3-(2-Amino­eth­yl)-2-[4-(trifluoro­meth­oxy)anilino]quinazolin-4(3H)-one

Cai, Z.-H.; Chen, X.-B.; Yang, X.-H.; Wang, X.

doi:10.1107/S1600536810024645

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Pages o1854-o1855

doi:10.1107/S1600536810024645

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3-(2-Aminoethyl)-2-[4-(trifluoromethoxy)anilino]quinazolin-4(3H)-one

Zhao-Hui Cai,^a Xiao-Bao Chen,^b Xu-Hong Yang ^a ^* and Xiang Wang ^c

^aDepartment of Chemistry and Life Science, Xianning College, Xianning 4371000, Hubei, People's Republic of China, ^bDepartment of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000, Hubei, People's Republic of China, and ^cCollege of Life and Environmental Science, Kaili University, Kaili 556000, Guizhou, People's Republic of China
^*Correspondence e-mail: chenxiaobao@yahoo.com.cn

(Received 18 June 2010; accepted 23 June 2010; online 30 June 2010)

In the title compound, C₁₇H₁₅F₃N₄O₂, the dihedral angle between the trifluoromethoxy-substituted benzene ring and the pyrimidinone ring is 45.1 (5)°, while that between the fused benzene ring and the pyrimidinone ring is 0.67 (1)°. Part of one of the benzene rings and its trifluoromethoxy substituent are disordered over two positions of approximately equal occupancy (0.51:0.49). Intermolecular N—H⋯O and N—H⋯N hydrogen bonds contribute to the stability of the crystal structure. A weak intramolecular C—H⋯F contact is also found. In addition, π–π stacking interactions, with centroid–centroid distances in the range 3.673 (6)–3.780 (8) Å, and weak C—H⋯π interactions are also observed.

Related literature

For the biological activity of quinazoline-4(3H)-one derivatives, see: Pandeya et al.(1999 ); Shiba et al. (1997 ), Malamas & Millen (1991 ); Mannschreck et al. (1984 ); Kung et al. (1999 ); Bartroli et al. (1998 ); Palmer et al. (1997 ); Tsou et al. (2001 ); Matsuno et al. (2002 ). For the synthesis of the title compound, see: Yang et al. (2008 ).

Experimental

Crystal data

C₁₇H₁₅F₃N₄O₂
M_r = 364.33
Orthorhombic, P b c n
a = 11.9675 (13) Å
b = 12.9579 (13) Å
c = 21.280 (2) Å
V = 3300.0 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 298 K
0.23 × 0.15 × 0.11 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.973, T_max = 0.987
15599 measured reflections
3076 independent reflections
2573 reflections with I > 2σ(I)
R_int = 0.083

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.164
S = 1.12
3076 reflections
311 parameters
19 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C7/C1/C2/N2/C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯N2ⁱ	0.86 (1)	2.40 (2)	3.150 (3)	145 (3)
N3—H3A⋯O1ⁱⁱ	0.86 (1)	2.46 (2)	3.147 (3)	137 (3)
C15—H15⋯F2	0.93	2.40	2.93 (3)	116
C12—H12⋯Cg1ⁱ	0.93	2.88	3.560 (3)	131
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); 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/S1600536810024645/sj5026sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810024645/sj5026Isup2.hkl

checkCIF report

Comment top

Quinazoline-4(3H)-one derivatives have numerous biological properties. Some of these activities include antimicrobial (Pandeya et al., 1999 and Shiba et al., 1997), antidiabetic (Malamas & Millen, 1991), anticonvulsant (Mannschreck et al., 1984), antibacterial (Kung et al., 1999), antifungal (Bartroli et al., 1998), protein tyrosine kinase inhibitors (Palmer et al., 1997), EGFR inhibitors (Tsou et al.,2001) and PDGFR phosphorylation inhibitors (Matsuno et al., 2002). We have recently focused on the synthesis of heterocyclic compounds using an aza-Wittig reaction. We have reported the synthesis of the title compound (Yang et al., 2008). We present here the crystal structure of the title compound, (I) (Fig. 1), which can be used as a precursor for obtaining bioactive molecules.

In the crystal structure, the fused benzene ring and the pyrimidinone ring are not completely co-planar, but are inclined at 0.67 (1) °. Significant and intermolecular N—H···O and N—H···N hydrogen bonds contribute strongly to the stability of the structure (Fig. 2). An intramolecular C—H···F hydrogen bond is also found. (Table 1). The crystal structure (Fig. 2) is also stabilized by weak intermolecular C—H···π hydrogen bonds (Table 1) and π— π stacking interactions with centroid-centroid separations of 3.673 (6), 3.779 (8), 3.674 (6) and 3.780 (8) Å for Cg1···Cg3ⁱ, Cg1···Cg4ⁱ, Cg3···Cg1ⁱⁱ and Cg4···Cg1ⁱⁱ, respectively, where Cg1, Cg3 and Cg4 are the centroids of the N1/C7/C1—C2/N2/C8, C11—C16 and C11—C13/C14'-C16' rings, respectively [symmetry code: (i) 3/2-X, 1/2+Y, Z, (ii) 3/2-X, -1/2+Y, Z,].

Related literature top

For the biological activity of quinazoline-4(3H)-one derivatives, see: Pandeya et al.(1999); Shiba et al. (1997), Malamas & Millen (1991); Mannschreck et al. (1984); Kung et al. (1999); Bartroli et al. (1998); Palmer et al. (1997); Tsou et al. (2001); Matsuno et al. (2002). For the synthesis of the title compound, see: Yang et al. (2008).

Experimental top

The title compound was prepared by a literature method (Yang et al., 2008). Single crystals suitable for X-ray diffraction were obtained from a methanol-dichloromethane (1:1 v/v) solution at room temperature.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 molecular structure of (I), showing the atom labelling schemeand with displacement ellipsoids drawn at the 50% probability level. Both disorder components are shown with bonds involving the minor disorder component drawn as dashed lines.
	Fig. 2. A partial view of the crystal packing of (I), showing the formation of N—H···N and N—H···O hydrogen-bonds as dashed lines.

3-(2-Aminoethyl)-2-[4-(trifluoromethoxy)anilino]quinazolin-4(3H)-one top

Crystal data top

C₁₇H₁₅F₃N₄O₂	F(000) = 1504
M_r = 364.33	D_x = 1.467 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 4600 reflections
a = 11.9675 (13) Å	θ = 2.5–23.5°
b = 12.9579 (13) Å	µ = 0.12 mm⁻¹
c = 21.280 (2) Å	T = 298 K
V = 3300.0 (6) Å³	Block, colorless
Z = 8	0.23 × 0.15 × 0.11 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3076 independent reflections
Radiation source: fine-focus sealed tube	2573 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.083
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −10→14
T_min = 0.973, T_max = 0.987	k = −15→14
15599 measured reflections	l = −25→25

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ²(F_o²) + (0.0809P)² + 0.8235P] where P = (F_o² + 2F_c²)/3
3076 reflections	(Δ/σ)_max < 0.001
311 parameters	Δρ_max = 0.39 e Å⁻³
19 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₇H₁₅F₃N₄O₂	V = 3300.0 (6) Å³
M_r = 364.33	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 11.9675 (13) Å	µ = 0.12 mm⁻¹
b = 12.9579 (13) Å	T = 298 K
c = 21.280 (2) Å	0.23 × 0.15 × 0.11 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3076 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	2573 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.987	R_int = 0.083
15599 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	19 restraints
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	Δρ_max = 0.39 e Å⁻³
3076 reflections	Δρ_min = −0.29 e Å⁻³
311 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)
C1	0.9187 (2)	1.31297 (18)	0.55231 (11)	0.0445 (6)
C2	0.9408 (2)	1.24194 (18)	0.60015 (11)	0.0443 (6)
C3	0.9930 (2)	1.2767 (2)	0.65508 (12)	0.0556 (7)
H3	1.0093	1.2304	0.6871	0.067*
C4	1.0200 (2)	1.3792 (2)	0.66172 (14)	0.0623 (7)
H4	1.0546	1.4014	0.6984	0.075*
C5	0.9967 (2)	1.4498 (2)	0.61481 (14)	0.0631 (8)
H5	1.0156	1.5189	0.6199	0.076*
C6	0.9457 (2)	1.41721 (19)	0.56101 (14)	0.0549 (7)
H6	0.9286	1.4648	0.5297	0.066*
C7	0.8649 (2)	1.27789 (18)	0.49482 (11)	0.0453 (6)
C8	0.8673 (2)	1.10775 (18)	0.54329 (10)	0.0425 (6)
C9	0.7649 (2)	1.1385 (2)	0.44173 (12)	0.0522 (6)
H9A	0.7257	1.1979	0.4249	0.063*
H9B	0.7092	1.0915	0.4585	0.063*
C10	0.8258 (2)	1.0850 (2)	0.38838 (11)	0.0555 (7)
H10A	0.7795	1.0861	0.3510	0.067*
H10B	0.8943	1.1220	0.3791	0.067*
C11	0.8519 (2)	0.92710 (18)	0.57795 (12)	0.0463 (6)
C12	0.8785 (2)	0.82950 (18)	0.55666 (12)	0.0463 (6)
H12	0.8970	0.8200	0.5146	0.056*
C13	0.8781 (2)	0.74562 (19)	0.59680 (13)	0.0523 (7)
H13	0.8987	0.6808	0.5821	0.063*
C14	0.8473 (13)	0.7581 (8)	0.6583 (5)	0.065 (5)	0.51
C15	0.812 (2)	0.855 (2)	0.6764 (13)	0.071 (6)	0.51
H15	0.7805	0.8616	0.7161	0.085*	0.51
C16	0.8208 (17)	0.9417 (9)	0.6397 (8)	0.050 (3)	0.51
H16	0.8065	1.0072	0.6558	0.060*	0.51
C17	0.8238 (9)	0.6670 (8)	0.7538 (5)	0.0637 (12)	0.51
O2	0.8387 (12)	0.6644 (9)	0.6922 (5)	0.089 (4)	0.51
F1	0.8935 (8)	0.7216 (9)	0.7869 (6)	0.119 (4)	0.51
F2	0.7234 (6)	0.7043 (7)	0.7658 (5)	0.122 (4)	0.51
F3	0.8159 (10)	0.5681 (5)	0.7691 (4)	0.082 (2)	0.51
C14'	0.8582 (12)	0.7631 (9)	0.6591 (6)	0.063 (5)	0.49
C15'	0.842 (3)	0.8590 (19)	0.6855 (14)	0.071 (6)	0.49
H15'	0.8374	0.8700	0.7286	0.085*	0.49
C16'	0.834 (3)	0.9368 (16)	0.6418 (13)	0.101 (8)	0.49
H16'	0.8148	1.0020	0.6566	0.121*	0.49
C17'	0.8114 (10)	0.6564 (9)	0.7475 (6)	0.0637 (12)	0.49
O2'	0.8747 (11)	0.6749 (8)	0.6976 (5)	0.070 (3)	0.49
F1'	0.8435 (10)	0.7198 (6)	0.7928 (4)	0.105 (4)	0.49
F2'	0.7057 (9)	0.6717 (8)	0.7373 (5)	0.122 (4)	0.49
F3'	0.8383 (15)	0.5654 (9)	0.7708 (7)	0.145 (6)	0.49
N1	0.83729 (16)	1.17338 (14)	0.49385 (9)	0.0428 (5)
N2	0.91631 (18)	1.13823 (14)	0.59417 (9)	0.0469 (5)
N3	0.8525 (2)	0.97796 (19)	0.40455 (11)	0.0605 (6)
H3A	0.7992 (19)	0.936 (2)	0.3949 (14)	0.073*
H3B	0.9115 (17)	0.952 (2)	0.3871 (14)	0.073*
N4	0.8435 (2)	1.00667 (16)	0.53333 (9)	0.0510 (6)
H4A	0.843 (2)	0.988 (2)	0.4945 (6)	0.061*
O1	0.84285 (17)	1.33377 (14)	0.45034 (9)	0.0620 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0419 (13)	0.0403 (12)	0.0513 (13)	0.0033 (10)	0.0089 (11)	0.0027 (10)
C2	0.0470 (13)	0.0410 (13)	0.0449 (13)	−0.0008 (10)	0.0068 (10)	0.0003 (10)
C3	0.0640 (17)	0.0577 (16)	0.0452 (13)	−0.0084 (13)	0.0010 (12)	−0.0015 (11)
C4	0.0643 (18)	0.0622 (18)	0.0604 (16)	−0.0108 (14)	0.0069 (14)	−0.0154 (14)
C5	0.0644 (18)	0.0428 (14)	0.082 (2)	−0.0098 (12)	0.0113 (16)	−0.0141 (13)
C6	0.0550 (15)	0.0397 (13)	0.0702 (17)	0.0013 (11)	0.0113 (13)	0.0066 (12)
C7	0.0455 (13)	0.0415 (13)	0.0490 (13)	0.0078 (10)	0.0076 (11)	0.0077 (10)
C8	0.0465 (13)	0.0402 (12)	0.0410 (12)	0.0001 (10)	0.0031 (10)	0.0038 (10)
C9	0.0521 (15)	0.0527 (15)	0.0519 (13)	0.0026 (11)	−0.0113 (12)	0.0054 (11)
C10	0.0634 (16)	0.0601 (16)	0.0431 (13)	−0.0049 (13)	−0.0077 (12)	0.0038 (12)
C11	0.0535 (14)	0.0399 (13)	0.0455 (13)	−0.0049 (10)	−0.0006 (11)	0.0033 (10)
C12	0.0491 (14)	0.0431 (13)	0.0466 (13)	−0.0014 (10)	−0.0007 (11)	−0.0015 (10)
C13	0.0601 (16)	0.0386 (13)	0.0583 (16)	0.0076 (11)	−0.0039 (13)	−0.0029 (11)
C14	0.121 (10)	0.032 (7)	0.043 (7)	−0.017 (6)	−0.026 (6)	−0.002 (4)
C15	0.118 (13)	0.063 (7)	0.033 (7)	−0.014 (7)	0.003 (6)	−0.004 (4)
C16	0.097 (7)	0.014 (4)	0.040 (6)	−0.001 (4)	0.011 (5)	0.001 (4)
C17	0.084 (3)	0.054 (2)	0.053 (2)	0.002 (2)	−0.004 (2)	0.0146 (19)
O2	0.167 (12)	0.046 (3)	0.055 (3)	−0.033 (5)	−0.014 (5)	0.013 (2)
F1	0.111 (6)	0.144 (6)	0.101 (6)	0.025 (4)	−0.036 (4)	−0.008 (4)
F2	0.084 (5)	0.107 (6)	0.177 (9)	0.021 (4)	0.060 (6)	0.059 (6)
F3	0.132 (5)	0.045 (3)	0.070 (4)	0.001 (3)	0.018 (3)	0.038 (3)
C14'	0.071 (6)	0.050 (9)	0.069 (9)	0.024 (5)	0.032 (6)	0.027 (6)
C15'	0.139 (17)	0.036 (6)	0.037 (8)	0.003 (8)	0.006 (9)	0.006 (5)
C16'	0.164 (19)	0.075 (11)	0.064 (12)	0.026 (9)	0.035 (11)	0.001 (8)
C17'	0.084 (3)	0.054 (2)	0.053 (2)	0.002 (2)	−0.004 (2)	0.0146 (19)
O2'	0.098 (6)	0.038 (4)	0.076 (5)	0.016 (4)	0.022 (5)	0.011 (3)
F1'	0.197 (12)	0.074 (4)	0.045 (3)	0.000 (5)	−0.031 (5)	−0.014 (2)
F2'	0.107 (5)	0.116 (7)	0.144 (7)	−0.005 (4)	−0.023 (5)	0.038 (5)
F3'	0.186 (11)	0.112 (8)	0.137 (9)	0.059 (6)	−0.005 (7)	0.054 (6)
N1	0.0465 (11)	0.0404 (11)	0.0416 (10)	0.0029 (8)	−0.0018 (8)	0.0038 (8)
N2	0.0591 (13)	0.0395 (11)	0.0421 (11)	−0.0024 (9)	−0.0030 (9)	0.0057 (8)
N3	0.0730 (17)	0.0565 (15)	0.0518 (13)	0.0004 (12)	−0.0036 (12)	−0.0049 (11)
N4	0.0754 (15)	0.0385 (11)	0.0389 (11)	−0.0060 (10)	−0.0015 (10)	0.0022 (9)
O1	0.0760 (13)	0.0527 (11)	0.0573 (11)	0.0087 (9)	−0.0023 (9)	0.0205 (9)

Geometric parameters (Å, º) top

C1—C2	1.398 (3)	C11—N4	1.405 (3)
C1—C6	1.401 (3)	C12—C13	1.382 (3)
C1—C7	1.455 (4)	C12—H12	0.9300
C2—N2	1.381 (3)	C13—C14'	1.366 (14)
C2—C3	1.399 (3)	C13—C14	1.369 (13)
C3—C4	1.374 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.38 (3)
C4—C5	1.382 (4)	C14—O2	1.416 (9)
C4—H4	0.9300	C15—C16	1.38 (4)
C5—C6	1.364 (4)	C15—H15	0.9300
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300	C17—F1	1.302 (9)
C7—O1	1.221 (3)	C17—F2	1.321 (9)
C7—N1	1.394 (3)	C17—O2	1.324 (9)
C8—N2	1.293 (3)	C17—F3	1.326 (8)
C8—N4	1.357 (3)	C14'—C15'	1.38 (3)
C8—N1	1.400 (3)	C14'—O2'	1.421 (8)
C9—N1	1.478 (3)	C15'—C16'	1.37 (4)
C9—C10	1.517 (4)	C15'—H15'	0.9300
C9—H9A	0.9700	C16'—H16'	0.9300
C9—H9B	0.9700	C17'—F2'	1.299 (9)
C10—N3	1.464 (4)	C17'—F3'	1.320 (9)
C10—H10A	0.9700	C17'—F1'	1.325 (9)
C10—H10B	0.9700	C17'—O2'	1.325 (9)
C11—C16	1.379 (18)	N3—H3A	0.862 (11)
C11—C12	1.381 (3)	N3—H3B	0.864 (11)
C11—C16'	1.38 (3)	N4—H4A	0.863 (11)

C2—C1—C6	119.7 (2)	C14—C13—C12	119.9 (5)
C2—C1—C7	119.4 (2)	C14'—C13—H13	121.6
C6—C1—C7	120.9 (2)	C14—C13—H13	120.1
N2—C2—C1	122.2 (2)	C12—C13—H13	120.1
N2—C2—C3	119.0 (2)	C13—C14—C15	117.3 (15)
C1—C2—C3	118.7 (2)	C13—C14—O2	113.9 (9)
C4—C3—C2	120.1 (3)	C15—C14—O2	127.9 (17)
C4—C3—H3	119.9	C14—C15—C16	124 (2)
C2—C3—H3	119.9	C14—C15—H15	117.9
C3—C4—C5	121.2 (3)	C16—C15—H15	117.9
C3—C4—H4	119.4	C15—C16—C11	116.7 (16)
C5—C4—H4	119.4	C15—C16—H16	121.7
C6—C5—C4	119.4 (2)	C11—C16—H16	121.7
C6—C5—H5	120.3	F1—C17—F2	106.2 (9)
C4—C5—H5	120.3	F1—C17—O2	117.7 (11)
C5—C6—C1	120.8 (3)	F2—C17—O2	108.9 (11)
C5—C6—H6	119.6	F1—C17—F3	116.0 (10)
C1—C6—H6	119.6	F2—C17—F3	104.0 (9)
O1—C7—N1	120.9 (2)	O2—C17—F3	103.2 (9)
O1—C7—C1	124.2 (2)	C17—O2—C14	119.5 (11)
N1—C7—C1	114.88 (19)	C13—C14'—C15'	124.8 (15)
N2—C8—N4	121.4 (2)	C13—C14'—O2'	113.7 (10)
N2—C8—N1	124.1 (2)	C15'—C14'—O2'	120.6 (16)
N4—C8—N1	114.5 (2)	C16'—C15'—C14'	113 (2)
N1—C9—C10	114.8 (2)	C16'—C15'—H15'	123.3
N1—C9—H9A	108.6	C14'—C15'—H15'	123.3
C10—C9—H9A	108.6	C15'—C16'—C11	126 (2)
N1—C9—H9B	108.6	C15'—C16'—H16'	117.0
C10—C9—H9B	108.6	C11—C16'—H16'	117.0
H9A—C9—H9B	107.5	F2'—C17'—F3'	115.9 (11)
N3—C10—C9	111.2 (2)	F2'—C17'—F1'	108.1 (9)
N3—C10—H10A	109.4	F3'—C17'—F1'	102.1 (10)
C9—C10—H10A	109.4	F2'—C17'—O2'	113.3 (11)
N3—C10—H10B	109.4	F3'—C17'—O2'	108.8 (11)
C9—C10—H10B	109.4	F1'—C17'—O2'	107.8 (10)
H10A—C10—H10B	108.0	C17'—O2'—C14'	121.8 (11)
C16—C11—C12	120.0 (6)	C7—N1—C8	121.2 (2)
C16—C11—C16'	7 (2)	C7—N1—C9	116.56 (19)
C12—C11—C16'	116.2 (10)	C8—N1—C9	121.9 (2)
C16—C11—N4	121.6 (6)	C8—N2—C2	118.07 (19)
C12—C11—N4	117.8 (2)	C10—N3—H3A	112 (2)
C16'—C11—N4	125.9 (10)	C10—N3—H3B	116 (2)
C11—C12—C13	121.1 (2)	H3A—N3—H3B	105 (3)
C11—C12—H12	119.4	C8—N4—C11	126.0 (2)
C13—C12—H12	119.4	C8—N4—H4A	115.3 (19)
C14'—C13—C14	6.1 (12)	C11—N4—H4A	115.9 (19)
C14'—C13—C12	118.0 (5)

C6—C1—C2—N2	−179.8 (2)	C15—C14—O2—C17	−20 (2)
C7—C1—C2—N2	1.9 (3)	C14—C13—C14'—C15'	−112 (10)
C6—C1—C2—C3	−2.0 (3)	C12—C13—C14'—C15'	−2 (2)
C7—C1—C2—C3	179.8 (2)	C14—C13—C14'—O2'	79 (9)
N2—C2—C3—C4	178.9 (2)	C12—C13—C14'—O2'	−171.7 (9)
C1—C2—C3—C4	1.0 (4)	C13—C14'—C15'—C16'	8 (3)
C2—C3—C4—C5	0.0 (4)	O2'—C14'—C15'—C16'	176 (2)
C3—C4—C5—C6	0.2 (4)	C14'—C15'—C16'—C11	−7 (4)
C4—C5—C6—C1	−1.2 (4)	C16—C11—C16'—C15'	124 (12)
C2—C1—C6—C5	2.2 (4)	C12—C11—C16'—C15'	1 (3)
C7—C1—C6—C5	−179.6 (2)	N4—C11—C16'—C15'	180 (2)
C2—C1—C7—O1	−179.5 (2)	F2'—C17'—O2'—C14'	43.8 (16)
C6—C1—C7—O1	2.3 (4)	F3'—C17'—O2'—C14'	174.2 (14)
C2—C1—C7—N1	1.6 (3)	F1'—C17'—O2'—C14'	−75.8 (15)
C6—C1—C7—N1	−176.6 (2)	C13—C14'—O2'—C17'	−144.6 (11)
N1—C9—C10—N3	78.7 (3)	C15'—C14'—O2'—C17'	45 (2)
C16—C11—C12—C13	−2.0 (10)	O1—C7—N1—C8	176.8 (2)
C16'—C11—C12—C13	5.1 (15)	C1—C7—N1—C8	−4.3 (3)
N4—C11—C12—C13	−173.9 (2)	O1—C7—N1—C9	−9.6 (3)
C11—C12—C13—C14'	−4.5 (8)	C1—C7—N1—C9	169.3 (2)
C11—C12—C13—C14	2.2 (8)	N2—C8—N1—C7	3.8 (4)
C14'—C13—C14—C15	77 (9)	N4—C8—N1—C7	−174.5 (2)
C12—C13—C14—C15	3.3 (19)	N2—C8—N1—C9	−169.5 (2)
C14'—C13—C14—O2	−113 (9)	N4—C8—N1—C9	12.2 (3)
C12—C13—C14—O2	173.4 (8)	C10—C9—N1—C7	100.9 (3)
C13—C14—C15—C16	−10 (3)	C10—C9—N1—C8	−85.5 (3)
O2—C14—C15—C16	−178.0 (19)	N4—C8—N2—C2	178.1 (2)
C14—C15—C16—C11	10 (3)	N1—C8—N2—C2	−0.1 (4)
C12—C11—C16—C15	−4 (2)	C1—C2—N2—C8	−2.7 (3)
C16'—C11—C16—C15	−64 (10)	C3—C2—N2—C8	179.4 (2)
N4—C11—C16—C15	168.0 (16)	N2—C8—N4—C11	10.1 (4)
F1—C17—O2—C14	−52.8 (17)	N1—C8—N4—C11	−171.5 (2)
F2—C17—O2—C14	68.0 (15)	C16—C11—N4—C8	39.3 (10)
F3—C17—O2—C14	178.0 (13)	C12—C11—N4—C8	−148.9 (2)
C13—C14—O2—C17	171.3 (11)	C16'—C11—N4—C8	32.2 (16)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/C7/C1/C2/N2/C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···N2ⁱ	0.86 (1)	2.40 (2)	3.150 (3)	145 (3)
N3—H3A···O1ⁱⁱ	0.86 (1)	2.46 (2)	3.147 (3)	137 (3)
C15—H15···F2	0.93	2.40	2.93 (3)	116
C12—H12···Cg1ⁱ	0.93	2.88	3.560 (3)	131

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅F₃N₄O₂
M_r	364.33
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	298
a, b, c (Å)	11.9675 (13), 12.9579 (13), 21.280 (2)
V (Å³)	3300.0 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.23 × 0.15 × 0.11

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.973, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	15599, 3076, 2573
R_int	0.083
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.164, 1.12
No. of reflections	3076
No. of parameters	311
No. of restraints	19
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.29

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/C7/C1/C2/N2/C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···N2ⁱ	0.864 (11)	2.40 (2)	3.150 (3)	145 (3)
N3—H3A···O1ⁱⁱ	0.862 (11)	2.46 (2)	3.147 (3)	137 (3)
C15—H15···F2	0.93	2.40	2.93 (3)	116
C12—H12···Cg1ⁱ	0.93	2.88	3.560 (3)	131

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

Acknowledgements

The authors are grateful to the Natural Science Foundation of Guizhou Educational Committee (grant No.20090079) for financial support, and acknowledge the Sophisticated Analytical Instrument Facility, Central China Normal University, Whuhan, for the data collection.

References

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Volume 66| Part 7| July 2010| Pages o1854-o1855

doi:10.1107/S1600536810024645

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