N'-[(E)-1-Phenyl-ethyl-idene]benzo-hydrazide.

The title compound, C(15)H(14)N(2)O, crystallized with two independent mol-ecules in the asymmetric unit. Both mol-ecules are non-planar and have an E configuration with respect to the C=N bond. The dihedral angles between the two benzene rings are 11.1 (2)° in one mol-ecule and 12.40 (19)° in the other. In the crystal structure, the mol-ecules are linked by N-H⋯O hydrogen bonds and weak C-H⋯O inter-actions into infinite one-dimensional chains along [1 0 0]. The crystal structure is further stabilized by N-H⋯O hydrogen bonds, weak C-H⋯O and very weak C-H⋯π inter-actions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background to the applications of hydrazone and benzohydrazide, see, for example: Bratenko et al. (1999 ▶); Raj et al. (2007 ▶); Rollas et al. (2002 ▶); Sridhar et al. (2003 ▶); Zhang et al. (2007 ▶).

Experimental

Crystal data

C15H14N2O

M = 238.28

Orthorhombic,

a = 8.2237 (6) Å

b = 5.5938 (4) Å

c = 52.839 (4) Å

V = 2430.7 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 100.0 (1) K

0.50 × 0.22 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.959, T max = 0.996

23699 measured reflections

3572 independent reflections

2925 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.159

S = 1.08

3572 reflections

327 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.30 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, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808029218/si2108sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029218/si2108Isup2.hkl

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

C15H14N2O	F(000) = 1008
Mr = 238.28	Dx = 1.302 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3572 reflections
a = 8.2237 (6) Å	θ = 0.8–30.0°
b = 5.5938 (4) Å	µ = 0.08 mm−1
c = 52.839 (4) Å	T = 100 K
V = 2430.7 (3) Å3	Plate, colorless
Z = 8	0.50 × 0.22 × 0.05 mm

Bruker SMART APEXII CCD area-detector diffractometer	3572 independent reflections
Radiation source: fine-focus sealed tube	2925 reflections with I > 2σ(I)
graphite	Rint = 0.069
Detector resolution: 8.33 pixels mm-1	θmax = 30.0°, θmin = 0.8°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −7→7
Tmin = 0.959, Tmax = 0.996	l = −74→73
23699 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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0598P)2 + 2.0097P] where P = (Fo2 + 2Fc2)/3
3572 reflections	(Δ/σ)max < 0.001
327 parameters	Δρmax = 0.29 e Å−3
1 restraint	Δρmin = −0.30 e Å−3

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

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
O2A	0.4444 (3)	−0.2422 (5)	0.28192 (5)	0.0225 (5)
N1A	0.5650 (4)	0.0608 (6)	0.24842 (6)	0.0211 (7)
N2A	0.6306 (4)	0.0417 (6)	0.27253 (6)	0.0201 (7)
H2NA	0.7358	0.0912	0.2746	0.024*
C1A	0.5851 (5)	0.4279 (7)	0.19173 (7)	0.0228 (8)
H1AA	0.6561	0.5481	0.1968	0.027*
C2A	0.5277 (5)	0.4246 (7)	0.16709 (7)	0.0248 (8)
H2AA	0.5604	0.5425	0.1558	0.030*
C3A	0.4219 (5)	0.2471 (7)	0.15916 (7)	0.0237 (8)
H3AA	0.3846	0.2445	0.1426	0.028*
C4A	0.3719 (6)	0.0726 (7)	0.17624 (8)	0.0259 (8)
H4AA	0.2996	−0.0457	0.1711	0.031*
C5A	0.4294 (5)	0.0744 (7)	0.20083 (7)	0.0221 (8)
H5AA	0.3959	−0.0440	0.2120	0.026*
C6A	0.5372 (5)	0.2515 (6)	0.20916 (7)	0.0183 (7)
C7A	0.6028 (4)	0.2496 (6)	0.23548 (7)	0.0186 (7)
C8A	0.5670 (5)	−0.1290 (6)	0.28767 (7)	0.0194 (7)
C9A	0.6454 (5)	−0.1709 (6)	0.31291 (7)	0.0192 (7)
C10A	0.6062 (5)	−0.3840 (7)	0.32523 (7)	0.0237 (8)
H10A	0.5381	−0.4942	0.3174	0.028*
C11A	0.6686 (6)	−0.4318 (7)	0.34912 (8)	0.0281 (9)
H11A	0.6405	−0.5727	0.3574	0.034*
C12A	0.7725 (5)	−0.2705 (7)	0.36069 (8)	0.0284 (9)
H12A	0.8161	−0.3045	0.3765	0.034*
C13A	0.8115 (5)	−0.0584 (7)	0.34857 (7)	0.0264 (8)
H13A	0.8798	0.0509	0.3565	0.032*
C14A	0.7494 (5)	−0.0079 (7)	0.32479 (7)	0.0223 (7)
H14A	0.7768	0.1343	0.3167	0.027*
C15A	0.7015 (5)	0.4561 (6)	0.24455 (8)	0.0240 (8)
H15A	0.6978	0.4627	0.2627	0.036*
H15B	0.6581	0.6016	0.2377	0.036*
H15C	0.8121	0.4370	0.2391	0.036*
O2B	0.7470 (3)	0.7474 (4)	0.48915 (5)	0.0219 (5)
N1B	0.8664 (4)	0.4422 (5)	0.52262 (6)	0.0191 (6)
N2B	0.9356 (4)	0.4640 (6)	0.49876 (6)	0.0217 (7)
H2NB	1.0056	0.4027	0.4934	0.026*
C1B	0.8836 (5)	0.0735 (7)	0.57897 (7)	0.0230 (8)
H1BA	0.9549	−0.0459	0.5738	0.028*
C2B	0.8256 (5)	0.0752 (7)	0.60357 (7)	0.0256 (8)
H2BA	0.8590	−0.0419	0.6149	0.031*
C3B	0.7171 (5)	0.2523 (7)	0.61138 (7)	0.0242 (8)
H3BA	0.6778	0.2529	0.6279	0.029*
C4B	0.6682 (5)	0.4275 (7)	0.59443 (7)	0.0233 (8)
H4BA	0.5953	0.5450	0.5996	0.028*
C5B	0.7273 (5)	0.4279 (6)	0.56996 (7)	0.0214 (8)
H5BA	0.6950	0.5472	0.5588	0.026*
C6B	0.8357 (5)	0.2499 (6)	0.56181 (7)	0.0178 (7)
C7B	0.9020 (5)	0.2528 (6)	0.53547 (7)	0.0181 (7)
C8B	0.8716 (5)	0.6352 (6)	0.48358 (7)	0.0191 (7)
C9B	0.9556 (5)	0.6867 (7)	0.45879 (7)	0.0200 (7)
C10B	0.9161 (5)	0.9028 (7)	0.44669 (8)	0.0239 (8)
H10B	0.8449	1.0098	0.4543	0.029*
C11B	0.9835 (5)	0.9560 (7)	0.42336 (7)	0.0248 (8)
H11B	0.9575	1.0990	0.4153	0.030*
C12B	1.0899 (5)	0.7967 (7)	0.41187 (7)	0.0258 (8)
H12B	1.1345	0.8333	0.3962	0.031*
C13B	1.1300 (5)	0.5833 (7)	0.42368 (7)	0.0249 (8)
H13B	1.2033	0.4785	0.4161	0.030*
C14B	1.0592 (5)	0.5268 (7)	0.44704 (7)	0.0228 (8)
H14B	1.0821	0.3809	0.4547	0.027*
C15B	1.0038 (5)	0.0472 (6)	0.52656 (7)	0.0215 (8)
H15D	1.0135	0.0531	0.5085	0.032*
H15E	0.9531	−0.1004	0.5314	0.032*
H15F	1.1099	0.0571	0.5341	0.032*

	U11	U22	U33	U12	U13	U23
O2A	0.0164 (13)	0.0242 (12)	0.0268 (13)	−0.0029 (11)	−0.0018 (11)	0.0001 (10)
N1A	0.0199 (17)	0.0221 (15)	0.0214 (15)	−0.0012 (12)	−0.0012 (13)	0.0022 (12)
N2A	0.0191 (17)	0.0198 (15)	0.0213 (16)	−0.0015 (12)	−0.0014 (13)	0.0019 (12)
C1A	0.023 (2)	0.0184 (16)	0.027 (2)	−0.0005 (14)	0.0004 (15)	0.0014 (14)
C2A	0.023 (2)	0.0258 (18)	0.0253 (19)	0.0017 (16)	−0.0004 (16)	0.0067 (15)
C3A	0.025 (2)	0.0271 (19)	0.0189 (17)	0.0047 (16)	−0.0020 (15)	0.0016 (14)
C4A	0.029 (2)	0.0225 (18)	0.0258 (18)	−0.0018 (16)	−0.0003 (16)	−0.0034 (15)
C5A	0.0199 (19)	0.0209 (17)	0.0254 (18)	−0.0009 (15)	0.0002 (15)	0.0020 (14)
C6A	0.0164 (17)	0.0182 (15)	0.0203 (16)	0.0023 (13)	0.0006 (13)	0.0000 (13)
C7A	0.0143 (17)	0.0199 (16)	0.0216 (17)	0.0029 (13)	−0.0002 (13)	−0.0012 (13)
C8A	0.0195 (18)	0.0158 (15)	0.0229 (18)	0.0009 (14)	0.0000 (15)	0.0001 (13)
C9A	0.0168 (18)	0.0188 (16)	0.0221 (17)	0.0005 (13)	0.0011 (14)	0.0027 (13)
C10A	0.025 (2)	0.0204 (17)	0.0261 (19)	0.0000 (15)	−0.0029 (16)	0.0017 (14)
C11A	0.028 (2)	0.0273 (19)	0.029 (2)	0.0009 (16)	0.0015 (17)	0.0061 (16)
C12A	0.028 (2)	0.034 (2)	0.0226 (18)	0.0027 (17)	−0.0020 (16)	0.0043 (16)
C13A	0.021 (2)	0.033 (2)	0.0253 (19)	−0.0016 (16)	0.0004 (16)	−0.0012 (15)
C14A	0.022 (2)	0.0233 (16)	0.0218 (18)	−0.0040 (16)	0.0001 (16)	0.0010 (14)
C15A	0.024 (2)	0.0192 (17)	0.029 (2)	0.0007 (15)	−0.0032 (16)	−0.0005 (14)
O2B	0.0192 (13)	0.0213 (12)	0.0253 (13)	0.0023 (11)	0.0021 (10)	0.0007 (10)
N1B	0.0182 (16)	0.0200 (14)	0.0193 (15)	−0.0017 (12)	0.0029 (12)	−0.0006 (11)
N2B	0.0213 (17)	0.0247 (15)	0.0190 (15)	0.0021 (13)	0.0058 (13)	−0.0008 (12)
C1B	0.0215 (19)	0.0189 (16)	0.028 (2)	0.0017 (14)	0.0004 (16)	0.0025 (15)
C2B	0.025 (2)	0.0252 (18)	0.027 (2)	0.0000 (16)	−0.0021 (17)	0.0070 (15)
C3B	0.022 (2)	0.0281 (18)	0.0221 (18)	−0.0019 (15)	0.0016 (15)	0.0002 (15)
C4B	0.024 (2)	0.0255 (18)	0.0210 (17)	0.0030 (16)	0.0015 (15)	−0.0030 (14)
C5B	0.026 (2)	0.0183 (15)	0.0205 (17)	0.0028 (14)	−0.0004 (15)	0.0012 (13)
C6B	0.0158 (17)	0.0142 (14)	0.0235 (16)	−0.0021 (13)	0.0002 (14)	0.0006 (12)
C7B	0.0155 (17)	0.0153 (16)	0.0237 (18)	−0.0002 (13)	−0.0012 (13)	−0.0028 (13)
C8B	0.0188 (18)	0.0181 (16)	0.0204 (17)	−0.0015 (14)	0.0005 (14)	−0.0018 (13)
C9B	0.0177 (18)	0.0219 (16)	0.0204 (16)	−0.0029 (14)	0.0015 (14)	−0.0035 (14)
C10B	0.0217 (19)	0.0229 (17)	0.027 (2)	0.0011 (15)	−0.0024 (15)	0.0000 (15)
C11B	0.028 (2)	0.0220 (18)	0.0240 (18)	−0.0030 (15)	−0.0011 (16)	0.0041 (14)
C12B	0.025 (2)	0.0319 (19)	0.0201 (17)	−0.0053 (16)	0.0006 (15)	0.0014 (15)
C13B	0.025 (2)	0.0270 (17)	0.0222 (18)	0.0012 (16)	0.0045 (16)	−0.0037 (14)
C14B	0.025 (2)	0.0201 (16)	0.0231 (18)	0.0018 (15)	−0.0015 (15)	−0.0001 (14)
C15B	0.0212 (19)	0.0185 (16)	0.0250 (18)	0.0035 (14)	0.0011 (15)	−0.0018 (14)

O2A—C8A	1.229 (5)	O2B—C8B	1.237 (5)
N1A—C7A	1.296 (5)	N1B—C7B	1.292 (5)
N1A—N2A	1.388 (4)	N1B—N2B	1.389 (4)
N2A—C8A	1.351 (5)	N2B—C8B	1.356 (5)
N2A—H2NA	0.9145	N2B—H2NB	0.7271
C1A—C2A	1.385 (5)	C1B—C2B	1.384 (5)
C1A—C6A	1.406 (5)	C1B—C6B	1.397 (5)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.385 (6)	C2B—C3B	1.395 (6)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.392 (6)	C3B—C4B	1.387 (5)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.382 (5)	C4B—C5B	1.381 (5)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.400 (5)	C5B—C6B	1.404 (5)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.492 (5)	C6B—C7B	1.495 (5)
C7A—C15A	1.491 (5)	C7B—C15B	1.498 (5)
C8A—C9A	1.499 (5)	C8B—C9B	1.509 (5)
C9A—C10A	1.396 (5)	C9B—C14B	1.382 (5)
C9A—C14A	1.399 (5)	C9B—C10B	1.406 (5)
C10A—C11A	1.388 (6)	C10B—C11B	1.384 (6)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.385 (6)	C11B—C12B	1.389 (6)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.386 (6)	C12B—C13B	1.387 (6)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.385 (5)	C13B—C14B	1.401 (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
C7A—N1A—N2A	117.0 (3)	C7B—N1B—N2B	117.1 (3)
C8A—N2A—N1A	116.6 (3)	C8B—N2B—N1B	116.1 (3)
C8A—N2A—H2NA	120.6	C8B—N2B—H2NB	114.2
N1A—N2A—H2NA	117.0	N1B—N2B—H2NB	129.5
C2A—C1A—C6A	120.7 (4)	C2B—C1B—C6B	120.5 (4)
C2A—C1A—H1AA	119.6	C2B—C1B—H1BA	119.8
C6A—C1A—H1AA	119.6	C6B—C1B—H1BA	119.8
C3A—C2A—C1A	120.5 (4)	C1B—C2B—C3B	120.2 (4)
C3A—C2A—H2AA	119.7	C1B—C2B—H2BA	119.9
C1A—C2A—H2AA	119.7	C3B—C2B—H2BA	119.9
C2A—C3A—C4A	119.5 (4)	C4B—C3B—C2B	119.7 (4)
C2A—C3A—H3AA	120.3	C4B—C3B—H3BA	120.1
C4A—C3A—H3AA	120.3	C2B—C3B—H3BA	120.1
C5A—C4A—C3A	120.2 (4)	C5B—C4B—C3B	120.2 (4)
C5A—C4A—H4AA	119.9	C5B—C4B—H4BA	119.9
C3A—C4A—H4AA	119.9	C3B—C4B—H4BA	119.9
C4A—C5A—C6A	121.1 (4)	C4B—C5B—C6B	120.6 (3)
C4A—C5A—H5AA	119.4	C4B—C5B—H5BA	119.7
C6A—C5A—H5AA	119.4	C6B—C5B—H5BA	119.7
C5A—C6A—C1A	117.9 (3)	C1B—C6B—C5B	118.8 (3)
C5A—C6A—C7A	121.1 (3)	C1B—C6B—C7B	120.6 (3)
C1A—C6A—C7A	121.0 (3)	C5B—C6B—C7B	120.6 (3)
N1A—C7A—C15A	126.3 (3)	N1B—C7B—C6B	114.5 (3)
N1A—C7A—C6A	114.3 (3)	N1B—C7B—C15B	126.2 (3)
C15A—C7A—C6A	119.4 (3)	C6B—C7B—C15B	119.2 (3)
O2A—C8A—N2A	122.4 (3)	O2B—C8B—N2B	122.6 (3)
O2A—C8A—C9A	119.5 (3)	O2B—C8B—C9B	119.3 (3)
N2A—C8A—C9A	118.1 (3)	N2B—C8B—C9B	118.1 (3)
C10A—C9A—C14A	119.2 (3)	C14B—C9B—C10B	119.7 (4)
C10A—C9A—C8A	116.7 (3)	C14B—C9B—C8B	123.3 (3)
C14A—C9A—C8A	124.1 (3)	C10B—C9B—C8B	116.9 (3)
C11A—C10A—C9A	120.2 (4)	C11B—C10B—C9B	119.8 (4)
C11A—C10A—H10A	119.9	C11B—C10B—H10B	120.1
C9A—C10A—H10A	119.9	C9B—C10B—H10B	120.1
C12A—C11A—C10A	120.2 (4)	C10B—C11B—C12B	120.3 (4)
C12A—C11A—H11A	119.9	C10B—C11B—H11B	119.9
C10A—C11A—H11A	119.9	C12B—C11B—H11B	119.9
C11A—C12A—C13A	119.7 (4)	C13B—C12B—C11B	120.4 (4)
C11A—C12A—H12A	120.1	C13B—C12B—H12B	119.8
C13A—C12A—H12A	120.1	C11B—C12B—H12B	119.8
C14A—C13A—C12A	120.6 (4)	C12B—C13B—C14B	119.4 (4)
C14A—C13A—H13A	119.7	C12B—C13B—H13B	120.3
C12A—C13A—H13A	119.7	C14B—C13B—H13B	120.3
C13A—C14A—C9A	120.0 (4)	C9B—C14B—C13B	120.4 (4)
C13A—C14A—H14A	120.0	C9B—C14B—H14B	119.8
C9A—C14A—H14A	120.0	C13B—C14B—H14B	119.8
C7A—C15A—H15A	109.5	C7B—C15B—H15D	109.5
C7A—C15A—H15B	109.5	C7B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
C7A—C15A—H15C	109.5	C7B—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—N1A—N2A—C8A	167.6 (3)	C7B—N1B—N2B—C8B	166.7 (3)
C6A—C1A—C2A—C3A	0.0 (6)	C6B—C1B—C2B—C3B	0.7 (6)
C1A—C2A—C3A—C4A	0.7 (6)	C1B—C2B—C3B—C4B	−0.3 (6)
C2A—C3A—C4A—C5A	−1.0 (6)	C2B—C3B—C4B—C5B	−0.5 (6)
C3A—C4A—C5A—C6A	0.6 (6)	C3B—C4B—C5B—C6B	0.9 (6)
C4A—C5A—C6A—C1A	0.1 (6)	C2B—C1B—C6B—C5B	−0.3 (6)
C4A—C5A—C6A—C7A	−178.3 (3)	C2B—C1B—C6B—C7B	178.1 (4)
C2A—C1A—C6A—C5A	−0.4 (6)	C4B—C5B—C6B—C1B	−0.5 (6)
C2A—C1A—C6A—C7A	178.0 (3)	C4B—C5B—C6B—C7B	−178.9 (4)
N2A—N1A—C7A—C15A	−4.2 (6)	N2B—N1B—C7B—C6B	174.9 (3)
N2A—N1A—C7A—C6A	176.2 (3)	N2B—N1B—C7B—C15B	−3.6 (6)
C5A—C6A—C7A—N1A	6.8 (5)	C1B—C6B—C7B—N1B	−170.8 (3)
C1A—C6A—C7A—N1A	−171.5 (3)	C5B—C6B—C7B—N1B	7.6 (5)
C5A—C6A—C7A—C15A	−172.8 (4)	C1B—C6B—C7B—C15B	7.8 (5)
C1A—C6A—C7A—C15A	8.8 (5)	C5B—C6B—C7B—C15B	−173.8 (3)
N1A—N2A—C8A—O2A	−9.0 (5)	N1B—N2B—C8B—O2B	−8.4 (5)
N1A—N2A—C8A—C9A	174.2 (3)	N1B—N2B—C8B—C9B	172.6 (3)
O2A—C8A—C9A—C10A	19.1 (5)	O2B—C8B—C9B—C14B	−158.2 (4)
N2A—C8A—C9A—C10A	−164.0 (3)	N2B—C8B—C9B—C14B	20.9 (6)
O2A—C8A—C9A—C14A	−158.9 (4)	O2B—C8B—C9B—C10B	17.6 (5)
N2A—C8A—C9A—C14A	18.0 (5)	N2B—C8B—C9B—C10B	−163.3 (3)
C14A—C9A—C10A—C11A	0.6 (6)	C14B—C9B—C10B—C11B	−1.2 (6)
C8A—C9A—C10A—C11A	−177.4 (4)	C8B—C9B—C10B—C11B	−177.2 (4)
C9A—C10A—C11A—C12A	−1.2 (6)	C9B—C10B—C11B—C12B	0.0 (6)
C10A—C11A—C12A—C13A	1.4 (6)	C10B—C11B—C12B—C13B	−0.2 (6)
C11A—C12A—C13A—C14A	−1.1 (6)	C11B—C12B—C13B—C14B	1.5 (6)
C12A—C13A—C14A—C9A	0.5 (6)	C10B—C9B—C14B—C13B	2.6 (6)
C10A—C9A—C14A—C13A	−0.3 (6)	C8B—C9B—C14B—C13B	178.3 (4)
C8A—C9A—C14A—C13A	177.6 (4)	C12B—C13B—C14B—C9B	−2.7 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2NA···O2Ai	0.91	1.95	2.857 (4)	170
N2B—H2NB···O2Bii	0.73	2.17	2.866 (4)	161
C14A—H14A···O2Ai	0.93	2.38	3.108 (5)	135
C14B—H14B···O2Bii	0.93	2.38	3.113 (5)	135
C15A—H15A···N2A	0.96	2.47	2.811 (5)	100
C15A—H15A···O2Ai	0.96	2.58	3.053 (5)	110
C15B—H15D···N2B	0.96	2.44	2.812 (5)	103
C15B—H15D···O2Bii	0.96	2.45	3.038 (5)	120
C1A—H1AA···Cg1ii	0.93	2.96	3.729 (4)	141
C4A—H4AA···Cg1iii	0.93	2.95	3.724 (5)	141
C1B—H1BA···Cg2i	0.93	2.88	3.726 (4)	141
C10A—H10A···Cg3iv	0.93	3.31	3.993 (4)	132
C10B—H10B···Cg4v	0.93	3.16	3.847 (4)	132
C4B—H4BA···Cg2vi	0.93	2.94	3.714 (4)	141
C13A—H13A···Cg3i	0.93	3.05	3.674 (4)	126
C13B—H13B···Cg4ii	0.93	3.07	3.755 (4)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H2NA⋯O2Ai	0.91	1.95	2.857 (4)	170
N2B—H2NB⋯O2Bii	0.73	2.17	2.866 (4)	161
C14A—H14A⋯O2Ai	0.93	2.38	3.108 (5)	135
C14B—H14B⋯O2Bii	0.93	2.38	3.113 (5)	135
C15A—H15A⋯O2Ai	0.96	2.58	3.053 (5)	110
C15B—H15D⋯O2Bii	0.96	2.44	3.038 (5)	120
C1A—H1AA⋯Cg1ii	0.93	2.96	3.729 (4)	141
C4A—H4AA⋯Cg1iii	0.93	2.95	3.724 (5)	141
C1B—H1BA⋯Cg2i	0.93	2.88	3.726 (4)	141
C4B—H4BA⋯Cg2iv	0.93	2.94	3.714 (4)	141

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 and Cg2 are the centroids of the C1A–C6A and C1B–C6B phenyl rings, respectively.