# 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 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1505819'
_audit_update_record             
;
2016-09-22 deposited with the CCDC.
2018-01-22 downloaded from the CCDC.
;
_audit_creation_date             2015-10-05
_audit_creation_method           
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_chemical_formula_moiety         'C10 H8 N2 S2, 2(C3 Cl3 N3)'
_chemical_formula_sum            'C16 H8 Cl6 N8 S2'
_chemical_formula_weight         589.12
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Cl 0.14873 0.16029 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
S 0.12424 0.12443 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

_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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_cell_length_a                   20.900(4)
_cell_length_b                   4.9614(10)
_cell_length_c                   24.079(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.14(3)
_cell_angle_gamma                90
_cell_volume                     2441.0(9)
_cell_formula_units_Z            4
_exptl_absorpt_coefficient_mu    0.898
_exptl_crystal_density_diffrn    1.6030
_exptl_crystal_F_000             1180.7900
_exptl_crystal_description       Block
_exptl_crystal_colour            'Light Yellow'
_diffrn_ambient_temperature      277(2)
_cell_measurement_temperature    277(2)
_cell_measurement_reflns_used    298
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      27.02
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_T_max  0.764
_exptl_absorpt_process_details   'SADABS v. 2.03 (Sheldrick, 2008)'
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11384
_diffrn_reflns_theta_full        27.479935
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.46
_diffrn_measured_fraction_theta_full 0.997857
_diffrn_measured_fraction_theta_max 0.997858
_diffrn_radiation_probe          ?
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku ip'
_diffrn_measurement_method       'φ and ω'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              26
_reflns_limit_h_min              -26
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              30
_reflns_limit_l_min              0
_reflns_number_gt                1595
_reflns_number_total             2795
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.743911
_refine_diff_density_min         -0.970019
_refine_diff_density_rms         0.143130
_refine_ls_d_res_high            0.770125
_refine_ls_d_res_low             5.885219
_refine_ls_goodness_of_fit_ref   1.017516
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    8
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2795
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.121220
_refine_ls_R_factor_gt           0.072842
_refine_ls_restrained_S_all      1.017516
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.243618
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_refinement_flags_posn
Cl1 Cl 0.03299(7) 1.1018(3) 0.42051(6) 0.0585(5) Uani 1.000000 .
Cl3 Cl 0.10675(9) 0.3994(4) 0.58617(7) 0.0711(6) Uani 1.000000 .
Cl2 Cl 0.24186(7) 0.5007(4) 0.42553(6) 0.0635(5) Uani 1.000000 .
S1 S 0.03767(9) 0.5624(4) 0.28433(8) 0.0729(6) Uani 1.000000 .
N4 N 0.0778(2) 0.7441(9) 0.50149(16) 0.0483(10) Uani 1.000000 .
N1 N 0.1366(2) 0.8859(11) 0.31427(18) 0.0587(13) Uani 1.000000 .
C4 C 0.1828(4) 1.0609(16) 0.3069(3) 0.0766(19) Uani 1.000000 .
H4 H 0.2155(4) 1.1077(16) 0.3380(3) 0.092(2) Uiso 1.000000 R
C3 C 0.1839(4) 1.1717(18) 0.2560(4) 0.091(3) Uani 1.000000 .
H3 H 0.2158(4) 1.2978(18) 0.2528(4) 0.109(3) Uiso 1.000000 R
C1 C 0.0910(4) 0.9195(16) 0.2147(3) 0.0733(19) Uani 1.000000 .
H1 H 0.0591(4) 0.8674(16) 0.1836(3) 0.088(2) Uiso 1.000000 R
C2 C 0.1380(5) 1.0991(17) 0.2090(3) 0.087(2) Uani 1.000000 .
H2 H 0.1390(5) 1.1722(17) 0.1736(3) 0.105(3) Uiso 1.000000 R
N2 N 0.1331(2) 0.7667(9) 0.42697(15) 0.0471(10) Uani 1.000000 .
N3 N 0.1676(2) 0.4718(9) 0.50201(17) 0.0506(11) Uani 1.000000 .
C7 C 0.1171(3) 0.5459(11) 0.5283(2) 0.0494(12) Uani 1.000000 .
C5 C 0.0819(2) 0.8664(11) 0.4500(2) 0.0472(12) Uani 1.000000 .
C11 C 0.0920(3) 0.8149(12) 0.2686(2) 0.0527(13) Uani 1.000000 .
C6 C 0.1778(2) 0.5849(11) 0.4524(2) 0.0468(12) Uani 1.000000 .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0622(9) 0.0656(10) 0.0510(8) 0.0122(7) 0.0194(6) 0.0051(6)
Cl3 0.0893(12) 0.0737(12) 0.0588(9) 0.0158(8) 0.0348(8) 0.0151(7)
Cl2 0.0598(9) 0.0817(12) 0.0546(8) 0.0140(7) 0.0242(7) 0.0012(7)
S1 0.0719(11) 0.0701(12) 0.0766(11) 0.0007(8) 0.0157(9) 0.0206(8)
N4 0.059(2) 0.047(3) 0.043(2) 0.009(2) 0.0196(19) 0.0029(18)
N1 0.060(3) 0.078(4) 0.042(2) 0.009(2) 0.017(2) -0.002(2)
C4 0.066(4) 0.090(6) 0.076(4) -0.002(4) 0.020(3) -0.012(4)
C3 0.099(6) 0.077(5) 0.117(6) -0.013(4) 0.067(5) -0.000(5)
C1 0.088(5) 0.087(5) 0.044(3) 0.006(4) 0.013(3) 0.007(3)
C2 0.117(6) 0.091(6) 0.064(4) -0.003(5) 0.041(4) 0.017(4)
N2 0.050(2) 0.056(3) 0.0372(19) 0.007(2) 0.0136(18) 0.0004(18)
N3 0.057(3) 0.056(3) 0.041(2) 0.004(2) 0.0156(19) -0.0003(18)
C7 0.058(3) 0.050(3) 0.044(3) 0.004(2) 0.018(2) -0.003(2)
C5 0.050(3) 0.053(3) 0.041(2) 0.004(2) 0.015(2) -0.004(2)
C11 0.055(3) 0.059(3) 0.047(3) 0.007(3) 0.018(2) -0.001(2)
C6 0.047(3) 0.056(3) 0.039(2) 0.005(2) 0.012(2) -0.004(2)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C5 1.615(6) .
Cl3 C7 1.626(5) .
Cl2 C6 1.658(5) .
S1 S1 2.029(4) 2
S1 C11 1.784(6) .
N4 C7 1.354(7) .
N4 C5 1.398(6) .
N1 C4 1.339(9) .
N1 C11 1.331(7) .
C4 H4 0.9300 .
C4 C3 1.348(10) .
C3 H3 0.9300 .
C3 C2 1.368(12) .
C1 H1 0.9300 .
C1 C2 1.353(10) .
C1 C11 1.394(8) .
C2 H2 0.9300 .
N2 C5 1.396(6) .
N2 C6 1.349(7) .
N3 C7 1.390(6) .
N3 C6 1.376(6) .

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
C5 N4 C7 126.4(4) . .
C11 N1 C4 117.5(5) . .
H4 C4 N1 118.8(4) . .
C3 C4 N1 122.4(7) . .
C3 C4 H4 118.8(5) . .
H3 C3 C4 119.9(5) . .
C2 C3 C4 120.1(7) . .
C2 C3 H3 119.9(4) . .
C2 C1 H1 121.0(4) . .
C11 C1 H1 121.0(4) . .
C11 C1 C2 118.1(7) . .
C1 C2 C3 119.1(6) . .
H2 C2 C3 120.5(4) . .
H2 C2 C1 120.5(4) . .
C6 N2 C5 124.9(4) . .
C6 N3 C7 123.9(5) . .
N4 C7 Cl3 123.8(4) . .
N3 C7 Cl3 121.5(4) . .
N3 C7 N4 114.7(4) . .
N4 C5 Cl1 123.6(4) . .
N2 C5 Cl1 123.2(4) . .
N2 C5 N4 113.2(4) . .
N1 C11 S1 112.1(4) . .
C1 C11 S1 125.0(5) . .
C1 C11 N1 122.8(6) . .
N2 C6 Cl2 122.0(4) . .
N3 C6 Cl2 121.4(4) . .
N3 C6 N2 116.6(4) . .
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1505820'
_audit_update_record             
;
2016-09-22 deposited with the CCDC.
2018-01-22 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT031_2                   
;
PROBLEM: Refined Extinction Parameter within Range ......      0.200 Sigma
RESPONSE: The cell and other parameters are fine enough however the data quality was not so good which is responsible for A and B level alerts
;
_vrf_DIFMX01_2                   
;
PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00
RESPONSE: The cell and other parameters are fine enough however the data quality was not so good which is responsible for A and B level alerts
;
_vrf_RFACG01_2                   
;
PROBLEM: The value of the R factor is > 0.15
RESPONSE: The cell and other parameters are fine enough however the data quality was not so good which is responsible for A and B level alerts
;
_vrf_RFACR01_2                   
;
PROBLEM: The value of the weighted R factor is > 0.35
RESPONSE: The cell and other parameters are fine enough however the data quality was not so good which is responsible for A and B level alerts
;
_vrf_SHFSU01_2                   
;
PROBLEM: The absolute value of parameter shift to su ratio > 0.10
RESPONSE: The cell and other parameters are fine enough however the data quality was not so good which is responsible for A and B level alerts
;
_vrf_PLAT080_2                   
;
PROBLEM: Maximum Shift/Error ............................       0.16 Why ?
RESPONSE: The cell and other parameters are fine enough however the data quality was not so good which is responsible for A and B level alerts
;
_vrf_PLAT084_2                   
;
PROBLEM: High wR2 Value (i.e. &gt; 0.25) ...................       0.45 Report
RESPONSE: The cell and other parameters are fine enough however the data quality was not so good which is responsible for A and B level alerts
;
_vrf_PLAT097_2                   
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.82 eA-3
RESPONSE: The cell and other parameters are fine enough however the data quality was not so good which is responsible for A and B level alerts
;
# Added during the CSD deposition process: Thursday 22 September 2016 11:08 AM
# end Validation Reply Form

_audit_creation_date             2015-10-05
_audit_creation_method           
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         '4(C6 H11 N3 O3)'
_chemical_formula_sum            'C6 H11 N3 O3'
_chemical_formula_weight         173.18
_chemical_melting_point          ?
_exptl_crystal_description       Block
_exptl_crystal_colour            white
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z+1/2'
4 '-x, y+1/2, -z'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z-1/2'
8 'x, -y-1/2, z'

_cell_length_a                   8.442(4)
_cell_length_b                   6.7270(13)
_cell_length_c                   14.467(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     821.6(5)
_cell_formula_units_Z            4
_diffrn_ambient_temperature      277(2)
_cell_measurement_temperature    277(2)
_cell_measurement_reflns_used    173
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.01
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.113
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5749
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.34
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku ip'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.329
_exptl_absorpt_correction_T_max  0.464
_exptl_absorpt_process_details   'SADABS v. 2.03 (Sheldrick, 2008)'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                521
_reflns_number_total             785
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.821
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.126
_refine_ls_extinction_coef       0.002(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.776
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         785
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1679
_refine_ls_R_factor_gt           0.1516
_refine_ls_restrained_S_all      1.776
_refine_ls_shift/su_max          0.157
_refine_ls_shift/su_mean         0.106
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4348
_refine_ls_wR_factor_ref         0.4455
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6650(8) 0.2500 -0.1348(5) 0.076(2) Uani 1 2 d S . .
O2 O 0.1597(8) 0.2500 -0.0351(6) 0.088(3) Uani 1 2 d S . .
O3 O 0.5577(7) 0.2500 0.1717(5) 0.069(2) Uani 1 2 d S . .
N1 N 0.4099(10) 0.2500 -0.0883(5) 0.060(2) Uani 1 2 d S . .
N2 N 0.3592(10) 0.2500 0.0730(5) 0.063(2) Uani 1 2 d S . .
N3 N 0.6244(9) 0.2500 0.0187(5) 0.056(2) Uani 1 2 d S . .
C1 C 0.5604(11) 0.2500 -0.0676(7) 0.057(3) Uani 1 2 d S . .
C2 C 0.6112(19) 0.2500 -0.2255(7) 0.101(5) Uani 1 2 d S . .
H2A H 0.5102 0.1871 -0.2344 0.122 Uiso 0.50 1 d PR . .
H2B H 0.6937 0.1946 -0.2594 0.122 Uiso 1 1 d R . .
H8A H 0.5783 0.3761 -0.2441 0.122 Uiso 1 1 d R . .
C3 C 0.3145(11) 0.2500 -0.0131(6) 0.056(2) Uani 1 2 d S . .
C4 C 0.0479(14) 0.2500 0.0387(8) 0.103(4) Uani 1 2 d S . .
H4A H 0.0800 0.1555 0.0848 0.154 Uiso 0.50 1 calc PR . .
H4B H -0.0547 0.2142 0.0153 0.154 Uiso 0.50 1 calc PR . .
H4C H 0.0430 0.3802 0.0657 0.154 Uiso 0.50 1 calc PR . .
C5 C 0.5141(11) 0.2500 0.0852(6) 0.056(2) Uani 1 2 d S . .
C6 C 0.7198(13) 0.2500 0.1945(7) 0.087(4) Uani 1 2 d S . .
H6A H 0.7772 0.1726 0.1499 0.131 Uiso 0.50 1 calc PR . .
H6B H 0.7338 0.1934 0.2548 0.131 Uiso 0.50 1 calc PR . .
H6C H 0.7589 0.3840 0.1943 0.131 Uiso 0.50 1 calc PR . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.091(6) 0.084(4) 0.053(4) 0.000 0.032(4) 0.000
O2 0.046(4) 0.137(7) 0.083(5) 0.000 -0.020(3) 0.000
O3 0.050(4) 0.095(5) 0.062(4) 0.000 -0.006(3) 0.000
N1 0.064(5) 0.065(4) 0.051(4) 0.000 -0.005(4) 0.000
N2 0.075(5) 0.063(4) 0.052(5) 0.000 0.003(4) 0.000
N3 0.043(4) 0.062(4) 0.062(5) 0.000 -0.009(3) 0.000
C1 0.055(5) 0.050(4) 0.067(6) 0.000 0.022(5) 0.000
C2 0.147(13) 0.092(7) 0.065(8) 0.000 0.036(8) 0.000
C3 0.050(5) 0.068(5) 0.049(5) 0.000 0.005(4) 0.000
C4 0.061(7) 0.173(13) 0.074(8) 0.000 -0.003(6) 0.000
C5 0.062(5) 0.051(4) 0.053(5) 0.000 -0.001(4) 0.000
C6 0.063(6) 0.129(10) 0.069(7) 0.000 -0.017(6) 0.000

_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
O1 C1 1.312(10) . ?
O1 C2 1.389(13) . ?
O2 C3 1.345(11) . ?
O2 C4 1.426(15) . ?
O3 C5 1.304(11) . ?
O3 C6 1.408(12) . ?
N1 C1 1.305(12) . ?
N1 C3 1.355(12) . ?
N2 C3 1.301(11) . ?
N2 C5 1.320(12) . ?
N3 C1 1.362(12) . ?
N3 C5 1.338(11) . ?
C2 H2A 0.9603 . ?
C2 H2B 0.9295 . ?
C2 H8A 0.9319 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?

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
C1 O1 C2 118.7(10) . . ?
C3 O2 C4 117.7(9) . . ?
C5 O3 C6 119.9(8) . . ?
C1 N1 C3 113.2(8) . . ?
C3 N2 C5 114.5(8) . . ?
C5 N3 C1 112.5(8) . . ?
O1 C1 N3 114.4(8) . . ?
N1 C1 O1 119.0(9) . . ?
N1 C1 N3 126.6(8) . . ?
O1 C2 H2A 114.6 . . ?
O1 C2 H2B 104.7 . . ?
O1 C2 H8A 111.7 . . ?
H2A C2 H2B 114.7 . . ?
H2A C2 H8A 95.6 . . ?
H2B C2 H8A 115.8 . . ?
O2 C3 N1 112.8(8) . . ?
N2 C3 O2 120.6(8) . . ?
N2 C3 N1 126.7(9) . . ?
O2 C4 H4A 109.5 . . ?
O2 C4 H4B 109.4 . . ?
O2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O3 C5 N2 114.0(8) . . ?
N3 C5 O3 119.5(8) . . ?
N3 C5 N2 126.4(9) . . ?
O3 C6 H6A 109.5 . . ?
O3 C6 H6B 109.4 . . ?
O3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1505822'
_audit_update_record             
;
2016-09-22 deposited with the CCDC.
2018-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H14 Cu N2 O7 S2'
_chemical_melting_point          ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue

_diffrn_ambient_temperature      277(2)
_chemical_formula_weight         401.89

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2021(13)
_cell_length_b                   9.469(3)
_cell_length_c                   11.699(3)
_cell_angle_alpha                66.533(13)
_cell_angle_beta                 80.57(3)
_cell_angle_gamma                81.58(3)
_cell_volume                     719.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    277(2)
_cell_measurement_reflns_used    340
_cell_measurement_theta_min      2.11
_cell_measurement_theta_max      28.20
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.856
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             410
_exptl_absorpt_coefficient_mu    1.845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5998
_exptl_absorpt_correction_T_max  0.7190
_exptl_absorpt_process_details   'SADABS v. 2.03 (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku ip'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5282
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_av_sigmaI/netI    0.1215
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2440
_reflns_number_gt                2042
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1289P)²+0.2290P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2440
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.2029
_refine_ls_wR_factor_gt          0.1744
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.010

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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.77626(9) 0.05293(6) 0.16456(5) 0.0250(3) Uani 1 1 d . . .
S2 S 1.14149(19) -0.15716(14) 0.13232(12) 0.0254(4) Uani 1 1 d . . .
S1 S 0.7266(2) 0.35776(16) 0.23147(15) 0.0370(4) Uani 1 1 d . . .
O5 O 0.6531(6) -0.1817(5) 0.2322(4) 0.0429(11) Uani 1 1 d . . .
H5A H 0.7369 -0.2494 0.2262 0.052 Uiso 1 1 d R . .
H5B H 0.5592 -0.1710 0.1939 0.052 Uiso 1 1 d R . .
O1 O 1.0276(5) -0.0528(4) 0.1908(3) 0.0292(9) Uani 1 1 d . . .
O4 O 1.2185(6) -0.0564(4) 0.0039(4) 0.0364(10) Uani 1 1 d . . .
O2 O 1.2996(6) -0.2327(5) 0.2056(4) 0.0399(11) Uani 1 1 d . . .
O3 O 1.0246(6) -0.2680(4) 0.1298(4) 0.0395(10) Uani 1 1 d . . .
N1 N 0.7623(7) 0.0473(5) 0.3387(4) 0.0280(10) Uani 1 1 d . . .
N2 N 0.5479(6) 0.2070(5) 0.1358(4) 0.0248(9) Uani 1 1 d . . .
C6 C 0.5339(8) 0.3307(5) 0.1686(5) 0.0250(11) Uani 1 1 d . . .
C5 C 0.7413(8) 0.1780(6) 0.3617(5) 0.0304(12) Uani 1 1 d . . .
C7 C 0.3809(9) 0.4358(6) 0.1497(5) 0.0322(13) Uani 1 1 d . . .
H7 H 0.3747 0.5199 0.1727 0.039 Uiso 1 1 calc R . .
C4 C 0.7345(10) 0.1771(8) 0.4806(6) 0.0440(16) Uani 1 1 d . . .
H4 H 0.7190 0.2695 0.4928 0.053 Uiso 1 1 calc R . .
C9 C 0.2458(9) 0.2892(6) 0.0642(6) 0.0348(13) Uani 1 1 d . . .
H9 H 0.1481 0.2725 0.0292 0.042 Uiso 1 1 calc R . .
C2 C 0.7694(10) -0.0968(8) 0.5594(6) 0.0448(16) Uani 1 1 d . . .
H2 H 0.7790 -0.1925 0.6256 0.054 Uiso 1 1 calc R . .
C1 C 0.7740(9) -0.0894(7) 0.4376(6) 0.0383(14) Uani 1 1 d . . .
H1 H 0.7853 -0.1808 0.4239 0.046 Uiso 1 1 calc R . .
C8 C 0.2331(8) 0.4166(6) 0.0955(6) 0.0360(14) Uani 1 1 d . . .
H8 H 0.1278 0.4883 0.0806 0.043 Uiso 1 1 calc R . .
C10 C 0.4041(9) 0.1883(6) 0.0854(5) 0.0337(13) Uani 1 1 d . . .
H10 H 0.4124 0.1028 0.0639 0.040 Uiso 1 1 calc R . .
C3 C 0.7509(10) 0.0364(8) 0.5823(5) 0.0452(16) Uani 1 1 d . . .
H3 H 0.7493 0.0327 0.6631 0.054 Uiso 1 1 calc R . .
O6 O 0.3386(19) 0.4855(11) 0.4559(11) 0.173(5) Uani 1 1 d . . .
H6A H 0.2540 0.4979 0.5066 0.207 Uiso 1 1 d R . .
H6B H 0.4065 0.4017 0.4978 0.207 Uiso 1 1 d R . .
O7 O 0.035(3) 0.4823(17) 0.3806(15) 0.269(10) Uani 1 1 d . . .
H7A H 0.1398 0.5215 0.3497 0.323 Uiso 1 1 d R . .
H7B H -0.0459 0.5463 0.3231 0.323 Uiso 1 1 d R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0263(5) 0.0280(4) 0.0230(5) -0.0137(3) -0.0045(3) 0.0040(3)
S2 0.0248(8) 0.0290(7) 0.0272(7) -0.0161(5) -0.0083(6) 0.0047(5)
S1 0.0384(9) 0.0319(8) 0.0463(9) -0.0166(6) -0.0152(7) -0.0043(6)
O5 0.036(2) 0.045(2) 0.052(3) -0.022(2) -0.007(2) -0.0053(19)
O1 0.028(2) 0.0367(19) 0.031(2) -0.0234(16) -0.0060(17) 0.0058(16)
O4 0.039(3) 0.043(2) 0.030(2) -0.0205(18) -0.0026(19) 0.0046(18)
O2 0.037(2) 0.040(2) 0.047(3) -0.0174(19) -0.023(2) 0.0070(18)
O3 0.036(2) 0.035(2) 0.056(3) -0.0260(19) -0.010(2) -0.0006(18)
N1 0.028(3) 0.032(2) 0.023(2) -0.0128(18) -0.0037(19) 0.0056(19)
N2 0.024(2) 0.031(2) 0.023(2) -0.0132(17) -0.0040(18) -0.0002(18)
C6 0.026(3) 0.024(2) 0.024(3) -0.010(2) -0.001(2) -0.001(2)
C5 0.026(3) 0.038(3) 0.032(3) -0.017(2) -0.008(2) -0.001(2)
C7 0.038(3) 0.029(3) 0.031(3) -0.013(2) -0.002(3) -0.001(2)
C4 0.042(4) 0.062(4) 0.044(4) -0.038(3) -0.008(3) 0.000(3)
C9 0.032(3) 0.037(3) 0.040(3) -0.018(2) -0.013(3) 0.005(2)
C2 0.044(4) 0.056(4) 0.026(3) -0.005(3) -0.006(3) -0.007(3)
C1 0.043(4) 0.041(3) 0.029(3) -0.012(2) -0.009(3) 0.005(3)
C8 0.027(3) 0.035(3) 0.040(3) -0.010(3) -0.009(3) 0.008(2)
C10 0.040(3) 0.033(3) 0.031(3) -0.015(2) -0.009(3) -0.001(2)
C3 0.046(4) 0.076(4) 0.020(3) -0.027(3) -0.002(3) -0.005(3)
O6 0.209(12) 0.121(7) 0.181(12) -0.087(8) 0.062(10) -0.008(8)
O7 0.35(3) 0.167(12) 0.230(18) -0.013(11) -0.013(18) -0.061(15)

_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
Cu1 O1 1.944(4) . ?
Cu1 O4 1.952(4) 2_755 ?
Cu1 N1 2.003(5) . ?
Cu1 N2 2.009(4) . ?
Cu1 O5 2.301(4) . ?
S2 O3 1.450(4) . ?
S2 O2 1.461(4) . ?
S2 O4 1.489(4) . ?
S2 O1 1.495(4) . ?
S1 C6 1.767(6) . ?
S1 C5 1.779(6) . ?
O5 H5A 0.8298 . ?
O5 H5B 0.8433 . ?
O4 Cu1 1.952(4) 2_755 ?
N1 C5 1.350(7) . ?
N1 C1 1.352(7) . ?
N2 C10 1.338(7) . ?
N2 C6 1.356(6) . ?
C6 C7 1.355(8) . ?
C5 C4 1.380(9) . ?
C7 C8 1.392(8) . ?
C7 H7 0.9300 . ?
C4 C3 1.393(9) . ?
C4 H4 0.9300 . ?
C9 C10 1.364(8) . ?
C9 C8 1.381(8) . ?
C9 H9 0.9300 . ?
C2 C3 1.374(10) . ?
C2 C1 1.394(9) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C8 H8 0.9300 . ?
C10 H10 0.9300 . ?
C3 H3 0.9300 . ?
O6 H6A 0.8086 . ?
O6 H6B 0.8745 . ?
O7 H7A 0.8500 . ?
O7 H7B 0.9277 . ?

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
O1 Cu1 O4 95.45(17) . 2_755 ?
O1 Cu1 N1 85.90(17) . . ?
O4 Cu1 N1 178.13(18) 2_755 . ?
O1 Cu1 N2 165.64(17) . . ?
O4 Cu1 N2 89.58(17) 2_755 . ?
N1 Cu1 N2 89.41(18) . . ?
O1 Cu1 O5 89.93(16) . . ?
O4 Cu1 O5 85.35(17) 2_755 . ?
N1 Cu1 O5 93.36(17) . . ?
N2 Cu1 O5 103.90(17) . . ?
O3 S2 O2 112.0(2) . . ?
O3 S2 O4 111.9(3) . . ?
O2 S2 O4 108.4(3) . . ?
O3 S2 O1 110.3(2) . . ?
O2 S2 O1 107.3(2) . . ?
O4 S2 O1 106.8(2) . . ?
C6 S1 C5 99.3(2) . . ?
Cu1 O5 H5A 110.5 . . ?
Cu1 O5 H5B 109.0 . . ?
H5A O5 H5B 114.9 . . ?
S2 O1 Cu1 130.1(2) . . ?
S2 O4 Cu1 135.3(3) . 2_755 ?
C5 N1 C1 117.9(5) . . ?
C5 N1 Cu1 121.8(4) . . ?
C1 N1 Cu1 120.3(4) . . ?
C10 N2 C6 118.4(5) . . ?
C10 N2 Cu1 120.4(4) . . ?
C6 N2 Cu1 121.2(4) . . ?
C7 C6 N2 121.9(5) . . ?
C7 C6 S1 119.8(4) . . ?
N2 C6 S1 118.2(4) . . ?
N1 C5 C4 122.8(5) . . ?
N1 C5 S1 117.8(4) . . ?
C4 C5 S1 119.4(4) . . ?
C6 C7 C8 119.3(5) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C5 C4 C3 119.4(6) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C10 C9 C8 118.8(5) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C3 C2 C1 120.4(6) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
N1 C1 C2 121.6(6) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C9 C8 C7 118.8(5) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
N2 C10 C9 122.8(5) . . ?
N2 C10 H10 118.6 . . ?
C9 C10 H10 118.6 . . ?
C2 C3 C4 117.9(5) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
H6A O6 H6B 105.3 . . ?
H7A O7 H7B 102.6 . . ?

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         1.001
_refine_diff_density_min         -0.935
_refine_diff_density_rms         0.163
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1505821'
_audit_update_record             
;
2016-09-22 deposited with the CCDC.
2018-01-22 downloaded from the CCDC.
;
_chemical_formula_moiety         'C10 H8 Cl2 Co N2 S'
_chemical_formula_sum            'C10 H8 Cl2 Co N2 S'
_chemical_formula_weight         318.07
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Co 0.35655 0.96576 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Cl 0.14873 0.16029 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
S 0.12424 0.12443 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_cell_length_a                   12.289(3)
_cell_length_b                   7.6775(15)
_cell_length_c                   14.314(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.80(3)
_cell_angle_gamma                90
_cell_volume                     1262.5(5)
_cell_formula_units_Z            4
_exptl_crystal_description       Block
_exptl_crystal_colour            pink
_diffrn_ambient_temperature      277(2)
_cell_measurement_temperature    277(2)
_cell_measurement_reflns_used    530
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      27.14
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_exptl_absorpt_coefficient_mu    1.919
_exptl_crystal_density_diffrn    1.6734
_exptl_crystal_F_000             639.2121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.329
_exptl_absorpt_correction_T_max  0.464
_exptl_absorpt_process_details   'SADABS v. 2.03 (Sheldrick, 2008)'
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11774
_diffrn_reflns_theta_full        27.433606
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         3.04
_diffrn_measured_fraction_theta_full 0.998606
_diffrn_measured_fraction_theta_max 0.998606
_diffrn_radiation_probe          ?
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku ip'
_diffrn_measurement_method       'φ and ω'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -15
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2401
_reflns_number_total             2865
_reflns_threshold_expression     I>=2u(I)
_refine_diff_density_max         0.435227
_refine_diff_density_min         -0.395557
_refine_diff_density_rms         0.059624
_refine_ls_d_res_high            0.771325
_refine_ls_d_res_low             6.690547
_refine_ls_goodness_of_fit_ref   0.873674
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2865
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.036159
_refine_ls_R_factor_gt           0.028651
_refine_ls_restrained_S_all      0.873674
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.113488
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_refinement_flags_posn
Co1 Co 0.75017(2) 0.89044(4) 0.22282(2) 0.04457(14) Uani 1.000000 .
S1 S 0.73356(6) 0.84563(10) 0.44375(5) 0.0631(2) Uani 1.000000 .
Cl1 Cl 0.84988(6) 0.64315(8) 0.23618(5) 0.05924(19) Uani 1.000000 .
Cl2 Cl 0.71480(6) 1.04124(9) 0.08165(4) 0.0656(2) Uani 1.000000 .
N2 N 0.59772(16) 0.8784(2) 0.24873(14) 0.0457(4) Uani 1.000000 .
N1 N 0.83184(14) 1.0489(2) 0.34052(12) 0.0422(4) Uani 1.000000 .
C9 C 0.4930(2) 0.8911(3) 0.1738(2) 0.0561(6) Uani 1.000000 .
C2 C 0.81766(18) 1.0251(3) 0.42915(15) 0.0448(5) Uani 1.000000 .
C3 C 0.8754(2) 1.1241(3) 0.51205(18) 0.0540(6) Uani 1.000000 .
C7 C 0.5986(2) 0.8683(3) 0.34275(18) 0.0480(5) Uani 1.000000 .
C6 C 0.90374(19) 1.1774(3) 0.33426(18) 0.0503(5) Uani 1.000000 .
C12 C 0.4972(2) 0.8624(3) 0.3636(2) 0.0613(6) Uani 1.000000 .
C10 C 0.3901(2) 0.8878(4) 0.1906(3) 0.0676(8) Uani 1.000000 .
C4 C 0.9522(2) 1.2510(3) 0.5051(2) 0.0617(6) Uani 1.000000 .
C0aa C 0.9658(2) 1.2784(3) 0.4150(2) 0.0586(6) Uani 1.000000 .
C11 C 0.3924(2) 0.8715(4) 0.2865(3) 0.0686(8) Uani 1.000000 .
H9 H 0.4909(2) 0.9023(3) 0.1085(2) 0.0673(7) Uiso 1.000000 R
H12 H 0.5001(2) 0.8525(3) 0.4292(2) 0.0736(8) Uiso 1.000000 R
H11 H 0.3233(2) 0.8665(4) 0.2992(3) 0.0824(9) Uiso 1.000000 R
H10 H 0.3196(2) 0.8967(4) 0.1375(3) 0.0811(9) Uiso 1.000000 R
H6 H 0.91169(19) 1.1985(3) 0.27303(18) 0.0604(6) Uiso 1.000000 R
H0aa H 1.0163(2) 1.3640(3) 0.4087(2) 0.0703(7) Uiso 1.000000 R
H4 H 0.9941(2) 1.3170(3) 0.5608(2) 0.0741(8) Uiso 1.000000 R
H3 H 0.8630(2) 1.1061(3) 0.57175(18) 0.0648(7) Uiso 1.000000 R

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Co1 0.0451(2) 0.0564(2) 0.03381(19) -0.00201(11) 0.01599(14) -0.00252(11)
S1 0.0627(4) 0.0822(4) 0.0416(3) -0.0088(3) 0.0150(3) 0.0185(3)
Cl1 0.0599(4) 0.0634(4) 0.0547(4) 0.0072(3) 0.0207(3) -0.0035(3)
Cl2 0.0863(5) 0.0745(4) 0.0402(3) 0.0022(3) 0.0275(3) 0.0068(3)
N2 0.0427(9) 0.0520(10) 0.0419(10) -0.0026(7) 0.0144(8) 0.0024(7)
N1 0.0407(8) 0.0491(9) 0.0357(8) 0.0028(7) 0.0123(7) 0.0007(7)
C9 0.0486(13) 0.0630(14) 0.0511(14) -0.0049(10) 0.0108(10) 0.0049(10)
C2 0.0428(10) 0.0535(12) 0.0356(9) 0.0094(9) 0.0108(8) 0.0049(8)
C3 0.0606(14) 0.0602(13) 0.0367(11) 0.0134(10) 0.0119(10) -0.0035(9)
C7 0.0505(12) 0.0504(11) 0.0462(12) -0.0047(9) 0.0209(10) 0.0030(9)
C6 0.0463(11) 0.0538(12) 0.0495(12) 0.0029(10) 0.0153(9) 0.0058(10)
C12 0.0627(15) 0.0676(15) 0.0650(16) -0.0073(12) 0.0366(13) 0.0023(12)
C10 0.0446(13) 0.0705(17) 0.080(2) -0.0033(11) 0.0123(13) 0.0120(13)
C4 0.0634(14) 0.0521(13) 0.0549(14) 0.0066(12) 0.0028(11) -0.0128(11)
C0aa 0.0552(13) 0.0488(11) 0.0626(15) -0.0002(11) 0.0097(11) -0.0002(11)
C11 0.0502(14) 0.0724(17) 0.092(2) -0.0028(11) 0.0364(14) 0.0082(14)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Co1 Cl1 2.2307(8) .
Co1 Cl2 2.2336(8) .
Co1 N2 2.037(2) .
Co1 N1 2.0311(18) .
S1 C2 1.779(2) .
S1 C7 1.780(3) .
N2 C9 1.355(3) .
N2 C7 1.344(3) .
N1 C2 1.353(3) .
N1 C6 1.348(3) .
C9 C10 1.368(4) .
C9 H9 0.9300 .
C2 C3 1.375(3) .
C3 C4 1.385(4) .
C3 H3 0.9300 .
C7 C12 1.381(3) .
C6 C0aa 1.376(3) .
C6 H6 0.9300 .
C12 C11 1.368(4) .
C12 H12 0.9300 .
C10 C11 1.369(5) .
C10 H10 0.9300 .
C4 C0aa 1.375(4) .
C4 H4 0.9300 .
C0aa H0aa 0.9300 .
C11 H11 0.9300 .

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
Cl2 Co1 Cl1 116.31(3) . .
N2 Co1 Cl1 117.30(5) . .
N2 Co1 Cl2 106.98(5) . .
N1 Co1 Cl1 110.13(5) . .
N1 Co1 Cl2 108.66(5) . .
N1 Co1 N2 95.25(7) . .
C7 S1 C2 103.98(10) . .
C9 N2 Co1 121.97(17) . .
C7 N2 Co1 120.25(15) . .
C7 N2 C9 117.7(2) . .
C2 N1 Co1 120.44(15) . .
C6 N1 Co1 121.71(15) . .
C6 N1 C2 117.83(19) . .
C10 C9 N2 122.5(3) . .
H9 C9 N2 118.75(14) . .
H9 C9 C10 118.75(18) . .
N1 C2 S1 119.24(16) . .
C3 C2 S1 118.02(18) . .
C3 C2 N1 122.4(2) . .
C4 C3 C2 118.9(2) . .
H3 C3 C2 120.56(15) . .
H3 C3 C4 120.56(15) . .
N2 C7 S1 119.54(17) . .
C12 C7 S1 118.2(2) . .
C12 C7 N2 122.1(2) . .
C0aa C6 N1 122.5(2) . .
H6 C6 N1 118.75(13) . .
H6 C6 C0aa 118.75(16) . .
C11 C12 C7 119.2(3) . .
H12 C12 C7 120.42(16) . .
H12 C12 C11 120.42(17) . .
C11 C10 C9 119.1(3) . .
H10 C10 C9 120.44(18) . .
H10 C10 C11 120.44(17) . .
C0aa C4 C3 119.2(2) . .
H4 C4 C3 120.40(15) . .
H4 C4 C0aa 120.40(15) . .
C4 C0aa C6 119.1(2) . .
H0aa C0aa C6 120.44(16) . .
H0aa C0aa C4 120.44(15) . .
C10 C11 C12 119.4(3) . .
H11 C11 C12 120.28(17) . .
H11 C11 C10 120.28(16) . .
