(1E,2E)-1,2-Bis[1-(2-methoxy-phen-yl)ethyl-idene]hydrazine.

There are two crystallographically independent mol-ecules in the asymmetric unit of the title compound, C(18)H(20)N(2)O(2). The two mol-ecules exist in an E,E configuration with respect to the two C=N double bonds. The dihedral angles between the two benzene rings in each mol-ecule are 16.89 (6) and 18.84 (6)°. In each mol-ecule, the two meth-oxy groups are coplanar with their attached benzene rings, with r.m.s. deviations of 0.0078 and 0.0336 Å in one mol-ecule, and 0.0163 and 0.0207 Å in the other. An intra-molecular C-H⋯O hydrogen bond is present in one mol-ecule. In the crystal structure, mol-ecules are arranged into ribbons along the c axis. These ribbons are further stacked along the a axis. The mol-ecules are consolidated by C⋯N [3.306 (2)-3.427 (2) Å] and C⋯O [3.3284 (16)-3.3863 (15) Å] short contacts. C-H⋯π inter-actions are also observed.

Related literature

For related structures, see: Jansrisewangwong et al. (2010 ▶); Zhao et al. (2006 ▶). For background to and biological activities of hydra­zones, see: El-Sherif (2009 ▶); Melnyk et al. (2006 ▶); Papakonstanti­nou-Garoufalias et al. (2002 ▶); Patole et al. (2003 ▶); Sridhar et al. (2002 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C18H20N2O2

M = 296.36

Triclinic,

a = 7.9695 (2) Å

b = 14.8028 (4) Å

c = 15.4704 (4) Å

α = 117.909 (1)°

β = 90.151 (1)°

γ = 91.979 (1)°

V = 1611.46 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.55 × 0.37 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.957, T max = 0.984

39016 measured reflections

9367 independent reflections

7773 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.123

S = 1.02

9367 reflections

405 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.24 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 datablocks global, I. DOI: 10.1107/S1600536810043266/rz2497sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043266/rz2497Isup2.hkl

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

C18H20N2O2	Z = 4
Mr = 296.36	F(000) = 632
Triclinic, P1	Dx = 1.222 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9695 (2) Å	Cell parameters from 9367 reflections
b = 14.8028 (4) Å	θ = 1.5–30.0°
c = 15.4704 (4) Å	µ = 0.08 mm−1
α = 117.909 (1)°	T = 100 K
β = 90.151 (1)°	Block, yellow
γ = 91.979 (1)°	0.55 × 0.37 × 0.20 mm
V = 1611.46 (7) Å3

Bruker APEXII CCD area-detector diffractometer	9367 independent reflections
Radiation source: sealed tube	7773 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 30.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
Tmin = 0.957, Tmax = 0.984	k = −20→20
39016 measured reflections	l = −21→21

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0567P)2 + 0.6198P] where P = (Fo2 + 2Fc2)/3
9367 reflections	(Δ/σ)max = 0.001
405 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.24 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 120.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
O1A	0.75936 (11)	0.36403 (6)	0.20160 (6)	0.02473 (18)
O2A	0.05444 (11)	0.30674 (7)	0.43253 (6)	0.02626 (18)
N1A	0.46008 (11)	0.14041 (7)	0.17196 (6)	0.01854 (18)
N2A	0.37331 (11)	0.12913 (7)	0.24477 (7)	0.01884 (18)
C1A	0.78882 (13)	0.27395 (9)	0.12023 (8)	0.0191 (2)
C2A	0.88899 (15)	0.26604 (10)	0.04349 (9)	0.0252 (2)
H2AA	0.9423	0.3241	0.0460	0.030*
C3A	0.90873 (16)	0.17096 (11)	−0.03661 (9)	0.0293 (3)
H3AA	0.9765	0.1655	−0.0875	0.035*
C4A	0.82876 (17)	0.08417 (10)	−0.04166 (9)	0.0288 (3)
H4AA	0.8434	0.0206	−0.0953	0.035*
C5A	0.72626 (14)	0.09266 (9)	0.03416 (8)	0.0217 (2)
H5AA	0.6701	0.0346	0.0299	0.026*
C6A	0.70634 (12)	0.18658 (8)	0.11623 (7)	0.01635 (19)
C7A	0.60121 (13)	0.19120 (8)	0.19741 (7)	0.01595 (19)
C8A	0.22915 (13)	0.16892 (9)	0.26668 (8)	0.0194 (2)
C9A	0.12412 (13)	0.13672 (9)	0.32803 (8)	0.0201 (2)
C10A	0.11483 (15)	0.03358 (10)	0.30463 (8)	0.0251 (2)
H10A	0.1765	−0.0125	0.2527	0.030*
C11A	0.01548 (16)	−0.00223 (11)	0.35703 (9)	0.0297 (3)
H11A	0.0111	−0.0713	0.3404	0.036*
C12A	−0.07677 (15)	0.06652 (11)	0.43420 (9)	0.0295 (3)
H12A	−0.1452	0.0431	0.4687	0.035*
C13A	−0.06803 (14)	0.16999 (11)	0.46046 (9)	0.0261 (2)
H13A	−0.1295	0.2156	0.5128	0.031*
C14A	0.03324 (13)	0.20564 (10)	0.40820 (8)	0.0217 (2)
C15A	0.8430 (2)	0.45433 (11)	0.20980 (12)	0.0457 (4)
H15A	0.8164	0.5115	0.2710	0.069*
H15B	0.8070	0.4664	0.1570	0.069*
H15C	0.9621	0.4460	0.2069	0.069*
C16A	0.66645 (14)	0.24582 (9)	0.30146 (8)	0.0200 (2)
H16A	0.6653	0.1990	0.3283	0.030*
H16B	0.5964	0.3018	0.3395	0.030*
H16C	0.7793	0.2715	0.3030	0.030*
C17A	0.15991 (16)	0.23508 (12)	0.22654 (10)	0.0323 (3)
H17A	0.1805	0.2051	0.1577	0.048*
H17B	0.2138	0.3020	0.2592	0.048*
H17C	0.0412	0.2404	0.2370	0.048*
C18A	−0.0294 (2)	0.37775 (12)	0.51799 (10)	0.0364 (3)
H18A	0.0057	0.4463	0.5331	0.055*
H18B	−0.0015	0.3658	0.5721	0.055*
H18C	−0.1486	0.3687	0.5061	0.055*
O1B	0.45456 (11)	0.82808 (7)	0.44885 (6)	0.02682 (19)
O2B	−0.27309 (11)	0.85346 (6)	0.18823 (6)	0.02520 (18)
N1B	0.11694 (11)	0.64386 (7)	0.25137 (7)	0.01901 (18)
N2B	0.03346 (11)	0.65363 (7)	0.17709 (7)	0.01845 (18)
C1B	0.46224 (13)	0.72673 (10)	0.42254 (8)	0.0221 (2)
C2B	0.55967 (14)	0.68929 (11)	0.47331 (9)	0.0259 (2)
H2BA	0.6262	0.7344	0.5266	0.031*
C3B	0.55744 (16)	0.58569 (11)	0.44459 (9)	0.0311 (3)
H3BA	0.6235	0.5615	0.4784	0.037*
C4B	0.45791 (18)	0.51747 (11)	0.36600 (10)	0.0323 (3)
H4BA	0.4555	0.4479	0.3474	0.039*
C5B	0.36140 (15)	0.55442 (10)	0.31511 (9)	0.0262 (2)
H5BA	0.2944	0.5087	0.2624	0.031*
C6B	0.36273 (13)	0.65829 (9)	0.34121 (8)	0.0204 (2)
C7B	0.26160 (13)	0.69058 (9)	0.27974 (8)	0.0192 (2)
C8B	−0.11241 (12)	0.69174 (8)	0.19615 (7)	0.01565 (19)
C9B	−0.21463 (12)	0.67896 (8)	0.10995 (7)	0.01684 (19)
C10B	−0.23044 (14)	0.58243 (9)	0.02918 (8)	0.0219 (2)
H10B	−0.1732	0.5287	0.0291	0.026*
C11B	−0.33037 (16)	0.56475 (10)	−0.05160 (9)	0.0290 (3)
H11B	−0.3420	0.4995	−0.1045	0.035*
C12B	−0.41238 (16)	0.64566 (11)	−0.05217 (9)	0.0313 (3)
H12B	−0.4786	0.6344	−0.1061	0.038*
C13B	−0.39686 (15)	0.74310 (10)	0.02671 (9)	0.0274 (3)
H13B	−0.4515	0.7969	0.0253	0.033*
C14B	−0.29881 (13)	0.75991 (9)	0.10809 (8)	0.0196 (2)
C15B	0.5555 (2)	0.89710 (12)	0.53241 (11)	0.0390 (3)
H15D	0.5325	0.9664	0.5484	0.058*
H15E	0.6722	0.8856	0.5176	0.058*
H15F	0.5293	0.8855	0.5870	0.058*
C16B	0.33209 (15)	0.76471 (12)	0.24739 (10)	0.0311 (3)
H16D	0.3033	0.7408	0.1797	0.047*
H16E	0.4521	0.7703	0.2558	0.047*
H16F	0.2861	0.8305	0.2860	0.047*
C17B	−0.18961 (14)	0.73647 (9)	0.29538 (8)	0.0216 (2)
H17D	−0.1033	0.7526	0.3444	0.032*
H17E	−0.2696	0.6877	0.2978	0.032*
H17F	−0.2453	0.7976	0.3074	0.032*
C18B	−0.3482 (2)	0.93885 (11)	0.18693 (12)	0.0457 (4)
H18D	−0.3197	0.9997	0.2466	0.069*
H18E	−0.4680	0.9277	0.1809	0.069*
H18F	−0.3074	0.9467	0.1324	0.069*

	U11	U22	U33	U12	U13	U23
O1A	0.0321 (4)	0.0190 (4)	0.0229 (4)	−0.0043 (3)	0.0011 (3)	0.0100 (3)
O2A	0.0248 (4)	0.0347 (5)	0.0257 (4)	0.0080 (3)	0.0060 (3)	0.0190 (4)
N1A	0.0171 (4)	0.0241 (5)	0.0169 (4)	0.0001 (3)	0.0025 (3)	0.0117 (4)
N2A	0.0171 (4)	0.0243 (5)	0.0175 (4)	−0.0023 (3)	0.0010 (3)	0.0120 (4)
C1A	0.0180 (5)	0.0228 (5)	0.0178 (5)	−0.0019 (4)	−0.0019 (4)	0.0109 (4)
C2A	0.0238 (5)	0.0316 (6)	0.0239 (5)	−0.0085 (5)	−0.0002 (4)	0.0167 (5)
C3A	0.0278 (6)	0.0402 (7)	0.0209 (5)	−0.0039 (5)	0.0068 (4)	0.0155 (5)
C4A	0.0332 (6)	0.0304 (6)	0.0192 (5)	−0.0004 (5)	0.0076 (5)	0.0086 (5)
C5A	0.0242 (5)	0.0225 (5)	0.0186 (5)	−0.0013 (4)	0.0029 (4)	0.0098 (4)
C6A	0.0143 (4)	0.0211 (5)	0.0159 (4)	−0.0002 (4)	−0.0001 (3)	0.0105 (4)
C7A	0.0160 (4)	0.0183 (5)	0.0159 (4)	0.0028 (4)	0.0020 (3)	0.0098 (4)
C8A	0.0160 (4)	0.0285 (6)	0.0170 (5)	−0.0019 (4)	−0.0010 (4)	0.0136 (4)
C9A	0.0138 (4)	0.0330 (6)	0.0178 (5)	−0.0029 (4)	−0.0017 (3)	0.0156 (4)
C10A	0.0235 (5)	0.0328 (6)	0.0191 (5)	−0.0060 (5)	−0.0015 (4)	0.0128 (5)
C11A	0.0303 (6)	0.0353 (7)	0.0271 (6)	−0.0111 (5)	−0.0030 (5)	0.0185 (5)
C12A	0.0226 (5)	0.0480 (8)	0.0264 (6)	−0.0080 (5)	−0.0009 (4)	0.0250 (6)
C13A	0.0166 (5)	0.0458 (7)	0.0221 (5)	0.0020 (5)	0.0026 (4)	0.0209 (5)
C14A	0.0146 (4)	0.0357 (6)	0.0211 (5)	0.0014 (4)	−0.0012 (4)	0.0184 (5)
C15A	0.0716 (11)	0.0246 (7)	0.0364 (8)	−0.0172 (7)	0.0054 (7)	0.0116 (6)
C16A	0.0192 (5)	0.0259 (5)	0.0167 (5)	−0.0003 (4)	−0.0003 (4)	0.0115 (4)
C17A	0.0230 (6)	0.0553 (9)	0.0363 (7)	0.0105 (5)	0.0073 (5)	0.0355 (7)
C18A	0.0446 (8)	0.0412 (8)	0.0298 (6)	0.0173 (6)	0.0119 (6)	0.0207 (6)
O1B	0.0247 (4)	0.0356 (5)	0.0264 (4)	−0.0053 (3)	−0.0075 (3)	0.0201 (4)
O2B	0.0325 (4)	0.0206 (4)	0.0231 (4)	0.0069 (3)	−0.0027 (3)	0.0103 (3)
N1B	0.0166 (4)	0.0256 (5)	0.0178 (4)	0.0042 (3)	−0.0004 (3)	0.0124 (4)
N2B	0.0162 (4)	0.0246 (5)	0.0176 (4)	0.0013 (3)	−0.0015 (3)	0.0124 (4)
C1B	0.0136 (4)	0.0387 (6)	0.0210 (5)	0.0017 (4)	0.0019 (4)	0.0197 (5)
C2B	0.0162 (5)	0.0473 (7)	0.0215 (5)	0.0029 (5)	−0.0004 (4)	0.0220 (5)
C3B	0.0276 (6)	0.0490 (8)	0.0256 (6)	0.0146 (5)	0.0020 (5)	0.0241 (6)
C4B	0.0372 (7)	0.0367 (7)	0.0278 (6)	0.0158 (6)	0.0020 (5)	0.0182 (5)
C5B	0.0261 (6)	0.0343 (6)	0.0202 (5)	0.0103 (5)	0.0016 (4)	0.0138 (5)
C6B	0.0134 (4)	0.0346 (6)	0.0180 (5)	0.0057 (4)	0.0027 (4)	0.0160 (4)
C7B	0.0144 (4)	0.0299 (6)	0.0172 (5)	0.0042 (4)	0.0014 (3)	0.0141 (4)
C8B	0.0150 (4)	0.0179 (5)	0.0161 (4)	−0.0010 (4)	−0.0012 (3)	0.0098 (4)
C9B	0.0134 (4)	0.0228 (5)	0.0168 (4)	0.0009 (4)	−0.0005 (3)	0.0113 (4)
C10B	0.0230 (5)	0.0244 (5)	0.0181 (5)	0.0027 (4)	−0.0012 (4)	0.0097 (4)
C11B	0.0328 (6)	0.0310 (6)	0.0184 (5)	0.0019 (5)	−0.0058 (4)	0.0076 (5)
C12B	0.0299 (6)	0.0427 (7)	0.0203 (5)	0.0069 (5)	−0.0065 (4)	0.0135 (5)
C13B	0.0263 (6)	0.0357 (7)	0.0234 (5)	0.0100 (5)	−0.0021 (4)	0.0160 (5)
C14B	0.0182 (5)	0.0239 (5)	0.0183 (5)	0.0035 (4)	0.0009 (4)	0.0112 (4)
C15B	0.0461 (8)	0.0438 (8)	0.0347 (7)	−0.0164 (6)	−0.0191 (6)	0.0262 (7)
C16B	0.0189 (5)	0.0542 (8)	0.0363 (7)	−0.0069 (5)	−0.0063 (5)	0.0354 (7)
C17B	0.0206 (5)	0.0295 (6)	0.0180 (5)	0.0055 (4)	0.0025 (4)	0.0135 (4)
C18B	0.0700 (11)	0.0272 (7)	0.0393 (8)	0.0196 (7)	−0.0090 (7)	0.0140 (6)

O1A—C1A	1.3673 (14)	O1B—C1B	1.3619 (15)
O1A—C15A	1.4237 (16)	O1B—C15B	1.4366 (16)
O2A—C14A	1.3656 (15)	O2B—C14B	1.3670 (14)
O2A—C18A	1.4325 (15)	O2B—C18B	1.4255 (15)
N1A—C7A	1.2835 (14)	N1B—C7B	1.2877 (14)
N1A—N2A	1.3954 (12)	N1B—N2B	1.3938 (12)
N2A—C8A	1.2821 (14)	N2B—C8B	1.2837 (13)
C1A—C2A	1.3935 (15)	C1B—C2B	1.4004 (15)
C1A—C6A	1.4053 (15)	C1B—C6B	1.4086 (16)
C2A—C3A	1.3875 (18)	C2B—C3B	1.382 (2)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.3828 (19)	C3B—C4B	1.385 (2)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.3904 (16)	C4B—C5B	1.3926 (16)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.3906 (15)	C5B—C6B	1.3946 (18)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.4876 (14)	C6B—C7B	1.4935 (14)
C7A—C16A	1.5044 (14)	C7B—C16B	1.4977 (17)
C8A—C9A	1.4929 (15)	C8B—C9B	1.4917 (13)
C8A—C17A	1.5013 (16)	C8B—C17B	1.5018 (14)
C9A—C10A	1.3935 (17)	C9B—C10B	1.3907 (15)
C9A—C14A	1.4052 (16)	C9B—C14B	1.4052 (15)
C10A—C11A	1.3936 (17)	C10B—C11B	1.3924 (15)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.3858 (19)	C11B—C12B	1.3876 (18)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.388 (2)	C12B—C13B	1.3870 (18)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.3990 (16)	C13B—C14B	1.3948 (15)
C13A—H13A	0.9300	C13B—H13B	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
C16A—H16A	0.9600	C16B—H16D	0.9600
C16A—H16B	0.9600	C16B—H16E	0.9600
C16A—H16C	0.9600	C16B—H16F	0.9600
C17A—H17A	0.9600	C17B—H17D	0.9600
C17A—H17B	0.9600	C17B—H17E	0.9600
C17A—H17C	0.9600	C17B—H17F	0.9600
C18A—H18A	0.9600	C18B—H18D	0.9600
C18A—H18B	0.9600	C18B—H18E	0.9600
C18A—H18C	0.9600	C18B—H18F	0.9600
C1A—O1A—C15A	117.43 (10)	C1B—O1B—C15B	116.31 (10)
C14A—O2A—C18A	116.57 (10)	C14B—O2B—C18B	117.64 (10)
C7A—N1A—N2A	116.67 (9)	C7B—N1B—N2B	116.99 (9)
C8A—N2A—N1A	116.75 (9)	C8B—N2B—N1B	117.11 (9)
O1A—C1A—C2A	124.13 (10)	O1B—C1B—C2B	123.31 (11)
O1A—C1A—C6A	115.45 (9)	O1B—C1B—C6B	116.88 (9)
C2A—C1A—C6A	120.40 (10)	C2B—C1B—C6B	119.79 (12)
C3A—C2A—C1A	119.57 (11)	C3B—C2B—C1B	120.34 (12)
C3A—C2A—H2AA	120.2	C3B—C2B—H2BA	119.8
C1A—C2A—H2AA	120.2	C1B—C2B—H2BA	119.8
C4A—C3A—C2A	120.79 (11)	C2B—C3B—C4B	120.68 (11)
C4A—C3A—H3AA	119.6	C2B—C3B—H3BA	119.7
C2A—C3A—H3AA	119.6	C4B—C3B—H3BA	119.7
C3A—C4A—C5A	119.47 (11)	C3B—C4B—C5B	119.11 (13)
C3A—C4A—H4AA	120.3	C3B—C4B—H4BA	120.4
C5A—C4A—H4AA	120.3	C5B—C4B—H4BA	120.4
C4A—C5A—C6A	121.10 (11)	C4B—C5B—C6B	121.66 (12)
C4A—C5A—H5AA	119.4	C4B—C5B—H5BA	119.2
C6A—C5A—H5AA	119.4	C6B—C5B—H5BA	119.2
C5A—C6A—C1A	118.64 (10)	C5B—C6B—C1B	118.39 (10)
C5A—C6A—C7A	119.18 (10)	C5B—C6B—C7B	118.06 (10)
C1A—C6A—C7A	122.16 (9)	C1B—C6B—C7B	123.53 (11)
N1A—C7A—C6A	115.93 (9)	N1B—C7B—C6B	114.65 (10)
N1A—C7A—C16A	123.32 (9)	N1B—C7B—C16B	123.60 (9)
C6A—C7A—C16A	120.57 (9)	C6B—C7B—C16B	121.53 (9)
N2A—C8A—C9A	115.31 (10)	N2B—C8B—C9B	115.69 (9)
N2A—C8A—C17A	123.59 (10)	N2B—C8B—C17B	124.37 (9)
C9A—C8A—C17A	120.83 (9)	C9B—C8B—C17B	119.59 (9)
C10A—C9A—C14A	118.35 (10)	C10B—C9B—C14B	118.76 (9)
C10A—C9A—C8A	118.65 (10)	C10B—C9B—C8B	118.58 (9)
C14A—C9A—C8A	123.00 (11)	C14B—C9B—C8B	122.64 (10)
C9A—C10A—C11A	121.69 (12)	C9B—C10B—C11B	121.21 (11)
C9A—C10A—H10A	119.2	C9B—C10B—H10B	119.4
C11A—C10A—H10A	119.2	C11B—C10B—H10B	119.4
C12A—C11A—C10A	119.09 (13)	C12B—C11B—C10B	119.19 (11)
C12A—C11A—H11A	120.5	C12B—C11B—H11B	120.4
C10A—C11A—H11A	120.5	C10B—C11B—H11B	120.4
C11A—C12A—C13A	120.65 (11)	C13B—C12B—C11B	120.86 (11)
C11A—C12A—H12A	119.7	C13B—C12B—H12B	119.6
C13A—C12A—H12A	119.7	C11B—C12B—H12B	119.6
C12A—C13A—C14A	120.00 (11)	C12B—C13B—C14B	119.64 (11)
C12A—C13A—H13A	120.0	C12B—C13B—H13B	120.2
C14A—C13A—H13A	120.0	C14B—C13B—H13B	120.2
O2A—C14A—C13A	123.34 (11)	O2B—C14B—C13B	123.88 (10)
O2A—C14A—C9A	116.44 (10)	O2B—C14B—C9B	115.77 (9)
C13A—C14A—C9A	120.19 (12)	C13B—C14B—C9B	120.31 (11)
O1A—C15A—H15A	109.5	O1B—C15B—H15D	109.5
O1A—C15A—H15B	109.5	O1B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
O1A—C15A—H15C	109.5	O1B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C7A—C16A—H16A	109.5	C7B—C16B—H16D	109.5
C7A—C16A—H16B	109.5	C7B—C16B—H16E	109.5
H16A—C16A—H16B	109.5	H16D—C16B—H16E	109.5
C7A—C16A—H16C	109.5	C7B—C16B—H16F	109.5
H16A—C16A—H16C	109.5	H16D—C16B—H16F	109.5
H16B—C16A—H16C	109.5	H16E—C16B—H16F	109.5
C8A—C17A—H17A	109.5	C8B—C17B—H17D	109.5
C8A—C17A—H17B	109.5	C8B—C17B—H17E	109.5
H17A—C17A—H17B	109.5	H17D—C17B—H17E	109.5
C8A—C17A—H17C	109.5	C8B—C17B—H17F	109.5
H17A—C17A—H17C	109.5	H17D—C17B—H17F	109.5
H17B—C17A—H17C	109.5	H17E—C17B—H17F	109.5
O2A—C18A—H18A	109.5	O2B—C18B—H18D	109.5
O2A—C18A—H18B	109.5	O2B—C18B—H18E	109.5
H18A—C18A—H18B	109.5	H18D—C18B—H18E	109.5
O2A—C18A—H18C	109.5	O2B—C18B—H18F	109.5
H18A—C18A—H18C	109.5	H18D—C18B—H18F	109.5
H18B—C18A—H18C	109.5	H18E—C18B—H18F	109.5
C7A—N1A—N2A—C8A	117.39 (11)	C7B—N1B—N2B—C8B	−121.46 (11)
C15A—O1A—C1A—C2A	−3.00 (17)	C15B—O1B—C1B—C2B	0.99 (16)
C15A—O1A—C1A—C6A	178.73 (12)	C15B—O1B—C1B—C6B	179.48 (11)
O1A—C1A—C2A—C3A	−179.01 (11)	O1B—C1B—C2B—C3B	177.84 (11)
C6A—C1A—C2A—C3A	−0.82 (17)	C6B—C1B—C2B—C3B	−0.61 (16)
C1A—C2A—C3A—C4A	0.69 (19)	C1B—C2B—C3B—C4B	−0.64 (18)
C2A—C3A—C4A—C5A	0.6 (2)	C2B—C3B—C4B—C5B	0.9 (2)
C3A—C4A—C5A—C6A	−1.75 (19)	C3B—C4B—C5B—C6B	0.11 (19)
C4A—C5A—C6A—C1A	1.61 (16)	C4B—C5B—C6B—C1B	−1.33 (17)
C4A—C5A—C6A—C7A	−177.40 (10)	C4B—C5B—C6B—C7B	177.19 (11)
O1A—C1A—C6A—C5A	178.03 (9)	O1B—C1B—C6B—C5B	−176.99 (10)
C2A—C1A—C6A—C5A	−0.31 (15)	C2B—C1B—C6B—C5B	1.56 (16)
O1A—C1A—C6A—C7A	−2.99 (14)	O1B—C1B—C6B—C7B	4.58 (15)
C2A—C1A—C6A—C7A	178.67 (10)	C2B—C1B—C6B—C7B	−176.86 (10)
N2A—N1A—C7A—C6A	169.23 (9)	N2B—N1B—C7B—C6B	−166.13 (9)
N2A—N1A—C7A—C16A	−5.92 (15)	N2B—N1B—C7B—C16B	8.60 (16)
C5A—C6A—C7A—N1A	−45.02 (14)	C5B—C6B—C7B—N1B	40.45 (14)
C1A—C6A—C7A—N1A	136.01 (11)	C1B—C6B—C7B—N1B	−141.12 (11)
C5A—C6A—C7A—C16A	130.28 (11)	C5B—C6B—C7B—C16B	−134.40 (12)
C1A—C6A—C7A—C16A	−48.69 (14)	C1B—C6B—C7B—C16B	44.04 (16)
N1A—N2A—C8A—C9A	167.25 (9)	N1B—N2B—C8B—C9B	−166.24 (9)
N1A—N2A—C8A—C17A	−6.81 (17)	N1B—N2B—C8B—C17B	6.97 (16)
N2A—C8A—C9A—C10A	−43.91 (14)	N2B—C8B—C9B—C10B	48.84 (14)
C17A—C8A—C9A—C10A	130.33 (12)	C17B—C8B—C9B—C10B	−124.72 (11)
N2A—C8A—C9A—C14A	136.44 (11)	N2B—C8B—C9B—C14B	−132.77 (11)
C17A—C8A—C9A—C14A	−49.33 (16)	C17B—C8B—C9B—C14B	53.67 (15)
C14A—C9A—C10A—C11A	1.51 (16)	C14B—C9B—C10B—C11B	−1.41 (17)
C8A—C9A—C10A—C11A	−178.16 (10)	C8B—C9B—C10B—C11B	177.04 (11)
C9A—C10A—C11A—C12A	0.19 (18)	C9B—C10B—C11B—C12B	1.50 (19)
C10A—C11A—C12A—C13A	−1.31 (18)	C10B—C11B—C12B—C13B	−0.5 (2)
C11A—C12A—C13A—C14A	0.68 (18)	C11B—C12B—C13B—C14B	−0.6 (2)
C18A—O2A—C14A—C13A	1.85 (15)	C18B—O2B—C14B—C13B	−1.54 (18)
C18A—O2A—C14A—C9A	−176.08 (10)	C18B—O2B—C14B—C9B	176.41 (12)
C12A—C13A—C14A—O2A	−176.79 (10)	C12B—C13B—C14B—O2B	178.53 (12)
C12A—C13A—C14A—C9A	1.07 (16)	C12B—C13B—C14B—C9B	0.67 (18)
C10A—C9A—C14A—O2A	175.87 (9)	C10B—C9B—C14B—O2B	−177.71 (10)
C8A—C9A—C14A—O2A	−4.47 (15)	C8B—C9B—C14B—O2B	3.90 (15)
C10A—C9A—C14A—C13A	−2.13 (15)	C10B—C9B—C14B—C13B	0.32 (16)
C8A—C9A—C14A—C13A	177.52 (10)	C8B—C9B—C14B—C13B	−178.07 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C17B—H17F···O2B	0.96	2.36	2.9918 (17)	123
C15B—H15E···Cg1i	0.96	2.83	3.5974 (17)	138
C18A—H18C···Cg2ii	0.96	2.90	3.6976 (17)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17B—H17F⋯O2B	0.96	2.36	2.9918 (17)	123
C15B—H15E⋯Cg1i	0.96	2.83	3.5974 (17)	138
C18A—H18C⋯Cg2ii	0.96	2.90	3.6976 (17)	141

Symmetry codes: (i) ; (ii) . Cg1 and Cg2 are the centroids of the C9A–C14A and C1B–C6B rings, respectively.