(E)-4-Meth-oxy-N'-(2,4,5-tri-meth-oxy-benzyl-idene)benzohydrazide hemihydrate.

The title compound crystallizes as a hemihydrate, C18H20N2O5·0.5H2O. The mol-ecule exists in an E conformation with respect to the C=N imine bond. The 4-meth-oxy-phenyl unit is disordered over two sets of sites with a refined occupancy ratio of 0.54 (2):0.46 (2). The dihedral angles between the benzene rings are 29.20 (9) and 26.59 (9)°, respectively, for the major and minor components of the 4-meth-oxy-substituted ring. All meth-oxy substituents lie close to the plane of the attached benzene rings [the Cmeth-yl-O-C-C torsion angles range from -4.0 (12) to 3.9 (2)°]. In the crystal, the components are linked into chains propagating along [001] via N-H⋯O and O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions.

Related literature

For standard bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Fun et al. (2012 ▶); Horkaew et al. (2011 ▶). For applications of benzohydrazide derivatives, see: Molyneux (2004 ▶); Raj et al. (2007 ▶); Sathyadevi et al. (2012 ▶); Wang et al. (2012 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C18H20N2O5·0.5H2O

M = 353.37

Monoclinic,

a = 13.4405 (3) Å

b = 16.9172 (3) Å

c = 7.6841 (2) Å

β = 96.084 (1)°

V = 1737.34 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.28 × 0.18 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.972, T max = 0.992

13808 measured reflections

4606 independent reflections

2993 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.138

S = 1.04

4606 reflections

293 parameters

264 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.31 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, PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814000531/lh5678sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814000531/lh5678Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814000531/lh5678Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C18H20N2O5·0.5H2O	F(000) = 748
Mr = 353.37	Dx = 1.351 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4606 reflections
a = 13.4405 (3) Å	θ = 1.9–29.0°
b = 16.9172 (3) Å	µ = 0.10 mm−1
c = 7.6841 (2) Å	T = 100 K
β = 96.084 (1)°	Plate, colorless
V = 1737.34 (7) Å3	0.28 × 0.18 × 0.08 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	4606 independent reflections
Radiation source: fine-focus sealed tube	2993 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 8.33 pixels mm-1	θmax = 29.0°, θmin = 1.9°
ω scans	h = −17→18
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −20→23
Tmin = 0.972, Tmax = 0.992	l = −10→10
13808 measured reflections

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0568P)2 + 0.440P] where P = (Fo2 + 2Fc2)/3
4606 reflections	(Δ/σ)max = 0.001
293 parameters	Δρmax = 0.34 e Å−3
264 restraints	Δρmin = −0.31 e Å−3

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	Occ. (<1)
O1	0.29968 (9)	0.15688 (7)	1.03678 (15)	0.0175 (3)
O3	0.55282 (9)	0.46403 (8)	0.75008 (15)	0.0213 (3)
O4	0.78081 (9)	0.49186 (8)	1.28062 (16)	0.0217 (3)
O5	0.69285 (10)	0.37759 (8)	1.42709 (16)	0.0244 (3)
N1	0.32902 (11)	0.25582 (9)	0.8489 (2)	0.0163 (3)
H1N1	0.3183 (16)	0.2756 (13)	0.741 (3)	0.033 (6)*
N2	0.41000 (11)	0.28402 (9)	0.95977 (18)	0.0166 (3)
O2A	−0.0765 (6)	0.0960 (5)	0.4836 (12)	0.0297 (14)	0.54 (2)
C1A	0.1810 (10)	0.1723 (12)	0.787 (2)	0.0149 (6)	0.54 (2)
C2A	0.1424 (9)	0.0957 (10)	0.8016 (18)	0.0163 (10)	0.54 (2)
H2BA	0.1757	0.0602	0.8798	0.020*	0.54 (2)
C3A	0.0560 (8)	0.0726 (7)	0.7023 (13)	0.0183 (15)	0.54 (2)
H3BA	0.0312	0.0218	0.7142	0.022*	0.54 (2)
C4A	0.0057 (6)	0.1252 (6)	0.5839 (14)	0.0202 (15)	0.54 (2)
C5A	0.0422 (10)	0.2013 (7)	0.569 (2)	0.0203 (7)	0.54 (2)
H5BA	0.0086	0.2369	0.4910	0.024*	0.54 (2)
C6A	0.1292 (12)	0.2241 (10)	0.670 (3)	0.0159 (8)	0.54 (2)
H6BA	0.1532	0.2753	0.6597	0.019*	0.54 (2)
C15A	−0.1282 (7)	0.1466 (6)	0.3551 (17)	0.043 (2)	0.54 (2)
H15D	−0.1855	0.1194	0.2988	0.065*	0.54 (2)
H15E	−0.0842	0.1607	0.2694	0.065*	0.54 (2)
H15F	−0.1495	0.1935	0.4107	0.065*	0.54 (2)
O2B	−0.0920 (6)	0.1119 (6)	0.5300 (14)	0.0279 (16)	0.46 (2)
C1B	0.1849 (12)	0.1741 (14)	0.783 (3)	0.0149 (6)	0.46 (2)
C2B	0.1382 (10)	0.1019 (12)	0.816 (2)	0.0163 (10)	0.46 (2)
H2AA	0.1695	0.0664	0.8959	0.020*	0.46 (2)
C3B	0.0463 (9)	0.0839 (8)	0.7286 (16)	0.023 (2)	0.46 (2)
H3AA	0.0154	0.0363	0.7508	0.028*	0.46 (2)
C4B	−0.0008 (8)	0.1368 (8)	0.6073 (17)	0.0228 (18)	0.46 (2)
C5B	0.0434 (12)	0.2084 (8)	0.575 (2)	0.0203 (7)	0.46 (2)
H5AA	0.0117	0.2440	0.4952	0.024*	0.46 (2)
C6B	0.1360 (14)	0.2261 (12)	0.664 (3)	0.0159 (8)	0.46 (2)
H6AA	0.1660	0.2742	0.6431	0.019*	0.46 (2)
C15B	−0.1472 (7)	0.1666 (6)	0.4161 (15)	0.034 (2)	0.46 (2)
H15A	−0.2100	0.1434	0.3716	0.051*	0.46 (2)
H15B	−0.1096	0.1793	0.3204	0.051*	0.46 (2)
H15C	−0.1592	0.2139	0.4796	0.051*	0.46 (2)
C7	0.27597 (13)	0.19396 (10)	0.8996 (2)	0.0150 (4)
C8	0.45543 (12)	0.34220 (10)	0.8953 (2)	0.0157 (4)
H8A	0.4335	0.3599	0.7832	0.019*
C9	0.54027 (13)	0.38105 (10)	0.9932 (2)	0.0158 (4)
C10	0.58893 (13)	0.44309 (10)	0.9176 (2)	0.0164 (4)
C11	0.67034 (13)	0.48128 (11)	1.0102 (2)	0.0180 (4)
H11A	0.7027	0.5222	0.9581	0.022*
C12	0.70267 (13)	0.45794 (11)	1.1801 (2)	0.0176 (4)
C13	0.65430 (13)	0.39560 (11)	1.2589 (2)	0.0184 (4)
C14	0.57447 (13)	0.35826 (10)	1.1662 (2)	0.0175 (4)
H14A	0.5424	0.3172	1.2185	0.021*
C16	0.60554 (14)	0.52397 (12)	0.6663 (2)	0.0235 (4)
H16A	0.5719	0.5343	0.5521	0.035*
H16B	0.6725	0.5064	0.6556	0.035*
H16C	0.6076	0.5715	0.7350	0.035*
C17	0.83064 (14)	0.55583 (11)	1.2041 (2)	0.0209 (4)
H17A	0.8844	0.5746	1.2859	0.031*
H17B	0.7839	0.5980	1.1752	0.031*
H17C	0.8570	0.5378	1.0998	0.031*
C18	0.64432 (16)	0.31540 (13)	1.5103 (3)	0.0299 (5)
H18A	0.6775	0.3071	1.6257	0.045*
H18B	0.6470	0.2678	1.4430	0.045*
H18C	0.5757	0.3295	1.5181	0.045*
O1W	0.9194 (3)	0.3907 (3)	0.5262 (5)	0.0688 (12)	0.50
H2W1	0.8632	0.3689	0.5354	0.103*	0.50
H1W1	0.9088	0.4310	0.4608	0.103*	0.50

	U11	U22	U33	U12	U13	U23
O1	0.0241 (7)	0.0158 (6)	0.0120 (6)	0.0003 (6)	−0.0013 (5)	0.0002 (5)
O3	0.0216 (7)	0.0246 (7)	0.0166 (7)	−0.0069 (6)	−0.0028 (5)	0.0070 (6)
O4	0.0245 (7)	0.0180 (7)	0.0211 (7)	−0.0073 (6)	−0.0048 (5)	0.0000 (6)
O5	0.0314 (7)	0.0232 (7)	0.0163 (7)	−0.0086 (6)	−0.0079 (5)	0.0035 (6)
N1	0.0190 (8)	0.0170 (8)	0.0118 (7)	−0.0027 (7)	−0.0037 (6)	0.0008 (6)
N2	0.0177 (7)	0.0174 (8)	0.0139 (7)	−0.0015 (7)	−0.0017 (6)	−0.0021 (6)
O2A	0.023 (2)	0.030 (3)	0.033 (3)	−0.0094 (18)	−0.0111 (19)	0.008 (2)
C1A	0.0169 (11)	0.0155 (12)	0.0127 (9)	−0.0008 (9)	0.0028 (9)	−0.0026 (8)
C2A	0.0180 (11)	0.016 (2)	0.0148 (18)	0.0016 (11)	0.0013 (12)	0.0020 (15)
C3A	0.020 (2)	0.013 (3)	0.021 (3)	−0.002 (2)	0.003 (2)	0.000 (2)
C4A	0.017 (2)	0.020 (3)	0.023 (3)	−0.009 (2)	−0.0001 (19)	0.001 (2)
C5A	0.0193 (9)	0.0210 (18)	0.0199 (12)	0.0010 (11)	−0.0009 (8)	0.0044 (14)
C6A	0.0162 (17)	0.0156 (11)	0.0162 (13)	−0.0025 (10)	0.0032 (13)	0.0015 (9)
C15A	0.032 (3)	0.039 (4)	0.052 (5)	−0.013 (3)	−0.025 (3)	0.018 (4)
O2B	0.020 (2)	0.029 (3)	0.032 (3)	−0.010 (2)	−0.010 (2)	0.010 (2)
C1B	0.0169 (11)	0.0155 (12)	0.0127 (9)	−0.0008 (9)	0.0028 (9)	−0.0026 (8)
C2B	0.0180 (11)	0.016 (2)	0.0148 (18)	0.0016 (11)	0.0013 (12)	0.0020 (15)
C3B	0.022 (3)	0.023 (4)	0.026 (3)	−0.008 (3)	0.002 (3)	0.001 (3)
C4B	0.018 (2)	0.026 (3)	0.023 (3)	−0.002 (2)	−0.004 (2)	0.004 (3)
C5B	0.0193 (9)	0.0210 (18)	0.0199 (12)	0.0010 (11)	−0.0009 (8)	0.0044 (14)
C6B	0.0162 (17)	0.0156 (11)	0.0162 (13)	−0.0025 (10)	0.0032 (13)	0.0015 (9)
C15B	0.024 (3)	0.039 (4)	0.037 (4)	−0.012 (3)	−0.012 (3)	0.012 (3)
C7	0.0175 (8)	0.0145 (9)	0.0132 (8)	0.0023 (7)	0.0022 (6)	−0.0040 (7)
C8	0.0170 (8)	0.0167 (9)	0.0133 (8)	0.0021 (8)	0.0004 (6)	0.0002 (7)
C9	0.0166 (8)	0.0148 (9)	0.0155 (9)	0.0013 (7)	−0.0001 (6)	−0.0022 (7)
C10	0.0180 (9)	0.0147 (9)	0.0159 (9)	0.0033 (7)	−0.0008 (7)	−0.0001 (7)
C11	0.0181 (9)	0.0146 (9)	0.0212 (9)	−0.0003 (8)	0.0019 (7)	0.0006 (8)
C12	0.0176 (9)	0.0145 (9)	0.0199 (9)	−0.0005 (7)	−0.0018 (7)	−0.0038 (7)
C13	0.0232 (9)	0.0176 (9)	0.0136 (9)	0.0007 (8)	−0.0019 (7)	−0.0024 (8)
C14	0.0202 (9)	0.0135 (9)	0.0186 (9)	−0.0005 (8)	0.0013 (7)	0.0002 (7)
C16	0.0239 (10)	0.0267 (11)	0.0194 (10)	−0.0063 (9)	0.0004 (8)	0.0054 (8)
C17	0.0220 (10)	0.0163 (10)	0.0244 (10)	−0.0040 (8)	0.0013 (8)	−0.0029 (8)
C18	0.0416 (12)	0.0283 (11)	0.0175 (10)	−0.0129 (10)	−0.0073 (8)	0.0045 (9)
O1W	0.059 (2)	0.083 (3)	0.064 (3)	0.011 (2)	0.006 (2)	0.031 (2)

O1—C7	1.239 (2)	C2B—C3B	1.374 (6)
O3—C10	1.373 (2)	C2B—H2AA	0.9300
O3—C16	1.429 (2)	C3B—C4B	1.395 (6)
O4—C12	1.363 (2)	C3B—H3AA	0.9300
O4—C17	1.431 (2)	C4B—C5B	1.383 (6)
O5—C13	1.375 (2)	C5B—C6B	1.388 (6)
O5—C18	1.425 (2)	C5B—H5AA	0.9300
N1—C7	1.347 (2)	C6B—H6AA	0.9300
N1—N2	1.393 (2)	C15B—H15A	0.9600
N1—H1N1	0.89 (2)	C15B—H15B	0.9600
N2—C8	1.285 (2)	C15B—H15C	0.9600
O2A—C4A	1.370 (5)	C8—C9	1.455 (2)
O2A—C15A	1.430 (5)	C8—H8A	0.9300
C1A—C6A	1.387 (5)	C9—C10	1.395 (3)
C1A—C2A	1.404 (5)	C9—C14	1.413 (2)
C1A—C7	1.511 (7)	C10—C11	1.398 (2)
C2A—C3A	1.377 (5)	C11—C12	1.389 (2)
C2A—H2BA	0.9300	C11—H11A	0.9300
C3A—C4A	1.395 (5)	C12—C13	1.409 (3)
C3A—H3BA	0.9300	C13—C14	1.377 (2)
C4A—C5A	1.388 (5)	C14—H14A	0.9300
C5A—C6A	1.389 (5)	C16—H16A	0.9600
C5A—H5BA	0.9300	C16—H16B	0.9600
C6A—H6BA	0.9300	C16—H16C	0.9600
C15A—H15D	0.9600	C17—H17A	0.9600
C15A—H15E	0.9600	C17—H17B	0.9600
C15A—H15F	0.9600	C17—H17C	0.9600
O2B—C4B	1.371 (5)	C18—H18A	0.9600
O2B—C15B	1.427 (6)	C18—H18B	0.9600
C1B—C6B	1.384 (6)	C18—H18C	0.9600
C1B—C2B	1.408 (6)	O1W—H2W1	0.8500
C1B—C7	1.475 (9)	O1W—H1W1	0.8500
C10—O3—C16	117.55 (14)	O2B—C15B—H15C	109.5
C12—O4—C17	116.85 (14)	H15A—C15B—H15C	109.5
C13—O5—C18	116.14 (14)	H15B—C15B—H15C	109.5
C7—N1—N2	119.49 (15)	O1—C7—N1	122.91 (16)
C7—N1—H1N1	121.5 (14)	O1—C7—C1B	121.5 (9)
N2—N1—H1N1	118.6 (14)	N1—C7—C1B	115.6 (9)
C8—N2—N1	113.50 (15)	O1—C7—C1A	119.5 (8)
C4A—O2A—C15A	118.5 (5)	N1—C7—C1A	117.6 (8)
C6A—C1A—C2A	118.2 (5)	N2—C8—C9	121.65 (16)
C6A—C1A—C7	123.6 (11)	N2—C8—H8A	119.2
C2A—C1A—C7	118.2 (11)	C9—C8—H8A	119.2
C3A—C2A—C1A	120.9 (6)	C10—C9—C14	118.47 (16)
C3A—C2A—H2BA	119.6	C10—C9—C8	120.03 (16)
C1A—C2A—H2BA	119.6	C14—C9—C8	121.49 (16)
C2A—C3A—C4A	120.2 (5)	O3—C10—C9	116.72 (15)
C2A—C3A—H3BA	119.9	O3—C10—C11	122.50 (16)
C4A—C3A—H3BA	119.9	C9—C10—C11	120.77 (16)
O2A—C4A—C5A	123.9 (6)	C12—C11—C10	119.79 (17)
O2A—C4A—C3A	116.4 (5)	C12—C11—H11A	120.1
C5A—C4A—C3A	119.7 (5)	C10—C11—H11A	120.1
C4A—C5A—C6A	119.6 (6)	O4—C12—C11	123.95 (16)
C4A—C5A—H5BA	120.2	O4—C12—C13	115.79 (16)
C6A—C5A—H5BA	120.2	C11—C12—C13	120.25 (16)
C1A—C6A—C5A	121.4 (6)	O5—C13—C14	125.45 (16)
C1A—C6A—H6BA	119.3	O5—C13—C12	115.12 (15)
C5A—C6A—H6BA	119.3	C14—C13—C12	119.43 (16)
C4B—O2B—C15B	116.7 (6)	C13—C14—C9	121.28 (17)
C6B—C1B—C2B	118.5 (6)	C13—C14—H14A	119.4
C6B—C1B—C7	124.2 (13)	C9—C14—H14A	119.4
C2B—C1B—C7	116.6 (13)	O3—C16—H16A	109.5
C3B—C2B—C1B	120.1 (7)	O3—C16—H16B	109.5
C3B—C2B—H2AA	119.9	H16A—C16—H16B	109.5
C1B—C2B—H2AA	119.9	O3—C16—H16C	109.5
C2B—C3B—C4B	120.2 (6)	H16A—C16—H16C	109.5
C2B—C3B—H3AA	119.9	H16B—C16—H16C	109.5
C4B—C3B—H3AA	119.9	O4—C17—H17A	109.5
O2B—C4B—C5B	124.9 (7)	O4—C17—H17B	109.5
O2B—C4B—C3B	114.5 (7)	H17A—C17—H17B	109.5
C5B—C4B—C3B	120.6 (6)	O4—C17—H17C	109.5
C4B—C5B—C6B	118.7 (7)	H17A—C17—H17C	109.5
C4B—C5B—H5AA	120.7	H17B—C17—H17C	109.5
C6B—C5B—H5AA	120.7	O5—C18—H18A	109.5
C1B—C6B—C5B	121.9 (7)	O5—C18—H18B	109.5
C1B—C6B—H6AA	119.1	H18A—C18—H18B	109.5
C5B—C6B—H6AA	119.1	O5—C18—H18C	109.5
O2B—C15B—H15A	109.5	H18A—C18—H18C	109.5
O2B—C15B—H15B	109.5	H18B—C18—H18C	109.5
H15A—C15B—H15B	109.5	H2W1—O1W—H1W1	107.7
C7—N1—N2—C8	178.86 (15)	C2B—C1B—C7—C1A	−37 (47)
C6A—C1A—C2A—C3A	0.6 (2)	C6A—C1A—C7—O1	156.2 (7)
C7—C1A—C2A—C3A	179.9 (16)	C2A—C1A—C7—O1	−23.0 (15)
C1A—C2A—C3A—C4A	0.3 (2)	C6A—C1A—C7—N1	−21.0 (13)
C15A—O2A—C4A—C5A	0.1 (11)	C2A—C1A—C7—N1	159.8 (7)
C15A—O2A—C4A—C3A	−177.4 (7)	C6A—C1A—C7—C1B	−48 (48)
C2A—C3A—C4A—O2A	176.5 (10)	C2A—C1A—C7—C1B	133 (49)
C2A—C3A—C4A—C5A	−1.0 (5)	N1—N2—C8—C9	178.38 (15)
O2A—C4A—C5A—C6A	−176.6 (11)	N2—C8—C9—C10	178.79 (16)
C3A—C4A—C5A—C6A	0.8 (6)	N2—C8—C9—C14	−2.2 (3)
C2A—C1A—C6A—C5A	−0.9 (5)	C16—O3—C10—C9	−176.08 (16)
C7—C1A—C6A—C5A	179.9 (17)	C16—O3—C10—C11	3.9 (2)
C4A—C5A—C6A—C1A	0.2 (6)	C14—C9—C10—O3	−179.31 (15)
C6B—C1B—C2B—C3B	0.6 (2)	C8—C9—C10—O3	−0.2 (2)
C7—C1B—C2B—C3B	171.5 (18)	C14—C9—C10—C11	0.7 (3)
C1B—C2B—C3B—C4B	0.4 (3)	C8—C9—C10—C11	179.74 (16)
C15B—O2B—C4B—C5B	−4.0 (12)	O3—C10—C11—C12	179.27 (16)
C15B—O2B—C4B—C3B	174.8 (7)	C9—C10—C11—C12	−0.7 (3)
C2B—C3B—C4B—O2B	−179.9 (11)	C17—O4—C12—C11	0.7 (2)
C2B—C3B—C4B—C5B	−1.1 (5)	C17—O4—C12—C13	−179.46 (15)
O2B—C4B—C5B—C6B	179.5 (13)	C10—C11—C12—O4	−179.64 (16)
C3B—C4B—C5B—C6B	0.8 (7)	C10—C11—C12—C13	0.5 (3)
C2B—C1B—C6B—C5B	−0.8 (5)	C18—O5—C13—C14	−0.6 (3)
C7—C1B—C6B—C5B	−171 (2)	C18—O5—C13—C12	179.22 (16)
C4B—C5B—C6B—C1B	0.1 (7)	O4—C12—C13—O5	0.0 (2)
N2—N1—C7—O1	−5.0 (2)	C11—C12—C13—O5	179.89 (16)
N2—N1—C7—C1B	173.2 (12)	O4—C12—C13—C14	179.86 (16)
N2—N1—C7—C1A	172.1 (10)	C11—C12—C13—C14	−0.3 (3)
C6B—C1B—C7—O1	157.6 (8)	O5—C13—C14—C9	−179.94 (16)
C2B—C1B—C7—O1	−12.7 (18)	C12—C13—C14—C9	0.2 (3)
C6B—C1B—C7—N1	−20.6 (15)	C10—C9—C14—C13	−0.4 (3)
C2B—C1B—C7—N1	169.0 (8)	C8—C9—C14—C13	−179.49 (16)
C6B—C1B—C7—C1A	133 (49)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.89 (2)	1.94 (2)	2.8086 (19)	166 (2)
O1W—H2W1···O5ii	0.85	2.36	3.068 (4)	141
O1W—H1W1···O4ii	0.85	2.33	3.036 (5)	141
C6A—H6BA···O1i	0.93	2.55	3.294 (17)	138
C8—H8A···O1i	0.93	2.49	3.2786 (19)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.89 (2)	1.94 (2)	2.8086 (19)	166 (2)
O1W—H2W1⋯O5ii	0.85	2.36	3.068 (4)	141
O1W—H1W1⋯O4ii	0.85	2.33	3.036 (5)	141
C6A—H6BA⋯O1i	0.93	2.55	3.294 (17)	138
C8—H8A⋯O1i	0.93	2.49	3.2786 (19)	143

Symmetry codes: (i) ; (ii) .