#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/02/2230251.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2230251
loop_
_publ_author_name
'Amirthaganesan, S.'
'Sundaramoorthy, S.'
'Velmurugan, D.'
'Jeong, Y. T.'
_publ_section_title
;
 Dimethyl
 2-(3-chlorophenyl)-6-hydroxy-6-methyl-4-(methylamino)cyclohex-3-ene-1,3-dicarboxylate
;
_journal_coeditor_code           BT5540
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1424
_journal_paper_doi               10.1107/S1600536811017089
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C18 H22 Cl N O5'
_chemical_formula_moiety         'C18 H22 Cl N O5'
_chemical_formula_sum            'C18 H22 Cl N O5'
_chemical_formula_weight         367.82
_chemical_name_systematic
;
Dimethyl 2-(3-chlorophenyl)-6-hydroxy-6-methyl-4-(methylamino)cyclohex-3-ene-
1,3-dicarboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.890(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.962(3)
_cell_length_b                   9.118(4)
_cell_length_c                   17.704(5)
_cell_measurement_reflns_used    1222
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      1.76
_cell_volume                     1866.1(11)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker SMART APEXII area-detector diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17431
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         1.76
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.458
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4638
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0627P)²+0.4709P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1376
_reflns_number_gt                3337
_reflns_number_total             4638
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bt5540.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230251
_cod_database_fobs_code          2230251
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.20024(13) 0.2336(2) 0.66810(9) 0.0491(4) Uani d . 1 1 . .
H H1 0.2693 0.1975 0.6606 0.059 Uiso calc R 1 1 . .
C C2 0.10067(15) 0.1499(2) 0.64705(10) 0.0606(5) Uani d . 1 1 . .
C C3 -0.00304(16) 0.2004(3) 0.65606(12) 0.0762(7) Uani d . 1 1 . .
H H3 -0.0696 0.1434 0.6412 0.091 Uiso calc R 1 1 . .
C C4 -0.00607(16) 0.3366(4) 0.68751(14) 0.0845(8) Uani d . 1 1 . .
H H4 -0.0757 0.3722 0.6944 0.101 Uiso calc R 1 1 . .
C C5 0.09225(15) 0.4229(3) 0.70946(12) 0.0671(5) Uani d . 1 1 . .
H H5 0.0881 0.5157 0.7303 0.081 Uiso calc R 1 1 . .
C C6 0.19700(12) 0.37074(19) 0.70030(9) 0.0454(4) Uani d . 1 1 . .
C C7 0.30800(12) 0.45902(17) 0.72953(8) 0.0404(3) Uani d . 1 1 . .
H H7 0.2868 0.5589 0.7408 0.048 Uiso calc R 1 1 . .
C C8 0.37441(12) 0.38775(16) 0.80710(8) 0.0405(3) Uani d . 1 1 . .
H H8 0.3766 0.2816 0.7989 0.049 Uiso calc R 1 1 . .
C C9 0.49940(13) 0.44328(17) 0.83388(9) 0.0421(3) Uani d . 1 1 . .
C C10 0.56091(13) 0.39960(18) 0.77252(9) 0.0450(3) Uani d . 1 1 . .
H H10A 0.6358 0.4475 0.7843 0.054 Uiso calc R 1 1 . .
H H10B 0.5743 0.2946 0.7758 0.054 Uiso calc R 1 1 . .
C C11 0.49636(13) 0.43744(17) 0.68999(9) 0.0410(3) Uani d . 1 1 . .
C C12 0.38012(13) 0.46821(16) 0.67106(8) 0.0404(3) Uani d . 1 1 . .
C C13 0.32399(14) 0.51982(17) 0.59341(9) 0.0444(3) Uani d . 1 1 . .
C C14 0.15531(18) 0.6312(3) 0.51469(11) 0.0699(5) Uani d . 1 1 . .
H H14A 0.1977 0.7082 0.4976 0.105 Uiso calc R 1 1 . .
H H14B 0.0818 0.6681 0.5184 0.105 Uiso calc R 1 1 . .
H H14C 0.1435 0.5519 0.4778 0.105 Uiso calc R 1 1 . .
C C15 0.68410(14) 0.4189(2) 0.65474(11) 0.0597(5) Uani d . 1 1 . .
H H15A 0.7225 0.4980 0.6869 0.090 Uiso calc R 1 1 . .
H H15B 0.7075 0.4172 0.6068 0.090 Uiso calc R 1 1 . .
H H15C 0.7045 0.3276 0.6818 0.090 Uiso calc R 1 1 . .
C C16 0.56123(15) 0.3786(2) 0.91304(9) 0.0558(4) Uani d . 1 1 . .
H H16A 0.6418 0.4041 0.9251 0.084 Uiso calc R 1 1 . .
H H16B 0.5533 0.2738 0.9112 0.084 Uiso calc R 1 1 . .
H H16C 0.5276 0.4172 0.9526 0.084 Uiso calc R 1 1 . .
C C17 0.31063(14) 0.41559(19) 0.86895(9) 0.0469(4) Uani d . 1 1 . .
C C18 0.2187(3) 0.3077(3) 0.95785(16) 0.0975(9) Uani d . 1 1 . .
H H18A 0.2735 0.3321 1.0061 0.146 Uiso calc R 1 1 . .
H H18B 0.1814 0.2168 0.9638 0.146 Uiso calc R 1 1 . .
H H18C 0.1618 0.3840 0.9442 0.146 Uiso calc R 1 1 . .
N N1 0.56045(12) 0.43967(18) 0.63774(8) 0.0528(4) Uani d . 1 1 . .
H H1A 0.5244 0.4549 0.5897 0.063 Uiso calc R 1 1 . .
O O1 0.36279(10) 0.51675(14) 0.53585(7) 0.0560(3) Uani d . 1 1 . .
O O2 0.21941(10) 0.57946(15) 0.58975(7) 0.0584(3) Uani d . 1 1 . .
O O3 0.50425(11) 0.59997(12) 0.83719(7) 0.0542(3) Uani d . 1 1 . .
H H4A 0.4653 0.6298 0.8660 0.081 Uiso calc R 1 1 . .
O O4 0.29242(13) 0.53525(15) 0.89139(8) 0.0645(4) Uani d . 1 1 . .
O O5 0.27827(13) 0.29272(15) 0.89645(8) 0.0682(4) Uani d . 1 1 . .
Cl Cl1 0.10795(6) -0.02490(8) 0.60884(5) 0.1010(3) Uani d . 1 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 119.88(16) ?
C6 C1 H1 . . 120.1 ?
C2 C1 H1 . . 120.1 ?
C3 C2 C1 . . 121.8(2) ?
C3 C2 Cl1 . . 119.31(16) ?
C1 C2 Cl1 . . 118.94(16) ?
C4 C3 C2 . . 118.21(19) ?
C4 C3 H3 . . 120.9 ?
C2 C3 H3 . . 120.9 ?
C3 C4 C5 . . 121.43(19) ?
C3 C4 H4 . . 119.3 ?
C5 C4 H4 . . 119.3 ?
C4 C5 C6 . . 120.0(2) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C1 C6 C5 . . 118.74(17) ?
C1 C6 C7 . . 120.30(13) ?
C5 C6 C7 . . 120.86(17) ?
C12 C7 C6 . . 113.42(12) ?
C12 C7 C8 . . 112.29(12) ?
C6 C7 C8 . . 106.51(12) ?
C12 C7 H7 . . 108.1 ?
C6 C7 H7 . . 108.1 ?
C8 C7 H7 . . 108.1 ?
C17 C8 C9 . . 110.78(12) ?
C17 C8 C7 . . 109.55(12) ?
C9 C8 C7 . . 111.98(12) ?
C17 C8 H8 . . 108.1 ?
C9 C8 H8 . . 108.1 ?
C7 C8 H8 . . 108.1 ?
O3 C9 C10 . . 105.67(13) ?
O3 C9 C16 . . 110.09(13) ?
C10 C9 C16 . . 110.33(13) ?
O3 C9 C8 . . 111.62(12) ?
C10 C9 C8 . . 107.83(12) ?
C16 C9 C8 . . 111.13(14) ?
C11 C10 C9 . . 114.41(13) ?
C11 C10 H10A . . 108.7 ?
C9 C10 H10A . . 108.7 ?
C11 C10 H10B . . 108.7 ?
C9 C10 H10B . . 108.7 ?
H10A C10 H10B . . 107.6 ?
N1 C11 C12 . . 123.34(14) ?
N1 C11 C10 . . 115.45(13) ?
C12 C11 C10 . . 121.20(13) ?
C11 C12 C13 . . 119.52(14) ?
C11 C12 C7 . . 122.84(13) ?
C13 C12 C7 . . 117.55(13) ?
O1 C13 O2 . . 120.94(14) ?
O1 C13 C12 . . 127.01(15) ?
O2 C13 C12 . . 112.03(13) ?
O2 C14 H14A . . 109.5 ?
O2 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O2 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
N1 C15 H15A . . 109.5 ?
N1 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
N1 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C9 C16 H16A . . 109.5 ?
C9 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C9 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O4 C17 O5 . . 123.70(16) ?
O4 C17 C8 . . 124.20(15) ?
O5 C17 C8 . . 112.10(14) ?
O5 C18 H18A . . 109.5 ?
O5 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
O5 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C11 N1 C15 . . 126.10(14) ?
C11 N1 H1A . . 117.0 ?
C15 N1 H1A . . 117.0 ?
C13 O2 C14 . . 116.46(14) ?
C9 O3 H4A . . 109.5 ?
C17 O5 C18 . . 116.35(16) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.379(2) ?
C1 C2 . 1.383(2) ?
C1 H1 . 0.9300 ?
C2 C3 . 1.370(3) ?
C2 Cl1 . 1.743(2) ?
C3 C4 . 1.365(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.385(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.388(2) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.525(2) ?
C7 C12 . 1.511(2) ?
C7 C8 . 1.542(2) ?
C7 H7 . 0.9800 ?
C8 C17 . 1.508(2) ?
C8 C9 . 1.534(2) ?
C8 H8 . 0.9800 ?
C9 O3 . 1.430(2) ?
C9 C10 . 1.514(2) ?
C9 C16 . 1.525(2) ?
C10 C11 . 1.507(2) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 N1 . 1.345(2) ?
C11 C12 . 1.373(2) ?
C12 C13 . 1.445(2) ?
C13 O1 . 1.2237(19) ?
C13 O2 . 1.350(2) ?
C14 O2 . 1.433(2) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 N1 . 1.444(2) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 O4 . 1.200(2) ?
C17 O5 . 1.319(2) ?
C18 O5 . 1.451(2) ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
N1 H1A . 0.8600 ?
O3 H4A . 0.8200 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A O1 . 0.86 2.0 2.673(2) 134
O3 H4A O4 . 0.82 2.39 2.990(2) 131
C15 H15B O1 3_666 0.96 2.52 3.327(3) 142
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 1.1(3) ?
C6 C1 C2 Cl1 . . . . -178.36(12) ?
C1 C2 C3 C4 . . . . -0.7(3) ?
Cl1 C2 C3 C4 . . . . 178.76(17) ?
C2 C3 C4 C5 . . . . 0.4(3) ?
C3 C4 C5 C6 . . . . -0.6(3) ?
C2 C1 C6 C5 . . . . -1.2(2) ?
C2 C1 C6 C7 . . . . 175.25(15) ?
C4 C5 C6 C1 . . . . 1.0(3) ?
C4 C5 C6 C7 . . . . -175.46(17) ?
C1 C6 C7 C12 . . . . 49.45(19) ?
C5 C6 C7 C12 . . . . -134.17(16) ?
C1 C6 C7 C8 . . . . -74.57(17) ?
C5 C6 C7 C8 . . . . 101.81(17) ?
C12 C7 C8 C17 . . . . 165.93(13) ?
C6 C7 C8 C17 . . . . -69.36(16) ?
C12 C7 C8 C9 . . . . 42.61(17) ?
C6 C7 C8 C9 . . . . 167.32(12) ?
C17 C8 C9 O3 . . . . -69.40(16) ?
C7 C8 C9 O3 . . . . 53.22(16) ?
C17 C8 C9 C10 . . . . 174.96(12) ?
C7 C8 C9 C10 . . . . -62.42(16) ?
C17 C8 C9 C16 . . . . 53.92(17) ?
C7 C8 C9 C16 . . . . 176.54(13) ?
O3 C9 C10 C11 . . . . -70.31(16) ?
C16 C9 C10 C11 . . . . 170.72(14) ?
C8 C9 C10 C11 . . . . 49.17(18) ?
C9 C10 C11 N1 . . . . 161.63(14) ?
C9 C10 C11 C12 . . . . -17.9(2) ?
N1 C11 C12 C13 . . . . -6.3(2) ?
C10 C11 C12 C13 . . . . 173.14(14) ?
N1 C11 C12 C7 . . . . 177.30(14) ?
C10 C11 C12 C7 . . . . -3.2(2) ?
C6 C7 C12 C11 . . . . -130.26(16) ?
C8 C7 C12 C11 . . . . -9.5(2) ?
C6 C7 C12 C13 . . . . 53.32(18) ?
C8 C7 C12 C13 . . . . 174.13(13) ?
C11 C12 C13 O1 . . . . 13.8(3) ?
C7 C12 C13 O1 . . . . -169.67(15) ?
C11 C12 C13 O2 . . . . -164.39(14) ?
C7 C12 C13 O2 . . . . 12.1(2) ?
C9 C8 C17 O4 . . . . 62.5(2) ?
C7 C8 C17 O4 . . . . -61.5(2) ?
C9 C8 C17 O5 . . . . -116.62(15) ?
C7 C8 C17 O5 . . . . 119.35(15) ?
C12 C11 N1 C15 . . . . 175.24(17) ?
C10 C11 N1 C15 . . . . -4.3(2) ?
O1 C13 O2 C14 . . . . 3.0(2) ?
C12 C13 O2 C14 . . . . -178.66(16) ?
O4 C17 O5 C18 . . . . -0.7(3) ?
C8 C17 O5 C18 . . . . 178.47(18) ?
