3-[Bis(dimethyl­amino)­methyl­ene]-1,1-diphenyl­urea

Tiritiris, I.

doi:10.1107/S160053681204127X

organic compounds

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Volume 68| Part 11| November 2012| Page o3085

doi:10.1107/S160053681204127X

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3-[Bis(dimethylamino)methylene]-1,1-diphenylurea

Ioannis Tiritiris ^a ^*

^aFakultät Chemie/Organische Chemie, Hochschule Aalen, Beethovenstrasse 1, D-73430 Aalen, Germany
^*Correspondence e-mail: Ioannis.Tiritiris@htw-aalen.de

(Received 20 September 2012; accepted 1 October 2012; online 6 October 2012)

In the title compound, C₁₈H₂₂N₄O, the C=N and C—N bond lengths in the CN₃ unit are 1.3179 (11), 1.3551 (11) and 1.3737 (11) Å, indicating double- and single-bond character, respectively. The N—C—N angles are 115.91 (8), 118.20 (8) and 125.69 (8), showing a deviation of the CN₃ plane from an ideal trigonal–planar geometry. The bonds between the N atoms and the terminal C-methyl groups all have values close to a typical single bond [1.4529 (12)–1.4624 (12) Å]. The dihedral angle between the phenyl rings is 79.63 (4)°. In the crystal, the molecules are connected via weak C—H⋯O hydrogen bonds, generating chains along [100].

Related literature

For synthesis of N-dimethylcarbamoyl-N′,N′,N′′,N′′-tetramethylguanidine, see: Möllers et al. (2003 ). For the crystal structures of 2- and 5-azido-N-(diphenylcarbamoyl) proline methyl ester, see: Lynch et al. (1995 ).

Experimental

Crystal data

C₁₈H₂₂N₄O
M_r = 310.40
Monoclinic, P 2₁ /c
a = 7.9321 (3) Å
b = 17.0477 (9) Å
c = 12.2151 (6) Å
β = 98.583 (2)°
V = 1633.28 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.25 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII Duo diffractometer
51490 measured reflections
4990 independent reflections
4200 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.105
S = 1.04
4990 reflections
212 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O1ⁱ	0.95	2.59	3.3893 (12)	141
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681204127X/im2403sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681204127X/im2403Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681204127X/im2403Isup3.cml

checkCIF report

Comment top

3-[bis(dimethylamino)methylene]-1,1-diphenylurea - also known as N-diphenylcarbamoyl-N',N',N'',N''- tetramethylguanidine - is a guanidine derivative bearing an additional urea moiety. Similar to 3-[bis(dimethylamino)methylene]-1,1-dimethylurea (N-dimethylcarbamoyl- N',N',N'',N''-tetramethylguanidine; Möllers et al., 2003), it can be used as a ligand in coordination chemistry to coordinate transition metals through one imino nitrogen and one carbonyl oxygen atom. Therefore, it proved to be important to determine the hitherto unknown crystal structure of the free ligand, to enable comparative investigations. According to the structure analysis, the C1–N3 bond in the title compound is 1.3179 (11) Å, indicating double bond character. The bond lengths C1–N2 = 1.3551 (11) Å and C1–N1 = 1.3737 (11) Å are elongated and characteristic for C_imine–N_amine single bonds. The N–C1–N angles are: 115.91 (8)° (N1–C1–N2), 118.20 (8)° (N2–C1–N3) and 125.69 (8)° (N1–C1–N3), showing a deviation of the CN₃ plane from an ideal trigonal-planar geometry. Bonds between N atoms and terminal C-methyl groups all have values close to typical single bonds (1.4529 (12)–1.4624 (12) Å). The C–O bond length in the diphenylcarbamoyl group is C6–O1 = 1.2305 (11) Å, and shows the expected double-bond character. The N–C bond lengths in the carbamoyl moiety are: N3–C6 = 1.3722 (11) Å, N4–C6 = 1.4028 (11) Å, N4–C13 = 1.4266 (11) Å and N4–C7 = 1.4367 (11) Å. They agree very well with X-ray structural data of the compounds 2- and 5-azido-N- (diphenylcarbamoyl)proline methyl ester (Lynch et al., 1995). The dihedral angle C1–N3–C6–N4 is -161.69 (8)° and the angle between the planes N1/C1/N2 and O1/C6/N4 is 51.68 (8)°, which shows a significant twisting of the diphenylcarbamoyl group relative to the CN₃ plane (Fig. 1). Weak C–H···O hydrogen bonds between aromatic hydrogen atoms and carbonyl oxygen atoms of neighboring molecules have been determined [d(H···O) = 2.59 Å] (Tab. 1), generating a chain along the ab-plane (Fig. 2). On the other hand, intermolecular C–H···N hydrogen bonds play no prominent role in the stabilization of the crystal structure.

Related literature top

For synthesis of N-dimethylcarbamoyl-N',N',N'',N''-tetramethylguanidine, see: Möllers et al. (2003). For the crystal structures of 2- and 5-azido-N-(diphenylcarbamoyl) proline methyl ester, see: Lynch et al. (1995).

Experimental top

The title compound was obtained by heating two equivalents (60.4 mmol) of N',N',N'',N''-tetramethylguanidine with one equivalent (30.2 mmol) N,N-diphenylcarbamoyl chloride in acetonitrile for three hours under reflux. After cooling to room temperature the precipitated N',N',N'',N''-tetramethylguanidinium chloride was filtered off and the solvent was removed. The residue was redissolved in diethylether and the insoluble part was filtered off. After evaporation of the solvent a colorless solid was been obtained. The title compound crystallized from a saturated acetonitrile solution after several days at 273 K, forming colorless single crystals. Yield: 7.6 g (81%)

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); 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: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound with displacement ellipsoids at the 50% probability level.
	Fig. 2. C–H···O hydrogen bonds between the molecules, ab-view. Hydrogen bonds are indicated by dashed lines.

3-[Bis(dimethylamino)methylene]-1,1-diphenylurea top

Crystal data top

C₁₈H₂₂N₄O	F(000) = 664
M_r = 310.40	D_x = 1.262 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 427 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.9321 (3) Å	Cell parameters from 4990 reflections
b = 17.0477 (9) Å	θ = 2.1–30.5°
c = 12.2151 (6) Å	µ = 0.08 mm⁻¹
β = 98.583 (2)°	T = 100 K
V = 1633.28 (13) Å³	Block, colorless
Z = 4	0.25 × 0.20 × 0.15 mm

Data collection top

Bruker Kappa APEXII Duo diffractometer	4200 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.029
Graphite monochromator	θ_max = 30.5°, θ_min = 2.1°
ϕ scans, and ω scans	h = −11→11
51490 measured reflections	k = −24→24
4990 independent reflections	l = −17→16

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)] = 0.039	Hydrogen site location: difference Fourier map
wR(F²) = 0.105	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0541P)² + 0.4544P] where P = (F_o² + 2F_c²)/3
4990 reflections	(Δ/σ)_max < 0.001
212 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₈H₂₂N₄O	V = 1633.28 (13) Å³
M_r = 310.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.9321 (3) Å	µ = 0.08 mm⁻¹
b = 17.0477 (9) Å	T = 100 K
c = 12.2151 (6) Å	0.25 × 0.20 × 0.15 mm
β = 98.583 (2)°

Data collection top

Bruker Kappa APEXII Duo diffractometer	4200 reflections with I > 2σ(I)
51490 measured reflections	R_int = 0.029
4990 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.04	Δρ_max = 0.37 e Å⁻³
4990 reflections	Δρ_min = −0.23 e Å⁻³
212 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
C1	0.37589 (11)	0.11725 (5)	0.29192 (7)	0.01420 (17)
N1	0.44747 (10)	0.12889 (5)	0.40021 (7)	0.01682 (16)
C2	0.63269 (12)	0.12487 (6)	0.43072 (8)	0.0215 (2)
H2A	0.6820	0.0965	0.3733	0.032*
H2B	0.6606	0.0973	0.5015	0.032*
H2C	0.6796	0.1781	0.4379	0.032*
C3	0.36063 (13)	0.17835 (6)	0.47145 (8)	0.02078 (19)
H3A	0.3971	0.2329	0.4654	0.031*
H3B	0.3893	0.1608	0.5484	0.031*
H3C	0.2371	0.1746	0.4485	0.031*
N2	0.41847 (10)	0.04945 (4)	0.24502 (7)	0.01680 (16)
C4	0.47540 (14)	−0.02051 (6)	0.30890 (9)	0.0239 (2)
H4A	0.4702	−0.0110	0.3874	0.036*
H4B	0.5930	−0.0327	0.2992	0.036*
H4C	0.4013	−0.0648	0.2829	0.036*
C5	0.36459 (14)	0.03644 (6)	0.12745 (8)	0.0218 (2)
H5A	0.2532	0.0104	0.1162	0.033*
H5B	0.4483	0.0032	0.0982	0.033*
H5C	0.3560	0.0869	0.0886	0.033*
N3	0.26184 (10)	0.16304 (4)	0.23400 (7)	0.01607 (16)
C6	0.27494 (11)	0.24288 (5)	0.24670 (7)	0.01419 (16)
O1	0.40355 (8)	0.28089 (4)	0.28186 (6)	0.01803 (14)
N4	0.12115 (10)	0.28111 (4)	0.20749 (7)	0.01481 (15)
C7	−0.02172 (11)	0.23987 (5)	0.14776 (7)	0.01345 (16)
C8	−0.00729 (12)	0.20271 (5)	0.04806 (7)	0.01524 (17)
H8A	0.0983	0.2033	0.0202	0.018*
C9	−0.14748 (12)	0.16466 (5)	−0.01074 (8)	0.01697 (18)
H9A	−0.1369	0.1387	−0.0782	0.020*
C10	−0.30287 (12)	0.16456 (5)	0.02879 (8)	0.01796 (18)
H10A	−0.3989	0.1392	−0.0120	0.022*
C11	−0.31730 (12)	0.20166 (5)	0.12827 (8)	0.01758 (18)
H11A	−0.4232	0.2014	0.1557	0.021*
C12	−0.17678 (12)	0.23931 (5)	0.18795 (8)	0.01584 (17)
H12A	−0.1869	0.2645	0.2560	0.019*
C13	0.10260 (11)	0.36346 (5)	0.22264 (7)	0.01373 (16)
C14	0.01332 (12)	0.40811 (5)	0.13736 (8)	0.01772 (18)
H14A	−0.0281	0.3842	0.0683	0.021*
C15	−0.01532 (13)	0.48785 (5)	0.15331 (9)	0.0216 (2)
H15A	−0.0774	0.5178	0.0952	0.026*
C16	0.04600 (13)	0.52374 (5)	0.25311 (9)	0.0221 (2)
H16A	0.0259	0.5779	0.2638	0.026*
C17	0.13735 (13)	0.47939 (5)	0.33744 (8)	0.02066 (19)
H17A	0.1811	0.5038	0.4057	0.025*
C18	0.16545 (12)	0.39969 (5)	0.32295 (8)	0.01654 (18)
H18	0.2274	0.3700	0.3813	0.020*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0131 (4)	0.0118 (4)	0.0181 (4)	−0.0006 (3)	0.0039 (3)	0.0001 (3)
N1	0.0154 (4)	0.0174 (3)	0.0175 (4)	0.0034 (3)	0.0019 (3)	−0.0007 (3)
C2	0.0164 (4)	0.0251 (5)	0.0222 (5)	0.0006 (4)	−0.0001 (3)	0.0032 (4)
C3	0.0236 (5)	0.0201 (4)	0.0195 (4)	0.0025 (4)	0.0061 (4)	−0.0027 (3)
N2	0.0200 (4)	0.0120 (3)	0.0186 (4)	0.0032 (3)	0.0038 (3)	0.0001 (3)
C4	0.0307 (5)	0.0137 (4)	0.0288 (5)	0.0067 (4)	0.0097 (4)	0.0038 (4)
C5	0.0283 (5)	0.0174 (4)	0.0201 (4)	−0.0012 (4)	0.0047 (4)	−0.0049 (3)
N3	0.0155 (4)	0.0105 (3)	0.0212 (4)	0.0007 (3)	−0.0005 (3)	−0.0004 (3)
C6	0.0143 (4)	0.0125 (4)	0.0158 (4)	0.0007 (3)	0.0021 (3)	−0.0006 (3)
O1	0.0147 (3)	0.0144 (3)	0.0244 (3)	−0.0018 (2)	0.0008 (3)	−0.0017 (2)
N4	0.0140 (3)	0.0094 (3)	0.0201 (4)	0.0000 (3)	−0.0005 (3)	−0.0019 (3)
C7	0.0143 (4)	0.0092 (3)	0.0163 (4)	−0.0005 (3)	0.0004 (3)	0.0005 (3)
C8	0.0158 (4)	0.0138 (4)	0.0166 (4)	0.0002 (3)	0.0041 (3)	0.0000 (3)
C9	0.0213 (4)	0.0140 (4)	0.0151 (4)	−0.0003 (3)	0.0011 (3)	−0.0010 (3)
C10	0.0174 (4)	0.0132 (4)	0.0222 (4)	−0.0021 (3)	−0.0008 (3)	0.0004 (3)
C11	0.0146 (4)	0.0157 (4)	0.0229 (4)	−0.0009 (3)	0.0044 (3)	0.0018 (3)
C12	0.0176 (4)	0.0133 (4)	0.0170 (4)	0.0005 (3)	0.0040 (3)	−0.0005 (3)
C13	0.0132 (4)	0.0100 (4)	0.0187 (4)	−0.0005 (3)	0.0045 (3)	−0.0005 (3)
C14	0.0174 (4)	0.0137 (4)	0.0213 (4)	0.0006 (3)	0.0002 (3)	0.0002 (3)
C15	0.0199 (4)	0.0131 (4)	0.0309 (5)	0.0027 (3)	0.0011 (4)	0.0035 (4)
C16	0.0214 (5)	0.0116 (4)	0.0344 (5)	0.0012 (3)	0.0080 (4)	−0.0028 (4)
C17	0.0242 (5)	0.0155 (4)	0.0233 (5)	−0.0017 (3)	0.0070 (4)	−0.0055 (3)
C18	0.0196 (4)	0.0138 (4)	0.0169 (4)	−0.0008 (3)	0.0050 (3)	−0.0004 (3)

Geometric parameters (Å, º) top

C1—N3	1.3179 (11)	N4—C7	1.4367 (11)
C1—N2	1.3551 (11)	C7—C12	1.3907 (13)
C1—N1	1.3737 (11)	C7—C8	1.3925 (12)
N1—C3	1.4566 (12)	C8—C9	1.3909 (12)
N1—C2	1.4624 (12)	C8—H8A	0.9500
C2—H2A	0.9800	C9—C10	1.3893 (14)
C2—H2B	0.9800	C9—H9A	0.9500
C2—H2C	0.9800	C10—C11	1.3897 (14)
C3—H3A	0.9800	C10—H10A	0.9500
C3—H3B	0.9800	C11—C12	1.3940 (13)
C3—H3C	0.9800	C11—H11A	0.9500
N2—C5	1.4529 (12)	C12—H12A	0.9500
N2—C4	1.4594 (12)	C13—C14	1.3949 (12)
C4—H4A	0.9800	C13—C18	1.3961 (12)
C4—H4B	0.9800	C14—C15	1.3967 (13)
C4—H4C	0.9800	C14—H14A	0.9500
C5—H5A	0.9800	C15—C16	1.3857 (15)
C5—H5B	0.9800	C15—H15A	0.9500
C5—H5C	0.9800	C16—C17	1.3910 (14)
N3—C6	1.3722 (11)	C16—H16A	0.9500
C6—O1	1.2305 (11)	C17—C18	1.3923 (12)
C6—N4	1.4028 (11)	C17—H17A	0.9500
N4—C13	1.4266 (11)	C18—H18	0.9500

N3—C1—N2	118.20 (8)	C6—N4—C7	121.73 (7)
N3—C1—N1	125.69 (8)	C13—N4—C7	117.30 (7)
N2—C1—N1	115.91 (8)	C12—C7—C8	119.87 (8)
C1—N1—C3	119.63 (8)	C12—C7—N4	119.75 (8)
C1—N1—C2	119.59 (8)	C8—C7—N4	120.34 (8)
C3—N1—C2	114.93 (8)	C9—C8—C7	120.00 (9)
N1—C2—H2A	109.5	C9—C8—H8A	120.0
N1—C2—H2B	109.5	C7—C8—H8A	120.0
H2A—C2—H2B	109.5	C10—C9—C8	120.24 (8)
N1—C2—H2C	109.5	C10—C9—H9A	119.9
H2A—C2—H2C	109.5	C8—C9—H9A	119.9
H2B—C2—H2C	109.5	C9—C10—C11	119.76 (8)
N1—C3—H3A	109.5	C9—C10—H10A	120.1
N1—C3—H3B	109.5	C11—C10—H10A	120.1
H3A—C3—H3B	109.5	C10—C11—C12	120.20 (9)
N1—C3—H3C	109.5	C10—C11—H11A	119.9
H3A—C3—H3C	109.5	C12—C11—H11A	119.9
H3B—C3—H3C	109.5	C7—C12—C11	119.92 (8)
C1—N2—C5	119.54 (8)	C7—C12—H12A	120.0
C1—N2—C4	123.21 (8)	C11—C12—H12A	120.0
C5—N2—C4	115.19 (8)	C14—C13—C18	119.28 (8)
N2—C4—H4A	109.5	C14—C13—N4	119.39 (8)
N2—C4—H4B	109.5	C18—C13—N4	121.27 (8)
H4A—C4—H4B	109.5	C13—C14—C15	120.13 (9)
N2—C4—H4C	109.5	C13—C14—H14A	119.9
H4A—C4—H4C	109.5	C15—C14—H14A	119.9
H4B—C4—H4C	109.5	C16—C15—C14	120.62 (9)
N2—C5—H5A	109.5	C16—C15—H15A	119.7
N2—C5—H5B	109.5	C14—C15—H15A	119.7
H5A—C5—H5B	109.5	C15—C16—C17	119.15 (9)
N2—C5—H5C	109.5	C15—C16—H16A	120.4
H5A—C5—H5C	109.5	C17—C16—H16A	120.4
H5B—C5—H5C	109.5	C16—C17—C18	120.79 (9)
C1—N3—C6	119.50 (8)	C16—C17—H17A	119.6
O1—C6—N3	127.35 (8)	C18—C17—H17A	119.6
O1—C6—N4	120.53 (8)	C17—C18—C13	120.02 (9)
N3—C6—N4	112.02 (7)	C17—C18—H18	120.0
C6—N4—C13	120.94 (7)	C13—C18—H18	120.0

N3—C1—N1—C3	21.15 (14)	C12—C7—C8—C9	−0.43 (13)
N2—C1—N1—C3	−153.60 (9)	N4—C7—C8—C9	−178.31 (8)
N3—C1—N1—C2	−130.58 (10)	C7—C8—C9—C10	0.95 (13)
N2—C1—N1—C2	54.67 (12)	C8—C9—C10—C11	−0.94 (13)
N3—C1—N2—C5	11.89 (13)	C9—C10—C11—C12	0.41 (14)
N1—C1—N2—C5	−172.95 (8)	C8—C7—C12—C11	−0.09 (13)
N3—C1—N2—C4	−151.00 (9)	N4—C7—C12—C11	177.79 (8)
N1—C1—N2—C4	24.16 (13)	C10—C11—C12—C7	0.11 (13)
N2—C1—N3—C6	−146.79 (9)	C6—N4—C13—C14	140.27 (9)
N1—C1—N3—C6	38.57 (14)	C7—N4—C13—C14	−37.84 (12)
C1—N3—C6—O1	22.08 (15)	C6—N4—C13—C18	−42.63 (13)
C1—N3—C6—N4	−161.69 (8)	C7—N4—C13—C18	139.26 (9)
O1—C6—N4—C13	−9.58 (13)	C18—C13—C14—C15	−1.21 (14)
N3—C6—N4—C13	173.89 (8)	N4—C13—C14—C15	175.95 (9)
O1—C6—N4—C7	168.45 (8)	C13—C14—C15—C16	0.78 (15)
N3—C6—N4—C7	−8.08 (12)	C14—C15—C16—C17	0.25 (15)
C6—N4—C7—C12	121.44 (9)	C15—C16—C17—C18	−0.84 (15)
C13—N4—C7—C12	−60.46 (11)	C16—C17—C18—C13	0.40 (15)
C6—N4—C7—C8	−60.69 (12)	C14—C13—C18—C17	0.63 (14)
C13—N4—C7—C8	117.41 (9)	N4—C13—C18—C17	−176.47 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1ⁱ	0.95	2.59	3.3893 (12)	141

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₂N₄O
M_r	310.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.9321 (3), 17.0477 (9), 12.2151 (6)
β (°)	98.583 (2)
V (Å³)	1633.28 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Bruker Kappa APEXII Duo diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	51490, 4990, 4200
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.715

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.105, 1.04
No. of reflections	4990
No. of parameters	212
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.23

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1ⁱ	0.95	2.59	3.3893 (12)	141

Symmetry code: (i) x−1, y, z.

Acknowledgements

The author thanks Dr W. Frey (Institut für Organische Chemie, Universität Stuttgart) for the data collection.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, D-53002 Bonn, Germany. Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lynch, V. M., Hulme, C., Magnus, P. & Davis, B. E. (1995). Acta Cryst. C51, 2598–2601. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
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