2-[(E)-(2,4-Dimethyl-phen-yl)imino-meth-yl]phenol.

The asymmetric unit of the title compound, C(15)H(15)NO, contains two independent mol-ecules, both of which exist in trans configurations with respect to the C=N bonds [1.278 (2) and 1.279 (2) Å]. In each mol-ecule, intra-molecular O-H⋯N hydrogen bonds generate S(6) ring motifs. In one mol-ecule, the benzene rings form a dihedral angle of 13.38 (9)°, while in the other mol-ecule the dihedral angle is 30.60 (10)°. In the crystal, the two independent mol-ecules are linked via weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For general background to and the pharmacological activity of Schiff base compounds, see: Gallant et al. (2004 ▶); Kulkarni (1975 ▶); Zhao et al. (1988 ▶); Ma & Zhao (1988 ▶). For a related structure, see: Fun et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H15NO

M = 225.28

Orthorhombic,

a = 7.3161 (4) Å

b = 12.0287 (7) Å

c = 28.1634 (15) Å

V = 2478.5 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.51 × 0.35 × 0.32 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.963, T max = 0.976

39373 measured reflections

4117 independent reflections

3381 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.122

S = 1.02

4117 reflections

319 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.13 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811026110/lh5275sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026110/lh5275Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811026110/lh5275Isup3.cml

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

C15H15NO	F(000) = 960
Mr = 225.28	Dx = 1.207 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9995 reflections
a = 7.3161 (4) Å	θ = 2.8–29.8°
b = 12.0287 (7) Å	µ = 0.08 mm−1
c = 28.1634 (15) Å	T = 296 K
V = 2478.5 (2) Å3	Block, yellow
Z = 8	0.51 × 0.35 × 0.32 mm

Bruker SMART APEXII DUO CCD area-detector diffractometer	4117 independent reflections
Radiation source: fine-focus sealed tube	3381 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 30.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.963, Tmax = 0.976	k = −16→16
39373 measured reflections	l = −39→39

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0711P)2 + 0.1832P] where P = (Fo2 + 2Fc2)/3
4117 reflections	(Δ/σ)max = 0.001
319 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.13 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	0.9304 (2)	0.77108 (12)	−0.04120 (5)	0.0671 (4)
N1A	0.7924 (2)	0.91236 (11)	0.01797 (4)	0.0445 (3)
C1A	0.8636 (2)	0.83620 (14)	−0.07601 (5)	0.0485 (3)
C2A	0.8931 (3)	0.80560 (16)	−0.12313 (6)	0.0598 (5)
H2AA	0.9601	0.7419	−0.1301	0.072*
C3A	0.8235 (3)	0.86924 (18)	−0.15938 (6)	0.0656 (5)
H3AA	0.8439	0.8479	−0.1907	0.079*
C4A	0.7240 (3)	0.96424 (17)	−0.15021 (6)	0.0670 (5)
H4AA	0.6766	1.0063	−0.1750	0.080*
C5A	0.6955 (3)	0.99621 (16)	−0.10335 (6)	0.0573 (4)
H5AA	0.6293	1.0604	−0.0969	0.069*
C6A	0.7647 (2)	0.93353 (13)	−0.06593 (5)	0.0446 (3)
C7A	0.7319 (2)	0.96829 (14)	−0.01727 (5)	0.0465 (3)
H7AA	0.6653	1.0328	−0.0116	0.056*
C8A	0.7652 (2)	0.94552 (13)	0.06567 (5)	0.0416 (3)
C9A	0.7052 (3)	1.05078 (14)	0.07882 (5)	0.0505 (4)
H9AA	0.6770	1.1029	0.0556	0.061*
C10A	0.6870 (3)	1.07866 (16)	0.12636 (6)	0.0555 (4)
H10A	0.6461	1.1493	0.1345	0.067*
C11A	0.7287 (3)	1.00352 (17)	0.16175 (5)	0.0521 (4)
C12A	0.7875 (3)	0.89892 (15)	0.14813 (5)	0.0527 (4)
H12A	0.8136	0.8470	0.1716	0.063*
C13A	0.8095 (2)	0.86800 (14)	0.10087 (5)	0.0472 (3)
C14A	0.7152 (3)	1.0353 (2)	0.21353 (6)	0.0696 (6)
H14A	0.6420	0.9815	0.2300	0.104*
H14B	0.6597	1.1073	0.2163	0.104*
H14C	0.8354	1.0373	0.2272	0.104*
C15A	0.8789 (4)	0.75441 (16)	0.08827 (7)	0.0703 (6)
H15A	0.8982	0.7122	0.1168	0.105*
H15B	0.9922	0.7611	0.0713	0.105*
H15C	0.7908	0.7172	0.0686	0.105*
O1B	0.0454 (2)	0.23511 (11)	0.08434 (5)	0.0626 (3)
N1B	0.1838 (2)	0.08482 (12)	0.14035 (5)	0.0500 (3)
C1B	0.0999 (2)	0.16993 (14)	0.04804 (6)	0.0487 (4)
C2B	0.0575 (3)	0.20224 (15)	0.00174 (6)	0.0568 (4)
H2BA	−0.0090	0.2669	−0.0036	0.068*
C3B	0.1143 (3)	0.13803 (17)	−0.03601 (6)	0.0628 (5)
H3BA	0.0864	0.1603	−0.0668	0.075*
C4B	0.2116 (3)	0.04152 (17)	−0.02891 (6)	0.0620 (5)
H4BA	0.2514	−0.0001	−0.0548	0.074*
C5B	0.2499 (3)	0.00667 (16)	0.01675 (6)	0.0551 (4)
H5BA	0.3128	−0.0596	0.0215	0.066*
C6B	0.1953 (2)	0.06990 (13)	0.05584 (5)	0.0460 (3)
C7B	0.2336 (2)	0.03067 (14)	0.10346 (6)	0.0497 (4)
H7BA	0.2965	−0.0359	0.1073	0.060*
C8B	0.2118 (2)	0.04277 (15)	0.18674 (5)	0.0494 (4)
C9B	0.2152 (3)	−0.06991 (16)	0.19735 (6)	0.0582 (4)
H9BA	0.2036	−0.1216	0.1730	0.070*
C10B	0.2357 (3)	−0.10637 (17)	0.24352 (6)	0.0660 (5)
H10B	0.2388	−0.1823	0.2497	0.079*
C11B	0.2515 (3)	−0.03198 (19)	0.28073 (6)	0.0628 (5)
C12B	0.2454 (3)	0.07986 (19)	0.26989 (6)	0.0649 (5)
H12B	0.2544	0.1309	0.2946	0.078*
C13B	0.2264 (3)	0.11976 (16)	0.22389 (6)	0.0583 (4)
C14B	0.2744 (4)	−0.0720 (2)	0.33137 (6)	0.0847 (7)
H14D	0.3425	−0.1402	0.3315	0.127*
H14E	0.1563	−0.0843	0.3453	0.127*
H14F	0.3389	−0.0168	0.3494	0.127*
C15B	0.2263 (5)	0.24280 (17)	0.21427 (8)	0.0910 (9)
H15D	0.2594	0.2820	0.2427	0.137*
H15E	0.1065	0.2655	0.2043	0.137*
H15F	0.3130	0.2593	0.1897	0.137*
H1OA	0.906 (4)	0.802 (2)	−0.0136 (8)	0.092 (8)*
H1OB	0.068 (4)	0.201 (2)	0.1120 (8)	0.090 (8)*

	U11	U22	U33	U12	U13	U23
O1A	0.0892 (11)	0.0605 (7)	0.0517 (7)	0.0224 (8)	0.0009 (7)	−0.0004 (6)
N1A	0.0474 (7)	0.0463 (6)	0.0398 (6)	−0.0021 (6)	0.0024 (5)	−0.0014 (5)
C1A	0.0499 (8)	0.0489 (8)	0.0468 (8)	0.0004 (7)	0.0029 (7)	−0.0026 (6)
C2A	0.0665 (11)	0.0597 (10)	0.0532 (9)	0.0045 (9)	0.0070 (9)	−0.0120 (8)
C3A	0.0806 (14)	0.0739 (12)	0.0423 (8)	−0.0055 (11)	0.0055 (9)	−0.0090 (8)
C4A	0.0892 (15)	0.0693 (11)	0.0425 (8)	0.0027 (12)	−0.0034 (10)	0.0049 (8)
C5A	0.0730 (12)	0.0515 (8)	0.0475 (8)	0.0059 (9)	−0.0037 (9)	0.0005 (7)
C6A	0.0463 (8)	0.0476 (7)	0.0400 (7)	−0.0031 (7)	0.0008 (6)	−0.0021 (6)
C7A	0.0478 (8)	0.0484 (8)	0.0431 (7)	0.0021 (7)	0.0013 (6)	−0.0035 (6)
C8A	0.0401 (7)	0.0463 (7)	0.0384 (6)	−0.0028 (6)	0.0010 (6)	0.0001 (5)
C9A	0.0607 (9)	0.0476 (8)	0.0433 (7)	0.0029 (8)	−0.0003 (7)	0.0000 (6)
C10A	0.0637 (11)	0.0546 (9)	0.0481 (8)	0.0020 (9)	0.0027 (8)	−0.0074 (7)
C11A	0.0475 (8)	0.0673 (10)	0.0415 (7)	−0.0101 (8)	0.0026 (7)	−0.0053 (7)
C12A	0.0562 (9)	0.0599 (9)	0.0421 (7)	−0.0050 (8)	−0.0023 (7)	0.0070 (7)
C13A	0.0473 (8)	0.0489 (8)	0.0454 (7)	−0.0010 (7)	−0.0018 (7)	0.0022 (6)
C14A	0.0711 (12)	0.0956 (15)	0.0420 (8)	−0.0062 (13)	0.0044 (9)	−0.0117 (9)
C15A	0.0933 (16)	0.0566 (10)	0.0609 (10)	0.0196 (11)	−0.0087 (11)	0.0030 (8)
O1B	0.0783 (9)	0.0510 (6)	0.0586 (7)	0.0045 (7)	0.0039 (7)	−0.0023 (6)
N1B	0.0519 (8)	0.0539 (7)	0.0441 (6)	−0.0028 (7)	0.0005 (6)	0.0005 (6)
C1B	0.0487 (8)	0.0459 (7)	0.0516 (8)	−0.0080 (7)	0.0021 (7)	0.0006 (6)
C2B	0.0579 (10)	0.0540 (9)	0.0586 (9)	−0.0074 (8)	−0.0019 (8)	0.0120 (8)
C3B	0.0713 (12)	0.0709 (11)	0.0462 (8)	−0.0168 (10)	−0.0020 (8)	0.0085 (8)
C4B	0.0735 (12)	0.0650 (10)	0.0474 (8)	−0.0088 (10)	0.0080 (9)	−0.0035 (8)
C5B	0.0594 (10)	0.0540 (8)	0.0519 (8)	−0.0034 (8)	0.0074 (8)	−0.0017 (7)
C6B	0.0465 (8)	0.0477 (8)	0.0437 (7)	−0.0073 (7)	0.0023 (6)	0.0014 (6)
C7B	0.0511 (8)	0.0508 (8)	0.0471 (8)	−0.0019 (7)	0.0017 (7)	0.0023 (7)
C8B	0.0472 (8)	0.0584 (9)	0.0426 (7)	−0.0024 (8)	0.0015 (7)	−0.0010 (7)
C9B	0.0698 (12)	0.0562 (9)	0.0487 (8)	−0.0041 (9)	0.0006 (8)	−0.0015 (7)
C10B	0.0784 (14)	0.0643 (11)	0.0555 (9)	−0.0025 (11)	0.0019 (10)	0.0104 (8)
C11B	0.0599 (11)	0.0837 (13)	0.0449 (8)	0.0007 (11)	0.0037 (8)	0.0048 (8)
C12B	0.0729 (13)	0.0749 (11)	0.0470 (8)	0.0052 (11)	0.0024 (9)	−0.0097 (8)
C13B	0.0664 (11)	0.0595 (9)	0.0490 (8)	0.0038 (9)	0.0036 (8)	−0.0060 (7)
C14B	0.0918 (17)	0.1126 (19)	0.0496 (10)	0.0030 (17)	0.0001 (11)	0.0142 (11)
C15B	0.143 (3)	0.0597 (11)	0.0709 (12)	0.0069 (16)	0.0003 (17)	−0.0125 (10)

O1A—C1A	1.346 (2)	O1B—C1B	1.349 (2)
O1A—H1OA	0.88 (3)	O1B—H1OB	0.89 (2)
N1A—C7A	1.278 (2)	N1B—C7B	1.279 (2)
N1A—C8A	1.4155 (18)	N1B—C8B	1.416 (2)
C1A—C2A	1.394 (2)	C1B—C2B	1.395 (2)
C1A—C6A	1.405 (2)	C1B—C6B	1.408 (2)
C2A—C3A	1.374 (3)	C2B—C3B	1.378 (3)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.379 (3)	C3B—C4B	1.376 (3)
C3A—H3AA	0.9300	C3B—H3BA	0.9300
C4A—C5A	1.390 (2)	C4B—C5B	1.382 (2)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.391 (2)	C5B—C6B	1.396 (2)
C5A—H5AA	0.9300	C5B—H5BA	0.9300
C6A—C7A	1.453 (2)	C6B—C7B	1.449 (2)
C7A—H7AA	0.9300	C7B—H7BA	0.9300
C8A—C9A	1.390 (2)	C8B—C9B	1.388 (3)
C8A—C13A	1.399 (2)	C8B—C13B	1.401 (2)
C9A—C10A	1.387 (2)	C9B—C10B	1.380 (2)
C9A—H9AA	0.9300	C9B—H9BA	0.9300
C10A—C11A	1.379 (3)	C10B—C11B	1.383 (3)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—C12A	1.384 (3)	C11B—C12B	1.380 (3)
C11A—C14A	1.511 (2)	C11B—C14B	1.514 (2)
C12A—C13A	1.391 (2)	C12B—C13B	1.389 (2)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C15A	1.500 (2)	C13B—C15B	1.505 (3)
C14A—H14A	0.9600	C14B—H14D	0.9600
C14A—H14B	0.9600	C14B—H14E	0.9600
C14A—H14C	0.9600	C14B—H14F	0.9600
C15A—H15A	0.9600	C15B—H15D	0.9600
C15A—H15B	0.9600	C15B—H15E	0.9600
C15A—H15C	0.9600	C15B—H15F	0.9600
C1A—O1A—H1OA	109.1 (17)	C1B—O1B—H1OB	110.0 (17)
C7A—N1A—C8A	122.67 (14)	C7B—N1B—C8B	121.75 (15)
O1A—C1A—C2A	118.90 (16)	O1B—C1B—C2B	118.72 (16)
O1A—C1A—C6A	121.63 (14)	O1B—C1B—C6B	121.66 (15)
C2A—C1A—C6A	119.47 (15)	C2B—C1B—C6B	119.61 (16)
C3A—C2A—C1A	120.19 (17)	C3B—C2B—C1B	119.84 (18)
C3A—C2A—H2AA	119.9	C3B—C2B—H2BA	120.1
C1A—C2A—H2AA	119.9	C1B—C2B—H2BA	120.1
C2A—C3A—C4A	121.21 (16)	C4B—C3B—C2B	121.10 (17)
C2A—C3A—H3AA	119.4	C4B—C3B—H3BA	119.4
C4A—C3A—H3AA	119.4	C2B—C3B—H3BA	119.4
C3A—C4A—C5A	119.07 (18)	C3B—C4B—C5B	119.74 (18)
C3A—C4A—H4AA	120.5	C3B—C4B—H4BA	120.1
C5A—C4A—H4AA	120.5	C5B—C4B—H4BA	120.1
C4A—C5A—C6A	120.98 (18)	C4B—C5B—C6B	120.70 (18)
C4A—C5A—H5AA	119.5	C4B—C5B—H5BA	119.6
C6A—C5A—H5AA	119.5	C6B—C5B—H5BA	119.6
C5A—C6A—C1A	119.08 (14)	C5B—C6B—C1B	118.96 (15)
C5A—C6A—C7A	119.90 (15)	C5B—C6B—C7B	119.78 (16)
C1A—C6A—C7A	121.02 (14)	C1B—C6B—C7B	121.24 (15)
N1A—C7A—C6A	121.58 (15)	N1B—C7B—C6B	122.04 (16)
N1A—C7A—H7AA	119.2	N1B—C7B—H7BA	119.0
C6A—C7A—H7AA	119.2	C6B—C7B—H7BA	119.0
C9A—C8A—C13A	119.42 (14)	C9B—C8B—C13B	118.89 (16)
C9A—C8A—N1A	123.64 (14)	C9B—C8B—N1B	123.37 (15)
C13A—C8A—N1A	116.88 (14)	C13B—C8B—N1B	117.64 (16)
C10A—C9A—C8A	120.51 (15)	C10B—C9B—C8B	121.00 (17)
C10A—C9A—H9AA	119.7	C10B—C9B—H9BA	119.5
C8A—C9A—H9AA	119.7	C8B—C9B—H9BA	119.5
C11A—C10A—C9A	121.19 (17)	C9B—C10B—C11B	121.15 (18)
C11A—C10A—H10A	119.4	C9B—C10B—H10B	119.4
C9A—C10A—H10A	119.4	C11B—C10B—H10B	119.4
C10A—C11A—C12A	117.65 (15)	C12B—C11B—C10B	117.41 (17)
C10A—C11A—C14A	121.14 (18)	C12B—C11B—C14B	121.42 (19)
C12A—C11A—C14A	121.19 (17)	C10B—C11B—C14B	121.2 (2)
C11A—C12A—C13A	122.96 (16)	C11B—C12B—C13B	123.12 (18)
C11A—C12A—H12A	118.5	C11B—C12B—H12B	118.4
C13A—C12A—H12A	118.5	C13B—C12B—H12B	118.4
C12A—C13A—C8A	118.23 (15)	C12B—C13B—C8B	118.42 (18)
C12A—C13A—C15A	120.59 (15)	C12B—C13B—C15B	120.53 (18)
C8A—C13A—C15A	121.18 (14)	C8B—C13B—C15B	121.03 (16)
C11A—C14A—H14A	109.5	C11B—C14B—H14D	109.5
C11A—C14A—H14B	109.5	C11B—C14B—H14E	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
C11A—C14A—H14C	109.5	C11B—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5
C13A—C15A—H15A	109.5	C13B—C15B—H15D	109.5
C13A—C15A—H15B	109.5	C13B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
C13A—C15A—H15C	109.5	C13B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
O1A—C1A—C2A—C3A	178.71 (19)	O1B—C1B—C2B—C3B	178.93 (17)
C6A—C1A—C2A—C3A	−1.0 (3)	C6B—C1B—C2B—C3B	−2.1 (3)
C1A—C2A—C3A—C4A	0.1 (3)	C1B—C2B—C3B—C4B	0.5 (3)
C2A—C3A—C4A—C5A	0.6 (3)	C2B—C3B—C4B—C5B	1.5 (3)
C3A—C4A—C5A—C6A	−0.4 (3)	C3B—C4B—C5B—C6B	−1.8 (3)
C4A—C5A—C6A—C1A	−0.4 (3)	C4B—C5B—C6B—C1B	0.1 (3)
C4A—C5A—C6A—C7A	−179.54 (19)	C4B—C5B—C6B—C7B	178.76 (17)
O1A—C1A—C6A—C5A	−178.57 (17)	O1B—C1B—C6B—C5B	−179.27 (16)
C2A—C1A—C6A—C5A	1.1 (3)	C2B—C1B—C6B—C5B	1.8 (2)
O1A—C1A—C6A—C7A	0.5 (3)	O1B—C1B—C6B—C7B	2.1 (2)
C2A—C1A—C6A—C7A	−179.75 (17)	C2B—C1B—C6B—C7B	−176.81 (16)
C8A—N1A—C7A—C6A	178.82 (15)	C8B—N1B—C7B—C6B	176.07 (15)
C5A—C6A—C7A—N1A	179.56 (17)	C5B—C6B—C7B—N1B	−178.89 (17)
C1A—C6A—C7A—N1A	0.5 (3)	C1B—C6B—C7B—N1B	−0.3 (3)
C7A—N1A—C8A—C9A	−13.7 (2)	C7B—N1B—C8B—C9B	−29.7 (3)
C7A—N1A—C8A—C13A	169.08 (15)	C7B—N1B—C8B—C13B	153.98 (18)
C13A—C8A—C9A—C10A	−0.8 (3)	C13B—C8B—C9B—C10B	−1.1 (3)
N1A—C8A—C9A—C10A	−177.94 (16)	N1B—C8B—C9B—C10B	−177.34 (19)
C8A—C9A—C10A—C11A	0.4 (3)	C8B—C9B—C10B—C11B	0.7 (4)
C9A—C10A—C11A—C12A	−0.6 (3)	C9B—C10B—C11B—C12B	0.2 (4)
C9A—C10A—C11A—C14A	177.81 (18)	C9B—C10B—C11B—C14B	−179.9 (2)
C10A—C11A—C12A—C13A	1.3 (3)	C10B—C11B—C12B—C13B	−0.7 (4)
C14A—C11A—C12A—C13A	−177.09 (19)	C14B—C11B—C12B—C13B	179.3 (2)
C11A—C12A—C13A—C8A	−1.7 (3)	C11B—C12B—C13B—C8B	0.3 (3)
C11A—C12A—C13A—C15A	178.23 (19)	C11B—C12B—C13B—C15B	−178.2 (3)
C9A—C8A—C13A—C12A	1.4 (2)	C9B—C8B—C13B—C12B	0.6 (3)
N1A—C8A—C13A—C12A	178.78 (15)	N1B—C8B—C13B—C12B	177.06 (18)
C9A—C8A—C13A—C15A	−178.55 (18)	C9B—C8B—C13B—C15B	179.1 (2)
N1A—C8A—C13A—C15A	−1.2 (2)	N1B—C8B—C13B—C15B	−4.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1OA···N1A	0.88 (2)	1.80 (2)	2.5854 (19)	147 (2)
O1B—H1OB···N1B	0.90 (2)	1.82 (2)	2.604 (2)	145 (2)
C5A—H5AA···O1Bi	0.93	2.56	3.455 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1OA⋯N1A	0.88 (2)	1.80 (2)	2.5854 (19)	147 (2)
O1B—H1OB⋯N1B	0.90 (2)	1.82 (2)	2.604 (2)	145 (2)
C5A—H5AA⋯O1Bi	0.93	2.56	3.455 (2)	162

Symmetry code: (i) .