3-(2-Amino-5-nitro-anilino)-5,5-dimethyl-cyclo-hex-2-en-1-one 0.25-hydrate.

The asymmetric unit of the title compound, C(14)H(17)N(3)O(3)·0.25H(2)O, comprises two independent organic mol-ecules and a water mol-ecule lying on a crystallographic twofold rotation axis with 50% site occupancy. In both independent mol-ecules, the cyclo-hexene rings adopt envelope conformations but superposition of the two molecules shows that the flap atoms point in opposite directions. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds inter-connect adjacent mol-ecules into a three-dimensional network. Weak inter-molecular π-π aromatic stacking inter-actions [centroid-centroid distances = 3.4985 (9) and 3.6630 (9) Å] are also observed.

Related literature

For general background to (2-amino­phen­yl)amino­cyclo­hexene derivatives, see: Cortés et al. (2004 ▶); Tonkikh et al. (2004 ▶). For ring conformations and puckering analysis, see: Cremer & Pople (1975 ▶). For related structures, see: Ghalib et al. (2010 ▶); Mehdi et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C14H17N3O3·0.25H2O

M = 279.81

Monoclinic,

a = 18.9043 (1) Å

b = 16.7048 (1) Å

c = 17.8806 (2) Å

β = 102.443 (1)°

V = 5513.93 (8) Å3

Z = 16

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.36 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.966, T max = 0.991

58072 measured reflections

8086 independent reflections

5448 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.135

S = 1.06

8086 reflections

398 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.28 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/S1600536810033933/ci5160sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033933/ci5160Isup2.hkl

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

C14H17N3O3·0.25H2O	F(000) = 2376
Mr = 279.81	Dx = 1.348 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6071 reflections
a = 18.9043 (1) Å	θ = 2.2–24.2°
b = 16.7048 (1) Å	µ = 0.10 mm−1
c = 17.8806 (2) Å	T = 100 K
β = 102.443 (1)°	Needle, orange
V = 5513.93 (8) Å3	0.36 × 0.10 × 0.10 mm
Z = 16

Bruker SMART APEXII CCD area-detector diffractometer	8086 independent reflections
Radiation source: fine-focus sealed tube	5448 reflections with I > 2σ(I)
graphite	Rint = 0.072
φ and ω scans	θmax = 30.1°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −26→26
Tmin = 0.966, Tmax = 0.991	k = −23→23
58072 measured reflections	l = −25→25

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0547P)2 + 2.5234P] where P = (Fo2 + 2Fc2)/3
8086 reflections	(Δ/σ)max = 0.001
398 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.28 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	0.10407 (6)	0.88026 (7)	1.18606 (6)	0.0250 (2)
O2A	−0.00894 (8)	0.63989 (8)	0.87992 (10)	0.0560 (4)
O3A	−0.10784 (7)	0.66814 (8)	0.79713 (7)	0.0428 (3)
N1A	0.12683 (7)	0.89926 (8)	0.92807 (7)	0.0233 (3)
N2A	−0.04981 (8)	0.68814 (9)	0.83987 (9)	0.0345 (3)
N3A	0.02428 (8)	1.01243 (9)	0.86062 (9)	0.0296 (3)
C1A	0.03700 (8)	0.79493 (10)	0.88679 (9)	0.0247 (3)
H1AA	0.0693	0.7567	0.9120	0.030*
C2A	−0.03046 (9)	0.77211 (10)	0.84420 (9)	0.0261 (3)
C3A	−0.07831 (8)	0.82840 (10)	0.80490 (9)	0.0263 (3)
H3AA	−0.1221	0.8121	0.7742	0.032*
C4A	−0.06102 (8)	0.90791 (10)	0.81135 (9)	0.0260 (3)
H4AA	−0.0940	0.9455	0.7862	0.031*
C5A	0.00592 (8)	0.93374 (9)	0.85545 (8)	0.0226 (3)
C6A	0.05544 (8)	0.87464 (9)	0.89116 (8)	0.0213 (3)
C7A	0.15228 (8)	0.90426 (9)	1.00454 (8)	0.0211 (3)
C8A	0.22892 (8)	0.93365 (10)	1.02831 (9)	0.0240 (3)
H8AA	0.2287	0.9917	1.0291	0.029*
H8AB	0.2557	0.9168	0.9905	0.029*
C9A	0.26804 (8)	0.90297 (10)	1.10715 (9)	0.0237 (3)
C10A	0.21925 (8)	0.91886 (10)	1.16357 (9)	0.0264 (3)
H10A	0.2395	0.8914	1.2112	0.032*
H10B	0.2201	0.9758	1.1745	0.032*
C11A	0.14128 (8)	0.89301 (9)	1.13669 (9)	0.0219 (3)
C12A	0.11152 (8)	0.88643 (9)	1.05722 (8)	0.0219 (3)
H12A	0.0638	0.8698	1.0405	0.026*
C13A	0.33996 (9)	0.94785 (11)	1.13176 (10)	0.0305 (4)
H13A	0.3308	1.0043	1.1327	0.046*
H13B	0.3701	0.9370	1.0960	0.046*
H13C	0.3641	0.9304	1.1819	0.046*
C14A	0.28313 (9)	0.81308 (10)	1.10315 (10)	0.0324 (4)
H14A	0.3104	0.7951	1.1519	0.049*
H14B	0.3104	0.8034	1.0645	0.049*
H14C	0.2381	0.7845	1.0905	0.049*
O1B	0.23010 (6)	0.05262 (7)	0.34053 (6)	0.0273 (3)
O2B	0.12655 (7)	0.09396 (7)	0.01137 (7)	0.0373 (3)
O3B	0.06840 (7)	0.19146 (8)	−0.05509 (7)	0.0393 (3)
N1B	0.34019 (7)	0.22183 (8)	0.18568 (8)	0.0239 (3)
N2B	0.11744 (8)	0.16604 (9)	−0.00325 (8)	0.0299 (3)
N3B	0.31623 (8)	0.38637 (9)	0.15638 (8)	0.0262 (3)
C1B	0.22746 (8)	0.19536 (10)	0.09317 (9)	0.0247 (3)
H1BA	0.2346	0.1407	0.1010	0.030*
C2B	0.16734 (8)	0.22303 (10)	0.04083 (9)	0.0250 (3)
C3B	0.15569 (9)	0.30448 (10)	0.02732 (9)	0.0276 (3)
H3BA	0.1150	0.3224	−0.0076	0.033*
C4B	0.20513 (9)	0.35776 (10)	0.06638 (9)	0.0264 (3)
H4BA	0.1980	0.4122	0.0569	0.032*
C5B	0.26681 (8)	0.33224 (9)	0.12075 (8)	0.0234 (3)
C6B	0.27680 (8)	0.24929 (9)	0.13365 (9)	0.0231 (3)
C7B	0.34175 (8)	0.16652 (9)	0.24196 (9)	0.0220 (3)
C8B	0.41600 (8)	0.13787 (9)	0.28068 (9)	0.0243 (3)
H8BA	0.4500	0.1816	0.2823	0.029*
H8BB	0.4304	0.0954	0.2501	0.029*
C9B	0.42129 (8)	0.10673 (9)	0.36246 (9)	0.0243 (3)
C10B	0.35921 (9)	0.04699 (9)	0.36023 (9)	0.0259 (3)
H10C	0.3693	−0.0011	0.3339	0.031*
H10D	0.3578	0.0321	0.4123	0.031*
C11B	0.28568 (8)	0.07847 (9)	0.32102 (9)	0.0237 (3)
C12B	0.28102 (8)	0.13614 (10)	0.26177 (9)	0.0252 (3)
H12B	0.2357	0.1537	0.2358	0.030*
C13B	0.41499 (10)	0.17608 (11)	0.41657 (10)	0.0330 (4)
H13D	0.4195	0.1559	0.4677	0.049*
H13E	0.3687	0.2016	0.4002	0.049*
H13F	0.4528	0.2142	0.4158	0.049*
C14B	0.49440 (9)	0.06534 (11)	0.38949 (10)	0.0324 (4)
H14D	0.4997	0.0491	0.4419	0.049*
H14E	0.5326	0.1018	0.3853	0.049*
H14F	0.4968	0.0191	0.3582	0.049*
O1W	0.0000	0.80007 (11)	0.2500	0.0446 (5)
H1W1	0.0200 (13)	0.8311 (14)	0.2244 (13)	0.055 (7)*
H1NA	0.1562 (11)	0.9117 (12)	0.8972 (11)	0.037 (5)*
H2NA	−0.0127 (12)	1.0468 (13)	0.8460 (12)	0.047 (6)*
H3NA	0.0637 (11)	1.0285 (12)	0.8965 (11)	0.037 (5)*
H1NB	0.3824 (12)	0.2453 (13)	0.1855 (12)	0.047 (6)*
H2NB	0.3020 (11)	0.4365 (13)	0.1504 (11)	0.035 (5)*
H3NB	0.3455 (10)	0.3735 (11)	0.1998 (11)	0.030 (5)*

	U11	U22	U33	U12	U13	U23
O1A	0.0203 (5)	0.0317 (6)	0.0243 (5)	−0.0009 (4)	0.0073 (4)	0.0030 (4)
O2A	0.0471 (9)	0.0294 (8)	0.0832 (11)	0.0007 (7)	−0.0043 (8)	0.0026 (7)
O3A	0.0422 (8)	0.0446 (8)	0.0392 (7)	−0.0179 (6)	0.0038 (6)	−0.0100 (6)
N1A	0.0159 (6)	0.0323 (7)	0.0212 (6)	−0.0010 (5)	0.0031 (5)	0.0040 (5)
N2A	0.0322 (8)	0.0323 (8)	0.0385 (8)	−0.0055 (6)	0.0067 (7)	−0.0054 (6)
N3A	0.0222 (7)	0.0276 (8)	0.0365 (8)	0.0030 (6)	0.0010 (6)	0.0021 (6)
C1A	0.0213 (8)	0.0273 (8)	0.0256 (8)	0.0027 (6)	0.0056 (6)	0.0010 (6)
C2A	0.0235 (8)	0.0288 (8)	0.0266 (8)	−0.0029 (6)	0.0069 (6)	−0.0049 (6)
C3A	0.0180 (7)	0.0374 (9)	0.0228 (8)	−0.0009 (6)	0.0026 (6)	−0.0036 (6)
C4A	0.0199 (8)	0.0328 (9)	0.0242 (8)	0.0054 (6)	0.0026 (6)	0.0026 (6)
C5A	0.0190 (7)	0.0287 (8)	0.0203 (7)	0.0017 (6)	0.0049 (6)	0.0015 (6)
C6A	0.0162 (7)	0.0292 (8)	0.0183 (7)	−0.0001 (6)	0.0031 (5)	−0.0004 (6)
C7A	0.0167 (7)	0.0223 (7)	0.0234 (7)	0.0013 (6)	0.0022 (6)	0.0017 (6)
C8A	0.0169 (7)	0.0301 (8)	0.0252 (8)	−0.0026 (6)	0.0050 (6)	0.0022 (6)
C9A	0.0168 (7)	0.0306 (8)	0.0229 (7)	−0.0009 (6)	0.0025 (6)	0.0020 (6)
C10A	0.0196 (8)	0.0359 (9)	0.0234 (8)	−0.0052 (7)	0.0039 (6)	−0.0014 (6)
C11A	0.0183 (7)	0.0221 (8)	0.0256 (8)	0.0019 (6)	0.0054 (6)	0.0019 (6)
C12A	0.0151 (7)	0.0243 (8)	0.0259 (8)	−0.0010 (6)	0.0035 (6)	0.0017 (6)
C13A	0.0175 (8)	0.0447 (10)	0.0277 (8)	−0.0059 (7)	0.0016 (6)	−0.0023 (7)
C14A	0.0227 (8)	0.0339 (10)	0.0394 (10)	0.0035 (7)	0.0038 (7)	0.0039 (7)
O1B	0.0259 (6)	0.0278 (6)	0.0315 (6)	−0.0050 (5)	0.0136 (5)	−0.0037 (5)
O2B	0.0386 (7)	0.0312 (7)	0.0390 (7)	−0.0043 (5)	0.0018 (6)	0.0000 (5)
O3B	0.0266 (7)	0.0449 (8)	0.0406 (7)	0.0076 (6)	−0.0053 (5)	−0.0044 (6)
N1B	0.0192 (7)	0.0240 (7)	0.0290 (7)	−0.0004 (5)	0.0064 (5)	0.0032 (5)
N2B	0.0255 (7)	0.0338 (8)	0.0303 (7)	0.0007 (6)	0.0058 (6)	−0.0026 (6)
N3B	0.0298 (8)	0.0226 (7)	0.0254 (7)	0.0016 (6)	0.0042 (6)	0.0010 (5)
C1B	0.0250 (8)	0.0233 (8)	0.0273 (8)	0.0023 (6)	0.0090 (6)	0.0003 (6)
C2B	0.0223 (8)	0.0306 (8)	0.0228 (8)	0.0006 (6)	0.0066 (6)	−0.0023 (6)
C3B	0.0264 (8)	0.0332 (9)	0.0236 (8)	0.0072 (7)	0.0060 (6)	0.0010 (6)
C4B	0.0307 (9)	0.0249 (8)	0.0246 (8)	0.0059 (7)	0.0081 (7)	0.0015 (6)
C5B	0.0251 (8)	0.0249 (8)	0.0219 (7)	0.0014 (6)	0.0090 (6)	−0.0011 (6)
C6B	0.0211 (7)	0.0259 (8)	0.0233 (7)	0.0026 (6)	0.0068 (6)	0.0008 (6)
C7B	0.0216 (7)	0.0196 (7)	0.0255 (8)	0.0014 (6)	0.0066 (6)	−0.0004 (6)
C8B	0.0188 (7)	0.0232 (8)	0.0319 (8)	−0.0004 (6)	0.0075 (6)	0.0021 (6)
C9B	0.0218 (8)	0.0217 (8)	0.0291 (8)	0.0004 (6)	0.0054 (6)	0.0024 (6)
C10B	0.0263 (8)	0.0224 (8)	0.0301 (8)	−0.0015 (6)	0.0082 (7)	0.0012 (6)
C11B	0.0232 (8)	0.0229 (8)	0.0266 (8)	−0.0034 (6)	0.0090 (6)	−0.0058 (6)
C12B	0.0189 (7)	0.0277 (8)	0.0295 (8)	0.0015 (6)	0.0065 (6)	0.0015 (6)
C13B	0.0299 (9)	0.0326 (9)	0.0357 (9)	−0.0025 (7)	0.0055 (7)	−0.0053 (7)
C14B	0.0252 (9)	0.0332 (9)	0.0382 (10)	0.0021 (7)	0.0054 (7)	0.0070 (7)
O1W	0.0529 (12)	0.0203 (9)	0.0751 (15)	0.000	0.0454 (12)	0.000

O1A—C11A	1.2597 (17)	O2B—N2B	1.2363 (18)
O2A—N2A	1.233 (2)	O3B—N2B	1.2363 (18)
O3A—N2A	1.2400 (19)	N1B—C7B	1.3617 (19)
N1A—C7A	1.3507 (19)	N1B—C6B	1.425 (2)
N1A—C6A	1.4290 (19)	N1B—H1NB	0.89 (2)
N1A—H1NA	0.89 (2)	N2B—C2B	1.448 (2)
N2A—C2A	1.448 (2)	N3B—C5B	1.357 (2)
N3A—C5A	1.358 (2)	N3B—H2NB	0.88 (2)
N3A—H2NA	0.90 (2)	N3B—H3NB	0.88 (2)
N3A—H3NA	0.91 (2)	C1B—C6B	1.384 (2)
C1A—C6A	1.374 (2)	C1B—C2B	1.387 (2)
C1A—C2A	1.390 (2)	C1B—H1BA	0.93
C1A—H1AA	0.93	C2B—C3B	1.391 (2)
C2A—C3A	1.387 (2)	C3B—C4B	1.368 (2)
C3A—C4A	1.367 (2)	C3B—H3BA	0.93
C3A—H3AA	0.93	C4B—C5B	1.413 (2)
C4A—C5A	1.407 (2)	C4B—H4BA	0.93
C4A—H4AA	0.93	C5B—C6B	1.411 (2)
C5A—C6A	1.415 (2)	C7B—C12B	1.370 (2)
C7A—C12A	1.372 (2)	C7B—C8B	1.503 (2)
C7A—C8A	1.502 (2)	C8B—C9B	1.535 (2)
C8A—C9A	1.532 (2)	C8B—H8BA	0.97
C8A—H8AA	0.97	C8B—H8BB	0.97
C8A—H8AB	0.97	C9B—C14B	1.528 (2)
C9A—C10A	1.530 (2)	C9B—C13B	1.530 (2)
C9A—C13A	1.532 (2)	C9B—C10B	1.534 (2)
C9A—C14A	1.533 (2)	C10B—C11B	1.510 (2)
C10A—C11A	1.511 (2)	C10B—H10C	0.97
C10A—H10A	0.97	C10B—H10D	0.97
C10A—H10B	0.97	C11B—C12B	1.420 (2)
C11A—C12A	1.415 (2)	C12B—H12B	0.93
C12A—H12A	0.93	C13B—H13D	0.96
C13A—H13A	0.96	C13B—H13E	0.96
C13A—H13B	0.96	C13B—H13F	0.96
C13A—H13C	0.96	C14B—H14D	0.96
C14A—H14A	0.96	C14B—H14E	0.96
C14A—H14B	0.96	C14B—H14F	0.96
C14A—H14C	0.96	O1W—H1W1	0.83 (2)
O1B—C11B	1.2531 (18)
C7A—N1A—C6A	125.48 (13)	C7B—N1B—C6B	125.59 (13)
C7A—N1A—H1NA	118.7 (13)	C7B—N1B—H1NB	115.2 (14)
C6A—N1A—H1NA	115.8 (13)	C6B—N1B—H1NB	119.0 (14)
O2A—N2A—O3A	122.83 (16)	O2B—N2B—O3B	122.74 (14)
O2A—N2A—C2A	118.86 (15)	O2B—N2B—C2B	118.71 (14)
O3A—N2A—C2A	118.29 (15)	O3B—N2B—C2B	118.52 (14)
C5A—N3A—H2NA	115.3 (14)	C5B—N3B—H2NB	114.6 (13)
C5A—N3A—H3NA	119.4 (12)	C5B—N3B—H3NB	119.5 (12)
H2NA—N3A—H3NA	118.9 (19)	H2NB—N3B—H3NB	117.3 (18)
C6A—C1A—C2A	119.23 (15)	C6B—C1B—C2B	119.88 (15)
C6A—C1A—H1AA	120.4	C6B—C1B—H1BA	120.1
C2A—C1A—H1AA	120.4	C2B—C1B—H1BA	120.1
C3A—C2A—C1A	120.86 (15)	C1B—C2B—C3B	121.28 (15)
C3A—C2A—N2A	120.02 (15)	C1B—C2B—N2B	119.42 (15)
C1A—C2A—N2A	119.11 (15)	C3B—C2B—N2B	119.23 (14)
C4A—C3A—C2A	119.89 (15)	C4B—C3B—C2B	118.85 (15)
C4A—C3A—H3AA	120.1	C4B—C3B—H3BA	120.6
C2A—C3A—H3AA	120.1	C2B—C3B—H3BA	120.6
C3A—C4A—C5A	121.00 (15)	C3B—C4B—C5B	121.77 (15)
C3A—C4A—H4AA	119.5	C3B—C4B—H4BA	119.1
C5A—C4A—H4AA	119.5	C5B—C4B—H4BA	119.1
N3A—C5A—C4A	121.40 (15)	N3B—C5B—C6B	121.57 (15)
N3A—C5A—C6A	120.68 (14)	N3B—C5B—C4B	120.31 (15)
C4A—C5A—C6A	117.83 (14)	C6B—C5B—C4B	118.05 (14)
C1A—C6A—C5A	121.02 (14)	C1B—C6B—C5B	120.16 (14)
C1A—C6A—N1A	120.51 (14)	C1B—C6B—N1B	120.61 (14)
C5A—C6A—N1A	118.36 (14)	C5B—C6B—N1B	119.14 (14)
N1A—C7A—C12A	123.45 (14)	N1B—C7B—C12B	123.83 (14)
N1A—C7A—C8A	114.73 (13)	N1B—C7B—C8B	115.19 (13)
C12A—C7A—C8A	121.79 (13)	C12B—C7B—C8B	120.95 (14)
C7A—C8A—C9A	113.34 (12)	C7B—C8B—C9B	114.16 (12)
C7A—C8A—H8AA	108.9	C7B—C8B—H8BA	108.7
C9A—C8A—H8AA	108.9	C9B—C8B—H8BA	108.7
C7A—C8A—H8AB	108.9	C7B—C8B—H8BB	108.7
C9A—C8A—H8AB	108.9	C9B—C8B—H8BB	108.7
H8AA—C8A—H8AB	107.7	H8BA—C8B—H8BB	107.6
C10A—C9A—C13A	110.46 (13)	C14B—C9B—C13B	109.32 (14)
C10A—C9A—C8A	107.98 (12)	C14B—C9B—C10B	110.40 (13)
C13A—C9A—C8A	108.86 (13)	C13B—C9B—C10B	110.22 (13)
C10A—C9A—C14A	110.21 (13)	C14B—C9B—C8B	108.88 (13)
C13A—C9A—C14A	109.28 (13)	C13B—C9B—C8B	110.36 (13)
C8A—C9A—C14A	110.03 (13)	C10B—C9B—C8B	107.65 (13)
C11A—C10A—C9A	115.21 (13)	C11B—C10B—C9B	114.07 (13)
C11A—C10A—H10A	108.5	C11B—C10B—H10C	108.7
C9A—C10A—H10A	108.5	C9B—C10B—H10C	108.7
C11A—C10A—H10B	108.5	C11B—C10B—H10D	108.7
C9A—C10A—H10B	108.5	C9B—C10B—H10D	108.7
H10A—C10A—H10B	107.5	H10C—C10B—H10D	107.6
O1A—C11A—C12A	121.95 (14)	O1B—C11B—C12B	121.36 (15)
O1A—C11A—C10A	118.62 (13)	O1B—C11B—C10B	119.60 (14)
C12A—C11A—C10A	119.40 (13)	C12B—C11B—C10B	119.04 (13)
C7A—C12A—C11A	120.79 (14)	C7B—C12B—C11B	121.56 (15)
C7A—C12A—H12A	119.6	C7B—C12B—H12B	119.2
C11A—C12A—H12A	119.6	C11B—C12B—H12B	119.2
C9A—C13A—H13A	109.5	C9B—C13B—H13D	109.5
C9A—C13A—H13B	109.5	C9B—C13B—H13E	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
C9A—C13A—H13C	109.5	C9B—C13B—H13F	109.5
H13A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13B—C13A—H13C	109.5	H13E—C13B—H13F	109.5
C9A—C14A—H14A	109.5	C9B—C14B—H14D	109.5
C9A—C14A—H14B	109.5	C9B—C14B—H14E	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
C9A—C14A—H14C	109.5	C9B—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5
C6A—C1A—C2A—C3A	1.5 (2)	C6B—C1B—C2B—C3B	0.7 (2)
C6A—C1A—C2A—N2A	−179.83 (14)	C6B—C1B—C2B—N2B	177.76 (13)
O2A—N2A—C2A—C3A	−174.43 (16)	O2B—N2B—C2B—C1B	5.8 (2)
O3A—N2A—C2A—C3A	4.0 (2)	O3B—N2B—C2B—C1B	−172.66 (14)
O2A—N2A—C2A—C1A	6.9 (2)	O2B—N2B—C2B—C3B	−177.04 (14)
O3A—N2A—C2A—C1A	−174.71 (14)	O3B—N2B—C2B—C3B	4.5 (2)
C1A—C2A—C3A—C4A	−3.8 (2)	C1B—C2B—C3B—C4B	0.5 (2)
N2A—C2A—C3A—C4A	177.60 (14)	N2B—C2B—C3B—C4B	−176.64 (14)
C2A—C3A—C4A—C5A	2.1 (2)	C2B—C3B—C4B—C5B	−1.1 (2)
C3A—C4A—C5A—N3A	178.34 (15)	C3B—C4B—C5B—N3B	177.49 (14)
C3A—C4A—C5A—C6A	1.7 (2)	C3B—C4B—C5B—C6B	0.5 (2)
C2A—C1A—C6A—C5A	2.4 (2)	C2B—C1B—C6B—C5B	−1.2 (2)
C2A—C1A—C6A—N1A	−173.81 (13)	C2B—C1B—C6B—N1B	−177.79 (13)
N3A—C5A—C6A—C1A	179.38 (14)	N3B—C5B—C6B—C1B	−176.31 (14)
C4A—C5A—C6A—C1A	−3.9 (2)	C4B—C5B—C6B—C1B	0.6 (2)
N3A—C5A—C6A—N1A	−4.4 (2)	N3B—C5B—C6B—N1B	0.3 (2)
C4A—C5A—C6A—N1A	172.33 (13)	C4B—C5B—C6B—N1B	177.25 (13)
C7A—N1A—C6A—C1A	−77.9 (2)	C7B—N1B—C6B—C1B	−50.4 (2)
C7A—N1A—C6A—C5A	105.78 (17)	C7B—N1B—C6B—C5B	133.02 (16)
C6A—N1A—C7A—C12A	−0.5 (2)	C6B—N1B—C7B—C12B	−7.7 (2)
C6A—N1A—C7A—C8A	−178.66 (14)	C6B—N1B—C7B—C8B	170.43 (14)
N1A—C7A—C8A—C9A	−152.68 (14)	N1B—C7B—C8B—C9B	154.69 (13)
C12A—C7A—C8A—C9A	29.1 (2)	C12B—C7B—C8B—C9B	−27.1 (2)
C7A—C8A—C9A—C10A	−50.05 (18)	C7B—C8B—C9B—C14B	169.43 (13)
C7A—C8A—C9A—C13A	−170.00 (13)	C7B—C8B—C9B—C13B	−70.59 (17)
C7A—C8A—C9A—C14A	70.27 (17)	C7B—C8B—C9B—C10B	49.73 (17)
C13A—C9A—C10A—C11A	167.20 (14)	C14B—C9B—C10B—C11B	−169.64 (13)
C8A—C9A—C10A—C11A	48.27 (18)	C13B—C9B—C10B—C11B	69.49 (17)
C14A—C9A—C10A—C11A	−71.94 (18)	C8B—C9B—C10B—C11B	−50.92 (17)
C9A—C10A—C11A—O1A	157.90 (14)	C9B—C10B—C11B—O1B	−151.53 (14)
C9A—C10A—C11A—C12A	−24.2 (2)	C9B—C10B—C11B—C12B	29.4 (2)
N1A—C7A—C12A—C11A	−179.87 (14)	N1B—C7B—C12B—C11B	−179.99 (14)
C8A—C7A—C12A—C11A	−1.8 (2)	C8B—C7B—C12B—C11B	2.0 (2)
O1A—C11A—C12A—C7A	176.94 (14)	O1B—C11B—C12B—C7B	177.82 (14)
C10A—C11A—C12A—C7A	−0.9 (2)	C10B—C11B—C12B—C7B	−3.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···O1Bi	0.89 (2)	1.99 (2)	2.8678 (17)	172 (2)
N3A—H2NA···O1Aii	0.90 (2)	2.09 (2)	2.9874 (19)	176 (2)
N3A—H3NA···O2Biii	0.91 (2)	2.40 (2)	3.258 (2)	156 (2)
N1B—H1NB···O1Wiv	0.89 (2)	2.45 (2)	3.2651 (15)	152 (2)
N3B—H2NB···O1Bv	0.88 (2)	2.05 (2)	2.9161 (19)	169 (2)
N3B—H3NB···O1Avi	0.88 (2)	2.06 (2)	2.8963 (18)	159 (2)
C8A—H8AA···O2Biii	0.97	2.55	3.280 (2)	132
C8B—H8BA···O1Wiv	0.97	2.32	3.247 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1NA⋯O1Bi	0.89 (2)	1.99 (2)	2.8678 (17)	172 (2)
N3A—H2NA⋯O1Aii	0.90 (2)	2.09 (2)	2.9874 (19)	176 (2)
N3A—H3NA⋯O2Biii	0.91 (2)	2.40 (2)	3.258 (2)	156 (2)
N1B—H1NB⋯O1Wiv	0.89 (2)	2.45 (2)	3.2651 (15)	152 (2)
N3B—H2NB⋯O1Bv	0.88 (2)	2.05 (2)	2.9161 (19)	169 (2)
N3B—H3NB⋯O1Avi	0.88 (2)	2.06 (2)	2.8963 (18)	159 (2)
C8A—H8AA⋯O2Biii	0.97	2.55	3.280 (2)	132
C8B—H8BA⋯O1Wiv	0.97	2.32	3.247 (2)	160

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