#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/66/2236670.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_2236670
loop_
_publ_author_name
'Elder, Philip J. W.'
'Vargas-Baca, Ignacio'
_publ_section_title
;
 2,2'-Diiodoazobenzene
;
_journal_coeditor_code           TK5154
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3127
_journal_paper_doi               10.1107/S1600536812040718
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C12 H8 I2 N2'
_chemical_formula_moiety         'C12 H8 I2 N2'
_chemical_formula_sum            'C12 H8 I2 N2'
_chemical_formula_weight         433.877
_chemical_name_common            2,2'-Diiodoazobenzene
_chemical_name_systematic
;
(E)-bis(2-iodophenyl)diazene
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.5320(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.6306(3)
_cell_length_b                   18.1105(12)
_cell_length_c                   15.3748(10)
_cell_measurement_reflns_used    4767
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.60
_cell_measurement_theta_min      2.62
_cell_volume                     1275.10(14)
_computing_cell_refinement       'SMART (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16726
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    4.907
_exptl_absorpt_correction_T_max  0.8732
_exptl_absorpt_correction_T_min  0.3222
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.628
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.557
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0272
_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)+(0.0243P)²+0.9205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0546
_refine_ls_wR_factor_ref         0.0594
_reflns_number_gt                2536
_reflns_number_total             3186
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk5154.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c  '
_cod_database_code               2236670
_cod_database_fobs_code          2236670
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
_atom_site_symmetry_multiplicity
C C1 1.0033(6) 0.62044(15) 0.74337(19) 0.0362(6) Uani d . 1 1
C C2 1.1608(6) 0.67355(16) 0.7950(2) 0.0391(6) Uani d . 1 1
C C3 1.3471(7) 0.72094(17) 0.7587(2) 0.0469(7) Uani d . 1 1
C C4 1.3732(7) 0.71515(18) 0.6711(2) 0.0511(8) Uani d . 1 1
C C5 1.2147(7) 0.66291(18) 0.6191(2) 0.0447(7) Uani d . 1 1
C C6 1.0330(7) 0.61521(17) 0.6548(2) 0.0440(7) Uani d . 1 1
I I1 1.12360(6) 0.685129(15) 0.927841(16) 0.06511(10) Uani d . 1 1
H H1 1.4537 0.7564 0.7936 0.056 Uiso calc R 1 1
H H2 1.4983 0.7466 0.6468 0.061 Uiso calc R 1 1
H H3 1.2306 0.6599 0.5596 0.054 Uiso calc R 1 1
H H4 0.9297 0.5794 0.6196 0.053 Uiso calc R 1 1
N N1 0.8151(5) 0.57362(13) 0.78379(16) 0.0409(6) Uani d . 1 1
N N2 0.6804(5) 0.52810(14) 0.73326(16) 0.0400(5) Uani d . 1 1
C C7 0.4922(6) 0.48055(16) 0.77216(18) 0.0366(6) Uani d . 1 1
C C8 0.3371(6) 0.42818(16) 0.71848(19) 0.0380(6) Uani d . 1 1
C C9 0.1496(6) 0.37976(17) 0.7525(2) 0.0451(7) Uani d . 1 1
C C10 0.1187(7) 0.38397(18) 0.8396(2) 0.0511(8) Uani d . 1 1
C C11 0.2731(7) 0.43536(19) 0.8935(2) 0.0494(8) Uani d . 1 1
C C12 0.4562(7) 0.48416(18) 0.8602(2) 0.0480(8) Uani d . 1 1
I I2 0.37973(5) 0.421268(15) 0.585578(15) 0.06002(9) Uani d . 1 1
H H5 0.0457 0.3447 0.7163 0.054 Uiso calc R 1 1
H H6 -0.0076 0.3518 0.8624 0.061 Uiso calc R 1 1
H H7 0.2537 0.4371 0.9528 0.059 Uiso calc R 1 1
H H8 0.5561 0.5196 0.8967 0.058 Uiso calc R 1 1
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
C1 C2 C3 120.3(3)
C2 C3 C4 119.7(3)
C3 C4 C5 120.3(3)
C4 C5 C6 120.3(3)
C5 C6 C1 120.1(3)
C6 C1 C2 119.2(3)
C1 C2 I1 121.2(2)
C3 C2 I1 118.5(2)
C2 C3 H1 120.1
C4 C3 H1 120.1
C3 C4 H2 119.9
C5 C4 H2 119.9
C4 C5 H3 119.8
C6 C5 H3 119.8
C5 C6 H4 119.9
C1 C6 H4 119.9
C6 C1 N1 122.8(3)
C2 C1 N1 117.9(3)
C1 N1 N2 114.0(2)
N1 N2 C7 115.1(2)
C7 C8 C9 120.3(3)
C8 C9 C10 119.6(3)
C9 C10 C11 120.4(3)
C10 C11 C12 120.4(3)
C11 C12 C7 120.1(3)
C12 C7 N2 123.5(3)
C8 C7 C12 119.1(3)
C8 C7 N2 117.4(2)
C7 C8 I2 120.6(2)
C9 C8 I2 119.1(2)
C8 C9 H5 120.2
C10 C9 H5 120.2
C9 C10 H6 119.8
C11 C10 H6 119.8
C10 C11 H7 119.8
C12 C11 H7 119.8
C11 C12 H8 119.9
C7 C12 H8 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.384(4)
C2 C3 1.391(4)
C3 C4 1.374(5)
C4 C5 1.378(5)
C5 C6 1.375(4)
C6 C1 1.393(4)
C2 I1 2.085(3)
C3 H1 0.9300
C4 H2 0.9300
C5 H3 0.9300
C6 H4 0.9300
C1 N1 1.423(3)
N1 N2 1.236(3)
N2 C7 1.419(3)
C7 C8 1.386(4)
C8 C9 1.390(4)
C9 C10 1.370(4)
C10 C11 1.374(5)
C11 C12 1.374(4)
C12 C7 1.390(4)
C8 I2 2.086(3)
C9 H5 0.9300
C10 H6 0.9300
C11 H7 0.9300
C12 H8 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3689518
