#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/61/2016154.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_2016154
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          511
_chemical_name_systematic
;
4,4',6,6'-tetrachloro-2,2'-(piperazin-1,4-diyldimethylene)diphenol
;
_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'
_cell_angle_alpha                90.0000
_cell_angle_beta                 111.972(13)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   7.4861(13)
_cell_length_b                   17.2008(13)
_cell_length_c                   8.0283(19)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      14.9
_cell_measurement_theta_min      14.6
_cell_volume                     958.7(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.017
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2364
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_standards_decay_%        0.11
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.68
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1528
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/[0.0024Fo² + 1σ(Fo²)]/(4Fo²)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1248
_reflns_number_gt                1526
_reflns_number_total             2215
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            gg3104.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2016154
_cod_database_fobs_code          2016154
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +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 -0.32583(9) 0.14991(5) 0.08772(10) 0.0630(2) Uani d . 1.00
Cl Cl2 0.06831(14) 0.40389(4) 0.41664(14) 0.0731(2) Uani d . 1.00
O O1 -0.0072(2) 0.06476(10) 0.3491(2) 0.0507(5) Uani d . 1.00
N N1 0.3760(2) 0.05530(11) 0.5370(2) 0.0368(5) Uani d . 1.00
C C1 0.0181(3) 0.14211(13) 0.3645(3) 0.0389(6) Uani d . 1.00
C C2 -0.1247(3) 0.19103(16) 0.2520(3) 0.0433(6) Uani d . 1.00
C C3 -0.1097(3) 0.27050(16) 0.2659(4) 0.0504(7) Uani d . 1.00
C C4 0.0514(4) 0.30339(15) 0.3944(4) 0.0487(7) Uani d . 1.00
C C5 0.1980(3) 0.25661(15) 0.5046(3) 0.0447(6) Uani d . 1.00
C C6 0.1833(3) 0.17638(14) 0.4917(3) 0.0377(6) Uani d . 1.00
C C7 0.3389(3) 0.12623(15) 0.6210(3) 0.0449(6) Uani d . 1.00
C C8 0.4707(3) 0.07261(14) 0.4110(3) 0.0408(6) Uani d . 1.00
C C9 0.5036(4) -0.00153(15) 0.3248(3) 0.0419(6) Uani d . 1.00
H H1 0.0971 0.0416 0.4073 0.057 Uiso d R 1.00
H H2 -0.2093 0.3026 0.1883 0.063 Uiso c R 1.00
H H3 0.3100 0.2798 0.5902 0.055 Uiso c R 1.00
H H4 0.3002 0.1116 0.7167 0.052 Uiso c R 1.00
H H5 0.4546 0.1555 0.6673 0.052 Uiso c R 1.00
H H6 0.3919 0.1070 0.3208 0.050 Uiso c R 1.00
H H7 0.5915 0.0966 0.4744 0.050 Uiso c R 1.00
H H8 0.3828 -0.0252 0.2601 0.050 Uiso c R 1.00
H H9 0.5666 0.0102 0.2448 0.050 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 . . 111.78(19) no
C7 N1 C9 . 3_656 110.15(19) no
C8 N1 C9 . 3_656 109.3(2) no
O1 C1 C2 . . 119.36(19) no
O1 C1 C6 . . 122.56(19) no
C2 C1 C6 . . 118.1(2) no
Cl1 C2 C1 . . 118.86(19) no
Cl1 C2 C3 . . 119.24(18) no
C1 C2 C3 . . 121.9(2) no
C2 C3 C4 . . 119.4(2) no
Cl2 C4 C3 . . 119.6(2) no
Cl2 C4 C5 . . 120.26(19) no
C3 C4 C5 . . 120.2(2) no
C4 C5 C6 . . 120.7(2) no
C1 C6 C5 . . 119.8(2) no
C1 C6 C7 . . 120.2(2) no
C5 C6 C7 . . 119.93(19) no
N1 C7 C6 . . 112.88(19) no
N1 C8 C9 . . 110.3(2) no
N1 C9 C8 3_656 . 110.1(2) no
C1 O1 H1 . . 110.3 no
C2 C3 H2 . . 120.4 no
C4 C3 H2 . . 120.2 no
C4 C5 H3 . . 119.5 no
C6 C5 H3 . . 119.8 no
N1 C7 H4 . . 108.6 no
N1 C7 H5 . . 108.6 no
C6 C7 H4 . . 108.5 no
C6 C7 H5 . . 108.8 no
H4 C7 H5 . . 109.5 no
N1 C8 H6 . . 109.2 no
N1 C8 H7 . . 109.1 no
C9 C8 H6 . . 109.7 no
C9 C8 H7 . . 109.0 no
H6 C8 H7 . . 109.5 no
N1 C9 H8 3_656 . 109.5 no
N1 C9 H9 3_656 . 109.0 no
C8 C9 H8 . . 109.1 no
C8 C9 H9 . . 109.7 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 . 1.738(2) no
Cl2 C4 . 1.738(2) no
O1 C1 . 1.343(2) no
N1 C7 . 1.470(3) no
N1 C8 . 1.467(4) no
N1 C9 3_656 1.466(3) no
C1 C2 . 1.395(3) no
C1 C6 . 1.405(2) no
C2 C3 . 1.373(3) no
C3 C4 . 1.381(3) no
C4 C5 . 1.381(3) no
C5 C6 . 1.385(3) no
C6 C7 . 1.508(3) no
C8 C9 . 1.514(3) no
O1 H1 . 0.845 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 O1 3.419(2) 2_555 ?
O1 Cl2 3.419(2) 2_545 ?
O1 O1 3.263(2) 3_556 ?
C2 C4 3.581(5) 4_554 no
C4 C2 3.581(5) 4_555 no
Cl1 H3 2.989 4_454 ?
Cl1 H4 3.302 1_454 ?
Cl1 H5 3.155 1_454 ?
Cl1 H6 3.387 1_455 ?
Cl1 H7 3.507 1_455 ?
Cl1 H8 3.419 3_555 ?
Cl1 H9 2.962 1_455 ?
Cl2 H1 3.391 2_555 ?
Cl2 H4 2.784 4_554 ?
Cl2 H6 3.248 4_555 ?
Cl2 H8 3.364 2_555 ?
Cl2 H8 3.556 4_555 ?
O1 H1 2.934 3_556 ?
O1 H7 3.549 1_455 ?
O1 H9 3.124 1_455 ?
C3 H5 3.309 4_454 ?
C3 H7 3.433 4_454 ?
C4 H4 3.103 4_554 ?
C5 H4 3.520 4_554 ?
C5 H6 3.361 4_555 ?
C7 H2 3.444 4_655 ?
C8 H2 3.362 4_655 ?
C8 H3 3.494 4_554 ?
H1 Cl2 3.391 2_545 ?
H1 O1 2.934 3_556 ?
H1 H1 2.827 3_556 ?
H2 C7 3.444 4_454 ?
H2 C8 3.362 4_454 ?
H2 H5 2.561 4_454 ?
H2 H7 2.502 4_454 ?
H2 H8 3.321 2_555 ?
H3 Cl1 2.989 4_655 ?
H3 C8 3.494 4_555 ?
H3 H4 3.510 4_554 ?
H3 H6 2.598 4_555 ?
H4 Cl1 3.302 1_656 ?
H4 Cl2 2.784 4_555 ?
H4 C4 3.103 4_555 ?
H4 C5 3.520 4_555 ?
H4 H3 3.510 4_555 ?
H5 Cl1 3.155 1_656 ?
H5 C3 3.309 4_655 ?
H5 H2 2.561 4_655 ?
H6 Cl1 3.387 1_655 ?
H6 Cl2 3.248 4_554 ?
H6 C5 3.361 4_554 ?
H6 H3 2.598 4_554 ?
H7 Cl1 3.507 1_655 ?
H7 O1 3.549 1_655 ?
H7 C3 3.433 4_655 ?
H7 H2 2.502 4_655 ?
H8 Cl1 3.419 3_555 ?
H8 Cl2 3.364 2_545 ?
H8 Cl2 3.556 4_554 ?
H8 H2 3.321 2_545 ?
H9 Cl1 2.962 1_655 ?
H9 O1 3.124 1_655 ?
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 . 0.845 1.968 2.700(2) 145 yes
C7 H4 Cl2 4_555 0.950 2.784 3.688(3) 159 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 . . . 177.8(2) yes
C1 C6 C7 N1 . . . 39.8(3) yes
C5 C6 C7 N1 . . . -143.7(2) yes
C4 C5 C6 C1 . . . 0.4(4) yes
C7 N1 C8 C9 . . . -179.06(17) ?
C8 N1 C7 C6 . . . 70.4(2) ?
C7 N1 C9 C8 . 3_656 3_656 178.2(2) ?
C9 N1 C7 C6 3_656 . . -167.8(2) ?
C8 N1 C9 C8 . 3_656 3_656 -58.6(2) ?
C9 N1 C8 C9 3_656 . . 58.7(2) ?
O1 C1 C2 Cl1 . . . -3.2(4) ?
O1 C1 C2 C3 . . . 177.7(3) ?
O1 C1 C6 C5 . . . -178.0(2) ?
O1 C1 C6 C7 . . . -1.5(4) ?
C2 C1 C6 C5 . . . 1.4(4) ?
C6 C1 C2 Cl1 . . . 177.5(2) ?
C6 C1 C2 C3 . . . -1.7(4) ?
Cl1 C2 C3 C4 . . . -178.9(2) ?
C1 C2 C3 C4 . . . 0.2(5) ?
C2 C3 C4 Cl2 . . . -178.3(2) ?
C2 C3 C4 C5 . . . 1.6(5) ?
Cl2 C4 C5 C6 . . . 178.0(2) ?
C3 C4 C5 C6 . . . -1.9(5) ?
C4 C5 C6 C7 . . . -176.1(3) ?
N1 C8 C9 N1 . . 3_656 -59.2(2) ?
