The crystal structure of 4-(((3-bromo-5-(trifluoromethyl)pyridin-2-yl)oxy)methyl)benzonitrile, C28H16Br2F6N4O2
Lu, Zhi-Qiang; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 595–597; doi:10.1515/ncrs-2022-0140

data_8107162
_publ_section_title
;
 The crystal structure of
 4-(((3-bromo-5-(trifluoromethyl)pyridin-2-yl)oxy)methyl)benzonitrile,
 C28H16Br2F6N4O2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              595
_journal_page_last               597
_journal_paper_doi               10.1515/ncrs-2022-0140
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C14 H8 Br F3 N2 O'
_chemical_formula_sum            'C14 H8 Br F3 N2 O'
_chemical_formula_weight         357.13
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                96.950(4)
_cell_angle_beta                 105.376(4)
_cell_angle_gamma                106.772(5)
_cell_formula_units_Z            4
_cell_length_a                   8.0085(4)
_cell_length_b                   13.6578(7)
_cell_length_c                   14.1964(6)
_cell_measurement_reflns_used    4615
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0510
_cell_measurement_theta_min      2.4150
_cell_volume                     1400.32(13)
_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-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.876
_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     -9.00 107.00   0.50    3.19    --   24.18  57.00 -90.00  232
  2  \w     46.00 107.00   0.50    3.19    --   24.18 178.00-180.00  122
  3  \w     47.00 105.00   0.50    3.19    --   24.18 178.00  30.00  116
  4  \w    -29.00   4.00   0.50    3.19    --   24.18 -19.00-120.00   66
  5  \w    -22.00   4.00   0.50    3.19    --  -23.24 -99.00 -30.00   52
  6  \w     31.00  57.00   0.50    3.19    --   24.18-107.00 -22.00   52
  7  \w     43.00 107.00   0.50    3.19    --   24.18-178.00 120.00  128
  8  \w    -19.00   7.00   0.50    3.19    --  -23.24 -99.00 150.00   52
  9  \w    -66.00  21.00   0.50    3.19    --   24.18 -37.00 150.00  174
 10  \w    -87.00  -3.00   0.50    3.19    --  -23.24 107.00  76.00  168
 11  \w    -60.00   1.00   0.50    3.19    --   24.18 -19.00 -60.00  122
 12  \w    -66.00  19.00   0.50    3.19    --   24.18 -37.00-150.00  170
;
_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      -0.0664073000
_diffrn_orient_matrix_UB_12      -0.0032968000
_diffrn_orient_matrix_UB_13      -0.0457838000
_diffrn_orient_matrix_UB_21      0.0226116000
_diffrn_orient_matrix_UB_22      -0.0410364000
_diffrn_orient_matrix_UB_23      -0.0234473000
_diffrn_orient_matrix_UB_31      -0.0676986000
_diffrn_orient_matrix_UB_32      -0.0372612000
_diffrn_orient_matrix_UB_33      0.0129612000
_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  0.0556
_diffrn_reflns_av_unetI/netI     0.0857
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17870
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.700
_diffrn_reflns_theta_min         1.955
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.969
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.11725
_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    1.694
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.789
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     395
_refine_ls_number_reflns         6947
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1332
_refine_ls_R_factor_gt           0.0570
_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^)+(0.0547P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1268
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3806
_reflns_number_total             6947
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2022-0140_suppl.cif
_cod_data_source_block           a
_cod_depositor_comments
;

2025-04-22
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C28 H16 Br2 F6 N4 O2'
_cod_original_formula_weight         714.27
_cod_original_formula_moiety         '2(C14 H8 Br F3 N2 O)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1400.32(12)
_cod_database_code               8107162
_chemical_oxdiff_formula         CHON
_shelx_estimated_absorpt_t_max   0.574
_shelx_estimated_absorpt_t_min   0.524
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13), C17(H17), C20(H20),
 C23(H23), C24(H24), C26(H26), C27(H27)
;
_shelx_res_checksum              72728
_shelx_hkl_checksum              63020
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.977
_oxdiff_exptl_absorpt_empirical_full_min 0.469