#------------------------------------------------------------------------------
#$Date: 2019-11-25 00:57:18 +0200 (Mon, 25 Nov 2019) $
#$Revision: 239820 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/35/02/4350270.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_4350270
loop_
_publ_author_name
'Tesema, Yohannes T.'
'Pham, David M.'
'Franz, Katherine J.'
_publ_section_title
;
 Synthesis and characterization of copper(II) complexes of cysteinyldopa
 and benzothiazine model ligands related to pheomelanin.
;
_journal_issue                   16
_journal_name_full               'Inorganic chemistry'
_journal_page_first              6102
_journal_page_last               6104
_journal_paper_doi               10.1021/ic060262n
_journal_volume                  45
_journal_year                    2006
_chemical_formula_moiety         'C32 H44 Cu N2 O2 S2'
_chemical_formula_sum            'C32 H44 Cu N2 O2 S2'
_chemical_formula_weight         616.35
_chemical_name_common            '[Cu(zine)2]'
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 109.399(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.6592(7)
_cell_length_b                   8.9229(4)
_cell_length_c                   14.7668(8)
_cell_measurement_reflns_used    5385
_cell_measurement_temperature    174(2)
_cell_measurement_theta_max      27.11
_cell_measurement_theta_min      2.85
_cell_volume                     1573.31(15)
_computing_cell_refinement       SAINT
_computing_data_collection       'Apex II 1.0 Rev.27 (Bruker, 2004)'
_computing_data_reduction        'SAINT 7.12A (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL 5.1, XP (Sheldrick, 1994)'
_computing_publication_material  'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      174(2)
_diffrn_detector_area_resol_mean 0.75
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker KAPPA APEX II CCD'
_diffrn_measurement_method       'Area Detector'
_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    0.0571
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4096
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.857
_exptl_absorpt_correction_T_max  0.9747
_exptl_absorpt_correction_T_min  0.8680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS (Sheldrick, 2003)'
_exptl_crystal_colour            'Dark Brown '
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Football-shaped Plates'
_exptl_crystal_F_000             654
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         4096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0359
_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)+(0.0442P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0912
_reflns_number_gt                3086
_reflns_number_total             4096
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic060262nsi20060519_121754.cif
_cod_data_source_block           yt002
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1573.31(14)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4350270
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Cu1 Cu 0.0000 0.0000 0.0000 0.01887(11) Uani 1 2 d S
S1 S 0.05534(5) 0.32077(7) -0.25769(5) 0.02850(16) Uani 1 1 d .
O1 O 0.13577(13) -0.08371(16) -0.00417(11) 0.0214(4) Uani 1 1 d .
N1 N 0.01946(15) 0.14138(19) -0.09519(13) 0.0183(4) Uani 1 1 d .
C1 C 0.14612(18) 0.1787(2) -0.19146(16) 0.0184(5) Uani 1 1 d .
C2 C 0.11615(18) 0.1064(2) -0.11885(16) 0.0169(5) Uani 1 1 d .
C3 C 0.17273(18) -0.0204(2) -0.06873(16) 0.0182(5) Uani 1 1 d .
C4 C 0.26514(19) -0.0757(2) -0.09217(17) 0.0206(5) Uani 1 1 d .
C5 C 0.29314(19) 0.0002(2) -0.16271(16) 0.0214(5) Uani 1 1 d .
H5A H 0.3564 -0.0358 -0.1771 0.026 Uiso 1 1 calc R
C6 C 0.23770(18) 0.1247(2) -0.21507(16) 0.0191(5) Uani 1 1 d .
C7 C 0.0060(2) 0.3899(3) -0.16505(18) 0.0299(6) Uani 1 1 d .
H7A H 0.0673 0.4445 -0.1167 0.036 Uiso 1 1 calc R
H7B H -0.0561 0.4613 -0.1931 0.036 Uiso 1 1 calc R
C8 C -0.0335(2) 0.2656(3) -0.11749(16) 0.0251(5) Uani 1 1 d .
H8A H -0.1007 0.2788 -0.1031 0.030 Uiso 1 1 calc R
C9 C 0.3280(2) -0.2155(3) -0.04270(18) 0.0257(5) Uani 1 1 d .
C10 C 0.3762(2) -0.1891(3) 0.06575(18) 0.0355(6) Uani 1 1 d .
H10A H 0.4281 -0.1042 0.0788 0.053 Uiso 1 1 calc R
H10B H 0.4161 -0.2791 0.0972 0.053 Uiso 1 1 calc R
H10C H 0.3151 -0.1672 0.0907 0.053 Uiso 1 1 calc R
C11 C 0.2473(2) -0.3497(3) -0.0644(2) 0.0329(6) Uani 1 1 d .
H11A H 0.1876 -0.3313 -0.0372 0.049 Uiso 1 1 calc R
H11B H 0.2884 -0.4405 -0.0357 0.049 Uiso 1 1 calc R
H11C H 0.2144 -0.3628 -0.1340 0.049 Uiso 1 1 calc R
C12 C 0.4250(2) -0.2555(3) -0.0780(2) 0.0436(8) Uani 1 1 d .
H12A H 0.4797 -0.1736 -0.0627 0.065 Uiso 1 1 calc R
H12B H 0.3965 -0.2710 -0.1477 0.065 Uiso 1 1 calc R
H12C H 0.4611 -0.3475 -0.0463 0.065 Uiso 1 1 calc R
C13 C 0.2775(2) 0.1934(3) -0.29404(17) 0.0254(5) Uani 1 1 d .
C14 C 0.1843(2) 0.1834(3) -0.39204(17) 0.0355(6) Uani 1 1 d .
H14A H 0.1651 0.0780 -0.4080 0.053 Uiso 1 1 calc R
H14B H 0.2104 0.2285 -0.4413 0.053 Uiso 1 1 calc R
H14C H 0.1180 0.2373 -0.3893 0.053 Uiso 1 1 calc R
C15 C 0.3772(2) 0.1089(3) -0.30585(19) 0.0361(7) Uani 1 1 d .
H15A H 0.3570 0.0034 -0.3204 0.054 Uiso 1 1 calc R
H15B H 0.4411 0.1156 -0.2462 0.054 Uiso 1 1 calc R
H15C H 0.3974 0.1534 -0.3585 0.054 Uiso 1 1 calc R
C16 C 0.3138(2) 0.3569(3) -0.2700(2) 0.0407(7) Uani 1 1 d .
H16A H 0.3734 0.3613 -0.2075 0.061 Uiso 1 1 calc R
H16B H 0.2496 0.4163 -0.2677 0.061 Uiso 1 1 calc R
H16C H 0.3415 0.3976 -0.3195 0.061 Uiso 1 1 calc R
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'
S S 0.1246 0.1234 '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
O1 Cu1 O1 180.0 3 .
O1 Cu1 N1 84.22(7) 3 3
O1 Cu1 N1 95.79(7) . 3
O1 Cu1 N1 95.79(7) 3 .
O1 Cu1 N1 84.21(7) . .
N1 Cu1 N1 180.0 3 .
C1 S1 C7 98.73(11) . .
C3 O1 Cu1 113.45(13) . .
C8 N1 C2 123.33(19) . .
C8 N1 Cu1 124.09(15) . .
C2 N1 Cu1 111.07(13) . .
C6 C1 C2 119.1(2) . .
C6 C1 S1 123.16(16) . .
C2 C1 S1 117.32(16) . .
C1 C2 C3 123.30(19) . .
C1 C2 N1 124.16(19) . .
C3 C2 N1 112.18(18) . .
O1 C3 C2 118.82(19) . .
O1 C3 C4 123.23(19) . .
C2 C3 C4 117.93(19) . .
C5 C4 C3 117.0(2) . .
C5 C4 C9 122.4(2) . .
C3 C4 C9 120.58(19) . .
C4 C5 C6 126.6(2) . .
C4 C5 H5A 116.7 . .
C6 C5 H5A 116.7 . .
C1 C6 C5 116.04(19) . .
C1 C6 C13 123.8(2) . .
C5 C6 C13 120.17(19) . .
C8 C7 S1 111.17(16) . .
C8 C7 H7A 109.4 . .
S1 C7 H7A 109.4 . .
C8 C7 H7B 109.4 . .
S1 C7 H7B 109.4 . .
H7A C7 H7B 108.0 . .
N1 C8 C7 122.5(2) . .
N1 C8 H8A 118.7 . .
C7 C8 H8A 118.7 . .
C12 C9 C4 112.16(19) . .
C12 C9 C10 107.9(2) . .
C4 C9 C10 109.75(19) . .
C12 C9 C11 107.5(2) . .
C4 C9 C11 109.4(2) . .
C10 C9 C11 110.1(2) . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C9 C11 H11A 109.5 . .
C9 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C9 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C9 C12 H12A 109.5 . .
C9 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C9 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C15 C13 C14 105.6(2) . .
C15 C13 C16 107.5(2) . .
C14 C13 C16 110.5(2) . .
C15 C13 C6 112.30(19) . .
C14 C13 C6 110.37(19) . .
C16 C13 C6 110.51(19) . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C13 C16 H16A 109.5 . .
C13 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C13 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.8936(14) 3
Cu1 O1 1.8937(14) .
Cu1 N1 1.9640(17) 3
Cu1 N1 1.9641(17) .
S1 C1 1.771(2) .
S1 C7 1.791(2) .
O1 C3 1.320(2) .
N1 C8 1.281(3) .
N1 C2 1.415(3) .
C1 C6 1.402(3) .
C1 C2 1.407(3) .
C2 C3 1.411(3) .
C3 C4 1.414(3) .
C4 C5 1.383(3) .
C4 C9 1.528(3) .
C5 C6 1.402(3) .
C5 H5A 0.9500 .
C6 C13 1.542(3) .
C7 C8 1.486(3) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 H8A 0.9500 .
C9 C12 1.528(3) .
C9 C10 1.531(3) .
C9 C11 1.537(3) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C15 1.529(3) .
C13 C14 1.536(3) .
C13 C16 1.536(3) .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
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
_geom_torsion_site_symmetry_1
O1 Cu1 O1 C3 0(2) 3
N1 Cu1 O1 C3 175.66(14) 3
N1 Cu1 O1 C3 -4.33(14) .
O1 Cu1 N1 C8 15.76(19) 3
O1 Cu1 N1 C8 -164.24(19) .
N1 Cu1 N1 C8 149(2) 3
O1 Cu1 N1 C2 -177.89(14) 3
O1 Cu1 N1 C2 2.11(14) .
N1 Cu1 N1 C2 -44(2) 3
C7 S1 C1 C6 -155.3(2) .
C7 S1 C1 C2 32.06(19) .
C6 C1 C2 C3 -1.0(3) .
S1 C1 C2 C3 171.94(18) .
C6 C1 C2 N1 -173.68(19) .
S1 C1 C2 N1 -0.7(3) .
C8 N1 C2 C1 -19.8(3) .
Cu1 N1 C2 C1 173.71(17) .
C8 N1 C2 C3 166.8(2) .
Cu1 N1 C2 C3 0.3(2) .
Cu1 O1 C3 C2 5.9(3) .
Cu1 O1 C3 C4 -172.48(17) .
C1 C2 C3 O1 -177.54(19) .
N1 C2 C3 O1 -4.1(3) .
C1 C2 C3 C4 0.9(3) .
N1 C2 C3 C4 174.39(19) .
O1 C3 C4 C5 178.7(2) .
C2 C3 C4 C5 0.3(3) .
O1 C3 C4 C9 0.2(3) .
C2 C3 C4 C9 -178.2(2) .
C3 C4 C5 C6 -1.5(4) .
C9 C4 C5 C6 176.9(2) .
C2 C1 C6 C5 -0.1(3) .
S1 C1 C6 C5 -172.64(16) .
C2 C1 C6 C13 179.2(2) .
S1 C1 C6 C13 6.7(3) .
C4 C5 C6 C1 1.4(3) .
C4 C5 C6 C13 -178.0(2) .
C1 S1 C7 C8 -50.1(2) .
C2 N1 C8 C7 -4.2(4) .
Cu1 N1 C8 C7 160.53(18) .
S1 C7 C8 N1 42.3(3) .
C5 C4 C9 C12 1.9(3) .
C3 C4 C9 C12 -179.7(2) .
C5 C4 C9 C10 121.8(2) .
C3 C4 C9 C10 -59.9(3) .
C5 C4 C9 C11 -117.3(2) .
C3 C4 C9 C11 61.1(3) .
C1 C6 C13 C15 -178.4(2) .
C5 C6 C13 C15 0.9(3) .
C1 C6 C13 C14 -60.9(3) .
C5 C6 C13 C14 118.4(2) .
C1 C6 C13 C16 61.6(3) .
C5 C6 C13 C16 -119.0(2) .
