Dimethyl 2-(3-chloro­phen­yl)-6-hy­droxy-6-methyl-4-(methyl­amino)­cyclo­hex-3-ene-1,3-dicarboxyl­ate

Amirthaganesan, S.; Sundaramoorthy, S.; Velmurugan, D.; Jeong, Y.T.

doi:10.1107/S1600536811017089

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1424

doi:10.1107/S1600536811017089

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Dimethyl 2-(3-chlorophenyl)-6-hydroxy-6-methyl-4-(methylamino)cyclohex-3-ene-1,3-dicarboxylate

S. Amirthaganesan,^a S. Sundaramoorthy,^b D. Velmurugan ^b and Y. T. Jeong ^a ^*

^aDepartment of Image Science and Engineering, Pukyong National University, Busan, 608-739, Republic of Korea, and ^bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: ytjeong@pknu.ac.kr

(Received 2 May 2011; accepted 6 May 2011; online 14 May 2011)

In the title compound, C₁₈H₂₂ClNO₅, the cyclohexene ring adopts a distorted half-chair conformation. The molecular structure is stabilized by pairs of intramolecular N—H⋯O and O—H⋯O interactions, generating S(6) motifs. In the crystal, the molecules are linked by intermolecular C—H⋯O interactions, forming centrosymmetric dimers.

Related literature

For the synthesis see: Pandiarajan et al. (2005 ). For related structures, see: Amézquita-Valencia et al. (2009, 2010); Venter et al. (2010 ). For ring conformational analysis, see: Cremer & Pople (1975 ); Nardelli (1983 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₈H₂₂ClNO₅
M_r = 367.82
Monoclinic, P 2₁ /c
a = 11.962 (3) Å
b = 9.118 (4) Å
c = 17.704 (5) Å
β = 104.890 (3)°
V = 1866.1 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 293 K
0.25 × 0.22 × 0.2 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.944, T_max = 0.955
17431 measured reflections
4638 independent reflections
3337 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.138
S = 1.04
4638 reflections
231 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.86	2.0	2.673 (2)	134
O3—H4A⋯O4	0.82	2.39	2.990 (2)	131
C15—H15B⋯O1ⁱ	0.96	2.52	3.327 (3)	142
Symmetry code: (i) -x+1, -y+1, -z+1.

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: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811017089/bt5540sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811017089/bt5540Isup2.hkl

checkCIF report

Comment top

The title compound has been obtained as a minor product during the synthesis of 2,4-bismethoxycarbonyl-3-(3-chlorophenyl)- 5-hydroxy-5-methylcyclohexanone (Pandiarajan et al., 2005). The synthesized cyclohexanone has been purified by the recrystallization process in ethanol solvent. The expected compound regenerated and settled as powder along with some small crystals. The obtained crystals were analysed by single-crystal XRD and the results clearly evidence the formation of the title compound.

The ORTEP diagram of the title compound is shown in Fig.1. The cyclohexane ring adopts a distorted half-chair conformation with the puckering parameters (Cremer & Pople, 1975) and the smallest displacement asymmetry parameters (Nardelli, 1983) being q₂ = 0.4038 (16) Å, q₃ = -0.3083 (16) Å, Q_T = 0.5080 (16) Å, and θ = 127.36 (18)°. Atom Cl1 deviates from the plane of the C1—C6 benzene ring by 0.034 (1) Å.

The crystal packing is stabilized by C—H···O intermolecular interactions. The molecular structure is stabilized by N—H···O and O—H···O hydrogen bonds, wherein, atom N1 and O3 act as donor to O1 and O4, to generate S(6) motifs, respectively. In the crystal structure, the molecules at (x, y, z) and (1 - x,1 - y,1 - z) are linked by C(15)—H(15B) ···O(1) hydrogen bonds, generating a centrosymmetric dimeric ring motif R₂²(14) (Bernstein et al., 1995).

Related literature top

For the synthesis see: Pandiarajan et al. (2005). For related structures, see: Amézquita-Valencia et al. (2009, 2010); Venter et al. (2010). For ring conformational analysis, see: Cremer & Pople (1975); Nardelli (1983). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A mixture of 3-chlorobenzaldehyde (1 equvi) and methyl acetoacetate (2 equvi) and 40% methylamine solution (1 equvi) in ethanol was kept in hot water bath for about 30 minutes. It was kept aside for a day. The separated solid was recrystallized from ethanol.

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: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Perspective view of the molecule showing the thermal ellipsoids are drawn at 30% probability level.
	Fig. 2. The crystal packing of the molecules viewed along a face. For clarity, hydrogen atoms which are not involved in hydrogen bonding are omitted

Dimethyl 2-(3-chlorophenyl)-6-hydroxy-6-methyl-4-(methylamino)cyclohex-3-ene- 1,3-dicarboxylate top

Crystal data top

C₁₈H₂₂ClNO₅	F(000) = 776
M_r = 367.82	D_x = 1.309 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1222 reflections
a = 11.962 (3) Å	θ = 1.8–28.3°
b = 9.118 (4) Å	µ = 0.23 mm⁻¹
c = 17.704 (5) Å	T = 293 K
β = 104.890 (3)°	Block, colourless
V = 1866.1 (11) Å³	0.25 × 0.22 × 0.2 mm
Z = 4

Data collection top

Bruker SMART APEXII area-detector diffractometer	4638 independent reflections
Radiation source: fine-focus sealed tube	3337 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω and ϕ scans	θ_max = 28.3°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→15
T_min = 0.944, T_max = 0.955	k = −7→12
17431 measured reflections	l = −23→23

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0627P)² + 0.4709P] where P = (F_o² + 2F_c²)/3
4638 reflections	(Δ/σ)_max = 0.009
231 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

C₁₈H₂₂ClNO₅	V = 1866.1 (11) Å³
M_r = 367.82	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.962 (3) Å	µ = 0.23 mm⁻¹
b = 9.118 (4) Å	T = 293 K
c = 17.704 (5) Å	0.25 × 0.22 × 0.2 mm
β = 104.890 (3)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	4638 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3337 reflections with I > 2σ(I)
T_min = 0.944, T_max = 0.955	R_int = 0.024
17431 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.04	Δρ_max = 0.35 e Å⁻³
4638 reflections	Δρ_min = −0.46 e Å⁻³
231 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	0.20024 (13)	0.2336 (2)	0.66810 (9)	0.0491 (4)
H1	0.2693	0.1975	0.6606	0.059*
C2	0.10067 (15)	0.1499 (2)	0.64705 (10)	0.0606 (5)
C3	−0.00304 (16)	0.2004 (3)	0.65606 (12)	0.0762 (7)
H3	−0.0696	0.1434	0.6412	0.091*
C4	−0.00607 (16)	0.3366 (4)	0.68751 (14)	0.0845 (8)
H4	−0.0757	0.3722	0.6944	0.101*
C5	0.09225 (15)	0.4229 (3)	0.70946 (12)	0.0671 (5)
H5	0.0881	0.5157	0.7303	0.081*
C6	0.19700 (12)	0.37074 (19)	0.70030 (9)	0.0454 (4)
C7	0.30800 (12)	0.45902 (17)	0.72953 (8)	0.0404 (3)
H7	0.2868	0.5589	0.7408	0.048*
C8	0.37441 (12)	0.38775 (16)	0.80710 (8)	0.0405 (3)
H8	0.3766	0.2816	0.7989	0.049*
C9	0.49940 (13)	0.44328 (17)	0.83388 (9)	0.0421 (3)
C10	0.56091 (13)	0.39960 (18)	0.77252 (9)	0.0450 (3)
H10A	0.6358	0.4475	0.7843	0.054*
H10B	0.5743	0.2946	0.7758	0.054*
C11	0.49636 (13)	0.43744 (17)	0.68999 (9)	0.0410 (3)
C12	0.38012 (13)	0.46821 (16)	0.67106 (8)	0.0404 (3)
C13	0.32399 (14)	0.51982 (17)	0.59341 (9)	0.0444 (3)
C14	0.15531 (18)	0.6312 (3)	0.51469 (11)	0.0699 (5)
H14A	0.1977	0.7082	0.4976	0.105*
H14B	0.0818	0.6681	0.5184	0.105*
H14C	0.1435	0.5519	0.4778	0.105*
C15	0.68410 (14)	0.4189 (2)	0.65474 (11)	0.0597 (5)
H15A	0.7225	0.4980	0.6869	0.090*
H15B	0.7075	0.4172	0.6068	0.090*
H15C	0.7045	0.3276	0.6818	0.090*
C16	0.56123 (15)	0.3786 (2)	0.91304 (9)	0.0558 (4)
H16A	0.6418	0.4041	0.9251	0.084*
H16B	0.5533	0.2738	0.9112	0.084*
H16C	0.5276	0.4172	0.9526	0.084*
C17	0.31063 (14)	0.41559 (19)	0.86895 (9)	0.0469 (4)
C18	0.2187 (3)	0.3077 (3)	0.95785 (16)	0.0975 (9)
H18A	0.2735	0.3321	1.0061	0.146*
H18B	0.1814	0.2168	0.9638	0.146*
H18C	0.1618	0.3840	0.9442	0.146*
N1	0.56045 (12)	0.43967 (18)	0.63774 (8)	0.0528 (4)
H1A	0.5244	0.4549	0.5897	0.063*
O1	0.36279 (10)	0.51675 (14)	0.53585 (7)	0.0560 (3)
O2	0.21941 (10)	0.57946 (15)	0.58975 (7)	0.0584 (3)
O3	0.50425 (11)	0.59997 (12)	0.83719 (7)	0.0542 (3)
H4A	0.4653	0.6298	0.8660	0.081*
O4	0.29242 (13)	0.53525 (15)	0.89139 (8)	0.0645 (4)
O5	0.27827 (13)	0.29272 (15)	0.89645 (8)	0.0682 (4)
Cl1	0.10795 (6)	−0.02490 (8)	0.60884 (5)	0.1010 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0376 (8)	0.0622 (10)	0.0469 (8)	−0.0061 (7)	0.0098 (6)	0.0010 (8)
C2	0.0497 (9)	0.0767 (13)	0.0517 (10)	−0.0198 (9)	0.0062 (8)	0.0058 (9)
C3	0.0414 (10)	0.119 (2)	0.0647 (12)	−0.0225 (11)	0.0068 (8)	0.0159 (13)
C4	0.0342 (9)	0.140 (2)	0.0821 (15)	0.0098 (12)	0.0193 (9)	0.0128 (16)
C5	0.0430 (9)	0.0944 (15)	0.0655 (11)	0.0141 (10)	0.0169 (8)	−0.0020 (11)
C6	0.0350 (7)	0.0616 (10)	0.0400 (7)	0.0044 (7)	0.0102 (6)	0.0052 (7)
C7	0.0387 (7)	0.0420 (8)	0.0394 (7)	0.0054 (6)	0.0081 (6)	−0.0008 (6)
C8	0.0421 (7)	0.0376 (7)	0.0403 (7)	0.0038 (6)	0.0079 (6)	−0.0009 (6)
C9	0.0426 (8)	0.0385 (8)	0.0417 (7)	0.0042 (6)	0.0044 (6)	−0.0030 (6)
C10	0.0374 (7)	0.0481 (8)	0.0466 (8)	0.0037 (6)	0.0055 (6)	−0.0020 (7)
C11	0.0403 (7)	0.0386 (7)	0.0437 (8)	−0.0035 (6)	0.0102 (6)	−0.0024 (6)
C12	0.0397 (7)	0.0400 (7)	0.0403 (7)	−0.0017 (6)	0.0082 (6)	−0.0007 (6)
C13	0.0426 (8)	0.0434 (8)	0.0448 (8)	−0.0040 (6)	0.0067 (6)	−0.0010 (6)
C14	0.0613 (11)	0.0841 (14)	0.0560 (10)	0.0188 (10)	−0.0002 (9)	0.0116 (10)
C15	0.0439 (9)	0.0733 (12)	0.0662 (11)	0.0014 (8)	0.0220 (8)	0.0039 (9)
C16	0.0540 (9)	0.0634 (11)	0.0444 (8)	0.0121 (8)	0.0024 (7)	0.0013 (8)
C17	0.0467 (8)	0.0512 (9)	0.0415 (8)	0.0065 (7)	0.0089 (6)	0.0045 (7)
C18	0.119 (2)	0.0965 (19)	0.1025 (18)	0.0165 (16)	0.0740 (17)	0.0306 (15)
N1	0.0410 (7)	0.0695 (9)	0.0493 (8)	−0.0001 (6)	0.0142 (6)	0.0047 (7)
O1	0.0550 (7)	0.0707 (8)	0.0418 (6)	−0.0006 (6)	0.0115 (5)	0.0031 (6)
O2	0.0510 (7)	0.0724 (8)	0.0494 (6)	0.0148 (6)	0.0085 (5)	0.0126 (6)
O3	0.0582 (7)	0.0396 (6)	0.0613 (7)	0.0005 (5)	0.0093 (6)	−0.0078 (5)
O4	0.0821 (9)	0.0578 (8)	0.0607 (8)	0.0108 (7)	0.0313 (7)	−0.0045 (6)
O5	0.0826 (9)	0.0585 (8)	0.0754 (9)	0.0083 (7)	0.0420 (7)	0.0149 (7)
Cl1	0.0875 (4)	0.0874 (5)	0.1206 (5)	−0.0422 (3)	0.0133 (4)	−0.0251 (4)

Geometric parameters (Å, º) top

C1—C6	1.379 (2)	C11—N1	1.345 (2)
C1—C2	1.383 (2)	C11—C12	1.373 (2)
C1—H1	0.9300	C12—C13	1.445 (2)
C2—C3	1.370 (3)	C13—O1	1.2237 (19)
C2—Cl1	1.743 (2)	C13—O2	1.350 (2)
C3—C4	1.365 (4)	C14—O2	1.433 (2)
C3—H3	0.9300	C14—H14A	0.9600
C4—C5	1.385 (3)	C14—H14B	0.9600
C4—H4	0.9300	C14—H14C	0.9600
C5—C6	1.388 (2)	C15—N1	1.444 (2)
C5—H5	0.9300	C15—H15A	0.9600
C6—C7	1.525 (2)	C15—H15B	0.9600
C7—C12	1.511 (2)	C15—H15C	0.9600
C7—C8	1.542 (2)	C16—H16A	0.9600
C7—H7	0.9800	C16—H16B	0.9600
C8—C17	1.508 (2)	C16—H16C	0.9600
C8—C9	1.534 (2)	C17—O4	1.200 (2)
C8—H8	0.9800	C17—O5	1.319 (2)
C9—O3	1.430 (2)	C18—O5	1.451 (2)
C9—C10	1.514 (2)	C18—H18A	0.9600
C9—C16	1.525 (2)	C18—H18B	0.9600
C10—C11	1.507 (2)	C18—H18C	0.9600
C10—H10A	0.9700	N1—H1A	0.8600
C10—H10B	0.9700	O3—H4A	0.8200

C6—C1—C2	119.88 (16)	N1—C11—C12	123.34 (14)
C6—C1—H1	120.1	N1—C11—C10	115.45 (13)
C2—C1—H1	120.1	C12—C11—C10	121.20 (13)
C3—C2—C1	121.8 (2)	C11—C12—C13	119.52 (14)
C3—C2—Cl1	119.31 (16)	C11—C12—C7	122.84 (13)
C1—C2—Cl1	118.94 (16)	C13—C12—C7	117.55 (13)
C4—C3—C2	118.21 (19)	O1—C13—O2	120.94 (14)
C4—C3—H3	120.9	O1—C13—C12	127.01 (15)
C2—C3—H3	120.9	O2—C13—C12	112.03 (13)
C3—C4—C5	121.43 (19)	O2—C14—H14A	109.5
C3—C4—H4	119.3	O2—C14—H14B	109.5
C5—C4—H4	119.3	H14A—C14—H14B	109.5
C4—C5—C6	120.0 (2)	O2—C14—H14C	109.5
C4—C5—H5	120.0	H14A—C14—H14C	109.5
C6—C5—H5	120.0	H14B—C14—H14C	109.5
C1—C6—C5	118.74 (17)	N1—C15—H15A	109.5
C1—C6—C7	120.30 (13)	N1—C15—H15B	109.5
C5—C6—C7	120.86 (17)	H15A—C15—H15B	109.5
C12—C7—C6	113.42 (12)	N1—C15—H15C	109.5
C12—C7—C8	112.29 (12)	H15A—C15—H15C	109.5
C6—C7—C8	106.51 (12)	H15B—C15—H15C	109.5
C12—C7—H7	108.1	C9—C16—H16A	109.5
C6—C7—H7	108.1	C9—C16—H16B	109.5
C8—C7—H7	108.1	H16A—C16—H16B	109.5
C17—C8—C9	110.78 (12)	C9—C16—H16C	109.5
C17—C8—C7	109.55 (12)	H16A—C16—H16C	109.5
C9—C8—C7	111.98 (12)	H16B—C16—H16C	109.5
C17—C8—H8	108.1	O4—C17—O5	123.70 (16)
C9—C8—H8	108.1	O4—C17—C8	124.20 (15)
C7—C8—H8	108.1	O5—C17—C8	112.10 (14)
O3—C9—C10	105.67 (13)	O5—C18—H18A	109.5
O3—C9—C16	110.09 (13)	O5—C18—H18B	109.5
C10—C9—C16	110.33 (13)	H18A—C18—H18B	109.5
O3—C9—C8	111.62 (12)	O5—C18—H18C	109.5
C10—C9—C8	107.83 (12)	H18A—C18—H18C	109.5
C16—C9—C8	111.13 (14)	H18B—C18—H18C	109.5
C11—C10—C9	114.41 (13)	C11—N1—C15	126.10 (14)
C11—C10—H10A	108.7	C11—N1—H1A	117.0
C9—C10—H10A	108.7	C15—N1—H1A	117.0
C11—C10—H10B	108.7	C13—O2—C14	116.46 (14)
C9—C10—H10B	108.7	C9—O3—H4A	109.5
H10A—C10—H10B	107.6	C17—O5—C18	116.35 (16)

C6—C1—C2—C3	1.1 (3)	C8—C9—C10—C11	49.17 (18)
C6—C1—C2—Cl1	−178.36 (12)	C9—C10—C11—N1	161.63 (14)
C1—C2—C3—C4	−0.7 (3)	C9—C10—C11—C12	−17.9 (2)
Cl1—C2—C3—C4	178.76 (17)	N1—C11—C12—C13	−6.3 (2)
C2—C3—C4—C5	0.4 (3)	C10—C11—C12—C13	173.14 (14)
C3—C4—C5—C6	−0.6 (3)	N1—C11—C12—C7	177.30 (14)
C2—C1—C6—C5	−1.2 (2)	C10—C11—C12—C7	−3.2 (2)
C2—C1—C6—C7	175.25 (15)	C6—C7—C12—C11	−130.26 (16)
C4—C5—C6—C1	1.0 (3)	C8—C7—C12—C11	−9.5 (2)
C4—C5—C6—C7	−175.46 (17)	C6—C7—C12—C13	53.32 (18)
C1—C6—C7—C12	49.45 (19)	C8—C7—C12—C13	174.13 (13)
C5—C6—C7—C12	−134.17 (16)	C11—C12—C13—O1	13.8 (3)
C1—C6—C7—C8	−74.57 (17)	C7—C12—C13—O1	−169.67 (15)
C5—C6—C7—C8	101.81 (17)	C11—C12—C13—O2	−164.39 (14)
C12—C7—C8—C17	165.93 (13)	C7—C12—C13—O2	12.1 (2)
C6—C7—C8—C17	−69.36 (16)	C9—C8—C17—O4	62.5 (2)
C12—C7—C8—C9	42.61 (17)	C7—C8—C17—O4	−61.5 (2)
C6—C7—C8—C9	167.32 (12)	C9—C8—C17—O5	−116.62 (15)
C17—C8—C9—O3	−69.40 (16)	C7—C8—C17—O5	119.35 (15)
C7—C8—C9—O3	53.22 (16)	C12—C11—N1—C15	175.24 (17)
C17—C8—C9—C10	174.96 (12)	C10—C11—N1—C15	−4.3 (2)
C7—C8—C9—C10	−62.42 (16)	O1—C13—O2—C14	3.0 (2)
C17—C8—C9—C16	53.92 (17)	C12—C13—O2—C14	−178.66 (16)
C7—C8—C9—C16	176.54 (13)	O4—C17—O5—C18	−0.7 (3)
O3—C9—C10—C11	−70.31 (16)	C8—C17—O5—C18	178.47 (18)
C16—C9—C10—C11	170.72 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	2.0	2.673 (2)	134
O3—H4A···O4	0.82	2.39	2.990 (2)	131
C15—H15B···O1ⁱ	0.96	2.52	3.327 (3)	142

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₂ClNO₅
M_r	367.82
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.962 (3), 9.118 (4), 17.704 (5)
β (°)	104.890 (3)
V (Å³)	1866.1 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.25 × 0.22 × 0.2

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.944, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	17431, 4638, 3337
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.138, 1.04
No. of reflections	4638
No. of parameters	231
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.46

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	2.0	2.673 (2)	134
O3—H4A···O4	0.82	2.39	2.990 (2)	131
C15—H15B···O1ⁱ	0.96	2.52	3.327 (3)	142

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

This study was supported financially by Pukyong National University in the 2009 Post-Doc. Program. SS and DV thank the TBI X-ray Facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and the University Grants Commission (UGC&SAP) for financial support.

References

Amézquita-Valencia, M., Hernández-Ortega, S., Suárez-Ortiz, G. A. & Cabrera, A. (2010). Acta Cryst. E66, o500. Web of Science CSD CrossRef IUCr Journals Google Scholar
Amézquita-Valencia, M., Hernández-Ortega, S., Suárez-Ortiz, G. A., Toscano, R. A. & Cabrera, A. (2009). Acta Cryst. E65, o2728. Web of Science CrossRef IUCr Journals Google Scholar
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Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
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Pandiarajan, K., Sabapathy Mohan, R. T., Gomathi, R. & Muthukumaran, G. (2005). Mag. Reson. Chem. 43, 430–434. CrossRef CAS Google Scholar
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Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 67| Part 6| June 2011| Page o1424

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di­methyl 2-(3-chloro­phen­yl)-6-hy­dr­oxy-6-methyl-4-(methyl­amino)­cyclo­hex-3-ene-1,3-di­carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

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Acknowledgements

References

organic compounds

Dimethyl 2-(3-chlorophenyl)-6-hydroxy-6-methyl-4-(methylamino)cyclohex-3-ene-1,3-dicarboxylate