#------------------------------------------------------------------------------
#$Date: 2016-03-23 23:42:23 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179512 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/09/4340916.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_4340916
loop_
_publ_author_name
'Mahmudov, Kamran T.'
'Kopylovich, Maximilian N.'
'Sabbatini, Alessandra'
'Drew, Michael G. B.'
'Martins, Luísa M D R S'
'Pettinari, Claudio'
'Pombeiro, Armando J. L.'
_publ_section_title
;
 Cooperative metal-ligand assisted E/Z isomerization and cyano activation
 at Cu(II) and Co(II) complexes of arylhydrazones of active methylene
 nitriles.
;
_journal_issue                   18
_journal_name_full               'Inorganic chemistry'
_journal_page_first              9946
_journal_page_last               9958
_journal_paper_doi               10.1021/ic501704g
_journal_volume                  53
_journal_year                    2014
_chemical_formula_sum            'C16 H13 Cu N5 O5 S'
_chemical_formula_weight         450.91
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 104.720(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.0286(7)
_cell_length_b                   8.1750(6)
_cell_length_c                   20.3318(14)
_cell_measurement_reflns_used    13201
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      3.21
_cell_volume                     1772.9(2)
_computing_cell_refinement       'Crysalis, Oxford Diffraction'
_computing_data_collection       'Crysalis, Oxford Diffraction'
_computing_data_reduction        'Crysalis, Oxford Diffraction'
_computing_molecular_graphics    PLATON(Spek,2004)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Oxford Diffaction X-Calibur System'
_diffrn_measurement_method       '321 frames, counting time 10 s.'
_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  0.1017
_diffrn_reflns_av_sigmaI/netI    0.1121
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            12301
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.21
_diffrn_standards_decay_%        n/a
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_number         n/a
_exptl_absorpt_coefficient_mu    1.391
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             916
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.939
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         5146
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.1241
_refine_ls_R_factor_gt           0.0585
_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)+(0.0353P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1364
_reflns_number_gt                2771
_reflns_number_total             5146
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic501704g_si_003.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 4340912--4340921.cif.'
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               4340916
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Cu1 Cu 0.25661(4) 0.03121(5) 0.19799(2) 0.03917(16) Uani 1 1 d .
N31 N 0.4138(3) -0.0319(3) 0.16768(16) 0.0393(7) Uani 1 1 d .
C32 C 0.5195(4) -0.0749(5) 0.2112(2) 0.0523(11) Uani 1 1 d .
H32 H 0.5260 -0.0623 0.2574 0.063 Uiso 1 1 calc R
C33 C 0.6209(4) -0.1378(6) 0.1913(2) 0.0614(12) Uani 1 1 d .
H33 H 0.6933 -0.1676 0.2238 0.074 Uiso 1 1 calc R
C34 C 0.6146(4) -0.1560(4) 0.1238(2) 0.0443(9) Uani 1 1 d .
C35 C 0.5042(4) -0.1157(6) 0.0784(2) 0.0684(14) Uani 1 1 d .
H35 H 0.4951 -0.1295 0.0320 0.082 Uiso 1 1 calc R
C36 C 0.4071(4) -0.0550(6) 0.1018(2) 0.0700(14) Uani 1 1 d .
H36 H 0.3327 -0.0285 0.0702 0.084 Uiso 1 1 calc R
C37 C 0.7215(4) -0.2221(5) 0.0979(2) 0.0513(10) Uani 1 1 d .
C39 C 0.8226(4) -0.3183(6) 0.1424(3) 0.0775(15) Uani 1 1 d .
H39C H 0.8487 -0.4031 0.1164 0.116 Uiso 1 1 calc R
H39A H 0.7925 -0.3664 0.1784 0.116 Uiso 1 1 calc R
H39B H 0.8924 -0.2480 0.1615 0.116 Uiso 1 1 calc R
O38 O 0.7221(3) -0.1968(5) 0.03977(18) 0.0889(11) Uani 1 1 d .
C15 C 0.1712(4) 0.0294(4) 0.3465(2) 0.0395(9) Uani 1 1 d .
C16 C 0.1502(4) -0.0253(5) 0.4079(2) 0.0533(11) Uani 1 1 d .
H16 H 0.2143 -0.0198 0.4477 0.064 Uiso 1 1 calc R
C17 C 0.0355(5) -0.0867(6) 0.4096(3) 0.0653(13) Uani 1 1 d .
H17 H 0.0213 -0.1213 0.4506 0.078 Uiso 1 1 calc R
C18 C -0.0579(4) -0.0971(6) 0.3510(2) 0.0654(13) Uani 1 1 d .
H18 H -0.1353 -0.1405 0.3522 0.079 Uiso 1 1 calc R
C19 C -0.0385(4) -0.0435(5) 0.2898(2) 0.0584(12) Uani 1 1 d .
H19 H -0.1033 -0.0503 0.2504 0.070 Uiso 1 1 calc R
C20 C 0.0767(4) 0.0202(4) 0.2867(2) 0.0401(9) Uani 1 1 d .
N22 N -0.0068(3) 0.1217(4) 0.18163(16) 0.0434(7) Uani 1 1 d .
C23 C -0.0164(3) 0.1654(5) 0.11833(19) 0.0427(9) Uani 1 1 d .
C24 C 0.0809(4) 0.1678(4) 0.0816(2) 0.0415(9) Uani 1 1 d .
N241 N 0.0544(3) 0.2178(4) 0.01807(16) 0.0538(9) Uani 1 1 d .
H24B H 0.1117 0.2185 -0.0038 0.065 Uiso 1 1 calc R
H24A H -0.0203 0.2498 -0.0016 0.065 Uiso 1 1 calc R
C231 C -0.1400(4) 0.2184(6) 0.0831(2) 0.0573(11) Uani 1 1 d .
N21 N 0.0982(3) 0.0743(3) 0.22352(16) 0.0393(7) Uani 1 1 d .
N232 N -0.2371(4) 0.2608(6) 0.0543(2) 0.0889(14) Uani 1 1 d .
O11 O 0.3549(2) 0.0021(3) 0.29229(14) 0.0506(7) Uani 1 1 d .
O14 O 0.4054(3) 0.0656(3) 0.41103(14) 0.0575(8) Uani 1 1 d .
O25 O 0.1904(2) 0.1216(3) 0.10965(14) 0.0525(7) Uani 1 1 d .
S12 S 0.32209(9) 0.10098(12) 0.34653(5) 0.0410(2) Uani 1 1 d .
O13 O 0.3119(3) 0.2692(3) 0.32731(18) 0.0680(9) 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'
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
O25 Cu1 O11 162.01(12) .
O25 Cu1 N21 91.47(12) .
O11 Cu1 N21 94.06(12) .
O25 Cu1 N31 88.00(12) .
O11 Cu1 N31 87.92(12) .
N21 Cu1 N31 175.01(12) .
O25 Cu1 O13 97.21(12) 2_545
O11 Cu1 O13 100.09(12) 2_545
N21 Cu1 O13 87.85(11) 2_545
N31 Cu1 O13 87.29(11) 2_545
C32 N31 C36 116.7(3) .
C32 N31 Cu1 122.5(3) .
C36 N31 Cu1 120.1(3) .
N31 C32 C33 123.1(4) .
C34 C33 C32 119.8(4) .
C33 C34 C35 117.4(4) .
C33 C34 C37 123.0(4) .
C35 C34 C37 119.5(4) .
C34 C35 C36 119.6(4) .
N31 C36 C35 123.3(4) .
O38 C37 C39 120.3(4) .
O38 C37 C34 118.8(4) .
C39 C37 C34 120.9(4) .
C20 C15 C16 120.5(4) .
C20 C15 S12 121.1(3) .
C16 C15 S12 118.4(3) .
C17 C16 C15 120.2(4) .
C18 C17 C16 119.8(4) .
C17 C18 C19 120.7(4) .
C18 C19 C20 120.7(4) .
C15 C20 C19 118.2(4) .
C15 C20 N21 120.7(3) .
C19 C20 N21 121.2(4) .
N21 N22 C23 123.8(3) .
N22 C23 C231 113.6(3) .
N22 C23 C24 128.3(3) .
C231 C23 C24 118.1(4) .
O25 C24 N241 119.2(4) .
O25 C24 C23 120.9(3) .
N241 C24 C23 119.9(3) .
N232 C231 C23 178.9(5) .
N22 N21 C20 110.7(3) .
N22 N21 Cu1 125.2(2) .
C20 N21 Cu1 122.6(2) .
S12 O11 Cu1 118.77(15) .
C24 O25 Cu1 129.6(3) .
O13 S12 O14 115.77(19) .
O13 S12 O11 109.79(18) .
O14 S12 O11 110.55(17) .
O13 S12 C15 108.11(17) .
O14 S12 C15 108.69(18) .
O11 S12 C15 103.13(17) .
S12 O13 Cu1 164.52(19) 2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O25 1.908(3) .
Cu1 O11 1.962(3) .
Cu1 N21 1.976(3) .
Cu1 N31 2.048(3) .
Cu1 O13 2.286(3) 2_545
N31 C32 1.319(5) .
N31 C36 1.336(5) .
C32 C33 1.382(5) .
C33 C34 1.365(5) .
C34 C35 1.367(5) .
C34 C37 1.509(5) .
C35 C36 1.370(5) .
C37 O38 1.201(5) .
C37 C39 1.472(6) .
C15 C20 1.387(5) .
C15 C16 1.400(5) .
C15 S12 1.764(4) .
C16 C17 1.370(6) .
C17 C18 1.365(6) .
C18 C19 1.387(6) .
C19 C20 1.390(5) .
C20 N21 1.434(5) .
N22 N21 1.310(4) .
N22 C23 1.314(5) .
C23 C231 1.437(5) .
C23 C24 1.454(5) .
C24 O25 1.255(4) .
C24 N241 1.316(4) .
C231 N232 1.135(5) .
O11 S12 1.484(3) .
O14 S12 1.426(3) .
S12 O13 1.427(3) .
O13 Cu1 2.286(3) 2
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
N241 H24B O38 0.86 2.15 2.994(4) 168.2 3_655
N241 H24A O14 0.86 2.32 2.959(4) 131.8 4_565
