# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1052056'
_audit_update_record             
;
2015-04-12 deposited with the CCDC.
2015-06-18 downloaded from the CCDC.
;
_audit_creation_date             2014-07-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_chemical_formula_moiety         'C28 H20 Cu F6 N8 O6 S2, 2(H2 O)'
_chemical_formula_sum            'C28 H24 Cu F6 N8 O8 S2'
_chemical_formula_weight         842.22

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00300 0.00200 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
F 0.01700 0.01000 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
O 0.01100 0.00600 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
N 0.00600 0.00300 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
S 0.12500 0.12300 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
Cu 0.32000 1.26500 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19099998474
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_symmetry_Int_Tables_number      61
_cell_length_a                   17.9015(3)
_cell_length_b                   9.3530(2)
_cell_length_c                   19.7128(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3300.57(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293
_cell_measurement_reflns_used    14245
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      26.105

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.885
_exptl_crystal_density_diffrn    1.6947
_exptl_crystal_F_000             1708.0
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.665
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

_diffrn_measurement_device       KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      293
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14453
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         4.18
_diffrn_measured_fraction_theta_full 0.9929
_diffrn_measured_fraction_theta_max 0.9929
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  all
_diffrn_orient_matrix_type       X=UH

_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              22
_reflns_limit_h_min              0
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                2769
_reflns_number_total             3373
_reflns_threshold_expression     I>=2u(I)

_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_refine_diff_density_max         0.6066
_refine_diff_density_min         -0.6058
_refine_diff_density_rms         0.1042
_refine_ls_d_res_high            0.7989
_refine_ls_d_res_low             4.8744
_refine_ls_goodness_of_fit_ref   1.0520
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3373
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0574
_refine_ls_restrained_S_all      1.0515
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0773P)²+4.6192P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1429
_refine_ls_wR_factor_ref         0.1510
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O4-H4a = O4-H4b
 0.84 with sigma of 0.01
 H4a-H4b
 1.34 with sigma of 0.02
3. Others
 Fixed X: Cu1(0.5)
 Fixed Y: Cu1(0)
 Fixed Z: Cu1(0.5)
4.a Riding coordinates:
 C1(H1), C6(H6), C9(H9), C11(H11), C3(H3), C12(H12), C13(H13), C2(H2), C4(H4),
 C10(H10)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cu1 Cu 0.500000 0.000000 0.500000 0.0322(2) Uani 1.000000 2 S T P
S1 S 0.54058(5) -0.28709(11) 0.38813(5) 0.0528(3) Uani 1.000000 1 . . .
N3 N 0.58951(13) -0.0929(3) 0.53921(13) 0.0326(6) Uani 1.000000 1 . . .
N1 N 0.58106(13) 0.0990(3) 0.44593(13) 0.0310(6) Uani 1.000000 1 . . .
N2 N 0.65429(13) -0.0475(3) 0.51198(13) 0.0293(5) Uani 1.000000 1 . . .
C5 C 0.65088(15) 0.0591(3) 0.46133(15) 0.0289(6) Uani 1.000000 1 . . .
N4 N 0.60413(14) -0.1915(3) 0.58364(13) 0.0339(6) Uani 1.000000 1 . . .
C7 C 0.67964(16) -0.2103(3) 0.58571(15) 0.0303(6) Uani 1.000000 1 . . .
C1 C 0.57291(17) 0.1993(4) 0.39811(17) 0.0392(8) Uani 1.000000 1 . . .
H1 H 0.52398(17) 0.2315(4) 0.38534(17) 0.0470(9) Uiso 1.000000 1 R . .
C8 C 0.71414(16) -0.3108(3) 0.63333(15) 0.0309(6) Uani 1.000000 1 . . .
C6 C 0.71174(16) -0.1187(3) 0.54009(15) 0.0314(7) Uani 1.000000 1 . . .
H6 H 0.76183(16) -0.0985(3) 0.52559(15) 0.0377(8) Uiso 1.000000 1 R . .
O1 O 0.48807(15) -0.1884(4) 0.41626(15) 0.0598(8) Uani 1.000000 1 . . .
C9 C 0.79185(17) -0.3210(3) 0.63836(17) 0.0360(7) Uani 1.000000 1 . . .
H9 H 0.82311(17) -0.2641(3) 0.60943(17) 0.0432(8) Uiso 1.000000 1 R . .
C11 C 0.7789(2) -0.4927(4) 0.7275(2) 0.0468(9) Uani 1.000000 1 . . .
H11 H 0.8009(2) -0.5548(4) 0.7608(2) 0.0561(11) Uiso 1.000000 1 R . .
C3 C 0.70414(19) 0.2168(4) 0.38184(17) 0.0412(8) Uani 1.000000 1 . . .
H3 H 0.74595(19) 0.2584(4) 0.35858(17) 0.0494(9) Uiso 1.000000 1 R . .
C12 C 0.7021(2) -0.4835(4) 0.7223(2) 0.0526(10) Uani 1.000000 1 . . .
H12 H 0.6707(2) -0.5395(4) 0.7515(2) 0.0631(11) Uiso 1.000000 1 R . .
C13 C 0.67007(18) -0.3937(4) 0.67490(19) 0.0447(8) Uani 1.000000 1 . . .
H13 H 0.61668(18) -0.3892(4) 0.67098(19) 0.0536(10) Uiso 1.000000 1 R . .
O4 O 0.87870(18) -0.0506(5) 0.51254(19) 0.0725(9) Uani 1.000000 1 D . .
C2 C 0.63275(18) 0.2598(4) 0.36495(18) 0.0430(8) Uani 1.000000 1 . . .
H2 H 0.62427(18) 0.3314(4) 0.33089(18) 0.0516(10) Uiso 1.000000 1 R . .
C4 C 0.71413(17) 0.1143(4) 0.43110(17) 0.0359(7) Uani 1.000000 1 . . .
H4 H 0.76236(17) 0.0814(4) 0.44556(17) 0.0430(8) Uiso 1.000000 1 R . .
F2 F 0.45035(15) -0.3323(4) 0.28824(16) 0.0935(10) Uani 1.000000 1 . . .
C10 C 0.82291(18) -0.4132(4) 0.68519(19) 0.0426(8) Uani 1.000000 1 . . .
H10 H 0.87619(18) -0.4223(4) 0.68863(19) 0.0511(10) Uiso 1.000000 1 R . .
C14 C 0.5189(2) -0.2856(6) 0.2985(2) 0.0636(12) Uani 1.000000 1 . . .
F3 F 0.56495(18) -0.3647(4) 0.26352(17) 0.1108(13) Uani 1.000000 1 . . .
O3 O 0.5244(3) -0.4343(4) 0.4053(2) 0.1078(14) Uani 1.000000 1 . . .
O2 O 0.61613(17) -0.2469(5) 0.3928(2) 0.1067(16) Uani 1.000000 1 . . .
F1 F 0.5207(3) -0.1531(5) 0.2747(2) 0.1267(15) Uani 1.000000 1 . . .
H4a H 0.899(2) -0.008(5) 0.4799(16) 0.09(2) Uiso 1.000000 1 D . .
H4b H 0.9133(17) -0.063(6) 0.5406(17) 0.072(16) Uiso 1.000000 1 D . .


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 N3 1.980(2) 5_656 ?
Cu1 N3 1.980(2) . ?
Cu1 N1 2.024(2) 5_656 ?
Cu1 N1 2.024(2) . ?
Cu1 O1 2.424(3) . ?
Cu1 O1 2.424(3) 5_656 ?
S1 O1 1.429(3) . ?
S1 C14 1.809(5) . ?
S1 O3 1.447(4) . ?
S1 O2 1.407(3) . ?
N3 N2 1.346(3) . ?
N3 N4 1.299(4) . ?
N1 C5 1.339(4) . ?
N1 C1 1.338(4) . ?
N2 C5 1.413(4) . ?
N2 C6 1.344(4) . ?
C5 C4 1.380(4) . ?
N4 C7 1.364(4) . ?
C7 C8 1.465(4) . ?
C7 C6 1.369(4) . ?
C1 H1 0.9600 . ?
C1 C2 1.377(5) . ?
C8 C9 1.398(4) . ?
C8 C13 1.377(5) . ?
C6 H6 0.9599 . ?
C9 H9 0.9600 . ?
C9 C10 1.380(5) . ?
C11 H11 0.9599 . ?
C11 C12 1.383(5) . ?
C11 C10 1.367(5) . ?
C3 H3 0.9601 . ?
C3 C2 1.381(5) . ?
C3 C4 1.376(5) . ?
C12 H12 0.9599 . ?
C12 C13 1.380(5) . ?
C13 H13 0.9598 . ?
O4 H4a 0.840(10) . ?
O4 H4b 0.838(10) . ?
C2 H2 0.9600 . ?
C4 H4 0.9601 . ?
F2 C14 1.318(5) . ?
C10 H10 0.9600 . ?
C14 F3 1.305(5) . ?
C14 F1 1.327(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cu1 N3 180.0 . 5_656 ?
N1 Cu1 N3 79.98(10) . . ?
N1 Cu1 N3 79.98(10) 5_656 5_656 ?
N1 Cu1 N3 100.02(10) . 5_656 ?
N1 Cu1 N3 100.02(10) 5_656 . ?
N1 Cu1 N1 180.0 5_656 . ?
O1 Cu1 N3 91.04(10) 5_656 5_656 ?
O1 Cu1 N3 88.96(10) 5_656 . ?
O1 Cu1 N3 91.04(10) . . ?
O1 Cu1 N3 88.96(10) . 5_656 ?
O1 Cu1 N1 87.89(10) . 5_656 ?
O1 Cu1 N1 92.11(10) 5_656 5_656 ?
O1 Cu1 N1 87.89(10) 5_656 . ?
O1 Cu1 N1 92.11(10) . . ?
O1 Cu1 O1 180.0 5_656 . ?
C14 S1 O1 103.45(19) . . ?
O3 S1 O1 113.1(3) . . ?
O3 S1 C14 101.1(3) . . ?
O2 S1 O1 115.7(2) . . ?
O2 S1 C14 105.6(2) . . ?
O2 S1 O3 115.5(3) . . ?
N2 N3 Cu1 113.78(19) . 5_656 ?
N4 N3 Cu1 137.6(2) . 5_656 ?
N4 N3 N2 108.6(2) . . ?
C5 N1 Cu1 115.0(2) . 5_656 ?
C1 N1 Cu1 127.8(2) . 5_656 ?
C1 N1 C5 117.2(3) . . ?
C5 N2 N3 117.8(2) . . ?
C6 N2 N3 109.8(2) . . ?
C6 N2 C5 132.4(2) . . ?
N2 C5 N1 113.4(2) . . ?
C4 C5 N1 124.3(3) . . ?
C4 C5 N2 122.3(3) . . ?
C7 N4 N3 108.2(2) . . ?
C8 C7 N4 121.3(3) . . ?
C6 C7 N4 108.4(3) . . ?
C6 C7 C8 130.2(3) . . ?
H1 C1 N1 120.3 . . ?
C2 C1 N1 122.6(3) . . ?
C2 C1 H1 117.1(2) . . ?
C9 C8 C7 120.6(3) . . ?
C13 C8 C7 120.1(3) . . ?
C13 C8 C9 119.3(3) . . ?
C7 C6 N2 105.0(3) . . ?
H6 C6 N2 119.6 . . ?
H6 C6 C7 135.31(17) . . ?
S1 O1 Cu1 132.51(16) . 5_656 ?
H9 C9 C8 120.0 . . ?
C10 C9 C8 119.4(3) . . ?
C10 C9 H9 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 120.7(2) . . ?
C10 C11 C12 119.6(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 121.2(2) . . ?
C4 C3 C2 119.6(3) . . ?
H12 C12 C11 120.3 . . ?
C13 C12 C11 120.1(4) . . ?
C13 C12 H12 119.6(2) . . ?
C12 C13 C8 120.5(3) . . ?
H13 C13 C8 119.9 . . ?
H13 C13 C12 119.6(2) . . ?
H4b O4 H4a 104(2) . . ?
C3 C2 C1 119.1(3) . . ?
H2 C2 C1 119.7 . . ?
H2 C2 C3 121.2(2) . . ?
C3 C4 C5 117.3(3) . . ?
H4 C4 C5 119.3 . . ?
H4 C4 C3 123.4(2) . . ?
C11 C10 C9 121.1(3) . . ?
H10 C10 C9 120.2 . . ?
H10 C10 C11 118.7(2) . . ?
F2 C14 S1 110.4(3) . . ?
F3 C14 S1 112.1(3) . . ?
F3 C14 F2 108.6(4) . . ?
F1 C14 S1 110.4(4) . . ?
F1 C14 F2 106.2(4) . . ?
F1 C14 F3 109.0(4) . . ?

loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
O4 H4a 1 0.8400 0.0100 -0.0000
O4 H4b 1 0.8400 0.0100 0.0019
H4a H4b 1 1.3400 0.0200 0.0133

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1052058'
_audit_update_record             
;
2015-04-12 deposited with the CCDC.
2015-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H18 Cu F6 N10 O6 S2'
_chemical_formula_sum            'C26 H18 Cu F6 N10 O6 S2'
_chemical_formula_weight         808.16

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'

_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                   8.6034(3)
_cell_length_b                   9.2137(4)
_cell_length_c                   11.0129(5)
_cell_angle_alpha                111.653(2)
_cell_angle_beta                 92.753(2)
_cell_angle_gamma                102.528(2)
_cell_volume                     784.13(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    293
_cell_measurement_reflns_used    8013
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      25.028

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_F_000             407
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.925
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  KappaCCD2000
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 14
_diffrn_reflns_number            8674
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_av_R_equivalents  0.0889
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.010
_diffrn_reflns_theta_max         25.190
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             2708
_reflns_number_gt                2523
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000

_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       ?
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep (Johnson, 1976)'
_computing_publication_material  ?

_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.069(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2708
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1342
_refine_ls_wR_factor_gt          0.1289
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_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_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 0.0000 0.0000 0.5000 0.0365(2) Uani 1 2 d S . P . .
S2 S -0.27900(7) 0.03624(7) 0.26090(6) 0.0434(2) Uani 1 1 d . . . . .
N2 N 0.1343(2) 0.1828(2) 0.46624(18) 0.0362(4) Uani 1 1 d . . . . .
N3 N 0.2322(2) 0.1965(2) 0.38113(19) 0.0386(4) Uani 1 1 d . . . . .
N1 N -0.0634(2) 0.1882(2) 0.64086(19) 0.0368(4) Uani 1 1 d . . . . .
O1 O -0.2113(2) -0.0446(2) 0.33080(19) 0.0546(5) Uani 1 1 d . . . . .
C6 C 0.1175(2) 0.3294(2) 0.5457(2) 0.0342(5) Uani 1 1 d . . . . .
N4 N 0.2776(2) 0.3540(2) 0.40777(19) 0.0357(4) Uani 1 1 d . . . . .
C5 C 0.0147(2) 0.3351(3) 0.6465(2) 0.0353(5) Uani 1 1 d . . . . .
N5 N 0.4205(3) 0.5723(3) 0.3703(3) 0.0517(6) Uani 1 1 d . . . . .
C4 C -0.0010(3) 0.4774(3) 0.7434(2) 0.0428(6) Uani 1 1 d . . . . .
H4 H 0.0560 0.5794 0.7438 0.051 Uiso 1 1 d R U . . .
O3 O -0.4443(2) -0.0343(3) 0.2080(3) 0.0718(6) Uani 1 1 d . . . . .
C8 C 0.3851(2) 0.4124(3) 0.3299(2) 0.0398(5) Uani 1 1 d . . . . .
C7 C 0.2107(3) 0.4415(3) 0.5084(2) 0.0360(5) Uani 1 1 d . . . . .
H7 H 0.2149 0.5537 0.5543 0.043 Uiso 1 1 d R U . . .
C3 C -0.1002(3) 0.4664(3) 0.8351(3) 0.0515(6) Uani 1 1 d . . . . .
H3 H -0.1096 0.5628 0.9050 0.062 Uiso 1 1 d R U . . .
C12 C 0.5143(3) 0.6332(4) 0.2989(4) 0.0641(9) Uani 1 1 d . . . . .
H12 H 0.5465 0.7474 0.3209 0.077 Uiso 1 1 d R U . . .
O2 O -0.2292(3) 0.2078(2) 0.3218(2) 0.0739(7) Uani 1 1 d . . . . .
C1 C -0.1606(3) 0.1811(3) 0.7294(3) 0.0478(6) Uani 1 1 d . . . . .
H1 H -0.2182 0.0782 0.7271 0.057 Uiso 1 1 d R U . . .
C9 C 0.4377(3) 0.3090(3) 0.2270(3) 0.0523(6) Uani 1 1 d . . . . .
H9 H 0.4086 0.1958 0.2096 0.063 Uiso 1 1 d R U . . .
C2 C -0.1813(3) 0.3189(3) 0.8301(3) 0.0514(6) Uani 1 1 d . . . . .
H2 H -0.2543 0.3118 0.8921 0.062 Uiso 1 1 d R U . . .
F2 F -0.0209(2) 0.0635(4) 0.1487(2) 0.1101(9) Uani 1 1 d . . . . .
F1 F -0.1938(4) -0.1609(3) 0.0514(2) 0.1142(9) Uani 1 1 d . . . . .
F3 F -0.2337(3) 0.0470(3) 0.0309(2) 0.1046(8) Uani 1 1 d . . . . .
C13 C -0.1780(4) -0.0040(4) 0.1156(3) 0.0694(8) Uani 1 1 d . . . . .
C11 C 0.5713(3) 0.5400(5) 0.1913(4) 0.0668(8) Uani 1 1 d . . . . .
H11 H 0.6385 0.5914 0.1440 0.080 Uiso 1 1 d R U . . .
C10 C 0.5345(4) 0.3777(5) 0.1551(3) 0.0720(9) Uani 1 1 d . . . . .
H10 H 0.5707 0.3079 0.0795 0.086 Uiso 1 1 d 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
Cu1 N2 1.9922(17) 2_556 ?
Cu1 N2 1.9922(17) . ?
Cu1 N1 2.0535(19) . ?
Cu1 N1 2.0535(19) 2_556 ?
Cu1 O1 2.3941(17) . ?
Cu1 O1 2.3942(17) 2_556 ?
S2 O3 1.423(2) . ?
S2 O2 1.424(2) . ?
S2 O1 1.4336(18) . ?
S2 C13 1.814(3) . ?
N2 N3 1.312(3) . ?
N2 C6 1.355(3) . ?
N3 N4 1.332(3) . ?
N1 C1 1.325(3) . ?
N1 C5 1.351(3) . ?
C6 C7 1.366(3) . ?
C6 C5 1.445(3) . ?
N4 C7 1.346(3) . ?
N4 C8 1.442(3) . ?
C5 C4 1.391(3) . ?
N5 C8 1.330(3) . ?
N5 C12 1.333(4) . ?
C4 C3 1.371(4) . ?
C4 H4 0.9599 . ?
C8 C9 1.355(4) . ?
C7 H7 0.9600 . ?
C3 C2 1.366(4) . ?
C3 H3 0.9600 . ?
C12 C11 1.367(5) . ?
C12 H12 0.9600 . ?
C1 C2 1.397(4) . ?
C1 H1 0.9601 . ?
C9 C10 1.388(4) . ?
C9 H9 0.9601 . ?
C2 H2 0.9601 . ?
F2 C13 1.329(4) . ?
F1 C13 1.327(4) . ?
F3 C13 1.303(4) . ?
C11 C10 1.356(5) . ?
C11 H11 0.9601 . ?
C10 H10 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N2 180.00(10) 2_556 . ?
N2 Cu1 N1 99.23(7) 2_556 . ?
N2 Cu1 N1 80.77(7) . . ?
N2 Cu1 N1 80.77(7) 2_556 2_556 ?
N2 Cu1 N1 99.23(7) . 2_556 ?
N1 Cu1 N1 180.0 . 2_556 ?
N2 Cu1 O1 88.07(7) 2_556 . ?
N2 Cu1 O1 91.93(7) . . ?
N1 Cu1 O1 95.40(7) . . ?
N1 Cu1 O1 84.60(7) 2_556 . ?
N2 Cu1 O1 91.93(7) 2_556 2_556 ?
N2 Cu1 O1 88.07(7) . 2_556 ?
N1 Cu1 O1 84.60(7) . 2_556 ?
N1 Cu1 O1 95.40(7) 2_556 2_556 ?
O1 Cu1 O1 180.0 . 2_556 ?
O3 S2 O2 117.02(14) . . ?
O3 S2 O1 114.50(12) . . ?
O2 S2 O1 114.37(13) . . ?
O3 S2 C13 103.52(16) . . ?
O2 S2 C13 101.62(15) . . ?
O1 S2 C13 103.00(14) . . ?
N3 N2 C6 110.74(17) . . ?
N3 N2 Cu1 135.44(15) . . ?
C6 N2 Cu1 113.75(15) . . ?
N2 N3 N4 105.11(18) . . ?
C1 N1 C5 118.3(2) . . ?
C1 N1 Cu1 127.67(16) . . ?
C5 N1 Cu1 113.85(14) . . ?
S2 O1 Cu1 141.99(11) . . ?
N2 C6 C7 107.3(2) . . ?
N2 C6 C5 117.55(18) . . ?
C7 C6 C5 135.1(2) . . ?
N3 N4 C7 112.64(17) . . ?
N3 N4 C8 119.90(19) . . ?
C7 N4 C8 127.5(2) . . ?
N1 C5 C4 122.2(2) . . ?
N1 C5 C6 113.87(18) . . ?
C4 C5 C6 123.9(2) . . ?
C8 N5 C12 115.3(3) . . ?
C3 C4 C5 118.2(2) . . ?
C3 C4 H4 122.1 . . ?
C5 C4 H4 119.7 . . ?
N5 C8 C9 126.5(2) . . ?
N5 C8 N4 112.4(2) . . ?
C9 C8 N4 121.1(2) . . ?
N4 C7 C6 104.17(19) . . ?
N4 C7 H7 136.3 . . ?
C6 C7 H7 119.5 . . ?
C2 C3 C4 120.3(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.7 . . ?
N5 C12 C11 123.2(3) . . ?
N5 C12 H12 121.2 . . ?
C11 C12 H12 115.7 . . ?
N1 C1 C2 122.6(2) . . ?
N1 C1 H1 119.9 . . ?
C2 C1 H1 117.4 . . ?
C8 C9 C10 116.2(3) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 124.6 . . ?
C3 C2 C1 118.3(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 121.6 . . ?
F3 C13 F1 106.4(3) . . ?
F3 C13 F2 108.5(3) . . ?
F1 C13 F2 106.2(3) . . ?
F3 C13 S2 113.1(3) . . ?
F1 C13 S2 111.4(3) . . ?
F2 C13 S2 110.8(2) . . ?
C10 C11 C12 119.5(3) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 H11 119.1 . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10 122.1 . . ?
C9 C10 H10 118.5 . . ?

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.077

_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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1052059'
_audit_update_record             
;
2015-04-12 deposited with the CCDC.
2015-06-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H16 Cu F6 N4 O6 S2'
_chemical_formula_sum            'C22 H16 Cu F6 N4 O6 S2'
_chemical_formula_weight         674.05

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'
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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   10.0099(3)
_cell_length_b                   13.9540(5)
_cell_length_c                   18.8133(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.1196(14)
_cell_angle_gamma                90
_cell_volume                     2586.93(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293
_cell_measurement_reflns_used    3574
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_F_000             1356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    1.096
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4362
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.106
_diffrn_reflns_theta_max         23.910
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measured_fraction_theta_full 0.797
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_Laue_measured_fraction_full 0.797
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 0.797

_reflns_number_total             1868
_reflns_number_gt                1586
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_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       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep (Johnson, 1976)'
_computing_publication_material  ?

_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)+(0.1155P)²+1.1535P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0158(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1868
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1553
_refine_ls_wR_factor_gt          0.1427
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.742
_refine_diff_density_rms         0.096

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 0.31955(4) 0.2500 0.0428(4) Uani 1 2 d S T P . .
O1 O 0.3570(3) 0.4526(2) 0.20549(15) 0.0586(8) Uani 1 1 d . . . . .
F1 F 0.0911(4) 0.3804(3) 0.1357(3) 0.145(2) Uani 1 1 d . . . . .
S1 S 0.29492(11) 0.49562(7) 0.13815(5) 0.0489(4) Uani 1 1 d . . . . .
C1 C 0.6715(5) 0.3688(3) 0.1433(2) 0.0563(11) Uani 1 1 d . . . . .
H1 H 0.7248 0.4049 0.1816 0.068 Uiso 1 1 d R U . . .
N1 N 0.5652(3) 0.3189(2) 0.15713(17) 0.0421(8) Uani 1 1 d . . . . .
C11 C 0.1164(6) 0.4731(4) 0.1363(3) 0.0758(14) Uani 1 1 d . . . . .
C2 C 0.7057(5) 0.3709(3) 0.0761(3) 0.0630(12) Uani 1 1 d . . . . .
H2 H 0.7819 0.4079 0.0672 0.076 Uiso 1 1 d R U . . .
N2 N 0.3535(3) 0.2317(2) 0.19124(16) 0.0465(8) Uani 1 1 d . . . . .
O2 O 0.3233(4) 0.4475(3) 0.07550(17) 0.0867(13) Uani 1 1 d . . . . .
F2 F 0.0420(4) 0.5069(3) 0.0768(2) 0.1293(16) Uani 1 1 d . . . . .
C4 C 0.5252(5) 0.2649(3) 0.0359(2) 0.0566(12) Uani 1 1 d . . . . .
H4 H 0.4725 0.2256 -0.0005 0.068 Uiso 1 1 d R U . . .
C3 C 0.6306(5) 0.3186(3) 0.0218(2) 0.0609(13) Uani 1 1 d . . . . .
H3 H 0.6515 0.3203 -0.0261 0.073 Uiso 1 1 d R U . . .
O3 O 0.3031(4) 0.5978(2) 0.13710(19) 0.0755(10) Uani 1 1 d . . . . .
F3 F 0.0723(4) 0.5143(3) 0.1891(3) 0.1269(15) Uani 1 1 d . . . . .
C5 C 0.4916(4) 0.2669(3) 0.10417(18) 0.0420(9) Uani 1 1 d . . . . .
C6 C 0.3726(4) 0.2160(3) 0.12391(19) 0.0460(9) Uani 1 1 d . . . . .
C10 C 0.2466(5) 0.1904(3) 0.2138(3) 0.0611(12) Uani 1 1 d . . . . .
H10 H 0.2324 0.2015 0.2623 0.073 Uiso 1 1 d R U . . .
C8 C 0.1772(6) 0.1175(3) 0.1003(3) 0.0730(15) Uani 1 1 d . . . . .
H8 H 0.1154 0.0783 0.0678 0.088 Uiso 1 1 d R U . . .
C7 C 0.2862(5) 0.1591(3) 0.0767(3) 0.0597(12) Uani 1 1 d . . . . .
H7 H 0.3038 0.1498 0.0286 0.072 Uiso 1 1 d R U . . .
C9 C 0.1581(5) 0.1336(4) 0.1698(3) 0.0747(15) Uani 1 1 d . . . . .
H9 H 0.0837 0.1045 0.1877 0.090 Uiso 1 1 d 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
Cu1 N1 1.970(3) 2_655 ?
Cu1 N1 1.970(3) . ?
Cu1 N2 2.075(3) 2_655 ?
Cu1 N2 2.075(3) . ?
Cu1 O1 2.403(3) 2_655 ?
Cu1 O1 2.403(3) . ?
O1 S1 1.440(3) . ?
F1 C11 1.318(6) . ?
S1 O2 1.428(3) . ?
S1 O3 1.428(4) . ?
S1 C11 1.809(6) . ?
C1 N1 1.334(5) . ?
C1 C2 1.368(6) . ?
C1 H1 0.9600 . ?
N1 C5 1.343(5) . ?
C11 F3 1.289(7) . ?
C11 F2 1.318(6) . ?
C2 C3 1.367(7) . ?
C2 H2 0.9600 . ?
N2 C6 1.332(5) . ?
N2 C10 1.347(6) . ?
C4 C3 1.357(7) . ?
C4 C5 1.385(5) . ?
C4 H4 0.9599 . ?
C3 H3 0.9599 . ?
C5 C6 1.490(6) . ?
C6 C7 1.377(6) . ?
C10 C9 1.357(7) . ?
C10 H10 0.9600 . ?
C8 C9 1.373(8) . ?
C8 C7 1.376(8) . ?
C8 H8 0.9600 . ?
C7 H7 0.9600 . ?
C9 H9 0.9601 . ?

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 179.50(18) 2_655 . ?
N1 Cu1 N2 80.70(13) 2_655 2_655 ?
N1 Cu1 N2 99.00(12) . 2_655 ?
N1 Cu1 N2 99.00(12) 2_655 . ?
N1 Cu1 N2 80.70(13) . . ?
N2 Cu1 N2 107.59(17) 2_655 . ?
N1 Cu1 O1 87.95(11) 2_655 2_655 ?
N1 Cu1 O1 92.43(12) . 2_655 ?
N2 Cu1 O1 87.05(11) 2_655 2_655 ?
N2 Cu1 O1 164.57(11) . 2_655 ?
N1 Cu1 O1 92.44(12) 2_655 . ?
N1 Cu1 O1 87.95(11) . . ?
N2 Cu1 O1 164.57(11) 2_655 . ?
N2 Cu1 O1 87.05(11) . . ?
O1 Cu1 O1 78.86(14) 2_655 . ?
S1 O1 Cu1 140.09(18) . . ?
O2 S1 O3 116.0(2) . . ?
O2 S1 O1 114.34(19) . . ?
O3 S1 O1 114.3(2) . . ?
O2 S1 C11 104.0(3) . . ?
O3 S1 C11 103.4(2) . . ?
O1 S1 C11 102.5(2) . . ?
N1 C1 C2 121.9(4) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.1 . . ?
C1 N1 C5 119.3(3) . . ?
C1 N1 Cu1 124.8(3) . . ?
C5 N1 Cu1 115.9(3) . . ?
F3 C11 F2 106.0(5) . . ?
F3 C11 F1 110.7(6) . . ?
F2 C11 F1 105.3(5) . . ?
F3 C11 S1 112.2(4) . . ?
F2 C11 S1 111.2(5) . . ?
F1 C11 S1 111.0(4) . . ?
C3 C2 C1 119.0(4) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.6 . . ?
C6 N2 C10 118.9(4) . . ?
C6 N2 Cu1 113.4(3) . . ?
C10 N2 Cu1 127.7(3) . . ?
C3 C4 C5 119.6(4) . . ?
C3 C4 H4 121.7 . . ?
C5 C4 H4 118.7 . . ?
C4 C3 C2 119.6(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.4 . . ?
N1 C5 C4 120.6(4) . . ?
N1 C5 C6 115.6(3) . . ?
C4 C5 C6 123.8(4) . . ?
N2 C6 C7 122.0(4) . . ?
N2 C6 C5 114.4(3) . . ?
C7 C6 C5 123.6(4) . . ?
N2 C10 C9 121.8(5) . . ?
N2 C10 H10 119.3 . . ?
C9 C10 H10 118.9 . . ?
C9 C8 C7 119.3(5) . . ?
C9 C8 H8 121.1 . . ?
C7 C8 H8 119.6 . . ?
C8 C7 C6 118.6(5) . . ?
C8 C7 H7 122.3 . . ?
C6 C7 H7 119.1 . . ?
C10 C9 C8 119.4(5) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 120.7 . . ?

# start Validation Reply Form
_vrf_THETM01_shelxl              
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: Overall quality of the crystal is poor leading to a two-theta
maximum of 48 degrees. However, available data unambiguously establishes
the identity and stereochemistry of the molecule.
;
_vrf_PLAT019_shelxl              
;
PROBLEM: _diffrn_measured_fraction_theta_full/_max < 1.0      0.861 Report
RESPONSE: Overall quality of the crystal is poor.
;
# end Validation Reply Form

_shelxl_version_number           2013-4



