2-Fluoro-N′-[(2-meth­oxy­naphthalen-1-yl)methyl­idene]benzohydrazide

Li, H.-B.

doi:10.1107/S1600536812011580

organic compounds

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Volume 68| Part 4| April 2012| Page o1164

doi:10.1107/S1600536812011580

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2-Fluoro-N′-[(2-methoxynaphthalen-1-yl)methylidene]benzohydrazide

He-Bing Li ^a ^*

^aDepartment of Chemistry and Life Sciences, Xiangnan University, Chenzhou 423000, People's Republic of China
^*Correspondence e-mail: lihebing07@163.com

(Received 5 March 2012; accepted 17 March 2012; online 24 March 2012)

The asymmetric unit of the title compound, C₁₉H₁₅FN₂O₂, contains two molecules, A and B, in which the dihedral angles between the ring systems are 46.4 (2) and 17.24 (14)°, respectively. In the crystal, molecules are linked into [010] chains of alternating A and B species by N—H⋯O hydrogen bonds.

Related literature

For a related structure and background to hydrazones, see: Li (2011 ). For related structures, see: Qiu et al. (2006 ); Yang & Guo (2006 ); Yang (2006 ).

Experimental

Crystal data

C₁₉H₁₅FN₂O₂
M_r = 322.33
Monoclinic, P 2₁ /c
a = 9.462 (2) Å
b = 17.030 (3) Å
c = 20.470 (2) Å
β = 96.575 (2)°
V = 3276.9 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.18 × 0.18 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.983, T_max = 0.984
19271 measured reflections
6420 independent reflections
3070 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.188
S = 1.01
6420 reflections
441 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3ⁱ	0.90 (1)	2.02 (1)	2.901 (3)	166 (3)
N3—H3⋯O1ⁱⁱ	0.90 (1)	2.07 (2)	2.917 (3)	156 (3)
Symmetry codes: (i) x-1, y, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1998); 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/S1600536812011580/hb6672sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812011580/hb6672Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812011580/hb6672Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of hydrazones (Li, 2011), the structure of the title compound is now reported.

The bond lengths and bond angles in the title compound (Fig. 1) are comprable with those observed in similar compounds (Qiu et al., 2006; Yang & Guo, 2006; Yang, 2006). The dihedral angle between the C9—C18 naphthyl ring and C1—C1 benzene ring is 46.3 (2)° and the equivalent angle in the second molecule is 17.24 (14)°. In the crystal, the molecules are linked into chains along the b axis by N—H···O hydrogen bonds (Table 1 and Fig. 2).

Related literature top

For a related structure and background to hydrazones, see: Li (2011). For related structures, see: Qiu et al. (2006); Yang & Guo (2006); Yang (2006).

Experimental top

2-Methoxy-1-naphthaldehyde (0.1 mmol, 18.6 mg) and 2-fluorobenzohydrazide (0.1 mmol, 12.4 mg) were dissolved in methanol (10 ml). The mixture was stirred at room temperature for 10 min to give a clear colorless solution. Colourless needles of the title compound were formed by gradual evaporation of the solvent over a week at room temperature (yield 78%).

Structure description top

As part of our ongoing studies of hydrazones (Li, 2011), the structure of the title compound is now reported.

For a related structure and background to hydrazones, see: Li (2011). For related structures, see: Qiu et al. (2006); Yang & Guo (2006); Yang (2006).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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. The molecular structure of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.

2-Fluoro-N'-[(2-methoxynaphthalen-1-yl)methylidene]benzohydrazide top

Crystal data top

C₁₉H₁₅FN₂O₂	F(000) = 1344
M_r = 322.33	D_x = 1.307 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2255 reflections
a = 9.462 (2) Å	θ = 2.4–24.5°
b = 17.030 (3) Å	µ = 0.09 mm⁻¹
c = 20.470 (2) Å	T = 298 K
β = 96.575 (2)°	Cut from needle, colorless
V = 3276.9 (10) Å³	0.18 × 0.18 × 0.17 mm
Z = 8

Data collection top

Bruker SMART CCD diffractometer	6420 independent reflections
Radiation source: fine-focus sealed tube	3070 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.983, T_max = 0.984	k = −20→20
19271 measured reflections	l = −18→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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.188	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0767P)² + 0.7482P] where P = (F_o² + 2F_c²)/3
6420 reflections	(Δ/σ)_max < 0.001
441 parameters	Δρ_max = 0.53 e Å⁻³
2 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₉H₁₅FN₂O₂	V = 3276.9 (10) Å³
M_r = 322.33	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.462 (2) Å	µ = 0.09 mm⁻¹
b = 17.030 (3) Å	T = 298 K
c = 20.470 (2) Å	0.18 × 0.18 × 0.17 mm
β = 96.575 (2)°

Data collection top

Bruker SMART CCD diffractometer	6420 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3070 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.984	R_int = 0.060
19271 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	2 restraints
wR(F²) = 0.188	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.53 e Å⁻³
6420 reflections	Δρ_min = −0.30 e Å⁻³
441 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
F1	−0.0022 (4)	0.3477 (2)	0.06984 (17)	0.1590 (14)
F2	1.3946 (2)	0.57294 (11)	0.16914 (12)	0.0780 (7)
H1	−0.008 (4)	0.4855 (11)	0.2092 (17)	0.080*
H3	1.086 (4)	0.7327 (10)	0.2401 (18)	0.080*
N1	−0.0394 (3)	0.43870 (15)	0.22248 (13)	0.0457 (7)
N2	0.0044 (3)	0.41427 (15)	0.28601 (13)	0.0469 (7)
N3	1.0565 (3)	0.68423 (14)	0.22805 (13)	0.0468 (7)
N4	0.9273 (3)	0.65685 (15)	0.24414 (13)	0.0463 (7)
O1	−0.1478 (3)	0.32290 (13)	0.19477 (12)	0.0626 (7)
O2	0.1075 (3)	0.59232 (16)	0.39855 (13)	0.0798 (8)
O3	1.0985 (2)	0.57402 (13)	0.17140 (11)	0.0580 (6)
O4	0.7134 (3)	0.83626 (14)	0.29575 (15)	0.0837 (9)
C1	−0.1047 (6)	0.3992 (3)	0.0618 (3)	0.0899 (14)
C2	−0.1593 (4)	0.4240 (2)	0.11484 (17)	0.0554 (9)
C3	−0.2676 (6)	0.4823 (3)	0.1082 (3)	0.1151 (19)
H3A	−0.3091	0.5027	0.1436	0.138*
C4	−0.3049 (8)	0.5056 (3)	0.0437 (4)	0.153 (3)
H4	−0.3757	0.5434	0.0362	0.183*
C5	−0.2457 (11)	0.4774 (4)	−0.0104 (4)	0.167 (4)
H5	−0.2777	0.4956	−0.0524	0.200*
C6	−0.1433 (8)	0.4244 (4)	−0.0018 (2)	0.132 (3)
H6	−0.0995	0.4050	−0.0369	0.158*
C7	−0.1146 (3)	0.38962 (19)	0.18080 (15)	0.0427 (8)
C8	0.0679 (3)	0.4674 (2)	0.32235 (16)	0.0498 (8)
H8	0.0799	0.5165	0.3039	0.060*
C9	0.1224 (3)	0.4555 (2)	0.39083 (16)	0.0502 (9)
C10	0.1416 (4)	0.5229 (2)	0.42919 (18)	0.0646 (10)
C11	0.1938 (6)	0.5182 (3)	0.4958 (2)	0.1005 (16)
H11	0.2067	0.5637	0.5208	0.121*
C12	0.2255 (6)	0.4478 (3)	0.5238 (2)	0.1048 (17)
H12	0.2594	0.4457	0.5683	0.126*
C13	0.2088 (4)	0.3779 (3)	0.48811 (18)	0.0711 (11)
C14	0.2415 (5)	0.3050 (3)	0.5180 (2)	0.0904 (14)
H14	0.2767	0.3035	0.5623	0.109*
C15	0.2231 (4)	0.2367 (3)	0.4841 (2)	0.0800 (13)
H15	0.2438	0.1889	0.5049	0.096*
C16	0.1727 (4)	0.2394 (2)	0.4175 (2)	0.0681 (11)
H16	0.1596	0.1929	0.3938	0.082*
C17	0.1425 (3)	0.3090 (2)	0.38666 (18)	0.0556 (9)
H17	0.1114	0.3091	0.3419	0.067*
C18	0.1572 (3)	0.3809 (2)	0.42067 (16)	0.0517 (9)
C19	0.1272 (6)	0.6641 (2)	0.4349 (2)	0.1031 (16)
H19A	0.0739	0.6621	0.4720	0.155*
H19B	0.0947	0.7073	0.4071	0.155*
H19C	0.2263	0.6708	0.4499	0.155*
C20	1.3748 (4)	0.64862 (18)	0.15306 (17)	0.0503 (9)
C21	1.2493 (3)	0.68480 (17)	0.16285 (15)	0.0407 (7)
C22	1.2363 (4)	0.76311 (19)	0.14472 (17)	0.0535 (9)
H22	1.1536	0.7902	0.1510	0.064*
C23	1.3431 (4)	0.8014 (2)	0.11767 (19)	0.0644 (10)
H23	1.3308	0.8534	0.1046	0.077*
C24	1.4673 (4)	0.7636 (2)	0.1098 (2)	0.0735 (12)
H24	1.5400	0.7901	0.0921	0.088*
C25	1.4845 (4)	0.6864 (2)	0.1280 (2)	0.0708 (11)
H25	1.5690	0.6601	0.1233	0.085*
C26	1.1294 (3)	0.64171 (18)	0.18800 (15)	0.0424 (8)
C27	0.8576 (3)	0.70852 (19)	0.27226 (15)	0.0461 (8)
H27	0.9017	0.7568	0.2811	0.055*
C28	0.7151 (3)	0.69900 (18)	0.29183 (14)	0.0419 (7)
C29	0.6442 (4)	0.7680 (2)	0.30429 (17)	0.0538 (9)
C30	0.5059 (4)	0.7667 (2)	0.32251 (19)	0.0678 (11)
H30	0.4593	0.8136	0.3295	0.081*
C31	0.4411 (4)	0.6978 (2)	0.32980 (19)	0.0681 (11)
H31	0.3492	0.6976	0.3418	0.082*
C32	0.5078 (3)	0.6258 (2)	0.31977 (17)	0.0549 (9)
C33	0.4409 (4)	0.5537 (3)	0.3293 (2)	0.0742 (12)
H33	0.3506	0.5536	0.3431	0.089*
C34	0.5048 (4)	0.4843 (2)	0.3190 (2)	0.0772 (12)
H34	0.4589	0.4372	0.3257	0.093*
C35	0.6399 (4)	0.4842 (2)	0.29817 (19)	0.0663 (10)
H35	0.6836	0.4367	0.2904	0.080*
C36	0.7081 (4)	0.55235 (18)	0.28913 (17)	0.0534 (9)
H36	0.7987	0.5508	0.2757	0.064*
C37	0.6458 (3)	0.62534 (18)	0.29945 (14)	0.0422 (8)
C38	0.6786 (5)	0.9035 (2)	0.3292 (2)	0.0879 (14)
H38A	0.5837	0.9197	0.3132	0.132*
H38B	0.7442	0.9447	0.3220	0.132*
H38C	0.6838	0.8923	0.3754	0.132*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.181 (4)	0.188 (3)	0.119 (3)	0.030 (3)	0.062 (3)	−0.018 (2)
F2	0.0723 (14)	0.0502 (13)	0.1137 (19)	0.0092 (10)	0.0203 (13)	0.0088 (12)
N1	0.0481 (16)	0.0476 (17)	0.0404 (16)	−0.0057 (13)	0.0003 (13)	0.0044 (14)
N2	0.0487 (16)	0.0549 (17)	0.0366 (16)	−0.0028 (13)	0.0026 (13)	0.0052 (14)
N3	0.0456 (16)	0.0439 (16)	0.0534 (17)	−0.0090 (13)	0.0170 (13)	−0.0083 (14)
N4	0.0436 (16)	0.0489 (16)	0.0489 (17)	−0.0040 (13)	0.0160 (13)	−0.0021 (13)
O1	0.0756 (17)	0.0448 (14)	0.0638 (16)	−0.0116 (12)	−0.0074 (13)	0.0118 (12)
O2	0.112 (2)	0.0629 (18)	0.0635 (18)	−0.0032 (15)	0.0045 (16)	−0.0105 (15)
O3	0.0672 (15)	0.0424 (14)	0.0685 (16)	−0.0146 (11)	0.0257 (13)	−0.0102 (12)
O4	0.0845 (19)	0.0444 (15)	0.130 (3)	0.0030 (14)	0.0466 (18)	−0.0075 (15)
C1	0.106 (4)	0.081 (3)	0.082 (4)	0.007 (3)	0.008 (3)	0.003 (3)
C2	0.075 (2)	0.050 (2)	0.039 (2)	−0.0166 (19)	−0.0042 (19)	−0.0007 (17)
C3	0.131 (4)	0.092 (3)	0.105 (4)	0.018 (3)	−0.061 (3)	0.053 (3)
C4	0.221 (8)	0.092 (4)	0.125 (5)	0.026 (4)	−0.071 (6)	0.010 (4)
C5	0.278 (11)	0.105 (6)	0.092 (5)	−0.049 (6)	−0.088 (6)	0.040 (4)
C6	0.221 (8)	0.138 (6)	0.035 (3)	−0.055 (5)	0.008 (4)	0.001 (3)
C7	0.0421 (18)	0.0409 (19)	0.044 (2)	0.0030 (15)	0.0016 (15)	0.0016 (16)
C8	0.049 (2)	0.055 (2)	0.045 (2)	−0.0051 (17)	0.0051 (16)	0.0006 (17)
C9	0.0438 (19)	0.069 (2)	0.038 (2)	−0.0102 (17)	0.0039 (15)	−0.0053 (18)
C10	0.079 (3)	0.071 (3)	0.044 (2)	−0.012 (2)	0.0066 (19)	−0.003 (2)
C11	0.154 (5)	0.097 (4)	0.047 (3)	−0.019 (3)	−0.005 (3)	−0.019 (3)
C12	0.161 (5)	0.105 (4)	0.044 (3)	−0.014 (4)	−0.012 (3)	0.000 (3)
C13	0.086 (3)	0.088 (3)	0.038 (2)	−0.007 (2)	0.001 (2)	0.010 (2)
C14	0.109 (4)	0.111 (4)	0.050 (3)	0.001 (3)	0.002 (2)	0.020 (3)
C15	0.077 (3)	0.092 (3)	0.072 (3)	0.008 (2)	0.012 (2)	0.029 (3)
C16	0.053 (2)	0.074 (3)	0.077 (3)	0.0002 (19)	0.005 (2)	0.014 (2)
C17	0.049 (2)	0.065 (2)	0.052 (2)	−0.0016 (18)	0.0004 (17)	0.008 (2)
C18	0.0451 (19)	0.069 (3)	0.041 (2)	−0.0073 (17)	0.0056 (15)	0.0037 (19)
C19	0.145 (5)	0.071 (3)	0.098 (4)	−0.012 (3)	0.033 (3)	−0.027 (3)
C20	0.055 (2)	0.0336 (19)	0.063 (2)	0.0042 (16)	0.0136 (18)	0.0009 (16)
C21	0.0411 (18)	0.0403 (19)	0.0413 (18)	−0.0021 (14)	0.0076 (14)	−0.0017 (15)
C22	0.054 (2)	0.045 (2)	0.064 (2)	0.0011 (16)	0.0148 (18)	0.0060 (17)
C23	0.065 (2)	0.049 (2)	0.082 (3)	−0.0026 (19)	0.018 (2)	0.0143 (19)
C24	0.062 (3)	0.061 (3)	0.104 (3)	−0.008 (2)	0.039 (2)	0.006 (2)
C25	0.052 (2)	0.065 (3)	0.101 (3)	0.0006 (19)	0.032 (2)	0.000 (2)
C26	0.0468 (19)	0.0384 (19)	0.0424 (19)	−0.0009 (15)	0.0059 (15)	0.0013 (15)
C27	0.0460 (19)	0.0466 (19)	0.046 (2)	−0.0071 (16)	0.0083 (16)	0.0024 (16)
C28	0.0410 (18)	0.0499 (19)	0.0355 (17)	−0.0009 (15)	0.0079 (14)	−0.0034 (15)
C29	0.055 (2)	0.048 (2)	0.060 (2)	0.0018 (18)	0.0138 (18)	−0.0034 (18)
C30	0.057 (2)	0.064 (3)	0.084 (3)	0.017 (2)	0.017 (2)	−0.007 (2)
C31	0.047 (2)	0.081 (3)	0.079 (3)	0.004 (2)	0.020 (2)	−0.002 (2)
C32	0.043 (2)	0.066 (2)	0.057 (2)	−0.0038 (18)	0.0125 (16)	0.0014 (19)
C33	0.053 (2)	0.091 (3)	0.082 (3)	−0.012 (2)	0.023 (2)	0.003 (2)
C34	0.073 (3)	0.068 (3)	0.094 (3)	−0.024 (2)	0.023 (2)	0.003 (2)
C35	0.071 (3)	0.055 (2)	0.076 (3)	−0.006 (2)	0.023 (2)	0.002 (2)
C36	0.054 (2)	0.048 (2)	0.060 (2)	−0.0031 (17)	0.0193 (18)	−0.0012 (17)
C37	0.0404 (18)	0.051 (2)	0.0354 (18)	−0.0016 (15)	0.0047 (14)	0.0019 (15)
C38	0.107 (4)	0.054 (2)	0.104 (4)	0.006 (2)	0.016 (3)	−0.015 (2)

Geometric parameters (Å, º) top

F1—C1	1.304 (5)	C15—H15	0.9300
F2—C20	1.338 (3)	C16—C17	1.357 (5)
N1—C7	1.340 (4)	C16—H16	0.9300
N1—N2	1.383 (3)	C17—C18	1.407 (5)
N1—H1	0.903 (10)	C17—H17	0.9300
N2—C8	1.277 (4)	C19—H19A	0.9600
N3—C26	1.342 (4)	C19—H19B	0.9600
N3—N4	1.383 (3)	C19—H19C	0.9600
N3—H3	0.897 (10)	C20—C25	1.370 (5)
N4—C27	1.276 (4)	C20—C21	1.374 (4)
O1—C7	1.221 (3)	C21—C22	1.386 (4)
O2—C10	1.359 (4)	C21—C26	1.491 (4)
O2—C19	1.431 (4)	C22—C23	1.371 (4)
O3—C26	1.228 (3)	C22—H22	0.9300
O4—C29	1.356 (4)	C23—C24	1.366 (5)
O4—C38	1.392 (4)	C23—H23	0.9300
C1—C2	1.325 (6)	C24—C25	1.371 (5)
C1—C6	1.379 (7)	C24—H24	0.9300
C2—C3	1.421 (6)	C25—H25	0.9300
C2—C7	1.488 (4)	C27—C28	1.458 (4)
C3—C4	1.385 (8)	C27—H27	0.9300
C3—H3A	0.9300	C28—C29	1.390 (4)
C4—C5	1.383 (10)	C28—C37	1.432 (4)
C4—H4	0.9300	C29—C30	1.402 (5)
C5—C6	1.321 (9)	C30—C31	1.342 (5)
C5—H5	0.9300	C30—H30	0.9300
C6—H6	0.9300	C31—C32	1.404 (5)
C8—C9	1.451 (4)	C31—H31	0.9300
C8—H8	0.9300	C32—C33	1.406 (5)
C9—C10	1.392 (5)	C32—C37	1.415 (4)
C9—C18	1.431 (5)	C33—C34	1.355 (5)
C10—C11	1.398 (5)	C33—H33	0.9300
C11—C12	1.348 (6)	C34—C35	1.393 (5)
C11—H11	0.9300	C34—H34	0.9300
C12—C13	1.396 (6)	C35—C36	1.351 (4)
C12—H12	0.9300	C35—H35	0.9300
C13—C14	1.403 (5)	C36—C37	1.402 (4)
C13—C18	1.412 (5)	C36—H36	0.9300
C14—C15	1.355 (6)	C38—H38A	0.9600
C14—H14	0.9300	C38—H38B	0.9600
C15—C16	1.392 (6)	C38—H38C	0.9600

C7—N1—N2	119.4 (3)	O2—C19—H19B	109.5
C7—N1—H1	122 (2)	H19A—C19—H19B	109.5
N2—N1—H1	118 (2)	O2—C19—H19C	109.5
C8—N2—N1	113.9 (3)	H19A—C19—H19C	109.5
C26—N3—N4	119.6 (2)	H19B—C19—H19C	109.5
C26—N3—H3	120 (2)	F2—C20—C25	117.0 (3)
N4—N3—H3	120 (2)	F2—C20—C21	119.7 (3)
C27—N4—N3	113.1 (3)	C25—C20—C21	123.3 (3)
C10—O2—C19	119.5 (3)	C20—C21—C22	116.4 (3)
C29—O4—C38	119.8 (3)	C20—C21—C26	122.3 (3)
F1—C1—C2	117.7 (4)	C22—C21—C26	121.2 (3)
F1—C1—C6	116.3 (6)	C23—C22—C21	121.2 (3)
C2—C1—C6	126.0 (5)	C23—C22—H22	119.4
C1—C2—C3	119.3 (4)	C21—C22—H22	119.4
C1—C2—C7	121.4 (4)	C24—C23—C22	120.5 (3)
C3—C2—C7	119.2 (4)	C24—C23—H23	119.7
C4—C3—C2	113.2 (6)	C22—C23—H23	119.7
C4—C3—H3A	123.4	C23—C24—C25	119.8 (3)
C2—C3—H3A	123.4	C23—C24—H24	120.1
C5—C4—C3	125.6 (7)	C25—C24—H24	120.1
C5—C4—H4	117.2	C20—C25—C24	118.7 (3)
C3—C4—H4	117.2	C20—C25—H25	120.6
C6—C5—C4	119.2 (6)	C24—C25—H25	120.6
C6—C5—H5	120.4	O3—C26—N3	123.6 (3)
C4—C5—H5	120.4	O3—C26—C21	122.2 (3)
C5—C6—C1	116.8 (6)	N3—C26—C21	114.2 (3)
C5—C6—H6	121.6	N4—C27—C28	126.1 (3)
C1—C6—H6	121.6	N4—C27—H27	116.9
O1—C7—N1	124.3 (3)	C28—C27—H27	116.9
O1—C7—C2	121.7 (3)	C29—C28—C37	118.9 (3)
N1—C7—C2	114.0 (3)	C29—C28—C27	115.9 (3)
N2—C8—C9	123.7 (3)	C37—C28—C27	125.2 (3)
N2—C8—H8	118.1	O4—C29—C28	116.8 (3)
C9—C8—H8	118.1	O4—C29—C30	121.7 (3)
C10—C9—C18	118.9 (3)	C28—C29—C30	121.4 (3)
C10—C9—C8	116.0 (3)	C31—C30—C29	119.7 (3)
C18—C9—C8	125.1 (3)	C31—C30—H30	120.1
O2—C10—C9	116.7 (3)	C29—C30—H30	120.1
O2—C10—C11	122.6 (4)	C30—C31—C32	121.9 (3)
C9—C10—C11	120.7 (4)	C30—C31—H31	119.0
C12—C11—C10	120.2 (4)	C32—C31—H31	119.0
C12—C11—H11	119.9	C31—C32—C33	121.7 (3)
C10—C11—H11	119.9	C31—C32—C37	119.6 (3)
C11—C12—C13	121.9 (4)	C33—C32—C37	118.7 (3)
C11—C12—H12	119.0	C34—C33—C32	121.6 (3)
C13—C12—H12	119.0	C34—C33—H33	119.2
C12—C13—C14	121.3 (4)	C32—C33—H33	119.2
C12—C13—C18	119.2 (4)	C33—C34—C35	119.4 (4)
C14—C13—C18	119.5 (4)	C33—C34—H34	120.3
C15—C14—C13	121.9 (4)	C35—C34—H34	120.3
C15—C14—H14	119.1	C36—C35—C34	120.7 (4)
C13—C14—H14	119.1	C36—C35—H35	119.7
C14—C15—C16	118.8 (4)	C34—C35—H35	119.7
C14—C15—H15	120.6	C35—C36—C37	121.7 (3)
C16—C15—H15	120.6	C35—C36—H36	119.2
C17—C16—C15	121.0 (4)	C37—C36—H36	119.2
C17—C16—H16	119.5	C36—C37—C32	117.9 (3)
C15—C16—H16	119.5	C36—C37—C28	123.7 (3)
C16—C17—C18	121.7 (3)	C32—C37—C28	118.4 (3)
C16—C17—H17	119.2	O4—C38—H38A	109.5
C18—C17—H17	119.2	O4—C38—H38B	109.5
C17—C18—C13	117.1 (3)	H38A—C38—H38B	109.5
C17—C18—C9	123.8 (3)	O4—C38—H38C	109.5
C13—C18—C9	119.1 (3)	H38A—C38—H38C	109.5
O2—C19—H19A	109.5	H38B—C38—H38C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.90 (1)	2.02 (1)	2.901 (3)	166 (3)
N3—H3···O1ⁱⁱ	0.90 (1)	2.07 (2)	2.917 (3)	156 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅FN₂O₂
M_r	322.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.462 (2), 17.030 (3), 20.470 (2)
β (°)	96.575 (2)
V (Å³)	3276.9 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.18 × 0.18 × 0.17

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.983, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	19271, 6420, 3070
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.188, 1.01
No. of reflections	6420
No. of parameters	441
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.30

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), 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
N1—H1···O3ⁱ	0.903 (10)	2.017 (13)	2.901 (3)	166 (3)
N3—H3···O1ⁱⁱ	0.897 (10)	2.074 (18)	2.917 (3)	156 (3)

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

Acknowledgements

The author acknowledges a research grant from Xiangnan University.

References

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