Shortening CN⋯Br–Csp3 halogen bonds via π-stacking
Kupietz, Kamil; Gomila, Rosa M.; Roisnel, Thierry; Frontera, Antonio; Gramage-Doria, Rafael; CrystEngComm 26 (2024) 2131–2135; doi:10.1039/D4CE00307A

data_7248367
_publ_section_title
;
 Shortening C&#xE002;N&#x22EF;Br--Csp3 halogen bonds via \p-stacking
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              2131
_journal_page_last               2135
_journal_paper_doi               10.1039/D4CE00307A
_journal_volume                  26
_journal_year                    2024
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C8 H5 Br2 N'
_chemical_formula_sum            'C8 H5 Br2 N'
_chemical_formula_weight         274.95
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_update_record
;
2024-02-01 deposited with the CCDC.	2024-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7185(18)
_cell_length_b                   7.2021(9)
_cell_length_c                   8.8003(12)
_cell_measurement_reflns_used    4083
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4537
_cell_measurement_theta_min      2.7498
_cell_measurement_wavelength     0.710730
_cell_volume                     869.5(2)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2023)'
_computing_structure_refinement  'SHELXL-2019_2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      -0.0149689
_diffrn_orient_matrix_UB_12      0.0783379
_diffrn_orient_matrix_UB_13      -0.0522151
_diffrn_orient_matrix_UB_21      0.0423291
_diffrn_orient_matrix_UB_22      0.0805342
_diffrn_orient_matrix_UB_23      0.0463761
_diffrn_orient_matrix_UB_31      0.1313886
_diffrn_orient_matrix_UB_32      -0.0170205
_diffrn_orient_matrix_UB_33      -0.0208897
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7270
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_min         2.750
_diffrn_source_current           1.00
_diffrn_source_power             50.0
_diffrn_source_voltage           50.00
_exptl_absorpt_coefficient_mu    9.254
_exptl_absorpt_correction_T_max  0.435
_exptl_absorpt_correction_T_min  0.312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.100
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.721
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         1074
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0238
_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^)+(0.0155P)^2^+1.6587P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0523
_refine_ls_wR_factor_ref         0.0563
_reflns_number_gt                883
_reflns_number_total             1074
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d4ce00307a2.cif
_cod_data_source_block           KK007_2
_cod_depositor_comments          'Adding full bibliography for 7248367.cif.'
_cod_database_code               7248367
_shelx_res_checksum              46239