(E)-2-[2-(2-Nitro-phen-yl)ethen-yl]-8-quinolyl acetate.

The title compound, C(19)H(14)N(2)O(4), crystallizes with two molecules with very similar conformations in the asymmetric unit; the angles between the two ring systems are 8.7 (1) and 4.2 (1)°. In the crystal, inter-molecular π-π inter-actions [centroid-centroid distance 3.973 (1) Å] lead to a three-dimensional network.

Related literature

For the biological properties of 8-hydroxy­quinoline derivatives, see: Chen et al. (2002 ▶); Fakhfakh et al. (2003 ▶); Mekouar et al. (1998 ▶); Ouali et al. (2000 ▶); Storz et al. (2004 ▶); Zeng, Wang et al. (2006 ▶). For a related crystal structure, see: Zeng, OuYang et al. (2006 ▶).

Experimental

Crystal data

C19H14N2O4

M = 334.32

Orthorhombic,

a = 25.8466 (13) Å

b = 11.8451 (6) Å

c = 10.5870 (5) Å

V = 3241.3 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.47 × 0.45 × 0.26 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.956, T max = 0.975

17451 measured reflections

3731 independent reflections

2785 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.171

S = 1.04

3731 reflections

453 parameters

7 restraints

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; 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 datablocks I, global. DOI: 10.1107/S1600536809044158/wn2356sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044158/wn2356Isup2.hkl

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

C19H14N2O4	F(000) = 1392
Mr = 334.32	Dx = 1.370 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5386 reflections
a = 25.8466 (13) Å	θ = 2.3–26.3°
b = 11.8451 (6) Å	µ = 0.10 mm−1
c = 10.5870 (5) Å	T = 173 K
V = 3241.3 (3) Å3	Block, yellow
Z = 8	0.47 × 0.45 × 0.26 mm

Bruker SMART 1000 CCD diffractometer	3731 independent reflections
Radiation source: fine-focus sealed tube	2785 reflections with I > 2σ(I)
graphite	Rint = 0.039
ω scans	θmax = 27.1°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −29→33
Tmin = 0.956, Tmax = 0.975	k = −13→15
17451 measured reflections	l = −13→13

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.1126P)2 + 0.5654P] where P = (Fo2 + 2Fc2)/3
3731 reflections	(Δ/σ)max = 0.004
453 parameters	Δρmax = 0.56 e Å−3
7 restraints	Δρmin = −0.22 e Å−3

Experimental. 1H NMR (CDCl3, 300 MHz) δ 8.17–8.26 (m, 2H), 7.94 (d, J=7.5 Hz, 1H), 7.82 (d, J=7.8 Hz 1H), 7.64–7.70 (m, 4H), 7.47–7.53 (m, 3H), 2.58(s, 3H); IR (KBr, cm-1): 3067, 1723, 1577, 1520, 1457, 1175, 1128, 970, 850, 765, 708; ESI-MS m/z: 335.9 ([M+H]+); Elemental analysis: found C: 68.45, H: 4.40, N: 8.38 (%)

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
C1	0.79027 (14)	0.4406 (3)	0.2939 (4)	0.0354 (9)
H1	0.7753	0.5118	0.2748	0.043*
C2	0.83678 (14)	0.4416 (3)	0.3458 (4)	0.0347 (8)
H2	0.8522	0.3712	0.3664	0.042*
C3	0.92068 (14)	0.7392 (3)	0.4307 (4)	0.0337 (9)
C4	0.87102 (14)	0.7393 (3)	0.3743 (4)	0.0301 (8)
N5	0.84409 (11)	0.6440 (3)	0.3460 (3)	0.0299 (7)
C6	0.86607 (13)	0.5452 (3)	0.3734 (4)	0.0321 (8)
C7	0.91645 (16)	0.5376 (4)	0.4257 (4)	0.0383 (9)
H7	0.9315	0.4656	0.4403	0.046*
C8	0.94344 (14)	0.6324 (4)	0.4549 (4)	0.0396 (10)
H8	0.9770	0.6273	0.4910	0.048*
C9	0.94489 (16)	0.8434 (4)	0.4613 (4)	0.0432 (10)
H9	0.9779	0.8436	0.5007	0.052*
C10	0.92101 (17)	0.9425 (4)	0.4346 (4)	0.0447 (10)
H10	0.9372	1.0116	0.4569	0.054*
C11	0.87218 (16)	0.9444 (3)	0.3739 (4)	0.0393 (9)
H11	0.8560	1.0143	0.3544	0.047*
C12	0.84871 (14)	0.8454 (3)	0.3436 (4)	0.0310 (8)
O13	0.79975 (10)	0.8466 (2)	0.2896 (3)	0.0343 (6)
C14	0.75968 (15)	0.3408 (3)	0.2631 (4)	0.0360 (9)
C15	0.71059 (16)	0.3464 (4)	0.2113 (5)	0.0470 (11)
C16	0.67993 (18)	0.2511 (5)	0.1900 (6)	0.0594 (15)
H16	0.6458	0.2589	0.1576	0.071*
C17	0.6995 (2)	0.1471 (5)	0.2162 (5)	0.0580 (14)
H17	0.6794	0.0815	0.2005	0.070*
C18	0.74860 (19)	0.1373 (4)	0.2656 (5)	0.0492 (11)
H18	0.7623	0.0646	0.2834	0.059*
C19	0.77801 (16)	0.2319 (3)	0.2896 (4)	0.0395 (10)
H19	0.8116	0.2231	0.3249	0.047*
C20	0.79586 (15)	0.8136 (3)	0.1658 (4)	0.0330 (8)
O21	0.83315 (11)	0.7982 (2)	0.1009 (3)	0.0417 (7)
C22	0.74072 (15)	0.8026 (4)	0.1270 (5)	0.0473 (11)
H22A	0.7385	0.8011	0.0346	0.071*
H22B	0.7210	0.8670	0.1594	0.071*
H22C	0.7264	0.7324	0.1614	0.071*
N23	0.68857 (17)	0.4577 (5)	0.1744 (6)	0.0746 (17)
O24	0.7137 (2)	0.5202 (4)	0.1073 (7)	0.101 (2)
O25	0.64504 (18)	0.4750 (5)	0.2109 (7)	0.124 (2)
C26	0.46521 (13)	−0.0779 (3)	0.1266 (4)	0.0304 (8)
H26	0.4808	−0.0079	0.1483	0.036*
C27	0.41923 (15)	−0.0756 (3)	0.0705 (4)	0.0358 (9)
H27	0.4045	−0.1458	0.0459	0.043*
C28	0.33041 (14)	0.2153 (3)	−0.0099 (4)	0.0321 (8)
C29	0.37963 (13)	0.2194 (3)	0.0491 (4)	0.0290 (8)
N30	0.40900 (11)	0.1266 (3)	0.0752 (3)	0.0308 (7)
C31	0.38950 (14)	0.0269 (3)	0.0438 (4)	0.0318 (8)
C32	0.33986 (15)	0.0140 (3)	−0.0117 (4)	0.0378 (9)
H32	0.3268	−0.0592	−0.0298	0.045*
C33	0.31110 (15)	0.1068 (4)	−0.0387 (4)	0.0376 (9)
H33	0.2780	0.0988	−0.0768	0.045*
C34	0.30335 (15)	0.3162 (3)	−0.0367 (4)	0.0364 (9)
H34	0.2705	0.3132	−0.0767	0.044*
C35	0.32446 (16)	0.4174 (4)	−0.0053 (4)	0.0415 (10)
H35	0.3063	0.4849	−0.0247	0.050*
C36	0.37324 (15)	0.4241 (3)	0.0561 (4)	0.0383 (9)
H36	0.3876	0.4955	0.0772	0.046*
C37	0.39908 (14)	0.3276 (3)	0.0842 (4)	0.0314 (8)
O38	0.44801 (10)	0.3328 (2)	0.1386 (3)	0.0339 (6)
C39	0.49328 (13)	−0.1817 (3)	0.1570 (4)	0.0305 (8)
C40	0.54472 (14)	−0.1848 (3)	0.2014 (4)	0.0340 (9)
C41	0.57112 (16)	−0.2840 (4)	0.2254 (5)	0.0425 (11)
H41	0.6063	−0.2822	0.2513	0.051*
C42	0.54573 (16)	−0.3852 (4)	0.2111 (5)	0.0458 (10)
H42	0.5628	−0.4540	0.2311	0.055*
C43	0.49544 (15)	−0.3867 (3)	0.1678 (5)	0.0428 (10)
H43	0.4782	−0.4568	0.1564	0.051*
C44	0.46994 (14)	−0.2877 (3)	0.1411 (4)	0.0360 (9)
H44	0.4354	−0.2912	0.1109	0.043*
C45	0.45270 (15)	0.2938 (3)	0.2601 (4)	0.0345 (9)
O46	0.41633 (11)	0.2756 (3)	0.3261 (3)	0.0436 (7)
C47	0.50824 (17)	0.2795 (4)	0.2951 (5)	0.0510 (12)
H47A	0.5112	0.2715	0.3870	0.076*
H47B	0.5279	0.3458	0.2674	0.076*
H47C	0.5221	0.2118	0.2540	0.076*
N48	0.57481 (13)	−0.0810 (3)	0.2185 (4)	0.0428 (9)
O49	0.55389 (14)	0.0009 (3)	0.2665 (4)	0.0621 (10)
O50	0.62029 (12)	−0.0830 (3)	0.1858 (4)	0.0628 (10)

	U11	U22	U33	U12	U13	U23
C1	0.037 (2)	0.033 (2)	0.036 (2)	0.0056 (15)	−0.0016 (16)	−0.0013 (16)
C2	0.0349 (19)	0.0296 (19)	0.039 (2)	0.0053 (15)	0.0015 (16)	0.0038 (16)
C3	0.0286 (19)	0.049 (2)	0.023 (2)	−0.0057 (16)	−0.0027 (16)	0.0050 (16)
C4	0.0296 (19)	0.038 (2)	0.0223 (19)	−0.0017 (15)	0.0006 (15)	0.0022 (15)
N5	0.0253 (15)	0.0350 (17)	0.0293 (17)	0.0025 (12)	−0.0008 (13)	0.0008 (13)
C6	0.0279 (18)	0.036 (2)	0.032 (2)	0.0030 (15)	0.0030 (15)	0.0058 (16)
C7	0.039 (2)	0.045 (2)	0.031 (2)	0.0094 (17)	−0.0005 (17)	0.0089 (18)
C8	0.0250 (19)	0.059 (3)	0.035 (2)	0.0009 (17)	−0.0046 (16)	0.0100 (19)
C9	0.031 (2)	0.061 (3)	0.038 (2)	−0.0135 (19)	−0.0060 (18)	0.002 (2)
C10	0.048 (2)	0.049 (3)	0.037 (2)	−0.021 (2)	−0.0052 (19)	−0.0014 (19)
C11	0.040 (2)	0.037 (2)	0.040 (2)	−0.0045 (17)	−0.0010 (18)	−0.0002 (18)
C12	0.0263 (18)	0.038 (2)	0.029 (2)	−0.0030 (14)	0.0012 (15)	−0.0016 (15)
O13	0.0299 (13)	0.0375 (15)	0.0356 (15)	0.0027 (10)	−0.0024 (11)	−0.0036 (11)
C14	0.032 (2)	0.039 (2)	0.036 (2)	0.0017 (16)	0.0026 (16)	−0.0066 (17)
C15	0.039 (2)	0.060 (3)	0.042 (3)	0.0037 (19)	−0.004 (2)	−0.016 (2)
C16	0.036 (2)	0.089 (4)	0.054 (3)	−0.007 (2)	−0.006 (2)	−0.023 (3)
C17	0.062 (3)	0.067 (4)	0.046 (3)	−0.027 (3)	0.012 (2)	−0.008 (2)
C18	0.058 (3)	0.042 (2)	0.047 (3)	−0.011 (2)	0.010 (2)	0.001 (2)
C19	0.040 (2)	0.038 (2)	0.041 (3)	−0.0021 (17)	0.0066 (19)	0.0015 (18)
C20	0.0354 (19)	0.0249 (18)	0.039 (2)	0.0032 (14)	−0.0032 (17)	0.0015 (16)
O21	0.0397 (16)	0.0473 (16)	0.0382 (17)	0.0054 (12)	0.0026 (13)	0.0020 (13)
C22	0.036 (2)	0.061 (3)	0.044 (3)	0.0046 (19)	−0.0094 (19)	0.000 (2)
N23	0.045 (3)	0.089 (4)	0.090 (4)	0.028 (2)	−0.035 (3)	−0.039 (3)
O24	0.102 (4)	0.053 (2)	0.150 (5)	0.014 (2)	−0.063 (4)	−0.004 (3)
O25	0.077 (3)	0.167 (5)	0.126 (4)	0.071 (3)	−0.028 (3)	−0.049 (4)
C26	0.0292 (18)	0.0292 (18)	0.0326 (19)	−0.0033 (14)	0.0012 (15)	0.0004 (15)
C27	0.038 (2)	0.0288 (19)	0.041 (2)	0.0020 (15)	−0.0058 (17)	−0.0073 (16)
C28	0.0293 (19)	0.043 (2)	0.024 (2)	0.0012 (16)	−0.0011 (15)	−0.0016 (16)
C29	0.0227 (17)	0.036 (2)	0.028 (2)	0.0018 (14)	0.0017 (15)	0.0010 (15)
N30	0.0277 (15)	0.0323 (16)	0.0324 (18)	0.0018 (12)	−0.0006 (13)	−0.0036 (13)
C31	0.0308 (18)	0.035 (2)	0.029 (2)	−0.0003 (15)	−0.0018 (15)	−0.0031 (15)
C32	0.036 (2)	0.035 (2)	0.043 (2)	−0.0014 (16)	−0.0104 (17)	−0.0033 (17)
C33	0.0266 (18)	0.047 (2)	0.039 (2)	−0.0024 (16)	−0.0088 (16)	−0.0033 (19)
C34	0.031 (2)	0.043 (2)	0.035 (2)	0.0056 (16)	−0.0038 (17)	0.0001 (18)
C35	0.039 (2)	0.043 (2)	0.042 (3)	0.0125 (18)	0.0008 (18)	0.0050 (19)
C36	0.039 (2)	0.033 (2)	0.043 (2)	0.0005 (16)	0.0005 (18)	−0.0004 (18)
C37	0.0279 (18)	0.038 (2)	0.029 (2)	−0.0001 (14)	0.0028 (15)	−0.0016 (16)
O38	0.0295 (13)	0.0325 (13)	0.0398 (16)	−0.0051 (10)	−0.0011 (11)	0.0029 (12)
C39	0.0291 (18)	0.0318 (18)	0.031 (2)	−0.0006 (14)	0.0026 (15)	−0.0011 (16)
C40	0.0313 (19)	0.036 (2)	0.035 (2)	−0.0040 (15)	−0.0038 (17)	−0.0019 (17)
C41	0.032 (2)	0.045 (3)	0.051 (3)	0.0033 (17)	−0.006 (2)	0.000 (2)
C42	0.043 (2)	0.037 (2)	0.058 (3)	0.0068 (17)	0.000 (2)	0.000 (2)
C43	0.035 (2)	0.032 (2)	0.060 (3)	−0.0005 (16)	0.0018 (19)	−0.0030 (19)
C44	0.0267 (18)	0.039 (2)	0.042 (2)	−0.0043 (15)	0.0031 (16)	−0.0013 (18)
C45	0.038 (2)	0.0258 (18)	0.040 (2)	−0.0047 (15)	−0.0043 (17)	−0.0021 (16)
O46	0.0421 (17)	0.0522 (18)	0.0366 (17)	−0.0094 (13)	0.0040 (14)	−0.0005 (14)
C47	0.043 (3)	0.066 (3)	0.043 (3)	−0.004 (2)	−0.010 (2)	0.008 (2)
N48	0.045 (2)	0.0363 (19)	0.047 (2)	−0.0037 (15)	−0.0175 (17)	0.0026 (16)
O49	0.065 (2)	0.0429 (19)	0.079 (3)	−0.0009 (16)	−0.0301 (19)	−0.0133 (18)
O50	0.0353 (16)	0.062 (2)	0.091 (3)	−0.0134 (15)	−0.0157 (17)	0.009 (2)

C1—C2	1.322 (5)	C26—C27	1.329 (5)
C1—C14	1.459 (5)	C26—C39	1.464 (5)
C1—H1	0.9500	C26—H26	0.9500
C2—C6	1.471 (5)	C27—C31	1.465 (5)
C2—H2	0.9500	C27—H27	0.9500
C3—C4	1.415 (5)	C28—C33	1.412 (6)
C3—C8	1.418 (6)	C28—C34	1.414 (5)
C3—C9	1.421 (6)	C28—C29	1.418 (5)
C4—N5	1.361 (5)	C29—N30	1.364 (5)
C4—C12	1.420 (5)	C29—C37	1.426 (5)
N5—C6	1.332 (5)	N30—C31	1.327 (5)
C6—C7	1.418 (5)	C31—C32	1.419 (5)
C7—C8	1.358 (6)	C32—C33	1.358 (6)
C7—H7	0.9500	C32—H32	0.9500
C8—H8	0.9500	C33—H33	0.9500
C9—C10	1.357 (6)	C34—C35	1.358 (6)
C9—H9	0.9500	C34—H34	0.9500
C10—C11	1.417 (6)	C35—C36	1.420 (6)
C10—H10	0.9500	C35—H35	0.9500
C11—C12	1.358 (5)	C36—C37	1.357 (5)
C11—H11	0.9500	C36—H36	0.9500
C12—O13	1.389 (4)	C37—O38	1.391 (5)
O13—C20	1.372 (5)	O38—C45	1.372 (5)
C14—C15	1.384 (6)	C39—C44	1.403 (5)
C14—C19	1.403 (6)	C39—C40	1.411 (5)
C15—C16	1.397 (7)	C40—C41	1.382 (6)
C15—N23	1.488 (7)	C40—N48	1.466 (5)
C16—C17	1.361 (8)	C41—C42	1.375 (6)
C16—H16	0.9500	C41—H41	0.9500
C17—C18	1.377 (7)	C42—C43	1.378 (6)
C17—H17	0.9500	C42—H42	0.9500
C18—C19	1.378 (6)	C43—C44	1.375 (6)
C18—H18	0.9500	C43—H43	0.9500
C19—H19	0.9500	C44—H44	0.9500
C20—O21	1.197 (5)	C45—O46	1.191 (5)
C20—C22	1.489 (5)	C45—C47	1.492 (6)
C22—H22A	0.9800	C47—H47A	0.9800
C22—H22B	0.9800	C47—H47B	0.9800
C22—H22C	0.9800	C47—H47C	0.9800
N23—O25	1.207 (6)	N48—O49	1.222 (5)
N23—O24	1.215 (7)	N48—O50	1.226 (5)
C2—C1—C14	126.4 (4)	C27—C26—C39	123.9 (3)
C2—C1—H1	116.8	C27—C26—H26	118.0
C14—C1—H1	116.8	C39—C26—H26	118.0
C1—C2—C6	123.9 (3)	C26—C27—C31	124.9 (3)
C1—C2—H2	118.0	C26—C27—H27	117.6
C6—C2—H2	118.0	C31—C27—H27	117.6
C4—C3—C8	117.0 (4)	C33—C28—C34	123.4 (3)
C4—C3—C9	119.7 (4)	C33—C28—C29	116.3 (3)
C8—C3—C9	123.4 (4)	C34—C28—C29	120.2 (3)
N5—C4—C3	123.8 (3)	N30—C29—C28	124.1 (3)
N5—C4—C12	118.4 (3)	N30—C29—C37	118.4 (3)
C3—C4—C12	117.8 (3)	C28—C29—C37	117.5 (3)
C6—N5—C4	117.6 (3)	C31—N30—C29	117.1 (3)
N5—C6—C7	122.2 (4)	N30—C31—C32	122.9 (3)
N5—C6—C2	118.0 (3)	N30—C31—C27	119.4 (3)
C7—C6—C2	119.8 (3)	C32—C31—C27	117.7 (3)
C8—C7—C6	120.6 (4)	C33—C32—C31	119.7 (4)
C8—C7—H7	119.7	C33—C32—H32	120.2
C6—C7—H7	119.7	C31—C32—H32	120.2
C7—C8—C3	118.9 (4)	C32—C33—C28	119.9 (3)
C7—C8—H8	120.6	C32—C33—H33	120.1
C3—C8—H8	120.6	C28—C33—H33	120.1
C10—C9—C3	120.2 (4)	C35—C34—C28	119.9 (4)
C10—C9—H9	119.9	C35—C34—H34	120.1
C3—C9—H9	119.9	C28—C34—H34	120.1
C9—C10—C11	120.9 (4)	C34—C35—C36	121.2 (4)
C9—C10—H10	119.5	C34—C35—H35	119.4
C11—C10—H10	119.5	C36—C35—H35	119.4
C12—C11—C10	119.4 (4)	C37—C36—C35	119.3 (4)
C12—C11—H11	120.3	C37—C36—H36	120.3
C10—C11—H11	120.3	C35—C36—H36	120.3
C11—C12—O13	119.7 (3)	C36—C37—O38	120.1 (3)
C11—C12—C4	121.9 (4)	C36—C37—C29	121.8 (3)
O13—C12—C4	118.3 (3)	O38—C37—C29	117.9 (3)
C20—O13—C12	117.2 (3)	C45—O38—C37	117.0 (3)
C15—C14—C19	115.6 (4)	C44—C39—C40	114.9 (3)
C15—C14—C1	123.2 (4)	C44—C39—C26	120.8 (3)
C19—C14—C1	121.2 (4)	C40—C39—C26	124.2 (3)
C14—C15—C16	123.1 (5)	C41—C40—C39	123.3 (4)
C14—C15—N23	119.8 (4)	C41—C40—N48	115.3 (3)
C16—C15—N23	117.2 (4)	C39—C40—N48	121.3 (3)
C17—C16—C15	119.2 (4)	C42—C41—C40	119.0 (4)
C17—C16—H16	120.4	C42—C41—H41	120.5
C15—C16—H16	120.4	C40—C41—H41	120.5
C16—C17—C18	119.8 (4)	C41—C42—C43	119.8 (4)
C16—C17—H17	120.1	C41—C42—H42	120.1
C18—C17—H17	120.1	C43—C42—H42	120.1
C17—C18—C19	120.6 (5)	C44—C43—C42	120.7 (4)
C17—C18—H18	119.7	C44—C43—H43	119.7
C19—C18—H18	119.7	C42—C43—H43	119.7
C18—C19—C14	121.7 (4)	C43—C44—C39	122.2 (4)
C18—C19—H19	119.2	C43—C44—H44	118.9
C14—C19—H19	119.2	C39—C44—H44	118.9
O21—C20—O13	122.2 (4)	O46—C45—O38	122.7 (4)
O21—C20—C22	126.8 (4)	O46—C45—C47	126.4 (4)
O13—C20—C22	111.0 (3)	O38—C45—C47	110.9 (4)
C20—C22—H22A	109.5	C45—C47—H47A	109.5
C20—C22—H22B	109.5	C45—C47—H47B	109.5
H22A—C22—H22B	109.5	H47A—C47—H47B	109.5
C20—C22—H22C	109.5	C45—C47—H47C	109.5
H22A—C22—H22C	109.5	H47A—C47—H47C	109.5
H22B—C22—H22C	109.5	H47B—C47—H47C	109.5
O25—N23—O24	125.6 (7)	O49—N48—O50	123.8 (4)
O25—N23—C15	115.0 (7)	O49—N48—C40	118.9 (4)
O24—N23—C15	119.3 (4)	O50—N48—C40	117.3 (4)
C14—C1—C2—C6	179.3 (4)	C39—C26—C27—C31	177.4 (4)
C8—C3—C4—N5	1.8 (6)	C33—C28—C29—N30	2.0 (6)
C9—C3—C4—N5	−177.5 (4)	C34—C28—C29—N30	−178.1 (4)
C8—C3—C4—C12	−176.9 (4)	C33—C28—C29—C37	−177.3 (4)
C9—C3—C4—C12	3.8 (6)	C34—C28—C29—C37	2.6 (5)
C3—C4—N5—C6	0.1 (6)	C28—C29—N30—C31	−0.7 (6)
C12—C4—N5—C6	178.8 (3)	C37—C29—N30—C31	178.7 (4)
C4—N5—C6—C7	−2.5 (6)	C29—N30—C31—C32	−1.6 (6)
C4—N5—C6—C2	178.7 (3)	C29—N30—C31—C27	−179.5 (3)
C1—C2—C6—N5	0.9 (6)	C26—C27—C31—N30	0.9 (7)
C1—C2—C6—C7	−178.0 (4)	C26—C27—C31—C32	−177.2 (4)
N5—C6—C7—C8	2.9 (6)	N30—C31—C32—C33	2.3 (6)
C2—C6—C7—C8	−178.2 (4)	C27—C31—C32—C33	−179.7 (4)
C6—C7—C8—C3	−0.9 (6)	C31—C32—C33—C28	−0.8 (7)
C4—C3—C8—C7	−1.3 (6)	C34—C28—C33—C32	178.9 (4)
C9—C3—C8—C7	178.0 (4)	C29—C28—C33—C32	−1.2 (6)
C4—C3—C9—C10	−1.2 (7)	C33—C28—C34—C35	179.6 (4)
C8—C3—C9—C10	179.5 (4)	C29—C28—C34—C35	−0.4 (6)
C3—C9—C10—C11	−1.2 (7)	C28—C34—C35—C36	−0.9 (6)
C9—C10—C11—C12	0.9 (7)	C34—C35—C36—C37	−0.3 (6)
C10—C11—C12—O13	176.9 (4)	C35—C36—C37—O38	176.8 (4)
C10—C11—C12—C4	1.8 (6)	C35—C36—C37—C29	2.7 (6)
N5—C4—C12—C11	177.1 (4)	N30—C29—C37—C36	176.8 (4)
C3—C4—C12—C11	−4.1 (6)	C28—C29—C37—C36	−3.8 (6)
N5—C4—C12—O13	2.0 (6)	N30—C29—C37—O38	2.5 (5)
C3—C4—C12—O13	−179.3 (3)	C28—C29—C37—O38	−178.1 (3)
C11—C12—O13—C20	111.1 (4)	C36—C37—O38—C45	113.4 (4)
C4—C12—O13—C20	−73.7 (4)	C29—C37—O38—C45	−72.2 (4)
C2—C1—C14—C15	178.5 (4)	C27—C26—C39—C44	−7.5 (6)
C2—C1—C14—C19	1.1 (7)	C27—C26—C39—C40	171.5 (4)
C19—C14—C15—C16	2.1 (7)	C44—C39—C40—C41	1.3 (6)
C1—C14—C15—C16	−175.4 (4)	C26—C39—C40—C41	−177.7 (4)
C19—C14—C15—N23	−177.3 (4)	C44—C39—C40—N48	177.9 (4)
C1—C14—C15—N23	5.2 (7)	C26—C39—C40—N48	−1.2 (6)
C14—C15—C16—C17	−2.7 (8)	C39—C40—C41—C42	−3.1 (7)
N23—C15—C16—C17	176.7 (5)	N48—C40—C41—C42	−179.8 (4)
C15—C16—C17—C18	1.4 (8)	C40—C41—C42—C43	3.0 (8)
C16—C17—C18—C19	0.4 (8)	C41—C42—C43—C44	−1.3 (8)
C17—C18—C19—C14	−1.0 (7)	C42—C43—C44—C39	−0.4 (7)
C15—C14—C19—C18	−0.3 (7)	C40—C39—C44—C43	0.4 (6)
C1—C14—C19—C18	177.3 (4)	C26—C39—C44—C43	179.5 (4)
C12—O13—C20—O21	−9.5 (5)	C37—O38—C45—O46	−13.8 (5)
C12—O13—C20—C22	171.4 (3)	C37—O38—C45—C47	166.9 (3)
C14—C15—N23—O25	−132.0 (5)	C41—C40—N48—O49	−140.5 (4)
C16—C15—N23—O25	48.6 (7)	C39—C40—N48—O49	42.7 (6)
C14—C15—N23—O24	51.4 (7)	C41—C40—N48—O50	37.9 (6)
C16—C15—N23—O24	−128.0 (6)	C39—C40—N48—O50	−138.9 (4)