N'-(3-Methoxy-benzyl-idene)-4-nitro-benzohydrazide monohydrate.

There are two independent formula units in the asymmetric unit of the title compound, C(15)H(13)N(3)O(4)·H(2)O. The C=C-N-C torsion angle of the methyl-idenehydrazide group is 174.3 (2)° in one mol-ecule and 178.6 (2)° in the other. The dihedral angles between the two benzene rings in the two mol-ecules are 4.17 (12) and 3.58 (12)°. In the crystal structure, inter-molecular O-H⋯O, N-H⋯O and O-H⋯N hydrogen bonds link the components into a two-dimensional network and additional stabilization is provided by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the synthesis of related compounds, see: Zia-ur-Rehman et al. (2005 ▶, 2006 ▶). For the biological activity of benzohydrazides, see: Zia-ur-Rehman et al. (2009 ▶); Jiang et al. (1990 ▶); Ochiai & Ishida (1982 ▶); Guersoy et al. (1995 ▶); Farghaly & Moharram (1999 ▶). For related structures, see: Raj et al. (2008 ▶); Fun et al. (2008 ▶); Wang et al. (2008 ▶); Qiu et al. (2009 ▶).

Experimental

Crystal data

C15H13N3O4·H2O

M = 317.30

Triclinic,

a = 6.7162 (3) Å

b = 7.4929 (3) Å

c = 32.1141 (15) Å

α = 91.883 (2)°

β = 91.5697 (12)°

γ = 112.753 (2)°

V = 1488.12 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 173 K

0.10 × 0.04 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.989, T max = 0.997

10724 measured reflections

6546 independent reflections

5035 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.149

S = 1.17

6546 reflections

429 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.24 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010986/lh5018sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010986/lh5018Isup2.hkl

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

C15H13N3O4·H2O	Z = 4
Mr = 317.30	F(000) = 664
Triclinic, P1	Dx = 1.416 Mg m−3
Hall symbol: -P 1	Melting point: 506 K
a = 6.7162 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.4929 (3) Å	Cell parameters from 5661 reflections
c = 32.1141 (15) Å	θ = 1.0–27.5°
α = 91.883 (2)°	µ = 0.11 mm−1
β = 91.5697 (12)°	T = 173 K
γ = 112.753 (2)°	Needle, yellow
V = 1488.12 (11) Å3	0.10 × 0.04 × 0.03 mm

Nonius KappaCCD diffractometer	6546 independent reflections
Radiation source: fine-focus sealed tube	5035 reflections with I > 2σ(I)
graphite	Rint = 0.035
ω and φ scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −8→8
Tmin = 0.989, Tmax = 0.997	k = −9→9
10724 measured reflections	l = −41→41

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)] = 0.071	Hydrogen site location: difference Fourier map
wR(F2) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ2(Fo2) + (0.0216P)2 + 1.6183P] where P = (Fo2 + 2Fc2)/3
6546 reflections	(Δ/σ)max < 0.001
429 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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 > σ(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
O1	0.5409 (5)	0.3361 (4)	0.52359 (7)	0.0652 (7)
O2	0.2135 (5)	0.3034 (4)	0.53490 (8)	0.0782 (9)
O3	0.8790 (3)	0.8188 (3)	0.71569 (6)	0.0423 (5)
O4	0.8847 (3)	1.1025 (3)	0.92010 (6)	0.0383 (5)
O5	0.2433 (3)	0.6052 (3)	0.96336 (6)	0.0461 (5)
O6	0.5729 (3)	0.7096 (3)	0.98840 (6)	0.0432 (5)
O7	0.8929 (3)	0.4098 (3)	0.80674 (6)	0.0390 (5)
O8	0.1740 (4)	−0.1127 (4)	0.57904 (6)	0.0613 (7)
O9	0.0742 (3)	0.5580 (3)	0.72390 (7)	0.0437 (5)
H9A	−0.016 (5)	0.464 (5)	0.7397 (10)	0.052*
H9B	0.017 (5)	0.651 (5)	0.7228 (10)	0.052*
O10	0.0793 (3)	0.1569 (3)	0.77316 (7)	0.0468 (6)
H10A	0.002 (6)	0.218 (5)	0.7828 (11)	0.056*
H10B	0.005 (6)	0.052 (5)	0.7631 (11)	0.056*
N1	0.4053 (5)	0.3579 (4)	0.54538 (8)	0.0522 (7)
N2	0.5317 (4)	0.7257 (3)	0.73434 (6)	0.0327 (5)
H2N	0.3936	0.6645	0.7272	0.039*
N3	0.5961 (4)	0.8154 (3)	0.77402 (6)	0.0327 (5)
N4	0.4328 (4)	0.6279 (3)	0.96079 (7)	0.0334 (5)
N5	0.5518 (3)	0.2963 (3)	0.77803 (6)	0.0293 (5)
H5N	0.4142	0.2727	0.7811	0.035*
N6	0.6228 (3)	0.2498 (3)	0.74060 (6)	0.0305 (5)
C1	0.6020 (4)	0.6333 (4)	0.66505 (8)	0.0317 (6)
C2	0.3846 (5)	0.5612 (4)	0.65178 (8)	0.0379 (6)
H2	0.2801	0.5730	0.6698	0.045*
C3	0.3205 (5)	0.4724 (4)	0.61237 (9)	0.0424 (7)
H3	0.1729	0.4241	0.6030	0.051*
C4	0.4752 (5)	0.4557 (4)	0.58715 (8)	0.0379 (6)
C5	0.6907 (5)	0.5251 (4)	0.59902 (9)	0.0420 (7)
H5	0.7938	0.5119	0.5808	0.050*
C6	0.7534 (5)	0.6152 (4)	0.63848 (8)	0.0401 (7)
H6	0.9017	0.6650	0.6474	0.048*
C7	0.6827 (4)	0.7339 (4)	0.70724 (8)	0.0329 (6)
C8	0.4388 (4)	0.8124 (4)	0.79569 (8)	0.0343 (6)
H8	0.2963	0.7536	0.7836	0.041*
C9	0.4687 (4)	0.8960 (4)	0.83847 (8)	0.0297 (5)
C10	0.6675 (4)	0.9670 (4)	0.86004 (8)	0.0291 (5)
H10	0.7925	0.9669	0.8469	0.035*
C11	0.6828 (4)	1.0387 (3)	0.90111 (8)	0.0272 (5)
C12	0.5013 (4)	1.0433 (3)	0.92029 (8)	0.0298 (5)
H12	0.5129	1.0940	0.9482	0.036*
C13	0.3032 (4)	0.9734 (4)	0.89832 (8)	0.0333 (6)
H13	0.1787	0.9760	0.9112	0.040*
C14	0.2862 (4)	0.8998 (4)	0.85770 (8)	0.0350 (6)
H14	0.1501	0.8517	0.8428	0.042*
C15	0.9058 (5)	1.1692 (4)	0.96298 (8)	0.0408 (7)
H15A	1.0560	1.2070	0.9732	0.049*
H15B	0.8110	1.0650	0.9796	0.049*
H15C	0.8649	1.2811	0.9655	0.049*
C16	0.6180 (4)	0.4345 (3)	0.84904 (7)	0.0259 (5)
C17	0.7721 (4)	0.5258 (4)	0.88126 (8)	0.0299 (5)
H17	0.9191	0.5459	0.8777	0.036*
C18	0.7132 (4)	0.5871 (4)	0.91830 (8)	0.0312 (6)
H18	0.8175	0.6487	0.9403	0.037*
C19	0.4983 (4)	0.5564 (3)	0.92247 (7)	0.0272 (5)
C20	0.3404 (4)	0.4629 (4)	0.89158 (8)	0.0302 (5)
H20	0.1932	0.4408	0.8956	0.036*
C21	0.4029 (4)	0.4028 (4)	0.85474 (8)	0.0309 (5)
H21	0.2973	0.3390	0.8331	0.037*
C22	0.6997 (4)	0.3791 (3)	0.80989 (8)	0.0289 (5)
C23	0.4724 (4)	0.1688 (4)	0.71271 (8)	0.0323 (6)
H23	0.3278	0.1467	0.7192	0.039*
C24	0.5146 (4)	0.1086 (4)	0.67096 (8)	0.0310 (5)
C25	0.3371 (4)	0.0256 (4)	0.64343 (8)	0.0366 (6)
H25	0.1975	0.0102	0.6521	0.044*
C26	0.3616 (5)	−0.0352 (4)	0.60320 (8)	0.0398 (7)
C27	0.5630 (5)	−0.0151 (4)	0.59032 (8)	0.0374 (6)
H27	0.5803	−0.0569	0.5629	0.045*
C28	0.7408 (5)	0.0676 (4)	0.61821 (9)	0.0388 (6)
H28	0.8799	0.0810	0.6096	0.047*
C29	0.7193 (4)	0.1306 (4)	0.65817 (8)	0.0361 (6)
H29	0.8423	0.1881	0.6767	0.043*
C30	0.1873 (6)	−0.1784 (6)	0.53710 (9)	0.0624 (10)
H30A	0.0433	−0.2282	0.5232	0.075*
H30B	0.2426	−0.2817	0.5376	0.075*
H30C	0.2851	−0.0702	0.5219	0.075*

	U11	U22	U33	U12	U13	U23
O1	0.101 (2)	0.0737 (16)	0.0305 (12)	0.0446 (15)	0.0065 (12)	−0.0088 (11)
O2	0.0780 (19)	0.097 (2)	0.0421 (14)	0.0186 (16)	−0.0182 (13)	−0.0240 (14)
O3	0.0343 (10)	0.0517 (12)	0.0369 (11)	0.0137 (9)	−0.0009 (8)	−0.0129 (9)
O4	0.0299 (10)	0.0522 (12)	0.0313 (10)	0.0153 (9)	−0.0018 (8)	−0.0114 (8)
O5	0.0418 (12)	0.0508 (12)	0.0417 (12)	0.0136 (10)	0.0152 (9)	−0.0073 (9)
O6	0.0554 (13)	0.0420 (11)	0.0260 (10)	0.0132 (10)	−0.0029 (9)	−0.0087 (8)
O7	0.0277 (10)	0.0500 (12)	0.0368 (11)	0.0131 (9)	0.0046 (8)	−0.0116 (9)
O8	0.0517 (13)	0.106 (2)	0.0288 (11)	0.0356 (13)	−0.0095 (9)	−0.0207 (12)
O9	0.0313 (11)	0.0545 (13)	0.0409 (12)	0.0114 (10)	0.0061 (9)	0.0046 (10)
O10	0.0312 (11)	0.0570 (14)	0.0513 (13)	0.0186 (10)	−0.0053 (9)	−0.0228 (11)
N1	0.080 (2)	0.0484 (15)	0.0269 (13)	0.0243 (15)	−0.0034 (14)	−0.0049 (11)
N2	0.0337 (12)	0.0380 (12)	0.0236 (11)	0.0117 (10)	−0.0011 (9)	−0.0041 (9)
N3	0.0393 (12)	0.0369 (12)	0.0222 (11)	0.0156 (10)	0.0006 (9)	−0.0025 (9)
N4	0.0437 (13)	0.0256 (11)	0.0280 (11)	0.0102 (10)	0.0080 (10)	0.0002 (9)
N5	0.0288 (11)	0.0379 (12)	0.0230 (10)	0.0150 (9)	0.0043 (8)	−0.0028 (9)
N6	0.0374 (12)	0.0336 (11)	0.0226 (10)	0.0162 (10)	0.0052 (9)	−0.0008 (9)
C1	0.0368 (14)	0.0290 (13)	0.0279 (13)	0.0114 (11)	−0.0001 (11)	−0.0014 (10)
C2	0.0387 (15)	0.0423 (15)	0.0287 (14)	0.0116 (12)	0.0041 (11)	−0.0036 (11)
C3	0.0409 (16)	0.0458 (16)	0.0327 (15)	0.0091 (13)	−0.0029 (12)	−0.0033 (12)
C4	0.0546 (18)	0.0320 (14)	0.0252 (13)	0.0150 (13)	0.0005 (12)	−0.0008 (11)
C5	0.0532 (18)	0.0494 (17)	0.0306 (15)	0.0281 (15)	0.0067 (13)	−0.0038 (12)
C6	0.0425 (16)	0.0495 (17)	0.0310 (14)	0.0211 (14)	0.0007 (12)	−0.0029 (12)
C7	0.0354 (14)	0.0332 (14)	0.0304 (13)	0.0140 (11)	−0.0003 (11)	−0.0018 (11)
C8	0.0347 (14)	0.0392 (15)	0.0276 (13)	0.0132 (12)	−0.0019 (11)	−0.0017 (11)
C9	0.0355 (14)	0.0272 (12)	0.0263 (12)	0.0119 (10)	0.0039 (10)	0.0028 (10)
C10	0.0310 (13)	0.0314 (13)	0.0261 (13)	0.0132 (10)	0.0055 (10)	0.0006 (10)
C11	0.0282 (12)	0.0256 (12)	0.0276 (12)	0.0103 (10)	0.0017 (10)	0.0016 (10)
C12	0.0362 (14)	0.0286 (12)	0.0260 (12)	0.0140 (11)	0.0055 (10)	−0.0008 (10)
C13	0.0301 (13)	0.0369 (14)	0.0353 (14)	0.0148 (11)	0.0100 (11)	0.0041 (11)
C14	0.0330 (14)	0.0400 (15)	0.0329 (14)	0.0152 (12)	0.0006 (11)	0.0021 (11)
C15	0.0406 (16)	0.0427 (16)	0.0296 (14)	0.0068 (13)	−0.0042 (12)	−0.0069 (12)
C16	0.0281 (12)	0.0242 (12)	0.0255 (12)	0.0102 (10)	0.0019 (10)	0.0009 (9)
C17	0.0251 (12)	0.0325 (13)	0.0311 (13)	0.0102 (10)	0.0005 (10)	−0.0014 (10)
C18	0.0299 (13)	0.0330 (13)	0.0276 (13)	0.0096 (11)	−0.0049 (10)	−0.0044 (10)
C19	0.0349 (13)	0.0249 (12)	0.0216 (11)	0.0112 (10)	0.0050 (10)	0.0009 (9)
C20	0.0266 (12)	0.0352 (13)	0.0287 (13)	0.0121 (11)	0.0022 (10)	−0.0007 (10)
C21	0.0270 (12)	0.0380 (14)	0.0250 (12)	0.0103 (11)	−0.0007 (10)	−0.0045 (10)
C22	0.0312 (13)	0.0280 (12)	0.0275 (13)	0.0116 (10)	0.0025 (10)	−0.0009 (10)
C23	0.0362 (14)	0.0358 (14)	0.0265 (13)	0.0158 (11)	0.0044 (11)	−0.0011 (11)
C24	0.0405 (14)	0.0313 (13)	0.0229 (12)	0.0154 (11)	0.0038 (10)	0.0014 (10)
C25	0.0357 (14)	0.0471 (16)	0.0288 (14)	0.0183 (12)	0.0037 (11)	−0.0018 (12)
C26	0.0460 (16)	0.0493 (17)	0.0261 (14)	0.0214 (14)	−0.0036 (12)	−0.0041 (12)
C27	0.0512 (17)	0.0396 (15)	0.0241 (13)	0.0204 (13)	0.0061 (12)	0.0000 (11)
C28	0.0413 (16)	0.0403 (15)	0.0345 (15)	0.0151 (13)	0.0104 (12)	−0.0006 (12)
C29	0.0371 (15)	0.0376 (14)	0.0323 (14)	0.0131 (12)	0.0051 (11)	−0.0010 (11)
C30	0.065 (2)	0.092 (3)	0.0277 (16)	0.030 (2)	−0.0091 (15)	−0.0170 (17)

O1—N1	1.220 (4)	C9—C14	1.397 (4)
O2—N1	1.225 (4)	C10—C11	1.393 (3)
O3—C7	1.240 (3)	C10—H10	0.9500
O4—C11	1.368 (3)	C11—C12	1.393 (3)
O4—C15	1.433 (3)	C12—C13	1.388 (4)
O5—N4	1.223 (3)	C12—H12	0.9500
O6—N4	1.233 (3)	C13—C14	1.384 (4)
O7—C22	1.235 (3)	C13—H13	0.9500
O8—C26	1.370 (3)	C14—H14	0.9500
O8—C30	1.436 (3)	C15—H15A	0.9800
O9—H9A	0.91 (4)	C15—H15B	0.9800
O9—H9B	0.92 (3)	C15—H15C	0.9800
O10—H10A	0.87 (4)	C16—C21	1.389 (3)
O10—H10B	0.80 (4)	C16—C17	1.399 (3)
N1—C4	1.480 (3)	C16—C22	1.495 (3)
N2—C7	1.339 (3)	C17—C18	1.383 (3)
N2—N3	1.397 (3)	C17—H17	0.9500
N2—H2N	0.8800	C18—C19	1.382 (4)
N3—C8	1.274 (3)	C18—H18	0.9500
N4—C19	1.471 (3)	C19—C20	1.386 (3)
N5—C22	1.358 (3)	C20—C21	1.385 (3)
N5—N6	1.388 (3)	C20—H20	0.9500
N5—H5N	0.8800	C21—H21	0.9500
N6—C23	1.277 (3)	C23—C24	1.470 (3)
C1—C6	1.388 (4)	C23—H23	0.9500
C1—C2	1.395 (4)	C24—C25	1.386 (4)
C1—C7	1.508 (3)	C24—C29	1.395 (4)
C2—C3	1.387 (4)	C25—C26	1.391 (4)
C2—H2	0.9500	C25—H25	0.9500
C3—C4	1.375 (4)	C26—C27	1.379 (4)
C3—H3	0.9500	C27—C28	1.395 (4)
C4—C5	1.373 (4)	C27—H27	0.9500
C5—C6	1.391 (4)	C28—C29	1.384 (4)
C5—H5	0.9500	C28—H28	0.9500
C6—H6	0.9500	C29—H29	0.9500
C8—C9	1.467 (3)	C30—H30A	0.9800
C8—H8	0.9500	C30—H30B	0.9800
C9—C10	1.386 (4)	C30—H30C	0.9800
C11—O4—C15	117.2 (2)	C13—C14—C9	120.1 (2)
C26—O8—C30	117.7 (2)	C13—C14—H14	119.9
H9A—O9—H9B	106 (3)	C9—C14—H14	119.9
H10A—O10—H10B	112 (3)	O4—C15—H15A	109.5
O1—N1—O2	124.0 (3)	O4—C15—H15B	109.5
O1—N1—C4	118.4 (3)	H15A—C15—H15B	109.5
O2—N1—C4	117.5 (3)	O4—C15—H15C	109.5
C7—N2—N3	119.2 (2)	H15A—C15—H15C	109.5
C7—N2—H2N	120.4	H15B—C15—H15C	109.5
N3—N2—H2N	120.4	C21—C16—C17	119.3 (2)
C8—N3—N2	113.4 (2)	C21—C16—C22	124.1 (2)
O5—N4—O6	123.5 (2)	C17—C16—C22	116.5 (2)
O5—N4—C19	118.4 (2)	C18—C17—C16	120.8 (2)
O6—N4—C19	118.1 (2)	C18—C17—H17	119.6
C22—N5—N6	118.4 (2)	C16—C17—H17	119.6
C22—N5—H5N	120.8	C19—C18—C17	118.1 (2)
N6—N5—H5N	120.8	C19—C18—H18	120.9
C23—N6—N5	114.2 (2)	C17—C18—H18	120.9
C6—C1—C2	119.4 (2)	C18—C19—C20	122.7 (2)
C6—C1—C7	117.7 (2)	C18—C19—N4	119.2 (2)
C2—C1—C7	122.9 (2)	C20—C19—N4	118.1 (2)
C3—C2—C1	120.3 (3)	C21—C20—C19	118.3 (2)
C3—C2—H2	119.9	C21—C20—H20	120.9
C1—C2—H2	119.9	C19—C20—H20	120.9
C4—C3—C2	118.5 (3)	C20—C21—C16	120.8 (2)
C4—C3—H3	120.7	C20—C21—H21	119.6
C2—C3—H3	120.7	C16—C21—H21	119.6
C5—C4—C3	123.0 (3)	O7—C22—N5	122.0 (2)
C5—C4—N1	118.7 (3)	O7—C22—C16	121.2 (2)
C3—C4—N1	118.3 (3)	N5—C22—C16	116.7 (2)
C4—C5—C6	118.0 (3)	N6—C23—C24	122.5 (2)
C4—C5—H5	121.0	N6—C23—H23	118.8
C6—C5—H5	121.0	C24—C23—H23	118.8
C1—C6—C5	120.8 (3)	C25—C24—C29	119.6 (2)
C1—C6—H6	119.6	C25—C24—C23	116.5 (2)
C5—C6—H6	119.6	C29—C24—C23	123.9 (2)
O3—C7—N2	122.9 (2)	C24—C25—C26	120.6 (3)
O3—C7—C1	120.7 (2)	C24—C25—H25	119.7
N2—C7—C1	116.4 (2)	C26—C25—H25	119.7
N3—C8—C9	122.7 (2)	O8—C26—C27	125.0 (2)
N3—C8—H8	118.6	O8—C26—C25	114.7 (3)
C9—C8—H8	118.6	C27—C26—C25	120.3 (3)
C10—C9—C14	120.0 (2)	C26—C27—C28	118.9 (2)
C10—C9—C8	122.6 (2)	C26—C27—H27	120.5
C14—C9—C8	117.4 (2)	C28—C27—H27	120.5
C9—C10—C11	119.6 (2)	C29—C28—C27	121.5 (3)
C9—C10—H10	120.2	C29—C28—H28	119.3
C11—C10—H10	120.2	C27—C28—H28	119.3
O4—C11—C12	124.0 (2)	C28—C29—C24	119.2 (3)
O4—C11—C10	115.4 (2)	C28—C29—H29	120.4
C12—C11—C10	120.6 (2)	C24—C29—H29	120.4
C13—C12—C11	119.4 (2)	O8—C30—H30A	109.5
C13—C12—H12	120.3	O8—C30—H30B	109.5
C11—C12—H12	120.3	H30A—C30—H30B	109.5
C14—C13—C12	120.3 (2)	O8—C30—H30C	109.5
C14—C13—H13	119.8	H30A—C30—H30C	109.5
C12—C13—H13	119.8	H30B—C30—H30C	109.5
C7—N2—N3—C8	174.3 (2)	C8—C9—C14—C13	178.8 (2)
C22—N5—N6—C23	178.6 (2)	C21—C16—C17—C18	−1.0 (4)
C6—C1—C2—C3	0.0 (4)	C22—C16—C17—C18	178.3 (2)
C7—C1—C2—C3	179.1 (3)	C16—C17—C18—C19	−0.2 (4)
C1—C2—C3—C4	0.6 (4)	C17—C18—C19—C20	1.6 (4)
C2—C3—C4—C5	−0.8 (5)	C17—C18—C19—N4	−177.3 (2)
C2—C3—C4—N1	179.0 (3)	O5—N4—C19—C18	177.6 (2)
O1—N1—C4—C5	2.7 (4)	O6—N4—C19—C18	−1.6 (3)
O2—N1—C4—C5	−177.5 (3)	O5—N4—C19—C20	−1.4 (3)
O1—N1—C4—C3	−177.2 (3)	O6—N4—C19—C20	179.4 (2)
O2—N1—C4—C3	2.7 (4)	C18—C19—C20—C21	−1.7 (4)
C3—C4—C5—C6	0.3 (5)	N4—C19—C20—C21	177.3 (2)
N1—C4—C5—C6	−179.5 (3)	C19—C20—C21—C16	0.3 (4)
C2—C1—C6—C5	−0.5 (4)	C17—C16—C21—C20	1.0 (4)
C7—C1—C6—C5	−179.6 (3)	C22—C16—C21—C20	−178.3 (2)
C4—C5—C6—C1	0.3 (4)	N6—N5—C22—O7	−1.6 (4)
N3—N2—C7—O3	−0.3 (4)	N6—N5—C22—C16	177.5 (2)
N3—N2—C7—C1	179.8 (2)	C21—C16—C22—O7	−179.5 (3)
C6—C1—C7—O3	9.0 (4)	C17—C16—C22—O7	1.2 (4)
C2—C1—C7—O3	−170.1 (3)	C21—C16—C22—N5	1.4 (4)
C6—C1—C7—N2	−171.0 (3)	C17—C16—C22—N5	−177.9 (2)
C2—C1—C7—N2	9.9 (4)	N5—N6—C23—C24	180.0 (2)
N2—N3—C8—C9	179.2 (2)	N6—C23—C24—C25	−178.9 (3)
N3—C8—C9—C10	−6.7 (4)	N6—C23—C24—C29	1.1 (4)
N3—C8—C9—C14	174.2 (3)	C29—C24—C25—C26	−0.2 (4)
C14—C9—C10—C11	1.2 (4)	C23—C24—C25—C26	179.8 (3)
C8—C9—C10—C11	−177.9 (2)	C30—O8—C26—C27	0.1 (5)
C15—O4—C11—C12	3.1 (4)	C30—O8—C26—C25	179.9 (3)
C15—O4—C11—C10	−177.2 (2)	C24—C25—C26—O8	−179.3 (3)
C9—C10—C11—O4	178.9 (2)	C24—C25—C26—C27	0.6 (4)
C9—C10—C11—C12	−1.4 (4)	O8—C26—C27—C28	179.6 (3)
O4—C11—C12—C13	−179.5 (2)	C25—C26—C27—C28	−0.3 (4)
C10—C11—C12—C13	0.9 (4)	C26—C27—C28—C29	−0.4 (4)
C11—C12—C13—C14	−0.1 (4)	C27—C28—C29—C24	0.8 (4)
C12—C13—C14—C9	−0.2 (4)	C25—C24—C29—C28	−0.5 (4)
C10—C9—C14—C13	−0.3 (4)	C23—C24—C29—C28	179.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O9	0.88	1.98	2.839 (3)	166
N5—H5N···O10	0.88	2.08	2.930 (3)	163
C2—H2···O9	0.95	2.23	3.153 (3)	164
C8—H8···O9	0.95	2.45	3.277 (3)	145
C15—H15B···O6	0.98	2.55	3.443 (4)	151
C21—H21···O10	0.95	2.42	3.355 (3)	169
C23—H23···O10	0.95	2.46	3.295 (3)	147
O9—H9A···O7i	0.91 (4)	2.26 (3)	3.020 (3)	140 (3)
O9—H9A···N6i	0.91 (4)	2.34 (3)	3.093 (3)	140 (3)
O9—H9B···O3i	0.92 (3)	1.84 (4)	2.758 (3)	173 (3)
O10—H10A···O7i	0.87 (4)	1.99 (4)	2.846 (3)	167 (3)
O10—H10B···O3ii	0.80 (4)	2.17 (4)	2.925 (3)	158 (3)
C13—H13···O4i	0.95	2.52	3.390 (3)	153
C15—H15A···O6iii	0.98	2.59	3.560 (4)	171
C30—H30A···O2iv	0.98	2.40	3.322 (4)	156
C30—H30B···O1v	0.98	2.59	3.200 (4)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O9	0.88	1.98	2.839 (3)	166
N5—H5N⋯O10	0.88	2.08	2.930 (3)	163
C2—H2⋯O9	0.95	2.23	3.153 (3)	164
C8—H8⋯O9	0.95	2.45	3.277 (3)	145
C15—H15B⋯O6	0.98	2.55	3.443 (4)	151
C21—H21⋯O10	0.95	2.42	3.355 (3)	169
C23—H23⋯O10	0.95	2.46	3.295 (3)	147
O9—H9A⋯O7i	0.91 (4)	2.26 (3)	3.020 (3)	140 (3)
O9—H9A⋯N6i	0.91 (4)	2.34 (3)	3.093 (3)	140 (3)
O9—H9B⋯O3i	0.92 (3)	1.84 (4)	2.758 (3)	173 (3)
O10—H10A⋯O7i	0.87 (4)	1.99 (4)	2.846 (3)	167 (3)
O10—H10B⋯O3ii	0.80 (4)	2.17 (4)	2.925 (3)	158 (3)
C13—H13⋯O4i	0.95	2.52	3.390 (3)	153
C15—H15A⋯O6iii	0.98	2.59	3.560 (4)	171
C30—H30A⋯O2iv	0.98	2.40	3.322 (4)	156
C30—H30B⋯O1v	0.98	2.59	3.200 (4)	121

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