# Electronic Supplementary Material (ESI) for ChemComm.
# 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_cd214544
_database_code_depnum_ccdc_archive 'CCDC 1034135'
_audit_update_record             
;
2014-11-14 deposited with the CCDC.
2015-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 Cl Fe S'
_chemical_formula_weight         328.62

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'
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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.7825(6)
_cell_length_b                   8.6085(9)
_cell_length_c                   14.0430(14)
_cell_angle_alpha                99.114(2)
_cell_angle_beta                 99.532(2)
_cell_angle_gamma                94.734(2)
_cell_volume                     676.43(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2797
_cell_measurement_theta_min      4.823
_cell_measurement_theta_max      56.569

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.198
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    1.446
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6326
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4135
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.493
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2653
_reflns_number_gt                2476
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0410P)²+0.2130P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2653
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0773
_refine_ls_wR_factor_gt          0.0755
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.73365(4) 0.70350(3) 0.82041(2) 0.02832(11) Uani 1 1 d . . . . .
S1 S 0.53045(10) 1.05366(7) 0.82160(4) 0.04412(15) Uani 1 1 d . . . . .
Cl1 Cl -0.17615(11) 1.30127(8) 0.50675(4) 0.05375(17) Uani 1 1 d . . . . .
C1 C 0.9930(4) 0.5908(3) 0.88825(16) 0.0403(5) Uani 1 1 d . . . . .
H1 H 1.1057 0.5326 0.8561 0.048 Uiso 1 1 calc R U . . .
C2 C 1.0259(4) 0.7529(3) 0.92867(15) 0.0409(5) Uani 1 1 d . . . . .
H2 H 1.1651 0.8269 0.9301 0.049 Uiso 1 1 calc R U . . .
C3 C 0.8213(4) 0.7900(3) 0.96691(15) 0.0452(5) Uani 1 1 d . . . . .
H3 H 0.7939 0.8944 0.9996 0.054 Uiso 1 1 calc R U . . .
C4 C 0.6647(4) 0.6504(3) 0.94995(16) 0.0465(5) Uani 1 1 d . . . . .
H4 H 0.5089 0.6408 0.9687 0.056 Uiso 1 1 calc R U . . .
C5 C 0.7706(4) 0.5263(3) 0.90073(16) 0.0441(5) Uani 1 1 d . . . . .
H5 H 0.7020 0.4157 0.8797 0.053 Uiso 1 1 calc R U . . .
C6 C 0.5280(4) 0.6082(3) 0.68750(15) 0.0402(5) Uani 1 1 d . . . . .
H6 H 0.4617 0.4972 0.6665 0.048 Uiso 1 1 calc R U . . .
C7 C 0.7494(4) 0.6738(3) 0.67414(15) 0.0405(5) Uani 1 1 d . . . . .
H7 H 0.8632 0.6160 0.6423 0.049 Uiso 1 1 calc R U . . .
C8 C 0.7815(4) 0.8361(3) 0.71595(15) 0.0370(4) Uani 1 1 d . . . . .
H8 H 0.9197 0.9110 0.7174 0.044 Uiso 1 1 calc R U . . .
C9 C 0.5776(3) 0.8711(2) 0.75619(14) 0.0338(4) Uani 1 1 d . . . . .
C10 C 0.4203(3) 0.7288(3) 0.73788(15) 0.0372(4) Uani 1 1 d . . . . .
H10 H 0.2652 0.7170 0.7570 0.045 Uiso 1 1 calc R U . . .
C11 C 0.3403(3) 1.1271(2) 0.73068(15) 0.0341(4) Uani 1 1 d . . . . .
C12 C 0.3630(4) 1.1034(3) 0.63344(16) 0.0443(5) Uani 1 1 d . . . . .
H12 H 0.4849 1.0495 0.6140 0.053 Uiso 1 1 calc R U . . .
C13 C 0.2068(4) 1.1589(3) 0.56465(16) 0.0460(5) Uani 1 1 d . . . . .
H13 H 0.2228 1.1424 0.4991 0.055 Uiso 1 1 calc R U . . .
C14 C 0.0271(4) 1.2389(2) 0.59417(15) 0.0372(4) Uani 1 1 d . . . . .
C15 C 0.0048(4) 1.2673(3) 0.69015(16) 0.0411(5) Uani 1 1 d . . . . .
H15 H -0.1149 1.3239 0.7093 0.049 Uiso 1 1 calc R U . . .
C16 C 0.1615(4) 1.2114(3) 0.75912(15) 0.0403(5) Uani 1 1 d . . . . .
H16 H 0.1466 1.2304 0.8248 0.048 Uiso 1 1 calc R U . . .


_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 C9 2.0167(19) . ?
Fe1 C10 2.0308(19) . ?
Fe1 C8 2.036(2) . ?
Fe1 C3 2.037(2) . ?
Fe1 C4 2.037(2) . ?
Fe1 C1 2.039(2) . ?
Fe1 C5 2.041(2) . ?
Fe1 C2 2.043(2) . ?
Fe1 C6 2.047(2) . ?
Fe1 C7 2.047(2) . ?
S1 C9 1.756(2) . ?
S1 C11 1.773(2) . ?
Cl1 C14 1.736(2) . ?
C1 C2 1.405(3) . ?
C1 C5 1.408(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.417(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.407(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.417(3) . ?
C4 H4 0.9800 . ?
C5 H5 0.9800 . ?
C6 C7 1.409(3) . ?
C6 C10 1.410(3) . ?
C6 H6 0.9800 . ?
C7 C8 1.412(3) . ?
C7 H7 0.9800 . ?
C8 C9 1.423(3) . ?
C8 H8 0.9800 . ?
C9 C10 1.426(3) . ?
C10 H10 0.9800 . ?
C11 C12 1.378(3) . ?
C11 C16 1.387(3) . ?
C12 C13 1.380(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.361(3) . ?
C15 C16 1.385(3) . ?
C15 H15 0.9300 . ?
C16 H16 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
_geom_angle_publ_flag
C9 Fe1 C10 41.24(8) . . ?
C9 Fe1 C8 41.12(8) . . ?
C10 Fe1 C8 68.92(8) . . ?
C9 Fe1 C3 107.33(9) . . ?
C10 Fe1 C3 123.07(9) . . ?
C8 Fe1 C3 123.06(10) . . ?
C9 Fe1 C4 122.29(9) . . ?
C10 Fe1 C4 107.20(9) . . ?
C8 Fe1 C4 158.84(10) . . ?
C3 Fe1 C4 40.39(10) . . ?
C9 Fe1 C1 159.55(9) . . ?
C10 Fe1 C1 158.13(9) . . ?
C8 Fe1 C1 123.41(9) . . ?
C3 Fe1 C1 67.95(9) . . ?
C4 Fe1 C1 67.91(9) . . ?
C9 Fe1 C5 158.36(9) . . ?
C10 Fe1 C5 122.04(9) . . ?
C8 Fe1 C5 159.09(9) . . ?
C3 Fe1 C5 68.25(9) . . ?
C4 Fe1 C5 40.68(10) . . ?
C1 Fe1 C5 40.37(9) . . ?
C9 Fe1 C2 123.25(9) . . ?
C10 Fe1 C2 159.74(9) . . ?
C8 Fe1 C2 107.94(9) . . ?
C3 Fe1 C2 40.65(9) . . ?
C4 Fe1 C2 68.08(9) . . ?
C1 Fe1 C2 40.27(9) . . ?
C5 Fe1 C2 68.12(9) . . ?
C9 Fe1 C6 68.61(8) . . ?
C10 Fe1 C6 40.45(9) . . ?
C8 Fe1 C6 68.21(9) . . ?
C3 Fe1 C6 159.14(10) . . ?
C4 Fe1 C6 123.18(10) . . ?
C1 Fe1 C6 122.97(9) . . ?
C5 Fe1 C6 107.54(9) . . ?
C2 Fe1 C6 158.65(9) . . ?
C9 Fe1 C7 68.54(8) . . ?
C10 Fe1 C7 68.19(8) . . ?
C8 Fe1 C7 40.45(9) . . ?
C3 Fe1 C7 159.14(10) . . ?
C4 Fe1 C7 159.19(10) . . ?
C1 Fe1 C7 108.35(9) . . ?
C5 Fe1 C7 123.18(9) . . ?
C2 Fe1 C7 123.25(9) . . ?
C6 Fe1 C7 40.27(9) . . ?
C9 S1 C11 101.35(9) . . ?
C2 C1 C5 108.8(2) . . ?
C2 C1 Fe1 70.02(12) . . ?
C5 C1 Fe1 69.88(12) . . ?
C2 C1 H1 125.6 . . ?
C5 C1 H1 125.6 . . ?
Fe1 C1 H1 125.6 . . ?
C1 C2 C3 107.6(2) . . ?
C1 C2 Fe1 69.71(12) . . ?
C3 C2 Fe1 69.46(12) . . ?
C1 C2 H2 126.2 . . ?
C3 C2 H2 126.2 . . ?
Fe1 C2 H2 126.2 . . ?
C4 C3 C2 108.0(2) . . ?
C4 C3 Fe1 69.81(12) . . ?
C2 C3 Fe1 69.89(12) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
Fe1 C3 H3 126.0 . . ?
C3 C4 C5 108.2(2) . . ?
C3 C4 Fe1 69.80(12) . . ?
C5 C4 Fe1 69.79(12) . . ?
C3 C4 H4 125.9 . . ?
C5 C4 H4 125.9 . . ?
Fe1 C4 H4 125.9 . . ?
C1 C5 C4 107.4(2) . . ?
C1 C5 Fe1 69.74(12) . . ?
C4 C5 Fe1 69.53(12) . . ?
C1 C5 H5 126.3 . . ?
C4 C5 H5 126.3 . . ?
Fe1 C5 H5 126.3 . . ?
C7 C6 C10 108.37(19) . . ?
C7 C6 Fe1 69.89(12) . . ?
C10 C6 Fe1 69.16(11) . . ?
C7 C6 H6 125.8 . . ?
C10 C6 H6 125.8 . . ?
Fe1 C6 H6 125.8 . . ?
C6 C7 C8 108.48(18) . . ?
C6 C7 Fe1 69.84(12) . . ?
C8 C7 Fe1 69.33(12) . . ?
C6 C7 H7 125.8 . . ?
C8 C7 H7 125.8 . . ?
Fe1 C7 H7 125.8 . . ?
C7 C8 C9 107.66(19) . . ?
C7 C8 Fe1 70.22(12) . . ?
C9 C8 Fe1 68.72(11) . . ?
C7 C8 H8 126.2 . . ?
C9 C8 H8 126.2 . . ?
Fe1 C8 H8 126.2 . . ?
C8 C9 C10 107.75(18) . . ?
C8 C9 S1 126.71(16) . . ?
C10 C9 S1 125.49(16) . . ?
C8 C9 Fe1 70.16(11) . . ?
C10 C9 Fe1 69.91(11) . . ?
S1 C9 Fe1 123.33(11) . . ?
C6 C10 C9 107.75(18) . . ?
C6 C10 Fe1 70.38(11) . . ?
C9 C10 Fe1 68.85(11) . . ?
C6 C10 H10 126.1 . . ?
C9 C10 H10 126.1 . . ?
Fe1 C10 H10 126.1 . . ?
C12 C11 C16 119.0(2) . . ?
C12 C11 S1 122.69(16) . . ?
C16 C11 S1 118.30(16) . . ?
C11 C12 C13 120.7(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 119.2(2) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C15 C14 C13 121.07(19) . . ?
C15 C14 Cl1 119.80(16) . . ?
C13 C14 Cl1 119.12(17) . . ?
C14 C15 C16 119.60(19) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C11 120.29(19) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C1 C2 C3 0.0(2) . . . . ?
Fe1 C1 C2 C3 59.34(15) . . . . ?
C5 C1 C2 Fe1 -59.32(15) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
Fe1 C2 C3 C4 59.66(15) . . . . ?
C1 C2 C3 Fe1 -59.49(15) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
Fe1 C3 C4 C5 59.43(15) . . . . ?
C2 C3 C4 Fe1 -59.71(15) . . . . ?
C2 C1 C5 C4 -0.2(2) . . . . ?
Fe1 C1 C5 C4 -59.59(14) . . . . ?
C2 C1 C5 Fe1 59.40(15) . . . . ?
C3 C4 C5 C1 0.3(2) . . . . ?
Fe1 C4 C5 C1 59.73(14) . . . . ?
C3 C4 C5 Fe1 -59.44(15) . . . . ?
C10 C6 C7 C8 -0.1(2) . . . . ?
Fe1 C6 C7 C8 -58.72(14) . . . . ?
C10 C6 C7 Fe1 58.62(14) . . . . ?
C6 C7 C8 C9 0.3(2) . . . . ?
Fe1 C7 C8 C9 -58.72(14) . . . . ?
C6 C7 C8 Fe1 59.03(14) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
Fe1 C8 C9 C10 -60.07(14) . . . . ?
C7 C8 C9 S1 177.02(15) . . . . ?
Fe1 C8 C9 S1 117.36(16) . . . . ?
C7 C8 C9 Fe1 59.66(14) . . . . ?
C11 S1 C9 C8 102.08(18) . . . . ?
C11 S1 C9 C10 -80.94(19) . . . . ?
C11 S1 C9 Fe1 -168.87(12) . . . . ?
C7 C6 C10 C9 -0.2(2) . . . . ?
Fe1 C6 C10 C9 58.92(13) . . . . ?
C7 C6 C10 Fe1 -59.07(14) . . . . ?
C8 C9 C10 C6 0.3(2) . . . . ?
S1 C9 C10 C6 -177.12(15) . . . . ?
Fe1 C9 C10 C6 -59.88(14) . . . . ?
C8 C9 C10 Fe1 60.23(13) . . . . ?
S1 C9 C10 Fe1 -117.24(16) . . . . ?
C9 S1 C11 C12 -36.7(2) . . . . ?
C9 S1 C11 C16 143.12(17) . . . . ?
C16 C11 C12 C13 -1.7(4) . . . . ?
S1 C11 C12 C13 178.12(18) . . . . ?
C11 C12 C13 C14 0.1(4) . . . . ?
C12 C13 C14 C15 1.6(4) . . . . ?
C12 C13 C14 Cl1 -177.38(19) . . . . ?
C13 C14 C15 C16 -1.7(3) . . . . ?
Cl1 C14 C15 C16 177.27(17) . . . . ?
C14 C15 C16 C11 0.1(3) . . . . ?
C12 C11 C16 C15 1.6(3) . . . . ?
S1 C11 C16 C15 -178.24(17) . . . . ?

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.067

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_mo_dm14546_0m
_database_code_depnum_ccdc_archive 'CCDC 1034136'
_audit_update_record             
;
2015-04-24 deposited with the CCDC.
2015-05-12 downloaded from the CCDC.
;
_audit_creation_date             2015-04-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C8 H24 Cu N4, 2(C7 H6 F O3 S2), 2(H2 O)'
_chemical_formula_sum            'C22 H40 Cu F2 N4 O8 S4'
_chemical_formula_weight         718.36
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5312(15)
_cell_length_b                   8.2038(16)
_cell_length_c                   13.344(3)
_cell_angle_alpha                92.852(3)
_cell_angle_beta                 93.152(4)
_cell_angle_gamma                107.116(3)
_cell_volume                     784.9(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3444
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.37
_cell_measurement_theta_min      2.60
_shelx_estimated_absorpt_T_max   0.862
_shelx_estimated_absorpt_T_min   0.685
_exptl_absorpt_coefficient_mu    1.023
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0659 before and 0.0349 after correction.
The Ratio of minimum to maximum transmission is 0.6881.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             375
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5492
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         1.532
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2753
_reflns_number_total             3094
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.860
_refine_diff_density_min         -0.930
_refine_diff_density_rms         0.144
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3094
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0619
_refine_ls_restrained_S_all      1.138
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0926P)²+2.4990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1716
_refine_ls_wR_factor_ref         0.1777
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O4(H4D,H4E)
2.b Ternary CH refined with riding coordinates:
 N1(H1), N2(H2)
2.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.d Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C4(H4A,H4B,H4C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu -0.5000 0.0000 -0.5000 0.0165(2) Uani 1 2 d S T P . .
N1 N -0.2674(5) 0.1566(4) -0.4181(3) 0.0190(7) Uani 1 1 d . . . . .
H1 H -0.3085 0.2465 -0.3810 0.023 Uiso 1 1 calc R . . . .
N2 N -0.3989(5) 0.1370(4) -0.6184(3) 0.0198(7) Uani 1 1 d . . . . .
H2 H -0.5027 0.1740 -0.6503 0.024 Uiso 1 1 calc R . . . .
C1 C -0.1681(6) 0.0828(6) -0.3423(3) 0.0247(9) Uani 1 1 d . . . . .
H1A H -0.2479 0.0450 -0.2872 0.037 Uiso 1 1 calc GR . . . .
H1B H -0.0531 0.1696 -0.3158 0.037 Uiso 1 1 calc GR . . . .
H1C H -0.1375 -0.0151 -0.3738 0.037 Uiso 1 1 calc GR . . . .
C2 C -0.1393(6) 0.2450(6) -0.4916(3) 0.0237(9) Uani 1 1 d . . . . .
H2A H -0.0712 0.1685 -0.5193 0.028 Uiso 1 1 calc R . . . .
H2B H -0.0471 0.3484 -0.4584 0.028 Uiso 1 1 calc R . . . .
C3 C -0.2528(6) 0.2944(6) -0.5754(4) 0.0235(9) Uani 1 1 d . . . . .
H3A H -0.3117 0.3791 -0.5487 0.028 Uiso 1 1 calc R . . . .
H3B H -0.1713 0.3463 -0.6282 0.028 Uiso 1 1 calc R . . . .
C4 C -0.3273(7) 0.0480(6) -0.6981(4) 0.0264(10) Uani 1 1 d . . . . .
H4A H -0.2156 0.0222 -0.6712 0.040 Uiso 1 1 calc GR . . . .
H4B H -0.2958 0.1214 -0.7542 0.040 Uiso 1 1 calc GR . . . .
H4C H -0.4228 -0.0587 -0.7218 0.040 Uiso 1 1 calc GR . . . .
S1 S -0.08396(15) -0.43967(18) -0.20027(9) 0.0304(3) Uani 1 1 d . . . . .
S2 S -0.31172(14) -0.43622(14) -0.29549(8) 0.0204(3) Uani 1 1 d . . . . .
F1 F -0.1823(8) -0.1088(8) 0.1067(4) 0.0978(18) Uani 1 1 d . . . . .
O1 O -0.2240(5) -0.4028(5) -0.3898(2) 0.0342(8) Uani 1 1 d . . . . .
O2 O -0.4447(5) -0.6059(4) -0.2989(3) 0.0309(8) Uani 1 1 d . . . . .
O3 O -0.3850(5) -0.3041(4) -0.2570(2) 0.0291(7) Uani 1 1 d . . . . .
C5 C -0.1799(7) -0.4505(9) -0.0822(4) 0.0410(14) Uani 1 1 d . . . . .
C6 C -0.1534(9) -0.2729(12) -0.0321(5) 0.062(2) Uani 1 1 d . . . . .
H6 H -0.0997 -0.1720 -0.0652 0.074 Uiso 1 1 calc R . . . .
C7 C -0.2087(10) -0.2670(11) 0.0588(6) 0.063(2) Uani 1 1 d . . . . .
C8 C -0.2935(9) -0.4121(12) 0.1077(6) 0.065(2) Uani 1 1 d . . . . .
H8 H -0.3318 -0.3992 0.1735 0.078 Uiso 1 1 calc R . . . .
C9 C -0.3230(8) -0.5702(13) 0.0646(5) 0.061(2) Uani 1 1 d . . . . .
H9 H -0.3833 -0.6681 0.0986 0.073 Uiso 1 1 calc R . . . .
C10 C -0.2610(8) -0.5875(10) -0.0345(5) 0.0532(17) Uani 1 1 d . . . . .
C11 C -0.2889(11) -0.7521(12) -0.0818(6) 0.070(2) Uani 1 1 d . . . . .
H11A H -0.1699 -0.7625 -0.1029 0.105 Uiso 1 1 calc GR . . . .
H11B H -0.3773 -0.7689 -0.1408 0.105 Uiso 1 1 calc GR . . . .
H11C H -0.3389 -0.8388 -0.0345 0.105 Uiso 1 1 calc GR . . . .
O4 O -0.6740(4) 0.2090(4) -0.4642(3) 0.0254(7) Uani 1 1 d . . . . .
H4D H -0.7582 0.1137 -0.4636 0.038 Uiso 1 1 d G . . . .
H4E H -0.7029 0.2660 -0.5105 0.038 Uiso 1 1 d G . . . .


_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 N1 2.059(3) . ?
Cu1 N1 2.059(3) 2_454 ?
Cu1 N2 2.036(4) . ?
Cu1 N2 2.036(4) 2_454 ?
N1 H1 1.0000 . ?
N1 C1 1.481(5) . ?
N1 C2 1.477(5) . ?
N2 H2 1.0000 . ?
N2 C3 1.493(5) . ?
N2 C4 1.474(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.512(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
S1 S2 2.0857(15) . ?
S1 C5 1.764(5) . ?
S2 O1 1.454(3) . ?
S2 O2 1.453(3) . ?
S2 O3 1.439(3) . ?
F1 C7 1.372(9) . ?
C5 C6 1.526(11) . ?
C5 C10 1.324(9) . ?
C6 H6 0.9500 . ?
C6 C7 1.307(10) . ?
C7 C8 1.388(11) . ?
C8 H8 0.9500 . ?
C8 C9 1.343(12) . ?
C9 H9 0.9500 . ?
C9 C10 1.440(9) . ?
C10 C11 1.414(11) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
O4 H4D 0.8500 . ?
O4 H4E 0.8499 . ?

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 Cu1 N1 180.0 . 2_454 ?
N2 Cu1 N1 94.52(14) . 2_454 ?
N2 Cu1 N1 85.48(14) 2_454 2_454 ?
N2 Cu1 N1 85.48(14) . . ?
N2 Cu1 N1 94.52(14) 2_454 . ?
N2 Cu1 N2 180.0 . 2_454 ?
Cu1 N1 H1 106.5 . . ?
C1 N1 Cu1 119.3(3) . . ?
C1 N1 H1 106.5 . . ?
C2 N1 Cu1 106.6(3) . . ?
C2 N1 H1 106.5 . . ?
C2 N1 C1 110.8(3) . . ?
Cu1 N2 H2 107.3 . . ?
C3 N2 Cu1 106.6(3) . . ?
C3 N2 H2 107.3 . . ?
C4 N2 Cu1 116.7(3) . . ?
C4 N2 H2 107.3 . . ?
C4 N2 C3 111.1(3) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 110.0 . . ?
N1 C2 H2B 110.0 . . ?
N1 C2 C3 108.4(3) . . ?
H2A C2 H2B 108.4 . . ?
C3 C2 H2A 110.0 . . ?
C3 C2 H2B 110.0 . . ?
N2 C3 C2 108.4(3) . . ?
N2 C3 H3A 110.0 . . ?
N2 C3 H3B 110.0 . . ?
C2 C3 H3A 110.0 . . ?
C2 C3 H3B 110.0 . . ?
H3A C3 H3B 108.4 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C5 S1 S2 101.18(16) . . ?
O1 S2 S1 100.50(15) . . ?
O2 S2 S1 106.90(15) . . ?
O2 S2 O1 111.9(2) . . ?
O3 S2 S1 108.55(15) . . ?
O3 S2 O1 114.7(2) . . ?
O3 S2 O2 113.1(2) . . ?
C6 C5 S1 111.6(4) . . ?
C10 C5 S1 128.7(6) . . ?
C10 C5 C6 119.6(6) . . ?
C5 C6 H6 121.8 . . ?
C7 C6 C5 116.4(7) . . ?
C7 C6 H6 121.8 . . ?
F1 C7 C8 119.2(7) . . ?
C6 C7 F1 117.7(8) . . ?
C6 C7 C8 123.1(8) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 C7 121.9(8) . . ?
C9 C8 H8 119.1 . . ?
C8 C9 H9 120.8 . . ?
C8 C9 C10 118.4(8) . . ?
C10 C9 H9 120.8 . . ?
C5 C10 C9 120.5(8) . . ?
C5 C10 C11 119.6(7) . . ?
C11 C10 C9 119.9(7) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H4D O4 H4E 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4E O1 0.85 1.94 2.789(5) 176.5 2_454

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 N1 C2 C3 40.4(4) . . . . ?
Cu1 N2 C3 C2 41.2(4) . . . . ?
N1 C2 C3 N2 -55.5(4) . . . . ?
C1 N1 C2 C3 171.7(3) . . . . ?
C4 N2 C3 C2 -87.0(4) . . . . ?
S1 C5 C6 C7 -175.6(5) . . . . ?
S1 C5 C10 C9 176.9(4) . . . . ?
S1 C5 C10 C11 -4.0(8) . . . . ?
S2 S1 C5 C6 -90.4(4) . . . . ?
S2 S1 C5 C10 92.1(5) . . . . ?
F1 C7 C8 C9 -180.0(6) . . . . ?
C5 C6 C7 F1 178.4(6) . . . . ?
C5 C6 C7 C8 -2.3(10) . . . . ?
C6 C5 C10 C9 -0.5(8) . . . . ?
C6 C5 C10 C11 178.7(5) . . . . ?
C6 C7 C8 C9 0.7(11) . . . . ?
C7 C8 C9 C10 1.1(9) . . . . ?
C8 C9 C10 C5 -1.2(8) . . . . ?
C8 C9 C10 C11 179.7(6) . . . . ?
C10 C5 C6 C7 2.2(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
