Three polymorphs of 4-4'-diiodobenzalazine, and 4-chloro-4'-iodobenzalazine
Ojala, Charles R.; Ojala, William H.; Britton, Doyle; Cramer, Christopher J.; Acta Crystallographica Section C 63 (2007) o518–o523; doi:10.1107/S0108270107034786

data_2016143
_publ_section_title
;
 Three polymorphs of 4-4'-diiodobenzalazine, and
 4-chloro-4'-iodobenzalazine
;
_journal_coeditor_code           GA3056
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o518
_journal_page_last               o523
_journal_paper_doi               10.1107/S0108270107034786
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C14 H10 Cl I N2'
_chemical_formula_moiety         'C14 H10 Cl I N2'
_chemical_formula_sum            'C14 H10 Cl I N2'
_chemical_formula_weight         368.59
_chemical_name_systematic
;
1-(4-Chlorobenzylidene)-2-(4-iodobenzylidene)diazane
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.900(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.499(2)
_cell_length_b                   4.0006(7)
_cell_length_c                   14.717(3)
_cell_measurement_reflns_used    3282
_cell_measurement_temperature    174(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.8
_cell_volume                     676.9(2)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      174(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type
;
Bruker SMART 1K CCD area-detector diffractometer
;
_diffrn_measurement_method       '\w 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  0.032
_diffrn_reflns_av_sigmaI/netI    0.052
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7262
_diffrn_reflns_theta_full        28.21
_diffrn_reflns_theta_max         28.21
_diffrn_reflns_theta_min         1.77
_diffrn_standards_decay_%        'less than 1'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.545
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.42
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS; Sheldrick, 2003; Blessing, 1995
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.50
_refine_diff_density_min         -0.33
_refine_ls_abs_structure_details
;
Flack  (1983),
1476 Friedel pairs
;
_refine_ls_abs_structure_Flack   0.17(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3089
_refine_ls_number_restraints     109
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.063
_refine_ls_R_factor_gt           0.038
_refine_ls_shift/su_max          0.02
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 calc w=1/[\s^2^(Fo^2^)+(0.017P)^2^+0.681P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.066
_refine_ls_wR_factor_ref         0.072
_reflns_number_gt                2308
_reflns_number_total             3089
_reflns_threshold_expression     '>2\s(I) '
_cod_data_source_file            ga3056.cif
_cod_data_source_block           I,Cl
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               2016143
_cod_database_fobs_code          2016143