#------------------------------------------------------------------------------
#$Date: 2022-06-29 11:44:51 +0300 (Wed, 29 Jun 2022) $
#$Revision: 276382 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/55/8105556.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_8105556
loop_
_publ_author_name
'Li, Hong-Mei'
'Wang, Hao-Feng'
'Sun, Bei-Jing'
'Lou, Xin-Hua'
_publ_section_title
;
 Crystal structure of 5-bromo-2-(naphthalen-6-yl)pyridine, C15H10BrN
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              103
_journal_page_last               104
_journal_paper_doi               10.1515/ncrs-2018-0211
_journal_volume                  234
_journal_year                    2018
_chemical_formula_moiety         'C15 H10 Br N'
_chemical_formula_sum            'C15 H10 Br N'
_chemical_formula_weight         284.15
_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
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 113.521(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6929(9)
_cell_length_b                   5.9337(4)
_cell_length_c                   14.6256(11)
_cell_measurement_reflns_used    1491
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9210
_cell_measurement_theta_min      6.0950
_cell_volume                     1169.16(16)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -102.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  -30.0000 87

#__ type_ start__ end____ width___ exp.time_
  2 omega -102.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000   60.0000 87

#__ type_ start__ end____ width___ exp.time_
  3 omega   14.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8576   37.0000 -180.0000 94

#__ type_ start__ end____ width___ exp.time_
  4 omega   23.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8576  -37.0000  120.0000 35

#__ type_ start__ end____ width___ exp.time_
  5 omega   36.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8576   77.0000   30.0000 58

#__ type_ start__ end____ width___ exp.time_
  6 omega    0.00   25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8576  -99.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega   67.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8576 -156.0000  142.0000 44

#__ type_ start__ end____ width___ exp.time_
  8 omega   -2.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8576  -99.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   42.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8576  -99.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   63.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8576   77.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   20.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.8576   77.0000   60.0000 39

#__ type_ start__ end____ width___ exp.time_
 12 omega  125.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
 13 omega  111.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 66

#__ type_ start__ end____ width___ exp.time_
 14 omega   90.00  117.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   40.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 51

#__ type_ start__ end____ width___ exp.time_
 16 omega   42.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 50

#__ type_ start__ end____ width___ exp.time_
 17 omega   68.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -150.0000 47

#__ type_ start__ end____ width___ exp.time_
 18 omega   68.00  110.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 42

#__ type_ start__ end____ width___ exp.time_
 19 omega   37.00   65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
 20 omega   47.00  122.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -60.0000 75

#__ type_ start__ end____ width___ exp.time_
 21 omega   45.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1072506000
_diffrn_orient_matrix_UB_12      0.0239478000
_diffrn_orient_matrix_UB_13      -0.0078101000
_diffrn_orient_matrix_UB_21      0.0369185000
_diffrn_orient_matrix_UB_22      -0.0319105000
_diffrn_orient_matrix_UB_23      0.1136538000
_diffrn_orient_matrix_UB_31      0.0146814000
_diffrn_orient_matrix_UB_32      0.2565570000
_diffrn_orient_matrix_UB_33      0.0148433000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4263
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         6.086
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.560
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.062
_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     154
_refine_ls_number_reflns         2078
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0396
_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)+(0.0498P)²+0.6081P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1103
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1651
_reflns_number_total             2078
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0211_suppl.cif
_cod_data_source_block           2
_cod_database_code               8105556
_chemical_oxdiff_formula         C38H41N2O2Br1
_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   0.548
_shelx_estimated_absorpt_t_min   0.462
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C10(H10), C12(H12), C13(H13),
 C15(H15)
;
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
Br1 Br 0.55224(3) 0.57982(9) 0.68324(3) 0.0684(2) Uani 1 1 d . . . . .
C1 C 1.3067(2) 0.2805(6) 1.0306(2) 0.0460(8) Uani 1 1 d . . . . .
H1 H 1.3278 0.1460 1.0653 0.055 Uiso 1 1 calc R . . . .
C2 C 1.3753(2) 0.4336(7) 1.0287(3) 0.0498(9) Uani 1 1 d . . . . .
H2 H 1.4427 0.4024 1.0617 0.060 Uiso 1 1 calc R . . . .
C3 C 1.3449(3) 0.6360(6) 0.9776(3) 0.0497(9) Uani 1 1 d . . . . .
H3 H 1.3923 0.7385 0.9764 0.060 Uiso 1 1 calc R . . . .
C4 C 1.2463(2) 0.6867(6) 0.9288(3) 0.0439(8) Uani 1 1 d . . . . .
H4 H 1.2274 0.8235 0.8955 0.053 Uiso 1 1 calc R . . . .
C5 C 1.1730(2) 0.5323(5) 0.9289(2) 0.0369(7) Uani 1 1 d . . . . .
C6 C 1.2036(2) 0.3242(6) 0.9803(2) 0.0373(7) Uani 1 1 d . . . . .
C7 C 1.1299(2) 0.1704(6) 0.9792(2) 0.0414(8) Uani 1 1 d . . . . .
H7 H 1.1486 0.0340 1.0129 0.050 Uiso 1 1 calc R . . . .
C8 C 1.0318(2) 0.2190(5) 0.9296(2) 0.0391(7) Uani 1 1 d . . . . .
H8 H 0.9849 0.1136 0.9294 0.047 Uiso 1 1 calc R . . . .
C9 C 0.9991(2) 0.4255(5) 0.8784(2) 0.0333(7) Uani 1 1 d . . . . .
C10 C 1.0703(2) 0.5777(5) 0.8789(2) 0.0364(7) Uani 1 1 d . . . . .
H10 H 1.0502 0.7140 0.8456 0.044 Uiso 1 1 calc R . . . .
C11 C 0.8910(2) 0.4740(5) 0.8288(2) 0.0350(7) Uani 1 1 d . . . . .
C12 C 0.8538(2) 0.6739(6) 0.7784(3) 0.0436(8) Uani 1 1 d . . . . .
H12 H 0.8971 0.7836 0.7741 0.052 Uiso 1 1 calc R . . . .
C13 C 0.7527(2) 0.7101(6) 0.7346(3) 0.0451(8) Uani 1 1 d . . . . .
H13 H 0.7267 0.8430 0.7005 0.054 Uiso 1 1 calc R . . . .
C14 C 0.6917(2) 0.5428(6) 0.7432(2) 0.0435(8) Uani 1 1 d . . . . .
C15 C 0.7324(2) 0.3472(6) 0.7938(3) 0.0476(9) Uani 1 1 d . . . . .
H15 H 0.6900 0.2357 0.7986 0.057 Uiso 1 1 calc R . . . .
N1 N 0.8298(2) 0.3115(5) 0.8360(2) 0.0440(7) 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 0.0181 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'
Br Br -0.6763 1.2805 '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'
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 C1 H1 119.6 . .
C2 C1 C6 120.8(3) . .
C6 C1 H1 119.6 . .
C1 C2 H2 119.9 . .
C1 C2 C3 120.3(3) . .
C3 C2 H2 119.9 . .
C2 C3 H3 119.5 . .
C4 C3 C2 121.1(3) . .
C4 C3 H3 119.5 . .
C3 C4 H4 119.8 . .
C3 C4 C5 120.4(3) . .
C5 C4 H4 119.8 . .
C4 C5 C6 118.9(3) . .
C4 C5 C10 122.1(3) . .
C10 C5 C6 119.0(3) . .
C1 C6 C5 118.7(3) . .
C7 C6 C1 122.9(3) . .
C7 C6 C5 118.4(3) . .
C6 C7 H7 119.6 . .
C8 C7 C6 120.9(3) . .
C8 C7 H7 119.6 . .
C7 C8 H8 119.0 . .
C7 C8 C9 121.9(3) . .
C9 C8 H8 119.0 . .
C8 C9 C11 119.7(3) . .
C10 C9 C8 117.8(3) . .
C10 C9 C11 122.4(3) . .
C5 C10 H10 119.1 . .
C9 C10 C5 121.9(3) . .
C9 C10 H10 119.1 . .
C12 C11 C9 122.8(3) . .
N1 C11 C9 116.0(3) . .
N1 C11 C12 121.2(3) . .
C11 C12 H12 119.9 . .
C13 C12 C11 120.1(3) . .
C13 C12 H12 119.9 . .
C12 C13 H13 121.1 . .
C14 C13 C12 117.7(3) . .
C14 C13 H13 121.1 . .
C13 C14 Br1 119.9(3) . .
C13 C14 C15 119.8(3) . .
C15 C14 Br1 120.3(3) . .
C14 C15 H15 118.7 . .
N1 C15 C14 122.7(3) . .
N1 C15 H15 118.7 . .
C15 N1 C11 118.4(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C14 1.893(3) .
C1 H1 0.9300 .
C1 C2 1.365(5) .
C1 C6 1.420(4) .
C2 H2 0.9300 .
C2 C3 1.391(5) .
C3 H3 0.9300 .
C3 C4 1.369(5) .
C4 H4 0.9300 .
C4 C5 1.414(5) .
C5 C6 1.422(4) .
C5 C10 1.415(4) .
C6 C7 1.412(5) .
C7 H7 0.9300 .
C7 C8 1.361(4) .
C8 H8 0.9300 .
C8 C9 1.416(4) .
C9 C10 1.380(4) .
C9 C11 1.488(4) .
C10 H10 0.9300 .
C11 C12 1.389(5) .
C11 N1 1.351(4) .
C12 H12 0.9300 .
C12 C13 1.378(5) .
C13 H13 0.9300 .
C13 C14 1.377(5) .
C14 C15 1.378(5) .
C15 H15 0.9300 .
C15 N1 1.330(4) .
