#------------------------------------------------------------------------------
#$Date: 2016-03-23 23:42:23 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179512 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/09/4340915.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_4340915
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            'C30 H30 Cu N12 O12 S2'
_chemical_formula_weight         878.32
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.238(8)
_cell_angle_beta                 97.299(8)
_cell_angle_gamma                117.211(9)
_cell_formula_units_Z            1
_cell_length_a                   9.2685(9)
_cell_length_b                   10.0309(9)
_cell_length_c                   11.6641(10)
_cell_measurement_reflns_used    6483
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      3.14
_cell_volume                     910.66(18)
_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_publication_material  'SHELXL-97, PLATON'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device       'Oxford Diffaction X-Calibur System'
_diffrn_measurement_device_type  'CCD diffractometer'
_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  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0620
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6483
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.14
_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    0.794
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ABSPACK, Oxford Diffraction Ltd'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             451
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.860
_refine_diff_density_min         -0.791
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         5091
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0493
_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)+(0.0467P)²+0.3253P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1173
_reflns_number_gt                4080
_reflns_number_total             5091
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic501704g_si_008.cif
_cod_data_source_block           8
_cod_depositor_comments
'Adding full bibliography for 4340912--4340921.cif.'
_cod_original_cell_volume        910.66(14)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4340915
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.0000 0.0000 0.0000 0.01874(11) Uani 1 2 d S
S12 S -0.02318(8) 0.20942(7) -0.20498(5) 0.02432(14) Uani 1 1 d .
O11 O -0.0708(2) 0.0633(2) -0.17857(15) 0.0307(4) Uani 1 1 d .
O13 O 0.1496(3) 0.3266(3) -0.15410(19) 0.0615(8) Uani 1 1 d .
O14 O -0.1349(4) 0.2685(3) -0.17526(18) 0.0644(8) Uani 1 1 d .
C15 C -0.0602(3) 0.1613(3) -0.3650(2) 0.0220(5) Uani 1 1 d .
C16 C 0.0708(3) 0.2418(3) -0.4146(2) 0.0275(5) Uani 1 1 d .
H16 H 0.1742 0.3219 -0.3637 0.033 Uiso 1 1 calc R
C17 C 0.0481(4) 0.2034(3) -0.5393(2) 0.0322(6) Uani 1 1 d .
H17 H 0.1363 0.2566 -0.5720 0.039 Uiso 1 1 calc R
C18 C -0.1058(4) 0.0859(3) -0.6149(2) 0.0319(6) Uani 1 1 d .
H18 H -0.1208 0.0602 -0.6986 0.038 Uiso 1 1 calc R
C19 C -0.2380(4) 0.0061(3) -0.5676(2) 0.0281(5) Uani 1 1 d .
H19 H -0.3418 -0.0717 -0.6193 0.034 Uiso 1 1 calc R
C20 C -0.2156(3) 0.0420(3) -0.4423(2) 0.0217(5) Uani 1 1 d .
C23 C -0.6145(3) -0.2428(3) -0.4252(2) 0.0224(5) Uani 1 1 d .
C24 C -0.6209(3) -0.2159(3) -0.2968(2) 0.0227(5) Uani 1 1 d .
C32 C -0.1637(3) -0.3369(3) -0.1468(2) 0.0222(5) Uani 1 1 d .
H32 H -0.0605 -0.3150 -0.1623 0.027 Uiso 1 1 calc R
C33 C -0.2968(3) -0.4898(3) -0.1924(2) 0.0255(5) Uani 1 1 d .
H33 H -0.2827 -0.5702 -0.2359 0.031 Uiso 1 1 calc R
C34 C -0.4513(3) -0.5208(3) -0.1719(2) 0.0256(5) Uani 1 1 d .
H34 H -0.5433 -0.6222 -0.2033 0.031 Uiso 1 1 calc R
C35 C -0.4678(3) -0.3996(3) -0.1042(2) 0.0213(5) Uani 1 1 d .
H35 H -0.5706 -0.4179 -0.0897 0.026 Uiso 1 1 calc R
C36 C -0.3281(3) -0.2510(3) -0.05893(19) 0.0175(4) Uani 1 1 d .
C37 C -0.3216(3) -0.1108(3) 0.02251(19) 0.0172(4) Uani 1 1 d .
C231 C -0.7606(3) -0.3654(3) -0.5173(2) 0.0237(5) Uani 1 1 d .
N21 N -0.3482(3) -0.0424(2) -0.39324(17) 0.0232(4) Uani 1 1 d .
H21 H -0.3372 -0.0164 -0.3162 0.028 Uiso 1 1 calc R
N22 N -0.4883(3) -0.1610(2) -0.46718(17) 0.0237(4) Uani 1 1 d .
N25 N -0.7611(3) -0.3135(3) -0.27280(18) 0.0280(5) Uani 1 1 d .
H25A H -0.7687 -0.3019 -0.1990 0.034 Uiso 1 1 calc R
H25B H -0.8440 -0.3883 -0.3311 0.034 Uiso 1 1 calc R
N31 N -0.1789(2) -0.2196(2) -0.08114(16) 0.0177(4) Uani 1 1 d .
N38 N -0.4554(2) -0.1247(2) 0.05810(17) 0.0218(4) Uani 1 1 d .
H38A H -0.4506 -0.0452 0.1079 0.026 Uiso 1 1 calc R
H38B H -0.5478 -0.2134 0.0316 0.026 Uiso 1 1 calc R
N232 N -0.8805(3) -0.4635(3) -0.58823(19) 0.0311(5) Uani 1 1 d .
O24 O -0.4971(2) -0.1059(2) -0.21657(14) 0.0270(4) Uani 1 1 d .
O39 O -0.18411(19) 0.01666(18) 0.05906(14) 0.0204(3) Uani 1 1 d .
O1W O -0.1984(2) 0.3622(2) 0.03972(16) 0.0260(4) Uani 1 1 d D
H1 H -0.166(3) 0.339(3) -0.0219(19) 0.031 Uiso 1 1 d D
H2 H -0.164(4) 0.458(2) 0.065(2) 0.031 Uiso 1 1 d 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'
Cu Cu 0.3201 1.2651 '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'
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
N31 Cu1 N31 180.00(17) . 2
N31 Cu1 O39 97.56(7) . 2
N31 Cu1 O39 82.44(7) 2 2
N31 Cu1 O39 82.44(7) . .
N31 Cu1 O39 97.56(7) 2 .
O39 Cu1 O39 180.00(14) 2 .
N31 Cu1 O11 88.55(7) . .
N31 Cu1 O11 91.45(7) 2 .
O39 Cu1 O11 89.09(7) 2 .
O39 Cu1 O11 90.91(7) . .
N31 Cu1 O11 91.45(7) . 2
N31 Cu1 O11 88.55(7) 2 2
O39 Cu1 O11 90.91(7) 2 2
O39 Cu1 O11 89.09(7) . 2
O11 Cu1 O11 180.00(7) . 2
O13 S12 O11 114.71(13) . .
O13 S12 O14 112.26(18) . .
O11 S12 O14 111.03(14) . .
O13 S12 C15 107.36(12) . .
O11 S12 C15 105.54(11) . .
O14 S12 C15 105.18(12) . .
S12 O11 Cu1 133.36(11) . .
C16 C15 C20 119.4(2) . .
C16 C15 S12 118.9(2) . .
C20 C15 S12 121.70(17) . .
C17 C16 C15 120.4(3) . .
C18 C17 C16 119.8(2) . .
C17 C18 C19 120.7(2) . .
C18 C19 C20 119.9(3) . .
C19 C20 C15 119.7(2) . .
C19 C20 N21 120.3(2) . .
C15 C20 N21 120.0(2) . .
N22 C23 C231 114.1(2) . .
N22 C23 C24 126.8(2) . .
C231 C23 C24 119.0(2) . .
O24 C24 N25 122.9(2) . .
O24 C24 C23 119.5(2) . .
N25 C24 C23 117.5(2) . .
N31 C32 C33 122.0(2) . .
C34 C33 C32 118.7(2) . .
C33 C34 C35 119.5(2) . .
C36 C35 C34 118.5(2) . .
N31 C36 C35 122.3(2) . .
N31 C36 C37 112.56(19) . .
C35 C36 C37 125.1(2) . .
O39 C37 N38 122.0(2) . .
O39 C37 C36 118.08(19) . .
N38 C37 C36 119.82(19) . .
N232 C231 C23 177.7(3) . .
N22 N21 C20 118.77(19) . .
N21 N22 C23 120.7(2) . .
C32 N31 C36 119.1(2) . .
C32 N31 Cu1 127.27(16) . .
C36 N31 Cu1 113.53(15) . .
C37 O39 Cu1 113.38(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N31 1.9683(19) .
Cu1 N31 1.9683(19) 2
Cu1 O39 1.9812(16) 2
Cu1 O39 1.9812(16) .
Cu1 O11 2.4013(16) .
Cu1 O11 2.4013(16) 2
S12 O13 1.428(2) .
S12 O11 1.4397(17) .
S12 O14 1.452(2) .
S12 C15 1.771(2) .
C15 C16 1.393(3) .
C15 C20 1.399(3) .
C16 C17 1.385(4) .
C17 C18 1.380(4) .
C18 C19 1.382(4) .
C19 C20 1.393(3) .
C20 N21 1.410(3) .
C23 N22 1.311(3) .
C23 C231 1.431(3) .
C23 C24 1.479(3) .
C24 O24 1.241(3) .
C24 N25 1.331(3) .
C32 N31 1.337(3) .
C32 C33 1.384(3) .
C33 C34 1.385(3) .
C34 C35 1.385(3) .
C35 C36 1.380(3) .
C36 N31 1.344(3) .
C36 C37 1.492(3) .
C37 O39 1.257(3) .
C37 N38 1.314(3) .
C231 N232 1.144(3) .
N21 N22 1.309(3) .
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
N21 H21 O24 0.86 2.00 2.652(2) 131.4 .
N25 H25A O1W 0.86 2.09 2.903(3) 157.6 2_455
N25 H25B N232 0.86 2.22 2.994(3) 149.3 2_344
N38 H38A O24 0.86 2.04 2.878(3) 165.5 2_455
N38 H38B O1W 0.86 2.05 2.863(3) 156.6 2_455
O1W H1 O14 0.845(16) 1.886(16) 2.720(3) 169(3) .
O1W H2 O13 0.830(16) 2.122(17) 2.918(3) 161(3) 2_565
