#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:52:03 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179081 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/43/4304384.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_4304384
loop_
_publ_author_name
'Yohannes T. Tesema'
'David M. Pham'
'Katherine J. Franz'
_publ_contact_author_address
;
Department of Chemistry, Duke University, 
Box 90346, Durham, North Carolina 27708
;
_publ_contact_author_email       katherine.franz@duke.edu
_publ_contact_author_fax         '+1 919 660 1605'
_publ_contact_author_name        'Katherine J. Franz'
_publ_contact_author_phone       '+1 919 660 1541'
_publ_section_title
;
Counterions Influence Reactivity of Metal Ions with Cysteinyldopa Model
Compounds
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1087
_journal_page_last               1095
_journal_paper_doi               10.1021/ic701889w
_journal_volume                  47
_journal_year                    2008
_chemical_formula_moiety         'C32 H44 N2 Ni O2 S2'
_chemical_formula_sum            'C32 H44 N2 Ni O2 S2'
_chemical_formula_weight         611.52
_chemical_name_common            '[Ni(zine)2]'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_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                 108.518(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.6926(7)
_cell_length_b                   8.9361(5)
_cell_length_c                   14.6865(7)
_cell_measurement_reflns_used    6633
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.71
_cell_volume                     1579.53(15)
_computing_cell_refinement       SAINT
_computing_data_collection       'Apex II 2.0 Rev.2 (Bruker, 2005)'
_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      173(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3840
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         2.71
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS 1.5 (Sheldrick, 2004)'
_exptl_crystal_colour            'Dark Brown '
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plates
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3843
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0376
_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)+(0.0747P)²+0.2313P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1099
_reflns_number_gt                3228
_reflns_number_total             3843
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ic701889w-file002_4.cif
_cod_data_source_block           yt003
_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.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' 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      'P 21/c'
_cod_database_code               4304384
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.5000 0.0000 0.0000 0.01870(13) Uani 1 2 d S . .
S1 S 0.44703(6) -0.31554(8) 0.25725(5) 0.03153(19) Uani 1 1 d . . .
O1 O 0.36984(15) 0.0862(2) 0.00408(12) 0.0228(4) Uani 1 1 d . . .
N1 N 0.48124(17) -0.1377(2) 0.09034(14) 0.0204(5) Uani 1 1 d . . .
C1 C 0.3558(2) -0.1761(3) 0.19046(18) 0.0211(5) Uani 1 1 d . . .
C2 C 0.3863(2) -0.1031(3) 0.11764(17) 0.0179(5) Uani 1 1 d . . .
C3 C 0.3299(2) 0.0222(3) 0.06810(18) 0.0199(6) Uani 1 1 d . . .
C4 C 0.2368(2) 0.0768(3) 0.09053(18) 0.0227(6) Uani 1 1 d . . .
C5 C 0.2081(2) -0.0003(3) 0.1614(2) 0.0240(6) Uani 1 1 d . . .
H5A H 0.1445 0.0345 0.1759 0.029 Uiso 1 1 calc R . .
C6 C 0.2632(2) -0.1235(3) 0.21342(18) 0.0210(5) Uani 1 1 d . . .
C7 C 0.4990(3) -0.3838(3) 0.1646(2) 0.0345(7) Uani 1 1 d . . .
H7A H 0.5626 -0.4514 0.1934 0.041 Uiso 1 1 calc R . .
H7B H 0.4401 -0.4425 0.1177 0.041 Uiso 1 1 calc R . .
C8 C 0.5351(2) -0.2603(3) 0.11345(18) 0.0264(6) Uani 1 1 d . . .
H8A H 0.6012 -0.2730 0.0972 0.032 Uiso 1 1 calc R . .
C9 C 0.1744(3) 0.2166(3) 0.0411(2) 0.0311(7) Uani 1 1 d . . .
C10 C 0.1292(3) 0.1898(4) -0.0676(2) 0.0383(8) Uani 1 1 d . . .
H10A H 0.1911 0.1696 -0.0922 0.057 Uiso 1 1 calc R . .
H10B H 0.0888 0.2788 -0.0993 0.057 Uiso 1 1 calc R . .
H10C H 0.0787 0.1037 -0.0808 0.057 Uiso 1 1 calc R . .
C11 C 0.2541(3) 0.3513(3) 0.0637(2) 0.0376(8) Uani 1 1 d . . .
H11A H 0.3163 0.3319 0.0394 0.056 Uiso 1 1 calc R . .
H11B H 0.2825 0.3667 0.1334 0.056 Uiso 1 1 calc R . .
H11C H 0.2142 0.4411 0.0328 0.056 Uiso 1 1 calc R . .
C12 C 0.0756(3) 0.2550(4) 0.0761(3) 0.0493(10) Uani 1 1 d . . .
H12A H 0.1019 0.2674 0.1461 0.074 Uiso 1 1 calc R . .
H12B H 0.0209 0.1739 0.0588 0.074 Uiso 1 1 calc R . .
H12C H 0.0411 0.3483 0.0459 0.074 Uiso 1 1 calc R . .
C13 C 0.2227(2) -0.1931(3) 0.29265(19) 0.0275(6) Uani 1 1 d . . .
C14 C 0.1214(3) -0.1104(4) 0.3033(2) 0.0375(8) Uani 1 1 d . . .
H14A H 0.0590 -0.1199 0.2437 0.056 Uiso 1 1 calc R . .
H14B H 0.1396 -0.0044 0.3165 0.056 Uiso 1 1 calc R . .
H14C H 0.1009 -0.1542 0.3565 0.056 Uiso 1 1 calc R . .
C15 C 0.3132(3) -0.1833(4) 0.3912(2) 0.0396(8) Uani 1 1 d . . .
H15A H 0.3328 -0.0782 0.4068 0.059 Uiso 1 1 calc R . .
H15B H 0.3791 -0.2385 0.3892 0.059 Uiso 1 1 calc R . .
H15C H 0.2853 -0.2270 0.4403 0.059 Uiso 1 1 calc R . .
C16 C 0.1878(3) -0.3573(4) 0.2684(3) 0.0454(9) Uani 1 1 d . . .
H16A H 0.1278 -0.3617 0.2069 0.068 Uiso 1 1 calc R . .
H16B H 0.1620 -0.3997 0.3190 0.068 Uiso 1 1 calc R . .
H16C H 0.2517 -0.4149 0.2637 0.068 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'
Ni Ni 0.3393 1.1124 '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
O1 Ni1 O1 180.00(11) 3_655 . ?
O1 Ni1 N1 86.25(8) 3_655 3_655 ?
O1 Ni1 N1 93.75(8) . 3_655 ?
O1 Ni1 N1 93.75(8) 3_655 . ?
O1 Ni1 N1 86.25(8) . . ?
N1 Ni1 N1 180.00(15) 3_655 . ?
C1 S1 C7 98.72(13) . . ?
C3 O1 Ni1 112.99(16) . . ?
C8 N1 C2 122.8(2) . . ?
C8 N1 Ni1 124.86(17) . . ?
C2 N1 Ni1 111.48(16) . . ?
C6 C1 C2 118.7(2) . . ?
C6 C1 S1 123.56(19) . . ?
C2 C1 S1 117.26(19) . . ?
C3 C2 C1 123.1(2) . . ?
C3 C2 N1 111.5(2) . . ?
C1 C2 N1 125.2(2) . . ?
O1 C3 C2 117.6(2) . . ?
O1 C3 C4 123.5(2) . . ?
C2 C3 C4 118.9(2) . . ?
C5 C4 C3 116.2(2) . . ?
C5 C4 C9 122.6(2) . . ?
C3 C4 C9 121.1(2) . . ?
C4 C5 C6 126.6(2) . . ?
C4 C5 H5A 116.7 . . ?
C6 C5 H5A 116.7 . . ?
C5 C6 C1 116.5(2) . . ?
C5 C6 C13 120.0(2) . . ?
C1 C6 C13 123.5(2) . . ?
C8 C7 S1 112.12(19) . . ?
C8 C7 H7A 109.2 . . ?
S1 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
S1 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N1 C8 C7 123.1(2) . . ?
N1 C8 H8A 118.5 . . ?
C7 C8 H8A 118.5 . . ?
C4 C9 C10 109.4(2) . . ?
C4 C9 C12 112.2(2) . . ?
C10 C9 C12 107.9(3) . . ?
C4 C9 C11 109.2(3) . . ?
C10 C9 C11 110.4(2) . . ?
C12 C9 C11 107.6(3) . . ?
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 . . ?
C14 C13 C15 106.1(2) . . ?
C14 C13 C16 107.1(2) . . ?
C15 C13 C16 110.2(3) . . ?
C14 C13 C6 112.0(2) . . ?
C15 C13 C6 110.9(2) . . ?
C16 C13 C6 110.4(2) . . ?
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
_geom_bond_publ_flag
Ni1 O1 1.8408(17) 3_655 ?
Ni1 O1 1.8408(17) . ?
Ni1 N1 1.8792(19) 3_655 ?
Ni1 N1 1.8792(19) . ?
S1 C1 1.770(3) . ?
S1 C7 1.797(3) . ?
O1 C3 1.331(3) . ?
N1 C8 1.279(3) . ?
N1 C2 1.419(3) . ?
C1 C6 1.403(3) . ?
C1 C2 1.408(3) . ?
C2 C3 1.402(4) . ?
C3 C4 1.410(3) . ?
C4 C5 1.390(3) . ?
C4 C9 1.533(4) . ?
C5 C6 1.395(4) . ?
C5 H5A 0.9500 . ?
C6 C13 1.545(3) . ?
C7 C8 1.486(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9500 . ?
C9 C10 1.535(4) . ?
C9 C12 1.537(4) . ?
C9 C11 1.540(4) . ?
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 C14 1.532(4) . ?
C13 C15 1.538(4) . ?
C13 C16 1.542(4) . ?
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Ni1 O1 C3 34(76) 3_655 . . . ?
N1 Ni1 O1 C3 -176.36(18) 3_655 . . . ?
N1 Ni1 O1 C3 3.64(18) . . . . ?
O1 Ni1 N1 C8 -13.4(2) 3_655 . . . ?
O1 Ni1 N1 C8 166.6(2) . . . . ?
N1 Ni1 N1 C8 115(100) 3_655 . . . ?
O1 Ni1 N1 C2 177.12(17) 3_655 . . . ?
O1 Ni1 N1 C2 -2.88(17) . . . . ?
N1 Ni1 N1 C2 -54(100) 3_655 . . . ?
C7 S1 C1 C6 155.4(2) . . . . ?
C7 S1 C1 C2 -32.2(2) . . . . ?
C6 C1 C2 C3 1.4(4) . . . . ?
S1 C1 C2 C3 -171.3(2) . . . . ?
C6 C1 C2 N1 176.2(2) . . . . ?
S1 C1 C2 N1 3.4(4) . . . . ?
C8 N1 C2 C3 -168.1(2) . . . . ?
Ni1 N1 C2 C3 1.6(3) . . . . ?
C8 N1 C2 C1 16.6(4) . . . . ?
Ni1 N1 C2 C1 -173.6(2) . . . . ?
Ni1 O1 C3 C2 -3.7(3) . . . . ?
Ni1 O1 C3 C4 174.1(2) . . . . ?
C1 C2 C3 O1 176.7(2) . . . . ?
N1 C2 C3 O1 1.3(3) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
N1 C2 C3 C4 -176.6(2) . . . . ?
O1 C3 C4 C5 -177.9(2) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
O1 C3 C4 C9 0.1(4) . . . . ?
C2 C3 C4 C9 177.9(3) . . . . ?
C3 C4 C5 C6 1.4(4) . . . . ?
C9 C4 C5 C6 -176.6(3) . . . . ?
C4 C5 C6 C1 -1.2(4) . . . . ?
C4 C5 C6 C13 177.8(3) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
S1 C1 C6 C5 172.0(2) . . . . ?
C2 C1 C6 C13 -179.2(2) . . . . ?
S1 C1 C6 C13 -7.0(4) . . . . ?
C1 S1 C7 C8 48.4(3) . . . . ?
C2 N1 C8 C7 4.9(4) . . . . ?
Ni1 N1 C8 C7 -163.4(2) . . . . ?
S1 C7 C8 N1 -40.7(4) . . . . ?
C5 C4 C9 C10 -122.2(3) . . . . ?
C3 C4 C9 C10 59.9(4) . . . . ?
C5 C4 C9 C12 -2.4(4) . . . . ?
C3 C4 C9 C12 179.7(3) . . . . ?
C5 C4 C9 C11 116.8(3) . . . . ?
C3 C4 C9 C11 -61.1(3) . . . . ?
C5 C6 C13 C14 -0.2(4) . . . . ?
C1 C6 C13 C14 178.7(3) . . . . ?
C5 C6 C13 C15 -118.5(3) . . . . ?
C1 C6 C13 C15 60.4(3) . . . . ?
C5 C6 C13 C16 119.0(3) . . . . ?
C1 C6 C13 C16 -62.1(4) . . . . ?
