#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/86/2238628.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_2238628
loop_
_publ_author_name
'Wang, Xiao-Zhen'
_publ_section_title
;
 N,N'-Bis(3-bromo-2-hydroxybenzylidene)propane-1,3-diamine
;
_journal_coeditor_code           HB7137
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1584
_journal_paper_doi               10.1107/S1600536813025403
_journal_volume                  69
_journal_year                    2013
_chemical_formula_moiety         'C17 H16 Br2 N2 O2'
_chemical_formula_sum            'C17 H16 Br2 N2 O2'
_chemical_formula_weight         440.14
_chemical_name_systematic
;
N,N'-Bis(3-bromo-2-hydroxybenzylidene)propane-1,3-diamine
;
_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                 113.744(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.7790(10)
_cell_length_b                   10.1894(8)
_cell_length_c                   14.3953(12)
_cell_measurement_reflns_used    8352
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      2.5
_cell_volume                     1715.8(2)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD'
_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  0.0550
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19018
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.53
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.735
_exptl_absorpt_correction_T_max  0.4223
_exptl_absorpt_correction_T_min  0.4089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.725
_refine_diff_density_min         -1.009
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3728
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0537
_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)+(0.0633P)²+2.4024P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1409
_reflns_number_gt                2669
_reflns_number_total             3728
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7137.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2238628
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
Br Br1 0.30295(5) 0.46157(5) 0.10435(4) 0.0628(2) Uani d . 1 1
Br Br2 -0.37545(5) 0.26857(7) 0.63883(5) 0.0760(2) Uani d . 1 1
N N1 0.0868(3) 0.1060(3) 0.2505(2) 0.0387(8) Uani d . 1 1
N N2 -0.0781(3) 0.2245(4) 0.4529(3) 0.0454(9) Uani d . 1 1
O O1 0.1442(2) 0.2886(3) 0.1573(2) 0.0433(7) Uani d . 1 1
H H1 0.1017 0.2399 0.1714 0.065 Uiso calc R 1 1
O O2 -0.2045(3) 0.1922(3) 0.5504(3) 0.0514(8) Uani d . 1 1
H H2 -0.1583 0.1739 0.5261 0.077 Uiso calc R 1 1
C C1 0.2813(3) 0.1666(4) 0.2944(3) 0.0394(9) Uani d . 1 1
C C2 0.2528(3) 0.2639(4) 0.2194(3) 0.0365(9) Uani d . 1 1
C C3 0.3399(4) 0.3351(4) 0.2097(3) 0.0421(10) Uani d . 1 1
C C4 0.4525(4) 0.3144(5) 0.2741(4) 0.0562(13) Uani d . 1 1
H H4 0.5100 0.3641 0.2671 0.067 Uiso calc R 1 1
C C5 0.4797(4) 0.2202(6) 0.3486(4) 0.0644(15) Uani d . 1 1
H H5 0.5556 0.2072 0.3927 0.077 Uiso calc R 1 1
C C6 0.3956(4) 0.1454(5) 0.3583(4) 0.0560(12) Uani d . 1 1
H H6 0.4148 0.0803 0.4076 0.067 Uiso calc R 1 1
C C7 0.1924(4) 0.0872(4) 0.3054(3) 0.0417(10) Uani d . 1 1
H H7 0.2132 0.0209 0.3539 0.050 Uiso calc R 1 1
C C8 0.0013(4) 0.0262(4) 0.2677(4) 0.0472(11) Uani d . 1 1
H H8A 0.0393 -0.0419 0.3168 0.057 Uiso calc R 1 1
H H8B -0.0477 -0.0159 0.2048 0.057 Uiso calc R 1 1
C C9 -0.0711(4) 0.1100(5) 0.3066(3) 0.0440(10) Uani d . 1 1
H H9A -0.1066 0.1798 0.2585 0.053 Uiso calc R 1 1
H H9B -0.1315 0.0563 0.3112 0.053 Uiso calc R 1 1
C C10 -0.0019(4) 0.1693(6) 0.4094(3) 0.0546(12) Uani d . 1 1
H H10A 0.0462 0.1024 0.4544 0.065 Uiso calc R 1 1
H H10B 0.0472 0.2378 0.4026 0.065 Uiso calc R 1 1
C C11 -0.1054(4) 0.3460(5) 0.4441(3) 0.0440(10) Uani d . 1 1
H H11 -0.0739 0.4017 0.4111 0.053 Uiso calc R 1 1
C C12 -0.1838(3) 0.3993(4) 0.4838(3) 0.0372(9) Uani d . 1 1
C C13 -0.2308(3) 0.3159(4) 0.5356(3) 0.0353(9) Uani d . 1 1
C C14 -0.3080(4) 0.3746(5) 0.5709(3) 0.0429(10) Uani d . 1 1
C C15 -0.3355(4) 0.5048(5) 0.5559(4) 0.0594(13) Uani d . 1 1
H H15 -0.3870 0.5400 0.5799 0.071 Uiso calc R 1 1
C C16 -0.2879(5) 0.5853(5) 0.5054(4) 0.0679(15) Uani d . 1 1
H H16 -0.3074 0.6737 0.4953 0.081 Uiso calc R 1 1
C C17 -0.2116(5) 0.5328(5) 0.4708(4) 0.0580(13) Uani d . 1 1
H H17 -0.1779 0.5865 0.4383 0.070 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'
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
C7 N1 C8 119.2(4)
C11 N2 C10 122.1(4)
C2 O1 H1 109.5
C13 O2 H2 109.5
C6 C1 C2 119.7(4)
C6 C1 C7 119.9(4)
C2 C1 C7 120.3(4)
O1 C2 C3 119.7(4)
O1 C2 C1 121.7(4)
C3 C2 C1 118.6(4)
C4 C3 C2 121.2(4)
C4 C3 Br1 119.8(4)
C2 C3 Br1 119.0(3)
C5 C4 C3 119.9(5)
C5 C4 H4 120.1
C3 C4 H4 120.1
C6 C5 C4 120.4(4)
C6 C5 H5 119.8
C4 C5 H5 119.8
C5 C6 C1 120.2(5)
C5 C6 H6 119.9
C1 C6 H6 119.9
N1 C7 C1 121.8(4)
N1 C7 H7 119.1
C1 C7 H7 119.1
N1 C8 C9 110.9(3)
N1 C8 H8A 109.5
C9 C8 H8A 109.5
N1 C8 H8B 109.5
C9 C8 H8B 109.5
H8A C8 H8B 108.0
C10 C9 C8 112.5(4)
C10 C9 H9A 109.1
C8 C9 H9A 109.1
C10 C9 H9B 109.1
C8 C9 H9B 109.1
H9A C9 H9B 107.8
N2 C10 C9 110.2(4)
N2 C10 H10A 109.6
C9 C10 H10A 109.6
N2 C10 H10B 109.6
C9 C10 H10B 109.6
H10A C10 H10B 108.1
N2 C11 C12 122.1(4)
N2 C11 H11 119.0
C12 C11 H11 119.0
C17 C12 C13 121.0(4)
C17 C12 C11 119.5(4)
C13 C12 C11 119.5(4)
O2 C13 C14 121.6(4)
O2 C13 C12 122.2(4)
C14 C13 C12 116.2(4)
C15 C14 C13 121.8(4)
C15 C14 Br2 119.8(4)
C13 C14 Br2 118.4(3)
C14 C15 C16 121.1(5)
C14 C15 H15 119.4
C16 C15 H15 119.4
C17 C16 C15 119.1(5)
C17 C16 H16 120.5
C15 C16 H16 120.5
C16 C17 C12 120.7(5)
C16 C17 H17 119.7
C12 C17 H17 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.899(5)
Br2 C14 1.883(4)
N1 C7 1.274(5)
N1 C8 1.462(5)
N2 C11 1.279(6)
N2 C10 1.465(5)
O1 C2 1.337(5)
O1 H1 0.8200
O2 C13 1.300(5)
O2 H2 0.8200
C1 C6 1.394(6)
C1 C2 1.402(6)
C1 C7 1.454(6)
C2 C3 1.382(6)
C3 C4 1.378(6)
C4 C5 1.376(8)
C4 H4 0.9300
C5 C6 1.369(8)
C5 H5 0.9300
C6 H6 0.9300
C7 H7 0.9300
C8 C9 1.521(6)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.511(6)
C9 H9A 0.9700
C9 H9B 0.9700
C10 H10A 0.9700
C10 H10B 0.9700
C11 C12 1.443(6)
C11 H11 0.9300
C12 C17 1.400(6)
C12 C13 1.415(6)
C13 C14 1.412(6)
C14 C15 1.366(7)
C15 C16 1.388(8)
C15 H15 0.9300
C16 C17 1.370(8)
C16 H16 0.9300
C17 H17 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
O1 H1 N1 . 0.82 1.83 2.567(4) 148
O2 H2 N2 . 0.82 1.82 2.553(5) 149
C7 H7 O2 3_556 0.93 2.60 3.490(5) 161
