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#$Date: 2022-06-30 11:08:09 +0300 (Thu, 30 Jun 2022) $
#$Revision: 276435 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/55/8105580.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_8105580
loop_
_publ_author_name
'Li, Yi-Biao'
'Chen, Lu'
'Zhu, Zhong-Zhi'
'Huang, Yu-Bing'
'Chen, Xiu-Wen'
_publ_section_title
;
 Crystal structure of 2-(4-chlorophenyl)-3-phenyl-1,8-naphthyridine,
 C20H13N2Cl
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              179
_journal_page_last               180
_journal_paper_doi               10.1515/ncrs-2018-0275
_journal_volume                  234
_journal_year                    2018
_chemical_formula_moiety         'C20 H13 Cl N2'
_chemical_formula_sum            'C20 H13 Cl N2'
_chemical_formula_weight         316.77
_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
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 95.837(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.179(4)
_cell_length_b                   11.666(8)
_cell_length_c                   22.460(15)
_cell_measurement_reflns_used    3332
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.49
_cell_measurement_theta_min      2.52
_cell_volume                     1610.6(19)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_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_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            12531
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_min         1.823
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6630
_exptl_absorpt_correction_type   multi-scan'
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0948 before and 0.0390 after correction.
The Ratio of minimum to maximum transmission is 0.8893.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0507
_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)+(0.0871P)²+0.0305P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1599
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2062
_reflns_number_total             3334
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0275_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        1610.7(19)
_cod_database_code               8105580
_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
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C20(H20), C3(H3), C10(H10), C19(H19), C16(H16), C1(H1), C14(H14),
 C2(H2), C17(H17), C11(H11), C12(H12), C13(H13)
;
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
Cl1 Cl -0.11456(12) 0.32015(7) 0.44569(3) 0.1187(4) Uani 1 1 d . . . . .
N2 N 0.5456(3) 0.52907(13) 0.25657(7) 0.0610(4) Uani 1 1 d . . . . .
N1 N 0.7453(3) 0.51981(14) 0.17572(8) 0.0758(5) Uani 1 1 d . . . . .
C7 C 0.5828(3) 0.68933(15) 0.32489(8) 0.0562(5) Uani 1 1 d . . . . .
C15 C 0.3398(3) 0.51849(15) 0.34029(8) 0.0578(5) Uani 1 1 d . . . . .
C6 C 0.4945(3) 0.58075(16) 0.30515(8) 0.0567(5) Uani 1 1 d . . . . .
C5 C 0.6985(3) 0.57806(16) 0.22508(8) 0.0604(5) Uani 1 1 d . . . . .
C4 C 0.8038(3) 0.68094(15) 0.24322(8) 0.0584(5) Uani 1 1 d . . . . .
C8 C 0.7369(3) 0.73620(16) 0.29356(8) 0.0592(5) Uani 1 1 d . . . . .
H8 H 0.799135 0.806063 0.305676 0.071 Uiso 1 1 calc R . . . .
C9 C 0.5032(3) 0.75243(16) 0.37566(8) 0.0602(5) Uani 1 1 d . . . . .
C20 C 0.1545(3) 0.46851(17) 0.31188(9) 0.0650(5) Uani 1 1 d . . . . .
H20 H 0.124743 0.474992 0.270592 0.078 Uiso 1 1 calc R . . . .
C3 C 0.9663(4) 0.72223(19) 0.20942(9) 0.0719(6) Uani 1 1 d . . . . .
H3 H 1.038856 0.790201 0.220039 0.086 Uiso 1 1 calc R . . . .
C10 C 0.6345(4) 0.76961(19) 0.42816(9) 0.0750(6) Uani 1 1 d . . . . .
H10 H 0.775786 0.741038 0.432299 0.090 Uiso 1 1 calc R . . . .
C19 C 0.0141(3) 0.40930(19) 0.34424(11) 0.0766(6) Uani 1 1 d . . . . .
H19 H -0.112417 0.377764 0.324951 0.092 Uiso 1 1 calc R . . . .
C18 C 0.0596(4) 0.39664(19) 0.40461(11) 0.0751(6) Uani 1 1 d . . . . .
C16 C 0.3816(4) 0.5040(2) 0.40085(10) 0.0827(7) Uani 1 1 d . . . . .
H16 H 0.506759 0.536065 0.420588 0.099 Uiso 1 1 calc R . . . .
C1 C 0.9010(5) 0.5622(2) 0.14642(10) 0.0852(7) Uani 1 1 d . . . . .
H1 H 0.936922 0.521921 0.113051 0.102 Uiso 1 1 calc R . . . .
C14 C 0.2960(4) 0.7990(2) 0.37112(11) 0.0830(7) Uani 1 1 d . . . . .
H14 H 0.204910 0.788798 0.335938 0.100 Uiso 1 1 calc R . . . .
C2 C 1.0160(4) 0.6620(2) 0.16131(10) 0.0829(7) Uani 1 1 d . . . . .
H2 H 1.124782 0.686891 0.138660 0.099 Uiso 1 1 calc R . . . .
C17 C 0.2435(4) 0.4433(2) 0.43311(10) 0.0896(8) Uani 1 1 d . . . . .
H17 H 0.275308 0.434177 0.474199 0.108 Uiso 1 1 calc R . . . .
C11 C 0.5567(6) 0.8294(2) 0.47487(11) 0.0950(8) Uani 1 1 d . . . . .
H11 H 0.644985 0.839069 0.510578 0.114 Uiso 1 1 calc R . . . .
C12 C 0.3521(6) 0.8742(2) 0.46896(14) 0.1008(9) Uani 1 1 d . . . . .
H12 H 0.301837 0.914567 0.500487 0.121 Uiso 1 1 calc R . . . .
C13 C 0.2216(4) 0.8599(2) 0.41720(15) 0.1007(9) Uani 1 1 d . . . . .
H13 H 0.082487 0.891201 0.412951 0.121 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'
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'
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
C6 N2 C5 118.49(16) . .
C1 N1 C5 116.64(19) . .
C6 C7 C9 122.11(16) . .
C8 C7 C6 117.51(17) . .
C8 C7 C9 120.31(16) . .
C20 C15 C6 120.50(17) . .
C16 C15 C6 121.35(17) . .
C16 C15 C20 118.07(18) . .
N2 C6 C7 123.18(17) . .
N2 C6 C15 115.98(16) . .
C7 C6 C15 120.83(17) . .
N2 C5 C4 122.19(17) . .
N1 C5 N2 115.54(17) . .
N1 C5 C4 122.26(18) . .
C8 C4 C5 117.49(17) . .
C8 C4 C3 124.38(18) . .
C3 C4 C5 118.13(18) . .
C7 C8 C4 120.94(17) . .
C10 C9 C7 121.20(19) . .
C10 C9 C14 117.8(2) . .
C14 C9 C7 121.00(18) . .
C19 C20 C15 120.4(2) . .
C2 C3 C4 119.2(2) . .
C9 C10 C11 120.1(3) . .
C18 C19 C20 120.2(2) . .
C19 C18 Cl1 120.52(18) . .
C17 C18 Cl1 119.32(18) . .
C17 C18 C19 120.2(2) . .
C15 C16 C17 121.6(2) . .
N1 C1 C2 125.2(2) . .
C13 C14 C9 121.7(2) . .
C3 C2 C1 118.5(2) . .
C18 C17 C16 119.5(2) . .
C12 C11 C10 120.6(3) . .
C13 C12 C11 120.1(3) . .
C12 C13 C14 119.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C18 1.734(2) .
N2 C6 1.313(2) .
N2 C5 1.362(2) .
N1 C5 1.356(3) .
N1 C1 1.316(3) .
C7 C6 1.432(3) .
C7 C8 1.356(3) .
C7 C9 1.483(3) .
C15 C6 1.489(3) .
C15 C20 1.381(3) .
C15 C16 1.369(3) .
C5 C4 1.406(3) .
C4 C8 1.400(3) .
C4 C3 1.404(3) .
C9 C10 1.377(3) .
C9 C14 1.385(3) .
C20 C19 1.374(3) .
C3 C2 1.350(3) .
C10 C11 1.386(3) .
C19 C18 1.365(3) .
C18 C17 1.360(3) .
C16 C17 1.371(3) .
C1 C2 1.387(4) .
C14 C13 1.372(3) .
C11 C12 1.361(4) .
C12 C13 1.356(4) .
