(S)-O-[4-(2,2,4-Trimethyl­chroman-4-yl)phen­yl] N,N-dimethyl­thio­carbamate

Jacobs, T.; Bredenkamp, M.W.

doi:10.1107/S160053680705249X

(S)-O-[4-(2,2,4-Trimethylchroman-4-yl)phenyl] N,N-dimethylthiocarbamate

Crystallization of the (S)-enantiomer of the title compound, C₂₁H₂₆NO₂S, from methanol gave an unsolvated crystal structure in which one-dimensional strands of molecules are formed through a series of C—H

O and C—H

S hydrogen bonds, and C—H

π interactions.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705249X/lx2021sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680705249X/lx2021Isup2.hkl Contains datablock I

CCDC reference: 667448

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.003 Å
R factor = 0.041
wR factor = 0.109
Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.99
           From the CIF: _reflns_number_total               3574
           Count of symmetry unique reflns         2216
           Completeness (_total/calc)            161.28%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1358
           Fraction of Friedel pairs measured     0.613
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   3 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
   1 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

Comment top

In an ongoing investigation of Dianin's compound (4-p-hydroxyphenyl-2,2,4-trimethylchroman) (Flippen et al., 1970) and the inclusion chemistry of its derivatives, we synthesized the title compound (Fig. 1, I) (Esterhuysen et al., 2005; Lloyd et al.,2005; Lloyd & Bredenkamp, 2005; Lloyd et al., 2006; Jacobs et al., 2006).

The title compound was synthesized as a chirally pure intermediate from (S)-4-(4-Hydroxyphenyl)-2,2,4-trimethylchroman in the preparation of the resolved thiol derivative of Dianin's compound. Here we report the structure of the resolved dimethylthiocarbamate derivative, which is very different from the corresponding racemic structure (de Vries et al., 2005). The molecules form bilayer-type sheets in the [100] plane (Fig 2). The molecule packing is stabilized by C—H···O and C—H···S hydrogen bonds, and intermolecular C—H···π interactions (Table 1, Cg is the centroid of the C10—C15 benzene ring), with the dimethylthiocarbamate moieties associating and the chroman moieties pointing towards each other.

Related literature top

For related literature, see: Esterhuysen et al. (2005); Flippen et al. (1970); Hardy et al. (1979); Jacobs et al. (2006); Lloyd & Bredenkamp (2005); Lloyd, Alen, Bredenkamp et al. (2006); Lloyd, Alen, Jacobs et al. (2006); Lloyd et al. (2005); de Vries et al. (2005); Brienne & Jacques (1975). Cg is the centroid of the C10–C15 benzene ring

Experimental top

(S)-4-p-hydroxyphenyl-2,2,4-trimethylchroman was chirally resolved according to the literature method (Brienne & Jacques, 1975) from a racemic mixture of the compound. This chirally pure species was then converted into the title compound according to the literature method (Hardy et al., 1979). Single crystals suitable for X-ray analysis were obtained by slow evaporation from a methanol solution.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001; Atwood & Barbour, 2003); software used to prepare material for publication: X-SEED (Barbour, 2001; Atwood & Barbour, 2003).

Figures top

	Fig. 1. The molecular structure of (I), showing atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The bilayer-type packing of compound I, intermolecular interactions are shown as red dashed lines. Cg denotes the ring centroid. [Symmetry codes: (i) 1 - x, y - 1/2, -z; (ii) x, 1 + y, z; (iii) x, y - 1, z; (iv) 1 - x, y + 1/2, -z.]

(S)-O-[4-(2,2,4-Trimethylchroman-4-yl)phenyl] N,N-dimethylthiocarbamate top

Crystal data top

C₂₁H₂₅NO₂S	F(000) = 380
M_r = 355.48	D_x = 1.260 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1032 reflections
a = 6.5858 (5) Å	θ = 2.3–19.3°
b = 7.1397 (5) Å	µ = 0.19 mm⁻¹
c = 19.996 (1) Å	T = 100 K
β = 94.780 (1)°	Blocks, colourless
V = 936.95 (11) Å³	0.21 × 0.18 × 0.15 mm
Z = 2

Data collection top

Bruker APEX CCD area-detector diffractometer	3479 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.043
Graphite monochromator	θ_max = 27.0°, θ_min = 1.0°
Detector resolution: 10.0 pixels mm^-1	h = −6→8
ω scans	k = −8→9
5663 measured reflections	l = −25→23
3574 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0762P)² + 0.15P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3574 reflections	Δρ_max = 0.46 e Å⁻³
228 parameters	Δρ_min = −0.26 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1358 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (7)

Crystal data top

C₂₁H₂₅NO₂S	V = 936.95 (11) Å³
M_r = 355.48	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 6.5858 (5) Å	µ = 0.19 mm⁻¹
b = 7.1397 (5) Å	T = 100 K
c = 19.996 (1) Å	0.21 × 0.18 × 0.15 mm
β = 94.780 (1)°

Data collection top

Bruker APEX CCD area-detector diffractometer	3479 reflections with I > 2σ(I)
5663 measured reflections	R_int = 0.043
3574 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.109	Δρ_max = 0.46 e Å⁻³
S = 1.04	Δρ_min = −0.26 e Å⁻³
3574 reflections	Absolute structure: Flack (1983), 1358 Friedel pairs
228 parameters	Absolute structure parameter: 0.01 (7)
1 restraint

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
S	0.28200 (7)	0.52502 (8)	0.44057 (2)	0.02235 (14)
O1	0.8148 (2)	0.1302 (2)	0.07012 (7)	0.0197 (3)
O2	0.5200 (2)	0.7164 (2)	0.36253 (7)	0.0236 (3)
N	0.3274 (3)	0.8928 (3)	0.42094 (9)	0.0228 (4)
C1	0.9298 (3)	0.2663 (3)	0.11193 (9)	0.0179 (4)
C2	0.9973 (3)	0.1746 (3)	0.17922 (9)	0.0162 (4)
H2A	1.0753	0.2678	0.2076	0.019*
H2B	1.0911	0.0702	0.1710	0.019*
C3	0.8242 (3)	0.0978 (3)	0.21874 (9)	0.0148 (4)
C4	0.6675 (3)	0.0035 (3)	0.16921 (9)	0.0151 (4)
C5	0.5173 (3)	−0.1144 (3)	0.19136 (9)	0.0170 (4)
H5	0.5098	−0.1308	0.2382	0.020*
C6	0.3786 (3)	−0.2084 (3)	0.14704 (10)	0.0198 (4)
H6	0.2777	−0.2870	0.1636	0.024*
C7	0.3887 (3)	−0.1864 (3)	0.07831 (10)	0.0189 (4)
H7	0.2949	−0.2500	0.0476	0.023*
C8	0.5361 (3)	−0.0713 (3)	0.05506 (9)	0.0186 (4)
H8	0.5438	−0.0568	0.0081	0.022*
C9	0.6736 (3)	0.0237 (3)	0.09965 (9)	0.0159 (3)
C10	0.7311 (3)	0.2545 (3)	0.25958 (9)	0.0147 (4)
C11	0.5289 (3)	0.3112 (3)	0.24875 (9)	0.0165 (4)
H11	0.4411	0.2478	0.2161	0.020*
C12	0.4517 (3)	0.4591 (3)	0.28479 (10)	0.0179 (4)
H12	0.3137	0.4972	0.2765	0.021*
C13	0.5801 (3)	0.5485 (3)	0.33256 (9)	0.0181 (4)
C14	0.7813 (3)	0.4949 (3)	0.34578 (9)	0.0187 (4)
H14	0.8673	0.5576	0.3791	0.022*
C15	0.8553 (3)	0.3475 (3)	0.30932 (9)	0.0177 (4)
H15	0.9929	0.3090	0.3183	0.021*
C16	0.3755 (3)	0.7167 (3)	0.40763 (9)	0.0167 (4)
C17	1.1158 (3)	0.3091 (3)	0.07366 (10)	0.0224 (4)
H17A	1.0710	0.3600	0.0294	0.027*
H17B	1.1933	0.1937	0.0683	0.027*
H17C	1.2023	0.4010	0.0988	0.027*
C18	0.8008 (3)	0.4421 (3)	0.11708 (11)	0.0227 (4)
H18A	0.6748	0.4104	0.1374	0.027*
H18B	0.7672	0.4940	0.0721	0.027*
H18C	0.8773	0.5351	0.1450	0.027*
C19	0.9192 (3)	−0.0513 (3)	0.26836 (10)	0.0205 (4)
H19A	1.0249	0.0072	0.2989	0.025*
H19B	0.9799	−0.1517	0.2432	0.025*
H19C	0.8130	−0.1037	0.2944	0.025*
C20	0.4249 (4)	1.0515 (3)	0.39042 (11)	0.0298 (5)
H20A	0.5669	1.0611	0.4091	0.045*
H20B	0.3522	1.1670	0.3999	0.045*
H20C	0.4210	1.0328	0.3418	0.045*
C21	0.1799 (4)	0.9357 (4)	0.46943 (12)	0.0313 (5)
H21A	0.0415	0.9238	0.4477	0.047*
H21B	0.2015	1.0640	0.4859	0.047*
H21C	0.1978	0.8480	0.5072	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0260 (2)	0.0186 (2)	0.0239 (2)	−0.0034 (2)	0.01069 (18)	−0.0010 (2)
O1	0.0236 (7)	0.0221 (7)	0.0143 (6)	−0.0046 (6)	0.0065 (5)	−0.0005 (6)
O2	0.0322 (8)	0.0145 (7)	0.0267 (7)	−0.0010 (7)	0.0171 (6)	−0.0043 (6)
N	0.0322 (10)	0.0172 (9)	0.0205 (8)	0.0033 (8)	0.0119 (7)	−0.0025 (7)
C1	0.0183 (9)	0.0181 (10)	0.0178 (9)	−0.0012 (8)	0.0045 (7)	−0.0020 (8)
C2	0.0151 (8)	0.0158 (10)	0.0184 (9)	0.0018 (7)	0.0051 (6)	−0.0007 (7)
C3	0.0157 (9)	0.0152 (9)	0.0138 (8)	0.0002 (8)	0.0030 (7)	−0.0017 (7)
C4	0.0174 (8)	0.0121 (9)	0.0161 (8)	0.0022 (8)	0.0033 (6)	−0.0029 (8)
C5	0.0210 (9)	0.0158 (9)	0.0149 (8)	−0.0003 (8)	0.0058 (7)	−0.0008 (7)
C6	0.0212 (9)	0.0140 (9)	0.0252 (10)	−0.0009 (8)	0.0070 (8)	−0.0022 (8)
C7	0.0201 (9)	0.0137 (9)	0.0228 (9)	0.0007 (8)	0.0010 (7)	−0.0046 (8)
C8	0.0224 (9)	0.0188 (10)	0.0151 (8)	0.0038 (8)	0.0040 (7)	−0.0017 (8)
C9	0.0166 (8)	0.0142 (8)	0.0175 (8)	0.0024 (9)	0.0052 (6)	−0.0003 (8)
C10	0.0191 (9)	0.0126 (9)	0.0132 (8)	−0.0001 (8)	0.0068 (7)	0.0004 (7)
C11	0.0191 (9)	0.0157 (10)	0.0152 (8)	−0.0008 (8)	0.0043 (7)	−0.0013 (7)
C12	0.0176 (9)	0.0170 (10)	0.0201 (9)	0.0037 (8)	0.0078 (7)	0.0022 (7)
C13	0.0263 (9)	0.0119 (10)	0.0175 (8)	−0.0009 (8)	0.0106 (7)	−0.0017 (7)
C14	0.0235 (9)	0.0175 (10)	0.0157 (8)	−0.0043 (8)	0.0049 (7)	−0.0020 (7)
C15	0.0186 (9)	0.0203 (10)	0.0146 (8)	0.0009 (8)	0.0044 (7)	0.0012 (7)
C16	0.0183 (9)	0.0187 (10)	0.0137 (8)	0.0007 (8)	0.0043 (7)	−0.0008 (7)
C17	0.0235 (10)	0.0217 (11)	0.0234 (10)	−0.0022 (9)	0.0108 (8)	−0.0001 (8)
C18	0.0248 (10)	0.0198 (10)	0.0245 (10)	0.0045 (9)	0.0077 (8)	0.0050 (8)
C19	0.0232 (9)	0.0192 (10)	0.0193 (9)	0.0045 (9)	0.0017 (7)	0.0002 (8)
C20	0.0473 (13)	0.0154 (11)	0.0285 (11)	0.0012 (10)	0.0128 (9)	0.0003 (8)
C21	0.0375 (12)	0.0286 (12)	0.0305 (11)	0.0058 (11)	0.0188 (10)	−0.0068 (10)

Geometric parameters (Å, º) top

S—C16	1.659 (2)	C8—H8	0.9500
O1—C9	1.372 (2)	C10—C11	1.391 (3)
O1—C1	1.452 (2)	C10—C15	1.401 (3)
O2—C16	1.365 (2)	C11—C12	1.398 (3)
O2—C13	1.411 (2)	C11—H11	0.9500
N—C16	1.329 (3)	C12—C13	1.379 (3)
N—C20	1.461 (3)	C12—H12	0.9500
N—C21	1.461 (3)	C13—C14	1.383 (3)
C1—C18	1.525 (3)	C14—C15	1.392 (3)
C1—C17	1.529 (3)	C14—H14	0.9500
C1—C2	1.529 (3)	C15—H15	0.9500
C2—C3	1.541 (2)	C17—H17A	0.9800
C2—H2A	0.9900	C17—H17B	0.9800
C2—H2B	0.9900	C17—H17C	0.9800
C3—C4	1.526 (2)	C18—H18A	0.9800
C3—C10	1.542 (3)	C18—H18B	0.9800
C3—C19	1.551 (3)	C18—H18C	0.9800
C4—C5	1.399 (3)	C19—H19A	0.9800
C4—C9	1.402 (2)	C19—H19B	0.9800
C5—C6	1.391 (3)	C19—H19C	0.9800
C5—H5	0.9500	C20—H20A	0.9800
C6—C7	1.390 (3)	C20—H20B	0.9800
C6—H6	0.9500	C20—H20C	0.9800
C7—C8	1.382 (3)	C21—H21A	0.9800
C7—H7	0.9500	C21—H21B	0.9800
C8—C9	1.393 (3)	C21—H21C	0.9800

C9—O1—C1	117.53 (14)	C12—C11—H11	119.2
C16—O2—C13	121.16 (15)	C13—C12—C11	118.60 (18)
C16—N—C20	121.99 (17)	C13—C12—H12	120.7
C16—N—C21	120.92 (19)	C11—C12—H12	120.7
C20—N—C21	117.04 (18)	C12—C13—C14	121.78 (18)
O1—C1—C18	108.83 (17)	C12—C13—O2	120.66 (18)
O1—C1—C17	104.27 (15)	C14—C13—O2	116.86 (18)
C18—C1—C17	110.09 (17)	C13—C14—C15	118.75 (18)
O1—C1—C2	108.65 (16)	C13—C14—H14	120.6
C18—C1—C2	114.59 (16)	C15—C14—H14	120.6
C17—C1—C2	109.87 (16)	C14—C15—C10	121.39 (19)
C1—C2—C3	115.50 (16)	C14—C15—H15	119.3
C1—C2—H2A	108.4	C10—C15—H15	119.3
C3—C2—H2A	108.4	N—C16—O2	108.95 (17)
C1—C2—H2B	108.4	N—C16—S	126.74 (15)
C3—C2—H2B	108.4	O2—C16—S	124.30 (15)
H2A—C2—H2B	107.5	C1—C17—H17A	109.5
C4—C3—C2	108.26 (14)	C1—C17—H17B	109.5
C4—C3—C10	112.73 (15)	H17A—C17—H17B	109.5
C2—C3—C10	110.92 (16)	C1—C17—H17C	109.5
C4—C3—C19	109.12 (16)	H17A—C17—H17C	109.5
C2—C3—C19	107.21 (15)	H17B—C17—H17C	109.5
C10—C3—C19	108.45 (15)	C1—C18—H18A	109.5
C5—C4—C9	117.09 (17)	C1—C18—H18B	109.5
C5—C4—C3	121.19 (16)	H18A—C18—H18B	109.5
C9—C4—C3	121.65 (17)	C1—C18—H18C	109.5
C6—C5—C4	122.19 (17)	H18A—C18—H18C	109.5
C6—C5—H5	118.9	H18B—C18—H18C	109.5
C4—C5—H5	118.9	C3—C19—H19A	109.5
C7—C6—C5	119.49 (19)	C3—C19—H19B	109.5
C7—C6—H6	120.3	H19A—C19—H19B	109.5
C5—C6—H6	120.3	C3—C19—H19C	109.5
C8—C7—C6	119.52 (18)	H19A—C19—H19C	109.5
C8—C7—H7	120.2	H19B—C19—H19C	109.5
C6—C7—H7	120.2	N—C20—H20A	109.5
C7—C8—C9	120.77 (17)	N—C20—H20B	109.5
C7—C8—H8	119.6	H20A—C20—H20B	109.5
C9—C8—H8	119.6	N—C20—H20C	109.5
O1—C9—C8	114.96 (15)	H20A—C20—H20C	109.5
O1—C9—C4	124.07 (17)	H20B—C20—H20C	109.5
C8—C9—C4	120.93 (18)	N—C21—H21A	109.5
C11—C10—C15	117.86 (17)	N—C21—H21B	109.5
C11—C10—C3	123.12 (17)	H21A—C21—H21B	109.5
C15—C10—C3	119.02 (17)	N—C21—H21C	109.5
C10—C11—C12	121.60 (18)	H21A—C21—H21C	109.5
C10—C11—H11	119.2	H21B—C21—H21C	109.5

C9—O1—C1—C18	−81.6 (2)	C5—C4—C9—C8	−0.5 (3)
C9—O1—C1—C17	160.98 (17)	C3—C4—C9—C8	176.53 (18)
C9—O1—C1—C2	43.8 (2)	C4—C3—C10—C11	−4.1 (3)
O1—C1—C2—C3	−58.0 (2)	C2—C3—C10—C11	117.48 (19)
C18—C1—C2—C3	63.9 (2)	C19—C3—C10—C11	−125.04 (19)
C17—C1—C2—C3	−171.53 (17)	C4—C3—C10—C15	177.00 (16)
C1—C2—C3—C4	40.8 (2)	C2—C3—C10—C15	−61.4 (2)
C1—C2—C3—C10	−83.3 (2)	C19—C3—C10—C15	56.1 (2)
C1—C2—C3—C19	158.42 (16)	C15—C10—C11—C12	1.6 (3)
C2—C3—C4—C5	165.70 (17)	C3—C10—C11—C12	−177.26 (17)
C10—C3—C4—C5	−71.2 (2)	C10—C11—C12—C13	−0.7 (3)
C19—C3—C4—C5	49.3 (2)	C11—C12—C13—C14	−0.4 (3)
C2—C3—C4—C9	−11.2 (3)	C11—C12—C13—O2	169.79 (16)
C10—C3—C4—C9	111.9 (2)	C16—O2—C13—C12	72.1 (2)
C19—C3—C4—C9	−127.53 (19)	C16—O2—C13—C14	−117.3 (2)
C9—C4—C5—C6	−0.1 (3)	C12—C13—C14—C15	0.5 (3)
C3—C4—C5—C6	−177.08 (19)	O2—C13—C14—C15	−170.06 (17)
C4—C5—C6—C7	0.4 (3)	C13—C14—C15—C10	0.5 (3)
C5—C6—C7—C8	−0.1 (3)	C11—C10—C15—C14	−1.6 (3)
C6—C7—C8—C9	−0.4 (3)	C3—C10—C15—C14	177.39 (17)
C1—O1—C9—C8	165.62 (18)	C20—N—C16—O2	−0.9 (3)
C1—O1—C9—C4	−16.5 (3)	C21—N—C16—O2	−178.18 (19)
C7—C8—C9—O1	178.71 (18)	C20—N—C16—S	177.94 (17)
C7—C8—C9—C4	0.7 (3)	C21—N—C16—S	0.7 (3)
C5—C4—C9—O1	−178.26 (18)	C13—O2—C16—N	−171.51 (18)
C3—C4—C9—O1	−1.3 (3)	C13—O2—C16—S	9.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1ⁱ	0.95	2.55	3.414 (2)	151
C20—H20B···Sⁱⁱ	0.98	2.73	3.671 (2)	160
C20—H20C···Cgⁱⁱ	0.98	3.22	3.543 (3)	101

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₅NO₂S
M_r	355.48
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	6.5858 (5), 7.1397 (5), 19.996 (1)
β (°)	94.780 (1)
V (Å³)	936.95 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.21 × 0.18 × 0.15

Data collection
Diffractometer	Bruker APEX CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5663, 3574, 3479
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.109, 1.04
No. of reflections	3574
No. of parameters	228
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.26
Absolute structure	Flack (1983), 1358 Friedel pairs
Absolute structure parameter	0.01 (7)

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001; Atwood & Barbour, 2003).