#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007315.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_2007315
loop_
_publ_author_name
'Thirumurugan, R.'
'Shanmuga Sundara Raj, S.'
'Shanmugam, G.'
'Fun, H.-K.'
'Chinnakali, K.'
'Chantrapromma, S.'
'Marappan, M.'
'Kandaswamy, M.'
_publ_section_title
;
 5,5'-Dibromo-2,2'-dihydroxy-3,3'-(piperazine-1,4-diyldimethylene)dibenzaldehyde
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              780
_journal_page_last               781
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C20 H20 Br2 N2 O4'
_chemical_formula_sum            'C20 H20 Br2 N2 O4'
_chemical_formula_weight         512.20
_chemical_name_systematic
;
5,5'-Dibromo-2,2'-dihydroxy-3,3'-(piperazine-1,4-diyldimethylene)
dibenzaldehyde
;
_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'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 111.39(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.825(2)
_cell_length_b                   16.518(2)
_cell_length_c                   7.368(2)
_cell_measurement_reflns_used    34
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.55
_cell_measurement_theta_min      5.24
_cell_volume                     1000.1(4)
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4 diffractometer'
_diffrn_measurement_method       '\q/2\q 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  0.025
_diffrn_reflns_av_sigmaI/netI    0.0489
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            3016
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.47
_diffrn_standards_decay_%        <3
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.082
_exptl_absorpt_correction_T_max  0.48
_exptl_absorpt_correction_T_min  0.37
_exptl_absorpt_correction_type   'empirical \y scans (Siemens, 1994)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_description       'rectangular block'
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.426
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.935
_refine_ls_goodness_of_fit_obs   1.028
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_restrained_S_obs      1.028
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_obs          0.034
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w=1/[\s^2^(Fo^2^)+(0.0456P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.098
_refine_ls_wR_factor_obs         0.0805
_reflns_number_observed          1458
_reflns_number_total             2304
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    cf1222.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_database_code               2007315
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_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br 0.0323(2) 0.0686(2) 0.0646(3) -0.0054(2) -0.00536(15) 0.0049(2)
N 0.0289(11) 0.0357(12) 0.0446(14) -0.0085(9) 0.0108(10) -0.0076(12)
O1 0.072(2) 0.0354(13) 0.074(2) -0.0055(12) 0.0141(13) 0.0016(12)
O2 0.0316(10) 0.0412(12) 0.0541(14) -0.0043(10) -0.0033(10) 0.0004(12)
C1 0.0234(12) 0.050(2) 0.045(2) -0.0034(13) 0.0059(12) 0.002(2)
C2 0.038(2) 0.040(2) 0.038(2) -0.0067(13) 0.0105(13) 0.0006(14)
C3 0.0324(13) 0.037(2) 0.040(2) -0.0040(12) 0.0109(13) 0.0013(13)
C4 0.0280(13) 0.039(2) 0.038(2) -0.0045(11) 0.0086(12) 0.0005(13)
C5 0.0291(13) 0.038(2) 0.047(2) -0.0039(11) 0.0140(13) 0.0006(13)
C6 0.0289(14) 0.037(2) 0.049(2) 0.0053(12) 0.0095(13) 0.0073(14)
C7 0.044(2) 0.045(2) 0.049(2) 0.0015(15) 0.009(2) 0.008(2)
C8 0.0314(15) 0.040(2) 0.065(2) -0.0021(13) 0.012(2) -0.001(2)
C9 0.041(2) 0.050(2) 0.045(2) -0.0157(15) 0.0046(14) -0.012(2)
C10 0.044(2) 0.056(2) 0.052(2) -0.014(2) 0.017(2) -0.017(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_occupancy
_atom_site_type_symbol
Br 0.34855(4) 0.19202(2) 0.05819(5) 0.0616(2) Uani d 1 Br
N -0.3465(3) 0.03300(15) -0.4854(4) 0.0371(5) Uani d 1 N
O1 -0.1376(3) 0.40214(14) -0.3496(4) 0.0643(7) Uani d 1 O
O2 -0.3255(2) 0.18691(15) -0.5518(3) 0.0476(6) Uani d 1 O
C1 0.1347(3) 0.1897(2) -0.1312(5) 0.0412(7) Uani d 1 C
C2 0.0541(4) 0.2603(2) -0.1952(5) 0.0398(7) Uani d 1 C
C3 -0.1033(3) 0.2597(2) -0.3340(4) 0.0372(7) Uani d 1 C
C4 -0.1759(3) 0.1854(2) -0.4100(4) 0.0359(6) Uani d 1 C
C5 -0.0941(3) 0.1130(2) -0.3419(4) 0.0380(7) Uani d 1 C
C6 0.0607(3) 0.1157(2) -0.2015(5) 0.0395(7) Uani d 1 C
C7 -0.1916(4) 0.3360(2) -0.3993(5) 0.0482(8) Uani d 1 C
C8 -0.1685(4) 0.0332(2) -0.4306(6) 0.0469(8) Uani d 1 C
C9 -0.3949(4) 0.0270(2) -0.3167(5) 0.0485(8) Uani d 1 C
C10 -0.4241(4) -0.0322(2) -0.6242(6) 0.0506(8) Uani d 1 C
H2 0.098(4) 0.3085(18) -0.147(5) 0.041(9) Uiso d 1 H
H6 0.101(3) 0.0717(18) -0.153(4) 0.030(8) Uiso d 1 H
H7 -0.279(5) 0.332(2) -0.476(6) 0.069(13) Uiso d 1 H
H8A -0.123(4) -0.002(2) -0.346(5) 0.039(9) Uiso d 1 H
H8B -0.149(4) 0.024(2) -0.556(5) 0.059(10) Uiso d 1 H
H9A -0.341(4) 0.070(2) -0.230(5) 0.055(9) Uiso d 1 H
H9B -0.357(4) -0.025(2) -0.248(4) 0.053(9) Uiso d 1 H
H10A -0.398(5) -0.022(2) -0.731(6) 0.070(12) Uiso d 1 H
H10B -0.381(3) -0.080(2) -0.563(4) 0.037(8) Uiso d 1 H
H1O2 -0.358(4) 0.142(2) -0.564(5) 0.041(10) 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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 N C10 . 109.7(2) yes
C9 N C8 . 112.4(3) yes
C10 N C8 . 111.8(2) yes
C2 C1 C6 . 120.6(3) ?
C2 C1 Br . 119.5(2) ?
C6 C1 Br . 119.9(2) ?
C1 C2 C3 . 120.3(3) ?
C2 C3 C4 . 119.2(3) ?
C2 C3 C7 . 120.2(3) ?
C4 C3 C7 . 120.6(3) ?
O2 C4 C5 . 121.7(3) ?
O2 C4 C3 . 117.9(3) ?
C5 C4 C3 . 120.4(2) ?
C6 C5 C4 . 118.9(3) ?
C6 C5 C8 . 120.5(3) ?
C4 C5 C8 . 120.5(3) ?
C5 C6 C1 . 120.6(3) ?
O1 C7 C3 . 125.4(3) yes
N C8 C5 . 111.9(3) ?
N C9 C10 3_454 111.2(3) ?
N C10 C9 3_454 109.7(3) ?
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
Br C1 . 1.895(3) yes
N C9 . 1.458(4) yes
N C10 . 1.471(4) yes
N C8 . 1.473(3) yes
O1 C7 . 1.195(4) yes
O2 C4 . 1.353(3) yes
C1 C2 . 1.358(4) yes
C1 C6 . 1.393(4) ?
C2 C3 . 1.392(4) ?
C3 C4 . 1.403(4) ?
C3 C7 . 1.467(4) yes
C4 C5 . 1.393(4) ?
C5 C6 . 1.381(4) ?
C5 C8 . 1.510(4) ?
C9 C10 3_454 1.497(4) yes
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_site_symmetry_4
_geom_torsion
C6 C1 C2 C3 . -0.8(5)
Br C1 C2 C3 . -179.9(2)
C1 C2 C3 C4 . -1.4(5)
C1 C2 C3 C7 . 178.5(3)
C2 C3 C4 O2 . -176.7(3)
C7 C3 C4 O2 . 3.4(4)
C2 C3 C4 C5 . 2.5(5)
C7 C3 C4 C5 . -177.4(3)
O2 C4 C5 C6 . 177.8(3)
C3 C4 C5 C6 . -1.3(5)
O2 C4 C5 C8 . 2.3(5)
C3 C4 C5 C8 . -176.9(3)
C4 C5 C6 C1 . -0.9(5)
C8 C5 C6 C1 . 174.6(3)
C2 C1 C6 C5 . 2.0(5)
Br C1 C6 C5 . -178.9(2)
C2 C3 C7 O1 . 3.5(6)
C4 C3 C7 O1 . -176.6(4)
C9 N C8 C5 . -74.0(4)
C10 N C8 C5 . 162.1(3)
C6 C5 C8 N . 148.5(3)
C4 C5 C8 N . -36.1(5)
C10 N C9 C10 3_454 -58.5(4)
C8 N C9 C10 3_454 176.4(3)
C9 N C10 C9 3_454 57.6(4)
C8 N C10 C9 3_454 -177.0(3)