#------------------------------------------------------------------------------
#$Date: 2016-02-19 23:18:51 +0100 (vie 19 de feb de 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/61/2016142.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2016142
loop_
_publ_author_name
'Ojala, Charles R.'
'Ojala, William H.'
'Britton, Doyle'
'Cramer, Christopher J.'
_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 I2 N2'
_chemical_formula_moiety         'C14 H10 I2 N2'
_chemical_formula_sum            'C14 H10 I2 N2'
_chemical_formula_weight         460.04
_chemical_name_systematic
;
4-iodobenzaldehyde azine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 90.314(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.2077(17)
_cell_length_b                   4.1543(10)
_cell_length_c                   23.317(6)
_cell_measurement_reflns_used    3960
_cell_measurement_temperature    174(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.8
_cell_volume                     698.2(3)
_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 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type
;
Bruker SMART 1K CCD area-detector diffractometer
;
_diffrn_measurement_method       'ω 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  0.085
_diffrn_reflns_av_sigmaI/netI    0.057
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            7115
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.75
_diffrn_standards_decay_%        'less than 1'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.488
_exptl_absorpt_correction_T_max  0.84
_exptl_absorpt_correction_T_min  0.24
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003; Blessing, 1995)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    2.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         3.00
_refine_diff_density_min         -1.34
_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     82
_refine_ls_number_reflns         1601
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.065
_refine_ls_R_factor_gt           0.047
_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/[σ²(Fo²)+(0.064P)²+3.31P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.115
_refine_ls_wR_factor_ref         0.122
_reflns_number_gt                1290
_reflns_number_total             1601
_reflns_threshold_expression     ' >2σ(I) '
_cod_data_source_file            ga3056.cif
_cod_data_source_block           I,I-C
_cod_original_sg_symbol_H-M      'P 2(1)/c'
_cod_database_code               2016142
_cod_database_fobs_code          2016142
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
I I1 -0.36110(6) 0.86627(12) 0.308402(18) 0.02813(19) Uani d . 1
C C1 -0.1234(9) 0.7210(17) 0.3534(3) 0.0217(13) Uani d . 1
N N1 0.4138(8) 0.5574(16) 0.4905(2) 0.0305(14) Uani d . 1
C C2 0.0112(9) 0.5424(17) 0.3250(3) 0.0245(14) Uani d . 1
H H2 -0.0065 0.4805 0.2861 0.029 Uiso calc R 1
C C3 0.1724(9) 0.4558(19) 0.3545(3) 0.0270(14) Uani d . 1
H H3 0.2649 0.3335 0.3355 0.032 Uiso calc R 1
C C4 0.1998(9) 0.5447(18) 0.4110(3) 0.0259(14) Uani d . 1
C C5 0.0624(10) 0.7242(19) 0.4393(3) 0.0288(15) Uani d . 1
H H5 0.0803 0.7867 0.4781 0.035 Uiso calc R 1
C C6 -0.0992(10) 0.8102(18) 0.4105(3) 0.0291(16) Uani d . 1
H H6 -0.1928 0.9294 0.4296 0.035 Uiso calc R 1
C C7 0.3726(10) 0.4583(19) 0.4403(3) 0.0284(15) Uani d . 1
H H7 0.4579 0.3221 0.4211 0.034 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
I1 0.0228(3) 0.0252(3) 0.0363(3) 0.00290(19) -0.00815(17) -0.00015(18)
C1 0.016(3) 0.018(3) 0.031(3) 0.000(3) -0.007(2) 0.003(2)
N1 0.026(3) 0.034(4) 0.032(3) 0.004(3) -0.005(2) 0.000(3)
C2 0.025(3) 0.019(3) 0.030(3) -0.003(3) -0.004(2) 0.003(3)
C3 0.019(3) 0.032(4) 0.030(3) 0.003(3) 0.002(2) -0.001(3)
C4 0.020(3) 0.028(4) 0.030(3) -0.004(3) -0.003(2) 0.001(3)
C5 0.028(4) 0.029(4) 0.030(3) 0.005(3) -0.002(3) -0.003(3)
C6 0.028(3) 0.032(4) 0.028(3) 0.010(3) -0.002(3) -0.001(3)
C7 0.022(3) 0.027(4) 0.036(4) 0.003(3) -0.002(3) 0.003(3)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
C6 C1 C2 . 120.9(6)
C6 C1 I1 . 120.0(5)
C2 C1 I1 . 119.0(5)
C7 N1 N1 3_666 112.4(7)
C1 C2 C3 . 118.8(6)
C1 C2 H2 . 120.6
C3 C2 H2 . 120.6
C4 C3 C2 . 121.1(6)
C4 C3 H3 . 119.5
C2 C3 H3 . 119.5
C3 C4 C5 . 119.5(6)
C3 C4 C7 . 119.8(6)
C5 C4 C7 . 120.7(6)
C6 C5 C4 . 120.1(6)
C6 C5 H5 . 120.0
C4 C5 H5 . 120.0
C5 C6 C1 . 119.6(6)
C5 C6 H6 . 120.2
C1 C6 H6 . 120.2
N1 C7 C4 . 122.9(7)
N1 C7 H7 . 118.5
C4 C7 H7 . 118.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
I1 C1 . 2.094(6)
C1 C6 . 1.391(9)
C1 C2 . 1.392(10)
N1 C7 . 1.274(9)
N1 N1 3_666 1.400(12)
C2 C3 . 1.395(9)
C2 H2 . 0.9500
C3 C4 . 1.381(9)
C3 H3 . 0.9500
C4 C5 . 1.406(10)
C4 C7 . 1.463(9)
C5 C6 . 1.388(10)
C5 H5 . 0.9500
C6 H6 . 0.9500
C7 H7 . 0.9500
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion
C6 C1 C2 C3 . -0.5(10)
I1 C1 C2 C3 . 177.8(5)
C1 C2 C3 C4 . -0.1(11)
C2 C3 C4 C5 . 0.3(11)
C2 C3 C4 C7 . -178.2(7)
C3 C4 C5 C6 . 0.1(11)
C7 C4 C5 C6 . 178.6(7)
C4 C5 C6 C1 . -0.7(11)
C2 C1 C6 C5 . 0.9(11)
I1 C1 C6 C5 . -177.3(6)
N1 N1 C7 C4 3_666 -180.0(7)
C3 C4 C7 N1 . 173.4(7)
C5 C4 C7 N1 . -5.1(11)
