[N′-(5-Bromo-2-oxidobenzyl­idene-κO)-3-hydr­oxy-2-naphthohydrazidato-κ2N′,O]dimethyl­tin(IV)

Lee, S.M.; Mohd Ali, H.; Lo, K.M.

doi:10.1107/S1600536810001133

[N′-(5-Bromo-2-oxidobenzylidene-κO)-3-hydroxy-2-naphthohydrazidato-κ²N′,O]dimethyltin(IV)

The Sn^IV atom in the title compound, [Sn(CH₃)₂(C₁₈H₁₁BrN₂O₃)], shows a distorted cis-C₂NO₂Sn trigonal-bipyramidal coordination geometry, with an axial O—Sn—O angle of 155.27 (9)°. The presence of an intramolecular O—H

N hydrogen bond between the amido N atom and hydroxy H atom in the Schiff base ligand helps to stabilize the overall molecular structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810001133/sj2691sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810001133/sj2691Isup2.hkl Contains datablock I

CCDC reference: 765006

checkCIF report

Key indicators

Single-crystal X-ray study
T = 145 K
Mean (C-C) = 0.005 Å
R factor = 0.024
wR factor = 0.079
Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.94
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         97
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600        144

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)        100 Deg.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Related literature top

For related structures, see Lee et al. (2009a,b). For similar hydrazone dianions acting as O,N,O'-chelate ligands to tin in organotin compounds, see: Labib et al. (1996); Samanta et al. (2007).

Experimental top

The Schiff base ligand was prepared by the condensation reaction of 3-hydroxy-2-naphthoyl hydrazide with 5-bromosalicylaldehyde. The title compound was prepared by refluxing the Schiff base (0.74 g, 2.0 mmol) with dimethyltin oxide (0.32 g, 2.0 mmol) in toluene for 6 h. The solution was filtered and left for recrystallization for a week during which yellow crystals were obtained.

Structure description top

For related structures, see Lee et al. (2009a,b). For similar hydrazone dianions acting as O,N,O'-chelate ligands to tin in organotin compounds, see: Labib et al. (1996); Samanta et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 20080); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: pubCIF (Westrip, 2010).

Figures top

Fig. 1. The molecular structure of [N'-(5-bromo-2-oxidobenzylidene-κO)-3-hydroxy-2- naphthohydrazidato-κ²N',O]dimethyltin(IV) showing 70% probability displacement ellipsoids and the atom numbering. Hydrogen atoms are drawn as spheres of arbitrary radius.

[N'-(5-Bromo-2-oxidobenzylidene-κO)-3-hydroxy-2- naphthohydrazidato-κ²N',O]dimethyltin(IV) top

Crystal data top

[Sn(CH₃)₂(C₁₈H₁₁BrN₂O₃)]	Z = 2
M_r = 531.96	F(000) = 520
Triclinic, P1	D_x = 1.904 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8662 (5) Å	Cell parameters from 3900 reflections
b = 11.7998 (9) Å	θ = 2.5–30.6°
c = 11.9365 (9) Å	µ = 3.55 mm⁻¹
α = 87.464 (1)°	T = 145 K
β = 76.128 (1)°	Plate, yellow
γ = 81.213 (1)°	0.39 × 0.37 × 0.09 mm
V = 927.84 (12) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	4028 independent reflections
Radiation source: fine-focus sealed tube	3703 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.338, T_max = 0.740	k = −10→15
5350 measured reflections	l = −15→15

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0316P)² + 1.8608P] where P = (F_o² + 2F_c²)/3
4028 reflections	(Δ/σ)_max = 0.001
245 parameters	Δρ_max = 0.63 e Å⁻³
1 restraint	Δρ_min = −0.76 e Å⁻³

Crystal data top

[Sn(CH₃)₂(C₁₈H₁₁BrN₂O₃)]	γ = 81.213 (1)°
M_r = 531.96	V = 927.84 (12) Å³
Triclinic, P1	Z = 2
a = 6.8662 (5) Å	Mo Kα radiation
b = 11.7998 (9) Å	µ = 3.55 mm⁻¹
c = 11.9365 (9) Å	T = 145 K
α = 87.464 (1)°	0.39 × 0.37 × 0.09 mm
β = 76.128 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4028 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3703 reflections with I > 2σ(I)
T_min = 0.338, T_max = 0.740	R_int = 0.016
5350 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	1 restraint
wR(F²) = 0.079	H-atom parameters constrained
S = 1.14	Δρ_max = 0.63 e Å⁻³
4028 reflections	Δρ_min = −0.76 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
Sn1	0.75049 (3)	0.561594 (19)	0.670242 (18)	0.01412 (8)
Br1	0.57215 (5)	−0.06224 (3)	0.64595 (3)	0.02011 (9)
N1	0.5307 (4)	0.4692 (2)	0.7889 (2)	0.0141 (5)
N2	0.3995 (4)	0.5332 (3)	0.8788 (2)	0.0172 (6)
O1	0.8546 (4)	0.4001 (2)	0.5966 (2)	0.0202 (5)
O2	0.5723 (4)	0.6809 (2)	0.7987 (2)	0.0228 (5)
O3	0.1095 (4)	0.5698 (2)	1.0656 (2)	0.0219 (5)
H3	0.1750	0.5344	1.0054	0.033*
C1	0.6138 (5)	0.2791 (3)	0.6996 (3)	0.0141 (6)
C2	0.7792 (5)	0.3027 (3)	0.6092 (3)	0.0152 (6)
C3	0.8681 (5)	0.2152 (3)	0.5277 (3)	0.0188 (7)
H3A	0.9776	0.2288	0.4655	0.023*
C4	0.7999 (5)	0.1105 (3)	0.5364 (3)	0.0158 (6)
H4	0.8593	0.0541	0.4790	0.019*
C5	0.6435 (5)	0.0871 (3)	0.6295 (3)	0.0164 (6)
C6	0.5524 (5)	0.1702 (3)	0.7093 (3)	0.0154 (6)
H6	0.4459	0.1540	0.7723	0.019*
C7	0.5032 (5)	0.3630 (3)	0.7853 (3)	0.0150 (6)
H7	0.3999	0.3379	0.8450	0.018*
C8	0.4332 (5)	0.6410 (3)	0.8761 (3)	0.0164 (6)
C9	0.3027 (5)	0.7184 (3)	0.9668 (3)	0.0151 (6)
C10	0.1483 (5)	0.6797 (3)	1.0581 (3)	0.0147 (6)
C11	0.0383 (5)	0.7555 (3)	1.1419 (3)	0.0154 (6)
H11	−0.0602	0.7291	1.2037	0.018*
C12	0.0673 (5)	0.8711 (3)	1.1392 (3)	0.0139 (6)
C13	−0.0460 (5)	0.9515 (3)	1.2244 (3)	0.0189 (7)
H13	−0.1429	0.9267	1.2880	0.023*
C14	−0.0175 (5)	1.0647 (3)	1.2160 (3)	0.0190 (7)
H14	−0.0962	1.1174	1.2732	0.023*
C15	0.1279 (5)	1.1033 (3)	1.1232 (3)	0.0192 (7)
H15	0.1469	1.1816	1.1186	0.023*
C16	0.2407 (5)	1.0289 (3)	1.0405 (3)	0.0164 (6)
H16	0.3376	1.0558	0.9782	0.020*
C17	0.2153 (5)	0.9112 (3)	1.0461 (3)	0.0138 (6)
C18	0.3312 (5)	0.8320 (3)	0.9627 (3)	0.0152 (6)
H18	0.4322	0.8573	0.9017	0.018*
C19	1.0295 (5)	0.5826 (3)	0.7067 (3)	0.0201 (7)
H19A	1.0478	0.5367	0.7748	0.030*
H19B	1.0291	0.6637	0.7216	0.030*
H19C	1.1409	0.5572	0.6405	0.030*
C20	0.6241 (5)	0.6376 (3)	0.5344 (3)	0.0227 (7)
H20A	0.4933	0.6117	0.5391	0.034*
H20B	0.7165	0.6150	0.4601	0.034*
H20C	0.6040	0.7213	0.5412	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01425 (12)	0.01281 (13)	0.01497 (12)	−0.00358 (8)	−0.00180 (8)	−0.00023 (8)
Br1	0.02169 (17)	0.01283 (18)	0.02579 (18)	−0.00506 (13)	−0.00342 (14)	−0.00316 (13)
N1	0.0149 (12)	0.0107 (13)	0.0174 (13)	−0.0042 (10)	−0.0034 (10)	0.0001 (10)
N2	0.0154 (13)	0.0220 (15)	0.0131 (12)	−0.0028 (11)	−0.0010 (10)	−0.0018 (11)
O1	0.0197 (12)	0.0140 (12)	0.0244 (12)	−0.0038 (9)	0.0011 (10)	−0.0017 (10)
O2	0.0216 (12)	0.0197 (13)	0.0232 (12)	−0.0073 (10)	0.0054 (10)	−0.0029 (10)
O3	0.0292 (13)	0.0127 (12)	0.0214 (12)	−0.0114 (10)	0.0050 (10)	−0.0056 (9)
C1	0.0160 (14)	0.0122 (15)	0.0151 (14)	−0.0024 (12)	−0.0058 (12)	−0.0001 (12)
C2	0.0162 (15)	0.0134 (16)	0.0172 (15)	−0.0026 (12)	−0.0061 (12)	0.0000 (12)
C3	0.0164 (15)	0.0223 (18)	0.0160 (15)	−0.0008 (13)	−0.0022 (12)	0.0031 (13)
C4	0.0175 (15)	0.0133 (16)	0.0168 (15)	−0.0006 (12)	−0.0051 (12)	−0.0014 (12)
C5	0.0173 (15)	0.0141 (16)	0.0194 (16)	−0.0024 (12)	−0.0075 (12)	−0.0002 (13)
C6	0.0146 (14)	0.0159 (16)	0.0171 (15)	−0.0062 (12)	−0.0042 (12)	0.0015 (12)
C7	0.0157 (14)	0.0140 (16)	0.0168 (15)	−0.0063 (12)	−0.0049 (12)	0.0033 (12)
C8	0.0131 (14)	0.0223 (18)	0.0143 (15)	−0.0037 (12)	−0.0040 (12)	0.0021 (13)
C9	0.0151 (14)	0.0150 (16)	0.0157 (15)	−0.0012 (12)	−0.0051 (12)	−0.0013 (12)
C10	0.0181 (15)	0.0119 (15)	0.0155 (15)	−0.0045 (12)	−0.0047 (12)	−0.0025 (12)
C11	0.0154 (14)	0.0174 (17)	0.0139 (14)	−0.0057 (12)	−0.0024 (12)	−0.0015 (12)
C12	0.0139 (14)	0.0144 (16)	0.0149 (14)	−0.0036 (12)	−0.0050 (11)	−0.0022 (12)
C13	0.0145 (15)	0.0284 (19)	0.0137 (15)	−0.0037 (13)	−0.0029 (12)	0.0001 (13)
C14	0.0202 (16)	0.0201 (18)	0.0178 (16)	−0.0024 (13)	−0.0059 (13)	−0.0044 (13)
C15	0.0207 (16)	0.0173 (17)	0.0206 (16)	−0.0011 (13)	−0.0073 (13)	−0.0035 (13)
C16	0.0182 (15)	0.0120 (16)	0.0202 (16)	−0.0047 (12)	−0.0051 (12)	−0.0025 (12)
C17	0.0162 (14)	0.0134 (15)	0.0125 (14)	−0.0016 (12)	−0.0049 (11)	−0.0024 (12)
C18	0.0147 (14)	0.0176 (17)	0.0132 (14)	−0.0020 (12)	−0.0035 (11)	−0.0007 (12)
C19	0.0173 (15)	0.0249 (19)	0.0193 (16)	−0.0090 (14)	−0.0031 (13)	−0.0007 (14)
C20	0.0225 (17)	0.0223 (19)	0.0238 (17)	−0.0015 (14)	−0.0079 (14)	0.0017 (14)

Geometric parameters (Å, º) top

Sn1—O1	2.084 (2)	C8—C9	1.477 (5)
Sn1—C19	2.116 (3)	C9—C18	1.381 (5)
Sn1—C20	2.120 (3)	C9—C10	1.438 (4)
Sn1—O2	2.143 (2)	C10—C11	1.372 (5)
Sn1—N1	2.194 (3)	C11—C12	1.406 (5)
Br1—C5	1.890 (3)	C11—H11	0.9500
N1—C7	1.300 (4)	C12—C13	1.421 (5)
N1—N2	1.390 (4)	C12—C17	1.432 (4)
N2—C8	1.324 (5)	C13—C14	1.375 (5)
O1—C2	1.320 (4)	C13—H13	0.9500
O2—C8	1.290 (4)	C14—C15	1.412 (5)
O3—C10	1.358 (4)	C14—H14	0.9500
O3—H3	0.8400	C15—C16	1.360 (5)
C1—C6	1.404 (4)	C15—H15	0.9500
C1—C2	1.419 (4)	C16—C17	1.422 (5)
C1—C7	1.446 (5)	C16—H16	0.9500
C2—C3	1.413 (5)	C17—C18	1.405 (4)
C3—C4	1.377 (5)	C18—H18	0.9500
C3—H3A	0.9500	C19—H19A	0.9800
C4—C5	1.399 (5)	C19—H19B	0.9800
C4—H4	0.9500	C19—H19C	0.9800
C5—C6	1.367 (5)	C20—H20A	0.9800
C6—H6	0.9500	C20—H20B	0.9800
C7—H7	0.9500	C20—H20C	0.9800

O1—Sn1—C19	95.10 (12)	C18—C9—C8	118.2 (3)
O1—Sn1—C20	97.09 (13)	C10—C9—C8	122.5 (3)
C19—Sn1—C20	127.84 (14)	O3—C10—C11	118.6 (3)
O1—Sn1—O2	155.27 (9)	O3—C10—C9	122.3 (3)
C19—Sn1—O2	94.33 (12)	C11—C10—C9	119.2 (3)
C20—Sn1—O2	95.04 (13)	C10—C11—C12	121.9 (3)
O1—Sn1—N1	83.01 (10)	C10—C11—H11	119.0
C19—Sn1—N1	121.63 (12)	C12—C11—H11	119.0
C20—Sn1—N1	110.12 (12)	C11—C12—C13	123.0 (3)
O2—Sn1—N1	72.59 (10)	C11—C12—C17	119.2 (3)
C7—N1—N2	115.3 (3)	C13—C12—C17	117.8 (3)
C7—N1—Sn1	128.8 (2)	C14—C13—C12	121.0 (3)
N2—N1—Sn1	115.9 (2)	C14—C13—H13	119.5
C8—N2—N1	112.2 (3)	C12—C13—H13	119.5
C2—O1—Sn1	133.1 (2)	C13—C14—C15	120.6 (3)
C8—O2—Sn1	115.9 (2)	C13—C14—H14	119.7
C10—O3—H3	109.5	C15—C14—H14	119.7
C6—C1—C2	120.1 (3)	C16—C15—C14	120.3 (3)
C6—C1—C7	117.1 (3)	C16—C15—H15	119.9
C2—C1—C7	122.8 (3)	C14—C15—H15	119.9
O1—C2—C3	118.3 (3)	C15—C16—C17	120.7 (3)
O1—C2—C1	124.5 (3)	C15—C16—H16	119.6
C3—C2—C1	117.2 (3)	C17—C16—H16	119.6
C4—C3—C2	121.6 (3)	C18—C17—C16	122.1 (3)
C4—C3—H3A	119.2	C18—C17—C12	118.3 (3)
C2—C3—H3A	119.2	C16—C17—C12	119.6 (3)
C3—C4—C5	120.2 (3)	C9—C18—C17	121.9 (3)
C3—C4—H4	119.9	C9—C18—H18	119.0
C5—C4—H4	119.9	C17—C18—H18	119.0
C6—C5—C4	119.8 (3)	Sn1—C19—H19A	109.5
C6—C5—Br1	121.4 (2)	Sn1—C19—H19B	109.5
C4—C5—Br1	118.7 (3)	H19A—C19—H19B	109.5
C5—C6—C1	120.9 (3)	Sn1—C19—H19C	109.5
C5—C6—H6	119.5	H19A—C19—H19C	109.5
C1—C6—H6	119.5	H19B—C19—H19C	109.5
N1—C7—C1	126.6 (3)	Sn1—C20—H20A	109.5
N1—C7—H7	116.7	Sn1—C20—H20B	109.5
C1—C7—H7	116.7	H20A—C20—H20B	109.5
O2—C8—N2	123.4 (3)	Sn1—C20—H20C	109.5
O2—C8—C9	119.1 (3)	H20A—C20—H20C	109.5
N2—C8—C9	117.5 (3)	H20B—C20—H20C	109.5
C18—C9—C10	119.4 (3)

O1—Sn1—N1—C7	−5.4 (3)	Sn1—N1—C7—C1	−0.2 (5)
C19—Sn1—N1—C7	−97.1 (3)	C6—C1—C7—N1	−177.1 (3)
C20—Sn1—N1—C7	89.6 (3)	C2—C1—C7—N1	3.5 (5)
O2—Sn1—N1—C7	178.6 (3)	Sn1—O2—C8—N2	0.3 (4)
O1—Sn1—N1—N2	176.3 (2)	Sn1—O2—C8—C9	−179.4 (2)
C19—Sn1—N1—N2	84.6 (2)	N1—N2—C8—O2	0.0 (4)
C20—Sn1—N1—N2	−88.7 (2)	N1—N2—C8—C9	179.6 (3)
O2—Sn1—N1—N2	0.3 (2)	O2—C8—C9—C18	2.0 (4)
C7—N1—N2—C8	−178.8 (3)	N2—C8—C9—C18	−177.7 (3)
Sn1—N1—N2—C8	−0.3 (3)	O2—C8—C9—C10	−178.2 (3)
C19—Sn1—O1—C2	133.7 (3)	N2—C8—C9—C10	2.2 (5)
C20—Sn1—O1—C2	−97.1 (3)	C18—C9—C10—O3	178.5 (3)
O2—Sn1—O1—C2	21.7 (4)	C8—C9—C10—O3	−1.4 (5)
N1—Sn1—O1—C2	12.4 (3)	C18—C9—C10—C11	−2.7 (5)
O1—Sn1—O2—C8	−10.0 (4)	C8—C9—C10—C11	177.4 (3)
C19—Sn1—O2—C8	−122.1 (2)	O3—C10—C11—C12	−178.9 (3)
C20—Sn1—O2—C8	109.2 (2)	C9—C10—C11—C12	2.2 (5)
N1—Sn1—O2—C8	−0.3 (2)	C10—C11—C12—C13	179.4 (3)
Sn1—O1—C2—C3	166.5 (2)	C10—C11—C12—C17	0.2 (5)
Sn1—O1—C2—C1	−13.5 (5)	C11—C12—C13—C14	−177.7 (3)
C6—C1—C2—O1	−176.3 (3)	C17—C12—C13—C14	1.5 (5)
C7—C1—C2—O1	3.1 (5)	C12—C13—C14—C15	−1.0 (5)
C6—C1—C2—C3	3.7 (4)	C13—C14—C15—C16	0.4 (5)
C7—C1—C2—C3	−177.0 (3)	C14—C15—C16—C17	−0.3 (5)
O1—C2—C3—C4	178.9 (3)	C15—C16—C17—C18	−179.2 (3)
C1—C2—C3—C4	−1.1 (5)	C15—C16—C17—C12	0.9 (5)
C2—C3—C4—C5	−2.2 (5)	C11—C12—C17—C18	−2.1 (4)
C3—C4—C5—C6	2.8 (5)	C13—C12—C17—C18	178.7 (3)
C3—C4—C5—Br1	−174.0 (2)	C11—C12—C17—C16	177.8 (3)
C4—C5—C6—C1	−0.2 (5)	C13—C12—C17—C16	−1.4 (4)
Br1—C5—C6—C1	176.6 (2)	C10—C9—C18—C17	0.8 (5)
C2—C1—C6—C5	−3.1 (5)	C8—C9—C18—C17	−179.3 (3)
C7—C1—C6—C5	177.5 (3)	C16—C17—C18—C9	−178.3 (3)
N2—N1—C7—C1	178.1 (3)	C12—C17—C18—C9	1.6 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.84	1.88	2.611 (4)	144

Experimental details

Crystal data
Chemical formula	[Sn(CH₃)₂(C₁₈H₁₁BrN₂O₃)]
M_r	531.96
Crystal system, space group	Triclinic, P1
Temperature (K)	145
a, b, c (Å)	6.8662 (5), 11.7998 (9), 11.9365 (9)
α, β, γ (°)	87.464 (1), 76.128 (1), 81.213 (1)
V (Å³)	927.84 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.55
Crystal size (mm)	0.39 × 0.37 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.338, 0.740
No. of measured, independent and observed [I > 2σ(I)] reflections	5350, 4028, 3703
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.079, 1.14
No. of reflections	4028
No. of parameters	245
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.76

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 20080), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), pubCIF (Westrip, 2010).