#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:52:50 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179267 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/87/4318749.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4318749
loop_
_publ_author_name
'Sachindranath Paul'
'Anil Kumar Barik'
'Shie Ming Peng'
'Susanta Kumar Kar'
_publ_section_title
;
 Novel Copper(II) Induced Formation of a Porphyrinogen Derivative: X-ray
 Structural, Spectroscopic, and Electrochemical Studies of Porphyrinogen
 Complexes of Cu(II) and Co(III) Complex of a Trispyrazolyl Tripodal
 Ligand
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5803
_journal_page_last               5809
_journal_paper_doi               10.1021/ic0112185
_journal_volume                  41
_journal_year                    2002
_chemical_formula_sum            'C20 H26 Cl2 Cu N8 O13'
_chemical_formula_weight         720.93
_chemical_name_systematic
;
  ?
;
_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                 108.44(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.967(3)
_cell_length_b                   9.1563(18)
_cell_length_c                   14.858(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      10.18
_cell_measurement_theta_min      7.75
_cell_volume                     2706.0(11)
_computing_cell_refinement       'Enraf-Nonius CAD4'
_computing_data_collection       'Enraf-Nonius CAD4'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       'ω--2θ 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0482
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2385
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.088
_exptl_absorpt_correction_T_max  0.8187
_exptl_absorpt_correction_T_min  0.7322
_exptl_absorpt_correction_type   'empirical used psi-scan'
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.770
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1476
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2385
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0932P)²+1.2110P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1601
_reflns_number_gt                1523
_reflns_number_total             2385
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0112185_3.cif
_cod_data_source_block           ic7701
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z 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 
;
_cod_original_cell_volume        2706.0(10)
_cod_database_code               4318749
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 1.0000 0.68131(9) 0.7500 0.0415(3) Uani 1 2 d S . .
O1 O 1.0000 0.9366(6) 0.7500 0.0625(15) Uani 1 2 d S . .
H1 H 0.9719 0.9614 0.7297 0.07(2) Uiso 1 1 d R . .
O2 O 1.04095(19) 0.9257(4) 0.5842(3) 0.0595(10) Uani 1 1 d . . .
H2A H 1.0476 0.9428 0.6406 0.089 Uiso 1 1 calc R . .
O3 O 0.8707(3) 0.4063(4) 0.6404(3) 0.0940(16) Uani 1 1 d . . .
H3A H 0.8437 0.3509 0.6044 0.141 Uiso 1 1 calc R . .
N1 N 1.08782(18) 0.6692(4) 0.7328(3) 0.0452(9) Uani 1 1 d . . .
N2 N 1.14729(19) 0.6310(4) 0.7997(3) 0.0488(10) Uani 1 1 d . . .
N3 N 0.95878(19) 0.6658(4) 0.6130(3) 0.0457(10) Uani 1 1 d . . .
N4 N 0.98852(19) 0.6969(4) 0.5463(3) 0.0461(10) Uani 1 1 d . . .
C1 C 1.2701(3) 0.6124(9) 0.8223(5) 0.086(2) Uani 1 1 d . . .
H1B H 1.2708 0.5744 0.8829 0.130 Uiso 1 1 calc R . .
H1C H 1.2971 0.6991 0.8315 0.130 Uiso 1 1 calc R . .
H1D H 1.2877 0.5406 0.7894 0.130 Uiso 1 1 calc R . .
C2 C 1.1987(3) 0.6488(6) 0.7645(4) 0.0591(14) Uani 1 1 d . . .
C3 C 1.1722(3) 0.7063(6) 0.6752(4) 0.0593(14) Uani 1 1 d . . .
H3B H 1.1956 0.7332 0.6342 0.071 Uiso 1 1 calc R . .
C4 C 1.1034(2) 0.7164(5) 0.6583(4) 0.0471(12) Uani 1 1 d . . .
C5 C 1.0520(3) 0.7783(5) 0.5723(3) 0.0504(12) Uani 1 1 d . . .
H5A H 1.0701 0.7700 0.5192 0.060 Uiso 1 1 calc R . .
C6 C 0.9635(3) 0.7018(6) 0.3709(4) 0.0676(16) Uani 1 1 d . . .
H6A H 1.0082 0.7411 0.3877 0.101 Uiso 1 1 calc R . .
H6B H 0.9322 0.7714 0.3328 0.101 Uiso 1 1 calc R . .
H6C H 0.9613 0.6131 0.3356 0.101 Uiso 1 1 calc R . .
C7 C 0.9463(3) 0.6708(5) 0.4579(3) 0.0511(12) Uani 1 1 d . . .
C8 C 0.8888(3) 0.6157(6) 0.4692(3) 0.0567(14) Uani 1 1 d . . .
H8A H 0.8508 0.5845 0.4213 0.068 Uiso 1 1 calc R . .
C9 C 0.8978(2) 0.6151(5) 0.5660(3) 0.0486(12) Uani 1 1 d . . .
C10 C 0.8518(3) 0.5533(5) 0.6145(4) 0.0548(13) Uani 1 1 d . . .
H10A H 0.8058 0.5543 0.5702 0.066 Uiso 1 1 calc R . .
Cl Cl 1.16689(6) 1.02655(15) 0.91021(9) 0.0571(4) Uani 1 1 d . . .
O4 O 1.1347(3) 1.0459(9) 0.8133(4) 0.147(3) Uani 1 1 d . . .
O5 O 1.1160(3) 0.9918(8) 0.9467(5) 0.140(2) Uani 1 1 d . . .
O6 O 1.2007(3) 1.1464(7) 0.9547(6) 0.167(3) Uani 1 1 d . . .
O7 O 1.2117(3) 0.9082(7) 0.9243(5) 0.141(3) Uani 1 1 d . . .
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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu N1 173.4(2) 2_756 . ?
N1 Cu N3 89.09(16) 2_756 2_756 ?
N1 Cu N3 90.43(17) . 2_756 ?
N1 Cu N3 90.43(17) 2_756 . ?
N1 Cu N3 89.09(16) . . ?
N3 Cu N3 171.6(2) 2_756 . ?
N1 Cu O1 93.28(11) 2_756 . ?
N1 Cu O1 93.28(11) . . ?
N3 Cu O1 94.19(11) 2_756 . ?
N3 Cu O1 94.19(11) . . ?
C4 N1 N2 106.3(4) . . ?
C4 N1 Cu 126.0(3) . . ?
N2 N1 Cu 127.0(3) . . ?
C2 N2 N1 110.1(4) . . ?
C2 N2 C10 127.4(4) . 2_756 ?
N1 N2 C10 121.1(4) . 2_756 ?
C9 N3 N4 106.1(4) . . ?
C9 N3 Cu 127.4(4) . . ?
N4 N3 Cu 126.3(3) . . ?
C7 N4 N3 111.1(4) . . ?
C7 N4 C5 127.3(4) . . ?
N3 N4 C5 120.2(4) . . ?
N2 C2 C3 107.0(4) . . ?
N2 C2 C1 121.5(6) . . ?
C3 C2 C1 131.4(6) . . ?
C2 C3 C4 106.4(5) . . ?
N1 C4 C3 110.2(5) . . ?
N1 C4 C5 122.5(4) . . ?
C3 C4 C5 127.3(5) . . ?
O2 C5 N4 110.6(4) . . ?
O2 C5 C4 111.3(4) . . ?
N4 C5 C4 112.3(4) . . ?
N4 C7 C8 106.1(5) . . ?
N4 C7 C6 123.4(5) . . ?
C8 C7 C6 130.5(5) . . ?
C7 C8 C9 107.0(4) . . ?
N3 C9 C8 109.6(5) . . ?
N3 C9 C10 122.8(4) . . ?
C8 C9 C10 127.2(5) . . ?
O3 C10 N2 107.5(4) . 2_756 ?
O3 C10 C9 108.8(5) . . ?
N2 C10 C9 114.0(4) 2_756 . ?
O6 Cl O5 110.2(5) . . ?
O6 Cl O4 114.0(5) . . ?
O5 Cl O4 104.7(4) . . ?
O6 Cl O7 109.2(4) . . ?
O5 Cl O7 109.1(5) . . ?
O4 Cl O7 109.5(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu N1 1.941(4) 2_756 ?
Cu N1 1.941(4) . ?
Cu N3 1.949(4) 2_756 ?
Cu N3 1.949(4) . ?
Cu O1 2.338(5) . ?
O2 C5 1.391(6) . ?
O3 C10 1.421(6) . ?
N1 C4 1.322(6) . ?
N1 N2 1.371(5) . ?
N2 C2 1.348(7) . ?
N2 C10 1.455(6) 2_756 ?
N3 C9 1.330(6) . ?
N3 N4 1.357(6) . ?
N4 C7 1.354(6) . ?
N4 C5 1.467(6) . ?
C1 C2 1.509(7) . ?
C2 C3 1.371(8) . ?
C3 C4 1.386(7) . ?
C4 C5 1.498(7) . ?
C6 C7 1.475(8) . ?
C7 C8 1.366(8) . ?
C8 C9 1.390(7) . ?
C9 C10 1.487(7) . ?
C10 N2 1.455(6) 2_756 ?
Cl O6 1.359(6) . ?
Cl O5 1.378(5) . ?
Cl O4 1.395(5) . ?
Cl O7 1.407(5) . ?
