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#$Date: 2022-12-05 12:31:46 +0200 (Mon, 05 Dec 2022) $
#$Revision: 279701 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/63/8106325.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106325
loop_
_publ_author_name
'Ren, Tao-Wen'
'Xiao, Xing-Peng'
'Li, Bai-Yu'
'Zhao, Yu-Mei'
'Peng, Shao-Peng'
_publ_section_title
;
 Crystal structure of methyl
 4-(4-bromophenyl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate,
 C20H22BrNO3
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              863
_journal_page_last               864
_journal_paper_doi               10.1515/ncrs-2018-0060
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C20 H22 Br N O3'
_chemical_formula_sum            'C20 H22 Br N O3'
_chemical_formula_weight         404.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 111.355(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.597(2)
_cell_length_b                   18.236(5)
_cell_length_c                   11.640(3)
_cell_measurement_reflns_used    1600
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.71
_cell_measurement_theta_min      2.19
_cell_volume                     1897.3(8)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_collection       'Bruker Smart APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0710
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9434
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         2.185
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.184
_exptl_absorpt_correction_T_max  0.7077
_exptl_absorpt_correction_T_min  0.6005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0497
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0546P)²+0.4502P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1240
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1913
_reflns_number_total             3337
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0060_suppl.cif
_cod_data_source_block           a
_cod_database_code               8106325
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.708
_shelx_estimated_absorpt_t_min   0.600
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C13(H13A,H13B)
2.c Me refined with riding coordinates:
 C1(H1A,H1B,H1C), C5(H5A,H5B,H5C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
2.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C16(H16), C17(H17), C19(H19), C20(H20)
;
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2178(3) 0.31642(16) 0.4445(3) 0.0437(8) Uani 1 1 d . . . . .
H1 H 0.156682 0.326072 0.371137 0.052 Uiso 1 1 calc R . . . .
Br1 Br -0.04573(7) 0.05860(3) 0.85548(5) 0.0885(3) Uani 1 1 d . . . . .
O1 O 0.3753(4) 0.36240(15) 0.8710(3) 0.0718(9) Uani 1 1 d . . . . .
O2 O 0.2494(3) 0.45084(13) 0.7455(2) 0.0586(8) Uani 1 1 d . . . . .
O3 O 0.5493(3) 0.14298(14) 0.6953(2) 0.0617(8) Uani 1 1 d . . . . .
C1 C 0.2667(6) 0.4951(2) 0.8529(4) 0.0731(14) Uani 1 1 d . . . . .
H1A H 0.219089 0.541709 0.827288 0.110 Uiso 1 1 calc R . . . .
H1B H 0.221228 0.470487 0.903332 0.110 Uiso 1 1 calc R . . . .
H1C H 0.371173 0.502391 0.899529 0.110 Uiso 1 1 calc R . . . .
C2 C 0.3101(4) 0.3845(2) 0.7672(4) 0.0434(9) Uani 1 1 d . . . . .
C3 C 0.2908(4) 0.34053(18) 0.6568(3) 0.0373(9) Uani 1 1 d . . . . .
C4 C 0.2202(4) 0.36267(19) 0.5398(3) 0.0407(9) Uani 1 1 d . . . . .
C5 C 0.1398(5) 0.43307(19) 0.4947(4) 0.0587(12) Uani 1 1 d . . . . .
H5A H 0.100553 0.433372 0.406107 0.088 Uiso 1 1 calc R . . . .
H5B H 0.059153 0.437888 0.524358 0.088 Uiso 1 1 calc R . . . .
H5C H 0.208062 0.473292 0.524477 0.088 Uiso 1 1 calc R . . . .
C6 C 0.3070(4) 0.25692(19) 0.4613(3) 0.0381(9) Uani 1 1 d . . . . .
C7 C 0.3819(4) 0.23108(18) 0.5767(3) 0.0366(9) Uani 1 1 d . . . . .
C8 C 0.3544(4) 0.26328(18) 0.6859(3) 0.0364(9) Uani 1 1 d . . . . .
H8 H 0.451202 0.266870 0.754087 0.044 Uiso 1 1 calc R . . . .
C9 C 0.3177(4) 0.2239(2) 0.3471(3) 0.0484(10) Uani 1 1 d . . . . .
H9A H 0.387764 0.252257 0.322641 0.058 Uiso 1 1 calc R . . . .
H9B H 0.220577 0.226978 0.280985 0.058 Uiso 1 1 calc R . . . .
C10 C 0.3677(5) 0.1446(2) 0.3633(3) 0.0517(11) Uani 1 1 d . . . . .
C11 C 0.4040(6) 0.1193(3) 0.2525(4) 0.0877(17) Uani 1 1 d . . . . .
H11A H 0.316459 0.123751 0.178972 0.132 Uiso 1 1 calc R . . . .
H11B H 0.482649 0.149193 0.245146 0.132 Uiso 1 1 calc R . . . .
H11C H 0.435773 0.069010 0.263679 0.132 Uiso 1 1 calc R . . . .
C12 C 0.2409(5) 0.0966(2) 0.3705(4) 0.0712(13) Uani 1 1 d . . . . .
H12A H 0.155698 0.100987 0.295150 0.107 Uiso 1 1 calc R . . . .
H12B H 0.273115 0.046360 0.382222 0.107 Uiso 1 1 calc R . . . .
H12C H 0.214154 0.112141 0.438468 0.107 Uiso 1 1 calc R . . . .
C13 C 0.5030(5) 0.1383(2) 0.4811(3) 0.0644(13) Uani 1 1 d . . . . .
H13A H 0.529620 0.086976 0.496357 0.077 Uiso 1 1 calc R . . . .
H13B H 0.586354 0.163292 0.469829 0.077 Uiso 1 1 calc R . . . .
C14 C 0.4811(4) 0.1699(2) 0.5933(4) 0.0475(10) Uani 1 1 d . . . . .
C15 C 0.2546(4) 0.21449(18) 0.7278(3) 0.0359(9) Uani 1 1 d . . . . .
C16 C 0.1152(4) 0.1928(2) 0.6472(3) 0.0445(10) Uani 1 1 d . . . . .
H16 H 0.082118 0.209436 0.566156 0.053 Uiso 1 1 calc R . . . .
C17 C 0.0239(5) 0.1476(2) 0.6831(4) 0.0502(10) Uani 1 1 d . . . . .
H17 H -0.069257 0.133539 0.627118 0.060 Uiso 1 1 calc R . . . .
C18 C 0.0726(5) 0.1236(2) 0.8025(4) 0.0512(11) Uani 1 1 d . . . . .
C19 C 0.2088(6) 0.1441(2) 0.8854(4) 0.0642(13) Uani 1 1 d . . . . .
H19 H 0.241086 0.127451 0.966455 0.077 Uiso 1 1 calc R . . . .
C20 C 0.2981(5) 0.1901(2) 0.8473(3) 0.0539(11) Uani 1 1 d . . . . .
H20 H 0.390103 0.204856 0.904147 0.065 Uiso 1 1 calc R . . . .
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'
Br Br -0.2901 2.4595 '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_site_symmetry_1
_geom_angle_site_symmetry_3
C4 N1 H1 118.4 . .
C6 N1 H1 118.4 . .
C6 N1 C4 123.2(3) . .
C2 O2 C1 116.1(3) . .
O2 C1 H1A 109.5 . .
O2 C1 H1B 109.5 . .
O2 C1 H1C 109.5 . .
H1A C1 H1B 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
O1 C2 O2 121.7(3) . .
O1 C2 C3 123.2(4) . .
O2 C2 C3 115.1(4) . .
C2 C3 C8 113.4(3) . .
C4 C3 C2 125.5(3) . .
C4 C3 C8 121.1(3) . .
N1 C4 C5 112.7(3) . .
C3 C4 N1 118.9(3) . .
C3 C4 C5 128.4(3) . .
C4 C5 H5A 109.5 . .
C4 C5 H5B 109.5 . .
C4 C5 H5C 109.5 . .
H5A C5 H5B 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
N1 C6 C7 120.1(3) . .
N1 C6 C9 116.0(3) . .
C7 C6 C9 123.9(3) . .
C6 C7 C8 120.5(3) . .
C6 C7 C14 119.3(3) . .
C14 C7 C8 120.1(3) . .
C3 C8 H8 107.7 . .
C7 C8 C3 110.6(3) . .
C7 C8 H8 107.7 . .
C7 C8 C15 111.6(3) . .
C15 C8 C3 111.5(3) . .
C15 C8 H8 107.7 . .
C6 C9 H9A 108.9 . .
C6 C9 H9B 108.9 . .
C6 C9 C10 113.2(3) . .
H9A C9 H9B 107.7 . .
C10 C9 H9A 108.9 . .
C10 C9 H9B 108.9 . .
C9 C10 C11 110.0(3) . .
C9 C10 C12 109.4(4) . .
C11 C10 C12 107.8(4) . .
C13 C10 C9 108.3(3) . .
C13 C10 C11 111.1(3) . .
C13 C10 C12 110.3(3) . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11B 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12B 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C10 C13 H13A 108.7 . .
C10 C13 H13B 108.7 . .
H13A C13 H13B 107.6 . .
C14 C13 C10 114.3(3) . .
C14 C13 H13A 108.7 . .
C14 C13 H13B 108.7 . .
O3 C14 C7 122.3(3) . .
O3 C14 C13 119.3(3) . .
C7 C14 C13 118.4(3) . .
C16 C15 C8 121.3(3) . .
C20 C15 C8 121.5(3) . .
C20 C15 C16 117.2(3) . .
C15 C16 H16 118.9 . .
C17 C16 C15 122.2(3) . .
C17 C16 H16 118.9 . .
C16 C17 H17 120.6 . .
C18 C17 C16 118.8(4) . .
C18 C17 H17 120.6 . .
C17 C18 Br1 120.5(3) . .
C19 C18 Br1 118.4(3) . .
C19 C18 C17 121.1(4) . .
C18 C19 H19 120.5 . .
C18 C19 C20 119.0(4) . .
C20 C19 H19 120.5 . .
C15 C20 C19 121.8(4) . .
C15 C20 H20 119.1 . .
C19 C20 H20 119.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 H1 0.8600 .
N1 C4 1.387(4) .
N1 C6 1.351(4) .
Br1 C18 1.893(4) .
O1 C2 1.210(4) .
O2 C1 1.446(4) .
O2 C2 1.327(4) .
O3 C14 1.230(4) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C3 1.468(5) .
C3 C4 1.344(5) .
C3 C8 1.524(5) .
C4 C5 1.491(5) .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
C6 C7 1.356(4) .
C6 C9 1.497(5) .
C7 C8 1.508(4) .
C7 C14 1.434(5) .
C8 H8 0.9800 .
C8 C15 1.512(5) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C9 C10 1.514(5) .
C10 C11 1.525(5) .
C10 C12 1.525(6) .
C10 C13 1.511(5) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C13 C14 1.510(5) .
C15 C16 1.382(5) .
C15 C20 1.373(5) .
C16 H16 0.9300 .
C16 C17 1.374(5) .
C17 H17 0.9300 .
C17 C18 1.367(5) .
C18 C19 1.365(6) .
C19 H19 0.9300 .
C19 C20 1.382(5) .
C20 H20 0.9300 .
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
N1 C6 C7 C8 6.4(5) . . . .
N1 C6 C7 C14 -177.3(3) . . . .
N1 C6 C9 C10 -158.3(3) . . . .
Br1 C18 C19 C20 178.4(3) . . . .
O1 C2 C3 C4 -179.6(4) . . . .
O1 C2 C3 C8 2.7(5) . . . .
O2 C2 C3 C4 1.0(5) . . . .
O2 C2 C3 C8 -176.8(3) . . . .
C1 O2 C2 O1 0.4(6) . . . .
C1 O2 C2 C3 179.8(3) . . . .
C2 C3 C4 N1 176.5(3) . . . .
C2 C3 C4 C5 -3.5(6) . . . .
C2 C3 C8 C7 -159.7(3) . . . .
C2 C3 C8 C15 75.5(4) . . . .
C3 C8 C15 C16 68.8(4) . . . .
C3 C8 C15 C20 -110.9(4) . . . .
C4 N1 C6 C7 13.6(5) . . . .
C4 N1 C6 C9 -165.6(3) . . . .
C4 C3 C8 C7 22.5(5) . . . .
C4 C3 C8 C15 -102.3(4) . . . .
C6 N1 C4 C3 -13.7(5) . . . .
C6 N1 C4 C5 166.3(3) . . . .
C6 C7 C8 C3 -22.6(5) . . . .
C6 C7 C8 C15 102.1(4) . . . .
C6 C7 C14 O3 -178.3(4) . . . .
C6 C7 C14 C13 2.4(5) . . . .
C6 C9 C10 C11 -169.4(3) . . . .
C6 C9 C10 C12 72.4(4) . . . .
C6 C9 C10 C13 -47.8(5) . . . .
C7 C6 C9 C10 22.5(5) . . . .
C7 C8 C15 C16 -55.4(4) . . . .
C7 C8 C15 C20 124.9(4) . . . .
C8 C3 C4 N1 -6.0(5) . . . .
C8 C3 C4 C5 174.0(4) . . . .
C8 C7 C14 O3 -1.9(6) . . . .
C8 C7 C14 C13 178.8(3) . . . .
C8 C15 C16 C17 178.9(3) . . . .
C8 C15 C20 C19 -178.5(3) . . . .
C9 C6 C7 C8 -174.5(3) . . . .
C9 C6 C7 C14 1.9(5) . . . .
C9 C10 C13 C14 52.8(5) . . . .
C10 C13 C14 O3 149.4(4) . . . .
C10 C13 C14 C7 -31.3(6) . . . .
C11 C10 C13 C14 173.8(4) . . . .
C12 C10 C13 C14 -66.8(5) . . . .
C14 C7 C8 C3 161.0(3) . . . .
C14 C7 C8 C15 -74.2(4) . . . .
C15 C16 C17 C18 0.3(6) . . . .
C16 C15 C20 C19 1.8(6) . . . .
C16 C17 C18 Br1 -178.0(3) . . . .
C16 C17 C18 C19 0.3(6) . . . .
C17 C18 C19 C20 0.1(6) . . . .
C18 C19 C20 C15 -1.2(6) . . . .
C20 C15 C16 C17 -1.3(5) . . . .
