4,4′-Dimeth­oxy-2,2′-[2,2-dimethyl­propane-1,3-diylbis(nitrilo­methanylyl­idene)]diphenol

Kargar, H.; Kia, R.; Pahlavani, E.; Tahir, M.N.

doi:10.1107/S1600536811004776

4,4′-Dimethoxy-2,2′-[2,2-dimethylpropane-1,3-diylbis(nitrilomethanylylidene)]diphenol

H. Kargar, R. Kia, E. Pahlavani and M. N. Tahir

In the title compound, C₂₁H₂₆N₂O₄, the dihedral angle between the substituted benzene rings is 30.47 (15) °. Two strong intramolecular O—H

N hydrogen bonds generate two S(6) ring motifs.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811004776/tk2716sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536811004776/tk2716Isup2.hkl Contains datablock I

CCDC reference: 815668

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R factor = 0.031
wR factor = 0.058
Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT026_ALERT_3_A Ratio Observed / Unique Reflections too Low ....         29 Perc.

Author Response: The quality of the crystal was not optimal (very platy) and it was weakly diffracting. Although recrystallization was attempted repeatedly, better crystals were not obtained and we got these results with 3 min. exposure of X-ray per frame by a STOE IPDS 2T diffractometer.


Alert level B
GOODF01_ALERT_2_B  The least squares goodness of fit parameter lies
            outside the range 0.60 <> 4.00
            Goodness of fit given =      0.565
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.94

Author Response: The quality of the crystal was not optimal (very platy) and it was weakly diffracting. Although recrystallization was attempted repeatedly, better crystals were not obtained.

PLAT911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L=  0.594        211

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           24.99
           From the CIF: _diffrn_reflns_theta_full          24.99
           From the CIF: _reflns_number_total               3375
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         3586
           Completeness (_total/calc)             94.12%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.94
PLAT086_ALERT_2_C Unsatisfactory S Value (Too Low or Not Given) ..       0.56
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C16    --  C17     ..       5.64 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1

   1 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   6 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
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 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

Schiff base ligands are one of the most prevalent systems in coordination chemistry. As part of a general study of potentially tetradenate Schiff bases (Kargar et al., 2009; Kargar et al. 2010), we have determined the crystal structure of the title compound.

The asymmetric unit of the title compound, Fig. 1, comprises a potentially tetradenate Schiff base ligand. The bond lengths are comparable to previously reported structures (Kargar et al., 2009, Kargar et al., 2010). The dihedral angle between the two benzene rings is 30.47 (15) °. Strong intramolecular O—H···N hydrogen bonds (Table 1) generate two S(6) ring motifs (Bernstein et al., 1995).

Related literature top

For hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see: Kargar et al. (2009, 2010).

Experimental top

The title compound was synthesized by adding 5-methoxy-salicylaldehyde (4 mmol) to a solution of 2,2-dimethyl-1,3-propanediamine (2 mmol) in ethanol (20 ml). The mixture was refluxed with stirring for 30 min. The resultant yellow solution was filtered. Yellow crystals were obtained by slow evaporation of its ethanol solution at room temperature over several days.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2009); cell refinement: X-AREA (Stoe & Cie, 2009); data reduction: X-AREA (Stoe & Cie, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering. Intramolecular hydrogen bonds are drawn as dashed lines.

4,4'-Dimethoxy-2,2'-[2,2-dimethylpropane-1,3- diylbis(nitrilomethanylylidene)]diphenol top

Crystal data top

C₂₁H₂₆N₂O₄	F(000) = 792
M_r = 370.44	D_x = 1.204 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3220 reflections
a = 10.660 (2) Å	θ = 2.0–24.2°
b = 21.742 (4) Å	µ = 0.08 mm⁻¹
c = 9.2767 (19) Å	T = 296 K
β = 108.03 (3)°	Plate, yellow
V = 2044.5 (7) Å³	0.23 × 0.15 × 0.08 mm
Z = 4

Data collection top

Stoe IPDS 2T Image Plate diffractometer	3375 independent reflections
Radiation source: fine-focus sealed tube	967 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
Detector resolution: 0.15 mm pixels mm^-1	θ_max = 25.0°, θ_min = 2.0°
ω scans	h = −12→12
Absorption correction: multi-scan (MULABS in PLATON; Blessing, 1995)	k = −22→25
T_min = 0.965, T_max = 1.000	l = −11→10
7094 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.058	H-atom parameters constrained
S = 0.57	w = 1/[σ²(F_o²) + (0.0172P)²] where P = (F_o² + 2F_c²)/3
3375 reflections	(Δ/σ)_max = 0.001
246 parameters	Δρ_max = 0.08 e Å⁻³
0 restraints	Δρ_min = −0.11 e Å⁻³

Crystal data top

C₂₁H₂₆N₂O₄	V = 2044.5 (7) Å³
M_r = 370.44	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.660 (2) Å	µ = 0.08 mm⁻¹
b = 21.742 (4) Å	T = 296 K
c = 9.2767 (19) Å	0.23 × 0.15 × 0.08 mm
β = 108.03 (3)°

Data collection top

Stoe IPDS 2T Image Plate diffractometer	3375 independent reflections
Absorption correction: multi-scan (MULABS in PLATON; Blessing, 1995)	967 reflections with I > 2σ(I)
T_min = 0.965, T_max = 1.000	R_int = 0.054
7094 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.058	H-atom parameters constrained
S = 0.57	Δρ_max = 0.08 e Å⁻³
3375 reflections	Δρ_min = −0.11 e Å⁻³
246 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
O1	−0.05846 (17)	0.01529 (7)	0.75824 (19)	0.0807 (6)
H1	−0.0997	0.0250	0.6727	0.121*
O2	−0.1706 (2)	0.31943 (8)	0.4769 (2)	0.0874 (6)
H2	−0.2189	0.2892	0.4703	0.131*
O3	0.4634 (2)	0.07957 (10)	0.8988 (2)	0.1064 (8)
O4	0.3081 (2)	0.30533 (10)	0.9255 (3)	0.0936 (7)
N1	−0.1073 (3)	0.07562 (9)	0.5057 (3)	0.0629 (7)
N2	−0.2263 (3)	0.21006 (10)	0.5539 (3)	0.0662 (7)
C1	0.0688 (3)	0.03241 (12)	0.7858 (4)	0.0601 (8)
C2	0.1605 (3)	0.01492 (12)	0.9224 (3)	0.0685 (8)
H2A	0.1336	−0.0083	0.9917	0.082*
C3	0.2893 (3)	0.03161 (12)	0.9549 (3)	0.0750 (9)
H3A	0.3502	0.0195	1.0460	0.090*
C4	0.3300 (3)	0.06678 (14)	0.8524 (4)	0.0720 (9)
C5	0.2413 (3)	0.08523 (12)	0.7179 (3)	0.0705 (9)
H5A	0.2691	0.1088	0.6498	0.085*
C6	0.1091 (3)	0.06829 (11)	0.6844 (3)	0.0557 (8)
C7	0.0141 (3)	0.08981 (11)	0.5447 (3)	0.0621 (8)
H7A	0.0435	0.1151	0.4811	0.075*
C8	−0.1960 (3)	0.10405 (11)	0.3705 (3)	0.0689 (8)
H8A	−0.2106	0.0760	0.2856	0.083*
H8B	−0.1554	0.1410	0.3468	0.083*
C9	−0.3286 (3)	0.12057 (12)	0.3915 (3)	0.0647 (8)
C10	−0.3096 (2)	0.15556 (12)	0.5410 (3)	0.0686 (8)
H10A	−0.3951	0.1680	0.5473	0.082*
H10B	−0.2698	0.1282	0.6255	0.082*
C11	−0.1179 (3)	0.21062 (13)	0.6614 (3)	0.0647 (9)
H11A	−0.0969	0.1777	0.7287	0.078*
C12	−0.0261 (3)	0.26170 (13)	0.6810 (3)	0.0550 (8)
C13	−0.0544 (3)	0.31384 (15)	0.5877 (3)	0.0673 (9)
C14	0.0387 (4)	0.36057 (13)	0.6113 (4)	0.0794 (11)
H14A	0.0205	0.3954	0.5500	0.095*
C15	0.1556 (4)	0.35591 (14)	0.7224 (4)	0.0804 (10)
H15A	0.2167	0.3876	0.7359	0.096*
C16	0.1861 (4)	0.30500 (14)	0.8166 (4)	0.0677 (9)
C17	0.0946 (3)	0.25820 (12)	0.7948 (3)	0.0628 (8)
H17A	0.1140	0.2238	0.8573	0.075*
C18	−0.4084 (2)	0.06177 (12)	0.3967 (3)	0.0982 (10)
H18A	−0.3598	0.0366	0.4803	0.147*
H18B	−0.4234	0.0393	0.3038	0.147*
H18C	−0.4916	0.0729	0.4092	0.147*
C19	−0.4063 (3)	0.16042 (12)	0.2556 (3)	0.0975 (10)
H19A	−0.3572	0.1971	0.2522	0.146*
H19B	−0.4901	0.1713	0.2666	0.146*
H19C	−0.4199	0.1376	0.1634	0.146*
C20	0.5161 (3)	0.11165 (14)	0.7998 (4)	0.1184 (13)
H20A	0.6098	0.1155	0.8448	0.178*
H20B	0.4771	0.1518	0.7810	0.178*
H20C	0.4974	0.0896	0.7059	0.178*
C21	0.3454 (3)	0.25225 (13)	1.0160 (3)	0.1204 (13)
H21A	0.4318	0.2581	1.0868	0.181*
H21B	0.3463	0.2175	0.9525	0.181*
H21C	0.2834	0.2450	1.0703	0.181*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0710 (15)	0.0916 (13)	0.0825 (14)	−0.0025 (12)	0.0279 (14)	0.0249 (11)
O2	0.1028 (17)	0.0767 (14)	0.0822 (16)	0.0121 (13)	0.0279 (14)	0.0188 (12)
O3	0.0738 (17)	0.154 (2)	0.0852 (18)	−0.0283 (16)	0.0154 (16)	0.0102 (14)
O4	0.0945 (18)	0.0784 (16)	0.0994 (19)	−0.0159 (14)	0.0174 (16)	0.0104 (14)
N1	0.0633 (17)	0.0646 (15)	0.0623 (18)	0.0079 (15)	0.0216 (16)	0.0016 (13)
N2	0.078 (2)	0.0597 (16)	0.0666 (19)	0.0014 (16)	0.0305 (16)	−0.0021 (14)
C1	0.060 (2)	0.0550 (19)	0.070 (2)	0.0004 (17)	0.027 (2)	−0.0008 (17)
C2	0.081 (2)	0.070 (2)	0.062 (2)	0.006 (2)	0.034 (2)	0.0144 (17)
C3	0.076 (3)	0.085 (2)	0.063 (2)	0.003 (2)	0.021 (2)	0.0031 (18)
C4	0.061 (2)	0.084 (2)	0.073 (3)	−0.015 (2)	0.024 (2)	−0.007 (2)
C5	0.069 (2)	0.082 (2)	0.064 (2)	−0.0074 (19)	0.025 (2)	0.0053 (18)
C6	0.062 (2)	0.0521 (18)	0.059 (2)	0.0031 (17)	0.027 (2)	0.0024 (16)
C7	0.079 (2)	0.0551 (19)	0.063 (2)	−0.0008 (19)	0.036 (2)	0.0015 (16)
C8	0.072 (2)	0.077 (2)	0.060 (2)	0.0013 (18)	0.025 (2)	−0.0030 (17)
C9	0.058 (2)	0.0713 (19)	0.061 (2)	−0.0044 (18)	0.0138 (19)	−0.0057 (17)
C10	0.058 (2)	0.082 (2)	0.071 (2)	0.0058 (18)	0.0274 (18)	−0.0003 (17)
C11	0.086 (3)	0.058 (2)	0.062 (2)	0.003 (2)	0.039 (2)	−0.0006 (17)
C12	0.071 (2)	0.0477 (18)	0.053 (2)	0.0033 (18)	0.0293 (19)	−0.0010 (17)
C13	0.080 (3)	0.067 (2)	0.061 (2)	0.012 (2)	0.031 (2)	0.001 (2)
C14	0.112 (3)	0.051 (2)	0.089 (3)	0.004 (2)	0.050 (3)	0.017 (2)
C15	0.105 (3)	0.057 (2)	0.092 (3)	−0.007 (2)	0.048 (3)	0.002 (2)
C16	0.086 (3)	0.057 (2)	0.066 (2)	0.007 (2)	0.032 (2)	0.0060 (19)
C17	0.082 (2)	0.0454 (19)	0.065 (2)	−0.0025 (19)	0.029 (2)	0.0042 (16)
C18	0.085 (2)	0.099 (2)	0.102 (3)	−0.023 (2)	0.017 (2)	−0.015 (2)
C19	0.093 (2)	0.108 (2)	0.078 (2)	0.017 (2)	0.006 (2)	0.012 (2)
C20	0.082 (3)	0.161 (3)	0.113 (3)	−0.043 (2)	0.032 (2)	0.014 (2)
C21	0.114 (3)	0.098 (3)	0.119 (3)	−0.014 (2)	−0.008 (2)	0.028 (2)

Geometric parameters (Å, º) top

O1—C1	1.353 (3)	C9—C19	1.543 (3)
O1—H1	0.8074	C9—C18	1.544 (3)
O2—C13	1.348 (3)	C10—H10A	0.9700
O2—H2	0.8251	C10—H10B	0.9700
O3—C4	1.381 (3)	C11—C12	1.454 (3)
O3—C20	1.402 (3)	C11—H11A	0.9300
O4—C16	1.377 (3)	C12—C17	1.391 (3)
O4—C21	1.410 (3)	C12—C13	1.401 (3)
N1—C7	1.269 (3)	C13—C14	1.390 (3)
N1—C8	1.455 (3)	C14—C15	1.353 (4)
N2—C11	1.272 (3)	C14—H14A	0.9300
N2—C10	1.463 (3)	C15—C16	1.385 (3)
C1—C6	1.389 (3)	C15—H15A	0.9300
C1—C2	1.392 (3)	C16—C17	1.380 (3)
C2—C3	1.360 (3)	C17—H17A	0.9300
C2—H2A	0.9300	C18—H18A	0.9600
C3—C4	1.390 (3)	C18—H18B	0.9600
C3—H3A	0.9300	C18—H18C	0.9600
C4—C5	1.371 (3)	C19—H19A	0.9600
C5—C6	1.395 (3)	C19—H19B	0.9600
C5—H5A	0.9300	C19—H19C	0.9600
C6—C7	1.453 (3)	C20—H20A	0.9600
C7—H7A	0.9300	C20—H20B	0.9600
C8—C9	1.528 (3)	C20—H20C	0.9600
C8—H8A	0.9700	C21—H21A	0.9600
C8—H8B	0.9700	C21—H21B	0.9600
C9—C10	1.539 (3)	C21—H21C	0.9600

C1—O1—H1	108.8	N2—C11—C12	121.2 (3)
C13—O2—H2	112.9	N2—C11—H11A	119.4
C4—O3—C20	118.6 (3)	C12—C11—H11A	119.4
C16—O4—C21	117.4 (2)	C17—C12—C13	119.0 (3)
C7—N1—C8	118.4 (2)	C17—C12—C11	118.8 (3)
C11—N2—C10	116.9 (3)	C13—C12—C11	122.2 (3)
O1—C1—C6	121.9 (3)	O2—C13—C14	119.8 (3)
O1—C1—C2	118.5 (3)	O2—C13—C12	121.0 (3)
C6—C1—C2	119.5 (3)	C14—C13—C12	119.2 (3)
C3—C2—C1	120.3 (3)	C15—C14—C13	120.6 (3)
C3—C2—H2A	119.8	C15—C14—H14A	119.7
C1—C2—H2A	119.8	C13—C14—H14A	119.7
C2—C3—C4	120.1 (3)	C14—C15—C16	121.5 (3)
C2—C3—H3A	119.9	C14—C15—H15A	119.3
C4—C3—H3A	119.9	C16—C15—H15A	119.3
C5—C4—O3	125.3 (3)	O4—C16—C17	125.1 (3)
C5—C4—C3	120.7 (3)	O4—C16—C15	116.3 (3)
O3—C4—C3	114.0 (3)	C17—C16—C15	118.6 (3)
C4—C5—C6	119.3 (3)	C16—C17—C12	121.1 (3)
C4—C5—H5A	120.3	C16—C17—H17A	119.4
C6—C5—H5A	120.3	C12—C17—H17A	119.4
C1—C6—C5	120.0 (3)	C9—C18—H18A	109.5
C1—C6—C7	120.5 (3)	C9—C18—H18B	109.5
C5—C6—C7	119.4 (3)	H18A—C18—H18B	109.5
N1—C7—C6	123.0 (3)	C9—C18—H18C	109.5
N1—C7—H7A	118.5	H18A—C18—H18C	109.5
C6—C7—H7A	118.5	H18B—C18—H18C	109.5
N1—C8—C9	111.7 (2)	C9—C19—H19A	109.5
N1—C8—H8A	109.3	C9—C19—H19B	109.5
C9—C8—H8A	109.3	H19A—C19—H19B	109.5
N1—C8—H8B	109.3	C9—C19—H19C	109.5
C9—C8—H8B	109.3	H19A—C19—H19C	109.5
H8A—C8—H8B	107.9	H19B—C19—H19C	109.5
C8—C9—C10	111.2 (2)	O3—C20—H20A	109.5
C8—C9—C19	108.1 (2)	O3—C20—H20B	109.5
C10—C9—C19	110.3 (2)	H20A—C20—H20B	109.5
C8—C9—C18	110.4 (2)	O3—C20—H20C	109.5
C10—C9—C18	107.6 (2)	H20A—C20—H20C	109.5
C19—C9—C18	109.2 (2)	H20B—C20—H20C	109.5
N2—C10—C9	112.4 (2)	O4—C21—H21A	109.5
N2—C10—H10A	109.1	O4—C21—H21B	109.5
C9—C10—H10A	109.1	H21A—C21—H21B	109.5
N2—C10—H10B	109.1	O4—C21—H21C	109.5
C9—C10—H10B	109.1	H21A—C21—H21C	109.5
H10A—C10—H10B	107.9	H21B—C21—H21C	109.5

O1—C1—C2—C3	−179.5 (2)	C11—N2—C10—C9	−116.9 (3)
C6—C1—C2—C3	−1.5 (4)	C8—C9—C10—N2	54.6 (3)
C1—C2—C3—C4	0.6 (4)	C19—C9—C10—N2	−65.3 (3)
C20—O3—C4—C5	−2.9 (4)	C18—C9—C10—N2	175.7 (2)
C20—O3—C4—C3	176.3 (3)	C10—N2—C11—C12	177.96 (19)
C2—C3—C4—C5	0.2 (4)	N2—C11—C12—C17	−176.1 (3)
C2—C3—C4—O3	−179.0 (3)	N2—C11—C12—C13	3.0 (4)
O3—C4—C5—C6	179.1 (3)	C17—C12—C13—O2	−179.4 (2)
C3—C4—C5—C6	−0.1 (4)	C11—C12—C13—O2	1.5 (4)
O1—C1—C6—C5	179.6 (2)	C17—C12—C13—C14	0.1 (3)
C2—C1—C6—C5	1.7 (4)	C11—C12—C13—C14	−179.0 (2)
O1—C1—C6—C7	1.1 (4)	O2—C13—C14—C15	179.7 (3)
C2—C1—C6—C7	−176.8 (2)	C12—C13—C14—C15	0.2 (4)
C4—C5—C6—C1	−0.9 (4)	C13—C14—C15—C16	−0.4 (5)
C4—C5—C6—C7	177.6 (3)	C21—O4—C16—C17	3.8 (4)
C8—N1—C7—C6	174.6 (2)	C21—O4—C16—C15	−175.7 (2)
C1—C6—C7—N1	−2.5 (4)	C14—C15—C16—O4	179.9 (3)
C5—C6—C7—N1	179.0 (3)	C14—C15—C16—C17	0.3 (4)
C7—N1—C8—C9	−140.7 (2)	O4—C16—C17—C12	−179.6 (2)
N1—C8—C9—C10	48.8 (3)	C15—C16—C17—C12	−0.1 (4)
N1—C8—C9—C19	170.1 (2)	C13—C12—C17—C16	−0.1 (4)
N1—C8—C9—C18	−70.5 (3)	C11—C12—C17—C16	179.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.81	1.88	2.593 (3)	147
O2—H2···N2	0.83	1.90	2.604 (3)	143

Experimental details

Crystal data
Chemical formula	C₂₁H₂₆N₂O₄
M_r	370.44
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.660 (2), 21.742 (4), 9.2767 (19)
β (°)	108.03 (3)
V (Å³)	2044.5 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.23 × 0.15 × 0.08

Data collection
Diffractometer	Stoe IPDS 2T Image Plate diffractometer
Absorption correction	Multi-scan (MULABS in PLATON; Blessing, 1995)
T_min, T_max	0.965, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7094, 3375, 967
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.058, 0.57
No. of reflections	3375
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.08, −0.11

Computer programs: X-AREA (Stoe & Cie, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).