2-(4-Bromo­phen­yl)-3-phenyl­benzo[f]quinoline

Wang, X.-S.; Li, Q.; Zhang, M.-M.; Tu, S.-J.

doi:10.1107/S1600536807036975

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2-(4-Bromophenyl)-3-phenylbenzo[f]quinoline

X.-S. Wang, Q. Li, M.-M. Zhang and S.-J. Tu

The title compound, C₂₅H₁₆BrN, was synthesized by the reaction of N-arylidenenaphthalen-2-amine and phenylacetaldehyde in the presence of iodine. In the molecular structure, the benzoquinoline ring system makes dihedral angles of 61.1 (1) and 39.8 (1)°, respectively, with the phenyl and bromophenyl rings. The dihedral angle between these rings is 57.6 (1)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036975/is2196sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036975/is2196Isup2.hkl Contains datablock I

CCDC reference: 662407

checkCIF report

Key indicators

Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.004 Å
R factor = 0.042
wR factor = 0.084
Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.298     0.679
            Tmin and Tmax expected:      0.237     0.680
            RR =      1.260
            Please check that your absorption correction is appropriate.
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.28
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.78 mm
PLAT432_ALERT_2_C Short Inter X...Y Contact  C14    ..  C14     ..       3.17 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Quinoline and its derivatives represent an important class of nitrogen-containing heterocycles as they constitute useful intermediates in organic synthesis and are useful dyes (Brock et al., 1999). They are well known in the pharmaceutical industry and have been shown to possess a broad spectrum of biological activities including antiasthmatic activity (Sawada et al., 2004), anti-inflammatory activity (Fokialakis et al., 2002), antimalarial activity (Fossa et al., 2002) and anthelmintic agents (Sakata et al., 1988). We report here the crystal structure of the title compound, (I).

In (I), the benzoquinoline ring system (C1—C5/N1/C18—C25) makes dihedral angles of 61.1 (1) and 39.8 (1)° with the phenyl (C12—C17) and benzene (C6—C11) rings, respectively. The dihedral angle between the phenyl (C12—C17) and benzene (C6—C11) rings is 57.6 (1)°. There is no intermolecular hydrogen bond in the crystal.

Related literature top

For related literature, see: Brock et al. (1999); Fokialakis et al. (2002); Fossa et al. (2002); Sakata et al. (1988); Sawada et al. (2004).

Experimental top

The title compound was prepared by the reaction of N-arylidenenaphthalen-2-amine (0.62 g, 2 mmol) and phenylacetaldehyde (0.24 g, 2 mmol) in the presence of iodine (0.05 g) in THF at 340 K for 5 h (yield 72%; m.p. 478–480 K). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a DMF solution.

Elemental analysis calculated: C 73.18, H 3.93, N, 3.41%; found: C 73.25, H 3.88, N 3.20%. ¹H NMR (DMSO-d₆): 7.38 (d, J = 8.4 Hz, 2H, ArH), 7.39 (s, 5H, ArH), 7.52 (d, J = 8.4 Hz, 2H, ArH), 7.74–7.76 (m, 2H, ArH), 7.99 (d, J = 8.8 Hz, 1H, ArH), 8.09–8.11 (m, 1H, ArH), 8.17 (d, J = 8.8 Hz, 1H, ArH), 9.19 (d, J = 7.6 Hz, 1H, ArH), 9.21 (s, 1H, ArH); IR (cm^-1): 3056(ArH), 1678(C=N), 1603, 1584, 1566, 1487, 1472, 1431(phenyl ring).

Structure description top

For related literature, see: Brock et al. (1999); Fokialakis et al. (2002); Fossa et al. (2002); Sakata et al. (1988); Sawada et al. (2004).

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97 (please check); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.

2-(4-Bromophenyl)-3-phenylbenzo[f]quinoline top

Crystal data top

C₂₅H₁₆BrN	F(000) = 832
M_r = 410.30	D_x = 1.497 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 478–480 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71070 Å
a = 12.704 (2) Å	Cell parameters from 6717 reflections
b = 9.4917 (14) Å	θ = 3.0–25.3°
c = 15.142 (3) Å	µ = 2.27 mm⁻¹
β = 94.612 (4)°	T = 193 K
V = 1819.9 (5) Å³	Block, colorless
Z = 4	0.78 × 0.55 × 0.17 mm

Data collection top

Rigaku Mercury CCD diffractometer	3336 independent reflections
Radiation source: fine-focus sealed tube	3034 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.4°, θ_min = 3.0°
ω scans	h = −15→13
Absorption correction: multi-scan (Jacobson, 1998)	k = −11→11
T_min = 0.298, T_max = 0.679	l = −18→17
17280 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.084	H-atom parameters constrained
S = 1.17	w = 1/[σ²(F_o²) + (0.0252P)² + 1.5016P] where P = (F_o² + 2F_c²)/3
3336 reflections	(Δ/σ)_max < 0.001
245 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₅H₁₆BrN	V = 1819.9 (5) Å³
M_r = 410.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.704 (2) Å	µ = 2.27 mm⁻¹
b = 9.4917 (14) Å	T = 193 K
c = 15.142 (3) Å	0.78 × 0.55 × 0.17 mm
β = 94.612 (4)°

Data collection top

Rigaku Mercury CCD diffractometer	3336 independent reflections
Absorption correction: multi-scan (Jacobson, 1998)	3034 reflections with I > 2σ(I)
T_min = 0.298, T_max = 0.679	R_int = 0.042
17280 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.084	H-atom parameters constrained
S = 1.17	Δρ_max = 0.36 e Å⁻³
3336 reflections	Δρ_min = −0.30 e Å⁻³
245 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
Br1	0.41136 (3)	−0.18517 (3)	0.83655 (2)	0.04218 (13)
N1	0.03956 (17)	0.1754 (2)	0.57827 (14)	0.0277 (5)
C1	0.1407 (2)	0.1676 (3)	0.56232 (17)	0.0257 (6)
C2	0.1811 (2)	0.2330 (3)	0.48741 (17)	0.0245 (6)
C3	0.1113 (2)	0.3102 (3)	0.43206 (17)	0.0270 (6)
H3	0.1367	0.3569	0.3825	0.032*
C4	0.0041 (2)	0.3215 (3)	0.44696 (17)	0.0247 (6)
C5	−0.0276 (2)	0.2501 (3)	0.52243 (17)	0.0268 (6)
C6	0.2081 (2)	0.0849 (3)	0.62874 (17)	0.0258 (6)
C7	0.1673 (2)	−0.0381 (3)	0.66346 (18)	0.0294 (6)
H7	0.0978	−0.0677	0.6438	0.035*
C8	0.2262 (2)	−0.1175 (3)	0.72588 (18)	0.0303 (6)
H8	0.1980	−0.2012	0.7491	0.036*
C9	0.3270 (2)	−0.0729 (3)	0.75395 (17)	0.0286 (6)
C10	0.3691 (2)	0.0492 (3)	0.72268 (18)	0.0304 (6)
H10	0.4378	0.0793	0.7438	0.036*
C11	0.3088 (2)	0.1277 (3)	0.65955 (17)	0.0271 (6)
H11	0.3371	0.2119	0.6372	0.033*
C12	0.2918 (2)	0.2181 (3)	0.46368 (17)	0.0251 (6)
C13	0.3338 (2)	0.0866 (3)	0.44567 (18)	0.0312 (7)
H13	0.2925	0.0041	0.4513	0.037*
C14	0.4349 (2)	0.0755 (3)	0.41985 (19)	0.0354 (7)
H14	0.4621	−0.0145	0.4063	0.042*
C15	0.4972 (2)	0.1933 (3)	0.41337 (19)	0.0339 (7)
H15	0.5674	0.1845	0.3966	0.041*
C16	0.4569 (2)	0.3239 (3)	0.43142 (19)	0.0331 (7)
H16	0.4994	0.4056	0.4275	0.040*
C17	0.3545 (2)	0.3359 (3)	0.45528 (18)	0.0294 (6)
H17	0.3266	0.4266	0.4661	0.035*
C18	−0.1360 (2)	0.2552 (3)	0.54188 (19)	0.0311 (7)
H18	−0.1573	0.2086	0.5930	0.037*
C19	−0.2081 (2)	0.3251 (3)	0.48871 (19)	0.0325 (7)
H19	−0.2794	0.3269	0.5031	0.039*
C20	−0.1798 (2)	0.3970 (3)	0.41076 (18)	0.0293 (6)
C21	−0.2560 (2)	0.4670 (3)	0.35408 (19)	0.0360 (7)
H21	−0.3274	0.4687	0.3685	0.043*
C22	−0.2291 (3)	0.5324 (3)	0.2787 (2)	0.0408 (8)
H22	−0.2815	0.5799	0.2415	0.049*
C23	−0.1256 (3)	0.5294 (4)	0.2567 (2)	0.0435 (8)
H23	−0.1073	0.5736	0.2038	0.052*
C24	−0.0491 (2)	0.4632 (3)	0.3106 (2)	0.0389 (7)
H24	0.0217	0.4628	0.2946	0.047*
C25	−0.0736 (2)	0.3956 (3)	0.38919 (17)	0.0276 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0505 (2)	0.0406 (2)	0.03533 (19)	0.01776 (15)	0.00243 (14)	0.00900 (15)
N1	0.0279 (13)	0.0312 (13)	0.0238 (12)	−0.0001 (10)	0.0016 (10)	0.0020 (10)
C1	0.0287 (15)	0.0247 (14)	0.0237 (14)	−0.0015 (11)	0.0011 (12)	−0.0027 (12)
C2	0.0261 (14)	0.0255 (14)	0.0219 (14)	−0.0035 (11)	0.0015 (11)	−0.0030 (11)
C3	0.0311 (15)	0.0282 (14)	0.0216 (14)	−0.0030 (12)	0.0015 (12)	0.0012 (12)
C4	0.0249 (14)	0.0258 (14)	0.0230 (14)	−0.0012 (11)	0.0004 (11)	−0.0034 (12)
C5	0.0282 (15)	0.0282 (15)	0.0236 (14)	−0.0028 (12)	0.0002 (12)	−0.0031 (12)
C6	0.0305 (15)	0.0256 (14)	0.0217 (14)	0.0043 (12)	0.0045 (12)	−0.0017 (12)
C7	0.0334 (16)	0.0292 (15)	0.0260 (15)	−0.0020 (12)	0.0042 (12)	−0.0014 (12)
C8	0.0439 (18)	0.0227 (14)	0.0254 (15)	0.0043 (13)	0.0086 (13)	−0.0001 (12)
C9	0.0340 (16)	0.0309 (15)	0.0209 (14)	0.0113 (13)	0.0027 (12)	0.0005 (12)
C10	0.0299 (16)	0.0349 (16)	0.0264 (15)	0.0027 (12)	0.0025 (12)	−0.0009 (13)
C11	0.0320 (16)	0.0261 (14)	0.0233 (14)	−0.0017 (12)	0.0022 (12)	0.0021 (12)
C12	0.0252 (14)	0.0320 (15)	0.0175 (13)	−0.0002 (12)	−0.0012 (11)	0.0015 (12)
C13	0.0315 (16)	0.0310 (16)	0.0303 (15)	−0.0037 (13)	−0.0029 (13)	−0.0039 (13)
C14	0.0339 (17)	0.0361 (17)	0.0360 (17)	0.0065 (14)	0.0015 (14)	−0.0086 (14)
C15	0.0244 (15)	0.0477 (19)	0.0299 (15)	0.0039 (14)	0.0038 (12)	−0.0037 (14)
C16	0.0331 (16)	0.0351 (17)	0.0318 (16)	−0.0052 (13)	0.0070 (13)	0.0004 (13)
C17	0.0310 (16)	0.0284 (15)	0.0294 (15)	0.0019 (12)	0.0065 (13)	0.0007 (12)
C18	0.0293 (16)	0.0371 (16)	0.0272 (15)	−0.0006 (13)	0.0043 (13)	−0.0006 (13)
C19	0.0261 (15)	0.0397 (17)	0.0324 (16)	0.0007 (13)	0.0068 (13)	−0.0073 (14)
C20	0.0298 (15)	0.0301 (15)	0.0273 (15)	0.0039 (12)	−0.0016 (12)	−0.0083 (13)
C21	0.0328 (16)	0.0414 (18)	0.0332 (17)	0.0085 (14)	−0.0023 (13)	−0.0060 (14)
C22	0.0439 (19)	0.0441 (19)	0.0324 (17)	0.0140 (15)	−0.0098 (14)	−0.0032 (15)
C23	0.044 (2)	0.050 (2)	0.0352 (18)	0.0071 (16)	−0.0035 (15)	0.0135 (15)
C24	0.0341 (17)	0.0475 (19)	0.0349 (17)	−0.0005 (14)	0.0011 (14)	0.0095 (15)
C25	0.0286 (15)	0.0284 (15)	0.0252 (14)	−0.0003 (12)	−0.0022 (12)	−0.0023 (12)

Geometric parameters (Å, º) top

Br1—C9	1.906 (3)	C13—C14	1.376 (4)
N1—C1	1.328 (3)	C13—H13	0.9500
N1—C5	1.353 (3)	C14—C15	1.379 (4)
C1—C2	1.424 (4)	C14—H14	0.9500
C1—C6	1.491 (4)	C15—C16	1.376 (4)
C2—C3	1.380 (4)	C15—H15	0.9500
C2—C12	1.485 (4)	C16—C17	1.383 (4)
C3—C4	1.403 (4)	C16—H16	0.9500
C3—H3	0.9500	C17—H17	0.9500
C4—C5	1.415 (4)	C18—C19	1.344 (4)
C4—C25	1.448 (4)	C18—H18	0.9500
C5—C18	1.432 (4)	C19—C20	1.434 (4)
C6—C11	1.387 (4)	C19—H19	0.9500
C6—C7	1.398 (4)	C20—C21	1.407 (4)
C7—C8	1.381 (4)	C20—C25	1.414 (4)
C7—H7	0.9500	C21—C22	1.366 (4)
C8—C9	1.383 (4)	C21—H21	0.9500
C8—H8	0.9500	C22—C23	1.383 (4)
C9—C10	1.376 (4)	C22—H22	0.9500
C10—C11	1.392 (4)	C23—C24	1.370 (4)
C10—H10	0.9500	C23—H23	0.9500
C11—H11	0.9500	C24—C25	1.409 (4)
C12—C17	1.385 (4)	C24—H24	0.9500
C12—C13	1.393 (4)

C1—N1—C5	119.1 (2)	C14—C13—H13	119.8
N1—C1—C2	122.5 (2)	C12—C13—H13	119.8
N1—C1—C6	114.7 (2)	C13—C14—C15	120.8 (3)
C2—C1—C6	122.8 (2)	C13—C14—H14	119.6
C3—C2—C1	117.4 (2)	C15—C14—H14	119.6
C3—C2—C12	118.5 (2)	C16—C15—C14	119.4 (3)
C1—C2—C12	124.1 (2)	C16—C15—H15	120.3
C2—C3—C4	121.8 (2)	C14—C15—H15	120.3
C2—C3—H3	119.1	C15—C16—C17	119.9 (3)
C4—C3—H3	119.1	C15—C16—H16	120.0
C3—C4—C5	115.9 (2)	C17—C16—H16	120.0
C3—C4—C25	124.3 (2)	C16—C17—C12	121.2 (3)
C5—C4—C25	119.7 (2)	C16—C17—H17	119.4
N1—C5—C4	123.3 (2)	C12—C17—H17	119.4
N1—C5—C18	117.3 (2)	C19—C18—C5	120.9 (3)
C4—C5—C18	119.4 (2)	C19—C18—H18	119.6
C11—C6—C7	118.6 (3)	C5—C18—H18	119.6
C11—C6—C1	122.5 (2)	C18—C19—C20	121.6 (3)
C7—C6—C1	118.9 (2)	C18—C19—H19	119.2
C8—C7—C6	121.0 (3)	C20—C19—H19	119.2
C8—C7—H7	119.5	C21—C20—C25	119.1 (3)
C6—C7—H7	119.5	C21—C20—C19	121.4 (3)
C7—C8—C9	118.8 (3)	C25—C20—C19	119.5 (3)
C7—C8—H8	120.6	C22—C21—C20	121.2 (3)
C9—C8—H8	120.6	C22—C21—H21	119.4
C10—C9—C8	121.8 (3)	C20—C21—H21	119.4
C10—C9—Br1	118.9 (2)	C21—C22—C23	119.8 (3)
C8—C9—Br1	119.3 (2)	C21—C22—H22	120.1
C9—C10—C11	118.7 (3)	C23—C22—H22	120.1
C9—C10—H10	120.7	C24—C23—C22	120.6 (3)
C11—C10—H10	120.7	C24—C23—H23	119.7
C6—C11—C10	121.1 (3)	C22—C23—H23	119.7
C6—C11—H11	119.5	C23—C24—C25	121.2 (3)
C10—C11—H11	119.5	C23—C24—H24	119.4
C17—C12—C13	118.2 (2)	C25—C24—H24	119.4
C17—C12—C2	120.5 (2)	C24—C25—C20	118.1 (3)
C13—C12—C2	121.2 (2)	C24—C25—C4	123.1 (3)
C14—C13—C12	120.4 (3)	C20—C25—C4	118.8 (2)

C5—N1—C1—C2	−1.2 (4)	C1—C2—C12—C17	−122.9 (3)
C5—N1—C1—C6	179.0 (2)	C3—C2—C12—C13	−117.5 (3)
N1—C1—C2—C3	2.1 (4)	C1—C2—C12—C13	59.9 (4)
C6—C1—C2—C3	−178.2 (2)	C17—C12—C13—C14	−0.3 (4)
N1—C1—C2—C12	−175.3 (2)	C2—C12—C13—C14	177.0 (3)
C6—C1—C2—C12	4.4 (4)	C12—C13—C14—C15	1.6 (4)
C1—C2—C3—C4	−1.7 (4)	C13—C14—C15—C16	−1.2 (4)
C12—C2—C3—C4	175.9 (2)	C14—C15—C16—C17	−0.4 (4)
C2—C3—C4—C5	0.5 (4)	C15—C16—C17—C12	1.7 (4)
C2—C3—C4—C25	−177.1 (3)	C13—C12—C17—C16	−1.3 (4)
C1—N1—C5—C4	0.0 (4)	C2—C12—C17—C16	−178.6 (2)
C1—N1—C5—C18	179.7 (2)	N1—C5—C18—C19	−178.8 (3)
C3—C4—C5—N1	0.4 (4)	C4—C5—C18—C19	1.0 (4)
C25—C4—C5—N1	178.2 (2)	C5—C18—C19—C20	0.1 (4)
C3—C4—C5—C18	−179.4 (2)	C18—C19—C20—C21	178.3 (3)
C25—C4—C5—C18	−1.6 (4)	C18—C19—C20—C25	−0.4 (4)
N1—C1—C6—C11	−138.9 (3)	C25—C20—C21—C22	0.4 (4)
C2—C1—C6—C11	41.3 (4)	C19—C20—C21—C22	−178.4 (3)
N1—C1—C6—C7	39.0 (3)	C20—C21—C22—C23	0.6 (5)
C2—C1—C6—C7	−140.8 (3)	C21—C22—C23—C24	−1.1 (5)
C11—C6—C7—C8	−1.2 (4)	C22—C23—C24—C25	0.5 (5)
C1—C6—C7—C8	−179.3 (2)	C23—C24—C25—C20	0.5 (4)
C6—C7—C8—C9	0.2 (4)	C23—C24—C25—C4	178.5 (3)
C7—C8—C9—C10	1.2 (4)	C21—C20—C25—C24	−0.9 (4)
C7—C8—C9—Br1	−177.56 (19)	C19—C20—C25—C24	177.9 (3)
C8—C9—C10—C11	−1.5 (4)	C21—C20—C25—C4	−179.0 (2)
Br1—C9—C10—C11	177.3 (2)	C19—C20—C25—C4	−0.2 (4)
C7—C6—C11—C10	1.0 (4)	C3—C4—C25—C24	0.8 (4)
C1—C6—C11—C10	178.9 (2)	C5—C4—C25—C24	−176.8 (3)
C9—C10—C11—C6	0.4 (4)	C3—C4—C25—C20	178.8 (3)
C3—C2—C12—C17	59.8 (3)	C5—C4—C25—C20	1.2 (4)

Experimental details

Crystal data
Chemical formula	C₂₅H₁₆BrN
M_r	410.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	193
a, b, c (Å)	12.704 (2), 9.4917 (14), 15.142 (3)
β (°)	94.612 (4)
V (Å³)	1819.9 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.27
Crystal size (mm)	0.78 × 0.55 × 0.17

Data collection
Diffractometer	Rigaku Mercury CCD
Absorption correction	Multi-scan (Jacobson, 1998)
T_min, T_max	0.298, 0.679
No. of measured, independent and observed [I > 2σ(I)] reflections	17280, 3336, 3034
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.084, 1.17
No. of reflections	3336
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.30

Computer programs: CrystalClear (Rigaku, 1999), CrystalClear, CrystalStructure (Rigaku/MSC 2000), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97 (please check), SHELXL97.

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