# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_apx1821
_database_code_depnum_ccdc_archive 'CCDC 1429177'
_audit_update_record             
;
2015-11-30 deposited with the CCDC.
2015-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H22 Cl2 Co N2 O S'
_chemical_formula_weight         396.23

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

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

_cell_length_a                   7.127(2)
_cell_length_b                   11.307(4)
_cell_length_c                   11.422(4)
_cell_angle_alpha                98.291(3)
_cell_angle_beta                 107.707(3)
_cell_angle_gamma                94.031(4)
_cell_volume                     861.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(1)
_cell_measurement_reflns_used    6671
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      28.55

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             410
_exptl_absorpt_coefficient_mu    1.427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6742
_exptl_absorpt_correction_T_max  0.8705
_exptl_absorpt_process_details   'SADABS v. 2.03 (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 with APEXII CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9966
_diffrn_reflns_av_R_equivalents  0.0137
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         28.58
_reflns_number_total             4033
_reflns_number_gt                3792
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II, v. 7.0 (Bruker AXS, 2009)'
_computing_cell_refinement       'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_publication_material  'SHELXTL, v. 6.14, (Bruker AXS, 2000)'

_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)+(0.0336P)²+1.7349P] 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         4033
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0854
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.45607(4) 0.71156(3) -0.06585(3) 0.01201(9) Uani 1 1 d . . .
S1 S 0.37111(9) 0.89272(5) 0.33841(6) 0.01986(13) Uani 1 1 d . . .
Cl1 Cl 0.29194(8) 0.86854(5) -0.10731(6) 0.02145(13) Uani 1 1 d . . .
Cl2 Cl 0.25517(8) 0.54172(5) -0.09674(5) 0.01771(12) Uani 1 1 d . . .
N1 N 0.6959(3) 0.70277(16) -0.13614(16) 0.0110(3) Uani 1 1 d . . .
N2 N 0.6637(3) 0.75865(18) 0.11005(18) 0.0163(4) Uani 1 1 d . . .
H2 H 0.6975 0.6901 0.1400 0.020 Uiso 1 1 calc R . .
O1 O 0.5522(2) 0.65161(15) -0.40518(15) 0.0191(3) Uani 1 1 d . . .
C1 C 0.6983(3) 0.58320(19) -0.2100(2) 0.0154(4) Uani 1 1 d . . .
H1A H 0.6830 0.5204 -0.1629 0.018 Uiso 1 1 calc R . .
H1B H 0.8249 0.5804 -0.2250 0.018 Uiso 1 1 calc R . .
C2 C 0.5324(3) 0.5611(2) -0.3333(2) 0.0177(4) Uani 1 1 d . . .
H2A H 0.5353 0.4827 -0.3797 0.021 Uiso 1 1 calc R . .
H2B H 0.4057 0.5612 -0.3182 0.021 Uiso 1 1 calc R . .
C3 C 0.7080(3) 0.7960(2) -0.2141(2) 0.0137(4) Uani 1 1 d . . .
H3A H 0.8355 0.7999 -0.2283 0.016 Uiso 1 1 calc R . .
H3B H 0.6973 0.8741 -0.1703 0.016 Uiso 1 1 calc R . .
C4 C 0.5435(3) 0.7667(2) -0.3381(2) 0.0181(4) Uani 1 1 d . . .
H4A H 0.4162 0.7674 -0.3238 0.022 Uiso 1 1 calc R . .
H4B H 0.5546 0.8279 -0.3877 0.022 Uiso 1 1 calc R . .
C5 C 0.8729(3) 0.7267(2) -0.0207(2) 0.0133(4) Uani 1 1 d . . .
H5A H 0.9875 0.7589 -0.0401 0.016 Uiso 1 1 calc R . .
H5B H 0.9013 0.6518 0.0093 0.016 Uiso 1 1 calc R . .
C6 C 0.8357(3) 0.8151(2) 0.0799(2) 0.0157(4) Uani 1 1 d . . .
H6A H 0.9523 0.8321 0.1535 0.019 Uiso 1 1 calc R . .
H6B H 0.8053 0.8901 0.0505 0.019 Uiso 1 1 calc R . .
C7 C 0.6127(3) 0.8401(2) 0.2057(2) 0.0180(4) Uani 1 1 d . . .
H7A H 0.5739 0.9131 0.1746 0.022 Uiso 1 1 calc R . .
H7B H 0.7276 0.8621 0.2800 0.022 Uiso 1 1 calc R . .
C8 C 0.4427(3) 0.7783(2) 0.2382(2) 0.0182(4) Uani 1 1 d . . .
H8A H 0.4859 0.7122 0.2812 0.022 Uiso 1 1 calc R . .
H8B H 0.3323 0.7471 0.1633 0.022 Uiso 1 1 calc R . .
C9 C 0.2018(3) 0.8127(2) 0.3913(2) 0.0152(4) Uani 1 1 d . . .
C10 C 0.1241(3) 0.6930(2) 0.3459(2) 0.0185(4) Uani 1 1 d . . .
H10 H 0.1590 0.6494 0.2818 0.022 Uiso 1 1 calc R . .
C11 C -0.0065(4) 0.6387(2) 0.3969(3) 0.0260(5) Uani 1 1 d . . .
H11 H -0.0568 0.5580 0.3674 0.031 Uiso 1 1 calc R . .
C12 C -0.0628(4) 0.7026(3) 0.4910(3) 0.0291(6) Uani 1 1 d . . .
H12 H -0.1500 0.6653 0.5245 0.035 Uiso 1 1 calc R . .
C13 C 0.0120(4) 0.8225(3) 0.5346(2) 0.0261(5) Uani 1 1 d . . .
H13 H -0.0261 0.8662 0.5972 0.031 Uiso 1 1 calc R . .
C14 C 0.1431(4) 0.8778(2) 0.4858(2) 0.0210(5) Uani 1 1 d . . .
H14 H 0.1926 0.9585 0.5157 0.025 Uiso 1 1 calc R . .


_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
Co1 N2 2.069(2) . ?
Co1 N1 2.1005(19) . ?
Co1 Cl1 2.2227(8) . ?
Co1 Cl2 2.2301(8) . ?
S1 C9 1.757(2) . ?
S1 C8 1.807(2) . ?
N1 C3 1.488(3) . ?
N1 C1 1.491(3) . ?
N1 C5 1.497(3) . ?
N2 C7 1.474(3) . ?
N2 C6 1.496(3) . ?
O1 C2 1.426(3) . ?
O1 C4 1.427(3) . ?
C1 C2 1.513(3) . ?
C3 C4 1.513(3) . ?
C5 C6 1.510(3) . ?
C7 C8 1.524(3) . ?
C9 C10 1.387(3) . ?
C9 C14 1.404(3) . ?
C10 C11 1.392(3) . ?
C11 C12 1.384(4) . ?
C12 C13 1.383(4) . ?
C13 C14 1.382(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
_geom_angle_publ_flag
N2 Co1 N1 87.14(8) . . ?
N2 Co1 Cl1 108.09(6) . . ?
N1 Co1 Cl1 113.45(5) . . ?
N2 Co1 Cl2 115.40(6) . . ?
N1 Co1 Cl2 117.27(5) . . ?
Cl1 Co1 Cl2 112.77(3) . . ?
C9 S1 C8 103.94(11) . . ?
C3 N1 C1 107.96(17) . . ?
C3 N1 C5 109.26(16) . . ?
C1 N1 C5 109.10(16) . . ?
C3 N1 Co1 113.05(13) . . ?
C1 N1 Co1 114.07(13) . . ?
C5 N1 Co1 103.22(12) . . ?
C7 N2 C6 111.18(18) . . ?
C7 N2 Co1 118.28(15) . . ?
C6 N2 Co1 101.10(13) . . ?
C2 O1 C4 109.45(17) . . ?
N1 C1 C2 110.57(18) . . ?
O1 C2 C1 110.79(18) . . ?
N1 C3 C4 110.59(18) . . ?
O1 C4 C3 111.44(18) . . ?
N1 C5 C6 110.67(17) . . ?
N2 C6 C5 107.21(18) . . ?
N2 C7 C8 109.98(18) . . ?
C7 C8 S1 105.81(16) . . ?
C10 C9 C14 119.3(2) . . ?
C10 C9 S1 124.79(18) . . ?
C14 C9 S1 115.89(18) . . ?
C9 C10 C11 119.5(2) . . ?
C12 C11 C10 121.1(2) . . ?
C13 C12 C11 119.3(2) . . ?
C14 C13 C12 120.5(2) . . ?
C13 C14 C9 120.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.912
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.775
_refine_diff_density_min         -0.887
_refine_diff_density_rms         0.080
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0

#===========END======================
####################################################################### 
# 
# 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_apx1844
_database_code_depnum_ccdc_archive 'CCDC 1429178'
_audit_update_record             
;
2015-11-30 deposited with the CCDC.
2015-12-11 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT029_apx1844             
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.919 Note  
RESPONSE:  Missing data doesn't significantly affect structure quality 
with regards to connectivity and reasonable bond distances, angles, and
estimated standard deviations.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H30 Cl2 N2 Ni O2 S'
_chemical_formula_weight         456.10

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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'

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

_cell_length_a                   6.484(3)
_cell_length_b                   8.921(4)
_cell_length_c                   19.032(9)
_cell_angle_alpha                98.492(7)
_cell_angle_beta                 98.646(6)
_cell_angle_gamma                106.341(6)
_cell_volume                     1023.2(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(1)
_cell_measurement_reflns_used    854
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      23.74

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    1.325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7776
_exptl_absorpt_correction_T_max  0.9740
_exptl_absorpt_process_details   'SADABS v. 2.03 (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 with APEXII CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5970
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0869
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         28.46
_reflns_number_total             4198
_reflns_number_gt                2697
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II, v. 7.0 (Bruker AXS, 2009)'
_computing_cell_refinement       'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_publication_material  'SHELXTL, v. 6.14, (Bruker AXS, 2000)'

_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)+(0.0691P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4198
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0655
_refine_ls_wR_factor_ref         0.1539
_refine_ls_wR_factor_gt          0.1311
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.91656(10) 0.27849(8) 0.29286(3) 0.0160(2) Uani 1 1 d . . .
Cl1 Cl 1.1174(2) 0.12073(16) 0.23786(7) 0.0235(3) Uani 1 1 d . . .
Cl2 Cl 0.70117(19) 0.43956(15) 0.33719(7) 0.0204(3) Uani 1 1 d . . .
S1 S 0.9433(2) 0.39548(17) 0.18413(7) 0.0236(3) Uani 1 1 d . . .
N1 N 1.2032(6) 0.4602(5) 0.3370(2) 0.0200(10) Uani 1 1 d . . .
H1 H 1.3140 0.4246 0.3247 0.024 Uiso 1 1 calc R . .
N2 N 0.9897(6) 0.2015(5) 0.3993(2) 0.0181(10) Uani 1 1 d . . .
O1 O 0.6474(6) -0.0689(4) 0.42092(19) 0.0252(9) Uani 1 1 d . . .
O2 O 0.6096(5) 0.1140(4) 0.24472(19) 0.0179(8) Uani 1 1 d . . .
C1 C 0.7501(9) 0.5066(7) 0.1653(3) 0.0287(14) Uani 1 1 d . . .
H1A H 0.6010 0.4347 0.1552 0.034 Uiso 1 1 calc R . .
H1B H 0.7671 0.5878 0.2076 0.034 Uiso 1 1 calc R . .
C2 C 0.7901(8) 0.5834(7) 0.1016(3) 0.0247(13) Uani 1 1 d . . .
C3 C 0.7407(9) 0.4931(7) 0.0324(3) 0.0277(14) Uani 1 1 d . . .
H3 H 0.6796 0.3830 0.0251 0.033 Uiso 1 1 calc R . .
C4 C 0.7802(9) 0.5630(8) -0.0261(3) 0.0345(15) Uani 1 1 d . . .
H4 H 0.7474 0.5005 -0.0724 0.041 Uiso 1 1 calc R . .
C5 C 0.8685(10) 0.7258(8) -0.0156(4) 0.0423(18) Uani 1 1 d . . .
H5 H 0.8943 0.7733 -0.0551 0.051 Uiso 1 1 calc R . .
C6 C 0.9186(10) 0.8186(8) 0.0524(4) 0.0385(16) Uani 1 1 d . . .
H6 H 0.9766 0.9288 0.0591 0.046 Uiso 1 1 calc R . .
C7 C 0.8825(9) 0.7475(7) 0.1113(3) 0.0284(14) Uani 1 1 d . . .
H7 H 0.9204 0.8102 0.1577 0.034 Uiso 1 1 calc R . .
C8 C 1.1931(8) 0.5582(7) 0.2255(3) 0.0290(14) Uani 1 1 d . . .
H8A H 1.3189 0.5270 0.2153 0.035 Uiso 1 1 calc R . .
H8B H 1.1919 0.6504 0.2043 0.035 Uiso 1 1 calc R . .
C9 C 1.2154(9) 0.6029(7) 0.3065(3) 0.0304(14) Uani 1 1 d . . .
H9A H 1.3548 0.6843 0.3276 0.037 Uiso 1 1 calc R . .
H9B H 1.0986 0.6449 0.3174 0.037 Uiso 1 1 calc R . .
C10 C 1.2305(8) 0.4801(6) 0.4156(3) 0.0252(13) Uani 1 1 d . . .
H10A H 1.1183 0.5204 0.4321 0.030 Uiso 1 1 calc R . .
H10B H 1.3732 0.5547 0.4391 0.030 Uiso 1 1 calc R . .
C11 C 1.2100(8) 0.3177(6) 0.4331(3) 0.0253(13) Uani 1 1 d . . .
H11A H 1.3223 0.2787 0.4158 0.030 Uiso 1 1 calc R . .
H11B H 1.2338 0.3265 0.4853 0.030 Uiso 1 1 calc R . .
C12 C 0.8355(8) 0.2154(6) 0.4483(3) 0.0196(12) Uani 1 1 d . . .
H12A H 0.8099 0.3178 0.4499 0.023 Uiso 1 1 calc R . .
H12B H 0.9021 0.2120 0.4970 0.023 Uiso 1 1 calc R . .
C13 C 0.6181(9) 0.0842(7) 0.4245(3) 0.0259(13) Uani 1 1 d . . .
H13A H 0.5240 0.0977 0.4584 0.031 Uiso 1 1 calc R . .
H13B H 0.5464 0.0915 0.3771 0.031 Uiso 1 1 calc R . .
C14 C 1.0101(8) 0.0393(6) 0.3955(3) 0.0237(13) Uani 1 1 d . . .
H14A H 1.0817 0.0308 0.4426 0.028 Uiso 1 1 calc R . .
H14B H 1.1012 0.0218 0.3610 0.028 Uiso 1 1 calc R . .
C15 C 0.7887(8) -0.0875(6) 0.3727(3) 0.0238(13) Uani 1 1 d . . .
H15A H 0.7208 -0.0827 0.3244 0.029 Uiso 1 1 calc R . .
H15B H 0.8087 -0.1917 0.3706 0.029 Uiso 1 1 calc R . .
C16 C 0.5376(9) -0.0224(7) 0.1844(3) 0.0257(13) Uani 1 1 d . . .
H16A H 0.3941 -0.0903 0.1870 0.031 Uiso 1 1 calc R . .
H16B H 0.6390 -0.0840 0.1885 0.031 Uiso 1 1 calc R . .
C17 C 0.5255(10) 0.0280(8) 0.1125(3) 0.0387(16) Uani 1 1 d . . .
H17A H 0.4300 0.0928 0.1091 0.058 Uiso 1 1 calc R . .
H17B H 0.4691 -0.0648 0.0742 0.058 Uiso 1 1 calc R . .
H17C H 0.6695 0.0882 0.1081 0.058 Uiso 1 1 calc R . .
H2 H 0.511(13) 0.152(9) 0.245(4) 0.080 Uiso 1 1 d . . .


_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
Ni1 N1 2.054(4) . ?
Ni1 O2 2.089(4) . ?
Ni1 N2 2.259(4) . ?
Ni1 Cl1 2.4038(15) . ?
Ni1 Cl2 2.4192(15) . ?
Ni1 S1 2.4588(18) . ?
S1 C8 1.818(6) . ?
S1 C1 1.830(5) . ?
N1 C10 1.457(7) . ?
N1 C9 1.463(7) . ?
N2 C14 1.482(6) . ?
N2 C12 1.485(6) . ?
N2 C11 1.491(6) . ?
O1 C15 1.416(6) . ?
O1 C13 1.424(6) . ?
O2 C16 1.457(6) . ?
C1 C2 1.499(8) . ?
C2 C3 1.379(7) . ?
C2 C7 1.389(7) . ?
C3 C4 1.376(8) . ?
C4 C5 1.374(8) . ?
C5 C6 1.369(9) . ?
C6 C7 1.385(8) . ?
C8 C9 1.508(8) . ?
C10 C11 1.509(7) . ?
C12 C13 1.512(7) . ?
C14 C15 1.511(7) . ?
C16 C17 1.501(8) . ?

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
N1 Ni1 O2 173.38(15) . . ?
N1 Ni1 N2 82.72(16) . . ?
O2 Ni1 N2 101.77(15) . . ?
N1 Ni1 Cl1 90.53(12) . . ?
O2 Ni1 Cl1 94.22(10) . . ?
N2 Ni1 Cl1 91.08(11) . . ?
N1 Ni1 Cl2 91.29(12) . . ?
O2 Ni1 Cl2 83.60(10) . . ?
N2 Ni1 Cl2 94.01(11) . . ?
Cl1 Ni1 Cl2 174.78(5) . . ?
N1 Ni1 S1 83.50(13) . . ?
O2 Ni1 S1 92.54(11) . . ?
N2 Ni1 S1 164.72(11) . . ?
Cl1 Ni1 S1 82.48(5) . . ?
Cl2 Ni1 S1 92.86(5) . . ?
C8 S1 C1 100.7(3) . . ?
C8 S1 Ni1 95.45(19) . . ?
C1 S1 Ni1 114.33(19) . . ?
C10 N1 C9 116.9(4) . . ?
C10 N1 Ni1 107.1(3) . . ?
C9 N1 Ni1 112.6(3) . . ?
C14 N2 C12 106.4(4) . . ?
C14 N2 C11 107.5(4) . . ?
C12 N2 C11 108.8(4) . . ?
C14 N2 Ni1 117.0(3) . . ?
C12 N2 Ni1 115.0(3) . . ?
C11 N2 Ni1 101.7(3) . . ?
C15 O1 C13 109.5(4) . . ?
C16 O2 Ni1 132.9(3) . . ?
C2 C1 S1 110.4(4) . . ?
C3 C2 C7 118.4(5) . . ?
C3 C2 C1 121.0(5) . . ?
C7 C2 C1 120.6(5) . . ?
C4 C3 C2 121.2(6) . . ?
C5 C4 C3 119.6(6) . . ?
C6 C5 C4 120.6(6) . . ?
C5 C6 C7 119.6(6) . . ?
C6 C7 C2 120.6(6) . . ?
C9 C8 S1 111.8(4) . . ?
N1 C9 C8 108.5(5) . . ?
N1 C10 C11 106.7(4) . . ?
N2 C11 C10 111.6(4) . . ?
N2 C12 C13 112.5(4) . . ?
O1 C13 C12 111.2(4) . . ?
N2 C14 C15 111.6(4) . . ?
O1 C15 C14 112.2(4) . . ?
O2 C16 C17 111.9(5) . . ?

_diffrn_measured_fraction_theta_max 0.812
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.919
_refine_diff_density_max         0.649
_refine_diff_density_min         -0.697
_refine_diff_density_rms         0.124
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0

#============END===================
####################################################################### 
# 
# 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_apx2032
_database_code_depnum_ccdc_archive 'CCDC 1429179'
_audit_update_record             
;
2015-11-30 deposited with the CCDC.
2015-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H44 Cl4 Mn2 N4 O2 S2'
_chemical_formula_weight         784.47

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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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'

_cell_length_a                   12.171(3)
_cell_length_b                   11.594(3)
_cell_length_c                   24.657(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.927(2)
_cell_angle_gamma                90.00
_cell_volume                     3416.3(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(1)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      26.18

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1624
_exptl_absorpt_coefficient_mu    1.207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7943
_exptl_absorpt_correction_T_max  0.9311
_exptl_absorpt_process_details   'SADABS v. 2.03 (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 with APEXII CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34216
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         26.33
_reflns_number_total             6901
_reflns_number_gt                5742
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II, v. 7.0 (Bruker AXS, 2009)'
_computing_cell_refinement       'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_publication_material  'SHELXTL, v. 6.14, (Bruker AXS, 2000)'

_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)+(0.0553P)²+0.0000P] 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         6901
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1061
_refine_ls_wR_factor_gt          0.0996
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.59389(3) 1.10118(3) 0.966194(15) 0.01227(11) Uani 1 1 d . . .
Mn2 Mn 0.71020(3) 0.85123(3) 0.932141(16) 0.01335(11) Uani 1 1 d . . .
S1 S 0.84963(5) 1.15972(5) 1.19671(3) 0.01688(15) Uani 1 1 d . . .
S2 S 1.00539(6) 0.59512(6) 1.06974(3) 0.02176(17) Uani 1 1 d . . .
Cl1 Cl 0.54569(5) 0.96816(5) 0.88407(2) 0.01502(14) Uani 1 1 d . . .
Cl2 Cl 0.79411(5) 1.05539(5) 0.96219(2) 0.01481(14) Uani 1 1 d . . .
Cl3 Cl 0.61095(5) 0.90013(5) 1.02336(2) 0.01387(14) Uani 1 1 d . . .
Cl4 Cl 0.61995(6) 0.66547(5) 0.91694(3) 0.02110(16) Uani 1 1 d . . .
N1 N 0.63719(17) 1.19881(18) 1.04614(8) 0.0132(4) Uani 1 1 d . . .
H1 H 0.5771 1.1903 1.0629 0.016 Uiso 1 1 calc R . .
N2 N 0.57622(17) 1.29045(18) 0.93361(8) 0.0154(5) Uani 1 1 d . . .
N3 N 0.86151(17) 0.77286(19) 0.98794(9) 0.0156(5) Uani 1 1 d . . .
H3 H 0.8469 0.6959 0.9883 0.019 Uiso 1 1 calc R . .
N4 N 0.82660(17) 0.82210(18) 0.86698(9) 0.0157(5) Uani 1 1 d . . .
O1 O 0.58503(17) 1.30210(18) 0.81715(8) 0.0275(5) Uani 1 1 d . . .
O2 O 0.74548(16) 0.93741(17) 0.76231(7) 0.0230(4) Uani 1 1 d . . .
C1 C 0.8618(2) 1.0084(2) 1.20707(10) 0.0146(5) Uani 1 1 d . . .
C2 C 0.7957(2) 0.9252(2) 1.17574(11) 0.0179(6) Uani 1 1 d . . .
H2 H 0.7403 0.9473 1.1462 0.022 Uiso 1 1 calc R . .
C3 C 0.8125(2) 0.8092(2) 1.18864(11) 0.0213(6) Uani 1 1 d . . .
H3A H 0.7686 0.7540 1.1673 0.026 Uiso 1 1 calc R . .
C4 C 0.8937(2) 0.7749(2) 1.23282(12) 0.0222(6) Uani 1 1 d . . .
H4 H 0.9037 0.6971 1.2415 0.027 Uiso 1 1 calc R . .
C5 C 0.9603(2) 0.8578(2) 1.26415(12) 0.0223(6) Uani 1 1 d . . .
H5 H 1.0145 0.8351 1.2941 0.027 Uiso 1 1 calc R . .
C6 C 0.9462(2) 0.9737(2) 1.25104(11) 0.0182(6) Uani 1 1 d . . .
H6 H 0.9926 1.0284 1.2713 0.022 Uiso 1 1 calc R . .
C7 C 0.7217(2) 1.1802(2) 1.14676(10) 0.0165(5) Uani 1 1 d . . .
H7A H 0.6649 1.1285 1.1556 0.020 Uiso 1 1 calc R . .
H7B H 0.6956 1.2586 1.1497 0.020 Uiso 1 1 calc R . .
C8 C 0.7351(2) 1.1582(2) 1.08707(10) 0.0171(6) Uani 1 1 d . . .
H8A H 0.8018 1.1973 1.0805 0.020 Uiso 1 1 calc R . .
H8B H 0.7451 1.0762 1.0819 0.020 Uiso 1 1 calc R . .
C9 C 0.6429(2) 1.3232(2) 1.03425(11) 0.0188(6) Uani 1 1 d . . .
H9A H 0.7178 1.3423 1.0290 0.023 Uiso 1 1 calc R . .
H9B H 0.6280 1.3671 1.0656 0.023 Uiso 1 1 calc R . .
C10 C 0.5595(2) 1.3565(2) 0.98327(11) 0.0207(6) Uani 1 1 d . . .
H10A H 0.4844 1.3427 0.9897 0.025 Uiso 1 1 calc R . .
H10B H 0.5665 1.4383 0.9764 0.025 Uiso 1 1 calc R . .
C11 C 0.6754(2) 1.3347(2) 0.91297(11) 0.0188(6) Uani 1 1 d . . .
H11A H 0.7429 1.3171 0.9395 0.023 Uiso 1 1 calc R . .
H11B H 0.6700 1.4179 0.9090 0.023 Uiso 1 1 calc R . .
C12 C 0.6824(2) 1.2809(3) 0.85799(12) 0.0257(7) Uani 1 1 d . . .
H12A H 0.7472 1.3115 0.8453 0.031 Uiso 1 1 calc R . .
H12B H 0.6927 1.1983 0.8628 0.031 Uiso 1 1 calc R . .
C13 C 0.4885(2) 1.2598(3) 0.83518(12) 0.0270(7) Uani 1 1 d . . .
H13A H 0.4943 1.1767 0.8397 0.032 Uiso 1 1 calc R . .
H13B H 0.4226 1.2764 0.8074 0.032 Uiso 1 1 calc R . .
C14 C 0.4764(2) 1.3146(2) 0.88935(11) 0.0224(6) Uani 1 1 d . . .
H14A H 0.4675 1.3973 0.8844 0.027 Uiso 1 1 calc R . .
H14B H 0.4097 1.2848 0.9006 0.027 Uiso 1 1 calc R . .
C15 C 0.9458(2) 0.5419(2) 1.12545(11) 0.0172(5) Uani 1 1 d . . .
C16 C 1.0168(2) 0.5053(2) 1.17343(11) 0.0209(6) Uani 1 1 d . . .
H16 H 1.0940 0.5105 1.1764 0.025 Uiso 1 1 calc R . .
C17 C 0.9715(3) 0.4609(2) 1.21701(12) 0.0247(6) Uani 1 1 d . . .
H17 H 1.0187 0.4356 1.2490 0.030 Uiso 1 1 calc R . .
C18 C 0.8569(3) 0.4544(2) 1.21291(13) 0.0297(7) Uani 1 1 d . . .
H18 H 0.8272 0.4254 1.2422 0.036 Uiso 1 1 calc R . .
C19 C 0.7861(3) 0.4911(2) 1.16505(13) 0.0283(7) Uani 1 1 d . . .
H19 H 0.7090 0.4870 1.1625 0.034 Uiso 1 1 calc R . .
C20 C 0.8298(2) 0.5340(2) 1.12088(12) 0.0236(6) Uani 1 1 d . . .
H20 H 0.7823 0.5572 1.0886 0.028 Uiso 1 1 calc R . .
C21 C 0.9969(2) 0.7506(2) 1.07938(11) 0.0194(6) Uani 1 1 d . . .
H21A H 1.0008 0.7662 1.1184 0.023 Uiso 1 1 calc R . .
H21B H 1.0615 0.7865 1.0686 0.023 Uiso 1 1 calc R . .
C22 C 0.8911(2) 0.8068(2) 1.04683(11) 0.0184(6) Uani 1 1 d . . .
H22A H 0.8289 0.7876 1.0646 0.022 Uiso 1 1 calc R . .
H22B H 0.9005 0.8899 1.0488 0.022 Uiso 1 1 calc R . .
C23 C 0.9545(2) 0.7841(2) 0.95743(11) 0.0195(6) Uani 1 1 d . . .
H23A H 1.0171 0.7367 0.9747 0.023 Uiso 1 1 calc R . .
H23B H 0.9794 0.8636 0.9583 0.023 Uiso 1 1 calc R . .
C24 C 0.9149(2) 0.7460(2) 0.89834(11) 0.0191(6) Uani 1 1 d . . .
H24A H 0.9783 0.7447 0.8797 0.023 Uiso 1 1 calc R . .
H24B H 0.8860 0.6680 0.8982 0.023 Uiso 1 1 calc R . .
C25 C 0.8794(2) 0.9284(2) 0.84926(11) 0.0198(6) Uani 1 1 d . . .
H25A H 0.9399 0.9070 0.8307 0.024 Uiso 1 1 calc R . .
H25B H 0.9107 0.9740 0.8815 0.024 Uiso 1 1 calc R . .
C26 C 0.7940(2) 0.9995(2) 0.81062(11) 0.0214(6) Uani 1 1 d . . .
H26A H 0.7353 1.0234 0.8299 0.026 Uiso 1 1 calc R . .
H26B H 0.8298 1.0685 0.8000 0.026 Uiso 1 1 calc R . .
C27 C 0.6925(2) 0.8360(2) 0.77793(11) 0.0203(6) Uani 1 1 d . . .
H27A H 0.6595 0.7933 0.7450 0.024 Uiso 1 1 calc R . .
H27B H 0.6328 0.8580 0.7969 0.024 Uiso 1 1 calc R . .
C28 C 0.7750(2) 0.7595(2) 0.81526(11) 0.0196(6) Uani 1 1 d . . .
H28A H 0.7368 0.6911 0.8248 0.023 Uiso 1 1 calc R . .
H28B H 0.8332 0.7351 0.7958 0.023 Uiso 1 1 calc R . .


_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
Mn1 N1 2.247(2) . ?
Mn1 N2 2.333(2) . ?
Mn1 Cl2 2.5143(9) . ?
Mn1 Cl1 2.5245(8) . ?
Mn1 Cl3 2.5546(9) 3_677 ?
Mn1 Cl3 2.7116(8) . ?
Mn2 N3 2.269(2) . ?
Mn2 N4 2.359(2) . ?
Mn2 Cl4 2.4143(9) . ?
Mn2 Cl1 2.5204(8) . ?
Mn2 Cl2 2.6283(8) . ?
Mn2 Cl3 2.8052(8) . ?
S1 C1 1.775(3) . ?
S1 C7 1.809(3) . ?
S2 C15 1.780(3) . ?
S2 C21 1.824(3) . ?
Cl3 Mn1 2.5546(9) 3_677 ?
N1 C9 1.476(3) . ?
N1 C8 1.485(3) . ?
N2 C11 1.488(3) . ?
N2 C10 1.490(3) . ?
N2 C14 1.498(3) . ?
N3 C23 1.478(3) . ?
N3 C22 1.481(3) . ?
N4 C24 1.489(3) . ?
N4 C25 1.493(3) . ?
N4 C28 1.498(3) . ?
O1 C13 1.420(3) . ?
O1 C12 1.424(3) . ?
O2 C26 1.421(3) . ?
O2 C27 1.428(3) . ?
C1 C2 1.393(4) . ?
C1 C6 1.404(4) . ?
C2 C3 1.388(4) . ?
C3 C4 1.383(4) . ?
C4 C5 1.393(4) . ?
C5 C6 1.386(4) . ?
C7 C8 1.533(3) . ?
C9 C10 1.509(4) . ?
C11 C12 1.509(4) . ?
C13 C14 1.511(4) . ?
C15 C16 1.392(4) . ?
C15 C20 1.398(4) . ?
C16 C17 1.396(4) . ?
C17 C18 1.381(4) . ?
C18 C19 1.390(4) . ?
C19 C20 1.392(4) . ?
C21 C22 1.528(4) . ?
C23 C24 1.511(4) . ?
C25 C26 1.514(4) . ?
C27 C28 1.513(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
_geom_angle_publ_flag
N1 Mn1 N2 79.59(8) . . ?
N1 Mn1 Cl2 94.18(5) . . ?
N2 Mn1 Cl2 102.23(5) . . ?
N1 Mn1 Cl1 172.51(6) . . ?
N2 Mn1 Cl1 107.83(6) . . ?
Cl2 Mn1 Cl1 85.36(2) . . ?
N1 Mn1 Cl3 89.18(5) . 3_677 ?
N2 Mn1 Cl3 90.70(5) . 3_677 ?
Cl2 Mn1 Cl3 167.02(3) . 3_677 ?
Cl1 Mn1 Cl3 89.68(2) . 3_677 ?
N1 Mn1 Cl3 89.71(6) . . ?
N2 Mn1 Cl3 168.73(5) . . ?
Cl2 Mn1 Cl3 81.93(2) . . ?
Cl1 Mn1 Cl3 82.82(3) . . ?
Cl3 Mn1 Cl3 85.56(2) 3_677 . ?
N3 Mn2 N4 80.35(7) . . ?
N3 Mn2 Cl4 91.72(6) . . ?
N4 Mn2 Cl4 94.64(6) . . ?
N3 Mn2 Cl1 168.99(6) . . ?
N4 Mn2 Cl1 106.43(6) . . ?
Cl4 Mn2 Cl1 96.27(3) . . ?
N3 Mn2 Cl2 87.84(6) . . ?
N4 Mn2 Cl2 93.98(6) . . ?
Cl4 Mn2 Cl2 171.17(3) . . ?
Cl1 Mn2 Cl2 83.09(3) . . ?
N3 Mn2 Cl3 91.04(6) . . ?
N4 Mn2 Cl3 168.65(6) . . ?
Cl4 Mn2 Cl3 93.00(2) . . ?
Cl1 Mn2 Cl3 81.02(2) . . ?
Cl2 Mn2 Cl3 78.19(2) . . ?
C1 S1 C7 105.39(12) . . ?
C15 S2 C21 101.59(12) . . ?
Mn2 Cl1 Mn1 84.74(2) . . ?
Mn1 Cl2 Mn2 82.73(2) . . ?
Mn1 Cl3 Mn1 94.44(2) 3_677 . ?
Mn1 Cl3 Mn2 131.03(3) 3_677 . ?
Mn1 Cl3 Mn2 76.07(2) . . ?
C9 N1 C8 112.5(2) . . ?
C9 N1 Mn1 109.27(15) . . ?
C8 N1 Mn1 117.45(15) . . ?
C11 N2 C10 110.5(2) . . ?
C11 N2 C14 106.58(19) . . ?
C10 N2 C14 106.5(2) . . ?
C11 N2 Mn1 114.50(15) . . ?
C10 N2 Mn1 102.61(15) . . ?
C14 N2 Mn1 115.83(16) . . ?
C23 N3 C22 114.1(2) . . ?
C23 N3 Mn2 105.54(15) . . ?
C22 N3 Mn2 120.42(15) . . ?
C24 N4 C25 109.4(2) . . ?
C24 N4 C28 107.5(2) . . ?
C25 N4 C28 106.6(2) . . ?
C24 N4 Mn2 101.47(15) . . ?
C25 N4 Mn2 115.37(15) . . ?
C28 N4 Mn2 116.09(15) . . ?
C13 O1 C12 110.2(2) . . ?
C26 O2 C27 109.16(19) . . ?
C2 C1 C6 119.4(2) . . ?
C2 C1 S1 125.5(2) . . ?
C6 C1 S1 115.07(19) . . ?
C3 C2 C1 120.0(2) . . ?
C4 C3 C2 120.8(3) . . ?
C3 C4 C5 119.5(3) . . ?
C6 C5 C4 120.4(3) . . ?
C5 C6 C1 119.9(2) . . ?
C8 C7 S1 113.40(17) . . ?
N1 C8 C7 112.5(2) . . ?
N1 C9 C10 111.5(2) . . ?
N2 C10 C9 112.2(2) . . ?
N2 C11 C12 110.6(2) . . ?
O1 C12 C11 112.5(2) . . ?
O1 C13 C14 110.9(2) . . ?
N2 C14 C13 111.3(2) . . ?
C16 C15 C20 120.2(3) . . ?
C16 C15 S2 118.9(2) . . ?
C20 C15 S2 120.9(2) . . ?
C15 C16 C17 119.6(3) . . ?
C18 C17 C16 120.3(3) . . ?
C17 C18 C19 120.0(3) . . ?
C18 C19 C20 120.4(3) . . ?
C19 C20 C15 119.4(3) . . ?
C22 C21 S2 114.56(19) . . ?
N3 C22 C21 115.2(2) . . ?
N3 C23 C24 109.3(2) . . ?
N4 C24 C23 113.2(2) . . ?
N4 C25 C26 110.6(2) . . ?
O2 C26 C25 112.2(2) . . ?
O2 C27 C28 111.4(2) . . ?
N4 C28 C27 110.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.094
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0

#=============END=================
####################################################################### 
# 
# 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_apx1757as
_database_code_depnum_ccdc_archive 'CCDC 1429180'
_audit_update_record             
;
2015-11-30 deposited with the CCDC.
2015-12-11 downloaded from the CCDC.
;


# start Validation Reply Form
_vrf_CHEMW03_apx1757as           
;
PROBLEM: ALERT: The ratio of given/expected molecular weight as
RESPONSE: Chemical formula is correct.  Platon/Squeeze used to treat
disordered hexane solvent molecules.
;
# end Validation Reply Form


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H31 Cl2 Cu N2 O S'
_chemical_formula_weight         457.95

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P bca'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.2833(17)
_cell_length_b                   11.5401(15)
_cell_length_c                   26.694(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4091.9(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    140(1)
_cell_measurement_reflns_used    6251
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      23.88

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1920
_exptl_absorpt_coefficient_mu    1.440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6719
_exptl_absorpt_correction_T_max  0.9718
_exptl_absorpt_process_details   'SADABS v. 2.03 (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      140(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 with APEXII CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38636
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_sigmaI/netI    0.0340
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         25.77
_reflns_number_total             3921
_reflns_number_gt                3244
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX II, v. 7.0 (Bruker AXS, 2009)'
_computing_cell_refinement       'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT+, v. 7.66a (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL, v. 6.14, (Bruker AXS, 2000)'
_computing_publication_material  'SHELXTL, v. 6.14, (Bruker AXS, 2000)'

_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. 
;

# SQUEEZE RESULTS
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 0.000 190 39 hexane
2 0.000 0.000 0.500 190 39 hexane
3 0.500 0.500 0.500 190 39 hexane
4 0.000 0.500 1.000 190 39 hexane
_platon_squeeze_details          
;
;


_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)+(0.0330P)²+0.0000P] 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         3921
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0665
_refine_ls_wR_factor_gt          0.0633
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.425699(19) 0.05626(2) 0.727009(9) 0.01159(8) Uani 1 1 d . . .
Cl1 Cl 0.40381(4) 0.23909(5) 0.69848(2) 0.01608(13) Uani 1 1 d . . .
Cl2 Cl 0.60844(4) 0.01533(5) 0.71396(2) 0.01490(13) Uani 1 1 d . . .
S1 S 0.44814(4) 0.12448(5) 0.80971(2) 0.01499(13) Uani 1 1 d . . .
N1 N 0.36239(13) -0.01961(15) 0.66357(7) 0.0127(4) Uani 1 1 d . . .
N2 N 0.40771(13) -0.10039(16) 0.75900(7) 0.0124(4) Uani 1 1 d . . .
H2 H 0.4694 -0.1347 0.7585 0.015 Uiso 1 1 calc R . .
O1 O 0.27251(12) 0.01672(15) 0.56578(6) 0.0245(4) Uani 1 1 d . . .
C1 C 0.42050(16) 0.0153(2) 0.61848(8) 0.0159(5) Uani 1 1 d . . .
H1A H 0.4882 -0.0157 0.6209 0.019 Uiso 1 1 calc R . .
H1B H 0.4255 0.0991 0.6175 0.019 Uiso 1 1 calc R . .
C2 C 0.37258(18) -0.0270(2) 0.57060(9) 0.0228(6) Uani 1 1 d . . .
H2A H 0.4126 -0.0019 0.5422 0.027 Uiso 1 1 calc R . .
H2B H 0.3710 -0.1111 0.5705 0.027 Uiso 1 1 calc R . .
C3 C 0.21250(18) -0.0220(2) 0.60687(9) 0.0235(6) Uani 1 1 d . . .
H3A H 0.2089 -0.1059 0.6065 0.028 Uiso 1 1 calc R . .
H3B H 0.1446 0.0080 0.6033 0.028 Uiso 1 1 calc R . .
C4 C 0.25620(16) 0.0183(2) 0.65659(8) 0.0166(5) Uani 1 1 d . . .
H4A H 0.2531 0.1022 0.6582 0.020 Uiso 1 1 calc R . .
H4B H 0.2155 -0.0123 0.6837 0.020 Uiso 1 1 calc R . .
C5 C 0.37024(18) -0.14646(19) 0.67334(8) 0.0178(5) Uani 1 1 d . . .
H5A H 0.4386 -0.1723 0.6670 0.021 Uiso 1 1 calc R . .
H5B H 0.3256 -0.1881 0.6509 0.021 Uiso 1 1 calc R . .
C6 C 0.34233(17) -0.17210(19) 0.72665(8) 0.0158(5) Uani 1 1 d . . .
H6A H 0.2721 -0.1533 0.7325 0.019 Uiso 1 1 calc R . .
H6B H 0.3524 -0.2537 0.7339 0.019 Uiso 1 1 calc R . .
C7 C 0.37628(16) -0.0986(2) 0.81190(8) 0.0155(5) Uani 1 1 d . . .
H7A H 0.3814 -0.1757 0.8262 0.019 Uiso 1 1 calc R . .
H7B H 0.3069 -0.0730 0.8146 0.019 Uiso 1 1 calc R . .
C8 C 0.44479(17) -0.0160(2) 0.83959(8) 0.0171(5) Uani 1 1 d . . .
H8A H 0.5123 -0.0479 0.8407 0.021 Uiso 1 1 calc R . .
H8B H 0.4213 -0.0074 0.8738 0.021 Uiso 1 1 calc R . .
C9 C 0.32492(16) 0.1861(2) 0.82461(8) 0.0156(5) Uani 1 1 d . . .
H9A H 0.3149 0.2558 0.8049 0.019 Uiso 1 1 calc R . .
H9B H 0.2729 0.1311 0.8153 0.019 Uiso 1 1 calc R . .
C10 C 0.31431(16) 0.21509(19) 0.87895(8) 0.0156(5) Uani 1 1 d . . .
C11 C 0.28019(18) 0.1333(2) 0.91316(9) 0.0231(6) Uani 1 1 d . . .
H11 H 0.2611 0.0601 0.9021 0.028 Uiso 1 1 calc R . .
C12 C 0.2744(2) 0.1599(2) 0.96369(9) 0.0281(6) Uani 1 1 d . . .
H12 H 0.2529 0.1039 0.9864 0.034 Uiso 1 1 calc R . .
C13 C 0.30028(19) 0.2688(2) 0.98060(9) 0.0272(6) Uani 1 1 d . . .
H13 H 0.2961 0.2866 1.0145 0.033 Uiso 1 1 calc R . .
C14 C 0.33227(19) 0.3506(2) 0.94692(9) 0.0227(6) Uani 1 1 d . . .
H14 H 0.3490 0.4245 0.9581 0.027 Uiso 1 1 calc R . .
C15 C 0.33984(17) 0.3244(2) 0.89645(8) 0.0181(5) Uani 1 1 d . . .
H15 H 0.3622 0.3805 0.8741 0.022 Uiso 1 1 calc R . .


_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 N2 2.0135(18) . ?
Cu1 N1 2.0838(18) . ?
Cu1 Cl1 2.2619(6) . ?
Cu1 S1 2.3627(7) . ?
Cu1 Cl2 2.4974(7) . ?
S1 C8 1.807(2) . ?
S1 C9 1.828(2) . ?
N1 C1 1.485(3) . ?
N1 C4 1.489(3) . ?
N1 C5 1.491(3) . ?
N2 C7 1.473(3) . ?
N2 C6 1.478(3) . ?
O1 C3 1.427(3) . ?
O1 C2 1.428(3) . ?
C1 C2 1.509(3) . ?
C3 C4 1.521(3) . ?
C5 C6 1.500(3) . ?
C7 C8 1.511(3) . ?
C9 C10 1.495(3) . ?
C10 C15 1.387(3) . ?
C10 C11 1.390(3) . ?
C11 C12 1.385(3) . ?
C12 C13 1.379(4) . ?
C13 C14 1.371(3) . ?
C14 C15 1.384(3) . ?

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
N2 Cu1 N1 85.39(7) . . ?
N2 Cu1 Cl1 164.80(5) . . ?
N1 Cu1 Cl1 93.81(5) . . ?
N2 Cu1 S1 85.28(5) . . ?
N1 Cu1 S1 161.87(5) . . ?
Cl1 Cu1 S1 91.15(2) . . ?
N2 Cu1 Cl2 90.27(5) . . ?
N1 Cu1 Cl2 101.51(5) . . ?
Cl1 Cu1 Cl2 104.74(2) . . ?
S1 Cu1 Cl2 94.05(2) . . ?
C8 S1 C9 103.35(11) . . ?
C8 S1 Cu1 96.34(8) . . ?
C9 S1 Cu1 102.70(7) . . ?
C1 N1 C4 108.15(16) . . ?
C1 N1 C5 111.82(17) . . ?
C4 N1 C5 112.14(17) . . ?
C1 N1 Cu1 109.56(13) . . ?
C4 N1 Cu1 111.14(13) . . ?
C5 N1 Cu1 104.01(13) . . ?
C7 N2 C6 113.67(17) . . ?
C7 N2 Cu1 115.33(14) . . ?
C6 N2 Cu1 108.94(13) . . ?
C3 O1 C2 109.89(17) . . ?
N1 C1 C2 112.29(18) . . ?
O1 C2 C1 110.76(19) . . ?
O1 C3 C4 111.21(18) . . ?
N1 C4 C3 112.40(19) . . ?
N1 C5 C6 110.03(18) . . ?
N2 C6 C5 107.37(18) . . ?
N2 C7 C8 107.88(17) . . ?
C7 C8 S1 111.40(15) . . ?
C10 C9 S1 112.48(15) . . ?
C15 C10 C11 118.4(2) . . ?
C15 C10 C9 120.5(2) . . ?
C11 C10 C9 121.1(2) . . ?
C12 C11 C10 120.5(2) . . ?
C13 C12 C11 120.4(2) . . ?
C14 C13 C12 119.4(2) . . ?
C13 C14 C15 120.6(2) . . ?
C14 C15 C10 120.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.064
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0

#===============END======================
####################################################################### 
# 
# 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_fenns
_database_code_depnum_ccdc_archive 'CCDC 1429181'
_audit_update_record             
;
2015-11-30 deposited with the CCDC.
2015-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H22 Cl2 Fe N2 O S'
_chemical_formula_weight         393.15

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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'

_cell_length_a                   7.0525(6)
_cell_length_b                   21.2477(19)
_cell_length_c                   23.0147(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.269(4)
_cell_angle_gamma                90.00
_cell_volume                     3448.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9888
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      30.25

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1632
_exptl_absorpt_coefficient_mu    1.305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7050
_exptl_absorpt_correction_T_max  0.7578
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 with Apex II CCD detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            59050
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.30
_diffrn_reflns_theta_max         25.68
_reflns_number_total             6557
_reflns_number_gt                5061
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0297P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6557
_refine_ls_number_parameters     385
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0762
_refine_ls_wR_factor_gt          0.0700
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_restrained_S_all      1.163
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.54298(5) 0.138647(17) 0.666401(14) 0.01054(10) Uani 1 1 d . . .
Fe2 Fe 0.04786(5) 0.488376(17) 0.647915(15) 0.01195(10) Uani 1 1 d . . .
Cl1 Cl 0.70370(9) 0.12124(3) 0.74903(2) 0.01628(15) Uani 1 1 d . . .
Cl2 Cl 0.68089(8) 0.18042(3) 0.58756(2) 0.01508(14) Uani 1 1 d . . .
Cl3 Cl 0.19034(9) 0.44429(3) 0.57101(3) 0.01890(15) Uani 1 1 d . . .
Cl4 Cl 0.20425(9) 0.50723(3) 0.73122(3) 0.01710(15) Uani 1 1 d . . .
S1 S 0.81434(9) -0.03797(3) 0.54897(3) 0.01717(16) Uani 1 1 d . . .
S2 S 0.30869(10) 0.67146(4) 0.53240(3) 0.02357(17) Uani 1 1 d . . .
O1 O 0.2772(2) 0.30327(8) 0.71322(8) 0.0231(4) Uani 1 1 d . . .
O2 O -0.2250(3) 0.32392(9) 0.69449(8) 0.0248(5) Uani 1 1 d . . .
N1 N 0.2556(3) 0.17346(9) 0.67572(8) 0.0098(4) Uani 1 1 d . . .
N2 N 0.4038(3) 0.05793(10) 0.63113(8) 0.0105(5) Uani 1 1 d . . .
N3 N -0.2401(3) 0.45369(10) 0.65726(8) 0.0125(5) Uani 1 1 d . . .
N4 N -0.0897(3) 0.56941(10) 0.61307(9) 0.0133(5) Uani 1 1 d . . .
C1 C 0.2096(4) 0.19411(12) 0.73595(10) 0.0166(6) Uani 1 1 d . . .
H1A H 0.2407 0.1607 0.7631 0.020 Uiso 1 1 calc R . .
H1B H 0.0748 0.2025 0.7388 0.020 Uiso 1 1 calc R . .
C2 C 0.3192(4) 0.25258(13) 0.75178(11) 0.0240(7) Uani 1 1 d . . .
H2A H 0.2882 0.2649 0.7912 0.029 Uiso 1 1 calc R . .
H2B H 0.4540 0.2436 0.7504 0.029 Uiso 1 1 calc R . .
C3 C 0.3250(4) 0.28558(12) 0.65562(11) 0.0186(6) Uani 1 1 d . . .
H3A H 0.4600 0.2771 0.6536 0.022 Uiso 1 1 calc R . .
H3B H 0.2969 0.3201 0.6294 0.022 Uiso 1 1 calc R . .
C4 C 0.2164(3) 0.22800(11) 0.63671(10) 0.0137(6) Uani 1 1 d . . .
H4A H 0.0817 0.2372 0.6370 0.016 Uiso 1 1 calc R . .
H4B H 0.2516 0.2172 0.5973 0.016 Uiso 1 1 calc R . .
C5 C 0.1310(3) 0.12014(11) 0.65907(10) 0.0120(5) Uani 1 1 d . . .
H5A H 0.0085 0.1361 0.6467 0.014 Uiso 1 1 calc R . .
H5B H 0.1114 0.0931 0.6925 0.014 Uiso 1 1 calc R . .
C6 C 0.2188(3) 0.08255(12) 0.61043(10) 0.0129(5) Uani 1 1 d . . .
H6A H 0.1360 0.0480 0.5996 0.016 Uiso 1 1 calc R . .
H6B H 0.2370 0.1091 0.5766 0.016 Uiso 1 1 calc R . .
C7 C 0.5043(3) 0.02287(12) 0.58553(10) 0.0126(5) Uani 1 1 d . . .
H7A H 0.5360 0.0512 0.5539 0.015 Uiso 1 1 calc R . .
H7B H 0.4223 -0.0099 0.5702 0.015 Uiso 1 1 calc R . .
C8 C 0.6846(3) -0.00660(12) 0.60969(10) 0.0139(6) Uani 1 1 d . . .
H8A H 0.6538 -0.0399 0.6369 0.017 Uiso 1 1 calc R . .
H8B H 0.7599 0.0248 0.6298 0.017 Uiso 1 1 calc R . .
C9 C 1.0117(3) -0.07580(11) 0.58094(10) 0.0125(5) Uani 1 1 d . . .
C10 C 1.0546(4) -0.07518(12) 0.63969(10) 0.0150(6) Uani 1 1 d . . .
H10 H 0.9766 -0.0538 0.6655 0.018 Uiso 1 1 calc R . .
C11 C 1.2148(4) -0.10669(12) 0.66007(11) 0.0160(6) Uani 1 1 d . . .
H11 H 1.2428 -0.1066 0.6996 0.019 Uiso 1 1 calc R . .
C12 C 1.3319(4) -0.13801(12) 0.62212(11) 0.0168(6) Uani 1 1 d . . .
H12 H 1.4389 -0.1589 0.6359 0.020 Uiso 1 1 calc R . .
C13 C 1.2894(4) -0.13823(12) 0.56317(11) 0.0159(6) Uani 1 1 d . . .
H13 H 1.3684 -0.1593 0.5375 0.019 Uiso 1 1 calc R . .
C14 C 1.1311(3) -0.10738(12) 0.54243(10) 0.0131(6) Uani 1 1 d . . .
H14 H 1.1037 -0.1076 0.5029 0.016 Uiso 1 1 calc R . .
C15 C -0.2776(3) 0.39996(11) 0.61736(10) 0.0149(6) Uani 1 1 d . . .
H15A H -0.2381 0.4110 0.5784 0.018 Uiso 1 1 calc R . .
H15B H -0.4126 0.3912 0.6163 0.018 Uiso 1 1 calc R . .
C16 C -0.1718(4) 0.34193(12) 0.63721(12) 0.0219(6) Uani 1 1 d . . .
H16A H -0.1982 0.3076 0.6106 0.026 Uiso 1 1 calc R . .
H16B H -0.0366 0.3502 0.6363 0.026 Uiso 1 1 calc R . .
C17 C -0.1842(4) 0.37395(13) 0.73349(11) 0.0225(6) Uani 1 1 d . . .
H17A H -0.0490 0.3824 0.7333 0.027 Uiso 1 1 calc R . .
H17B H -0.2192 0.3616 0.7726 0.027 Uiso 1 1 calc R . .
C18 C -0.2905(4) 0.43321(12) 0.71697(10) 0.0173(6) Uani 1 1 d . . .
H18A H -0.4259 0.4255 0.7190 0.021 Uiso 1 1 calc R . .
H18B H -0.2597 0.4664 0.7443 0.021 Uiso 1 1 calc R . .
C19 C -0.3636(3) 0.50753(11) 0.64013(11) 0.0132(6) Uani 1 1 d . . .
H19A H -0.3834 0.5346 0.6735 0.016 Uiso 1 1 calc R . .
H19B H -0.4861 0.4918 0.6275 0.016 Uiso 1 1 calc R . .
C20 C -0.2749(3) 0.54505(12) 0.59164(10) 0.0142(6) Uani 1 1 d . . .
H20A H -0.2560 0.5185 0.5579 0.017 Uiso 1 1 calc R . .
H20B H -0.3571 0.5797 0.5807 0.017 Uiso 1 1 calc R . .
C21 C 0.0108(3) 0.60478(12) 0.56790(11) 0.0160(6) Uani 1 1 d . . .
H21A H -0.0717 0.6373 0.5524 0.019 Uiso 1 1 calc R . .
H21B H 0.0443 0.5766 0.5364 0.019 Uiso 1 1 calc R . .
C22 C 0.1899(3) 0.63486(13) 0.59274(10) 0.0162(6) Uani 1 1 d . . .
H22A H 0.2706 0.6032 0.6105 0.019 Uiso 1 1 calc R . .
H22B H 0.1579 0.6660 0.6219 0.019 Uiso 1 1 calc R . .
C23 C 0.5127(3) 0.70608(12) 0.56315(11) 0.0151(6) Uani 1 1 d . . .
C24 C 0.6301(4) 0.73741(13) 0.52430(11) 0.0189(6) Uani 1 1 d . . .
H24 H 0.5995 0.7380 0.4850 0.023 Uiso 1 1 calc R . .
C25 C 0.7916(4) 0.76764(13) 0.54364(12) 0.0242(7) Uani 1 1 d . . .
H25 H 0.8686 0.7888 0.5174 0.029 Uiso 1 1 calc R . .
C26 C 0.8390(4) 0.76654(13) 0.60199(12) 0.0237(7) Uani 1 1 d . . .
H26 H 0.9476 0.7870 0.6151 0.028 Uiso 1 1 calc R . .
C27 C 0.7248(4) 0.73494(12) 0.64058(11) 0.0192(6) Uani 1 1 d . . .
H27 H 0.7574 0.7340 0.6798 0.023 Uiso 1 1 calc R . .
C28 C 0.5615(4) 0.70438(12) 0.62174(10) 0.0162(6) Uani 1 1 d . . .
H28 H 0.4856 0.6830 0.6481 0.019 Uiso 1 1 calc R . .
H4 H -0.112(5) 0.5978(18) 0.6412(15) 0.080 Uiso 1 1 d . . .
H2 H 0.385(5) 0.0333(19) 0.6576(15) 0.080 Uiso 1 1 d . . .


_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
Fe1 N2 2.135(2) . ?
Fe1 N1 2.1689(19) . ?
Fe1 Cl1 2.2401(7) . ?
Fe1 Cl2 2.2456(7) . ?
Fe2 N4 2.131(2) . ?
Fe2 N3 2.172(2) . ?
Fe2 Cl4 2.2433(7) . ?
Fe2 Cl3 2.2443(7) . ?
S1 C9 1.765(2) . ?
S1 C8 1.802(2) . ?
S2 C23 1.761(2) . ?
S2 C22 1.802(2) . ?
O1 C3 1.420(3) . ?
O1 C2 1.426(3) . ?
O2 C17 1.420(3) . ?
O2 C16 1.425(3) . ?
N1 C5 1.483(3) . ?
N1 C4 1.491(3) . ?
N1 C1 1.491(3) . ?
N2 C7 1.472(3) . ?
N2 C6 1.483(3) . ?
N3 C18 1.486(3) . ?
N3 C19 1.490(3) . ?
N3 C15 1.488(3) . ?
N4 C21 1.468(3) . ?
N4 C20 1.487(3) . ?
C1 C2 1.507(4) . ?
C3 C4 1.507(3) . ?
C5 C6 1.510(3) . ?
C7 C8 1.520(3) . ?
C9 C10 1.384(3) . ?
C9 C14 1.397(3) . ?
C10 C11 1.393(3) . ?
C11 C12 1.376(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.378(3) . ?
C15 C16 1.511(3) . ?
C17 C18 1.513(4) . ?
C19 C20 1.509(3) . ?
C21 C22 1.525(3) . ?
C23 C28 1.391(3) . ?
C23 C24 1.391(4) . ?
C24 C25 1.379(4) . ?
C25 C26 1.383(4) . ?
C26 C27 1.376(4) . ?
C27 C28 1.390(3) . ?

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
N2 Fe1 N1 83.30(8) . . ?
N2 Fe1 Cl1 114.84(6) . . ?
N1 Fe1 Cl1 116.21(5) . . ?
N2 Fe1 Cl2 102.15(6) . . ?
N1 Fe1 Cl2 110.70(5) . . ?
Cl1 Fe1 Cl2 122.14(3) . . ?
N4 Fe2 N3 83.52(8) . . ?
N4 Fe2 Cl4 113.48(6) . . ?
N3 Fe2 Cl4 115.60(5) . . ?
N4 Fe2 Cl3 104.20(6) . . ?
N3 Fe2 Cl3 111.03(6) . . ?
Cl4 Fe2 Cl3 121.89(3) . . ?
C9 S1 C8 104.33(11) . . ?
C23 S2 C22 104.62(12) . . ?
C3 O1 C2 109.35(19) . . ?
C17 O2 C16 109.3(2) . . ?
C5 N1 C4 109.28(17) . . ?
C5 N1 C1 109.50(18) . . ?
C4 N1 C1 106.89(19) . . ?
C5 N1 Fe1 105.47(14) . . ?
C4 N1 Fe1 112.10(14) . . ?
C1 N1 Fe1 113.56(14) . . ?
C7 N2 C6 112.06(18) . . ?
C7 N2 Fe1 117.11(15) . . ?
C6 N2 Fe1 103.96(14) . . ?
C18 N3 C19 109.13(19) . . ?
C18 N3 C15 107.66(19) . . ?
C19 N3 C15 108.89(18) . . ?
C18 N3 Fe2 114.75(14) . . ?
C19 N3 Fe2 105.00(14) . . ?
C15 N3 Fe2 111.26(15) . . ?
C21 N4 C20 111.70(18) . . ?
C21 N4 Fe2 117.35(16) . . ?
C20 N4 Fe2 103.95(15) . . ?
N1 C1 C2 110.7(2) . . ?
O1 C2 C1 111.6(2) . . ?
O1 C3 C4 111.2(2) . . ?
N1 C4 C3 111.38(19) . . ?
N1 C5 C6 110.56(19) . . ?
N2 C6 C5 108.15(18) . . ?
N2 C7 C8 110.64(18) . . ?
C7 C8 S1 107.19(16) . . ?
C10 C9 C14 119.6(2) . . ?
C10 C9 S1 124.84(19) . . ?
C14 C9 S1 115.51(17) . . ?
C9 C10 C11 119.9(2) . . ?
C12 C11 C10 120.5(2) . . ?
C11 C12 C13 119.6(2) . . ?
C14 C13 C12 120.5(2) . . ?
C13 C14 C9 119.9(2) . . ?
N3 C15 C16 110.69(19) . . ?
O2 C16 C15 111.5(2) . . ?
O2 C17 C18 111.5(2) . . ?
N3 C18 C17 110.8(2) . . ?
N3 C19 C20 110.96(19) . . ?
N4 C20 C19 107.75(19) . . ?
N4 C21 C22 110.56(19) . . ?
C21 C22 S2 106.22(16) . . ?
C28 C23 C24 119.4(2) . . ?
C28 C23 S2 125.2(2) . . ?
C24 C23 S2 115.42(18) . . ?
C25 C24 C23 120.6(2) . . ?
C26 C25 C24 120.1(3) . . ?
C27 C26 C25 119.7(2) . . ?
C26 C27 C28 120.9(2) . . ?
C23 C28 C27 119.4(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.081

#===============END====================
