(E)-1-(2,4-Dinitro-phen-yl)-2-[1-(4-fluoro-phen-yl)ethyl-idene]hydrazine.

The title compound, C(14)H(11)FN(4)O(4), crystallizes with two essentially planar mol-ecules in the asymmetric unit; the dihedral angles between the benzene rings are 1.57 (15) and 6.17 (15)°. In each mol-ecule, an intra-molecular N-H⋯O hydrogen bond generates an S(6) ring. In the crystal, mol-ecules are linked by weak C-H⋯O and C-H⋯F inter-actions into sheets lying parallel to (120). O⋯C [2.980 (4) Å] and O⋯N [2.892 (3) Å] short contacts also occur.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Chantrapromma et al. (2011 ▶); Fun et al. (2011 ▶); Nilwanna et al. (2011 ▶). For background to the bio­logical activity of hydro­zones, see: Cui et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H11FN4O4

M = 318.27

Triclinic,

a = 8.8278 (3) Å

b = 10.9177 (4) Å

c = 15.2698 (6) Å

α = 100.649 (3)°

β = 104.948 (3)°

γ = 94.177 (3)°

V = 1386.10 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.32 × 0.30 × 0.04 mm

Data collection

Bruker APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.962, T max = 0.996

19163 measured reflections

5084 independent reflections

3438 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.144

S = 1.09

5084 reflections

425 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812000815/hb6595sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000815/hb6595Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000815/hb6595Isup3.cml

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

C14H11FN4O4	Z = 4
Mr = 318.27	F(000) = 656
Triclinic, P1	Dx = 1.525 Mg m−3
Hall symbol: -P 1	Melting point = 507–508 K
a = 8.8278 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.9177 (4) Å	Cell parameters from 5084 reflections
c = 15.2698 (6) Å	θ = 1.4–25.5°
α = 100.649 (3)°	µ = 0.12 mm−1
β = 104.948 (3)°	T = 100 K
γ = 94.177 (3)°	Plate, orange
V = 1386.10 (9) Å3	0.32 × 0.30 × 0.04 mm

Bruker APEX DUO CCD diffractometer	5084 independent reflections
Radiation source: sealed tube	3438 reflections with I > 2σ(I)
graphite	Rint = 0.062
φ and ω scans	θmax = 25.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.962, Tmax = 0.996	k = −13→13
19163 measured reflections	l = −18→18

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) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0581P)2 + 0.5322P] where P = (Fo2 + 2Fc2)/3
5084 reflections	(Δ/σ)max = 0.001
425 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
F1A	−0.1138 (2)	1.38191 (18)	0.72609 (13)	0.0384 (5)
O1A	0.3270 (2)	0.92455 (19)	1.22388 (13)	0.0232 (5)
O2A	0.4748 (3)	0.7798 (2)	1.25503 (14)	0.0327 (6)
O3A	0.6854 (2)	0.54065 (19)	1.03711 (14)	0.0248 (5)
O4A	0.6408 (3)	0.5739 (2)	0.89707 (14)	0.0302 (6)
N1A	0.2023 (3)	1.0454 (2)	0.99313 (15)	0.0172 (6)
N2A	0.2674 (3)	0.9835 (2)	1.06150 (17)	0.0187 (6)
H1NA	0.265 (4)	0.999 (3)	1.119 (2)	0.046 (11)*
N3A	0.4076 (3)	0.8423 (2)	1.20111 (16)	0.0217 (6)
N4A	0.6260 (3)	0.5974 (2)	0.97652 (17)	0.0203 (6)
C1A	0.3535 (3)	0.8886 (3)	1.04164 (19)	0.0176 (7)
C2A	0.4241 (3)	0.8195 (3)	1.10755 (18)	0.0168 (7)
C3A	0.5136 (3)	0.7243 (3)	1.08624 (19)	0.0184 (7)
H3A	0.5611	0.6795	1.1317	0.022*
C4A	0.5318 (3)	0.6963 (3)	0.99885 (19)	0.0173 (7)
C5A	0.4620 (3)	0.7613 (3)	0.93140 (19)	0.0186 (7)
H5A	0.4753	0.7402	0.8708	0.022*
C6A	0.3753 (3)	0.8549 (3)	0.95216 (19)	0.0199 (7)
H6A	0.3284	0.8984	0.9057	0.024*
C7A	0.1274 (3)	1.1388 (3)	1.01561 (19)	0.0196 (7)
C8A	0.0606 (3)	1.2029 (3)	0.9396 (2)	0.0199 (7)
C9A	−0.0301 (3)	1.3018 (3)	0.9510 (2)	0.0233 (7)
H9A	−0.0515	1.3280	1.0090	0.028*
C10A	−0.0891 (4)	1.3619 (3)	0.8797 (2)	0.0267 (8)
H10A	−0.1507	1.4287	0.8879	0.032*
C11A	−0.0561 (4)	1.3223 (3)	0.7965 (2)	0.0260 (7)
C12A	0.0323 (3)	1.2265 (3)	0.7816 (2)	0.0256 (7)
H12A	0.0530	1.2017	0.7233	0.031*
C13A	0.0904 (4)	1.1669 (3)	0.8530 (2)	0.0225 (7)
H13A	0.1517	1.1002	0.8435	0.027*
C14A	0.1104 (4)	1.1822 (3)	1.1112 (2)	0.0260 (8)
H14A	0.2150	1.1981	1.1563	0.039*
H14B	0.0443	1.1171	1.1259	0.039*
H14C	0.0608	1.2598	1.1141	0.039*
F1B	0.8852 (2)	0.33781 (18)	0.22701 (13)	0.0398 (5)
O1B	0.4912 (3)	0.8092 (2)	0.72701 (13)	0.0279 (5)
O2B	0.3390 (3)	0.9487 (2)	0.75796 (13)	0.0313 (6)
O3B	0.0791 (2)	1.1726 (2)	0.53970 (14)	0.0298 (5)
O4B	0.0896 (3)	1.1249 (2)	0.39717 (14)	0.0304 (6)
N1B	0.5742 (3)	0.6777 (2)	0.49060 (16)	0.0207 (6)
N2B	0.5224 (3)	0.7463 (2)	0.56024 (18)	0.0213 (6)
H1NB	0.550 (4)	0.730 (3)	0.613 (2)	0.037 (10)*
N3B	0.3997 (3)	0.8863 (2)	0.70341 (16)	0.0234 (6)
N4B	0.1260 (3)	1.1111 (2)	0.47797 (17)	0.0241 (6)
C1B	0.4235 (3)	0.8318 (3)	0.54087 (19)	0.0199 (7)
C2B	0.3639 (3)	0.9045 (3)	0.60923 (18)	0.0194 (7)
C3B	0.2684 (3)	0.9967 (3)	0.5887 (2)	0.0208 (7)
H3B	0.2318	1.0457	0.6354	0.025*
C4B	0.2279 (3)	1.0158 (3)	0.50028 (19)	0.0186 (7)
C5B	0.2787 (3)	0.9430 (3)	0.42980 (19)	0.0206 (7)
H5B	0.2467	0.9561	0.3682	0.025*
C6B	0.3737 (3)	0.8539 (3)	0.45026 (19)	0.0205 (7)
H6B	0.4075	0.8051	0.4023	0.025*
C7B	0.6699 (3)	0.5988 (3)	0.5147 (2)	0.0205 (7)
C8B	0.7261 (3)	0.5269 (3)	0.4389 (2)	0.0223 (7)
C9B	0.8137 (4)	0.4275 (3)	0.4514 (2)	0.0252 (7)
H9B	0.8379	0.4035	0.5096	0.030*
C10B	0.8665 (4)	0.3627 (3)	0.3798 (2)	0.0281 (8)
H10B	0.9259	0.2946	0.3885	0.034*
C11B	0.8308 (4)	0.3995 (3)	0.2966 (2)	0.0279 (8)
C12B	0.7444 (4)	0.4969 (3)	0.2808 (2)	0.0301 (8)
H12B	0.7212	0.5202	0.2223	0.036*
C13B	0.6921 (4)	0.5602 (3)	0.3525 (2)	0.0257 (7)
H13B	0.6319	0.6276	0.3427	0.031*
C14B	0.7249 (4)	0.5802 (3)	0.6127 (2)	0.0298 (8)
H14D	0.7731	0.6609	0.6544	0.045*
H14E	0.8031	0.5207	0.6164	0.045*
H14F	0.6345	0.5470	0.6312	0.045*

	U11	U22	U33	U12	U13	U23
F1A	0.0397 (12)	0.0405 (12)	0.0411 (12)	0.0156 (10)	0.0087 (9)	0.0230 (10)
O1A	0.0298 (13)	0.0258 (13)	0.0175 (11)	0.0094 (10)	0.0126 (10)	0.0029 (9)
O2A	0.0506 (16)	0.0371 (14)	0.0176 (11)	0.0195 (12)	0.0133 (11)	0.0129 (11)
O3A	0.0231 (12)	0.0232 (12)	0.0298 (12)	0.0056 (10)	0.0068 (10)	0.0096 (10)
O4A	0.0372 (14)	0.0340 (14)	0.0250 (12)	0.0134 (11)	0.0178 (11)	0.0037 (10)
N1A	0.0149 (14)	0.0205 (14)	0.0192 (13)	0.0068 (11)	0.0063 (10)	0.0076 (11)
N2A	0.0236 (15)	0.0207 (15)	0.0161 (13)	0.0090 (12)	0.0095 (11)	0.0063 (11)
N3A	0.0271 (15)	0.0229 (15)	0.0169 (13)	0.0028 (12)	0.0085 (12)	0.0054 (12)
N4A	0.0187 (14)	0.0190 (14)	0.0237 (14)	0.0021 (11)	0.0076 (11)	0.0038 (12)
C1A	0.0160 (16)	0.0187 (17)	0.0193 (15)	−0.0001 (13)	0.0071 (13)	0.0048 (13)
C2A	0.0199 (17)	0.0186 (16)	0.0120 (14)	0.0012 (13)	0.0060 (12)	0.0015 (12)
C3A	0.0144 (16)	0.0181 (17)	0.0208 (16)	−0.0017 (13)	0.0011 (13)	0.0058 (13)
C4A	0.0160 (16)	0.0166 (16)	0.0204 (16)	0.0020 (13)	0.0078 (13)	0.0024 (13)
C5A	0.0211 (17)	0.0215 (17)	0.0157 (15)	0.0023 (14)	0.0094 (13)	0.0042 (13)
C6A	0.0204 (18)	0.0230 (18)	0.0174 (15)	0.0016 (14)	0.0064 (13)	0.0057 (13)
C7A	0.0141 (16)	0.0236 (18)	0.0208 (16)	−0.0004 (14)	0.0061 (13)	0.0030 (13)
C8A	0.0139 (16)	0.0203 (17)	0.0236 (16)	−0.0003 (13)	0.0039 (13)	0.0025 (13)
C9A	0.0217 (18)	0.0205 (18)	0.0293 (17)	0.0019 (14)	0.0125 (14)	0.0018 (14)
C10A	0.0190 (18)	0.0195 (18)	0.042 (2)	0.0068 (14)	0.0085 (15)	0.0057 (15)
C11A	0.0224 (18)	0.0265 (19)	0.0308 (18)	0.0062 (15)	0.0027 (14)	0.0157 (15)
C12A	0.0213 (18)	0.033 (2)	0.0248 (17)	0.0045 (15)	0.0081 (14)	0.0097 (15)
C13A	0.0235 (18)	0.0224 (18)	0.0249 (17)	0.0064 (14)	0.0100 (14)	0.0072 (14)
C14A	0.0309 (19)	0.0259 (19)	0.0244 (17)	0.0087 (15)	0.0131 (15)	0.0037 (14)
F1B	0.0374 (12)	0.0395 (13)	0.0394 (11)	0.0146 (10)	0.0131 (9)	−0.0070 (9)
O1B	0.0352 (14)	0.0316 (14)	0.0193 (11)	0.0074 (11)	0.0068 (10)	0.0108 (10)
O2B	0.0405 (14)	0.0401 (15)	0.0168 (11)	0.0054 (11)	0.0161 (10)	0.0033 (10)
O3B	0.0299 (13)	0.0322 (14)	0.0301 (13)	0.0082 (11)	0.0157 (11)	0.0009 (10)
O4B	0.0368 (14)	0.0355 (14)	0.0229 (12)	0.0156 (11)	0.0084 (10)	0.0115 (10)
N1B	0.0231 (15)	0.0203 (15)	0.0197 (13)	0.0030 (12)	0.0090 (11)	0.0022 (11)
N2B	0.0254 (16)	0.0256 (15)	0.0150 (14)	0.0051 (12)	0.0070 (12)	0.0066 (12)
N3B	0.0272 (16)	0.0280 (16)	0.0153 (13)	−0.0014 (13)	0.0083 (12)	0.0039 (12)
N4B	0.0222 (15)	0.0267 (16)	0.0245 (15)	0.0020 (12)	0.0104 (12)	0.0033 (12)
C1B	0.0191 (17)	0.0210 (17)	0.0194 (16)	−0.0026 (14)	0.0048 (13)	0.0064 (13)
C2B	0.0232 (18)	0.0238 (18)	0.0118 (14)	−0.0012 (14)	0.0071 (13)	0.0037 (13)
C3B	0.0188 (17)	0.0236 (18)	0.0211 (16)	0.0006 (14)	0.0104 (13)	0.0010 (13)
C4B	0.0173 (17)	0.0217 (17)	0.0192 (15)	0.0034 (13)	0.0081 (13)	0.0057 (13)
C5B	0.0218 (18)	0.0250 (18)	0.0154 (15)	0.0016 (14)	0.0061 (13)	0.0042 (13)
C6B	0.0256 (18)	0.0225 (18)	0.0144 (15)	0.0010 (14)	0.0093 (13)	0.0017 (13)
C7B	0.0159 (17)	0.0215 (18)	0.0231 (16)	−0.0005 (14)	0.0016 (13)	0.0084 (14)
C8B	0.0166 (17)	0.0236 (18)	0.0257 (17)	0.0000 (14)	0.0032 (13)	0.0080 (14)
C9B	0.0223 (18)	0.0210 (18)	0.0309 (18)	0.0027 (14)	0.0033 (14)	0.0079 (14)
C10B	0.0176 (18)	0.0217 (18)	0.041 (2)	0.0056 (14)	0.0015 (15)	0.0050 (15)
C11B	0.0212 (18)	0.0248 (19)	0.0331 (19)	0.0023 (15)	0.0072 (15)	−0.0048 (15)
C12B	0.032 (2)	0.032 (2)	0.0258 (17)	0.0075 (16)	0.0073 (15)	0.0064 (15)
C13B	0.0280 (19)	0.0222 (18)	0.0276 (17)	0.0093 (15)	0.0063 (15)	0.0064 (14)
C14B	0.032 (2)	0.037 (2)	0.0239 (17)	0.0096 (16)	0.0063 (15)	0.0136 (15)

F1A—C11A	1.365 (3)	F1B—C11B	1.363 (3)
O1A—N3A	1.241 (3)	O1B—N3B	1.246 (3)
O2A—N3A	1.229 (3)	O2B—N3B	1.232 (3)
O3A—N4A	1.235 (3)	O3B—N4B	1.233 (3)
O4A—N4A	1.235 (3)	O4B—N4B	1.233 (3)
N1A—C7A	1.296 (3)	N1B—C7B	1.286 (4)
N1A—N2A	1.373 (3)	N1B—N2B	1.381 (3)
N2A—C1A	1.364 (3)	N2B—C1B	1.345 (4)
N2A—H1NA	0.87 (4)	N2B—H1NB	0.84 (3)
N3A—C2A	1.451 (3)	N3B—C2B	1.445 (3)
N4A—C4A	1.454 (3)	N4B—C4B	1.455 (4)
C1A—C2A	1.412 (4)	C1B—C6B	1.411 (4)
C1A—C6A	1.414 (4)	C1B—C2B	1.427 (4)
C2A—C3A	1.392 (4)	C2B—C3B	1.388 (4)
C3A—C4A	1.366 (4)	C3B—C4B	1.363 (4)
C3A—H3A	0.9500	C3B—H3B	0.9500
C4A—C5A	1.397 (4)	C4B—C5B	1.405 (4)
C5A—C6A	1.360 (4)	C5B—C6B	1.358 (4)
C5A—H5A	0.9500	C5B—H5B	0.9500
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—C8A	1.480 (4)	C7B—C8B	1.491 (4)
C7A—C14A	1.499 (4)	C7B—C14B	1.506 (4)
C8A—C9A	1.402 (4)	C8B—C9B	1.391 (4)
C8A—C13A	1.406 (4)	C8B—C13B	1.397 (4)
C9A—C10A	1.382 (4)	C9B—C10B	1.392 (4)
C9A—H9A	0.9500	C9B—H9B	0.9500
C10A—C11A	1.376 (4)	C10B—C11B	1.370 (4)
C10A—H10A	0.9500	C10B—H10B	0.9500
C11A—C12A	1.370 (4)	C11B—C12B	1.374 (4)
C12A—C13A	1.377 (4)	C12B—C13B	1.384 (4)
C12A—H12A	0.9500	C12B—H12B	0.9500
C13A—H13A	0.9500	C13B—H13B	0.9500
C14A—H14A	0.9800	C14B—H14D	0.9800
C14A—H14B	0.9800	C14B—H14E	0.9800
C14A—H14C	0.9800	C14B—H14F	0.9800
C7A—N1A—N2A	117.2 (2)	C7B—N1B—N2B	116.2 (2)
C1A—N2A—N1A	118.9 (2)	C1B—N2B—N1B	119.9 (2)
C1A—N2A—H1NA	113 (2)	C1B—N2B—H1NB	122 (2)
N1A—N2A—H1NA	128 (2)	N1B—N2B—H1NB	118 (2)
O2A—N3A—O1A	122.4 (2)	O2B—N3B—O1B	122.2 (2)
O2A—N3A—C2A	118.7 (2)	O2B—N3B—C2B	118.5 (2)
O1A—N3A—C2A	118.8 (2)	O1B—N3B—C2B	119.3 (2)
O3A—N4A—O4A	123.5 (2)	O3B—N4B—O4B	123.3 (3)
O3A—N4A—C4A	118.7 (2)	O3B—N4B—C4B	119.0 (2)
O4A—N4A—C4A	117.8 (2)	O4B—N4B—C4B	117.7 (2)
N2A—C1A—C2A	122.7 (2)	N2B—C1B—C6B	120.8 (3)
N2A—C1A—C6A	120.4 (3)	N2B—C1B—C2B	122.7 (3)
C2A—C1A—C6A	116.9 (3)	C6B—C1B—C2B	116.5 (3)
C3A—C2A—C1A	121.7 (2)	C3B—C2B—C1B	121.6 (3)
C3A—C2A—N3A	115.7 (2)	C3B—C2B—N3B	116.5 (2)
C1A—C2A—N3A	122.5 (2)	C1B—C2B—N3B	121.9 (3)
C4A—C3A—C2A	118.9 (3)	C4B—C3B—C2B	118.9 (3)
C4A—C3A—H3A	120.6	C4B—C3B—H3B	120.6
C2A—C3A—H3A	120.6	C2B—C3B—H3B	120.6
C3A—C4A—C5A	121.1 (3)	C3B—C4B—C5B	121.5 (3)
C3A—C4A—N4A	119.0 (3)	C3B—C4B—N4B	119.2 (3)
C5A—C4A—N4A	119.9 (2)	C5B—C4B—N4B	119.3 (2)
C6A—C5A—C4A	120.2 (3)	C6B—C5B—C4B	119.6 (3)
C6A—C5A—H5A	119.9	C6B—C5B—H5B	120.2
C4A—C5A—H5A	119.9	C4B—C5B—H5B	120.2
C5A—C6A—C1A	121.2 (3)	C5B—C6B—C1B	121.8 (3)
C5A—C6A—H6A	119.4	C5B—C6B—H6B	119.1
C1A—C6A—H6A	119.4	C1B—C6B—H6B	119.1
N1A—C7A—C8A	115.0 (2)	N1B—C7B—C8B	115.4 (3)
N1A—C7A—C14A	123.6 (3)	N1B—C7B—C14B	123.2 (3)
C8A—C7A—C14A	121.4 (3)	C8B—C7B—C14B	121.4 (3)
C9A—C8A—C13A	117.7 (3)	C9B—C8B—C13B	118.4 (3)
C9A—C8A—C7A	122.3 (3)	C9B—C8B—C7B	122.0 (3)
C13A—C8A—C7A	119.9 (3)	C13B—C8B—C7B	119.6 (3)
C10A—C9A—C8A	121.5 (3)	C8B—C9B—C10B	121.0 (3)
C10A—C9A—H9A	119.3	C8B—C9B—H9B	119.5
C8A—C9A—H9A	119.3	C10B—C9B—H9B	119.5
C11A—C10A—C9A	118.1 (3)	C11B—C10B—C9B	118.4 (3)
C11A—C10A—H10A	121.0	C11B—C10B—H10B	120.8
C9A—C10A—H10A	121.0	C9B—C10B—H10B	120.8
F1A—C11A—C12A	118.9 (3)	F1B—C11B—C10B	118.5 (3)
F1A—C11A—C10A	118.2 (3)	F1B—C11B—C12B	118.8 (3)
C12A—C11A—C10A	122.9 (3)	C10B—C11B—C12B	122.7 (3)
C11A—C12A—C13A	118.6 (3)	C11B—C12B—C13B	118.3 (3)
C11A—C12A—H12A	120.7	C11B—C12B—H12B	120.9
C13A—C12A—H12A	120.7	C13B—C12B—H12B	120.9
C12A—C13A—C8A	121.2 (3)	C12B—C13B—C8B	121.2 (3)
C12A—C13A—H13A	119.4	C12B—C13B—H13B	119.4
C8A—C13A—H13A	119.4	C8B—C13B—H13B	119.4
C7A—C14A—H14A	109.5	C7B—C14B—H14D	109.5
C7A—C14A—H14B	109.5	C7B—C14B—H14E	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
C7A—C14A—H14C	109.5	C7B—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5
C7A—N1A—N2A—C1A	−176.9 (3)	C7B—N1B—N2B—C1B	179.3 (3)
N1A—N2A—C1A—C2A	−179.7 (3)	N1B—N2B—C1B—C6B	−1.1 (4)
N1A—N2A—C1A—C6A	0.1 (4)	N1B—N2B—C1B—C2B	179.1 (3)
N2A—C1A—C2A—C3A	−179.0 (3)	N2B—C1B—C2B—C3B	176.6 (3)
C6A—C1A—C2A—C3A	1.2 (4)	C6B—C1B—C2B—C3B	−3.2 (4)
N2A—C1A—C2A—N3A	1.4 (4)	N2B—C1B—C2B—N3B	−3.3 (4)
C6A—C1A—C2A—N3A	−178.4 (3)	C6B—C1B—C2B—N3B	176.9 (3)
O2A—N3A—C2A—C3A	1.6 (4)	O2B—N3B—C2B—C3B	3.1 (4)
O1A—N3A—C2A—C3A	−178.8 (3)	O1B—N3B—C2B—C3B	−176.5 (3)
O2A—N3A—C2A—C1A	−178.8 (3)	O2B—N3B—C2B—C1B	−177.0 (3)
O1A—N3A—C2A—C1A	0.8 (4)	O1B—N3B—C2B—C1B	3.4 (4)
C1A—C2A—C3A—C4A	−0.7 (4)	C1B—C2B—C3B—C4B	1.6 (4)
N3A—C2A—C3A—C4A	178.9 (3)	N3B—C2B—C3B—C4B	−178.5 (3)
C2A—C3A—C4A—C5A	−0.2 (4)	C2B—C3B—C4B—C5B	1.0 (4)
C2A—C3A—C4A—N4A	179.6 (2)	C2B—C3B—C4B—N4B	179.1 (3)
O3A—N4A—C4A—C3A	0.7 (4)	O3B—N4B—C4B—C3B	0.2 (4)
O4A—N4A—C4A—C3A	−180.0 (3)	O4B—N4B—C4B—C3B	−179.0 (3)
O3A—N4A—C4A—C5A	−179.5 (3)	O3B—N4B—C4B—C5B	178.4 (3)
O4A—N4A—C4A—C5A	−0.1 (4)	O4B—N4B—C4B—C5B	−0.8 (4)
C3A—C4A—C5A—C6A	0.5 (4)	C3B—C4B—C5B—C6B	−1.8 (4)
N4A—C4A—C5A—C6A	−179.3 (3)	N4B—C4B—C5B—C6B	−179.9 (3)
C4A—C5A—C6A—C1A	0.0 (4)	C4B—C5B—C6B—C1B	0.0 (4)
N2A—C1A—C6A—C5A	179.4 (3)	N2B—C1B—C6B—C5B	−177.5 (3)
C2A—C1A—C6A—C5A	−0.8 (4)	C2B—C1B—C6B—C5B	2.4 (4)
N2A—N1A—C7A—C8A	179.5 (2)	N2B—N1B—C7B—C8B	−179.2 (2)
N2A—N1A—C7A—C14A	0.6 (4)	N2B—N1B—C7B—C14B	−0.2 (4)
N1A—C7A—C8A—C9A	176.9 (3)	N1B—C7B—C8B—C9B	−171.8 (3)
C14A—C7A—C8A—C9A	−4.1 (4)	C14B—C7B—C8B—C9B	9.2 (4)
N1A—C7A—C8A—C13A	−4.5 (4)	N1B—C7B—C8B—C13B	8.9 (4)
C14A—C7A—C8A—C13A	174.5 (3)	C14B—C7B—C8B—C13B	−170.2 (3)
C13A—C8A—C9A—C10A	0.2 (4)	C13B—C8B—C9B—C10B	0.1 (4)
C7A—C8A—C9A—C10A	178.8 (3)	C7B—C8B—C9B—C10B	−179.3 (3)
C8A—C9A—C10A—C11A	−0.1 (4)	C8B—C9B—C10B—C11B	0.3 (5)
C9A—C10A—C11A—F1A	−179.8 (3)	C9B—C10B—C11B—F1B	178.7 (3)
C9A—C10A—C11A—C12A	−0.1 (5)	C9B—C10B—C11B—C12B	−0.4 (5)
F1A—C11A—C12A—C13A	179.9 (3)	F1B—C11B—C12B—C13B	−178.9 (3)
C10A—C11A—C12A—C13A	0.2 (5)	C10B—C11B—C12B—C13B	0.2 (5)
C11A—C12A—C13A—C8A	−0.1 (4)	C11B—C12B—C13B—C8B	0.2 (5)
C9A—C8A—C13A—C12A	−0.1 (4)	C9B—C8B—C13B—C12B	−0.4 (5)
C7A—C8A—C13A—C12A	−178.7 (3)	C7B—C8B—C13B—C12B	179.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H1NA···O1A	0.87 (3)	1.90 (3)	2.609 (3)	137 (3)
N2B—H1NB···O1B	0.84 (3)	2.01 (3)	2.603 (3)	128 (3)
C5A—H5A···O1B	0.95	2.48	3.329 (3)	148
C5B—H5B···O1Ai	0.95	2.46	3.253 (3)	141
C6A—H6A···O2B	0.95	2.44	3.260 (4)	144
C6B—H6B···O2Ai	0.95	2.44	3.305 (4)	151
C10A—H10A···O4Aii	0.95	2.53	3.466 (4)	169
C10B—H10B···O4Biii	0.95	2.43	3.379 (4)	174
C13B—H13B···O2Ai	0.95	2.58	3.487 (4)	159
C14B—H14E···F1Aiii	0.98	2.47	3.205 (4)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H1NA⋯O1A	0.87 (3)	1.90 (3)	2.609 (3)	137 (3)
N2B—H1NB⋯O1B	0.84 (3)	2.01 (3)	2.603 (3)	128 (3)
C5A—H5A⋯O1B	0.95	2.48	3.329 (3)	148
C5B—H5B⋯O1Ai	0.95	2.46	3.253 (3)	141
C6A—H6A⋯O2B	0.95	2.44	3.260 (4)	144
C6B—H6B⋯O2Ai	0.95	2.44	3.305 (4)	151
C10A—H10A⋯O4Aii	0.95	2.53	3.466 (4)	169
C10B—H10B⋯O4Biii	0.95	2.43	3.379 (4)	174
C13B—H13B⋯O2Ai	0.95	2.58	3.487 (4)	159
C14B—H14E⋯F1Aiii	0.98	2.47	3.205 (4)	131

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