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#$Date: 2022-05-16 10:39:59 +0300 (Mon, 16 May 2022) $
#$Revision: 275440 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/52/8105262.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_8105262
loop_
_publ_author_name
'Li, Xiao-Hong'
'Wu, Wei-Na'
_publ_section_title
;
 Crystal structure of
 2-(5-chloro-quinolin-8-yloxy)-N-quinolin-8-yl-acetamide, C20H14N3O2Cl
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              703
_journal_page_last               704
_journal_paper_doi               10.1515/ncrs-2019-0907
_journal_volume                  235
_journal_year                    2020
_chemical_formula_sum            'C20 H14 Cl N3 O2'
_chemical_formula_weight         363.79
_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                 116.313(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.954(8)
_cell_length_b                   8.246(4)
_cell_length_c                   14.383(7)
_cell_measurement_reflns_used    495
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.88
_cell_measurement_theta_min      2.26
_cell_volume                     1696.1(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7607
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.424
_exptl_absorpt_coefficient_mu    0.245
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2970
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0420P)²+0.3074P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0909
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2305
_reflns_number_total             2970
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0907_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        1696.1(15)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8105262
_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_min   0.941
_shelx_estimated_absorpt_t_max   0.964
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 1.37482(3) 0.59180(7) 1.02415(5) 0.0847(2) Uani 1 1 d . . . . .
O1 O 0.99629(7) 0.35932(12) 0.91121(9) 0.0522(3) Uani 1 1 d . . . . .
O2 O 0.85161(8) 0.02429(14) 0.87801(11) 0.0758(4) Uani 1 1 d . . . . .
N1 N 1.01771(9) 0.64942(15) 0.85088(10) 0.0512(3) Uani 1 1 d . . . . .
N2 N 0.82200(8) 0.28954(15) 0.83867(10) 0.0471(3) Uani 1 1 d . . . . .
H2A H 0.8493 0.3822 0.8485 0.057 Uiso 1 1 calc R U . . .
N3 N 0.74690(10) 0.56434(16) 0.74687(11) 0.0564(4) Uani 1 1 d . . . . .
C1 C 1.02877(13) 0.7962(2) 0.82335(13) 0.0583(4) Uani 1 1 d . . . . .
H1B H 0.9753 0.8562 0.7842 0.070 Uiso 1 1 calc R U . . .
C2 C 1.11432(14) 0.8680(2) 0.84840(14) 0.0621(5) Uani 1 1 d . . . . .
H2B H 1.1176 0.9734 0.8272 0.075 Uiso 1 1 calc R U . . .
C3 C 1.19299(13) 0.7832(2) 0.90388(14) 0.0588(5) Uani 1 1 d . . . . .
H3B H 1.2512 0.8296 0.9215 0.071 Uiso 1 1 calc R U . . .
C4 C 1.18649(11) 0.62391(19) 0.93503(12) 0.0472(4) Uani 1 1 d . . . . .
C5 C 1.26297(11) 0.5229(2) 0.99161(13) 0.0550(4) Uani 1 1 d . . . . .
C6 C 1.25081(12) 0.3734(2) 1.02066(14) 0.0599(5) Uani 1 1 d . . . . .
H6A H 1.3027 0.3088 1.0582 0.072 Uiso 1 1 calc R U . . .
C7 C 1.16193(12) 0.3135(2) 0.99557(13) 0.0559(4) Uani 1 1 d . . . . .
H7A H 1.1548 0.2102 1.0170 0.067 Uiso 1 1 calc R U . . .
C8 C 1.08570(10) 0.40544(18) 0.93997(12) 0.0444(4) Uani 1 1 d . . . . .
C9 C 1.09599(10) 0.56358(18) 0.90752(11) 0.0434(4) Uani 1 1 d . . . . .
C10 C 0.98043(11) 0.19559(18) 0.92655(13) 0.0491(4) Uani 1 1 d . . . . .
H10A H 1.0076 0.1722 1.0002 0.059 Uiso 1 1 calc R U . . .
H10B H 1.0101 0.1260 0.8955 0.059 Uiso 1 1 calc R U . . .
C11 C 0.87781(11) 0.16225(18) 0.87853(12) 0.0486(4) Uani 1 1 d . . . . .
C12 C 0.72521(11) 0.29172(19) 0.78317(12) 0.0472(4) Uani 1 1 d . . . . .
C13 C 0.66768(12) 0.1642(2) 0.77282(14) 0.0606(5) Uani 1 1 d . . . . .
H13A H 0.6925 0.0659 0.8049 0.073 Uiso 1 1 calc R U . . .
C14 C 0.57134(13) 0.1811(3) 0.71406(17) 0.0747(6) Uani 1 1 d . . . . .
H14A H 0.5327 0.0930 0.7073 0.090 Uiso 1 1 calc R U . . .
C15 C 0.53291(13) 0.3210(3) 0.66713(17) 0.0778(6) Uani 1 1 d . . . . .
H15A H 0.4684 0.3288 0.6286 0.093 Uiso 1 1 calc R U . . .
C16 C 0.58979(12) 0.4558(2) 0.67592(14) 0.0625(5) Uani 1 1 d . . . . .
C17 C 0.55674(15) 0.6065(3) 0.62992(18) 0.0836(6) Uani 1 1 d . . . . .
H17A H 0.4929 0.6222 0.5899 0.100 Uiso 1 1 calc R U . . .
C18 C 0.61644(17) 0.7285(3) 0.64318(19) 0.0873(7) Uani 1 1 d . . . . .
H18A H 0.5944 0.8292 0.6131 0.105 Uiso 1 1 calc R U . . .
C19 C 0.71158(14) 0.7029(2) 0.70247(16) 0.0717(5) Uani 1 1 d . . . . .
H19A H 0.7523 0.7886 0.7110 0.086 Uiso 1 1 calc R U . . .
C20 C 0.68685(11) 0.4417(2) 0.73451(12) 0.0493(4) Uani 1 1 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C8 O1 C10 117.40(11) . .
C1 N1 C9 117.03(15) . .
C11 N2 C12 128.24(13) . .
C11 N2 H2A 115.9 . .
C12 N2 H2A 115.9 . .
C19 N3 C20 117.58(16) . .
N1 C1 C2 124.57(17) . .
N1 C1 H1B 117.7 . .
C2 C1 H1B 117.7 . .
C3 C2 C1 119.07(17) . .
C3 C2 H2B 120.5 . .
C1 C2 H2B 120.5 . .
C2 C3 C4 119.52(17) . .
C2 C3 H3B 120.2 . .
C4 C3 H3B 120.2 . .
C5 C4 C3 124.88(16) . .
C5 C4 C9 118.26(15) . .
C3 C4 C9 116.86(15) . .
C6 C5 C4 121.17(15) . .
C6 C5 Cl1 119.46(14) . .
C4 C5 Cl1 119.37(14) . .
C5 C6 C7 121.10(16) . .
C5 C6 H6A 119.5 . .
C7 C6 H6A 119.5 . .
C8 C7 C6 120.08(16) . .
C8 C7 H7A 120.0 . .
C6 C7 H7A 120.0 . .
O1 C8 C7 124.99(14) . .
O1 C8 C9 114.72(13) . .
C7 C8 C9 120.29(15) . .
N1 C9 C4 122.92(14) . .
N1 C9 C8 118.00(14) . .
C4 C9 C8 119.08(14) . .
O1 C10 C11 109.89(12) . .
O1 C10 H10A 109.7 . .
C11 C10 H10A 109.7 . .
O1 C10 H10B 109.7 . .
C11 C10 H10B 109.7 . .
H10A C10 H10B 108.2 . .
O2 C11 N2 125.12(15) . .
O2 C11 C10 118.71(14) . .
N2 C11 C10 116.17(13) . .
C13 C12 N2 125.27(15) . .
C13 C12 C20 119.83(16) . .
N2 C12 C20 114.91(14) . .
C12 C13 C14 119.86(18) . .
C12 C13 H13A 120.1 . .
C14 C13 H13A 120.1 . .
C15 C14 C13 121.81(19) . .
C15 C14 H14A 119.1 . .
C13 C14 H14A 119.1 . .
C14 C15 C16 120.19(18) . .
C14 C15 H15A 119.9 . .
C16 C15 H15A 119.9 . .
C17 C16 C20 116.31(19) . .
C17 C16 C15 124.63(19) . .
C20 C16 C15 119.06(18) . .
C18 C17 C16 120.4(2) . .
C18 C17 H17A 119.8 . .
C16 C17 H17A 119.8 . .
C17 C18 C19 119.2(2) . .
C17 C18 H18A 120.4 . .
C19 C18 H18A 120.4 . .
N3 C19 C18 123.3(2) . .
N3 C19 H19A 118.3 . .
C18 C19 H19A 118.3 . .
N3 C20 C16 123.21(16) . .
N3 C20 C12 117.53(15) . .
C16 C20 C12 119.26(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C5 1.7281(19) .
O1 C8 1.3517(19) .
O1 C10 1.4089(19) .
O2 C11 1.2109(19) .
N1 C1 1.309(2) .
N1 C9 1.3499(19) .
N2 C11 1.331(2) .
N2 C12 1.389(2) .
N2 H2A 0.8600 .
N3 C19 1.308(2) .
N3 C20 1.349(2) .
C1 C2 1.381(3) .
C1 H1B 0.9300 .
C2 C3 1.346(3) .
C2 H2B 0.9300 .
C3 C4 1.406(2) .
C3 H3B 0.9300 .
C4 C5 1.402(2) .
C4 C9 1.408(2) .
C5 C6 1.343(3) .
C6 C7 1.389(2) .
C6 H6A 0.9300 .
C7 C8 1.353(2) .
C7 H7A 0.9300 .
C8 C9 1.419(2) .
C10 C11 1.493(2) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C12 C13 1.360(2) .
C12 C20 1.419(2) .
C13 C14 1.395(3) .
C13 H13A 0.9300 .
C14 C15 1.339(3) .
C14 H14A 0.9300 .
C15 C16 1.405(3) .
C15 H15A 0.9300 .
C16 C17 1.396(3) .
C16 C20 1.402(2) .
C17 C18 1.340(3) .
C17 H17A 0.9300 .
C18 C19 1.389(3) .
C18 H18A 0.9300 .
C19 H19A 0.9300 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O1 0.86 2.11 2.565(2) 112.1 .
