 (2)	0.009 (2)	−0.001 (2)
C6A	0.058 (3)	0.054 (3)	0.049 (4)	−0.004 (2)	0.026 (3)	0.006 (3)
C7A	0.054 (3)	0.020 (2)	0.057 (3)	0.0067 (19)	0.011 (2)	0.001 (2)
C8A	0.057 (3)	0.034 (2)	0.069 (4)	0.011 (2)	0.014 (3)	0.003 (3)
C9A	0.083 (4)	0.058 (4)	0.096 (5)	0.030 (3)	0.034 (4)	0.013 (4)
C10A	0.130 (7)	0.049 (3)	0.104 (6)	0.018 (4)	0.071 (5)	−0.001 (4)
C11A	0.133 (7)	0.059 (4)	0.064 (5)	0.003 (4)	0.026 (4)	−0.019 (4)
C12A	0.084 (4)	0.037 (3)	0.074 (4)	0.001 (3)	0.010 (3)	0.000 (3)
C13A	0.049 (3)	0.035 (2)	0.066 (4)	0.012 (2)	0.006 (3)	−0.002 (3)
C14A	0.044 (2)	0.0183 (19)	0.046 (3)	0.0033 (17)	0.011 (2)	0.0020 (19)
C15A	0.052 (3)	0.033 (2)	0.053 (3)	0.001 (2)	0.009 (2)	0.005 (2)
C16A	0.078 (4)	0.045 (3)	0.058 (4)	0.008 (3)	0.006 (3)	0.017 (3)
C17A	0.089 (4)	0.040 (3)	0.064 (4)	0.001 (3)	0.026 (3)	0.013 (3)
C18A	0.056 (3)	0.041 (3)	0.090 (5)	−0.002 (2)	0.029 (3)	0.005 (3)
C19A	0.047 (3)	0.031 (2)	0.077 (4)	0.006 (2)	0.014 (3)	0.001 (3)
C20A	0.046 (3)	0.024 (2)	0.046 (3)	0.0010 (19)	0.006 (2)	0.005 (2)
O1B	0.076 (3)	0.089 (3)	0.037 (2)	0.046 (2)	0.0033 (19)	−0.011 (2)
O2B	0.066 (3)	0.106 (3)	0.066 (3)	0.038 (2)	−0.018 (2)	−0.025 (3)
O3B	0.050 (2)	0.070 (3)	0.049 (2)	−0.0013 (18)	0.0046 (18)	0.023 (2)
O4B	0.054 (2)	0.102 (3)	0.058 (3)	0.008 (2)	−0.010 (2)	0.035 (2)
N1B	0.041 (2)	0.050 (2)	0.0261 (19)	0.0065 (17)	0.0119 (15)	−0.0007 (17)
N2B	0.042 (2)	0.051 (2)	0.0225 (19)	−0.0003 (17)	0.0075 (15)	0.0030 (17)
N3B	0.035 (2)	0.067 (3)	0.049 (3)	0.002 (2)	0.0186 (18)	0.000 (2)
N4B	0.060 (3)	0.058 (3)	0.023 (2)	−0.0022 (19)	0.0011 (19)	−0.0015 (17)
C1B	0.039 (2)	0.050 (3)	0.026 (3)	0.0040 (17)	0.018 (2)	0.0017 (17)
C2B	0.038 (2)	0.060 (3)	0.044 (3)	0.012 (2)	0.007 (2)	0.006 (2)
C3B	0.043 (3)	0.060 (3)	0.042 (3)	−0.010 (2)	0.009 (2)	−0.002 (2)
C4B	0.045 (3)	0.059 (3)	0.031 (3)	0.006 (2)	0.001 (2)	0.010 (2)
C5B	0.055 (3)	0.052 (3)	0.031 (3)	−0.009 (2)	0.003 (2)	−0.005 (2)
C6B	0.061 (3)	0.058 (3)	0.031 (3)	0.001 (2)	0.023 (2)	0.002 (2)
C7B	0.060 (3)	0.042 (3)	0.032 (3)	−0.005 (2)	0.013 (2)	0.004 (2)
C8B	0.060 (3)	0.056 (3)	0.049 (3)	0.007 (3)	0.021 (3)	0.005 (3)
C9B	0.081 (4)	0.072 (4)	0.094 (5)	0.016 (3)	0.048 (4)	0.007 (4)
C10B	0.156 (8)	0.078 (5)	0.069 (5)	0.021 (5)	0.058 (5)	−0.013 (4)
C11B	0.137 (7)	0.084 (5)	0.048 (4)	0.015 (5)	0.023 (4)	−0.009 (4)
C12B	0.095 (4)	0.077 (4)	0.035 (3)	0.001 (4)	0.010 (3)	−0.005 (3)
C13B	0.054 (3)	0.048 (3)	0.035 (3)	0.004 (2)	0.006 (2)	−0.006 (2)
C14B	0.041 (2)	0.040 (2)	0.029 (2)	0.0048 (19)	0.0040 (19)	−0.007 (2)
C15B	0.037 (2)	0.048 (3)	0.040 (3)	−0.001 (2)	0.0039 (19)	0.002 (2)
C16B	0.056 (3)	0.053 (3)	0.043 (3)	0.001 (2)	0.004 (2)	0.010 (3)
C17B	0.064 (3)	0.060 (3)	0.051 (3)	0.000 (3)	0.018 (3)	0.018 (3)
C18B	0.050 (3)	0.059 (3)	0.061 (4)	−0.005 (2)	0.018 (2)	−0.003 (3)
C19B	0.037 (2)	0.057 (3)	0.056 (3)	0.005 (2)	0.005 (2)	−0.004 (3)
C20B	0.049 (3)	0.045 (3)	0.033 (3)	0.003 (2)	−0.002 (2)	0.003 (2)

Geometric parameters (Å, º)

O1A—C13A	1.291 (7)	O1B—C13B	1.298 (6)
O1A—H1O1	0.82 (2)	O1B—H2O1	0.83 (2)
O2A—C13A	1.201 (6)	O2B—C13B	1.204 (6)
O3A—C20A	1.301 (6)	O3B—C20B	1.309 (6)
O3A—H1O3	0.82 (2)	O3B—H2O3	0.84 (2)
O4A—C20A	1.200 (6)	O4B—C20B	1.218 (5)
N1A—C3A	1.461 (6)	N1B—C1B	1.472 (6)
N1A—C4A	1.475 (6)	N1B—C3B	1.476 (6)
N1A—C1A	1.479 (5)	N1B—C4B	1.477 (5)
N2A—C5A	1.471 (6)	N2B—C1B	1.464 (5)
N2A—C1A	1.476 (6)	N2B—C2B	1.468 (6)
N2A—C2A	1.488 (5)	N2B—C5B	1.483 (6)
N3A—C2A	1.463 (6)	N3B—C3B	1.451 (6)
N3A—C3A	1.464 (6)	N3B—C2B	1.456 (7)
N3A—C6A	1.478 (7)	N3B—C6B	1.463 (6)
N4A—C4A	1.454 (6)	N4B—C5B	1.453 (6)
N4A—C6A	1.468 (7)	N4B—C4B	1.455 (6)
N4A—C5A	1.470 (6)	N4B—C6B	1.465 (7)
C1A—H1AA	0.9800	C1B—H1BA	0.9800
C1A—H1AB	0.9800	C1B—H1BB	0.9800
C2A—H2AA	0.9800	C2B—H2BA	0.9800
C2A—H2AB	0.9800	C2B—H2BB	0.9800
C3A—H3AA	0.9800	C3B—H3BA	0.9800
C3A—H3AB	0.9800	C3B—H3BB	0.9800
C4A—H4AA	0.9800	C4B—H4BA	0.9800
C4A—H4AB	0.9800	C4B—H4BB	0.9800
C5A—H5AA	0.9800	C5B—H5BA	0.9800
C5A—H5AB	0.9800	C5B—H5BB	0.9800
C6A—H6AA	0.9800	C6B—H6BA	0.9800
C6A—H6AB	0.9800	C6B—H6BB	0.9800
C7A—C12A	1.367 (8)	C7B—C8B	1.377 (7)
C7A—C8A	1.376 (7)	C7B—C12B	1.386 (7)
C7A—C13A	1.496 (7)	C7B—C13B	1.481 (7)
C8A—C9A	1.395 (8)	C8B—C9B	1.396 (7)
C8A—H8AA	0.9400	C8B—H8BA	0.9400
C9A—C10A	1.362 (10)	C9B—C10B	1.394 (11)
C9A—H9AA	0.9400	C9B—H9BA	0.9400
C10A—C11A	1.378 (11)	C10B—C11B	1.340 (11)
C10A—H10A	0.9400	C10B—H10B	0.9400
C11A—C12A	1.371 (9)	C11B—C12B	1.374 (9)
C11A—H11A	0.9400	C11B—H11B	0.9400
C12A—H12A	0.9400	C12B—H12B	0.9400
C14A—C19A	1.362 (7)	C14B—C15B	1.385 (6)
C14A—C15A	1.379 (6)	C14B—C19B	1.386 (7)
C14A—C20A	1.511 (6)	C14B—C20B	1.472 (7)
C15A—C16A	1.380 (7)	C15B—C16B	1.382 (7)
C15A—H15A	0.9400	C15B—H15B	0.9400
C16A—C17A	1.362 (8)	C16B—C17B	1.385 (7)
C16A—H16A	0.9400	C16B—H16B	0.9400
C17A—C18A	1.359 (8)	C17B—C18B	1.361 (7)
C17A—H17A	0.9400	C17B—H17B	0.9400
C18A—C19A	1.411 (8)	C18B—C19B	1.376 (8)
C18A—H18A	0.9400	C18B—H18B	0.9400
C19A—H19A	0.9400	C19B—H19B	0.9400
C13A—O1A—H1O1	114 (4)	C13B—O1B—H2O1	113 (5)
C20A—O3A—H1O3	108 (5)	C20B—O3B—H2O3	119 (5)
C3A—N1A—C4A	108.4 (4)	C1B—N1B—C3B	107.7 (4)
C3A—N1A—C1A	108.4 (4)	C1B—N1B—C4B	108.2 (4)
C4A—N1A—C1A	107.5 (4)	C3B—N1B—C4B	108.8 (3)
C5A—N2A—C1A	107.9 (4)	C1B—N2B—C2B	108.7 (4)
C5A—N2A—C2A	108.9 (4)	C1B—N2B—C5B	107.8 (4)
C1A—N2A—C2A	107.3 (4)	C2B—N2B—C5B	108.4 (3)
C2A—N3A—C3A	108.6 (4)	C3B—N3B—C2B	108.4 (4)
C2A—N3A—C6A	108.2 (4)	C3B—N3B—C6B	108.7 (4)
C3A—N3A—C6A	107.9 (4)	C2B—N3B—C6B	108.4 (4)
C4A—N4A—C6A	107.8 (4)	C5B—N4B—C4B	108.4 (4)
C4A—N4A—C5A	108.4 (4)	C5B—N4B—C6B	108.0 (4)
C6A—N4A—C5A	108.5 (4)	C4B—N4B—C6B	108.1 (4)
N2A—C1A—N1A	112.0 (4)	N2B—C1B—N1B	111.3 (4)
N2A—C1A—H1AA	109.2	N2B—C1B—H1BA	109.4
N1A—C1A—H1AA	109.2	N1B—C1B—H1BA	109.4
N2A—C1A—H1AB	109.2	N2B—C1B—H1BB	109.4
N1A—C1A—H1AB	109.2	N1B—C1B—H1BB	109.4
H1AA—C1A—H1AB	107.9	H1BA—C1B—H1BB	108.0
N3A—C2A—N2A	111.8 (3)	N3B—C2B—N2B	111.4 (4)
N3A—C2A—H2AA	109.3	N3B—C2B—H2BA	109.3
N2A—C2A—H2AA	109.3	N2B—C2B—H2BA	109.3
N3A—C2A—H2AB	109.3	N3B—C2B—H2BB	109.3
N2A—C2A—H2AB	109.3	N2B—C2B—H2BB	109.3
H2AA—C2A—H2AB	107.9	H2BA—C2B—H2BB	108.0
N1A—C3A—N3A	112.0 (3)	N3B—C3B—N1B	111.6 (4)
N1A—C3A—H3AA	109.2	N3B—C3B—H3BA	109.3
N3A—C3A—H3AA	109.2	N1B—C3B—H3BA	109.3
N1A—C3A—H3AB	109.2	N3B—C3B—H3BB	109.3
N3A—C3A—H3AB	109.2	N1B—C3B—H3BB	109.3
H3AA—C3A—H3AB	107.9	H3BA—C3B—H3BB	108.0
N4A—C4A—N1A	112.4 (4)	N4B—C4B—N1B	111.8 (4)
N4A—C4A—H4AA	109.1	N4B—C4B—H4BA	109.3
N1A—C4A—H4AA	109.1	N1B—C4B—H4BA	109.3
N4A—C4A—H4AB	109.1	N4B—C4B—H4BB	109.3
N1A—C4A—H4AB	109.1	N1B—C4B—H4BB	109.3
H4AA—C4A—H4AB	107.8	H4BA—C4B—H4BB	107.9
N4A—C5A—N2A	111.8 (4)	N4B—C5B—N2B	111.9 (4)
N4A—C5A—H5AA	109.3	N4B—C5B—H5BA	109.2
N2A—C5A—H5AA	109.3	N2B—C5B—H5BA	109.2
N4A—C5A—H5AB	109.3	N4B—C5B—H5BB	109.2
N2A—C5A—H5AB	109.3	N2B—C5B—H5BB	109.2
H5AA—C5A—H5AB	107.9	H5BA—C5B—H5BB	107.9
N4A—C6A—N3A	112.3 (4)	N3B—C6B—N4B	112.5 (4)
N4A—C6A—H6AA	109.1	N3B—C6B—H6BA	109.1
N3A—C6A—H6AA	109.1	N4B—C6B—H6BA	109.1
N4A—C6A—H6AB	109.1	N3B—C6B—H6BB	109.1
N3A—C6A—H6AB	109.1	N4B—C6B—H6BB	109.1
H6AA—C6A—H6AB	107.9	H6BA—C6B—H6BB	107.8
C12A—C7A—C8A	120.2 (5)	C8B—C7B—C12B	120.0 (5)
C12A—C7A—C13A	118.9 (5)	C8B—C7B—C13B	121.5 (5)
C8A—C7A—C13A	120.8 (5)	C12B—C7B—C13B	118.5 (5)
C7A—C8A—C9A	119.1 (6)	C7B—C8B—C9B	119.8 (6)
C7A—C8A—H8AA	120.4	C7B—C8B—H8BA	120.1
C9A—C8A—H8AA	120.4	C9B—C8B—H8BA	120.1
C10A—C9A—C8A	120.2 (6)	C10B—C9B—C8B	118.8 (7)
C10A—C9A—H9AA	119.9	C10B—C9B—H9BA	120.6
C8A—C9A—H9AA	119.9	C8B—C9B—H9BA	120.6
C9A—C10A—C11A	120.1 (6)	C11B—C10B—C9B	120.6 (6)
C9A—C10A—H10A	120.0	C11B—C10B—H10B	119.7
C11A—C10A—H10A	120.0	C9B—C10B—H10B	119.7
C12A—C11A—C10A	119.9 (7)	C10B—C11B—C12B	121.4 (7)
C12A—C11A—H11A	120.1	C10B—C11B—H11B	119.3
C10A—C11A—H11A	120.1	C12B—C11B—H11B	119.3
C7A—C12A—C11A	120.4 (6)	C11B—C12B—C7B	119.4 (7)
C7A—C12A—H12A	119.8	C11B—C12B—H12B	120.3
C11A—C12A—H12A	119.8	C7B—C12B—H12B	120.3
O2A—C13A—O1A	123.3 (5)	O2B—C13B—O1B	122.1 (5)
O2A—C13A—C7A	122.4 (5)	O2B—C13B—C7B	123.3 (5)
O1A—C13A—C7A	114.3 (4)	O1B—C13B—C7B	114.5 (4)
C19A—C14A—C15A	120.7 (5)	C15B—C14B—C19B	118.8 (5)
C19A—C14A—C20A	119.6 (4)	C15B—C14B—C20B	120.2 (4)
C15A—C14A—C20A	119.7 (4)	C19B—C14B—C20B	121.0 (4)
C14A—C15A—C16A	119.8 (5)	C16B—C15B—C14B	120.5 (5)
C14A—C15A—H15A	120.1	C16B—C15B—H15B	119.7
C16A—C15A—H15A	120.1	C14B—C15B—H15B	119.7
C17A—C16A—C15A	119.3 (5)	C15B—C16B—C17B	119.5 (5)
C17A—C16A—H16A	120.3	C15B—C16B—H16B	120.3
C15A—C16A—H16A	120.3	C17B—C16B—H16B	120.3
C18A—C17A—C16A	122.0 (5)	C18B—C17B—C16B	120.4 (5)
C18A—C17A—H17A	119.0	C18B—C17B—H17B	119.8
C16A—C17A—H17A	119.0	C16B—C17B—H17B	119.8
C17A—C18A—C19A	118.8 (5)	C17B—C18B—C19B	120.3 (5)
C17A—C18A—H18A	120.6	C17B—C18B—H18B	119.9
C19A—C18A—H18A	120.6	C19B—C18B—H18B	119.9
C14A—C19A—C18A	119.4 (5)	C18B—C19B—C14B	120.5 (5)
C14A—C19A—H19A	120.3	C18B—C19B—H19B	119.7
C18A—C19A—H19A	120.3	C14B—C19B—H19B	119.7
O4A—C20A—O3A	124.0 (5)	O4B—C20B—O3B	122.4 (5)
O4A—C20A—C14A	121.8 (4)	O4B—C20B—C14B	122.2 (5)
O3A—C20A—C14A	114.2 (4)	O3B—C20B—C14B	115.2 (4)
C5A—N2A—C1A—N1A	58.9 (5)	C2B—N2B—C1B—N1B	−58.5 (5)
C2A—N2A—C1A—N1A	−58.3 (5)	C5B—N2B—C1B—N1B	58.8 (5)
C3A—N1A—C1A—N2A	58.6 (5)	C3B—N1B—C1B—N2B	58.5 (5)
C4A—N1A—C1A—N2A	−58.4 (5)	C4B—N1B—C1B—N2B	−58.9 (5)
C3A—N3A—C2A—N2A	−59.2 (5)	C3B—N3B—C2B—N2B	−59.3 (5)
C6A—N3A—C2A—N2A	57.7 (5)	C6B—N3B—C2B—N2B	58.6 (5)
C5A—N2A—C2A—N3A	−57.7 (5)	C1B—N2B—C2B—N3B	58.6 (5)
C1A—N2A—C2A—N3A	58.8 (5)	C5B—N2B—C2B—N3B	−58.3 (5)
C4A—N1A—C3A—N3A	58.1 (5)	C2B—N3B—C3B—N1B	60.0 (5)
C1A—N1A—C3A—N3A	−58.3 (5)	C6B—N3B—C3B—N1B	−57.7 (5)
C2A—N3A—C3A—N1A	58.9 (5)	C1B—N1B—C3B—N3B	−59.5 (5)
C6A—N3A—C3A—N1A	−58.2 (5)	C4B—N1B—C3B—N3B	57.5 (5)
C6A—N4A—C4A—N1A	58.2 (5)	C5B—N4B—C4B—N1B	−58.9 (5)
C5A—N4A—C4A—N1A	−59.0 (5)	C6B—N4B—C4B—N1B	58.0 (5)
C3A—N1A—C4A—N4A	−58.4 (5)	C1B—N1B—C4B—N4B	58.7 (5)
C1A—N1A—C4A—N4A	58.6 (5)	C3B—N1B—C4B—N4B	−57.9 (5)
C4A—N4A—C5A—N2A	58.9 (5)	C4B—N4B—C5B—N2B	59.1 (5)
C6A—N4A—C5A—N2A	−57.9 (5)	C6B—N4B—C5B—N2B	−57.8 (5)
C1A—N2A—C5A—N4A	−58.6 (5)	C1B—N2B—C5B—N4B	−59.2 (5)
C2A—N2A—C5A—N4A	57.5 (5)	C2B—N2B—C5B—N4B	58.3 (5)
C4A—N4A—C6A—N3A	−58.5 (5)	C3B—N3B—C6B—N4B	58.7 (6)
C5A—N4A—C6A—N3A	58.7 (5)	C2B—N3B—C6B—N4B	−59.0 (5)
C2A—N3A—C6A—N4A	−58.8 (5)	C5B—N4B—C6B—N3B	58.5 (6)
C3A—N3A—C6A—N4A	58.6 (5)	C4B—N4B—C6B—N3B	−58.6 (5)
C12A—C7A—C8A—C9A	1.1 (8)	C12B—C7B—C8B—C9B	1.8 (8)
C13A—C7A—C8A—C9A	−176.0 (5)	C13B—C7B—C8B—C9B	−177.5 (5)
C7A—C8A—C9A—C10A	−2.1 (9)	C7B—C8B—C9B—C10B	−2.3 (9)
C8A—C9A—C10A—C11A	1.6 (10)	C8B—C9B—C10B—C11B	2.3 (11)
C9A—C10A—C11A—C12A	−0.1 (11)	C9B—C10B—C11B—C12B	−1.7 (13)
C8A—C7A—C12A—C11A	0.4 (8)	C10B—C11B—C12B—C7B	1.0 (11)
C13A—C7A—C12A—C11A	177.6 (5)	C8B—C7B—C12B—C11B	−1.1 (9)
C10A—C11A—C12A—C7A	−0.9 (10)	C13B—C7B—C12B—C11B	178.2 (5)
C12A—C7A—C13A—O2A	−9.8 (8)	C8B—C7B—C13B—O2B	165.7 (6)
C8A—C7A—C13A—O2A	167.4 (6)	C12B—C7B—C13B—O2B	−13.5 (8)
C12A—C7A—C13A—O1A	171.4 (5)	C8B—C7B—C13B—O1B	−11.2 (7)
C8A—C7A—C13A—O1A	−11.4 (7)	C12B—C7B—C13B—O1B	169.5 (5)
C19A—C14A—C15A—C16A	−0.8 (7)	C19B—C14B—C15B—C16B	1.8 (7)
C20A—C14A—C15A—C16A	−178.7 (4)	C20B—C14B—C15B—C16B	−179.7 (4)
C14A—C15A—C16A—C17A	−0.7 (8)	C14B—C15B—C16B—C17B	−1.5 (8)
C15A—C16A—C17A—C18A	1.7 (9)	C15B—C16B—C17B—C18B	1.2 (9)
C16A—C17A—C18A—C19A	−1.2 (9)	C16B—C17B—C18B—C19B	−1.2 (9)
C15A—C14A—C19A—C18A	1.2 (7)	C17B—C18B—C19B—C14B	1.5 (8)
C20A—C14A—C19A—C18A	179.2 (4)	C15B—C14B—C19B—C18B	−1.8 (7)
C17A—C18A—C19A—C14A	−0.2 (8)	C20B—C14B—C19B—C18B	179.7 (4)
C19A—C14A—C20A—O4A	−4.0 (7)	C15B—C14B—C20B—O4B	171.3 (5)
C15A—C14A—C20A—O4A	174.0 (5)	C19B—C14B—C20B—O4B	−10.3 (7)
C19A—C14A—C20A—O3A	176.3 (4)	C15B—C14B—C20B—O3B	−4.5 (7)
C15A—C14A—C20A—O3A	−5.7 (6)	C19B—C14B—C20B—O3B	173.9 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1O1···N1A	0.82 (4)	1.86 (4)	2.666 (6)	171 (5)
O3A—H1O3···N2A	0.82 (4)	1.81 (5)	2.608 (5)	165 (5)
O1B—H2O1···N1B	0.83 (6)	1.83 (6)	2.660 (6)	175 (7)
O3B—H2O3···N2B	0.84 (6)	1.80 (6)	2.628 (5)	167 (5)
C2A—H2AA···O4A^i	0.98	2.49	3.145 (6)	124
C5A—H5AA···O2A^ii	0.98	2.59	3.227 (7)	123
C2B—H2BA···O4B^i	0.98	2.53	3.188 (6)	124
C5B—H5BA···O2B^iii	0.98	2.57	3.243 (7)	126
C3A—H3AB···Cg17^iv	0.98	2.81	3.775 (5)	169
C10A—H10A···Cg16^v	0.94	2.99	3.855 (7)	154
C10B—H10B···Cg17^vi	0.94	2.87	3.681 (8)	145
C5A—H5AB···Cg15^iv	0.98	2.90	3.831 (5)	159
C17A—H17A···Cg18^vii	0.94	2.91	3.775 (6)	154
C3B—H3BB···Cg18^viii	0.98	2.83	3.801 (5)	171
C5B—H5BB···Cg16^viii	0.98	2.92	3.841 (6)	157

Symmetry codes: (i) x−1, y, z; (ii) x+1/2, −y+1, z+1/2; (iii) x+1/2, −y+2, z+1/2; (iv) x−1/2, −y+1, z+1/2; (v) x−1/2, −y+1, z−1/2; (vi) x+1, y, z; (vii) x−1/2, −y+2, z−1/2; (viii) x−1/2, −y+2, z+1/2.

Hexamethylenetetramine bis(benzoic acid) (1533069)

Crystal data

C6H12N4·2(C7H6O2)	F(000) = 816
Mr = 384.43	Dx = 1.304 Mg m^−3
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
a = 6.1457 (8) Å	Cell parameters from 7036 reflections
b = 26.765 (3) Å	θ = 2.9–28.1°
c = 12.0716 (16) Å	µ = 0.09 mm^−1
β = 99.654 (2)°	T = 250 K
V = 1957.6 (4) Å^3	Block, colourless
Z = 4	0.76 × 0.39 × 0.21 mm

Data collection

Bruker APEX Duo CCD area detector diffractometer	4828 independent reflections
Radiation source: fine-focus sealed tube	3264 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
φ and ω scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (TWINABS; Sheldrick, 2012)	h = −8→8
Tmin = 0.755, Tmax = 0.937	k = 0→35
6406 measured reflections	l = 0→16

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.051	w = 1/[σ^2(Fo^2) + (0.0476P)^2 + 0.380P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.128	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.18 e Å^−3
4828 reflections	Δρmin = −0.15 e Å^−3
522 parameters	Absolute structure: No quotients, so Flack parameter determined by classical intensity fit
6 restraints	Absolute structure parameter: −1.6 (11)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1A	0.6788 (5)	0.38153 (13)	0.4623 (3)	0.0726 (10)
O2A	0.4072 (5)	0.39984 (14)	0.3254 (3)	0.0924 (13)
O3A	0.4235 (4)	0.60988 (11)	0.3977 (2)	0.0565 (8)
O4A	0.7820 (5)	0.60473 (12)	0.4601 (3)	0.0727 (9)
N1A	0.4764 (4)	0.45020 (11)	0.5681 (2)	0.0414 (7)
N2A	0.3942 (4)	0.53901 (10)	0.5439 (2)	0.0384 (7)
N3A	0.1336 (5)	0.48355 (13)	0.6123 (3)	0.0488 (8)
N4A	0.4832 (6)	0.50426 (13)	0.7311 (3)	0.0515 (9)
C1A	0.4953 (6)	0.49486 (13)	0.4992 (3)	0.0435 (9)
H1AA	0.4222	0.4886	0.4219	0.052*
H1AB	0.6515	0.5016	0.4977	0.052*
C2A	0.1599 (5)	0.52745 (14)	0.5442 (4)	0.0493 (10)
H2AA	0.0891	0.5562	0.5737	0.059*
H2AB	0.0857	0.5216	0.4669	0.059*
C3A	0.2393 (6)	0.44142 (14)	0.5681 (3)	0.0481 (9)
H3AA	0.1656	0.4348	0.4910	0.058*
H3AB	0.2221	0.4118	0.6134	0.058*
C4A	0.5828 (6)	0.46128 (16)	0.6839 (3)	0.0511 (10)
H4AA	0.5713	0.4319	0.7312	0.061*
H4AB	0.7398	0.4680	0.6848	0.061*
C5A	0.5050 (6)	0.54757 (14)	0.6607 (3)	0.0473 (9)
H5AA	0.6618	0.5545	0.6614	0.057*
H5AB	0.4398	0.5768	0.6914	0.057*
C6A	0.2490 (7)	0.49339 (17)	0.7265 (4)	0.0558 (11)
H6AA	0.1787	0.5218	0.7577	0.067*
H6AB	0.2339	0.4642	0.7737	0.067*
C7A	0.6919 (6)	0.34695 (14)	0.2839 (3)	0.0465 (9)
C8A	0.9077 (7)	0.33086 (15)	0.3186 (4)	0.0596 (11)
H8AA	0.9820	0.3379	0.3916	0.072*
C9A	1.0108 (9)	0.30435 (19)	0.2440 (5)	0.0827 (17)
H9AA	1.1574	0.2937	0.2662	0.099*
C10A	0.9038 (12)	0.2935 (2)	0.1394 (6)	0.099 (2)
H10A	0.9761	0.2754	0.0896	0.118*
C11A	0.6868 (11)	0.3091 (2)	0.1057 (5)	0.0875 (17)
H11A	0.6111	0.3011	0.0336	0.105*
C12A	0.5844 (8)	0.33605 (15)	0.1784 (4)	0.0631 (11)
H12A	0.4388	0.3472	0.1555	0.076*
C13A	0.5781 (6)	0.37862 (15)	0.3590 (4)	0.0518 (10)
C14A	0.6618 (5)	0.65384 (13)	0.2985 (3)	0.0383 (8)
C15A	0.4874 (6)	0.66734 (14)	0.2175 (3)	0.0469 (9)
H15A	0.3447	0.6560	0.2226	0.056*
C16A	0.5190 (7)	0.69728 (16)	0.1287 (4)	0.0619 (11)
H16A	0.3985	0.7060	0.0733	0.074*
C17A	0.7243 (8)	0.71422 (16)	0.1213 (4)	0.0663 (13)
H17A	0.7450	0.7351	0.0612	0.080*
C18A	0.9023 (7)	0.70114 (16)	0.2010 (4)	0.0628 (12)
H18A	1.0440	0.7130	0.1952	0.075*
C19A	0.8725 (6)	0.67045 (14)	0.2900 (4)	0.0528 (10)
H19A	0.9939	0.6610	0.3441	0.063*
C20A	0.6294 (6)	0.62049 (13)	0.3948 (3)	0.0417 (8)
O1B	1.4442 (6)	0.88365 (12)	0.7162 (3)	0.0717 (10)
O2B	1.1789 (6)	0.90126 (13)	0.5775 (3)	0.0881 (13)
O3B	1.1836 (5)	1.11033 (11)	0.6504 (3)	0.0585 (8)
O4B	1.5397 (5)	1.10825 (13)	0.7183 (3)	0.0780 (10)
N1B	1.2381 (5)	0.95177 (10)	0.8205 (3)	0.0408 (7)
N2B	1.1537 (5)	1.04034 (10)	0.7986 (2)	0.0402 (7)
N3B	0.8947 (5)	0.98443 (13)	0.8663 (3)	0.0504 (8)
N4B	1.2443 (6)	1.00401 (10)	0.9848 (3)	0.0467 (8)
C1B	1.2573 (6)	0.99707 (11)	0.7535 (3)	0.0382 (9)
H1BA	1.4137	1.0043	0.7534	0.046*
H1BB	1.1865	0.9912	0.6756	0.046*
C2B	0.9188 (6)	1.02840 (14)	0.7991 (3)	0.0504 (10)
H2BA	0.8475	1.0569	0.8291	0.060*
H2BB	0.8443	1.0227	0.7218	0.060*
C3B	1.0008 (6)	0.94246 (13)	0.8194 (3)	0.0501 (10)
H3BA	0.9276	0.9366	0.7420	0.060*
H3BB	0.9837	0.9123	0.8632	0.060*
C4B	1.3429 (6)	0.96158 (13)	0.9371 (3)	0.0491 (10)
H4BA	1.3287	0.9319	0.9829	0.059*
H4BB	1.5006	0.9680	0.9393	0.059*
C5B	1.2634 (7)	1.04821 (13)	0.9162 (3)	0.0472 (9)
H5BA	1.4197	1.0559	0.9174	0.057*
H5BB	1.1958	1.0768	0.9480	0.057*
C6B	1.0084 (7)	0.99315 (15)	0.9809 (3)	0.0543 (11)
H6BA	0.9931	0.9635	1.0267	0.065*
H6BB	0.9387	1.0213	1.0132	0.065*
C7B	1.4633 (7)	0.84761 (11)	0.5422 (3)	0.0444 (9)
C8B	1.6777 (7)	0.83275 (14)	0.5771 (4)	0.0562 (11)
H8BA	1.7519	0.8420	0.6487	0.067*
C9B	1.7858 (10)	0.80394 (17)	0.5069 (5)	0.0819 (16)
H9BA	1.9328	0.7939	0.5303	0.098*
C10B	1.6753 (13)	0.7907 (2)	0.4043 (6)	0.100 (2)
H10B	1.7463	0.7708	0.3569	0.120*
C11B	1.4627 (13)	0.8057 (2)	0.3687 (5)	0.097 (2)
H11B	1.3892	0.7963	0.2971	0.117*
C12B	1.3556 (9)	0.83441 (16)	0.4368 (4)	0.0711 (13)
H12B	1.2099	0.8450	0.4118	0.085*
C13B	1.3477 (7)	0.87933 (13)	0.6132 (3)	0.0487 (9)
C14B	1.4232 (6)	1.15406 (11)	0.5521 (3)	0.0367 (8)
C15B	1.2495 (6)	1.16462 (12)	0.4663 (3)	0.0432 (9)
H15B	1.1082	1.1519	0.4697	0.052*
C16B	1.2823 (7)	1.19361 (13)	0.3760 (3)	0.0533 (10)
H16B	1.1641	1.2003	0.3177	0.064*
C17B	1.4882 (8)	1.21261 (15)	0.3716 (4)	0.0612 (11)
H17B	1.5096	1.2330	0.3109	0.073*
C18B	1.6619 (7)	1.20223 (14)	0.4544 (4)	0.0610 (11)
H18B	1.8029	1.2149	0.4500	0.073*
C19B	1.6305 (7)	1.17284 (15)	0.5458 (4)	0.0544 (10)
H19B	1.7501	1.1658	0.6030	0.065*
C20B	1.3884 (7)	1.12257 (12)	0.6487 (3)	0.0455 (9)
H1O1	0.609 (7)	0.4031 (14)	0.495 (4)	0.086 (17)*
H1O3	0.416 (10)	0.5865 (15)	0.443 (4)	0.11 (2)*
H2O1	1.383 (9)	0.9045 (16)	0.753 (4)	0.10 (2)*
H2O3	1.177 (14)	1.090 (2)	0.702 (5)	0.18 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.072 (2)	0.086 (2)	0.058 (2)	0.0413 (18)	0.0070 (17)	−0.0091 (17)
O2A	0.061 (2)	0.122 (3)	0.086 (3)	0.046 (2)	−0.0142 (18)	−0.026 (2)
O3A	0.0454 (15)	0.0682 (19)	0.0562 (18)	−0.0020 (13)	0.0093 (13)	0.0258 (15)
O4A	0.0519 (17)	0.087 (2)	0.074 (2)	0.0020 (16)	−0.0055 (15)	0.0365 (18)
N1A	0.0355 (16)	0.0503 (16)	0.0413 (17)	0.0048 (13)	0.0144 (13)	0.0053 (13)
N2A	0.0339 (15)	0.0471 (16)	0.0370 (17)	−0.0007 (12)	0.0137 (12)	0.0048 (13)
N3A	0.0300 (15)	0.062 (2)	0.060 (2)	−0.0062 (14)	0.0218 (14)	0.0028 (17)
N4A	0.054 (2)	0.069 (2)	0.0312 (19)	−0.0023 (15)	0.0073 (15)	0.0036 (14)
C1A	0.0365 (19)	0.065 (2)	0.034 (2)	−0.0020 (15)	0.0205 (16)	0.0024 (15)
C2A	0.0318 (18)	0.056 (2)	0.061 (3)	0.0073 (15)	0.0093 (17)	0.0049 (19)
C3A	0.0391 (19)	0.051 (2)	0.056 (2)	−0.0089 (16)	0.0122 (16)	0.0018 (18)
C4A	0.0357 (19)	0.070 (3)	0.046 (2)	0.0071 (17)	0.0035 (16)	0.0163 (19)
C5A	0.046 (2)	0.058 (2)	0.039 (2)	−0.0103 (17)	0.0071 (16)	−0.0027 (17)
C6A	0.056 (2)	0.069 (3)	0.050 (3)	−0.003 (2)	0.034 (2)	0.0024 (19)
C7A	0.051 (2)	0.0411 (19)	0.049 (2)	0.0052 (16)	0.0139 (17)	0.0025 (16)
C8A	0.052 (2)	0.055 (2)	0.075 (3)	0.014 (2)	0.019 (2)	0.009 (2)
C9A	0.082 (4)	0.071 (3)	0.106 (5)	0.031 (3)	0.050 (3)	0.020 (3)
C10A	0.142 (6)	0.074 (3)	0.098 (5)	0.021 (4)	0.074 (4)	−0.002 (3)
C11A	0.126 (5)	0.081 (4)	0.058 (3)	−0.002 (3)	0.023 (3)	−0.011 (3)
C12A	0.076 (3)	0.050 (2)	0.064 (3)	0.005 (2)	0.013 (2)	0.002 (2)
C13A	0.046 (2)	0.050 (2)	0.059 (3)	0.0082 (17)	0.0085 (19)	−0.0057 (19)
C14A	0.0324 (17)	0.0404 (18)	0.044 (2)	0.0008 (13)	0.0111 (15)	−0.0028 (15)
C15A	0.041 (2)	0.050 (2)	0.050 (2)	0.0014 (16)	0.0104 (17)	0.0067 (17)
C16A	0.063 (3)	0.071 (3)	0.051 (3)	0.006 (2)	0.009 (2)	0.016 (2)
C17A	0.082 (3)	0.056 (3)	0.068 (3)	0.007 (2)	0.032 (3)	0.020 (2)
C18A	0.051 (2)	0.060 (2)	0.086 (3)	−0.007 (2)	0.036 (2)	0.004 (2)
C19A	0.041 (2)	0.048 (2)	0.072 (3)	0.0078 (17)	0.0180 (19)	0.0070 (19)
C20A	0.0400 (19)	0.0402 (18)	0.045 (2)	0.0051 (15)	0.0071 (16)	0.0070 (16)
O1B	0.090 (3)	0.072 (2)	0.0488 (19)	0.0457 (18)	0.0010 (17)	−0.0095 (15)
O2B	0.077 (2)	0.091 (2)	0.084 (3)	0.0405 (19)	−0.019 (2)	−0.028 (2)
O3B	0.0592 (19)	0.0572 (17)	0.0562 (19)	−0.0005 (13)	0.0009 (15)	0.0245 (14)
O4B	0.066 (2)	0.090 (2)	0.069 (2)	0.0078 (17)	−0.0135 (17)	0.0353 (18)
N1B	0.0494 (19)	0.0302 (14)	0.0431 (17)	0.0047 (12)	0.0091 (14)	−0.0011 (12)
N2B	0.0537 (19)	0.0300 (14)	0.0355 (16)	0.0014 (12)	0.0035 (13)	0.0032 (12)
N3B	0.0411 (17)	0.0561 (19)	0.056 (2)	−0.0010 (15)	0.0128 (15)	0.0016 (17)
N4B	0.062 (2)	0.0464 (18)	0.0298 (18)	−0.0021 (14)	0.0013 (15)	0.0010 (12)
C1B	0.046 (2)	0.0282 (17)	0.041 (2)	0.0020 (12)	0.0070 (17)	0.0026 (12)
C2B	0.041 (2)	0.055 (2)	0.054 (2)	0.0125 (16)	0.0027 (17)	0.0076 (18)
C3B	0.056 (2)	0.0381 (19)	0.057 (2)	−0.0138 (16)	0.0101 (18)	−0.0027 (17)
C4B	0.056 (2)	0.046 (2)	0.042 (2)	0.0116 (17)	−0.0019 (17)	0.0125 (17)
C5B	0.060 (2)	0.0339 (17)	0.046 (2)	−0.0060 (16)	0.0033 (18)	−0.0076 (15)
C6B	0.077 (3)	0.052 (2)	0.040 (2)	0.000 (2)	0.029 (2)	0.0019 (17)
C7B	0.066 (3)	0.0228 (15)	0.045 (2)	−0.0010 (16)	0.0110 (18)	0.0024 (14)
C8B	0.073 (3)	0.038 (2)	0.061 (3)	0.0059 (19)	0.021 (2)	−0.0021 (18)
C9B	0.099 (4)	0.059 (3)	0.097 (4)	0.018 (3)	0.045 (3)	−0.002 (3)
C10B	0.168 (7)	0.064 (3)	0.083 (4)	0.025 (4)	0.066 (4)	−0.008 (3)
C11B	0.170 (7)	0.071 (4)	0.052 (3)	0.010 (4)	0.020 (4)	−0.016 (3)
C12B	0.100 (4)	0.059 (3)	0.050 (3)	0.003 (3)	0.003 (2)	−0.005 (2)
C13B	0.059 (2)	0.0381 (19)	0.048 (2)	0.0068 (17)	0.0057 (19)	−0.0033 (17)
C14B	0.047 (2)	0.0217 (14)	0.0400 (19)	0.0031 (13)	0.0027 (15)	−0.0016 (13)
C15B	0.050 (2)	0.0332 (17)	0.044 (2)	0.0002 (15)	−0.0006 (16)	0.0052 (15)
C16B	0.066 (3)	0.041 (2)	0.049 (2)	−0.0010 (18)	−0.0010 (18)	0.0087 (18)
C17B	0.079 (3)	0.045 (2)	0.062 (3)	−0.002 (2)	0.018 (2)	0.010 (2)
C18B	0.057 (3)	0.046 (2)	0.081 (3)	−0.0085 (19)	0.013 (2)	−0.001 (2)
C19B	0.044 (2)	0.051 (2)	0.065 (3)	0.0004 (18)	0.0012 (18)	−0.003 (2)
C20B	0.057 (2)	0.0333 (17)	0.043 (2)	0.0061 (16)	0.0002 (18)	0.0018 (15)

Geometric parameters (Å, º)

O1A—C13A	1.297 (5)	O1B—C13B	1.289 (5)
O1A—H1O1	0.85 (2)	O1B—H2O1	0.84 (2)
O2A—C13A	1.203 (5)	O2B—C13B	1.207 (5)
O3A—C20A	1.303 (4)	O3B—C20B	1.304 (5)
O3A—H1O3	0.84 (2)	O3B—H2O3	0.84 (2)
O4A—C20A	1.197 (4)	O4B—C20B	1.207 (4)
N1A—C4A	1.471 (5)	N1B—C4B	1.471 (4)
N1A—C1A	1.472 (4)	N1B—C1B	1.473 (4)
N1A—C3A	1.476 (4)	N1B—C3B	1.477 (5)
N2A—C2A	1.474 (4)	N2B—C1B	1.470 (4)
N2A—C5A	1.477 (4)	N2B—C2B	1.479 (5)
N2A—C1A	1.479 (4)	N2B—C5B	1.481 (5)
N3A—C3A	1.447 (5)	N3B—C2B	1.452 (5)
N3A—C2A	1.459 (5)	N3B—C6B	1.459 (5)
N3A—C6A	1.465 (5)	N3B—C3B	1.460 (5)
N4A—C5A	1.456 (5)	N4B—C4B	1.451 (5)
N4A—C6A	1.461 (5)	N4B—C5B	1.460 (5)
N4A—C4A	1.463 (5)	N4B—C6B	1.472 (5)
C1A—H1AA	0.9800	C1B—H1BA	0.9800
C1A—H1AB	0.9800	C1B—H1BB	0.9800
C2A—H2AA	0.9800	C2B—H2BA	0.9800
C2A—H2AB	0.9800	C2B—H2BB	0.9800
C3A—H3AA	0.9800	C3B—H3BA	0.9800
C3A—H3AB	0.9800	C3B—H3BB	0.9800
C4A—H4AA	0.9800	C4B—H4BA	0.9800
C4A—H4AB	0.9800	C4B—H4BB	0.9800
C5A—H5AA	0.9800	C5B—H5BA	0.9800
C5A—H5AB	0.9800	C5B—H5BB	0.9800
C6A—H6AA	0.9800	C6B—H6BA	0.9800
C6A—H6AB	0.9800	C6B—H6BB	0.9800
C7A—C12A	1.364 (6)	C7B—C8B	1.373 (6)
C7A—C8A	1.391 (6)	C7B—C12B	1.378 (6)
C7A—C13A	1.498 (5)	C7B—C13B	1.471 (5)
C8A—C9A	1.381 (6)	C8B—C9B	1.394 (6)
C8A—H8AA	0.9400	C8B—H8BA	0.9400
C9A—C10A	1.355 (8)	C9B—C10B	1.356 (9)
C9A—H9AA	0.9400	C9B—H9BA	0.9400
C10A—C11A	1.392 (9)	C10B—C11B	1.366 (9)
C10A—H10A	0.9400	C10B—H10B	0.9400
C11A—C12A	1.369 (7)	C11B—C12B	1.372 (7)
C11A—H11A	0.9400	C11B—H11B	0.9400
C12A—H12A	0.9400	C12B—H12B	0.9400
C14A—C15A	1.373 (5)	C14B—C19B	1.383 (5)
C14A—C19A	1.389 (5)	C14B—C15B	1.386 (5)
C14A—C20A	1.505 (5)	C14B—C20B	1.483 (5)
C15A—C16A	1.378 (5)	C15B—C16B	1.380 (5)
C15A—H15A	0.9400	C15B—H15B	0.9400
C16A—C17A	1.358 (6)	C16B—C17B	1.373 (6)
C16A—H16A	0.9400	C16B—H16B	0.9400
C17A—C18A	1.375 (7)	C17B—C18B	1.363 (6)
C17A—H17A	0.9400	C17B—H17B	0.9400
C18A—C19A	1.389 (6)	C18B—C19B	1.394 (6)
C18A—H18A	0.9400	C18B—H18B	0.9400
C19A—H19A	0.9400	C19B—H19B	0.9400
C13A—O1A—H1O1	107 (4)	C13B—O1B—H2O1	113 (4)
C20A—O3A—H1O3	110 (4)	C20B—O3B—H2O3	110 (6)
C4A—N1A—C1A	108.0 (3)	C4B—N1B—C1B	108.4 (3)
C4A—N1A—C3A	108.3 (3)	C4B—N1B—C3B	108.1 (3)
C1A—N1A—C3A	107.5 (3)	C1B—N1B—C3B	107.7 (3)
C2A—N2A—C5A	108.9 (3)	C1B—N2B—C2B	108.4 (3)
C2A—N2A—C1A	107.7 (3)	C1B—N2B—C5B	108.2 (3)
C5A—N2A—C1A	108.5 (3)	C2B—N2B—C5B	108.3 (3)
C3A—N3A—C2A	108.7 (3)	C2B—N3B—C6B	108.8 (3)
C3A—N3A—C6A	108.1 (3)	C2B—N3B—C3B	108.2 (3)
C2A—N3A—C6A	107.7 (3)	C6B—N3B—C3B	108.4 (3)
C5A—N4A—C6A	108.8 (3)	C4B—N4B—C5B	109.3 (3)
C5A—N4A—C4A	108.3 (3)	C4B—N4B—C6B	107.9 (3)
C6A—N4A—C4A	107.6 (3)	C5B—N4B—C6B	108.3 (3)
N1A—C1A—N2A	111.4 (3)	N2B—C1B—N1B	111.4 (3)
N1A—C1A—H1AA	109.4	N2B—C1B—H1BA	109.3
N2A—C1A—H1AA	109.4	N1B—C1B—H1BA	109.3
N1A—C1A—H1AB	109.4	N2B—C1B—H1BB	109.3
N2A—C1A—H1AB	109.4	N1B—C1B—H1BB	109.3
H1AA—C1A—H1AB	108.0	H1BA—C1B—H1BB	108.0
N3A—C2A—N2A	111.8 (3)	N3B—C2B—N2B	111.6 (3)
N3A—C2A—H2AA	109.3	N3B—C2B—H2BA	109.3
N2A—C2A—H2AA	109.3	N2B—C2B—H2BA	109.3
N3A—C2A—H2AB	109.3	N3B—C2B—H2BB	109.3
N2A—C2A—H2AB	109.3	N2B—C2B—H2BB	109.3
H2AA—C2A—H2AB	107.9	H2BA—C2B—H2BB	108.0
N3A—C3A—N1A	112.3 (3)	N3B—C3B—N1B	111.8 (3)
N3A—C3A—H3AA	109.1	N3B—C3B—H3BA	109.3
N1A—C3A—H3AA	109.1	N1B—C3B—H3BA	109.3
N3A—C3A—H3AB	109.1	N3B—C3B—H3BB	109.3
N1A—C3A—H3AB	109.1	N1B—C3B—H3BB	109.3
H3AA—C3A—H3AB	107.9	H3BA—C3B—H3BB	107.9
N4A—C4A—N1A	112.4 (3)	N4B—C4B—N1B	112.0 (3)
N4A—C4A—H4AA	109.1	N4B—C4B—H4BA	109.2
N1A—C4A—H4AA	109.1	N1B—C4B—H4BA	109.2
N4A—C4A—H4AB	109.1	N4B—C4B—H4BB	109.2
N1A—C4A—H4AB	109.1	N1B—C4B—H4BB	109.2
H4AA—C4A—H4AB	107.9	H4BA—C4B—H4BB	107.9
N4A—C5A—N2A	111.1 (3)	N4B—C5B—N2B	111.2 (3)
N4A—C5A—H5AA	109.4	N4B—C5B—H5BA	109.4
N2A—C5A—H5AA	109.4	N2B—C5B—H5BA	109.4
N4A—C5A—H5AB	109.4	N4B—C5B—H5BB	109.4
N2A—C5A—H5AB	109.4	N2B—C5B—H5BB	109.4
H5AA—C5A—H5AB	108.0	H5BA—C5B—H5BB	108.0
N4A—C6A—N3A	112.9 (3)	N3B—C6B—N4B	112.0 (3)
N4A—C6A—H6AA	109.0	N3B—C6B—H6BA	109.2
N3A—C6A—H6AA	109.0	N4B—C6B—H6BA	109.2
N4A—C6A—H6AB	109.0	N3B—C6B—H6BB	109.2
N3A—C6A—H6AB	109.0	N4B—C6B—H6BB	109.2
H6AA—C6A—H6AB	107.8	H6BA—C6B—H6BB	107.9
C12A—C7A—C8A	120.2 (4)	C8B—C7B—C12B	119.8 (4)
C12A—C7A—C13A	119.0 (4)	C8B—C7B—C13B	121.4 (4)
C8A—C7A—C13A	120.7 (4)	C12B—C7B—C13B	118.8 (4)
C9A—C8A—C7A	118.7 (5)	C7B—C8B—C9B	120.3 (5)
C9A—C8A—H8AA	120.6	C7B—C8B—H8BA	119.9
C7A—C8A—H8AA	120.6	C9B—C8B—H8BA	119.9
C10A—C9A—C8A	121.0 (5)	C10B—C9B—C8B	118.9 (6)
C10A—C9A—H9AA	119.5	C10B—C9B—H9BA	120.5
C8A—C9A—H9AA	119.5	C8B—C9B—H9BA	120.5
C9A—C10A—C11A	120.0 (5)	C9B—C10B—C11B	121.1 (5)
C9A—C10A—H10A	120.0	C9B—C10B—H10B	119.5
C11A—C10A—H10A	120.0	C11B—C10B—H10B	119.5
C12A—C11A—C10A	119.5 (5)	C10B—C11B—C12B	120.4 (5)
C12A—C11A—H11A	120.3	C10B—C11B—H11B	119.8
C10A—C11A—H11A	120.3	C12B—C11B—H11B	119.8
C7A—C12A—C11A	120.6 (5)	C11B—C12B—C7B	119.5 (5)
C7A—C12A—H12A	119.7	C11B—C12B—H12B	120.2
C11A—C12A—H12A	119.7	C7B—C12B—H12B	120.2
O2A—C13A—O1A	123.0 (4)	O2B—C13B—O1B	122.0 (4)
O2A—C13A—C7A	122.2 (4)	O2B—C13B—C7B	122.8 (4)
O1A—C13A—C7A	114.8 (3)	O1B—C13B—C7B	115.1 (3)
C15A—C14A—C19A	119.3 (3)	C19B—C14B—C15B	119.0 (3)
C15A—C14A—C20A	121.2 (3)	C19B—C14B—C20B	120.4 (3)
C19A—C14A—C20A	119.5 (3)	C15B—C14B—C20B	120.6 (3)
C14A—C15A—C16A	120.8 (4)	C16B—C15B—C14B	120.6 (4)
C14A—C15A—H15A	119.6	C16B—C15B—H15B	119.7
C16A—C15A—H15A	119.6	C14B—C15B—H15B	119.7
C17A—C16A—C15A	119.9 (4)	C17B—C16B—C15B	119.8 (4)
C17A—C16A—H16A	120.0	C17B—C16B—H16B	120.1
C15A—C16A—H16A	120.0	C15B—C16B—H16B	120.1
C16A—C17A—C18A	120.5 (4)	C18B—C17B—C16B	120.6 (4)
C16A—C17A—H17A	119.7	C18B—C17B—H17B	119.7
C18A—C17A—H17A	119.7	C16B—C17B—H17B	119.7
C17A—C18A—C19A	119.9 (4)	C17B—C18B—C19B	120.0 (4)
C17A—C18A—H18A	120.0	C17B—C18B—H18B	120.0
C19A—C18A—H18A	120.0	C19B—C18B—H18B	120.0
C14A—C19A—C18A	119.5 (4)	C14B—C19B—C18B	120.0 (4)
C14A—C19A—H19A	120.3	C14B—C19B—H19B	120.0
C18A—C19A—H19A	120.3	C18B—C19B—H19B	120.0
O4A—C20A—O3A	124.3 (4)	O4B—C20B—O3B	122.8 (4)
O4A—C20A—C14A	121.8 (3)	O4B—C20B—C14B	122.2 (4)
O3A—C20A—C14A	113.9 (3)	O3B—C20B—C14B	114.9 (3)
C4A—N1A—C1A—N2A	−57.7 (4)	C2B—N2B—C1B—N1B	−58.4 (4)
C3A—N1A—C1A—N2A	59.0 (4)	C5B—N2B—C1B—N1B	58.9 (4)
C2A—N2A—C1A—N1A	−59.3 (4)	C4B—N1B—C1B—N2B	−58.3 (4)
C5A—N2A—C1A—N1A	58.4 (4)	C3B—N1B—C1B—N2B	58.5 (4)
C3A—N3A—C2A—N2A	−58.8 (4)	C6B—N3B—C2B—N2B	58.3 (4)
C6A—N3A—C2A—N2A	58.1 (4)	C3B—N3B—C2B—N2B	−59.4 (4)
C5A—N2A—C2A—N3A	−58.7 (4)	C1B—N2B—C2B—N3B	58.8 (4)
C1A—N2A—C2A—N3A	58.8 (4)	C5B—N2B—C2B—N3B	−58.3 (4)
C2A—N3A—C3A—N1A	58.9 (4)	C2B—N3B—C3B—N1B	60.0 (4)
C6A—N3A—C3A—N1A	−57.8 (4)	C6B—N3B—C3B—N1B	−58.0 (4)
C4A—N1A—C3A—N3A	57.5 (4)	C4B—N1B—C3B—N3B	57.7 (4)
C1A—N1A—C3A—N3A	−58.9 (4)	C1B—N1B—C3B—N3B	−59.3 (4)
C5A—N4A—C4A—N1A	−59.7 (4)	C5B—N4B—C4B—N1B	−58.4 (4)
C6A—N4A—C4A—N1A	57.8 (4)	C6B—N4B—C4B—N1B	59.2 (4)
C1A—N1A—C4A—N4A	58.6 (4)	C1B—N1B—C4B—N4B	57.9 (4)
C3A—N1A—C4A—N4A	−57.5 (4)	C3B—N1B—C4B—N4B	−58.7 (4)
C6A—N4A—C5A—N2A	−57.3 (4)	C4B—N4B—C5B—N2B	58.6 (4)
C4A—N4A—C5A—N2A	59.4 (4)	C6B—N4B—C5B—N2B	−58.7 (4)
C2A—N2A—C5A—N4A	57.7 (4)	C1B—N2B—C5B—N4B	−58.7 (4)
C1A—N2A—C5A—N4A	−59.2 (4)	C2B—N2B—C5B—N4B	58.5 (4)
C5A—N4A—C6A—N3A	58.6 (4)	C2B—N3B—C6B—N4B	−58.7 (4)
C4A—N4A—C6A—N3A	−58.6 (4)	C3B—N3B—C6B—N4B	58.8 (4)
C3A—N3A—C6A—N4A	58.9 (4)	C4B—N4B—C6B—N3B	−59.3 (4)
C2A—N3A—C6A—N4A	−58.4 (4)	C5B—N4B—C6B—N3B	58.9 (4)
C12A—C7A—C8A—C9A	0.8 (6)	C12B—C7B—C8B—C9B	−0.7 (6)
C13A—C7A—C8A—C9A	−176.0 (4)	C13B—C7B—C8B—C9B	−178.1 (4)
C7A—C8A—C9A—C10A	−0.9 (7)	C7B—C8B—C9B—C10B	−0.4 (7)
C8A—C9A—C10A—C11A	0.0 (9)	C8B—C9B—C10B—C11B	1.0 (9)
C9A—C10A—C11A—C12A	1.0 (9)	C9B—C10B—C11B—C12B	−0.4 (10)
C8A—C7A—C12A—C11A	0.2 (7)	C10B—C11B—C12B—C7B	−0.8 (8)
C13A—C7A—C12A—C11A	177.1 (4)	C8B—C7B—C12B—C11B	1.3 (7)
C10A—C11A—C12A—C7A	−1.1 (8)	C13B—C7B—C12B—C11B	178.7 (4)
C12A—C7A—C13A—O2A	−9.4 (6)	C8B—C7B—C13B—O2B	164.5 (4)
C8A—C7A—C13A—O2A	167.5 (5)	C12B—C7B—C13B—O2B	−12.9 (6)
C12A—C7A—C13A—O1A	171.0 (4)	C8B—C7B—C13B—O1B	−13.0 (6)
C8A—C7A—C13A—O1A	−12.1 (6)	C12B—C7B—C13B—O1B	169.6 (4)
C19A—C14A—C15A—C16A	−0.4 (6)	C19B—C14B—C15B—C16B	−0.3 (5)
C20A—C14A—C15A—C16A	−179.0 (4)	C20B—C14B—C15B—C16B	−179.5 (3)
C14A—C15A—C16A—C17A	−0.7 (6)	C14B—C15B—C16B—C17B	−0.7 (6)
C15A—C16A—C17A—C18A	0.9 (7)	C15B—C16B—C17B—C18B	1.4 (7)
C16A—C17A—C18A—C19A	−0.1 (7)	C16B—C17B—C18B—C19B	−1.2 (7)
C15A—C14A—C19A—C18A	1.2 (6)	C15B—C14B—C19B—C18B	0.5 (6)
C20A—C14A—C19A—C18A	179.9 (3)	C20B—C14B—C19B—C18B	179.7 (3)
C17A—C18A—C19A—C14A	−0.9 (6)	C17B—C18B—C19B—C14B	0.2 (6)
C15A—C14A—C20A—O4A	173.0 (4)	C19B—C14B—C20B—O4B	−7.4 (6)
C19A—C14A—C20A—O4A	−5.6 (6)	C15B—C14B—C20B—O4B	171.8 (4)
C15A—C14A—C20A—O3A	−5.4 (5)	C19B—C14B—C20B—O3B	174.7 (3)
C19A—C14A—C20A—O3A	176.0 (3)	C15B—C14B—C20B—O3B	−6.0 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1O1···N1A	0.85 (4)	1.81 (4)	2.663 (4)	177 (4)
O3A—H1O3···N2A	0.84 (4)	1.78 (4)	2.618 (4)	177 (6)
O1B—H2O1···N1B	0.84 (5)	1.82 (5)	2.655 (5)	175 (5)
O3B—H2O3···N2B	0.83 (6)	1.79 (6)	2.618 (4)	173 (7)
C2A—H2AA···O4A^i	0.98	2.50	3.148 (5)	123
C5A—H5AA···O2A^ii	0.98	2.59	3.224 (5)	123
C2B—H2BA···O4B^i	0.98	2.53	3.191 (5)	125
C5B—H5BA···O2B^iii	0.98	2.56	3.236 (5)	126
C3A—H3AB···Cg17^iv	0.98	2.83	3.798 (4)	169
C5A—H5AB···Cg15^iv	0.98	2.92	3.848 (4)	159
C10A—H10A···Cg16^v	0.94	3.00	3.856 (7)	152
C10B—H10B···Cg17^vi	0.94	2.91	3.713 (6)	144
C17A—H17A···Cg18^vii	0.94	2.90	3.770 (5)	153
C3B—H3BB···Cg18^viii	0.98	2.84	3.807 (4)	171
C5B—H5BB···Cg16^viii	0.98	2.92	3.840 (4)	157

Symmetry codes: (i) x−1, y, z; (ii) x+1/2, −y+1, z+1/2; (iii) x+1/2, −y+2, z+1/2; (iv) x−1/2, −y+1, z+1/2; (v) x−1/2, −y+1, z−1/2; (vi) x+1, y, z; (vii) x−1/2, −y+2, z−1/2; (viii) x−1/2, −y+2, z+1/2.

Hexamethylenetetramine bis(benzoic acid) (1533070)

Crystal data

C6H12N4·2(C7H6O2)	Dx = 1.303 Mg m^−3
Mr = 384.43	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Fmm2	Cell parameters from 1844 reflections
a = 10.1183 (18) Å	θ = 3.0–23.8°
b = 27.015 (5) Å	µ = 0.09 mm^−1
c = 7.1684 (13) Å	T = 260 K
V = 1959.5 (6) Å^3	Block, colourless
Z = 4	0.76 × 0.39 × 0.21 mm
F(000) = 816

Data collection

Bruker APEX Duo CCD area detector diffractometer	1191 independent reflections
Radiation source: fine-focus sealed tube	1004 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
φ and ω scans	θmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→13
Tmin = 0.860, Tmax = 0.937	k = −34→34
4726 measured reflections	l = −9→9

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.049	w = 1/[σ^2(Fo^2) + (0.0559P)^2 + 1.217P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.137	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.11 e Å^−3
1191 reflections	Δρmin = −0.14 e Å^−3
103 parameters	Absolute structure: Flack x determined using 382 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
2 restraints	Absolute structure parameter: 0.1 (6)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.5820 (7)	0.6126 (2)	0.6928 (8)	0.0835 (17)	0.5
H1O1	0.557 (7)	0.597 (3)	0.600 (8)	0.12 (3)*	0.5
O2	0.3726 (6)	0.6044 (3)	0.7737 (12)	0.121 (3)	0.5
C4	0.4757 (6)	0.62132 (19)	0.7979 (8)	0.056 (2)	0.5
C5	0.5051 (10)	0.65328 (12)	0.9615 (5)	0.0605 (12)	0.5
C6	0.6342 (9)	0.6662 (2)	1.0067 (9)	0.081 (3)	0.5
H6A	0.7039	0.6553	0.9328	0.097*	0.5
C7	0.6590 (7)	0.6955 (3)	1.1623 (10)	0.104 (3)	0.5
H7A	0.7453	0.7042	1.1925	0.124*	0.5
C8	0.5547 (8)	0.71181 (17)	1.2727 (6)	0.118 (5)	0.5
H8A	0.5713	0.7314	1.3768	0.142*	0.5
C9	0.4257 (7)	0.6988 (3)	1.2274 (8)	0.097 (3)	0.5
H9A	0.3560	0.7098	1.3013	0.116*	0.5
C10	0.4009 (8)	0.6696 (3)	1.0719 (9)	0.081 (2)	0.5
H10A	0.3146	0.6609	1.0416	0.097*	0.5
N1	0.5000	0.54393 (12)	0.4453 (4)	0.0794 (11)
N2	0.3816 (3)	0.5000	0.2092 (5)	0.0939 (14)
C1	0.3838 (5)	0.54284 (17)	0.3256 (5)	0.1231 (19)
H1A	0.3050	0.5433	0.4025	0.148*
H1B	0.3829	0.5723	0.2481	0.148*
C2	0.5000	0.5000	0.5611 (6)	0.0559 (12)
H2A	0.4198	0.5000	0.6352	0.067*
C3	0.5000	0.5000	0.0949 (8)	0.0813 (19)
H3A	0.5000	0.5294	0.0175	0.098*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.072 (4)	0.100 (4)	0.079 (4)	−0.024 (3)	0.010 (3)	−0.034 (3)
O2	0.080 (4)	0.160 (6)	0.123 (6)	−0.041 (4)	0.010 (4)	−0.065 (5)
C4	0.034 (6)	0.059 (2)	0.075 (3)	−0.006 (2)	−0.001 (2)	−0.004 (2)
C5	0.068 (3)	0.0469 (17)	0.066 (2)	−0.018 (6)	0.008 (9)	0.0013 (17)
C6	0.087 (6)	0.064 (4)	0.092 (7)	−0.007 (3)	−0.014 (5)	−0.016 (4)
C7	0.111 (6)	0.084 (4)	0.116 (8)	−0.019 (5)	−0.013 (5)	−0.031 (5)
C8	0.173 (13)	0.090 (5)	0.092 (6)	0.003 (6)	−0.006 (6)	−0.034 (5)
C9	0.118 (8)	0.096 (6)	0.076 (5)	0.012 (6)	0.016 (5)	−0.018 (5)
C10	0.082 (5)	0.071 (4)	0.089 (6)	−0.005 (4)	0.007 (5)	−0.003 (4)
N1	0.134 (3)	0.0583 (17)	0.0463 (17)	0.000	0.000	−0.0016 (15)
N2	0.0586 (19)	0.170 (4)	0.0532 (18)	0.000	−0.0194 (17)	0.000
C1	0.145 (4)	0.163 (4)	0.0612 (18)	0.097 (3)	−0.010 (2)	0.005 (2)
C2	0.064 (3)	0.066 (3)	0.037 (2)	0.000	0.000	0.000
C3	0.109 (5)	0.098 (5)	0.036 (2)	0.000	0.000	0.000

Geometric parameters (Å, º)

O1—C4	1.334 (8)	C10—H10A	0.9300
O1—H1O1	0.83 (3)	N1—C2	1.448 (4)
O2—C4	1.153 (9)	N1—C1	1.456 (4)
C4—C5	1.486 (7)	N1—C1^i	1.456 (4)
C5—C6	1.3900	N2—C1^ii	1.427 (5)
C5—C10	1.3900	N2—C1	1.427 (5)
C6—C7	1.3900	N2—C3	1.452 (5)
C6—H6A	0.9300	C1—H1A	0.9700
C7—C8	1.3900	C1—H1B	0.9700
C7—H7A	0.9300	C2—N1^iii	1.448 (4)
C8—C9	1.3900	C2—H2A	0.9700
C8—H8A	0.9300	C3—N2^iii	1.452 (5)
C9—C10	1.3900	C3—H3A	0.9700
C9—H9A	0.9300
C4—O1—H1O1	107 (6)	C9—C10—H10A	120.0
O2—C4—O1	125.1 (7)	C5—C10—H10A	120.0
O2—C4—C5	122.1 (7)	C2—N1—C1	108.7 (3)
O1—C4—C5	112.7 (6)	C2—N1—C1^i	108.7 (3)
C6—C5—C10	120.0	C1—N1—C1^i	107.7 (4)
C6—C5—C4	121.2 (6)	C1^ii—N2—C1	108.4 (4)
C10—C5—C4	118.8 (6)	C1^ii—N2—C3	108.5 (3)
C7—C6—C5	120.0	C1—N2—C3	108.5 (3)
C7—C6—H6A	120.0	N2—C1—N1	112.0 (3)
C5—C6—H6A	120.0	N2—C1—H1A	109.2
C6—C7—C8	120.0	N1—C1—H1A	109.2
C6—C7—H7A	120.0	N2—C1—H1B	109.2
C8—C7—H7A	120.0	N1—C1—H1B	109.2
C9—C8—C7	120.0	H1A—C1—H1B	107.9
C9—C8—H8A	120.0	N1—C2—N1^iii	110.1 (4)
C7—C8—H8A	120.0	N1—C2—H2A	108.3
C8—C9—C10	120.0	N1^iii—C2—H2A	108.3
C8—C9—H9A	120.0	N2^iii—C3—N2	111.3 (4)
C10—C9—H9A	120.0	N2^iii—C3—H3A	108.9
C9—C10—C5	120.0	N2—C3—H3A	108.9
O2—C4—C5—C6	168.5 (8)	C6—C5—C10—C9	0.0
O1—C4—C5—C6	−7.8 (7)	C4—C5—C10—C9	179.0 (3)
O2—C4—C5—C10	−10.4 (10)	C1^ii—N2—C1—N1	58.5 (6)
O1—C4—C5—C10	173.3 (6)	C3—N2—C1—N1	−59.1 (4)
C10—C5—C6—C7	0.0	C2—N1—C1—N2	−59.2 (4)
C4—C5—C6—C7	−178.9 (4)	C1^i—N1—C1—N2	58.5 (6)
C5—C6—C7—C8	0.0	C1—N1—C2—N1^iii	58.5 (2)
C6—C7—C8—C9	0.0	C1^i—N1—C2—N1^iii	−58.5 (2)
C7—C8—C9—C10	0.0	C1^ii—N2—C3—N2^iii	−58.8 (2)
C8—C9—C10—C5	0.0	C1—N2—C3—N2^iii	58.8 (2)

Symmetry codes: (i) −x+1, y, z; (ii) x, −y+1, z; (iii) −x+1, −y+1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.83 (6)	1.90 (7)	2.698 (6)	161 (7)

Hexamethylenetetramine bis(benzoic acid) (1533071)

Crystal data

C6H12N4·2(C7H6O2)	Dx = 1.288 Mg m^−3
Mr = 384.43	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Fmm2	Cell parameters from 1825 reflections
a = 10.1464 (11) Å	θ = 3.0–23.4°
b = 27.166 (3) Å	µ = 0.09 mm^−1
c = 7.1898 (8) Å	T = 280 K
V = 1981.8 (4) Å^3	Block, colourless
Z = 4	0.76 × 0.39 × 0.21 mm
F(000) = 816

Data collection

Bruker APEX Duo CCD area detector diffractometer	1044 independent reflections
Radiation source: fine-focus sealed tube	837 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→13
Tmin = 0.819, Tmax = 0.937	k = −34→34
4852 measured reflections	l = −9→7

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.044	w = 1/[σ^2(Fo^2) + (0.0557P)^2 + 1.006P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.128	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.10 e Å^−3
1044 reflections	Δρmin = −0.11 e Å^−3
103 parameters	Absolute structure: Flack x determined using 263 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
2 restraints	Absolute structure parameter: −0.8 (7)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.4182 (7)	0.3876 (3)	0.8081 (9)	0.0930 (19)	0.5
H1O1	0.450 (14)	0.401 (4)	0.902 (11)	0.24 (8)*	0.5
O2	0.6266 (7)	0.3959 (3)	0.7257 (13)	0.135 (3)	0.5
C4	0.5241 (7)	0.37906 (19)	0.7022 (9)	0.063 (2)	0.5
C5	0.4939 (10)	0.34680 (11)	0.5389 (5)	0.0648 (12)	0.5
C6	0.3655 (9)	0.3335 (2)	0.4940 (9)	0.088 (3)	0.5
H6A	0.2958	0.3442	0.5677	0.106*	0.5
C7	0.3414 (7)	0.3042 (3)	0.3392 (10)	0.115 (3)	0.5
H7A	0.2555	0.2953	0.3093	0.138*	0.5
C8	0.4456 (8)	0.28822 (16)	0.2292 (6)	0.121 (4)	0.5
H8A	0.4294	0.2686	0.1257	0.145*	0.5
C9	0.5740 (7)	0.3015 (3)	0.2740 (9)	0.108 (3)	0.5
H9A	0.6437	0.2909	0.2004	0.129*	0.5
C10	0.5982 (8)	0.3308 (3)	0.4288 (9)	0.088 (3)	0.5
H10A	0.6841	0.3398	0.4588	0.106*	0.5
N1	0.5000	0.45617 (11)	1.0543 (4)	0.0836 (11)
N2	0.6185 (3)	0.5000	1.2901 (5)	0.0974 (13)
C1	0.6164 (4)	0.45733 (16)	1.1739 (5)	0.1245 (17)
H1A	0.6175	0.4281	1.2513	0.149*
H1B	0.6950	0.4569	1.0972	0.149*
C2	0.5000	0.5000	0.9387 (7)	0.0632 (12)
H2A	0.4211	0.5000	0.8626	0.076*
C3	0.5000	0.5000	1.4046 (8)	0.0878 (18)
H3A	0.5000	0.5301	1.4770	0.105*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.083 (4)	0.111 (4)	0.085 (4)	−0.028 (3)	0.014 (3)	−0.035 (3)
O2	0.090 (4)	0.176 (6)	0.138 (7)	−0.048 (4)	0.011 (4)	−0.075 (5)
C4	0.046 (8)	0.064 (2)	0.079 (3)	−0.003 (2)	0.001 (3)	−0.003 (2)
C5	0.074 (3)	0.0510 (16)	0.069 (2)	−0.013 (6)	0.009 (9)	0.0015 (17)
C6	0.095 (6)	0.072 (4)	0.098 (7)	−0.010 (3)	−0.014 (5)	−0.016 (4)
C7	0.125 (6)	0.097 (4)	0.123 (8)	−0.024 (5)	−0.008 (6)	−0.035 (5)
C8	0.169 (12)	0.098 (5)	0.095 (6)	−0.001 (5)	−0.008 (6)	−0.036 (5)
C9	0.137 (8)	0.106 (6)	0.080 (5)	0.013 (6)	0.018 (6)	−0.022 (5)
C10	0.088 (6)	0.081 (5)	0.096 (7)	−0.005 (3)	0.005 (5)	0.002 (4)
N1	0.138 (3)	0.0635 (17)	0.0496 (18)	0.000	0.000	−0.0011 (15)
N2	0.0637 (19)	0.171 (4)	0.0572 (18)	0.000	−0.0203 (18)	0.000
C1	0.140 (3)	0.165 (4)	0.069 (2)	0.089 (3)	−0.012 (2)	0.007 (2)
C2	0.072 (3)	0.076 (3)	0.042 (2)	0.000	0.000	0.000
C3	0.119 (5)	0.104 (4)	0.040 (3)	0.000	0.000	0.000

Geometric parameters (Å, º)

O1—C4	1.337 (10)	C10—H10A	0.9300
O1—H1O1	0.83 (3)	N1—C2	1.452 (4)
O2—C4	1.148 (11)	N1—C1^i	1.461 (4)
C4—C5	1.497 (7)	N1—C1	1.461 (4)
C5—C6	1.3900	N2—C1^ii	1.429 (4)
C5—C10	1.3900	N2—C1	1.429 (4)
C6—C7	1.3900	N2—C3	1.457 (5)
C6—H6A	0.9300	C1—H1A	0.9700
C7—C8	1.3900	C1—H1B	0.9700
C7—H7A	0.9300	C2—N1^iii	1.452 (4)
C8—C9	1.3900	C2—H2A	0.9700
C8—H8A	0.9300	C3—N2^iii	1.457 (5)
C9—C10	1.3900	C3—H3A	0.9700
C9—H9A	0.9300
C4—O1—H1O1	103 (10)	C9—C10—H10A	120.0
O2—C4—O1	125.1 (7)	C5—C10—H10A	120.0
O2—C4—C5	122.2 (7)	C2—N1—C1^i	108.6 (3)
O1—C4—C5	112.6 (7)	C2—N1—C1	108.6 (3)
C6—C5—C10	120.0	C1^i—N1—C1	107.8 (3)
C6—C5—C4	121.7 (6)	C1^ii—N2—C1	108.4 (4)
C10—C5—C4	118.3 (6)	C1^ii—N2—C3	108.5 (3)
C7—C6—C5	120.0	C1—N2—C3	108.5 (3)
C7—C6—H6A	120.0	N2—C1—N1	112.0 (3)
C5—C6—H6A	120.0	N2—C1—H1A	109.2
C6—C7—C8	120.0	N1—C1—H1A	109.2
C6—C7—H7A	120.0	N2—C1—H1B	109.2
C8—C7—H7A	120.0	N1—C1—H1B	109.2
C9—C8—C7	120.0	H1A—C1—H1B	107.9
C9—C8—H8A	120.0	N1—C2—N1^iii	110.2 (4)
C7—C8—H8A	120.0	N1—C2—H2A	108.8
C8—C9—C10	120.0	N1^iii—C2—H2A	108.8
C8—C9—H9A	120.0	N2—C3—N2^iii	111.2 (4)
C10—C9—H9A	120.0	N2—C3—H3A	107.6
C9—C10—C5	120.0	N2^iii—C3—H3A	107.6
O2—C4—C5—C6	−168.9 (9)	C6—C5—C10—C9	0.0
O1—C4—C5—C6	7.8 (8)	C4—C5—C10—C9	−178.9 (3)
O2—C4—C5—C10	9.9 (10)	C1^ii—N2—C1—N1	−58.7 (6)
O1—C4—C5—C10	−173.3 (6)	C3—N2—C1—N1	59.0 (4)
C10—C5—C6—C7	0.0	C2—N1—C1—N2	59.2 (4)
C4—C5—C6—C7	178.8 (4)	C1^i—N1—C1—N2	−58.3 (5)
C5—C6—C7—C8	0.0	C1^i—N1—C2—N1^iii	58.49 (19)
C6—C7—C8—C9	0.0	C1—N1—C2—N1^iii	−58.50 (19)
C7—C8—C9—C10	0.0	C1^ii—N2—C3—N2^iii	58.8 (2)
C8—C9—C10—C5	0.0	C1—N2—C3—N2^iii	−58.8 (2)

Symmetry codes: (i) −x+1, y, z; (ii) x, −y+1, z; (iii) −x+1, −y+1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.83 (11)	1.92 (10)	2.700 (8)	155 (11)

Hexamethylenetetramine bis(benzoic acid) (1533072)

Crystal data

C6H12N4·2(C7H6O2)	Dx = 1.276 Mg m^−3
Mr = 384.43	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Fmm2	Cell parameters from 1750 reflections
a = 10.1732 (13) Å	θ = 3.0–23.3°
b = 27.291 (4) Å	µ = 0.09 mm^−1
c = 7.2049 (9) Å	T = 300 K
V = 2000.4 (4) Å^3	Block, colourless
Z = 4	0.76 × 0.39 × 0.21 mm
F(000) = 816

Data collection

Bruker APEX Duo CCD area detector diffractometer	1100 independent reflections
Radiation source: fine-focus sealed tube	874 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→13
Tmin = 0.827, Tmax = 0.937	k = −35→35
4853 measured reflections	l = −7→9

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.0578P)^2 + 0.7615P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.132	(Δ/σ)max < 0.001
S = 1.07	Δρmax = 0.07 e Å^−3
1100 reflections	Δρmin = −0.11 e Å^−3
103 parameters	Absolute structure: Flack x determined using 288 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
2 restraints	Absolute structure parameter: 0.0 (6)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.4192 (7)	0.3877 (3)	0.8077 (9)	0.0999 (19)	0.5
H1O1	0.453 (17)	0.398 (5)	0.904 (13)	0.27 (9)*	0.5
O2	0.6267 (6)	0.3959 (4)	0.7254 (13)	0.146 (3)	0.5
C4	0.5244 (6)	0.37915 (19)	0.7021 (8)	0.069 (2)	0.5
C5	0.4943 (10)	0.34679 (12)	0.5396 (5)	0.0698 (12)	0.5
C6	0.3660 (9)	0.3337 (3)	0.4954 (9)	0.094 (3)	0.5
H6A	0.2967	0.3445	0.5689	0.113*	0.5
C7	0.3414 (7)	0.3044 (3)	0.3413 (11)	0.125 (3)	0.5
H7A	0.2556	0.2957	0.3118	0.150*	0.5
C8	0.4450 (8)	0.28830 (16)	0.2315 (6)	0.132 (5)	0.5
H8A	0.4285	0.2687	0.1284	0.158*	0.5
C9	0.5733 (7)	0.3014 (3)	0.2756 (9)	0.118 (3)	0.5
H9A	0.6426	0.2906	0.2021	0.142*	0.5
C10	0.5979 (8)	0.3306 (3)	0.4297 (10)	0.096 (3)	0.5
H10A	0.6838	0.3394	0.4592	0.115*	0.5
N1	0.5000	0.45628 (11)	1.0541 (4)	0.0878 (11)
N2	0.6184 (3)	0.5000	1.2889 (5)	0.1020 (12)
C1	0.6162 (4)	0.45742 (15)	1.1737 (5)	0.1260 (16)
H1A	0.6170	0.4284	1.2514	0.151*
H1B	0.6946	0.4569	1.0972	0.151*
C2	0.5000	0.5000	0.9386 (6)	0.0686 (13)
H2A	0.4207	0.5000	0.8639	0.082*
C3	0.5000	0.5000	1.4038 (8)	0.0958 (19)
H3A	0.5000	0.5298	1.4774	0.115*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.090 (4)	0.117 (4)	0.092 (5)	−0.031 (3)	0.016 (3)	−0.038 (4)
O2	0.095 (4)	0.187 (7)	0.155 (8)	−0.048 (4)	0.015 (4)	−0.083 (5)
C4	0.053 (7)	0.070 (2)	0.086 (3)	−0.005 (2)	−0.001 (3)	−0.003 (2)
C5	0.081 (3)	0.0554 (17)	0.073 (2)	−0.013 (7)	0.007 (9)	0.0012 (18)
C6	0.100 (6)	0.080 (4)	0.102 (7)	−0.008 (3)	−0.013 (5)	−0.021 (4)
C7	0.134 (7)	0.108 (5)	0.134 (9)	−0.021 (5)	−0.008 (6)	−0.042 (6)
C8	0.189 (13)	0.102 (5)	0.104 (6)	−0.009 (5)	−0.007 (6)	−0.038 (5)
C9	0.149 (8)	0.117 (7)	0.089 (6)	0.009 (6)	0.021 (6)	−0.029 (6)
C10	0.097 (6)	0.087 (5)	0.102 (7)	−0.007 (4)	0.007 (5)	0.000 (5)
N1	0.141 (3)	0.0691 (18)	0.0535 (18)	0.000	0.000	−0.0011 (16)
N2	0.0726 (18)	0.170 (4)	0.0637 (19)	0.000	−0.0234 (17)	0.000
C1	0.139 (3)	0.162 (4)	0.077 (2)	0.083 (3)	−0.013 (2)	0.006 (2)
C2	0.079 (3)	0.082 (3)	0.045 (3)	0.000	0.000	0.000
C3	0.131 (5)	0.114 (5)	0.043 (3)	0.000	0.000	0.000

Geometric parameters (Å, º)

O1—C4	1.334 (9)	C10—H10A	0.9300
O1—H1O1	0.83 (3)	N1—C2	1.455 (4)
O2—C4	1.149 (10)	N1—C1	1.463 (4)
C4—C5	1.498 (7)	N1—C1^i	1.463 (4)
C5—C6	1.3900	N2—C1^ii	1.428 (4)
C5—C10	1.3900	N2—C1	1.428 (4)
C6—C7	1.3900	N2—C3	1.462 (5)
C6—H6A	0.9300	C1—H1A	0.9700
C7—C8	1.3900	C1—H1B	0.9700
C7—H7A	0.9300	C2—N1^iii	1.455 (4)
C8—C9	1.3900	C2—H2A	0.9700
C8—H8A	0.9300	C3—N2^iii	1.462 (5)
C9—C10	1.3900	C3—H3A	0.9700
C9—H9A	0.9300
C4—O1—H1O1	102 (10)	C9—C10—H10A	120.0
O2—C4—O1	125.0 (7)	C5—C10—H10A	120.0
O2—C4—C5	122.3 (7)	C2—N1—C1	108.6 (3)
O1—C4—C5	112.7 (6)	C2—N1—C1^i	108.6 (2)
C6—C5—C10	120.0	C1—N1—C1^i	107.8 (3)
C6—C5—C4	121.5 (6)	C1^ii—N2—C1	108.9 (4)
C10—C5—C4	118.5 (6)	C1^ii—N2—C3	108.4 (3)
C5—C6—C7	120.0	C1—N2—C3	108.4 (3)
C5—C6—H6A	120.0	N2—C1—N1	111.9 (3)
C7—C6—H6A	120.0	N2—C1—H1A	109.2
C8—C7—C6	120.0	N1—C1—H1A	109.2
C8—C7—H7A	120.0	N2—C1—H1B	109.2
C6—C7—H7A	120.0	N1—C1—H1B	109.2
C9—C8—C7	120.0	H1A—C1—H1B	107.9
C9—C8—H8A	120.0	N1^iii—C2—N1	110.2 (4)
C7—C8—H8A	120.0	N1^iii—C2—H2A	108.5
C10—C9—C8	120.0	N1—C2—H2A	108.5
C10—C9—H9A	120.0	N2—C3—N2^iii	111.0 (4)
C8—C9—H9A	120.0	N2—C3—H3A	108.0
C9—C10—C5	120.0	N2^iii—C3—H3A	108.0
O2—C4—C5—C6	−168.7 (9)	C6—C5—C10—C9	0.0
O1—C4—C5—C6	8.2 (8)	C4—C5—C10—C9	−178.7 (3)
O2—C4—C5—C10	9.9 (10)	C1^ii—N2—C1—N1	−58.5 (6)
O1—C4—C5—C10	−173.1 (6)	C3—N2—C1—N1	59.3 (4)
C10—C5—C6—C7	0.0	C2—N1—C1—N2	58.9 (4)
C4—C5—C6—C7	178.7 (4)	C1^i—N1—C1—N2	−58.6 (5)
C5—C6—C7—C8	0.0	C1—N1—C2—N1^iii	−58.48 (19)
C6—C7—C8—C9	0.0	C1^i—N1—C2—N1^iii	58.48 (19)
C7—C8—C9—C10	0.0	C1^ii—N2—C3—N2^iii	59.0 (2)
C8—C9—C10—C5	0.0	C1—N2—C3—N2^iii	−59.0 (2)

Symmetry codes: (i) −x+1, y, z; (ii) x, −y+1, z; (iii) −x+1, −y+1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.82 (13)	1.98 (12)	2.707 (8)	147 (13)

Hexamethylenetetramine bis(4-methylbenzoic acid) (1533073)

Crystal data

2(C8H8O2)·C6H12N4	F(000) = 880
Mr = 412.48	Dx = 1.323 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.1425 (4) Å	Cell parameters from 9593 reflections
b = 28.0850 (18) Å	θ = 2.9–28.3°
c = 12.1822 (8) Å	µ = 0.09 mm^−1
β = 99.6957 (12)°	T = 100 K
V = 2071.6 (2) Å^3	Block, colourless
Z = 4	0.38 × 0.18 × 0.13 mm

Data collection

Bruker APEX Duo CCD area detector diffractometer	4998 independent reflections
Radiation source: fine-focus sealed tube	4100 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
φ and ω scans	θmax = 28.3°, θmin = 1.5°
Absorption correction: multi-scan (TWINABS; Sheldrick, 2012)	h = −8→8
Tmin = 0.885, Tmax = 0.967	k = 0→36
6265 measured reflections	l = 0→16

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.121	w = 1/[σ^2(Fo^2) + (0.0557P)^2 + 0.7009P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
4998 reflections	Δρmax = 0.36 e Å^−3
282 parameters	Δρmin = −0.22 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.86258 (18)	0.64597 (4)	0.28594 (10)	0.0223 (3)
O2	0.50255 (19)	0.65158 (4)	0.21784 (10)	0.0285 (3)
O3	0.59938 (19)	0.86065 (4)	0.21667 (10)	0.0262 (3)
O4	0.8878 (2)	0.84366 (5)	0.34800 (10)	0.0320 (3)
N1	0.8917 (2)	0.71160 (4)	0.13904 (10)	0.0173 (3)
N2	0.7975 (2)	0.79569 (4)	0.11100 (10)	0.0174 (3)
N3	0.7985 (2)	0.74354 (5)	−0.04924 (11)	0.0211 (3)
N4	1.1472 (2)	0.76568 (5)	0.06872 (11)	0.0211 (3)
C1	0.7830 (2)	0.75317 (5)	0.18076 (12)	0.0173 (3)
H1A	0.8540	0.7601	0.2583	0.021*
H1B	0.6258	0.7456	0.1814	0.021*
C2	0.6917 (3)	0.78430 (6)	−0.00492 (13)	0.0205 (3)
H2A	0.5336	0.7770	−0.0063	0.025*
H2B	0.7009	0.8124	−0.0530	0.025*
C3	0.7823 (3)	0.70224 (5)	0.02226 (12)	0.0200 (3)
H3A	0.8527	0.6744	−0.0073	0.024*
H3B	0.6247	0.6945	0.0214	0.024*
C4	1.1271 (2)	0.72397 (6)	0.13865 (14)	0.0210 (3)
H4A	1.2010	0.7306	0.2158	0.025*
H4B	1.2026	0.6965	0.1105	0.025*
C5	1.0355 (2)	0.80590 (5)	0.11195 (13)	0.0193 (3)
H5A	1.0496	0.8344	0.0660	0.023*
H5B	1.1082	0.8129	0.1891	0.023*
C6	1.0337 (3)	0.75493 (6)	−0.04482 (13)	0.0226 (3)
H6A	1.1078	0.7276	−0.0743	0.027*
H6B	1.0467	0.7827	−0.0933	0.027*
C7	0.6120 (2)	0.60799 (5)	0.38500 (12)	0.0170 (3)
C8	0.7831 (2)	0.59586 (5)	0.47010 (13)	0.0186 (3)
H8A	0.9296	0.6057	0.4663	0.022*
C9	0.7414 (3)	0.56935 (5)	0.56097 (13)	0.0197 (3)
H9A	0.8598	0.5611	0.6186	0.024*
C10	0.5280 (3)	0.55483 (5)	0.56803 (13)	0.0200 (3)
C11	0.3576 (3)	0.56703 (5)	0.48201 (14)	0.0213 (3)
H11A	0.2112	0.5570	0.4855	0.026*
C12	0.3973 (2)	0.59358 (5)	0.39145 (13)	0.0194 (3)
H12A	0.2787	0.6019	0.3341	0.023*
C13	0.6531 (2)	0.63711 (5)	0.28769 (12)	0.0177 (3)
C14	0.6023 (2)	0.89207 (5)	0.39676 (12)	0.0183 (3)
C15	0.3851 (3)	0.90790 (5)	0.36796 (13)	0.0208 (3)
H15A	0.3038	0.9013	0.2961	0.025*
C16	0.2879 (3)	0.93339 (6)	0.44493 (14)	0.0234 (3)
H16A	0.1400	0.9442	0.4248	0.028*
C17	0.4031 (3)	0.94328 (5)	0.55042 (13)	0.0238 (3)
C18	0.6204 (3)	0.92707 (6)	0.57832 (14)	0.0252 (4)
H18A	0.7018	0.9337	0.6501	0.030*
C19	0.7185 (3)	0.90150 (6)	0.50256 (13)	0.0222 (3)
H19A	0.8658	0.8904	0.5230	0.027*
C20	0.7115 (2)	0.86323 (5)	0.31887 (13)	0.0191 (3)
C21	0.4771 (3)	0.52763 (6)	0.66749 (14)	0.0257 (4)
H21A	0.6147	0.5155	0.7110	0.038*
H21B	0.3791	0.5009	0.6420	0.038*
H21C	0.4043	0.5488	0.7140	0.038*
C22	0.2970 (3)	0.97108 (6)	0.63318 (15)	0.0306 (4)
H22A	0.3566	0.9603	0.7088	0.046*
H22B	0.1369	0.9660	0.6183	0.046*
H22C	0.3286	1.0051	0.6263	0.046*
H1O3	0.674 (4)	0.8423 (8)	0.179 (2)	0.064 (8)*
H1O1	0.869 (4)	0.6654 (8)	0.2281 (17)	0.065 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0212 (5)	0.0238 (6)	0.0222 (6)	0.0000 (4)	0.0041 (4)	0.0079 (5)
O2	0.0241 (6)	0.0314 (6)	0.0277 (6)	0.0006 (5)	−0.0018 (5)	0.0109 (5)
O3	0.0299 (6)	0.0284 (6)	0.0200 (6)	0.0127 (5)	0.0035 (5)	−0.0037 (5)
O4	0.0266 (6)	0.0383 (7)	0.0291 (7)	0.0129 (5)	−0.0011 (5)	−0.0099 (5)
N1	0.0195 (6)	0.0158 (6)	0.0169 (6)	0.0009 (5)	0.0041 (5)	0.0009 (5)
N2	0.0190 (6)	0.0159 (6)	0.0181 (6)	0.0011 (5)	0.0051 (5)	0.0007 (5)
N3	0.0268 (7)	0.0208 (7)	0.0159 (6)	−0.0022 (5)	0.0044 (5)	−0.0001 (5)
N4	0.0203 (6)	0.0197 (6)	0.0250 (7)	−0.0003 (5)	0.0084 (5)	0.0002 (5)
C1	0.0204 (7)	0.0164 (7)	0.0165 (7)	0.0003 (5)	0.0066 (5)	0.0012 (5)
C2	0.0216 (7)	0.0212 (8)	0.0181 (7)	0.0023 (6)	0.0019 (6)	0.0034 (6)
C3	0.0253 (7)	0.0171 (7)	0.0175 (7)	−0.0030 (6)	0.0034 (6)	−0.0019 (6)
C4	0.0177 (7)	0.0192 (7)	0.0262 (8)	0.0028 (6)	0.0043 (6)	0.0020 (6)
C5	0.0193 (7)	0.0166 (7)	0.0225 (8)	−0.0019 (6)	0.0051 (6)	−0.0010 (6)
C6	0.0279 (8)	0.0215 (8)	0.0211 (8)	−0.0003 (6)	0.0122 (6)	0.0004 (6)
C7	0.0207 (7)	0.0130 (6)	0.0176 (7)	0.0011 (5)	0.0043 (5)	−0.0015 (5)
C8	0.0183 (7)	0.0176 (7)	0.0200 (8)	0.0004 (5)	0.0038 (6)	0.0009 (6)
C9	0.0222 (7)	0.0175 (7)	0.0188 (7)	0.0018 (6)	0.0014 (6)	−0.0002 (6)
C10	0.0271 (8)	0.0140 (7)	0.0210 (8)	0.0003 (6)	0.0097 (6)	−0.0024 (6)
C11	0.0189 (7)	0.0180 (7)	0.0282 (9)	−0.0002 (6)	0.0076 (6)	−0.0015 (6)
C12	0.0177 (7)	0.0173 (7)	0.0225 (8)	0.0021 (6)	0.0017 (6)	−0.0022 (6)
C13	0.0211 (7)	0.0137 (6)	0.0177 (7)	0.0014 (5)	0.0018 (6)	−0.0014 (5)
C14	0.0239 (7)	0.0130 (6)	0.0193 (7)	0.0004 (6)	0.0077 (6)	0.0017 (5)
C15	0.0251 (8)	0.0184 (7)	0.0196 (8)	0.0014 (6)	0.0055 (6)	0.0020 (6)
C16	0.0249 (8)	0.0206 (8)	0.0267 (8)	0.0047 (6)	0.0097 (6)	0.0028 (6)
C17	0.0339 (8)	0.0170 (7)	0.0234 (8)	0.0001 (6)	0.0135 (7)	0.0016 (6)
C18	0.0343 (9)	0.0234 (8)	0.0184 (8)	−0.0003 (7)	0.0058 (6)	−0.0009 (6)
C19	0.0257 (8)	0.0199 (8)	0.0213 (8)	0.0014 (6)	0.0043 (6)	0.0012 (6)
C20	0.0221 (7)	0.0153 (7)	0.0204 (7)	0.0013 (6)	0.0050 (6)	0.0003 (6)
C21	0.0339 (9)	0.0215 (8)	0.0242 (8)	−0.0023 (6)	0.0125 (7)	0.0007 (6)
C22	0.0423 (10)	0.0249 (9)	0.0286 (9)	0.0025 (7)	0.0174 (8)	−0.0034 (7)

Geometric parameters (Å, º)

O1—C13	1.3145 (18)	C7—C8	1.389 (2)
O1—H1O1	0.898 (16)	C7—C12	1.394 (2)
O2—C13	1.2161 (18)	C7—C13	1.496 (2)
O3—C20	1.3193 (19)	C8—C9	1.393 (2)
O3—H1O3	0.869 (17)	C8—H8A	0.9500
O4—C20	1.2132 (19)	C9—C10	1.389 (2)
N1—C1	1.4768 (18)	C9—H9A	0.9500
N1—C4	1.4879 (19)	C10—C11	1.393 (2)
N1—C3	1.4909 (19)	C10—C21	1.509 (2)
N2—C1	1.4770 (18)	C11—C12	1.387 (2)
N2—C2	1.4865 (19)	C11—H11A	0.9500
N2—C5	1.4879 (18)	C12—H12A	0.9500
N3—C3	1.464 (2)	C14—C19	1.390 (2)
N3—C2	1.466 (2)	C14—C15	1.394 (2)
N3—C6	1.472 (2)	C14—C20	1.490 (2)
N4—C5	1.465 (2)	C15—C16	1.392 (2)
N4—C4	1.466 (2)	C15—H15A	0.9500
N4—C6	1.471 (2)	C16—C17	1.387 (2)
C1—H1A	0.9900	C16—H16A	0.9500
C1—H1B	0.9900	C17—C18	1.397 (2)
C2—H2A	0.9900	C17—C22	1.507 (2)
C2—H2B	0.9900	C18—C19	1.385 (2)
C3—H3A	0.9900	C18—H18A	0.9500
C3—H3B	0.9900	C19—H19A	0.9500
C4—H4A	0.9900	C21—H21A	0.9800
C4—H4B	0.9900	C21—H21B	0.9800
C5—H5A	0.9900	C21—H21C	0.9800
C5—H5B	0.9900	C22—H22A	0.9800
C6—H6A	0.9900	C22—H22B	0.9800
C6—H6B	0.9900	C22—H22C	0.9800
C13—O1—H1O1	107.5 (17)	C12—C7—C13	119.38 (13)
C20—O3—H1O3	107.0 (18)	C7—C8—C9	120.45 (14)
C1—N1—C4	108.19 (11)	C7—C8—H8A	119.8
C1—N1—C3	108.09 (11)	C9—C8—H8A	119.8
C4—N1—C3	108.68 (11)	C10—C9—C8	120.53 (14)
C1—N2—C2	108.27 (11)	C10—C9—H9A	119.7
C1—N2—C5	107.79 (11)	C8—C9—H9A	119.7
C2—N2—C5	108.69 (11)	C9—C10—C11	118.57 (14)
C3—N3—C2	108.65 (12)	C9—C10—C21	121.57 (14)
C3—N3—C6	108.36 (12)	C11—C10—C21	119.83 (14)
C2—N3—C6	108.30 (12)	C12—C11—C10	121.32 (14)
C5—N4—C4	108.48 (12)	C12—C11—H11A	119.3
C5—N4—C6	108.66 (12)	C10—C11—H11A	119.3
C4—N4—C6	108.03 (12)	C11—C12—C7	119.72 (14)
N1—C1—N2	111.51 (11)	C11—C12—H12A	120.1
N1—C1—H1A	109.3	C7—C12—H12A	120.1
N2—C1—H1A	109.3	O2—C13—O1	123.81 (14)
N1—C1—H1B	109.3	O2—C13—C7	121.82 (14)
N2—C1—H1B	109.3	O1—C13—C7	114.36 (12)
H1A—C1—H1B	108.0	C19—C14—C15	119.54 (14)
N3—C2—N2	111.52 (12)	C19—C14—C20	118.57 (14)
N3—C2—H2A	109.3	C15—C14—C20	121.83 (14)
N2—C2—H2A	109.3	C16—C15—C14	119.71 (15)
N3—C2—H2B	109.3	C16—C15—H15A	120.1
N2—C2—H2B	109.3	C14—C15—H15A	120.1
H2A—C2—H2B	108.0	C17—C16—C15	121.17 (15)
N3—C3—N1	111.30 (12)	C17—C16—H16A	119.4
N3—C3—H3A	109.4	C15—C16—H16A	119.4
N1—C3—H3A	109.4	C16—C17—C18	118.53 (14)
N3—C3—H3B	109.4	C16—C17—C22	120.88 (15)
N1—C3—H3B	109.4	C18—C17—C22	120.59 (15)
H3A—C3—H3B	108.0	C19—C18—C17	120.80 (15)
N4—C4—N1	111.44 (12)	C19—C18—H18A	119.6
N4—C4—H4A	109.3	C17—C18—H18A	119.6
N1—C4—H4A	109.3	C18—C19—C14	120.25 (15)
N4—C4—H4B	109.3	C18—C19—H19A	119.9
N1—C4—H4B	109.3	C14—C19—H19A	119.9
H4A—C4—H4B	108.0	O4—C20—O3	123.33 (14)
N4—C5—N2	111.56 (12)	O4—C20—C14	122.37 (14)
N4—C5—H5A	109.3	O3—C20—C14	114.30 (13)
N2—C5—H5A	109.3	C10—C21—H21A	109.5
N4—C5—H5B	109.3	C10—C21—H21B	109.5
N2—C5—H5B	109.3	H21A—C21—H21B	109.5
H5A—C5—H5B	108.0	C10—C21—H21C	109.5
N4—C6—N3	112.68 (12)	H21A—C21—H21C	109.5
N4—C6—H6A	109.1	H21B—C21—H21C	109.5
N3—C6—H6A	109.1	C17—C22—H22A	109.5
N4—C6—H6B	109.1	C17—C22—H22B	109.5
N3—C6—H6B	109.1	H22A—C22—H22B	109.5
H6A—C6—H6B	107.8	C17—C22—H22C	109.5
C8—C7—C12	119.40 (14)	H22A—C22—H22C	109.5
C8—C7—C13	121.21 (13)	H22B—C22—H22C	109.5
C4—N1—C1—N2	58.80 (15)	C7—C8—C9—C10	−0.2 (2)
C3—N1—C1—N2	−58.72 (15)	C8—C9—C10—C11	0.5 (2)
C2—N2—C1—N1	58.51 (15)	C8—C9—C10—C21	−177.76 (14)
C5—N2—C1—N1	−58.91 (15)	C9—C10—C11—C12	−0.8 (2)
C3—N3—C2—N2	59.35 (15)	C21—C10—C11—C12	177.50 (14)
C6—N3—C2—N2	−58.16 (16)	C10—C11—C12—C7	0.8 (2)
C1—N2—C2—N3	−58.60 (15)	C8—C7—C12—C11	−0.5 (2)
C5—N2—C2—N3	58.23 (15)	C13—C7—C12—C11	−179.28 (13)
C2—N3—C3—N1	−59.55 (15)	C8—C7—C13—O2	−173.28 (14)
C6—N3—C3—N1	57.92 (16)	C12—C7—C13—O2	5.4 (2)
C1—N1—C3—N3	59.13 (15)	C8—C7—C13—O1	5.7 (2)
C4—N1—C3—N3	−58.07 (15)	C12—C7—C13—O1	−175.54 (13)
C5—N4—C4—N1	59.28 (16)	C19—C14—C15—C16	0.7 (2)
C6—N4—C4—N1	−58.34 (16)	C20—C14—C15—C16	177.87 (14)
C1—N1—C4—N4	−58.75 (15)	C14—C15—C16—C17	−0.2 (2)
C3—N1—C4—N4	58.38 (16)	C15—C16—C17—C18	0.0 (2)
C4—N4—C5—N2	−59.72 (15)	C15—C16—C17—C22	179.73 (15)
C6—N4—C5—N2	57.49 (16)	C16—C17—C18—C19	−0.3 (2)
C1—N2—C5—N4	59.32 (15)	C22—C17—C18—C19	179.99 (15)
C2—N2—C5—N4	−57.82 (16)	C17—C18—C19—C14	0.8 (2)
C5—N4—C6—N3	−58.34 (16)	C15—C14—C19—C18	−1.0 (2)
C4—N4—C6—N3	59.16 (16)	C20—C14—C19—C18	−178.24 (14)
C3—N3—C6—N4	−59.13 (16)	C19—C14—C20—O4	7.8 (2)
C2—N3—C6—N4	58.56 (16)	C15—C14—C20—O4	−169.39 (15)
C12—C7—C8—C9	0.3 (2)	C19—C14—C20—O3	−172.65 (13)
C13—C7—C8—C9	178.98 (13)	C15—C14—C20—O3	10.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···N2	0.87 (2)	1.79 (2)	2.6447 (17)	169 (2)
O1—H1O1···N1	0.90 (2)	1.71 (2)	2.5961 (17)	168 (2)
C1—H1A···O4	0.99	2.58	3.253 (2)	125
C3—H3B···O4^i	0.99	2.59	3.211 (2)	121
C4—H4B···O2^ii	0.99	2.43	3.1037 (19)	125
C3—H3A···Cg2^iii	0.99	2.77	3.7117 (16)	160
C5—H5A···Cg1^iii	0.99	2.62	3.5925 (16)	169
C21—H21B···Cg1^iv	0.98	2.77	3.5161 (18)	133
C22—H22C···Cg2^v	0.98	2.77	3.6773 (19)	153

Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x+1, y, z; (iii) x+1/2, −y+3/2, z−1/2; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y+2, −z+1.

Hexamethylenetetramine bis(4-methylbenzoic acid) (1533074)

Crystal data

2(C8H8O2)·C6H12N4	F(000) = 880
Mr = 412.48	Dx = 1.289 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.202 (2) Å	Cell parameters from 9903 reflections
b = 28.482 (10) Å	θ = 2.7–27.9°
c = 12.225 (4) Å	µ = 0.09 mm^−1
β = 100.276 (7)°	T = 250 K
V = 2124.9 (13) Å^3	Block, colourless
Z = 4	0.38 × 0.18 × 0.13 mm

Data collection

Bruker APEX Duo CCD area detector diffractometer	5101 independent reflections
Radiation source: fine-focus sealed tube	3518 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
φ and ω scans	θmax = 28.3°, θmin = 1.4°
Absorption correction: multi-scan (TWINABS; Sheldrick, 2012)	h = −8→8
Tmin = 0.869, Tmax = 0.967	k = 0→37
7003 measured reflections	l = 0→16

Refinement

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.151	w = 1/[σ^2(Fo^2) + (0.0446P)^2 + 0.8061P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
5101 reflections	Δρmax = 0.20 e Å^−3
282 parameters	Δρmin = −0.19 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.8535 (3)	0.64682 (6)	0.29434 (15)	0.0547 (5)
O2	0.5008 (3)	0.65279 (7)	0.22439 (16)	0.0713 (6)
O3	0.5970 (3)	0.85896 (7)	0.22531 (15)	0.0635 (5)
O4	0.8831 (3)	0.84455 (8)	0.35495 (18)	0.0858 (7)
N1	0.8856 (3)	0.71191 (6)	0.14667 (14)	0.0403 (4)
N2	0.7959 (3)	0.79484 (6)	0.12000 (15)	0.0402 (4)
N3	0.7899 (4)	0.74382 (7)	−0.04001 (17)	0.0503 (5)
N4	1.1379 (3)	0.76474 (7)	0.07661 (18)	0.0503 (5)
C1	0.7821 (4)	0.75295 (7)	0.18887 (18)	0.0402 (5)
H1A	0.8543	0.7594	0.2654	0.048*
H1B	0.6278	0.7459	0.1899	0.048*
C2	0.6882 (4)	0.78391 (9)	0.00511 (19)	0.0495 (6)
H2A	0.5330	0.7771	0.0042	0.059*
H2B	0.6967	0.8114	−0.0422	0.059*
C3	0.7750 (4)	0.70318 (8)	0.03073 (19)	0.0486 (6)
H3A	0.8426	0.6760	0.0011	0.058*
H3B	0.6205	0.6958	0.0299	0.058*
C4	1.1172 (4)	0.72388 (9)	0.1460 (2)	0.0510 (6)
H4A	1.1913	0.7303	0.2223	0.061*
H4B	1.1899	0.6970	0.1183	0.061*
C5	1.0296 (4)	0.80430 (8)	0.1202 (2)	0.0474 (6)
H5A	1.0429	0.8322	0.0750	0.057*
H5B	1.1033	0.8110	0.1964	0.057*
C6	1.0217 (5)	0.75462 (8)	−0.0361 (2)	0.0560 (7)
H6A	1.0338	0.7818	−0.0837	0.067*
H6B	1.0922	0.7279	−0.0660	0.067*
C7	0.6035 (4)	0.60892 (7)	0.38948 (17)	0.0381 (4)
C8	0.7700 (4)	0.59660 (8)	0.47546 (19)	0.0447 (5)
H8A	0.9145	0.6062	0.4740	0.054*
C9	0.7250 (4)	0.57022 (8)	0.5637 (2)	0.0512 (6)
H9A	0.8399	0.5621	0.6217	0.061*
C10	0.5152 (4)	0.55568 (8)	0.5682 (2)	0.0510 (6)
C11	0.3501 (4)	0.56802 (9)	0.4817 (2)	0.0548 (6)
H11A	0.2060	0.5580	0.4829	0.066*
C12	0.3917 (4)	0.59470 (8)	0.3935 (2)	0.0482 (6)
H12A	0.2762	0.6032	0.3363	0.058*
C13	0.6465 (4)	0.63802 (7)	0.29467 (18)	0.0425 (5)
C14	0.6007 (4)	0.89171 (7)	0.40248 (18)	0.0429 (5)
C15	0.3863 (4)	0.90673 (8)	0.3743 (2)	0.0508 (6)
H15A	0.3044	0.8995	0.3040	0.061*
C16	0.2920 (5)	0.93230 (9)	0.4494 (2)	0.0593 (7)
H16A	0.1459	0.9423	0.4292	0.071*
C17	0.4067 (5)	0.94347 (8)	0.5532 (2)	0.0582 (7)
C18	0.6207 (5)	0.92797 (9)	0.5805 (2)	0.0630 (7)
H18A	0.7026	0.9352	0.6508	0.076*
C19	0.7167 (5)	0.90208 (9)	0.5064 (2)	0.0561 (6)
H19A	0.8619	0.8915	0.5272	0.067*
C20	0.7084 (4)	0.86300 (8)	0.32595 (19)	0.0468 (5)
C21	0.4626 (5)	0.52812 (10)	0.6657 (2)	0.0714 (9)
H21A	0.5943	0.5128	0.7040	0.107*
H21B	0.3523	0.5046	0.6392	0.107*
H21C	0.4075	0.5493	0.7165	0.107*
C22	0.3035 (6)	0.97145 (10)	0.6347 (3)	0.0823 (10)
H22A	0.3780	0.9647	0.7097	0.123*
H22B	0.1500	0.9630	0.6273	0.123*
H22C	0.3160	1.0047	0.6197	0.123*
H1O3	0.672 (5)	0.8402 (10)	0.190 (2)	0.097 (12)*
H1O1	0.860 (5)	0.6662 (9)	0.239 (2)	0.094 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0519 (10)	0.0556 (10)	0.0561 (11)	−0.0001 (8)	0.0082 (8)	0.0214 (9)
O2	0.0584 (11)	0.0794 (14)	0.0687 (12)	−0.0011 (9)	−0.0085 (9)	0.0327 (10)
O3	0.0736 (12)	0.0687 (12)	0.0469 (10)	0.0313 (10)	0.0070 (9)	−0.0097 (9)
O4	0.0682 (12)	0.1073 (17)	0.0739 (14)	0.0397 (12)	−0.0089 (10)	−0.0343 (12)
N1	0.0470 (10)	0.0349 (9)	0.0397 (10)	0.0018 (8)	0.0097 (8)	0.0024 (7)
N2	0.0466 (10)	0.0346 (9)	0.0408 (10)	0.0028 (8)	0.0116 (8)	0.0013 (7)
N3	0.0664 (14)	0.0500 (12)	0.0347 (11)	−0.0049 (10)	0.0099 (9)	0.0008 (8)
N4	0.0431 (11)	0.0508 (11)	0.0612 (13)	−0.0021 (9)	0.0206 (9)	0.0018 (10)
C1	0.0443 (13)	0.0402 (11)	0.0387 (12)	−0.0001 (9)	0.0143 (9)	0.0016 (8)
C2	0.0514 (13)	0.0501 (14)	0.0457 (13)	0.0058 (11)	0.0048 (10)	0.0105 (11)
C3	0.0631 (15)	0.0404 (12)	0.0428 (13)	−0.0077 (11)	0.0105 (11)	−0.0045 (10)
C4	0.0436 (12)	0.0511 (14)	0.0586 (15)	0.0100 (11)	0.0096 (11)	0.0039 (12)
C5	0.0515 (13)	0.0395 (12)	0.0524 (14)	−0.0076 (10)	0.0127 (11)	−0.0019 (10)
C6	0.0762 (19)	0.0518 (14)	0.0480 (16)	−0.0011 (12)	0.0327 (13)	−0.0004 (11)
C7	0.0448 (12)	0.0296 (9)	0.0403 (11)	0.0035 (9)	0.0084 (9)	−0.0021 (9)
C8	0.0443 (12)	0.0438 (12)	0.0461 (13)	0.0026 (10)	0.0082 (10)	0.0068 (10)
C9	0.0616 (15)	0.0470 (13)	0.0442 (13)	0.0024 (11)	0.0074 (11)	0.0061 (11)
C10	0.0702 (16)	0.0366 (12)	0.0513 (14)	0.0003 (11)	0.0249 (12)	−0.0013 (10)
C11	0.0493 (14)	0.0452 (13)	0.0754 (18)	−0.0030 (11)	0.0256 (13)	−0.0019 (13)
C12	0.0429 (12)	0.0426 (12)	0.0583 (15)	0.0040 (10)	0.0072 (11)	−0.0006 (11)
C13	0.0481 (13)	0.0334 (11)	0.0445 (12)	0.0023 (9)	0.0038 (10)	0.0015 (9)
C14	0.0572 (14)	0.0304 (10)	0.0430 (13)	0.0037 (10)	0.0144 (10)	0.0034 (9)
C15	0.0599 (15)	0.0464 (13)	0.0476 (14)	0.0067 (11)	0.0140 (11)	−0.0020 (11)
C16	0.0653 (16)	0.0558 (15)	0.0620 (17)	0.0145 (13)	0.0256 (13)	0.0028 (13)
C17	0.088 (2)	0.0417 (13)	0.0522 (16)	0.0060 (13)	0.0322 (14)	0.0024 (11)
C18	0.090 (2)	0.0569 (16)	0.0422 (14)	0.0037 (15)	0.0121 (13)	−0.0052 (12)
C19	0.0665 (16)	0.0513 (14)	0.0492 (14)	0.0069 (12)	0.0067 (12)	−0.0018 (12)
C20	0.0559 (14)	0.0382 (11)	0.0462 (13)	0.0066 (10)	0.0085 (11)	−0.0024 (10)
C21	0.105 (2)	0.0540 (15)	0.0654 (18)	−0.0085 (15)	0.0425 (17)	0.0038 (13)
C22	0.120 (3)	0.0669 (18)	0.073 (2)	0.0083 (18)	0.0516 (19)	−0.0089 (15)

Geometric parameters (Å, º)

O1—C13	1.309 (3)	C7—C8	1.381 (3)
O1—H1O1	0.882 (17)	C7—C12	1.384 (3)
O2—C13	1.206 (3)	C7—C13	1.487 (3)
O3—C20	1.304 (3)	C8—C9	1.384 (3)
O3—H1O3	0.871 (18)	C8—H8A	0.9400
O4—C20	1.199 (3)	C9—C10	1.376 (3)
N1—C1	1.471 (3)	C9—H9A	0.9400
N1—C4	1.477 (3)	C10—C11	1.379 (4)
N1—C3	1.481 (3)	C10—C21	1.511 (3)
N2—C1	1.472 (3)	C11—C12	1.381 (4)
N2—C5	1.474 (3)	C11—H11A	0.9400
N2—C2	1.477 (3)	C12—H12A	0.9400
N3—C3	1.458 (3)	C14—C19	1.376 (3)
N3—C2	1.459 (3)	C14—C15	1.381 (3)
N3—C6	1.463 (3)	C14—C20	1.488 (3)
N4—C4	1.459 (3)	C15—C16	1.381 (3)
N4—C5	1.460 (3)	C15—H15A	0.9400
N4—C6	1.466 (3)	C16—C17	1.376 (4)
C1—H1A	0.9800	C16—H16A	0.9400
C1—H1B	0.9800	C17—C18	1.382 (4)
C2—H2A	0.9800	C17—C22	1.505 (3)
C2—H2B	0.9800	C18—C19	1.382 (4)
C3—H3A	0.9800	C18—H18A	0.9400
C3—H3B	0.9800	C19—H19A	0.9400
C4—H4A	0.9800	C21—H21A	0.9700
C4—H4B	0.9800	C21—H21B	0.9700
C5—H5A	0.9800	C21—H21C	0.9700
C5—H5B	0.9800	C22—H22A	0.9700
C6—H6A	0.9800	C22—H22B	0.9700
C6—H6B	0.9800	C22—H22C	0.9700
C13—O1—H1O1	108 (2)	C12—C7—C13	119.6 (2)
C20—O3—H1O3	106 (2)	C7—C8—C9	120.3 (2)
C1—N1—C4	107.72 (17)	C7—C8—H8A	119.9
C1—N1—C3	108.19 (17)	C9—C8—H8A	119.9
C4—N1—C3	108.56 (17)	C10—C9—C8	121.2 (2)
C1—N2—C5	107.76 (17)	C10—C9—H9A	119.4
C1—N2—C2	108.09 (17)	C8—C9—H9A	119.4
C5—N2—C2	108.55 (17)	C9—C10—C11	118.1 (2)
C3—N3—C2	108.6 (2)	C9—C10—C21	121.7 (2)
C3—N3—C6	108.3 (2)	C11—C10—C21	120.1 (2)
C2—N3—C6	108.17 (19)	C10—C11—C12	121.5 (2)
C4—N4—C5	108.00 (19)	C10—C11—H11A	119.3
C4—N4—C6	108.08 (19)	C12—C11—H11A	119.3
C5—N4—C6	108.29 (19)	C11—C12—C7	120.0 (2)
N1—C1—N2	111.71 (16)	C11—C12—H12A	120.0
N1—C1—H1A	109.3	C7—C12—H12A	120.0
N2—C1—H1A	109.3	O2—C13—O1	122.8 (2)
N1—C1—H1B	109.3	O2—C13—C7	122.3 (2)
N2—C1—H1B	109.3	O1—C13—C7	114.93 (19)
H1A—C1—H1B	107.9	C19—C14—C15	119.0 (2)
N3—C2—N2	111.82 (18)	C19—C14—C20	118.6 (2)
N3—C2—H2A	109.3	C15—C14—C20	122.3 (2)
N2—C2—H2A	109.3	C14—C15—C16	120.1 (2)
N3—C2—H2B	109.3	C14—C15—H15A	120.0
N2—C2—H2B	109.3	C16—C15—H15A	120.0
H2A—C2—H2B	107.9	C17—C16—C15	121.6 (3)
N3—C3—N1	111.52 (18)	C17—C16—H16A	119.2
N3—C3—H3A	109.3	C15—C16—H16A	119.2
N1—C3—H3A	109.3	C16—C17—C18	117.7 (2)
N3—C3—H3B	109.3	C16—C17—C22	121.4 (3)
N1—C3—H3B	109.3	C18—C17—C22	120.8 (3)
H3A—C3—H3B	108.0	C17—C18—C19	121.3 (3)
N4—C4—N1	111.95 (18)	C17—C18—H18A	119.3
N4—C4—H4A	109.2	C19—C18—H18A	119.3
N1—C4—H4A	109.2	C14—C19—C18	120.3 (3)
N4—C4—H4B	109.2	C14—C19—H19A	119.9
N1—C4—H4B	109.2	C18—C19—H19A	119.9
H4A—C4—H4B	107.9	O4—C20—O3	122.6 (2)
N4—C5—N2	112.01 (17)	O4—C20—C14	122.6 (2)
N4—C5—H5A	109.2	O3—C20—C14	114.8 (2)
N2—C5—H5A	109.2	C10—C21—H21A	109.5
N4—C5—H5B	109.2	C10—C21—H21B	109.5
N2—C5—H5B	109.2	H21A—C21—H21B	109.5
H5A—C5—H5B	107.9	C10—C21—H21C	109.5
N3—C6—N4	112.80 (17)	H21A—C21—H21C	109.5
N3—C6—H6A	109.0	H21B—C21—H21C	109.5
N4—C6—H6A	109.0	C17—C22—H22A	109.5
N3—C6—H6B	109.0	C17—C22—H22B	109.5
N4—C6—H6B	109.0	H22A—C22—H22B	109.5
H6A—C6—H6B	107.8	C17—C22—H22C	109.5
C8—C7—C12	118.9 (2)	H22A—C22—H22C	109.5
C8—C7—C13	121.4 (2)	H22B—C22—H22C	109.5
C4—N1—C1—N2	58.8 (2)	C7—C8—C9—C10	0.0 (4)
C3—N1—C1—N2	−58.4 (2)	C8—C9—C10—C11	0.2 (4)
C5—N2—C1—N1	−58.8 (2)	C8—C9—C10—C21	−178.1 (2)
C2—N2—C1—N1	58.3 (2)	C9—C10—C11—C12	−0.8 (4)
C3—N3—C2—N2	59.2 (2)	C21—C10—C11—C12	177.5 (2)
C6—N3—C2—N2	−58.1 (2)	C10—C11—C12—C7	1.2 (4)
C1—N2—C2—N3	−58.6 (2)	C8—C7—C12—C11	−1.0 (3)
C5—N2—C2—N3	58.0 (2)	C13—C7—C12—C11	−179.5 (2)
C2—N3—C3—N1	−59.1 (3)	C8—C7—C13—O2	−172.9 (2)
C6—N3—C3—N1	58.2 (2)	C12—C7—C13—O2	5.6 (3)
C1—N1—C3—N3	58.7 (2)	C8—C7—C13—O1	6.2 (3)
C4—N1—C3—N3	−58.0 (2)	C12—C7—C13—O1	−175.4 (2)
C5—N4—C4—N1	59.3 (2)	C19—C14—C15—C16	0.9 (4)
C6—N4—C4—N1	−57.6 (2)	C20—C14—C15—C16	178.3 (2)
C1—N1—C4—N4	−59.1 (2)	C14—C15—C16—C17	0.0 (4)
C3—N1—C4—N4	57.9 (2)	C15—C16—C17—C18	−0.4 (4)
C4—N4—C5—N2	−59.4 (2)	C15—C16—C17—C22	179.9 (2)
C6—N4—C5—N2	57.4 (2)	C16—C17—C18—C19	−0.1 (4)
C1—N2—C5—N4	59.1 (2)	C22—C17—C18—C19	179.7 (2)
C2—N2—C5—N4	−57.7 (2)	C15—C14—C19—C18	−1.3 (4)
C3—N3—C6—N4	−59.0 (3)	C20—C14—C19—C18	−178.9 (2)
C2—N3—C6—N4	58.6 (3)	C17—C18—C19—C14	0.9 (4)
C4—N4—C6—N3	58.6 (3)	C19—C14—C20—O4	7.8 (4)
C5—N4—C6—N3	−58.2 (3)	C15—C14—C20—O4	−169.7 (3)
C12—C7—C8—C9	0.4 (3)	C19—C14—C20—O3	−173.0 (2)
C13—C7—C8—C9	178.8 (2)	C15—C14—C20—O3	9.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···N2	0.87 (3)	1.80 (3)	2.661 (3)	171 (3)
O1—H1O1···N1	0.88 (3)	1.75 (3)	2.620 (3)	170 (2)
C3—H3B···O4^i	0.98	2.63	3.242 (3)	120
C4—H4B···O2^ii	0.98	2.47	3.141 (3)	126
C3—H3A···Cg2^iii	0.98	2.87	3.815 (3)	161
C5—H5A···Cg1^iii	0.98	2.71	3.683 (3)	170
C21—H21B···Cg1^iv	0.97	2.97	3.599 (3)	124
C22—H22C···Cg2^v	0.97	2.84	3.732 (4)	153

Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x+1, y, z; (iii) x−1/2, −y+1/2, z−3/2; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y+2, −z+1.

Hexamethylenetetramine bis(4-methylbenzoic acid) (1533075)

Crystal data

2(C8H8O2)·C6H12N4	Dx = 1.274 Mg m^−3
Mr = 412.48	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Cmcm	Cell parameters from 2689 reflections
a = 10.1948 (13) Å	θ = 2.8–25.9°
b = 7.3566 (9) Å	µ = 0.09 mm^−1
c = 28.679 (4) Å	T = 280 K
V = 2150.9 (5) Å^3	Block, colourless
Z = 4	0.38 × 0.18 × 0.13 mm
F(000) = 880

Data collection

Bruker APEX Duo CCD area detector diffractometer	1403 independent reflections
Radiation source: fine-focus sealed tube	960 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 28.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.919, Tmax = 0.967	k = −9→9
10210 measured reflections	l = −37→33

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.080	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.243	w = 1/[σ^2(Fo^2) + (0.090P)^2 + 2.2465P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
1403 reflections	Δρmax = 0.32 e Å^−3
112 parameters	Δρmin = −0.32 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.0866 (8)	−0.0326 (10)	0.6450 (3)	0.0781 (18)	0.5
H1O1	0.066 (6)	0.063 (12)	0.663 (3)	0.12 (3)*	0.5
O2	−0.1241 (8)	−0.0868 (14)	0.6518 (4)	0.115 (4)	0.5
C4	−0.0227 (10)	−0.1280 (7)	0.63717 (15)	0.057 (3)	0.5
C5	0.0024 (12)	−0.2955 (3)	0.60850 (8)	0.0576 (11)	0.5
C6	0.1273 (10)	−0.3573 (11)	0.5973 (3)	0.0671 (19)	0.5
H6A	0.2007	−0.2929	0.6073	0.080*	0.5
C7	0.1426 (4)	−0.5153 (11)	0.5713 (3)	0.074 (2)	0.5
H7A	0.2262	−0.5567	0.5639	0.089*	0.5
C8	0.0330 (3)	−0.6115 (4)	0.55647 (10)	0.061 (2)	0.5
C9	−0.0920 (3)	−0.5497 (10)	0.5676 (3)	0.072 (2)	0.5
H9A	−0.1653	−0.6141	0.5577	0.086*	0.5
C10	−0.1073 (8)	−0.3917 (11)	0.5936 (3)	0.072 (2)	0.5
H10A	−0.1909	−0.3504	0.6011	0.087*	0.5
C11	0.0466 (7)	−0.7869 (7)	0.5286 (2)	0.100 (3)	0.5
H11A	0.1355	−0.8224	0.5223	0.150*	0.5
H11B	0.0058	−0.8814	0.5465	0.150*	0.5
H11C	0.0011	−0.7773	0.4993	0.150*	0.5
N1	0.0000	0.2162 (4)	0.70891 (10)	0.0933 (13)
N2	0.1172 (3)	0.4485 (4)	0.7500	0.1049 (15)
C1	0.1143 (4)	0.3332 (4)	0.70966 (17)	0.150 (2)
H1A	0.1928	0.2587	0.7092	0.180*
H1B	0.1146	0.4081	0.6818	0.180*
C2	0.0000	0.1040 (5)	0.7500	0.0550 (10)
H2A	0.0763	0.0253	0.7500	0.066*
C3	0.0000	0.5583 (6)	0.7500	0.0769 (16)
H3A	0.0000	0.6342	0.7224	0.092*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.083 (4)	0.067 (4)	0.084 (3)	−0.011 (3)	0.019 (3)	−0.026 (3)
O2	0.086 (5)	0.115 (7)	0.144 (6)	−0.010 (4)	0.030 (4)	−0.065 (5)
C4	0.058 (8)	0.063 (2)	0.051 (2)	−0.001 (3)	0.002 (2)	−0.0019 (17)
C5	0.073 (2)	0.0550 (18)	0.0446 (17)	−0.008 (10)	−0.016 (7)	0.0021 (15)
C6	0.080 (5)	0.067 (4)	0.054 (4)	0.001 (3)	0.004 (3)	−0.013 (3)
C7	0.084 (5)	0.069 (4)	0.069 (4)	0.003 (4)	−0.003 (5)	−0.015 (3)
C8	0.074 (6)	0.057 (2)	0.053 (2)	0.000 (2)	0.0013 (19)	0.0003 (18)
C9	0.068 (5)	0.071 (5)	0.076 (4)	−0.010 (4)	0.007 (4)	−0.013 (4)
C10	0.063 (4)	0.077 (5)	0.076 (5)	0.000 (4)	0.013 (3)	−0.006 (4)
C11	0.160 (9)	0.064 (3)	0.076 (3)	0.002 (3)	0.002 (3)	−0.013 (3)
N1	0.186 (4)	0.0462 (15)	0.0478 (16)	0.000	0.000	−0.0029 (13)
N2	0.069 (2)	0.0540 (18)	0.192 (5)	−0.0159 (16)	0.000	0.000
C1	0.198 (4)	0.0579 (17)	0.193 (4)	−0.008 (2)	0.138 (4)	0.002 (2)
C2	0.072 (3)	0.039 (2)	0.054 (2)	0.000	0.000	0.000
C3	0.114 (4)	0.038 (2)	0.078 (3)	0.000	0.000	0.000

Geometric parameters (Å, º)

O1—C4	1.337 (12)	C11—H11A	0.9600
O1—H1O1	0.90 (9)	C11—H11B	0.9600
O2—C4	1.155 (14)	C11—H11C	0.9600
C4—C5	1.503 (6)	N1—C2	1.439 (4)
C5—C6	1.3900	N1—C1	1.449 (4)
C5—C10	1.3900	N1—C1^i	1.449 (4)
C6—C7	1.3900	N2—C1	1.435 (4)
C6—H6A	0.9300	N2—C1^ii	1.435 (4)
C7—C8	1.3900	N2—C3	1.442 (4)
C7—H7A	0.9300	C1—H1A	0.9700
C8—C9	1.3900	C1—H1B	0.9700
C8—C11	1.525 (6)	C2—N1^ii	1.439 (4)
C9—C10	1.3900	C2—H2A	0.9700
C9—H9A	0.9300	C3—N2^iii	1.442 (4)
C10—H10A	0.9300	C3—H3A	0.9700
C4—O1—H1O1	108 (4)	C8—C11—H11B	107.0
O2—C4—O1	123.2 (6)	H11A—C11—H11B	108.2
O2—C4—C5	124.4 (8)	C8—C11—H11C	110.6
O1—C4—C5	112.4 (9)	H11A—C11—H11C	108.2
C6—C5—C10	120.0	H11B—C11—H11C	108.2
C6—C5—C4	123.4 (8)	C2—N1—C1	109.2 (3)
C10—C5—C4	116.6 (8)	C2—N1—C1^i	109.2 (3)
C5—C6—C7	120.0	C1—N1—C1^i	107.1 (3)
C5—C6—H6A	120.0	C1—N2—C1^ii	107.5 (4)
C7—C6—H6A	120.0	C1—N2—C3	108.3 (3)
C8—C7—C6	120.0	C1^ii—N2—C3	108.3 (3)
C8—C7—H7A	120.0	N2—C1—N1	112.3 (3)
C6—C7—H7A	120.0	N2—C1—H1A	109.1
C9—C8—C7	120.0	N1—C1—H1A	109.1
C9—C8—C11	118.7 (4)	N2—C1—H1B	109.1
C7—C8—C11	121.2 (4)	N1—C1—H1B	109.1
C8—C9—C10	120.0	H1A—C1—H1B	107.9
C8—C9—H9A	120.0	N1^ii—C2—N1	110.0 (3)
C10—C9—H9A	120.0	N1^ii—C2—H2A	110.0
C9—C10—C5	120.0	N1—C2—H2A	110.0
C9—C10—H10A	120.0	N2—C3—N2^iii	111.9 (4)
C5—C10—H10A	120.0	N2—C3—H3A	108.8
C8—C11—H11A	114.5	N2^iii—C3—H3A	108.8
O2—C4—C5—C6	−169.8 (9)	C8—C9—C10—C5	0.0
O1—C4—C5—C6	8.7 (8)	C6—C5—C10—C9	0.0
O2—C4—C5—C10	9.1 (10)	C4—C5—C10—C9	−178.9 (3)
O1—C4—C5—C10	−172.4 (7)	C1^ii—N2—C1—N1	57.8 (6)
C10—C5—C6—C7	0.0	C3—N2—C1—N1	−59.0 (4)
C4—C5—C6—C7	178.9 (3)	C2—N1—C1—N2	−59.3 (4)
C5—C6—C7—C8	0.0	C1^i—N1—C1—N2	58.8 (6)
C6—C7—C8—C9	0.0	C1—N1—C2—N1^ii	58.38 (19)
C6—C7—C8—C11	−179.0 (3)	C1^i—N1—C2—N1^ii	−58.38 (19)
C7—C8—C9—C10	0.0	C1—N2—C3—N2^iii	58.12 (19)
C11—C8—C9—C10	179.0 (3)	C1^ii—N2—C3—N2^iii	−58.12 (19)

Symmetry codes: (i) −x, y, z; (ii) x, y, −z+3/2; (iii) −x, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.90 (9)	1.86 (8)	2.737 (8)	165 (7)
C11—H11C···Cg7^iv	0.96	2.90	3.655 (6)	136
C11—H11C···Cg7^v	0.96	2.90	3.702 (6)	141

Symmetry codes: (iv) x, −y−1, −z+1; (v) −x, −y−1, −z+1.

Hexamethylenetetramine bis(4-methylbenzoic acid) (1533076)

Crystal data

2(C8H8O2)·C6H12N4	Dx = 1.271 Mg m^−3
Mr = 412.48	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Cmcm	Cell parameters from 2577 reflections
a = 10.1958 (13) Å	θ = 2.8–23.4°
b = 7.3592 (9) Å	µ = 0.09 mm^−1
c = 28.718 (4) Å	T = 290 K
V = 2154.8 (5) Å^3	Block, colourless
Z = 4	0.38 × 0.18 × 0.13 mm
F(000) = 880

Data collection

Bruker APEX Duo CCD area detector diffractometer	1537 independent reflections
Radiation source: fine-focus sealed tube	1010 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 29.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.906, Tmax = 0.967	k = −10→9
10890 measured reflections	l = −39→38

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.079	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.242	w = 1/[σ^2(Fo^2) + (0.0875P)^2 + 1.9708P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
1537 reflections	Δρmax = 0.29 e Å^−3
112 parameters	Δρmin = −0.27 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.0854 (7)	−0.0348 (10)	0.6449 (3)	0.0806 (16)	0.5
H1O1	0.067 (5)	0.065 (10)	0.661 (2)	0.11 (2)*	0.5
O2	−0.1254 (7)	−0.0883 (13)	0.6522 (4)	0.120 (3)	0.5
C4	−0.0239 (8)	−0.1290 (7)	0.63718 (14)	0.060 (2)	0.5
C5	0.0015 (12)	−0.2965 (3)	0.60865 (8)	0.0604 (10)	0.5
C6	0.1264 (9)	−0.3572 (10)	0.5971 (3)	0.0710 (18)	0.5
H6A	0.1997	−0.2924	0.6069	0.085*	0.5
C7	0.1418 (4)	−0.5149 (10)	0.5711 (3)	0.076 (2)	0.5
H7A	0.2254	−0.5555	0.5634	0.092*	0.5
C8	0.0323 (3)	−0.6119 (3)	0.55649 (9)	0.064 (2)	0.5
C9	−0.0927 (4)	−0.5512 (10)	0.5680 (3)	0.0751 (19)	0.5
H9A	−0.1660	−0.6161	0.5583	0.090*	0.5
C10	−0.1081 (8)	−0.3935 (10)	0.5941 (3)	0.0745 (19)	0.5
H10A	−0.1917	−0.3529	0.6018	0.089*	0.5
C11	0.0450 (8)	−0.7872 (7)	0.52848 (19)	0.109 (4)	0.5
H11A	0.1320	−0.8291	0.5216	0.163*	0.5
H11B	0.0026	−0.8823	0.5457	0.163*	0.5
H11C	−0.0003	−0.7771	0.4993	0.163*	0.5
N1	0.0000	0.2148 (4)	0.70895 (9)	0.0944 (12)
N2	0.1173 (3)	0.4461 (4)	0.7500	0.1074 (14)
C1	0.1143 (4)	0.3310 (4)	0.70970 (16)	0.1499 (19)
H1A	0.1927	0.2562	0.7093	0.180*
H1B	0.1149	0.4059	0.6819	0.180*
C2	0.0000	0.1026 (5)	0.7500	0.0574 (10)
H2A	0.0748	0.0211	0.7500	0.069*
C3	0.0000	0.5568 (6)	0.7500	0.0817 (16)
H3A	0.0000	0.6279	0.7216	0.098*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.084 (4)	0.071 (3)	0.086 (3)	−0.011 (3)	0.016 (3)	−0.028 (3)
O2	0.089 (4)	0.123 (7)	0.147 (6)	−0.012 (3)	0.033 (3)	−0.069 (5)
C4	0.061 (7)	0.065 (2)	0.0532 (19)	−0.003 (2)	0.004 (2)	−0.0031 (16)
C5	0.078 (2)	0.0566 (16)	0.0461 (16)	−0.004 (11)	−0.018 (7)	0.0027 (15)
C6	0.086 (5)	0.070 (4)	0.057 (4)	−0.003 (3)	0.006 (3)	−0.011 (3)
C7	0.089 (5)	0.070 (4)	0.070 (3)	−0.001 (4)	0.000 (4)	−0.013 (3)
C8	0.077 (6)	0.058 (2)	0.056 (2)	−0.0010 (19)	0.0029 (19)	−0.0001 (16)
C9	0.071 (5)	0.070 (4)	0.085 (4)	−0.009 (4)	0.005 (4)	−0.012 (4)
C10	0.067 (4)	0.075 (4)	0.082 (5)	−0.003 (3)	0.012 (3)	−0.008 (4)
C11	0.179 (11)	0.065 (3)	0.081 (3)	0.004 (3)	0.002 (4)	−0.015 (2)
N1	0.186 (4)	0.0476 (14)	0.0497 (14)	0.000	0.000	−0.0028 (11)
N2	0.073 (2)	0.0569 (17)	0.192 (4)	−0.0156 (15)	0.000	0.000
C1	0.199 (4)	0.0613 (16)	0.190 (4)	−0.008 (2)	0.135 (3)	0.003 (2)
C2	0.075 (3)	0.0399 (18)	0.057 (2)	0.000	0.000	0.000
C3	0.123 (4)	0.040 (2)	0.082 (3)	0.000	0.000	0.000

Geometric parameters (Å, º)

O1—C4	1.331 (10)	C11—H11A	0.9600
O1—H1O1	0.89 (8)	C11—H11B	0.9600
O2—C4	1.161 (11)	C11—H11C	0.9600
C4—C5	1.503 (6)	N1—C2	1.439 (3)
C5—C6	1.3900	N1—C1	1.446 (4)
C5—C10	1.3900	N1—C1^i	1.446 (4)
C6—C7	1.3900	N2—C1^ii	1.434 (4)
C6—H6A	0.9300	N2—C1	1.434 (4)
C7—C8	1.3900	N2—C3	1.447 (4)
C7—H7A	0.9300	C1—H1A	0.9700
C8—C9	1.3900	C1—H1B	0.9700
C8—C11	1.526 (5)	C2—N1^ii	1.439 (3)
C9—C10	1.3900	C2—H2A	0.9700
C9—H9A	0.9300	C3—N2^iii	1.447 (4)
C10—H10A	0.9300	C3—H3A	0.9700
C4—O1—H1O1	110 (4)	C8—C11—H11B	107.9
O2—C4—O1	123.4 (6)	H11A—C11—H11B	106.8
O2—C4—C5	124.6 (8)	C8—C11—H11C	110.7
O1—C4—C5	112.0 (8)	H11A—C11—H11C	106.8
C6—C5—C10	120.0	H11B—C11—H11C	106.8
C6—C5—C4	123.4 (8)	C2—N1—C1	109.1 (2)
C10—C5—C4	116.5 (8)	C2—N1—C1^i	109.1 (2)
C5—C6—C7	120.0	C1—N1—C1^i	107.5 (3)
C5—C6—H6A	120.0	C1^ii—N2—C1	107.6 (3)
C7—C6—H6A	120.0	C1^ii—N2—C3	108.4 (3)
C8—C7—C6	120.0	C1—N2—C3	108.4 (3)
C8—C7—H7A	120.0	N2—C1—N1	112.2 (3)
C6—C7—H7A	120.0	N2—C1—H1A	109.2
C7—C8—C9	120.0	N1—C1—H1A	109.2
C7—C8—C11	121.6 (4)	N2—C1—H1B	109.2
C9—C8—C11	118.4 (4)	N1—C1—H1B	109.2
C8—C9—C10	120.0	H1A—C1—H1B	107.9
C8—C9—H9A	120.0	N1^ii—C2—N1	110.0 (3)
C10—C9—H9A	120.0	N1^ii—C2—H2A	110.8
C9—C10—C5	120.0	N1—C2—H2A	110.8
C9—C10—H10A	120.0	N2^iii—C3—N2	111.5 (3)
C5—C10—H10A	120.0	N2^iii—C3—H3A	107.7
C8—C11—H11A	117.3	N2—C3—H3A	107.7
O2—C4—C5—C6	−169.7 (9)	C8—C9—C10—C5	0.0
O1—C4—C5—C6	7.9 (8)	C6—C5—C10—C9	0.0
O2—C4—C5—C10	9.5 (10)	C4—C5—C10—C9	−179.3 (2)
O1—C4—C5—C10	−172.9 (6)	C1^ii—N2—C1—N1	58.0 (5)
C10—C5—C6—C7	0.0	C3—N2—C1—N1	−59.0 (4)
C4—C5—C6—C7	179.2 (3)	C2—N1—C1—N2	−59.4 (4)
C5—C6—C7—C8	0.0	C1^i—N1—C1—N2	58.8 (5)
C6—C7—C8—C9	0.0	C1—N1—C2—N1^ii	58.55 (18)
C6—C7—C8—C11	−179.0 (3)	C1^i—N1—C2—N1^ii	−58.55 (18)
C7—C8—C9—C10	0.0	C1^ii—N2—C3—N2^iii	−58.22 (18)
C11—C8—C9—C10	179.0 (3)	C1—N2—C3—N2^iii	58.22 (18)

Symmetry codes: (i) −x, y, z; (ii) x, y, −z+3/2; (iii) −x, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.89 (7)	1.89 (6)	2.742 (8)	160 (6)
C11—H11C···Cg1^iv	0.96	2.91	3.662 (6)	136
C11—H11C···Cg1^v	0.96	2.91	3.705 (6)	141

Symmetry codes: (iv) x, −y−1, −z+1; (v) −x, −y−1, −z+1.