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_2243003
_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          'C11 H4 Br F4 N O'
_chemical_formula_moiety         'C11 H4 Br F4 N O'
_chemical_formula_sum            'C11 H4 Br F4 N O'
_chemical_formula_weight         322.06
_chemical_name_systematic
;
4-(4-Bromophenoxy)-2,3,5,6-tetrafluoropyridine
;
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 113.585(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3530(5)
_cell_length_b                   5.8584(2)
_cell_length_c                   14.8863(6)
_cell_measurement_reflns_used    7652
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      31.9003
_cell_measurement_theta_min      2.6434
_cell_volume                     1067.24(7)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0398
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19174
_diffrn_reflns_theta_full        31.50
_diffrn_reflns_theta_max         31.50
_diffrn_reflns_theta_min         1.74
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    3.893
_exptl_absorpt_correction_T_max  0.72
_exptl_absorpt_correction_T_min  0.21
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2017)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.004
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.838
_refine_diff_density_min         -0.772
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         3544
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0825
_reflns_number_gt                3013
_reflns_number_total             3544
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7833sup1.cif
_cod_data_source_block           II
_cod_database_code               2243003
_cod_database_fobs_code          2243003
_shelx_hkl_checksum              60029
_shelx_res_checksum              79083