#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/63/2216383.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_2216383
loop_
_publ_author_name
'Fengke Yang'
'Yan Wang'
'Zhantao Zhang'
_publ_section_title
;
 4-Bromo-2-{[2-(2-hydroxybenzylideneamino)phenylimino]phenylmethyl}phenol
;
_journal_coeditor_code           CV2333
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4608
_journal_page_last               o4608
_journal_paper_doi               10.1107/S1600536807055018
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C26 H19 Br N2 O2'
_chemical_formula_moiety         'C26 H19 Br N2 O2'
_chemical_formula_sum            'C26 H19 Br N2 O2'
_chemical_formula_weight         471.34
_chemical_name_systematic
;
4-Bromo-2-{[2-(2-hydroxybenzylideneamino)phenylimino]phenylmethyl}phenol
;
_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                90.87(3)
_cell_angle_beta                 108.79(3)
_cell_angle_gamma                94.09(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1682(18)
_cell_length_b                   9.7011(19)
_cell_length_c                   12.986(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      4
_cell_volume                     1089.8(4)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'NRCVAX (Gabe et al.,  1989)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1990)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       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  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4501
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.66
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.911
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.302
_refine_ls_extinction_coef       0.0051(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3742
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0342
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0443P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0907
_reflns_number_gt                2837
_reflns_number_total             3742
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2333.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.

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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2216383
_cod_database_fobs_code          2216383
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
Br Br1 0.10044(3) 0.19363(3) 0.02361(3) 0.06928(16) Uani d . 1
O O1 -0.4811(3) 0.3545(2) 0.0968(2) 0.0759(7) Uani d . 1
O O2 -0.2232(3) 0.3849(3) 0.4416(2) 0.0907(8) Uani d . 1
N N1 -0.4694(3) 0.2214(2) 0.41956(17) 0.0535(6) Uani d . 1
N N2 -0.4777(3) 0.1461(2) 0.21221(16) 0.0518(5) Uani d . 1
C C1 -0.3534(3) 0.3110(3) 0.0812(2) 0.0536(7) Uani d . 1
C C2 -0.2881(3) 0.3884(3) 0.0147(2) 0.0619(8) Uani d . 1
H H2C -0.3349 0.4655 -0.0183 0.074 Uiso calc R 1
C C3 -0.1559(3) 0.3518(3) -0.0024(2) 0.0562(7) Uani d . 1
H H3A -0.1128 0.4043 -0.0462 0.067 Uiso calc R 1
C C4 -0.0870(3) 0.2371(3) 0.0456(2) 0.0474(6) Uani d . 1
C C5 -0.1511(3) 0.1557(3) 0.10858(19) 0.0462(6) Uani d . 1
H H5A -0.1042 0.0773 0.1389 0.055 Uiso calc R 1
C C6 -0.2872(3) 0.1906(2) 0.12716(18) 0.0436(6) Uani d . 1
C C7 -0.3600(3) 0.1023(3) 0.19163(18) 0.0442(6) Uani d . 1
C C8 -0.2987(3) -0.0321(3) 0.2296(2) 0.0487(6) Uani d . 1
C C9 -0.3297(4) -0.1462(3) 0.1588(3) 0.0759(9) Uani d . 1
H H9A -0.3842 -0.1378 0.0855 0.091 Uiso calc R 1
C C10 -0.2800(5) -0.2733(4) 0.1967(4) 0.0986(13) Uani d . 1
H H10A -0.3017 -0.3502 0.1491 0.118 Uiso calc R 1
C C11 -0.1981(5) -0.2849(4) 0.3055(4) 0.1011(14) Uani d . 1
H H11A -0.1650 -0.3700 0.3312 0.121 Uiso calc R 1
C C12 -0.1656(4) -0.1727(4) 0.3750(3) 0.0879(11) Uani d . 1
H H12A -0.1094 -0.1811 0.4480 0.106 Uiso calc R 1
C C13 -0.2157(3) -0.0453(3) 0.3376(2) 0.0647(8) Uani d . 1
H H13A -0.1932 0.0312 0.3857 0.078 Uiso calc R 1
C C14 -0.2425(4) 0.4371(3) 0.5333(2) 0.0647(8) Uani d . 1
C C15 -0.1351(4) 0.5408(3) 0.5954(3) 0.0794(9) Uani d . 1
H H15A -0.0526 0.5739 0.5733 0.095 Uiso calc R 1
C C16 -0.1522(4) 0.5937(3) 0.6893(3) 0.0823(10) Uani d . 1
H H16A -0.0805 0.6626 0.7304 0.099 Uiso calc R 1
C C17 -0.2734(4) 0.5464(4) 0.7236(3) 0.0815(10) Uani d . 1
H H17A -0.2829 0.5829 0.7875 0.098 Uiso calc R 1
C C18 -0.3795(4) 0.4459(3) 0.6633(2) 0.0716(9) Uani d . 1
H H18A -0.4617 0.4147 0.6864 0.086 Uiso calc R 1
C C19 -0.3663(3) 0.3888(3) 0.5670(2) 0.0546(7) Uani d . 1
C C20 -0.4790(3) 0.2801(3) 0.5055(2) 0.0580(7) Uani d . 1
H H20A -0.5612 0.2521 0.5296 0.070 Uiso d R 1
C C21 -0.5766(3) 0.1108(3) 0.3638(2) 0.0495(6) Uani d . 1
C C22 -0.6821(3) 0.0394(3) 0.4052(2) 0.0671(8) Uani d . 1
H H22A -0.6867 0.0666 0.4730 0.081 Uiso d R 1
C C23 -0.7793(3) -0.0705(3) 0.3476(3) 0.0684(8) Uani d . 1
H H23A -0.8508 -0.1147 0.3756 0.082 Uiso calc R 1
C C24 -0.7710(3) -0.1143(3) 0.2498(2) 0.0647(8) Uani d . 1
H H24A -0.8352 -0.1896 0.2118 0.078 Uiso calc R 1
C C25 -0.6669(3) -0.0467(3) 0.2071(2) 0.0617(7) Uani d . 1
H H25A -0.6617 -0.0770 0.1401 0.074 Uiso calc R 1
C C26 -0.5700(3) 0.0657(3) 0.2628(2) 0.0474(6) Uani d . 1
H H1 -0.500(4) 0.301(3) 0.139(3) 0.080(11) Uiso d . 1
H H2 -0.290(4) 0.323(4) 0.415(3) 0.105(14) 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
C1 O1 H1 . . 104(2)
C14 O2 H2 . . 110(3)
C20 N1 C21 . . 121.4(2)
C7 N2 C26 . . 123.7(2)
O1 C1 C2 . . 117.7(2)
O1 C1 C6 . . 122.4(2)
C2 C1 C6 . . 119.9(2)
C3 C2 C1 . . 120.7(3)
C3 C2 H2C . . 119.6
C1 C2 H2C . . 119.6
C2 C3 C4 . . 119.7(2)
C2 C3 H3A . . 120.1
C4 C3 H3A . . 120.1
C3 C4 C5 . . 121.1(2)
C3 C4 Br1 . . 118.32(19)
C5 C4 Br1 . . 120.6(2)
C4 C5 C6 . . 120.3(2)
C4 C5 H5A . . 119.8
C6 C5 H5A . . 119.8
C1 C6 C5 . . 118.1(2)
C1 C6 C7 . . 120.8(2)
C5 C6 C7 . . 121.1(2)
N2 C7 C6 1 . 117.6(2)
N2 C7 C6 . . 117.6(2)
N2 C7 C8 1 . 122.2(2)
N2 C7 C8 . . 122.2(2)
C6 C7 C8 . . 120.2(2)
C13 C8 C9 . . 119.3(3)
C13 C8 C7 . . 119.8(2)
C9 C8 C7 . . 120.8(2)
C8 C9 C10 . . 120.3(3)
C8 C9 H9A . . 119.9
C10 C9 H9A . . 119.9
C11 C10 C9 . . 119.6(4)
C11 C10 H10A . . 120.2
C9 C10 H10A . . 120.2
C12 C11 C10 . . 120.3(4)
C12 C11 H11A . . 119.8
C10 C11 H11A . . 119.8
C11 C12 C13 . . 120.3(4)
C11 C12 H12A . . 119.8
C13 C12 H12A . . 119.8
C8 C13 C12 . . 120.1(3)
C8 C13 H13A . . 119.9
C12 C13 H13A . . 119.9
O2 C14 C19 . . 121.4(3)
O2 C14 C15 . . 118.9(3)
C19 C14 C15 . . 119.7(3)
C16 C15 C14 . . 119.6(3)
C16 C15 H15A . . 120.2
C14 C15 H15A . . 120.2
C15 C16 C17 . . 121.2(3)
C15 C16 H16A . . 119.4
C17 C16 H16A . . 119.4
C18 C17 C16 . . 119.7(3)
C18 C17 H17A . . 120.1
C16 C17 H17A . . 120.1
C17 C18 C19 . . 120.9(3)
C17 C18 H18A . . 119.5
C19 C18 H18A . . 119.5
C14 C19 C18 . . 118.8(3)
C14 C19 C20 . . 121.3(2)
C18 C19 C20 . . 119.9(3)
N1 C20 C19 1 . 122.4(2)
N1 C20 C19 . . 122.4(2)
N1 C20 H20A 1 . 118.8
N1 C20 H20A . . 118.8
C19 C20 H20A . . 118.8
C22 C21 C26 . . 118.0(2)
C22 C21 N1 . 1 124.7(2)
C26 C21 N1 . 1 117.2(2)
C22 C21 N1 . . 124.7(2)
C26 C21 N1 . . 117.2(2)
C23 C22 C21 . . 121.3(3)
C23 C22 H22A . . 119.4
C21 C22 H22A . . 119.3
C24 C23 C22 . . 120.2(3)
C24 C23 H23A . . 119.9
C22 C23 H23A . . 119.9
C23 C24 C25 . . 119.9(3)
C23 C24 H24A . . 120.1
C25 C24 H24A . . 120.1
C24 C25 C26 . . 120.8(3)
C24 C25 H25A . . 119.6
C26 C25 H25A . . 119.6
C25 C26 C21 . . 119.7(2)
C25 C26 N2 . 1 120.5(2)
C21 C26 N2 . 1 119.3(2)
C25 C26 N2 . . 120.5(2)
C21 C26 N2 . . 119.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C4 . 1.905(2)
O1 C1 . 1.346(3)
O1 H1 . 0.80(3)
O2 C14 . 1.354(3)
O2 H2 . 0.81(3)
N1 C20 . 1.276(3)
N1 C21 . 1.418(3)
N2 C7 . 1.291(3)
N2 C26 . 1.427(3)
C1 C2 . 1.399(4)
C1 C6 . 1.406(3)
C2 C3 . 1.370(4)
C2 H2C . 0.9300
C3 C4 . 1.376(4)
C3 H3A . 0.9300
C4 C5 . 1.379(3)
C5 C6 . 1.407(3)
C5 H5A . 0.9300
C6 C7 . 1.477(3)
C7 N2 1 1.291(3)
C7 C8 . 1.485(4)
C8 C13 . 1.377(4)
C8 C9 . 1.380(4)
C9 C10 . 1.387(5)
C9 H9A . 0.9300
C10 C11 . 1.381(6)
C10 H10A . 0.9300
C11 C12 . 1.355(5)
C11 H11A . 0.9300
C12 C13 . 1.389(4)
C12 H12A . 0.9300
C13 H13A . 0.9300
C14 C19 . 1.397(4)
C14 C15 . 1.398(4)
C15 C16 . 1.375(4)
C15 H15A . 0.9300
C16 C17 . 1.377(5)
C16 H16A . 0.9300
C17 C18 . 1.364(4)
C17 H17A . 0.9300
C18 C19 . 1.404(4)
C18 H18A . 0.9300
C19 C20 . 1.451(4)
C20 N1 1 1.276(3)
C20 H20A . 0.9300
C21 C22 . 1.398(3)
C21 C26 . 1.398(3)
C21 N1 1 1.418(3)
C22 C23 . 1.379(4)
C22 H22A . 0.9300
C23 C24 . 1.359(4)
C23 H23A . 0.9300
C24 C25 . 1.383(4)
C24 H24A . 0.9300
C25 C26 . 1.388(4)
C25 H25A . 0.9300
C26 N2 1 1.427(3)
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
_geom_hbond_publ_flag
O1 H1 N2 1 0.80(3) 1.79(3) 2.530(3) 154(3) yes
O2 H2 N1 1 0.81(3) 1.87(3) 2.596(3) 148(3) yes
C2 H2C O1 2_465 0.93 2.51 3.419(4) 165.6 yes
C15 H15A O2 2_566 0.93 2.60 3.497(4) 162.0 yes
