#------------------------------------------------------------------------------
#$Date: 2015-10-09 15:14:41 +0300 (Fri, 09 Oct 2015) $
#$Revision: 161929 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/64/7036419.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_7036419
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         'C13 H11 Cu N3 O4 S'
_chemical_formula_sum            'C13 H11 Cu N3 O4 S'
_chemical_formula_weight         368.85
_chemical_name_common
'[2-methylsulfanyl phenyl]pyridine-2-carboxamide nitrate copper(II)'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-05-21 deposited with the CCDC.
2015-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.102(5)
_cell_length_b                   9.142(5)
_cell_length_c                   20.9440(12)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      30.593
_cell_measurement_theta_min      2.431
_cell_volume                     1359.8(12)
_computing_cell_refinement       'SAINT (Bruker, 2011)'
_computing_data_collection       'Apex2 (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2011)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Apex II'
_diffrn_measurement_method       'ω and φ'
_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  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            21518
_diffrn_reflns_theta_full        30.59
_diffrn_reflns_theta_max         30.59
_diffrn_reflns_theta_min         2.43
_exptl_absorpt_coefficient_mu    1.782
_exptl_absorpt_correction_T_max  0.836
_exptl_absorpt_correction_T_min  0.674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2007)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.802
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.018(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    conr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         4161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0164
_refine_ls_R_factor_gt           0.0158
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0227P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0422
_refine_ls_wR_factor_ref         0.0424
_reflns_number_gt                4042
_reflns_number_total             4161
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5dt02184g2.cif
_cod_data_source_block           fb54
_cod_depositor_comments
'Adding full bibliography for 7036418--7036421.cif.'
_cod_original_cell_volume        1359.9(12)
_cod_database_code               7036419
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cu1 Cu -0.21899(2) 0.427380(15) 1.049729(6) 0.01259(4) Uani 1 1 d .
N1 N -0.16681(14) 0.28705(11) 1.12182(5) 0.01279(19) Uani 1 1 d .
N2 N -0.13500(14) 0.26263(11) 0.99896(5) 0.01277(19) Uani 1 1 d .
N3 N -0.18393(16) 0.66261(11) 1.13242(5) 0.0163(2) Uani 1 1 d .
O1 O 0.02626(11) 0.04220(9) 1.00670(4) 0.01355(16) Uani 1 1 d .
O2 O -0.31081(12) 0.58743(9) 1.10207(4) 0.01684(17) Uani 1 1 d .
O3 O -0.23982(16) 0.76083(10) 1.16809(4) 0.0239(2) Uani 1 1 d .
O4 O -0.01570(14) 0.63182(12) 1.12477(5) 0.0254(2) Uani 1 1 d .
S1 S -0.02265(4) 0.55612(3) 0.971343(14) 0.01380(6) Uani 1 1 d .
C1 C -0.18978(17) 0.30755(13) 1.18420(6) 0.0150(2) Uani 1 1 d .
H1 H -0.2425 0.3972 1.1986 0.018 Uiso 1 1 calc R
C2 C -0.13939(17) 0.20247(15) 1.22912(6) 0.0177(2) Uani 1 1 d .
H2 H -0.1540 0.2207 1.2735 0.021 Uiso 1 1 calc R
C3 C -0.06751(16) 0.07080(16) 1.20756(6) 0.0171(2) Uani 1 1 d .
H3 H -0.0354 -0.0040 1.2371 0.021 Uiso 1 1 calc R
C4 C -0.04238(16) 0.04828(13) 1.14222(6) 0.0151(2) Uani 1 1 d .
H4 H 0.0075 -0.0413 1.1267 0.018 Uiso 1 1 calc R
C5 C -0.09180(16) 0.15929(13) 1.10066(6) 0.0124(2) Uani 1 1 d .
C6 C -0.06302(16) 0.14856(12) 1.02978(6) 0.0118(2) Uani 1 1 d .
C7 C -0.11840(16) 0.28251(13) 0.93257(6) 0.0123(2) Uani 1 1 d .
C8 C -0.15772(18) 0.17302(14) 0.88773(6) 0.0157(2) Uani 1 1 d .
H8 H -0.1897 0.0772 0.9015 0.019 Uiso 1 1 calc R
C9 C -0.14966(18) 0.20545(14) 0.82295(6) 0.0175(2) Uani 1 1 d .
H9 H -0.1789 0.1319 0.7925 0.021 Uiso 1 1 calc R
C10 C -0.09888(18) 0.34524(15) 0.80219(6) 0.0177(2) Uani 1 1 d .
H10 H -0.0917 0.3658 0.7578 0.021 Uiso 1 1 calc R
C11 C -0.05898(16) 0.45408(14) 0.84637(6) 0.0159(2) Uani 1 1 d .
H11 H -0.0226 0.5488 0.8323 0.019 Uiso 1 1 calc R
C12 C -0.07250(15) 0.42385(14) 0.91115(5) 0.0137(2) Uani 1 1 d .
C13 C -0.15659(19) 0.71401(13) 0.94564(7) 0.0196(2) Uani 1 1 d .
H13A H -0.1117 0.7459 0.9036 0.029 Uiso 1 1 calc R
H13B H -0.1404 0.7935 0.9765 0.029 Uiso 1 1 calc R
H13C H -0.2902 0.6880 0.9428 0.029 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
N2 Cu1 O2 177.71(4) . .
N2 Cu1 N1 81.93(5) . .
O2 Cu1 N1 96.81(5) . .
N2 Cu1 O1 93.28(4) . 4_457
O2 Cu1 O1 86.05(4) . 4_457
N1 Cu1 O1 129.81(4) . 4_457
N2 Cu1 S1 80.26(4) . .
O2 Cu1 S1 101.96(4) . .
N1 Cu1 S1 134.57(4) . .
O1 Cu1 S1 92.74(4) 4_457 .
N2 Cu1 C6 24.79(4) . .
O2 Cu1 C6 154.16(4) . .
N1 Cu1 C6 57.43(4) . .
O1 Cu1 C6 111.25(4) 4_457 .
S1 Cu1 C6 96.40(4) . .
C1 N1 C5 119.33(11) . .
C1 N1 Cu1 128.58(9) . .
C5 N1 Cu1 112.03(8) . .
C6 N2 C7 123.30(10) . .
C6 N2 Cu1 117.52(9) . .
C7 N2 Cu1 117.88(8) . .
O3 N3 O4 123.67(11) . .
O3 N3 O2 117.26(12) . .
O4 N3 O2 119.06(11) . .
C6 O1 Cu1 121.90(8) . 4_557
N3 O2 Cu1 116.23(8) . .
C12 S1 C13 103.07(7) . .
C12 S1 Cu1 92.00(5) . .
C13 S1 Cu1 106.42(6) . .
N1 C1 C2 122.37(12) . .
N1 C1 H1 118.8 . .
C2 C1 H1 118.8 . .
C3 C2 C1 118.36(12) . .
C3 C2 H2 120.8 . .
C1 C2 H2 120.8 . .
C2 C3 C4 119.72(12) . .
C2 C3 H3 120.1 . .
C4 C3 H3 120.1 . .
C5 C4 C3 118.48(12) . .
C5 C4 H4 120.8 . .
C3 C4 H4 120.8 . .
N1 C5 C4 121.70(11) . .
N1 C5 C6 115.60(10) . .
C4 C5 C6 122.68(11) . .
O1 C6 N2 127.90(12) . .
O1 C6 C5 119.94(10) . .
N2 C6 C5 112.12(10) . .
O1 C6 Cu1 163.18(8) . .
N2 C6 Cu1 37.70(6) . .
C5 C6 Cu1 74.94(6) . .
C8 C7 C12 119.27(11) . .
C8 C7 N2 123.61(11) . .
C12 C7 N2 116.96(10) . .
C9 C8 C7 119.60(12) . .
C9 C8 H8 120.2 . .
C7 C8 H8 120.2 . .
C8 C9 C10 120.63(12) . .
C8 C9 H9 119.7 . .
C10 C9 H9 119.7 . .
C11 C10 C9 120.05(12) . .
C11 C10 H10 120.0 . .
C9 C10 H10 120.0 . .
C10 C11 C12 119.66(12) . .
C10 C11 H11 120.2 . .
C12 C11 H11 120.2 . .
C11 C12 C7 120.72(11) . .
C11 C12 S1 122.86(10) . .
C7 C12 S1 116.35(9) . .
S1 C13 H13A 109.5 . .
S1 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
S1 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N2 1.9378(12) .
Cu1 O2 1.9411(11) .
Cu1 N1 2.0156(11) .
Cu1 O1 2.1789(13) 4_457
Cu1 S1 2.4546(7) .
Cu1 C6 2.8105(17) .
N1 C1 1.3301(16) .
N1 C5 1.3581(16) .
N2 C6 1.3286(16) .
N2 C7 1.4073(16) .
N3 O3 1.2336(14) .
N3 O4 1.2379(17) .
N3 O2 1.2994(14) .
O1 C6 1.2575(14) .
O1 Cu1 2.1790(13) 4_557
S1 C12 1.7823(13) .
S1 C13 1.8106(15) .
C1 C2 1.3914(18) .
C1 H1 0.9500 .
C2 C3 1.383(2) .
C2 H2 0.9500 .
C3 C4 1.3952(17) .
C3 H3 0.9500 .
C4 C5 1.3824(17) .
C4 H4 0.9500 .
C5 C6 1.5017(17) .
C7 C8 1.4007(17) .
C7 C12 1.4062(19) .
C8 C9 1.3898(18) .
C8 H8 0.9500 .
C9 C10 1.397(2) .
C9 H9 0.9500 .
C10 C11 1.3881(18) .
C10 H10 0.9500 .
C11 C12 1.3879(16) .
C11 H11 0.9500 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 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
N2 Cu1 N1 C1 -178.86(11) .
O2 Cu1 N1 C1 -0.79(11) .
O1 Cu1 N1 C1 -91.31(11) 4_457
S1 Cu1 N1 C1 113.44(10) .
C6 Cu1 N1 C1 177.11(12) .
N2 Cu1 N1 C5 3.94(8) .
O2 Cu1 N1 C5 -177.99(8) .
O1 Cu1 N1 C5 91.48(9) 4_457
S1 Cu1 N1 C5 -63.76(9) .
C6 Cu1 N1 C5 -0.09(7) .
O2 Cu1 N2 C6 -64.9(11) .
N1 Cu1 N2 C6 -8.12(9) .
O1 Cu1 N2 C6 -137.88(9) 4_457
S1 Cu1 N2 C6 129.91(9) .
O2 Cu1 N2 C7 127.7(10) .
N1 Cu1 N2 C7 -175.52(9) .
O1 Cu1 N2 C7 54.73(9) 4_457
S1 Cu1 N2 C7 -37.49(8) .
C6 Cu1 N2 C7 -167.40(15) .
O3 N3 O2 Cu1 -176.98(8) .
O4 N3 O2 Cu1 2.32(14) .
N2 Cu1 O2 N3 132.9(10) .
N1 Cu1 O2 N3 76.39(8) .
O1 Cu1 O2 N3 -153.97(8) 4_457
S1 Cu1 O2 N3 -62.00(8) .
C6 Cu1 O2 N3 72.33(12) .
N2 Cu1 S1 C12 30.54(5) .
O2 Cu1 S1 C12 -148.87(5) .
N1 Cu1 S1 C12 98.89(6) .
O1 Cu1 S1 C12 -62.33(5) 4_457
C6 Cu1 S1 C12 49.42(5) .
N2 Cu1 S1 C13 134.79(6) .
O2 Cu1 S1 C13 -44.61(6) .
N1 Cu1 S1 C13 -156.86(6) .
O1 Cu1 S1 C13 41.93(5) 4_457
C6 Cu1 S1 C13 153.67(5) .
C5 N1 C1 C2 0.07(18) .
Cu1 N1 C1 C2 -176.95(9) .
N1 C1 C2 C3 -1.72(19) .
C1 C2 C3 C4 1.83(18) .
C2 C3 C4 C5 -0.39(18) .
C1 N1 C5 C4 1.48(17) .
Cu1 N1 C5 C4 178.97(9) .
C1 N1 C5 C6 -177.33(10) .
Cu1 N1 C5 C6 0.16(13) .
C3 C4 C5 N1 -1.31(18) .
C3 C4 C5 C6 177.42(11) .
Cu1 O1 C6 N2 56.60(15) 4_557
Cu1 O1 C6 C5 -120.84(10) 4_557
Cu1 O1 C6 Cu1 29.5(3) 4_557
C7 N2 C6 O1 -0.90(19) .
Cu1 N2 C6 O1 -167.56(9) .
C7 N2 C6 C5 176.70(10) .
Cu1 N2 C6 C5 10.04(13) .
C7 N2 C6 Cu1 166.66(16) .
N1 C5 C6 O1 171.37(10) .
C4 C5 C6 O1 -7.43(17) .
N1 C5 C6 N2 -6.45(15) .
C4 C5 C6 N2 174.75(11) .
N1 C5 C6 Cu1 -0.11(9) .
C4 C5 C6 Cu1 -178.91(12) .
N2 Cu1 C6 O1 36.0(3) .
O2 Cu1 C6 O1 -148.8(3) .
N1 Cu1 C6 O1 -153.6(3) .
O1 Cu1 C6 O1 81.9(3) 4_457
S1 Cu1 C6 O1 -13.5(3) .
O2 Cu1 C6 N2 175.23(10) .
N1 Cu1 C6 N2 170.45(10) .
O1 Cu1 C6 N2 45.93(10) 4_457
S1 Cu1 C6 N2 -49.53(9) .
N2 Cu1 C6 C5 -170.37(12) .
O2 Cu1 C6 C5 4.86(12) .
N1 Cu1 C6 C5 0.08(6) .
O1 Cu1 C6 C5 -124.44(7) 4_457
S1 Cu1 C6 C5 140.10(6) .
C6 N2 C7 C8 48.37(18) .
Cu1 N2 C7 C8 -145.02(10) .
C6 N2 C7 C12 -136.24(12) .
Cu1 N2 C7 C12 30.37(14) .
C12 C7 C8 C9 0.39(18) .
N2 C7 C8 C9 175.67(11) .
C7 C8 C9 C10 1.36(19) .
C8 C9 C10 C11 -1.1(2) .
C9 C10 C11 C12 -0.94(19) .
C10 C11 C12 C7 2.71(18) .
C10 C11 C12 S1 179.59(9) .
C8 C7 C12 C11 -2.44(17) .
N2 C7 C12 C11 -178.03(11) .
C8 C7 C12 S1 -179.51(9) .
N2 C7 C12 S1 4.89(14) .
C13 S1 C12 C11 49.09(12) .
Cu1 S1 C12 C11 156.46(10) .
C13 S1 C12 C7 -133.90(10) .
Cu1 S1 C12 C7 -26.53(9) .
