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#$Date: 2022-11-18 11:34:45 +0200 (Fri, 18 Nov 2022) $
#$Revision: 279390 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/61/8106156.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_8106156
loop_
_publ_author_name
'Fernández-Galleguillos, Carlos'
'Bórquez, Jorge'
'Cárdenas, Alejandro'
'Brito, Iván'
_publ_section_title
;
 Crystal structure of
 3-(2-chloro-6-methoxyquinolin-3-yl)-5-phenylisoxazole (C19H13ClN2O2)
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              371
_journal_page_last               372
_journal_paper_doi               10.1515/ncrs-2017-0258
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C19 H13 Cl N2 O2'
_chemical_formula_sum            'C19 H13 Cl N2 O2'
_chemical_formula_weight         336.76
_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   geom
_cell_angle_alpha                90
_cell_angle_beta                 106.770(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2461(18)
_cell_length_b                   15.967(2)
_cell_length_c                   9.2864(13)
_cell_measurement_reflns_used    7384
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      58.93
_cell_measurement_theta_min      4.10
_cell_volume                     1596.6(4)
_computing_cell_refinement
'Bruker. APEX3, SAINT Bruker AXS Inc., Madison, Wisconsin,USA (2016)[8]'
_computing_data_collection
'Bruker. APEX3, SAINT Bruker AXS Inc., Madison, Wisconsin,USA (2016)[8]'
_computing_data_reduction
'Bruker. APEX3, SAINT Bruker AXS Inc., Madison, Wisconsin,USA (2016)[8]'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009) [9]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009) [9]'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)[10]'
_computing_structure_solution    'ShelXT (Sheldrick, 2016)[11]'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.788
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker D8-Venture I\mS'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1491
_diffrn_reflns_av_unetI/netI     0.1031
_diffrn_reflns_Laue_measured_fraction_full 0.788
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11188
_diffrn_reflns_point_group_measured_fraction_full 0.788
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         58.932
_diffrn_reflns_theta_min         4.105
_exptl_absorpt_coefficient_mu    2.232
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       0.0055(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.378
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2277
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.378
_refine_ls_R_factor_all          0.1735
_refine_ls_R_factor_gt           0.0670
_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)+(0.0200P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1606
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1195
_reflns_number_total             2277
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0258_suppl.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8106156
_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.
;
_shelxl_version_number           2013-4
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
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
Cl1 Cl 0.17596(15) -0.06489(9) 0.02408(16) 0.0712(6) Uani 1 1 d . . . . .
O1 O 0.6291(4) 0.1976(3) -0.3235(4) 0.0733(13) Uani 1 1 d . . . . .
O2 O 0.2765(4) 0.1596(2) 0.4132(4) 0.0707(12) Uani 1 1 d . . . . .
N1 N 0.3151(4) -0.0117(3) -0.1336(5) 0.0574(13) Uani 1 1 d . . . . .
N2 N 0.3396(5) 0.1461(3) 0.3031(5) 0.0688(15) Uani 1 1 d . . . . .
C1 C 0.2735(5) 0.0090(4) -0.0221(6) 0.0551(16) Uani 1 1 d . . . . .
C2 C 0.3923(5) 0.0426(4) -0.1745(5) 0.0517(15) Uani 1 1 d . . . . .
C3 C 0.4266(5) 0.1212(3) -0.1037(6) 0.0490(14) Uani 1 1 d . . . . .
C4 C 0.5052(5) 0.1745(3) -0.1522(6) 0.0568(16) Uani 1 1 d . . . . .
H4 H 0.5262 0.2264 -0.1066 0.068 Uiso 1 1 calc R U . . .
C5 C 0.5513(6) 0.1507(4) -0.2665(6) 0.0570(16) Uani 1 1 d . . . . .
C6 C 0.6806(6) 0.2718(4) -0.2434(7) 0.084(2) Uani 1 1 d . . . . .
H6A H 0.7386 0.2964 -0.2892 0.126 Uiso 1 1 calc R U . . .
H6B H 0.7225 0.2578 -0.1407 0.126 Uiso 1 1 calc R U . . .
H6C H 0.6152 0.3110 -0.2464 0.126 Uiso 1 1 calc R U . . .
C7 C 0.5203(6) 0.0717(4) -0.3348(6) 0.0630(17) Uani 1 1 d . . . . .
H7 H 0.5539 0.0555 -0.4111 0.076 Uiso 1 1 calc R U . . .
C8 C 0.4427(6) 0.0191(4) -0.2916(6) 0.0655(17) Uani 1 1 d . . . . .
H8 H 0.4225 -0.0325 -0.3389 0.079 Uiso 1 1 calc R U . . .
C9 C 0.3769(5) 0.1399(3) 0.0150(6) 0.0551(15) Uani 1 1 d . . . . .
H9 H 0.3957 0.1912 0.0636 0.066 Uiso 1 1 calc R U . . .
C10 C 0.3022(5) 0.0855(4) 0.0616(6) 0.0530(15) Uani 1 1 d . . . . .
C11 C 0.2604(6) 0.1042(4) 0.1959(6) 0.0571(16) Uani 1 1 d . . . . .
C12 C 0.1636(5) 0.1236(4) 0.3664(6) 0.0549(16) Uani 1 1 d . . . . .
C13 C 0.1492(6) 0.0889(4) 0.2317(6) 0.0618(17) Uani 1 1 d . . . . .
H13 H 0.0798 0.0604 0.1735 0.074 Uiso 1 1 calc R U . . .
C14 C 0.0862(6) 0.1302(3) 0.4665(6) 0.0571(16) Uani 1 1 d . . . . .
C15 C -0.0326(6) 0.0995(4) 0.4251(7) 0.0714(19) Uani 1 1 d . . . . .
H15 H -0.0633 0.0745 0.3312 0.086 Uiso 1 1 calc R U . . .
C16 C -0.1079(7) 0.1047(4) 0.5187(8) 0.086(2) Uani 1 1 d . . . . .
H16 H -0.1889 0.0846 0.4873 0.103 Uiso 1 1 calc R U . . .
C17 C -0.0620(8) 0.1396(5) 0.6576(9) 0.088(2) Uani 1 1 d . . . . .
H17 H -0.1113 0.1415 0.7225 0.106 Uiso 1 1 calc R U . . .
C18 C 0.0555(8) 0.1719(4) 0.7027(8) 0.092(2) Uani 1 1 d . . . . .
H18 H 0.0852 0.1965 0.7971 0.111 Uiso 1 1 calc R U . . .
C19 C 0.1302(7) 0.1678(4) 0.6079(7) 0.079(2) Uani 1 1 d . . . . .
H19 H 0.2099 0.1901 0.6383 0.095 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C5 O1 C6 117.4(4) . .
C12 O2 N2 108.9(4) . .
C1 N1 C2 117.9(5) . .
C11 N2 O2 104.7(4) . .
N1 C1 C10 125.0(5) . .
N1 C1 Cl1 114.9(5) . .
C10 C1 Cl1 120.1(4) . .
N1 C2 C8 118.5(5) . .
N1 C2 C3 123.1(5) . .
C8 C2 C3 118.4(5) . .
C4 C3 C9 123.9(5) . .
C4 C3 C2 120.3(5) . .
C9 C3 C2 115.8(5) . .
C5 C4 C3 120.1(5) . .
C5 C4 H4 120.0 . .
C3 C4 H4 120.0 . .
C4 C5 O1 125.3(6) . .
C4 C5 C7 120.0(5) . .
O1 C5 C7 114.7(5) . .
O1 C6 H6A 109.5 . .
O1 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
O1 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C8 C7 C5 121.2(5) . .
C8 C7 H7 119.4 . .
C5 C7 H7 119.4 . .
C7 C8 C2 120.0(6) . .
C7 C8 H8 120.0 . .
C2 C8 H8 120.0 . .
C10 C9 C3 122.4(5) . .
C10 C9 H9 118.8 . .
C3 C9 H9 118.8 . .
C9 C10 C1 115.7(5) . .
C9 C10 C11 120.8(5) . .
C1 C10 C11 123.4(5) . .
N2 C11 C13 111.4(5) . .
N2 C11 C10 115.5(5) . .
C13 C11 C10 133.1(6) . .
C13 C12 O2 109.2(5) . .
C13 C12 C14 134.3(6) . .
O2 C12 C14 116.6(5) . .
C12 C13 C11 105.9(5) . .
C12 C13 H13 127.1 . .
C11 C13 H13 127.1 . .
C15 C14 C19 118.0(5) . .
C15 C14 C12 120.8(6) . .
C19 C14 C12 121.2(6) . .
C14 C15 C16 121.9(6) . .
C14 C15 H15 119.1 . .
C16 C15 H15 119.1 . .
C17 C16 C15 119.2(7) . .
C17 C16 H16 120.4 . .
C15 C16 H16 120.4 . .
C16 C17 C18 120.8(7) . .
C16 C17 H17 119.6 . .
C18 C17 H17 119.6 . .
C17 C18 C19 119.9(7) . .
C17 C18 H18 120.1 . .
C19 C18 H18 120.1 . .
C18 C19 C14 120.2(6) . .
C18 C19 H19 119.9 . .
C14 C19 H19 119.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C1 1.746(5) .
O1 C5 1.369(6) .
O1 C6 1.429(6) .
O2 C12 1.347(6) .
O2 N2 1.418(5) .
N1 C1 1.296(6) .
N1 C2 1.356(6) .
N2 C11 1.311(6) .
C1 C10 1.434(7) .
C2 C8 1.414(7) .
C2 C3 1.418(7) .
C3 C4 1.392(7) .
C3 C9 1.404(6) .
C4 C5 1.363(7) .
C4 H4 0.9300 .
C5 C7 1.409(7) .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C7 C8 1.354(7) .
C7 H7 0.9300 .
C8 H8 0.9300 .
C9 C10 1.362(7) .
C9 H9 0.9300 .
C10 C11 1.484(7) .
C11 C13 1.406(7) .
C12 C13 1.334(7) .
C12 C14 1.449(7) .
C13 H13 0.9300 .
C14 C15 1.369(7) .
C14 C19 1.398(7) .
C15 C16 1.380(8) .
C15 H15 0.9300 .
C16 C17 1.363(9) .
C16 H16 0.9300 .
C17 C18 1.367(9) .
C17 H17 0.9300 .
C18 C19 1.383(8) .
C18 H18 0.9300 .
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
C12 O2 N2 C11 1.1(6) . . . .
C2 N1 C1 C10 0.5(8) . . . .
C2 N1 C1 Cl1 -179.4(4) . . . .
C1 N1 C2 C8 177.2(5) . . . .
C1 N1 C2 C3 -1.7(8) . . . .
N1 C2 C3 C4 -179.2(5) . . . .
C8 C2 C3 C4 1.9(8) . . . .
N1 C2 C3 C9 0.9(8) . . . .
C8 C2 C3 C9 -178.0(5) . . . .
C9 C3 C4 C5 178.7(5) . . . .
C2 C3 C4 C5 -1.2(8) . . . .
C3 C4 C5 O1 -179.9(5) . . . .
C3 C4 C5 C7 -0.5(8) . . . .
C6 O1 C5 C4 9.6(8) . . . .
C6 O1 C5 C7 -169.8(5) . . . .
C4 C5 C7 C8 1.6(9) . . . .
O1 C5 C7 C8 -179.0(5) . . . .
C5 C7 C8 C2 -0.8(9) . . . .
N1 C2 C8 C7 -179.8(5) . . . .
C3 C2 C8 C7 -0.9(8) . . . .
C4 C3 C9 C10 -178.7(5) . . . .
C2 C3 C9 C10 1.2(8) . . . .
C3 C9 C10 C1 -2.2(8) . . . .
C3 C9 C10 C11 174.6(5) . . . .
N1 C1 C10 C9 1.4(8) . . . .
Cl1 C1 C10 C9 -178.6(4) . . . .
N1 C1 C10 C11 -175.3(5) . . . .
Cl1 C1 C10 C11 4.6(7) . . . .
O2 N2 C11 C13 -0.7(6) . . . .
O2 N2 C11 C10 177.1(4) . . . .
C9 C10 C11 N2 -33.0(8) . . . .
C1 C10 C11 N2 143.5(6) . . . .
C9 C10 C11 C13 144.2(6) . . . .
C1 C10 C11 C13 -39.3(9) . . . .
N2 O2 C12 C13 -1.1(6) . . . .
N2 O2 C12 C14 179.2(4) . . . .
O2 C12 C13 C11 0.6(6) . . . .
C14 C12 C13 C11 -179.7(6) . . . .
N2 C11 C13 C12 0.1(7) . . . .
C10 C11 C13 C12 -177.2(6) . . . .
C13 C12 C14 C15 -3.3(10) . . . .
O2 C12 C14 C15 176.4(5) . . . .
C13 C12 C14 C19 176.7(6) . . . .
O2 C12 C14 C19 -3.7(8) . . . .
C19 C14 C15 C16 -0.2(9) . . . .
C12 C14 C15 C16 179.7(5) . . . .
C14 C15 C16 C17 -1.5(10) . . . .
C15 C16 C17 C18 2.2(11) . . . .
C16 C17 C18 C19 -1.2(11) . . . .
C17 C18 C19 C14 -0.5(10) . . . .
C15 C14 C19 C18 1.2(9) . . . .
C12 C14 C19 C18 -178.7(6) . . . .
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{51bb7ca4-1341-4e16-8f23-973795cdc619} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{51bb7ca4-1341-4e16-8f23-973795cdc619} '_publcif_info_datablock.publ_exptl'
loop_
_publcif_info_cif.paper_type
EE
