2,2'-[1,1'-(Heptane-1,7-diyldioxy-dinitrilo)diethyl-idyne]di-1-naphthol.

The mol-ecule of the title compound, C(31)H(34)N(2)O(4), adopts an L-shaped configuration, in which the naphthalene units are approximately perpendicular, making a dihedral angle of 87.89 (3)°. Intramolecular H-bonds are formed between the OH substituents and the N atoms at each end of the molecule. In the crystal structure, each mol-ecule links six other mol-ecules into an infinite three-dimensional network supra-molecular structure, which is built from one-dimensional zigzag chains via weak C-H⋯π stacking and inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the potential medical applications of Schiff base compounds, see: Huang et al. (2002 ▶). For the properties of Salen-type bis­oxime compounds, see: Darensbourg et al. (2004 ▶); Dong et al. (2008a ▶,b ▶); Karthikeyan et al. (2006 ▶); Zhang et al. (2007 ▶).

Experimental

Crystal data

C31H34N2O4

M = 498.60

Monoclinic,

a = 11.1670 (12) Å

b = 30.992 (3) Å

c = 8.0562 (10) Å

β = 106.999 (2)°

V = 2666.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.43 × 0.18 × 0.16 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.966, T max = 0.987

6926 measured reflections

2351 independent reflections

1294 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.120

S = 1.04

2351 reflections

334 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 1996 ▶); cell refinement: SAINT (Bruker, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022727/at2813sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022727/at2813Isup2.hkl

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

C31H34N2O4	F(000) = 1064
Mr = 498.60	Dx = 1.242 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1335 reflections
a = 11.1670 (12) Å	θ = 2.6–20.4°
b = 30.992 (3) Å	µ = 0.08 mm−1
c = 8.0562 (10) Å	T = 298 K
β = 106.999 (2)°	Needle-shaped, colourless
V = 2666.4 (5) Å3	0.43 × 0.18 × 0.16 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	2351 independent reflections
Radiation source: fine-focus sealed tube	1294 reflections with I > 2σ(I)
graphite	Rint = 0.055
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
Tmin = 0.966, Tmax = 0.987	k = −36→26
6926 measured reflections	l = −9→9

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0485P)2] where P = (Fo2 + 2Fc2)/3
2351 reflections	(Δ/σ)max < 0.001
334 parameters	Δρmax = 0.13 e Å−3
2 restraints	Δρmin = −0.15 e Å−3

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
N1	0.5072 (4)	−0.01344 (13)	0.4193 (6)	0.0563 (12)
N2	0.3241 (4)	0.34282 (14)	0.1038 (7)	0.0672 (14)
O1	0.5541 (3)	0.02813 (10)	0.4627 (5)	0.0638 (11)
O2	0.2551 (4)	0.33008 (11)	0.2159 (6)	0.0829 (14)
O3	0.3391 (3)	−0.06591 (10)	0.2602 (5)	0.0653 (11)
H3	0.3708	−0.0422	0.2893	0.098*
O4	0.4023 (4)	0.32932 (10)	−0.1543 (6)	0.0712 (12)
H4	0.3672	0.3234	−0.0809	0.107*
C1	0.4564 (5)	0.05779 (15)	0.3800 (8)	0.0613 (15)
H1A	0.3840	0.0529	0.4210	0.074*
H1B	0.4314	0.0533	0.2554	0.074*
C2	0.5032 (5)	0.10340 (15)	0.4216 (8)	0.0545 (14)
H2A	0.5781	0.1078	0.3858	0.065*
H2B	0.5245	0.1083	0.5458	0.065*
C3	0.4027 (5)	0.13488 (14)	0.3276 (8)	0.0603 (15)
H3A	0.3848	0.1300	0.2038	0.072*
H3B	0.3269	0.1285	0.3585	0.072*
C4	0.4333 (5)	0.18204 (15)	0.3637 (8)	0.0581 (15)
H4A	0.4531	0.1872	0.4875	0.070*
H4B	0.5068	0.1892	0.3283	0.070*
C5	0.3270 (5)	0.21085 (15)	0.2698 (7)	0.0617 (16)
H5A	0.2550	0.2040	0.3093	0.074*
H5B	0.3049	0.2041	0.1470	0.074*
C6	0.3514 (6)	0.25888 (16)	0.2920 (9)	0.0715 (17)
H6A	0.3762	0.2660	0.4145	0.086*
H6B	0.4197	0.2666	0.2460	0.086*
C7	0.2364 (6)	0.28434 (16)	0.1993 (10)	0.079 (2)
H7A	0.2116	0.2768	0.0772	0.095*
H7B	0.1685	0.2764	0.2456	0.095*
C8	0.7100 (5)	−0.03440 (16)	0.6125 (9)	0.081 (2)
H8A	0.7385	−0.0071	0.5824	0.121*
H8B	0.7672	−0.0567	0.6022	0.121*
H8C	0.7061	−0.0333	0.7299	0.121*
C9	0.5832 (5)	−0.04386 (16)	0.4933 (7)	0.0504 (13)
C10	0.4203 (4)	−0.09722 (15)	0.3404 (7)	0.0473 (13)
C11	0.5372 (4)	−0.08821 (15)	0.4514 (7)	0.0477 (14)
C12	0.6146 (5)	−0.12319 (17)	0.5284 (8)	0.0590 (15)
H12	0.6940	−0.1178	0.6033	0.071*
C13	0.5745 (5)	−0.16512 (16)	0.4945 (8)	0.0606 (16)
H13	0.6272	−0.1876	0.5464	0.073*
C14	0.4557 (5)	−0.17435 (15)	0.3833 (7)	0.0503 (14)
C15	0.3764 (4)	−0.14046 (15)	0.3028 (7)	0.0473 (13)
C16	0.2572 (5)	−0.14951 (17)	0.1906 (8)	0.0631 (15)
H16	0.2050	−0.1271	0.1360	0.076*
C17	0.2182 (6)	−0.1910 (2)	0.1617 (9)	0.0742 (18)
H17	0.1383	−0.1969	0.0893	0.089*
C18	0.2957 (6)	−0.22464 (19)	0.2384 (9)	0.078 (2)
H18	0.2672	−0.2529	0.2162	0.093*
C19	0.4118 (6)	−0.21739 (15)	0.3449 (8)	0.0645 (16)
H19	0.4632	−0.2405	0.3933	0.077*
C20	0.3147 (5)	0.41367 (17)	0.2330 (8)	0.0735 (18)
H20A	0.2608	0.4356	0.1663	0.110*
H20B	0.3881	0.4269	0.3090	0.110*
H20C	0.2710	0.3981	0.3005	0.110*
C21	0.3522 (4)	0.38312 (17)	0.1130 (8)	0.0563 (15)
C22	0.4417 (5)	0.37085 (14)	−0.1341 (8)	0.0536 (15)
C23	0.4214 (5)	0.39749 (16)	−0.0081 (8)	0.0568 (15)
C24	0.4688 (5)	0.44061 (15)	0.0014 (9)	0.0667 (17)
H24	0.4555	0.4592	0.0850	0.080*
C25	0.5314 (5)	0.45511 (19)	−0.1051 (9)	0.0721 (19)
H25	0.5620	0.4832	−0.0931	0.087*
C26	0.5518 (5)	0.4283 (2)	−0.2361 (9)	0.0665 (16)
C27	0.5071 (4)	0.38519 (17)	−0.2497 (8)	0.0561 (15)
C28	0.5259 (5)	0.35823 (19)	−0.3813 (9)	0.0729 (17)
H28	0.4946	0.3302	−0.3931	0.088*
C29	0.5895 (6)	0.3728 (2)	−0.4915 (10)	0.084 (2)
H29	0.6024	0.3548	−0.5769	0.101*
C30	0.6349 (5)	0.4149 (3)	−0.4751 (10)	0.086 (2)
H30	0.6787	0.4246	−0.5499	0.103*
C31	0.6171 (5)	0.4419 (2)	−0.3538 (10)	0.077 (2)
H31	0.6481	0.4699	−0.3469	0.093*

	U11	U22	U33	U12	U13	U23
N1	0.062 (3)	0.038 (3)	0.063 (3)	−0.003 (2)	0.008 (2)	0.002 (2)
N2	0.073 (3)	0.042 (3)	0.087 (4)	0.006 (2)	0.025 (3)	0.009 (3)
O1	0.060 (2)	0.038 (2)	0.084 (3)	0.0017 (17)	0.007 (2)	0.0032 (19)
O2	0.101 (3)	0.043 (3)	0.120 (4)	0.012 (2)	0.056 (3)	0.015 (2)
O3	0.059 (2)	0.045 (2)	0.080 (3)	0.0047 (18)	0.002 (2)	0.0083 (19)
O4	0.083 (3)	0.040 (2)	0.087 (3)	−0.004 (2)	0.021 (2)	−0.004 (2)
C1	0.066 (3)	0.044 (3)	0.070 (4)	0.010 (3)	0.014 (3)	0.004 (3)
C2	0.062 (3)	0.039 (3)	0.059 (4)	0.000 (2)	0.012 (3)	−0.001 (3)
C3	0.071 (4)	0.039 (3)	0.066 (4)	−0.001 (3)	0.013 (3)	0.002 (3)
C4	0.068 (3)	0.042 (3)	0.065 (4)	−0.006 (3)	0.020 (3)	0.000 (3)
C5	0.069 (3)	0.047 (3)	0.069 (5)	0.003 (3)	0.018 (3)	0.002 (3)
C6	0.089 (4)	0.042 (3)	0.085 (5)	0.002 (3)	0.027 (4)	0.006 (3)
C7	0.085 (4)	0.042 (3)	0.119 (6)	0.007 (3)	0.043 (4)	0.012 (4)
C8	0.064 (4)	0.054 (4)	0.101 (6)	−0.001 (3)	−0.013 (4)	0.002 (3)
C9	0.050 (3)	0.044 (3)	0.054 (4)	0.000 (3)	0.011 (3)	0.004 (3)
C10	0.049 (3)	0.045 (3)	0.048 (4)	0.008 (2)	0.014 (3)	0.006 (3)
C11	0.044 (3)	0.037 (3)	0.061 (4)	0.004 (2)	0.014 (3)	0.003 (3)
C12	0.053 (3)	0.047 (3)	0.070 (4)	0.005 (3)	0.006 (3)	0.001 (3)
C13	0.064 (4)	0.047 (4)	0.069 (4)	0.018 (3)	0.016 (3)	0.004 (3)
C14	0.058 (3)	0.041 (3)	0.052 (4)	0.001 (3)	0.017 (3)	−0.001 (3)
C15	0.049 (3)	0.044 (3)	0.050 (4)	0.001 (3)	0.015 (3)	0.002 (3)
C16	0.058 (3)	0.052 (3)	0.075 (4)	−0.005 (3)	0.013 (3)	−0.003 (3)
C17	0.069 (4)	0.063 (4)	0.080 (5)	−0.018 (3)	0.005 (4)	−0.009 (4)
C18	0.097 (5)	0.048 (4)	0.089 (6)	−0.017 (3)	0.028 (5)	−0.013 (4)
C19	0.088 (4)	0.039 (3)	0.066 (5)	0.004 (3)	0.022 (4)	0.002 (3)
C20	0.079 (4)	0.055 (4)	0.082 (5)	0.017 (3)	0.015 (4)	−0.003 (3)
C21	0.054 (3)	0.040 (3)	0.066 (4)	0.012 (2)	0.002 (3)	0.007 (3)
C22	0.053 (3)	0.034 (3)	0.064 (4)	0.007 (2)	0.001 (3)	0.004 (3)
C23	0.055 (3)	0.037 (3)	0.069 (4)	0.005 (2)	0.004 (3)	0.002 (3)
C24	0.075 (4)	0.035 (3)	0.077 (5)	0.000 (3)	0.001 (4)	−0.007 (3)
C25	0.076 (4)	0.046 (4)	0.086 (6)	−0.013 (3)	0.010 (4)	0.004 (4)
C26	0.054 (3)	0.066 (4)	0.070 (5)	−0.001 (3)	0.002 (3)	0.020 (3)
C27	0.046 (3)	0.051 (4)	0.061 (4)	0.006 (3)	0.000 (3)	0.004 (3)
C28	0.066 (4)	0.072 (4)	0.073 (5)	0.013 (3)	0.009 (4)	0.002 (4)
C29	0.069 (4)	0.094 (6)	0.083 (6)	0.014 (4)	0.013 (4)	0.003 (4)
C30	0.060 (4)	0.105 (6)	0.090 (6)	0.016 (4)	0.018 (4)	0.031 (5)
C31	0.059 (4)	0.082 (5)	0.084 (6)	0.002 (3)	0.010 (4)	0.008 (4)

N1—C9	1.292 (6)	C11—C12	1.412 (7)
N1—O1	1.396 (5)	C12—C13	1.376 (7)
N2—C21	1.285 (6)	C12—H12	0.9300
N2—O2	1.404 (6)	C13—C14	1.396 (7)
O1—C1	1.433 (6)	C13—H13	0.9300
O2—C7	1.433 (6)	C14—C15	1.405 (6)
O3—C10	1.356 (5)	C14—C19	1.424 (7)
O3—H3	0.8200	C15—C16	1.401 (7)
O4—C22	1.355 (5)	C16—C17	1.357 (7)
O4—H4	0.8200	C16—H16	0.9300
C1—C2	1.511 (6)	C17—C18	1.379 (8)
C1—H1A	0.9700	C17—H17	0.9300
C1—H1B	0.9700	C18—C19	1.348 (9)
C2—C3	1.513 (7)	C18—H18	0.9300
C2—H2A	0.9700	C19—H19	0.9300
C2—H2B	0.9700	C20—C21	1.498 (7)
C3—C4	1.510 (6)	C20—H20A	0.9600
C3—H3A	0.9700	C20—H20B	0.9600
C3—H3B	0.9700	C20—H20C	0.9600
C4—C5	1.501 (7)	C21—C23	1.479 (7)
C4—H4A	0.9700	C22—C23	1.378 (7)
C4—H4B	0.9700	C22—C27	1.412 (7)
C5—C6	1.515 (7)	C23—C24	1.431 (6)
C5—H5A	0.9700	C24—C25	1.333 (8)
C5—H5B	0.9700	C24—H24	0.9300
C6—C7	1.506 (8)	C25—C26	1.414 (8)
C6—H6A	0.9700	C25—H25	0.9300
C6—H6B	0.9700	C26—C27	1.418 (7)
C7—H7A	0.9700	C26—C31	1.420 (8)
C7—H7B	0.9700	C27—C28	1.413 (8)
C8—C9	1.489 (7)	C28—C29	1.366 (8)
C8—H8A	0.9600	C28—H28	0.9300
C8—H8B	0.9600	C29—C30	1.390 (8)
C8—H8C	0.9600	C29—H29	0.9300
C9—C11	1.472 (6)	C30—C31	1.345 (9)
C10—C11	1.377 (6)	C30—H30	0.9300
C10—C15	1.429 (6)	C31—H31	0.9300
C9—N1—O1	114.2 (4)	C13—C12—C11	121.1 (5)
C21—N2—O2	114.0 (4)	C13—C12—H12	119.5
N1—O1—C1	107.2 (4)	C11—C12—H12	119.5
N2—O2—C7	108.1 (4)	C12—C13—C14	120.9 (5)
C10—O3—H3	109.5	C12—C13—H13	119.5
C22—O4—H4	109.5	C14—C13—H13	119.5
O1—C1—C2	109.3 (4)	C13—C14—C15	119.7 (4)
O1—C1—H1A	109.8	C13—C14—C19	122.3 (5)
C2—C1—H1A	109.8	C15—C14—C19	118.0 (5)
O1—C1—H1B	109.8	C16—C15—C14	120.0 (4)
C2—C1—H1B	109.8	C16—C15—C10	121.8 (4)
H1A—C1—H1B	108.3	C14—C15—C10	118.2 (4)
C1—C2—C3	109.5 (4)	C17—C16—C15	119.8 (5)
C1—C2—H2A	109.8	C17—C16—H16	120.1
C3—C2—H2A	109.8	C15—C16—H16	120.1
C1—C2—H2B	109.8	C16—C17—C18	120.8 (6)
C3—C2—H2B	109.8	C16—C17—H17	119.6
H2A—C2—H2B	108.2	C18—C17—H17	119.6
C4—C3—C2	115.8 (4)	C19—C18—C17	121.3 (5)
C4—C3—H3A	108.3	C19—C18—H18	119.3
C2—C3—H3A	108.3	C17—C18—H18	119.3
C4—C3—H3B	108.3	C18—C19—C14	120.1 (5)
C2—C3—H3B	108.3	C18—C19—H19	120.0
H3A—C3—H3B	107.4	C14—C19—H19	120.0
C5—C4—C3	112.2 (4)	C21—C20—H20A	109.5
C5—C4—H4A	109.2	C21—C20—H20B	109.5
C3—C4—H4A	109.2	H20A—C20—H20B	109.5
C5—C4—H4B	109.2	C21—C20—H20C	109.5
C3—C4—H4B	109.2	H20A—C20—H20C	109.5
H4A—C4—H4B	107.9	H20B—C20—H20C	109.5
C4—C5—C6	115.9 (5)	N2—C21—C23	114.9 (5)
C4—C5—H5A	108.3	N2—C21—C20	122.8 (5)
C6—C5—H5A	108.3	C23—C21—C20	122.3 (5)
C4—C5—H5B	108.3	O4—C22—C23	122.7 (5)
C6—C5—H5B	108.3	O4—C22—C27	115.6 (5)
H5A—C5—H5B	107.4	C23—C22—C27	121.7 (5)
C7—C6—C5	111.0 (5)	C22—C23—C24	117.4 (5)
C7—C6—H6A	109.4	C22—C23—C21	122.4 (5)
C5—C6—H6A	109.4	C24—C23—C21	120.2 (5)
C7—C6—H6B	109.4	C25—C24—C23	122.4 (6)
C5—C6—H6B	109.4	C25—C24—H24	118.8
H6A—C6—H6B	108.0	C23—C24—H24	118.8
O2—C7—C6	113.1 (5)	C24—C25—C26	120.7 (6)
O2—C7—H7A	109.0	C24—C25—H25	119.6
C6—C7—H7A	109.0	C26—C25—H25	119.6
O2—C7—H7B	109.0	C25—C26—C27	118.8 (6)
C6—C7—H7B	109.0	C25—C26—C31	123.3 (6)
H7A—C7—H7B	107.8	C27—C26—C31	117.8 (7)
C9—C8—H8A	109.5	C22—C27—C28	121.8 (5)
C9—C8—H8B	109.5	C22—C27—C26	118.9 (6)
H8A—C8—H8B	109.5	C28—C27—C26	119.2 (6)
C9—C8—H8C	109.5	C29—C28—C27	120.8 (6)
H8A—C8—H8C	109.5	C29—C28—H28	119.6
H8B—C8—H8C	109.5	C27—C28—H28	119.6
N1—C9—C11	115.9 (4)	C28—C29—C30	119.5 (7)
N1—C9—C8	121.8 (5)	C28—C29—H29	120.2
C11—C9—C8	122.3 (4)	C30—C29—H29	120.2
O3—C10—C11	122.6 (4)	C31—C30—C29	121.7 (7)
O3—C10—C15	115.4 (4)	C31—C30—H30	119.1
C11—C10—C15	122.0 (4)	C29—C30—H30	119.1
C10—C11—C12	118.1 (4)	C30—C31—C26	120.9 (7)
C10—C11—C9	122.6 (4)	C30—C31—H31	119.5
C12—C11—C9	119.2 (4)	C26—C31—H31	119.5
C9—N1—O1—C1	−176.2 (5)	C15—C16—C17—C18	−1.5 (10)
C21—N2—O2—C7	−176.8 (5)	C16—C17—C18—C19	0.4 (11)
N1—O1—C1—C2	−179.4 (4)	C17—C18—C19—C14	1.4 (10)
O1—C1—C2—C3	177.3 (5)	C13—C14—C19—C18	179.1 (6)
C1—C2—C3—C4	177.0 (5)	C15—C14—C19—C18	−2.0 (8)
C2—C3—C4—C5	−178.1 (5)	O2—N2—C21—C23	−178.1 (4)
C3—C4—C5—C6	−177.4 (5)	O2—N2—C21—C20	0.0 (7)
C4—C5—C6—C7	−177.3 (5)	O4—C22—C23—C24	179.3 (4)
N2—O2—C7—C6	76.5 (7)	C27—C22—C23—C24	0.2 (7)
C5—C6—C7—O2	−179.8 (5)	O4—C22—C23—C21	−1.4 (8)
O1—N1—C9—C11	179.8 (4)	C27—C22—C23—C21	179.5 (4)
O1—N1—C9—C8	−0.7 (7)	N2—C21—C23—C22	6.9 (7)
O3—C10—C11—C12	180.0 (5)	C20—C21—C23—C22	−171.2 (5)
C15—C10—C11—C12	0.3 (8)	N2—C21—C23—C24	−173.8 (5)
O3—C10—C11—C9	0.5 (8)	C20—C21—C23—C24	8.0 (7)
C15—C10—C11—C9	−179.2 (5)	C22—C23—C24—C25	−0.5 (7)
N1—C9—C11—C10	−0.1 (8)	C21—C23—C24—C25	−179.8 (5)
C8—C9—C11—C10	−179.6 (6)	C23—C24—C25—C26	1.2 (9)
N1—C9—C11—C12	−179.5 (5)	C24—C25—C26—C27	−1.5 (8)
C8—C9—C11—C12	1.0 (8)	C24—C25—C26—C31	179.7 (5)
C10—C11—C12—C13	−0.3 (8)	O4—C22—C27—C28	2.2 (7)
C9—C11—C12—C13	179.2 (5)	C23—C22—C27—C28	−178.7 (5)
C11—C12—C13—C14	−0.2 (9)	O4—C22—C27—C26	−179.7 (4)
C12—C13—C14—C15	0.8 (8)	C23—C22—C27—C26	−0.6 (7)
C12—C13—C14—C19	179.7 (5)	C25—C26—C27—C22	1.2 (7)
C13—C14—C15—C16	179.8 (6)	C31—C26—C27—C22	−179.9 (5)
C19—C14—C15—C16	0.9 (7)	C25—C26—C27—C28	179.4 (5)
C13—C14—C15—C10	−0.8 (7)	C31—C26—C27—C28	−1.8 (7)
C19—C14—C15—C10	−179.8 (5)	C22—C27—C28—C29	−180.0 (5)
O3—C10—C15—C16	−0.1 (7)	C26—C27—C28—C29	1.9 (8)
C11—C10—C15—C16	179.7 (5)	C27—C28—C29—C30	−0.8 (9)
O3—C10—C15—C14	−179.4 (4)	C28—C29—C30—C31	−0.5 (10)
C11—C10—C15—C14	0.3 (7)	C29—C30—C31—C26	0.6 (9)
C14—C15—C16—C17	0.8 (8)	C25—C26—C31—C30	179.4 (6)
C10—C15—C16—C17	−178.5 (6)	C27—C26—C31—C30	0.6 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1	0.82	1.81	2.530 (5)	146
O4—H4···N2	0.82	1.80	2.514 (7)	145
C30—H30···O3i	0.93	2.69	3.598 (8)	165
C20—H20A···O1ii	0.96	2.66	3.572 (7)	159
C29—H29···Cg1iii	0.93	3.40	4.161 (1)	141
C20—H20B···Cg2iv	0.96	3.54	4.203 (1)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N1	0.82	1.81	2.530 (5)	146
O4—H4⋯N2	0.82	1.80	2.514 (7)	145
C30—H30⋯O3i	0.93	2.69	3.598 (8)	165
C20—H20A⋯O1ii	0.96	2.66	3.572 (7)	159
C29—H29⋯Cg1iii	0.93	3.40	4.161 (1)	141
C20—H20B⋯Cg2iv	0.96	3.54	4.203 (1)	128

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1 and Cg2 are centroids of the C10–C15 and C14–C19 rings.