4-[3-(Trifluoro­meth­yl)phen­yl]-5,6,7,8-tetra­hydro­cinnolin-3(2H)-one

Wang, X.; Zou, X.-M.; Zhu, Y.-Q.; Hu, X.-H.; Yang, H.-Z.

doi:10.1107/S1600536808000871

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page o464

doi:10.1107/S1600536808000871

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4-[3-(Trifluoromethyl)phenyl]-5,6,7,8-tetrahydrocinnolin-3(2H)-one

Xin Wang,^a Xiao-Mao Zou,^a ^* You-Quan Zhu,^a Xu-Hong Hu ^a and Hua-Zheng Yang ^a ^*

^aState Key Laboratory and Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, People's Republic of China
^*Correspondence e-mail: wanggengmin@tju.edu.cn, nk_yanghz@126.com

(Received 24 December 2007; accepted 10 January 2008; online 18 January 2008)

The title compound, C₁₅H₁₃F₃N₂O, contains one benzene ring, one cyclohexane ring and a pyridazine ring. The dihedral angle formed by the pyridazine ring with the benzene ring is 61.5 (2)°. The crystal structure is stabilized by two intermolecular hydrogen bonds (N—H⋯O and C—H⋯F). The cyclohexane ring adopts a screw-boat conformation. The CF₃ group is disordered over two positions; the site occupancy factors are ca 0.6 and 0.4.

Related literature

For related literature, see: Heinisch & Kopelent (1992 ); Kolar & Tisler (1999 ).

Experimental

Crystal data

C₁₅H₁₃F₃N₂O
M_r = 294.27
Monoclinic, C 2/c
a = 8.929 (3) Å
b = 11.443 (4) Å
c = 27.448 (8) Å
β = 94.232 (6)°
V = 2796.6 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 294 (2) K
0.22 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.975, T_max = 0.982
7053 measured reflections
2485 independent reflections
1098 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.211
S = 1.02
2485 reflections
223 parameters
85 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.91 (4)	1.88 (4)	2.783 (5)	178 (5)
C12—H12⋯F3′ⁱⁱ	0.93	2.51	3.362	152
Symmetry codes: (i) -x+2, -y, -z; (ii) $[{5 \over 2} - x, {1 \over 2} + y, {1 \over 2} - z]$ .

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808000871/at2529sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808000871/at2529Isup2.hkl

checkCIF report

Comment top

Many pyridazine derivatives have been found to exhibit biological activities such as insecticidal, fungicidal, herbicidal, plant-growth regulatory activity, etc. (Heinisch & Kopelent, 1992). For example, pyridate, credazine and maleic hydrazide (Kolar & Tisler, 1999) have been commercialized as herbicides. In order to discover new biologically active pyridazine compounds, the title compound, (I), was synthesized and its structure is reported here.

In the molecule of (I) (Fig. 1), the central pyridazine ring (C1—C8/N1/N2) is approximately coplanar with the cyclohexane ring (C1—C6) [dihedral angle = 4.36 (29)°] and the largest deviation from the mean plane is 0.306 (6) Å for atom C4. The dihedral angle formed by the heterocycle and the benzene ring (C9—C14) is 61.50 (18)°. The molecule is further stabilized by intermolecular N—H···O and C—H···F hydrogen bonds(Table 1). Glide-related molecules are linked via C—H···F hydrogen-bonded chains along the c axis. Part of the chain structure is shown in Fig. 2.

Related literature top

For related literature, see: Heinisch & Kopelent (1992); Kolar & Tisler (1999).

Experimental top

4-(3-(Trifluoromethyl)phenyl)-4,4a,5,6,7,8-hexahydrocinnolin-3(2H)-one (1.5 mmol), and 0.5 g anhydrous copper(II) chloride were mixed in acetonitrile (40 ml), refluxed for 2 h. Water (20 ml) were then added. The organic layer was washed successively with saturated sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfateThe solvent was then evaporated in vacuo. The residue was purified via column chromatography. single crystals of (I) suitable for X-ray analysis were grown from ethyl acetate and petroleum ether at room temperature.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. View of the title compound with 30% probability ellipsoid.
	Fig. 2. Intermolecular hydrogen-bonding interactions (dashed lines) in the structure of (I). H atoms not involved in hydrogen bonding have been omitted.

4-[3-(Trifluoromethyl)phenyl]-5,6,7,8-tetrahydrocinnolin-3(2H)-one top

Crystal data top

C₁₅H₁₃F₃N₂O	F(000) = 1216
M_r = 294.27	D_x = 1.398 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1012 reflections
a = 8.929 (3) Å	θ = 2.9–20.2°
b = 11.443 (4) Å	µ = 0.12 mm⁻¹
c = 27.448 (8) Å	T = 294 K
β = 94.232 (6)°	Prism, colourless
V = 2796.6 (15) Å³	0.22 × 0.20 × 0.16 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	2485 independent reflections
Radiation source: fine-focus sealed tube	1098 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.975, T_max = 0.982	k = −13→8
7053 measured reflections	l = −32→32

Refinement top

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)] = 0.068	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.212	w = 1/[σ²(F_o²) + (0.0738P)² + 4.8514P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
2485 reflections	Δρ_max = 0.32 e Å⁻³
223 parameters	Δρ_min = −0.27 e Å⁻³
85 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0029 (8)

Crystal data top

C₁₅H₁₃F₃N₂O	V = 2796.6 (15) Å³
M_r = 294.27	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 8.929 (3) Å	µ = 0.12 mm⁻¹
b = 11.443 (4) Å	T = 294 K
c = 27.448 (8) Å	0.22 × 0.20 × 0.16 mm
β = 94.232 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2485 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1098 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.982	R_int = 0.061
7053 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	85 restraints
wR(F²) = 0.212	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.32 e Å⁻³
2485 reflections	Δρ_min = −0.27 e Å⁻³
223 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	Occ. (<1)
F1	1.1701 (18)	0.1095 (16)	0.2649 (5)	0.144 (5)	0.429 (9)
F2	1.3627 (15)	0.1988 (12)	0.2422 (6)	0.167 (5)	0.429 (9)
F3	1.274 (2)	0.0347 (12)	0.2066 (5)	0.139 (5)	0.429 (9)
F1'	1.2515 (15)	0.1731 (11)	0.2699 (3)	0.152 (4)	0.571 (9)
F2'	1.3577 (10)	0.0982 (12)	0.2113 (4)	0.130 (4)	0.571 (9)
F3'	1.1498 (13)	0.0330 (10)	0.2327 (5)	0.170 (4)	0.571 (9)
O1	1.0587 (4)	0.0810 (3)	0.05160 (12)	0.0661 (10)
N1	0.6764 (5)	0.0930 (3)	0.00974 (15)	0.0601 (11)
N2	0.8244 (5)	0.0709 (4)	0.01511 (15)	0.0579 (11)
C1	0.6214 (5)	0.1615 (4)	0.04183 (19)	0.0547 (13)
C2	0.4543 (5)	0.1771 (5)	0.0370 (2)	0.0755 (16)
H2A	0.4236	0.1960	0.0033	0.091*
H2B	0.4074	0.1035	0.0446	0.091*
C3	0.3977 (7)	0.2691 (7)	0.0689 (3)	0.120 (3)
H3A	0.4001	0.3431	0.0518	0.144*
H3B	0.2935	0.2522	0.0739	0.144*
C4	0.4780 (7)	0.2826 (7)	0.1160 (3)	0.103 (2)
H4A	0.4599	0.2141	0.1356	0.124*
H4B	0.4373	0.3496	0.1322	0.124*
C5	0.6424 (6)	0.2986 (5)	0.11490 (19)	0.0708 (16)
H5A	0.6891	0.2872	0.1476	0.085*
H5B	0.6622	0.3784	0.1053	0.085*
C6	0.7142 (5)	0.2159 (4)	0.08030 (17)	0.0533 (13)
C7	0.8642 (5)	0.1920 (4)	0.08449 (15)	0.0480 (12)
C8	0.9248 (6)	0.1122 (4)	0.05062 (16)	0.0497 (12)
C9	0.9705 (5)	0.2428 (4)	0.12244 (17)	0.0539 (13)
C10	0.9951 (6)	0.3607 (5)	0.1261 (2)	0.0813 (18)
H10	0.9450	0.4107	0.1036	0.098*
C11	1.0930 (7)	0.4069 (6)	0.1624 (3)	0.111 (3)
H11	1.1075	0.4872	0.1647	0.133*
C12	1.1682 (7)	0.3337 (8)	0.1950 (3)	0.110 (3)
H12	1.2339	0.3643	0.2196	0.133*
C13	1.1474 (6)	0.2162 (7)	0.1915 (2)	0.083 (2)
C14	1.0497 (5)	0.1703 (5)	0.15529 (17)	0.0650 (15)
H14	1.0369	0.0898	0.1530	0.078*
C15	1.2323 (9)	0.1368 (8)	0.2247 (2)	0.114 (3)
H2	0.862 (5)	0.023 (4)	−0.0072 (14)	0.081 (18)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.165 (9)	0.167 (9)	0.102 (7)	0.031 (7)	0.032 (7)	0.026 (7)
F2	0.139 (8)	0.198 (9)	0.157 (8)	0.018 (7)	−0.044 (7)	0.025 (7)
F3	0.150 (9)	0.146 (8)	0.118 (7)	0.075 (7)	−0.004 (7)	0.012 (6)
F1'	0.179 (8)	0.207 (8)	0.064 (4)	−0.003 (7)	−0.021 (5)	0.006 (5)
F2'	0.102 (5)	0.166 (8)	0.123 (6)	0.071 (5)	0.011 (5)	0.020 (6)
F3'	0.158 (7)	0.185 (7)	0.157 (7)	0.032 (6)	−0.052 (6)	0.061 (6)
O1	0.057 (2)	0.068 (2)	0.071 (2)	0.0144 (17)	−0.0021 (17)	−0.0177 (19)
N1	0.059 (3)	0.052 (3)	0.068 (3)	0.002 (2)	−0.004 (2)	−0.001 (2)
N2	0.058 (3)	0.053 (3)	0.061 (3)	0.007 (2)	−0.005 (2)	−0.010 (2)
C1	0.053 (3)	0.045 (3)	0.065 (3)	0.000 (2)	−0.004 (3)	0.004 (3)
C2	0.054 (3)	0.071 (4)	0.099 (4)	0.002 (3)	−0.004 (3)	0.003 (4)
C3	0.059 (4)	0.150 (7)	0.147 (7)	0.020 (4)	−0.005 (4)	−0.044 (6)
C4	0.068 (4)	0.135 (6)	0.109 (5)	0.009 (4)	0.021 (4)	−0.014 (5)
C5	0.065 (3)	0.078 (4)	0.070 (3)	0.018 (3)	0.002 (3)	−0.009 (3)
C6	0.059 (3)	0.046 (3)	0.055 (3)	0.006 (2)	0.004 (2)	0.007 (2)
C7	0.056 (3)	0.041 (3)	0.047 (3)	0.006 (2)	0.001 (2)	0.002 (2)
C8	0.055 (3)	0.042 (3)	0.051 (3)	0.005 (2)	0.000 (3)	−0.002 (2)
C9	0.056 (3)	0.056 (3)	0.049 (3)	0.013 (2)	0.000 (2)	−0.009 (3)
C10	0.076 (4)	0.062 (4)	0.102 (5)	0.008 (3)	−0.020 (3)	−0.019 (3)
C11	0.091 (5)	0.085 (5)	0.152 (7)	0.013 (4)	−0.026 (5)	−0.055 (5)
C12	0.074 (4)	0.150 (7)	0.104 (5)	0.032 (5)	−0.020 (4)	−0.063 (6)
C13	0.064 (4)	0.131 (6)	0.051 (3)	0.039 (4)	−0.009 (3)	−0.017 (4)
C14	0.069 (3)	0.076 (4)	0.049 (3)	0.021 (3)	0.002 (3)	−0.002 (3)
C15	0.102 (6)	0.155 (7)	0.080 (5)	0.016 (5)	−0.025 (4)	−0.003 (5)

Geometric parameters (Å, º) top

F1—C15	1.310 (9)	C4—H4A	0.9700
F2—C15	1.416 (9)	C4—H4B	0.9700
F3—C15	1.333 (9)	C5—C6	1.516 (7)
F1'—C15	1.308 (8)	C5—H5A	0.9700
F2'—C15	1.282 (8)	C5—H5B	0.9700
F3'—C15	1.423 (9)	C6—C7	1.363 (6)
O1—C8	1.246 (5)	C7—C8	1.437 (6)
N1—C1	1.302 (6)	C7—C9	1.476 (6)
N1—N2	1.343 (5)	C9—C10	1.370 (7)
N2—C8	1.360 (6)	C9—C14	1.381 (6)
N2—H2	0.91 (4)	C10—C11	1.382 (8)
C1—C6	1.435 (6)	C10—H10	0.9300
C1—C2	1.499 (6)	C11—C12	1.364 (9)
C2—C3	1.481 (8)	C11—H11	0.9300
C2—H2A	0.9700	C12—C13	1.360 (9)
C2—H2B	0.9700	C12—H12	0.9300
C3—C4	1.441 (8)	C13—C14	1.377 (7)
C3—H3A	0.9700	C13—C15	1.459 (9)
C3—H3B	0.9700	C14—H14	0.9300
C4—C5	1.482 (7)

C1—N1—N2	117.2 (4)	C10—C9—C14	118.2 (5)
N1—N2—C8	127.2 (4)	C10—C9—C7	122.0 (5)
N1—N2—H2	117 (3)	C14—C9—C7	119.7 (5)
C8—N2—H2	116 (3)	C9—C10—C11	121.2 (6)
N1—C1—C6	122.2 (4)	C9—C10—H10	119.4
N1—C1—C2	115.8 (5)	C11—C10—H10	119.4
C6—C1—C2	122.0 (5)	C12—C11—C10	119.5 (7)
C3—C2—C1	114.4 (5)	C12—C11—H11	120.2
C3—C2—H2A	108.7	C10—C11—H11	120.2
C1—C2—H2A	108.7	C13—C12—C11	120.2 (6)
C3—C2—H2B	108.7	C13—C12—H12	119.9
C1—C2—H2B	108.7	C11—C12—H12	119.9
H2A—C2—H2B	107.6	C12—C13—C14	120.2 (6)
C4—C3—C2	115.9 (6)	C12—C13—C15	120.6 (7)
C4—C3—H3A	108.3	C14—C13—C15	119.1 (7)
C2—C3—H3A	108.3	C13—C14—C9	120.6 (6)
C4—C3—H3B	108.3	C13—C14—H14	119.7
C2—C3—H3B	108.3	C9—C14—H14	119.7
H3A—C3—H3B	107.4	F2'—C15—F1'	109.0 (9)
C3—C4—C5	115.0 (6)	F2'—C15—F1	126.4 (9)
C3—C4—H4A	108.5	F1'—C15—F1	46.3 (8)
C5—C4—H4A	108.5	F2'—C15—F3	47.0 (8)
C3—C4—H4B	108.5	F1'—C15—F3	127.7 (10)
C5—C4—H4B	108.5	F1—C15—F3	104.7 (12)
H4A—C4—H4B	107.5	F2'—C15—F2	63.7 (8)
C4—C5—C6	113.7 (5)	F1'—C15—F2	58.2 (8)
C4—C5—H5A	108.8	F1—C15—F2	102.9 (11)
C6—C5—H5A	108.8	F3—C15—F2	108.7 (12)
C4—C5—H5B	108.8	F2'—C15—F3'	103.3 (10)
C6—C5—H5B	108.8	F1'—C15—F3'	98.7 (10)
H5A—C5—H5B	107.7	F1—C15—F3'	54.2 (8)
C7—C6—C1	119.0 (4)	F3—C15—F3'	59.2 (9)
C7—C6—C5	122.0 (4)	F2—C15—F3'	142.0 (8)
C1—C6—C5	118.9 (4)	F2'—C15—C13	117.3 (7)
C6—C7—C8	119.2 (4)	F1'—C15—C13	114.9 (8)
C6—C7—C9	123.9 (4)	F1—C15—C13	116.2 (9)
C8—C7—C9	116.9 (4)	F3—C15—C13	117.3 (8)
O1—C8—N2	119.7 (4)	F2—C15—C13	106.0 (8)
O1—C8—C7	125.1 (4)	F3'—C15—C13	111.4 (7)
N2—C8—C7	115.2 (4)

C1—N1—N2—C8	0.0 (7)	C8—C7—C9—C10	119.0 (5)
N2—N1—C1—C6	2.7 (6)	C6—C7—C9—C14	119.2 (5)
N2—N1—C1—C2	−175.5 (4)	C8—C7—C9—C14	−60.3 (6)
N1—C1—C2—C3	−170.9 (5)	C14—C9—C10—C11	−1.9 (9)
C6—C1—C2—C3	10.9 (8)	C7—C9—C10—C11	178.7 (5)
C1—C2—C3—C4	−34.6 (9)	C9—C10—C11—C12	0.9 (10)
C2—C3—C4—C5	52.9 (10)	C10—C11—C12—C13	0.3 (11)
C3—C4—C5—C6	−44.3 (8)	C11—C12—C13—C14	−0.4 (10)
N1—C1—C6—C7	−2.3 (7)	C11—C12—C13—C15	177.2 (7)
C2—C1—C6—C7	175.7 (4)	C12—C13—C14—C9	−0.6 (8)
N1—C1—C6—C5	177.4 (4)	C15—C13—C14—C9	−178.3 (5)
C2—C1—C6—C5	−4.5 (7)	C10—C9—C14—C13	1.8 (8)
C4—C5—C6—C7	−159.9 (5)	C7—C9—C14—C13	−178.9 (5)
C4—C5—C6—C1	20.4 (7)	C12—C13—C15—F2'	−90.7 (11)
C1—C6—C7—C8	−0.6 (6)	C14—C13—C15—F2'	86.9 (12)
C5—C6—C7—C8	179.6 (4)	C12—C13—C15—F1'	39.4 (13)
C1—C6—C7—C9	179.9 (4)	C14—C13—C15—F1'	−142.9 (10)
C5—C6—C7—C9	0.2 (7)	C12—C13—C15—F1	91.1 (14)
N1—N2—C8—O1	177.9 (4)	C14—C13—C15—F1	−91.3 (14)
N1—N2—C8—C7	−2.7 (7)	C12—C13—C15—F3	−144.0 (13)
C6—C7—C8—O1	−177.8 (4)	C14—C13—C15—F3	33.7 (15)
C9—C7—C8—O1	1.7 (7)	C12—C13—C15—F2	−22.5 (12)
C6—C7—C8—N2	2.9 (6)	C14—C13—C15—F2	155.2 (10)
C9—C7—C8—N2	−177.6 (4)	C12—C13—C15—F3'	150.6 (10)
C6—C7—C9—C10	−61.5 (7)	C14—C13—C15—F3'	−31.8 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.91 (4)	1.88 (4)	2.783 (5)	178 (5)
C12—H12···F3′ⁱⁱ	0.93	2.51	3.362	152

Symmetry codes: (i) −x+2, −y, −z; (ii) −x+5/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃F₃N₂O
M_r	294.27
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	294
a, b, c (Å)	8.929 (3), 11.443 (4), 27.448 (8)
β (°)	94.232 (6)
V (Å³)	2796.6 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.22 × 0.20 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.975, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	7053, 2485, 1098
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.212, 1.02
No. of reflections	2485
No. of parameters	223
No. of restraints	85
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.27

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.91 (4)	1.88 (4)	2.783 (5)	178 (5)
C12—H12···F3'ⁱⁱ	0.93	2.51	3.362	152

Symmetry codes: (i) −x+2, −y, −z; (ii) −x+5/2, y+1/2, −z+1/2.

Acknowledgements

This work was supported by the National Key Project for Basic Research (grant No. 20772067).

References

Bruker (1999). SMART (Version 5.618) and SAINT (Version 6.45). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Kolar, P. & Tisler, M. (1999). Adv. Heterocycl. Chem. 75, 167–241. CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar