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_7214468
_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_moiety         'C11 H8 I1 N3 O1'
_chemical_formula_sum            'C11 H8 I N3 O'
_chemical_formula_weight         325.10
_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                78.850(11)
_cell_angle_beta                 85.640(11)
_cell_angle_gamma                70.594(11)
_cell_formula_units_Z            2
_cell_length_a                   5.9550(8)
_cell_length_b                   7.7126(11)
_cell_length_c                   12.9998(17)
_cell_measurement_reflns_used    998
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.22
_cell_measurement_theta_min      1.60
_cell_volume                     552.47(14)
_computing_cell_refinement       'SAINTPlus (Bruker, 1998a)'
_computing_data_collection       'SMART (Bruker, 1998b)'
_computing_data_reduction        'SAINTPlus (Bruker, 1998a)'
_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_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6693
_diffrn_reflns_theta_full        29.22
_diffrn_reflns_theta_max         29.22
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    2.879
_exptl_absorpt_correction_T_max  0.776
_exptl_absorpt_correction_T_min  0.720
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'shape of crystal determined optically'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.954
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0271P)^2^+0.2837P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0692
_reflns_number_gt                2591
_reflns_number_total             2920
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce41856a2.cif
_cod_data_source_block           new
_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        552.47(13)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C11 H8 I1 N3 O1'
_cod_database_code               7214468