(E)-Benzaldehyde O-{[3-(pyridin-3-yl)isoxazol-5-yl]meth-yl}oxime.

The asymmetric unit of the title compound, C(16)H(13)N(3)O(2), contains two independent mol-ecules in which the pyridine and benzene rings form dihedral angles of 81.7 (2) and 79.8 (2)°, indicating the twist in the mol-ecules. In the crystal, weak C-H⋯N inter-actions link mol-ecules into chains along [100].

Related literature

For organic synthesis of isoxazole systems, see: Giomi et al. (2008 ▶); Chukanov & Reznikov (2011 ▶). For the biological activity of isoxazole systems, see: Meyers et al. (2011 ▶); Basappa et al. (2003 ▶); Lee et al. (2009 ▶); Talley et al. (2000 ▶); Farrerons et al. (2003 ▶); Edgard et al. (2004 ▶); For hydrogen-bond graph-set motifs, see: Etter (1990 ▶). For hydrogen bonding, see: Nardelli (1995 ▶).

Experimental

Crystal data

C16H13N3O2

M = 279.29

Orthorhombic,

a = 19.364 (12) Å

b = 4.459 (3) Å

c = 31.775 (19) Å

V = 2744 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.40 × 0.01 × 0.01 mm

Data collection

Rigaku Saturn724+ diffractometer

17573 measured reflections

4762 independent reflections

3544 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.136

S = 0.99

4762 reflections

379 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku, 2011 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812010732/vm2159sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010732/vm2159Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812010732/vm2159Isup3.cml

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

C16H13N3O2	Dx = 1.352 Mg m−3
Mr = 279.29	Melting point: 322(1) K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2c -2n	Cell parameters from 4687 reflections
a = 19.364 (12) Å	θ = 2.5–25.1°
b = 4.459 (3) Å	µ = 0.09 mm−1
c = 31.775 (19) Å	T = 100 K
V = 2744 (3) Å3	Needle, colourless
Z = 8	0.40 × 0.01 × 0.01 mm
F(000) = 1168

Rigaku Saturn724+ diffractometer	3544 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.086
Confocal monochromator	θmax = 25.0°, θmin = 3.8°
Detector resolution: 28.5714 pixels mm-1	h = −22→20
profile data from ω–scans	k = −4→5
17573 measured reflections	l = −37→37
4762 independent 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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0521P)2] where P = (Fo2 + 2Fc2)/3
4762 reflections	(Δ/σ)max < 0.001
379 parameters	Δρmax = 0.32 e Å−3
1 restraint	Δρmin = −0.25 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
O1	0.42469 (12)	1.0263 (6)	−0.10487 (8)	0.0291 (6)
O2	0.54055 (14)	0.8039 (6)	−0.04845 (8)	0.0312 (7)
O3	0.66365 (12)	1.0298 (6)	0.27422 (8)	0.0289 (6)
O4	0.78145 (14)	0.8318 (6)	0.21677 (8)	0.0341 (7)
N1	0.36765 (16)	0.8518 (7)	−0.08969 (10)	0.0272 (8)
N2	0.56013 (16)	0.6236 (8)	−0.01381 (9)	0.0310 (8)
N3	0.57737 (19)	0.2015 (7)	0.10467 (11)	0.0317 (8)
N4	0.60742 (16)	0.8498 (7)	0.25889 (10)	0.0283 (8)
N5	0.80334 (18)	0.6730 (8)	0.18076 (10)	0.0335 (9)
N6	0.82896 (17)	0.3085 (9)	0.05894 (11)	0.0363 (9)
C1	0.3367 (2)	0.7268 (9)	−0.12076 (13)	0.0251 (9)
H1	0.3528	0.7638	−0.1485	0.030*
C2	0.27783 (18)	0.5302 (8)	−0.11453 (11)	0.0236 (9)
C3	0.25108 (19)	0.3751 (9)	−0.14916 (12)	0.0268 (9)
H3	0.2716	0.4005	−0.1761	0.032*
C4	0.1950 (2)	0.1849 (9)	−0.14465 (14)	0.0335 (10)
H4	0.1774	0.0803	−0.1684	0.040*
C5	0.1645 (2)	0.1470 (10)	−0.10568 (13)	0.0350 (10)
H5	0.1262	0.0156	−0.1027	0.042*
C6	0.1894 (2)	0.2993 (10)	−0.07096 (13)	0.0328 (11)
H6	0.1679	0.2754	−0.0443	0.039*
C7	0.2467 (2)	0.4896 (9)	−0.07537 (12)	0.0304 (9)
H7	0.2644	0.5917	−0.0515	0.037*
C8	0.4554 (2)	1.1802 (9)	−0.06927 (12)	0.0290 (10)
H8A	0.4201	1.3090	−0.0558	0.035*
H8B	0.4932	1.3113	−0.0794	0.035*
C9	0.48330 (17)	0.9676 (8)	−0.03760 (11)	0.0222 (8)
C10	0.4652 (2)	0.9032 (9)	0.00232 (11)	0.0282 (9)
H10	0.4280	0.9851	0.0180	0.034*
C11	0.51395 (19)	0.6865 (9)	0.01587 (12)	0.0226 (9)
C12	0.51848 (18)	0.5373 (9)	0.05737 (12)	0.0261 (9)
C13	0.47154 (19)	0.6129 (10)	0.08933 (12)	0.0303 (10)
H13	0.4355	0.7529	0.0842	0.036*
C14	0.47866 (19)	0.4803 (10)	0.12829 (13)	0.0345 (10)
H14	0.4474	0.5266	0.1504	0.041*
C15	0.5324 (2)	0.2773 (10)	0.13475 (13)	0.0347 (10)
H15	0.5373	0.1889	0.1618	0.042*
C16	0.5701 (2)	0.3278 (9)	0.06674 (12)	0.0294 (9)
H16	0.6014	0.2725	0.0451	0.035*
C17	0.5772 (2)	0.7288 (9)	0.29060 (12)	0.0248 (10)
H17	0.5929	0.7721	0.3183	0.030*
C18	0.51797 (18)	0.5220 (8)	0.28453 (11)	0.0240 (9)
C19	0.4886 (2)	0.4702 (9)	0.24531 (12)	0.0306 (10)
H19	0.5060	0.5698	0.2211	0.037*
C20	0.4334 (2)	0.2713 (9)	0.24168 (13)	0.0311 (10)
H20	0.4138	0.2329	0.2148	0.037*
C21	0.40688 (19)	0.1297 (9)	0.27672 (12)	0.0318 (10)
H21	0.3689	−0.0038	0.2740	0.038*
C22	0.4360 (2)	0.1830 (10)	0.31618 (12)	0.0295 (10)
H22	0.4181	0.0857	0.3404	0.035*
C23	0.4910 (2)	0.3773 (9)	0.31983 (13)	0.0291 (9)
H23	0.5109	0.4131	0.3467	0.035*
C24	0.6926 (2)	1.1897 (9)	0.23951 (12)	0.0296 (10)
H24A	0.7290	1.3259	0.2501	0.036*
H24B	0.6561	1.3147	0.2265	0.036*
C25	0.72282 (18)	0.9900 (9)	0.20662 (12)	0.0253 (9)
C26	0.7059 (2)	0.9344 (9)	0.16578 (12)	0.0279 (9)
H26	0.6675	1.0106	0.1505	0.034*
C27	0.7574 (2)	0.7403 (9)	0.15124 (13)	0.0246 (9)
C28	0.76501 (19)	0.6134 (9)	0.10804 (12)	0.0266 (9)
C29	0.7201 (2)	0.7057 (10)	0.07652 (12)	0.0319 (10)
H29	0.6832	0.8394	0.0824	0.038*
C30	0.7309 (2)	0.5954 (10)	0.03557 (13)	0.0376 (10)
H30	0.7012	0.6526	0.0132	0.045*
C31	0.7852 (2)	0.4038 (11)	0.02849 (13)	0.0397 (11)
H31	0.7924	0.3338	0.0006	0.048*
C32	0.8173 (2)	0.4122 (10)	0.09790 (12)	0.0326 (10)
H32	0.8465	0.3441	0.1199	0.039*

	U11	U22	U33	U12	U13	U23
O1	0.0330 (15)	0.0331 (17)	0.0211 (14)	−0.0047 (12)	−0.0017 (11)	0.0032 (12)
O2	0.0334 (16)	0.0400 (18)	0.0201 (16)	0.0057 (13)	0.0006 (13)	0.0018 (12)
O3	0.0346 (15)	0.0343 (18)	0.0179 (14)	−0.0090 (12)	0.0007 (11)	−0.0008 (12)
O4	0.0330 (17)	0.045 (2)	0.0239 (16)	−0.0007 (14)	−0.0060 (12)	−0.0055 (13)
N1	0.0316 (19)	0.028 (2)	0.0220 (18)	0.0003 (15)	−0.0010 (14)	0.0018 (14)
N2	0.033 (2)	0.041 (2)	0.0196 (18)	0.0037 (16)	−0.0030 (15)	0.0085 (15)
N3	0.036 (2)	0.038 (2)	0.0212 (19)	0.0052 (16)	−0.0026 (15)	0.0035 (16)
N4	0.0289 (18)	0.030 (2)	0.0260 (19)	−0.0003 (15)	0.0003 (15)	−0.0065 (16)
N5	0.034 (2)	0.046 (2)	0.0210 (18)	0.0077 (15)	−0.0015 (14)	−0.0038 (16)
N6	0.0274 (19)	0.053 (3)	0.029 (2)	0.0053 (16)	0.0036 (16)	−0.0066 (17)
C1	0.032 (2)	0.023 (2)	0.020 (2)	0.0047 (17)	−0.0016 (17)	0.0012 (16)
C2	0.027 (2)	0.020 (2)	0.024 (2)	0.0047 (16)	−0.0036 (16)	0.0051 (16)
C3	0.031 (2)	0.028 (2)	0.021 (2)	0.0078 (17)	0.0020 (17)	0.0032 (18)
C4	0.037 (3)	0.028 (3)	0.035 (3)	−0.0016 (19)	−0.010 (2)	0.004 (2)
C5	0.028 (2)	0.036 (3)	0.041 (3)	−0.0002 (18)	0.000 (2)	0.008 (2)
C6	0.029 (2)	0.039 (3)	0.031 (3)	0.006 (2)	0.003 (2)	0.0066 (19)
C7	0.037 (2)	0.031 (3)	0.023 (2)	0.0008 (18)	−0.0017 (17)	0.0052 (18)
C8	0.037 (2)	0.031 (3)	0.019 (2)	−0.0045 (19)	−0.0066 (17)	0.0017 (17)
C9	0.023 (2)	0.020 (2)	0.024 (2)	−0.0016 (16)	−0.0039 (16)	−0.0039 (15)
C10	0.028 (2)	0.039 (3)	0.018 (2)	0.0017 (18)	0.0031 (16)	−0.0046 (17)
C11	0.024 (2)	0.026 (2)	0.018 (2)	−0.0064 (16)	0.0026 (16)	0.0011 (16)
C12	0.025 (2)	0.032 (2)	0.0208 (19)	−0.0007 (17)	−0.0051 (16)	−0.0038 (17)
C13	0.029 (2)	0.038 (3)	0.024 (2)	0.0004 (18)	0.0002 (17)	0.0034 (18)
C14	0.033 (2)	0.046 (3)	0.024 (2)	−0.001 (2)	−0.0008 (18)	−0.0052 (18)
C15	0.041 (2)	0.044 (3)	0.019 (2)	−0.002 (2)	0.0017 (18)	0.0037 (18)
C16	0.026 (2)	0.035 (3)	0.027 (2)	−0.0025 (18)	−0.0054 (16)	0.0008 (18)
C17	0.036 (2)	0.025 (2)	0.014 (2)	0.0029 (17)	0.0004 (17)	−0.0042 (16)
C18	0.033 (2)	0.015 (2)	0.024 (2)	0.0027 (16)	0.0024 (17)	−0.0062 (15)
C19	0.033 (2)	0.033 (3)	0.025 (2)	0.0061 (19)	0.0018 (18)	0.0039 (18)
C20	0.035 (2)	0.034 (3)	0.025 (2)	−0.0041 (19)	−0.0078 (19)	−0.0029 (17)
C21	0.027 (2)	0.036 (3)	0.032 (2)	0.0031 (18)	0.003 (2)	−0.005 (2)
C22	0.027 (2)	0.040 (3)	0.022 (2)	0.0090 (18)	0.0093 (18)	0.0007 (18)
C23	0.034 (2)	0.029 (3)	0.024 (2)	0.0014 (18)	0.0052 (18)	−0.0033 (18)
C24	0.035 (2)	0.030 (2)	0.024 (2)	−0.0016 (18)	0.0057 (18)	0.0065 (18)
C25	0.031 (2)	0.021 (2)	0.024 (2)	−0.0023 (16)	0.0039 (16)	0.0039 (16)
C26	0.028 (2)	0.030 (2)	0.026 (2)	0.0018 (18)	−0.0011 (16)	0.0017 (17)
C27	0.028 (2)	0.025 (2)	0.020 (2)	−0.0051 (17)	0.0043 (17)	0.0035 (15)
C28	0.027 (2)	0.028 (2)	0.025 (2)	−0.0042 (17)	0.0024 (16)	0.0010 (17)
C29	0.029 (2)	0.044 (3)	0.023 (2)	0.0012 (19)	0.0037 (17)	−0.0007 (19)
C30	0.037 (2)	0.050 (3)	0.025 (2)	−0.002 (2)	−0.0027 (19)	−0.004 (2)
C31	0.033 (2)	0.062 (3)	0.025 (2)	−0.002 (2)	0.0015 (19)	−0.008 (2)
C32	0.032 (2)	0.042 (3)	0.023 (2)	−0.002 (2)	0.0023 (17)	0.0002 (19)

O1—N1	1.435 (4)	C12—C16	1.400 (5)
O1—C8	1.451 (5)	C12—C13	1.404 (5)
O2—C9	1.371 (4)	C13—C14	1.379 (5)
O2—N2	1.415 (4)	C13—H13	0.9500
O3—C24	1.428 (5)	C14—C15	1.395 (6)
O3—N4	1.438 (4)	C14—H14	0.9500
O4—C25	1.375 (4)	C15—H15	0.9500
O4—N5	1.411 (4)	C16—H16	0.9500
N1—C1	1.282 (5)	C17—C18	1.484 (5)
N2—C11	1.330 (5)	C17—H17	0.9500
N3—C15	1.336 (5)	C18—C19	1.390 (5)
N3—C16	1.338 (5)	C18—C23	1.395 (5)
N4—C17	1.284 (5)	C19—C20	1.394 (6)
N5—C27	1.327 (5)	C19—H19	0.9500
N6—C32	1.341 (5)	C20—C21	1.379 (6)
N6—C31	1.355 (5)	C20—H20	0.9500
C1—C2	1.452 (5)	C21—C22	1.396 (5)
C1—H1	0.9500	C21—H21	0.9500
C2—C7	1.394 (5)	C22—C23	1.378 (6)
C2—C3	1.399 (5)	C22—H22	0.9500
C3—C4	1.386 (6)	C23—H23	0.9500
C3—H3	0.9500	C24—C25	1.493 (5)
C4—C5	1.382 (6)	C24—H24A	0.9900
C4—H4	0.9500	C24—H24B	0.9900
C5—C6	1.383 (6)	C25—C26	1.361 (5)
C5—H5	0.9500	C26—C27	1.400 (6)
C6—C7	1.404 (6)	C26—H26	0.9500
C6—H6	0.9500	C27—C28	1.492 (6)
C7—H7	0.9500	C28—C29	1.388 (5)
C8—C9	1.484 (5)	C28—C32	1.391 (6)
C8—H8A	0.9900	C29—C30	1.407 (5)
C8—H8B	0.9900	C29—H29	0.9500
C9—C10	1.347 (5)	C30—C31	1.373 (5)
C10—C11	1.417 (5)	C30—H30	0.9500
C10—H10	0.9500	C31—H31	0.9500
C11—C12	1.479 (5)	C32—H32	0.9500
N1—O1—C8	108.1 (3)	N3—C15—H15	118.5
C9—O2—N2	108.9 (3)	C14—C15—H15	118.5
C24—O3—N4	108.3 (3)	N3—C16—C12	123.2 (4)
C25—O4—N5	108.4 (3)	N3—C16—H16	118.4
C1—N1—O1	109.6 (3)	C12—C16—H16	118.4
C11—N2—O2	104.6 (3)	N4—C17—C18	120.8 (3)
C15—N3—C16	118.0 (4)	N4—C17—H17	119.6
C17—N4—O3	108.3 (3)	C18—C17—H17	119.6
C27—N5—O4	105.0 (3)	C19—C18—C23	119.4 (3)
C32—N6—C31	116.5 (4)	C19—C18—C17	122.4 (3)
N1—C1—C2	121.6 (4)	C23—C18—C17	118.2 (3)
N1—C1—H1	119.2	C18—C19—C20	119.6 (4)
C2—C1—H1	119.2	C18—C19—H19	120.2
C7—C2—C3	118.5 (3)	C20—C19—H19	120.2
C7—C2—C1	122.7 (4)	C21—C20—C19	120.7 (4)
C3—C2—C1	118.8 (3)	C21—C20—H20	119.7
C4—C3—C2	120.7 (4)	C19—C20—H20	119.7
C4—C3—H3	119.6	C20—C21—C22	119.8 (4)
C2—C3—H3	119.6	C20—C21—H21	120.1
C5—C4—C3	120.2 (4)	C22—C21—H21	120.1
C5—C4—H4	119.9	C23—C22—C21	119.7 (4)
C3—C4—H4	119.9	C23—C22—H22	120.2
C4—C5—C6	120.4 (4)	C21—C22—H22	120.2
C4—C5—H5	119.8	C22—C23—C18	120.8 (4)
C6—C5—H5	119.8	C22—C23—H23	119.6
C5—C6—C7	119.5 (4)	C18—C23—H23	119.6
C5—C6—H6	120.2	O3—C24—C25	113.4 (3)
C7—C6—H6	120.2	O3—C24—H24A	108.9
C2—C7—C6	120.6 (4)	C25—C24—H24A	108.9
C2—C7—H7	119.7	O3—C24—H24B	108.9
C6—C7—H7	119.7	C25—C24—H24B	108.9
O1—C8—C9	112.1 (3)	H24A—C24—H24B	107.7
O1—C8—H8A	109.2	C26—C25—O4	109.2 (3)
C9—C8—H8A	109.2	C26—C25—C24	132.9 (4)
O1—C8—H8B	109.2	O4—C25—C24	117.8 (3)
C9—C8—H8B	109.2	C25—C26—C27	104.8 (3)
H8A—C8—H8B	107.9	C25—C26—H26	127.6
C10—C9—O2	109.5 (3)	C27—C26—H26	127.6
C10—C9—C8	132.9 (4)	N5—C27—C26	112.6 (4)
O2—C9—C8	117.6 (3)	N5—C27—C28	119.9 (4)
C9—C10—C11	105.0 (3)	C26—C27—C28	127.5 (4)
C9—C10—H10	127.5	C29—C28—C32	118.7 (4)
C11—C10—H10	127.5	C29—C28—C27	119.3 (4)
N2—C11—C10	112.1 (3)	C32—C28—C27	122.0 (3)
N2—C11—C12	119.8 (3)	C28—C29—C30	118.0 (4)
C10—C11—C12	128.1 (3)	C28—C29—H29	121.0
C16—C12—C13	117.9 (4)	C30—C29—H29	121.0
C16—C12—C11	122.2 (3)	C31—C30—C29	118.9 (4)
C13—C12—C11	119.9 (3)	C31—C30—H30	120.5
C14—C13—C12	118.8 (4)	C29—C30—H30	120.5
C14—C13—H13	120.6	N6—C31—C30	123.8 (4)
C12—C13—H13	120.6	N6—C31—H31	118.1
C13—C14—C15	119.0 (4)	C30—C31—H31	118.1
C13—C14—H14	120.5	N6—C32—C28	124.0 (4)
C15—C14—H14	120.5	N6—C32—H32	118.0
N3—C15—C14	123.0 (4)	C28—C32—H32	118.0
C8—O1—N1—C1	176.2 (3)	C13—C12—C16—N3	−1.3 (6)
C9—O2—N2—C11	0.2 (4)	C11—C12—C16—N3	176.5 (4)
C24—O3—N4—C17	−173.8 (3)	O3—N4—C17—C18	−178.3 (3)
C25—O4—N5—C27	−0.4 (4)	N4—C17—C18—C19	−5.9 (6)
O1—N1—C1—C2	178.5 (3)	N4—C17—C18—C23	174.6 (4)
N1—C1—C2—C7	7.0 (6)	C23—C18—C19—C20	−1.0 (6)
N1—C1—C2—C3	−173.1 (3)	C17—C18—C19—C20	179.5 (4)
C7—C2—C3—C4	−0.1 (5)	C18—C19—C20—C21	1.2 (6)
C1—C2—C3—C4	179.9 (4)	C19—C20—C21—C22	−0.8 (6)
C2—C3—C4—C5	0.3 (6)	C20—C21—C22—C23	0.1 (6)
C3—C4—C5—C6	0.3 (6)	C21—C22—C23—C18	0.1 (6)
C4—C5—C6—C7	−1.0 (6)	C19—C18—C23—C22	0.4 (6)
C3—C2—C7—C6	−0.6 (5)	C17—C18—C23—C22	179.9 (4)
C1—C2—C7—C6	179.4 (4)	N4—O3—C24—C25	−62.8 (4)
C5—C6—C7—C2	1.1 (6)	N5—O4—C25—C26	1.0 (4)
N1—O1—C8—C9	62.2 (4)	N5—O4—C25—C24	−176.6 (3)
N2—O2—C9—C10	0.3 (4)	O3—C24—C25—C26	114.7 (5)
N2—O2—C9—C8	178.1 (3)	O3—C24—C25—O4	−68.4 (4)
O1—C8—C9—C10	−113.6 (5)	O4—C25—C26—C27	−1.1 (4)
O1—C8—C9—O2	69.3 (4)	C24—C25—C26—C27	175.9 (4)
O2—C9—C10—C11	−0.7 (4)	O4—N5—C27—C26	−0.3 (5)
C8—C9—C10—C11	−178.0 (4)	O4—N5—C27—C28	179.1 (3)
O2—N2—C11—C10	−0.6 (4)	C25—C26—C27—N5	0.9 (5)
O2—N2—C11—C12	−179.8 (3)	C25—C26—C27—C28	−178.5 (4)
C9—C10—C11—N2	0.8 (5)	N5—C27—C28—C29	−174.5 (4)
C9—C10—C11—C12	179.9 (4)	C26—C27—C28—C29	4.8 (6)
N2—C11—C12—C16	−0.4 (6)	N5—C27—C28—C32	3.3 (6)
C10—C11—C12—C16	−179.4 (4)	C26—C27—C28—C32	−177.4 (4)
N2—C11—C12—C13	177.3 (3)	C32—C28—C29—C30	−1.4 (6)
C10—C11—C12—C13	−1.7 (6)	C27—C28—C29—C30	176.4 (4)
C16—C12—C13—C14	0.5 (6)	C28—C29—C30—C31	−0.3 (6)
C11—C12—C13—C14	−177.2 (3)	C32—N6—C31—C30	−0.1 (7)
C12—C13—C14—C15	0.4 (6)	C29—C30—C31—N6	1.1 (7)
C16—N3—C15—C14	0.1 (6)	C31—N6—C32—C28	−1.8 (6)
C13—C14—C15—N3	−0.8 (6)	C29—C28—C32—N6	2.6 (6)
C15—N3—C16—C12	0.9 (6)	C27—C28—C32—N6	−175.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···N3i	0.95	2.43	3.374 (5)	174
C10—H10···N6ii	0.95	2.49	3.443 (5)	179

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C26—H26⋯N3i	0.95	2.43	3.374 (5)	174
C10—H10⋯N6ii	0.95	2.49	3.443 (5)	179

Symmetry codes: (i) ; (ii) .