# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_Cu-acac-tmen_NTf2
_database_code_depnum_ccdc_archive 'CCDC 1509500'
_audit_update_record             
;
2016-10-12 deposited with the CCDC.
2017-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H23 Cu N2 O2, C2 F6 N O4 S2'
_chemical_formula_sum            'C13 H23 Cu F6 N3 O6 S2'
_chemical_formula_weight         559.00

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.9813(2)
_cell_length_b                   14.3100(4)
_cell_length_c                   15.7212(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.972(2)
_cell_angle_gamma                90
_cell_volume                     2228.89(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2676
_cell_measurement_theta_min      2.9820
_cell_measurement_theta_max      27.3540

_exptl_crystal_description       blocks
_exptl_crystal_colour            'Dark blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_F_000             1140
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    1.251
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_T_max  0.818
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            7579
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.610
_diffrn_reflns_theta_max         28.107
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.823
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.823
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             4464
_reflns_number_gt                3711
_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       'CrysAlisPro, Rigaku OD'
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_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)+(0.0321P)²+1.0140P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0040(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4464
_refine_ls_number_parameters     287
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0789
_refine_ls_wR_factor_gt          0.0727
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
Cu1 Cu 0.67208(3) 0.50466(2) 0.27063(2) 0.02165(10) Uani 1 1 d . . . . .
N1 N 0.48293(19) 0.55307(14) 0.23278(12) 0.0248(4) Uani 1 1 d . . . . .
C2 C 0.4321(3) 0.5839(2) 0.31310(18) 0.0413(7) Uani 1 1 d . . . . .
H2A H 0.4039 0.5287 0.3445 0.050 Uiso 1 1 calc R U . . .
H2B H 0.3523 0.6246 0.2991 0.050 Uiso 1 1 calc R U . . .
C3 C 0.5386(3) 0.6358(2) 0.36797(18) 0.0395(7) Uani 1 1 d . . . . .
H3A H 0.5552 0.6965 0.3410 0.047 Uiso 1 1 calc R U . . .
H3B H 0.5082 0.6482 0.4245 0.047 Uiso 1 1 calc R U . . .
N4 N 0.66497(19) 0.58098(13) 0.37960(12) 0.0228(4) Uani 1 1 d . . . . .
C5 C 0.3891(3) 0.48219(19) 0.19093(19) 0.0386(7) Uani 1 1 d . . . . .
H5A H 0.4220 0.4607 0.1380 0.058 Uiso 1 1 calc R U . . .
H5B H 0.2992 0.5099 0.1773 0.058 Uiso 1 1 calc R U . . .
H5C H 0.3839 0.4291 0.2297 0.058 Uiso 1 1 calc R U . . .
C6 C 0.4929(3) 0.6301(2) 0.17197(18) 0.0419(7) Uani 1 1 d . . . . .
H6A H 0.5563 0.6772 0.1982 0.063 Uiso 1 1 calc R U . . .
H6B H 0.4038 0.6587 0.1574 0.063 Uiso 1 1 calc R U . . .
H6C H 0.5252 0.6059 0.1198 0.063 Uiso 1 1 calc R U . . .
C7 C 0.7815(3) 0.64619(19) 0.39347(18) 0.0390(7) Uani 1 1 d . . . . .
H7A H 0.8658 0.6104 0.3998 0.058 Uiso 1 1 calc R U . . .
H7B H 0.7755 0.6829 0.4455 0.058 Uiso 1 1 calc R U . . .
H7C H 0.7799 0.6883 0.3442 0.058 Uiso 1 1 calc R U . . .
C8 C 0.6705(3) 0.51934(18) 0.45475(16) 0.0354(6) Uani 1 1 d . . . . .
H8A H 0.5931 0.4767 0.4479 0.053 Uiso 1 1 calc R U . . .
H8B H 0.6678 0.5572 0.5065 0.053 Uiso 1 1 calc R U . . .
H8C H 0.7544 0.4830 0.4599 0.053 Uiso 1 1 calc R U . . .
O9 O 0.85114(17) 0.46770(13) 0.31326(11) 0.0326(4) Uani 1 1 d . . . . .
C9 C 0.9349(3) 0.43015(17) 0.26821(18) 0.0331(6) Uani 1 1 d . . . . .
C10 C 0.9074(3) 0.40622(18) 0.18274(18) 0.0377(7) Uani 1 1 d . . . . .
H10A H 0.9779 0.3782 0.1561 0.045 Uiso 1 1 calc R U . . .
C11 C 0.7847(3) 0.41997(17) 0.13289(16) 0.0334(6) Uani 1 1 d . . . . .
O11 O 0.67958(18) 0.45446(12) 0.15924(10) 0.0311(4) Uani 1 1 d . . . . .
C12 C 1.0740(3) 0.4141(2) 0.3150(2) 0.0504(8) Uani 1 1 d . . . . .
H12A H 1.1178 0.4745 0.3288 0.076 Uiso 1 1 calc R U . . .
H12B H 1.1279 0.3780 0.2785 0.076 Uiso 1 1 calc R U . . .
H12C H 1.0668 0.3795 0.3680 0.076 Uiso 1 1 calc R U . . .
C13 C 0.7694(4) 0.3947(2) 0.03936(17) 0.0505(8) Uani 1 1 d . . . . .
H13A H 0.6817 0.3646 0.0237 0.076 Uiso 1 1 calc R U . . .
H13B H 0.8417 0.3516 0.0284 0.076 Uiso 1 1 calc R U . . .
H13C H 0.7748 0.4514 0.0050 0.076 Uiso 1 1 calc R U . . .
N20 N 0.6288(2) 0.27233(14) 0.45820(12) 0.0255(4) Uani 1 1 d . . . . .
S21 S 0.60690(6) 0.26759(4) 0.35746(4) 0.02607(15) Uani 1 1 d . . . . .
O23 O 0.70251(19) 0.21676(15) 0.31624(11) 0.0452(5) Uani 1 1 d . . . . .
O22 O 0.56780(19) 0.35847(13) 0.32570(11) 0.0401(5) Uani 1 1 d . . . . .
C24 C 0.4502(3) 0.2008(2) 0.33739(17) 0.0413(7) Uani 1 1 d . . . . .
F25 F 0.4161(2) 0.19064(18) 0.25452(11) 0.0892(8) Uani 1 1 d . . . . .
F27 F 0.35047(17) 0.24416(14) 0.36938(13) 0.0638(5) Uani 1 1 d . . . . .
F26 F 0.4629(2) 0.11755(12) 0.37301(12) 0.0602(5) Uani 1 1 d . . . . .
S28 S 0.72214(6) 0.20454(4) 0.51819(4) 0.02286(14) Uani 1 1 d . . . . .
O29 O 0.67394(17) 0.20181(13) 0.59971(10) 0.0355(4) Uani 1 1 d . . . . .
O30 O 0.76094(19) 0.12001(11) 0.48099(11) 0.0364(4) Uani 1 1 d . . . . .
C31 C 0.8779(2) 0.27166(18) 0.53802(15) 0.0285(5) Uani 1 1 d . . . . .
F32 F 0.96816(15) 0.22489(11) 0.59032(10) 0.0444(4) Uani 1 1 d . . . . .
F33 F 0.92962(17) 0.28827(12) 0.46597(10) 0.0510(5) Uani 1 1 d . . . . .
F34 F 0.85766(16) 0.35316(10) 0.57421(10) 0.0429(4) Uani 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 O11 1.9027(16) . ?
Cu1 O9 1.9059(17) . ?
Cu1 N1 2.0311(19) . ?
Cu1 N4 2.0401(18) . ?
Cu1 O22 2.5354(18) . ?
Cu1 O23 3.614(2) 2_655 ?
N1 C6 1.471(3) . ?
N1 C5 1.480(3) . ?
N1 C2 1.484(3) . ?
C2 C3 1.485(4) . ?
C3 N4 1.477(3) . ?
N4 C8 1.470(3) . ?
N4 C7 1.486(3) . ?
O9 C9 1.278(3) . ?
C9 C10 1.382(4) . ?
C9 C12 1.508(4) . ?
C10 C11 1.386(4) . ?
C11 O11 1.273(3) . ?
C11 C13 1.504(4) . ?
N20 S21 1.5737(19) . ?
N20 S28 1.577(2) . ?
S21 O23 1.4177(19) . ?
S21 O22 1.4302(19) . ?
S21 C24 1.828(3) . ?
C24 F25 1.314(3) . ?
C24 F26 1.316(3) . ?
C24 F27 1.323(3) . ?
S28 O30 1.4178(17) . ?
S28 O29 1.4231(17) . ?
S28 C31 1.822(3) . ?
C31 F33 1.322(3) . ?
C31 F34 1.324(3) . ?
C31 F32 1.325(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O11 Cu1 O9 94.52(7) . . ?
O11 Cu1 N1 89.89(8) . . ?
O9 Cu1 N1 175.06(8) . . ?
O11 Cu1 N4 169.82(8) . . ?
O9 Cu1 N4 88.85(7) . . ?
N1 Cu1 N4 86.42(8) . . ?
O11 Cu1 O22 93.81(7) . . ?
O9 Cu1 O22 93.28(7) . . ?
N1 Cu1 O22 88.62(7) . . ?
N4 Cu1 O22 95.59(7) . . ?
O11 Cu1 O23 85.13(6) . 2_655 ?
O9 Cu1 O23 90.74(6) . 2_655 ?
N1 Cu1 O23 87.43(6) . 2_655 ?
N4 Cu1 O23 85.22(6) . 2_655 ?
O22 Cu1 O23 175.91(5) . 2_655 ?
C6 N1 C5 108.3(2) . . ?
C6 N1 C2 112.8(2) . . ?
C5 N1 C2 108.6(2) . . ?
C6 N1 Cu1 108.21(15) . . ?
C5 N1 Cu1 114.34(16) . . ?
C2 N1 Cu1 104.72(15) . . ?
N1 C2 C3 110.4(2) . . ?
N4 C3 C2 110.3(2) . . ?
C8 N4 C3 111.5(2) . . ?
C8 N4 C7 107.84(19) . . ?
C3 N4 C7 109.0(2) . . ?
C8 N4 Cu1 110.60(15) . . ?
C3 N4 Cu1 107.24(14) . . ?
C7 N4 Cu1 110.67(15) . . ?
C9 O9 Cu1 124.79(17) . . ?
O9 C9 C10 125.2(2) . . ?
O9 C9 C12 114.8(3) . . ?
C10 C9 C12 119.9(2) . . ?
C9 C10 C11 124.9(2) . . ?
O11 C11 C10 125.3(2) . . ?
O11 C11 C13 114.9(3) . . ?
C10 C11 C13 119.8(2) . . ?
C11 O11 Cu1 124.87(17) . . ?
S21 N20 S28 125.11(13) . . ?
O23 S21 O22 118.50(12) . . ?
O23 S21 N20 117.60(11) . . ?
O22 S21 N20 108.11(11) . . ?
O23 S21 C24 105.20(14) . . ?
O22 S21 C24 102.93(13) . . ?
N20 S21 C24 101.98(12) . . ?
S21 O22 Cu1 139.78(12) . . ?
F25 C24 F26 108.8(3) . . ?
F25 C24 F27 108.2(3) . . ?
F26 C24 F27 107.5(2) . . ?
F25 C24 S21 109.99(19) . . ?
F26 C24 S21 111.3(2) . . ?
F27 C24 S21 110.9(2) . . ?
O30 S28 O29 119.15(11) . . ?
O30 S28 N20 116.71(11) . . ?
O29 S28 N20 108.40(10) . . ?
O30 S28 C31 104.49(12) . . ?
O29 S28 C31 103.60(11) . . ?
N20 S28 C31 102.02(11) . . ?
F33 C31 F34 107.8(2) . . ?
F33 C31 F32 108.4(2) . . ?
F34 C31 F32 107.8(2) . . ?
F33 C31 S28 111.21(17) . . ?
F34 C31 S28 111.48(17) . . ?
F32 C31 S28 109.98(17) . . ?

_refine_diff_density_max         0.505
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_Cu-acac-tmen_NO3
_database_code_depnum_ccdc_archive 'CCDC 1508197'
_audit_update_record             
;
2016-10-05 deposited with the CCDC.
2017-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H23 Cu N2 O2, N O3, H2 O'
_chemical_formula_sum            'C11 H25 Cu N3 O6'
_chemical_formula_weight         358.88

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.2712(6)
_cell_length_b                   30.314(2)
_cell_length_c                   13.759(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.934(11)
_cell_angle_gamma                90
_cell_volume                     3317.3(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    24961
_cell_measurement_theta_min      3.6886
_cell_measurement_theta_max      31.7503

_exptl_crystal_description       blocks
_exptl_crystal_colour            'Dark blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_F_000             1512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    1.345
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94061
_exptl_absorpt_correction_T_max  1.06498
_exptl_absorpt_process_details   
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.30.2 (release 11-05-2006 CrysAlis171 .NET) 
(compiled May 11 2006,17:41:17) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'OD Xcalibur 3'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 15.9863
_diffrn_reflns_number            43191
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.697
_diffrn_reflns_theta_max         31.857
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             10559
_reflns_number_gt                8199
_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       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_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)+(0.0364P)²+0.9553P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10559
_refine_ls_number_parameters     407
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0757
_refine_ls_wR_factor_gt          0.0726
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.006
_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
Cu1A Cu 0.30592(2) 0.57935(2) 0.35178(2) 0.02150(4) Uani 1 1 d . . . . .
N1A N 0.05954(15) 0.58855(4) 0.28044(9) 0.0234(2) Uani 1 1 d . . . . .
C2A C 0.05181(19) 0.59779(5) 0.17326(11) 0.0288(3) Uani 1 1 d . . . . .
H2AA H 0.0853 0.6287 0.1663 0.035 Uiso 1 1 calc R U . . .
H2AB H -0.0647 0.5937 0.1304 0.035 Uiso 1 1 calc R U . . .
C3A C 0.16845(19) 0.56688(5) 0.13919(11) 0.0284(3) Uani 1 1 d . . . . .
H3AA H 0.1255 0.5363 0.1365 0.034 Uiso 1 1 calc R U . . .
H3AB H 0.1741 0.5752 0.0706 0.034 Uiso 1 1 calc R U . . .
N4A N 0.33927(15) 0.56950(4) 0.21157(9) 0.0225(2) Uani 1 1 d . . . . .
C5A C -0.0174(2) 0.62550(5) 0.32191(13) 0.0331(3) Uani 1 1 d . . . . .
H5AA H 0.0404 0.6530 0.3148 0.050 Uiso 1 1 calc R U . . .
H5AB H -0.0071 0.6201 0.3936 0.050 Uiso 1 1 calc R U . . .
H5AC H -0.1365 0.6279 0.2849 0.050 Uiso 1 1 calc R U . . .
C6A C -0.0321(2) 0.54737(5) 0.28932(13) 0.0343(3) Uani 1 1 d . . . . .
H6AA H 0.0199 0.5225 0.2637 0.051 Uiso 1 1 calc R U . . .
H6AB H -0.1498 0.5502 0.2497 0.051 Uiso 1 1 calc R U . . .
H6AC H -0.0269 0.5422 0.3604 0.051 Uiso 1 1 calc R U . . .
C7A C 0.4320(2) 0.52813(5) 0.20635(12) 0.0309(3) Uani 1 1 d . . . . .
H7AA H 0.3701 0.5031 0.2233 0.046 Uiso 1 1 calc R U . . .
H7AB H 0.5439 0.5296 0.2545 0.046 Uiso 1 1 calc R U . . .
H7AC H 0.4435 0.5244 0.1378 0.046 Uiso 1 1 calc R U . . .
C8A C 0.4344(2) 0.60683(5) 0.18549(12) 0.0309(3) Uani 1 1 d . . . . .
H8AA H 0.3689 0.6340 0.1818 0.046 Uiso 1 1 calc R U . . .
H8AB H 0.4556 0.6013 0.1199 0.046 Uiso 1 1 calc R U . . .
H8AC H 0.5418 0.6100 0.2375 0.046 Uiso 1 1 calc R U . . .
O9A O 0.53779(13) 0.56596(4) 0.41214(7) 0.0272(2) Uani 1 1 d . . . . .
C9A C 0.60550(18) 0.55958(4) 0.50573(11) 0.0247(3) Uani 1 1 d . . . . .
C10A C 0.5220(2) 0.56071(5) 0.58133(11) 0.0280(3) Uani 1 1 d . . . . .
H10A H 0.5874 0.5569 0.6493 0.034 Uiso 1 1 calc R U . . .
C11A C 0.34979(19) 0.56706(5) 0.56394(10) 0.0255(3) Uani 1 1 d . . . . .
O11A O 0.24713(13) 0.57508(4) 0.47782(7) 0.0290(2) Uani 1 1 d . . . . .
C12A C 0.7903(2) 0.54960(6) 0.53410(12) 0.0355(3) Uani 1 1 d . . . . .
H12A H 0.8083 0.5203 0.5088 0.053 Uiso 1 1 calc R U . . .
H12B H 0.8350 0.5502 0.6078 0.053 Uiso 1 1 calc R U . . .
H12C H 0.8483 0.5718 0.5042 0.053 Uiso 1 1 calc R U . . .
C13A C 0.2723(2) 0.56381(6) 0.65063(12) 0.0365(4) Uani 1 1 d . . . . .
H13A H 0.1846 0.5863 0.6430 0.055 Uiso 1 1 calc R U . . .
H13B H 0.3592 0.5686 0.7144 0.055 Uiso 1 1 calc R U . . .
H13C H 0.2228 0.5345 0.6510 0.055 Uiso 1 1 calc R U . . .
Cu1B Cu 0.11011(2) 0.74914(2) 0.09260(2) 0.02821(5) Uani 1 1 d . . . . .
N1B N 0.03535(17) 0.79407(4) 0.18095(10) 0.0315(3) Uani 1 1 d . . . . .
C2B C 0.1777(2) 0.82528(6) 0.21619(15) 0.0445(4) Uani 1 1 d . . . . .
H2BA H 0.2613 0.8128 0.2756 0.053 Uiso 1 1 calc R U . . .
H2BB H 0.1362 0.8535 0.2367 0.053 Uiso 1 1 calc R U . . .
C3B C 0.2586(2) 0.83342(5) 0.13256(16) 0.0432(4) Uani 1 1 d . . . . .
H3BA H 0.1794 0.8493 0.0764 0.052 Uiso 1 1 calc R U . . .
H3BB H 0.3602 0.8519 0.1577 0.052 Uiso 1 1 calc R U . . .
N4B N 0.30545(16) 0.79042(4) 0.09592(11) 0.0311(3) Uani 1 1 d . . . . .
C5B C -0.0052(3) 0.77377(7) 0.26892(14) 0.0454(4) Uani 1 1 d . . . . .
H5BA H 0.0944 0.7586 0.3107 0.068 Uiso 1 1 calc R U . . .
H5BB H -0.0968 0.7525 0.2455 0.068 Uiso 1 1 calc R U . . .
H5BC H -0.0399 0.7968 0.3090 0.068 Uiso 1 1 calc R U . . .
C6B C -0.1158(2) 0.81688(6) 0.11896(14) 0.0380(4) Uani 1 1 d . . . . .
H6BA H -0.0882 0.8323 0.0629 0.057 Uiso 1 1 calc R U . . .
H6BB H -0.1548 0.8383 0.1609 0.057 Uiso 1 1 calc R U . . .
H6BC H -0.2047 0.7952 0.0919 0.057 Uiso 1 1 calc R U . . .
C7B C 0.3349(3) 0.79688(7) -0.00410(15) 0.0480(5) Uani 1 1 d . . . . .
H7BA H 0.2334 0.8091 -0.0510 0.072 Uiso 1 1 calc R U . . .
H7BB H 0.3621 0.7685 -0.0298 0.072 Uiso 1 1 calc R U . . .
H7BC H 0.4288 0.8174 0.0021 0.072 Uiso 1 1 calc R U . . .
C8B C 0.4594(2) 0.77223(6) 0.16597(15) 0.0401(4) Uani 1 1 d . . . . .
H8BA H 0.4420 0.7687 0.2332 0.060 Uiso 1 1 calc R U . . .
H8BB H 0.5535 0.7924 0.1701 0.060 Uiso 1 1 calc R U . . .
H8BC H 0.4848 0.7435 0.1411 0.060 Uiso 1 1 calc R U . . .
O9B O 0.19690(13) 0.70700(3) 0.01657(8) 0.0281(2) Uani 1 1 d . . . . .
C9B C 0.11189(18) 0.67528(4) -0.03345(10) 0.0235(3) Uani 1 1 d . . . . .
C10B C -0.05090(18) 0.66359(4) -0.03264(11) 0.0250(3) Uani 1 1 d . . . . .
H10B H -0.1029 0.6397 -0.0745 0.030 Uiso 1 1 calc R U . . .
C11B C -0.14224(18) 0.68442(4) 0.02508(11) 0.0244(3) Uani 1 1 d . . . . .
O11B O -0.09115(13) 0.71689(4) 0.08442(8) 0.0299(2) Uani 1 1 d . . . . .
C12B C 0.1991(2) 0.64946(5) -0.09752(13) 0.0344(3) Uani 1 1 d . . . . .
H12D H 0.2344 0.6695 -0.1437 0.052 Uiso 1 1 calc R U . . .
H12E H 0.1217 0.6274 -0.1368 0.052 Uiso 1 1 calc R U . . .
H12F H 0.2979 0.6347 -0.0539 0.052 Uiso 1 1 calc R U . . .
C13B C -0.3157(2) 0.66851(6) 0.02227(14) 0.0369(4) Uani 1 1 d . . . . .
H13D H -0.3132 0.6545 0.0868 0.055 Uiso 1 1 calc R U . . .
H13E H -0.3537 0.6471 -0.0326 0.055 Uiso 1 1 calc R U . . .
H13F H -0.3933 0.6936 0.0108 0.055 Uiso 1 1 calc R U . . .
N20 N 0.35964(17) 0.69335(4) 0.34641(10) 0.0301(3) Uani 1 1 d . . . . .
O21 O 0.39870(16) 0.65595(4) 0.38534(9) 0.0379(3) Uani 1 1 d . . . . .
O22 O 0.26004(15) 0.69658(4) 0.26008(9) 0.0378(3) Uani 1 1 d . . . . .
O23 O 0.42133(18) 0.72709(4) 0.39438(10) 0.0467(3) Uani 1 1 d . . . . .
N30 N 0.3379(2) 0.43859(5) 0.06192(11) 0.0366(3) Uani 1 1 d . . . . .
O31 O 0.19465(18) 0.45453(5) 0.03001(11) 0.0544(4) Uani 1 1 d . . . . .
O32 O 0.3773(2) 0.41888(4) 0.14444(10) 0.0519(4) Uani 1 1 d . . . . .
O33 O 0.4408(2) 0.44268(5) 0.01171(12) 0.0583(4) Uani 1 1 d . . . . .
O40 O 0.07177(17) 0.43592(5) 0.21903(10) 0.0543(4) Uani 1 1 d D . . . .
H40A H 0.1380(5) 0.4319(6) 0.1776(3) 0.071(8) Uiso 1 1 d D . . . .
H40B H -0.0139(6) 0.4505(2) 0.1767(5) 0.052(6) Uiso 1 1 d D . . . .
O50 O 0.77158(19) 0.47281(5) 0.10670(12) 0.0604(4) Uani 1 1 d D . . . .
H50A H 0.6698(4) 0.4600(2) 0.0852(15) 0.055(7) Uiso 1 1 d D . . . .
H50B H 0.7763(17) 0.49738(12) 0.0709(4) 0.077(8) Uiso 1 1 d 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
Cu1A O9A 1.9126(10) . ?
Cu1A O11A 1.9297(11) . ?
Cu1A N1A 2.0238(12) . ?
Cu1A N4A 2.0443(12) . ?
Cu1A O21 2.4495(11) . ?
N1A C5A 1.4779(19) . ?
N1A C6A 1.4827(19) . ?
N1A C2A 1.4851(18) . ?
C2A C3A 1.509(2) . ?
C3A N4A 1.4906(18) . ?
N4A C8A 1.4776(19) . ?
N4A C7A 1.4821(18) . ?
O9A C9A 1.2702(17) . ?
C9A C10A 1.398(2) . ?
C9A C12A 1.501(2) . ?
C10A C11A 1.391(2) . ?
C11A O11A 1.2774(17) . ?
C11A C13A 1.504(2) . ?
Cu1B O11B 1.9069(10) . ?
Cu1B O9B 1.9114(10) . ?
Cu1B N1B 2.0317(13) . ?
Cu1B N4B 2.0342(13) . ?
Cu1B O22 2.7960(12) . ?
Cu1B O23 2.8385(14) 4_575 ?
N1B C5B 1.476(2) . ?
N1B C6B 1.478(2) . ?
N1B C2B 1.484(2) . ?
C2B C3B 1.502(3) . ?
C3B N4B 1.487(2) . ?
N4B C7B 1.475(2) . ?
N4B C8B 1.476(2) . ?
O9B C9B 1.2756(17) . ?
C9B C10B 1.395(2) . ?
C9B C12B 1.503(2) . ?
C10B C11B 1.389(2) . ?
C11B O11B 1.2747(17) . ?
C11B C13B 1.504(2) . ?
N20 O23 1.2479(16) . ?
N20 O22 1.2497(17) . ?
N20 O21 1.2577(17) . ?
N30 O33 1.241(2) . ?
N30 O31 1.243(2) . ?
N30 O32 1.2447(19) . ?

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
O9A Cu1A O11A 93.76(4) . . ?
O9A Cu1A N1A 174.87(5) . . ?
O11A Cu1A N1A 88.65(5) . . ?
O9A Cu1A N4A 89.99(5) . . ?
O11A Cu1A N4A 166.14(5) . . ?
N1A Cu1A N4A 86.63(5) . . ?
O9A Cu1A O21 83.94(4) . . ?
O11A Cu1A O21 92.14(4) . . ?
N1A Cu1A O21 100.51(4) . . ?
N4A Cu1A O21 101.53(4) . . ?
C5A N1A C6A 108.80(12) . . ?
C5A N1A C2A 109.55(12) . . ?
C6A N1A C2A 110.91(12) . . ?
C5A N1A Cu1A 113.59(9) . . ?
C6A N1A Cu1A 108.26(9) . . ?
C2A N1A Cu1A 105.71(9) . . ?
N1A C2A C3A 109.54(12) . . ?
N4A C3A C2A 109.21(11) . . ?
C8A N4A C7A 108.60(12) . . ?
C8A N4A C3A 110.41(12) . . ?
C7A N4A C3A 109.33(11) . . ?
C8A N4A Cu1A 109.64(9) . . ?
C7A N4A Cu1A 112.03(9) . . ?
C3A N4A Cu1A 106.83(9) . . ?
C9A O9A Cu1A 125.66(10) . . ?
O9A C9A C10A 125.47(14) . . ?
O9A C9A C12A 115.36(13) . . ?
C10A C9A C12A 119.17(13) . . ?
C11A C10A C9A 124.54(13) . . ?
O11A C11A C10A 125.05(13) . . ?
O11A C11A C13A 115.39(14) . . ?
C10A C11A C13A 119.56(13) . . ?
C11A O11A Cu1A 125.39(10) . . ?
O11B Cu1B O9B 94.48(4) . . ?
O11B Cu1B N1B 88.56(5) . . ?
O9B Cu1B N1B 175.68(5) . . ?
O11B Cu1B N4B 172.64(5) . . ?
O9B Cu1B N4B 90.47(5) . . ?
N1B Cu1B N4B 86.82(5) . . ?
O11B Cu1B O22 86.50(4) . . ?
O9B Cu1B O22 85.53(4) . . ?
N1B Cu1B O22 91.60(5) . . ?
N4B Cu1B O22 99.33(5) . . ?
O11B Cu1B O23 80.35(5) . 4_575 ?
O9B Cu1B O23 80.45(4) . 4_575 ?
N1B Cu1B O23 103.13(5) . 4_575 ?
N4B Cu1B O23 95.13(5) . 4_575 ?
O22 Cu1B O23 159.90(4) . 4_575 ?
C5B N1B C6B 108.77(14) . . ?
C5B N1B C2B 109.64(15) . . ?
C6B N1B C2B 111.09(14) . . ?
C5B N1B Cu1B 112.71(10) . . ?
C6B N1B Cu1B 108.46(10) . . ?
C2B N1B Cu1B 106.17(10) . . ?
N1B C2B C3B 109.56(14) . . ?
N4B C3B C2B 109.17(14) . . ?
C7B N4B C8B 108.97(14) . . ?
C7B N4B C3B 108.97(14) . . ?
C8B N4B C3B 111.37(14) . . ?
C7B N4B Cu1B 113.22(11) . . ?
C8B N4B Cu1B 108.79(10) . . ?
C3B N4B Cu1B 105.52(10) . . ?
C9B O9B Cu1B 124.39(9) . . ?
O9B C9B C10B 125.26(13) . . ?
O9B C9B C12B 115.28(13) . . ?
C10B C9B C12B 119.46(13) . . ?
C11B C10B C9B 124.52(13) . . ?
O11B C11B C10B 125.49(13) . . ?
O11B C11B C13B 114.22(14) . . ?
C10B C11B C13B 120.29(13) . . ?
C11B O11B Cu1B 124.35(10) . . ?
O23 N20 O22 120.39(13) . . ?
O23 N20 O21 119.58(13) . . ?
O22 N20 O21 120.04(12) . . ?
N20 O21 Cu1A 138.05(10) . . ?
N20 O22 Cu1B 148.80(9) . . ?
O33 N30 O31 119.84(16) . . ?
O33 N30 O32 120.53(18) . . ?
O31 N30 O32 119.63(16) . . ?

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
O40 H40A N30 0.9000(2) 2.599(4) 3.484(2) 167.7(15) .
O40 H40A O31 0.9000(2) 2.310(8) 3.093(2) 145.3(11) .
O40 H40A O32 0.9000(2) 2.186(3) 3.021(2) 154.1(4) .
O40 H40B O50 0.9000(1) 1.896(3) 2.774(2) 164.7(7) 1_455
O50 H50A O33 0.9000(1) 1.958(5) 2.840(2) 166.0(16) .
O50 H50B N30 0.9000(1) 2.655(5) 3.502(2) 157.1(11) 3_665
O50 H50B O31 0.9000(1) 2.072(3) 2.959(2) 168.4(8) 3_665
O50 H50B O33 0.9000(1) 2.588(10) 3.276(2) 133.8(11) 3_665

_refine_diff_density_max         0.394
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_Cu-acac-tmen_OTf
_database_code_depnum_ccdc_archive 'CCDC 1508196'
_audit_update_record             
;
2016-10-05 deposited with the CCDC.
2017-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H23 Cu N2 O2, C F3 O3 S'
_chemical_formula_sum            'C12 H23 Cu F3 N2 O5 S'
_chemical_formula_weight         427.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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                   8.8800(14)
_cell_length_b                   13.920(2)
_cell_length_c                   14.969(3)
_cell_angle_alpha                93.461(15)
_cell_angle_beta                 98.617(15)
_cell_angle_gamma                91.736(13)
_cell_volume                     1824.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    19668
_cell_measurement_theta_min      2.9900
_cell_measurement_theta_max      70.7782

_exptl_crystal_description       'platy needles'
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_F_000             884
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    3.265
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.66992
_exptl_absorpt_correction_T_max  1.15404
_exptl_absorpt_process_details   
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.29.9 (release 23-03-2006 CrysAlis171 .NET) 
(compiled Mar 23 2006,23:39:28) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'OD Xcalibur PX Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 8.2556
_diffrn_reflns_number            43913
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.992
_diffrn_reflns_theta_max         70.896
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6961
_reflns_number_gt                5400
_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       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_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)+(0.0550P)²] 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         6961
_refine_ls_number_parameters     445
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0803
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_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
Cu1A Cu 0.33821(3) 0.37355(2) 0.72128(2) 0.03450(9) Uani 1 1 d . . . . .
N1A N 0.52098(19) 0.30690(12) 0.78618(12) 0.0350(4) Uani 1 1 d . . . . .
C2A C 0.5572(2) 0.23337(15) 0.71762(15) 0.0401(5) Uani 1 1 d . . . . .
H2AA H 0.4812 0.1789 0.7110 0.048 Uiso 1 1 calc R U . . .
H2AB H 0.6591 0.2083 0.7375 0.048 Uiso 1 1 calc R U . . .
C3A C 0.5553(2) 0.27751(16) 0.62813(15) 0.0420(5) Uani 1 1 d . . . . .
H3AA H 0.6403 0.3261 0.6326 0.050 Uiso 1 1 calc R U . . .
H3AB H 0.5691 0.2270 0.5809 0.050 Uiso 1 1 calc R U . . .
N4A N 0.40790(19) 0.32382(12) 0.60280(11) 0.0339(4) Uani 1 1 d . . . . .
C5A C 0.4928(3) 0.25952(17) 0.86826(16) 0.0470(5) Uani 1 1 d . . . . .
H5AA H 0.4646 0.3078 0.9126 0.071 Uiso 1 1 calc R U . . .
H5AB H 0.5855 0.2287 0.8944 0.071 Uiso 1 1 calc R U . . .
H5AC H 0.4097 0.2107 0.8521 0.071 Uiso 1 1 calc R U . . .
C6A C 0.6485(3) 0.38008(16) 0.81281(18) 0.0485(6) Uani 1 1 d . . . . .
H6AA H 0.6661 0.4143 0.7598 0.073 Uiso 1 1 calc R U . . .
H6AB H 0.7412 0.3479 0.8367 0.073 Uiso 1 1 calc R U . . .
H6AC H 0.6219 0.4262 0.8595 0.073 Uiso 1 1 calc R U . . .
C7A C 0.4293(3) 0.40465(16) 0.54468(15) 0.0458(5) Uani 1 1 d . . . . .
H7AA H 0.5035 0.4525 0.5780 0.069 Uiso 1 1 calc R U . . .
H7AB H 0.3317 0.4348 0.5280 0.069 Uiso 1 1 calc R U . . .
H7AC H 0.4669 0.3799 0.4898 0.069 Uiso 1 1 calc R U . . .
C8A C 0.2939(3) 0.25326(17) 0.55192(16) 0.0476(6) Uani 1 1 d . . . . .
H8AA H 0.1937 0.2819 0.5432 0.071 Uiso 1 1 calc R U . . .
H8AB H 0.2889 0.1956 0.5860 0.071 Uiso 1 1 calc R U . . .
H8AC H 0.3234 0.2355 0.4928 0.071 Uiso 1 1 calc R U . . .
O9A O 0.16555(16) 0.42970(10) 0.65306(10) 0.0391(3) Uani 1 1 d . . . . .
C9A C 0.0639(2) 0.47442(14) 0.68920(15) 0.0377(5) Uani 1 1 d . . . . .
C10A C 0.0724(3) 0.50081(15) 0.78024(16) 0.0420(5) Uani 1 1 d . . . . .
H10A H -0.0107 0.5342 0.7986 0.050 Uiso 1 1 calc R U . . .
C11A C 0.1924(2) 0.48259(14) 0.84731(15) 0.0379(5) Uani 1 1 d . . . . .
O11A O 0.30870(17) 0.43556(10) 0.83460(10) 0.0404(3) Uani 1 1 d . . . . .
C12A C -0.0743(3) 0.49839(18) 0.62393(17) 0.0515(6) Uani 1 1 d . . . . .
H12A H -0.0420 0.5347 0.5755 0.077 Uiso 1 1 calc R U . . .
H12B H -0.1417 0.5374 0.6562 0.077 Uiso 1 1 calc R U . . .
H12C H -0.1291 0.4387 0.5977 0.077 Uiso 1 1 calc R U . . .
C13A C 0.1907(3) 0.51802(17) 0.94438(16) 0.0505(6) Uani 1 1 d . . . . .
H13A H 0.1851 0.4628 0.9815 0.076 Uiso 1 1 calc R U . . .
H13B H 0.1018 0.5574 0.9479 0.076 Uiso 1 1 calc R U . . .
H13C H 0.2840 0.5569 0.9668 0.076 Uiso 1 1 calc R U . . .
S20A S 0.03526(6) 0.19284(4) 0.73808(4) 0.04053(13) Uani 1 1 d . . . . .
O21A O 0.18923(17) 0.22642(11) 0.73475(11) 0.0481(4) Uani 1 1 d . . . . .
O22A O -0.08094(18) 0.25536(13) 0.70103(13) 0.0586(5) Uani 1 1 d . . . . .
O23A O 0.0047(2) 0.09208(12) 0.71372(12) 0.0588(5) Uani 1 1 d . . . . .
C20A C 0.0272(3) 0.20143(16) 0.85997(17) 0.0442(5) Uani 1 1 d . . . . .
F21A F -0.10948(18) 0.16947(12) 0.87674(11) 0.0666(4) Uani 1 1 d . . . . .
F22A F 0.13096(18) 0.14856(11) 0.90451(10) 0.0641(4) Uani 1 1 d . . . . .
F23A F 0.0483(2) 0.29074(10) 0.89506(11) 0.0663(4) Uani 1 1 d . . . . .
Cu1B Cu 0.31087(3) 0.87197(2) 0.73260(2) 0.03251(9) Uani 1 1 d . . . . .
N1B N 0.15799(19) 0.82694(12) 0.81212(12) 0.0347(4) Uani 1 1 d . . . . .
C2B C 0.0426(3) 0.76486(19) 0.75060(17) 0.0528(6) Uani 1 1 d . . . . .
H2BA H 0.0839 0.7007 0.7396 0.063 Uiso 1 1 calc R U . . .
H2BB H -0.0500 0.7561 0.7792 0.063 Uiso 1 1 calc R U . . .
C3B C 0.0032(3) 0.8099(2) 0.66386(17) 0.0547(6) Uani 1 1 d . . . . .
H3BA H -0.0518 0.8695 0.6738 0.066 Uiso 1 1 calc R U . . .
H3BB H -0.0652 0.7653 0.6208 0.066 Uiso 1 1 calc R U . . .
N4B N 0.14398(19) 0.83370(13) 0.62426(12) 0.0368(4) Uani 1 1 d . . . . .
C5B C 0.2258(3) 0.76894(16) 0.88656(15) 0.0450(5) Uani 1 1 d . . . . .
H5BA H 0.2699 0.7117 0.8611 0.067 Uiso 1 1 calc R U . . .
H5BB H 0.1466 0.7491 0.9215 0.067 Uiso 1 1 calc R U . . .
H5BC H 0.3058 0.8076 0.9263 0.067 Uiso 1 1 calc R U . . .
C6B C 0.0912(3) 0.91215(17) 0.85216(17) 0.0504(6) Uani 1 1 d . . . . .
H6BA H 0.0428 0.9504 0.8037 0.076 Uiso 1 1 calc R U . . .
H6BB H 0.1717 0.9515 0.8909 0.076 Uiso 1 1 calc R U . . .
H6BC H 0.0146 0.8912 0.8885 0.076 Uiso 1 1 calc R U . . .
C7B C 0.1103(3) 0.91443(18) 0.56552(17) 0.0524(6) Uani 1 1 d . . . . .
H7BA H 0.0831 0.9704 0.6018 0.079 Uiso 1 1 calc R U . . .
H7BB H 0.0250 0.8953 0.5176 0.079 Uiso 1 1 calc R U . . .
H7BC H 0.2004 0.9311 0.5382 0.079 Uiso 1 1 calc R U . . .
C8B C 0.1901(3) 0.75172(19) 0.56999(17) 0.0595(7) Uani 1 1 d . . . . .
H8BA H 0.2001 0.6954 0.6063 0.089 Uiso 1 1 calc R U . . .
H8BB H 0.2883 0.7676 0.5509 0.089 Uiso 1 1 calc R U . . .
H8BC H 0.1129 0.7373 0.5164 0.089 Uiso 1 1 calc R U . . .
O9B O 0.43703(16) 0.92337(10) 0.65173(10) 0.0394(3) Uani 1 1 d . . . . .
C9B C 0.5716(2) 0.96090(14) 0.67721(14) 0.0339(4) Uani 1 1 d . . . . .
C10B C 0.6415(2) 0.97862(14) 0.76557(14) 0.0352(4) Uani 1 1 d . . . . .
H10B H 0.7434 1.0043 0.7752 0.042 Uiso 1 1 calc R U . . .
C11B C 0.5748(2) 0.96189(14) 0.84140(14) 0.0354(4) Uani 1 1 d . . . . .
O11B O 0.43984(16) 0.92615(10) 0.84002(9) 0.0385(3) Uani 1 1 d . . . . .
C12B C 0.6553(2) 0.98866(17) 0.60119(15) 0.0431(5) Uani 1 1 d . . . . .
H12D H 0.6705 0.9309 0.5634 0.065 Uiso 1 1 calc R U . . .
H12E H 0.7545 1.0193 0.6267 0.065 Uiso 1 1 calc R U . . .
H12F H 0.5952 1.0339 0.5643 0.065 Uiso 1 1 calc R U . . .
C13B C 0.6621(3) 0.98773(17) 0.93452(15) 0.0445(5) Uani 1 1 d . . . . .
H13D H 0.6160 1.0427 0.9625 0.067 Uiso 1 1 calc R U . . .
H13E H 0.7683 1.0048 0.9297 0.067 Uiso 1 1 calc R U . . .
H13F H 0.6587 0.9325 0.9719 0.067 Uiso 1 1 calc R U . . .
S20B S 0.56018(6) 0.66980(4) 0.73180(3) 0.03740(12) Uani 1 1 d . . . . .
O21B O 0.42282(17) 0.72110(11) 0.73715(11) 0.0454(4) Uani 1 1 d . . . . .
O22B O 0.67183(19) 0.71950(14) 0.68971(12) 0.0605(5) Uani 1 1 d . . . . .
O23B O 0.5345(2) 0.56893(12) 0.70537(12) 0.0616(5) Uani 1 1 d . . . . .
C20B C 0.6465(2) 0.67021(15) 0.85062(15) 0.0398(5) Uani 1 1 d . . . . .
F21B F 0.77542(15) 0.62164(11) 0.85982(10) 0.0566(4) Uani 1 1 d . . . . .
F22B F 0.55485(16) 0.62844(11) 0.90019(10) 0.0605(4) Uani 1 1 d . . . . .
F23B F 0.6831(2) 0.75831(10) 0.88641(11) 0.0688(5) Uani 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
Cu1A O11A 1.9135(15) . ?
Cu1A O9A 1.9246(14) . ?
Cu1A N1A 2.0411(17) . ?
Cu1A N4A 2.0527(17) . ?
Cu1A O21A 2.4395(16) . ?
Cu1A O23B 3.226(2) . ?
N1A C5A 1.479(3) . ?
N1A C2A 1.482(3) . ?
N1A C6A 1.491(3) . ?
C2A C3A 1.505(3) . ?
C3A N4A 1.485(3) . ?
N4A C8A 1.479(3) . ?
N4A C7A 1.488(3) . ?
O9A C9A 1.279(3) . ?
C9A C10A 1.380(3) . ?
C9A C12A 1.509(3) . ?
C10A C11A 1.391(3) . ?
C11A O11A 1.271(3) . ?
C11A C13A 1.508(3) . ?
S20A O23A 1.4350(17) . ?
S20A O22A 1.4391(17) . ?
S20A O21A 1.4404(16) . ?
S20A C20A 1.833(3) . ?
C20A F23A 1.317(3) . ?
C20A F22A 1.323(3) . ?
C20A F21A 1.344(3) . ?
Cu1B O9B 1.9221(14) . ?
Cu1B O11B 1.9274(15) . ?
Cu1B N1B 2.0434(17) . ?
Cu1B N4B 2.0585(17) . ?
Cu1B O21B 2.3510(15) . ?
Cu1B O23A 4.152(2) 1_565 ?
N1B C6B 1.477(3) . ?
N1B C5B 1.481(3) . ?
N1B C2B 1.487(3) . ?
C2B C3B 1.476(3) . ?
C3B N4B 1.498(3) . ?
N4B C8B 1.465(3) . ?
N4B C7B 1.479(3) . ?
O9B C9B 1.283(2) . ?
C9B C10B 1.379(3) . ?
C9B C12B 1.512(3) . ?
C10B C11B 1.385(3) . ?
C11B O11B 1.280(2) . ?
C11B C13B 1.507(3) . ?
S20B O22B 1.4342(18) . ?
S20B O23B 1.4377(17) . ?
S20B O21B 1.4418(15) . ?
S20B C20B 1.828(2) . ?
C20B F23B 1.319(3) . ?
C20B F22B 1.325(3) . ?
C20B F21B 1.340(2) . ?

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
O11A Cu1A O9A 94.46(6) . . ?
O11A Cu1A N1A 89.38(7) . . ?
O9A Cu1A N1A 175.96(7) . . ?
O11A Cu1A N4A 168.81(7) . . ?
O9A Cu1A N4A 89.96(7) . . ?
N1A Cu1A N4A 86.47(7) . . ?
O11A Cu1A O21A 96.36(6) . . ?
O9A Cu1A O21A 91.64(6) . . ?
N1A Cu1A O21A 86.69(6) . . ?
N4A Cu1A O21A 93.77(6) . . ?
O11A Cu1A O23B 83.07(6) . . ?
O9A Cu1A O23B 88.40(6) . . ?
N1A Cu1A O23B 93.30(6) . . ?
N4A Cu1A O23B 86.79(6) . . ?
O21A Cu1A O23B 179.43(5) . . ?
C5A N1A C2A 109.46(16) . . ?
C5A N1A C6A 108.17(18) . . ?
C2A N1A C6A 111.77(17) . . ?
C5A N1A Cu1A 114.89(13) . . ?
C2A N1A Cu1A 104.15(13) . . ?
C6A N1A Cu1A 108.43(13) . . ?
N1A C2A C3A 109.67(17) . . ?
N4A C3A C2A 109.70(17) . . ?
C8A N4A C3A 110.30(17) . . ?
C8A N4A C7A 108.68(17) . . ?
C3A N4A C7A 109.77(17) . . ?
C8A N4A Cu1A 110.54(13) . . ?
C3A N4A Cu1A 106.84(13) . . ?
C7A N4A Cu1A 110.71(13) . . ?
C9A O9A Cu1A 123.76(14) . . ?
O9A C9A C10A 125.4(2) . . ?
O9A C9A C12A 114.9(2) . . ?
C10A C9A C12A 119.7(2) . . ?
C9A C10A C11A 125.5(2) . . ?
O11A C11A C10A 125.1(2) . . ?
O11A C11A C13A 114.4(2) . . ?
C10A C11A C13A 120.5(2) . . ?
C11A O11A Cu1A 124.67(15) . . ?
O23A S20A O22A 115.28(12) . . ?
O23A S20A O21A 114.81(11) . . ?
O22A S20A O21A 114.93(10) . . ?
O23A S20A C20A 102.92(11) . . ?
O22A S20A C20A 104.13(11) . . ?
O21A S20A C20A 102.29(10) . . ?
S20A O21A Cu1A 141.13(10) . . ?
F23A C20A F22A 108.1(2) . . ?
F23A C20A F21A 107.0(2) . . ?
F22A C20A F21A 107.08(19) . . ?
F23A C20A S20A 112.13(16) . . ?
F22A C20A S20A 111.49(16) . . ?
F21A C20A S20A 110.85(16) . . ?
O9B Cu1B O11B 93.88(6) . . ?
O9B Cu1B N1B 173.54(7) . . ?
O11B Cu1B N1B 89.00(7) . . ?
O9B Cu1B N4B 89.91(7) . . ?
O11B Cu1B N4B 168.88(7) . . ?
N1B Cu1B N4B 86.22(7) . . ?
O9B Cu1B O21B 95.20(6) . . ?
O11B Cu1B O21B 94.25(6) . . ?
N1B Cu1B O21B 90.35(6) . . ?
N4B Cu1B O21B 95.81(7) . . ?
O9B Cu1B O23A 95.51(5) . 1_565 ?
O11B Cu1B O23A 96.33(5) . 1_565 ?
N1B Cu1B O23A 78.41(6) . 1_565 ?
N4B Cu1B O23A 72.88(6) . 1_565 ?
O21B Cu1B O23A 164.38(5) . 1_565 ?
C6B N1B C5B 108.36(17) . . ?
C6B N1B C2B 112.49(19) . . ?
C5B N1B C2B 108.19(17) . . ?
C6B N1B Cu1B 108.91(13) . . ?
C5B N1B Cu1B 113.62(13) . . ?
C2B N1B Cu1B 105.35(13) . . ?
C3B C2B N1B 109.77(19) . . ?
C2B C3B N4B 110.6(2) . . ?
C8B N4B C7B 108.93(19) . . ?
C8B N4B C3B 111.9(2) . . ?
C7B N4B C3B 107.74(19) . . ?
C8B N4B Cu1B 110.47(14) . . ?
C7B N4B Cu1B 111.79(14) . . ?
C3B N4B Cu1B 105.96(13) . . ?
C9B O9B Cu1B 124.05(14) . . ?
O9B C9B C10B 125.85(19) . . ?
O9B C9B C12B 114.95(18) . . ?
C10B C9B C12B 119.19(18) . . ?
C9B C10B C11B 125.13(19) . . ?
O11B C11B C10B 125.12(19) . . ?
O11B C11B C13B 115.05(19) . . ?
C10B C11B C13B 119.82(19) . . ?
C11B O11B Cu1B 124.42(14) . . ?
O22B S20B O23B 115.91(12) . . ?
O22B S20B O21B 114.73(11) . . ?
O23B S20B O21B 114.16(11) . . ?
O22B S20B C20B 104.10(11) . . ?
O23B S20B C20B 103.13(11) . . ?
O21B S20B C20B 102.41(10) . . ?
S20B O21B Cu1B 145.63(10) . . ?
S20B O23B Cu1A 147.01(11) . . ?
F23B C20B F22B 108.34(19) . . ?
F23B C20B F21B 106.66(19) . . ?
F22B C20B F21B 106.63(18) . . ?
F23B C20B S20B 111.91(16) . . ?
F22B C20B S20B 111.80(16) . . ?
F21B C20B S20B 111.21(15) . . ?

_refine_diff_density_max         0.558
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_Cu-acac-tmen-H2O_NO3
_database_code_depnum_ccdc_archive 'CCDC 1508198'
_audit_update_record             
;
2016-10-05 deposited with the CCDC.
2017-08-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H25 Cu N2 O3, N O3, H2 O'
_chemical_formula_sum            'C11 H27 Cu N3 O7'
_chemical_formula_weight         376.89

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   8.64296(15)
_cell_length_b                   8.32174(17)
_cell_length_c                   24.6040(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.6569(17)
_cell_angle_gamma                90
_cell_volume                     1769.51(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    10709
_cell_measurement_theta_min      3.3899
_cell_measurement_theta_max      32.7418

_exptl_crystal_description       blocks
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_F_000             796
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    1.268
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.640
_exptl_absorpt_correction_T_max  0.856
_exptl_absorpt_process_details   
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) 
(compiled May  6 2009,17:20:42) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'OD Xcalibur 3'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 15.9825
_diffrn_reflns_number            20827
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.399
_diffrn_reflns_theta_max         32.821
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             10378
_reflns_number_gt                8042
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.892
_reflns_Friedel_fraction_max     0.923
_reflns_Friedel_fraction_full    0.999

_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       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0298P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.464(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         10378
_refine_ls_number_parameters     459
_refine_ls_number_restraints     148
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0594
_refine_ls_wR_factor_gt          0.0577
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.003
_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
Cu1A Cu 0.40188(3) 0.57337(16) 0.38348(2) 0.02391(8) Uani 1 1 d . . . . .
N1A N 0.2620(2) 0.3948(3) 0.35535(9) 0.0316(5) Uani 1 1 d . . . . .
C2A C 0.3545(3) 0.3130(4) 0.31287(13) 0.0448(7) Uani 1 1 d . . . . .
H2AA H 0.3079 0.2072 0.3043 0.054 Uiso 1 1 calc R U . . .
H2AB H 0.3537 0.3784 0.2793 0.054 Uiso 1 1 calc R U . . .
C3A C 0.5151(3) 0.2906(4) 0.33213(14) 0.0483(8) Uani 1 1 d . . . . .
H3AA H 0.5787 0.2481 0.3022 0.058 Uiso 1 1 calc R U . . .
H3AB H 0.5174 0.2113 0.3621 0.058 Uiso 1 1 calc R U . . .
N4A N 0.5809(2) 0.4450(3) 0.35144(9) 0.0281(5) Uani 1 1 d . . . . .
C5A C 0.1174(3) 0.4557(5) 0.32981(13) 0.0450(8) Uani 1 1 d . . . . .
H5AA H 0.1430 0.5263 0.2993 0.067 Uiso 1 1 calc R U . . .
H5AB H 0.0554 0.3650 0.3165 0.067 Uiso 1 1 calc R U . . .
H5AC H 0.0583 0.5162 0.3567 0.067 Uiso 1 1 calc R U . . .
C6A C 0.2207(4) 0.2892(4) 0.40100(13) 0.0550(9) Uani 1 1 d . . . . .
H6AA H 0.3152 0.2479 0.4184 0.082 Uiso 1 1 calc R U . . .
H6AB H 0.1611 0.3504 0.4276 0.082 Uiso 1 1 calc R U . . .
H6AC H 0.1582 0.1992 0.3874 0.082 Uiso 1 1 calc R U . . .
C7A C 0.7045(3) 0.4127(4) 0.39209(12) 0.0433(8) Uani 1 1 d . . . . .
H7AA H 0.7482 0.5147 0.4049 0.065 Uiso 1 1 calc R U . . .
H7AB H 0.6612 0.3538 0.4229 0.065 Uiso 1 1 calc R U . . .
H7AC H 0.7861 0.3482 0.3754 0.065 Uiso 1 1 calc R U . . .
C8A C 0.6505(3) 0.5373(4) 0.30632(11) 0.0367(7) Uani 1 1 d . . . . .
H8AA H 0.5710 0.5604 0.2787 0.055 Uiso 1 1 calc R U . . .
H8AB H 0.6930 0.6384 0.3204 0.055 Uiso 1 1 calc R U . . .
H8AC H 0.7336 0.4739 0.2900 0.055 Uiso 1 1 calc R U . . .
O9A O 0.54954(19) 0.7191(3) 0.41590(8) 0.0322(4) Uani 1 1 d . . . . .
C9A C 0.5140(3) 0.8474(3) 0.44064(10) 0.0290(5) Uani 1 1 d . . . . .
C10A C 0.3669(3) 0.8859(4) 0.45776(11) 0.0352(6) Uani 1 1 d . . . . .
H10A H 0.3531 0.9873 0.4748 0.042 Uiso 1 1 calc R U . . .
C11A C 0.2375(3) 0.7880(4) 0.45210(10) 0.0341(6) Uani 1 1 d . . . . .
O11A O 0.23470(19) 0.6519(3) 0.42829(7) 0.0323(5) Uani 1 1 d . . . . .
C12A C 0.6460(3) 0.9616(4) 0.45138(12) 0.0444(7) Uani 1 1 d . . . . .
H12A H 0.7251 0.9080 0.4738 0.067 Uiso 1 1 calc R U . . .
H12B H 0.6077 1.0565 0.4706 0.067 Uiso 1 1 calc R U . . .
H12C H 0.6913 0.9946 0.4168 0.067 Uiso 1 1 calc R U . . .
C13A C 0.0864(3) 0.8372(5) 0.47685(14) 0.0578(9) Uani 1 1 d . . . . .
H13A H 0.0032 0.8271 0.4496 0.087 Uiso 1 1 calc R U . . .
H13B H 0.0933 0.9491 0.4891 0.087 Uiso 1 1 calc R U . . .
H13C H 0.0641 0.7676 0.5079 0.087 Uiso 1 1 calc R U . . .
O20A O 0.34261(19) 0.74435(19) 0.31485(8) 0.0325(5) Uani 1 1 d D . . . .
H20A H 0.2501(5) 0.7850(12) 0.3241(6) 0.073(12) Uiso 1 1 d D . . . .
H20B H 0.4266(5) 0.8024(8) 0.3061(5) 0.009(5) Uiso 1 1 d D . . . .
Cu1B Cu 0.09530(3) 0.59675(16) 0.11341(2) 0.02304(8) Uani 1 1 d . . . . .
N1B N -0.0447(2) 0.7553(3) 0.15223(10) 0.0356(6) Uani 1 1 d D . . . .
C2B C 0.0570(5) 0.9005(5) 0.16453(18) 0.0446(12) Uani 0.768(7) 1 d D . P A 1
H2BA H 0.0611 0.9715 0.1323 0.054 Uiso 0.768(7) 1 calc R U P A 1
H2BB H 0.0133 0.9625 0.1951 0.054 Uiso 0.768(7) 1 calc R U P A 1
C3B C 0.2135(4) 0.8447(6) 0.17894(18) 0.0396(11) Uani 0.768(7) 1 d D . P A 1
H3BA H 0.2826 0.9379 0.1853 0.048 Uiso 0.768(7) 1 calc R U P A 1
H3BB H 0.2106 0.7800 0.2127 0.048 Uiso 0.768(7) 1 calc R U P A 1
C2" C 0.0578(10) 0.8316(13) 0.1945(4) 0.025(3) Uiso 0.232(7) 1 d D . P A 2
H2"A H 0.0951 0.7515 0.2213 0.029 Uiso 0.232(7) 1 calc R U P A 2
H2"B H 0.0033 0.9189 0.2138 0.029 Uiso 0.232(7) 1 calc R U P A 2
C3" C 0.1892(12) 0.8966(13) 0.1613(5) 0.028(3) Uiso 0.232(7) 1 d D . P A 2
H3"A H 0.2633 0.9558 0.1848 0.034 Uiso 0.232(7) 1 calc R U P A 2
H3"B H 0.1493 0.9709 0.1330 0.034 Uiso 0.232(7) 1 calc R U P A 2
N4B N 0.2715(2) 0.7468(3) 0.13398(9) 0.0305(5) Uani 1 1 d D . . . .
C5B C -0.1140(6) 0.6874(6) 0.19915(18) 0.0411(11) Uani 0.768(7) 1 d D . P A 1
H5BA H -0.0329 0.6499 0.2243 0.062 Uiso 0.768(7) 1 calc R U P A 1
H5BB H -0.1772 0.7689 0.2172 0.062 Uiso 0.768(7) 1 calc R U P A 1
H5BC H -0.1796 0.5966 0.1883 0.062 Uiso 0.768(7) 1 calc R U P A 1
C6B C -0.1696(7) 0.8131(7) 0.1135(2) 0.0448(14) Uani 0.768(7) 1 d D . P A 1
H6BA H -0.1218 0.8599 0.0812 0.067 Uiso 0.768(7) 1 calc R U P A 1
H6BB H -0.2352 0.7223 0.1027 0.067 Uiso 0.768(7) 1 calc R U P A 1
H6BC H -0.2327 0.8947 0.1315 0.067 Uiso 0.768(7) 1 calc R U P A 1
C7B C 0.3169(10) 0.8427(11) 0.0865(3) 0.0426(17) Uani 0.768(7) 1 d D . P A 1
H7BA H 0.3546 0.7710 0.0579 0.064 Uiso 0.768(7) 1 calc R U P A 1
H7BB H 0.2272 0.9030 0.0728 0.064 Uiso 0.768(7) 1 calc R U P A 1
H7BC H 0.3992 0.9178 0.0971 0.064 Uiso 0.768(7) 1 calc R U P A 1
C8B C 0.4130(6) 0.6556(6) 0.1537(2) 0.0428(11) Uani 0.768(7) 1 d D . P A 1
H8BA H 0.4531 0.5896 0.1241 0.064 Uiso 0.768(7) 1 calc R U P A 1
H8BB H 0.4927 0.7320 0.1657 0.064 Uiso 0.768(7) 1 calc R U P A 1
H8BC H 0.3847 0.5862 0.1842 0.064 Uiso 0.768(7) 1 calc R U P A 1
C5" C -0.1536(18) 0.6476(19) 0.1920(6) 0.032(4) Uiso 0.232(7) 1 d D . P A 2
H5"A H -0.0883 0.5770 0.2144 0.048 Uiso 0.232(7) 1 calc R U P A 2
H5"B H -0.2133 0.7188 0.2156 0.048 Uiso 0.232(7) 1 calc R U P A 2
H5"C H -0.2247 0.5823 0.1699 0.048 Uiso 0.232(7) 1 calc R U P A 2
C6" C -0.147(2) 0.851(2) 0.1223(8) 0.043(6) Uiso 0.232(7) 1 d D . P A 2
H6"A H -0.2056 0.7835 0.0966 0.064 Uiso 0.232(7) 1 calc R U P A 2
H6"B H -0.2195 0.9038 0.1470 0.064 Uiso 0.232(7) 1 calc R U P A 2
H6"C H -0.0894 0.9325 0.1023 0.064 Uiso 0.232(7) 1 calc R U P A 2
C7" C 0.340(3) 0.818(3) 0.0839(7) 0.030(5) Uiso 0.232(7) 1 d D . P A 2
H7"A H 0.2571 0.8627 0.0609 0.046 Uiso 0.232(7) 1 calc R U P A 2
H7"B H 0.4122 0.9041 0.0942 0.046 Uiso 0.232(7) 1 calc R U P A 2
H7"C H 0.3952 0.7348 0.0638 0.046 Uiso 0.232(7) 1 calc R U P A 2
C8" C 0.387(2) 0.680(3) 0.1693(7) 0.050(6) Uiso 0.232(7) 1 d D . P A 2
H8"A H 0.3368 0.6346 0.2015 0.074 Uiso 0.232(7) 1 calc R U P A 2
H8"B H 0.4424 0.5948 0.1502 0.074 Uiso 0.232(7) 1 calc R U P A 2
H8"C H 0.4594 0.7641 0.1805 0.074 Uiso 0.232(7) 1 calc R U P A 2
O9B O 0.22932(18) 0.4834(3) 0.06352(7) 0.0297(4) Uani 1 1 d . . . . .
C9B C 0.1969(3) 0.3479(4) 0.04213(10) 0.0290(6) Uani 1 1 d . . . . .
C10B C 0.0509(3) 0.2775(4) 0.04189(10) 0.0304(5) Uani 1 1 d . . . . .
H10B H 0.0405 0.1750 0.0252 0.036 Uiso 1 1 calc R U . . .
C11B C -0.0807(3) 0.3454(3) 0.06409(10) 0.0292(6) Uani 1 1 d . . . . .
O11B O -0.08509(18) 0.4798(3) 0.08825(7) 0.0288(4) Uani 1 1 d . . . . .
C12B C 0.3292(3) 0.2628(4) 0.01589(12) 0.0432(7) Uani 1 1 d . . . . .
H12D H 0.3830 0.3372 -0.0083 0.065 Uiso 1 1 calc R U . . .
H12E H 0.2899 0.1713 -0.0052 0.065 Uiso 1 1 calc R U . . .
H12F H 0.4014 0.2243 0.0440 0.065 Uiso 1 1 calc R U . . .
C13B C -0.2325(3) 0.2568(4) 0.06067(12) 0.0398(6) Uani 1 1 d . . . . .
H13D H -0.2492 0.1981 0.0946 0.060 Uiso 1 1 calc R U . . .
H13E H -0.2302 0.1808 0.0303 0.060 Uiso 1 1 calc R U . . .
H13F H -0.3168 0.3340 0.0549 0.060 Uiso 1 1 calc R U . . .
O20B O 0.1410(2) 0.42439(15) 0.18257(8) 0.0335(5) Uani 1 1 d D . . . .
H20C H 0.2155(6) 0.3547(7) 0.1731(5) 0.028(7) Uiso 1 1 d D . . . .
H20D H 0.0672(7) 0.3607(8) 0.1965(4) 0.21(3) Uiso 1 1 d D . . . .
N30 N -0.0306(3) 0.9516(4) 0.32351(10) 0.0361(6) Uani 1 1 d . . . . .
O31 O 0.1026(3) 0.9785(3) 0.31036(13) 0.0792(9) Uani 1 1 d . . . . .
O32 O -0.1341(2) 1.0534(3) 0.31528(9) 0.0544(6) Uani 1 1 d . . . . .
O33 O -0.0678(3) 0.8225(4) 0.34385(13) 0.0841(9) Uani 1 1 d . . . . .
N40 N 0.5106(2) 0.2043(3) 0.17355(9) 0.0301(5) Uani 1 1 d . . . . .
O41 O 0.3814(2) 0.2163(3) 0.15321(11) 0.0592(6) Uani 1 1 d . . . . .
O42 O 0.5768(2) 0.0709(3) 0.17375(9) 0.0496(5) Uani 1 1 d . . . . .
O43 O 0.5760(2) 0.3219(3) 0.19298(10) 0.0607(7) Uani 1 1 d . . . . .
O50 O 0.5789(2) 0.9285(3) 0.27753(9) 0.0488(6) Uani 1 1 d D . . . .
H50A H 0.6722(5) 0.919(4) 0.2939(4) 0.099(15) Uiso 1 1 d D . . . .
H50B H 0.568(3) 0.9775(10) 0.24511(17) 0.064(11) Uiso 1 1 d D . . . .
O60 O -0.1034(2) 0.2512(2) 0.22077(9) 0.0472(6) Uani 1 1 d D . . . .
H60A H -0.1944(5) 0.2124(13) 0.2084(5) 0.073(12) Uiso 1 1 d D . . . .
H60B H -0.104(4) 0.1855(7) 0.24981(18) 0.078(13) Uiso 1 1 d 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
Cu1A O9A 1.9267(18) . ?
Cu1A O11A 1.9407(17) . ?
Cu1A N1A 2.032(2) . ?
Cu1A N4A 2.045(2) . ?
Cu1A O20A 2.262(2) . ?
N1A C6A 1.473(4) . ?
N1A C5A 1.481(4) . ?
N1A C2A 1.488(4) . ?
C2A C3A 1.474(4) . ?
C3A N4A 1.481(4) . ?
N4A C7A 1.480(3) . ?
N4A C8A 1.483(3) . ?
O9A C9A 1.269(3) . ?
C9A C10A 1.382(4) . ?
C9A C12A 1.506(4) . ?
C10A C11A 1.389(4) . ?
C11A O11A 1.275(3) . ?
C11A C13A 1.505(3) . ?
Cu1B O11B 1.9338(17) . ?
Cu1B O9B 1.9420(17) . ?
Cu1B N4B 2.029(2) . ?
Cu1B N1B 2.036(2) . ?
Cu1B O20B 2.257(2) . ?
N1B C6" 1.396(13) . ?
N1B C5B 1.424(5) . ?
N1B C2" 1.500(8) . ?
N1B C6B 1.510(5) . ?
N1B C2B 1.522(4) . ?
N1B C5" 1.634(12) . ?
C2B C3B 1.470(6) . ?
C3B N4B 1.467(4) . ?
C2" C3" 1.507(13) . ?
C3" N4B 1.588(10) . ?
N4B C8" 1.426(13) . ?
N4B C7B 1.472(6) . ?
N4B C7" 1.496(14) . ?
N4B C8B 1.514(5) . ?
O9B C9B 1.274(3) . ?
C9B C10B 1.391(3) . ?
C9B C12B 1.498(3) . ?
C10B C11B 1.387(3) . ?
C11B O11B 1.267(3) . ?
C11B C13B 1.506(3) . ?
N30 O31 1.221(3) . ?
N30 O33 1.229(3) . ?
N30 O32 1.247(3) . ?
N40 O41 1.223(3) . ?
N40 O43 1.224(3) . ?
N40 O42 1.249(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O9A Cu1A O11A 92.69(8) . . ?
O9A Cu1A N1A 171.85(9) . . ?
O11A Cu1A N1A 89.74(8) . . ?
O9A Cu1A N4A 89.31(8) . . ?
O11A Cu1A N4A 165.02(9) . . ?
N1A Cu1A N4A 86.36(9) . . ?
O9A Cu1A O20A 93.24(8) . . ?
O11A Cu1A O20A 92.79(7) . . ?
N1A Cu1A O20A 94.41(8) . . ?
N4A Cu1A O20A 101.92(8) . . ?
C6A N1A C5A 108.5(2) . . ?
C6A N1A C2A 113.5(3) . . ?
C5A N1A C2A 108.4(2) . . ?
C6A N1A Cu1A 108.96(17) . . ?
C5A N1A Cu1A 113.0(2) . . ?
C2A N1A Cu1A 104.55(16) . . ?
C3A C2A N1A 110.1(2) . . ?
C2A C3A N4A 110.5(3) . . ?
C7A N4A C3A 109.3(2) . . ?
C7A N4A C8A 107.7(2) . . ?
C3A N4A C8A 111.5(2) . . ?
C7A N4A Cu1A 112.20(17) . . ?
C3A N4A Cu1A 106.73(16) . . ?
C8A N4A Cu1A 109.47(17) . . ?
C9A O9A Cu1A 124.45(17) . . ?
O9A C9A C10A 124.7(2) . . ?
O9A C9A C12A 115.4(2) . . ?
C10A C9A C12A 119.9(2) . . ?
C9A C10A C11A 125.2(2) . . ?
O11A C11A C10A 125.3(2) . . ?
O11A C11A C13A 114.6(3) . . ?
C10A C11A C13A 120.1(3) . . ?
C11A O11A Cu1A 123.33(17) . . ?
O11B Cu1B O9B 92.16(7) . . ?
O11B Cu1B N4B 171.78(9) . . ?
O9B Cu1B N4B 90.29(8) . . ?
O11B Cu1B N1B 89.73(8) . . ?
O9B Cu1B N1B 166.78(10) . . ?
N4B Cu1B N1B 86.13(9) . . ?
O11B Cu1B O20B 93.14(8) . . ?
O9B Cu1B O20B 93.87(8) . . ?
N4B Cu1B O20B 94.52(8) . . ?
N1B Cu1B O20B 99.09(9) . . ?
C6" N1B C2" 119.5(8) . . ?
C5B N1B C6B 109.5(3) . . ?
C5B N1B C2B 113.7(3) . . ?
C6B N1B C2B 106.2(3) . . ?
C6" N1B C5" 105.1(9) . . ?
C2" N1B C5" 99.0(6) . . ?
C6" N1B Cu1B 120.0(10) . . ?
C5B N1B Cu1B 112.4(2) . . ?
C2" N1B Cu1B 104.5(4) . . ?
C6B N1B Cu1B 109.6(3) . . ?
C2B N1B Cu1B 105.25(17) . . ?
C5" N1B Cu1B 106.0(7) . . ?
C3B C2B N1B 109.0(3) . . ?
N4B C3B C2B 108.4(3) . . ?
N1B C2" C3" 102.6(8) . . ?
C2" C3" N4B 107.0(8) . . ?
C3B N4B C7B 113.2(4) . . ?
C8" N4B C7" 112.2(11) . . ?
C3B N4B C8B 108.5(3) . . ?
C7B N4B C8B 107.8(4) . . ?
C8" N4B C3" 111.2(8) . . ?
C7" N4B C3" 102.7(10) . . ?
C8" N4B Cu1B 115.3(10) . . ?
C3B N4B Cu1B 105.52(18) . . ?
C7B N4B Cu1B 110.0(4) . . ?
C7" N4B Cu1B 110.0(13) . . ?
C8B N4B Cu1B 111.9(2) . . ?
C3" N4B Cu1B 104.5(4) . . ?
C9B O9B Cu1B 124.12(16) . . ?
O9B C9B C10B 124.7(2) . . ?
O9B C9B C12B 115.5(2) . . ?
C10B C9B C12B 119.8(2) . . ?
C11B C10B C9B 125.1(2) . . ?
O11B C11B C10B 125.0(2) . . ?
O11B C11B C13B 115.3(2) . . ?
C10B C11B C13B 119.8(2) . . ?
C11B O11B Cu1B 124.46(16) . . ?
O31 N30 O33 121.3(3) . . ?
O31 N30 O32 120.6(3) . . ?
O33 N30 O32 118.0(3) . . ?
O41 N40 O43 120.7(2) . . ?
O41 N40 O42 119.3(3) . . ?
O43 N40 O42 120.0(2) . . ?

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
O20A H20A O31 0.9000(1) 2.078(9) 2.847(3) 142.7(12) .
O20A H20B O50 0.9000(1) 1.830(3) 2.721(3) 170.0(11) .
O20B H20C O41 0.9000(1) 1.907(3) 2.806(3) 176.9(7) .
O20B H20D O60 0.9000(1) 1.839(3) 2.732(3) 171.8(8) .
O50 H50A N30 0.9000(2) 2.676(6) 3.552(3) 164.9(19) 1_655
O50 H50A O32 0.9000(2) 2.08(2) 2.836(3) 142(3) 1_655
O50 H50B N40 0.9000(1) 2.624(5) 3.483(3) 159.7(9) 1_565
O50 H50B O42 0.9000(1) 1.922(4) 2.815(3) 171(2) 1_565
O60 H60A N40 0.9000(1) 2.681(4) 3.541(3) 160.3(9) 1_455
O60 H60A O42 0.9000(1) 2.447(3) 3.340(3) 172.0(9) 1_455
O60 H60A O43 0.9000(1) 2.213(8) 2.907(3) 133.6(9) 1_455
O60 H60B O32 0.9000(1) 1.970(5) 2.864(3) 172(3) 1_545

_refine_diff_density_max         0.402
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.047

