Ethyl 4-oxo-8-trifluoro-methyl-1,4-dihydro-quinoline-3-carboxyl-ate.

The asymmetric unit of the title compound, C13H10F3NO3, contains two independent mol-ecules with similar conformations. In the crystal, N-H⋯O hydrogen bonds link alternating independent mol-ecules into chains in [-110]. In the chain, the quinoline planes of the independent mol-ecules are almost perpendicular to each other, forming a dihedral angle of 89.8 (1)°. π-π inter-actions between the aromatic rings of quinoline bicycles related by inversion centres [for two independent centrosymmetric dimers, the shortest centroid-centroid distances are 3.495 (1) and 3.603 (1) Å] link the hydrogen-bonded chains into layers parallel to (110). Weak C-H⋯F and C-H⋯O inter-actions further consolidate the crystal packing.

Related literature

For background information about the pharmacological properties of quinoline derivatives, see: Holla et al. (2006 ▶); Bekhit et al. (2004 ▶); Kaur et al. (2010 ▶); Isloor et al. (2009 ▶); Vijesh et al. (2011 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶). For the synthesis of the title compound, see: Thomas et al. (2011 ▶).

Experimental

Crystal data

C13H10F3NO3

M = 285.22

Triclinic,

a = 9.8248 (3) Å

b = 11.0222 (3) Å

c = 12.3450 (4) Å

α = 72.934 (1)°

β = 74.167 (1)°

γ = 74.059 (1)°

V = 1201.67 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 200 K

0.53 × 0.38 × 0.32 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.928, T max = 0.956

21419 measured reflections

5963 independent reflections

5051 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.116

S = 1.04

5963 reflections

371 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812045321/cv5354sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812045321/cv5354Isup2.cdx

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812045321/cv5354Isup3.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812045321/cv5354Isup4.cml

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

C13H10F3NO3	Z = 4
Mr = 285.22	F(000) = 584
Triclinic, P1	Dx = 1.577 Mg m−3
Hall symbol: -P 1	Melting point = 570–568 K
a = 9.8248 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.0222 (3) Å	Cell parameters from 9882 reflections
c = 12.3450 (4) Å	θ = 2.5–28.3°
α = 72.934 (1)°	µ = 0.14 mm−1
β = 74.167 (1)°	T = 200 K
γ = 74.059 (1)°	Platelet, colourless
V = 1201.67 (6) Å3	0.53 × 0.38 × 0.32 mm

Bruker APEXII CCD diffractometer	5963 independent reflections
Radiation source: fine-focus sealed tube	5051 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
φ and ω scans	θmax = 28.3°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→13
Tmin = 0.928, Tmax = 0.956	k = −14→14
21419 measured reflections	l = −16→16

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0593P)2 + 0.3846P] where P = (Fo2 + 2Fc2)/3
5963 reflections	(Δ/σ)max < 0.001
371 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

	x	y	z	Uiso*/Ueq
F11	0.33975 (9)	0.25175 (8)	0.03791 (8)	0.0439 (2)
F12	0.44442 (10)	0.35929 (10)	0.09612 (10)	0.0568 (3)
F13	0.47655 (10)	0.37218 (10)	−0.08575 (9)	0.0631 (3)
F21	0.16132 (9)	0.25934 (8)	0.55061 (8)	0.0470 (2)
F22	0.05981 (10)	0.16771 (11)	0.71858 (8)	0.0581 (3)
F23	0.01521 (11)	0.13966 (11)	0.56807 (11)	0.0657 (3)
O11	−0.20937 (11)	0.70312 (9)	0.17938 (8)	0.0405 (2)
O12	−0.33287 (11)	0.58234 (11)	0.40381 (10)	0.0474 (3)
O13	−0.19356 (10)	0.39636 (9)	0.48120 (8)	0.0360 (2)
O21	0.71392 (13)	−0.18698 (10)	0.68194 (9)	0.0488 (3)
O22	0.83982 (11)	−0.07326 (11)	0.79574 (11)	0.0533 (3)
O23	0.69974 (11)	0.11050 (11)	0.84210 (9)	0.0445 (2)
N1	0.12165 (11)	0.38724 (9)	0.19918 (9)	0.0270 (2)
H1	0.190 (2)	0.3151 (18)	0.2098 (16)	0.046 (5)*
N2	0.38130 (11)	0.12577 (10)	0.69417 (9)	0.0276 (2)
H2	0.3130 (19)	0.1915 (17)	0.7026 (15)	0.039 (4)*
C101	0.13071 (12)	0.48491 (11)	0.09948 (10)	0.0248 (2)
C102	0.25053 (13)	0.47904 (12)	0.00530 (11)	0.0291 (2)
C103	0.25240 (14)	0.57880 (13)	−0.09286 (11)	0.0341 (3)
H103	0.3331	0.5743	−0.1560	0.041*
C104	0.13755 (15)	0.68645 (13)	−0.10101 (11)	0.0345 (3)
H104	0.1399	0.7543	−0.1695	0.041*
C105	0.02133 (14)	0.69401 (11)	−0.00978 (11)	0.0307 (2)
H105	−0.0566	0.7675	−0.0154	0.037*
C106	0.01622 (12)	0.59419 (11)	0.09183 (10)	0.0251 (2)
C107	0.37692 (14)	0.36615 (14)	0.01239 (12)	0.0372 (3)
C108	−0.11013 (12)	0.60598 (11)	0.18858 (10)	0.0269 (2)
C109	−0.10586 (12)	0.49925 (11)	0.28998 (10)	0.0255 (2)
C110	0.00998 (12)	0.39563 (11)	0.28906 (10)	0.0261 (2)
H110	0.0107	0.3260	0.3562	0.031*
C111	−0.22344 (12)	0.50028 (11)	0.39440 (10)	0.0281 (2)
C112	−0.29520 (15)	0.38902 (15)	0.59208 (11)	0.0383 (3)
H11A	−0.2959	0.2970	0.6318	0.046*
H11B	−0.3939	0.4329	0.5794	0.046*
C113	−0.25346 (18)	0.45247 (16)	0.66662 (13)	0.0459 (3)
H11C	−0.1546	0.4106	0.6770	0.069*
H11D	−0.3202	0.4435	0.7423	0.069*
H11E	−0.2583	0.5448	0.6292	0.069*
C201	0.36760 (13)	0.02791 (11)	0.65228 (10)	0.0278 (2)
C202	0.24340 (14)	0.03303 (13)	0.61281 (11)	0.0333 (3)
C203	0.23449 (18)	−0.07003 (15)	0.57567 (13)	0.0445 (3)
H203	0.1504	−0.0669	0.5502	0.053*
C204	0.3472 (2)	−0.17898 (15)	0.57496 (14)	0.0498 (4)
H204	0.3396	−0.2497	0.5494	0.060*
C205	0.46903 (18)	−0.18417 (13)	0.61103 (12)	0.0423 (3)
H205	0.5461	−0.2582	0.6093	0.051*
C206	0.48144 (14)	−0.08153 (11)	0.65054 (10)	0.0309 (3)
C207	0.12056 (14)	0.14904 (15)	0.61157 (12)	0.0390 (3)
C208	0.61343 (14)	−0.09151 (12)	0.69029 (10)	0.0322 (3)
C209	0.61215 (13)	0.01330 (12)	0.73845 (10)	0.0295 (2)
C210	0.49545 (13)	0.11609 (11)	0.73754 (10)	0.0277 (2)
H210	0.4959	0.1844	0.7697	0.033*
C211	0.73085 (13)	0.00904 (13)	0.79296 (11)	0.0341 (3)
C212	0.79490 (17)	0.11036 (17)	0.91340 (13)	0.0465 (4)
H21A	0.8003	0.2007	0.9067	0.056*
H21B	0.8936	0.0623	0.8857	0.056*
C213	0.74080 (19)	0.04817 (17)	1.03738 (13)	0.0484 (4)
H21C	0.6426	0.0950	1.0643	0.073*
H21D	0.8048	0.0511	1.0846	0.073*
H21E	0.7395	−0.0424	1.0444	0.073*

	U11	U22	U33	U12	U13	U23
F11	0.0417 (4)	0.0334 (4)	0.0518 (5)	−0.0007 (3)	−0.0053 (4)	−0.0137 (4)
F12	0.0366 (4)	0.0627 (6)	0.0764 (7)	0.0050 (4)	−0.0282 (5)	−0.0237 (5)
F13	0.0424 (5)	0.0589 (6)	0.0598 (6)	0.0010 (4)	0.0196 (4)	−0.0110 (5)
F21	0.0428 (5)	0.0386 (4)	0.0502 (5)	−0.0027 (3)	−0.0098 (4)	−0.0021 (4)
F22	0.0385 (5)	0.0789 (7)	0.0411 (5)	0.0022 (4)	0.0011 (4)	−0.0130 (5)
F23	0.0512 (6)	0.0676 (7)	0.0894 (8)	−0.0103 (5)	−0.0422 (6)	−0.0120 (6)
O11	0.0428 (5)	0.0338 (5)	0.0311 (5)	0.0145 (4)	−0.0083 (4)	−0.0078 (4)
O12	0.0306 (5)	0.0467 (6)	0.0462 (6)	0.0050 (4)	0.0015 (4)	−0.0042 (5)
O13	0.0353 (5)	0.0409 (5)	0.0252 (4)	−0.0031 (4)	−0.0036 (3)	−0.0049 (4)
O21	0.0574 (6)	0.0394 (5)	0.0384 (5)	0.0243 (5)	−0.0201 (5)	−0.0154 (4)
O22	0.0336 (5)	0.0522 (6)	0.0669 (8)	0.0066 (5)	−0.0198 (5)	−0.0091 (5)
O23	0.0421 (5)	0.0527 (6)	0.0424 (6)	−0.0029 (4)	−0.0195 (4)	−0.0136 (5)
N1	0.0258 (5)	0.0247 (5)	0.0271 (5)	0.0029 (4)	−0.0081 (4)	−0.0061 (4)
N2	0.0264 (5)	0.0251 (5)	0.0278 (5)	0.0028 (4)	−0.0066 (4)	−0.0078 (4)
C101	0.0260 (5)	0.0251 (5)	0.0254 (5)	−0.0036 (4)	−0.0083 (4)	−0.0082 (4)
C102	0.0270 (5)	0.0310 (6)	0.0305 (6)	−0.0051 (4)	−0.0058 (4)	−0.0101 (5)
C103	0.0346 (6)	0.0402 (7)	0.0286 (6)	−0.0128 (5)	−0.0019 (5)	−0.0094 (5)
C104	0.0448 (7)	0.0322 (6)	0.0274 (6)	−0.0126 (5)	−0.0099 (5)	−0.0020 (5)
C105	0.0381 (6)	0.0250 (5)	0.0299 (6)	−0.0034 (4)	−0.0130 (5)	−0.0055 (4)
C106	0.0283 (5)	0.0241 (5)	0.0243 (5)	−0.0021 (4)	−0.0094 (4)	−0.0076 (4)
C107	0.0269 (6)	0.0407 (7)	0.0392 (7)	−0.0036 (5)	−0.0005 (5)	−0.0118 (6)
C108	0.0285 (5)	0.0263 (5)	0.0258 (5)	0.0023 (4)	−0.0099 (4)	−0.0094 (4)
C109	0.0253 (5)	0.0264 (5)	0.0251 (5)	−0.0016 (4)	−0.0079 (4)	−0.0079 (4)
C110	0.0274 (5)	0.0252 (5)	0.0248 (5)	−0.0017 (4)	−0.0090 (4)	−0.0050 (4)
C111	0.0260 (5)	0.0299 (5)	0.0291 (6)	−0.0049 (4)	−0.0063 (4)	−0.0086 (4)
C112	0.0366 (7)	0.0491 (8)	0.0279 (6)	−0.0163 (6)	−0.0004 (5)	−0.0061 (5)
C113	0.0509 (8)	0.0551 (9)	0.0326 (7)	−0.0138 (7)	−0.0049 (6)	−0.0128 (6)
C201	0.0341 (6)	0.0260 (5)	0.0197 (5)	−0.0044 (4)	−0.0050 (4)	−0.0026 (4)
C202	0.0383 (6)	0.0350 (6)	0.0250 (6)	−0.0102 (5)	−0.0082 (5)	−0.0010 (5)
C203	0.0595 (9)	0.0459 (8)	0.0352 (7)	−0.0221 (7)	−0.0159 (6)	−0.0045 (6)
C204	0.0807 (12)	0.0363 (7)	0.0400 (8)	−0.0201 (7)	−0.0168 (8)	−0.0093 (6)
C205	0.0650 (9)	0.0265 (6)	0.0319 (6)	−0.0031 (6)	−0.0107 (6)	−0.0074 (5)
C206	0.0424 (7)	0.0249 (5)	0.0202 (5)	−0.0009 (5)	−0.0062 (5)	−0.0038 (4)
C207	0.0313 (6)	0.0496 (8)	0.0348 (7)	−0.0095 (6)	−0.0103 (5)	−0.0042 (6)
C208	0.0381 (6)	0.0282 (6)	0.0200 (5)	0.0072 (5)	−0.0064 (4)	−0.0032 (4)
C209	0.0283 (5)	0.0296 (6)	0.0233 (5)	0.0018 (4)	−0.0053 (4)	−0.0029 (4)
C210	0.0279 (5)	0.0269 (5)	0.0247 (5)	−0.0012 (4)	−0.0046 (4)	−0.0057 (4)
C211	0.0295 (6)	0.0372 (6)	0.0282 (6)	−0.0037 (5)	−0.0066 (5)	0.0010 (5)
C212	0.0445 (8)	0.0630 (9)	0.0355 (7)	−0.0223 (7)	−0.0154 (6)	−0.0003 (6)
C213	0.0564 (9)	0.0523 (9)	0.0335 (7)	−0.0136 (7)	−0.0072 (6)	−0.0055 (6)

F11—C107	1.3341 (16)	C108—C109	1.4457 (16)
F12—C107	1.3470 (17)	C109—C110	1.3735 (15)
F13—C107	1.3310 (16)	C109—C111	1.4782 (16)
F21—C207	1.3307 (17)	C110—H110	0.9500
F22—C207	1.3437 (17)	C112—C113	1.498 (2)
F23—C207	1.3285 (16)	C112—H11A	0.9900
O11—C108	1.2351 (14)	C112—H11B	0.9900
O12—C111	1.2029 (15)	C113—H11C	0.9800
O13—C111	1.3464 (15)	C113—H11D	0.9800
O13—C112	1.4529 (15)	C113—H11E	0.9800
O21—C208	1.2370 (15)	C201—C206	1.4027 (16)
O22—C211	1.1994 (16)	C201—C202	1.4141 (17)
O23—C211	1.3495 (18)	C202—C203	1.375 (2)
O23—C212	1.4479 (17)	C202—C207	1.4976 (19)
N1—C110	1.3355 (15)	C203—C204	1.393 (2)
N1—C101	1.3773 (15)	C203—H203	0.9500
N1—H1	0.892 (19)	C204—C205	1.368 (2)
N2—C210	1.3358 (15)	C204—H204	0.9500
N2—C201	1.3763 (15)	C205—C206	1.4017 (18)
N2—H2	0.851 (18)	C205—H205	0.9500
C101—C106	1.4043 (15)	C206—C208	1.4737 (18)
C101—C102	1.4132 (16)	C208—C209	1.4420 (18)
C102—C103	1.3765 (18)	C209—C210	1.3727 (15)
C102—C107	1.4981 (17)	C209—C211	1.4815 (17)
C103—C104	1.3956 (19)	C210—H210	0.9500
C103—H103	0.9500	C212—C213	1.495 (2)
C104—C105	1.3712 (18)	C212—H21A	0.9900
C104—H104	0.9500	C212—H21B	0.9900
C105—C106	1.4044 (16)	C213—H21C	0.9800
C105—H105	0.9500	C213—H21D	0.9800
C106—C108	1.4757 (16)	C213—H21E	0.9800
C111—O13—C112	117.59 (10)	H11C—C113—H11D	109.5
C211—O23—C212	117.55 (12)	C112—C113—H11E	109.5
C110—N1—C101	121.95 (10)	H11C—C113—H11E	109.5
C110—N1—H1	114.9 (12)	H11D—C113—H11E	109.5
C101—N1—H1	123.2 (12)	N2—C201—C206	118.05 (11)
C210—N2—C201	121.93 (10)	N2—C201—C202	122.66 (11)
C210—N2—H2	115.4 (11)	C206—C201—C202	119.28 (11)
C201—N2—H2	122.2 (11)	C203—C202—C201	119.74 (13)
N1—C101—C106	118.41 (10)	C203—C202—C207	119.36 (13)
N1—C101—C102	122.48 (10)	C201—C202—C207	120.90 (11)
C106—C101—C102	119.12 (10)	C202—C203—C204	120.80 (14)
C103—C102—C101	119.82 (11)	C202—C203—H203	119.6
C103—C102—C107	119.71 (11)	C204—C203—H203	119.6
C101—C102—C107	120.46 (11)	C205—C204—C203	120.02 (13)
C102—C103—C104	121.00 (12)	C205—C204—H204	120.0
C102—C103—H103	119.5	C203—C204—H204	120.0
C104—C103—H103	119.5	C204—C205—C206	120.81 (13)
C105—C104—C103	119.78 (11)	C204—C205—H205	119.6
C105—C104—H104	120.1	C206—C205—H205	119.6
C103—C104—H104	120.1	C205—C206—C201	119.33 (13)
C104—C105—C106	120.70 (11)	C205—C206—C208	119.22 (12)
C104—C105—H105	119.7	C201—C206—C208	121.44 (11)
C106—C105—H105	119.7	F23—C207—F21	106.70 (11)
C101—C106—C105	119.58 (11)	F23—C207—F22	106.69 (12)
C101—C106—C108	121.19 (10)	F21—C207—F22	105.13 (12)
C105—C106—C108	119.22 (10)	F23—C207—C202	112.96 (13)
F13—C107—F11	106.66 (11)	F21—C207—C202	113.00 (11)
F13—C107—F12	106.61 (11)	F22—C207—C202	111.81 (11)
F11—C107—F12	105.45 (12)	O21—C208—C209	125.29 (13)
F13—C107—C102	112.78 (12)	O21—C208—C206	119.16 (12)
F11—C107—C102	113.23 (10)	C209—C208—C206	115.54 (10)
F12—C107—C102	111.58 (11)	C210—C209—C208	118.91 (11)
O11—C108—C109	124.72 (11)	C210—C209—C211	119.79 (11)
O11—C108—C106	119.80 (11)	C208—C209—C211	121.25 (11)
C109—C108—C106	115.48 (10)	N2—C210—C209	123.90 (11)
C110—C109—C108	119.21 (10)	N2—C210—H210	118.0
C110—C109—C111	119.66 (10)	C209—C210—H210	118.0
C108—C109—C111	121.13 (10)	O22—C211—O23	123.44 (13)
N1—C110—C109	123.71 (10)	O22—C211—C209	125.73 (13)
N1—C110—H110	118.1	O23—C211—C209	110.82 (10)
C109—C110—H110	118.1	O23—C212—C213	110.57 (12)
O12—C111—O13	122.73 (11)	O23—C212—H21A	109.5
O12—C111—C109	125.78 (11)	C213—C212—H21A	109.5
O13—C111—C109	111.49 (10)	O23—C212—H21B	109.5
O13—C112—C113	110.26 (11)	C213—C212—H21B	109.5
O13—C112—H11A	109.6	H21A—C212—H21B	108.1
C113—C112—H11A	109.6	C212—C213—H21C	109.5
O13—C112—H11B	109.6	C212—C213—H21D	109.5
C113—C112—H11B	109.6	H21C—C213—H21D	109.5
H11A—C112—H11B	108.1	C212—C213—H21E	109.5
C112—C113—H11C	109.5	H21C—C213—H21E	109.5
C112—C113—H11D	109.5	H21D—C213—H21E	109.5
C110—N1—C101—C106	−2.05 (16)	C210—N2—C201—C206	−3.23 (17)
C110—N1—C101—C102	177.88 (10)	C210—N2—C201—C202	175.92 (11)
N1—C101—C102—C103	178.98 (11)	N2—C201—C202—C203	−177.79 (12)
C106—C101—C102—C103	−1.09 (17)	C206—C201—C202—C203	1.35 (18)
N1—C101—C102—C107	−2.20 (17)	N2—C201—C202—C207	1.81 (18)
C106—C101—C102—C107	177.73 (11)	C206—C201—C202—C207	−179.05 (11)
C101—C102—C103—C104	0.15 (18)	C201—C202—C203—C204	−0.8 (2)
C107—C102—C103—C104	−178.67 (12)	C207—C202—C203—C204	179.55 (13)
C102—C103—C104—C105	0.53 (19)	C202—C203—C204—C205	−0.3 (2)
C103—C104—C105—C106	−0.26 (19)	C203—C204—C205—C206	0.9 (2)
N1—C101—C106—C105	−178.71 (10)	C204—C205—C206—C201	−0.4 (2)
C102—C101—C106—C105	1.35 (16)	C204—C205—C206—C208	179.11 (13)
N1—C101—C106—C108	0.99 (16)	N2—C201—C206—C205	178.44 (11)
C102—C101—C106—C108	−178.94 (10)	C202—C201—C206—C205	−0.74 (18)
C104—C105—C106—C101	−0.69 (17)	N2—C201—C206—C208	−1.05 (17)
C104—C105—C106—C108	179.60 (11)	C202—C201—C206—C208	179.77 (11)
C103—C102—C107—F13	−4.70 (18)	C203—C202—C207—F23	−2.68 (18)
C101—C102—C107—F13	176.48 (11)	C201—C202—C207—F23	177.71 (12)
C103—C102—C107—F11	−125.94 (13)	C203—C202—C207—F21	−123.94 (14)
C101—C102—C107—F11	55.24 (16)	C201—C202—C207—F21	56.46 (16)
C103—C102—C107—F12	115.27 (14)	C203—C202—C207—F22	117.68 (14)
C101—C102—C107—F12	−63.55 (15)	C201—C202—C207—F22	−61.92 (16)
C101—C106—C108—O11	−179.90 (11)	C205—C206—C208—O21	3.99 (18)
C105—C106—C108—O11	−0.19 (17)	C201—C206—C208—O21	−176.53 (12)
C101—C106—C108—C109	0.70 (16)	C205—C206—C208—C209	−175.03 (11)
C105—C106—C108—C109	−179.60 (10)	C201—C206—C208—C209	4.46 (17)
O11—C108—C109—C110	179.19 (12)	O21—C208—C209—C210	177.19 (12)
C106—C108—C109—C110	−1.43 (15)	C206—C208—C209—C210	−3.86 (16)
O11—C108—C109—C111	−1.12 (18)	O21—C208—C209—C211	−5.5 (2)
C106—C108—C109—C111	178.25 (10)	C206—C208—C209—C211	173.49 (11)
C101—N1—C110—C109	1.34 (17)	C201—N2—C210—C209	3.95 (18)
C108—C109—C110—N1	0.50 (17)	C208—C209—C210—N2	−0.11 (18)
C111—C109—C110—N1	−179.19 (10)	C211—C209—C210—N2	−177.50 (11)
C112—O13—C111—O12	−3.68 (18)	C212—O23—C211—O22	−7.8 (2)
C112—O13—C111—C109	175.91 (10)	C212—O23—C211—C209	171.24 (11)
C110—C109—C111—O12	−176.54 (12)	C210—C209—C211—O22	−177.47 (13)
C108—C109—C111—O12	3.78 (19)	C208—C209—C211—O22	5.2 (2)
C110—C109—C111—O13	3.89 (15)	C210—C209—C211—O23	3.55 (16)
C108—C109—C111—O13	−175.80 (10)	C208—C209—C211—O23	−173.77 (11)
C111—O13—C112—C113	−90.46 (14)	C211—O23—C212—C213	−91.90 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O21i	0.892 (19)	1.875 (19)	2.6588 (13)	145.5 (16)
N2—H2···O11ii	0.851 (18)	2.011 (17)	2.7178 (13)	139.9 (16)
N2—H2···O12ii	0.851 (18)	2.487 (17)	3.0380 (15)	123.2 (14)
C212—H21B···F22iii	0.99	2.46	3.0909 (18)	121
C204—H204···O13iv	0.95	2.60	3.4691 (18)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O21i	0.892 (19)	1.875 (19)	2.6588 (13)	145.5 (16)
N2—H2⋯O11ii	0.851 (18)	2.011 (17)	2.7178 (13)	139.9 (16)
N2—H2⋯O12ii	0.851 (18)	2.487 (17)	3.0380 (15)	123.2 (14)
C212—H21B⋯F22iii	0.99	2.46	3.0909 (18)	121
C204—H204⋯O13iv	0.95	2.60	3.4691 (18)	153

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