Crystal structures and Hirshfeld surface analysis of a series of 4-<i>O</i>-arylperfluoropyridines
Peloquin, Andrew J.; Corley, Cynthia A.; Adas, Sonya K.; Balaich, Gary J.; Iacono, Scott T.; Acta Crystallographica Section E 75 (2019) 1102–1107; doi:10.1107/S2056989019009344

data_2243005
_publ_section_title
;
 Crystal structures and Hirshfeld surface analysis of a series of
 4-<i>O</i>-arylperfluoropyridines
;
_journal_coeditor_code           HB7833
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1102
_journal_page_last               1107
_journal_paper_doi               10.1107/S2056989019009344
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C15 H6 Br F4 N O'
_chemical_formula_moiety         'C15 H6 Br F4 N O'
_chemical_formula_sum            'C15 H6 Br F4 N O'
_chemical_formula_weight         372.12
_chemical_name_systematic
;
4-[(6-Bromonaphthalen-2-yl)oxy]-2,3,5,6-tetrafluoropyridine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 101.401(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.0135(3)
_cell_length_b                   7.4994(4)
_cell_length_c                   14.6318(7)
_cell_measurement_reflns_used    7392
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      27.3803
_cell_measurement_theta_min      3.0652
_cell_volume                     646.84(6)
_computing_cell_refinement
;
SAINT (Bruker, 2017)
;
_computing_data_collection
;
APEX3 (Bruker, 2017)
;
_computing_data_reduction
;
SAINT (Bruker, 2017)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>, 2008)
;
_computing_publication_material
;
<i>publCIF</i> (Westrip, 2010)
;
_computing_structure_refinement
;
<i>SHELXL2016/6</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'Omega Scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12954
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         1.42
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    3.226
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.63
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2017)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.911
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.297
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.465
_refine_ls_abs_structure_details
;
Refined as an inversion twin
;
_refine_ls_abs_structure_Flack   0.171(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2775
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.143
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0305
_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^)+(0.0174P)^2^+0.1470P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0568
_refine_ls_wR_factor_ref         0.0575
_reflns_number_gt                2566
_reflns_number_total             2775
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7833sup1.cif
_cod_data_source_block           IV
_cod_database_code               2243005
_cod_database_fobs_code          2243005
_shelx_hkl_checksum              34239
_shelx_res_checksum              6251