Acta Crystallographica Section E
Acta Crystallographica
Section E CRYSTALLOGRAPHIC COMMUNICATIONS

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5-(2,4-Dichlorobenzamido)-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazole-3-carbonitrile

P. Zhong, X.-H. Zhang, H.-P. Xiao and M.-L. Hu

The title compound, C₁₈H₇Cl₄F₃N₄O, is a tricyclic amide with an overall U shape, each of the three rings being planar. The dihedral angle between the pyrazole and attached benzene ring is 90.1 (1)°. Intermolecular N—H

N hydrogen bonds, with an N(amide)

N(cyano) separation of 3.068 (6) Å, link the molecules.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027054/hg6237sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027054/hg6237Isup2.hkl Contains datablock I

CCDC reference: 287593

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.008 Å
R factor = 0.093
wR factor = 0.244
Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT213_ALERT_2_A Atom F3      has ADP max/min Ratio .............       6.30 prolat

Author Response: see _publ_section_exptl_refinement

PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for         C1

Author Response: see _publ_section_exptl_refinement


Alert level C
PLAT213_ALERT_2_C Atom F1      has ADP max/min Ratio .............       3.80 prolat

Author Response: see _publ_section_exptl_refinement

PLAT213_ALERT_2_C Atom F2      has ADP max/min Ratio .............       3.60 prolat

Author Response: see _publ_section_exptl_refinement

PLAT230_ALERT_2_C Hirshfeld Test Diff for    F2     -   C1      ..       6.37 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14

Author Response: see _publ_section_exptl_refinement

PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16

Author Response: see _publ_section_exptl_refinement

PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.08
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C8     -   C11    ...       1.44 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         41
            N2  -C8  -C11 -N3   -143.00 12.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         42
            C9  -C8  -C11 -N3     33.00 13.00   1.555   1.555   1.555   1.555

   2 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The title compound, (I), is an intermediate for the synthesis of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethyl-thiopyrazole, 5-amino-3-cyano-1-(2,6-dichloro-4- trifluoromethylphenyl)-4-trifluoromethylsulphenylpyrazole and 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4- trifluoromethylsulfonyl pyrazole, which are all good insecticides (Hatton et al., 1993). The structure of (I) is shown in Fig. 1. The molecule contains three planar groups, forming an overall U shape. All bond lengths and angles are in agreement with those observed in similar compounds (Zhang et al., 2005; Zhong et al., 2005) The dihedral angles between the pyrazole and the C2–C7 and C13–C18 benzene rings are 90.1 (1) and 112.8 (1)°, respectively.

Experimental top

Following the method of Hatton et al. (1993), the reaction of 2,6-dichloro-4- trifluoromethylamine with a suspension of nitrosyl sulfuric acid, followed by reaction with a solution of ethyl 2,3-dicyanopropionate in acetic acid, gave 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole, which was then refluxed with 2,4-dichlorobenzoyl chloride and pyridine in chloroform overnight to give the title compound, (I). Please give details of quantities of reagents, reaction conditions etc. Single crystals suitable for X-ray analysis were obtained by slow evaporation of an acetone solution (m.p. 505–506 K). IR (KBr, cm⁻¹): ν 3420, 2252, 1705, 1627,1554, 1380, 1307, 1191, 881; ¹H NMR (CDCl₃, p.p.m.): δ 10.22 (s,1H), 8.10 (s, 2H), 7.55 (d, 2H), 7.50 (d, 1H), 7.40 (s, 1H); ¹³C NMR (CDCl₃, p.p.m.): δ 163.9 (1 C), 140.7 (1 C), 137.5 (1 C), 137.4 (1 C), 136.7 (1 C), 135.3 (1 C), 134.8 (1 C), 134.7 (1 C), 132.7 (1 C), 131.4 (1 C), 130.4 (1 C), 128.4 (1 C), 128.3 (1 C), 127.5 (1 C), 127.4 (2 C), 127.3 (1 C), 125.1 (1 C).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

Figures top

[Figure 1]

Fig. 1. The structure of (I), showing the atom-numbering scheme and with displacement ellipsoids for non-H atoms at the 50% probability level.

5-(2,4-Dichlorobenzamido)-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]- 1H-pyrazole-3-carbonitrile top

Crystal data top

C₁₈H₇Cl₄F₃N₄O	F(000) = 984
M_r = 494.08	D_x = 1.564 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 505 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.7760 (11) Å	Cell parameters from 1812 reflections
b = 16.4530 (16) Å	θ = 2.8–24.3°
c = 16.6220 (16) Å	µ = 0.61 mm⁻¹
β = 99.31 (3)°	T = 298 K
V = 2098.6 (5) Å³	Block, colorless
Z = 4	0.35 × 0.27 × 0.17 mm

Data collection top

Bruker APEX area-detector diffractometer	3779 independent reflections
Radiation source: fine-focus sealed tube	3196 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 25.2°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −9→8
T_min = 0.815, T_max = 0.904	k = −17→19
10608 measured reflections	l = −18→19

Refinement top

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)] = 0.093	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.244	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.1073P)² + 5.2953P] where P = (F_o² + 2F_c²)/3
3779 reflections	(Δ/σ)_max < 0.001
271 parameters	Δρ_max = 1.02 e Å⁻³
0 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

C₁₈H₇Cl₄F₃N₄O	V = 2098.6 (5) Å³
M_r = 494.08	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.7760 (11) Å	µ = 0.61 mm⁻¹
b = 16.4530 (16) Å	T = 298 K
c = 16.6220 (16) Å	0.35 × 0.27 × 0.17 mm
β = 99.31 (3)°

Data collection top

Bruker APEX area-detector diffractometer	3779 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	3196 reflections with I > 2σ(I)
T_min = 0.815, T_max = 0.904	R_int = 0.023
10608 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.093	0 restraints
wR(F²) = 0.244	H-atom parameters constrained
S = 1.07	Δρ_max = 1.02 e Å⁻³
3779 reflections	Δρ_min = −0.69 e Å⁻³
271 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.85543 (18)	0.91195 (11)	0.22140 (10)	0.0767 (5)
Cl2	0.3192 (2)	0.72751 (11)	0.27660 (11)	0.0820 (5)
Cl3	0.9410 (4)	0.73550 (16)	0.05278 (14)	0.1392 (12)
Cl4	0.7241 (3)	0.49917 (13)	−0.15813 (9)	0.0939 (7)
O1	0.9513 (6)	0.5777 (3)	0.2392 (2)	0.0816 (14)
F1	0.0914 (11)	0.9348 (5)	0.0479 (6)	0.237 (5)
F2	0.1704 (16)	1.0236 (5)	0.1032 (6)	0.261 (6)
F3	0.2869 (10)	0.9906 (9)	0.0181 (6)	0.335 (9)
N1	0.6910 (5)	0.7792 (2)	0.3001 (2)	0.0449 (9)
N2	0.7298 (6)	0.8052 (3)	0.3781 (2)	0.0504 (10)
N3	0.9928 (7)	0.7688 (3)	0.5611 (3)	0.0726 (15)
N4	0.7663 (6)	0.6815 (3)	0.2071 (2)	0.0544 (11)
H4	0.6938	0.7041	0.1691	0.065*
C1	0.2354 (10)	0.9653 (5)	0.0729 (5)	0.085 (2)
C2	0.3539 (7)	0.9168 (3)	0.1324 (3)	0.0535 (13)
C3	0.2871 (6)	0.8542 (3)	0.1729 (3)	0.0527 (13)
H3	0.1683	0.8429	0.1631	0.063*
C4	0.3983 (6)	0.8088 (3)	0.2280 (3)	0.0469 (11)
C5	0.5741 (6)	0.8257 (3)	0.2430 (2)	0.0393 (10)
C6	0.6372 (6)	0.8890 (3)	0.2017 (3)	0.0454 (11)
C7	0.5268 (7)	0.9348 (3)	0.1460 (3)	0.0516 (12)
H7	0.5700	0.9772	0.1182	0.062*
C8	0.8497 (6)	0.7522 (3)	0.4112 (3)	0.0454 (11)
C9	0.8913 (7)	0.6949 (3)	0.3565 (3)	0.0517 (12)
H9	0.9725	0.6531	0.3661	0.062*
C10	0.7853 (6)	0.7139 (3)	0.2845 (3)	0.0436 (11)
C11	0.9263 (7)	0.7620 (3)	0.4954 (3)	0.0549 (13)
C12	0.8574 (7)	0.6152 (3)	0.1881 (3)	0.0531 (12)
C13	0.8246 (7)	0.5903 (3)	0.1004 (3)	0.0507 (12)
C14	0.8574 (8)	0.6381 (4)	0.0366 (3)	0.0651 (15)
C15	0.8280 (9)	0.6100 (4)	−0.0433 (3)	0.0728 (17)
H15	0.8531	0.6426	−0.0856	0.087*
C16	0.7623 (7)	0.5346 (4)	−0.0585 (3)	0.0573 (14)
C17	0.7324 (10)	0.4848 (4)	0.0033 (4)	0.0770 (18)
H17	0.6906	0.4323	−0.0076	0.092*
C18	0.7651 (10)	0.5136 (3)	0.0823 (3)	0.0734 (18)
H18	0.7458	0.4794	0.1245	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0423 (7)	0.1033 (13)	0.0825 (11)	−0.0104 (7)	0.0046 (7)	0.0070 (9)
Cl2	0.0810 (11)	0.0840 (11)	0.0812 (11)	−0.0192 (8)	0.0142 (8)	0.0197 (9)
Cl3	0.215 (3)	0.1225 (18)	0.0915 (15)	−0.102 (2)	0.0596 (17)	−0.0308 (13)
Cl4	0.1062 (14)	0.1224 (16)	0.0481 (9)	0.0302 (11)	−0.0022 (8)	−0.0317 (9)
O1	0.110 (3)	0.086 (3)	0.044 (2)	0.052 (3)	−0.003 (2)	0.001 (2)
F1	0.172 (6)	0.208 (8)	0.267 (10)	−0.032 (6)	−0.153 (7)	0.126 (7)
F2	0.332 (12)	0.166 (7)	0.226 (9)	0.162 (8)	−0.128 (9)	−0.013 (7)
F3	0.158 (6)	0.65 (2)	0.216 (8)	0.207 (10)	0.090 (6)	0.340 (13)
N1	0.050 (2)	0.054 (2)	0.0269 (18)	0.0114 (18)	−0.0046 (16)	−0.0026 (16)
N2	0.062 (3)	0.061 (3)	0.0250 (18)	0.007 (2)	−0.0003 (17)	−0.0046 (17)
N3	0.092 (4)	0.086 (4)	0.031 (2)	−0.014 (3)	−0.016 (2)	0.011 (2)
N4	0.066 (3)	0.061 (3)	0.032 (2)	0.023 (2)	−0.0080 (18)	−0.0019 (18)
C1	0.082 (5)	0.091 (5)	0.069 (4)	0.032 (4)	−0.024 (4)	0.020 (4)
C2	0.057 (3)	0.060 (3)	0.040 (3)	0.014 (2)	−0.003 (2)	0.000 (2)
C3	0.036 (2)	0.074 (3)	0.045 (3)	0.005 (2)	−0.004 (2)	−0.004 (2)
C4	0.051 (3)	0.051 (3)	0.038 (2)	0.002 (2)	0.005 (2)	−0.003 (2)
C5	0.043 (2)	0.047 (2)	0.026 (2)	0.008 (2)	−0.0006 (17)	−0.0060 (18)
C6	0.040 (2)	0.056 (3)	0.039 (2)	0.002 (2)	0.0005 (19)	−0.003 (2)
C7	0.058 (3)	0.057 (3)	0.039 (3)	0.004 (2)	0.005 (2)	0.007 (2)
C8	0.054 (3)	0.051 (3)	0.027 (2)	0.000 (2)	−0.0066 (19)	0.0018 (19)
C9	0.057 (3)	0.053 (3)	0.040 (3)	0.013 (2)	−0.008 (2)	0.003 (2)
C10	0.051 (3)	0.048 (3)	0.030 (2)	0.006 (2)	−0.0007 (19)	−0.0022 (19)
C11	0.070 (3)	0.054 (3)	0.037 (3)	−0.007 (3)	−0.002 (2)	0.004 (2)
C12	0.061 (3)	0.058 (3)	0.039 (3)	0.015 (3)	0.002 (2)	−0.003 (2)
C13	0.054 (3)	0.055 (3)	0.042 (3)	0.015 (2)	0.006 (2)	−0.003 (2)
C14	0.072 (4)	0.073 (4)	0.052 (3)	−0.016 (3)	0.018 (3)	−0.008 (3)
C15	0.085 (4)	0.091 (5)	0.046 (3)	−0.011 (4)	0.022 (3)	−0.002 (3)
C16	0.054 (3)	0.074 (4)	0.042 (3)	0.019 (3)	0.003 (2)	−0.016 (3)
C17	0.115 (5)	0.055 (3)	0.059 (4)	0.008 (3)	0.008 (3)	−0.013 (3)
C18	0.124 (6)	0.050 (3)	0.046 (3)	0.011 (3)	0.013 (3)	0.002 (2)

Geometric parameters (Å, º) top

Cl1—C6	1.718 (5)	C3—H3	0.9300
Cl2—C4	1.726 (5)	C4—C5	1.378 (7)
Cl3—C14	1.733 (6)	C5—C6	1.381 (7)
Cl4—C16	1.735 (5)	C6—C7	1.380 (7)
O1—C12	1.197 (6)	C7—H7	0.9300
F1—C1	1.235 (10)	C8—C9	1.385 (7)
F2—C1	1.230 (11)	C8—C11	1.439 (6)
F3—C1	1.132 (9)	C9—C10	1.375 (6)
N1—C10	1.349 (6)	C9—H9	0.9300
N1—N2	1.352 (5)	C12—C13	1.496 (7)
N1—C5	1.425 (5)	C13—C18	1.361 (8)
N2—C8	1.330 (6)	C13—C14	1.377 (8)
N3—C11	1.135 (6)	C14—C15	1.390 (8)
N4—C12	1.366 (6)	C15—C16	1.350 (9)
N4—C10	1.377 (6)	C15—H15	0.9300
N4—H4	0.8600	C16—C17	1.363 (9)
C1—C2	1.473 (7)	C17—C18	1.380 (8)
C2—C7	1.359 (7)	C17—H17	0.9300
C2—C3	1.377 (8)	C18—H18	0.9300
C3—C4	1.375 (7)

C10—N1—N2	113.1 (4)	N2—C8—C9	113.4 (4)
C10—N1—C5	127.4 (4)	N2—C8—C11	118.8 (4)
N2—N1—C5	119.2 (4)	C9—C8—C11	127.8 (5)
C8—N2—N1	102.9 (4)	C10—C9—C8	104.2 (4)
C12—N4—C10	122.9 (4)	C10—C9—H9	127.9
C12—N4—H4	118.5	C8—C9—H9	127.9
C10—N4—H4	118.5	N1—C10—C9	106.4 (4)
F3—C1—F2	105.4 (11)	N1—C10—N4	120.5 (4)
F3—C1—F1	107.4 (9)	C9—C10—N4	133.1 (4)
F2—C1—F1	92.5 (9)	N3—C11—C8	177.3 (7)
F3—C1—C2	118.4 (7)	O1—C12—N4	121.8 (5)
F2—C1—C2	113.7 (7)	O1—C12—C13	122.6 (5)
F1—C1—C2	116.1 (7)	N4—C12—C13	115.5 (4)
C7—C2—C3	121.6 (5)	C18—C13—C14	117.3 (5)
C7—C2—C1	119.2 (6)	C18—C13—C12	117.8 (5)
C3—C2—C1	119.2 (6)	C14—C13—C12	124.8 (5)
C4—C3—C2	119.1 (5)	C13—C14—C15	121.5 (6)
C4—C3—H3	120.5	C13—C14—Cl3	121.4 (4)
C2—C3—H3	120.5	C15—C14—Cl3	117.1 (5)
C3—C4—C5	120.7 (5)	C16—C15—C14	119.0 (6)
C3—C4—Cl2	120.0 (4)	C16—C15—H15	120.5
C5—C4—Cl2	119.3 (4)	C14—C15—H15	120.5
C4—C5—C6	118.9 (4)	C15—C16—C17	121.1 (5)
C4—C5—N1	121.3 (4)	C15—C16—Cl4	119.3 (5)
C6—C5—N1	119.7 (4)	C17—C16—Cl4	119.6 (5)
C7—C6—C5	120.9 (4)	C16—C17—C18	118.9 (6)
C7—C6—Cl1	119.7 (4)	C16—C17—H17	120.6
C5—C6—Cl1	119.4 (3)	C18—C17—H17	120.6
C2—C7—C6	118.9 (5)	C13—C18—C17	122.2 (6)
C2—C7—H7	120.5	C13—C18—H18	118.9
C6—C7—H7	120.5	C17—C18—H18	118.9

C10—N1—N2—C8	−1.4 (5)	C11—C8—C9—C10	−177.8 (5)
C5—N1—N2—C8	−175.3 (4)	N2—N1—C10—C9	0.7 (6)
F3—C1—C2—C7	32.5 (15)	C5—N1—C10—C9	174.0 (5)
F2—C1—C2—C7	−92.0 (11)	N2—N1—C10—N4	−177.7 (4)
F1—C1—C2—C7	162.4 (9)	C5—N1—C10—N4	−4.4 (8)
F3—C1—C2—C3	−147.4 (12)	C8—C9—C10—N1	0.3 (6)
F2—C1—C2—C3	88.2 (11)	C8—C9—C10—N4	178.4 (5)
F1—C1—C2—C3	−17.4 (12)	C12—N4—C10—N1	−179.5 (5)
C7—C2—C3—C4	−0.3 (8)	C12—N4—C10—C9	2.6 (9)
C1—C2—C3—C4	179.6 (6)	N2—C8—C11—N3	−143 (12)
C2—C3—C4—C5	0.4 (7)	C9—C8—C11—N3	33 (13)
C2—C3—C4—Cl2	−177.5 (4)	C10—N4—C12—O1	5.1 (9)
C3—C4—C5—C6	−0.2 (7)	C10—N4—C12—C13	−177.9 (5)
Cl2—C4—C5—C6	177.7 (3)	O1—C12—C13—C18	55.2 (8)
C3—C4—C5—N1	179.9 (4)	N4—C12—C13—C18	−121.8 (6)
Cl2—C4—C5—N1	−2.2 (6)	O1—C12—C13—C14	−121.8 (7)
C10—N1—C5—C4	93.6 (6)	N4—C12—C13—C14	61.2 (7)
N2—N1—C5—C4	−93.5 (5)	C18—C13—C14—C15	1.2 (9)
C10—N1—C5—C6	−86.3 (6)	C12—C13—C14—C15	178.2 (6)
N2—N1—C5—C6	86.6 (5)	C18—C13—C14—Cl3	−177.6 (5)
C4—C5—C6—C7	−0.1 (7)	C12—C13—C14—Cl3	−0.6 (8)
N1—C5—C6—C7	179.8 (4)	C13—C14—C15—C16	1.4 (10)
C4—C5—C6—Cl1	178.7 (4)	Cl3—C14—C15—C16	−179.7 (5)
N1—C5—C6—Cl1	−1.4 (6)	C14—C15—C16—C17	−3.0 (10)
C3—C2—C7—C6	0.0 (8)	C14—C15—C16—Cl4	179.7 (5)
C1—C2—C7—C6	−179.8 (5)	C15—C16—C17—C18	2.0 (10)
C5—C6—C7—C2	0.2 (7)	Cl4—C16—C17—C18	179.3 (5)
Cl1—C6—C7—C2	−178.6 (4)	C14—C13—C18—C17	−2.2 (10)
N1—N2—C8—C9	1.6 (6)	C12—C13—C18—C17	−179.5 (6)
N1—N2—C8—C11	178.5 (4)	C16—C17—C18—C13	0.7 (11)
N2—C8—C9—C10	−1.2 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N3ⁱ	0.86	2.23	3.068 (6)	166

Symmetry code: (i) x−1/2, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₇Cl₄F₃N₄O
M_r	494.08
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.7760 (11), 16.4530 (16), 16.6220 (16)
β (°)	99.31 (3)
V (Å³)	2098.6 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.61
Crystal size (mm)	0.35 × 0.27 × 0.17

Data collection
Diffractometer	Bruker APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.815, 0.904
No. of measured, independent and observed [I > 2σ(I)] reflections	10608, 3779, 3196
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.093, 0.244, 1.07
No. of reflections	3779
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.02, −0.69

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2002), SHELXL97.

Selected geometric parameters (Å, º) top

O1—C12	1.197 (6)	N4—C10	1.377 (6)
F1—C1	1.235 (10)	C1—C2	1.473 (7)
N1—C10	1.349 (6)	C5—C6	1.381 (7)
N1—N2	1.352 (5)	C8—C9	1.385 (7)
N1—C5	1.425 (5)	C13—C18	1.361 (8)
N2—C8	1.330 (6)	C13—C14	1.377 (8)
N4—C12	1.366 (6)

C10—N1—N2	113.1 (4)	N2—C8—C9	113.4 (4)
C10—N1—C5	127.4 (4)	C10—C9—C8	104.2 (4)
N2—N1—C5	119.2 (4)	N1—C10—N4	120.5 (4)
C8—N2—N1	102.9 (4)	C9—C10—N4	133.1 (4)
F3—C1—F2	105.4 (11)	O1—C12—N4	121.8 (5)
C7—C2—C3	121.6 (5)	N4—C12—C13	115.5 (4)
C7—C2—C1	119.2 (6)	C18—C13—C14	117.3 (5)
C3—C4—C5	120.7 (5)	C15—C14—Cl3	117.1 (5)
C6—C5—N1	119.7 (4)	C16—C17—C18	118.9 (6)
C2—C7—C6	118.9 (5)	C13—C18—C17	122.2 (6)

C10—N1—N2—C8	−1.4 (5)	N1—C5—C6—C7	179.8 (4)
C5—N1—N2—C8	−175.3 (4)	C3—C2—C7—C6	0.0 (8)
F1—C1—C2—C7	162.4 (9)	N2—N1—C10—N4	−177.7 (4)
C7—C2—C3—C4	−0.3 (8)	C12—N4—C10—N1	−179.5 (5)
C3—C4—C5—N1	179.9 (4)	N4—C12—C13—C14	61.2 (7)
N2—N1—C5—C4	−93.5 (5)	Cl3—C14—C15—C16	−179.7 (5)
C10—N1—C5—C6	−86.3 (6)	C16—C17—C18—C13	0.7 (11)
N2—N1—C5—C6	86.6 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N3ⁱ	0.86	2.23	3.068 (6)	166

Symmetry code: (i) x−1/2, −y+3/2, z−1/2.

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