#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:52:15 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301804 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/47/2214710.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_2214710
loop_
_publ_author_name
'Yamu Xia'
'Qi Wang'
'Jia You'
_publ_section_title
;
 2-[(2-Aminophenylimino)phenylmethyl]-4-bromophenol
;
_journal_coeditor_code           HG2255
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3529
_journal_page_last               o3529
_journal_paper_doi               10.1107/S1600536807034228
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C19 H15 Br N2 O'
_chemical_formula_moiety         'C19 H15 Br N2 O'
_chemical_formula_sum            'C19 H15 Br N2 O'
_chemical_formula_weight         367.23
_chemical_name_systematic
;
2-[(2-Aminophenylimino)phenylmethyl]-4-bromophenol
;
_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                68.94(3)
_cell_angle_beta                 85.40(3)
_cell_angle_gamma                78.31(3)
_cell_formula_units_Z            2
_cell_length_a                   8.4504(17)
_cell_length_b                   9.4206(19)
_cell_length_c                   11.141(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      4
_cell_volume                     810.5(3)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'NRCVAX (Gabe et al.,  1989)'
_computing_molecular_graphics    'SHELXTL/PC (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 0.979
_diffrn_measured_fraction_theta_max 0.979
_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  0.0180
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3365
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.96
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.542
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.275
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0383
_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)+(0.05P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.0987
_reflns_number_gt                2094
_reflns_number_total             2785
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2255.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               2214710
_cod_database_fobs_code          2214710
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 0.82601(5) 0.79635(4) -0.41528(3) 0.07530(19) Uani d . 1
O O1 0.1888(2) 0.8105(2) -0.1436(2) 0.0624(6) Uani d . 1
H H1 0.2000 0.7754 -0.0624 0.075 Uiso d R 1
N N1 0.1382(3) 0.9926(3) 0.1374(3) 0.0688(8) Uani d . 1
H H1A 0.1667 1.0127 0.0581 0.083 Uiso calc R 1
H H1B 0.0732 1.0614 0.1604 0.083 Uiso calc R 1
N N2 0.3303(3) 0.7716(3) 0.0581(2) 0.0517(6) Uani d . 1
C C1 0.9008(5) 0.6305(5) 0.2237(4) 0.0752(10) Uani d . 1
H H1C 0.9945 0.6028 0.2716 0.090 Uiso calc R 1
C C2 0.8721(4) 0.5433(4) 0.1568(3) 0.0674(9) Uani d . 1
H H2B 0.9468 0.4547 0.1601 0.081 Uiso calc R 1
C C3 0.7361(4) 0.5825(4) 0.0847(3) 0.0554(8) Uani d . 1
H H3A 0.7197 0.5218 0.0386 0.066 Uiso calc R 1
C C4 0.6232(4) 0.7126(3) 0.0804(3) 0.0454(7) Uani d . 1
C C5 0.6508(4) 0.8013(4) 0.1486(3) 0.0559(8) Uani d . 1
H H5A 0.5755 0.8891 0.1468 0.067 Uiso calc R 1
C C6 0.7894(5) 0.7604(5) 0.2197(3) 0.0708(10) Uani d . 1
H H6A 0.8078 0.8211 0.2652 0.085 Uiso calc R 1
C C7 0.4709(3) 0.7531(3) 0.0073(3) 0.0441(7) Uani d . 1
C C8 0.4763(3) 0.7798(3) -0.1316(3) 0.0449(7) Uani d . 1
C C9 0.6214(4) 0.7812(3) -0.1996(3) 0.0518(7) Uani d . 1
H H9A 0.7169 0.7688 -0.1577 0.062 Uiso calc R 1
C C10 0.6255(4) 0.8009(3) -0.3276(3) 0.0552(8) Uani d . 1
C C11 0.4869(4) 0.8210(4) -0.3928(3) 0.0601(9) Uani d . 1
H H11A 0.4913 0.8332 -0.4796 0.072 Uiso calc R 1
C C12 0.3429(4) 0.8230(4) -0.3288(3) 0.0591(8) Uani d . 1
H H12A 0.2485 0.8371 -0.3727 0.071 Uiso calc R 1
C C13 0.3342(4) 0.8041(3) -0.1989(3) 0.0500(7) Uani d . 1
C C14 0.3017(3) 0.7385(3) 0.1922(3) 0.0478(7) Uani d . 1
C C15 0.1967(3) 0.8507(4) 0.2275(3) 0.0505(7) Uani d . 1
C C16 0.1562(4) 0.8156(4) 0.3567(3) 0.0607(9) Uani d . 1
H H16A 0.0891 0.8903 0.3833 0.073 Uiso calc R 1
C C17 0.2127(4) 0.6739(4) 0.4455(3) 0.0657(9) Uani d . 1
H H17A 0.1807 0.6521 0.5310 0.079 Uiso calc R 1
C C18 0.3161(4) 0.5631(4) 0.4103(3) 0.0646(9) Uani d . 1
H H18A 0.3555 0.4669 0.4713 0.078 Uiso calc R 1
C C19 0.3607(4) 0.5967(4) 0.2831(3) 0.0585(8) Uani d . 1
H H19A 0.4316 0.5227 0.2581 0.070 Uiso calc R 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
C13 O1 H1 108.9
C15 N1 H1A 120.0
C15 N1 H1B 120.0
H1A N1 H1B 120.0
C7 N2 C14 124.1(3)
C2 C1 C6 119.1(4)
C2 C1 H1C 120.5
C6 C1 H1C 120.5
C1 C2 C3 121.6(3)
C1 C2 H2B 119.2
C3 C2 H2B 119.2
C2 C3 C4 119.8(3)
C2 C3 H3A 120.1
C4 C3 H3A 120.1
C5 C4 C3 119.1(3)
C5 C4 C7 120.3(3)
C3 C4 C7 120.6(3)
C6 C5 C4 120.1(3)
C6 C5 H5A 119.9
C4 C5 H5A 119.9
C1 C6 C5 120.4(3)
C1 C6 H6A 119.8
C5 C6 H6A 119.8
N2 C7 C8 116.4(3)
N2 C7 C4 123.2(2)
C8 C7 C4 120.3(2)
C9 C8 C13 118.0(3)
C9 C8 C7 121.2(3)
C13 C8 C7 120.7(3)
C10 C9 C8 120.7(3)
C10 C9 H9A 119.6
C8 C9 H9A 119.6
C9 C10 C11 121.2(3)
C9 C10 Br1 119.4(3)
C11 C10 Br1 119.4(2)
C12 C11 C10 119.1(3)
C12 C11 H11A 120.5
C10 C11 H11A 120.5
C11 C12 C13 121.2(3)
C11 C12 H12A 119.4
C13 C12 H12A 119.4
O1 C13 C12 117.7(3)
O1 C13 C8 122.6(3)
C12 C13 C8 119.7(3)
C19 C14 C15 120.5(3)
C19 C14 N2 122.5(3)
C15 C14 N2 116.7(3)
N1 C15 C14 120.8(3)
N1 C15 C16 121.5(3)
C14 C15 C16 117.7(3)
C17 C16 C15 121.3(3)
C17 C16 H16A 119.4
C15 C16 H16A 119.4
C16 C17 C18 120.9(3)
C16 C17 H17A 119.6
C18 C17 H17A 119.6
C17 C18 C19 118.8(3)
C17 C18 H18A 120.6
C19 C18 H18A 120.6
C18 C19 C14 120.8(3)
C18 C19 H19A 119.6
C14 C19 H19A 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C10 1.887(3)
O1 C13 1.330(4)
O1 H1 0.8499
N1 C15 1.373(4)
N1 H1A 0.8600
N1 H1B 0.8600
N2 C7 1.281(3)
N2 C14 1.423(3)
C1 C2 1.356(5)
C1 C6 1.373(6)
C1 H1C 0.9300
C2 C3 1.366(5)
C2 H2B 0.9300
C3 C4 1.380(4)
C3 H3A 0.9300
C4 C5 1.377(4)
C4 C7 1.487(4)
C5 C6 1.376(5)
C5 H5A 0.9300
C6 H6A 0.9300
C7 C8 1.475(4)
C8 C9 1.389(4)
C8 C13 1.401(4)
C9 C10 1.369(4)
C9 H9A 0.9300
C10 C11 1.372(5)
C11 C12 1.361(4)
C11 H11A 0.9300
C12 C13 1.391(4)
C12 H12A 0.9300
C14 C19 1.378(4)
C14 C15 1.387(4)
C15 C16 1.387(4)
C16 C17 1.363(5)
C16 H16A 0.9300
C17 C18 1.370(5)
C17 H17A 0.9300
C18 C19 1.375(4)
C18 H18A 0.9300
C19 H19A 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
_geom_hbond_publ_flag
N1 H1B O1 2_575 0.86 2.28 3.011(3) 142.4 yes
O1 H1 N2 1 0.85 1.79 2.505(3) 140.6 yes
N1 H1A N2 1 0.86 2.41 2.734(4) 103.1 yes
N1 H1B Cg1 2_675 0.86 3.20 3.799(2) 129 yes
C19 H19A Cg2 2_665 0.93 2.98 3.800(3) 148 yes
C1 H1C Cg3 1_655 0.93 2.76 3.557(3) 145 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655296
2 PubChem 136059352
