Using Halogen···Halogen Interactions to Direct Noncentrosymmetric Crystal Packing in Dipolar Organic Molecules
Saha, Binoy K.; Nangia, Ashwini; Nicoud, Jean-François; Crystal Growth & Design 6 (2006) 1278–; doi:10.1021/cg060117k

data_4508710
_publ_section_title
;
 Using Halogen&#x00B7;&#x00B7;&#x00B7;Halogen Interactions to Direct
 Noncentrosymmetric Crystal Packing in Dipolar Organic Molecules
;
_journal_issue                   6
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              1278
_journal_paper_doi               10.1021/cg060117k
_journal_volume                  6
_journal_year                    2006
_chemical_formula_moiety         'C5 H4 Br N O'
_chemical_formula_sum            'C5 H4 Br N O'
_chemical_formula_weight         174.00
_chemical_name_common            2-bromo-3-hydroxypyridine
_chemical_name_systematic
; 
 2-bromo-3-hydroxypyridine
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5563(12)
_cell_length_b                   12.7285(13)
_cell_length_c                   3.8875(4)
_cell_measurement_reflns_used    1751
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.01
_cell_measurement_theta_min      3.20
_cell_volume                     571.83(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  '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  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            1950
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    7.074
_exptl_absorpt_correction_T_max  0.4375
_exptl_absorpt_correction_T_min  0.2254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.021
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.028(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     77
_refine_ls_number_reflns         833
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0207
_refine_ls_R_factor_gt           0.0198
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0342P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0502
_refine_ls_wR_factor_ref         0.0507
_reflns_number_gt                797
_reflns_number_total             833
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060117ksup1.cif
_cod_data_source_block           an275
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               4508710