#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:52:50 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179267 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/87/4318748.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_4318748
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 Cu N10 O11'
_chemical_formula_weight         646.05
_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                 107.58(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.476(3)
_cell_length_b                   9.4116(8)
_cell_length_c                   14.204(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11.00
_cell_measurement_theta_min      8.80
_cell_volume                     2482.0(7)
_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      293(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    0.0437
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2194
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 3
_diffrn_standards_interval_time  60
_exptl_absorpt_coefficient_mu    0.964
_exptl_absorpt_correction_T_max  0.6731
_exptl_absorpt_correction_T_min  0.6252
_exptl_absorpt_correction_type   'empirical used psi-scan'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.729
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1332
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.773
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0653P)²+2.0819P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1227
_reflns_number_gt                1571
_reflns_number_total             2194
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0112185_2.cif
_cod_data_source_block           ic7699
_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_database_code               4318748
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 -0.31752(7) 0.2500 0.0343(2) Uani 1 2 d S . .
O1 O 1.0000 -0.0796(6) 0.2500 0.091(2) Uani 1 2 d S . .
H1 H 0.967(2) -0.055(5) 0.220(4) 0.062(17) Uiso 1 1 d . . .
O2 O 1.04985(15) -0.0846(3) 0.0775(2) 0.0561(8) Uani 1 1 d . . .
H2 H 1.0354 -0.0739 0.1256 0.084 Uiso 1 1 calc R . .
O3 O 0.85486(18) -0.5882(3) 0.1242(2) 0.0623(8) Uani 1 1 d . . .
H3 H 0.8208 -0.6352 0.0907 0.093 Uiso 1 1 calc R . .
N1 N 1.09587(15) -0.3331(3) 0.2337(2) 0.0365(7) Uani 1 1 d . . .
N2 N 1.15825(15) -0.3753(3) 0.3012(2) 0.0350(7) Uani 1 1 d . . .
N3 N 0.95772(15) -0.3363(3) 0.1070(2) 0.0351(7) Uani 1 1 d . . .
N4 N 0.99059(15) -0.3043(3) 0.03757(19) 0.0358(7) Uani 1 1 d . . .
C1 C 1.2881(2) -0.4131(5) 0.3174(3) 0.0560(12) Uani 1 1 d . . .
H1A H 1.3013 -0.3774 0.3837 0.084 Uiso 1 1 calc R . .
H1B H 1.3212 -0.3781 0.2847 0.084 Uiso 1 1 calc R . .
H1C H 1.2894 -0.5150 0.3187 0.084 Uiso 1 1 calc R . .
C2 C 1.21388(18) -0.3646(4) 0.2630(3) 0.0384(9) Uani 1 1 d . . .
C3 C 1.18686(19) -0.3096(4) 0.1696(3) 0.0419(9) Uani 1 1 d . . .
H3A H 1.2124 -0.2886 0.1256 0.050 Uiso 1 1 calc R . .
C4 C 1.11369(19) -0.2920(4) 0.1545(3) 0.0370(8) Uani 1 1 d . . .
C5 C 1.05988(19) -0.2290(5) 0.0638(3) 0.0430(10) Uani 1 1 d . . .
H5A H 1.0797 -0.2386 0.0084 0.052 Uiso 1 1 calc R . .
C6 C 0.9661(2) -0.2964(5) -0.1450(3) 0.0501(11) Uani 1 1 d . . .
H6A H 1.0100 -0.3453 -0.1418 0.075 Uiso 1 1 calc R . .
H6B H 0.9730 -0.1960 -0.1498 0.075 Uiso 1 1 calc R . .
H6C H 0.9285 -0.3281 -0.2020 0.075 Uiso 1 1 calc R . .
C7 C 0.9455(2) -0.3273(4) -0.0541(2) 0.0369(8) Uani 1 1 d . . .
C8 C 0.8827(2) -0.3782(4) -0.0429(3) 0.0408(9) Uani 1 1 d . . .
H8A H 0.8418 -0.4051 -0.0931 0.049 Uiso 1 1 calc R . .
C9 C 0.89176(18) -0.3820(4) 0.0580(2) 0.0338(8) Uani 1 1 d . . .
C10 C 0.84023(19) -0.4431(4) 0.1057(3) 0.0414(9) Uani 1 1 d . . .
H10A H 0.7915 -0.4337 0.0598 0.050 Uiso 1 1 calc R . .
N5 N 0.83489(18) 0.0408(4) 0.0829(2) 0.0521(9) Uani 1 1 d . . .
O4 O 0.79568(16) 0.1309(4) 0.0282(2) 0.0627(8) Uani 1 1 d . . .
O5 O 0.8124(2) -0.0776(4) 0.0902(3) 0.0892(12) Uani 1 1 d . . .
O6 O 0.8953(2) 0.0785(5) 0.1325(3) 0.1060(16) 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'
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 171.40(18) 2_755 . ?
N1 Cu N3 89.89(12) 2_755 . ?
N1 Cu N3 89.33(12) . . ?
N1 Cu N3 89.33(12) 2_755 2_755 ?
N1 Cu N3 89.89(12) . 2_755 ?
N3 Cu N3 169.61(18) . 2_755 ?
N1 Cu O1 94.30(9) 2_755 . ?
N1 Cu O1 94.30(9) . . ?
N3 Cu O1 95.20(9) . . ?
N3 Cu O1 95.20(9) 2_755 . ?
C4 N1 N2 105.9(3) . . ?
C4 N1 Cu 125.5(2) . . ?
N2 N1 Cu 128.4(2) . . ?
C2 N2 N1 110.4(3) . . ?
C2 N2 C10 126.5(3) . 2_755 ?
N1 N2 C10 122.3(3) . 2_755 ?
C9 N3 N4 106.4(3) . . ?
C9 N3 Cu 127.5(2) . . ?
N4 N3 Cu 126.1(2) . . ?
C7 N4 N3 110.6(3) . . ?
C7 N4 C5 127.0(3) . . ?
N3 N4 C5 121.3(3) . . ?
N2 C2 C3 107.2(3) . . ?
N2 C2 C1 122.5(4) . . ?
C3 C2 C1 130.2(4) . . ?
C2 C3 C4 105.8(3) . . ?
N1 C4 C3 110.6(3) . . ?
N1 C4 C5 122.9(3) . . ?
C3 C4 C5 126.4(3) . . ?
O2 C5 N4 110.4(3) . . ?
O2 C5 C4 110.7(3) . . ?
N4 C5 C4 111.9(3) . . ?
N4 C7 C8 106.8(3) . . ?
N4 C7 C6 122.5(3) . . ?
C8 C7 C6 130.7(3) . . ?
C7 C8 C9 106.8(3) . . ?
N3 C9 C8 109.4(3) . . ?
N3 C9 C10 124.3(3) . . ?
C8 C9 C10 125.9(3) . . ?
O3 C10 N2 107.9(3) . 2_755 ?
O3 C10 C9 109.6(3) . . ?
N2 C10 C9 114.3(3) 2_755 . ?
O5 N5 O6 121.6(4) . . ?
O5 N5 O4 120.7(4) . . ?
O6 N5 O4 117.6(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 1.955(3) 2_755 ?
Cu N1 1.955(3) . ?
Cu N3 1.955(3) . ?
Cu N3 1.955(3) 2_755 ?
Cu O1 2.240(5) . ?
O2 C5 1.395(5) . ?
O3 C10 1.403(5) . ?
N1 C4 1.332(4) . ?
N1 N2 1.359(4) . ?
N2 C2 1.354(4) . ?
N2 C10 1.461(5) 2_755 ?
N3 C9 1.334(4) . ?
N3 N4 1.362(4) . ?
N4 C7 1.350(4) . ?
N4 C5 1.469(4) . ?
C1 C2 1.490(5) . ?
C2 C3 1.371(5) . ?
C3 C4 1.386(5) . ?
C4 C5 1.515(5) . ?
C6 C7 1.492(5) . ?
C7 C8 1.367(5) . ?
C8 C9 1.391(5) . ?
C9 C10 1.486(5) . ?
C10 N2 1.461(5) 2_755 ?
N5 O5 1.213(5) . ?
N5 O6 1.227(5) . ?
N5 O4 1.244(5) . ?
