Cyclo-hexane-1,3-diyl bis-(N-phenyl-carbamate).

The asymmetric unit of the title compound, C(20)H(22)N(2)O(4), comprises two crystallographically independent mol-ecules (A and B) with slightly different geometries. The dihedral angle between the two terminal phenyl rings is 61.7 (1)° in mol-ecule A and 29.6 (1)° in B. The cyclo-hexane rings adopt chair conformations. In the crystal packing, inter-molecular N-H⋯O hydrogen bonds inter-connect adjacent mol-ecules into a ladder-like structure along the c axis incorporating R(2) (2)(20) ring motifs. The crystal packing is further stabilized by weak inter-molecular C-H⋯π inter-actions.

Related literature

For general background and the synthesis of carbamates, see: Banerjee et al. (1978 ▶); Ghalib et al. (2010 ▶); Graia et al. (2009 ▶); Ibuka et al. (1985 ▶); Lapidus et al. (1987 ▶); Loev & Kormendy (1963 ▶); Niu et al. (2007 ▶). For ring conformation and puckering analysis, see: Cremer & Pople (1975 ▶). For graph-set motifs, see: Bernstein et al. (1995 ▶). For a related structure, see: Ghalib et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C20H22N2O4

M = 354.40

Monoclinic,

a = 38.356 (7) Å

b = 9.5453 (16) Å

c = 9.8472 (16) Å

β = 91.034 (3)°

V = 3604.7 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.55 × 0.15 × 0.13 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.951, T max = 0.988

30037 measured reflections

10472 independent reflections

6630 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.180

S = 1.08

10472 reflections

485 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033817/ci5161sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033817/ci5161Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H22N2O4	F(000) = 1504
Mr = 354.40	Dx = 1.306 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3229 reflections
a = 38.356 (7) Å	θ = 3.0–32.1°
b = 9.5453 (16) Å	µ = 0.09 mm−1
c = 9.8472 (16) Å	T = 100 K
β = 91.034 (3)°	Needle, colourless
V = 3604.7 (10) Å3	0.55 × 0.15 × 0.13 mm
Z = 8

Bruker APEXII DUO CCD area-detector diffractometer	10472 independent reflections
Radiation source: fine-focus sealed tube	6630 reflections with I > 2σ(I)
graphite	Rint = 0.057
φ and ω scans	θmax = 30.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −51→53
Tmin = 0.951, Tmax = 0.988	k = −11→13
30037 measured reflections	l = −13→13

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0587P)2 + 2.1169P] where P = (Fo2 + 2Fc2)/3
10472 reflections	(Δ/σ)max = 0.001
485 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1A	0.32324 (4)	0.22226 (16)	0.31570 (14)	0.0210 (3)
O2A	0.35690 (3)	0.27958 (16)	0.49976 (14)	0.0213 (3)
O3A	0.47863 (3)	0.24586 (16)	0.53335 (14)	0.0218 (3)
O4A	0.51876 (4)	0.22687 (17)	0.36729 (14)	0.0259 (3)
N1A	0.30419 (4)	0.19662 (19)	0.53465 (18)	0.0198 (4)
N2A	0.53147 (4)	0.17410 (19)	0.59053 (17)	0.0194 (4)
C1A	0.25950 (5)	0.0743 (2)	0.3965 (2)	0.0215 (4)
H1AA	0.2760	0.0475	0.3335	0.026*
C2A	0.22478 (6)	0.0356 (2)	0.3788 (2)	0.0265 (5)
H2AA	0.2180	−0.0166	0.3031	0.032*
C3A	0.20014 (6)	0.0740 (3)	0.4726 (2)	0.0290 (5)
H3AA	0.1769	0.0486	0.4594	0.035*
C4A	0.21015 (6)	0.1504 (3)	0.5862 (2)	0.0296 (5)
H4AA	0.1937	0.1747	0.6501	0.036*
C5A	0.24475 (5)	0.1909 (2)	0.6053 (2)	0.0235 (4)
H5AA	0.2514	0.2426	0.6816	0.028*
C6A	0.26940 (5)	0.1536 (2)	0.5095 (2)	0.0194 (4)
C7A	0.32746 (5)	0.2314 (2)	0.4382 (2)	0.0165 (4)
C8A	0.38682 (5)	0.3068 (2)	0.4156 (2)	0.0180 (4)
H8AA	0.3848	0.2531	0.3310	0.022*
C9A	0.38944 (5)	0.4620 (2)	0.3841 (2)	0.0213 (4)
H9AA	0.3875	0.5155	0.4673	0.026*
H9AB	0.3704	0.4891	0.3235	0.026*
C10A	0.42429 (5)	0.4948 (2)	0.3174 (2)	0.0213 (4)
H10A	0.4252	0.4481	0.2300	0.026*
H10B	0.4260	0.5949	0.3017	0.026*
C11A	0.45518 (5)	0.4471 (2)	0.4063 (2)	0.0210 (4)
H11A	0.4768	0.4662	0.3603	0.025*
H11B	0.4554	0.4987	0.4912	0.025*
C12A	0.45230 (5)	0.2912 (2)	0.4349 (2)	0.0176 (4)
H12A	0.4548	0.2383	0.3503	0.021*
C13A	0.41781 (5)	0.2548 (2)	0.4998 (2)	0.0172 (4)
H13A	0.4171	0.2963	0.5897	0.021*
H13B	0.4162	0.1539	0.5101	0.021*
C14A	0.51069 (5)	0.2170 (2)	0.4859 (2)	0.0180 (4)
C15A	0.56754 (5)	0.1433 (2)	0.5863 (2)	0.0179 (4)
C16A	0.58223 (5)	0.0713 (2)	0.6959 (2)	0.0206 (4)
H16A	0.5681	0.0404	0.7656	0.025*
C17A	0.61787 (6)	0.0451 (2)	0.7023 (2)	0.0255 (5)
H17A	0.6275	−0.0020	0.7767	0.031*
C18A	0.63918 (5)	0.0888 (2)	0.5979 (2)	0.0259 (5)
H18A	0.6631	0.0721	0.6022	0.031*
C19A	0.62432 (5)	0.1581 (2)	0.4871 (2)	0.0240 (5)
H19A	0.6384	0.1858	0.4159	0.029*
C20A	0.58872 (5)	0.1867 (2)	0.4809 (2)	0.0195 (4)
H20A	0.5791	0.2345	0.4069	0.023*
O1B	−0.02136 (4)	0.77244 (17)	0.13203 (14)	0.0242 (3)
O2B	0.01910 (3)	0.75338 (16)	−0.03230 (14)	0.0207 (3)
O3B	0.14054 (3)	0.71216 (15)	0.00059 (14)	0.0189 (3)
O4B	0.17604 (4)	0.74059 (17)	0.18627 (14)	0.0242 (3)
N1B	−0.03341 (4)	0.82633 (18)	−0.09211 (17)	0.0179 (3)
N2B	0.19386 (4)	0.78876 (19)	−0.03047 (18)	0.0184 (4)
C1B	−0.09132 (5)	0.8200 (2)	0.0143 (2)	0.0191 (4)
H1BA	−0.0825	0.7705	0.0888	0.023*
C2B	−0.12654 (5)	0.8537 (2)	0.0058 (2)	0.0232 (4)
H2BA	−0.1412	0.8270	0.0754	0.028*
C3B	−0.14022 (5)	0.9265 (2)	−0.1049 (2)	0.0243 (5)
H3BA	−0.1639	0.9480	−0.1099	0.029*
C4B	−0.11823 (5)	0.9667 (2)	−0.2078 (2)	0.0233 (4)
H4BA	−0.1272	1.0157	−0.2822	0.028*
C5B	−0.08294 (5)	0.9346 (2)	−0.2011 (2)	0.0195 (4)
H5BA	−0.0684	0.9622	−0.2707	0.023*
C6B	−0.06928 (5)	0.8607 (2)	−0.08937 (19)	0.0157 (4)
C7B	−0.01295 (5)	0.7830 (2)	0.0140 (2)	0.0172 (4)
C8B	0.04525 (5)	0.7077 (2)	0.06741 (19)	0.0165 (4)
H8BA	0.0429	0.7617	0.1514	0.020*
C9B	0.04178 (5)	0.5521 (2)	0.0974 (2)	0.0184 (4)
H9BA	0.0412	0.4998	0.0129	0.022*
H9BB	0.0202	0.5348	0.1441	0.022*
C10B	0.07256 (5)	0.5031 (2)	0.1857 (2)	0.0192 (4)
H10C	0.0703	0.4034	0.2029	0.023*
H10D	0.0721	0.5512	0.2724	0.023*
C11B	0.10739 (5)	0.5314 (2)	0.1179 (2)	0.0194 (4)
H11C	0.1264	0.5028	0.1780	0.023*
H11D	0.1088	0.4774	0.0348	0.023*
C12B	0.11062 (5)	0.6861 (2)	0.08605 (19)	0.0160 (4)
H12B	0.1130	0.7398	0.1706	0.019*
C13B	0.07986 (5)	0.7408 (2)	0.0023 (2)	0.0168 (4)
H13C	0.0821	0.8415	−0.0080	0.020*
H13D	0.0803	0.6992	−0.0875	0.020*
C14B	0.17103 (5)	0.7465 (2)	0.0642 (2)	0.0162 (4)
C15B	0.22895 (5)	0.8287 (2)	−0.00429 (19)	0.0178 (4)
C16B	0.24314 (6)	0.9297 (2)	−0.0886 (2)	0.0247 (5)
H16B	0.2294	0.9715	−0.1560	0.030*
C17B	0.27798 (6)	0.9682 (3)	−0.0719 (3)	0.0342 (6)
H17B	0.2877	1.0338	−0.1299	0.041*
C18B	0.29811 (6)	0.9090 (3)	0.0306 (3)	0.0374 (6)
H18B	0.3212	0.9362	0.0428	0.045*
C19B	0.28398 (6)	0.8100 (3)	0.1147 (3)	0.0337 (6)
H19B	0.2976	0.7708	0.1839	0.040*
C20B	0.24941 (5)	0.7677 (2)	0.0972 (2)	0.0251 (5)
H20B	0.2401	0.6992	0.1532	0.030*
H1NA	0.3111 (6)	0.219 (2)	0.612 (2)	0.014 (6)*
H2NA	0.5227 (7)	0.181 (3)	0.676 (3)	0.048 (8)*
H1NB	−0.0234 (7)	0.824 (3)	−0.177 (3)	0.038 (7)*
H2NB	0.1855 (6)	0.795 (3)	−0.114 (3)	0.031 (7)*

	U11	U22	U33	U12	U13	U23
O1A	0.0194 (7)	0.0295 (8)	0.0140 (7)	−0.0001 (6)	−0.0018 (5)	0.0010 (6)
O2A	0.0154 (6)	0.0328 (8)	0.0156 (7)	−0.0043 (6)	0.0008 (5)	−0.0037 (6)
O3A	0.0153 (6)	0.0357 (9)	0.0142 (7)	0.0044 (6)	−0.0003 (5)	0.0007 (6)
O4A	0.0215 (7)	0.0415 (9)	0.0147 (7)	0.0057 (7)	0.0007 (6)	0.0019 (7)
N1A	0.0174 (8)	0.0301 (10)	0.0118 (8)	−0.0032 (7)	−0.0010 (6)	−0.0028 (7)
N2A	0.0176 (8)	0.0271 (9)	0.0136 (8)	0.0022 (7)	−0.0005 (6)	0.0017 (7)
C1A	0.0207 (9)	0.0231 (10)	0.0206 (10)	−0.0015 (8)	−0.0035 (8)	0.0004 (8)
C2A	0.0260 (11)	0.0282 (12)	0.0251 (11)	−0.0075 (9)	−0.0090 (9)	0.0016 (9)
C3A	0.0187 (10)	0.0334 (13)	0.0346 (13)	−0.0067 (9)	−0.0050 (9)	0.0081 (10)
C4A	0.0204 (10)	0.0326 (12)	0.0361 (13)	−0.0001 (9)	0.0058 (9)	0.0038 (10)
C5A	0.0204 (10)	0.0276 (11)	0.0225 (11)	−0.0009 (8)	0.0020 (8)	−0.0022 (9)
C6A	0.0166 (9)	0.0199 (10)	0.0214 (10)	−0.0024 (7)	−0.0017 (8)	0.0027 (8)
C7A	0.0155 (9)	0.0179 (9)	0.0161 (10)	0.0012 (7)	−0.0032 (7)	−0.0013 (7)
C8A	0.0158 (8)	0.0230 (10)	0.0154 (9)	−0.0015 (7)	0.0021 (7)	−0.0004 (8)
C9A	0.0209 (9)	0.0215 (10)	0.0215 (10)	0.0025 (8)	−0.0017 (8)	0.0009 (8)
C10A	0.0281 (10)	0.0168 (10)	0.0190 (10)	−0.0029 (8)	−0.0010 (8)	0.0000 (8)
C11A	0.0204 (9)	0.0241 (11)	0.0185 (10)	−0.0056 (8)	0.0028 (8)	−0.0012 (8)
C12A	0.0157 (9)	0.0240 (10)	0.0131 (9)	0.0014 (7)	−0.0025 (7)	−0.0007 (8)
C13A	0.0169 (9)	0.0204 (10)	0.0143 (9)	0.0000 (7)	0.0014 (7)	0.0019 (7)
C14A	0.0157 (9)	0.0222 (10)	0.0161 (9)	0.0010 (7)	0.0006 (7)	−0.0013 (8)
C15A	0.0186 (9)	0.0178 (9)	0.0173 (10)	0.0013 (7)	−0.0015 (7)	−0.0030 (8)
C16A	0.0244 (10)	0.0201 (10)	0.0172 (10)	0.0033 (8)	−0.0023 (8)	−0.0026 (8)
C17A	0.0276 (11)	0.0243 (11)	0.0243 (11)	0.0062 (9)	−0.0076 (9)	−0.0041 (9)
C18A	0.0184 (10)	0.0280 (12)	0.0310 (12)	0.0037 (8)	−0.0049 (9)	−0.0061 (10)
C19A	0.0210 (10)	0.0222 (11)	0.0288 (12)	0.0001 (8)	0.0021 (8)	−0.0021 (9)
C20A	0.0205 (9)	0.0199 (10)	0.0181 (10)	0.0015 (8)	−0.0001 (8)	0.0010 (8)
O1B	0.0218 (7)	0.0381 (9)	0.0128 (7)	0.0066 (6)	−0.0001 (6)	0.0021 (6)
O2B	0.0144 (6)	0.0333 (8)	0.0145 (7)	0.0035 (6)	−0.0014 (5)	0.0018 (6)
O3B	0.0142 (6)	0.0283 (8)	0.0142 (7)	−0.0040 (6)	0.0004 (5)	−0.0019 (6)
O4B	0.0204 (7)	0.0407 (9)	0.0115 (7)	−0.0029 (6)	−0.0017 (5)	0.0021 (6)
N1B	0.0164 (8)	0.0256 (9)	0.0116 (8)	0.0022 (7)	0.0000 (6)	0.0010 (7)
N2B	0.0148 (7)	0.0281 (9)	0.0123 (8)	−0.0021 (7)	−0.0012 (6)	0.0010 (7)
C1B	0.0202 (9)	0.0201 (10)	0.0170 (10)	0.0005 (8)	−0.0010 (8)	−0.0016 (8)
C2B	0.0197 (9)	0.0252 (11)	0.0249 (11)	0.0004 (8)	0.0025 (8)	−0.0029 (9)
C3B	0.0178 (9)	0.0238 (11)	0.0312 (12)	0.0037 (8)	−0.0046 (8)	−0.0030 (9)
C4B	0.0252 (10)	0.0210 (10)	0.0233 (11)	0.0038 (8)	−0.0083 (8)	−0.0021 (8)
C5B	0.0244 (10)	0.0196 (10)	0.0145 (9)	0.0019 (8)	−0.0023 (8)	0.0003 (8)
C6B	0.0158 (8)	0.0174 (9)	0.0139 (9)	0.0009 (7)	−0.0028 (7)	−0.0034 (7)
C7B	0.0174 (9)	0.0195 (10)	0.0146 (9)	0.0001 (7)	−0.0002 (7)	−0.0018 (8)
C8B	0.0151 (8)	0.0223 (10)	0.0121 (9)	0.0012 (7)	−0.0020 (7)	0.0001 (7)
C9B	0.0174 (9)	0.0223 (10)	0.0154 (9)	−0.0038 (7)	−0.0008 (7)	−0.0009 (8)
C10B	0.0222 (9)	0.0184 (10)	0.0169 (10)	−0.0032 (8)	−0.0003 (8)	0.0015 (8)
C11B	0.0197 (9)	0.0204 (10)	0.0179 (10)	0.0027 (8)	−0.0010 (7)	0.0017 (8)
C12B	0.0136 (8)	0.0210 (10)	0.0134 (9)	−0.0011 (7)	0.0007 (7)	0.0002 (7)
C13B	0.0162 (9)	0.0183 (10)	0.0159 (10)	−0.0013 (7)	−0.0022 (7)	0.0019 (7)
C14B	0.0145 (8)	0.0202 (10)	0.0138 (9)	0.0001 (7)	−0.0002 (7)	0.0001 (7)
C15B	0.0163 (9)	0.0235 (10)	0.0137 (9)	−0.0022 (8)	0.0014 (7)	−0.0048 (8)
C16B	0.0256 (10)	0.0243 (11)	0.0242 (11)	−0.0037 (9)	0.0001 (8)	0.0014 (9)
C17B	0.0333 (12)	0.0316 (13)	0.0379 (14)	−0.0133 (10)	0.0046 (11)	−0.0009 (11)
C18B	0.0209 (11)	0.0450 (15)	0.0462 (16)	−0.0111 (10)	−0.0010 (10)	−0.0063 (13)
C19B	0.0217 (11)	0.0485 (16)	0.0306 (13)	0.0002 (10)	−0.0066 (9)	−0.0002 (11)
C20B	0.0181 (9)	0.0359 (12)	0.0212 (11)	−0.0019 (9)	−0.0020 (8)	0.0044 (9)

O1A—C7A	1.218 (2)	O1B—C7B	1.216 (2)
O2A—C7A	1.352 (2)	O2B—C7B	1.349 (2)
O2A—C8A	1.451 (2)	O2B—C8B	1.457 (2)
O3A—C14A	1.352 (2)	O3B—C14B	1.357 (2)
O3A—C12A	1.453 (2)	O3B—C12B	1.457 (2)
O4A—C14A	1.218 (2)	O4B—C14B	1.215 (2)
N1A—C7A	1.356 (2)	N1B—C7B	1.360 (3)
N1A—C6A	1.414 (3)	N1B—C6B	1.415 (2)
N1A—H1NA	0.83 (2)	N1B—H1NB	0.92 (3)
N2A—C14A	1.354 (3)	N2B—C14B	1.352 (2)
N2A—C15A	1.416 (2)	N2B—C15B	1.418 (2)
N2A—H2NA	0.92 (3)	N2B—H2NB	0.88 (3)
C1A—C2A	1.390 (3)	C1B—C2B	1.390 (3)
C1A—C6A	1.392 (3)	C1B—C6B	1.393 (2)
C1A—H1AA	0.93	C1B—H1BA	0.93
C2A—C3A	1.383 (3)	C2B—C3B	1.387 (3)
C2A—H2AA	0.93	C2B—H2BA	0.93
C3A—C4A	1.383 (3)	C3B—C4B	1.384 (3)
C3A—H3AA	0.93	C3B—H3BA	0.93
C4A—C5A	1.392 (3)	C4B—C5B	1.388 (3)
C4A—H4AA	0.93	C4B—H4BA	0.93
C5A—C6A	1.394 (3)	C5B—C6B	1.400 (3)
C5A—H5AA	0.93	C5B—H5BA	0.93
C8A—C9A	1.517 (3)	C8B—C13B	1.518 (2)
C8A—C13A	1.520 (3)	C8B—C9B	1.520 (3)
C8A—H8AA	0.98	C8B—H8BA	0.98
C9A—C10A	1.532 (3)	C9B—C10B	1.527 (3)
C9A—H9AA	0.97	C9B—H9BA	0.97
C9A—H9AB	0.97	C9B—H9BB	0.97
C10A—C11A	1.530 (3)	C10B—C11B	1.528 (3)
C10A—H10A	0.97	C10B—H10C	0.97
C10A—H10B	0.97	C10B—H10D	0.97
C11A—C12A	1.519 (3)	C11B—C12B	1.515 (3)
C11A—H11A	0.97	C11B—H11C	0.97
C11A—H11B	0.97	C11B—H11D	0.97
C12A—C13A	1.520 (2)	C12B—C13B	1.520 (3)
C12A—H12A	0.98	C12B—H12B	0.98
C13A—H13A	0.97	C13B—H13C	0.97
C13A—H13B	0.97	C13B—H13D	0.97
C15A—C16A	1.390 (3)	C15B—C20B	1.388 (3)
C15A—C20A	1.393 (3)	C15B—C16B	1.390 (3)
C16A—C17A	1.390 (3)	C16B—C17B	1.393 (3)
C16A—H16A	0.93	C16B—H16B	0.93
C17A—C18A	1.389 (3)	C17B—C18B	1.381 (4)
C17A—H17A	0.93	C17B—H17B	0.93
C18A—C19A	1.390 (3)	C18B—C19B	1.375 (3)
C18A—H18A	0.93	C18B—H18B	0.93
C19A—C20A	1.393 (3)	C19B—C20B	1.394 (3)
C19A—H19A	0.93	C19B—H19B	0.93
C20A—H20A	0.93	C20B—H20B	0.93
C7A—O2A—C8A	117.89 (15)	C7B—O2B—C8B	117.06 (14)
C14A—O3A—C12A	117.13 (15)	C14B—O3B—C12B	117.12 (14)
C7A—N1A—C6A	125.41 (18)	C7B—N1B—C6B	127.13 (16)
C7A—N1A—H1NA	112.3 (15)	C7B—N1B—H1NB	116.4 (17)
C6A—N1A—H1NA	121.2 (15)	C6B—N1B—H1NB	116.2 (17)
C14A—N2A—C15A	127.07 (16)	C14B—N2B—C15B	125.39 (18)
C14A—N2A—H2NA	117.3 (18)	C14B—N2B—H2NB	115.7 (16)
C15A—N2A—H2NA	114.6 (18)	C15B—N2B—H2NB	118.8 (16)
C2A—C1A—C6A	119.43 (19)	C2B—C1B—C6B	119.5 (2)
C2A—C1A—H1AA	120.3	C2B—C1B—H1BA	120.2
C6A—C1A—H1AA	120.3	C6B—C1B—H1BA	120.2
C3A—C2A—C1A	120.7 (2)	C3B—C2B—C1B	121.13 (19)
C3A—C2A—H2AA	119.6	C3B—C2B—H2BA	119.4
C1A—C2A—H2AA	119.6	C1B—C2B—H2BA	119.4
C2A—C3A—C4A	119.8 (2)	C4B—C3B—C2B	119.13 (19)
C2A—C3A—H3AA	120.1	C4B—C3B—H3BA	120.4
C4A—C3A—H3AA	120.1	C2B—C3B—H3BA	120.4
C3A—C4A—C5A	120.4 (2)	C3B—C4B—C5B	120.7 (2)
C3A—C4A—H4AA	119.8	C3B—C4B—H4BA	119.6
C5A—C4A—H4AA	119.8	C5B—C4B—H4BA	119.6
C4A—C5A—C6A	119.6 (2)	C4B—C5B—C6B	119.94 (18)
C4A—C5A—H5AA	120.2	C4B—C5B—H5BA	120.0
C6A—C5A—H5AA	120.2	C6B—C5B—H5BA	120.0
C1A—C6A—C5A	120.07 (19)	C1B—C6B—C5B	119.55 (18)
C1A—C6A—N1A	122.74 (18)	C1B—C6B—N1B	123.52 (18)
C5A—C6A—N1A	117.16 (19)	C5B—C6B—N1B	116.87 (16)
O1A—C7A—O2A	124.28 (17)	O1B—C7B—O2B	124.40 (19)
O1A—C7A—N1A	126.79 (19)	O1B—C7B—N1B	126.90 (18)
O2A—C7A—N1A	108.94 (17)	O2B—C7B—N1B	108.70 (15)
O2A—C8A—C9A	110.34 (15)	O2B—C8B—C13B	104.44 (15)
O2A—C8A—C13A	104.39 (15)	O2B—C8B—C9B	111.20 (16)
C9A—C8A—C13A	112.13 (17)	C13B—C8B—C9B	111.45 (15)
O2A—C8A—H8AA	110.0	O2B—C8B—H8BA	109.9
C9A—C8A—H8AA	110.0	C13B—C8B—H8BA	109.9
C13A—C8A—H8AA	110.0	C9B—C8B—H8BA	109.9
C8A—C9A—C10A	110.43 (16)	C8B—C9B—C10B	109.91 (16)
C8A—C9A—H9AA	109.6	C8B—C9B—H9BA	109.7
C10A—C9A—H9AA	109.6	C10B—C9B—H9BA	109.7
C8A—C9A—H9AB	109.6	C8B—C9B—H9BB	109.7
C10A—C9A—H9AB	109.6	C10B—C9B—H9BB	109.7
H9AA—C9A—H9AB	108.1	H9BA—C9B—H9BB	108.2
C11A—C10A—C9A	111.48 (16)	C9B—C10B—C11B	111.69 (16)
C11A—C10A—H10A	109.3	C9B—C10B—H10C	109.3
C9A—C10A—H10A	109.3	C11B—C10B—H10C	109.3
C11A—C10A—H10B	109.3	C9B—C10B—H10D	109.3
C9A—C10A—H10B	109.3	C11B—C10B—H10D	109.3
H10A—C10A—H10B	108.0	H10C—C10B—H10D	107.9
C12A—C11A—C10A	109.87 (17)	C12B—C11B—C10B	109.78 (16)
C12A—C11A—H11A	109.7	C12B—C11B—H11C	109.7
C10A—C11A—H11A	109.7	C10B—C11B—H11C	109.7
C12A—C11A—H11B	109.7	C12B—C11B—H11D	109.7
C10A—C11A—H11B	109.7	C10B—C11B—H11D	109.7
H11A—C11A—H11B	108.2	H11C—C11B—H11D	108.2
O3A—C12A—C11A	111.31 (16)	O3B—C12B—C11B	110.74 (15)
O3A—C12A—C13A	104.54 (15)	O3B—C12B—C13B	103.88 (14)
C11A—C12A—C13A	111.63 (16)	C11B—C12B—C13B	112.44 (16)
O3A—C12A—H12A	109.7	O3B—C12B—H12B	109.9
C11A—C12A—H12A	109.7	C11B—C12B—H12B	109.9
C13A—C12A—H12A	109.7	C13B—C12B—H12B	109.9
C12A—C13A—C8A	111.94 (16)	C8B—C13B—C12B	112.05 (16)
C12A—C13A—H13A	109.2	C8B—C13B—H13C	109.2
C8A—C13A—H13A	109.2	C12B—C13B—H13C	109.2
C12A—C13A—H13B	109.2	C8B—C13B—H13D	109.2
C8A—C13A—H13B	109.2	C12B—C13B—H13D	109.2
H13A—C13A—H13B	107.9	H13C—C13B—H13D	107.9
O4A—C14A—O3A	124.35 (19)	O4B—C14B—N2B	127.10 (19)
O4A—C14A—N2A	126.63 (18)	O4B—C14B—O3B	124.41 (16)
O3A—C14A—N2A	109.01 (16)	N2B—C14B—O3B	108.48 (16)
C16A—C15A—C20A	119.49 (18)	C20B—C15B—C16B	119.92 (19)
C16A—C15A—N2A	117.55 (17)	C20B—C15B—N2B	122.74 (18)
C20A—C15A—N2A	122.91 (19)	C16B—C15B—N2B	117.30 (19)
C17A—C16A—C15A	120.56 (19)	C15B—C16B—C17B	119.9 (2)
C17A—C16A—H16A	119.7	C15B—C16B—H16B	120.1
C15A—C16A—H16A	119.7	C17B—C16B—H16B	120.1
C18A—C17A—C16A	120.3 (2)	C18B—C17B—C16B	120.0 (2)
C18A—C17A—H17A	119.9	C18B—C17B—H17B	120.0
C16A—C17A—H17A	119.9	C16B—C17B—H17B	120.0
C17A—C18A—C19A	119.06 (19)	C19B—C18B—C17B	120.0 (2)
C17A—C18A—H18A	120.5	C19B—C18B—H18B	120.0
C19A—C18A—H18A	120.5	C17B—C18B—H18B	120.0
C18A—C19A—C20A	121.02 (19)	C18B—C19B—C20B	120.6 (2)
C18A—C19A—H19A	119.5	C18B—C19B—H19B	119.7
C20A—C19A—H19A	119.5	C20B—C19B—H19B	119.7
C15A—C20A—C19A	119.6 (2)	C15B—C20B—C19B	119.5 (2)
C15A—C20A—H20A	120.2	C15B—C20B—H20B	120.3
C19A—C20A—H20A	120.2	C19B—C20B—H20B	120.3
C6A—C1A—C2A—C3A	−0.6 (3)	C6B—C1B—C2B—C3B	0.5 (3)
C1A—C2A—C3A—C4A	−0.7 (3)	C1B—C2B—C3B—C4B	−0.4 (3)
C2A—C3A—C4A—C5A	1.2 (4)	C2B—C3B—C4B—C5B	0.1 (3)
C3A—C4A—C5A—C6A	−0.3 (3)	C3B—C4B—C5B—C6B	0.1 (3)
C2A—C1A—C6A—C5A	1.5 (3)	C2B—C1B—C6B—C5B	−0.3 (3)
C2A—C1A—C6A—N1A	179.8 (2)	C2B—C1B—C6B—N1B	−177.38 (19)
C4A—C5A—C6A—C1A	−1.1 (3)	C4B—C5B—C6B—C1B	0.0 (3)
C4A—C5A—C6A—N1A	−179.5 (2)	C4B—C5B—C6B—N1B	177.30 (18)
C7A—N1A—C6A—C1A	34.4 (3)	C7B—N1B—C6B—C1B	−18.0 (3)
C7A—N1A—C6A—C5A	−147.2 (2)	C7B—N1B—C6B—C5B	164.83 (19)
C8A—O2A—C7A—O1A	−7.5 (3)	C8B—O2B—C7B—O1B	−1.0 (3)
C8A—O2A—C7A—N1A	172.67 (16)	C8B—O2B—C7B—N1B	178.74 (16)
C6A—N1A—C7A—O1A	−5.5 (3)	C6B—N1B—C7B—O1B	−3.8 (3)
C6A—N1A—C7A—O2A	174.33 (18)	C6B—N1B—C7B—O2B	176.52 (18)
C7A—O2A—C8A—C9A	99.4 (2)	C7B—O2B—C8B—C13B	−157.19 (16)
C7A—O2A—C8A—C13A	−139.95 (17)	C7B—O2B—C8B—C9B	82.5 (2)
O2A—C8A—C9A—C10A	169.92 (16)	O2B—C8B—C9B—C10B	171.80 (14)
C13A—C8A—C9A—C10A	54.0 (2)	C13B—C8B—C9B—C10B	55.7 (2)
C8A—C9A—C10A—C11A	−56.4 (2)	C8B—C9B—C10B—C11B	−57.9 (2)
C9A—C10A—C11A—C12A	57.4 (2)	C9B—C10B—C11B—C12B	57.0 (2)
C14A—O3A—C12A—C11A	−83.1 (2)	C14B—O3B—C12B—C11B	−93.5 (2)
C14A—O3A—C12A—C13A	156.25 (17)	C14B—O3B—C12B—C13B	145.54 (16)
C10A—C11A—C12A—O3A	−172.51 (14)	C10B—C11B—C12B—O3B	−170.03 (15)
C10A—C11A—C12A—C13A	−56.1 (2)	C10B—C11B—C12B—C13B	−54.3 (2)
O3A—C12A—C13A—C8A	174.99 (15)	O2B—C8B—C13B—C12B	−174.04 (15)
C11A—C12A—C13A—C8A	54.5 (2)	C9B—C8B—C13B—C12B	−53.9 (2)
O2A—C8A—C13A—C12A	−172.95 (15)	O3B—C12B—C13B—C8B	173.31 (15)
C9A—C8A—C13A—C12A	−53.5 (2)	C11B—C12B—C13B—C8B	53.5 (2)
C12A—O3A—C14A—O4A	0.2 (3)	C15B—N2B—C14B—O4B	3.0 (3)
C12A—O3A—C14A—N2A	−178.81 (16)	C15B—N2B—C14B—O3B	−177.74 (18)
C15A—N2A—C14A—O4A	5.8 (4)	C12B—O3B—C14B—O4B	9.2 (3)
C15A—N2A—C14A—O3A	−175.19 (18)	C12B—O3B—C14B—N2B	−170.07 (16)
C14A—N2A—C15A—C16A	−165.8 (2)	C14B—N2B—C15B—C20B	33.7 (3)
C14A—N2A—C15A—C20A	16.8 (3)	C14B—N2B—C15B—C16B	−148.7 (2)
C20A—C15A—C16A—C17A	1.4 (3)	C20B—C15B—C16B—C17B	0.8 (3)
N2A—C15A—C16A—C17A	−176.11 (19)	N2B—C15B—C16B—C17B	−176.9 (2)
C15A—C16A—C17A—C18A	−1.0 (3)	C15B—C16B—C17B—C18B	−1.9 (4)
C16A—C17A—C18A—C19A	−0.5 (3)	C16B—C17B—C18B—C19B	1.3 (4)
C17A—C18A—C19A—C20A	1.5 (3)	C17B—C18B—C19B—C20B	0.3 (4)
C16A—C15A—C20A—C19A	−0.4 (3)	C16B—C15B—C20B—C19B	0.8 (3)
N2A—C15A—C20A—C19A	176.97 (19)	N2B—C15B—C20B—C19B	178.4 (2)
C18A—C19A—C20A—C15A	−1.1 (3)	C18B—C19B—C20B—C15B	−1.4 (4)

Cg1 and Cg2 are the centroids of C15A–C20A and C1B–C6B phenyl rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···O1Ai	0.83 (2)	2.13 (2)	2.953 (2)	174 (2)
N2A—H2NA···O4Ai	0.91 (3)	2.09 (3)	2.934 (2)	154 (2)
N1B—H1NB···O1Bii	0.93 (3)	2.10 (3)	2.920 (2)	147 (2)
N2B—H2NB···O4Bii	0.88 (3)	2.02 (3)	2.874 (2)	163 (3)
C13A—H13B···Cg1iii	0.97	2.86	3.734 (2)	151
C13B—H13C···Cg2iv	0.97	2.86	3.732 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of C15A–C20A and C1B–C6B phenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1NA⋯O1Ai	0.83 (2)	2.13 (2)	2.953 (2)	174 (2)
N2A—H2NA⋯O4Ai	0.91 (3)	2.09 (3)	2.934 (2)	154 (2)
N1B—H1NB⋯O1Bii	0.93 (3)	2.10 (3)	2.920 (2)	147 (2)
N2B—H2NB⋯O4Bii	0.88 (3)	2.02 (3)	2.874 (2)	163 (3)
C13A—H13B⋯Cg1iii	0.97	2.86	3.734 (2)	151
C13B—H13C⋯Cg2iv	0.97	2.86	3.732 (2)	150

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .