#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:31:46 +0200 (vie 13 de oct de 2017) $
#$Revision: 201979 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/39/2233966.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_2233966
loop_
_publ_author_name
'Ji, Hao'
'Ma, Hua-Ping'
'Yang, Yong-An'
'Zhu, Hai-Liang'
_publ_section_title
;
 2-[(4-Bromophenylimino)methyl]-4,6-diiodophenol
;
_journal_coeditor_code           QM2053
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o788
_journal_paper_doi               10.1107/S160053681200551X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C13 H8 Br I2 N O'
_chemical_formula_moiety         'C13 H8 Br I2 N O'
_chemical_formula_sum            'C13 H8 Br I2 N O'
_chemical_formula_weight         527.91
_chemical_name_systematic
;
2-[(4-Bromophenylimino)methyl]-4,6-diiodophenol
;
_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                91.093(2)
_cell_angle_beta                 99.873(2)
_cell_angle_gamma                114.570(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9870(13)
_cell_length_b                   8.9811(14)
_cell_length_c                   11.3907(18)
_cell_measurement_reflns_used    1027
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.1
_cell_measurement_theta_min      2.5
_cell_volume                     728.4(2)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6174
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.82
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    7.048
_exptl_absorpt_correction_T_max  0.4178
_exptl_absorpt_correction_T_min  0.3804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.262
_refine_diff_density_min         -0.764
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3125
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0319
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0399P)²+1.2928P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0939
_reflns_number_gt                2425
_reflns_number_total             3125
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qm2053.cif
_cod_data_source_block           I
_cod_database_code               2233966
_cod_database_fobs_code          2233966
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
I I1 0.87298(7) 0.30448(5) -0.38474(3) 0.06516(15) Uani d . 1 1
Br Br1 0.27660(10) 0.16630(8) 0.47166(5) 0.0712(2) Uani d . 1 1
I I2 1.20768(6) 1.02378(4) -0.20734(4) 0.06502(15) Uani d . 1 1
N N1 0.6508(5) 0.3888(5) 0.0440(3) 0.0403(9) Uani d . 1 1
O O1 0.7124(6) 0.2911(4) -0.1515(3) 0.0532(9) Uani d . 1 1
H H1 0.6635 0.2839 -0.0929 0.080 Uiso calc R 1 1
C C1 0.8487(7) 0.5748(6) -0.0729(4) 0.0390(10) Uani d . 1 1
C C2 0.8205(6) 0.4496(6) -0.1604(4) 0.0380(10) Uani d . 1 1
C C3 0.9082(7) 0.4926(6) -0.2583(4) 0.0421(11) Uani d . 1 1
C C4 1.0185(7) 0.6550(6) -0.2713(4) 0.0444(11) Uani d . 1 1
H H4 1.0764 0.6820 -0.3371 0.053 Uiso calc R 1 1
C C5 1.0422(7) 0.7773(6) -0.1854(4) 0.0418(11) Uani d . 1 1
C C6 0.9621(7) 0.7389(6) -0.0865(4) 0.0416(11) Uani d . 1 1
H H6 0.9830 0.8220 -0.0282 0.050 Uiso calc R 1 1
C C7 0.7600(7) 0.5360(6) 0.0313(4) 0.0419(11) Uani d . 1 1
H H7 0.7836 0.6202 0.0894 0.050 Uiso calc R 1 1
C C8 0.5660(6) 0.3466(6) 0.1464(4) 0.0397(10) Uani d . 1 1
C C9 0.5782(8) 0.4581(7) 0.2364(5) 0.0554(14) Uani d . 1 1
H H9 0.6453 0.5703 0.2325 0.066 Uiso calc R 1 1
C C10 0.4912(8) 0.4041(7) 0.3323(5) 0.0548(14) Uani d . 1 1
H H10 0.4986 0.4796 0.3922 0.066 Uiso calc R 1 1
C C11 0.3947(7) 0.2400(7) 0.3386(4) 0.0469(12) Uani d . 1 1
C C12 0.3773(8) 0.1262(7) 0.2497(5) 0.0547(14) Uani d . 1 1
H H12 0.3098 0.0143 0.2545 0.066 Uiso calc R 1 1
C C13 0.4618(8) 0.1808(7) 0.1527(5) 0.0517(13) Uani d . 1 1
H H13 0.4484 0.1048 0.0910 0.062 Uiso calc R 1 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 0.0980(3) 0.0439(2) 0.0485(2) 0.0182(2) 0.0335(2) 0.00210(15)
Br1 0.0904(5) 0.0621(4) 0.0500(3) 0.0110(3) 0.0415(3) 0.0074(3)
I2 0.0833(3) 0.0366(2) 0.0657(3) 0.01060(18) 0.0292(2) 0.01196(16)
N1 0.041(2) 0.044(2) 0.039(2) 0.0172(18) 0.0162(17) 0.0086(17)
O1 0.067(2) 0.0355(18) 0.047(2) 0.0065(16) 0.0266(18) 0.0060(15)
C1 0.041(3) 0.042(3) 0.037(2) 0.018(2) 0.0134(19) 0.0135(19)
C2 0.039(2) 0.036(2) 0.038(2) 0.0129(19) 0.0105(19) 0.0054(18)
C3 0.049(3) 0.044(3) 0.036(2) 0.020(2) 0.013(2) 0.007(2)
C4 0.053(3) 0.043(3) 0.040(2) 0.019(2) 0.018(2) 0.013(2)
C5 0.047(3) 0.032(2) 0.046(3) 0.013(2) 0.018(2) 0.012(2)
C6 0.044(3) 0.040(3) 0.043(2) 0.019(2) 0.010(2) 0.004(2)
C7 0.049(3) 0.043(3) 0.040(2) 0.022(2) 0.017(2) 0.008(2)
C8 0.037(2) 0.047(3) 0.038(2) 0.017(2) 0.0153(19) 0.010(2)
C9 0.070(4) 0.041(3) 0.049(3) 0.012(3) 0.028(3) 0.005(2)
C10 0.070(4) 0.047(3) 0.042(3) 0.016(3) 0.022(3) -0.002(2)
C11 0.049(3) 0.051(3) 0.038(2) 0.015(2) 0.019(2) 0.007(2)
C12 0.063(3) 0.043(3) 0.053(3) 0.011(2) 0.027(3) 0.007(2)
C13 0.063(3) 0.045(3) 0.049(3) 0.020(3) 0.026(3) 0.005(2)
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'
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C7 N1 C8 122.4(4)
C2 O1 H1 109.5
C6 C1 C2 119.6(4)
C6 C1 C7 119.6(4)
C2 C1 C7 120.8(4)
O1 C2 C3 119.6(4)
O1 C2 C1 121.7(4)
C3 C2 C1 118.7(4)
C4 C3 C2 121.2(4)
C4 C3 I1 120.4(3)
C2 C3 I1 118.4(4)
C3 C4 C5 119.3(4)
C3 C4 H4 120.3
C5 C4 H4 120.3
C6 C5 C4 121.0(4)
C6 C5 I2 120.1(4)
C4 C5 I2 118.9(3)
C5 C6 C1 120.2(4)
C5 C6 H6 119.9
C1 C6 H6 119.9
N1 C7 C1 121.2(4)
N1 C7 H7 119.4
C1 C7 H7 119.4
C9 C8 C13 118.8(4)
C9 C8 N1 125.0(5)
C13 C8 N1 116.1(4)
C8 C9 C10 120.4(5)
C8 C9 H9 119.8
C10 C9 H9 119.8
C11 C10 C9 119.7(5)
C11 C10 H10 120.1
C9 C10 H10 120.1
C10 C11 C12 121.3(5)
C10 C11 Br1 119.5(4)
C12 C11 Br1 119.2(4)
C11 C12 C13 118.9(5)
C11 C12 H12 120.6
C13 C12 H12 120.6
C8 C13 C12 120.8(5)
C8 C13 H13 119.6
C12 C13 H13 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C3 2.093(5)
Br1 C11 1.907(5)
I2 C5 2.101(5)
N1 C7 1.273(6)
N1 C8 1.427(6)
O1 C2 1.340(6)
O1 H1 0.8200
C1 C6 1.401(7)
C1 C2 1.406(7)
C1 C7 1.460(6)
C2 C3 1.394(6)
C3 C4 1.382(7)
C4 C5 1.387(7)
C4 H4 0.9300
C5 C6 1.369(7)
C6 H6 0.9300
C7 H7 0.9300
C8 C9 1.382(7)
C8 C13 1.382(7)
C9 C10 1.382(7)
C9 H9 0.9300
C10 C11 1.360(8)
C10 H10 0.9300
C11 C12 1.373(7)
C12 C13 1.385(7)
C12 H12 0.9300
C13 H13 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 N1 0.82 1.85 2.576(5) 147.5
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12715790
