(E)-1-(2,4-Dinitro-phen-yl)-2-[1-(3-meth-oxy-phen-yl)ethyl-idene]hydrazine.

There are two crystallographically independent mol-ecules in the asymmetric unit of the title compound, C(15)H(14)N(4)O(5), with different conformations for the meth-oxy groups. The mol-ecules are both slightly twisted, the dihedral angles between two benzene rings being 8.37 (18)° in one and 7.31 (18)° in the other. In both mol-ecules, the two nitro groups are essentially coplanar with their bound benzene ring, with the r.m.s. deviation of the dinitro-benzene plane being 0.0310 (3) Å in one mol-ecule and 0.0650 (3) Å in the other. In each mol-ecule, an intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions and stacked along the a axis through π-π inter-actions, with centroid-centroid distances of 3.651 (2) and 3.721 (2) Å. The crystal studied was a non-merohedral twin with a refined minor component of 20.1 (3)%.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Chantrapromma et al. (2012 ▶); Fun et al. (2010 ▶); Nilwanna et al. (2011 ▶). For background to the biological activity of hydro­zones, see: Bendre et al. (1998 ▶); El-Sherif (2009 ▶); Gokce et al. (2009 ▶); Molyneux (2004 ▶); Sathyadevi et al. (2012 ▶); Xia et al. (2008 ▶).

Experimental

Crystal data

C15H14N4O5

M = 330.30

Triclinic,

a = 7.5612 (13) Å

b = 10.4517 (18) Å

c = 19.516 (3) Å

α = 76.034 (4)°

β = 89.531 (4)°

γ = 84.052 (4)°

V = 1488.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.33 × 0.14 × 0.05 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.964, T max = 0.994

7846 measured reflections

7846 independent reflections

5592 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.086

wR(F 2) = 0.296

S = 1.11

7846 reflections

444 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.59 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 datablock(s) global, I. DOI: 10.1107/S1600536812026979/is5147sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026979/is5147Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812026979/is5147Isup3.cml

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

C15H14N4O5	Z = 4
Mr = 330.30	F(000) = 688
Triclinic, P1	Dx = 1.474 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5612 (13) Å	Cell parameters from 7846 reflections
b = 10.4517 (18) Å	θ = 1.1–29.0°
c = 19.516 (3) Å	µ = 0.11 mm−1
α = 76.034 (4)°	T = 100 K
β = 89.531 (4)°	Plate, orange
γ = 84.052 (4)°	0.33 × 0.14 × 0.05 mm
V = 1488.4 (4) Å3

Bruker SMART APEXII DUO CCD area-detector diffractometer	7846 independent reflections
Radiation source: fine-focus sealed tube	5592 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
φ and ω scans	θmax = 29.0°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.964, Tmax = 0.994	k = −13→14
7846 measured reflections	l = −12→26

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)] = 0.086	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.296	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.1531P)2 + 2.363P] where P = (Fo2 + 2Fc2)/3
7846 reflections	(Δ/σ)max = 0.001
444 parameters	Δρmax = 0.53 e Å−3
2 restraints	Δρmin = −0.59 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	0.5983 (4)	0.0757 (3)	0.79029 (14)	0.0199 (6)
O2A	0.7040 (4)	−0.0325 (3)	0.89291 (14)	0.0181 (6)
O3A	0.6439 (4)	0.1398 (3)	1.09429 (14)	0.0196 (6)
O4A	0.4793 (4)	0.3241 (3)	1.09095 (15)	0.0233 (6)
O5A	−0.0748 (4)	0.8559 (3)	0.67880 (16)	0.0231 (6)
N1A	0.4046 (4)	0.3030 (3)	0.77458 (15)	0.0128 (6)
H1NA	0.442 (6)	0.238 (3)	0.756 (2)	0.019*
N2A	0.3056 (4)	0.4176 (3)	0.73966 (16)	0.0146 (6)
N3A	0.6176 (4)	0.0642 (3)	0.85475 (16)	0.0136 (6)
N4A	0.5456 (4)	0.2375 (3)	1.06297 (16)	0.0154 (6)
C1A	0.4380 (5)	0.2851 (4)	0.84447 (18)	0.0127 (7)
C2A	0.5381 (4)	0.1691 (4)	0.88527 (18)	0.0125 (6)
C3A	0.5721 (4)	0.1543 (4)	0.95672 (18)	0.0126 (7)
H3A	0.6389	0.0787	0.9827	0.015*
C4A	0.5064 (4)	0.2520 (4)	0.98843 (18)	0.0128 (7)
C5A	0.4078 (5)	0.3681 (4)	0.95041 (19)	0.0152 (7)
H5A	0.3643	0.4335	0.9730	0.018*
C6A	0.3764 (5)	0.3842 (4)	0.87965 (18)	0.0139 (7)
H6A	0.3131	0.4620	0.8542	0.017*
C7A	0.2916 (5)	0.4404 (4)	0.67163 (18)	0.0131 (7)
C8A	0.3760 (5)	0.3548 (4)	0.62647 (19)	0.0183 (7)
H8A	0.4529	0.2834	0.6552	0.027*
H8B	0.4442	0.4068	0.5905	0.027*
H8C	0.2853	0.3194	0.6048	0.027*
C9A	0.1823 (5)	0.5658 (4)	0.63623 (18)	0.0138 (7)
C10A	0.1036 (5)	0.6493 (4)	0.67685 (19)	0.0157 (7)
H10A	0.1173	0.6256	0.7257	0.019*
C11A	0.0055 (5)	0.7671 (4)	0.6442 (2)	0.0168 (7)
C12A	−0.0155 (5)	0.8030 (4)	0.5704 (2)	0.0207 (8)
H12A	−0.0797	0.8830	0.5483	0.025*
C13A	0.0596 (6)	0.7191 (4)	0.5309 (2)	0.0227 (8)
H13A	0.0440	0.7424	0.4821	0.027*
C14A	0.1580 (5)	0.6005 (4)	0.56287 (19)	0.0189 (8)
H14A	0.2075	0.5445	0.5357	0.023*
C15A	−0.0621 (5)	0.8217 (4)	0.7541 (2)	0.0223 (8)
H15A	−0.1352	0.8862	0.7723	0.033*
H15B	0.0593	0.8200	0.7686	0.033*
H15C	−0.1019	0.7358	0.7720	0.033*
O1B	0.3655 (4)	0.3835 (3)	0.45297 (14)	0.0202 (6)
O2B	0.4931 (4)	0.1929 (3)	0.51179 (14)	0.0258 (7)
O3B	0.8328 (4)	−0.0989 (3)	0.39840 (15)	0.0215 (6)
O4B	0.7842 (4)	−0.0858 (3)	0.28765 (15)	0.0234 (6)
O5B	0.1203 (4)	0.6180 (3)	−0.00270 (14)	0.0187 (6)
N1B	0.3221 (4)	0.4301 (3)	0.31624 (16)	0.0150 (6)
H1NB	0.288 (6)	0.456 (5)	0.3542 (17)	0.022*
N2B	0.2573 (4)	0.4970 (3)	0.25056 (16)	0.0140 (6)
N3B	0.4467 (4)	0.2707 (3)	0.45574 (16)	0.0161 (6)
N4B	0.7603 (4)	−0.0432 (3)	0.34084 (17)	0.0167 (6)
C1B	0.4252 (4)	0.3144 (4)	0.32377 (18)	0.0124 (7)
C2B	0.4874 (5)	0.2337 (4)	0.39022 (18)	0.0121 (6)
C3B	0.5970 (5)	0.1153 (4)	0.39627 (19)	0.0136 (7)
H3B	0.6383	0.0645	0.4402	0.016*
C4B	0.6422 (4)	0.0759 (4)	0.33599 (18)	0.0128 (7)
C5B	0.5822 (5)	0.1513 (4)	0.26873 (19)	0.0145 (7)
H5B	0.6129	0.1218	0.2285	0.017*
C6B	0.4787 (5)	0.2677 (4)	0.26357 (18)	0.0131 (7)
H6B	0.4418	0.3185	0.2191	0.016*
C7B	0.1651 (4)	0.6103 (4)	0.24548 (18)	0.0129 (7)
C8B	0.1308 (5)	0.6726 (4)	0.3065 (2)	0.0193 (8)
H8D	0.1039	0.6061	0.3475	0.029*
H8E	0.0319	0.7399	0.2952	0.029*
H8F	0.2345	0.7117	0.3160	0.029*
C9B	0.0979 (5)	0.6790 (4)	0.17307 (19)	0.0136 (7)
C10B	0.1345 (5)	0.6197 (4)	0.11704 (19)	0.0144 (7)
H10B	0.2000	0.5369	0.1250	0.017*
C11B	0.0731 (5)	0.6842 (4)	0.0492 (2)	0.0147 (7)
C12B	−0.0255 (5)	0.8084 (4)	0.0359 (2)	0.0170 (7)
H12B	−0.0668	0.8509	−0.0095	0.020*
C13B	−0.0604 (5)	0.8667 (4)	0.0919 (2)	0.0183 (7)
H13B	−0.1250	0.9498	0.0838	0.022*
C14B	−0.0003 (5)	0.8030 (4)	0.1601 (2)	0.0166 (7)
H14B	−0.0259	0.8434	0.1971	0.020*
C15B	0.0306 (6)	0.6672 (4)	−0.0701 (2)	0.0216 (8)
H15D	0.0630	0.6079	−0.0998	0.032*
H15E	0.0645	0.7535	−0.0919	0.032*
H15F	−0.0957	0.6730	−0.0635	0.032*

	U11	U22	U33	U12	U13	U23
O1A	0.0298 (14)	0.0200 (14)	0.0094 (12)	0.0053 (11)	−0.0047 (10)	−0.0060 (10)
O2A	0.0204 (13)	0.0123 (13)	0.0192 (13)	0.0049 (10)	−0.0053 (10)	−0.0018 (10)
O3A	0.0217 (13)	0.0195 (14)	0.0148 (12)	0.0016 (11)	−0.0053 (10)	−0.0002 (11)
O4A	0.0352 (16)	0.0217 (15)	0.0124 (12)	0.0048 (12)	−0.0008 (11)	−0.0064 (11)
O5A	0.0258 (14)	0.0187 (15)	0.0221 (14)	0.0074 (11)	−0.0007 (11)	−0.0040 (12)
N1A	0.0162 (14)	0.0105 (14)	0.0102 (14)	0.0036 (11)	−0.0039 (11)	−0.0015 (11)
N2A	0.0177 (14)	0.0137 (15)	0.0113 (14)	0.0022 (12)	−0.0046 (11)	−0.0023 (12)
N3A	0.0145 (14)	0.0131 (15)	0.0129 (14)	0.0011 (11)	−0.0005 (11)	−0.0038 (12)
N4A	0.0208 (15)	0.0144 (15)	0.0106 (14)	−0.0020 (12)	0.0000 (11)	−0.0021 (12)
C1A	0.0143 (15)	0.0129 (17)	0.0114 (16)	−0.0030 (13)	0.0018 (12)	−0.0031 (13)
C2A	0.0142 (15)	0.0134 (17)	0.0103 (15)	0.0000 (12)	0.0020 (12)	−0.0045 (13)
C3A	0.0116 (15)	0.0131 (17)	0.0123 (16)	−0.0022 (12)	0.0000 (12)	−0.0012 (13)
C4A	0.0129 (15)	0.0132 (17)	0.0106 (15)	−0.0007 (13)	−0.0003 (12)	0.0001 (13)
C5A	0.0189 (17)	0.0141 (18)	0.0124 (16)	−0.0002 (13)	0.0016 (13)	−0.0036 (13)
C6A	0.0174 (16)	0.0116 (17)	0.0114 (16)	0.0028 (13)	−0.0007 (12)	−0.0020 (13)
C7A	0.0159 (16)	0.0121 (17)	0.0110 (15)	−0.0006 (13)	−0.0008 (12)	−0.0026 (13)
C8A	0.0268 (19)	0.0173 (19)	0.0099 (16)	0.0026 (15)	−0.0002 (13)	−0.0037 (14)
C9A	0.0156 (16)	0.0128 (17)	0.0111 (16)	−0.0013 (13)	−0.0036 (12)	0.0005 (13)
C10A	0.0178 (16)	0.0157 (18)	0.0129 (16)	−0.0044 (14)	−0.0027 (13)	−0.0011 (14)
C11A	0.0150 (16)	0.0164 (18)	0.0191 (18)	−0.0014 (14)	0.0014 (13)	−0.0047 (15)
C12A	0.0229 (19)	0.0181 (19)	0.0172 (18)	0.0029 (15)	−0.0048 (14)	0.0015 (15)
C13A	0.029 (2)	0.025 (2)	0.0107 (17)	−0.0002 (16)	−0.0047 (14)	0.0008 (15)
C14A	0.0234 (18)	0.021 (2)	0.0103 (16)	0.0003 (15)	−0.0016 (13)	−0.0021 (14)
C15A	0.0220 (18)	0.024 (2)	0.0209 (19)	0.0018 (16)	0.0050 (15)	−0.0076 (16)
O1B	0.0289 (14)	0.0166 (14)	0.0147 (13)	0.0064 (11)	0.0003 (10)	−0.0066 (11)
O2B	0.0438 (18)	0.0211 (15)	0.0091 (12)	0.0063 (13)	0.0032 (11)	−0.0009 (11)
O3B	0.0248 (14)	0.0194 (14)	0.0169 (13)	0.0063 (11)	−0.0050 (11)	−0.0012 (11)
O4B	0.0310 (15)	0.0211 (15)	0.0178 (14)	0.0088 (12)	−0.0018 (11)	−0.0089 (12)
O5B	0.0233 (13)	0.0187 (14)	0.0136 (13)	0.0026 (11)	−0.0026 (10)	−0.0051 (11)
N1B	0.0193 (15)	0.0147 (15)	0.0098 (14)	0.0031 (12)	−0.0009 (11)	−0.0029 (12)
N2B	0.0140 (13)	0.0140 (15)	0.0118 (14)	0.0018 (11)	0.0000 (11)	−0.0001 (12)
N3B	0.0212 (15)	0.0158 (16)	0.0106 (14)	0.0002 (12)	0.0018 (11)	−0.0026 (12)
N4B	0.0182 (14)	0.0141 (16)	0.0171 (15)	0.0020 (12)	0.0006 (11)	−0.0040 (12)
C1B	0.0127 (15)	0.0120 (17)	0.0126 (16)	−0.0002 (12)	0.0004 (12)	−0.0034 (13)
C2B	0.0152 (15)	0.0137 (17)	0.0075 (15)	−0.0005 (13)	0.0015 (12)	−0.0029 (13)
C3B	0.0153 (16)	0.0132 (17)	0.0110 (15)	−0.0008 (13)	−0.0004 (12)	−0.0007 (13)
C4B	0.0132 (15)	0.0102 (16)	0.0136 (16)	0.0026 (12)	−0.0008 (12)	−0.0019 (13)
C5B	0.0146 (16)	0.0168 (18)	0.0130 (16)	−0.0019 (13)	−0.0016 (12)	−0.0048 (14)
C6B	0.0165 (16)	0.0121 (17)	0.0088 (15)	0.0003 (13)	−0.0015 (12)	0.0005 (13)
C7B	0.0114 (14)	0.0128 (17)	0.0137 (16)	0.0007 (12)	0.0006 (12)	−0.0024 (13)
C8B	0.0223 (18)	0.0192 (19)	0.0165 (17)	0.0050 (15)	−0.0016 (14)	−0.0075 (15)
C9B	0.0122 (15)	0.0140 (17)	0.0134 (16)	−0.0010 (13)	0.0002 (12)	−0.0015 (13)
C10B	0.0131 (15)	0.0128 (17)	0.0160 (17)	0.0012 (13)	0.0000 (12)	−0.0019 (14)
C11B	0.0137 (15)	0.0126 (17)	0.0181 (17)	−0.0028 (13)	0.0001 (13)	−0.0035 (14)
C12B	0.0149 (16)	0.0154 (18)	0.0193 (18)	0.0004 (13)	−0.0034 (13)	−0.0019 (14)
C13B	0.0192 (17)	0.0120 (17)	0.0211 (19)	0.0021 (14)	0.0010 (14)	−0.0006 (14)
C14B	0.0169 (16)	0.0155 (18)	0.0160 (17)	0.0005 (13)	0.0025 (13)	−0.0022 (14)
C15B	0.026 (2)	0.024 (2)	0.0146 (17)	−0.0027 (16)	−0.0031 (14)	−0.0044 (15)

O1A—N3A	1.243 (4)	O1B—N3B	1.261 (4)
O2A—N3A	1.229 (4)	O2B—N3B	1.224 (4)
O3A—N4A	1.232 (4)	O3B—N4B	1.236 (4)
O4A—N4A	1.228 (4)	O4B—N4B	1.230 (4)
O5A—C11A	1.367 (5)	O5B—C11B	1.383 (5)
O5A—C15A	1.427 (5)	O5B—C15B	1.438 (5)
N1A—C1A	1.353 (4)	N1B—C1B	1.347 (5)
N1A—N2A	1.374 (4)	N1B—N2B	1.370 (4)
N1A—H1NA	0.868 (19)	N1B—H1NB	0.873 (19)
N2A—C7A	1.294 (5)	N2B—C7B	1.293 (5)
N3A—C2A	1.447 (5)	N3B—C2B	1.444 (4)
N4A—C4A	1.456 (4)	N4B—C4B	1.439 (5)
C1A—C6A	1.414 (5)	C1B—C6B	1.418 (5)
C1A—C2A	1.425 (5)	C1B—C2B	1.419 (5)
C2A—C3A	1.388 (5)	C2B—C3B	1.397 (5)
C3A—C4A	1.367 (5)	C3B—C4B	1.367 (5)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.402 (5)	C4B—C5B	1.409 (5)
C5A—C6A	1.370 (5)	C5B—C6B	1.360 (5)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—C9A	1.492 (5)	C7B—C9B	1.489 (5)
C7A—C8A	1.496 (5)	C7B—C8B	1.498 (5)
C8A—H8A	0.9600	C8B—H8D	0.9600
C8A—H8B	0.9600	C8B—H8E	0.9600
C8A—H8C	0.9600	C8B—H8F	0.9600
C9A—C14A	1.398 (5)	C9B—C14B	1.393 (5)
C9A—C10A	1.401 (5)	C9B—C10B	1.394 (5)
C10A—C11A	1.382 (5)	C10B—C11B	1.393 (5)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.402 (5)	C11B—C12B	1.395 (5)
C12A—C13A	1.380 (6)	C12B—C13B	1.384 (6)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.386 (6)	C13B—C14B	1.394 (5)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15C	0.9600	C15B—H15F	0.9600
C11A—O5A—C15A	117.4 (3)	C11B—O5B—C15B	116.8 (3)
C1A—N1A—N2A	118.3 (3)	C1B—N1B—N2B	119.4 (3)
C1A—N1A—H1NA	117 (3)	C1B—N1B—H1NB	118 (3)
N2A—N1A—H1NA	125 (3)	N2B—N1B—H1NB	122 (3)
C7A—N2A—N1A	117.6 (3)	C7B—N2B—N1B	117.2 (3)
O2A—N3A—O1A	122.0 (3)	O2B—N3B—O1B	122.2 (3)
O2A—N3A—C2A	119.2 (3)	O2B—N3B—C2B	119.4 (3)
O1A—N3A—C2A	118.7 (3)	O1B—N3B—C2B	118.4 (3)
O4A—N4A—O3A	123.7 (3)	O4B—N4B—O3B	122.7 (3)
O4A—N4A—C4A	117.9 (3)	O4B—N4B—C4B	118.6 (3)
O3A—N4A—C4A	118.3 (3)	O3B—N4B—C4B	118.6 (3)
N1A—C1A—C6A	120.4 (3)	N1B—C1B—C6B	120.2 (3)
N1A—C1A—C2A	122.4 (3)	N1B—C1B—C2B	123.3 (3)
C6A—C1A—C2A	117.2 (3)	C6B—C1B—C2B	116.4 (3)
C3A—C2A—C1A	121.1 (3)	C3B—C2B—C1B	122.0 (3)
C3A—C2A—N3A	116.2 (3)	C3B—C2B—N3B	115.6 (3)
C1A—C2A—N3A	122.7 (3)	C1B—C2B—N3B	122.3 (3)
C4A—C3A—C2A	119.3 (3)	C4B—C3B—C2B	118.3 (3)
C4A—C3A—H3A	120.3	C4B—C3B—H3B	120.8
C2A—C3A—H3A	120.3	C2B—C3B—H3B	120.8
C3A—C4A—C5A	121.7 (3)	C3B—C4B—C5B	122.0 (3)
C3A—C4A—N4A	119.2 (3)	C3B—C4B—N4B	119.2 (3)
C5A—C4A—N4A	119.1 (3)	C5B—C4B—N4B	118.8 (3)
C6A—C5A—C4A	119.2 (3)	C6B—C5B—C4B	119.0 (3)
C6A—C5A—H5A	120.4	C6B—C5B—H5B	120.5
C4A—C5A—H5A	120.4	C4B—C5B—H5B	120.5
C5A—C6A—C1A	121.4 (3)	C5B—C6B—C1B	122.2 (3)
C5A—C6A—H6A	119.3	C5B—C6B—H6B	118.9
C1A—C6A—H6A	119.3	C1B—C6B—H6B	118.9
N2A—C7A—C9A	115.5 (3)	N2B—C7B—C9B	115.1 (3)
N2A—C7A—C8A	126.2 (3)	N2B—C7B—C8B	123.7 (3)
C9A—C7A—C8A	118.2 (3)	C9B—C7B—C8B	121.2 (3)
C7A—C8A—H8A	109.5	C7B—C8B—H8D	109.5
C7A—C8A—H8B	109.5	C7B—C8B—H8E	109.5
H8A—C8A—H8B	109.5	H8D—C8B—H8E	109.5
C7A—C8A—H8C	109.5	C7B—C8B—H8F	109.5
H8A—C8A—H8C	109.5	H8D—C8B—H8F	109.5
H8B—C8A—H8C	109.5	H8E—C8B—H8F	109.5
C14A—C9A—C10A	119.8 (3)	C14B—C9B—C10B	119.1 (3)
C14A—C9A—C7A	120.5 (3)	C14B—C9B—C7B	120.9 (3)
C10A—C9A—C7A	119.7 (3)	C10B—C9B—C7B	119.9 (3)
C11A—C10A—C9A	119.9 (3)	C11B—C10B—C9B	120.1 (3)
C11A—C10A—H10A	120.0	C11B—C10B—H10B	120.0
C9A—C10A—H10A	120.0	C9B—C10B—H10B	120.0
O5A—C11A—C10A	124.5 (3)	O5B—C11B—C10B	115.3 (3)
O5A—C11A—C12A	115.4 (3)	O5B—C11B—C12B	123.6 (3)
C10A—C11A—C12A	120.2 (4)	C10B—C11B—C12B	121.0 (3)
C13A—C12A—C11A	119.6 (4)	C13B—C12B—C11B	118.4 (3)
C13A—C12A—H12A	120.2	C13B—C12B—H12B	120.8
C11A—C12A—H12A	120.2	C11B—C12B—H12B	120.8
C12A—C13A—C14A	121.0 (4)	C12B—C13B—C14B	121.1 (4)
C12A—C13A—H13A	119.5	C12B—C13B—H13B	119.4
C14A—C13A—H13A	119.5	C14B—C13B—H13B	119.4
C13A—C14A—C9A	119.5 (4)	C9B—C14B—C13B	120.2 (4)
C13A—C14A—H14A	120.2	C9B—C14B—H14B	119.9
C9A—C14A—H14A	120.2	C13B—C14B—H14B	119.9
O5A—C15A—H15A	109.5	O5B—C15B—H15D	109.5
O5A—C15A—H15B	109.5	O5B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
O5A—C15A—H15C	109.5	O5B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C1A—N1A—N2A—C7A	172.4 (3)	C1B—N1B—N2B—C7B	−177.2 (3)
N2A—N1A—C1A—C6A	−1.9 (5)	N2B—N1B—C1B—C6B	5.4 (5)
N2A—N1A—C1A—C2A	179.5 (3)	N2B—N1B—C1B—C2B	−175.2 (3)
N1A—C1A—C2A—C3A	179.2 (3)	N1B—C1B—C2B—C3B	−178.8 (3)
C6A—C1A—C2A—C3A	0.5 (5)	C6B—C1B—C2B—C3B	0.7 (5)
N1A—C1A—C2A—N3A	2.5 (5)	N1B—C1B—C2B—N3B	−0.9 (5)
C6A—C1A—C2A—N3A	−176.2 (3)	C6B—C1B—C2B—N3B	178.5 (3)
O2A—N3A—C2A—C3A	2.4 (5)	O2B—N3B—C2B—C3B	−7.3 (5)
O1A—N3A—C2A—C3A	−176.6 (3)	O1B—N3B—C2B—C3B	172.1 (3)
O2A—N3A—C2A—C1A	179.2 (3)	O2B—N3B—C2B—C1B	174.7 (3)
O1A—N3A—C2A—C1A	0.2 (5)	O1B—N3B—C2B—C1B	−5.9 (5)
C1A—C2A—C3A—C4A	0.8 (5)	C1B—C2B—C3B—C4B	−1.2 (5)
N3A—C2A—C3A—C4A	177.7 (3)	N3B—C2B—C3B—C4B	−179.1 (3)
C2A—C3A—C4A—C5A	−1.1 (5)	C2B—C3B—C4B—C5B	0.3 (5)
C2A—C3A—C4A—N4A	−178.7 (3)	C2B—C3B—C4B—N4B	177.7 (3)
O4A—N4A—C4A—C3A	−177.2 (3)	O4B—N4B—C4B—C3B	171.9 (3)
O3A—N4A—C4A—C3A	3.2 (5)	O3B—N4B—C4B—C3B	−7.7 (5)
O4A—N4A—C4A—C5A	5.2 (5)	O4B—N4B—C4B—C5B	−10.6 (5)
O3A—N4A—C4A—C5A	−174.4 (3)	O3B—N4B—C4B—C5B	169.8 (3)
C3A—C4A—C5A—C6A	0.0 (5)	C3B—C4B—C5B—C6B	1.1 (5)
N4A—C4A—C5A—C6A	177.6 (3)	N4B—C4B—C5B—C6B	−176.3 (3)
C4A—C5A—C6A—C1A	1.3 (5)	C4B—C5B—C6B—C1B	−1.7 (5)
N1A—C1A—C6A—C5A	179.7 (3)	N1B—C1B—C6B—C5B	−179.8 (3)
C2A—C1A—C6A—C5A	−1.5 (5)	C2B—C1B—C6B—C5B	0.8 (5)
N1A—N2A—C7A—C9A	179.8 (3)	N1B—N2B—C7B—C9B	179.9 (3)
N1A—N2A—C7A—C8A	−1.3 (5)	N1B—N2B—C7B—C8B	1.7 (5)
N2A—C7A—C9A—C14A	180.0 (3)	N2B—C7B—C9B—C14B	−178.8 (3)
C8A—C7A—C9A—C14A	1.0 (5)	C8B—C7B—C9B—C14B	−0.5 (5)
N2A—C7A—C9A—C10A	0.1 (5)	N2B—C7B—C9B—C10B	0.6 (5)
C8A—C7A—C9A—C10A	−179.0 (3)	C8B—C7B—C9B—C10B	178.9 (3)
C14A—C9A—C10A—C11A	−1.4 (5)	C14B—C9B—C10B—C11B	0.0 (5)
C7A—C9A—C10A—C11A	178.5 (3)	C7B—C9B—C10B—C11B	−179.4 (3)
C15A—O5A—C11A—C10A	−2.6 (5)	C15B—O5B—C11B—C10B	167.7 (3)
C15A—O5A—C11A—C12A	178.0 (3)	C15B—O5B—C11B—C12B	−13.8 (5)
C9A—C10A—C11A—O5A	−179.3 (3)	C9B—C10B—C11B—O5B	178.6 (3)
C9A—C10A—C11A—C12A	0.1 (5)	C9B—C10B—C11B—C12B	0.0 (5)
O5A—C11A—C12A—C13A	−179.4 (3)	O5B—C11B—C12B—C13B	−178.2 (3)
C10A—C11A—C12A—C13A	1.1 (6)	C10B—C11B—C12B—C13B	0.3 (5)
C11A—C12A—C13A—C14A	−1.0 (6)	C11B—C12B—C13B—C14B	−0.6 (5)
C12A—C13A—C14A—C9A	−0.3 (6)	C10B—C9B—C14B—C13B	−0.2 (5)
C10A—C9A—C14A—C13A	1.5 (6)	C7B—C9B—C14B—C13B	179.2 (3)
C7A—C9A—C14A—C13A	−178.4 (3)	C12B—C13B—C14B—C9B	0.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···O1A	0.87 (3)	1.94 (4)	2.611 (4)	133 (3)
N1B—H1NB···O1B	0.88 (4)	1.96 (3)	2.611 (4)	130 (4)
C5B—H5B···O3Ai	0.93	2.59	3.462 (5)	156
C6B—H6B···O4Ai	0.93	2.50	3.277 (4)	141
C8A—H8C···O3Bii	0.96	2.57	3.376 (5)	142
C8B—H8E···O4Biii	0.96	2.45	3.402 (5)	170
C12B—H12B···O2Aiv	0.93	2.57	3.447 (5)	157
C13A—H13A···O3Biii	0.93	2.48	3.204 (5)	135
C13B—H13B···O3Aiv	0.93	2.55	3.448 (5)	162
C14B—H14B···O4Biii	0.93	2.47	3.338 (5)	155
C15B—H15E···O3Av	0.96	2.57	3.301 (5)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1NA⋯O1A	0.87 (3)	1.94 (4)	2.611 (4)	133 (3)
N1B—H1NB⋯O1B	0.88 (4)	1.96 (3)	2.611 (4)	130 (4)
C5B—H5B⋯O3A i	0.93	2.59	3.462 (5)	156
C6B—H6B⋯O4A i	0.93	2.50	3.277 (4)	141
C8A—H8C⋯O3B ii	0.96	2.57	3.376 (5)	142
C8B—H8E⋯O4B iii	0.96	2.45	3.402 (5)	170
C12B—H12B⋯O2A iv	0.93	2.57	3.447 (5)	157
C13A—H13A⋯O3B iii	0.93	2.48	3.204 (5)	135
C13B—H13B⋯O3A iv	0.93	2.55	3.448 (5)	162
C14B—H14B⋯O4B iii	0.93	2.47	3.338 (5)	155
C15B—H15E⋯O3A v	0.96	2.57	3.301 (5)	133

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