(5-Benzoyl-2-methyl-4-{[1-(pyridin-4-yl)-1H-1,2,3-triazol-4-yl]meth-oxy}-1-benzofuran-7-yl)(phen-yl)methanone.

The crystal structure of the title compound, C(31)H(22)N(4)O(4), features weak C-H⋯O inter-actions. The dihedral angle between the fused benzene and furan rings is 2.49 (15)°, while that between the triazole and pyridine rings is 10.23(18)°.

Related literature

For bioactive nnitro­gen-linked heterocyclic compounds, see: Anderson et al. (2004 ▶); Ha et al. (2009 ▶); Liu et al. (2011 ▶); Tan et al. (2012 ▶); Venkatesan et al. (2010 ▶); Yim et al. (2010 ▶). For the bioactivity of benzofuran analogues substituted by heterocyclic moieties, see: El-Shehry et al. (2010 ▶); Kaldrikyan et al. (2009 ▶); Saberi et al. (2006 ▶). For a related structure, see: Liu et al. (2012 ▶).

Experimental

Crystal data

C31H22N4O4

M = 514.53

Triclinic,

a = 10.11 (2) Å

b = 10.87 (3) Å

c = 11.64 (3) Å

α = 94.73 (4)°

β = 92.07 (3)°

γ = 92.05 (4)°

V = 1273 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.38 × 0.22 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.966, T max = 0.988

9629 measured reflections

4699 independent reflections

2743 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.200

S = 0.85

4699 reflections

353 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812023720/ds2193sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023720/ds2193Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812023720/ds2193Isup3.cml

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

C31H22N4O4	Z = 2
Mr = 514.53	F(000) = 536
Triclinic, P1	Dx = 1.343 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.11 (2) Å	Cell parameters from 1346 reflections
b = 10.87 (3) Å	θ = 2.5–21.0°
c = 11.64 (3) Å	µ = 0.09 mm−1
α = 94.73 (4)°	T = 296 K
β = 92.07 (3)°	Block, colourless
γ = 92.05 (4)°	0.38 × 0.22 × 0.13 mm
V = 1273 (5) Å3

Bruker SMART CCD area-detector diffractometer	4699 independent reflections
Radiation source: fine-focus sealed tube	2743 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
phi and ω scans	θmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.966, Tmax = 0.988	k = −12→13
9629 measured reflections	l = −14→14

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.200	H-atom parameters constrained
S = 0.85	w = 1/[σ2(Fo2) + (0.1P)2 + 0.4387P] where P = (Fo2 + 2Fc2)/3
4699 reflections	(Δ/σ)max < 0.001
353 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.17 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
N1	0.4387 (2)	−0.1220 (2)	−0.3567 (2)	0.0473 (6)
N2	0.5280 (3)	−0.1333 (3)	−0.2672 (2)	0.0622 (8)
N3	0.4837 (3)	−0.0696 (3)	−0.1759 (2)	0.0614 (8)
N4	0.5183 (3)	−0.2859 (3)	−0.6907 (3)	0.0806 (10)
O1	0.20278 (18)	−0.01035 (18)	−0.05837 (16)	0.0467 (5)
O2	−0.0057 (2)	−0.2440 (2)	0.12502 (19)	0.0610 (6)
O3	0.1408 (2)	0.0551 (2)	0.48995 (19)	0.0654 (7)
O4	0.19574 (18)	0.30077 (17)	0.25525 (16)	0.0464 (5)
C1	0.1656 (3)	0.1786 (3)	0.2199 (2)	0.0406 (7)
C2	0.1172 (3)	0.0928 (3)	0.2923 (2)	0.0425 (7)
C3	0.0985 (3)	−0.0274 (3)	0.2403 (2)	0.0448 (7)
H3	0.0657	−0.0882	0.2846	0.054*
C4	0.1268 (2)	−0.0616 (3)	0.1240 (2)	0.0405 (7)
C5	0.1774 (3)	0.0282 (3)	0.0540 (2)	0.0398 (7)
C6	0.1954 (2)	0.1526 (3)	0.1030 (2)	0.0401 (7)
C7	0.2451 (3)	0.2700 (3)	0.0659 (2)	0.0448 (7)
H7	0.2711	0.2844	−0.0078	0.054*
C8	0.2462 (3)	0.3540 (3)	0.1584 (2)	0.0452 (7)
C9	0.2956 (3)	0.0639 (3)	−0.1195 (3)	0.0516 (8)
H9A	0.3597	0.1067	−0.0648	0.062*
H9B	0.2482	0.1253	−0.1586	0.062*
C10	0.3658 (3)	−0.0175 (3)	−0.2056 (2)	0.0465 (7)
C11	0.3382 (3)	−0.0494 (3)	−0.3205 (3)	0.0474 (7)
H11	0.2660	−0.0265	−0.3646	0.057*
C12	0.4637 (3)	−0.1773 (3)	−0.4698 (3)	0.0491 (7)
C13	0.5661 (4)	−0.2603 (4)	−0.4842 (3)	0.0738 (11)
H13	0.6175	−0.2813	−0.4214	0.089*
C14	0.5883 (4)	−0.3104 (4)	−0.5955 (4)	0.0874 (13)
H14	0.6567	−0.3648	−0.6046	0.105*
C15	0.4212 (4)	−0.2071 (4)	−0.6724 (3)	0.0698 (10)
H15	0.3701	−0.1886	−0.7363	0.084*
C16	0.3902 (3)	−0.1506 (3)	−0.5659 (3)	0.0567 (8)
H16	0.3216	−0.0960	−0.5596	0.068*
C17	0.0912 (3)	−0.1942 (3)	0.0833 (3)	0.0468 (7)
C18	0.1739 (3)	−0.2720 (3)	0.0022 (2)	0.0448 (7)
C19	0.1132 (3)	−0.3795 (3)	−0.0558 (3)	0.0547 (8)
H19	0.0227	−0.3952	−0.0504	0.066*
C20	0.1884 (4)	−0.4627 (3)	−0.1214 (3)	0.0639 (9)
H20	0.1477	−0.5333	−0.1595	0.077*
C21	0.3240 (4)	−0.4402 (3)	−0.1299 (3)	0.0683 (10)
H21	0.3739	−0.4959	−0.1733	0.082*
C22	0.3846 (3)	−0.3340 (3)	−0.0732 (3)	0.0627 (9)
H22	0.4752	−0.3188	−0.0788	0.075*
C23	0.3098 (3)	−0.2500 (3)	−0.0078 (3)	0.0520 (8)
H23	0.3510	−0.1789	0.0293	0.062*
C24	0.0941 (3)	0.1209 (3)	0.4186 (2)	0.0456 (7)
C25	0.0118 (3)	0.2283 (3)	0.4561 (2)	0.0447 (7)
C26	−0.0814 (3)	0.2755 (3)	0.3805 (3)	0.0522 (8)
H26	−0.0883	0.2445	0.3035	0.063*
C27	−0.1641 (4)	0.3690 (3)	0.4208 (3)	0.0676 (10)
H27	−0.2274	0.3984	0.3710	0.081*
C28	−0.1517 (4)	0.4178 (3)	0.5349 (3)	0.0737 (11)
H28	−0.2062	0.4803	0.5614	0.088*
C29	−0.0573 (4)	0.3730 (3)	0.6102 (3)	0.0698 (10)
H29	−0.0478	0.4067	0.6863	0.084*
C30	0.0217 (3)	0.2784 (3)	0.5712 (3)	0.0571 (8)
H30	0.0825	0.2474	0.6221	0.068*
C31	0.2916 (4)	0.4852 (3)	0.1780 (3)	0.0660 (10)
H31A	0.3324	0.5105	0.1101	0.099*
H31B	0.3547	0.4950	0.2421	0.099*
H31C	0.2171	0.5351	0.1946	0.099*

	U11	U22	U33	U12	U13	U23
N1	0.0469 (13)	0.0519 (15)	0.0426 (14)	0.0057 (11)	0.0023 (11)	−0.0015 (12)
N2	0.0580 (16)	0.087 (2)	0.0416 (15)	0.0196 (15)	−0.0011 (12)	−0.0016 (14)
N3	0.0566 (16)	0.083 (2)	0.0443 (16)	0.0135 (14)	0.0016 (12)	−0.0016 (14)
N4	0.080 (2)	0.090 (2)	0.066 (2)	0.0052 (18)	0.0064 (17)	−0.0285 (18)
O1	0.0542 (12)	0.0487 (12)	0.0367 (11)	−0.0012 (9)	0.0065 (9)	0.0000 (9)
O2	0.0587 (13)	0.0587 (14)	0.0641 (15)	−0.0120 (11)	0.0105 (11)	−0.0002 (11)
O3	0.0742 (15)	0.0765 (16)	0.0481 (14)	0.0220 (12)	0.0009 (11)	0.0133 (12)
O4	0.0534 (12)	0.0416 (12)	0.0440 (12)	0.0014 (9)	0.0062 (9)	0.0006 (9)
C1	0.0412 (15)	0.0398 (16)	0.0409 (16)	0.0028 (12)	0.0037 (12)	0.0013 (13)
C2	0.0448 (15)	0.0470 (17)	0.0362 (16)	0.0024 (13)	0.0034 (12)	0.0048 (13)
C3	0.0465 (16)	0.0443 (17)	0.0449 (17)	0.0009 (13)	0.0060 (13)	0.0093 (13)
C4	0.0378 (14)	0.0431 (16)	0.0410 (16)	0.0015 (12)	0.0025 (12)	0.0055 (13)
C5	0.0368 (14)	0.0465 (17)	0.0357 (16)	0.0038 (12)	0.0005 (11)	0.0016 (12)
C6	0.0366 (14)	0.0433 (17)	0.0407 (16)	0.0020 (12)	0.0002 (12)	0.0054 (13)
C7	0.0474 (16)	0.0479 (18)	0.0393 (16)	0.0001 (13)	0.0063 (12)	0.0037 (13)
C8	0.0488 (16)	0.0446 (17)	0.0432 (17)	0.0023 (13)	0.0078 (13)	0.0068 (14)
C9	0.0605 (19)	0.0501 (18)	0.0438 (18)	−0.0023 (15)	0.0129 (14)	−0.0003 (14)
C10	0.0493 (17)	0.0476 (17)	0.0427 (17)	0.0017 (13)	0.0057 (13)	0.0022 (14)
C11	0.0465 (16)	0.0529 (18)	0.0430 (17)	0.0071 (14)	0.0022 (13)	0.0035 (14)
C12	0.0529 (17)	0.0502 (18)	0.0427 (17)	0.0005 (14)	0.0035 (13)	−0.0057 (14)
C13	0.072 (2)	0.080 (3)	0.066 (2)	0.026 (2)	−0.0107 (18)	−0.019 (2)
C14	0.081 (3)	0.094 (3)	0.081 (3)	0.027 (2)	−0.007 (2)	−0.038 (2)
C15	0.080 (2)	0.081 (3)	0.045 (2)	0.003 (2)	0.0019 (17)	−0.0092 (18)
C16	0.062 (2)	0.061 (2)	0.0470 (19)	0.0081 (16)	0.0018 (15)	−0.0014 (15)
C17	0.0452 (16)	0.0491 (18)	0.0457 (17)	−0.0031 (14)	−0.0022 (13)	0.0055 (14)
C18	0.0489 (16)	0.0412 (17)	0.0443 (17)	0.0021 (13)	−0.0028 (13)	0.0046 (13)
C19	0.0511 (18)	0.0520 (19)	0.059 (2)	−0.0061 (15)	−0.0065 (15)	−0.0002 (16)
C20	0.080 (2)	0.051 (2)	0.057 (2)	−0.0020 (18)	−0.0036 (18)	−0.0091 (16)
C21	0.080 (2)	0.067 (2)	0.057 (2)	0.0141 (19)	0.0093 (18)	−0.0092 (18)
C22	0.0550 (19)	0.061 (2)	0.073 (2)	0.0063 (16)	0.0108 (16)	0.0037 (18)
C23	0.0523 (17)	0.0480 (18)	0.0551 (19)	0.0005 (14)	0.0007 (14)	0.0027 (15)
C24	0.0467 (16)	0.0507 (18)	0.0398 (17)	−0.0002 (13)	0.0014 (13)	0.0068 (14)
C25	0.0482 (16)	0.0480 (17)	0.0388 (16)	−0.0016 (13)	0.0094 (13)	0.0067 (13)
C26	0.0605 (19)	0.0560 (19)	0.0406 (17)	0.0045 (15)	0.0101 (14)	0.0016 (14)
C27	0.074 (2)	0.070 (2)	0.062 (2)	0.0198 (19)	0.0130 (17)	0.0144 (19)
C28	0.092 (3)	0.062 (2)	0.068 (3)	0.010 (2)	0.030 (2)	−0.0012 (19)
C29	0.082 (3)	0.076 (3)	0.050 (2)	0.005 (2)	0.0135 (19)	−0.0058 (19)
C30	0.064 (2)	0.066 (2)	0.0414 (18)	0.0011 (17)	0.0065 (15)	0.0019 (15)
C31	0.085 (2)	0.050 (2)	0.062 (2)	−0.0033 (17)	0.0115 (18)	−0.0044 (17)

N1—C11	1.366 (4)	C13—C14	1.391 (6)
N1—N2	1.369 (4)	C13—H13	0.9300
N1—C12	1.437 (5)	C14—H14	0.9300
N2—N3	1.320 (4)	C15—C16	1.388 (5)
N3—C10	1.383 (4)	C15—H15	0.9300
N4—C15	1.337 (5)	C16—H16	0.9300
N4—C14	1.343 (6)	C17—C18	1.509 (5)
O1—C5	1.376 (4)	C18—C23	1.397 (5)
O1—C9	1.458 (4)	C18—C19	1.410 (5)
O2—C17	1.236 (4)	C19—C20	1.398 (5)
O3—C24	1.232 (4)	C19—H19	0.9300
O4—C1	1.378 (4)	C20—C21	1.392 (6)
O4—C8	1.412 (4)	C20—H20	0.9300
C1—C2	1.395 (4)	C21—C22	1.393 (5)
C1—C6	1.412 (5)	C21—H21	0.9300
C2—C3	1.398 (5)	C22—C23	1.401 (5)
C2—C24	1.505 (5)	C22—H22	0.9300
C3—C4	1.416 (5)	C23—H23	0.9300
C3—H3	0.9300	C24—C25	1.503 (5)
C4—C5	1.416 (4)	C25—C30	1.402 (5)
C4—C17	1.507 (5)	C25—C26	1.405 (5)
C5—C6	1.426 (5)	C26—C27	1.401 (5)
C6—C7	1.459 (5)	C26—H26	0.9300
C7—C8	1.352 (4)	C27—C28	1.389 (6)
C7—H7	0.9300	C27—H27	0.9300
C8—C31	1.480 (5)	C28—C29	1.399 (6)
C9—C10	1.497 (4)	C28—H28	0.9300
C9—H9A	0.9700	C29—C30	1.382 (5)
C9—H9B	0.9700	C29—H29	0.9300
C10—C11	1.369 (5)	C30—H30	0.9300
C11—H11	0.9300	C31—H31A	0.9600
C12—C16	1.376 (5)	C31—H31B	0.9600
C12—C13	1.402 (5)	C31—H31C	0.9600
C11—N1—N2	110.2 (3)	N4—C15—H15	117.3
C11—N1—C12	130.0 (3)	C16—C15—H15	117.3
N2—N1—C12	119.7 (3)	C12—C16—C15	118.3 (3)
N3—N2—N1	106.9 (3)	C12—C16—H16	120.8
N2—N3—C10	109.4 (3)	C15—C16—H16	120.8
C15—N4—C14	115.0 (3)	O2—C17—C4	117.9 (3)
C5—O1—C9	118.3 (2)	O2—C17—C18	118.5 (3)
C1—O4—C8	106.1 (2)	C4—C17—C18	123.5 (3)
O4—C1—C2	123.9 (3)	C23—C18—C19	118.8 (3)
O4—C1—C6	110.6 (2)	C23—C18—C17	123.1 (3)
C2—C1—C6	125.5 (3)	C19—C18—C17	117.8 (3)
C1—C2—C3	114.7 (3)	C20—C19—C18	120.4 (3)
C1—C2—C24	124.6 (3)	C20—C19—H19	119.8
C3—C2—C24	120.7 (3)	C18—C19—H19	119.8
C2—C3—C4	123.5 (3)	C21—C20—C19	120.3 (3)
C2—C3—H3	118.2	C21—C20—H20	119.8
C4—C3—H3	118.2	C19—C20—H20	119.8
C5—C4—C3	119.9 (3)	C22—C21—C20	119.7 (3)
C5—C4—C17	125.1 (3)	C22—C21—H21	120.2
C3—C4—C17	114.9 (2)	C20—C21—H21	120.2
O1—C5—C4	117.3 (3)	C21—C22—C23	120.3 (3)
O1—C5—C6	124.3 (3)	C21—C22—H22	119.8
C4—C5—C6	118.3 (3)	C23—C22—H22	119.8
C1—C6—C5	118.1 (3)	C18—C23—C22	120.5 (3)
C1—C6—C7	104.9 (3)	C18—C23—H23	119.7
C5—C6—C7	136.9 (3)	C22—C23—H23	119.7
C8—C7—C6	107.4 (3)	O3—C24—C25	120.7 (3)
C8—C7—H7	126.3	O3—C24—C2	120.1 (3)
C6—C7—H7	126.3	C25—C24—C2	119.3 (3)
C7—C8—O4	110.9 (3)	C30—C25—C26	118.7 (3)
C7—C8—C31	133.4 (3)	C30—C25—C24	119.5 (3)
O4—C8—C31	115.6 (3)	C26—C25—C24	121.7 (3)
O1—C9—C10	109.8 (3)	C27—C26—C25	120.2 (3)
O1—C9—H9A	109.7	C27—C26—H26	119.9
C10—C9—H9A	109.7	C25—C26—H26	119.9
O1—C9—H9B	109.7	C28—C27—C26	120.1 (3)
C10—C9—H9B	109.7	C28—C27—H27	120.0
H9A—C9—H9B	108.2	C26—C27—H27	120.0
C11—C10—N3	107.9 (3)	C27—C28—C29	120.1 (4)
C11—C10—C9	131.1 (3)	C27—C28—H28	120.0
N3—C10—C9	121.0 (3)	C29—C28—H28	120.0
N1—C11—C10	105.6 (3)	C30—C29—C28	119.8 (3)
N1—C11—H11	127.2	C30—C29—H29	120.1
C10—C11—H11	127.2	C28—C29—H29	120.1
C16—C12—C13	118.5 (3)	C29—C30—C25	121.2 (3)
C16—C12—N1	121.7 (3)	C29—C30—H30	119.4
C13—C12—N1	119.8 (3)	C25—C30—H30	119.4
C14—C13—C12	117.9 (3)	C8—C31—H31A	109.5
C14—C13—H13	121.0	C8—C31—H31B	109.5
C12—C13—H13	121.0	H31A—C31—H31B	109.5
N4—C14—C13	124.9 (4)	C8—C31—H31C	109.5
N4—C14—H14	117.6	H31A—C31—H31C	109.5
C13—C14—H14	117.6	H31B—C31—H31C	109.5
N4—C15—C16	125.4 (4)
C11—N1—N2—N3	0.5 (3)	N2—N1—C12—C16	−168.3 (3)
C12—N1—N2—N3	177.1 (3)	C11—N1—C12—C13	−172.8 (3)
N1—N2—N3—C10	0.3 (4)	N2—N1—C12—C13	11.3 (4)
C8—O4—C1—C2	177.6 (2)	C16—C12—C13—C14	0.5 (5)
C8—O4—C1—C6	−0.1 (3)	N1—C12—C13—C14	−179.0 (3)
O4—C1—C2—C3	−177.4 (2)	C15—N4—C14—C13	0.0 (6)
C6—C1—C2—C3	0.0 (4)	C12—C13—C14—N4	−0.5 (7)
O4—C1—C2—C24	−1.4 (4)	C14—N4—C15—C16	0.6 (6)
C6—C1—C2—C24	176.0 (3)	C13—C12—C16—C15	−0.1 (5)
C1—C2—C3—C4	0.5 (4)	N1—C12—C16—C15	179.5 (3)
C24—C2—C3—C4	−175.7 (2)	N4—C15—C16—C12	−0.5 (6)
C2—C3—C4—C5	0.3 (4)	C5—C4—C17—O2	−144.0 (3)
C2—C3—C4—C17	−176.2 (2)	C3—C4—C17—O2	32.3 (4)
C9—O1—C5—C4	−158.5 (2)	C5—C4—C17—C18	41.3 (4)
C9—O1—C5—C6	23.3 (4)	C3—C4—C17—C18	−142.4 (3)
C3—C4—C5—O1	−179.9 (2)	O2—C17—C18—C23	−149.1 (3)
C17—C4—C5—O1	−3.7 (4)	C4—C17—C18—C23	25.6 (4)
C3—C4—C5—C6	−1.6 (4)	O2—C17—C18—C19	23.6 (4)
C17—C4—C5—C6	174.6 (2)	C4—C17—C18—C19	−161.7 (3)
O4—C1—C6—C5	176.4 (2)	C23—C18—C19—C20	0.4 (5)
C2—C1—C6—C5	−1.3 (4)	C17—C18—C19—C20	−172.6 (3)
O4—C1—C6—C7	−1.1 (3)	C18—C19—C20—C21	0.1 (5)
C2—C1—C6—C7	−178.7 (3)	C19—C20—C21—C22	−0.3 (5)
O1—C5—C6—C1	−179.8 (2)	C20—C21—C22—C23	0.0 (5)
C4—C5—C6—C1	2.0 (4)	C19—C18—C23—C22	−0.7 (5)
O1—C5—C6—C7	−3.4 (5)	C17—C18—C23—C22	171.9 (3)
C4—C5—C6—C7	178.4 (3)	C21—C22—C23—C18	0.5 (5)
C1—C6—C7—C8	1.9 (3)	C1—C2—C24—O3	−128.6 (3)
C5—C6—C7—C8	−174.9 (3)	C3—C2—C24—O3	47.1 (4)
C6—C7—C8—O4	−2.0 (3)	C1—C2—C24—C25	52.4 (4)
C6—C7—C8—C31	176.2 (3)	C3—C2—C24—C25	−131.8 (3)
C1—O4—C8—C7	1.3 (3)	O3—C24—C25—C30	20.2 (4)
C1—O4—C8—C31	−177.2 (2)	C2—C24—C25—C30	−160.8 (3)
C5—O1—C9—C10	149.1 (2)	O3—C24—C25—C26	−155.7 (3)
N2—N3—C10—C11	−0.9 (4)	C2—C24—C25—C26	23.2 (4)
N2—N3—C10—C9	−177.8 (3)	C30—C25—C26—C27	−1.2 (4)
O1—C9—C10—C11	93.6 (4)	C24—C25—C26—C27	174.8 (3)
O1—C9—C10—N3	−90.4 (4)	C25—C26—C27—C28	1.8 (5)
N2—N1—C11—C10	−1.0 (3)	C26—C27—C28—C29	−0.5 (5)
C12—N1—C11—C10	−177.2 (3)	C27—C28—C29—C30	−1.2 (6)
N3—C10—C11—N1	1.2 (3)	C28—C29—C30—C25	1.8 (5)
C9—C10—C11—N1	177.6 (3)	C26—C25—C30—C29	−0.5 (5)
C11—N1—C12—C16	7.6 (5)	C24—C25—C30—C29	−176.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O3i	0.93	2.33	3.225 (10)	161
C16—H16···O3i	0.93	2.55	3.473 (10)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O3i	0.93	2.33	3.225 (10)	161
C16—H16⋯O3i	0.93	2.55	3.473 (10)	171

Symmetry code: (i) .