Ethyl (2E,4Z)-5-diethyl­amino-2-(phenyl­sulfon­yl)penta-2,4-dienoate

Song, G.-Q.; Yu, P.-P.; Huang, X.-F.

doi:10.1107/S1600536812023483

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1919

doi:10.1107/S1600536812023483

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Ethyl (2E,4Z)-5-diethylamino-2-(phenylsulfonyl)penta-2,4-dienoate

Guo-Qiang Song,^a Pei-Pei Yu ^a and Xian-Feng Huang ^a ^*

^aSchool of Pharmaceutical Engineering and Life Science, Changzhou University, Changzhou 213164, People's Republic of China
^*Correspondence e-mail: xianfenghh@163.com

(Received 4 April 2012; accepted 23 May 2012; online 31 May 2012)

In the title compound, C₁₇H₂₃NO₄S, the pentadiene group adopts a planar conformation, with an r.m.s. deviation of 0.0410 (14) Å. The phenyl ring makes a dihedral angle of 85.73 (11)° with the pentadiene group, while the pentadiene group makes dihedral angles of 11.38 (11) and 14.08 (10)°, respectively, with the amino and ester groups. In the crystal, molecules are linked via pairs of C—H⋯O interactions, forming inversion dimers.

Related literature

For background information on pentadienoates, see: Sorbetti et al. (2007 ). For structural data of pentadienoates, see: Ceard et al. (2002 ). For details of weak hydrogen-bonding interactions, see: Steiner (2002 ).

Experimental

Crystal data

C₁₇H₂₃NO₄S
M_r = 337.42
Monoclinic, P 2₁ /n
a = 14.489 (2) Å
b = 8.2989 (12) Å
c = 16.706 (3) Å
β = 114.313 (3)°
V = 1830.6 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 296 K
0.28 × 0.24 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.669, T_max = 0.746
11618 measured reflections
4183 independent reflections
2977 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.168
S = 1.04
4183 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯O1ⁱ	0.93	2.41	3.277 (3)	155
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: APEX2 and SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 2005 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812023483/pk2405sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812023483/pk2405Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812023483/pk2405Isup3.cml

checkCIF report

Comment top

Analogues of pentadienoate have been used widely in perfumes, lubricants, as pharmaceutical intermediates and in other chemical industries (Ceard et al., 2002; Sorbetti et al., 2007). In this work, we report the crystal structure of the title compound, C₁₇H₂₃NO₄S, (I). In the crystal (Fig. 1), the pentadiene group adopts a planar conformation with an r.m.s. deviation of 0.0410 (14) Å. The phenyl ring makes a dihedral angle of 85.73 (11)° with the pentadiene group. The dihedral angle of pentadiene with the amino group (atoms N1, C14, C16) is 11.38 (11)° and the dihedral angle between pentadiene and the ester group (atoms C8, O3, O4) is 14.08 (10)°. The crystal structure exhibits weak intermolecular C—H···O hydrogen bonds (Steiner, 2002; Table 1) between pairs of inversion related (-x, 1-y, 1-z) molecules to produce a weakly hydrogen-bonded dimer as shown in Fig. 2.

Related literature top

For background information on pentadienoates, see: Sorbetti et al. (2007). For structural data of pentadienoates, see: Ceard et al. (2002). For details of weak hydrogen-bonding interactions, see: Steiner (2002).

Experimental top

The title compound was prepared by stirring a mixture of malonaldehyde bis(dimethyl acetal) (411 mg, 2.5 mmol), ethanamine (366 mg, 2.5 mmol) and acetic acid (300 mg, 5 mmol) under reflux for 1 h. After cooling, ethyl 2-(phenylsulfonyl)acetate (428 mg, 1.87 mmol), DMF (1.5 ml) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 761 mg, 5 mmol) were added and stirred for 6 h. Then the reaction mixture was added dropwise to ice water (20 ml) to give a yellow solid (259 mg), which was dissolved in 2-propanol. Pale yellow rhomboid-shaped crystals of (I) formed upon evaporation after 7d.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 and SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids.
	Fig. 2. Crystal packing diagram of (I) with weak hydrogen bonds indicated as dashed lines.

Ethyl (2E,4Z)-5-diethylamino-2-(phenylsulfonyl)penta-2,4-dienoate top

Crystal data top

C₁₇H₂₃NO₄S	F(000) = 720
M_r = 337.42	D_x = 1.224 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3554 reflections
a = 14.489 (2) Å	θ = 2.7–25.5°
b = 8.2989 (12) Å	µ = 0.20 mm⁻¹
c = 16.706 (3) Å	T = 296 K
β = 114.313 (3)°	Block, pale yellow
V = 1830.6 (5) Å³	0.28 × 0.24 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	4183 independent reflections
Radiation source: fine-focus sealed tube	2977 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 27.6°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −18→18
T_min = 0.669, T_max = 0.746	k = −10→10
11618 measured reflections	l = −21→19

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.168	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0806P)² + 0.7143P] where P = (F_o² + 2F_c²)/3
4183 reflections	(Δ/σ)_max < 0.001
211 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₁₇H₂₃NO₄S	V = 1830.6 (5) Å³
M_r = 337.42	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.489 (2) Å	µ = 0.20 mm⁻¹
b = 8.2989 (12) Å	T = 296 K
c = 16.706 (3) Å	0.28 × 0.24 × 0.20 mm
β = 114.313 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4183 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2977 reflections with I > 2σ(I)
T_min = 0.669, T_max = 0.746	R_int = 0.031
11618 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.168	H-atom parameters constrained
S = 1.04	Δρ_max = 0.47 e Å⁻³
4183 reflections	Δρ_min = −0.44 e Å⁻³
211 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
S1	0.11499 (4)	0.59041 (7)	0.39164 (4)	0.04777 (19)
O1	0.02067 (12)	0.5770 (2)	0.40107 (12)	0.0639 (5)
O2	0.12167 (17)	0.7075 (2)	0.33125 (13)	0.0767 (6)
O3	0.38118 (13)	0.6802 (3)	0.58018 (13)	0.0790 (7)
O4	0.33628 (15)	0.6001 (3)	0.44145 (14)	0.0809 (7)
N1	0.22370 (15)	0.6412 (3)	0.79523 (13)	0.0586 (5)
C1	0.13732 (16)	0.3988 (3)	0.35660 (15)	0.0445 (5)
C2	0.1630 (2)	0.3849 (3)	0.28691 (19)	0.0635 (7)
H2A	0.1709	0.4763	0.2581	0.076*
C3	0.1772 (2)	0.2316 (4)	0.2595 (2)	0.0825 (10)
H3A	0.1942	0.2202	0.2119	0.099*
C4	0.1661 (2)	0.0986 (4)	0.3026 (2)	0.0787 (9)
H4A	0.1764	−0.0032	0.2844	0.094*
C5	0.1404 (3)	0.1130 (3)	0.3716 (2)	0.0789 (9)
H5A	0.1338	0.0213	0.4009	0.095*
C6	0.1240 (2)	0.2627 (3)	0.39856 (18)	0.0623 (7)
H6A	0.1041	0.2724	0.4446	0.075*
C7	0.21004 (16)	0.6228 (3)	0.49653 (15)	0.0455 (5)
C8	0.31330 (19)	0.6342 (3)	0.50106 (17)	0.0572 (6)
C9	0.4909 (2)	0.6711 (6)	0.5980 (3)	0.1000 (12)
H9A	0.5311	0.6566	0.6604	0.120*
H9B	0.5027	0.5796	0.5673	0.120*
C10	0.5202 (4)	0.8158 (8)	0.5691 (4)	0.153 (2)
H10A	0.5916	0.8128	0.5836	0.229*
H10B	0.5053	0.9064	0.5975	0.229*
H10C	0.4836	0.8258	0.5066	0.229*
C11	0.18153 (17)	0.6212 (3)	0.56550 (15)	0.0453 (5)
H11A	0.1130	0.6014	0.5493	0.054*
C12	0.23716 (17)	0.6439 (3)	0.65536 (15)	0.0480 (5)
H12A	0.3055	0.6710	0.6780	0.058*
C13	0.18773 (18)	0.6250 (3)	0.70915 (16)	0.0522 (6)
H13A	0.1197	0.5969	0.6813	0.063*
C14	0.1598 (3)	0.6048 (4)	0.8424 (2)	0.0772 (9)
H14A	0.1037	0.5372	0.8056	0.093*
H14B	0.1993	0.5447	0.8953	0.093*
C15	0.1196 (3)	0.7509 (5)	0.8664 (3)	0.1104 (14)
H15A	0.0789	0.7212	0.8971	0.166*
H15B	0.0788	0.8094	0.8141	0.166*
H15C	0.1748	0.8175	0.9035	0.166*
C16	0.32789 (19)	0.6914 (3)	0.84751 (16)	0.0595 (6)
H16A	0.3300	0.7548	0.8970	0.071*
H16B	0.3504	0.7597	0.8119	0.071*
C17	0.3990 (3)	0.5521 (4)	0.8809 (3)	0.0984 (11)
H17A	0.4649	0.5909	0.9193	0.148*
H17B	0.4034	0.4962	0.8323	0.148*
H17C	0.3744	0.4799	0.9126	0.148*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0517 (3)	0.0390 (3)	0.0470 (3)	0.0037 (2)	0.0147 (2)	−0.0007 (2)
O1	0.0429 (9)	0.0721 (12)	0.0661 (11)	0.0088 (8)	0.0118 (8)	−0.0138 (9)
O2	0.1097 (16)	0.0469 (10)	0.0628 (12)	0.0035 (10)	0.0246 (11)	0.0143 (9)
O3	0.0504 (10)	0.1203 (18)	0.0705 (12)	−0.0272 (11)	0.0292 (9)	−0.0313 (12)
O4	0.0694 (12)	0.1177 (18)	0.0694 (12)	−0.0237 (11)	0.0426 (10)	−0.0264 (12)
N1	0.0557 (12)	0.0719 (14)	0.0515 (12)	−0.0186 (10)	0.0256 (10)	−0.0151 (10)
C1	0.0456 (11)	0.0395 (11)	0.0466 (12)	−0.0035 (9)	0.0172 (9)	−0.0058 (9)
C2	0.0724 (17)	0.0638 (16)	0.0657 (16)	−0.0099 (13)	0.0399 (14)	−0.0077 (13)
C3	0.088 (2)	0.092 (2)	0.090 (2)	−0.0117 (18)	0.0583 (19)	−0.0339 (19)
C4	0.0771 (19)	0.0543 (16)	0.112 (3)	−0.0126 (14)	0.0456 (19)	−0.0323 (17)
C5	0.095 (2)	0.0443 (15)	0.104 (2)	−0.0059 (14)	0.047 (2)	−0.0028 (15)
C6	0.0828 (19)	0.0460 (13)	0.0643 (16)	−0.0011 (12)	0.0366 (14)	0.0006 (12)
C7	0.0447 (11)	0.0422 (11)	0.0499 (12)	−0.0043 (9)	0.0197 (10)	−0.0079 (9)
C8	0.0533 (13)	0.0644 (15)	0.0590 (15)	−0.0143 (12)	0.0284 (12)	−0.0131 (12)
C9	0.0607 (18)	0.154 (4)	0.091 (2)	−0.019 (2)	0.0365 (18)	−0.023 (3)
C10	0.114 (4)	0.185 (6)	0.178 (5)	−0.061 (4)	0.079 (4)	−0.030 (4)
C11	0.0413 (11)	0.0406 (11)	0.0544 (13)	−0.0010 (9)	0.0203 (10)	−0.0077 (10)
C12	0.0435 (11)	0.0493 (12)	0.0522 (13)	−0.0061 (10)	0.0205 (10)	−0.0104 (10)
C13	0.0470 (12)	0.0545 (14)	0.0549 (13)	−0.0104 (10)	0.0208 (10)	−0.0143 (11)
C14	0.082 (2)	0.092 (2)	0.0699 (18)	−0.0248 (17)	0.0428 (16)	−0.0180 (16)
C15	0.102 (3)	0.121 (3)	0.137 (3)	−0.019 (2)	0.079 (3)	−0.033 (3)
C16	0.0630 (15)	0.0623 (16)	0.0482 (13)	−0.0171 (12)	0.0177 (11)	−0.0118 (12)
C17	0.080 (2)	0.078 (2)	0.115 (3)	−0.0047 (18)	0.018 (2)	0.005 (2)

Geometric parameters (Å, º) top

S1—O2	1.4324 (19)	C9—C10	1.423 (7)
S1—O1	1.4429 (18)	C9—H9A	0.9700
S1—C7	1.747 (2)	C9—H9B	0.9700
S1—C1	1.770 (2)	C10—H10A	0.9600
O3—C8	1.338 (3)	C10—H10B	0.9600
O3—C9	1.494 (4)	C10—H10C	0.9600
O4—C8	1.206 (3)	C11—C12	1.394 (3)
N1—C13	1.319 (3)	C11—H11A	0.9300
N1—C16	1.459 (3)	C12—C13	1.369 (3)
N1—C14	1.473 (3)	C12—H12A	0.9300
C1—C2	1.365 (3)	C13—H13A	0.9300
C1—C6	1.384 (3)	C14—C15	1.471 (5)
C2—C3	1.396 (4)	C14—H14A	0.9700
C2—H2A	0.9300	C14—H14B	0.9700
C3—C4	1.363 (5)	C15—H15A	0.9600
C3—H3A	0.9300	C15—H15B	0.9600
C4—C5	1.355 (5)	C15—H15C	0.9600
C4—H4A	0.9300	C16—C17	1.495 (4)
C5—C6	1.375 (4)	C16—H16A	0.9700
C5—H5A	0.9300	C16—H16B	0.9700
C6—H6A	0.9300	C17—H17A	0.9600
C7—C11	1.375 (3)	C17—H17B	0.9600
C7—C8	1.470 (3)	C17—H17C	0.9600

O2—S1—O1	118.10 (12)	C9—C10—H10A	109.5
O2—S1—C7	110.37 (12)	C9—C10—H10B	109.5
O1—S1—C7	107.05 (11)	H10A—C10—H10B	109.5
O2—S1—C1	107.58 (11)	C9—C10—H10C	109.5
O1—S1—C1	106.07 (11)	H10A—C10—H10C	109.5
C7—S1—C1	107.10 (10)	H10B—C10—H10C	109.5
C8—O3—C9	118.1 (2)	C7—C11—C12	131.4 (2)
C13—N1—C16	121.9 (2)	C7—C11—H11A	114.3
C13—N1—C14	120.6 (2)	C12—C11—H11A	114.3
C16—N1—C14	117.5 (2)	C13—C12—C11	117.7 (2)
C2—C1—C6	120.5 (2)	C13—C12—H12A	121.2
C2—C1—S1	120.57 (19)	C11—C12—H12A	121.2
C6—C1—S1	118.88 (18)	N1—C13—C12	128.7 (2)
C1—C2—C3	119.0 (3)	N1—C13—H13A	115.7
C1—C2—H2A	120.5	C12—C13—H13A	115.7
C3—C2—H2A	120.5	C15—C14—N1	112.5 (3)
C4—C3—C2	120.0 (3)	C15—C14—H14A	109.1
C4—C3—H3A	120.0	N1—C14—H14A	109.1
C2—C3—H3A	120.0	C15—C14—H14B	109.1
C5—C4—C3	120.7 (3)	N1—C14—H14B	109.1
C5—C4—H4A	119.6	H14A—C14—H14B	107.8
C3—C4—H4A	119.6	C14—C15—H15A	109.5
C4—C5—C6	120.2 (3)	C14—C15—H15B	109.5
C4—C5—H5A	119.9	H15A—C15—H15B	109.5
C6—C5—H5A	119.9	C14—C15—H15C	109.5
C5—C6—C1	119.5 (3)	H15A—C15—H15C	109.5
C5—C6—H6A	120.3	H15B—C15—H15C	109.5
C1—C6—H6A	120.3	N1—C16—C17	112.8 (2)
C11—C7—C8	127.5 (2)	N1—C16—H16A	109.0
C11—C7—S1	117.03 (17)	C17—C16—H16A	109.0
C8—C7—S1	115.27 (17)	N1—C16—H16B	109.0
O4—C8—O3	122.8 (2)	C17—C16—H16B	109.0
O4—C8—C7	124.3 (2)	H16A—C16—H16B	107.8
O3—C8—C7	112.8 (2)	C16—C17—H17A	109.5
C10—C9—O3	109.3 (4)	C16—C17—H17B	109.5
C10—C9—H9A	109.8	H17A—C17—H17B	109.5
O3—C9—H9A	109.8	C16—C17—H17C	109.5
C10—C9—H9B	109.8	H17A—C17—H17C	109.5
O3—C9—H9B	109.8	H17B—C17—H17C	109.5
H9A—C9—H9B	108.3

O2—S1—C1—C2	4.3 (2)	C1—S1—C7—C8	64.6 (2)
O1—S1—C1—C2	131.5 (2)	C9—O3—C8—O4	−7.0 (5)
C7—S1—C1—C2	−114.4 (2)	C9—O3—C8—C7	170.3 (3)
O2—S1—C1—C6	−172.9 (2)	C11—C7—C8—O4	163.0 (3)
O1—S1—C1—C6	−45.7 (2)	S1—C7—C8—O4	−11.1 (4)
C7—S1—C1—C6	68.4 (2)	C11—C7—C8—O3	−14.3 (4)
C6—C1—C2—C3	−1.0 (4)	S1—C7—C8—O3	171.59 (19)
S1—C1—C2—C3	−178.2 (2)	C8—O3—C9—C10	86.6 (4)
C1—C2—C3—C4	−0.5 (5)	C8—C7—C11—C12	6.7 (4)
C2—C3—C4—C5	0.7 (5)	S1—C7—C11—C12	−179.3 (2)
C3—C4—C5—C6	0.7 (5)	C7—C11—C12—C13	−176.0 (2)
C4—C5—C6—C1	−2.2 (5)	C16—N1—C13—C12	2.6 (4)
C2—C1—C6—C5	2.4 (4)	C14—N1—C13—C12	−175.8 (3)
S1—C1—C6—C5	179.6 (2)	C11—C12—C13—N1	−179.4 (2)
O2—S1—C7—C11	132.99 (19)	C13—N1—C14—C15	−101.9 (3)
O1—S1—C7—C11	3.2 (2)	C16—N1—C14—C15	79.6 (4)
C1—S1—C7—C11	−110.18 (18)	C13—N1—C16—C17	−91.9 (3)
O2—S1—C7—C8	−52.3 (2)	C14—N1—C16—C17	86.6 (3)
O1—S1—C7—C8	177.97 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1ⁱ	0.93	2.41	3.277 (3)	155

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₃NO₄S
M_r	337.42
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	14.489 (2), 8.2989 (12), 16.706 (3)
β (°)	114.313 (3)
V (Å³)	1830.6 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.28 × 0.24 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.669, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	11618, 4183, 2977
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.653

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.168, 1.04
No. of reflections	4183
No. of parameters	211
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.44

Computer programs: APEX2 (Bruker, 2007), APEX2 and SAINT (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1ⁱ	0.93	2.41	3.277 (3)	155.1

Symmetry code: (i) −x, −y+1, −z+1.

References

Brandenburg, K. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ceard, S., Roche, D., Gaumet, V., Gardette, D., Metin, J. & Madesclaire, M. (2002). J. Mol. Struct. 608, 27–33. CAS Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sorbetti, J. M., Clary, K. N., Rankic, D. A., Wulff, J. E., Parvez, M. & Back, T. G. (2007). J. Org. Chem. 72, 3326–3331. Web of Science CSD CrossRef PubMed CAS Google Scholar
Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48–76. Web of Science CrossRef CAS Google Scholar

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Volume 68| Part 6| June 2012| Page o1919

doi:10.1107/S1600536812023483

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