#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/61/2016155.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_2016155
loop_
_publ_author_name
'Kubono, Koji'
'Yokoi, Kunihiko'
_publ_section_title
;
 Monoclinic and orthorhombic polymorphs of
 4,4',6,6'-tetrachloro-2,2'-(piperazine-1,4-diyldimethylene)diphenol
;
_journal_coeditor_code           GG3104
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o535
_journal_page_last               o537
_journal_paper_doi               10.1107/S0108270107035408
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C18 H18 Cl4 N2 O2'
_chemical_formula_moiety         'C18 H18 Cl4 N2 O2 '
_chemical_formula_sum            'C18 H18 Cl4 N2 O2'
_chemical_formula_weight         436.14
_chemical_melting_point          512
_chemical_name_systematic
;
4,4',6,6'-tetrachloro-2,2'-(piperazin-1,4-diyldimethylene)diphenol
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   10.360(3)
_cell_length_b                   12.1910(17)
_cell_length_c                   15.332(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      17.5
_cell_measurement_theta_min      15.2
_cell_volume                     1936.4(9)
_computing_cell_refinement       WinAFC
_computing_data_collection       'WinAFC (Rigaku/MSC, 2006)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2006)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  CrystalStructure
_computing_structure_refinement  'CRYSTALS (Betteridge et al.,  2003)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3228
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_standards_decay_%        0.33
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.46
_refine_diff_density_min         -0.68
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1925
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[0.0016Fo² + 1σ(Fo²)]/(4Fo²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1060
_reflns_number_gt                1922
_reflns_number_total             2222
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            gg3104.cif
_cod_data_source_block           II
_cod_original_formula_sum        'C18 H18 Cl4 N2 O2 '
_cod_database_code               2016155
_cod_database_fobs_code          2016155
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,+Z
3 +X,-Y,1/2+Z
4 1/2-X,1/2-Y,1/2+Z
5 -X,-Y,-Z
6 1/2+X,1/2-Y,-Z
7 -X,+Y,1/2-Z
8 1/2+X,1/2+Y,1/2-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
Cl Cl1 0.67952(7) 0.32132(7) 0.74258(5) 0.0668(2) Uani d . 1.00
Cl Cl2 1.03086(9) 0.60741(6) 0.61907(6) 0.0763(3) Uani d . 1.00
O O1 0.85718(16) 0.15637(15) 0.67709(13) 0.0581(6) Uani d . 1.00
N N1 1.02653(18) 0.08975(15) 0.55792(14) 0.0392(6) Uani d . 1.00
C C1 0.8963(2) 0.2602(2) 0.65875(17) 0.0398(8) Uani d . 1.00
C C2 0.8225(2) 0.3481(2) 0.68730(16) 0.0427(8) Uani d . 1.00
C C3 0.8617(2) 0.4545(2) 0.67455(18) 0.0462(8) Uani d . 1.00
C C4 0.9758(2) 0.4732(2) 0.63139(17) 0.0454(8) Uani d . 1.00
C C5 1.0483(2) 0.3877(2) 0.59957(18) 0.0439(8) Uani d . 1.00
C C6 1.0107(2) 0.2803(2) 0.61378(17) 0.0381(7) Uani d . 1.00
C C7 1.0980(2) 0.1875(2) 0.58674(19) 0.0490(8) Uani d . 1.00
C C8 0.9626(2) 0.10652(19) 0.47390(18) 0.0457(8) Uani d . 1.00
C C9 0.8880(2) 0.00578(18) 0.44803(17) 0.0459(8) Uani d . 1.00
H H1 0.9009 0.1135 0.6455 0.070 Uiso d R 1.00
H H2 0.8110 0.5139 0.6954 0.055 Uiso c R 1.00
H H3 1.1243 0.4029 0.5671 0.053 Uiso c R 1.00
H H4 1.1494 0.1674 0.6355 0.059 Uiso c R 1.00
H H5 1.1522 0.2116 0.5406 0.059 Uiso c R 1.00
H H6 0.9074 0.1685 0.4779 0.055 Uiso c R 1.00
H H7 1.0261 0.1192 0.4304 0.055 Uiso c R 1.00
H H8 0.8251 -0.0073 0.4919 0.055 Uiso c R 1.00
H H9 0.8462 0.0161 0.3935 0.055 Uiso c R 1.00
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
Cl Cl 0.148 0.159
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, 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
_geom_angle_publ_flag
C7 N1 C8 . . 112.29(18) no
C7 N1 C9 . 5_756 110.98(18) no
C8 N1 C9 . 5_756 109.25(19) no
O1 C1 C2 . . 119.4(2) no
O1 C1 C6 . . 121.4(2) no
C2 C1 C6 . . 119.3(2) no
Cl1 C2 C1 . . 118.6(2) no
Cl1 C2 C3 . . 119.9(2) no
C1 C2 C3 . . 121.5(2) no
C2 C3 C4 . . 118.7(2) no
Cl2 C4 C3 . . 119.4(2) no
Cl2 C4 C5 . . 119.6(2) no
C3 C4 C5 . . 121.0(2) no
C4 C5 C6 . . 120.5(2) no
C1 C6 C5 . . 119.0(2) no
C1 C6 C7 . . 121.0(2) no
C5 C6 C7 . . 119.9(2) no
N1 C7 C6 . . 112.90(19) no
N1 C8 C9 . . 110.53(19) no
N1 C9 C8 5_756 . 110.76(19) no
C1 O1 H1 . . 107.3 no
C2 C3 H2 . . 121.0 no
C4 C3 H2 . . 121.0 no
C4 C5 H3 . . 119.0 no
C6 C5 H3 . . 120.0 no
N1 C7 H4 . . 108.0 no
N1 C7 H5 . . 109.0 no
C6 C7 H4 . . 108.0 no
C6 C7 H5 . . 109.0 no
H4 C7 H5 . . 110.0 no
N1 C8 H6 . . 109.0 no
N1 C8 H7 . . 109.0 no
C9 C8 H6 . . 111.0 no
C9 C8 H7 . . 108.0 no
H6 C8 H7 . . 109.0 no
N1 C9 H8 5_756 . 108.9 no
N1 C9 H9 5_756 . 109.0 no
C8 C9 H8 . . 107.7 no
C8 C9 H9 . . 111.0 no
H8 C9 H9 . . 109.5 no
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
Cl1 C2 . 1.737(2) no
Cl2 C4 . 1.743(2) no
O1 C1 . 1.358(3) no
N1 C7 . 1.470(3) no
N1 C8 . 1.463(3) no
N1 C9 5_756 1.466(2) no
C1 C2 . 1.387(3) no
C1 C6 . 1.393(3) no
C2 C3 . 1.373(3) no
C3 C4 . 1.374(4) no
C4 C5 . 1.375(3) no
C5 C6 . 1.383(3) no
C6 C7 . 1.507(3) no
C8 C9 . 1.504(3) no
O1 H1 . 0.844 no
C3 H2 . 0.950 no
C5 H3 . 0.950 no
C7 H4 . 0.950 no
C7 H5 . 0.950 no
C8 H6 . 0.950 no
C8 H7 . 0.950 no
C9 H8 . 0.950 no
C9 H9 . 0.950 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl2 C5 3.451(2) 5_766 ?
O1 C3 3.347(3) 2_645 ?
C1 C1 3.528(3) 7_756 no
C2 C5 3.564(3) 7_756 no
C3 O1 3.347(3) 2_655 ?
C3 C4 3.427(3) 7_756 no
C4 C3 3.427(3) 7_756 no
C5 Cl2 3.451(2) 5_766 ?
C5 C2 3.564(3) 7_756 no
Cl1 H4 3.190 7_756 ?
Cl1 H7 3.180 6_456 ?
Cl1 H9 3.058 4_655 ?
Cl2 H2 3.470 7_756 ?
Cl2 H3 3.280 5_766 ?
Cl2 H4 3.400 2_755 ?
Cl2 H6 3.180 5_766 ?
Cl2 H7 3.470 5_766 ?
O1 H2 2.480 2_645 ?
O1 H4 2.880 7_756 ?
C1 H4 3.380 7_756 ?
C2 H4 3.510 7_756 ?
C2 H7 3.580 6_456 ?
C3 H1 3.370 2_655 ?
C3 H8 3.435 2_655 ?
C4 H2 3.490 7_756 ?
C4 H3 3.550 5_766 ?
C5 H8 3.510 6_556 ?
C5 H9 3.304 6_556 ?
C8 H3 3.560 6_456 ?
C9 H3 2.960 6_456 ?
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 N1 . 0.844 1.892 2.660(2) 151 yes
C3 H2 O1 2_655 0.950 2.480 3.347(3) 152 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_1
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 C1 C6 C7 . . . 176.0(2) yes
C1 C6 C7 N1 . . . 38.0(3) yes
C5 C6 C7 N1 . . . -146.7(2) yes
C4 C5 C6 C1 . . . 1.8(3) yes
C7 N1 C8 C9 . . . -178.54(19) ?
C8 N1 C7 C6 . . . 70.7(2) ?
C7 N1 C9 C8 . 5_756 5_756 177.6(2) ?
C9 N1 C7 C6 5_756 . . -166.7(2) ?
C8 N1 C9 C8 . 5_756 5_756 -58.0(2) ?
C9 N1 C8 C9 5_756 . . 57.9(2) ?
O1 C1 C2 Cl1 . . . -2.1(3) ?
O1 C1 C2 C3 . . . 176.4(2) ?
O1 C1 C6 C5 . . . -177.7(2) ?
C2 C1 C6 C5 . . . 0.6(3) ?
C6 C1 C2 Cl1 . . . 179.55(19) ?
C6 C1 C2 C3 . . . -2.0(3) ?
Cl1 C2 C3 C4 . . . 179.4(2) ?
C1 C2 C3 C4 . . . 0.9(3) ?
C2 C3 C4 Cl2 . . . -177.0(2) ?
C2 C3 C4 C5 . . . 1.5(4) ?
Cl2 C4 C5 C6 . . . 175.6(2) ?
C3 C4 C5 C6 . . . -2.9(4) ?
C4 C5 C6 C7 . . . -173.7(2) ?
O1 C1 C6 C7 . . . -2.3(3) ?
N1 C8 C9 N1 . . 5_756 -58.8(2) ?
