# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_CuL2
_database_code_depnum_ccdc_archive 'CCDC 1844563'
loop_
_audit_author_name
_audit_author_address
'Oscar Enrique Piro'
;Universidad Nacional de La Plata
Argentina
;
_audit_update_record             
;
2019-03-20 deposited with the CCDC.	2019-04-03 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
bis[2-methoxy-6-(thiophen-2-ylmethyliminomethyl)phenolate]copper(II)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 Cu N2 O4 S2'
_chemical_formula_weight         556.13

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'
Cu Cu 0.3201 1.2651 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.2558(3)
_cell_length_b                   10.5965(5)
_cell_length_c                   11.1192(5)
_cell_angle_alpha                99.818(4)
_cell_angle_beta                 91.255(4)
_cell_angle_gamma                102.935(4)
_cell_volume                     593.54(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2923
_cell_measurement_theta_min      3.7200
_cell_measurement_theta_max      28.5920
_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_F_000             287
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.133
_shelx_estimated_absorpt_T_min   0.722
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_T_min  0.97710
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.904
_oxdiff_exptl_absorpt_empirical_full_max 1.194
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_reflns_number            8440
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.973
_diffrn_reflns_theta_max         28.842
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.864
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2685
_reflns_number_gt                2267
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;There was a rotational disorder of the five-member thiophene ring which 
splits into a dominant (0.74 occupancy) conformer and a second minor one 
rotated from the first in 180 degrees around the linking C-C sigma-bond. This 
disorder was modeled in terms of two such rings and refined such that their 
occupancies summed up to one.,There was a rotational disorder of the five-member thiophene ring which splits into a dominant (0.74 occupancy) conformer and a second minor one rotated from the first in 180 degrees around the linking C-C sigma-bond. This disorder was modeled in terms of two such rings and refined such that their occupancies summed up to one.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0218P)²+0.1968P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2685
_refine_ls_number_parameters     207
_refine_ls_number_restraints     67
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0732
_refine_ls_wR_factor_gt          0.0691
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.090(3) 0.205(3) 0.6149(11) 0.0319(7) Uani 0.745(3) 1 d D U P A 1
C2 C 1.1640(16) 0.1994(10) 0.7300(8) 0.057(2) Uani 0.745(3) 1 d D . P A 1
H2 H 1.3302 0.2437 0.7634 0.068 Uiso 0.745(3) 1 calc R U P A 1
C3 C 0.9928(9) 0.1279(6) 0.7969(5) 0.0472(13) Uani 0.745(3) 1 d D . P A 1
H3 H 1.0251 0.1190 0.8773 0.057 Uiso 0.745(3) 1 calc R U P A 1
C4 C 0.7688(11) 0.0721(6) 0.7279(4) 0.0451(13) Uani 0.745(3) 1 d D . P A 1
H4 H 0.6249 0.0181 0.7551 0.054 Uiso 0.745(3) 1 calc R U P A 1
C5 C 1.2335(4) 0.2671(2) 0.5169(2) 0.0342(5) Uani 1 1 d D . . . .
H5AA H 1.3799 0.3373 0.5541 0.041 Uiso 0.745(3) 1 calc R U P A 1
H5AB H 1.3025 0.2018 0.4639 0.041 Uiso 0.745(3) 1 calc R U P A 1
H5BC H 1.3748 0.3376 0.5583 0.041 Uiso 0.255(3) 1 calc R U P A 2
H5BD H 1.3092 0.2045 0.4640 0.041 Uiso 0.255(3) 1 calc R U P A 2
C6 C 0.9626(4) 0.24743(19) 0.34118(19) 0.0334(5) Uani 1 1 d . . . . .
H6 H 1.0213 0.1707 0.3189 0.040 Uiso 1 1 calc R U . . .
C7 C 0.7738(4) 0.27018(19) 0.25805(19) 0.0316(4) Uani 1 1 d . . . . .
C8 C 0.6572(4) 0.37844(19) 0.28542(18) 0.0300(4) Uani 1 1 d . . . . .
C9 C 0.4638(4) 0.3912(2) 0.1982(2) 0.0337(5) Uani 1 1 d . . . . .
C10 C 0.4012(4) 0.3026(2) 0.0912(2) 0.0427(6) Uani 1 1 d . . . . .
H10 H 0.2761 0.3126 0.0353 0.051 Uiso 1 1 calc R U . . .
C11 C 0.5230(5) 0.1972(2) 0.0644(2) 0.0485(6) Uani 1 1 d . . . . .
H11 H 0.4802 0.1381 -0.0091 0.058 Uiso 1 1 calc R U . . .
C12 C 0.7038(4) 0.1813(2) 0.1463(2) 0.0413(5) Uani 1 1 d . . . . .
H12 H 0.7828 0.1107 0.1284 0.050 Uiso 1 1 calc R U . . .
C13 C 0.1910(5) 0.5274(2) 0.1448(2) 0.0514(6) Uani 1 1 d . . . . .
H13A H 0.2856 0.5427 0.0738 0.077 Uiso 1 1 calc R U . . .
H13B H 0.1336 0.6050 0.1790 0.077 Uiso 1 1 calc R U . . .
H13C H 0.0419 0.4551 0.1220 0.077 Uiso 1 1 calc R U . . .
N N 1.0608(3) 0.32103(15) 0.44344(15) 0.0310(4) Uani 1 1 d . . . . .
O1 O 0.7146(3) 0.46694(14) 0.38410(14) 0.0401(4) Uani 1 1 d . . . . .
O2 O 0.3571(3) 0.49681(15) 0.23310(15) 0.0450(4) Uani 1 1 d . . . . .
S S 0.7782(2) 0.11183(16) 0.58283(14) 0.0504(4) Uani 0.745(3) 1 d D . P A 1
Cu Cu 1.0000 0.5000 0.5000 0.03035(12) Uani 1 2 d S . P . .
C1A C 1.080(8) 0.201(8) 0.608(3) 0.0318(8) Uani 0.255(3) 1 d D U P A 2
C2A C 0.832(3) 0.128(2) 0.5965(17) 0.057(4) Uani 0.255(3) 1 d D U P A 2
H2A H 0.7293 0.1153 0.5245 0.069 Uiso 0.255(3) 1 calc R U P A 2
C3A C 0.738(4) 0.074(2) 0.6935(15) 0.045(3) Uani 0.255(3) 1 d D U P A 2
H3A H 0.5729 0.0194 0.6952 0.054 Uiso 0.255(3) 1 calc R U P A 2
C4A C 0.920(3) 0.111(2) 0.7852(18) 0.046(3) Uani 0.255(3) 1 d D U P A 2
H4A H 0.8948 0.0845 0.8605 0.055 Uiso 0.255(3) 1 calc R U P A 2
SA S 1.2126(13) 0.2141(8) 0.7520(6) 0.0470(12) Uani 0.255(3) 1 d D U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
C1 C2 1.344(11) . ?
C1 C5 1.498(5) . ?
C1 S 1.709(8) . ?
C2 C3 1.362(10) . ?
C3 C4 1.349(5) . ?
C4 S 1.734(4) . ?
C5 N 1.475(2) . ?
C5 C1A 1.478(12) . ?
C6 N 1.288(2) . ?
C6 C7 1.428(3) . ?
C7 C8 1.410(3) . ?
C7 C12 1.411(3) . ?
C8 O1 1.297(2) . ?
C8 C9 1.433(3) . ?
C9 O2 1.364(2) . ?
C9 C10 1.367(3) . ?
C10 C11 1.401(3) . ?
C11 C12 1.358(3) . ?
C13 O2 1.425(2) . ?
N Cu 1.9919(16) . ?
O1 Cu 1.8866(13) . ?
Cu O1 1.8866(13) 2_766 ?
Cu N 1.9919(16) 2_766 ?
C1A C2A 1.35(2) . ?
C1A SA 1.71(2) . ?
C2A C3A 1.360(18) . ?
C3A C4A 1.326(14) . ?
C4A SA 1.764(15) . ?

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
C2 C1 C5 132.3(8) . . ?
C2 C1 S 107.9(5) . . ?
C5 C1 S 119.6(5) . . ?
C1 C2 C3 119.3(7) . . ?
C4 C3 C2 109.0(6) . . ?
C3 C4 S 112.6(4) . . ?
N C5 C1A 109(3) . . ?
N C5 C1 111.4(9) . . ?
N C6 C7 127.44(18) . . ?
C8 C7 C12 119.82(19) . . ?
C8 C7 C6 121.55(18) . . ?
C12 C7 C6 118.63(19) . . ?
O1 C8 C7 124.11(18) . . ?
O1 C8 C9 118.22(18) . . ?
C7 C8 C9 117.67(18) . . ?
O2 C9 C10 125.59(19) . . ?
O2 C9 C8 113.83(17) . . ?
C10 C9 C8 120.6(2) . . ?
C9 C10 C11 120.9(2) . . ?
C12 C11 C10 119.8(2) . . ?
C11 C12 C7 121.2(2) . . ?
C6 N C5 115.89(17) . . ?
C6 N Cu 123.48(14) . . ?
C5 N Cu 120.59(12) . . ?
C8 O1 Cu 129.01(13) . . ?
C9 O2 C13 117.33(17) . . ?
C1 S C4 91.2(3) . . ?
O1 Cu O1 180.0 . 2_766 ?
O1 Cu N 91.25(6) . . ?
O1 Cu N 88.75(6) 2_766 . ?
O1 Cu N 88.75(6) . 2_766 ?
O1 Cu N 91.25(6) 2_766 2_766 ?
N Cu N 180.0 . 2_766 ?
C2A C1A C5 129.5(19) . . ?
C2A C1A SA 110.1(10) . . ?
C5 C1A SA 120.4(16) . . ?
C1A C2A C3A 118.1(16) . . ?
C4A C3A C2A 108.8(16) . . ?
C3A C4A SA 114.3(15) . . ?
C1A SA C4A 88.6(9) . . ?

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
C5 C1 C2 C3 -176(2) . . . . ?
S C1 C2 C3 -1(3) . . . . ?
C1 C2 C3 C4 1(2) . . . . ?
C2 C3 C4 S -0.6(8) . . . . ?
C2 C1 C5 N -144(3) . . . . ?
S C1 C5 N 41(2) . . . . ?
N C6 C7 C8 -4.3(3) . . . . ?
N C6 C7 C12 175.8(2) . . . . ?
C12 C7 C8 O1 -178.0(2) . . . . ?
C6 C7 C8 O1 2.1(3) . . . . ?
C12 C7 C8 C9 1.8(3) . . . . ?
C6 C7 C8 C9 -178.11(18) . . . . ?
O1 C8 C9 O2 -1.6(3) . . . . ?
C7 C8 C9 O2 178.62(18) . . . . ?
O1 C8 C9 C10 178.2(2) . . . . ?
C7 C8 C9 C10 -1.6(3) . . . . ?
O2 C9 C10 C11 -179.9(2) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C9 C10 C11 C12 0.7(4) . . . . ?
C10 C11 C12 C7 -0.6(4) . . . . ?
C8 C7 C12 C11 -0.7(3) . . . . ?
C6 C7 C12 C11 179.2(2) . . . . ?
C7 C6 N C5 174.26(19) . . . . ?
C7 C6 N Cu -8.0(3) . . . . ?
C1A C5 N C6 -95(3) . . . . ?
C1 C5 N C6 -98.1(11) . . . . ?
C1A C5 N Cu 87(3) . . . . ?
C1 C5 N Cu 84.1(11) . . . . ?
C7 C8 O1 Cu 13.5(3) . . . . ?
C9 C8 O1 Cu -166.30(14) . . . . ?
C10 C9 O2 C13 -8.4(3) . . . . ?
C8 C9 O2 C13 171.37(18) . . . . ?
C2 C1 S C4 0(2) . . . . ?
C5 C1 S C4 176(2) . . . . ?
C3 C4 S C1 0.1(12) . . . . ?
C8 O1 Cu N -19.25(19) . . . . ?
C8 O1 Cu N 160.75(19) . . . 2_766 ?
N C5 C1A C2A 38(10) . . . . ?
N C5 C1A SA -141(5) . . . . ?
C5 C1A C2A C3A 177(6) . . . . ?
SA C1A C2A C3A -3(8) . . . . ?
C1A C2A C3A C4A 2(6) . . . . ?
C2A C3A C4A SA 0(3) . . . . ?
C2A C1A SA C4A 2(6) . . . . ?
C5 C1A SA C4A -178(6) . . . . ?
C3A C4A SA C1A -1(4) . . . . ?

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.052


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ZnL2
_database_code_depnum_ccdc_archive 'CCDC 1844564'
loop_
_audit_author_name
_audit_author_address
'Oscar Enrique Piro'
;Universidad Nacional de La Plata
Argentina
;
_audit_update_record             
;
2019-03-20 deposited with the CCDC.	2019-04-03 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
bis[2-methoxy-6-(thiophen-2-ylmethyliminomethyl)phenolate]zinc(II)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 N2 O4 S2 Zn'
_chemical_formula_weight         557.96

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.6363(10)
_cell_length_b                   5.3423(3)
_cell_length_c                   20.8134(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.814(4)
_cell_angle_gamma                90
_cell_volume                     2433.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2016
_cell_measurement_theta_min      4.3070
_cell_measurement_theta_max      28.3590
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.033
_exptl_absorpt_coefficient_mu    1.218
_shelx_estimated_absorpt_T_min   0.746
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_T_min  0.85739
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.875
_oxdiff_exptl_absorpt_empirical_full_max 1.142
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_reflns_number            5382
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.081
_diffrn_reflns_theta_max         29.011
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.819
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2652
_reflns_number_gt                2098
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;There was a slight rotational disorder of the five-member thiophene ring which 
splits into a dominant (0.83 occupancy) conformer and a second minor one 
rotated from the first in 180 degrees around the linking C-C sigma-bond. This 
disorder was modeled in terms of two such rings and refined such that their 
occupancies summed up to one.,There was a rotational disorder of the five-member thiophene ring which splits into a dominant (0.74 occupancy) conformer and a second minor one rotated from the first in 180 degrees around the linking C-C sigma-bond. This disorder was modeled in terms of two such rings and refined such that their occupancies summed up to one.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0332P)²+0.9014P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2652
_refine_ls_number_parameters     206
_refine_ls_number_restraints     49
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.0845
_refine_ls_wR_factor_gt          0.0780
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6302(2) 0.9269(13) 0.6842(3) 0.0287(11) Uani 0.825(3) 1 d D U P A 1
C2 C 0.6659(5) 1.0224(16) 0.6478(5) 0.045(2) Uani 0.825(3) 1 d D . P A 1
H2 H 0.6559 1.1681 0.6230 0.054 Uiso 0.825(3) 1 calc R U P A 1
C3 C 0.7195(3) 0.8868(11) 0.6500(4) 0.0402(12) Uani 0.825(3) 1 d D . P A 1
H3 H 0.7479 0.9301 0.6266 0.048 Uiso 0.825(3) 1 calc R U P A 1
C4 C 0.7246(2) 0.6861(10) 0.6902(3) 0.0390(12) Uani 0.825(3) 1 d D . P A 1
H4 H 0.7568 0.5728 0.6976 0.047 Uiso 0.825(3) 1 calc R U P A 1
C5 C 0.57093(10) 1.0223(5) 0.69487(11) 0.0360(6) Uani 1 1 d D . . . .
H5AA H 0.5771 1.0748 0.7407 0.043 Uiso 0.825(3) 1 calc R U P A 1
H5AB H 0.5575 1.1666 0.6666 0.043 Uiso 0.825(3) 1 calc R U P A 1
H5BC H 0.5720 1.0928 0.7381 0.043 Uiso 0.175(3) 1 calc R U P A 2
H5BD H 0.5597 1.1554 0.6623 0.043 Uiso 0.175(3) 1 calc R U P A 2
C6 C 0.49741(10) 0.7899(5) 0.61757(10) 0.0325(5) Uani 1 1 d . . . . .
H6 H 0.5091 0.8971 0.5878 0.039 Uiso 1 1 calc R U . . .
C7 C 0.45237(10) 0.6038(4) 0.58849(10) 0.0310(5) Uani 1 1 d . . . . .
C8 C 0.42724(9) 0.4309(4) 0.62529(10) 0.0292(5) Uani 1 1 d . . . . .
C9 C 0.38308(10) 0.2575(5) 0.58875(10) 0.0332(5) Uani 1 1 d . . . . .
C10 C 0.36606(11) 0.2599(5) 0.52040(11) 0.0416(6) Uani 1 1 d . . . . .
H10 H 0.3374 0.1450 0.4976 0.050 Uiso 1 1 calc R U . . .
C11 C 0.39144(12) 0.4335(5) 0.48502(11) 0.0482(7) Uani 1 1 d . . . . .
H11 H 0.3796 0.4342 0.4388 0.058 Uiso 1 1 calc R U . . .
C12 C 0.43334(12) 0.6013(5) 0.51801(11) 0.0437(6) Uani 1 1 d . . . . .
H12 H 0.4499 0.7166 0.4940 0.052 Uiso 1 1 calc R U . . .
C13 C 0.31664(12) -0.0845(5) 0.59369(14) 0.0504(7) Uani 1 1 d . . . . .
H13A H 0.2804 0.0014 0.5699 0.076 Uiso 1 1 calc R U . . .
H13B H 0.3068 -0.1961 0.6256 0.076 Uiso 1 1 calc R U . . .
H13C H 0.3331 -0.1786 0.5630 0.076 Uiso 1 1 calc R U . . .
N N 0.52348(8) 0.8266(3) 0.67947(8) 0.0294(4) Uani 1 1 d . . . . .
O1 O 0.44100(7) 0.4201(3) 0.69018(7) 0.0389(4) Uani 1 1 d . . . . .
O2 O 0.36058(8) 0.0928(3) 0.62710(8) 0.0454(4) Uani 1 1 d . . . . .
S S 0.66404(6) 0.6641(3) 0.72627(8) 0.0412(3) Uani 0.825(3) 1 d D . P A 1
Zn Zn 0.5000 0.62576(8) 0.7500 0.03450(14) Uani 1 2 d S T P . .
C1A C 0.6333(12) 0.931(6) 0.6953(18) 0.0288(12) Uani 0.175(3) 1 d D U P A 2
C2A C 0.6566(11) 0.702(5) 0.7128(15) 0.043(5) Uani 0.175(3) 1 d D U P A 2
H2A H 0.6364 0.5790 0.7307 0.051 Uiso 0.175(3) 1 calc R U P A 2
C3A C 0.7142(12) 0.666(6) 0.7013(15) 0.040(4) Uani 0.175(3) 1 d D U P A 2
H3A H 0.7416 0.5412 0.7207 0.048 Uiso 0.175(3) 1 calc R U P A 2
C4A C 0.7245(15) 0.837(6) 0.658(2) 0.039(5) Uani 0.175(3) 1 d D U P A 2
H4A H 0.7578 0.8322 0.6397 0.046 Uiso 0.175(3) 1 calc R U P A 2
SA S 0.6696(6) 1.068(2) 0.6407(7) 0.0381(17) Uani 0.175(3) 1 d D U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
C1 C2 1.342(9) . ?
C1 C5 1.503(4) . ?
C1 S 1.727(5) . ?
C2 C3 1.403(10) . ?
C3 C4 1.346(5) . ?
C4 S 1.727(4) . ?
C5 N 1.474(3) . ?
C5 C1A 1.492(14) . ?
C6 N 1.288(3) . ?
C6 C7 1.442(3) . ?
C7 C8 1.409(3) . ?
C7 C12 1.419(3) . ?
C8 O1 1.307(2) . ?
C8 C9 1.431(3) . ?
C9 O2 1.371(3) . ?
C9 C10 1.375(3) . ?
C10 C11 1.396(4) . ?
C11 C12 1.357(4) . ?
C13 O2 1.420(3) . ?
N Zn 1.9971(18) . ?
O1 Zn 1.9211(15) . ?
Zn O1 1.9211(15) 2_656 ?
Zn N 1.9971(18) 2_656 ?
C1A C2A 1.35(2) . ?
C1A SA 1.73(2) . ?
C2A C3A 1.398(19) . ?
C3A C4A 1.343(17) . ?
C4A SA 1.722(18) . ?

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
C2 C1 C5 130.1(6) . . ?
C2 C1 S 110.0(4) . . ?
C5 C1 S 119.8(3) . . ?
C1 C2 C3 115.2(6) . . ?
C4 C3 C2 111.5(5) . . ?
C3 C4 S 111.9(4) . . ?
N C5 C1A 113.9(16) . . ?
N C5 C1 110.8(4) . . ?
N C6 C7 128.3(2) . . ?
C8 C7 C12 119.8(2) . . ?
C8 C7 C6 124.34(19) . . ?
C12 C7 C6 115.8(2) . . ?
O1 C8 C7 124.6(2) . . ?
O1 C8 C9 118.0(2) . . ?
C7 C8 C9 117.37(19) . . ?
O2 C9 C10 124.1(2) . . ?
O2 C9 C8 114.78(18) . . ?
C10 C9 C8 121.1(2) . . ?
C9 C10 C11 120.5(2) . . ?
C12 C11 C10 120.0(2) . . ?
C11 C12 C7 121.2(2) . . ?
C6 N C5 116.60(19) . . ?
C6 N Zn 120.90(16) . . ?
C5 N Zn 122.49(14) . . ?
C8 O1 Zn 125.94(15) . . ?
C9 O2 C13 117.45(18) . . ?
C1 S C4 91.3(2) . . ?
O1 Zn O1 110.23(10) . 2_656 ?
O1 Zn N 95.88(7) . . ?
O1 Zn N 120.81(7) 2_656 . ?
O1 Zn N 120.81(7) . 2_656 ?
O1 Zn N 95.88(7) 2_656 2_656 ?
N Zn N 114.99(10) . 2_656 ?
C2A C1A C5 127(2) . . ?
C2A C1A SA 110.2(14) . . ?
C5 C1A SA 117.8(15) . . ?
C1A C2A C3A 113.3(18) . . ?
C4A C3A C2A 110(2) . . ?
C3A C4A SA 113.0(18) . . ?
C1A SA C4A 89.8(11) . . ?

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
C5 C1 C2 C3 178.6(7) . . . . ?
S C1 C2 C3 2.4(13) . . . . ?
C1 C2 C3 C4 -1.2(13) . . . . ?
C2 C3 C4 S -0.6(9) . . . . ?
C2 C1 C5 N 126.9(10) . . . . ?
S C1 C5 N -57.3(5) . . . . ?
N C6 C7 C8 2.4(4) . . . . ?
N C6 C7 C12 -177.6(2) . . . . ?
C12 C7 C8 O1 -179.0(2) . . . . ?
C6 C7 C8 O1 1.0(4) . . . . ?
C12 C7 C8 C9 0.3(3) . . . . ?
C6 C7 C8 C9 -179.8(2) . . . . ?
O1 C8 C9 O2 -1.2(3) . . . . ?
C7 C8 C9 O2 179.6(2) . . . . ?
O1 C8 C9 C10 179.4(2) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
O2 C9 C10 C11 -179.7(2) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C10 C11 C12 C7 0.2(4) . . . . ?
C8 C7 C12 C11 -0.5(4) . . . . ?
C6 C7 C12 C11 179.6(2) . . . . ?
C7 C6 N C5 176.4(2) . . . . ?
C7 C6 N Zn -3.5(3) . . . . ?
C1A C5 N C6 -87.6(13) . . . . ?
C1 C5 N C6 -78.9(3) . . . . ?
C1A C5 N Zn 92.4(13) . . . . ?
C1 C5 N Zn 101.0(3) . . . . ?
C7 C8 O1 Zn -2.4(3) . . . . ?
C9 C8 O1 Zn 178.37(15) . . . . ?
C10 C9 O2 C13 -0.5(3) . . . . ?
C8 C9 O2 C13 -179.9(2) . . . . ?
C2 C1 S C4 -2.3(8) . . . . ?
C5 C1 S C4 -178.9(5) . . . . ?
C3 C4 S C1 1.7(6) . . . . ?
N C5 C1A C2A -32(4) . . . . ?
N C5 C1A SA 121(2) . . . . ?
C5 C1A C2A C3A 174(3) . . . . ?
SA C1A C2A C3A 19(4) . . . . ?
C1A C2A C3A C4A -18(5) . . . . ?
C2A C3A C4A SA 9(5) . . . . ?
C2A C1A SA C4A -12(4) . . . . ?
C5 C1A SA C4A -169(3) . . . . ?
C3A C4A SA C1A 2(4) . . . . ?

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.057


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
