2-Chloro-N-[2-(2-fluoro-benzo-yl)-4-nitro-phen-yl]-N-methyl-acetamide.

The title compound, C(16)H(12)ClFN(2)O(4), crystallizes with two mol-ecules in the asymmetric unit in which the dihedral angles between the mean planes of the two benzene rings are 65.1 (7) and 65.6 (6)°. In each mol-ecule, the nitro group displays rotational disorder over two orientations in a 0.503 (11):0.497 (11) ratio and the Cl atom is disordered in a 0.432 (5):0.568 (5) ratio. In one mol-ecule, the F atoms is statistically disordered over two positions. The crystal packing features weak inter-molecular C-H⋯O and C-H⋯Cl inter-actions, which form a layered network.

Related literature

For anti-anaphylactic and disease-related agents, see: Evans et al. (1987 ▶). For an inter­mediate in the synthesis of flunitra­zepam (systematic name: 6-(2-fluoro­phen­yl)-2-methyl-9-nitro-2,5-diaza­bicyclo­[5.4.0]undeca-5,8,10,12-tetraen-3-one), see: Malanciuc et al. (2009 ▶). For related structures, see: Dutkiewicz et al. (2010 ▶); Jasinski et al. (2009 ▶); Khan et al. (2010 ▶); Malathy Sony et al. (2005a ▶,b ▶); Prasanna & Guru Row (2000 ▶). For standard bond lengths, see Allen et al. (1987 ▶).

Experimental

Crystal data

C16H12ClFN2O4

M = 350.73

Triclinic,

a = 8.1339 (6) Å

b = 10.9639 (8) Å

c = 17.8690 (11) Å

α = 81.251 (6)°

β = 82.239 (6)°

γ = 87.937 (6)°

V = 1560.38 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 200 K

0.24 × 0.16 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.936, T max = 0.967

13030 measured reflections

6373 independent reflections

3774 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.172

S = 1.03

6373 reflections

448 parameters

16 restraints

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.36 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811034969/im2312sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034969/im2312Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034969/im2312Isup3.cml

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

C16H12ClFN2O4	Z = 4
Mr = 350.73	F(000) = 720
Triclinic, P1	Dx = 1.493 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1339 (6) Å	Cell parameters from 2929 reflections
b = 10.9639 (8) Å	θ = 3.1–32.4°
c = 17.8690 (11) Å	µ = 0.28 mm−1
α = 81.251 (6)°	T = 200 K
β = 82.239 (6)°	Block, colorless
γ = 87.937 (6)°	0.24 × 0.16 × 0.12 mm
V = 1560.38 (19) Å3

Oxford Diffraction Xcalibur Eos Gemini diffractometer	6373 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3774 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 16.1500 pixels mm-1	θmax = 26.4°, θmin = 3.1°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −12→13
Tmin = 0.936, Tmax = 0.967	l = −22→21
13030 measured 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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0665P)2 + 0.3335P] where P = (Fo2 + 2Fc2)/3
6373 reflections	(Δ/σ)max = 0.012
448 parameters	Δρmax = 0.32 e Å−3
16 restraints	Δρmin = −0.36 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	Occ. (<1)
C1	0.6305 (4)	0.5284 (3)	0.37754 (17)	0.0528 (9)
H1A	0.5092	0.5222	0.3930	0.063*
H1B	0.6554	0.6170	0.3618	0.063*
C2	0.6740 (4)	0.4643 (3)	0.30868 (17)	0.0397 (7)
C3	0.6349 (4)	0.4613 (2)	0.17778 (16)	0.0357 (7)
C4	0.7948 (4)	0.4601 (3)	0.13956 (18)	0.0409 (7)
H4	0.8838	0.4889	0.1612	0.049*
C5	0.8253 (4)	0.4175 (3)	0.07052 (18)	0.0447 (8)
H5	0.9352	0.4142	0.0449	0.054*
C6	0.6941 (4)	0.3797 (3)	0.03924 (17)	0.0444 (8)
C7	0.5340 (4)	0.3788 (3)	0.07590 (17)	0.0431 (8)
H7	0.4455	0.3525	0.0529	0.052*
C8	0.5044 (4)	0.4168 (3)	0.14665 (17)	0.0379 (7)
C9	0.3307 (4)	0.4051 (3)	0.18774 (19)	0.0448 (8)
C10	0.3030 (4)	0.3575 (3)	0.27043 (19)	0.0434 (8)
C11	0.3959 (4)	0.2618 (3)	0.3054 (2)	0.0508 (9)
C12	0.3721 (5)	0.2190 (4)	0.3814 (2)	0.0683 (11)
H12	0.4374	0.1526	0.4030	0.082*
C13	0.2500 (6)	0.2752 (4)	0.4261 (2)	0.0799 (13)
H13	0.2326	0.2486	0.4797	0.096*
C14	0.1531 (5)	0.3689 (4)	0.3946 (3)	0.0760 (13)
H14	0.0692	0.4065	0.4263	0.091*
C15	0.1775 (4)	0.4089 (4)	0.3168 (2)	0.0598 (10)
H15	0.1078	0.4720	0.2950	0.072*
C16	0.5018 (4)	0.6286 (3)	0.24344 (19)	0.0491 (8)
H16A	0.4059	0.6184	0.2833	0.074*
H16B	0.4633	0.6481	0.1933	0.074*
H16C	0.5702	0.6961	0.2516	0.074*
C17	0.8713 (5)	0.0822 (3)	0.37310 (19)	0.0630 (10)
H17A	0.8236	0.1665	0.3629	0.076*
H17B	0.9934	0.0900	0.3682	0.076*
C18	0.8310 (4)	0.0101 (3)	0.31241 (19)	0.0455 (8)
C19	0.8622 (4)	−0.0031 (3)	0.17869 (17)	0.0411 (7)
C20	0.7930 (5)	0.0703 (3)	0.1207 (2)	0.0652 (10)
H20	0.7735	0.1555	0.1237	0.078*
C21	0.7519 (6)	0.0231 (4)	0.0590 (2)	0.0734 (12)
H21	0.7064	0.0745	0.0189	0.088*
C22	0.7787 (4)	−0.1018 (3)	0.05717 (19)	0.0540 (9)
C23	0.8398 (4)	−0.1771 (3)	0.11459 (18)	0.0435 (8)
H23	0.8512	−0.2631	0.1127	0.052*
C24	0.8858 (4)	−0.1294 (3)	0.17617 (17)	0.0378 (7)
C25	0.9562 (4)	−0.2199 (3)	0.23510 (17)	0.0388 (7)
C26	1.0948 (4)	−0.1857 (3)	0.27359 (18)	0.0399 (7)
C27	1.1021 (4)	−0.2291 (3)	0.3501 (2)	0.0531 (9)
H31	1.0170	−0.2814	0.3778	0.064*	0.50
C28	1.2290 (6)	−0.1986 (4)	0.3868 (2)	0.0709 (11)
H28	1.2299	−0.2281	0.4396	0.085*
C29	1.3531 (5)	−0.1262 (4)	0.3474 (3)	0.0747 (13)
H29	1.4411	−0.1053	0.3729	0.090*
C30	1.3528 (4)	−0.0830 (3)	0.2716 (3)	0.0655 (11)
H30	1.4407	−0.0336	0.2437	0.079*
C32	1.0045 (5)	0.1643 (3)	0.2218 (2)	0.0575 (10)
H32A	0.9343	0.2371	0.2294	0.086*
H32B	1.0555	0.1722	0.1684	0.086*
H32C	1.0916	0.1578	0.2552	0.086*
N1	0.6014 (3)	0.5132 (2)	0.24675 (13)	0.0349 (6)
N2	0.7239 (4)	0.3326 (3)	−0.03396 (17)	0.0622 (9)
N3	0.9025 (3)	0.0527 (2)	0.24041 (14)	0.0408 (6)
N4	0.7393 (4)	−0.1532 (4)	−0.00907 (19)	0.0699 (9)
O1	0.7643 (3)	0.3733 (2)	0.30914 (13)	0.0539 (6)
O2	0.6212 (9)	0.2889 (10)	−0.0650 (6)	0.0682 (10)	0.503 (11)
O3	0.8746 (8)	0.3465 (9)	−0.0608 (4)	0.0682 (10)	0.503 (11)
O2A	0.5898 (8)	0.3148 (10)	−0.0579 (6)	0.0682 (10)	0.497 (11)
O3A	0.8581 (8)	0.3038 (9)	−0.0666 (5)	0.0682 (10)	0.497 (11)
O4	0.2145 (3)	0.4335 (3)	0.15219 (15)	0.0671 (7)
O5	0.7432 (3)	−0.0798 (2)	0.32668 (13)	0.0598 (7)
O6	0.6964 (13)	−0.0882 (7)	−0.0642 (5)	0.0802 (18)	0.503 (11)
O7	0.775 (2)	−0.2652 (7)	−0.0057 (5)	0.0802 (18)	0.503 (11)
O6A	0.6291 (12)	−0.0950 (8)	−0.0452 (5)	0.0802 (18)	0.497 (11)
O7A	0.7985 (19)	−0.2503 (8)	−0.0264 (6)	0.0802 (18)	0.497 (11)
O8	0.9024 (3)	−0.32484 (19)	0.24960 (14)	0.0583 (7)
F1	0.5148 (2)	0.20503 (17)	0.26090 (12)	0.0662 (6)
F2	0.9848 (4)	−0.3000 (3)	0.39096 (18)	0.0501 (9)	0.50
F2A	1.2279 (7)	−0.0727 (5)	0.1659 (4)	0.1118 (19)	0.50
Cl1	0.7252 (8)	0.4779 (4)	0.45561 (19)	0.0750 (4)	0.432 (5)
Cl2	0.8013 (6)	0.0204 (5)	0.46559 (17)	0.0750 (4)	0.432 (5)
Cl1A	0.7034 (6)	0.4317 (3)	0.45940 (14)	0.0750 (4)	0.568 (5)
Cl2A	0.7300 (5)	0.0317 (4)	0.45918 (13)	0.0750 (4)	0.568 (5)
C31	1.2222 (4)	−0.1128 (3)	0.2367 (2)	0.0509 (9)
H31A	1.2206	−0.0810	0.1843	0.061*	0.50

	U11	U22	U33	U12	U13	U23
C1	0.053 (2)	0.063 (2)	0.0410 (18)	0.0030 (17)	−0.0029 (16)	−0.0080 (16)
C2	0.0333 (17)	0.0402 (18)	0.0450 (18)	−0.0049 (14)	−0.0034 (14)	−0.0045 (14)
C3	0.0358 (16)	0.0265 (15)	0.0444 (17)	0.0022 (12)	−0.0076 (14)	−0.0023 (13)
C4	0.0337 (17)	0.0350 (17)	0.0520 (19)	−0.0020 (13)	−0.0042 (14)	−0.0010 (14)
C5	0.0420 (18)	0.0380 (17)	0.0484 (19)	0.0056 (14)	0.0035 (15)	0.0015 (15)
C6	0.054 (2)	0.0348 (17)	0.0411 (17)	0.0102 (14)	−0.0026 (16)	−0.0008 (14)
C7	0.051 (2)	0.0329 (17)	0.0482 (18)	0.0036 (14)	−0.0151 (16)	−0.0074 (14)
C8	0.0362 (17)	0.0332 (16)	0.0460 (17)	0.0030 (12)	−0.0099 (14)	−0.0080 (13)
C9	0.0365 (18)	0.0419 (18)	0.060 (2)	0.0009 (14)	−0.0116 (16)	−0.0168 (16)
C10	0.0318 (17)	0.0420 (18)	0.058 (2)	−0.0080 (14)	−0.0018 (15)	−0.0150 (15)
C11	0.043 (2)	0.0416 (19)	0.066 (2)	−0.0086 (15)	0.0026 (17)	−0.0086 (17)
C12	0.071 (3)	0.058 (2)	0.068 (3)	−0.008 (2)	0.001 (2)	0.009 (2)
C13	0.083 (3)	0.085 (3)	0.064 (3)	−0.021 (3)	0.014 (3)	−0.004 (2)
C14	0.061 (3)	0.087 (3)	0.076 (3)	−0.003 (2)	0.017 (2)	−0.022 (3)
C15	0.040 (2)	0.068 (2)	0.072 (3)	−0.0051 (17)	0.0019 (18)	−0.017 (2)
C16	0.050 (2)	0.0418 (19)	0.058 (2)	0.0097 (15)	−0.0119 (17)	−0.0141 (16)
C17	0.080 (3)	0.053 (2)	0.060 (2)	0.0080 (19)	−0.011 (2)	−0.0182 (18)
C18	0.0444 (19)	0.0406 (19)	0.052 (2)	0.0103 (15)	−0.0063 (16)	−0.0103 (15)
C19	0.0424 (18)	0.0344 (17)	0.0465 (18)	−0.0006 (13)	−0.0052 (15)	−0.0070 (14)
C20	0.093 (3)	0.0361 (19)	0.071 (2)	0.0108 (18)	−0.032 (2)	−0.0048 (18)
C21	0.107 (3)	0.053 (2)	0.065 (2)	0.007 (2)	−0.042 (2)	0.001 (2)
C22	0.061 (2)	0.054 (2)	0.050 (2)	−0.0052 (17)	−0.0132 (18)	−0.0119 (17)
C23	0.0443 (18)	0.0379 (17)	0.0496 (19)	−0.0034 (14)	−0.0060 (15)	−0.0104 (15)
C24	0.0353 (16)	0.0313 (16)	0.0463 (17)	−0.0012 (12)	−0.0038 (14)	−0.0057 (13)
C25	0.0376 (17)	0.0305 (16)	0.0481 (18)	−0.0015 (13)	−0.0031 (14)	−0.0069 (13)
C26	0.0368 (17)	0.0294 (16)	0.0551 (19)	0.0012 (13)	−0.0084 (15)	−0.0099 (14)
C27	0.058 (2)	0.048 (2)	0.057 (2)	0.0092 (17)	−0.0190 (18)	−0.0144 (17)
C28	0.084 (3)	0.067 (3)	0.072 (3)	0.020 (2)	−0.036 (2)	−0.024 (2)
C29	0.057 (3)	0.070 (3)	0.115 (4)	0.014 (2)	−0.039 (3)	−0.049 (3)
C30	0.040 (2)	0.052 (2)	0.110 (4)	−0.0059 (17)	−0.006 (2)	−0.031 (2)
C32	0.070 (2)	0.0360 (18)	0.067 (2)	−0.0078 (16)	−0.0020 (19)	−0.0130 (16)
N1	0.0324 (13)	0.0309 (13)	0.0445 (14)	0.0010 (10)	−0.0107 (11)	−0.0106 (11)
N2	0.084 (2)	0.0527 (19)	0.0444 (18)	0.0192 (17)	0.0021 (17)	−0.0048 (14)
N3	0.0432 (15)	0.0307 (13)	0.0497 (15)	−0.0001 (11)	−0.0049 (12)	−0.0106 (11)
N4	0.074 (2)	0.081 (3)	0.061 (2)	−0.0025 (19)	−0.0255 (18)	−0.0142 (19)
O1	0.0547 (14)	0.0482 (14)	0.0569 (14)	0.0132 (11)	−0.0104 (12)	−0.0023 (11)
O2	0.0908 (18)	0.065 (4)	0.0550 (16)	0.0240 (17)	−0.0022 (13)	−0.0412 (18)
O3	0.0908 (18)	0.065 (4)	0.0550 (16)	0.0240 (17)	−0.0022 (13)	−0.0412 (18)
O2A	0.0908 (18)	0.065 (4)	0.0550 (16)	0.0240 (17)	−0.0022 (13)	−0.0412 (18)
O3A	0.0908 (18)	0.065 (4)	0.0550 (16)	0.0240 (17)	−0.0022 (13)	−0.0412 (18)
O4	0.0392 (14)	0.091 (2)	0.0759 (17)	0.0017 (13)	−0.0212 (13)	−0.0155 (15)
O5	0.0565 (15)	0.0591 (15)	0.0610 (15)	−0.0140 (12)	0.0073 (12)	−0.0096 (12)
O6	0.088 (4)	0.103 (2)	0.057 (3)	0.002 (3)	−0.022 (3)	−0.026 (2)
O7	0.088 (4)	0.103 (2)	0.057 (3)	0.002 (3)	−0.022 (3)	−0.026 (2)
O6A	0.088 (4)	0.103 (2)	0.057 (3)	0.002 (3)	−0.022 (3)	−0.026 (2)
O7A	0.088 (4)	0.103 (2)	0.057 (3)	0.002 (3)	−0.022 (3)	−0.026 (2)
O8	0.0678 (16)	0.0332 (12)	0.0758 (16)	−0.0164 (11)	−0.0232 (13)	0.0017 (11)
F1	0.0638 (13)	0.0448 (11)	0.0829 (15)	0.0077 (9)	0.0073 (11)	−0.0042 (10)
F2	0.056 (2)	0.055 (2)	0.0343 (18)	−0.0175 (18)	−0.0003 (17)	0.0099 (16)
F2A	0.095 (4)	0.092 (4)	0.139 (5)	−0.020 (3)	0.016 (4)	−0.012 (4)
Cl1	0.0919 (13)	0.0855 (10)	0.0464 (5)	0.0205 (15)	−0.0146 (5)	−0.0069 (6)
Cl2	0.0919 (13)	0.0855 (10)	0.0464 (5)	0.0205 (15)	−0.0146 (5)	−0.0069 (6)
Cl1A	0.0919 (13)	0.0855 (10)	0.0464 (5)	0.0205 (15)	−0.0146 (5)	−0.0069 (6)
Cl2A	0.0919 (13)	0.0855 (10)	0.0464 (5)	0.0205 (15)	−0.0146 (5)	−0.0069 (6)
C31	0.049 (2)	0.0389 (19)	0.061 (2)	−0.0036 (15)	0.0027 (18)	−0.0052 (17)

C1—C2	1.503 (4)	C17—H17B	0.9900
C1—Cl1	1.694 (6)	C18—O5	1.213 (4)
C1—Cl1A	1.825 (5)	C18—N3	1.359 (4)
C1—H1A	0.9900	C19—C20	1.382 (5)
C1—H1B	0.9900	C19—C24	1.398 (4)
C2—O1	1.217 (4)	C19—N3	1.420 (4)
C2—N1	1.354 (4)	C20—C21	1.371 (5)
C3—C4	1.385 (4)	C20—H20	0.9500
C3—C8	1.398 (4)	C21—C22	1.383 (5)
C3—N1	1.424 (4)	C21—H21	0.9500
C4—C5	1.373 (4)	C22—C23	1.353 (5)
C4—H4	0.9500	C22—N4	1.463 (5)
C5—C6	1.374 (5)	C23—C24	1.387 (4)
C5—H5	0.9500	C23—H23	0.9500
C6—C7	1.376 (4)	C24—C25	1.491 (4)
C6—N2	1.465 (4)	C25—O8	1.224 (3)
C7—C8	1.378 (4)	C25—C26	1.484 (4)
C7—H7	0.9500	C26—C31	1.365 (4)
C8—C9	1.502 (4)	C26—C27	1.386 (4)
C9—O4	1.214 (4)	C27—C28	1.372 (5)
C9—C10	1.480 (5)	C27—H31	0.9500
C10—C15	1.385 (4)	C28—C29	1.357 (6)
C10—C11	1.390 (5)	C28—H28	0.9500
C11—C12	1.359 (5)	C29—C30	1.366 (6)
C11—F1	1.361 (4)	C29—H29	0.9500
C12—C13	1.377 (6)	C30—C31	1.375 (5)
C12—H12	0.9500	C30—H30	0.9500
C13—C14	1.370 (6)	C32—N3	1.473 (4)
C13—H13	0.9500	C32—H32A	0.9800
C14—C15	1.383 (5)	C32—H32B	0.9800
C14—H14	0.9500	C32—H32C	0.9800
C15—H15	0.9500	N2—O2	1.212 (7)
C16—N1	1.476 (4)	N2—O3A	1.221 (6)
C16—H16A	0.9800	N2—O2A	1.256 (7)
C16—H16B	0.9800	N2—O3	1.260 (6)
C16—H16C	0.9800	N4—O6	1.208 (7)
C17—C18	1.512 (5)	N4—O7A	1.218 (7)
C17—Cl2	1.717 (5)	N4—O7	1.245 (7)
C17—Cl2A	1.817 (4)	N4—O6A	1.272 (6)
C17—H17A	0.9900	C31—H31A	0.9500
C2—C1—Cl1	117.8 (3)	N3—C18—C17	114.8 (3)
C2—C1—Cl1A	108.3 (3)	C20—C19—C24	119.6 (3)
C2—C1—H1A	107.9	C20—C19—N3	118.2 (3)
Cl1—C1—H1A	107.9	C24—C19—N3	122.2 (3)
Cl1A—C1—H1A	99.7	C21—C20—C19	121.5 (3)
C2—C1—H1B	107.9	C21—C20—H20	119.2
Cl1—C1—H1B	107.9	C19—C20—H20	119.2
Cl1A—C1—H1B	124.8	C20—C21—C22	117.9 (4)
H1A—C1—H1B	107.2	C20—C21—H21	121.1
O1—C2—N1	122.4 (3)	C22—C21—H21	121.1
O1—C2—C1	122.5 (3)	C23—C22—C21	122.0 (3)
N1—C2—C1	115.0 (3)	C23—C22—N4	119.4 (3)
C4—C3—C8	119.9 (3)	C21—C22—N4	118.6 (3)
C4—C3—N1	120.3 (3)	C22—C23—C24	120.4 (3)
C8—C3—N1	119.7 (3)	C22—C23—H23	119.8
C5—C4—C3	120.3 (3)	C24—C23—H23	119.8
C5—C4—H4	119.8	C23—C24—C19	118.5 (3)
C3—C4—H4	119.8	C23—C24—C25	116.1 (3)
C4—C5—C6	118.8 (3)	C19—C24—C25	125.4 (3)
C4—C5—H5	120.6	O8—C25—C26	119.9 (3)
C6—C5—H5	120.6	O8—C25—C24	119.2 (3)
C5—C6—C7	122.3 (3)	C26—C25—C24	120.9 (2)
C5—C6—N2	119.8 (3)	C31—C26—C27	116.2 (3)
C7—C6—N2	117.8 (3)	C31—C26—C25	123.0 (3)
C8—C7—C6	118.8 (3)	C27—C26—C25	120.8 (3)
C8—C7—H7	120.6	C28—C27—C26	121.7 (4)
C6—C7—H7	120.6	C28—C27—H31	119.1
C7—C8—C3	119.7 (3)	C26—C27—H31	119.1
C7—C8—C9	117.4 (3)	C29—C28—C27	119.7 (4)
C3—C8—C9	122.9 (3)	C29—C28—H28	120.1
O4—C9—C10	120.9 (3)	C27—C28—H28	120.1
O4—C9—C8	119.3 (3)	C30—C29—C28	120.7 (4)
C10—C9—C8	119.8 (3)	C30—C29—H29	119.7
C15—C10—C11	116.9 (3)	C28—C29—H29	119.7
C15—C10—C9	119.4 (3)	C29—C30—C31	118.3 (4)
C11—C10—C9	123.7 (3)	C29—C30—H30	120.8
C12—C11—F1	117.7 (3)	C31—C30—H30	120.8
C12—C11—C10	123.7 (3)	N3—C32—H32A	109.5
F1—C11—C10	118.5 (3)	N3—C32—H32B	109.5
C11—C12—C13	117.6 (4)	H32A—C32—H32B	109.5
C11—C12—H12	121.2	N3—C32—H32C	109.5
C13—C12—H12	121.2	H32A—C32—H32C	109.5
C14—C13—C12	121.1 (4)	H32B—C32—H32C	109.5
C14—C13—H13	119.4	C2—N1—C3	120.1 (2)
C12—C13—H13	119.4	C2—N1—C16	123.0 (2)
C13—C14—C15	120.0 (4)	C3—N1—C16	116.5 (2)
C13—C14—H14	120.0	O2—N2—O3A	105.4 (5)
C15—C14—H14	120.0	O3A—N2—O2A	122.1 (4)
C10—C15—C14	120.4 (4)	O2—N2—O3	124.8 (4)
C10—C15—H15	119.8	O2A—N2—O3	137.8 (7)
C14—C15—H15	119.8	O2—N2—C6	126.2 (5)
N1—C16—H16A	109.5	O3A—N2—C6	126.5 (5)
N1—C16—H16B	109.5	O2A—N2—C6	111.2 (4)
H16A—C16—H16B	109.5	O3—N2—C6	108.9 (5)
N1—C16—H16C	109.5	C18—N3—C19	119.0 (2)
H16A—C16—H16C	109.5	C18—N3—C32	122.9 (3)
H16B—C16—H16C	109.5	C19—N3—C32	117.6 (2)
C18—C17—Cl2	115.6 (3)	O6—N4—O7A	110.7 (7)
C18—C17—Cl2A	107.1 (3)	O6—N4—O7	125.0 (5)
C18—C17—H17A	108.4	O7A—N4—O6A	120.9 (6)
Cl2—C17—H17A	108.4	O7—N4—O6A	126.4 (9)
Cl2A—C17—H17A	96.2	O6—N4—C22	121.7 (5)
C18—C17—H17B	108.4	O7A—N4—C22	123.0 (6)
Cl2—C17—H17B	108.4	O7—N4—C22	112.7 (6)
Cl2A—C17—H17B	127.7	O6A—N4—C22	116.0 (5)
H17A—C17—H17B	107.4	C26—C31—C30	123.3 (4)
O5—C18—N3	122.3 (3)	C26—C31—H31A	118.4
O5—C18—C17	122.8 (3)	C30—C31—H31A	118.4
Cl1—C1—C2—O1	5.3 (5)	C20—C19—C24—C25	−178.9 (3)
Cl1A—C1—C2—O1	−9.9 (4)	N3—C19—C24—C25	−0.9 (4)
Cl1—C1—C2—N1	−176.5 (3)	C23—C24—C25—O8	−35.0 (4)
Cl1A—C1—C2—N1	168.3 (2)	C19—C24—C25—O8	144.5 (3)
C8—C3—C4—C5	1.2 (4)	C23—C24—C25—C26	142.3 (3)
N1—C3—C4—C5	−175.7 (3)	C19—C24—C25—C26	−38.2 (4)
C3—C4—C5—C6	1.9 (4)	O8—C25—C26—C31	139.5 (3)
C4—C5—C6—C7	−2.4 (5)	C24—C25—C26—C31	−37.7 (4)
C4—C5—C6—N2	−179.3 (3)	O8—C25—C26—C27	−39.4 (4)
C5—C6—C7—C8	−0.2 (5)	C24—C25—C26—C27	143.4 (3)
N2—C6—C7—C8	176.7 (3)	C31—C26—C27—C28	1.1 (5)
C6—C7—C8—C3	3.4 (4)	C25—C26—C27—C28	−179.9 (3)
C6—C7—C8—C9	−175.2 (3)	C26—C27—C28—C29	−1.4 (6)
C4—C3—C8—C7	−3.9 (4)	C27—C28—C29—C30	0.2 (6)
N1—C3—C8—C7	173.1 (3)	C28—C29—C30—C31	1.3 (6)
C4—C3—C8—C9	174.7 (3)	O1—C2—N1—C3	−2.6 (4)
N1—C3—C8—C9	−8.4 (4)	C1—C2—N1—C3	179.2 (2)
C7—C8—C9—O4	−42.2 (4)	O1—C2—N1—C16	−175.3 (3)
C3—C8—C9—O4	139.2 (3)	C1—C2—N1—C16	6.5 (4)
C7—C8—C9—C10	136.9 (3)	C4—C3—N1—C2	−61.7 (4)
C3—C8—C9—C10	−41.7 (4)	C8—C3—N1—C2	121.3 (3)
O4—C9—C10—C15	−39.3 (4)	C4—C3—N1—C16	111.4 (3)
C8—C9—C10—C15	141.7 (3)	C8—C3—N1—C16	−65.6 (3)
O4—C9—C10—C11	140.2 (3)	C5—C6—N2—O2	174.7 (8)
C8—C9—C10—C11	−38.9 (4)	C7—C6—N2—O2	−2.3 (9)
C15—C10—C11—C12	−1.4 (5)	C5—C6—N2—O3A	12.5 (8)
C9—C10—C11—C12	179.1 (3)	C7—C6—N2—O3A	−164.5 (7)
C15—C10—C11—F1	176.8 (3)	C5—C6—N2—O2A	−172.9 (6)
C9—C10—C11—F1	−2.7 (4)	C7—C6—N2—O2A	10.0 (7)
F1—C11—C12—C13	−179.0 (3)	C5—C6—N2—O3	−6.4 (6)
C10—C11—C12—C13	−0.8 (5)	C7—C6—N2—O3	176.6 (5)
C11—C12—C13—C14	1.6 (6)	O5—C18—N3—C19	5.5 (5)
C12—C13—C14—C15	−0.3 (7)	C17—C18—N3—C19	−175.3 (3)
C11—C10—C15—C14	2.8 (5)	O5—C18—N3—C32	177.7 (3)
C9—C10—C15—C14	−177.7 (3)	C17—C18—N3—C32	−3.1 (4)
C13—C14—C15—C10	−2.1 (6)	C20—C19—N3—C18	120.9 (3)
Cl2—C17—C18—O5	6.0 (5)	C24—C19—N3—C18	−57.1 (4)
Cl2A—C17—C18—O5	−13.0 (4)	C20—C19—N3—C32	−51.8 (4)
Cl2—C17—C18—N3	−173.1 (3)	C24—C19—N3—C32	130.2 (3)
Cl2A—C17—C18—N3	167.8 (3)	C23—C22—N4—O6	−174.4 (7)
C24—C19—C20—C21	−2.3 (6)	C21—C22—N4—O6	5.8 (8)
N3—C19—C20—C21	179.6 (3)	C23—C22—N4—O7A	−20.9 (10)
C19—C20—C21—C22	1.3 (6)	C21—C22—N4—O7A	159.2 (10)
C20—C21—C22—C23	1.6 (6)	C23—C22—N4—O7	−2.8 (9)
C20—C21—C22—N4	−178.6 (3)	C21—C22—N4—O7	177.3 (8)
C21—C22—C23—C24	−3.3 (5)	C23—C22—N4—O6A	154.2 (7)
N4—C22—C23—C24	176.8 (3)	C21—C22—N4—O6A	−25.7 (8)
C22—C23—C24—C19	2.2 (4)	C27—C26—C31—C30	0.4 (5)
C22—C23—C24—C25	−178.3 (3)	C25—C26—C31—C30	−178.6 (3)
C20—C19—C24—C23	0.6 (4)	C29—C30—C31—C26	−1.6 (5)
N3—C19—C24—C23	178.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C32—H32A···O1	0.98	2.48	3.383 (4)	154.
C29—H29···O5i	0.95	2.50	3.194 (5)	130.
C28—H28···Cl1Aii	0.95	2.74	3.543 (6)	143.
C17—H17A···O1	0.99	2.38	3.348 (4)	165.
C16—H16B···O2iii	0.98	2.47	3.45 (1)	176.
C7—H7···O7iv	0.95	2.37	3.31 (2)	173.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C32—H32A⋯O1	0.98	2.48	3.383 (4)	154
C29—H29⋯O5i	0.95	2.50	3.194 (5)	130
C28—H28⋯Cl1Aii	0.95	2.74	3.543 (6)	143
C17—H17A⋯O1	0.99	2.38	3.348 (4)	165
C16—H16B⋯O2iii	0.98	2.47	3.45 (1)	176
C7—H7⋯O7iv	0.95	2.37	3.31 (2)	173

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