#------------------------------------------------------------------------------
#$Date: 2015-10-09 15:14:41 +0300 (Fri, 09 Oct 2015) $
#$Revision: 161929 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/64/7036421.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_7036421
loop_
_publ_author_name
'Maji, Ram Chandra'
'Bhandari, Anirban'
'Singh, Ravindra'
'Roy, Suprakash'
'Chatterjee, Sudip K.'
'Bowles, Faye L.'
'Ghiassi, Kamran B.'
'Maji, Milan'
'Olmstead, Marilyn M.'
'Patra, Apurba K.'
_publ_section_title
;
 Copper coordinated ligand thioether-S and NO2(-) oxidation: relevance to
 the CuM site of hydroxylases.
;
_journal_issue                   40
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              17587
_journal_page_last               17599
_journal_paper_doi               10.1039/c5dt02184g
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         'C15 H14 Cu N3 O2 S, Cl O4'
_chemical_formula_sum            'C15 H14 Cl Cu N3 O6 S'
_chemical_formula_weight         463.34
_chemical_name_common            4
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-05-21 deposited with the CCDC.
2015-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.540(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.8284(12)
_cell_length_b                   8.0746(11)
_cell_length_c                   12.3897(16)
_cell_measurement_reflns_used    9914
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      30.6
_cell_measurement_theta_min      2.34
_cell_volume                     871.0(2)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'Apex2 (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Apex II'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13792
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.655
_diffrn_reflns_theta_min         2.339
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.567
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2013)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.767
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             470
_exptl_crystal_size_max          0.374
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.035(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         5344
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0208
_refine_ls_R_factor_gt           0.0198
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0194P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0492
_refine_ls_wR_factor_ref         0.0496
_reflns_Friedel_coverage         0.879
_reflns_friedel_fraction_full    1.000
_reflns_friedel_fraction_max     1.000
_reflns_number_gt                5168
_reflns_number_total             5344
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5dt02184g2.cif
_cod_data_source_block           kbg22
_cod_depositor_comments
'Adding full bibliography for 7036418--7036421.cif.'
_cod_database_code               7036421
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.592
_shelx_estimated_absorpt_t_max   0.867
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cu1 Cu 0.37672(3) 0.86587(3) 0.63067(2) 0.01145(6) Uani 1 1 d . .
S1 S 0.10096(6) 0.67507(6) 0.50042(4) 0.01245(10) Uani 1 1 d . .
O1 O 0.65262(17) 0.60168(19) 0.46407(12) 0.0141(3) Uani 1 1 d . .
O2 O 0.15519(17) 0.81058(18) 0.58470(12) 0.0143(3) Uani 1 1 d . .
N1 N 0.5947(2) 0.8242(2) 0.70044(14) 0.0119(3) Uani 1 1 d . .
N2 N 0.44212(19) 0.7456(2) 0.50863(14) 0.0114(3) Uani 1 1 d . .
N3 N 0.3181(2) 0.9730(2) 0.76158(15) 0.0167(4) Uani 1 1 d . .
C1 C 0.6653(2) 0.8693(3) 0.80028(15) 0.0152(3) Uani 1 1 d . .
H1 H 0.6125 0.9386 0.8437 0.018 Uiso 1 1 calc R U
C2 C 0.8140(3) 0.8175(3) 0.84216(18) 0.0183(4) Uani 1 1 d . .
H2 H 0.8631 0.8542 0.9121 0.022 Uiso 1 1 calc R U
C3 C 0.8892(3) 0.7123(3) 0.78097(18) 0.0188(4) Uani 1 1 d . .
H3 H 0.9898 0.6739 0.8088 0.023 Uiso 1 1 calc R U
C4 C 0.8153(2) 0.6631(3) 0.67756(17) 0.0150(4) Uani 1 1 d . .
H4 H 0.8642 0.5902 0.6339 0.018 Uiso 1 1 calc R U
C5 C 0.6688(2) 0.7232(2) 0.64012(16) 0.0114(4) Uani 1 1 d . .
C6 C 0.5845(2) 0.6828(2) 0.52712(16) 0.0110(3) Uani 1 1 d . .
C7 C 0.3559(2) 0.7403(2) 0.40159(16) 0.0118(4) Uani 1 1 d . .
C8 C 0.4196(2) 0.7763(3) 0.30804(18) 0.0141(4) Uani 1 1 d . .
H8 H 0.5266 0.7975 0.3149 0.017 Uiso 1 1 calc R U
C9 C 0.3281(3) 0.7814(3) 0.20510(18) 0.0164(4) Uani 1 1 d . .
H9 H 0.3736 0.8046 0.1424 0.020 Uiso 1 1 calc R U
C10 C 0.1704(3) 0.7528(3) 0.19309(18) 0.0178(4) Uani 1 1 d . .
H10 H 0.1087 0.7566 0.1226 0.021 Uiso 1 1 calc R U
C11 C 0.1041(2) 0.7187(3) 0.28460(17) 0.0162(4) Uani 1 1 d . .
H11 H -0.0035 0.7010 0.2774 0.019 Uiso 1 1 calc R U
C12 C 0.1967(2) 0.7106(3) 0.38734(16) 0.0125(4) Uani 1 1 d . .
C13 C 0.1883(2) 0.4859(3) 0.55491(18) 0.0156(4) Uani 1 1 d . .
H13A H 0.1588 0.3958 0.5027 0.023 Uiso 1 1 calc R U
H13B H 0.1536 0.4601 0.6242 0.023 Uiso 1 1 calc R U
H13C H 0.3003 0.4983 0.5677 0.023 Uiso 1 1 calc R U
C14 C 0.2828(2) 1.0089(3) 0.84324(18) 0.0161(4) Uani 1 1 d . .
C15 C 0.2377(3) 1.0546(3) 0.94635(19) 0.0207(5) Uani 1 1 d . .
H15A H 0.1548 0.9816 0.9610 0.031 Uiso 1 1 calc R U
H15B H 0.2017 1.1696 0.9425 0.031 Uiso 1 1 calc R U
H15C H 0.3260 1.0436 1.0053 0.031 Uiso 1 1 calc R U
Cl1 Cl 0.31003(6) 0.52253(6) 0.88398(4) 0.01514(10) Uani 1 1 d . .
O3 O 0.3917(2) 0.5927(2) 0.80377(15) 0.0268(4) Uani 1 1 d . .
O4 O 0.1878(2) 0.4184(2) 0.82976(15) 0.0280(4) Uani 1 1 d . .
O5 O 0.2449(2) 0.6531(3) 0.94178(16) 0.0313(5) Uani 1 1 d . .
O6 O 0.4145(2) 0.4241(2) 0.96064(14) 0.0257(4) 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'
S S 0.1246 0.1234 '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_3
N2 Cu1 N3 175.46(8) .
N2 Cu1 O2 93.96(7) .
N3 Cu1 O2 87.39(7) .
N2 Cu1 N1 82.24(7) .
N3 Cu1 N1 94.75(7) .
O2 Cu1 N1 155.76(7) .
N2 Cu1 O1 92.30(7) 2_656
N3 Cu1 O1 92.00(7) 2_656
O2 Cu1 O1 91.03(6) 2_656
N1 Cu1 O1 112.97(6) 2_656
O2 S1 C12 106.64(9) .
O2 S1 C13 106.59(9) .
C12 S1 C13 101.74(10) .
C12 S1 Cu1 83.97(7) .
C13 S1 Cu1 88.61(7) .
C6 O1 Cu1 138.79(14) 2_646
S1 O2 Cu1 122.33(9) .
C1 N1 C5 118.90(18) .
C1 N1 Cu1 128.22(15) .
C5 N1 Cu1 112.48(14) .
C6 N2 C7 119.50(17) .
C6 N2 Cu1 116.30(14) .
C7 N2 Cu1 123.73(13) .
C14 N3 Cu1 168.80(19) .
N1 C1 C2 121.8(2) .
C2 C1 Cu1 152.83(16) .
N1 C1 H1 119.1 .
C2 C1 H1 119.1 .
Cu1 C1 H1 87.9 .
C3 C2 C1 119.3(2) .
C3 C2 H2 120.3 .
C1 C2 H2 120.3 .
C2 C3 C4 119.1(2) .
C2 C3 H3 120.5 .
C4 C3 H3 120.5 .
C5 C4 C3 118.4(2) .
C5 C4 H4 120.8 .
C3 C4 H4 120.8 .
N1 C5 C4 122.52(19) .
N1 C5 C6 115.86(17) .
C4 C5 C6 121.60(18) .
C4 C5 Cu1 162.93(15) .
C6 C5 Cu1 75.04(11) .
O1 C6 N2 128.87(19) .
O1 C6 C5 118.69(18) .
N2 C6 C5 112.43(17) .
O1 C6 Cu1 167.40(15) .
C5 C6 Cu1 73.91(11) .
N2 C6 Cu1 112.45(13) 2_646
C5 C6 Cu1 129.73(13) 2_646
Cu1 C6 Cu1 145.15(7) 2_646
C8 C7 C12 117.47(18) .
C8 C7 N2 122.78(18) .
C12 C7 N2 119.56(18) .
C8 C7 Cu1 138.18(14) .
C12 C7 Cu1 94.59(12) .
C9 C8 C7 120.8(2) .
C9 C8 H8 119.6 .
C7 C8 H8 119.6 .
C8 C9 C10 120.7(2) .
C8 C9 H9 119.7 .
C10 C9 H9 119.7 .
C11 C10 C9 119.6(2) .
C11 C10 H10 120.2 .
C9 C10 H10 120.2 .
C10 C11 C12 119.5(2) .
C10 C11 H11 120.3 .
C12 C11 H11 120.3 .
C11 C12 C7 121.87(19) .
C11 C12 S1 116.35(16) .
C7 C12 S1 121.64(15) .
C11 C12 Cu1 155.08(15) .
C7 C12 Cu1 61.08(11) .
S1 C12 Cu1 64.81(6) .
S1 C13 Cu1 61.00(6) .
S1 C13 H13A 109.5 .
Cu1 C13 H13A 151.6 .
S1 C13 H13B 109.5 .
Cu1 C13 H13B 98.8 .
H13A C13 H13B 109.5 .
S1 C13 H13C 109.5 .
Cu1 C13 H13C 56.8 .
H13A C13 H13C 109.5 .
H13B C13 H13C 109.5 .
N3 C14 C15 179.8(3) .
C15 C14 Cu1 172.98(17) .
C14 C15 H15A 109.5 .
C14 C15 H15B 109.5 .
H15A C15 H15B 109.5 .
C14 C15 H15C 109.5 .
H15A C15 H15C 109.5 .
H15B C15 H15C 109.5 .
O3 Cl1 O4 109.27(11) .
O3 Cl1 O5 109.95(12) .
O4 Cl1 O5 109.07(12) .
O3 Cl1 O6 109.42(11) .
O4 Cl1 O6 109.36(12) .
O5 Cl1 O6 109.75(12) .
Cl1 O3 Cu1 143.08(11) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N2 1.9625(17) .
Cu1 N3 1.9812(19) .
Cu1 O2 1.9948(15) .
Cu1 N1 2.0035(18) .
Cu1 O1 2.2292(15) 2_656
S1 O2 1.5334(16) .
S1 C12 1.775(2) .
S1 C13 1.792(2) .
O1 C6 1.248(2) .
O1 Cu1 2.2292(15) 2_646
N1 C1 1.340(3) .
N1 C5 1.346(3) .
N2 C6 1.340(2) .
N2 C7 1.416(3) .
N3 C14 1.144(3) .
C1 C2 1.394(3) .
C1 H1 0.9500 .
C2 C3 1.380(3) .
C2 H2 0.9500 .
C3 C4 1.396(3) .
C3 H3 0.9500 .
C4 C5 1.388(3) .
C4 H4 0.9500 .
C5 C6 1.508(3) .
C6 Cu1 3.273(2) 2_646
C7 C8 1.400(3) .
C7 C12 1.408(3) .
C8 C9 1.392(3) .
C8 H8 0.9500 .
C9 C10 1.395(3) .
C9 H9 0.9500 .
C10 C11 1.387(3) .
C10 H10 0.9500 .
C11 C12 1.396(3) .
C11 H11 0.9500 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 C15 1.448(3) .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
Cl1 O3 1.4374(18) .
Cl1 O4 1.4431(17) .
Cl1 O5 1.446(2) .
Cl1 O6 1.4471(17) .
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_4
C12 S1 O2 Cu1 -48.50(13) . .
C13 S1 O2 Cu1 59.60(13) . .
C5 N1 C1 C2 1.4(3) . .
Cu1 N1 C1 C2 173.59(16) . .
C5 N1 C1 Cu1 -172.2(3) . .
N1 C1 C2 C3 -2.2(3) . .
Cu1 C1 C2 C3 5.1(5) . .
C1 C2 C3 C4 1.3(3) . .
C2 C3 C4 C5 0.4(3) . .
C1 N1 C5 C4 0.4(3) . .
Cu1 N1 C5 C4 -173.01(16) . .
C1 N1 C5 C6 -177.82(18) . .
Cu1 N1 C5 C6 8.8(2) . .
C1 N1 C5 Cu1 173.4(2) . .
C3 C4 C5 N1 -1.2(3) . .
C3 C4 C5 C6 176.85(19) . .
C3 C4 C5 Cu1 -17.1(6) . .
Cu1 O1 C6 N2 -59.2(3) 2_646 .
Cu1 O1 C6 C5 122.26(19) 2_646 .
Cu1 O1 C6 Cu1 -58.3(8) 2_646 .
C7 N2 C6 O1 -7.9(3) . .
Cu1 N2 C6 O1 179.68(17) . .
C7 N2 C6 C5 170.70(17) . .
Cu1 N2 C6 C5 -1.7(2) . .
C7 N2 C6 Cu1 172.4(3) . .
C7 N2 C6 Cu1 -32.6(2) . 2_646
Cu1 N2 C6 Cu1 155.03(8) . 2_646
N1 C5 C6 O1 173.88(18) . .
C4 C5 C6 O1 -4.3(3) . .
Cu1 C5 C6 O1 179.88(19) . .
N1 C5 C6 N2 -4.9(2) . .
C4 C5 C6 N2 176.90(19) . .
Cu1 C5 C6 N2 1.10(14) . .
N1 C5 C6 Cu1 -6.00(14) . .
C4 C5 C6 Cu1 175.80(19) . .
N1 C5 C6 Cu1 -156.55(13) . 2_646
C4 C5 C6 Cu1 25.2(3) . 2_646
Cu1 C5 C6 Cu1 -150.56(13) . 2_646
C6 N2 C7 C8 -42.3(3) . .
Cu1 N2 C7 C8 129.46(18) . .
C6 N2 C7 C12 142.8(2) . .
Cu1 N2 C7 C12 -45.4(2) . .
C6 N2 C7 Cu1 -171.8(3) . .
C12 C7 C8 C9 -0.3(3) . .
N2 C7 C8 C9 -175.3(2) . .
Cu1 C7 C8 C9 -136.06(19) . .
C7 C8 C9 C10 0.8(3) . .
C8 C9 C10 C11 -0.1(3) . .
C9 C10 C11 C12 -1.1(3) . .
C10 C11 C12 C7 1.7(3) . .
C10 C11 C12 S1 177.41(18) . .
C10 C11 C12 Cu1 90.9(4) . .
C8 C7 C12 C11 -1.0(3) . .
N2 C7 C12 C11 174.17(19) . .
Cu1 C7 C12 C11 151.23(18) . .
C8 C7 C12 S1 -176.45(16) . .
N2 C7 C12 S1 -1.3(3) . .
Cu1 C7 C12 S1 -24.27(17) . .
C8 C7 C12 Cu1 -152.2(2) . .
N2 C7 C12 Cu1 22.94(13) . .
O2 S1 C12 C11 -128.13(16) . .
C13 S1 C12 C11 120.38(17) . .
Cu1 S1 C12 C11 -152.31(17) . .
O2 S1 C12 C7 47.61(19) . .
C13 S1 C12 C7 -63.89(19) . .
Cu1 S1 C12 C7 23.43(16) . .
O2 S1 C12 Cu1 24.18(7) . .
C13 S1 C12 Cu1 -87.32(8) . .
O2 S1 C13 Cu1 -27.99(6) . .
C12 S1 C13 Cu1 83.55(7) . .
O4 Cl1 O3 Cu1 78.5(2) . .
O5 Cl1 O3 Cu1 -41.1(2) . .
O6 Cl1 O3 Cu1 -161.74(16) . .
