(E)-4-Meth-oxy-N'-(3,4,5-trimeth-oxy-benzyl-idene)benzohydrazide.

In the asymmetric unit of the title compound, C(18)H(20)N(2)O(5), there are two crystallographic independent mol-ecules. Both mol-ecules are twisted; the dihedral angle between the two benzene rings is 7.2 (5)° in one mol-ecule, whereas it is 85.9 (4)° in the other. Of the three meth-oxy groups in the 3,4,5-trimeth-oxy-phenyl unit, two meth-oxy groups at meta positions are approximately coplanar with the benzene plane [C-O-C-C torsion angles of -2.3 (13)-4.8 (11)°], but the other meth-oxy, at the para position, is out of the plane [C-O-C-C of 72.8 (9)° in one mol-ecule and -77.5 (9)° in the other]. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds and weak C-H⋯O inter-actions into tapes along the b axis. C-H⋯π inter-actions are also present.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Fun et al. (2011 ▶); Horkaew et al. (2011 ▶); Promdet et al. (2011 ▶). For background and applications of benzohydrazide derivatives, see: Angelusiu et al. (2010 ▶); Bedia et al. (2006 ▶); Loncle et al. (2004 ▶); Melnyk et al. (2006 ▶); Raj et al. (2007 ▶).

Experimental

Crystal data

C18H20N2O5

M = 344.36

Monoclinic,

a = 13.3344 (17) Å

b = 5.0484 (6) Å

c = 25.767 (3) Å

β = 98.250 (2)°

V = 1716.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 297 K

0.26 × 0.25 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.975, T max = 0.990

12488 measured reflections

3361 independent reflections

2671 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.090

wR(F 2) = 0.275

S = 1.05

3361 reflections

453 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.75 e Å−3

Δρmin = −0.47 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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/S1600536812003534/is5059sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003534/is5059Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812003534/is5059Isup3.cml

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

C18H20N2O5	F(000) = 728
Mr = 344.36	Dx = 1.332 Mg m−3
Monoclinic, P21	Melting point = 464–465 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 13.3344 (17) Å	Cell parameters from 3361 reflections
b = 5.0484 (6) Å	θ = 1.6–25.0°
c = 25.767 (3) Å	µ = 0.10 mm−1
β = 98.250 (2)°	T = 297 K
V = 1716.6 (4) Å3	Block, colorless
Z = 4	0.26 × 0.25 × 0.11 mm

Bruker SMART APEXII CCD area-detector diffractometer	3361 independent reflections
Radiation source: fine-focus sealed tube	2671 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 8.33 pixels mm-1	θmax = 25.0°, θmin = 1.6°
ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→6
Tmin = 0.975, Tmax = 0.990	l = −30→30
12488 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)] = 0.090	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.275	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1357P)2 + 4.5571P] where P = (Fo2 + 2Fc2)/3
3361 reflections	(Δ/σ)max = 0.001
453 parameters	Δρmax = 0.75 e Å−3
1 restraint	Δρmin = −0.47 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 > 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	0.3343 (7)	−0.3991 (18)	0.6742 (3)	0.078 (2)
O2A	0.6531 (5)	0.112 (2)	0.5437 (3)	0.080 (3)
O3A	−0.0197 (4)	−0.2248 (13)	0.8547 (2)	0.0443 (14)
O4A	0.0405 (4)	0.0695 (13)	0.93724 (19)	0.0450 (14)
O5A	0.1905 (4)	0.4311 (15)	0.9377 (2)	0.0543 (17)
N1A	0.3208 (5)	0.0316 (19)	0.6969 (3)	0.055 (2)
H1NA	0.3373	0.1922	0.6909	0.066*
N2A	0.2568 (5)	−0.0252 (18)	0.7341 (3)	0.053 (2)
C1A	0.4361 (7)	−0.083 (2)	0.6382 (3)	0.053 (2)
C2A	0.4404 (8)	−0.243 (4)	0.5919 (4)	0.101 (4)
H2A	0.4008	−0.3925	0.5830	0.121*
C3A	0.5149 (8)	−0.139 (4)	0.5609 (4)	0.101 (4)
H3A	0.5156	−0.2111	0.5278	0.121*
C4A	0.5852 (6)	0.060 (3)	0.5768 (3)	0.063 (3)
C5A	0.5800 (7)	0.192 (3)	0.6231 (3)	0.065 (3)
H5A	0.6257	0.3269	0.6340	0.078*
C6A	0.5070 (7)	0.123 (3)	0.6530 (4)	0.077 (4)
H6A	0.5037	0.2148	0.6841	0.093*
C7A	0.3549 (8)	−0.1670 (18)	0.6713 (4)	0.054 (2)
C8A	0.2406 (7)	0.1708 (19)	0.7608 (3)	0.045 (2)
H8AA	0.2653	0.3358	0.7528	0.054*
C9A	0.1820 (6)	0.1442 (17)	0.8058 (3)	0.0377 (19)
C10A	0.1069 (5)	−0.0388 (17)	0.8060 (3)	0.0376 (18)
H10A	0.0892	−0.1480	0.7771	0.045*
C11A	0.0568 (5)	−0.0620 (15)	0.8494 (3)	0.0321 (16)
C12A	0.0869 (6)	0.1012 (18)	0.8933 (3)	0.0373 (18)
C13A	0.1640 (5)	0.2884 (17)	0.8925 (3)	0.0337 (17)
C14A	0.2105 (5)	0.3152 (17)	0.8482 (3)	0.0364 (18)
H14A	0.2597	0.4442	0.8466	0.044*
C15A	0.7253 (8)	0.309 (3)	0.5574 (4)	0.086 (4)
H15C	0.7754	0.3023	0.5342	0.129*
H15B	0.7573	0.2815	0.5928	0.129*
H15A	0.6929	0.4796	0.5547	0.129*
C16A	−0.0507 (6)	−0.413 (2)	0.8128 (3)	0.048 (2)
H16C	−0.0986	−0.5353	0.8237	0.072*
H16B	0.0075	−0.5075	0.8048	0.072*
H16A	−0.0817	−0.3192	0.7822	0.072*
C17A	−0.0268 (7)	0.284 (2)	0.9456 (4)	0.058 (3)
H17C	−0.0591	0.2464	0.9758	0.088*
H17B	−0.0775	0.3028	0.9153	0.088*
H17A	0.0112	0.4454	0.9512	0.088*
C18A	0.2695 (6)	0.619 (2)	0.9396 (4)	0.056 (3)
H18C	0.2762	0.7116	0.9724	0.085*
H18B	0.2542	0.7425	0.9113	0.085*
H18A	0.3319	0.5292	0.9364	0.085*
O1B	0.8368 (6)	−0.3520 (12)	0.6791 (3)	0.064 (2)
O2B	1.1551 (5)	0.082 (2)	0.5408 (2)	0.071 (2)
O3B	0.6942 (4)	−0.0861 (15)	0.9327 (2)	0.0526 (16)
O4B	0.5447 (4)	0.2633 (13)	0.93709 (19)	0.0432 (14)
O5B	0.4755 (4)	0.5755 (13)	0.8561 (2)	0.0453 (14)
N1B	0.8346 (5)	0.0774 (14)	0.7016 (2)	0.0397 (15)
H1NB	0.8270	0.2117	0.6812	0.048*
N2B	0.7795 (5)	0.0341 (15)	0.7419 (2)	0.0402 (16)
C1B	0.9427 (6)	−0.0541 (16)	0.6400 (3)	0.0367 (17)
C2B	0.9451 (7)	−0.1879 (19)	0.5939 (3)	0.051 (2)
H2B	0.8949	−0.3130	0.5839	0.061*
C3B	1.0160 (7)	−0.149 (2)	0.5623 (3)	0.053 (2)
H3B	1.0173	−0.2531	0.5326	0.064*
C4B	1.0878 (6)	0.052 (2)	0.5750 (3)	0.052 (2)
C5B	1.0874 (6)	0.195 (2)	0.6201 (3)	0.048 (2)
H5B	1.1358	0.3256	0.6293	0.058*
C6B	1.0139 (6)	0.143 (2)	0.6523 (3)	0.047 (2)
H6B	1.0129	0.2431	0.6825	0.056*
C7B	0.8691 (7)	−0.1257 (18)	0.6757 (3)	0.045 (2)
C8B	0.7321 (5)	0.241 (2)	0.7552 (3)	0.0399 (19)
H8B	0.7299	0.3951	0.7354	0.048*
C9B	0.6815 (5)	0.2261 (18)	0.8023 (3)	0.0395 (19)
C10B	0.7130 (5)	0.061 (2)	0.8438 (3)	0.0406 (19)
H10B	0.7669	−0.0535	0.8417	0.049*
C11B	0.6668 (5)	0.0605 (19)	0.8886 (3)	0.0392 (18)
C12B	0.5874 (5)	0.2440 (18)	0.8921 (3)	0.0340 (17)
C13B	0.5554 (5)	0.4060 (18)	0.8500 (3)	0.0348 (17)
C14B	0.6028 (5)	0.4086 (19)	0.8057 (3)	0.0399 (19)
H14B	0.5832	0.5282	0.7787	0.048*
C15B	1.2275 (8)	0.293 (3)	0.5513 (4)	0.086 (4)
H15D	1.2581	0.3281	0.5204	0.129*
H15E	1.2790	0.2425	0.5795	0.129*
H15F	1.1939	0.4499	0.5609	0.129*
C16B	0.7757 (6)	−0.263 (2)	0.9328 (4)	0.052 (2)
H16D	0.7973	−0.3246	0.9679	0.078*
H16E	0.8309	−0.1749	0.9199	0.078*
H16F	0.7544	−0.4118	0.9106	0.078*
C17B	0.4744 (7)	0.062 (2)	0.9456 (3)	0.059 (3)
H17D	0.4641	0.0629	0.9817	0.088*
H17E	0.5006	−0.1078	0.9372	0.088*
H17F	0.4111	0.0932	0.9237	0.088*
C18B	0.4404 (6)	0.746 (2)	0.8154 (3)	0.050 (2)
H18D	0.3865	0.8527	0.8252	0.075*
H18E	0.4158	0.6453	0.7846	0.075*
H18F	0.4947	0.8590	0.8082	0.075*

	U11	U22	U33	U12	U13	U23
O1A	0.111 (6)	0.058 (5)	0.076 (5)	−0.016 (5)	0.054 (4)	−0.001 (4)
O2A	0.064 (4)	0.122 (8)	0.058 (4)	−0.021 (5)	0.028 (3)	−0.003 (5)
O3A	0.047 (3)	0.042 (3)	0.046 (3)	−0.009 (3)	0.014 (3)	−0.004 (3)
O4A	0.060 (3)	0.045 (3)	0.036 (3)	0.007 (3)	0.023 (2)	0.011 (3)
O5A	0.058 (3)	0.061 (4)	0.045 (3)	−0.017 (4)	0.010 (3)	−0.010 (3)
N1A	0.055 (4)	0.064 (5)	0.053 (4)	−0.006 (4)	0.028 (3)	0.007 (4)
N2A	0.052 (4)	0.061 (6)	0.048 (4)	−0.005 (4)	0.017 (3)	−0.001 (4)
C1A	0.056 (5)	0.058 (6)	0.047 (5)	−0.007 (5)	0.017 (4)	−0.003 (5)
C2A	0.076 (5)	0.179 (12)	0.052 (4)	−0.006 (7)	0.025 (4)	−0.037 (7)
C3A	0.076 (5)	0.179 (12)	0.052 (4)	−0.006 (7)	0.025 (4)	−0.037 (7)
C4A	0.043 (4)	0.101 (9)	0.047 (5)	−0.002 (6)	0.009 (4)	−0.002 (6)
C5A	0.055 (5)	0.095 (9)	0.049 (5)	−0.002 (6)	0.015 (4)	−0.013 (6)
C6A	0.059 (6)	0.128 (12)	0.047 (5)	−0.001 (7)	0.014 (5)	−0.014 (7)
C7A	0.070 (6)	0.029 (5)	0.061 (5)	0.017 (5)	0.006 (5)	−0.016 (4)
C8A	0.057 (5)	0.047 (5)	0.034 (4)	0.007 (4)	0.014 (4)	0.000 (4)
C9A	0.038 (4)	0.042 (5)	0.036 (4)	0.007 (4)	0.014 (3)	−0.002 (4)
C10A	0.036 (4)	0.038 (5)	0.039 (4)	0.007 (4)	0.007 (3)	−0.002 (4)
C11A	0.035 (4)	0.022 (4)	0.039 (4)	0.005 (3)	0.008 (3)	0.006 (3)
C12A	0.043 (4)	0.034 (4)	0.036 (4)	0.010 (4)	0.009 (3)	0.005 (4)
C13A	0.030 (3)	0.034 (4)	0.037 (4)	0.009 (3)	0.005 (3)	−0.005 (4)
C14A	0.033 (4)	0.036 (5)	0.042 (4)	0.007 (4)	0.010 (3)	0.001 (4)
C15A	0.066 (6)	0.115 (12)	0.081 (7)	−0.029 (8)	0.023 (6)	0.027 (8)
C16A	0.048 (4)	0.044 (5)	0.050 (5)	−0.002 (5)	−0.002 (4)	−0.010 (5)
C17A	0.076 (6)	0.045 (6)	0.063 (5)	0.009 (5)	0.038 (5)	0.001 (5)
C18A	0.050 (5)	0.061 (6)	0.054 (5)	−0.009 (5)	−0.006 (4)	−0.015 (5)
O1B	0.100 (6)	0.023 (3)	0.076 (5)	−0.001 (3)	0.039 (4)	0.005 (3)
O2B	0.063 (4)	0.104 (6)	0.052 (3)	0.008 (5)	0.028 (3)	0.001 (5)
O3B	0.060 (3)	0.064 (4)	0.035 (3)	0.018 (4)	0.010 (3)	0.010 (3)
O4B	0.050 (3)	0.046 (3)	0.037 (3)	−0.001 (3)	0.018 (2)	0.000 (3)
O5B	0.049 (3)	0.044 (3)	0.045 (3)	0.021 (3)	0.013 (2)	0.004 (3)
N1B	0.056 (4)	0.030 (4)	0.037 (3)	0.010 (3)	0.020 (3)	0.001 (3)
N2B	0.042 (3)	0.040 (4)	0.041 (3)	−0.004 (3)	0.015 (3)	0.007 (3)
C1B	0.044 (4)	0.025 (4)	0.044 (4)	0.013 (3)	0.015 (3)	0.006 (3)
C2B	0.060 (5)	0.043 (5)	0.051 (5)	−0.008 (5)	0.012 (4)	−0.010 (4)
C3B	0.059 (5)	0.057 (6)	0.046 (5)	−0.001 (5)	0.021 (4)	−0.015 (4)
C4B	0.047 (4)	0.072 (7)	0.038 (4)	0.007 (5)	0.008 (3)	0.000 (5)
C5B	0.047 (5)	0.051 (6)	0.049 (5)	−0.002 (4)	0.014 (4)	0.002 (4)
C6B	0.047 (5)	0.051 (6)	0.043 (4)	0.003 (4)	0.013 (4)	−0.006 (4)
C7B	0.057 (5)	0.030 (5)	0.051 (5)	0.008 (4)	0.016 (4)	0.007 (4)
C8B	0.035 (4)	0.046 (5)	0.040 (4)	−0.003 (4)	0.011 (3)	−0.001 (4)
C9B	0.034 (4)	0.044 (5)	0.041 (4)	−0.005 (4)	0.008 (3)	−0.009 (4)
C10B	0.034 (4)	0.047 (5)	0.042 (4)	0.009 (4)	0.011 (3)	−0.009 (4)
C11B	0.039 (4)	0.038 (4)	0.040 (4)	0.006 (4)	0.004 (3)	−0.001 (4)
C12B	0.034 (4)	0.038 (4)	0.032 (4)	0.006 (4)	0.010 (3)	−0.002 (4)
C13B	0.030 (3)	0.040 (4)	0.037 (4)	0.001 (4)	0.013 (3)	−0.010 (4)
C14B	0.040 (4)	0.048 (5)	0.032 (4)	0.002 (4)	0.007 (3)	−0.003 (4)
C15B	0.061 (6)	0.124 (12)	0.081 (7)	−0.032 (8)	0.040 (6)	−0.035 (9)
C16B	0.052 (5)	0.038 (5)	0.063 (5)	0.012 (4)	0.004 (4)	0.010 (5)
C17B	0.072 (6)	0.060 (6)	0.053 (5)	−0.002 (6)	0.033 (5)	0.008 (6)
C18B	0.047 (5)	0.051 (5)	0.051 (5)	0.015 (5)	0.004 (4)	−0.009 (5)

O1A—C7A	1.208 (13)	O1B—C7B	1.229 (11)
O2A—C4A	1.355 (10)	O2B—C4B	1.354 (9)
O2A—C15A	1.394 (15)	O2B—C15B	1.438 (15)
O3A—C11A	1.333 (9)	O3B—C11B	1.361 (10)
O3A—C16A	1.452 (10)	O3B—C16B	1.408 (10)
O4A—C12A	1.376 (8)	O4B—C12B	1.366 (8)
O4A—C17A	1.442 (11)	O4B—C17B	1.422 (11)
O5A—C13A	1.371 (9)	O5B—C18B	1.386 (11)
O5A—C18A	1.412 (11)	O5B—C13B	1.394 (9)
N1A—C7A	1.315 (12)	N1B—C7B	1.340 (11)
N1A—N2A	1.401 (9)	N1B—N2B	1.374 (8)
N1A—H1NA	0.8600	N1B—H1NB	0.8545
N2A—C8A	1.243 (12)	N2B—C8B	1.290 (11)
C1A—C6A	1.422 (17)	C1B—C2B	1.371 (11)
C1A—C2A	1.449 (16)	C1B—C6B	1.380 (12)
C1A—C7A	1.532 (13)	C1B—C7B	1.483 (11)
C2A—C3A	1.459 (18)	C2B—C3B	1.349 (11)
C2A—H2A	0.9300	C2B—H2B	0.9300
C3A—C4A	1.39 (2)	C3B—C4B	1.402 (14)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.377 (14)	C4B—C5B	1.367 (12)
C5A—C6A	1.370 (13)	C5B—C6B	1.395 (11)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—H6A	0.9300	C6B—H6B	0.9300
C8A—C9A	1.493 (10)	C8B—C9B	1.474 (10)
C8A—H8AA	0.9300	C8B—H8B	0.9300
C9A—C10A	1.363 (11)	C9B—C10B	1.371 (12)
C9A—C14A	1.403 (11)	C9B—C14B	1.408 (11)
C10A—C11A	1.388 (10)	C10B—C11B	1.385 (10)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.409 (11)	C11B—C12B	1.420 (11)
C12A—C13A	1.398 (11)	C12B—C13B	1.376 (11)
C13A—C14A	1.381 (10)	C13B—C14B	1.382 (9)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15C	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15A	0.9600	C15B—H15F	0.9600
C16A—H16C	0.9600	C16B—H16D	0.9600
C16A—H16B	0.9600	C16B—H16E	0.9600
C16A—H16A	0.9600	C16B—H16F	0.9600
C17A—H17C	0.9600	C17B—H17D	0.9600
C17A—H17B	0.9600	C17B—H17E	0.9600
C17A—H17A	0.9600	C17B—H17F	0.9600
C18A—H18C	0.9600	C18B—H18D	0.9600
C18A—H18B	0.9600	C18B—H18E	0.9600
C18A—H18A	0.9600	C18B—H18F	0.9600
C4A—O2A—C15A	118.7 (9)	C4B—O2B—C15B	116.7 (8)
C11A—O3A—C16A	117.9 (6)	C11B—O3B—C16B	117.5 (6)
C12A—O4A—C17A	113.5 (6)	C12B—O4B—C17B	116.3 (7)
C13A—O5A—C18A	118.9 (6)	C18B—O5B—C13B	118.5 (6)
C7A—N1A—N2A	118.3 (9)	C7B—N1B—N2B	120.9 (7)
C7A—N1A—H1NA	120.8	C7B—N1B—H1NB	108.7
N2A—N1A—H1NA	120.8	N2B—N1B—H1NB	124.3
C8A—N2A—N1A	112.9 (8)	C8B—N2B—N1B	114.0 (7)
C6A—C1A—C2A	121.8 (9)	C2B—C1B—C6B	116.9 (7)
C6A—C1A—C7A	123.3 (8)	C2B—C1B—C7B	121.2 (8)
C2A—C1A—C7A	114.9 (10)	C6B—C1B—C7B	121.9 (8)
C1A—C2A—C3A	111.1 (15)	C3B—C2B—C1B	123.9 (9)
C1A—C2A—H2A	124.5	C3B—C2B—H2B	118.0
C3A—C2A—H2A	124.5	C1B—C2B—H2B	118.0
C4A—C3A—C2A	125.6 (11)	C2B—C3B—C4B	118.6 (8)
C4A—C3A—H3A	117.2	C2B—C3B—H3B	120.7
C2A—C3A—H3A	117.2	C4B—C3B—H3B	120.7
O2A—C4A—C5A	124.9 (11)	O2B—C4B—C5B	125.4 (10)
O2A—C4A—C3A	116.0 (9)	O2B—C4B—C3B	114.9 (8)
C5A—C4A—C3A	119.1 (9)	C5B—C4B—C3B	119.6 (8)
C6A—C5A—C4A	119.6 (11)	C4B—C5B—C6B	119.7 (9)
C6A—C5A—H5A	120.2	C4B—C5B—H5B	120.2
C4A—C5A—H5A	120.2	C6B—C5B—H5B	120.2
C5A—C6A—C1A	122.2 (10)	C1B—C6B—C5B	121.2 (8)
C5A—C6A—H6A	118.9	C1B—C6B—H6B	119.4
C1A—C6A—H6A	118.9	C5B—C6B—H6B	119.4
O1A—C7A—N1A	127.7 (10)	O1B—C7B—N1B	121.8 (8)
O1A—C7A—C1A	119.1 (9)	O1B—C7B—C1B	122.8 (8)
N1A—C7A—C1A	113.0 (9)	N1B—C7B—C1B	115.3 (8)
N2A—C8A—C9A	120.8 (8)	N2B—C8B—C9B	118.5 (8)
N2A—C8A—H8AA	119.6	N2B—C8B—H8B	120.7
C9A—C8A—H8AA	119.6	C9B—C8B—H8B	120.7
C10A—C9A—C14A	122.1 (7)	C10B—C9B—C14B	119.8 (7)
C10A—C9A—C8A	122.1 (7)	C10B—C9B—C8B	123.1 (7)
C14A—C9A—C8A	115.9 (7)	C14B—C9B—C8B	116.8 (8)
C9A—C10A—C11A	120.0 (7)	C9B—C10B—C11B	121.8 (7)
C9A—C10A—H10A	120.0	C9B—C10B—H10B	119.1
C11A—C10A—H10A	120.0	C11B—C10B—H10B	119.1
O3A—C11A—C10A	126.8 (7)	O3B—C11B—C10B	126.8 (7)
O3A—C11A—C12A	114.4 (6)	O3B—C11B—C12B	114.5 (6)
C10A—C11A—C12A	118.8 (7)	C10B—C11B—C12B	118.4 (7)
O4A—C12A—C13A	120.6 (7)	O4B—C12B—C13B	120.5 (7)
O4A—C12A—C11A	118.8 (7)	O4B—C12B—C11B	120.4 (7)
C13A—C12A—C11A	120.6 (7)	C13B—C12B—C11B	119.2 (6)
O5A—C13A—C14A	123.9 (7)	C12B—C13B—C14B	122.0 (7)
O5A—C13A—C12A	116.4 (6)	C12B—C13B—O5B	115.6 (6)
C14A—C13A—C12A	119.7 (7)	C14B—C13B—O5B	122.4 (7)
C13A—C14A—C9A	118.7 (7)	C13B—C14B—C9B	118.5 (8)
C13A—C14A—H14A	120.6	C13B—C14B—H14B	120.7
C9A—C14A—H14A	120.6	C9B—C14B—H14B	120.7
O2A—C15A—H15C	109.5	O2B—C15B—H15D	109.5
O2A—C15A—H15B	109.5	O2B—C15B—H15E	109.5
H15C—C15A—H15B	109.5	H15D—C15B—H15E	109.5
O2A—C15A—H15A	109.5	O2B—C15B—H15F	109.5
H15C—C15A—H15A	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15A	109.5	H15E—C15B—H15F	109.5
O3A—C16A—H16C	109.5	O3B—C16B—H16D	109.5
O3A—C16A—H16B	109.5	O3B—C16B—H16E	109.5
H16C—C16A—H16B	109.5	H16D—C16B—H16E	109.5
O3A—C16A—H16A	109.5	O3B—C16B—H16F	109.5
H16C—C16A—H16A	109.5	H16D—C16B—H16F	109.5
H16B—C16A—H16A	109.5	H16E—C16B—H16F	109.5
O4A—C17A—H17C	109.5	O4B—C17B—H17D	109.5
O4A—C17A—H17B	109.5	O4B—C17B—H17E	109.5
H17C—C17A—H17B	109.5	H17D—C17B—H17E	109.5
O4A—C17A—H17A	109.5	O4B—C17B—H17F	109.5
H17C—C17A—H17A	109.5	H17D—C17B—H17F	109.5
H17B—C17A—H17A	109.5	H17E—C17B—H17F	109.5
O5A—C18A—H18C	109.5	O5B—C18B—H18D	109.5
O5A—C18A—H18B	109.5	O5B—C18B—H18E	109.5
H18C—C18A—H18B	109.5	H18D—C18B—H18E	109.5
O5A—C18A—H18A	109.5	O5B—C18B—H18F	109.5
H18C—C18A—H18A	109.5	H18D—C18B—H18F	109.5
H18B—C18A—H18A	109.5	H18E—C18B—H18F	109.5
C7A—N1A—N2A—C8A	170.6 (9)	C7B—N1B—N2B—C8B	−165.1 (8)
C6A—C1A—C2A—C3A	−7.8 (19)	C6B—C1B—C2B—C3B	4.3 (14)
C7A—C1A—C2A—C3A	176.2 (11)	C7B—C1B—C2B—C3B	−173.6 (9)
C1A—C2A—C3A—C4A	10 (2)	C1B—C2B—C3B—C4B	−4.5 (15)
C15A—O2A—C4A—C5A	1.6 (18)	C15B—O2B—C4B—C5B	−4.3 (15)
C15A—O2A—C4A—C3A	−180.0 (12)	C15B—O2B—C4B—C3B	177.6 (9)
C2A—C3A—C4A—O2A	174.8 (15)	C2B—C3B—C4B—O2B	−178.8 (9)
C2A—C3A—C4A—C5A	−7 (2)	C2B—C3B—C4B—C5B	3.0 (14)
O2A—C4A—C5A—C6A	179.2 (12)	O2B—C4B—C5B—C6B	−179.6 (9)
C3A—C4A—C5A—C6A	0.9 (18)	C3B—C4B—C5B—C6B	−1.6 (14)
C4A—C5A—C6A—C1A	0.6 (18)	C2B—C1B—C6B—C5B	−2.6 (12)
C2A—C1A—C6A—C5A	3.4 (19)	C7B—C1B—C6B—C5B	175.2 (8)
C7A—C1A—C6A—C5A	179.0 (11)	C4B—C5B—C6B—C1B	1.4 (14)
N2A—N1A—C7A—O1A	3.5 (16)	N2B—N1B—C7B—O1B	15.2 (14)
N2A—N1A—C7A—C1A	−171.2 (7)	N2B—N1B—C7B—C1B	−169.2 (6)
C6A—C1A—C7A—O1A	−142.0 (12)	C2B—C1B—C7B—O1B	29.8 (14)
C2A—C1A—C7A—O1A	33.9 (15)	C6B—C1B—C7B—O1B	−148.0 (10)
C6A—C1A—C7A—N1A	33.2 (14)	C2B—C1B—C7B—N1B	−145.7 (9)
C2A—C1A—C7A—N1A	−150.8 (11)	C6B—C1B—C7B—N1B	36.5 (11)
N1A—N2A—C8A—C9A	−174.4 (7)	N1B—N2B—C8B—C9B	−172.2 (6)
N2A—C8A—C9A—C10A	−31.3 (13)	N2B—C8B—C9B—C10B	27.5 (12)
N2A—C8A—C9A—C14A	147.3 (9)	N2B—C8B—C9B—C14B	−158.0 (7)
C14A—C9A—C10A—C11A	−0.7 (12)	C14B—C9B—C10B—C11B	2.6 (13)
C8A—C9A—C10A—C11A	177.8 (7)	C8B—C9B—C10B—C11B	177.0 (8)
C16A—O3A—C11A—C10A	4.8 (11)	C16B—O3B—C11B—C10B	−2.3 (13)
C16A—O3A—C11A—C12A	−175.8 (7)	C16B—O3B—C11B—C12B	−177.2 (8)
C9A—C10A—C11A—O3A	177.8 (7)	C9B—C10B—C11B—O3B	−177.2 (8)
C9A—C10A—C11A—C12A	−1.7 (11)	C9B—C10B—C11B—C12B	−2.5 (13)
C17A—O4A—C12A—C13A	72.8 (9)	C17B—O4B—C12B—C13B	103.9 (10)
C17A—O4A—C12A—C11A	−108.5 (9)	C17B—O4B—C12B—C11B	−77.5 (9)
O3A—C11A—C12A—O4A	3.5 (10)	O3B—C11B—C12B—O4B	0.1 (12)
C10A—C11A—C12A—O4A	−177.0 (7)	C10B—C11B—C12B—O4B	−175.3 (8)
O3A—C11A—C12A—C13A	−177.7 (7)	O3B—C11B—C12B—C13B	178.6 (8)
C10A—C11A—C12A—C13A	1.8 (11)	C10B—C11B—C12B—C13B	3.3 (12)
C18A—O5A—C13A—C14A	0.3 (12)	O4B—C12B—C13B—C14B	174.1 (8)
C18A—O5A—C13A—C12A	178.5 (7)	C11B—C12B—C13B—C14B	−4.5 (13)
O4A—C12A—C13A—O5A	1.0 (11)	O4B—C12B—C13B—O5B	−3.0 (11)
C11A—C12A—C13A—O5A	−177.7 (7)	C11B—C12B—C13B—O5B	178.4 (7)
O4A—C12A—C13A—C14A	179.3 (7)	C18B—O5B—C13B—C12B	179.2 (8)
C11A—C12A—C13A—C14A	0.5 (11)	C18B—O5B—C13B—C14B	2.2 (12)
O5A—C13A—C14A—C9A	175.3 (7)	C12B—C13B—C14B—C9B	4.6 (12)
C12A—C13A—C14A—C9A	−2.9 (11)	O5B—C13B—C14B—C9B	−178.5 (7)
C10A—C9A—C14A—C13A	3.0 (12)	C10B—C9B—C14B—C13B	−3.6 (12)
C8A—C9A—C14A—C13A	−175.6 (7)	C8B—C9B—C14B—C13B	−178.2 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···O1Ai	0.86	2.11	2.944 (13)	164
N1B—H1NB···O1Bi	0.85	2.21	2.939 (9)	144
C8B—H8B···O1Bi	0.93	2.52	3.287 (11)	140
C15B—H15D···O2Aii	0.96	2.60	3.498 (14)	156
C17B—H17D···O4Biii	0.96	2.60	3.420 (10)	144
C16A—H16B···Cg1iv	0.96	2.66	3.429 (10)	138
C16B—H16F···Cg2iv	0.96	2.77	3.697 (10)	162
C18A—H18B···Cg1i	0.96	2.85	3.739 (10)	155
C18B—H18F···Cg2i	0.96	2.74	3.583 (10)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C9A–C14A and C9B–C14B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1NA⋯O1Ai	0.86	2.11	2.944 (13)	164
N1B—H1NB⋯O1Bi	0.85	2.21	2.939 (9)	144
C8B—H8B⋯O1Bi	0.93	2.52	3.287 (11)	140
C15B—H15D⋯O2Aii	0.96	2.60	3.498 (14)	156
C17B—H17D⋯O4Biii	0.96	2.60	3.420 (10)	144
C16A—H16B⋯Cg1iv	0.96	2.66	3.429 (10)	138
C16B—H16F⋯Cg2iv	0.96	2.77	3.697 (10)	162
C18A—H18B⋯Cg1i	0.96	2.85	3.739 (10)	155
C18B—H18F⋯Cg2i	0.96	2.74	3.583 (10)	146

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