#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/78/2007831.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_2007831
loop_
_publ_author_name
'Elerman, Yalc̨in'
'Elmali, Ayhan'
'Kabak, Mehmet'
'Svoboda, Ingrid'
_publ_section_title
;
 N,N'-Bis(5-bromo-2-hydroxybenzylidene)-1,3-propanediamine
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1701
_journal_page_last               1703
_journal_paper_doi               10.1107/S0108270198005046
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C17 H16 Br2 N2 O2'
_chemical_formula_sum            'C17 H16 Br2 N2 O2'
_chemical_formula_weight         440.14
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 96.350(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.438(2)
_cell_length_b                   8.9020(10)
_cell_length_c                   17.189(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      12.30
_cell_measurement_theta_min      3.41
_cell_volume                     1739.5(5)
_computing_cell_refinement       'Nonius Diffractometer Control Software'
_computing_data_collection
'Nonius Diffractometer Control Software (Nonius, 1993)'
_computing_data_reduction        'REDU4 (Stoe, 1991)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      300(2)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_av_sigmaI/netI    0.1008
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6580
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         2.04
_diffrn_standards_decay_%        2.7
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.670
_exptl_absorpt_correction_T_max  0.627
_exptl_absorpt_correction_T_min  0.272
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   ' (North, Phillips & Mathews, 1968) '
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.467
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.980
_refine_ls_goodness_of_fit_obs   1.090
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.983
_refine_ls_restrained_S_obs      1.090
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_obs          0.0365
_refine_ls_shift/esd_max         0.006
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0364P)²+0.3240P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0967
_refine_ls_wR_factor_obs         0.0727
_reflns_number_observed          1674
_reflns_number_total             3405
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            jz1285.cif
_cod_data_source_block           jz1285
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0364P)^2^+0.3240P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0364P)^2^+0.3240P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2007831
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, -z-1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
O1 -0.3847(3) -0.1497(3) 0.8649(2) 0.0727(10) Uani d . 1 . O
H1O -0.436(5) -0.113(6) 0.821(4) 0.100 Uiso d . 1 . H
C1 -0.2760(3) -0.0954(4) 0.8612(3) 0.0502(10) Uani d . 1 . C
C2 -0.1854(4) -0.1408(5) 0.9164(3) 0.0578(11) Uani d . 1 . C
H2 -0.2006(4) -0.2085(5) 0.9552(3) 0.100 Uiso calc R 1 . H
C3 -0.0738(4) -0.0869(4) 0.9143(3) 0.0557(11) Uani d . 1 . C
H3 -0.0130(4) -0.1201(4) 0.9506(3) 0.100 Uiso calc R 1 . H
C4 -0.0519(3) 0.0178(5) 0.8576(3) 0.0523(11) Uani d . 1 . C
Br1 0.10155(3) 0.09952(6) 0.85939(3) 0.0742(2) Uani d . 1 . Br
C5 -0.1403(3) 0.0646(5) 0.8035(3) 0.0520(10) Uani d . 1 . C
H5 -0.1245(3) 0.1341(5) 0.7657(3) 0.100 Uiso calc R 1 . H
C6 -0.2540(3) 0.0096(4) 0.8042(2) 0.0463(10) Uani d . 1 . C
C7 -0.3480(3) 0.0602(5) 0.7466(3) 0.0548(11) Uani d . 1 . C
H7 -0.3313(3) 0.1284(5) 0.7084(3) 0.100 Uiso calc R 1 . H
N1 -0.4522(3) 0.0132(4) 0.7474(2) 0.0579(9) Uani d . 1 . N
C8 -0.5451(3) 0.0646(5) 0.6882(3) 0.0644(12) Uani d . 1 . C
H8A -0.5824(3) -0.0213(5) 0.6610(3) 0.100 Uiso calc R 1 . H
H8B -0.5115(3) 0.1270(5) 0.6501(3) 0.100 Uiso calc R 1 . H
C9 -0.6362(4) 0.1540(5) 0.7269(3) 0.0623(12) Uani d . 1 . C
H9A -0.6638(4) 0.0943(5) 0.7684(3) 0.100 Uiso calc R 1 . H
H9B -0.5997(4) 0.2440(5) 0.7503(3) 0.100 Uiso calc R 1 . H
C10 -0.7402(4) 0.1980(5) 0.6691(3) 0.0668(13) Uani d . 1 . C
H10A -0.7915(4) 0.2644(5) 0.6945(3) 0.100 Uiso calc R 1 . H
H10B -0.7124(4) 0.2523(5) 0.6258(3) 0.100 Uiso calc R 1 . H
N2 -0.8067(3) 0.0663(4) 0.6391(2) 0.0531(9) Uani d . 1 . N
C11 -0.9185(3) 0.0747(4) 0.6301(2) 0.0488(10) Uani d . 1 . C
H11 -0.9540(3) 0.1634(4) 0.6439(2) 0.100 Uiso calc R 1 . H
C12 -0.9924(3) -0.0483(4) 0.5994(2) 0.0438(9) Uani d . 1 . C
C13 -1.1147(3) -0.0315(5) 0.5894(2) 0.0512(10) Uani d . 1 . C
H13 -1.1481(3) 0.0589(5) 0.6026(2) 0.100 Uiso calc R 1 . H
C14 -1.1855(4) -0.1463(5) 0.5604(3) 0.0560(11) Uani d . 1 . C
Br2 -1.35053(4) -0.11914(6) 0.54553(3) 0.0793(2) Uani d . 1 . Br
C15 -1.1361(4) -0.2816(5) 0.5396(3) 0.0663(13) Uani d . 1 . C
H15 -1.1840(4) -0.3598(5) 0.5192(3) 0.100 Uiso calc R 1 . H
C16 -1.0163(4) -0.2982(5) 0.5494(3) 0.0701(13) Uani d . 1 . C
H16 -0.9838(4) -0.3895(5) 0.5366(3) 0.100 Uiso calc R 1 . H
C17 -0.9431(4) -0.1839(5) 0.5775(3) 0.0536(11) Uani d . 1 . C
O2 -0.8262(3) -0.2042(4) 0.5846(2) 0.0738(10) Uani d . 1 . O
H2O -0.801(5) -0.118(6) 0.601(4) 0.100 Uiso d . 1 . H
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
_geom_angle_publ_flag
C1 O1 H1O 109.(3) ?
O1 C1 C2 119.3(4) y
O1 C1 C6 121.0(4) y
C2 C1 C6 119.7(4) ?
C3 C2 C1 120.6(4) ?
C3 C2 H2 119.7(3) ?
C1 C2 H2 119.7(3) ?
C2 C3 C4 119.6(4) ?
C2 C3 H3 120.2(3) ?
C4 C3 H3 120.2(2) ?
C5 C4 C3 120.3(4) ?
C5 C4 Br1 120.7(3) y
C3 C4 Br1 119.0(3) y
C4 C5 C6 120.7(4) ?
C4 C5 H5 119.6(2) ?
C6 C5 H5 119.6(3) ?
C5 C6 C1 118.9(4) ?
C5 C6 C7 120.5(4) ?
C1 C6 C7 120.6(3) ?
N1 C7 C6 121.2(4) y
N1 C7 H7 119.4(3) ?
C6 C7 H7 119.4(2) ?
C7 N1 C8 120.2(4) y
N1 C8 C9 109.9(4) y
N1 C8 H8A 109.7(2) ?
C9 C8 H8A 109.7(2) ?
N1 C8 H8B 109.7(2) ?
C9 C8 H8B 109.7(3) ?
H8A C8 H8B 108.2 ?
C10 C9 C8 112.0(4) ?
C10 C9 H9A 109.2(3) ?
C8 C9 H9A 109.2(3) ?
C10 C9 H9B 109.2(2) ?
C8 C9 H9B 109.2(2) ?
H9A C9 H9B 107.9 ?
N2 C10 C9 111.3(4) y
N2 C10 H10A 109.4(2) ?
C9 C10 H10A 109.4(3) ?
N2 C10 H10B 109.4(2) ?
C9 C10 H10B 109.4(3) ?
H10A C10 H10B 108.0 ?
C11 N2 C10 118.1(3) y
N2 C11 C12 122.5(4) y
N2 C11 H11 118.7(2) ?
C12 C11 H11 118.7(2) ?
C13 C12 C17 119.0(4) ?
C13 C12 C11 120.0(4) ?
C17 C12 C11 120.9(3) ?
C14 C13 C12 120.7(4) ?
C14 C13 H13 119.6(2) ?
C12 C13 H13 119.6(3) ?
C13 C14 C15 120.0(4) ?
C13 C14 Br2 119.8(3) y
C15 C14 Br2 120.2(3) y
C16 C15 C14 119.4(4) ?
C16 C15 H15 120.3(3) ?
C14 C15 H15 120.3(3) ?
C15 C16 C17 121.8(4) ?
C15 C16 H16 119.1(3) ?
C17 C16 H16 119.1(3) ?
O2 C17 C16 119.8(4) y
O2 C17 C12 121.2(4) y
C16 C17 C12 119.0(4) ?
C17 O2 H2O 102.(4) ?
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
O1 C1 . 1.342(5) y
O1 H1O . 0.96(6) ?
C1 C2 . 1.386(6) ?
C1 C6 . 1.396(6) ?
C2 C3 . 1.367(6) ?
C2 H2 . 0.93 ?
C3 C4 . 1.391(6) ?
C3 H3 . 0.93 ?
C4 C5 . 1.361(6) ?
C4 Br1 . 1.897(4) y
C5 C6 . 1.391(5) ?
C5 H5 . 0.93 ?
C6 C7 . 1.450(6) ?
C7 N1 . 1.265(5) y
C7 H7 . 0.93 ?
N1 C8 . 1.461(5) y
C8 C9 . 1.521(6) ?
C8 H8A . 0.97 ?
C8 H8B . 0.97 ?
C9 C10 . 1.515(6) ?
C9 H9A . 0.97 ?
C9 H9B . 0.97 ?
C10 N2 . 1.460(5) y
C10 H10A . 0.97 ?
C10 H10B . 0.97 ?
N2 C11 . 1.273(5) y
C11 C12 . 1.447(5) ?
C11 H11 . 0.93 ?
C12 C13 . 1.398(5) ?
C12 C17 . 1.402(5) ?
C13 C14 . 1.363(6) ?
C13 H13 . 0.93 ?
C14 C15 . 1.394(6) ?
C14 Br2 . 1.892(4) y
C15 C16 . 1.370(7) ?
C15 H15 . 0.93 ?
C16 C17 . 1.371(6) ?
C16 H16 . 0.93 ?
C17 O2 . 1.341(5) y
O2 H2O . 0.86(5) ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 C1 C2 C3 -179.7(4)
C6 C1 C2 C3 -1.8(7)
C1 C2 C3 C4 1.9(7)
C2 C3 C4 C5 -1.2(6)
C2 C3 C4 Br1 176.5(3)
C3 C4 C5 C6 0.5(6)
Br1 C4 C5 C6 -177.3(3)
C4 C5 C6 C1 -0.4(6)
C4 C5 C6 C7 179.8(4)
O1 C1 C6 C5 178.9(4)
C2 C1 C6 C5 1.0(6)
O1 C1 C6 C7 -1.3(6)
C2 C1 C6 C7 -179.1(4)
C5 C6 C7 N1 -178.7(4)
C1 C6 C7 N1 1.5(7)
C6 C7 N1 C8 -179.3(4)
C7 N1 C8 C9 -115.7(5)
N1 C8 C9 C10 -174.9(4)
C8 C9 C10 N2 65.7(5)
C9 C10 N2 C11 139.8(4)
C10 N2 C11 C12 178.8(4)
N2 C11 C12 C13 -178.6(4)
N2 C11 C12 C17 -0.4(6)
C17 C12 C13 C14 1.6(6)
C11 C12 C13 C14 179.9(4)
C12 C13 C14 C15 -0.8(6)
C12 C13 C14 Br2 -178.8(3)
C13 C14 C15 C16 0.8(7)
Br2 C14 C15 C16 178.7(4)
C14 C15 C16 C17 -1.6(8)
C15 C16 C17 O2 -178.7(4)
C15 C16 C17 C12 2.4(7)
C13 C12 C17 O2 178.7(4)
C11 C12 C17 O2 0.4(6)
C13 C12 C17 C16 -2.3(6)
C11 C12 C17 C16 179.4(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652215
