Ethyl 2-[(2,4-difluoro-phen-yl)hydrazinyl-idene]-3-oxobutano-ate.

The asymmetric unit of the title compound, C(12)H(12)F(2)N(2)O(3), contains two mol-ecules, both of which exist in an E conformation with respect to their C=N bonds [1.321 (6) and 1.310 (6) Å]. The mol-ecular conformations are supported by intra-molecular N-H⋯O hydrogen bonds, which generate S(6) rings. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯F hydrogen bonds into layers lying parallel to (001). The crystal studied was an inversion twin with a 0.58 (1):0.42 (1) domain ratio.

Related literature

For the biological activity of oxobutano­ate derivatives, see: Billington et al. (1979 ▶); Stancho et al. (2008 ▶). For the biological activity of pyrazole derivatives, see: Rai et al. (2008 ▶); Girisha et al. (2010 ▶); Isloor et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C12H12F2N2O3

M = 270.24

Orthorhombic,

a = 21.814 (4) Å

b = 9.0079 (15) Å

c = 13.188 (2) Å

V = 2591.4 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.38 × 0.32 × 0.31 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.957, T max = 0.964

14829 measured reflections

3855 independent reflections

1903 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.219

S = 1.02

3855 reflections

356 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.24 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/S1600536812000803/hb6590sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000803/hb6590Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812000803/hb6590Isup3.cml

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

C12H12F2N2O3	F(000) = 1120
Mr = 270.24	Dx = 1.385 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3499 reflections
a = 21.814 (4) Å	θ = 2.3–29.8°
b = 9.0079 (15) Å	µ = 0.12 mm−1
c = 13.188 (2) Å	T = 296 K
V = 2591.4 (8) Å3	Block, yellow
Z = 8	0.38 × 0.32 × 0.31 mm

Bruker SMART APEXII DUO CCD diffractometer	3855 independent reflections
Radiation source: fine-focus sealed tube	1903 reflections with I > 2σ(I)
graphite	Rint = 0.058
φ and ω scans	θmax = 29.9°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −25→30
Tmin = 0.957, Tmax = 0.964	k = −12→11
14829 measured reflections	l = −18→18

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)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.219	w = 1/[σ2(Fo2) + (0.1013P)2 + 0.7683P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
3855 reflections	Δρmax = 0.22 e Å−3
356 parameters	Δρmin = −0.24 e Å−3
1 restraint	Absolute structure: Flack (1983), 3406 Friedel pairs
Primary atom site location: structure-invariant direct methods

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	0.02111 (12)	−0.0552 (3)	0.4291 (4)	0.0738 (10)
F2A	−0.01712 (16)	0.4553 (4)	0.4498 (5)	0.1088 (16)
O1A	0.31436 (14)	0.0724 (4)	0.4235 (4)	0.0659 (10)
O2A	0.16259 (16)	−0.2942 (4)	0.4261 (4)	0.0719 (11)
O3A	0.34608 (17)	−0.1594 (5)	0.4477 (5)	0.0828 (14)
N1A	0.14227 (16)	−0.0160 (5)	0.4336 (4)	0.0500 (10)
N2A	0.20161 (16)	0.0028 (5)	0.4353 (4)	0.0478 (10)
C1A	0.1253 (2)	0.2526 (6)	0.4428 (6)	0.0642 (16)
H1AA	0.1673	0.2701	0.4442	0.077*
C2A	0.0849 (3)	0.3703 (6)	0.4469 (6)	0.0700 (15)
H2AA	0.0991	0.4675	0.4510	0.084*
C3A	0.0232 (2)	0.3402 (6)	0.4448 (6)	0.0712 (16)
C4A	−0.0002 (2)	0.2000 (6)	0.4385 (6)	0.0633 (13)
H4AA	−0.0423	0.1829	0.4365	0.076*
C5A	0.0411 (2)	0.0857 (6)	0.4353 (5)	0.0512 (11)
C6A	0.10348 (19)	0.1081 (6)	0.4367 (4)	0.0469 (11)
C7A	0.2391 (2)	−0.1124 (5)	0.4330 (5)	0.0483 (11)
C8A	0.3050 (2)	−0.0713 (6)	0.4356 (5)	0.0529 (13)
C9A	0.3782 (2)	0.1211 (7)	0.4260 (6)	0.0685 (16)
H9AA	0.4024	0.0646	0.3779	0.082*
H9AB	0.3952	0.1066	0.4932	0.082*
C11A	0.2181 (2)	−0.2672 (6)	0.4285 (5)	0.0606 (13)
C12A	0.2620 (3)	−0.3935 (6)	0.4238 (10)	0.104 (3)
H12A	0.2397	−0.4853	0.4220	0.156*
H12B	0.2880	−0.3917	0.4825	0.156*
H12C	0.2866	−0.3849	0.3638	0.156*
C10A	0.3790 (4)	0.2822 (9)	0.3988 (8)	0.113 (4)
H10A	0.4204	0.3180	0.3999	0.169*
H10B	0.3549	0.3369	0.4468	0.169*
H10C	0.3622	0.2951	0.3321	0.169*
F1B	−0.12910 (11)	−0.0552 (3)	0.1789 (3)	0.0686 (8)
F2B	−0.16421 (16)	0.4584 (4)	0.1702 (5)	0.1085 (14)
O1B	0.16419 (13)	0.0704 (4)	0.1812 (4)	0.0613 (10)
O2B	0.01257 (17)	−0.2955 (4)	0.1951 (5)	0.0810 (14)
O3B	0.19708 (15)	−0.1614 (4)	0.1938 (4)	0.0756 (12)
N1B	−0.00755 (16)	−0.0181 (4)	0.1844 (4)	0.0491 (9)
N2B	0.05230 (15)	−0.0004 (4)	0.1842 (4)	0.0479 (9)
C1B	−0.0234 (2)	0.2521 (6)	0.1778 (6)	0.0622 (13)
H1BA	0.0187	0.2693	0.1788	0.075*
C2B	−0.0629 (2)	0.3694 (6)	0.1749 (7)	0.0731 (16)
H2BA	−0.0482	0.4663	0.1725	0.088*
C3B	−0.1250 (2)	0.3412 (6)	0.1756 (6)	0.0677 (15)
C4B	−0.1493 (2)	0.2016 (6)	0.1751 (5)	0.0605 (13)
H4BA	−0.1914	0.1856	0.1721	0.073*
C5B	−0.1080 (2)	0.0857 (5)	0.1793 (5)	0.0489 (11)
C6B	−0.04523 (19)	0.1069 (5)	0.1792 (5)	0.0445 (10)
C7B	0.0894 (2)	−0.1147 (5)	0.1874 (4)	0.0465 (10)
C8B	0.1558 (2)	−0.0748 (6)	0.1879 (5)	0.0486 (11)
C9B	0.2268 (2)	0.1242 (6)	0.1836 (7)	0.0652 (14)
H9BA	0.2501	0.0813	0.1281	0.078*
H9BB	0.2463	0.0959	0.2469	0.078*
C11B	0.0684 (2)	−0.2708 (6)	0.1888 (5)	0.0584 (12)
C12B	0.1127 (3)	−0.3974 (6)	0.1820 (8)	0.0829 (18)
H12D	0.0909	−0.4895	0.1883	0.124*
H12E	0.1422	−0.3895	0.2357	0.124*
H12F	0.1333	−0.3944	0.1178	0.124*
C10B	0.2255 (3)	0.2861 (7)	0.1742 (12)	0.121 (3)
H10D	0.2661	0.3249	0.1833	0.182*
H10E	0.1988	0.3268	0.2249	0.182*
H10F	0.2107	0.3128	0.1081	0.182*
H1NB	−0.0208 (19)	−0.115 (5)	0.189 (4)	0.045 (12)*
H1NA	0.127 (2)	−0.104 (6)	0.433 (5)	0.056 (15)*

	U11	U22	U33	U12	U13	U23
F1A	0.0420 (15)	0.066 (2)	0.114 (3)	−0.0146 (13)	−0.003 (2)	−0.001 (2)
F2A	0.070 (2)	0.079 (3)	0.177 (5)	0.0320 (18)	0.000 (3)	−0.003 (3)
O1A	0.0297 (15)	0.057 (2)	0.111 (3)	−0.0035 (15)	−0.002 (2)	0.005 (2)
O2A	0.052 (2)	0.059 (2)	0.104 (3)	−0.0139 (17)	0.005 (3)	−0.002 (3)
O3A	0.0406 (18)	0.073 (3)	0.134 (4)	0.0115 (18)	−0.006 (2)	0.008 (3)
N1A	0.0301 (16)	0.051 (2)	0.069 (3)	−0.0065 (17)	−0.004 (2)	−0.001 (2)
N2A	0.0309 (18)	0.056 (2)	0.056 (2)	−0.0023 (17)	−0.002 (2)	0.001 (2)
C1A	0.038 (2)	0.059 (4)	0.095 (4)	−0.007 (2)	0.000 (3)	0.005 (4)
C2A	0.055 (3)	0.058 (3)	0.098 (4)	−0.002 (2)	0.002 (4)	−0.002 (4)
C3A	0.053 (3)	0.066 (4)	0.095 (4)	0.019 (3)	0.002 (4)	−0.003 (4)
C4A	0.039 (2)	0.075 (4)	0.076 (3)	0.004 (2)	0.000 (3)	0.004 (4)
C5A	0.036 (2)	0.059 (3)	0.059 (3)	−0.004 (2)	−0.003 (3)	0.003 (3)
C6A	0.032 (2)	0.054 (3)	0.054 (3)	−0.0031 (19)	−0.002 (3)	0.001 (3)
C7A	0.036 (2)	0.048 (2)	0.061 (3)	−0.0008 (19)	0.000 (3)	0.000 (3)
C8A	0.037 (2)	0.061 (3)	0.061 (3)	−0.001 (2)	−0.002 (3)	0.003 (3)
C9A	0.033 (2)	0.076 (4)	0.097 (4)	−0.010 (2)	−0.003 (3)	−0.006 (4)
C11A	0.058 (3)	0.051 (3)	0.072 (3)	−0.002 (2)	0.000 (3)	0.003 (3)
C12A	0.077 (5)	0.049 (3)	0.185 (9)	0.007 (3)	0.004 (6)	−0.008 (6)
C10A	0.062 (4)	0.084 (5)	0.191 (11)	−0.021 (4)	0.000 (5)	0.006 (6)
F1B	0.0406 (15)	0.0605 (17)	0.105 (2)	−0.0105 (13)	−0.004 (2)	0.003 (2)
F2B	0.073 (2)	0.078 (2)	0.175 (4)	0.0353 (17)	0.001 (3)	0.003 (3)
O1B	0.0300 (15)	0.055 (2)	0.099 (3)	−0.0035 (13)	−0.001 (2)	0.003 (2)
O2B	0.048 (2)	0.057 (2)	0.139 (4)	−0.0121 (16)	0.006 (3)	0.004 (3)
O3B	0.0375 (17)	0.065 (2)	0.124 (4)	0.0095 (15)	−0.001 (2)	0.005 (3)
N1B	0.0292 (17)	0.046 (2)	0.072 (2)	−0.0036 (15)	−0.003 (2)	0.000 (3)
N2B	0.0308 (16)	0.058 (2)	0.055 (2)	−0.0046 (16)	−0.001 (2)	0.000 (2)
C1B	0.042 (3)	0.055 (3)	0.089 (4)	−0.005 (2)	−0.002 (3)	−0.007 (3)
C2B	0.051 (3)	0.056 (3)	0.112 (5)	0.002 (2)	−0.005 (4)	−0.001 (4)
C3B	0.052 (3)	0.059 (3)	0.093 (4)	0.015 (2)	−0.002 (4)	−0.007 (4)
C4B	0.041 (2)	0.069 (3)	0.072 (3)	0.002 (2)	−0.004 (3)	0.001 (3)
C5B	0.039 (2)	0.052 (3)	0.056 (3)	−0.001 (2)	−0.006 (3)	−0.001 (3)
C6B	0.033 (2)	0.050 (2)	0.051 (2)	−0.0036 (17)	−0.003 (3)	0.001 (3)
C7B	0.037 (2)	0.048 (2)	0.055 (3)	−0.0013 (19)	−0.001 (3)	0.003 (3)
C8B	0.036 (2)	0.052 (3)	0.058 (3)	0.0005 (19)	−0.001 (3)	0.006 (3)
C9B	0.028 (2)	0.075 (3)	0.093 (4)	−0.009 (2)	−0.001 (3)	0.000 (4)
C11B	0.051 (3)	0.055 (3)	0.069 (3)	−0.005 (2)	−0.001 (3)	−0.002 (3)
C12B	0.064 (3)	0.049 (3)	0.136 (5)	0.001 (3)	−0.009 (5)	0.002 (5)
C10B	0.069 (4)	0.063 (4)	0.232 (10)	−0.026 (3)	−0.017 (7)	0.000 (7)

F1A—C5A	1.345 (6)	F1B—C5B	1.350 (5)
F2A—C3A	1.362 (6)	F2B—C3B	1.360 (6)
O1A—C8A	1.320 (7)	O1B—C8B	1.324 (6)
O1A—C9A	1.460 (6)	O1B—C9B	1.450 (5)
O2A—C11A	1.236 (6)	O2B—C11B	1.241 (6)
O3A—C8A	1.208 (6)	O3B—C8B	1.194 (6)
N1A—N2A	1.306 (5)	N1B—N2B	1.315 (5)
N1A—C6A	1.403 (6)	N1B—C6B	1.396 (6)
N1A—H1NA	0.86 (6)	N1B—H1NB	0.92 (5)
N2A—C7A	1.321 (6)	N2B—C7B	1.310 (6)
C1A—C2A	1.379 (8)	C1B—C2B	1.364 (8)
C1A—C6A	1.389 (7)	C1B—C6B	1.392 (7)
C1A—H1AA	0.9300	C1B—H1BA	0.9300
C2A—C3A	1.373 (8)	C2B—C3B	1.379 (7)
C2A—H2AA	0.9300	C2B—H2BA	0.9300
C3A—C4A	1.365 (8)	C3B—C4B	1.365 (8)
C4A—C5A	1.370 (7)	C4B—C5B	1.381 (7)
C4A—H4AA	0.9300	C4B—H4BA	0.9300
C5A—C6A	1.375 (6)	C5B—C6B	1.383 (6)
C7A—C11A	1.469 (7)	C7B—C11B	1.479 (7)
C7A—C8A	1.485 (7)	C7B—C8B	1.492 (6)
C9A—C10A	1.495 (10)	C9B—C10B	1.464 (8)
C9A—H9AA	0.9700	C9B—H9BA	0.9700
C9A—H9AB	0.9700	C9B—H9BB	0.9700
C11A—C12A	1.488 (8)	C11B—C12B	1.497 (7)
C12A—H12A	0.9600	C12B—H12D	0.9600
C12A—H12B	0.9600	C12B—H12E	0.9600
C12A—H12C	0.9600	C12B—H12F	0.9600
C10A—H10A	0.9600	C10B—H10D	0.9600
C10A—H10B	0.9600	C10B—H10E	0.9600
C10A—H10C	0.9600	C10B—H10F	0.9600
C8A—O1A—C9A	116.1 (4)	C8B—O1B—C9B	117.3 (3)
N2A—N1A—C6A	119.6 (4)	N2B—N1B—C6B	119.1 (4)
N2A—N1A—H1NA	120 (3)	N2B—N1B—H1NB	115 (3)
C6A—N1A—H1NA	121 (3)	C6B—N1B—H1NB	126 (3)
N1A—N2A—C7A	120.8 (4)	C7B—N2B—N1B	121.2 (4)
C2A—C1A—C6A	120.3 (5)	C2B—C1B—C6B	120.8 (5)
C2A—C1A—H1AA	119.9	C2B—C1B—H1BA	119.6
C6A—C1A—H1AA	119.9	C6B—C1B—H1BA	119.6
C3A—C2A—C1A	118.2 (5)	C1B—C2B—C3B	118.5 (5)
C3A—C2A—H2AA	120.9	C1B—C2B—H2BA	120.7
C1A—C2A—H2AA	120.9	C3B—C2B—H2BA	120.7
F2A—C3A—C4A	117.7 (5)	F2B—C3B—C4B	118.0 (5)
F2A—C3A—C2A	118.8 (5)	F2B—C3B—C2B	118.3 (5)
C4A—C3A—C2A	123.5 (5)	C4B—C3B—C2B	123.5 (5)
C3A—C4A—C5A	116.7 (5)	C3B—C4B—C5B	116.3 (4)
C3A—C4A—H4AA	121.6	C3B—C4B—H4BA	121.9
C5A—C4A—H4AA	121.6	C5B—C4B—H4BA	121.9
F1A—C5A—C4A	119.8 (4)	F1B—C5B—C4B	119.3 (4)
F1A—C5A—C6A	117.4 (4)	F1B—C5B—C6B	117.9 (4)
C4A—C5A—C6A	122.8 (5)	C4B—C5B—C6B	122.8 (4)
C5A—C6A—C1A	118.5 (5)	C5B—C6B—C1B	118.0 (4)
C5A—C6A—N1A	118.7 (4)	C5B—C6B—N1B	118.1 (4)
C1A—C6A—N1A	122.8 (4)	C1B—C6B—N1B	123.8 (4)
N2A—C7A—C11A	123.6 (4)	N2B—C7B—C11B	123.8 (4)
N2A—C7A—C8A	113.8 (4)	N2B—C7B—C8B	114.2 (4)
C11A—C7A—C8A	122.6 (4)	C11B—C7B—C8B	122.0 (4)
O3A—C8A—O1A	123.1 (5)	O3B—C8B—O1B	123.0 (4)
O3A—C8A—C7A	123.9 (5)	O3B—C8B—C7B	125.1 (5)
O1A—C8A—C7A	113.0 (4)	O1B—C8B—C7B	111.9 (4)
O1A—C9A—C10A	107.3 (5)	O1B—C9B—C10B	108.2 (4)
O1A—C9A—H9AA	110.3	O1B—C9B—H9BA	110.1
C10A—C9A—H9AA	110.3	C10B—C9B—H9BA	110.1
O1A—C9A—H9AB	110.3	O1B—C9B—H9BB	110.1
C10A—C9A—H9AB	110.3	C10B—C9B—H9BB	110.1
H9AA—C9A—H9AB	108.5	H9BA—C9B—H9BB	108.4
O2A—C11A—C7A	119.6 (5)	O2B—C11B—C7B	118.4 (5)
O2A—C11A—C12A	118.6 (5)	O2B—C11B—C12B	120.0 (5)
C7A—C11A—C12A	121.8 (5)	C7B—C11B—C12B	121.6 (4)
C11A—C12A—H12A	109.5	C11B—C12B—H12D	109.5
C11A—C12A—H12B	109.5	C11B—C12B—H12E	109.5
H12A—C12A—H12B	109.5	H12D—C12B—H12E	109.5
C11A—C12A—H12C	109.5	C11B—C12B—H12F	109.5
H12A—C12A—H12C	109.5	H12D—C12B—H12F	109.5
H12B—C12A—H12C	109.5	H12E—C12B—H12F	109.5
C9A—C10A—H10A	109.5	C9B—C10B—H10D	109.5
C9A—C10A—H10B	109.5	C9B—C10B—H10E	109.5
H10A—C10A—H10B	109.5	H10D—C10B—H10E	109.5
C9A—C10A—H10C	109.5	C9B—C10B—H10F	109.5
H10A—C10A—H10C	109.5	H10D—C10B—H10F	109.5
H10B—C10A—H10C	109.5	H10E—C10B—H10F	109.5
C6A—N1A—N2A—C7A	179.7 (6)	C6B—N1B—N2B—C7B	−178.9 (6)
C6A—C1A—C2A—C3A	0.0 (12)	C6B—C1B—C2B—C3B	1.4 (12)
C1A—C2A—C3A—F2A	179.3 (7)	C1B—C2B—C3B—F2B	−178.4 (7)
C1A—C2A—C3A—C4A	−0.2 (13)	C1B—C2B—C3B—C4B	−2.6 (13)
F2A—C3A—C4A—C5A	−178.9 (7)	F2B—C3B—C4B—C5B	179.2 (7)
C2A—C3A—C4A—C5A	0.7 (12)	C2B—C3B—C4B—C5B	3.3 (12)
C3A—C4A—C5A—F1A	−180.0 (7)	C3B—C4B—C5B—F1B	−179.9 (6)
C3A—C4A—C5A—C6A	−1.0 (10)	C3B—C4B—C5B—C6B	−3.0 (11)
F1A—C5A—C6A—C1A	179.8 (6)	F1B—C5B—C6B—C1B	178.9 (6)
C4A—C5A—C6A—C1A	0.9 (10)	C4B—C5B—C6B—C1B	1.9 (10)
F1A—C5A—C6A—N1A	−1.3 (9)	F1B—C5B—C6B—N1B	−3.5 (9)
C4A—C5A—C6A—N1A	179.7 (6)	C4B—C5B—C6B—N1B	179.5 (6)
C2A—C1A—C6A—C5A	−0.4 (10)	C2B—C1B—C6B—C5B	−1.1 (11)
C2A—C1A—C6A—N1A	−179.2 (7)	C2B—C1B—C6B—N1B	−178.5 (7)
N2A—N1A—C6A—C5A	−179.7 (5)	N2B—N1B—C6B—C5B	179.8 (6)
N2A—N1A—C6A—C1A	−0.8 (9)	N2B—N1B—C6B—C1B	−2.7 (10)
N1A—N2A—C7A—C11A	−0.1 (10)	N1B—N2B—C7B—C11B	1.7 (9)
N1A—N2A—C7A—C8A	−179.9 (5)	N1B—N2B—C7B—C8B	−179.3 (5)
C9A—O1A—C8A—O3A	−0.3 (10)	C9B—O1B—C8B—O3B	−1.4 (9)
C9A—O1A—C8A—C7A	179.6 (6)	C9B—O1B—C8B—C7B	178.4 (6)
N2A—C7A—C8A—O3A	169.7 (7)	N2B—C7B—C8B—O3B	177.5 (6)
C11A—C7A—C8A—O3A	−10.1 (11)	C11B—C7B—C8B—O3B	−3.4 (10)
N2A—C7A—C8A—O1A	−10.2 (9)	N2B—C7B—C8B—O1B	−2.3 (8)
C11A—C7A—C8A—O1A	170.0 (6)	C11B—C7B—C8B—O1B	176.8 (5)
C8A—O1A—C9A—C10A	173.4 (6)	C8B—O1B—C9B—C10B	179.4 (8)
N2A—C7A—C11A—O2A	0.5 (11)	N2B—C7B—C11B—O2B	−5.7 (10)
C8A—C7A—C11A—O2A	−179.8 (7)	C8B—C7B—C11B—O2B	175.2 (6)
N2A—C7A—C11A—C12A	178.7 (8)	N2B—C7B—C11B—C12B	173.8 (7)
C8A—C7A—C11A—C12A	−1.6 (12)	C8B—C7B—C11B—C12B	−5.2 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1B—H1NB···O2B	0.92 (4)	1.78 (4)	2.541 (5)	138 (4)
N1A—H1NA···O2A	0.86 (5)	1.88 (5)	2.547 (6)	133 (4)
C2A—H2AA···O2Ai	0.93	2.58	3.476 (7)	163
C4A—H4AA···O3Aii	0.93	2.45	3.375 (6)	173
C2B—H2BA···O2Bi	0.93	2.54	3.449 (6)	166
C4B—H4BA···O3Bii	0.93	2.46	3.380 (6)	170
C10A—H10A···F2Aiii	0.96	2.54	3.343 (9)	141
C10B—H10D···F2Biii	0.96	2.48	3.330 (7)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1B—H1NB⋯O2B	0.92 (4)	1.78 (4)	2.541 (5)	138 (4)
N1A—H1NA⋯O2A	0.86 (5)	1.88 (5)	2.547 (6)	133 (4)
C2A—H2AA⋯O2Ai	0.93	2.58	3.476 (7)	163
C4A—H4AA⋯O3Aii	0.93	2.45	3.375 (6)	173
C2B—H2BA⋯O2Bi	0.93	2.54	3.449 (6)	166
C4B—H4BA⋯O3Bii	0.93	2.46	3.380 (6)	170
C10A—H10A⋯F2Aiii	0.96	2.54	3.343 (9)	141
C10B—H10D⋯F2Biii	0.96	2.48	3.330 (7)	148

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