#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/37/2223783.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_2223783
loop_
_publ_author_name
'Li, Li-Min'
'Jian, Fang-Fang'
'Li, Yu-Feng'
_publ_section_title
;
 Bis(hexamethylenetetramine)bis(trichloroacetato)copper(II)
;
_journal_coeditor_code           HB5145
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1469
_journal_paper_doi               10.1107/S1600536809043736
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Cu (C2 Cl3 O2)2 (C6 H12 N4)2]'
_chemical_formula_moiety         'C16 H24 Cl6 Cu N8 O4'
_chemical_formula_sum            'C16 H24 Cl6 Cu N8 O4'
_chemical_formula_weight         668.67
_chemical_name_systematic
;
Bis(hexamethylenetetramine)bis(trichloroacetato)copper(II)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 121.36(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.291(5)
_cell_length_b                   6.4759(13)
_cell_length_c                   20.702(4)
_cell_measurement_reflns_used    2740
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.31
_cell_volume                     2666.3(13)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 3
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_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  0.0225
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12444
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.31
_diffrn_standards_interval_count 0
_diffrn_standards_number         200
_exptl_absorpt_coefficient_mu    1.460
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1356
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.524
_refine_diff_density_min         -0.980
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3048
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.176
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0574
_refine_ls_shift/su_max          0.042
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1275P)²+3.9764P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1795
_refine_ls_wR_factor_ref         0.1842
_reflns_number_gt                2740
_reflns_number_total             3048
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5145.cif
_cod_data_source_block           I
_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 
;
_cod_original_cell_volume        2666.3(9)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2223783
_cod_database_fobs_code          2223783
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.0000 0.79415(8) 0.2500 0.0315(2) Uani d S 1 . .
O O1 0.06660(12) 0.7420(4) 0.35558(14) 0.0428(6) Uani d . 1 . .
O O2 0.01619(16) 0.4397(5) 0.33908(17) 0.0669(9) Uani d . 1 . .
N N1 0.07476(12) 0.8907(4) 0.23307(14) 0.0303(5) Uani d . 1 . .
N N2 0.15738(18) 1.1697(5) 0.2701(2) 0.0483(7) Uani d . 1 . .
N N3 0.10588(16) 1.0194(5) 0.14402(17) 0.0445(7) Uani d . 1 . .
N N4 0.18698(16) 0.8189(5) 0.2547(2) 0.0477(8) Uani d . 1 . .
C C1 0.10233(18) 1.0882(5) 0.27694(19) 0.0396(7) Uani d . 1 . .
H H1A 0.0667 1.1900 0.2584 0.047 Uiso calc R 1 . .
H H1B 0.1183 1.0629 0.3299 0.047 Uiso calc R 1 . .
C C2 0.1318(2) 1.2073(6) 0.1894(3) 0.0499(9) Uani d . 1 . .
H H2A 0.0962 1.3096 0.1704 0.060 Uiso calc R 1 . .
H H2B 0.1678 1.2629 0.1840 0.060 Uiso calc R 1 . .
C C3 0.1605(2) 0.8664(7) 0.1743(2) 0.0519(9) Uani d . 1 . .
H H3A 0.1967 0.9186 0.1687 0.062 Uiso calc R 1 . .
H H3B 0.1439 0.7402 0.1449 0.062 Uiso calc R 1 . .
C C4 0.13189(18) 0.7387(5) 0.2620(2) 0.0406(7) Uani d . 1 . .
H H4A 0.1485 0.7085 0.3147 0.049 Uiso calc R 1 . .
H H4B 0.1156 0.6108 0.2337 0.049 Uiso calc R 1 . .
C C5 0.21037(19) 1.0132(7) 0.2968(2) 0.0547(10) Uani d . 1 . .
H H5A 0.2277 0.9861 0.3500 0.066 Uiso calc R 1 . .
H H5B 0.2470 1.0670 0.2924 0.066 Uiso calc R 1 . .
C C6 0.05198(17) 0.9380(6) 0.15232(18) 0.0410(7) Uani d . 1 . .
H H6A 0.0346 0.8129 0.1225 0.049 Uiso calc R 1 . .
H H6B 0.0157 1.0379 0.1328 0.049 Uiso calc R 1 . .
C C7 0.1155(2) 0.5072(6) 0.45812(19) 0.0579(10) Uani d DU 1 . .
C C8 0.05989(16) 0.5630(6) 0.37587(17) 0.0378(7) Uani d . 1 A .
Cl Cl1 0.1084(2) 0.6786(5) 0.51998(15) 0.0872(9) Uani d PDU 0.749(7) A 1
Cl Cl2 0.1139(3) 0.2478(4) 0.48019(19) 0.1149(15) Uani d PDU 0.749(7) A 1
Cl Cl3 0.19694(13) 0.5452(9) 0.47005(18) 0.1191(16) Uani d PDU 0.749(7) A 1
Cl Cl1' 0.1398(7) 0.7198(12) 0.5194(5) 0.102(2) Uani d PDU 0.251(7) A -2
Cl Cl2' 0.0839(6) 0.2990(15) 0.4873(5) 0.106(2) Uani d PDU 0.251(7) A -2
Cl Cl3' 0.1851(4) 0.430(2) 0.4518(6) 0.133(3) Uani d PDU 0.251(7) A -2
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'
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
O1 Cu1 O1 . 2 159.95(17) y
O1 Cu1 N1 . 2 96.49(11) ?
O1 Cu1 N1 2 2 89.63(10) ?
O1 Cu1 N1 . . 89.63(10) y
O1 Cu1 N1 2 . 96.49(11) y
N1 Cu1 N1 2 . 144.38(14) y
C8 O1 Cu1 . . 111.6(2) ?
C6 N1 C4 . . 107.7(2) ?
C6 N1 C1 . . 107.0(3) ?
C4 N1 C1 . . 107.7(3) ?
C6 N1 Cu1 . . 114.51(19) ?
C4 N1 Cu1 . . 112.75(19) ?
C1 N1 Cu1 . . 106.88(18) ?
C1 N2 C5 . . 108.8(3) ?
C1 N2 C2 . . 108.3(3) ?
C5 N2 C2 . . 107.9(3) ?
C6 N3 C2 . . 108.7(3) ?
C6 N3 C3 . . 108.3(3) ?
C2 N3 C3 . . 108.1(3) ?
C4 N4 C5 . . 108.6(3) ?
C4 N4 C3 . . 108.4(3) ?
C5 N4 C3 . . 107.5(3) ?
N2 C1 N1 . . 111.6(3) ?
N2 C1 H1A . . 109.3 ?
N1 C1 H1A . . 109.3 ?
N2 C1 H1B . . 109.3 ?
N1 C1 H1B . . 109.3 ?
H1A C1 H1B . . 108.0 ?
N3 C2 N2 . . 112.3(3) ?
N3 C2 H2A . . 109.2 ?
N2 C2 H2A . . 109.2 ?
N3 C2 H2B . . 109.2 ?
N2 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
N3 C3 N4 . . 112.4(3) ?
N3 C3 H3A . . 109.1 ?
N4 C3 H3A . . 109.1 ?
N3 C3 H3B . . 109.1 ?
N4 C3 H3B . . 109.1 ?
H3A C3 H3B . . 107.8 ?
N4 C4 N1 . . 111.6(3) ?
N4 C4 H4A . . 109.3 ?
N1 C4 H4A . . 109.3 ?
N4 C4 H4B . . 109.3 ?
N1 C4 H4B . . 109.3 ?
H4A C4 H4B . . 108.0 ?
N2 C5 N4 . . 112.9(3) ?
N2 C5 H5A . . 109.0 ?
N4 C5 H5A . . 109.0 ?
N2 C5 H5B . . 109.0 ?
N4 C5 H5B . . 109.0 ?
H5A C5 H5B . . 107.8 ?
N3 C6 N1 . . 112.3(3) ?
N3 C6 H6A . . 109.1 ?
N1 C6 H6A . . 109.1 ?
N3 C6 H6B . . 109.1 ?
N1 C6 H6B . . 109.1 ?
H6A C6 H6B . . 107.9 ?
C8 C7 Cl2 . . 113.0(3) ?
C8 C7 Cl1' . . 112.4(4) ?
Cl2 C7 Cl1' . . 127.5(4) ?
C8 C7 Cl3' . . 105.0(4) ?
Cl2 C7 Cl3' . . 83.9(5) ?
Cl1' C7 Cl3' . . 108.3(5) ?
C8 C7 Cl1 . . 108.0(3) ?
Cl2 C7 Cl1 . . 113.0(3) ?
Cl1' C7 Cl1 . . 25.7(4) ?
Cl3' C7 Cl1 . . 131.9(4) ?
C8 C7 Cl2' . . 106.9(4) ?
Cl2 C7 Cl2' . . 27.9(4) ?
Cl1' C7 Cl2' . . 112.5(5) ?
Cl3' C7 Cl2' . . 111.6(5) ?
Cl1 C7 Cl2' . . 91.0(4) ?
C8 C7 Cl3 . . 109.7(3) ?
Cl2 C7 Cl3 . . 105.1(3) ?
Cl1' C7 Cl3 . . 82.7(5) ?
Cl3' C7 Cl3 . . 26.5(4) ?
Cl1 C7 Cl3 . . 107.8(3) ?
Cl2' C7 Cl3 . . 130.4(5) ?
O2 C8 O1 . . 127.3(3) ?
O2 C8 C7 . . 119.2(3) ?
O1 C8 C7 . . 113.5(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
Cu1 O1 . 1.941(3) y
Cu1 O1 2 1.941(3) ?
Cu1 N1 2 2.045(2) ?
Cu1 N1 . 2.045(2) y
O1 C8 . 1.270(4) ?
O2 C8 . 1.203(5) ?
N1 C6 . 1.499(4) ?
N1 C4 . 1.506(4) ?
N1 C1 . 1.505(4) ?
N2 C1 . 1.460(5) ?
N2 C5 . 1.465(6) ?
N2 C2 . 1.473(6) ?
N3 C6 . 1.452(4) ?
N3 C2 . 1.462(5) ?
N3 C3 . 1.470(5) ?
N4 C4 . 1.463(5) ?
N4 C5 . 1.465(6) ?
N4 C3 . 1.477(5) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 C8 . 1.553(5) ?
C7 Cl2 . 1.747(5) ?
C7 Cl1' . 1.754(7) ?
C7 Cl3' . 1.764(7) ?
C7 Cl1 . 1.766(5) ?
C7 Cl2' . 1.786(7) ?
C7 Cl3 . 1.797(5) ?
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
C1 H1A O2 2_565 0.97 2.52 3.416(5) 153
