Strengthening N⋯X halogen bonding via nitrogen substitution in the aromatic framework of halogen-substituted arylpyrazinamides
Khavasi, Hamid Reza; Hosseini, Mahdieh; Tehrani, Alireza Azhdari; Naderi, Soheila; CrystEngComm 16 (2014) 4546–; doi:10.1039/c3ce41856a

data_7214461
_publ_section_title
;
 Strengthening N&#x22EF;X halogen bonding via nitrogen substitution in the
 aromatic framework of halogen-substituted arylpyrazinamides
;
_journal_issue                   21
_journal_name_full               CrystEngComm
_journal_page_first              4546
_journal_paper_doi               10.1039/c3ce41856a
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C11 H8 Br N3 O'
_chemical_formula_weight         278.10
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.489(7)
_cell_angle_beta                 96.656(7)
_cell_angle_gamma                110.390(8)
_cell_formula_units_Z            2
_cell_length_a                   5.8743(6)
_cell_length_b                   7.5065(7)
_cell_length_c                   13.3959(9)
_cell_measurement_reflns_used    4449
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      1.58
_cell_volume                     531.44(9)
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_av_sigmaI/netI    0.0730
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4449
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.58
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.847
_exptl_absorpt_correction_T_max  0.7861
_exptl_absorpt_correction_T_min  0.4451
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'shape of crystal determined optically'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0669P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1186
_reflns_number_gt                1566
_reflns_number_total             2096
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce41856a2.cif
_cod_data_source_block           kh744
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 7214461--7214468.cif.
;
_cod_original_cell_volume        531.44(8)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C11 H8 Br1 N3 O1'
_cod_database_code               7214461