#------------------------------------------------------------------------------
#$Date: 2016-03-25 10:13:15 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179744 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/40/7004089.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_7004089
loop_
_publ_author_name
'Bates, Gareth W.'
'Gale, Philip A.'
'Light, Mark E.'
'Ogden, Mark I.'
'Warriner, Colin N.'
_publ_section_title
;
 Structural diversity in the first metal complexes of
 2,5-dicarboxamidopyrroles and 2,5-dicarbothioamidopyrroles
;
_journal_issue                   31
_journal_name_full               'Dalton Transactions'
_journal_page_first              4106
_journal_page_last               4112
_journal_paper_doi               10.1039/b802506a
_journal_year                    2008
_chemical_formula_sum            'C28 H44 Cl4 Co N6 O6'
_chemical_formula_weight         761.42
_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                 124.112(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.3090(6)
_cell_length_b                   21.0300(14)
_cell_length_c                   13.4079(6)
_cell_measurement_reflns_used    3678
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     3573.9(3)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'CAMERON (Watkin, et al., 1993)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker-Nonius CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans to fill the asymmetric unit'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_sigmaI/netI    0.0522
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24246
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.826
_exptl_absorpt_correction_T_max  0.8521
_exptl_absorpt_correction_T_min  0.6727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;
_exptl_crystal_colour            Pink
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1588
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         4072
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0385
_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)+(0.0420P)²+3.1184P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0909
_reflns_number_gt                3005
_reflns_number_total             4072
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b802506a.txt
_cod_data_source_block           2006sot1194
_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 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7004089
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
C1 C -0.1137(2) 0.20667(19) 0.0696(3) 0.0577(10) Uani 1 1 d . . .
H1A H -0.1538 0.1894 -0.0124 0.086 Uiso 1 1 calc R . .
H1B H -0.1537 0.2413 0.0750 0.086 Uiso 1 1 calc R . .
H1C H -0.1015 0.1730 0.1267 0.086 Uiso 1 1 calc R . .
C2 C -0.00862(18) 0.23181(14) 0.0999(2) 0.0354(6) Uani 1 1 d . . .
H2A H 0.0311 0.2496 0.1825 0.042 Uiso 1 1 calc R . .
H2B H -0.0216 0.2668 0.0438 0.042 Uiso 1 1 calc R . .
C3 C 0.05912(16) 0.18056(12) 0.0923(2) 0.0254(5) Uani 1 1 d . . .
H3A H 0.0683 0.1440 0.1438 0.031 Uiso 1 1 calc R . .
H3B H 0.0228 0.1652 0.0082 0.031 Uiso 1 1 calc R . .
C4 C 0.16668(16) 0.20737(11) 0.13317(19) 0.0212(5) Uani 1 1 d . . .
H4A H 0.1567 0.2504 0.0983 0.025 Uiso 1 1 calc R . .
H4B H 0.2092 0.2120 0.2219 0.025 Uiso 1 1 calc R . .
C5 C 0.20937(15) 0.17430(10) -0.00862(18) 0.0164(4) Uani 1 1 d . . .
C10 C 0.54817(15) 0.08965(10) 0.09671(18) 0.0169(4) Uani 1 1 d . . .
C11 C 0.71566(16) 0.05644(12) 0.12607(19) 0.0248(5) Uani 1 1 d . . .
H11A H 0.7310 0.0226 0.1851 0.030 Uiso 1 1 calc R . .
H11B H 0.7550 0.0951 0.1710 0.030 Uiso 1 1 calc R . .
C12 C 0.75048(16) 0.03529(11) 0.04574(19) 0.0226(5) Uani 1 1 d . . .
H12A H 0.7360 0.0697 -0.0121 0.027 Uiso 1 1 calc R . .
H12B H 0.7089 -0.0024 -0.0010 0.027 Uiso 1 1 calc R . .
C13 C 0.86761(17) 0.01881(13) 0.1176(2) 0.0293(6) Uani 1 1 d . . .
H13A H 0.9090 0.0561 0.1665 0.035 Uiso 1 1 calc R . .
H13B H 0.8816 -0.0165 0.1735 0.035 Uiso 1 1 calc R . .
C14 C 0.9038(2) -0.00037(14) 0.0374(2) 0.0382(7) Uani 1 1 d . . .
H14A H 0.8623 -0.0369 -0.0122 0.057 Uiso 1 1 calc R . .
H14B H 0.9786 -0.0120 0.0874 0.057 Uiso 1 1 calc R . .
H14C H 0.8939 0.0353 -0.0150 0.057 Uiso 1 1 calc R . .
N1 N 0.22606(13) 0.16895(9) 0.09993(15) 0.0178(4) Uani 1 1 d . . .
H1 H 0.2736 0.1419 0.1523 0.021 Uiso 1 1 calc R . .
N3 N 0.60209(13) 0.06993(10) 0.05228(16) 0.0240(4) Uani 1 1 d . . .
H3 H 0.5677 0.0646 -0.0261 0.029 Uiso 1 1 calc R . .
O1 O 0.13456(10) 0.20612(7) -0.09104(12) 0.0207(3) Uani 1 1 d . . .
O2 O 0.59168(10) 0.09561(7) 0.20863(12) 0.0179(3) Uani 1 1 d . . .
O3 O 0.44266(12) 0.22805(8) 0.30328(14) 0.0205(3) Uani 1 1 d . . .
H98 H 0.502(2) 0.2499(14) 0.355(2) 0.041 Uiso 1 1 d . . .
H99 H 0.405(2) 0.2524(14) 0.238(3) 0.041 Uiso 1 1 d . . .
C6 C 0.28587(15) 0.14286(10) -0.02669(17) 0.0150(4) Uani 1 1 d . . .
C7 C 0.27031(15) 0.12475(10) -0.13610(18) 0.0183(5) Uani 1 1 d . . .
C8 C 0.36583(16) 0.10183(11) -0.11021(18) 0.0189(5) Uani 1 1 d . . .
C9 C 0.43671(15) 0.10582(10) 0.01505(17) 0.0168(4) Uani 1 1 d . . .
N2 N 0.38768(12) 0.13101(8) 0.06520(14) 0.0153(4) Uani 1 1 d . . .
Cl1 Cl 0.15577(4) 0.12719(3) -0.27848(4) 0.02749(15) Uani 1 1 d . . .
Cl2 Cl 0.38946(4) 0.07455(3) -0.21398(5) 0.02913(16) Uani 1 1 d . . .
Co1 Co 0.5000 0.149895(19) 0.2500 0.01458(12) Uani 1 2 d S . .
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'
Co Co 0.3494 0.9721 '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
C1 C2 C3 113.0(2) . . ?
C4 C3 C2 110.5(2) . . ?
N1 C4 C3 114.70(18) . . ?
O1 C5 N1 121.99(19) . . ?
O1 C5 C6 120.80(18) . . ?
N1 C5 C6 117.16(18) . . ?
O2 C10 N3 121.27(18) . . ?
O2 C10 C9 118.98(18) . . ?
N3 C10 C9 119.74(18) . . ?
N3 C11 C12 109.53(17) . . ?
C11 C12 C13 112.10(18) . . ?
C14 C13 C12 112.4(2) . . ?
C5 N1 C4 121.03(18) . . ?
C10 N3 C11 123.92(18) . . ?
C10 O2 Co1 112.41(12) . . ?
N2 C6 C7 109.51(18) . . ?
N2 C6 C5 122.91(18) . . ?
C7 C6 C5 127.46(18) . . ?
C8 C7 C6 107.24(17) . . ?
C8 C7 Cl1 124.27(16) . . ?
C6 C7 Cl1 128.48(16) . . ?
C7 C8 C9 106.18(18) . . ?
C7 C8 Cl2 125.74(15) . . ?
C9 C8 Cl2 128.08(16) . . ?
N2 C9 C8 110.10(17) . . ?
N2 C9 C10 117.09(17) . . ?
C8 C9 C10 132.79(19) . . ?
C6 N2 C9 106.97(16) . . ?
C6 N2 Co1 142.30(14) . . ?
C9 N2 Co1 109.85(12) . . ?
O2 Co1 O2 114.51(8) 2_655 . ?
O2 Co1 N2 89.01(6) 2_655 . ?
O2 Co1 N2 79.29(6) . . ?
O2 Co1 N2 79.29(6) 2_655 2_655 ?
O2 Co1 N2 89.01(6) . 2_655 ?
N2 Co1 N2 158.36(10) . 2_655 ?
O2 Co1 O3 82.61(6) 2_655 . ?
O2 Co1 O3 161.81(6) . . ?
N2 Co1 O3 108.39(6) . . ?
N2 Co1 O3 88.26(6) 2_655 . ?
O2 Co1 O3 161.81(6) 2_655 2_655 ?
O2 Co1 O3 82.61(6) . 2_655 ?
N2 Co1 O3 88.26(6) . 2_655 ?
N2 Co1 O3 108.39(6) 2_655 2_655 ?
O3 Co1 O3 81.20(8) . 2_655 ?
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
C1 C2 1.516(4) . ?
C2 C3 1.538(3) . ?
C3 C4 1.522(3) . ?
C4 N1 1.460(3) . ?
C5 O1 1.249(2) . ?
C5 N1 1.334(3) . ?
C5 C6 1.478(3) . ?
C10 O2 1.261(2) . ?
C10 N3 1.326(3) . ?
C10 C9 1.460(3) . ?
C11 N3 1.467(3) . ?
C11 C12 1.512(3) . ?
C12 C13 1.525(3) . ?
C13 C14 1.515(3) . ?
O2 Co1 2.1104(14) . ?
O3 Co1 2.1646(16) . ?
C6 N2 1.362(2) . ?
C6 C7 1.401(3) . ?
C7 C8 1.386(3) . ?
C7 Cl1 1.7225(19) . ?
C8 C9 1.400(3) . ?
C8 Cl2 1.721(2) . ?
C9 N2 1.365(3) . ?
N2 Co1 2.1155(16) . ?
Co1 O2 2.1104(14) 2_655 ?
Co1 N2 2.1155(16) 2_655 ?
Co1 O3 2.1646(16) 2_655 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.88 2.09 2.953(2) 167.1 2_655
N3 H3 Cl2 0.88 2.47 3.2119(18) 141.7 .
O3 H98 O1 0.90(3) 1.97(3) 2.808(2) 156(2) 8_556
O3 H99 O1 0.89(3) 1.92(3) 2.764(2) 158(2) 7
O3 H99 Cl1 0.89(3) 2.85(3) 3.3297(17) 115(2) 7
