Crystal structure of 2-(4-bromobenzyloxy)-6-chloropyridine, C12H9BrClNO
Lu, Zhi-Qiang; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 345–346; doi:10.1515/ncrs-2022-0026

data_8105692
_publ_section_title
;
 Crystal structure of 2-(4-bromobenzyloxy)-6-chloropyridine, C12H9BrClNO
;
_journal_issue                   3
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              345
_journal_page_last               346
_journal_paper_doi               10.1515/ncrs-2022-0026
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C12 H9 Br Cl N O'
_chemical_formula_sum            'C12 H9 Br Cl N O'
_chemical_formula_weight         298.56
_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     dual
_cell_angle_alpha                90
_cell_angle_beta                 99.028(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.3665(3)
_cell_length_b                   22.5576(17)
_cell_length_c                   12.1286(10)
_cell_measurement_reflns_used    2232
_cell_measurement_temperature    293
_cell_measurement_theta_max      28.0910
_cell_measurement_theta_min      2.4710
_cell_volume                     1179.84(16)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -36.00   1.00   0.50    4.30    --   24.02 -19.00 -60.00   74
  2  \w     -7.00  35.00   0.50    4.30    --  -23.08 -99.00-180.00   84
  3  \w     28.00  53.00   0.50    4.30    --   24.02-119.00-157.00   50
  4  \w     55.00 106.00   0.50    4.30    --   24.02-178.00-150.00  102
  5  \w     63.00  88.00   0.50    4.30    --   24.02-156.00  45.00   50
  6  \w    -66.00  20.00   0.50    4.30    --   24.02 -37.00   0.00  172
  7  \w    -66.00  15.00   0.50    4.30    --   24.02 -37.00  90.00  162
  8  \w    -86.00 -61.00   0.50    4.30    --  -23.08-156.00  45.00   50
  9  \w    -58.00 -33.00   0.50    4.30    --  -23.08 156.00  83.00   50
 10  \w     55.00  80.00   0.50    4.30    --   24.02 156.00  83.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0286286000
_diffrn_orient_matrix_UB_12      -0.0133130000
_diffrn_orient_matrix_UB_13      0.0536493000
_diffrn_orient_matrix_UB_21      -0.0355503000
_diffrn_orient_matrix_UB_22      -0.0282078000
_diffrn_orient_matrix_UB_23      -0.0244836000
_diffrn_orient_matrix_UB_31      0.1579672000
_diffrn_orient_matrix_UB_32      -0.0039299000
_diffrn_orient_matrix_UB_33      -0.0055988000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0802
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8608
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.634
_diffrn_reflns_theta_min         1.925
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.687
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
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    1.681
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1288
_refine_ls_R_factor_gt           0.0595
_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/[\s^2^(Fo^2^)+(0.0553P)^2^+0.2298P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1451
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1526
_reflns_number_total             2921
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0026_suppl.cif
_cod_data_source_block           pei7
_cod_database_code               8105692
_chemical_oxdiff_formula         CHON
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C11(H11), C12(H12)
;