#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/08/2220803.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_2220803
loop_
_publ_author_name
'Li, Zhan-Xian'
'Yang, Hui'
'Yu, Ming'
'Shi, Qiu-Zhi'
'Yu, Ming-Ming'
_publ_section_title
;
 (E)-2-[(2-Amino-4,5-dibromophenyl)iminomethyl]-6-methoxyphenol
;
_journal_coeditor_code           HG2454
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o241
_journal_paper_doi               10.1107/S1600536808044164
_journal_volume                  65
_journal_year                    2009
_chemical_formula_moiety         'C14 H12 Br2 N2 O2'
_chemical_formula_sum            'C14 H12 Br2 N2 O2'
_chemical_formula_weight         400.08
_chemical_name_systematic
;
(E)-2-[(2-Amino-4,5-dibromophenyl)iminomethyl]-6-methoxyphenol
;
_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                100.351(5)
_cell_angle_beta                 97.218(5)
_cell_angle_gamma                109.967(3)
_cell_formula_units_Z            2
_cell_length_a                   6.9500(4)
_cell_length_b                   7.4383(4)
_cell_length_c                   14.7877(10)
_cell_measurement_reflns_used    3154
_cell_measurement_temperature    292(3)
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      1.43
_cell_volume                     692.21(8)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      292(3)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART 1K CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6557
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         1.43
_exptl_absorpt_coefficient_mu    5.857
_exptl_absorpt_correction_T_max  0.275
_exptl_absorpt_correction_T_min  0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.919
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.599
_refine_diff_density_min         -0.462
_refine_ls_extinction_coef       0.0093(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0252
_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)+(0.0379P)²+0.3429P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0707
_reflns_number_gt                2695
_reflns_number_total             3154
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2454.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2220803
_cod_database_fobs_code          2220803
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_disorder_assembly
_atom_site_disorder_group
Br Br1 0.04544(4) 0.75243(4) 0.476886(17) 0.05025(11) Uani d . 1 . .
Br Br2 0.48830(4) 0.77615(4) 0.397735(17) 0.04846(10) Uani d . 1 . .
O O2 -0.2559(2) 0.1156(3) -0.08390(11) 0.0429(4) Uani d . 1 . .
H H2 -0.2248 0.1805 -0.0295 0.064 Uiso calc R 1 . .
O O1 -0.3008(3) -0.0863(3) -0.25537(11) 0.0458(4) Uani d . 1 . .
N N1 -0.0125(3) 0.3290(3) 0.07626(12) 0.0310(4) Uani d . 1 . .
C C9 0.0126(3) 0.4297(3) 0.17005(14) 0.0287(4) Uani d . 1 . .
C C5 0.2944(3) 0.2066(4) -0.09082(17) 0.0378(5) Uani d . 1 . .
H H5 0.4265 0.2712 -0.0525 0.045 Uiso calc R 1 . .
N N2 -0.3662(3) 0.2994(3) 0.14823(17) 0.0429(5) Uani d . 1 . .
C C2 -0.0994(3) 0.0097(3) -0.20552(14) 0.0318(4) Uani d . 1 . .
C C8 0.1432(3) 0.3179(3) 0.04022(15) 0.0334(5) Uani d . 1 . .
H H8 0.2770 0.3794 0.0771 0.040 Uiso calc R 1 . .
C C14 -0.1716(3) 0.4098(3) 0.20455(15) 0.0314(4) Uani d . 1 . .
C C6 0.1178(3) 0.2131(3) -0.05579(14) 0.0298(4) Uani d . 1 . .
C C10 0.2057(3) 0.5418(3) 0.22926(15) 0.0316(4) Uani d . 1 . .
H H10 0.3274 0.5541 0.2067 0.038 Uiso calc R 1 . .
C C7 -0.0805(3) 0.1144(3) -0.11378(14) 0.0298(4) Uani d . 1 . .
C C13 -0.1544(3) 0.5092(3) 0.29647(16) 0.0351(5) Uani d . 1 . .
H H13 -0.2750 0.5003 0.3195 0.042 Uiso calc R 1 . .
C C3 0.0768(4) 0.0078(3) -0.23831(16) 0.0375(5) Uani d . 1 . .
H H3 0.0639 -0.0598 -0.2995 0.045 Uiso calc R 1 . .
C C1 -0.3285(4) -0.1801(4) -0.35196(16) 0.0471(6) Uani d . 1 . .
H H1A -0.4751 -0.2415 -0.3792 0.071 Uiso calc R 1 . .
H H1B -0.2670 -0.2781 -0.3566 0.071 Uiso calc R 1 . .
H H1C -0.2621 -0.0836 -0.3849 0.071 Uiso calc R 1 . .
C C11 0.2199(3) 0.6352(3) 0.32091(15) 0.0320(4) Uani d . 1 . .
C C12 0.0382(4) 0.6204(3) 0.35391(15) 0.0329(4) Uani d . 1 . .
C C4 0.2745(4) 0.1064(4) -0.18074(17) 0.0403(5) Uani d . 1 . .
H H4 0.3927 0.1039 -0.2035 0.048 Uiso calc R 1 . .
H H2A -0.360(4) 0.212(4) 0.105(2) 0.043(7) Uiso d . 1 . .
H H2B -0.455(5) 0.251(4) 0.177(2) 0.049(8) Uiso d . 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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O2 H2 . . 109.5 ?
C2 O1 C1 . . 117.15(19) ?
C8 N1 C9 . . 122.27(18) ?
C10 C9 C14 . . 119.32(18) ?
C10 C9 N1 . . 124.08(19) ?
C14 C9 N1 . . 116.59(18) ?
C4 C5 C6 . . 120.7(2) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C14 N2 H2A . . 111.2(19) ?
C14 N2 H2B . . 114(2) ?
H2A N2 H2B . . 111(3) ?
O1 C2 C3 . . 125.3(2) ?
O1 C2 C7 . . 114.79(19) ?
C3 C2 C7 . . 119.9(2) ?
N1 C8 C6 . . 122.43(19) ?
N1 C8 H8 . . 118.8 ?
C6 C8 H8 . . 118.8 ?
N2 C14 C13 . . 120.2(2) ?
N2 C14 C9 . . 121.2(2) ?
C13 C14 C9 . . 118.57(19) ?
C7 C6 C5 . . 119.27(19) ?
C7 C6 C8 . . 121.15(19) ?
C5 C6 C8 . . 119.57(19) ?
C11 C10 C9 . . 121.3(2) ?
C11 C10 H10 . . 119.3 ?
C9 C10 H10 . . 119.3 ?
O2 C7 C6 . . 121.88(18) ?
O2 C7 C2 . . 118.60(18) ?
C6 C7 C2 . . 119.52(19) ?
C12 C13 C14 . . 121.3(2) ?
C12 C13 H13 . . 119.4 ?
C14 C13 H13 . . 119.4 ?
C2 C3 C4 . . 120.7(2) ?
C2 C3 H3 . . 119.7 ?
C4 C3 H3 . . 119.7 ?
O1 C1 H1A . . 109.5 ?
O1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
O1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C10 C11 C12 . . 119.28(19) ?
C10 C11 Br2 . . 118.48(16) ?
C12 C11 Br2 . . 122.23(16) ?
C13 C12 C11 . . 120.21(19) ?
C13 C12 Br1 . . 118.15(16) ?
C11 C12 Br1 . . 121.63(16) ?
C5 C4 C3 . . 119.9(2) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C12 . 1.891(2) ?
Br2 C11 . 1.890(2) ?
O2 C7 . 1.350(3) ?
O2 H2 . 0.8200 ?
O1 C2 . 1.372(3) ?
O1 C1 . 1.430(3) ?
N1 C8 . 1.285(3) ?
N1 C9 . 1.411(3) ?
C9 C10 . 1.393(3) ?
C9 C14 . 1.408(3) ?
C5 C4 . 1.368(3) ?
C5 C6 . 1.403(3) ?
C5 H5 . 0.9300 ?
N2 C14 . 1.382(3) ?
N2 H2A . 0.84(3) ?
N2 H2B . 0.81(3) ?
C2 C3 . 1.376(3) ?
C2 C7 . 1.404(3) ?
C8 C6 . 1.449(3) ?
C8 H8 . 0.9300 ?
C14 C13 . 1.395(3) ?
C6 C7 . 1.400(3) ?
C10 C11 . 1.382(3) ?
C10 H10 . 0.9300 ?
C13 C12 . 1.379(3) ?
C13 H13 . 0.9300 ?
C3 C4 . 1.394(3) ?
C3 H3 . 0.9300 ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C11 C12 . 1.388(3) ?
C4 H4 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2 H2 N1 . 0.82 1.8788 2.608(2) 147.41
N2 H2A N1 . 0.84(3) 2.39(3) 2.756(3) 107(2)
N2 H2B O1 2_455 0.81(3) 2.30(3) 3.114(3) 174.19
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741510
