3-Nitro-N-(8-quinol-yl)benzamide.

The title compound, C(16)H(11)N(3)O(3), crystallizes with two independent mol-ecules which are almost identical to each other in the asymmetric unit. The dihedral angle between the quinoline ring system and the nitro-benzene ring is 51.04 (9)° in one of the mol-ecules and 48.91 (9)° in the other. The crystal packing is stabilized by C-H⋯O hydrogen bonds and π-π inter-actions, with a centroid-centroid distance of 3.6010 (15) Å.

Related literature

For general background, see: Oku et al. (1998 ▶, 1999 ▶). For a related structure, see: Lei et al. (2008 ▶).

Experimental

Crystal data

C16H11N3O3

M = 293.28

Monoclinic,

a = 7.3783 (14) Å

b = 23.878 (5) Å

c = 7.4371 (14) Å

β = 90.775 (3)°

V = 1310.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 93 (2) K

0.40 × 0.30 × 0.23 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: none

10838 measured reflections

3071 independent reflections

2860 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.075

S = 1.14

3071 reflections

397 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.19 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037811/ci2717sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037811/ci2717Isup2.hkl

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

C16H11N3O3	F000 = 608
Mr = 293.28	Dx = 1.487 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4482 reflections
a = 7.3783 (14) Å	θ = 3.2–27.5º
b = 23.878 (5) Å	µ = 0.11 mm−1
c = 7.4371 (14) Å	T = 93 (2) K
β = 90.775 (3)º	Block, white
V = 1310.2 (4) Å3	0.40 × 0.30 × 0.23 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	2860 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Monochromator: graphite	θmax = 27.5º
T = 93(2) K	θmin = 3.2º
ω scans	h = −9→9
Absorption correction: none	k = −31→30
10838 measured reflections	l = −9→9
3071 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.075	w = 1/[σ2(Fo2) + (0.0354P)2] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max = 0.001
3071 reflections	Δρmax = 0.19 e Å−3
397 parameters	Δρmin = −0.19 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	0.3802 (2)	0.19096 (7)	0.4467 (2)	0.0229 (4)
O2	0.1871 (3)	0.35241 (8)	0.0594 (2)	0.0334 (4)
O3	0.1573 (2)	0.43422 (7)	0.1784 (2)	0.0308 (4)
N1	0.9400 (3)	0.22508 (8)	0.7724 (3)	0.0202 (4)
N2	0.6102 (3)	0.21775 (8)	0.6364 (3)	0.0195 (4)
H2N	0.6600	0.2477	0.6850	0.023*
N3	0.2028 (3)	0.38491 (8)	0.1864 (3)	0.0220 (4)
C2	1.1064 (3)	0.23028 (11)	0.8387 (3)	0.0233 (5)
H2	1.1537	0.2670	0.8546	0.028*
C3	1.2169 (3)	0.18492 (11)	0.8868 (3)	0.0263 (5)
H3	1.3365	0.1910	0.9315	0.032*
C4	1.1508 (3)	0.13180 (11)	0.8688 (3)	0.0255 (5)
H4	1.2237	0.1006	0.9024	0.031*
C5	0.8918 (3)	0.07037 (10)	0.7766 (3)	0.0224 (5)
H5	0.9567	0.0374	0.8082	0.027*
C6	0.7193 (3)	0.06662 (10)	0.7085 (3)	0.0237 (5)
H6	0.6655	0.0307	0.6949	0.028*
C7	0.6189 (3)	0.11439 (10)	0.6579 (3)	0.0218 (5)
H7	0.4997	0.1105	0.6097	0.026*
C8	0.6946 (3)	0.16665 (9)	0.6785 (3)	0.0181 (5)
C9	0.8739 (3)	0.17209 (9)	0.7526 (3)	0.0181 (5)
C10	0.9734 (3)	0.12345 (10)	0.7999 (3)	0.0206 (5)
C11	0.4622 (3)	0.22707 (10)	0.5310 (3)	0.0184 (5)
C12	0.4060 (3)	0.28758 (9)	0.5227 (3)	0.0165 (5)
C13	0.3286 (3)	0.30764 (9)	0.3644 (3)	0.0178 (5)
H13	0.3102	0.2836	0.2640	0.021*
C14	0.2792 (3)	0.36325 (9)	0.3560 (3)	0.0169 (4)
C15	0.3002 (3)	0.39973 (10)	0.4987 (3)	0.0205 (5)
H15	0.2654	0.4379	0.4883	0.025*
C16	0.3735 (3)	0.37886 (10)	0.6575 (3)	0.0207 (5)
H16	0.3869	0.4027	0.7591	0.025*
C17	0.4276 (3)	0.32341 (10)	0.6691 (3)	0.0188 (5)
H17	0.4798	0.3097	0.7779	0.023*
O1A	0.6075 (2)	0.26160 (7)	0.0420 (2)	0.0221 (4)
O2A	0.4490 (2)	0.06211 (8)	0.1206 (3)	0.0371 (5)
O3A	0.6518 (3)	0.00459 (8)	0.2183 (3)	0.0488 (6)
N1A	0.8655 (3)	0.35147 (8)	0.5612 (2)	0.0213 (4)
N2A	0.7920 (3)	0.29510 (8)	0.2650 (3)	0.0189 (4)
H2NA	0.8755	0.2849	0.3440	0.023*
N3A	0.6014 (3)	0.05199 (8)	0.1811 (3)	0.0268 (5)
C2A	0.9074 (3)	0.37849 (11)	0.7114 (3)	0.0267 (6)
H2A	0.9586	0.3578	0.8086	0.032*
C3A	0.8798 (3)	0.43636 (12)	0.7346 (3)	0.0299 (6)
H3A	0.9132	0.4540	0.8446	0.036*
C4A	0.8049 (3)	0.46662 (11)	0.5980 (3)	0.0273 (6)
H4A	0.7831	0.5055	0.6130	0.033*
C5A	0.6826 (3)	0.46776 (10)	0.2831 (3)	0.0241 (5)
H5A	0.6603	0.5069	0.2881	0.029*
C6A	0.6403 (3)	0.43863 (10)	0.1308 (3)	0.0235 (5)
H6A	0.5880	0.4578	0.0309	0.028*
C7A	0.6729 (3)	0.38034 (10)	0.1186 (3)	0.0217 (5)
H7A	0.6420	0.3606	0.0115	0.026*
C8A	0.7486 (3)	0.35259 (9)	0.2608 (3)	0.0174 (5)
C9A	0.7935 (3)	0.38198 (10)	0.4228 (3)	0.0185 (5)
C10A	0.7595 (3)	0.44004 (10)	0.4334 (3)	0.0211 (5)
C11A	0.7202 (3)	0.25366 (10)	0.1617 (3)	0.0185 (5)
C12A	0.7870 (3)	0.19612 (10)	0.2061 (3)	0.0174 (5)
C13A	0.6706 (3)	0.15156 (10)	0.1700 (3)	0.0189 (5)
H13A	0.5544	0.1578	0.1174	0.023*
C14A	0.7274 (3)	0.09834 (10)	0.2121 (3)	0.0194 (5)
C15A	0.8969 (3)	0.08665 (10)	0.2844 (3)	0.0231 (5)
H15A	0.9326	0.0492	0.3099	0.028*
C16A	1.0131 (3)	0.13095 (10)	0.3186 (3)	0.0226 (5)
H16A	1.1307	0.1242	0.3674	0.027*
C17A	0.9574 (3)	0.18545 (10)	0.2814 (3)	0.0204 (5)
H17A	1.0366	0.2158	0.3077	0.025*

	U11	U22	U33	U12	U13	U23
O1	0.0230 (9)	0.0215 (9)	0.0242 (9)	0.0012 (7)	−0.0047 (7)	−0.0039 (7)
O2	0.0457 (11)	0.0319 (10)	0.0223 (9)	0.0074 (9)	−0.0102 (8)	−0.0034 (8)
O3	0.0382 (11)	0.0207 (9)	0.0333 (10)	0.0058 (8)	−0.0072 (8)	0.0065 (8)
N1	0.0173 (10)	0.0224 (10)	0.0209 (10)	−0.0028 (8)	0.0014 (8)	0.0017 (9)
N2	0.0215 (10)	0.0154 (10)	0.0214 (10)	0.0025 (8)	−0.0044 (8)	−0.0030 (8)
N3	0.0189 (10)	0.0249 (11)	0.0222 (10)	0.0011 (8)	−0.0008 (8)	0.0029 (9)
C2	0.0187 (11)	0.0264 (14)	0.0247 (13)	−0.0039 (10)	0.0010 (10)	0.0014 (11)
C3	0.0187 (12)	0.0359 (14)	0.0242 (13)	−0.0010 (11)	−0.0007 (10)	0.0016 (11)
C4	0.0209 (12)	0.0329 (14)	0.0228 (12)	0.0065 (11)	0.0003 (10)	0.0021 (11)
C5	0.0242 (12)	0.0197 (12)	0.0233 (12)	0.0043 (10)	0.0008 (10)	0.0020 (10)
C6	0.0298 (13)	0.0166 (12)	0.0248 (12)	−0.0005 (10)	0.0026 (10)	−0.0013 (10)
C7	0.0222 (12)	0.0198 (12)	0.0233 (12)	−0.0008 (9)	−0.0003 (10)	−0.0022 (10)
C8	0.0201 (11)	0.0178 (11)	0.0165 (11)	0.0016 (9)	0.0027 (9)	0.0005 (9)
C9	0.0206 (11)	0.0185 (12)	0.0152 (11)	0.0017 (9)	0.0038 (9)	0.0004 (9)
C10	0.0212 (12)	0.0233 (12)	0.0175 (12)	0.0029 (10)	0.0023 (9)	0.0014 (10)
C11	0.0191 (11)	0.0190 (11)	0.0170 (11)	−0.0009 (9)	0.0010 (9)	−0.0002 (10)
C12	0.0125 (10)	0.0180 (11)	0.0188 (11)	−0.0009 (9)	−0.0006 (9)	−0.0001 (9)
C13	0.0144 (10)	0.0196 (11)	0.0195 (11)	−0.0028 (9)	0.0003 (9)	−0.0022 (9)
C14	0.0135 (10)	0.0207 (11)	0.0166 (11)	−0.0022 (8)	−0.0011 (8)	0.0043 (9)
C15	0.0185 (11)	0.0177 (12)	0.0252 (13)	0.0001 (9)	0.0023 (10)	0.0009 (10)
C16	0.0224 (12)	0.0186 (12)	0.0212 (12)	−0.0022 (9)	0.0009 (10)	−0.0022 (10)
C17	0.0164 (11)	0.0219 (12)	0.0181 (12)	−0.0006 (9)	0.0000 (9)	0.0002 (9)
O1A	0.0235 (8)	0.0199 (8)	0.0229 (9)	0.0015 (7)	−0.0048 (7)	0.0002 (7)
O2A	0.0302 (11)	0.0256 (10)	0.0551 (12)	−0.0065 (8)	−0.0173 (9)	0.0057 (9)
O3A	0.0509 (14)	0.0158 (9)	0.0787 (15)	−0.0034 (9)	−0.0272 (12)	0.0107 (10)
N1A	0.0175 (10)	0.0261 (11)	0.0203 (10)	−0.0014 (8)	−0.0005 (8)	0.0019 (8)
N2A	0.0182 (10)	0.0166 (10)	0.0216 (10)	0.0010 (8)	−0.0046 (8)	0.0015 (8)
N3A	0.0304 (12)	0.0208 (11)	0.0290 (12)	−0.0007 (9)	−0.0063 (10)	0.0023 (9)
C2A	0.0210 (12)	0.0384 (15)	0.0206 (12)	−0.0023 (11)	−0.0020 (10)	−0.0013 (11)
C3A	0.0277 (14)	0.0364 (15)	0.0257 (13)	−0.0091 (12)	0.0030 (11)	−0.0106 (12)
C4A	0.0229 (13)	0.0242 (13)	0.0347 (14)	−0.0054 (10)	0.0047 (11)	−0.0061 (11)
C5A	0.0189 (11)	0.0170 (12)	0.0365 (14)	−0.0011 (9)	0.0040 (10)	0.0045 (10)
C6A	0.0217 (12)	0.0204 (12)	0.0284 (13)	0.0013 (10)	−0.0020 (10)	0.0076 (11)
C7A	0.0214 (11)	0.0214 (12)	0.0224 (12)	−0.0009 (9)	0.0001 (10)	0.0022 (10)
C8A	0.0158 (10)	0.0154 (11)	0.0210 (12)	−0.0009 (9)	0.0019 (9)	0.0012 (9)
C9A	0.0144 (10)	0.0198 (11)	0.0214 (11)	−0.0024 (9)	0.0027 (9)	0.0017 (9)
C10A	0.0171 (11)	0.0203 (12)	0.0260 (12)	−0.0032 (9)	0.0029 (9)	−0.0026 (10)
C11A	0.0173 (11)	0.0199 (12)	0.0183 (12)	0.0005 (9)	0.0012 (10)	−0.0001 (10)
C12A	0.0192 (11)	0.0165 (11)	0.0164 (11)	0.0001 (9)	0.0015 (9)	0.0005 (9)
C13A	0.0224 (12)	0.0203 (12)	0.0138 (11)	0.0016 (9)	−0.0022 (9)	0.0010 (9)
C14A	0.0206 (11)	0.0188 (12)	0.0188 (11)	−0.0016 (9)	−0.0018 (9)	0.0003 (9)
C15A	0.0258 (12)	0.0196 (12)	0.0236 (13)	0.0023 (10)	−0.0026 (10)	−0.0004 (10)
C16A	0.0184 (12)	0.0242 (13)	0.0251 (12)	0.0030 (10)	−0.0038 (10)	0.0006 (10)
C17A	0.0184 (11)	0.0218 (12)	0.0211 (11)	−0.0010 (9)	0.0001 (9)	−0.0006 (10)

O1—C11	1.222 (3)	O1A—C11A	1.224 (3)
O2—N3	1.227 (2)	O2A—N3A	1.230 (3)
O3—N3	1.225 (3)	O3A—N3A	1.222 (3)
N1—C2	1.323 (3)	N1A—C2A	1.323 (3)
N1—C9	1.363 (3)	N1A—C9A	1.363 (3)
N2—C11	1.354 (3)	N2A—C11A	1.356 (3)
N2—C8	1.403 (3)	N2A—C8A	1.410 (3)
N2—H2N	0.88	N2A—H2NA	0.88
N3—C14	1.469 (3)	N3A—C14A	1.462 (3)
C2—C3	1.399 (3)	C2A—C3A	1.408 (4)
C2—H2	0.95	C2A—H2A	0.95
C3—C4	1.365 (3)	C3A—C4A	1.358 (4)
C3—H3	0.95	C3A—H3A	0.95
C4—C10	1.414 (3)	C4A—C10A	1.415 (3)
C4—H4	0.95	C4A—H4A	0.95
C5—C6	1.366 (3)	C5A—C6A	1.362 (3)
C5—C10	1.413 (3)	C5A—C10A	1.412 (3)
C5—H5	0.95	C5A—H5A	0.95
C6—C7	1.409 (3)	C6A—C7A	1.416 (3)
C6—H6	0.95	C6A—H6A	0.95
C7—C8	1.375 (3)	C7A—C8A	1.361 (3)
C7—H7	0.95	C7A—H7A	0.95
C8—C9	1.432 (3)	C8A—C9A	1.429 (3)
C9—C10	1.416 (3)	C9A—C10A	1.411 (3)
C11—C12	1.504 (3)	C11A—C12A	1.495 (3)
C12—C13	1.387 (3)	C12A—C13A	1.391 (3)
C12—C17	1.392 (3)	C12A—C17A	1.393 (3)
C13—C14	1.378 (3)	C13A—C14A	1.373 (3)
C13—H13	0.95	C13A—H13A	0.95
C14—C15	1.380 (3)	C14A—C15A	1.383 (3)
C15—C16	1.385 (3)	C15A—C16A	1.383 (3)
C15—H15	0.95	C15A—H15A	0.95
C16—C17	1.385 (3)	C16A—C17A	1.391 (3)
C16—H16	0.95	C16A—H16A	0.95
C17—H17	0.95	C17A—H17A	0.95
C2—N1—C9	117.2 (2)	C2A—N1A—C9A	117.5 (2)
C11—N2—C8	128.63 (19)	C11A—N2A—C8A	127.67 (18)
C11—N2—H2N	115.7	C11A—N2A—H2NA	116.2
C8—N2—H2N	115.7	C8A—N2A—H2NA	116.2
O3—N3—O2	123.2 (2)	O3A—N3A—O2A	122.6 (2)
O3—N3—C14	118.80 (19)	O3A—N3A—C14A	118.3 (2)
O2—N3—C14	118.03 (19)	O2A—N3A—C14A	119.05 (19)
N1—C2—C3	123.9 (2)	N1A—C2A—C3A	123.3 (2)
N1—C2—H2	118.1	N1A—C2A—H2A	118.3
C3—C2—H2	118.1	C3A—C2A—H2A	118.3
C4—C3—C2	119.2 (2)	C4A—C3A—C2A	119.2 (2)
C4—C3—H3	120.4	C4A—C3A—H3A	120.4
C2—C3—H3	120.4	C2A—C3A—H3A	120.4
C3—C4—C10	119.6 (2)	C3A—C4A—C10A	119.8 (2)
C3—C4—H4	120.2	C3A—C4A—H4A	120.1
C10—C4—H4	120.2	C10A—C4A—H4A	120.1
C6—C5—C10	119.8 (2)	C6A—C5A—C10A	120.3 (2)
C6—C5—H5	120.1	C6A—C5A—H5A	119.9
C10—C5—H5	120.1	C10A—C5A—H5A	119.9
C5—C6—C7	122.0 (2)	C5A—C6A—C7A	121.2 (2)
C5—C6—H6	119.0	C5A—C6A—H6A	119.4
C7—C6—H6	119.0	C7A—C6A—H6A	119.4
C8—C7—C6	119.6 (2)	C8A—C7A—C6A	119.8 (2)
C8—C7—H7	120.2	C8A—C7A—H7A	120.1
C6—C7—H7	120.2	C6A—C7A—H7A	120.1
C7—C8—N2	125.8 (2)	C7A—C8A—N2A	125.6 (2)
C7—C8—C9	119.8 (2)	C7A—C8A—C9A	120.2 (2)
N2—C8—C9	114.33 (19)	N2A—C8A—C9A	114.17 (18)
N1—C9—C10	123.4 (2)	N1A—C9A—C10A	123.4 (2)
N1—C9—C8	116.94 (19)	N1A—C9A—C8A	117.2 (2)
C10—C9—C8	119.6 (2)	C10A—C9A—C8A	119.3 (2)
C5—C10—C4	124.2 (2)	C9A—C10A—C5A	119.1 (2)
C5—C10—C9	119.1 (2)	C9A—C10A—C4A	116.7 (2)
C4—C10—C9	116.7 (2)	C5A—C10A—C4A	124.3 (2)
O1—C11—N2	124.8 (2)	O1A—C11A—N2A	123.7 (2)
O1—C11—C12	121.5 (2)	O1A—C11A—C12A	121.4 (2)
N2—C11—C12	113.66 (19)	N2A—C11A—C12A	114.84 (19)
C13—C12—C17	119.5 (2)	C13A—C12A—C17A	119.3 (2)
C13—C12—C11	118.46 (19)	C13A—C12A—C11A	117.4 (2)
C17—C12—C11	122.01 (19)	C17A—C12A—C11A	123.4 (2)
C14—C13—C12	118.5 (2)	C14A—C13A—C12A	118.6 (2)
C14—C13—H13	120.8	C14A—C13A—H13A	120.7
C12—C13—H13	120.8	C12A—C13A—H13A	120.7
C15—C14—C13	123.1 (2)	C13A—C14A—C15A	123.2 (2)
C15—C14—N3	118.4 (2)	C13A—C14A—N3A	118.3 (2)
C13—C14—N3	118.4 (2)	C15A—C14A—N3A	118.6 (2)
C14—C15—C16	117.8 (2)	C14A—C15A—C16A	118.2 (2)
C14—C15—H15	121.1	C14A—C15A—H15A	120.9
C16—C15—H15	121.1	C16A—C15A—H15A	120.9
C17—C16—C15	120.4 (2)	C15A—C16A—C17A	119.9 (2)
C17—C16—H16	119.8	C15A—C16A—H16A	120.1
C15—C16—H16	119.8	C17A—C16A—H16A	120.1
C16—C17—C12	120.6 (2)	C16A—C17A—C12A	120.9 (2)
C16—C17—H17	119.7	C16A—C17A—H17A	119.5
C12—C17—H17	119.7	C12A—C17A—H17A	119.5
C9—N1—C2—C3	0.7 (3)	C9A—N1A—C2A—C3A	0.5 (3)
N1—C2—C3—C4	−1.3 (4)	N1A—C2A—C3A—C4A	0.7 (4)
C2—C3—C4—C10	0.8 (3)	C2A—C3A—C4A—C10A	−1.4 (4)
C10—C5—C6—C7	0.8 (4)	C10A—C5A—C6A—C7A	−0.4 (4)
C5—C6—C7—C8	−0.6 (4)	C5A—C6A—C7A—C8A	−0.3 (4)
C6—C7—C8—N2	−179.1 (2)	C6A—C7A—C8A—N2A	−178.4 (2)
C6—C7—C8—C9	−0.5 (3)	C6A—C7A—C8A—C9A	0.7 (3)
C11—N2—C8—C7	−17.4 (4)	C11A—N2A—C8A—C7A	−22.8 (4)
C11—N2—C8—C9	164.0 (2)	C11A—N2A—C8A—C9A	158.1 (2)
C2—N1—C9—C10	0.4 (3)	C2A—N1A—C9A—C10A	−1.0 (3)
C2—N1—C9—C8	−179.2 (2)	C2A—N1A—C9A—C8A	180.0 (2)
C7—C8—C9—N1	−178.9 (2)	C7A—C8A—C9A—N1A	178.7 (2)
N2—C8—C9—N1	−0.2 (3)	N2A—C8A—C9A—N1A	−2.1 (3)
C7—C8—C9—C10	1.5 (3)	C7A—C8A—C9A—C10A	−0.4 (3)
N2—C8—C9—C10	−179.8 (2)	N2A—C8A—C9A—C10A	178.8 (2)
C6—C5—C10—C4	−179.9 (2)	N1A—C9A—C10A—C5A	−179.3 (2)
C6—C5—C10—C9	0.2 (3)	C8A—C9A—C10A—C5A	−0.3 (3)
C3—C4—C10—C5	−179.7 (2)	N1A—C9A—C10A—C4A	0.3 (3)
C3—C4—C10—C9	0.2 (3)	C8A—C9A—C10A—C4A	179.3 (2)
N1—C9—C10—C5	179.1 (2)	C6A—C5A—C10A—C9A	0.7 (3)
C8—C9—C10—C5	−1.4 (3)	C6A—C5A—C10A—C4A	−178.9 (2)
N1—C9—C10—C4	−0.8 (3)	C3A—C4A—C10A—C9A	1.0 (3)
C8—C9—C10—C4	178.7 (2)	C3A—C4A—C10A—C5A	−179.5 (2)
C8—N2—C11—O1	−3.3 (4)	C8A—N2A—C11A—O1A	2.6 (4)
C8—N2—C11—C12	177.7 (2)	C8A—N2A—C11A—C12A	−176.5 (2)
O1—C11—C12—C13	−31.9 (3)	O1A—C11A—C12A—C13A	−27.5 (3)
N2—C11—C12—C13	147.2 (2)	N2A—C11A—C12A—C13A	151.7 (2)
O1—C11—C12—C17	147.3 (2)	O1A—C11A—C12A—C17A	152.8 (2)
N2—C11—C12—C17	−33.6 (3)	N2A—C11A—C12A—C17A	−28.0 (3)
C17—C12—C13—C14	1.5 (3)	C17A—C12A—C13A—C14A	0.7 (3)
C11—C12—C13—C14	−179.2 (2)	C11A—C12A—C13A—C14A	−179.0 (2)
C12—C13—C14—C15	−1.1 (3)	C12A—C13A—C14A—C15A	−1.8 (3)
C12—C13—C14—N3	178.03 (19)	C12A—C13A—C14A—N3A	177.4 (2)
O3—N3—C14—C15	−1.3 (3)	O3A—N3A—C14A—C13A	179.9 (2)
O2—N3—C14—C15	178.9 (2)	O2A—N3A—C14A—C13A	−0.8 (3)
O3—N3—C14—C13	179.5 (2)	O3A—N3A—C14A—C15A	−0.9 (3)
O2—N3—C14—C13	−0.2 (3)	O2A—N3A—C14A—C15A	178.4 (2)
C13—C14—C15—C16	−0.4 (3)	C13A—C14A—C15A—C16A	1.2 (4)
N3—C14—C15—C16	−179.57 (19)	N3A—C14A—C15A—C16A	−178.0 (2)
C14—C15—C16—C17	1.6 (3)	C14A—C15A—C16A—C17A	0.4 (3)
C15—C16—C17—C12	−1.2 (3)	C15A—C16A—C17A—C12A	−1.4 (3)
C13—C12—C17—C16	−0.4 (3)	C13A—C12A—C17A—C16A	0.8 (3)
C11—C12—C17—C16	−179.7 (2)	C11A—C12A—C17A—C16A	−179.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2i	0.95	2.56	3.395 (3)	147
C2A—H2A···O2i	0.95	2.50	3.346 (3)	148
C4—H4···O2Ai	0.95	2.48	3.317 (3)	146
C16—H16···O3Aii	0.95	2.46	3.147 (3)	130
C16A—H16A···O1iii	0.95	2.50	3.198 (3)	130
C17—H17···O1Aiv	0.95	2.45	3.396 (3)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2i	0.95	2.56	3.395 (3)	147
C2A—H2A⋯O2i	0.95	2.50	3.346 (3)	148
C4—H4⋯O2Ai	0.95	2.48	3.317 (3)	146
C16—H16⋯O3Aii	0.95	2.46	3.147 (3)	130
C16A—H16A⋯O1iii	0.95	2.50	3.198 (3)	130
C17—H17⋯O1Aiv	0.95	2.45	3.396 (3)	172

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .