#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/60/2206086.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_2206086
loop_
_publ_author_name
'Yu-Ling Li'
'Bai-Xiang Du'
'Xiang-Shan Wang'
'Mei-Mei Zhang'
'Zhao-Sen Zeng'
_publ_section_title
;Methyl
 4-(3-chlorophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1634
_journal_page_last               o1636
_journal_paper_doi               10.1107/S1600536805012821
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C20 H22 Cl N O3'
_chemical_formula_moiety         'C20 H22 Cl N O3'
_chemical_formula_sum            'C20 H22 Cl N O3'
_chemical_formula_weight         359.84
_chemical_melting_point          482.0(10)
_chemical_name_systematic
;
Methyl 2,7,7-trimethyl-5-oxo-4-(3-chlorophenyl)-1,4,5,6,7,8-
hexahydroquinoline-3-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 107.286(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2293(17)
_cell_length_b                   16.506(3)
_cell_length_c                   12.354(2)
_cell_measurement_reflns_used    7337
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     1797.0(5)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2003)'
_computing_molecular_graphics    SHELXL97
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_sigmaI/netI    0.027
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19907
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.0
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.13
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4094
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.13
_refine_ls_R_factor_all          0.067
_refine_ls_R_factor_gt           0.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0513P)²+0.8384P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.124
_refine_ls_wR_factor_ref         0.130
_reflns_number_gt                3542
_reflns_number_total             4094
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk6221.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '481-483' was changed to '482.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '481-483' was changed to '482.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     '-p 2yn'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2206086
_cod_database_fobs_code          2206086
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_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_type_symbol
Cl1 0.42561(8) 0.83658(5) 0.97230(5) 0.0676(2) Uani d . 1 Cl
O1 0.74803(15) 0.84424(8) 0.63521(10) 0.0355(3) Uani d . 1 O
O2 0.39170(17) 0.51038(8) 0.62478(12) 0.0411(3) Uani d . 1 O
O3 0.53551(16) 0.59756(8) 0.74972(11) 0.0360(3) Uani d . 1 O
N1 0.37375(17) 0.69091(9) 0.37348(12) 0.0280(3) Uani d . 1 N
H1 0.3103 0.6883 0.3045 0.034 Uiso calc R 1 H
C1 0.47526(19) 0.75342(10) 0.40013(14) 0.0242(3) Uani d . 1 C
C2 0.55465(18) 0.76813(10) 0.50995(13) 0.0240(3) Uani d . 1 C
C3 0.52104(19) 0.72203(10) 0.60563(13) 0.0242(3) Uani d . 1 C
H3 0.6194 0.7103 0.6647 0.029 Uiso calc R 1 H
C4 0.44457(19) 0.64163(10) 0.56190(14) 0.0247(3) Uani d . 1 C
C5 0.3670(2) 0.63121(10) 0.45127(15) 0.0269(4) Uani d . 1 C
C6 0.67119(19) 0.82958(10) 0.53680(14) 0.0262(4) Uani d . 1 C
C7 0.7018(2) 0.87509(12) 0.43979(15) 0.0320(4) Uani d . 1 C
H7A 0.7811 0.8459 0.4161 0.038 Uiso calc R 1 H
H7B 0.7424 0.9293 0.4670 0.038 Uiso calc R 1 H
C8 0.5620(2) 0.88561(11) 0.33615(14) 0.0285(4) Uani d . 1 C
C9 0.4937(2) 0.80157(11) 0.30207(14) 0.0283(4) Uani d . 1 C
H9A 0.3933 0.8078 0.2448 0.034 Uiso calc R 1 H
H9B 0.5599 0.7712 0.2663 0.034 Uiso calc R 1 H
C10 0.4216(2) 0.77125(10) 0.66031(14) 0.0261(4) Uani d . 1 C
C11 0.4642(2) 0.78227(12) 0.77730(15) 0.0328(4) Uani d . 1 C
H11 0.5571 0.7604 0.8238 0.039 Uiso calc R 1 H
C12 0.3703(3) 0.82533(12) 0.82534(17) 0.0383(5) Uani d . 1 C
C13 0.2352(3) 0.85818(12) 0.76177(18) 0.0404(5) Uani d . 1 C
H13 0.1732 0.8882 0.7965 0.049 Uiso calc R 1 H
C14 0.1919(3) 0.84636(12) 0.64544(18) 0.0415(5) Uani d . 1 C
H14 0.0981 0.8677 0.5997 0.050 Uiso calc R 1 H
C15 0.2844(2) 0.80368(12) 0.59544(16) 0.0348(4) Uani d . 1 C
H15 0.2535 0.7965 0.5155 0.042 Uiso calc R 1 H
C16 0.4504(2) 0.57638(11) 0.64373(15) 0.0279(4) Uani d . 1 C
C17 0.5478(3) 0.53704(13) 0.83609(17) 0.0409(5) Uani d . 1 C
H17A 0.4465 0.5241 0.8414 0.061 Uiso calc R 1 H
H17B 0.6110 0.5579 0.9092 0.061 Uiso calc R 1 H
H17C 0.5944 0.4880 0.8165 0.061 Uiso calc R 1 H
C18 0.2688(2) 0.56078(11) 0.39892(16) 0.0356(4) Uani d . 1 C
H18A 0.3294 0.5110 0.4132 0.053 Uiso calc R 1 H
H18B 0.2274 0.5694 0.3170 0.053 Uiso calc R 1 H
H18C 0.1852 0.5559 0.4323 0.053 Uiso calc R 1 H
C19 0.4459(3) 0.94103(12) 0.36408(17) 0.0417(5) Uani d . 1 C
H19A 0.3544 0.9438 0.2988 0.063 Uiso calc R 1 H
H19B 0.4891 0.9954 0.3817 0.063 Uiso calc R 1 H
H19C 0.4196 0.9195 0.4297 0.063 Uiso calc R 1 H
C20 0.6085(3) 0.92225(14) 0.23794(16) 0.0422(5) Uani d . 1 C
H20A 0.5184 0.9292 0.1724 0.063 Uiso calc R 1 H
H20B 0.6804 0.8860 0.2177 0.063 Uiso calc R 1 H
H20C 0.6564 0.9750 0.2607 0.063 Uiso calc R 1 H
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C16 O3 C17 115.55(15) ?
C1 N1 C5 122.47(14) yes
C1 N1 H1 118.8 ?
C5 N1 H1 118.8 ?
C2 C1 N1 120.22(15) yes
C2 C1 C9 123.69(15) yes
N1 C1 C9 116.08(14) ?
C1 C2 C6 119.94(15) yes
C1 C2 C3 121.01(15) yes
C6 C2 C3 119.05(14) ?
C2 C3 C4 109.98(13) yes
C2 C3 C10 111.59(13) ?
C4 C3 C10 110.15(14) ?
C2 C3 H3 108.3 ?
C4 C3 H3 108.3 ?
C10 C3 H3 108.3 ?
C5 C4 C16 120.19(15) ?
C5 C4 C3 121.28(15) yes
C16 C4 C3 118.46(14) ?
C4 C5 N1 119.29(15) yes
C4 C5 C18 127.30(16) ?
N1 C5 C18 113.41(15) ?
O1 C6 C2 122.29(16) ?
O1 C6 C7 119.69(16) ?
C2 C6 C7 117.99(15) ?
C6 C7 C8 114.15(15) ?
C6 C7 H7A 108.7 ?
C8 C7 H7A 108.7 ?
C6 C7 H7B 108.7 ?
C8 C7 H7B 108.7 ?
H7A C7 H7B 107.6 ?
C19 C8 C20 108.94(16) ?
C19 C8 C9 110.30(16) ?
C20 C8 C9 109.29(15) ?
C19 C8 C7 110.65(15) ?
C20 C8 C7 110.04(16) ?
C9 C8 C7 107.60(14) ?
C1 C9 C8 113.22(14) ?
C1 C9 H9A 108.9 ?
C8 C9 H9A 108.9 ?
C1 C9 H9B 108.9 ?
C8 C9 H9B 108.9 ?
H9A C9 H9B 107.7 ?
C15 C10 C11 118.48(17) ?
C15 C10 C3 121.00(15) ?
C11 C10 C3 120.49(16) ?
C12 C11 C10 119.48(18) ?
C12 C11 H11 120.3 ?
C10 C11 H11 120.3 ?
C13 C12 C11 122.40(18) ?
C13 C12 Cl1 119.29(16) ?
C11 C12 Cl1 118.30(17) ?
C12 C13 C14 118.10(19) ?
C12 C13 H13 121.0 ?
C14 C13 H13 121.0 ?
C15 C14 C13 120.5(2) ?
C15 C14 H14 119.7 ?
C13 C14 H14 119.7 ?
C14 C15 C10 121.03(18) ?
C14 C15 H15 119.5 ?
C10 C15 H15 119.5 ?
O2 C16 O3 121.12(16) ?
O2 C16 C4 127.30(17) ?
O3 C16 C4 111.57(15) ?
O3 C17 H17A 109.5 ?
O3 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
O3 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
C5 C18 H18A 109.5 ?
C5 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C5 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
C8 C19 H19A 109.5 ?
C8 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C8 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
C8 C20 H20A 109.5 ?
C8 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
C8 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C12 1.744(2) ?
O1 C6 1.236(2) yes
O2 C16 1.208(2) ?
O3 C16 1.358(2) ?
O3 C17 1.441(2) ?
N1 C1 1.366(2) yes
N1 C5 1.391(2) yes
N1 H1 0.8800 ?
C1 C2 1.359(2) yes
C1 C9 1.500(2) yes
C2 C6 1.444(2) yes
C2 C3 1.513(2) yes
C3 C4 1.525(2) ?
C3 C10 1.526(2) ?
C3 H3 1.0000 ?
C4 C5 1.352(2) yes
C4 C16 1.467(2) ?
C5 C18 1.498(2) ?
C6 C7 1.510(2) ?
C7 C8 1.534(2) ?
C7 H7A 0.9900 ?
C7 H7B 0.9900 ?
C8 C19 1.524(3) ?
C8 C20 1.527(3) ?
C8 C9 1.530(2) ?
C9 H9A 0.9900 ?
C9 H9B 0.9900 ?
C10 C15 1.389(3) ?
C10 C11 1.392(2) ?
C11 C12 1.384(3) ?
C11 H11 0.9500 ?
C12 C13 1.372(3) ?
C13 C14 1.386(3) ?
C13 H13 0.9500 ?
C14 C15 1.385(3) ?
C14 H14 0.9500 ?
C15 H15 0.9500 ?
C17 H17A 0.9800 ?
C17 H17B 0.9800 ?
C17 H17C 0.9800 ?
C18 H18A 0.9800 ?
C18 H18B 0.9800 ?
C18 H18C 0.9800 ?
C19 H19A 0.9800 ?
C19 H19B 0.9800 ?
C19 H19C 0.9800 ?
C20 H20A 0.9800 ?
C20 H20B 0.9800 ?
C20 H20C 0.9800 ?
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 H1 O1 4_575 0.88 2.07 2.8841(19) 154
C20 H20A Cl1 1_554 0.98 2.81 3.511(2) 129
C13 H13 O2 2_556 0.95 2.39 3.260(2) 152
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
_geom_torsion_publ_flag
C5 N1 C1 C2 -12.4(2) yes
C5 N1 C1 C9 166.38(15) ?
N1 C1 C2 C6 174.55(15) ?
C9 C1 C2 C6 -4.2(3) yes
N1 C1 C2 C3 -6.6(2) yes
C9 C1 C2 C3 174.68(15) ?
C1 C2 C3 C4 23.1(2) ?
C6 C2 C3 C4 -158.05(15) ?
C1 C2 C3 C10 -99.45(18) ?
C6 C2 C3 C10 79.41(19) ?
C2 C3 C4 C5 -24.2(2) yes
C10 C3 C4 C5 99.24(18) ?
C2 C3 C4 C16 158.82(14) ?
C10 C3 C4 C16 -77.79(18) ?
C16 C4 C5 N1 -174.42(15) ?
C3 C4 C5 N1 8.6(2) ?
C16 C4 C5 C18 6.2(3) ?
C3 C4 C5 C18 -170.78(17) ?
C1 N1 C5 C4 11.3(2) yes
C1 N1 C5 C18 -169.19(16) ?
C1 C2 C6 O1 -178.82(17) ?
C3 C2 C6 O1 2.3(3) ?
C1 C2 C6 C7 -0.7(2) yes
C3 C2 C6 C7 -179.61(15) ?
O1 C6 C7 C8 -150.63(17) ?
C2 C6 C7 C8 31.2(2) yes
C6 C7 C8 C19 66.9(2) ?
C6 C7 C8 C20 -172.67(16) ?
C6 C7 C8 C9 -53.7(2) yes
C2 C1 C9 C8 -21.5(2) ?
N1 C1 C9 C8 159.72(15) ?
C19 C8 C9 C1 -72.60(19) ?
C20 C8 C9 C1 167.66(16) ?
C7 C8 C9 C1 48.2(2) yes
C2 C3 C10 C15 53.8(2) ?
C4 C3 C10 C15 -68.6(2) ?
C2 C3 C10 C11 -128.43(17) ?
C4 C3 C10 C11 109.13(18) ?
C15 C10 C11 C12 -0.5(3) ?
C3 C10 C11 C12 -178.29(16) ?
C10 C11 C12 C13 -0.1(3) ?
C10 C11 C12 Cl1 178.97(14) ?
C11 C12 C13 C14 0.9(3) ?
Cl1 C12 C13 C14 -178.19(16) ?
C12 C13 C14 C15 -1.1(3) ?
C13 C14 C15 C10 0.5(3) ?
C11 C10 C15 C14 0.3(3) ?
C3 C10 C15 C14 178.09(17) ?
C17 O3 C16 O2 -1.0(3) ?
C17 O3 C16 C4 -179.98(15) ?
C5 C4 C16 O2 0.0(3) ?
C3 C4 C16 O2 177.07(17) ?
C5 C4 C16 O3 178.89(15) ?
C3 C4 C16 O3 -4.0(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2124612
