6-Methyl-2-p-tolyl-4-[3-(trifluoro­meth­yl)phen­yl]pyridazin-3(2H)-one

Niu, Z.-X.; Zhu, Y.-Q.; Hu, F.-Z.; Hu, X.-H.; Yang, H.-Z.

doi:10.1107/S1600536808005928

organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o675

doi:10.1107/S1600536808005928

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6-Methyl-2-p-tolyl-4-[3-(trifluoromethyl)phenyl]pyridazin-3(2H)-one

Zi-Xia Niu,^a You-Quan Zhu,^a Fang-Zhong Hu,^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: zyq8165@nankai.edu.cn

(Received 12 February 2008; accepted 3 March 2008; online 7 March 2008)

In the title molecule, C₁₉H₁₅F₃N₂O, the benzene rings of the tolyl and trifluoromethylphenyl groups form dihedral angles of 64.1 (2) and 38.5 (2)°, respectively, with the pyridazine ring. The CF₃ group is disordered over two orientations, with site-occupancy factors of ca 0.56 and 0.44.

Related literature

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

Experimental

Crystal data

C₁₉H₁₅F₃N₂O
M_r = 344.33
Monoclinic, C 2/c
a = 20.902 (6) Å
b = 4.2898 (13) Å
c = 37.683 (11) Å
β = 101.534 (5)°
V = 3310.6 (17) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 294 (2) K
0.52 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.945, T_max = 0.983
7702 measured reflections
2907 independent reflections
1988 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.170
S = 1.05
2907 reflections
256 parameters
51 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.25 e Å⁻³

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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005928/ci2564sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808005928/ci2564Isup2.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 was synthesized and its structure is reported here.

In the molecule of the title compound (Fig. 1), the central pyridazine ring (C9—C12/N1/N2) forms dihedral angles of 64.1 (2)° and 38.5 (2)°, respectively, with the C1—C6 and C13—C18 benzene rings. The C2—C1—N1—N2, C2—C1—N1—C12, C6—C1—N1—N2, C6—C1—N1—C12, C10—C11—C13—C14, C12—C11—C13—C14, C10—C11—C13—C18 and C12—C11—C13—C18 torsion angles are -115.7 (3), 65.2 (4), 64.5 (4), -114.6 (3), -38.5 (5), 140.2 (3), 141.6 (3) and -39.7 (5)°, respectively. No significant hydrogen bonding interactions are observed in the crystal structure.

Related literature top

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

Experimental top

A mixture of ethyl 2-(3-trifluoromethylphenyl)-4-oxopentanoate (2.3 mmol) and 4-methylphenylhydrazine (2.3 mmol) and glacial acetic acid (1 ml) was stirred at room temperature for 2 h. The precipitate formed was filtered and recrystallized from ethanol. Single crystals suitable for X-ray analysis were grown from a ethyl acetate-petroleum ether (3:1 v/v) solution 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. Only one disorder component is shown.

6-Methyl-2-p-tolyl-4-[3-(trifluoromethyl)phenyl]pyridazin- 3(2H)-one top

Crystal data top

C₁₉H₁₅F₃N₂O	F(000) = 1424
M_r = 344.33	D_x = 1.382 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2694 reflections
a = 20.902 (6) Å	θ = 2.2–26.2°
b = 4.2898 (13) Å	µ = 0.11 mm⁻¹
c = 37.683 (11) Å	T = 294 K
β = 101.534 (5)°	Block, colourless
V = 3310.6 (17) Å³	0.52 × 0.20 × 0.16 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	2907 independent reflections
Radiation source: fine-focus sealed tube	1988 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→17
T_min = 0.945, T_max = 0.983	k = −5→4
7702 measured reflections	l = −36→44

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.170	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0755P)² + 3.8729P] where P = (F_o² + 2F_c²)/3
2907 reflections	(Δ/σ)_max = 0.002
256 parameters	Δρ_max = 0.20 e Å⁻³
51 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₉H₁₅F₃N₂O	V = 3310.6 (17) Å³
M_r = 344.33	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 20.902 (6) Å	µ = 0.11 mm⁻¹
b = 4.2898 (13) Å	T = 294 K
c = 37.683 (11) Å	0.52 × 0.20 × 0.16 mm
β = 101.534 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2907 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1988 reflections with I > 2σ(I)
T_min = 0.945, T_max = 0.983	R_int = 0.035
7702 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	51 restraints
wR(F²) = 0.170	H-atom parameters constrained
S = 1.05	Δρ_max = 0.20 e Å⁻³
2907 reflections	Δρ_min = −0.25 e Å⁻³
256 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)
O1	0.15529 (10)	0.4998 (7)	0.16676 (6)	0.0680 (8)
N1	0.22749 (11)	0.2163 (6)	0.14191 (6)	0.0444 (6)
N2	0.24743 (11)	0.0589 (6)	0.11419 (7)	0.0474 (7)
C1	0.27804 (13)	0.2541 (8)	0.17437 (8)	0.0423 (7)
C2	0.27033 (14)	0.1120 (9)	0.20615 (8)	0.0529 (9)
H2	0.2336	−0.0092	0.2067	0.064*
C3	0.31796 (14)	0.1520 (9)	0.23731 (8)	0.0530 (9)
H3	0.3127	0.0567	0.2587	0.064*
C4	0.37291 (14)	0.3305 (8)	0.23708 (8)	0.0498 (8)
C5	0.37977 (15)	0.4657 (9)	0.20447 (9)	0.0583 (9)
H5	0.4170	0.5823	0.2037	0.070*
C6	0.33258 (14)	0.4312 (8)	0.17308 (8)	0.0514 (8)
H6	0.3377	0.5256	0.1516	0.062*
C7	0.42303 (18)	0.3813 (12)	0.27183 (9)	0.0780 (12)
H7A	0.4027	0.3520	0.2923	0.117*
H7B	0.4400	0.5894	0.2721	0.117*
H7C	0.4581	0.2344	0.2730	0.117*
C8	0.22624 (17)	−0.1579 (10)	0.05424 (9)	0.0675 (10)
H8A	0.2697	−0.2353	0.0627	0.101*
H8B	0.2261	−0.0166	0.0345	0.101*
H8C	0.1974	−0.3291	0.0462	0.101*
C9	0.20357 (14)	0.0106 (8)	0.08460 (8)	0.0471 (8)
C10	0.13750 (14)	0.1112 (8)	0.08120 (8)	0.0475 (8)
H10	0.1075	0.0670	0.0600	0.057*
C11	0.11739 (13)	0.2704 (8)	0.10827 (8)	0.0432 (7)
C12	0.16574 (13)	0.3414 (8)	0.14129 (8)	0.0469 (8)
C13	0.04906 (13)	0.3800 (8)	0.10537 (8)	0.0445 (8)
C14	0.01367 (14)	0.4972 (7)	0.07268 (8)	0.0463 (8)
H14	0.0333	0.5083	0.0526	0.056*
C15	−0.05036 (14)	0.5971 (8)	0.06965 (9)	0.0488 (8)
C16	−0.08032 (16)	0.5813 (9)	0.09917 (10)	0.0613 (10)
H16	−0.1233	0.6468	0.0972	0.074*
C17	−0.04563 (16)	0.4667 (11)	0.13184 (10)	0.0695 (11)
H17	−0.0656	0.4552	0.1517	0.083*
C18	0.01841 (15)	0.3695 (10)	0.13515 (9)	0.0599 (10)
H18	0.0413	0.2966	0.1573	0.072*
C19	−0.08649 (16)	0.7180 (8)	0.03406 (11)	0.0651 (10)
F1	−0.0909 (6)	0.5095 (13)	0.00586 (14)	0.100 (3)	0.564 (15)
F2	−0.1439 (3)	0.841 (3)	0.0327 (3)	0.119 (4)	0.564 (15)
F3	−0.0530 (5)	0.943 (2)	0.0207 (3)	0.083 (3)	0.564 (15)
F1'	−0.1325 (6)	0.5147 (17)	0.0190 (3)	0.100 (4)	0.436 (15)
F2'	−0.1258 (5)	0.955 (2)	0.0415 (3)	0.080 (3)	0.436 (15)
F3'	−0.0510 (6)	0.834 (3)	0.0126 (3)	0.095 (4)	0.436 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0453 (12)	0.105 (2)	0.0480 (14)	0.0123 (13)	−0.0030 (10)	−0.0287 (14)
N1	0.0358 (12)	0.0615 (17)	0.0327 (13)	0.0009 (12)	−0.0004 (10)	−0.0072 (12)
N2	0.0439 (14)	0.0591 (17)	0.0378 (14)	0.0016 (12)	0.0047 (11)	−0.0052 (12)
C1	0.0339 (14)	0.056 (2)	0.0336 (16)	0.0044 (14)	−0.0004 (12)	−0.0054 (14)
C2	0.0406 (16)	0.071 (2)	0.0455 (19)	−0.0073 (16)	0.0049 (14)	0.0000 (17)
C3	0.0484 (18)	0.072 (2)	0.0375 (17)	0.0012 (17)	0.0049 (14)	0.0023 (16)
C4	0.0384 (16)	0.067 (2)	0.0390 (18)	0.0033 (15)	−0.0039 (13)	−0.0042 (16)
C5	0.0400 (16)	0.081 (3)	0.050 (2)	−0.0136 (17)	−0.0008 (15)	0.0027 (18)
C6	0.0443 (17)	0.067 (2)	0.0405 (17)	−0.0022 (16)	0.0029 (14)	0.0062 (16)
C7	0.061 (2)	0.117 (4)	0.046 (2)	−0.017 (2)	−0.0133 (17)	0.003 (2)
C8	0.066 (2)	0.085 (3)	0.050 (2)	0.006 (2)	0.0058 (17)	−0.019 (2)
C9	0.0447 (17)	0.056 (2)	0.0370 (16)	−0.0016 (15)	0.0000 (13)	−0.0030 (15)
C10	0.0441 (16)	0.057 (2)	0.0360 (17)	−0.0083 (15)	−0.0044 (13)	−0.0038 (15)
C11	0.0370 (15)	0.0545 (19)	0.0344 (16)	−0.0029 (14)	−0.0021 (12)	0.0016 (14)
C12	0.0371 (15)	0.064 (2)	0.0374 (17)	0.0014 (15)	0.0011 (13)	−0.0063 (16)
C13	0.0344 (15)	0.058 (2)	0.0372 (16)	−0.0064 (14)	−0.0019 (13)	−0.0015 (15)
C14	0.0399 (16)	0.0546 (19)	0.0419 (17)	−0.0078 (14)	0.0021 (13)	−0.0041 (15)
C15	0.0392 (16)	0.052 (2)	0.0497 (19)	−0.0034 (14)	−0.0043 (14)	−0.0023 (15)
C16	0.0383 (16)	0.079 (3)	0.065 (2)	0.0013 (17)	0.0052 (16)	−0.009 (2)
C17	0.0475 (19)	0.107 (3)	0.055 (2)	−0.001 (2)	0.0135 (16)	0.000 (2)
C18	0.0441 (17)	0.090 (3)	0.0422 (18)	−0.0023 (18)	0.0011 (14)	0.0086 (19)
C19	0.059 (2)	0.055 (2)	0.071 (3)	0.0049 (19)	−0.010 (2)	0.002 (2)
F1	0.141 (7)	0.080 (3)	0.056 (3)	−0.001 (4)	−0.034 (3)	0.005 (2)
F2	0.044 (3)	0.190 (9)	0.117 (6)	0.025 (4)	0.004 (3)	0.065 (6)
F3	0.098 (5)	0.083 (4)	0.065 (5)	−0.008 (4)	0.012 (3)	0.011 (3)
F1'	0.098 (6)	0.079 (4)	0.091 (6)	−0.012 (4)	−0.055 (5)	−0.008 (4)
F2'	0.066 (5)	0.069 (4)	0.094 (5)	0.021 (4)	−0.011 (4)	0.005 (3)
F3'	0.087 (5)	0.155 (9)	0.044 (5)	0.050 (6)	0.016 (4)	0.024 (6)

Geometric parameters (Å, º) top

O1—C12	1.231 (4)	C9—C10	1.428 (4)
N1—N2	1.377 (3)	C10—C11	1.362 (4)
N1—C12	1.394 (4)	C10—H10	0.93
N1—C1	1.457 (3)	C11—C12	1.470 (4)
N2—C9	1.311 (4)	C11—C13	1.487 (4)
C1—C6	1.379 (4)	C13—C14	1.398 (4)
C1—C2	1.382 (4)	C13—C18	1.400 (4)
C2—C3	1.390 (4)	C14—C15	1.388 (4)
C2—H2	0.93	C14—H14	0.93
C3—C4	1.382 (5)	C15—C16	1.383 (5)
C3—H3	0.93	C15—C19	1.494 (5)
C4—C5	1.392 (5)	C16—C17	1.388 (5)
C4—C7	1.520 (4)	C16—H16	0.93
C5—C6	1.388 (4)	C17—C18	1.384 (5)
C5—H5	0.93	C17—H17	0.93
C6—H6	0.93	C18—H18	0.93
C7—H7A	0.96	C19—F3'	1.300 (7)
C7—H7B	0.96	C19—F2	1.303 (6)
C7—H7C	0.96	C19—F1'	1.337 (6)
C8—C9	1.508 (4)	C19—F3	1.347 (6)
C8—H8A	0.96	C19—F2'	1.370 (6)
C8—H8B	0.96	C19—F1	1.377 (6)
C8—H8C	0.96

N2—N1—C12	126.6 (2)	O1—C12—N1	120.5 (3)
N2—N1—C1	114.4 (2)	O1—C12—C11	125.1 (3)
C12—N1—C1	119.0 (2)	N1—C12—C11	114.3 (3)
C9—N2—N1	117.2 (2)	C14—C13—C18	118.2 (3)
C6—C1—C2	120.9 (3)	C14—C13—C11	120.7 (3)
C6—C1—N1	119.9 (3)	C18—C13—C11	121.2 (3)
C2—C1—N1	119.2 (3)	C15—C14—C13	121.0 (3)
C1—C2—C3	119.3 (3)	C15—C14—H14	119.5
C1—C2—H2	120.3	C13—C14—H14	119.5
C3—C2—H2	120.3	C16—C15—C14	120.2 (3)
C4—C3—C2	121.3 (3)	C16—C15—C19	120.7 (3)
C4—C3—H3	119.4	C14—C15—C19	119.1 (3)
C2—C3—H3	119.4	C15—C16—C17	119.4 (3)
C3—C4—C5	118.0 (3)	C15—C16—H16	120.3
C3—C4—C7	120.3 (3)	C17—C16—H16	120.3
C5—C4—C7	121.7 (3)	C18—C17—C16	120.7 (3)
C6—C5—C4	121.8 (3)	C18—C17—H17	119.6
C6—C5—H5	119.1	C16—C17—H17	119.6
C4—C5—H5	119.1	C17—C18—C13	120.5 (3)
C1—C6—C5	118.7 (3)	C17—C18—H18	119.7
C1—C6—H6	120.6	C13—C18—H18	119.7
C5—C6—H6	120.6	F3'—C19—F2	117.1 (7)
C4—C7—H7A	109.5	F3'—C19—F1'	115.9 (8)
C4—C7—H7B	109.5	F2—C19—F1'	70.8 (5)
H7A—C7—H7B	109.5	F3'—C19—F3	24.5 (7)
C4—C7—H7C	109.5	F2—C19—F3	103.7 (7)
H7A—C7—H7C	109.5	F1'—C19—F3	133.8 (7)
H7B—C7—H7C	109.5	F3'—C19—F2'	106.5 (8)
C9—C8—H8A	109.5	F2—C19—F2'	28.5 (5)
C9—C8—H8B	109.5	F1'—C19—F2'	99.3 (6)
H8A—C8—H8B	109.5	F3—C19—F2'	85.6 (6)
C9—C8—H8C	109.5	F3'—C19—F1	74.2 (6)
H8A—C8—H8C	109.5	F2—C19—F1	108.3 (5)
H8B—C8—H8C	109.5	F1'—C19—F1	47.0 (4)
N2—C9—C10	121.9 (3)	F3—C19—F1	97.8 (5)
N2—C9—C8	116.7 (3)	F2'—C19—F1	133.5 (5)
C10—C9—C8	121.4 (3)	F3'—C19—C15	116.2 (6)
C11—C10—C9	121.5 (3)	F2—C19—C15	118.2 (5)
C11—C10—H10	119.3	F1'—C19—C15	110.2 (5)
C9—C10—H10	119.3	F3—C19—C15	112.1 (5)
C10—C11—C12	118.4 (3)	F2'—C19—C15	106.8 (5)
C10—C11—C13	122.6 (3)	F1—C19—C15	114.3 (3)
C12—C11—C13	119.0 (3)

C12—N1—N2—C9	−2.8 (5)	C10—C11—C12—N1	−4.0 (4)
C1—N1—N2—C9	178.3 (3)	C13—C11—C12—N1	177.3 (3)
N2—N1—C1—C6	64.5 (4)	C10—C11—C13—C14	−38.5 (5)
C12—N1—C1—C6	−114.6 (3)	C12—C11—C13—C14	140.2 (3)
N2—N1—C1—C2	−115.7 (3)	C10—C11—C13—C18	141.6 (3)
C12—N1—C1—C2	65.2 (4)	C12—C11—C13—C18	−39.7 (5)
C6—C1—C2—C3	0.8 (5)	C18—C13—C14—C15	−0.7 (5)
N1—C1—C2—C3	−178.9 (3)	C11—C13—C14—C15	179.3 (3)
C1—C2—C3—C4	−0.1 (5)	C13—C14—C15—C16	−0.2 (5)
C2—C3—C4—C5	−1.0 (5)	C13—C14—C15—C19	−179.5 (3)
C2—C3—C4—C7	177.6 (3)	C14—C15—C16—C17	0.4 (5)
C3—C4—C5—C6	1.6 (5)	C19—C15—C16—C17	179.7 (3)
C7—C4—C5—C6	−177.0 (4)	C15—C16—C17—C18	0.2 (6)
C2—C1—C6—C5	−0.3 (5)	C16—C17—C18—C13	−1.1 (6)
N1—C1—C6—C5	179.5 (3)	C14—C13—C18—C17	1.3 (5)
C4—C5—C6—C1	−0.9 (5)	C11—C13—C18—C17	−178.7 (3)
N1—N2—C9—C10	−1.1 (5)	C16—C15—C19—F3'	155.1 (8)
N1—N2—C9—C8	179.1 (3)	C14—C15—C19—F3'	−25.6 (9)
N2—C9—C10—C11	1.9 (5)	C16—C15—C19—F2	7.9 (9)
C8—C9—C10—C11	−178.3 (3)	C14—C15—C19—F2	−172.7 (8)
C9—C10—C11—C12	0.8 (5)	C16—C15—C19—F1'	−70.5 (9)
C9—C10—C11—C13	179.5 (3)	C14—C15—C19—F1'	108.8 (8)
N2—N1—C12—O1	−174.0 (3)	C16—C15—C19—F3	128.5 (6)
C1—N1—C12—O1	5.0 (5)	C14—C15—C19—F3	−52.2 (6)
N2—N1—C12—C11	5.2 (5)	C16—C15—C19—F2'	36.4 (7)
C1—N1—C12—C11	−175.9 (3)	C14—C15—C19—F2'	−144.3 (6)
C10—C11—C12—O1	175.2 (3)	C16—C15—C19—F1	−121.3 (7)
C13—C11—C12—O1	−3.6 (5)	C14—C15—C19—F1	58.0 (7)

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅F₃N₂O
M_r	344.33
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	294
a, b, c (Å)	20.902 (6), 4.2898 (13), 37.683 (11)
β (°)	101.534 (5)
V (Å³)	3310.6 (17)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.52 × 0.20 × 0.16

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.945, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	7702, 2907, 1988
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.170, 1.05
No. of reflections	2907
No. of parameters	256
No. of restraints	51
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.25

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

References

Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Heinisch, G. & Kopelent, H. (1992). Prog. Med. Chem. 29, 141–183. CrossRef PubMed CAS Google Scholar
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