# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2019

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

data_2
_audit_block_doi                 10.5517/ccdc.csd.cc1kk9jy
_database_code_depnum_ccdc_archive 'CCDC 1446600'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C6CC04884F 2016
_audit_update_record             
;
2016-01-11 deposited with the CCDC.	2019-04-29 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 H36 Cu N6 O8'
_chemical_formula_weight         480.03

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'
Cu Cu 0.3201 1.2651 '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                   9.4885(3)
_cell_length_b                   10.1789(3)
_cell_length_c                   11.6397(4)
_cell_angle_alpha                85.237(2)
_cell_angle_beta                 74.9220(10)
_cell_angle_gamma                77.7440(10)
_cell_volume                     1060.29(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5359
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             510
_exptl_absorpt_coefficient_mu    1.083
_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      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6913
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3721
_reflns_number_gt                3520
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0697P)²+0.6698P] 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         3721
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.1001
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.003

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 0.69631(3) 0.72271(2) 0.74552(2) 0.01928(12) Uani 1 1 d . . .
C1 C 1.0107(3) 0.6516(3) 0.6059(3) 0.0423(7) Uani 1 1 d . . .
H1A H 0.9714 0.5791 0.5868 0.063 Uiso 1 1 calc R . .
H1B H 1.0508 0.6259 0.6740 0.063 Uiso 1 1 calc R . .
H1C H 1.0881 0.6717 0.5394 0.063 Uiso 1 1 calc R . .
C2 C 0.9466(3) 0.8811(3) 0.6755(3) 0.0367(6) Uani 1 1 d . . .
H2A H 0.8763 0.9653 0.6739 0.044 Uiso 1 1 calc R . .
H2B H 1.0398 0.8911 0.6199 0.044 Uiso 1 1 calc R . .
C3 C 0.9723(3) 0.8576(3) 0.7989(3) 0.0398(6) Uani 1 1 d . . .
H3A H 1.0409 0.7726 0.8016 0.048 Uiso 1 1 calc R . .
H3B H 1.0189 0.9281 0.8147 0.048 Uiso 1 1 calc R . .
C4 C 0.8318(3) 0.8553(3) 0.8957(3) 0.0369(6) Uani 1 1 d . . .
H4A H 0.8525 0.8630 0.9719 0.044 Uiso 1 1 calc R . .
H4B H 0.7573 0.9333 0.8844 0.044 Uiso 1 1 calc R . .
C5 C 0.8760(3) 0.6126(3) 0.9292(3) 0.0392(6) Uani 1 1 d . . .
H5A H 0.9035 0.6293 0.9997 0.059 Uiso 1 1 calc R . .
H5B H 0.9632 0.5971 0.8642 0.059 Uiso 1 1 calc R . .
H5C H 0.8310 0.5349 0.9428 0.059 Uiso 1 1 calc R . .
C6 C 0.6319(3) 0.7423(3) 0.9998(2) 0.0363(6) Uani 1 1 d . . .
H6A H 0.6475 0.7822 1.0672 0.044 Uiso 1 1 calc R . .
H6B H 0.6117 0.6533 1.0245 0.044 Uiso 1 1 calc R . .
C7 C 0.5013(3) 0.8276(3) 0.9612(2) 0.0345(6) Uani 1 1 d . . .
H7A H 0.4122 0.8314 1.0257 0.041 Uiso 1 1 calc R . .
H7B H 0.5183 0.9185 0.9427 0.041 Uiso 1 1 calc R . .
C8 C 0.4119(3) 0.6504(3) 0.8915(3) 0.0380(6) Uani 1 1 d . . .
H8A H 0.4841 0.5781 0.9134 0.057 Uiso 1 1 calc R . .
H8B H 0.3801 0.6239 0.8266 0.057 Uiso 1 1 calc R . .
H8C H 0.3276 0.6713 0.9584 0.057 Uiso 1 1 calc R . .
C9 C 0.3743(3) 0.8774(3) 0.8057(3) 0.0342(6) Uani 1 1 d . . .
H9A H 0.4066 0.9622 0.8018 0.041 Uiso 1 1 calc R . .
H9B H 0.2765 0.8871 0.8605 0.041 Uiso 1 1 calc R . .
C10 C 0.3608(3) 0.8504(3) 0.6841(3) 0.0400(6) Uani 1 1 d . . .
H10A H 0.2831 0.9194 0.6633 0.048 Uiso 1 1 calc R . .
H10B H 0.3306 0.7646 0.6873 0.048 Uiso 1 1 calc R . .
C11 C 0.5032(3) 0.8475(3) 0.5875(2) 0.0363(6) Uani 1 1 d . . .
H11A H 0.4796 0.8531 0.5108 0.044 Uiso 1 1 calc R . .
H11B H 0.5422 0.9267 0.5936 0.044 Uiso 1 1 calc R . .
C12 C 0.5689(3) 0.6048(3) 0.5699(3) 0.0385(6) Uani 1 1 d . . .
H12A H 0.5320 0.6198 0.4996 0.058 Uiso 1 1 calc R . .
H12B H 0.4905 0.5882 0.6370 0.058 Uiso 1 1 calc R . .
H12C H 0.6498 0.5284 0.5595 0.058 Uiso 1 1 calc R . .
C13 C 0.7532(3) 0.7374(3) 0.4900(2) 0.0391(6) Uani 1 1 d . . .
H13A H 0.7194 0.7749 0.4202 0.047 Uiso 1 1 calc R . .
H13B H 0.8142 0.6489 0.4711 0.047 Uiso 1 1 calc R . .
C14 C 0.8441(3) 0.8262(3) 0.5221(2) 0.0377(6) Uani 1 1 d . . .
H14A H 0.9320 0.8292 0.4576 0.045 Uiso 1 1 calc R . .
H14B H 0.7861 0.9169 0.5339 0.045 Uiso 1 1 calc R . .
N1 N 0.8893(2) 0.7731(2) 0.63317(18) 0.0274(4) Uani 1 1 d . . .
N2 N 0.7682(2) 0.7313(2) 0.89994(18) 0.0274(4) Uani 1 1 d . . .
N3 N 0.4796(2) 0.7710(2) 0.85455(17) 0.0248(4) Uani 1 1 d . . .
N4 N 0.6226(2) 0.7259(2) 0.59083(18) 0.0270(4) Uani 1 1 d . . .
N5 N 0.6328(3) 0.2067(2) 0.6900(2) 0.0375(5) Uani 1 1 d . . .
N6 N 0.0088(3) 0.2261(2) 0.8136(2) 0.0405(6) Uani 1 1 d . . .
O1 O 0.7434(3) 0.4976(2) 0.7553(2) 0.0437(5) Uani 1 1 d . . .
O2 O 0.5673(2) 0.3152(2) 0.7403(2) 0.0555(6) Uani 1 1 d . . .
O3 O 0.5923(3) 0.1019(3) 0.7284(3) 0.0745(8) Uani 1 1 d . . .
O4 O 0.7354(3) 0.2053(3) 0.6021(3) 0.0865(10) Uani 1 1 d . . .
O5 O 0.0102(3) 0.3422(2) 0.7677(3) 0.0629(7) Uani 1 1 d . . .
O6 O 0.1273(3) 0.1458(3) 0.8021(3) 0.0665(7) Uani 1 1 d . . .
O7 O -0.1089(4) 0.1976(4) 0.8682(4) 0.1171(16) Uani 1 1 d . . .
O1W O 0.2652(3) 0.4549(3) 0.7486(2) 0.0552(6) Uani 1 1 d . . .
H1WA H 0.208(4) 0.410(4) 0.756(3) 0.050(11) Uiso 1 1 d . . .
H1Y H 0.824(5) 0.452(4) 0.765(4) 0.067(12) Uiso 1 1 d . . .
H1X H 0.697(5) 0.455(4) 0.743(3) 0.054(12) Uiso 1 1 d . . .
H1WB H 0.340(5) 0.402(4) 0.754(3) 0.056(11) 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
Cu1 N4 2.090(2) . ?
Cu1 N1 2.090(2) . ?
Cu1 N2 2.096(2) . ?
Cu1 N3 2.0968(19) . ?
Cu1 O1 2.238(2) . ?
C1 N1 1.492(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.493(3) . ?
C2 C3 1.511(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.508(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N2 1.502(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N2 1.487(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 N2 1.488(3) . ?
C6 C7 1.503(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N3 1.489(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N3 1.487(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 N3 1.493(3) . ?
C9 C10 1.506(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.513(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N4 1.495(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N4 1.489(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N4 1.487(3) . ?
C13 C14 1.501(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N1 1.491(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
N5 O4 1.213(3) . ?
N5 O3 1.221(3) . ?
N5 O2 1.255(3) . ?
N6 O7 1.214(4) . ?
N6 O6 1.225(3) . ?
N6 O5 1.256(3) . ?
O1 H1Y 0.84(5) . ?
O1 H1X 0.73(4) . ?
O1W H1WA 0.76(4) . ?
O1W H1WB 0.81(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
N4 Cu1 N1 85.72(8) . . ?
N4 Cu1 N2 176.79(7) . . ?
N1 Cu1 N2 93.36(8) . . ?
N4 Cu1 N3 93.34(8) . . ?
N1 Cu1 N3 152.88(8) . . ?
N2 Cu1 N3 86.07(8) . . ?
N4 Cu1 O1 91.67(8) . . ?
N1 Cu1 O1 104.75(8) . . ?
N2 Cu1 O1 91.54(9) . . ?
N3 Cu1 O1 102.37(8) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 115.3(2) . . ?
N1 C2 H2A 108.5 . . ?
C3 C2 H2A 108.5 . . ?
N1 C2 H2B 108.5 . . ?
C3 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C4 C3 C2 113.6(2) . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
N2 C4 C3 114.5(2) . . ?
N2 C4 H4A 108.6 . . ?
C3 C4 H4A 108.6 . . ?
N2 C4 H4B 108.6 . . ?
C3 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C7 110.0(2) . . ?
N2 C6 H6A 109.7 . . ?
C7 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C7 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N3 C7 C6 110.4(2) . . ?
N3 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
N3 C7 H7B 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 C10 114.6(2) . . ?
N3 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
N3 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 C11 113.8(2) . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
N4 C11 C10 115.1(2) . . ?
N4 C11 H11A 108.5 . . ?
C10 C11 H11A 108.5 . . ?
N4 C11 H11B 108.5 . . ?
C10 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
N4 C12 H12A 109.5 . . ?
N4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C13 C14 110.1(2) . . ?
N4 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
N4 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
N1 C14 C13 109.9(2) . . ?
N1 C14 H14A 109.7 . . ?
C13 C14 H14A 109.7 . . ?
N1 C14 H14B 109.7 . . ?
C13 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C1 N1 C14 109.5(2) . . ?
C1 N1 C2 109.4(2) . . ?
C14 N1 C2 106.9(2) . . ?
C1 N1 Cu1 110.91(15) . . ?
C14 N1 Cu1 104.16(15) . . ?
C2 N1 Cu1 115.69(16) . . ?
C5 N2 C6 106.4(2) . . ?
C5 N2 C4 108.9(2) . . ?
C6 N2 C4 108.5(2) . . ?
C5 N2 Cu1 116.90(16) . . ?
C6 N2 Cu1 105.56(15) . . ?
C4 N2 Cu1 110.24(16) . . ?
C8 N3 C7 109.2(2) . . ?
C8 N3 C9 109.4(2) . . ?
C7 N3 C9 106.53(19) . . ?
C8 N3 Cu1 112.22(15) . . ?
C7 N3 Cu1 103.35(14) . . ?
C9 N3 Cu1 115.63(15) . . ?
C13 N4 C12 106.6(2) . . ?
C13 N4 C11 108.4(2) . . ?
C12 N4 C11 108.9(2) . . ?
C13 N4 Cu1 105.93(15) . . ?
C12 N4 Cu1 116.75(16) . . ?
C11 N4 Cu1 109.89(15) . . ?
O4 N5 O3 119.5(3) . . ?
O4 N5 O2 120.4(3) . . ?
O3 N5 O2 120.1(3) . . ?
O7 N6 O6 122.3(3) . . ?
O7 N6 O5 119.3(3) . . ?
O6 N6 O5 118.4(3) . . ?
Cu1 O1 H1Y 123(3) . . ?
Cu1 O1 H1X 126(3) . . ?
H1Y O1 H1X 111(4) . . ?
H1WA O1W H1WB 103(4) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.807
_refine_diff_density_min         -0.874
_refine_diff_density_rms         0.126
####################################################################### 
# 
# 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_ok
_database_code_depnum_ccdc_archive 'CCDC 1855255'
loop_
_audit_author_name
_audit_author_address
'Junyu Shen'
;University
China
;
_audit_update_record             
;
2018-07-11 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H21 B2 Cu F8 O S4'
_chemical_formula_weight         522.67

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'
B B 0.0013 0.0007 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Ama2

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

_cell_length_a                   12.8692(17)
_cell_length_b                   14.1500(18)
_cell_length_c                   10.8460(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1975.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4278
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      30.77

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    1.599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7002
_exptl_absorpt_correction_T_max  0.8565
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker,2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5004
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1779
_reflns_number_gt                1751
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0426P)²+11.0487P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_number_reflns         1779
_refine_ls_number_parameters     129
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.1077
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
Cu1 Cu 0.2500 0.76076(5) 0.51974(7) 0.0223(2) Uani 1 2 d S . .
S1 S 0.38010(9) 0.80581(10) 0.65466(14) 0.0306(3) Uani 1 1 d . . .
S2 S 0.37725(13) 0.74343(11) 0.36842(13) 0.0417(4) Uani 1 1 d . . .
F1 F 0.4436(3) 0.5571(3) 0.6415(4) 0.0637(11) Uani 1 1 d . . .
F2 F 0.4335(5) 0.4460(4) 0.5016(5) 0.111(2) Uani 1 1 d . . .
F3 F 0.2500 1.1186(5) 0.5819(6) 0.075(2) Uani 1 2 d S . .
F4 F 0.2500 1.1736(5) 0.3929(9) 0.096(3) Uani 1 2 d S . .
F5 F 0.3377(3) 1.0408(3) 0.4381(5) 0.0689(13) Uani 1 1 d . . .
O1W O 0.2500 0.6118(4) 0.5693(7) 0.0480(16) Uani 1 2 d S . .
H1W H 0.3037 0.5871 0.6017 0.072 Uiso 0.50 1 d PR . .
C1 C 0.2500 0.8346(7) 0.1968(9) 0.077(4) Uani 1 2 d S . .
H1A H 0.2500 0.7731 0.1574 0.092 Uiso 1 2 calc SR . .
H1B H 0.2500 0.8817 0.1319 0.092 Uiso 1 2 calc SR . .
C2 C 0.3521(8) 0.8448(5) 0.2703(7) 0.069(2) Uani 1 1 d . . .
H2A H 0.3484 0.9012 0.3209 0.083 Uiso 1 1 calc R . .
H2B H 0.4094 0.8524 0.2131 0.083 Uiso 1 1 calc R . .
C3 C 0.4949(5) 0.7767(5) 0.4521(8) 0.0580(19) Uani 1 1 d . . .
H3A H 0.5240 0.7207 0.4904 0.070 Uiso 1 1 calc R . .
H3B H 0.5456 0.8004 0.3936 0.070 Uiso 1 1 calc R . .
C4 C 0.4779(4) 0.8496(5) 0.5487(6) 0.0463(15) Uani 1 1 d . . .
H4A H 0.4546 0.9081 0.5112 0.056 Uiso 1 1 calc R . .
H4B H 0.5422 0.8618 0.5924 0.056 Uiso 1 1 calc R . .
C5 C 0.3459(5) 0.9182(4) 0.7308(6) 0.0470(15) Uani 1 1 d . . .
H5A H 0.4028 0.9372 0.7839 0.056 Uiso 1 1 calc R . .
H5B H 0.3372 0.9667 0.6684 0.056 Uiso 1 1 calc R . .
C6 C 0.2500 0.9124(7) 0.8049(8) 0.051(2) Uani 1 2 d S . .
H6A H 0.2500 0.8533 0.8501 0.062 Uiso 1 2 calc SR . .
H6B H 0.2500 0.9634 0.8647 0.062 Uiso 1 2 calc SR . .
B1 B 0.5000 0.5000 0.5620(10) 0.042(2) Uani 1 2 d S . .
B2 B 0.2500 1.0927(7) 0.4572(10) 0.036(2) Uani 1 2 d S . .


_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 O1W 2.176(5) . ?
Cu1 S1 2.3133(15) . ?
Cu1 S1 2.3133(15) 4 ?
Cu1 S2 2.3314(15) 4 ?
Cu1 S2 2.3314(15) . ?
S1 C4 1.813(6) . ?
S1 C5 1.846(7) . ?
S2 C2 1.815(7) . ?
S2 C3 1.827(8) . ?
F1 B1 1.386(8) . ?
F2 B1 1.321(8) . ?
F3 B2 1.401(12) . ?
F4 B2 1.341(12) . ?
F5 B2 1.362(7) . ?
O1W H1W 0.8500 . ?
C1 C2 1.543(10) . ?
C1 C2 1.543(10) 4 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.486(10) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.475(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C5 1.475(8) 4 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
B1 F2 1.321(8) 2_665 ?
B1 F1 1.386(8) 2_665 ?
B2 F5 1.362(7) 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
O1W Cu1 S1 96.35(14) . . ?
O1W Cu1 S1 96.35(14) . 4 ?
S1 Cu1 S1 92.74(8) . 4 ?
O1W Cu1 S2 94.14(15) . 4 ?
S1 Cu1 S2 169.33(6) . 4 ?
S1 Cu1 S2 88.05(5) 4 4 ?
O1W Cu1 S2 94.14(15) . . ?
S1 Cu1 S2 88.05(5) . . ?
S1 Cu1 S2 169.33(6) 4 . ?
S2 Cu1 S2 89.24(9) 4 . ?
C4 S1 C5 98.9(3) . . ?
C4 S1 Cu1 101.3(2) . . ?
C5 S1 Cu1 110.4(2) . . ?
C2 S2 C3 103.6(4) . . ?
C2 S2 Cu1 101.8(3) . . ?
C3 S2 Cu1 101.8(2) . . ?
Cu1 O1W H1W 120.0 . . ?
C2 C1 C2 116.7(8) . 4 ?
C2 C1 H1A 108.1 . . ?
C2 C1 H1A 108.1 4 . ?
C2 C1 H1B 108.1 . . ?
C2 C1 H1B 108.1 4 . ?
H1A C1 H1B 107.3 . . ?
C1 C2 S2 112.4(6) . . ?
C1 C2 H2A 109.1 . . ?
S2 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
S2 C2 H2B 109.1 . . ?
H2A C2 H2B 107.9 . . ?
C4 C3 S2 114.0(5) . . ?
C4 C3 H3A 108.8 . . ?
S2 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
S2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 S1 108.2(5) . . ?
C3 C4 H4A 110.1 . . ?
S1 C4 H4A 110.1 . . ?
C3 C4 H4B 110.1 . . ?
S1 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
C6 C5 S1 113.3(5) . . ?
C6 C5 H5A 108.9 . . ?
S1 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
S1 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C5 C6 C5 113.6(7) 4 . ?
C5 C6 H6A 108.9 4 . ?
C5 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 4 . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
F2 B1 F2 120.5(10) . 2_665 ?
F2 B1 F1 108.1(3) . 2_665 ?
F2 B1 F1 107.8(4) 2_665 2_665 ?
F2 B1 F1 107.8(4) . . ?
F2 B1 F1 108.1(3) 2_665 . ?
F1 B1 F1 103.2(8) 2_665 . ?
F4 B2 F5 112.4(6) . 4 ?
F4 B2 F5 112.4(6) . . ?
F5 B2 F5 112.0(8) 4 . ?
F4 B2 F3 106.1(9) . . ?
F5 B2 F3 106.7(6) 4 . ?
F5 B2 F3 106.7(6) . . ?

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
O1W H1W F1 0.85 1.90 2.723(4) 163.0 .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.961
_refine_diff_density_min         -0.882
_refine_diff_density_rms         0.098
