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#$Date: 2022-06-28 11:05:40 +0300 (Tue, 28 Jun 2022) $
#$Revision: 276309 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/55/8105541.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_8105541
loop_
_publ_author_name
'Zheng, Feng'
'Quan, Ji-Shu'
'Cui, Xiang-Dan'
'Jin, Xue-Feng'
'Yin, Xue-Zhe'
_publ_section_title
;
 Crystal structural of diethyl
 4-(3,5-dibromo-4-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate,
 C19H21Br2NO5
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              59
_journal_page_last               60
_journal_paper_doi               10.1515/ncrs-2018-0152
_journal_volume                  234
_journal_year                    2018
_chemical_formula_moiety         'C19 H21 Br2 N O5'
_chemical_formula_sum            'C19 H21 Br2 N O5'
_chemical_formula_weight         503.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 104.807(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.657(5)
_cell_length_b                   17.150(5)
_cell_length_c                   13.889(4)
_cell_measurement_reflns_used    1417
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.08
_cell_measurement_theta_min      2.43
_cell_volume                     1993.6(14)
_computing_cell_refinement       'SAINT v7.60A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.1058
_diffrn_reflns_av_unetI/netI     0.1453
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9761
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.375
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.096
_exptl_absorpt_correction_T_max  0.458
_exptl_absorpt_correction_T_min  0.359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.17
_refine_diff_density_max         1.110
_refine_diff_density_min         -0.945
_refine_diff_density_rms         0.136
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.901
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3493
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.901
_refine_ls_R_factor_all          0.1307
_refine_ls_R_factor_gt           0.0646
_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)+(0.0793P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1523
_refine_ls_wR_factor_ref         0.1732
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1911
_reflns_number_total             3493
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0152_suppl.cif
_cod_data_source_block           a
_cod_database_code               8105541
_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.
;
_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. Restrained distances
 O5-H5
 0.83 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B)
3.c Me refined with riding coordinates:
 C1(H1A,H1B,H1C), C4(H4A,H4B,H4C), C10(H10A,H10B,H10C), C13(H13A,H13B,H13C)
3.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C15(H15), C19(H19)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.5943(7) 0.1264(4) -0.0028(4) 0.0465(17) Uani 1 1 d . . . . .
H1 H 0.627845 0.147614 -0.049849 0.056 Uiso 1 1 calc R . . . .
Br1 Br 0.90836(9) 0.31691(5) 0.33162(5) 0.0489(3) Uani 1 1 d . . . . .
Br2 Br 0.66838(11) 0.10642(6) 0.57107(5) 0.0674(4) Uani 1 1 d . . . . .
O1 O 0.2408(6) 0.1233(3) 0.1981(4) 0.0492(14) Uani 1 1 d . . . . .
O2 O 0.1676(6) 0.2006(4) 0.0669(4) 0.0640(17) Uani 1 1 d . . . . .
O3 O 0.6523(7) -0.0576(3) 0.2504(4) 0.0608(16) Uani 1 1 d . . . . .
O4 O 0.8539(8) -0.0548(4) 0.1784(5) 0.0750(19) Uani 1 1 d . . . . .
O5 O 0.8605(7) 0.2383(4) 0.5244(3) 0.0509(15) Uani 1 1 d D . . . .
C1 C 0.3741(9) 0.2150(5) -0.0589(5) 0.055(2) Uani 1 1 d . . . . .
H1A H 0.430926 0.221301 -0.109435 0.082 Uiso 1 1 calc R . . . .
H1B H 0.267859 0.196796 -0.088842 0.082 Uiso 1 1 calc R . . . .
H1C H 0.368901 0.264237 -0.026945 0.082 Uiso 1 1 calc R . . . .
C2 C 0.4600(8) 0.1566(4) 0.0171(5) 0.0395(18) Uani 1 1 d . . . . .
C3 C 0.6813(8) 0.0636(5) 0.0477(5) 0.0430(19) Uani 1 1 d . . . . .
C4 C 0.8041(9) 0.0325(5) 0.0010(5) 0.055(2) Uani 1 1 d . . . . .
H4A H 0.803914 0.062268 -0.057546 0.082 Uiso 1 1 calc R . . . .
H4B H 0.907272 0.036017 0.047293 0.082 Uiso 1 1 calc R . . . .
H4C H 0.780798 -0.021103 -0.017091 0.082 Uiso 1 1 calc R . . . .
C5 C 0.6429(8) 0.0386(4) 0.1307(4) 0.0327(16) Uani 1 1 d . . . . .
C6 C 0.5229(8) 0.0802(4) 0.1749(5) 0.0337(17) Uani 1 1 d . . . . .
H6 H 0.455516 0.040699 0.194952 0.040 Uiso 1 1 calc R . . . .
C7 C 0.4154(8) 0.1331(4) 0.0985(5) 0.0350(17) Uani 1 1 d . . . . .
C8 C 0.2649(8) 0.1573(5) 0.1158(5) 0.0422(19) Uani 1 1 d . . . . .
C9 C 0.0961(10) 0.1397(6) 0.2267(6) 0.064(3) Uani 1 1 d . . . . .
H9A H 0.004214 0.124090 0.174119 0.076 Uiso 1 1 calc R . . . .
H9B H 0.088070 0.195094 0.238435 0.076 Uiso 1 1 calc R . . . .
C10 C 0.1000(11) 0.0955(6) 0.3187(7) 0.079(3) Uani 1 1 d . . . . .
H10A H 0.004123 0.105673 0.339242 0.118 Uiso 1 1 calc R . . . .
H10B H 0.107496 0.040776 0.306331 0.118 Uiso 1 1 calc R . . . .
H10C H 0.191034 0.111511 0.370403 0.118 Uiso 1 1 calc R . . . .
C11 C 0.7313(10) -0.0275(5) 0.1851(6) 0.049(2) Uani 1 1 d . . . . .
C12 C 0.7312(13) -0.1189(6) 0.3162(7) 0.087(3) Uani 1 1 d . . . . .
H12A H 0.799024 -0.148569 0.283817 0.104 Uiso 1 1 calc R . . . .
H12B H 0.651585 -0.154122 0.329795 0.104 Uiso 1 1 calc R . . . .
C13 C 0.8276(14) -0.0875(7) 0.4097(7) 0.103(4) Uani 1 1 d . . . . .
H13A H 0.878323 -0.129507 0.451781 0.155 Uiso 1 1 calc R . . . .
H13B H 0.907697 -0.053356 0.396585 0.155 Uiso 1 1 calc R . . . .
H13C H 0.760408 -0.058904 0.442516 0.155 Uiso 1 1 calc R . . . .
C14 C 0.6093(8) 0.1249(4) 0.2676(5) 0.0322(16) Uani 1 1 d . . . . .
C15 C 0.6997(8) 0.1911(4) 0.2609(5) 0.0351(17) Uani 1 1 d . . . . .
H15 H 0.703836 0.209201 0.198509 0.042 Uiso 1 1 calc R . . . .
C16 C 0.7829(8) 0.2301(4) 0.3449(5) 0.0373(18) Uani 1 1 d . . . . .
C17 C 0.7811(8) 0.2041(4) 0.4390(5) 0.0372(18) Uani 1 1 d . . . . .
C18 C 0.6849(8) 0.1409(5) 0.4454(5) 0.0389(18) Uani 1 1 d . . . . .
C19 C 0.6004(8) 0.1025(4) 0.3608(5) 0.0395(18) Uani 1 1 d . . . . .
H19 H 0.535879 0.060471 0.367297 0.047 Uiso 1 1 calc R . . . .
H5 H 0.944(5) 0.261(4) 0.526(5) 0.04(3) Uiso 1 1 d D . . . .
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'
Br Br -0.2901 2.4595 '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_site_symmetry_1
_geom_angle_site_symmetry_3
C2 N1 H1 117.6 . .
C2 N1 C3 124.7(6) . .
C3 N1 H1 117.6 . .
C8 O1 C9 119.1(6) . .
C11 O3 C12 117.3(7) . .
C17 O5 H5 119(5) . .
H1A C1 H1B 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
N1 C2 C1 113.8(6) . .
C7 C2 N1 119.9(7) . .
C7 C2 C1 126.3(7) . .
N1 C3 C4 114.5(6) . .
C5 C3 N1 117.1(7) . .
C5 C3 C4 128.5(7) . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4B 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C3 C5 C6 122.8(7) . .
C3 C5 C11 118.4(7) . .
C11 C5 C6 118.6(6) . .
C5 C6 H6 108.0 . .
C5 C6 C7 111.0(5) . .
C5 C6 C14 109.9(5) . .
C7 C6 H6 108.0 . .
C14 C6 H6 108.0 . .
C14 C6 C7 111.8(6) . .
C2 C7 C6 120.6(6) . .
C2 C7 C8 121.2(7) . .
C8 C7 C6 118.1(6) . .
O1 C8 C7 111.1(6) . .
O2 C8 O1 120.8(7) . .
O2 C8 C7 128.1(7) . .
O1 C9 H9A 110.1 . .
O1 C9 H9B 110.1 . .
O1 C9 C10 108.1(7) . .
H9A C9 H9B 108.4 . .
C10 C9 H9A 110.1 . .
C10 C9 H9B 110.1 . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10B 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
O3 C11 C5 110.5(7) . .
O4 C11 O3 120.8(8) . .
O4 C11 C5 128.7(8) . .
O3 C12 H12A 109.3 . .
O3 C12 H12B 109.3 . .
O3 C12 C13 111.4(9) . .
H12A C12 H12B 108.0 . .
C13 C12 H12A 109.3 . .
C13 C12 H12B 109.3 . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C15 C14 C6 121.1(6) . .
C19 C14 C6 121.6(6) . .
C19 C14 C15 117.3(6) . .
C14 C15 H15 119.3 . .
C16 C15 C14 121.3(6) . .
C16 C15 H15 119.3 . .
C15 C16 Br1 119.4(5) . .
C15 C16 C17 120.8(7) . .
C17 C16 Br1 119.7(5) . .
O5 C17 C16 124.4(7) . .
O5 C17 C18 117.7(6) . .
C18 C17 C16 117.8(6) . .
C17 C18 Br2 119.7(5) . .
C19 C18 Br2 119.3(6) . .
C19 C18 C17 121.0(6) . .
C14 C19 C18 121.6(7) . .
C14 C19 H19 119.2 . .
C18 C19 H19 119.2 . .
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 C2 1.364(9) .
N1 C3 1.397(9) .
Br1 C16 1.879(7) .
Br2 C18 1.883(7) .
O1 C8 1.345(8) .
O1 C9 1.436(8) .
O2 C8 1.196(8) .
O3 C11 1.368(9) .
O3 C12 1.446(10) .
O4 C11 1.185(9) .
O5 C17 1.345(8) .
O5 H5 0.81(2) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C1 C2 1.507(10) .
C2 C7 1.346(9) .
C3 C4 1.479(10) .
C3 C5 1.349(9) .
C4 H4A 0.9600 .
C4 H4B 0.9600 .
C4 H4C 0.9600 .
C5 C6 1.514(9) .
C5 C11 1.465(10) .
C6 H6 0.9800 .
C6 C7 1.520(9) .
C6 C14 1.519(9) .
C7 C8 1.445(9) .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C9 C10 1.478(11) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C12 C13 1.456(13) .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 C15 1.395(9) .
C14 C19 1.372(9) .
C15 H15 0.9300 .
C15 C16 1.379(9) .
C16 C17 1.384(9) .
C17 C18 1.383(10) .
C18 C19 1.381(9) .
C19 H19 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 C2 C7 C6 7.0(10) . . . .
N1 C2 C7 C8 -173.0(6) . . . .
N1 C3 C5 C6 -5.9(10) . . . .
N1 C3 C5 C11 179.7(6) . . . .
Br1 C16 C17 O5 2.2(10) . . . .
Br1 C16 C17 C18 178.9(5) . . . .
Br2 C18 C19 C14 -179.5(5) . . . .
O5 C17 C18 Br2 0.4(9) . . . .
O5 C17 C18 C19 -179.7(6) . . . .
C1 C2 C7 C6 -173.4(7) . . . .
C1 C2 C7 C8 6.6(11) . . . .
C2 N1 C3 C4 169.4(7) . . . .
C2 N1 C3 C5 -10.0(10) . . . .
C2 C7 C8 O1 176.3(6) . . . .
C2 C7 C8 O2 -3.0(12) . . . .
C3 N1 C2 C1 -170.3(6) . . . .
C3 N1 C2 C7 9.4(11) . . . .
C3 C5 C6 C7 19.4(9) . . . .
C3 C5 C6 C14 -104.9(7) . . . .
C3 C5 C11 O3 -164.4(6) . . . .
C3 C5 C11 O4 15.5(12) . . . .
C4 C3 C5 C6 174.9(7) . . . .
C4 C3 C5 C11 0.5(11) . . . .
C5 C6 C7 C2 -19.8(9) . . . .
C5 C6 C7 C8 160.3(6) . . . .
C5 C6 C14 C15 70.1(8) . . . .
C5 C6 C14 C19 -110.7(7) . . . .
C6 C5 C11 O3 21.0(9) . . . .
C6 C5 C11 O4 -159.1(8) . . . .
C6 C7 C8 O1 -3.8(9) . . . .
C6 C7 C8 O2 177.0(8) . . . .
C6 C14 C15 C16 -177.7(6) . . . .
C6 C14 C19 C18 176.9(6) . . . .
C7 C6 C14 C15 -53.7(8) . . . .
C7 C6 C14 C19 125.5(7) . . . .
C8 O1 C9 C10 -179.8(7) . . . .
C9 O1 C8 O2 0.0(11) . . . .
C9 O1 C8 C7 -179.3(6) . . . .
C11 O3 C12 C13 90.9(10) . . . .
C11 C5 C6 C7 -166.2(6) . . . .
C11 C5 C6 C14 69.5(8) . . . .
C12 O3 C11 O4 5.4(11) . . . .
C12 O3 C11 C5 -174.7(7) . . . .
C14 C6 C7 C2 103.5(7) . . . .
C14 C6 C7 C8 -76.5(8) . . . .
C14 C15 C16 Br1 177.9(5) . . . .
C14 C15 C16 C17 0.9(10) . . . .
C15 C14 C19 C18 -3.8(10) . . . .
C15 C16 C17 O5 179.2(6) . . . .
C15 C16 C17 C18 -4.2(10) . . . .
C16 C17 C18 Br2 -176.5(5) . . . .
C16 C17 C18 C19 3.5(11) . . . .
C17 C18 C19 C14 0.6(11) . . . .
C19 C14 C15 C16 3.1(10) . . . .
