# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_sad
_database_code_depnum_ccdc_archive 'CCDC 2014603'
loop_
_audit_author_name
_audit_author_address
'Christian Philouze'
;CNRS
France
;
_audit_update_record             
;
2020-07-07 deposited with the CCDC.	2020-09-03 downloaded from the CCDC.
;
_audit_creation_date             2020-07-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H46 Cu N2 O4'
_chemical_formula_sum            'C32 H46 Cu N2 O4'
_chemical_formula_weight         586.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c'
_space_group_name_Hall           '-R 3 2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'y, x, -z+1/2'
'-x+y, -x, z'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'-x+y+2/3, -x+1/3, z+1/3'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'-x+y+1/3, -x+2/3, z+2/3'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'-y, -x, z-1/2'
'x-y, x, -z'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'x-y+2/3, x+1/3, -z+1/3'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'x-y+1/3, x+2/3, -z+2/3'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   29.373(4)
_cell_length_b                   29.373(4)
_cell_length_c                   20.654(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     15433(5)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    30288
_cell_measurement_temperature    200
_cell_measurement_theta_max      24.999
_cell_measurement_theta_min      2.337
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.204758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.6119 before and 0.0955 after correction.
The Ratio of minimum to maximum transmission is 0.2048.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.135
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             5634
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            30288
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.337
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'APEX II'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'κ-geometry 4 circles diffractometer'
_diffrn_measurement_device_type  'Bruker-AXS-enraf-nonius KappaAPEXII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    'Montel optic'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec ISG250'
_diffrn_source_target            Mo
_diffrn_source_type              'Microfocus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2269
_reflns_number_total             3013
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    ?
_refine_diff_density_max         0.668
_refine_diff_density_min         -1.192
_refine_diff_density_rms         0.148
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3013
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0684
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1481P)²+15.6062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1861
_refine_ls_wR_factor_ref         0.2187
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C3(H3)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C12(H12A,H12B,H12C), C15(H15A,H15B,
 H15C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.60731(2) 0.66667 0.4167 0.0356(3) Uani 1 2 d S T P . .
O1 O 0.54687(10) 0.63961(11) 0.46986(13) 0.0450(7) Uani 1 1 d . . . . .
O2 O 0.48589(12) 0.49835(10) 0.67065(12) 0.0514(7) Uani 1 1 d . . . . .
N1 N 0.62036(11) 0.60820(11) 0.43440(12) 0.0344(7) Uani 1 1 d . . . . .
C6 C 0.49326(13) 0.59939(14) 0.56215(16) 0.0369(8) Uani 1 1 d . . . . .
C1 C 0.53328(14) 0.60544(14) 0.51676(16) 0.0379(8) Uani 1 1 d . . . . .
C2 C 0.55633(14) 0.57347(13) 0.52438(16) 0.0356(8) Uani 1 1 d . . . . .
C16 C 0.71455(14) 0.63690(14) 0.42345(17) 0.0381(8) Uani 1 1 d . . . . .
H16A H 0.7372 0.6230 0.4083 0.046 Uiso 1 1 calc R . . . .
H16B H 0.7117 0.6324 0.4711 0.046 Uiso 1 1 calc R . . . .
C8 C 0.46401(16) 0.62961(16) 0.5531(2) 0.0494(10) Uani 1 1 d . . . . .
C5 C 0.48171(14) 0.56416(14) 0.61187(16) 0.0401(8) Uani 1 1 d . . . . .
H5 H 0.4570 0.5613 0.6435 0.048 Uiso 1 1 calc R . . . .
C7 C 0.59488(14) 0.57458(13) 0.48063(16) 0.0370(8) Uani 1 1 d . . . . .
H7 H 0.6029 0.5473 0.4860 0.044 Uiso 1 1 calc R . . . .
C4 C 0.50409(15) 0.53235(14) 0.61858(16) 0.0405(8) Uani 1 1 d . . . . .
C11 C 0.50197(19) 0.68915(17) 0.5526(2) 0.0622(12) Uani 1 1 d . . . . .
H11A H 0.5204 0.7000 0.5942 0.093 Uiso 1 1 calc GR . . . .
H11B H 0.4822 0.7074 0.5457 0.093 Uiso 1 1 calc GR . . . .
H11C H 0.5276 0.6981 0.5177 0.093 Uiso 1 1 calc GR . . . .
C14 C 0.65432(15) 0.61389(16) 0.32482(18) 0.0445(9) Uani 1 1 d . . . . .
H14A H 0.6204 0.5867 0.3075 0.067 Uiso 1 1 calc GR . . . .
H14B H 0.6829 0.6150 0.2991 0.067 Uiso 1 1 calc GR . . . .
H14C H 0.6563 0.6482 0.3227 0.067 Uiso 1 1 calc GR . . . .
C13 C 0.65958(14) 0.60110(14) 0.39551(19) 0.0383(9) Uani 1 1 d . . . . .
C3 C 0.54037(15) 0.53622(14) 0.57499(17) 0.0397(8) Uani 1 1 d . . . . .
H3 H 0.5550 0.5139 0.5785 0.048 Uiso 1 1 calc R . . . .
C12 C 0.50156(18) 0.45971(16) 0.67423(19) 0.0495(10) Uani 1 1 d . . . . .
H12A H 0.4907 0.4384 0.6347 0.074 Uiso 1 1 calc GR . . . .
H12B H 0.4849 0.4370 0.7118 0.074 Uiso 1 1 calc GR . . . .
H12C H 0.5399 0.4771 0.6786 0.074 Uiso 1 1 calc GR . . . .
C15 C 0.65002(17) 0.54524(15) 0.3979(2) 0.0508(10) Uani 1 1 d . . . . .
H15A H 0.6594 0.5383 0.4409 0.076 Uiso 1 1 calc GR . . . .
H15B H 0.6717 0.5410 0.3651 0.076 Uiso 1 1 calc GR . . . .
H15C H 0.6128 0.5204 0.3893 0.076 Uiso 1 1 calc GR . . . .
C9 C 0.4334(2) 0.6120(2) 0.4881(2) 0.0681(13) Uani 1 1 d . . . . .
H9A H 0.4580 0.6183 0.4527 0.102 Uiso 1 1 calc GR . . . .
H9B H 0.4155 0.6321 0.4805 0.102 Uiso 1 1 calc GR . . . .
H9C H 0.4074 0.5744 0.4902 0.102 Uiso 1 1 calc GR . . . .
C10 C 0.42407(19) 0.6181(2) 0.6078(3) 0.0657(12) Uani 1 1 d . . . . .
H10A H 0.3990 0.5802 0.6094 0.099 Uiso 1 1 calc GR . . . .
H10B H 0.4051 0.6371 0.5995 0.099 Uiso 1 1 calc GR . . . .
H10C H 0.4426 0.6295 0.6492 0.099 Uiso 1 1 calc GR . . . .


_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 O1 1.892(2) . ?
Cu1 O1 1.892(2) 11_565 ?
Cu1 N1 1.972(3) 11_565 ?
Cu1 N1 1.972(3) . ?
O1 C1 1.306(4) . ?
O2 C4 1.381(4) . ?
O2 C12 1.424(5) . ?
N1 C7 1.307(4) . ?
N1 C13 1.502(4) . ?
C6 C1 1.443(5) . ?
C6 C8 1.524(5) . ?
C6 C5 1.375(5) . ?
C1 C2 1.415(5) . ?
C2 C7 1.436(5) . ?
C2 C3 1.413(5) . ?
C16 C16 1.540(7) 11_565 ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C13 1.532(5) . ?
C8 C11 1.534(6) . ?
C8 C9 1.553(6) . ?
C8 C10 1.538(6) . ?
C5 H5 0.9500 . ?
C5 C4 1.392(6) . ?
C7 H7 0.9500 . ?
C4 C3 1.356(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14 C13 1.535(5) . ?
C13 C15 1.521(5) . ?
C3 H3 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
O1 Cu1 O1 86.49(15) . 11_565 ?
O1 Cu1 N1 147.24(12) . 11_565 ?
O1 Cu1 N1 147.24(12) 11_565 . ?
O1 Cu1 N1 94.39(11) . . ?
O1 Cu1 N1 94.39(11) 11_565 11_565 ?
N1 Cu1 N1 101.93(17) 11_565 . ?
C1 O1 Cu1 128.0(2) . . ?
C4 O2 C12 117.0(3) . . ?
C7 N1 Cu1 120.4(2) . . ?
C7 N1 C13 118.4(3) . . ?
C13 N1 Cu1 121.2(2) . . ?
C1 C6 C8 120.7(3) . . ?
C5 C6 C1 117.2(3) . . ?
C5 C6 C8 122.1(3) . . ?
O1 C1 C6 119.6(3) . . ?
O1 C1 C2 121.9(3) . . ?
C2 C1 C6 118.5(3) . . ?
C1 C2 C7 123.3(3) . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 C7 115.8(3) . . ?
C16 C16 H16A 107.1 11_565 . ?
C16 C16 H16B 107.1 11_565 . ?
H16A C16 H16B 106.8 . . ?
C13 C16 C16 121.1(3) . 11_565 ?
C13 C16 H16A 107.1 . . ?
C13 C16 H16B 107.1 . . ?
C6 C8 C11 111.4(3) . . ?
C6 C8 C9 108.2(3) . . ?
C6 C8 C10 111.8(3) . . ?
C11 C8 C9 110.1(4) . . ?
C11 C8 C10 107.2(4) . . ?
C10 C8 C9 108.0(4) . . ?
C6 C5 H5 118.0 . . ?
C6 C5 C4 123.9(3) . . ?
C4 C5 H5 118.0 . . ?
N1 C7 C2 128.6(3) . . ?
N1 C7 H7 115.7 . . ?
C2 C7 H7 115.7 . . ?
O2 C4 C5 114.9(3) . . ?
C3 C4 O2 125.6(3) . . ?
C3 C4 C5 119.5(3) . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
N1 C13 C16 108.8(3) . . ?
N1 C13 C14 107.3(3) . . ?
N1 C13 C15 113.0(3) . . ?
C16 C13 C14 113.0(3) . . ?
C15 C13 C16 106.9(3) . . ?
C15 C13 C14 108.0(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.0 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.126 1025.3 341.2 ?
2 0.333 0.667 -0.376 1025.3 341.2 ?
3 0.667 0.333 -0.710 1025.3 341.2 ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_sad_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2014605'
loop_
_audit_author_name
_audit_author_address
'Christian Philouze'
;CNRS
France
;
_audit_update_record             
;
2020-07-07 deposited with the CCDC.	2020-09-03 downloaded from the CCDC.
;
_audit_creation_date             2020-07-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H40 N2 O4'
_chemical_formula_sum            'C36 H40 N2 O4'
_chemical_formula_weight         564.70
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.432(5)
_cell_length_b                   11.329(2)
_cell_length_c                   13.480(3)
_cell_angle_alpha                90
_cell_angle_beta                 117.10(3)
_cell_angle_gamma                90
_cell_volume                     3049.7(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17098
_cell_measurement_temperature    200
_cell_measurement_theta_max      29.999
_cell_measurement_theta_min      2.361
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.539845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.2608 before and 0.0627 after correction.
The Ratio of minimum to maximum transmission is 0.5398.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17098
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         2.361
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'APEX II'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'κ-geometry 4 circles diffractometer'
_diffrn_measurement_device_type  'Bruker-AXS-enraf-nonius KappaAPEXII'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_collimation    'Montel optic'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec ISG250'
_diffrn_source_target            Mo
_diffrn_source_type              'Microfocus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3342
_reflns_number_total             4398
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    ?
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         4398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0537
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0640P)²+2.2407P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1526
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C5(H5), C17(H17), C14(H14), C16(H16), C15(H15)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C11(H11A,H11B,H11C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.60130(5) 0.57136(8) 0.71740(9) 0.0306(2) Uani 1 1 d . . . . .
H1 H 0.5709 0.6226 0.6967 0.046 Uiso 1 1 calc GR . . . .
O2 O 0.49522(6) 0.13136(9) 0.56185(10) 0.0370(3) Uani 1 1 d . . . . .
N1 N 0.48128(6) 0.65556(10) 0.63357(9) 0.0240(2) Uani 1 1 d . . . . .
C2 C 0.50392(7) 0.45177(11) 0.61827(11) 0.0221(3) Uani 1 1 d . . . . .
C1 C 0.57378(7) 0.46397(11) 0.67971(11) 0.0226(3) Uani 1 1 d . . . . .
C13 C 0.43743(7) 0.74815(11) 0.62766(11) 0.0228(3) Uani 1 1 d . . . . .
C18 C 0.46438(7) 0.83840(11) 0.70743(10) 0.0229(3) Uani 1 1 d . . . . .
C6 C 0.61585(7) 0.36419(11) 0.70500(11) 0.0235(3) Uani 1 1 d . . . . .
C4 C 0.51636(7) 0.24404(11) 0.59881(12) 0.0263(3) Uani 1 1 d . . . . .
C7 C 0.45909(7) 0.55075(11) 0.60099(11) 0.0235(3) Uani 1 1 d . . . . .
H7 H 0.4121 0.5377 0.5646 0.028 Uiso 1 1 calc R . . . .
C8 C 0.69169(7) 0.37374(12) 0.77877(13) 0.0297(3) Uani 1 1 d . . . . .
C3 C 0.47524(7) 0.34064(11) 0.57755(11) 0.0244(3) Uani 1 1 d . . . . .
H3 H 0.4281 0.3325 0.5359 0.029 Uiso 1 1 calc R . . . .
C5 C 0.58538(7) 0.25637(11) 0.66300(12) 0.0262(3) Uani 1 1 d . . . . .
H5 H 0.6127 0.1880 0.6787 0.031 Uiso 1 1 calc R . . . .
C17 C 0.42274(8) 0.93093(12) 0.70541(12) 0.0289(3) Uani 1 1 d . . . . .
H17 H 0.4404 0.9927 0.7586 0.035 Uiso 1 1 calc R . . . .
C14 C 0.37064(7) 0.75340(12) 0.54768(12) 0.0286(3) Uani 1 1 d . . . . .
H14 H 0.3528 0.6934 0.4927 0.034 Uiso 1 1 calc R . . . .
C16 C 0.35616(8) 0.93393(13) 0.62706(14) 0.0332(3) Uani 1 1 d . . . . .
H16 H 0.3282 0.9967 0.6276 0.040 Uiso 1 1 calc R . . . .
C15 C 0.33015(8) 0.84552(13) 0.54780(13) 0.0333(3) Uani 1 1 d . . . . .
H15 H 0.2845 0.8481 0.4935 0.040 Uiso 1 1 calc R . . . .
C12 C 0.42685(8) 0.11606(14) 0.48606(15) 0.0392(4) Uani 1 1 d . . . . .
H12A H 0.4155 0.1654 0.4202 0.059 Uiso 1 1 calc GR . . . .
H12B H 0.3992 0.1392 0.5219 0.059 Uiso 1 1 calc GR . . . .
H12C H 0.4185 0.0330 0.4636 0.059 Uiso 1 1 calc GR . . . .
C11 C 0.72329(8) 0.46091(15) 0.72934(17) 0.0402(4) Uani 1 1 d . . . . .
H11A H 0.7171 0.4318 0.6568 0.060 Uiso 1 1 calc GR . . . .
H11B H 0.7712 0.4684 0.7798 0.060 Uiso 1 1 calc GR . . . .
H11C H 0.7017 0.5382 0.7199 0.060 Uiso 1 1 calc GR . . . .
C9 C 0.70487(9) 0.41423(18) 0.89582(14) 0.0445(4) Uani 1 1 d . . . . .
H9A H 0.6851 0.4925 0.8911 0.067 Uiso 1 1 calc GR . . . .
H9B H 0.7533 0.4181 0.9442 0.067 Uiso 1 1 calc GR . . . .
H9C H 0.6846 0.3579 0.9268 0.067 Uiso 1 1 calc GR . . . .
C10 C 0.72696(8) 0.25499(14) 0.79069(17) 0.0435(4) Uani 1 1 d . . . . .
H10A H 0.7092 0.1974 0.8246 0.065 Uiso 1 1 calc GR . . . .
H10B H 0.7752 0.2647 0.8381 0.065 Uiso 1 1 calc GR . . . .
H10C H 0.7191 0.2269 0.7170 0.065 Uiso 1 1 calc GR . . . .


_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
O1 H1 0.8400 . ?
O1 C1 1.3542(15) . ?
O2 C4 1.3739(16) . ?
O2 C12 1.414(2) . ?
N1 C13 1.4153(17) . ?
N1 C7 1.2851(17) . ?
C2 C1 1.4065(19) . ?
C2 C7 1.4525(18) . ?
C2 C3 1.4066(17) . ?
C1 C6 1.4113(18) . ?
C13 C18 1.4054(18) . ?
C13 C14 1.392(2) . ?
C18 C18 1.483(3) 2_656 ?
C18 C17 1.3960(19) . ?
C6 C8 1.5341(19) . ?
C6 C5 1.3882(18) . ?
C4 C3 1.3747(19) . ?
C4 C5 1.395(2) . ?
C7 H7 0.9500 . ?
C8 C11 1.534(2) . ?
C8 C9 1.537(2) . ?
C8 C10 1.532(2) . ?
C3 H3 0.9500 . ?
C5 H5 0.9500 . ?
C17 H17 0.9500 . ?
C17 C16 1.382(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(2) . ?
C16 H16 0.9500 . ?
C16 C15 1.385(2) . ?
C15 H15 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
C1 O1 H1 109.5 . . ?
C4 O2 C12 117.23(12) . . ?
C7 N1 C13 120.96(12) . . ?
C1 C2 C7 121.52(11) . . ?
C3 C2 C1 120.44(12) . . ?
C3 C2 C7 117.92(12) . . ?
O1 C1 C2 120.29(11) . . ?
O1 C1 C6 119.25(12) . . ?
C2 C1 C6 120.44(11) . . ?
C18 C13 N1 116.77(12) . . ?
C14 C13 N1 123.40(12) . . ?
C14 C13 C18 119.84(12) . . ?
C13 C18 C18 121.90(11) . 2_656 ?
C17 C18 C13 118.72(12) . . ?
C17 C18 C18 119.38(10) . 2_656 ?
C1 C6 C8 121.48(11) . . ?
C5 C6 C1 117.09(12) . . ?
C5 C6 C8 121.40(12) . . ?
O2 C4 C3 125.18(13) . . ?
O2 C4 C5 114.86(12) . . ?
C3 C4 C5 119.96(12) . . ?
N1 C7 C2 121.77(13) . . ?
N1 C7 H7 119.1 . . ?
C2 C7 H7 119.1 . . ?
C6 C8 C9 108.94(14) . . ?
C11 C8 C6 111.06(13) . . ?
C11 C8 C9 110.06(14) . . ?
C10 C8 C6 111.92(11) . . ?
C10 C8 C11 106.99(14) . . ?
C10 C8 C9 107.81(14) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.15(12) . . ?
C4 C3 H3 120.4 . . ?
C6 C5 C4 122.85(12) . . ?
C6 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C18 C17 H17 119.5 . . ?
C16 C17 C18 120.93(13) . . ?
C16 C17 H17 119.5 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.43(13) . . ?
C15 C14 H14 119.8 . . ?
C17 C16 H16 120.0 . . ?
C17 C16 C15 120.05(14) . . ?
C15 C16 H16 120.0 . . ?
C14 C15 C16 120.02(14) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.84 1.83 2.5813(17) 148.1 .

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sad_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2014609'
loop_
_audit_author_name
_audit_author_address
'Christian Philouze'
;CNRS
France
;
_audit_update_record             
;
2020-07-07 deposited with the CCDC.	2020-09-03 downloaded from the CCDC.
;
_audit_creation_date             2020-07-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C19 H30 N O)'
_chemical_formula_sum            'C38 H60 N2 O2'
_chemical_formula_weight         576.88
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

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

_cell_length_a                   10.267(2)
_cell_length_b                   11.826(2)
_cell_length_c                   15.541(3)
_cell_angle_alpha                76.67(3)
_cell_angle_beta                 83.43(3)
_cell_angle_gamma                80.89(3)
_cell_volume                     1807.0(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    34614
_cell_measurement_temperature    200
_cell_measurement_theta_max      68.006
_cell_measurement_theta_min      3.878
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.488
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.714399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.0477 before and 0.0292 after correction.
The Ratio of minimum to maximum transmission is 0.7144.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.060
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.71
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            34614
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.006
_diffrn_reflns_theta_min         3.878
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            KappaCCD
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device       'κ-geometry 4 circles diffractometer'
_diffrn_measurement_device_type  'Bruker-AXS-Nonius kappaCCD'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_source_target            Cu
_diffrn_source_type              'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5198
_reflns_number_total             6303
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    ?
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         6303
_refine_ls_number_restraints     150
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0679P)²+0.5145P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1314
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C14C-C12A
 1.53 with sigma of 0.02
 C14A-C12A
 1.53 with sigma of 0.02
 C12A-C13C
 1.53 with sigma of 0.02
 C15C-C12A
 1.53 with sigma of 0.02
 C15A-C12A
 1.53 with sigma of 0.02
 C12A-C13A
 1.53 with sigma of 0.02
 C13D-C12B
 1.53 with sigma of 0.02
 C13B-C12B
 1.53 with sigma of 0.02
 C15B-C12B
 1.53 with sigma of 0.02
 C15D-C12B
 1.53 with sigma of 0.02
 C12B-C14B
 1.53 with sigma of 0.02
 C12B-C14D
 1.53 with sigma of 0.02
3. Rigid bond restraints
 C14C, C14A, C13C, C13A, C15C, C15A, C12A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C13B, C13D, C15B, C15D, C12B, C14B, C14D
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C15A \\sim C14C \\sim C14A \\sim C13C \\sim C13A \\sim C15C \\sim C12A: within
1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
C13D \\sim C13B \\sim C15B \\sim C15D \\sim C14B \\sim C14D \\sim C12B: within
1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
5. Others
 Sof(C13C)=Sof(H13J)=Sof(H13K)=Sof(H13L)=Sof(C14C)=Sof(H14J)=Sof(H14K)=
 Sof(H14L)=Sof(C15C)=Sof(H15J)=Sof(H15K)=Sof(H15L)=1-FVAR(1)
 Sof(C14A)=Sof(H14G)=Sof(H14H)=Sof(H14I)=Sof(C13A)=Sof(H13G)=Sof(H13H)=
 Sof(H13I)=Sof(C15A)=Sof(H15G)=Sof(H15H)=Sof(H15I)=FVAR(1)
 Sof(C15D)=Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(C14D)=Sof(H14A)=Sof(H14B)=
 Sof(H14C)=Sof(C13D)=Sof(H13A)=Sof(H13B)=Sof(H13C)=1-FVAR(2)
 Sof(C13B)=Sof(H13D)=Sof(H13E)=Sof(H13F)=Sof(C15B)=Sof(H15D)=Sof(H15E)=
 Sof(H15F)=Sof(C14B)=Sof(H14D)=Sof(H14E)=Sof(H14F)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C19B(H19A,H19B), C19A(H19C,H19D)
6.b Aromatic/amide H refined with riding coordinates:
 C7B(H7B), C3A(H3A), C5A(H5A), C3B(H3B), C7A(H7A), C5B(H5B)
6.c Idealised Me refined as rotating group:
 C17B(H17A,H17B,H17C), C11B(H11A,H11B,H11C), C18B(H18A,H18B,H18C), C9B(H9BA,
 H9BB,H9BC), C11A(H11D,H11E,H11F), C17A(H17D,H17E,H17F), C18A(H18D,H18E,H18F),
 C10B(H10A,H10B,H10C), C10A(H10D,H10E,H10F), C15D(H15A,H15B,H15C), C14D(H14A,
 H14B,H14C), C13D(H13A,H13B,H13C), C9A(H9AA,H9AB,H9AC), C14A(H14G,H14H,H14I),
 C13A(H13G,H13H,H13I), C15A(H15G,H15H,H15I), C13C(H13J,H13K,H13L), C14C(H14J,
 H14K,H14L), C15C(H15J,H15K,H15L), C13B(H13D,H13E,H13F), C15B(H15D,H15E,H15F),
 C14B(H14D,H14E,H14F)
6.d Idealised tetrahedral OH refined as rotating group:
 O1B(H1B), O1A(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1B O 0.94562(10) 0.33590(9) 0.17865(7) 0.0395(2) Uani 1 1 d . . . . .
H1B H 0.9480 0.3021 0.1364 0.059 Uiso 1 1 calc GR . . . .
O1A O 0.50221(10) 0.07938(9) 0.11967(7) 0.0420(3) Uani 1 1 d . . . . .
H1A H 0.4830 0.1520 0.1011 0.063 Uiso 1 1 calc GR . . . .
N1B N 0.87722(12) 0.21223(10) 0.08277(8) 0.0342(3) Uani 1 1 d . . . . .
N1A N 0.36682(12) 0.28410(10) 0.09735(8) 0.0384(3) Uani 1 1 d . . . . .
C2B C 0.74526(14) 0.25129(12) 0.21230(9) 0.0337(3) Uani 1 1 d . . . . .
C1B C 0.83412(13) 0.31899(12) 0.23191(9) 0.0328(3) Uani 1 1 d . . . . .
C16B C 0.90713(14) 0.15897(12) 0.00371(9) 0.0351(3) Uani 1 1 d . . . . .
C6B C 0.80694(14) 0.36826(13) 0.30784(10) 0.0357(3) Uani 1 1 d . . . . .
C1A C 0.39811(14) 0.03616(13) 0.17048(9) 0.0347(3) Uani 1 1 d . . . . .
C19B C 0.97588(15) 0.03369(12) 0.03676(9) 0.0360(3) Uani 1 1 d . . . . .
H19A H 1.0526 0.0375 0.0687 0.043 Uiso 1 1 calc R . . . .
H19B H 0.9135 -0.0107 0.0798 0.043 Uiso 1 1 calc R . . . .
C2A C 0.27951(14) 0.11173(12) 0.18093(9) 0.0351(3) Uani 1 1 d . . . . .
C16A C 0.35533(15) 0.41396(12) 0.06565(11) 0.0397(3) Uani 1 1 d . . . . .
C7B C 0.77252(14) 0.19963(12) 0.13440(9) 0.0346(3) Uani 1 1 d . . . . .
H7B H 0.7103 0.1553 0.1218 0.041 Uiso 1 1 calc R . . . .
C3A C 0.17136(15) 0.06939(13) 0.23496(10) 0.0371(3) Uani 1 1 d . . . . .
H3A H 0.0916 0.1211 0.2407 0.045 Uiso 1 1 calc R . . . .
C4A C 0.17850(15) -0.04613(13) 0.28004(9) 0.0370(3) Uani 1 1 d . . . . .
C6A C 0.40814(15) -0.08296(12) 0.21413(10) 0.0365(3) Uani 1 1 d . . . . .
C12A C 0.06516(16) -0.09344(14) 0.34400(10) 0.0430(4) Uani 1 1 d D U . . .
C5A C 0.29816(15) -0.11905(13) 0.26784(10) 0.0380(3) Uani 1 1 d . . . . .
H5A H 0.3042 -0.1988 0.2986 0.046 Uiso 1 1 calc R . . . .
C3B C 0.63048(15) 0.23130(14) 0.26794(10) 0.0404(3) Uani 1 1 d . . . . .
H3B H 0.5712 0.1855 0.2538 0.049 Uiso 1 1 calc R . . . .
C8B C 0.90225(16) 0.44272(14) 0.33054(10) 0.0423(4) Uani 1 1 d . . . . .
C7A C 0.26971(15) 0.23687(13) 0.14178(10) 0.0380(3) Uani 1 1 d . . . . .
H7A H 0.1879 0.2851 0.1497 0.046 Uiso 1 1 calc R . . . .
C5B C 0.69208(15) 0.34462(15) 0.36030(10) 0.0423(4) Uani 1 1 d . . . . .
H5B H 0.6729 0.3767 0.4118 0.051 Uiso 1 1 calc R . . . .
C8A C 0.53642(16) -0.16759(14) 0.20415(11) 0.0436(4) Uani 1 1 d . . . . .
C19A C 0.49092(15) 0.43552(12) 0.01826(11) 0.0406(3) Uani 1 1 d . . . . .
H19C H 0.5071 0.3946 -0.0316 0.049 Uiso 1 1 calc R . . . .
H19D H 0.5592 0.3995 0.0602 0.049 Uiso 1 1 calc R . . . .
C4B C 0.60191(15) 0.27684(16) 0.34303(10) 0.0444(4) Uani 1 1 d . . . . .
C12B C 0.47946(18) 0.2548(2) 0.40775(12) 0.0675(6) Uani 1 1 d D U . . .
C17B C 0.78229(17) 0.15800(16) -0.04073(11) 0.0509(4) Uani 1 1 d . . . . .
H17A H 0.7292 0.1010 -0.0027 0.076 Uiso 1 1 calc GR . . . .
H17B H 0.8071 0.1362 -0.0981 0.076 Uiso 1 1 calc GR . . . .
H17C H 0.7305 0.2362 -0.0499 0.076 Uiso 1 1 calc GR . . . .
C11B C 1.03526(17) 0.36705(17) 0.35095(12) 0.0512(4) Uani 1 1 d . . . . .
H11A H 1.0216 0.3017 0.4013 0.077 Uiso 1 1 calc GR . . . .
H11B H 1.0957 0.4149 0.3657 0.077 Uiso 1 1 calc GR . . . .
H11C H 1.0736 0.3362 0.2989 0.077 Uiso 1 1 calc GR . . . .
C18B C 1.0000(2) 0.23482(15) -0.05840(12) 0.0552(5) Uani 1 1 d . . . . .
H18A H 0.9567 0.3162 -0.0722 0.083 Uiso 1 1 calc GR . . . .
H18B H 1.0220 0.2061 -0.1133 0.083 Uiso 1 1 calc GR . . . .
H18C H 1.0812 0.2311 -0.0297 0.083 Uiso 1 1 calc GR . . . .
C9B C 0.9239(2) 0.54619(15) 0.25246(12) 0.0545(4) Uani 1 1 d . . . . .
H9BA H 0.9610 0.5163 0.1997 0.082 Uiso 1 1 calc GR . . . .
H9BB H 0.9855 0.5927 0.2675 0.082 Uiso 1 1 calc GR . . . .
H9BC H 0.8392 0.5956 0.2403 0.082 Uiso 1 1 calc GR . . . .
C11A C 0.64903(17) -0.12895(16) 0.24232(13) 0.0530(4) Uani 1 1 d . . . . .
H11D H 0.6647 -0.0505 0.2091 0.079 Uiso 1 1 calc GR . . . .
H11E H 0.7298 -0.1845 0.2374 0.079 Uiso 1 1 calc GR . . . .
H11F H 0.6247 -0.1272 0.3049 0.079 Uiso 1 1 calc GR . . . .
C17A C 0.24540(18) 0.45687(15) 0.00343(14) 0.0579(5) Uani 1 1 d . . . . .
H17D H 0.2641 0.4184 -0.0470 0.087 Uiso 1 1 calc GR . . . .
H17E H 0.2402 0.5420 -0.0181 0.087 Uiso 1 1 calc GR . . . .
H17F H 0.1609 0.4379 0.0353 0.087 Uiso 1 1 calc GR . . . .
C18A C 0.3278(2) 0.47070(15) 0.14606(13) 0.0596(5) Uani 1 1 d . . . . .
H18D H 0.2439 0.4506 0.1783 0.089 Uiso 1 1 calc GR . . . .
H18E H 0.3221 0.5561 0.1261 0.089 Uiso 1 1 calc GR . . . .
H18F H 0.3997 0.4418 0.1853 0.089 Uiso 1 1 calc GR . . . .
C10B C 0.8483(2) 0.49371(19) 0.41201(13) 0.0604(5) Uani 1 1 d . . . . .
H10A H 0.7626 0.5419 0.4008 0.091 Uiso 1 1 calc GR . . . .
H10B H 0.9107 0.5422 0.4235 0.091 Uiso 1 1 calc GR . . . .
H10C H 0.8372 0.4295 0.4637 0.091 Uiso 1 1 calc GR . . . .
C10A C 0.57404(19) -0.16987(17) 0.10606(13) 0.0556(4) Uani 1 1 d . . . . .
H10D H 0.5039 -0.1984 0.0825 0.083 Uiso 1 1 calc GR . . . .
H10E H 0.6573 -0.2222 0.1005 0.083 Uiso 1 1 calc GR . . . .
H10F H 0.5850 -0.0905 0.0725 0.083 Uiso 1 1 calc GR . . . .
C15D C 0.518(2) 0.174(3) 0.4952(12) 0.128(6) Uani 0.36(5) 1 d D U P A 2
H15A H 0.5551 0.0963 0.4850 0.191 Uiso 0.36(5) 1 calc GR . P A 2
H15B H 0.4392 0.1674 0.5372 0.191 Uiso 0.36(5) 1 calc GR . P A 2
H15C H 0.5838 0.2066 0.5196 0.191 Uiso 0.36(5) 1 calc GR . P A 2
C14D C 0.3844(13) 0.1971(19) 0.3695(16) 0.053(4) Uani 0.36(5) 1 d D U P A 2
H14A H 0.3547 0.2488 0.3144 0.080 Uiso 0.36(5) 1 calc GR . P A 2
H14B H 0.3079 0.1828 0.4123 0.080 Uiso 0.36(5) 1 calc GR . P A 2
H14C H 0.4294 0.1224 0.3571 0.080 Uiso 0.36(5) 1 calc GR . P A 2
C13D C 0.403(3) 0.363(3) 0.437(3) 0.117(7) Uani 0.36(5) 1 d D U P A 2
H13A H 0.4593 0.3924 0.4719 0.175 Uiso 0.36(5) 1 calc GR . P A 2
H13B H 0.3233 0.3412 0.4744 0.175 Uiso 0.36(5) 1 calc GR . P A 2
H13C H 0.3787 0.4234 0.3853 0.175 Uiso 0.36(5) 1 calc GR . P A 2
C9A C 0.52042(19) -0.29362(15) 0.25376(15) 0.0620(5) Uani 1 1 d . . . . .
H9AA H 0.4991 -0.2956 0.3171 0.093 Uiso 1 1 calc GR . . . .
H9AB H 0.6032 -0.3454 0.2455 0.093 Uiso 1 1 calc GR . . . .
H9AC H 0.4488 -0.3202 0.2303 0.093 Uiso 1 1 calc GR . . . .
C14A C 0.0316(3) -0.2042(3) 0.3239(2) 0.0693(9) Uani 0.847(7) 1 d D U P B 1
H14G H 0.0023 -0.1870 0.2638 0.104 Uiso 0.847(7) 1 calc GR . P B 1
H14H H -0.0394 -0.2338 0.3668 0.104 Uiso 0.847(7) 1 calc GR . P B 1
H14I H 0.1101 -0.2637 0.3280 0.104 Uiso 0.847(7) 1 calc GR . P B 1
C13A C -0.0622(2) -0.0043(2) 0.33921(19) 0.0577(8) Uani 0.847(7) 1 d D U P B 1
H13G H -0.0454 0.0668 0.3558 0.086 Uiso 0.847(7) 1 calc GR . P B 1
H13H H -0.1325 -0.0387 0.3802 0.086 Uiso 0.847(7) 1 calc GR . P B 1
H13I H -0.0898 0.0157 0.2786 0.086 Uiso 0.847(7) 1 calc GR . P B 1
C15A C 0.1062(4) -0.1186(3) 0.4391(2) 0.0671(9) Uani 0.847(7) 1 d D U P B 1
H15G H 0.1827 -0.1802 0.4459 0.101 Uiso 0.847(7) 1 calc GR . P B 1
H15H H 0.0324 -0.1447 0.4809 0.101 Uiso 0.847(7) 1 calc GR . P B 1
H15I H 0.1298 -0.0471 0.4513 0.101 Uiso 0.847(7) 1 calc GR . P B 1
C13C C -0.0526(15) -0.073(2) 0.2951(14) 0.101(8) Uani 0.153(7) 1 d D U P B 2
H13J H -0.0701 0.0108 0.2670 0.152 Uiso 0.153(7) 1 calc GR . P B 2
H13K H -0.1285 -0.0953 0.3361 0.152 Uiso 0.153(7) 1 calc GR . P B 2
H13L H -0.0381 -0.1193 0.2495 0.152 Uiso 0.153(7) 1 calc GR . P B 2
C14C C 0.101(2) -0.2343(12) 0.3713(19) 0.100(7) Uani 0.153(7) 1 d D U P B 2
H14J H 0.1129 -0.2666 0.3178 0.150 Uiso 0.153(7) 1 calc GR . P B 2
H14K H 0.0290 -0.2673 0.4113 0.150 Uiso 0.153(7) 1 calc GR . P B 2
H14L H 0.1831 -0.2544 0.4014 0.150 Uiso 0.153(7) 1 calc GR . P B 2
C15C C 0.079(4) -0.058(3) 0.4282(14) 0.125(10) Uani 0.153(7) 1 d D U P B 2
H15J H 0.1690 -0.0866 0.4463 0.188 Uiso 0.153(7) 1 calc GR . P B 2
H15K H 0.0150 -0.0929 0.4745 0.188 Uiso 0.153(7) 1 calc GR . P B 2
H15L H 0.0628 0.0272 0.4190 0.188 Uiso 0.153(7) 1 calc GR . P B 2
C13B C 0.4000(10) 0.3773(10) 0.4119(11) 0.092(3) Uani 0.64(5) 1 d D U P A 1
H13D H 0.4553 0.4240 0.4330 0.138 Uiso 0.64(5) 1 calc GR . P A 1
H13E H 0.3205 0.3674 0.4526 0.138 Uiso 0.64(5) 1 calc GR . P A 1
H13F H 0.3743 0.4177 0.3525 0.138 Uiso 0.64(5) 1 calc GR . P A 1
C15B C 0.5304(13) 0.1856(17) 0.4975(5) 0.127(4) Uani 0.64(5) 1 d D U P A 1
H15D H 0.5918 0.1163 0.4883 0.191 Uiso 0.64(5) 1 calc GR . P A 1
H15E H 0.4554 0.1610 0.5387 0.191 Uiso 0.64(5) 1 calc GR . P A 1
H15F H 0.5763 0.2358 0.5224 0.191 Uiso 0.64(5) 1 calc GR . P A 1
C14B C 0.3888(11) 0.1836(16) 0.3768(11) 0.082(3) Uani 0.64(5) 1 d D U P A 1
H14D H 0.3550 0.2276 0.3205 0.123 Uiso 0.64(5) 1 calc GR . P A 1
H14E H 0.3144 0.1692 0.4216 0.123 Uiso 0.64(5) 1 calc GR . P A 1
H14F H 0.4388 0.1085 0.3687 0.123 Uiso 0.64(5) 1 calc GR . P A 1


_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
O1B H1B 0.8400 . ?
O1B C1B 1.3472(17) . ?
O1A H1A 0.8400 . ?
O1A C1A 1.3495(18) . ?
N1B C16B 1.4866(17) . ?
N1B C7B 1.2727(19) . ?
N1A C16A 1.4907(19) . ?
N1A C7A 1.274(2) . ?
C2B C1B 1.405(2) . ?
C2B C7B 1.458(2) . ?
C2B C3B 1.398(2) . ?
C1B C6B 1.414(2) . ?
C16B C19B 1.536(2) . ?
C16B C17B 1.527(2) . ?
C16B C18B 1.519(2) . ?
C6B C8B 1.534(2) . ?
C6B C5B 1.383(2) . ?
C1A C2A 1.409(2) . ?
C1A C6A 1.409(2) . ?
C19B C19B 1.533(3) 2_755 ?
C19B H19A 0.9900 . ?
C19B H19B 0.9900 . ?
C2A C3A 1.399(2) . ?
C2A C7A 1.457(2) . ?
C16A C19A 1.529(2) . ?
C16A C17A 1.519(2) . ?
C16A C18A 1.529(2) . ?
C7B H7B 0.9500 . ?
C3A H3A 0.9500 . ?
C3A C4A 1.379(2) . ?
C4A C12A 1.530(2) . ?
C4A C5A 1.406(2) . ?
C6A C5A 1.388(2) . ?
C6A C8A 1.539(2) . ?
C12A C14A 1.513(3) . ?
C12A C13A 1.542(3) . ?
C12A C15A 1.534(3) . ?
C12A C13C 1.458(14) . ?
C12A C14C 1.614(14) . ?
C12A C15C 1.488(16) . ?
C5A H5A 0.9500 . ?
C3B H3B 0.9500 . ?
C3B C4B 1.378(2) . ?
C8B C11B 1.532(2) . ?
C8B C9B 1.536(2) . ?
C8B C10B 1.536(2) . ?
C7A H7A 0.9500 . ?
C5B H5B 0.9500 . ?
C5B C4B 1.401(2) . ?
C8A C11A 1.532(2) . ?
C8A C10A 1.534(2) . ?
C8A C9A 1.537(2) . ?
C19A C19A 1.533(3) 2_665 ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C4B C12B 1.534(2) . ?
C12B C15D 1.522(16) . ?
C12B C14D 1.517(14) . ?
C12B C13D 1.524(16) . ?
C12B C13B 1.558(9) . ?
C12B C15B 1.548(9) . ?
C12B C14B 1.531(10) . ?
C17B H17A 0.9800 . ?
C17B H17B 0.9800 . ?
C17B H17C 0.9800 . ?
C11B H11A 0.9800 . ?
C11B H11B 0.9800 . ?
C11B H11C 0.9800 . ?
C18B H18A 0.9800 . ?
C18B H18B 0.9800 . ?
C18B H18C 0.9800 . ?
C9B H9BA 0.9800 . ?
C9B H9BB 0.9800 . ?
C9B H9BC 0.9800 . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 0.9800 . ?
C17A H17D 0.9800 . ?
C17A H17E 0.9800 . ?
C17A H17F 0.9800 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
C10B H10A 0.9800 . ?
C10B H10B 0.9800 . ?
C10B H10C 0.9800 . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C15D H15A 0.9800 . ?
C15D H15B 0.9800 . ?
C15D H15C 0.9800 . ?
C14D H14A 0.9800 . ?
C14D H14B 0.9800 . ?
C14D H14C 0.9800 . ?
C13D H13A 0.9800 . ?
C13D H13B 0.9800 . ?
C13D H13C 0.9800 . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
C14A H14G 0.9800 . ?
C14A H14H 0.9800 . ?
C14A H14I 0.9800 . ?
C13A H13G 0.9800 . ?
C13A H13H 0.9800 . ?
C13A H13I 0.9800 . ?
C15A H15G 0.9800 . ?
C15A H15H 0.9800 . ?
C15A H15I 0.9800 . ?
C13C H13J 0.9800 . ?
C13C H13K 0.9800 . ?
C13C H13L 0.9800 . ?
C14C H14J 0.9800 . ?
C14C H14K 0.9800 . ?
C14C H14L 0.9800 . ?
C15C H15J 0.9800 . ?
C15C H15K 0.9800 . ?
C15C H15L 0.9800 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?

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
C1B O1B H1B 109.5 . . ?
C1A O1A H1A 109.5 . . ?
C7B N1B C16B 122.51(12) . . ?
C7A N1A C16A 120.27(13) . . ?
C1B C2B C7B 120.45(13) . . ?
C3B C2B C1B 120.36(13) . . ?
C3B C2B C7B 119.18(13) . . ?
O1B C1B C2B 119.82(12) . . ?
O1B C1B C6B 120.21(13) . . ?
C2B C1B C6B 119.97(13) . . ?
N1B C16B C19B 106.28(11) . . ?
N1B C16B C17B 111.97(12) . . ?
N1B C16B C18B 104.90(12) . . ?
C17B C16B C19B 110.98(13) . . ?
C18B C16B C19B 111.68(13) . . ?
C18B C16B C17B 110.81(14) . . ?
C1B C6B C8B 120.94(13) . . ?
C5B C6B C1B 116.74(13) . . ?
C5B C6B C8B 122.32(13) . . ?
O1A C1A C2A 119.42(13) . . ?
O1A C1A C6A 120.54(13) . . ?
C2A C1A C6A 120.03(13) . . ?
C16B C19B H19A 108.7 . . ?
C16B C19B H19B 108.7 . . ?
C19B C19B C16B 114.35(15) 2_755 . ?
C19B C19B H19A 108.7 2_755 . ?
C19B C19B H19B 108.7 2_755 . ?
H19A C19B H19B 107.6 . . ?
C1A C2A C7A 121.08(13) . . ?
C3A C2A C1A 120.38(13) . . ?
C3A C2A C7A 118.36(13) . . ?
N1A C16A C19A 104.38(12) . . ?
N1A C16A C17A 110.19(13) . . ?
N1A C16A C18A 108.74(13) . . ?
C19A C16A C18A 110.64(14) . . ?
C17A C16A C19A 111.87(14) . . ?
C17A C16A C18A 110.80(15) . . ?
N1B C7B C2B 121.89(13) . . ?
N1B C7B H7B 119.1 . . ?
C2B C7B H7B 119.1 . . ?
C2A C3A H3A 119.4 . . ?
C4A C3A C2A 121.16(14) . . ?
C4A C3A H3A 119.4 . . ?
C3A C4A C12A 122.47(14) . . ?
C3A C4A C5A 116.89(14) . . ?
C5A C4A C12A 120.58(13) . . ?
C1A C6A C8A 121.24(13) . . ?
C5A C6A C1A 116.77(13) . . ?
C5A C6A C8A 121.98(13) . . ?
C4A C12A C13A 112.23(14) . . ?
C4A C12A C15A 108.8(2) . . ?
C4A C12A C14C 107.6(6) . . ?
C14A C12A C4A 111.22(15) . . ?
C14A C12A C13A 107.39(19) . . ?
C14A C12A C15A 109.8(2) . . ?
C15A C12A C13A 107.3(2) . . ?
C13C C12A C4A 108.1(7) . . ?
C13C C12A C14C 105.3(14) . . ?
C13C C12A C15C 127.8(18) . . ?
C15C C12A C4A 104.8(10) . . ?
C15C C12A C14C 101.9(17) . . ?
C4A C5A H5A 117.6 . . ?
C6A C5A C4A 124.74(13) . . ?
C6A C5A H5A 117.6 . . ?
C2B C3B H3B 119.4 . . ?
C4B C3B C2B 121.12(14) . . ?
C4B C3B H3B 119.4 . . ?
C6B C8B C9B 110.23(13) . . ?
C6B C8B C10B 111.87(13) . . ?
C11B C8B C6B 109.75(13) . . ?
C11B C8B C9B 109.47(14) . . ?
C11B C8B C10B 107.93(15) . . ?
C10B C8B C9B 107.53(14) . . ?
N1A C7A C2A 122.44(14) . . ?
N1A C7A H7A 118.8 . . ?
C2A C7A H7A 118.8 . . ?
C6B C5B H5B 117.6 . . ?
C6B C5B C4B 124.74(13) . . ?
C4B C5B H5B 117.6 . . ?
C11A C8A C6A 109.87(13) . . ?
C11A C8A C10A 109.55(15) . . ?
C11A C8A C9A 108.07(15) . . ?
C10A C8A C6A 110.36(14) . . ?
C10A C8A C9A 107.46(15) . . ?
C9A C8A C6A 111.46(14) . . ?
C16A C19A C19A 115.59(15) . 2_665 ?
C16A C19A H19C 108.4 . . ?
C16A C19A H19D 108.4 . . ?
C19A C19A H19C 108.4 2_665 . ?
C19A C19A H19D 108.4 2_665 . ?
H19C C19A H19D 107.4 . . ?
C3B C4B C5B 117.07(14) . . ?
C3B C4B C12B 123.27(15) . . ?
C5B C4B C12B 119.65(14) . . ?
C4B C12B C13B 106.7(6) . . ?
C4B C12B C15B 106.8(5) . . ?
C15D C12B C4B 111.1(9) . . ?
C14D C12B C4B 111.0(7) . . ?
C14D C12B C15D 107.6(14) . . ?
C14D C12B C13D 108.7(13) . . ?
C13D C12B C4B 115.4(13) . . ?
C13D C12B C15D 102(2) . . ?
C15B C12B C13B 113.7(8) . . ?
C14B C12B C4B 112.8(5) . . ?
C14B C12B C13B 107.8(7) . . ?
C14B C12B C15B 109.1(9) . . ?
C16B C17B H17A 109.5 . . ?
C16B C17B H17B 109.5 . . ?
C16B C17B H17C 109.5 . . ?
H17A C17B H17B 109.5 . . ?
H17A C17B H17C 109.5 . . ?
H17B C17B H17C 109.5 . . ?
C8B C11B H11A 109.5 . . ?
C8B C11B H11B 109.5 . . ?
C8B C11B H11C 109.5 . . ?
H11A C11B H11B 109.5 . . ?
H11A C11B H11C 109.5 . . ?
H11B C11B H11C 109.5 . . ?
C16B C18B H18A 109.5 . . ?
C16B C18B H18B 109.5 . . ?
C16B C18B H18C 109.5 . . ?
H18A C18B H18B 109.5 . . ?
H18A C18B H18C 109.5 . . ?
H18B C18B H18C 109.5 . . ?
C8B C9B H9BA 109.5 . . ?
C8B C9B H9BB 109.5 . . ?
C8B C9B H9BC 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
C8A C11A H11D 109.5 . . ?
C8A C11A H11E 109.5 . . ?
C8A C11A H11F 109.5 . . ?
H11D C11A H11E 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
C16A C17A H17D 109.5 . . ?
C16A C17A H17E 109.5 . . ?
C16A C17A H17F 109.5 . . ?
H17D C17A H17E 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
C16A C18A H18D 109.5 . . ?
C16A C18A H18E 109.5 . . ?
C16A C18A H18F 109.5 . . ?
H18D C18A H18E 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
C8B C10B H10A 109.5 . . ?
C8B C10B H10B 109.5 . . ?
C8B C10B H10C 109.5 . . ?
H10A C10B H10B 109.5 . . ?
H10A C10B H10C 109.5 . . ?
H10B C10B H10C 109.5 . . ?
C8A C10A H10D 109.5 . . ?
C8A C10A H10E 109.5 . . ?
C8A C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C12B C15D H15A 109.5 . . ?
C12B C15D H15B 109.5 . . ?
C12B C15D H15C 109.5 . . ?
H15A C15D H15B 109.5 . . ?
H15A C15D H15C 109.5 . . ?
H15B C15D H15C 109.5 . . ?
C12B C14D H14A 109.5 . . ?
C12B C14D H14B 109.5 . . ?
C12B C14D H14C 109.5 . . ?
H14A C14D H14B 109.5 . . ?
H14A C14D H14C 109.5 . . ?
H14B C14D H14C 109.5 . . ?
C12B C13D H13A 109.5 . . ?
C12B C13D H13B 109.5 . . ?
C12B C13D H13C 109.5 . . ?
H13A C13D H13B 109.5 . . ?
H13A C13D H13C 109.5 . . ?
H13B C13D H13C 109.5 . . ?
C8A C9A H9AA 109.5 . . ?
C8A C9A H9AB 109.5 . . ?
C8A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C12A C14A H14G 109.5 . . ?
C12A C14A H14H 109.5 . . ?
C12A C14A H14I 109.5 . . ?
H14G C14A H14H 109.5 . . ?
H14G C14A H14I 109.5 . . ?
H14H C14A H14I 109.5 . . ?
C12A C13A H13G 109.5 . . ?
C12A C13A H13H 109.5 . . ?
C12A C13A H13I 109.5 . . ?
H13G C13A H13H 109.5 . . ?
H13G C13A H13I 109.5 . . ?
H13H C13A H13I 109.5 . . ?
C12A C15A H15G 109.5 . . ?
C12A C15A H15H 109.5 . . ?
C12A C15A H15I 109.5 . . ?
H15G C15A H15H 109.5 . . ?
H15G C15A H15I 109.5 . . ?
H15H C15A H15I 109.5 . . ?
C12A C13C H13J 109.5 . . ?
C12A C13C H13K 109.5 . . ?
C12A C13C H13L 109.5 . . ?
H13J C13C H13K 109.5 . . ?
H13J C13C H13L 109.5 . . ?
H13K C13C H13L 109.5 . . ?
C12A C14C H14J 109.5 . . ?
C12A C14C H14K 109.5 . . ?
C12A C14C H14L 109.5 . . ?
H14J C14C H14K 109.5 . . ?
H14J C14C H14L 109.5 . . ?
H14K C14C H14L 109.5 . . ?
C12A C15C H15J 109.5 . . ?
C12A C15C H15K 109.5 . . ?
C12A C15C H15L 109.5 . . ?
H15J C15C H15K 109.5 . . ?
H15J C15C H15L 109.5 . . ?
H15K C15C H15L 109.5 . . ?
C12B C13B H13D 109.5 . . ?
C12B C13B H13E 109.5 . . ?
C12B C13B H13F 109.5 . . ?
H13D C13B H13E 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C12B C15B H15D 109.5 . . ?
C12B C15B H15E 109.5 . . ?
C12B C15B H15F 109.5 . . ?
H15D C15B H15E 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C12B C14B H14D 109.5 . . ?
C12B C14B H14E 109.5 . . ?
C12B C14B H14F 109.5 . . ?
H14D C14B H14E 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1B H1B N1B 0.84 1.77 2.5341(16) 149.7 .
O1A H1A N1A 0.84 1.80 2.5634(18) 149.8 .

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sad_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2014606'
loop_
_audit_author_name
_audit_author_address
'Christian Philouze'
;CNRS
France
;
_audit_update_record             
;
2020-07-07 deposited with the CCDC.	2020-09-03 downloaded from the CCDC.
;
_audit_creation_date             2020-07-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H50 Cu N2 O2, C2.5 H6'
_chemical_formula_sum            'C44.50 H56 Cu N2 O2'
_chemical_formula_weight         714.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+3/4, x+1/4, z+1/4'
'-x+1/2, -y, z+1/2'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'-x+1, -y+1/2, z+1'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'y-3/4, -x-1/4, -z-1/4'
'x-1/2, y, -z-1/2'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'x, y+1/2, -z'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   22.352(3)
_cell_length_b                   22.352(3)
_cell_length_c                   33.005(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     16489(6)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    53484
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.499
_cell_measurement_theta_min      2.468
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.566
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.074012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.2201 before and 0.0731 after correction.
The Ratio of minimum to maximum transmission is 0.0740.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.151
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             6112
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0897
_diffrn_reflns_av_unetI/netI     0.0731
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            53484
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.468
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'APEX II'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'κ-geometry 4 circles diffractometer'
_diffrn_measurement_device_type  'Bruker-AXS-enraf-nonius KappaAPEXII'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_collimation    'Montel optic'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec ISG250'
_diffrn_source_target            Mo
_diffrn_source_type              'Microfocus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5520
_reflns_number_total             9388
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    ?
_refine_diff_density_max         0.627
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     474
_refine_ls_number_reflns         9388
_refine_ls_number_restraints     44
_refine_ls_R_factor_all          0.1204
_refine_ls_R_factor_gt           0.0593
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0732P)²+25.7279P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1720
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C44B-C45B
 1.5 with sigma of 0.02
 C44A-C45A
 1.5 with sigma of 0.02
 C43-C45A
 2.5 with sigma of 0.02
 C43-C45B
 2.5 with sigma of 0.02
 C44B-C43
 1.5 with sigma of 0.02
 C44A-C43
 1.5 with sigma of 0.02
 C44B-C44B_$1
 2.5 with sigma of 0.02
 C43-C45B
 2.5 with sigma of 0.02
3. Rigid bond restraints
 C43, C44B, C45A, C44A, C45B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C45A \\sim C44B \\sim C43 \\sim C44A \\sim C45B: within 1.7A with sigma of 0.04
and sigma for terminal atoms of 0.08
5. Others
 Sof(H43D)=Sof(H43E)=Sof(H43F)=Sof(C44A)=Sof(H44A)=Sof(H44B)=1-FVAR(1)
 Sof(C45A)=Sof(H45A)=Sof(H45B)=0.5*(1-FVAR(2))
 Sof(C45B)=Sof(H45C)=Sof(H45D)=0.5*FVAR(2)
 Sof(H43A)=Sof(H43B)=Sof(H43C)=Sof(C44B)=Sof(H44C)=Sof(H44D)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C45A(H45A,H45B), C44A(H44A,H44B), C45B(H45C,H45D), C44B(H44C,H44D)
6.b Me refined with riding coordinates:
 C43(H43D,H43E,H43F), C43(H43A,H43B,H43C)
6.c Aromatic/amide H refined with riding coordinates:
 C31(H31), C5(H5), C7(H7), C18(H18), C19(H19), C28(H28), C3(H3), C17(H17),
 C27(H27), C20(H20), C24(H24), C33(H33), C26(H26), C25(H25)
6.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C38(H38A,H38B,
 H38C), C37(H37A,H37B,H37C), C36(H36A,H36B,H36C), C14(H14A,H14B,H14C), C40(H40A,
 H40B,H40C), C11(H11A,H11B,H11C), C9(H9A,H9B,H9C), C41(H41A,H41B,H41C),
 C42(H42A,H42B,H42C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.75869(2) 0.37456(2) 0.58405(2) 0.03070(13) Uani 1 1 d . . . . .
O1 O 0.71696(10) 0.30208(10) 0.57670(7) 0.0363(5) Uani 1 1 d . . . . .
O2 O 0.68869(10) 0.40981(11) 0.60589(7) 0.0392(6) Uani 1 1 d . . . . .
N1 N 0.81370(11) 0.35800(12) 0.53921(8) 0.0298(6) Uani 1 1 d . . . . .
N2 N 0.81012(12) 0.42705(12) 0.61592(8) 0.0320(6) Uani 1 1 d . . . . .
C1 C 0.72722(14) 0.25819(14) 0.55186(9) 0.0299(7) Uani 1 1 d . . . . .
C30 C 0.73143(14) 0.49143(15) 0.64232(9) 0.0310(7) Uani 1 1 d . . . . .
C31 C 0.72199(15) 0.54399(15) 0.66548(10) 0.0339(7) Uani 1 1 d . . . . .
H31 H 0.7558 0.5643 0.6762 0.041 Uiso 1 1 calc R . . . .
C39 C 0.65356(17) 0.62247(16) 0.69783(11) 0.0422(8) Uani 1 1 d . . . . .
C4 C 0.74522(16) 0.16152(15) 0.49606(10) 0.0345(7) Uani 1 1 d . . . . .
C29 C 0.68205(15) 0.45932(15) 0.62631(9) 0.0324(7) Uani 1 1 d . . . . .
C16 C 0.85046(14) 0.40534(15) 0.52364(10) 0.0313(7) Uani 1 1 d . . . . .
C21 C 0.89423(14) 0.43218(15) 0.54770(10) 0.0329(7) Uani 1 1 d . . . . .
C2 C 0.77265(14) 0.25976(14) 0.52220(9) 0.0298(7) Uani 1 1 d . . . . .
C12 C 0.74942(17) 0.11051(15) 0.46537(11) 0.0397(8) Uani 1 1 d . . . . .
C5 C 0.70076(15) 0.16040(15) 0.52620(10) 0.0348(7) Uani 1 1 d . . . . .
H5 H 0.6760 0.1259 0.5277 0.042 Uiso 1 1 calc R . . . .
C7 C 0.81024(14) 0.31004(15) 0.51713(9) 0.0309(7) Uani 1 1 d . . . . .
H7 H 0.8365 0.3086 0.4945 0.037 Uiso 1 1 calc R . . . .
C18 C 0.87612(16) 0.46926(17) 0.46761(11) 0.0404(8) Uani 1 1 d . . . . .
H18 H 0.8705 0.4813 0.4403 0.049 Uiso 1 1 calc R . . . .
C19 C 0.91876(16) 0.49709(17) 0.49138(12) 0.0438(9) Uani 1 1 d . . . . .
H19 H 0.9424 0.5286 0.4805 0.053 Uiso 1 1 calc R . . . .
C34 C 0.62327(15) 0.48206(15) 0.63406(9) 0.0316(7) Uani 1 1 d . . . . .
C28 C 0.79122(14) 0.47106(15) 0.63818(9) 0.0314(7) Uani 1 1 d . . . . .
H28 H 0.8207 0.4919 0.6534 0.038 Uiso 1 1 calc R . . . .
C3 C 0.78070(15) 0.21153(15) 0.49499(10) 0.0332(7) Uani 1 1 d . . . . .
H3 H 0.8117 0.2139 0.4753 0.040 Uiso 1 1 calc R . . . .
C35 C 0.56820(15) 0.44873(17) 0.61869(10) 0.0383(8) Uani 1 1 d . . . . .
C17 C 0.84173(15) 0.42397(16) 0.48377(10) 0.0356(7) Uani 1 1 d . . . . .
H17 H 0.8119 0.4053 0.4676 0.043 Uiso 1 1 calc R . . . .
C6 C 0.69033(15) 0.20542(14) 0.55372(10) 0.0326(7) Uani 1 1 d . . . . .
C23 C 0.87119(14) 0.40956(15) 0.62154(10) 0.0315(7) Uani 1 1 d . . . . .
C22 C 0.91064(14) 0.41020(15) 0.58887(10) 0.0327(7) Uani 1 1 d . . . . .
C15 C 0.7492(3) 0.04994(18) 0.48669(14) 0.0682(14) Uani 1 1 d . . . . .
H15A H 0.7820 0.0484 0.5063 0.102 Uiso 1 1 calc GR . . . .
H15B H 0.7543 0.0180 0.4666 0.102 Uiso 1 1 calc GR . . . .
H15C H 0.7110 0.0445 0.5008 0.102 Uiso 1 1 calc GR . . . .
C27 C 0.96977(16) 0.39224(17) 0.59593(11) 0.0416(8) Uani 1 1 d . . . . .
H27 H 0.9977 0.3929 0.5743 0.050 Uiso 1 1 calc R . . . .
C20 C 0.92691(15) 0.47897(16) 0.53095(11) 0.0380(8) Uani 1 1 d . . . . .
H20 H 0.9557 0.4990 0.5472 0.046 Uiso 1 1 calc R . . . .
C32 C 0.66673(16) 0.56642(15) 0.67289(10) 0.0353(7) Uani 1 1 d . . . . .
C10 C 0.6079(2) 0.14072(19) 0.58383(14) 0.0601(12) Uani 1 1 d . . . . .
H10A H 0.5892 0.1360 0.5572 0.090 Uiso 1 1 calc GR . . . .
H10B H 0.5770 0.1394 0.6049 0.090 Uiso 1 1 calc GR . . . .
H10C H 0.6366 0.1082 0.5882 0.090 Uiso 1 1 calc GR . . . .
C24 C 0.89032(16) 0.39172(16) 0.65955(10) 0.0379(8) Uani 1 1 d . . . . .
H24 H 0.8630 0.3917 0.6816 0.045 Uiso 1 1 calc R . . . .
C13 C 0.6948(2) 0.1141(2) 0.43748(14) 0.0701(14) Uani 1 1 d . . . . .
H13A H 0.6582 0.1098 0.4536 0.105 Uiso 1 1 calc GR . . . .
H13B H 0.6968 0.0820 0.4174 0.105 Uiso 1 1 calc GR . . . .
H13C H 0.6945 0.1529 0.4236 0.105 Uiso 1 1 calc GR . . . .
C33 C 0.61790(16) 0.53373(15) 0.65653(10) 0.0347(7) Uani 1 1 d . . . . .
H33 H 0.5787 0.5486 0.6614 0.042 Uiso 1 1 calc R . . . .
C26 C 0.98820(16) 0.37360(18) 0.63377(12) 0.0455(9) Uani 1 1 d . . . . .
H26 H 1.0282 0.3606 0.6378 0.055 Uiso 1 1 calc R . . . .
C38 C 0.51068(17) 0.4823(2) 0.62883(13) 0.0530(10) Uani 1 1 d . . . . .
H38A H 0.5075 0.4871 0.6583 0.079 Uiso 1 1 calc GR . . . .
H38B H 0.4762 0.4595 0.6188 0.079 Uiso 1 1 calc GR . . . .
H38C H 0.5114 0.5217 0.6159 0.079 Uiso 1 1 calc GR . . . .
C37 C 0.56473(17) 0.38677(18) 0.63898(13) 0.0485(10) Uani 1 1 d . . . . .
H37A H 0.6022 0.3651 0.6343 0.073 Uiso 1 1 calc GR . . . .
H37B H 0.5314 0.3641 0.6274 0.073 Uiso 1 1 calc GR . . . .
H37C H 0.5584 0.3917 0.6682 0.073 Uiso 1 1 calc GR . . . .
C36 C 0.57091(18) 0.4417(2) 0.57251(12) 0.0544(11) Uani 1 1 d . . . . .
H36A H 0.5757 0.4811 0.5599 0.082 Uiso 1 1 calc GR . . . .
H36B H 0.5338 0.4232 0.5628 0.082 Uiso 1 1 calc GR . . . .
H36C H 0.6050 0.4162 0.5653 0.082 Uiso 1 1 calc GR . . . .
C8 C 0.64044(16) 0.20079(16) 0.58572(12) 0.0423(8) Uani 1 1 d . . . . .
C14 C 0.8052(2) 0.11378(19) 0.43963(14) 0.0614(12) Uani 1 1 d . . . . .
H14A H 0.8063 0.1522 0.4253 0.092 Uiso 1 1 calc GR . . . .
H14B H 0.8050 0.0810 0.4199 0.092 Uiso 1 1 calc GR . . . .
H14C H 0.8406 0.1103 0.4570 0.092 Uiso 1 1 calc GR . . . .
C40 C 0.6194(2) 0.66726(19) 0.67106(15) 0.0655(13) Uani 1 1 d . . . . .
H40A H 0.6428 0.6757 0.6466 0.098 Uiso 1 1 calc GR . . . .
H40B H 0.6129 0.7045 0.6862 0.098 Uiso 1 1 calc GR . . . .
H40C H 0.5807 0.6501 0.6633 0.098 Uiso 1 1 calc GR . . . .
C11 C 0.6675(2) 0.2069(2) 0.62821(12) 0.0608(12) Uani 1 1 d . . . . .
H11A H 0.7002 0.1781 0.6314 0.091 Uiso 1 1 calc GR . . . .
H11B H 0.6366 0.1990 0.6486 0.091 Uiso 1 1 calc GR . . . .
H11C H 0.6830 0.2476 0.6318 0.091 Uiso 1 1 calc GR . . . .
C25 C 0.94854(16) 0.37395(17) 0.66560(11) 0.0414(8) Uani 1 1 d . . . . .
H25 H 0.9614 0.3619 0.6918 0.050 Uiso 1 1 calc R . . . .
C9 C 0.59376(18) 0.25020(19) 0.57788(16) 0.0599(12) Uani 1 1 d . . . . .
H9A H 0.6132 0.2894 0.5793 0.090 Uiso 1 1 calc GR . . . .
H9B H 0.5622 0.2479 0.5984 0.090 Uiso 1 1 calc GR . . . .
H9C H 0.5762 0.2447 0.5509 0.090 Uiso 1 1 calc GR . . . .
C41 C 0.6148(2) 0.6060(2) 0.73429(13) 0.0606(12) Uani 1 1 d . . . . .
H41A H 0.5766 0.5896 0.7248 0.091 Uiso 1 1 calc GR . . . .
H41B H 0.6074 0.6418 0.7507 0.091 Uiso 1 1 calc GR . . . .
H41C H 0.6356 0.5760 0.7508 0.091 Uiso 1 1 calc GR . . . .
C42 C 0.7106(2) 0.65218(18) 0.71246(13) 0.0538(10) Uani 1 1 d . . . . .
H42A H 0.7317 0.6252 0.7310 0.081 Uiso 1 1 calc GR . . . .
H42B H 0.7006 0.6894 0.7267 0.081 Uiso 1 1 calc GR . . . .
H42C H 0.7363 0.6612 0.6892 0.081 Uiso 1 1 calc GR . . . .
C43 C 0.5949(4) 0.2336(5) 0.7349(3) 0.166(4) Uani 1 1 d D U . . .
H43D H 0.6153 0.2003 0.7485 0.249 Uiso 0.701(12) 1 calc R . . A 2
H43E H 0.6208 0.2496 0.7135 0.249 Uiso 0.701(12) 1 calc R . . A 2
H43F H 0.5863 0.2651 0.7547 0.249 Uiso 0.701(12) 1 calc R . . A 2
H43A H 0.6259 0.2503 0.7172 0.249 Uiso 0.299(12) 1 calc R . . A 1
H43B H 0.6126 0.2237 0.7613 0.249 Uiso 0.299(12) 1 calc R . . A 1
H43C H 0.5784 0.1973 0.7226 0.249 Uiso 0.299(12) 1 calc R . . A 1
C45A C 0.5000 0.2500 0.6956(6) 0.155(7) Uani 0.701(12) 2 d DS TU P A 2
H45A H 0.4752 0.2245 0.6777 0.186 Uiso 0.350(6) 1 calc R . . A 2
H45B H 0.5248 0.2755 0.6777 0.186 Uiso 0.350(6) 1 calc R . . A 2
C44A C 0.5388(4) 0.2122(5) 0.7171(3) 0.122(4) Uani 0.701(12) 1 d D U . A 2
H44A H 0.5494 0.1789 0.6986 0.146 Uiso 0.701(12) 1 calc R . . A 2
H44B H 0.5152 0.1944 0.7394 0.146 Uiso 0.701(12) 1 calc R . . A 2
C45B C 0.5000 0.2500 0.7684(9) 0.229(17) Uani 0.299(12) 2 d DS TU P A 1
H45C H 0.5181 0.2189 0.7859 0.275 Uiso 0.150(6) 1 calc R . . A 1
H45D H 0.4819 0.2811 0.7859 0.275 Uiso 0.150(6) 1 calc R . . A 1
C44B C 0.5474(6) 0.2775(9) 0.7405(11) 0.213(12) Uani 0.299(12) 1 d D U . A 1
H44C H 0.5294 0.2880 0.7140 0.256 Uiso 0.299(12) 1 calc R . . A 1
H44D H 0.5637 0.3145 0.7528 0.256 Uiso 0.299(12) 1 calc R . . A 1


_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 O1 1.885(2) . ?
Cu1 O2 1.894(2) . ?
Cu1 N1 1.959(3) . ?
Cu1 N2 1.951(3) . ?
O1 C1 1.299(4) . ?
O2 C29 1.304(4) . ?
N1 C16 1.435(4) . ?
N1 C7 1.299(4) . ?
N2 C28 1.298(4) . ?
N2 C23 1.432(4) . ?
C1 C2 1.411(4) . ?
C1 C6 1.441(4) . ?
C30 C31 1.418(5) . ?
C30 C29 1.419(4) . ?
C30 C28 1.418(4) . ?
C31 H31 0.9500 . ?
C31 C32 1.355(5) . ?
C39 C32 1.528(5) . ?
C39 C40 1.538(6) . ?
C39 C41 1.528(5) . ?
C39 C42 1.516(5) . ?
C4 C12 1.528(5) . ?
C4 C5 1.407(5) . ?
C4 C3 1.371(5) . ?
C29 C34 1.432(5) . ?
C16 C21 1.396(4) . ?
C16 C17 1.394(5) . ?
C21 C22 1.491(5) . ?
C21 C20 1.390(5) . ?
C2 C7 1.413(4) . ?
C2 C3 1.415(4) . ?
C12 C15 1.526(5) . ?
C12 C13 1.531(6) . ?
C12 C14 1.511(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.376(5) . ?
C7 H7 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.382(5) . ?
C18 C17 1.378(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.380(5) . ?
C34 C35 1.526(5) . ?
C34 C33 1.378(5) . ?
C28 H28 0.9500 . ?
C3 H3 0.9500 . ?
C35 C38 1.525(5) . ?
C35 C37 1.540(5) . ?
C35 C36 1.534(5) . ?
C17 H17 0.9500 . ?
C6 C8 1.539(5) . ?
C23 C22 1.393(4) . ?
C23 C24 1.384(5) . ?
C22 C27 1.401(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C27 H27 0.9500 . ?
C27 C26 1.379(5) . ?
C20 H20 0.9500 . ?
C32 C33 1.420(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 C8 1.528(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.375(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C33 H33 0.9500 . ?
C26 H26 0.9500 . ?
C26 C25 1.375(5) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C8 C11 1.534(6) . ?
C8 C9 1.541(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C25 H25 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43D 0.9800 . ?
C43 H43E 0.9800 . ?
C43 H43F 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C43 C44A 1.467(11) . ?
C43 C44B 1.459(19) . ?
C45A H45A 0.9900 . ?
C45A H45B 0.9900 . ?
C45A C44A 1.404(11) 7_554 ?
C45A C44A 1.404(11) . ?
C44A H44A 0.9900 . ?
C44A H44B 0.9900 . ?
C45B H45C 0.9900 . ?
C45B H45D 0.9900 . ?
C45B C44B 1.532(18) 7_554 ?
C45B C44B 1.532(18) . ?
C44B H44C 0.9900 . ?
C44B H44D 0.9900 . ?

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
O1 Cu1 O2 89.87(10) . . ?
O1 Cu1 N1 92.92(10) . . ?
O1 Cu1 N2 151.38(11) . . ?
O2 Cu1 N1 152.17(11) . . ?
O2 Cu1 N2 91.80(11) . . ?
N2 Cu1 N1 98.70(11) . . ?
C1 O1 Cu1 130.0(2) . . ?
C29 O2 Cu1 130.1(2) . . ?
C16 N1 Cu1 119.4(2) . . ?
C7 N1 Cu1 122.9(2) . . ?
C7 N1 C16 116.2(3) . . ?
C28 N2 Cu1 124.7(2) . . ?
C28 N2 C23 116.3(3) . . ?
C23 N2 Cu1 117.9(2) . . ?
O1 C1 C2 123.1(3) . . ?
O1 C1 C6 119.4(3) . . ?
C2 C1 C6 117.5(3) . . ?
C31 C30 C29 120.3(3) . . ?
C31 C30 C28 117.3(3) . . ?
C28 C30 C29 122.3(3) . . ?
C30 C31 H31 118.7 . . ?
C32 C31 C30 122.7(3) . . ?
C32 C31 H31 118.7 . . ?
C32 C39 C40 108.7(3) . . ?
C41 C39 C32 109.6(3) . . ?
C41 C39 C40 109.2(4) . . ?
C42 C39 C32 111.6(3) . . ?
C42 C39 C40 108.4(3) . . ?
C42 C39 C41 109.4(3) . . ?
C5 C4 C12 119.9(3) . . ?
C3 C4 C12 123.8(3) . . ?
C3 C4 C5 116.2(3) . . ?
O2 C29 C30 122.2(3) . . ?
O2 C29 C34 119.9(3) . . ?
C30 C29 C34 117.9(3) . . ?
C21 C16 N1 121.0(3) . . ?
C17 C16 N1 118.6(3) . . ?
C17 C16 C21 120.5(3) . . ?
C16 C21 C22 123.3(3) . . ?
C20 C21 C16 117.7(3) . . ?
C20 C21 C22 118.7(3) . . ?
C1 C2 C7 122.0(3) . . ?
C1 C2 C3 120.9(3) . . ?
C7 C2 C3 117.1(3) . . ?
C4 C12 C13 108.1(3) . . ?
C15 C12 C4 110.9(3) . . ?
C15 C12 C13 108.7(4) . . ?
C14 C12 C4 112.8(3) . . ?
C14 C12 C15 107.8(4) . . ?
C14 C12 C13 108.5(4) . . ?
C4 C5 H5 117.5 . . ?
C6 C5 C4 125.0(3) . . ?
C6 C5 H5 117.5 . . ?
N1 C7 C2 128.7(3) . . ?
N1 C7 H7 115.6 . . ?
C2 C7 H7 115.6 . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.7(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.7(3) . . ?
C20 C19 H19 120.1 . . ?
C29 C34 C35 120.5(3) . . ?
C33 C34 C29 118.3(3) . . ?
C33 C34 C35 121.2(3) . . ?
N2 C28 C30 127.2(3) . . ?
N2 C28 H28 116.4 . . ?
C30 C28 H28 116.4 . . ?
C4 C3 C2 122.1(3) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C34 C35 C37 109.6(3) . . ?
C34 C35 C36 110.4(3) . . ?
C38 C35 C34 111.6(3) . . ?
C38 C35 C37 107.7(3) . . ?
C38 C35 C36 107.6(3) . . ?
C36 C35 C37 110.0(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C1 C6 C8 119.9(3) . . ?
C5 C6 C1 118.3(3) . . ?
C5 C6 C8 121.8(3) . . ?
C22 C23 N2 120.0(3) . . ?
C24 C23 N2 119.4(3) . . ?
C24 C23 C22 120.6(3) . . ?
C23 C22 C21 123.6(3) . . ?
C23 C22 C27 117.7(3) . . ?
C27 C22 C21 118.6(3) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C22 C27 H27 119.4 . . ?
C26 C27 C22 121.3(3) . . ?
C26 C27 H27 119.4 . . ?
C21 C20 H20 119.1 . . ?
C19 C20 C21 121.9(3) . . ?
C19 C20 H20 119.1 . . ?
C31 C32 C39 125.2(3) . . ?
C31 C32 C33 116.2(3) . . ?
C33 C32 C39 118.6(3) . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.5(3) . . ?
C25 C24 H24 119.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C34 C33 C32 124.7(3) . . ?
C34 C33 H33 117.7 . . ?
C32 C33 H33 117.7 . . ?
C27 C26 H26 120.1 . . ?
C25 C26 C27 119.9(3) . . ?
C25 C26 H26 120.1 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C6 C8 C9 109.1(3) . . ?
C10 C8 C6 112.1(3) . . ?
C10 C8 C11 107.7(3) . . ?
C10 C8 C9 107.5(3) . . ?
C11 C8 C6 109.6(3) . . ?
C11 C8 C9 110.9(3) . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.1(3) . . ?
C26 C25 H25 120.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C39 C42 H42A 109.5 . . ?
C39 C42 H42B 109.5 . . ?
C39 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
H43D C43 H43E 109.5 . . ?
H43D C43 H43F 109.5 . . ?
H43E C43 H43F 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C44A C43 H43D 109.5 . . ?
C44A C43 H43E 109.5 . . ?
C44A C43 H43F 109.5 . . ?
C44B C43 H43A 109.5 . . ?
C44B C43 H43B 109.5 . . ?
C44B C43 H43C 109.5 . . ?
H45A C45A H45B 107.0 . . ?
C44A C45A H45A 107.5 7_554 . ?
C44A C45A H45A 107.5 . . ?
C44A C45A H45B 107.5 7_554 . ?
C44A C45A H45B 107.5 . . ?
C44A C45A C44A 119.3(16) . 7_554 ?
C43 C44A H44A 106.7 . . ?
C43 C44A H44B 106.7 . . ?
C45A C44A C43 122.3(10) . . ?
C45A C44A H44A 106.7 . . ?
C45A C44A H44B 106.7 . . ?
H44A C44A H44B 106.6 . . ?
H45C C45B H45D 108.7 . . ?
C44B C45B H45C 110.5 7_554 . ?
C44B C45B H45C 110.5 . . ?
C44B C45B H45D 110.5 7_554 . ?
C44B C45B H45D 110.5 . . ?
C44B C45B C44B 106(2) 7_554 . ?
C43 C44B C45B 108.0(15) . . ?
C43 C44B H44C 110.1 . . ?
C43 C44B H44D 110.1 . . ?
C45B C44B H44C 110.1 . . ?
C45B C44B H44D 110.1 . . ?
H44C C44B H44D 108.4 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.250 0.125 440.9 22.1 ?
2 0.000 0.750 -0.125 440.9 22.1 ?
3 0.500 0.250 0.375 440.9 22.1 ?
4 0.500 0.750 0.625 440.9 22.1 ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sad_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2014608'
loop_
_audit_author_name
_audit_author_address
'Christian Philouze'
;CNRS
France
;
_audit_update_record             
;
2020-07-07 deposited with the CCDC.	2020-09-03 downloaded from the CCDC.
;
_audit_creation_date             2020-07-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H38 Cu N2 O4, Sb F6, 0.36(C H2 Cl2)'
_chemical_formula_sum            'C36.36 H38.71 Cl0.71 Cu F6 N2 O4 Sb'
_chemical_formula_weight         892.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
Cl Cl 0.3639 0.7018 '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'
F F 0.0727 0.0534 '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'
Sb Sb -0.0562 5.8946 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c e'
_space_group_name_Hall           '-C 2bc 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'x+1/2, -y, z-1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   22.840(5)
_cell_length_b                   25.399(5)
_cell_length_c                   16.261(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     9433(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    41090
_cell_measurement_temperature    200
_cell_measurement_theta_max      67.994
_cell_measurement_theta_min      3.763
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.959
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.320915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.1547 before and 0.0523 after correction.
The Ratio of minimum to maximum transmission is 0.3209.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             3592
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            41090
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.994
_diffrn_reflns_theta_min         3.763
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            KappaCCD
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       '4 circles diffractometer'
_diffrn_measurement_device_type  'Bruker-AXS-enraf-nonius KappaCCD'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_collimation    ?
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_source_target            Cu
_diffrn_source_type              'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3638
_reflns_number_total             4385
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'ShelXT-2016 (Sheldrick, 2008)'
_refine_diff_density_max         0.840
_refine_diff_density_min         -1.413
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4385
_refine_ls_number_restraints     86
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0571
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1280P)²+10.6247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1801
_refine_ls_wR_factor_ref         0.1934
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F3-F4
 2.6 with sigma of 0.02
 F1-F4
 2.6 with sigma of 0.02
 Sb3-F4
 1.8 with sigma of 0.02
 F2-F4
 3.8 with sigma of 0.02
 F00N-F00Q
 2.6 with sigma of 0.02
 F00N-F00P
 2.6 with sigma of 0.02
 F00R-F00P
 2.6 with sigma of 0.02
 F00N-F00R
 2.6 with sigma of 0.02
 F00P-F00Q
 2.6 with sigma of 0.02
 F3-F4
 2.6 with sigma of 0.02
 F3-F1
 2.6 with sigma of 0.02
 F3-F2
 2.6 with sigma of 0.02
 F1-F4
 2.6 with sigma of 0.02
 F1-F2
 2.6 with sigma of 0.02
 Sb3-F4
 1.8 with sigma of 0.02
 F3-Sb3
 1.8 with sigma of 0.02
 F1-Sb3
 1.8 with sigma of 0.02
 F2-Sb3
 1.8 with sigma of 0.02
 F7-Sb2
 1.8 with sigma of 0.02
 F6-Sb2
 1.8 with sigma of 0.02
 Sb2-F5
 1.8 with sigma of 0.02
 Sb2-F8
 1.8 with sigma of 0.02
 Sb2-F9
 1.8 with sigma of 0.02
 F7-F5
 2.6 with sigma of 0.02
 F7-F6
 2.6 with sigma of 0.02
 F7-F8
 2.6 with sigma of 0.02
 F7-F9
 2.6 with sigma of 0.02
 F8-F5
 2.6 with sigma of 0.02
 F8-F6
 2.6 with sigma of 0.02
 F9-F5
 2.6 with sigma of 0.02
 F9-F6
 2.6 with sigma of 0.02
3. Rigid bond restraints
 Sb3, F1, F3, F4, F2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F7, F6, Sb2, F5, F9, F8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F6, Sb2, F5, F7, F8, F9
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Sb3 \\sim F1 \\sim F3 \\sim F4 \\sim F2: within 1.7A with sigma of 0.04 and
sigma for terminal atoms of 0.08
F6 \\sim Sb2 \\sim F5 \\sim F7 \\sim F8 \\sim F9: within 1.7A with sigma of
0.004 and sigma for terminal atoms of 0.008
Uanis(F9) \\sim Ueq, Uanis(F7) \\sim Ueq, Uanis(F6) \\sim Ueq: with sigma of
0.05 and sigma for terminal atoms of 0.1
Uanis(F5) \\sim Ueq, Uanis(F8) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.02
5. Others
 Sof(C5)=Sof(H5A)=Sof(H5B)=0.5*FVAR(2)
 Sof(Cl1)=FVAR(1)
 Fixed Sof: Sb1(0.35) F00N(0.7) F00P(0.7) F00Q(0.35) F00R(0.35) Sb3(0.125)
 F3(0.25) F2(0.125) F1(0.25) F4(0.125) Sb2(0.025) F5(0.025) F6(0.025) F7(0.05)
 F8(0.025) F9(0.025)
6.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
6.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C00B(H00B), C00D(H00D), C00F(H00F), C00G(H00G), C00I(H00I),
 C00J(H00J)
6.c Idealised Me refined as rotating group:
 C00K(H00A,H00C,H00E), C00L(H00H,H00K,H00L), C00M(H00M,H00N,H00O), C00O(H00P,
 H00Q,H00R)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu01 Cu 0.7500 0.26965(2) 0.7500 0.0331(2) Uani 1 2 d S T P . .
Sb1 Sb 0.5000 0.31385(5) 0.56702(6) 0.0857(3) Uani 0.7 2 d S T P A 1
O003 O 0.72314(11) 0.21390(8) 0.67917(13) 0.0397(5) Uani 1 1 d . . . . .
O004 O 0.65633(13) 0.22598(9) 0.35722(15) 0.0495(6) Uani 1 1 d . . . . .
N005 N 0.70220(11) 0.32161(9) 0.69071(15) 0.0329(5) Uani 1 1 d . . . . .
C006 C 0.68162(14) 0.31383(11) 0.61770(18) 0.0341(6) Uani 1 1 d . . . . .
H006 H 0.6604 0.3413 0.5943 0.041 Uiso 1 1 calc R . . . .
C007 C 0.68828(14) 0.26686(11) 0.56891(18) 0.0341(6) Uani 1 1 d . . . . .
C008 C 0.68026(15) 0.36767(11) 0.73327(18) 0.0352(6) Uani 1 1 d . . . . .
C009 C 0.71823(15) 0.40727(11) 0.75901(18) 0.0367(7) Uani 1 1 d . . . . .
C00A C 0.70582(14) 0.21761(11) 0.60405(18) 0.0357(6) Uani 1 1 d . . . . .
C00B C 0.68421(15) 0.17660(12) 0.47260(19) 0.0404(7) Uani 1 1 d . . . . .
H00B H 0.6822 0.1469 0.4394 0.048 Uiso 1 1 calc R . . . .
C00C C 0.70004(16) 0.17075(12) 0.55324(19) 0.0397(7) Uani 1 1 d . . . . .
C00D C 0.67081(15) 0.27065(11) 0.48683(19) 0.0376(7) Uani 1 1 d . . . . .
H00D H 0.6592 0.3029 0.4652 0.045 Uiso 1 1 calc R . . . .
C00E C 0.67085(16) 0.22608(12) 0.43802(19) 0.0399(7) Uani 1 1 d . . . . .
C00F C 0.69404(16) 0.45045(12) 0.8004(2) 0.0458(8) Uani 1 1 d . . . . .
H00F H 0.7185 0.4774 0.8182 0.055 Uiso 1 1 calc R . . . .
C00G C 0.62070(16) 0.37108(13) 0.7477(2) 0.0446(7) Uani 1 1 d . . . . .
H00G H 0.5960 0.3443 0.7299 0.053 Uiso 1 1 calc R . . . .
C00H C 0.70848(19) 0.11590(12) 0.5916(2) 0.0498(9) Uani 1 1 d . . . . .
C00I C 0.63462(18) 0.45381(14) 0.8153(3) 0.0557(9) Uani 1 1 d . . . . .
H00I H 0.6194 0.4827 0.8434 0.067 Uiso 1 1 calc R . . . .
C00J C 0.59782(17) 0.41425(14) 0.7885(3) 0.0552(9) Uani 1 1 d . . . . .
H00J H 0.5577 0.4166 0.7978 0.066 Uiso 1 1 calc R . . . .
C00K C 0.61978(19) 0.26843(15) 0.3273(2) 0.0535(9) Uani 1 1 d . . . . .
H00A H 0.6038 0.2591 0.2747 0.080 Uiso 1 1 calc GR . . . .
H00C H 0.6428 0.2998 0.3220 0.080 Uiso 1 1 calc GR . . . .
H00E H 0.5884 0.2745 0.3655 0.080 Uiso 1 1 calc GR . . . .
C00L C 0.6628(2) 0.10838(14) 0.6592(2) 0.0627(11) Uani 1 1 d . . . . .
H00H H 0.6667 0.1359 0.6993 0.094 Uiso 1 1 calc GR . . . .
H00K H 0.6685 0.0748 0.6851 0.094 Uiso 1 1 calc GR . . . .
H00L H 0.6243 0.1097 0.6355 0.094 Uiso 1 1 calc GR . . . .
C00M C 0.7710(2) 0.11004(14) 0.6268(3) 0.0617(11) Uani 1 1 d . . . . .
H00M H 0.7991 0.1145 0.5834 0.092 Uiso 1 1 calc GR . . . .
H00N H 0.7754 0.0757 0.6506 0.092 Uiso 1 1 calc GR . . . .
H00O H 0.7774 0.1363 0.6683 0.092 Uiso 1 1 calc GR . . . .
F00N F 0.5577(2) 0.2755(2) 0.6201(4) 0.0991(15) Uani 0.7 1 d D . . A 1
C00O C 0.6997(3) 0.07212(13) 0.5274(2) 0.0668(13) Uani 1 1 d . . . . .
H00P H 0.6614 0.0752 0.5036 0.100 Uiso 1 1 calc GR . . . .
H00Q H 0.7036 0.0384 0.5535 0.100 Uiso 1 1 calc GR . . . .
H00R H 0.7288 0.0755 0.4851 0.100 Uiso 1 1 calc GR . . . .
F00P F 0.5591(3) 0.3525(3) 0.5179(4) 0.125(2) Uani 0.7 1 d D . . A 1
F00Q F 0.5000 0.2671(6) 0.4810(6) 0.137(4) Uani 0.7 2 d DS T P A 1
F00R F 0.5000 0.3609(4) 0.6550(5) 0.121(3) Uani 0.7 2 d DS T P A 1
Sb3 Sb 0.5000 0.27335(19) 0.57772(18) 0.1078(10) Uani 0.25 2 d DS TU P B 2
F3 F 0.5564(7) 0.2280(9) 0.6095(12) 0.172(9) Uani 0.25 1 d D U . B 2
F2 F 0.5000 0.3032(13) 0.6840(11) 0.241(18) Uani 0.25 2 d DS TU P B 2
F1 F 0.5557(8) 0.3214(7) 0.5492(15) 0.161(8) Uani 0.25 1 d D U . B 2
F4 F 0.5000 0.2463(12) 0.4735(10) 0.180(15) Uani 0.25 2 d DS TU P B 2
Cl1 Cl 0.6518(3) 0.4737(2) 0.5787(3) 0.119(3) Uani 0.357(7) 1 d . . . . .
Sb2 Sb 0.5000 0.3676(4) 0.5127(9) 0.095(3) Uani 0.05 2 d DS TU P C 3
F5 F 0.5000 0.3067(16) 0.454(4) 0.094(15) Uani 0.05 2 d DS TU P C 3
F6 F 0.5000 0.4297(16) 0.571(4) 0.16(3) Uani 0.05 2 d DS TU P C 3
F7 F 0.5803(5) 0.3688(10) 0.5126(18) 0.139(17) Uani 0.05 1 d D U . C 3
F8 F 0.5000 0.331(2) 0.609(2) 0.125(15) Uani 0.05 2 d DS TU P C 3
F9 F 0.5000 0.406(2) 0.417(3) 0.14(3) Uani 0.05 2 d DS TU P C 3
C5 C 0.6116(14) 0.5000 0.5000 0.128(11) Uani 0.357(7) 2 d S T P . .
H5A H 0.5865 0.5273 0.5223 0.153 Uiso 0.178(4) 1 calc R . . . .
H5B H 0.5864 0.4727 0.4777 0.153 Uiso 0.178(4) 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu01 O003 1.926(2) . ?
Cu01 O003 1.926(2) 7_646 ?
Cu01 N005 1.965(2) . ?
Cu01 N005 1.965(3) 7_646 ?
Sb1 F00N 1.851(6) . ?
Sb1 F00N 1.851(6) 12_655 ?
Sb1 F00P 1.850(6) 12_655 ?
Sb1 F00P 1.850(6) . ?
Sb1 F00Q 1.834(9) . ?
Sb1 F00R 1.864(7) . ?
O003 C00A 1.287(4) . ?
O004 C00E 1.355(4) . ?
O004 C00K 1.447(4) . ?
N005 C006 1.292(4) . ?
N005 C008 1.448(4) . ?
C006 H006 0.9300 . ?
C006 C007 1.441(4) . ?
C007 C00A 1.433(4) . ?
C007 C00D 1.396(4) . ?
C008 C009 1.392(4) . ?
C008 C00G 1.383(5) . ?
C009 C009 1.481(7) 7_646 ?
C009 C00F 1.400(4) . ?
C00A C00C 1.455(4) . ?
C00B H00B 0.9300 . ?
C00B C00C 1.368(5) . ?
C00B C00E 1.410(5) . ?
C00C C00H 1.539(4) . ?
C00D H00D 0.9300 . ?
C00D C00E 1.382(4) . ?
C00F H00F 0.9300 . ?
C00F C00I 1.381(6) . ?
C00G H00G 0.9300 . ?
C00G C00J 1.384(5) . ?
C00H C00L 1.527(6) . ?
C00H C00M 1.546(6) . ?
C00H C00O 1.538(4) . ?
C00I H00I 0.9300 . ?
C00I C00J 1.381(5) . ?
C00J H00J 0.9300 . ?
C00K H00A 0.9600 . ?
C00K H00C 0.9600 . ?
C00K H00E 0.9600 . ?
C00L H00H 0.9600 . ?
C00L H00K 0.9600 . ?
C00L H00L 0.9600 . ?
C00M H00M 0.9600 . ?
C00M H00N 0.9600 . ?
C00M H00O 0.9600 . ?
C00O H00P 0.9600 . ?
C00O H00Q 0.9600 . ?
C00O H00R 0.9600 . ?
Sb3 F3 1.804(13) . ?
Sb3 F3 1.804(13) 12_655 ?
Sb3 F2 1.887(13) . ?
Sb3 F1 1.822(13) . ?
Sb3 F1 1.822(13) 12_655 ?
Sb3 F4 1.829(11) . ?
Cl1 C5 1.711(18) . ?
Sb2 F5 1.814(17) . ?
Sb2 F6 1.841(17) . ?
Sb2 F7 1.834(13) 12_655 ?
Sb2 F7 1.834(13) . ?
Sb2 F8 1.826(18) . ?
Sb2 F9 1.840(18) . ?
C5 Cl1 1.711(18) 4_566 ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?

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
O003 Cu01 O003 85.33(13) . 7_646 ?
O003 Cu01 N005 91.34(10) 7_646 7_646 ?
O003 Cu01 N005 164.60(11) . 7_646 ?
O003 Cu01 N005 91.34(10) . . ?
O003 Cu01 N005 164.60(11) 7_646 . ?
N005 Cu01 N005 95.64(14) 7_646 . ?
F00N Sb1 F00N 90.7(4) 12_655 . ?
F00N Sb1 F00R 88.8(3) . . ?
F00N Sb1 F00R 88.8(3) 12_655 . ?
F00P Sb1 F00N 177.7(3) 12_655 . ?
F00P Sb1 F00N 87.7(3) 12_655 12_655 ?
F00P Sb1 F00N 177.7(3) . 12_655 ?
F00P Sb1 F00N 87.7(3) . . ?
F00P Sb1 F00P 93.8(5) . 12_655 ?
F00P Sb1 F00R 89.5(3) 12_655 . ?
F00P Sb1 F00R 89.5(3) . . ?
F00Q Sb1 F00N 90.9(4) . . ?
F00Q Sb1 F00N 90.9(4) . 12_655 ?
F00Q Sb1 F00P 90.8(4) . . ?
F00Q Sb1 F00P 90.8(4) . 12_655 ?
F00Q Sb1 F00R 179.6(6) . . ?
C00A O003 Cu01 127.71(18) . . ?
C00E O004 C00K 117.7(3) . . ?
C006 N005 Cu01 123.37(19) . . ?
C006 N005 C008 115.9(3) . . ?
C008 N005 Cu01 120.01(19) . . ?
N005 C006 H006 116.8 . . ?
N005 C006 C007 126.5(3) . . ?
C007 C006 H006 116.8 . . ?
C00A C007 C006 122.2(3) . . ?
C00D C007 C006 116.1(3) . . ?
C00D C007 C00A 121.4(3) . . ?
C009 C008 N005 120.8(3) . . ?
C00G C008 N005 118.1(3) . . ?
C00G C008 C009 121.1(3) . . ?
C008 C009 C009 123.4(2) . 7_646 ?
C008 C009 C00F 117.7(3) . . ?
C00F C009 C009 118.8(2) . 7_646 ?
O003 C00A C007 121.9(3) . . ?
O003 C00A C00C 120.5(3) . . ?
C007 C00A C00C 117.5(3) . . ?
C00C C00B H00B 118.8 . . ?
C00C C00B C00E 122.4(3) . . ?
C00E C00B H00B 118.8 . . ?
C00A C00C C00H 119.9(3) . . ?
C00B C00C C00A 118.6(3) . . ?
C00B C00C C00H 121.4(3) . . ?
C007 C00D H00D 120.3 . . ?
C00E C00D C007 119.5(3) . . ?
C00E C00D H00D 120.3 . . ?
O004 C00E C00B 116.0(3) . . ?
O004 C00E C00D 123.9(3) . . ?
C00D C00E C00B 120.1(3) . . ?
C009 C00F H00F 119.3 . . ?
C00I C00F C009 121.4(3) . . ?
C00I C00F H00F 119.3 . . ?
C008 C00G H00G 119.9 . . ?
C008 C00G C00J 120.1(3) . . ?
C00J C00G H00G 119.9 . . ?
C00C C00H C00M 110.7(3) . . ?
C00L C00H C00C 108.6(3) . . ?
C00L C00H C00M 110.7(3) . . ?
C00L C00H C00O 108.0(3) . . ?
C00O C00H C00C 111.3(3) . . ?
C00O C00H C00M 107.6(3) . . ?
C00F C00I H00I 120.1 . . ?
C00J C00I C00F 119.8(3) . . ?
C00J C00I H00I 120.1 . . ?
C00G C00J H00J 120.1 . . ?
C00I C00J C00G 119.9(4) . . ?
C00I C00J H00J 120.1 . . ?
O004 C00K H00A 109.5 . . ?
O004 C00K H00C 109.5 . . ?
O004 C00K H00E 109.5 . . ?
H00A C00K H00C 109.5 . . ?
H00A C00K H00E 109.5 . . ?
H00C C00K H00E 109.5 . . ?
C00H C00L H00H 109.5 . . ?
C00H C00L H00K 109.5 . . ?
C00H C00L H00L 109.5 . . ?
H00H C00L H00K 109.5 . . ?
H00H C00L H00L 109.5 . . ?
H00K C00L H00L 109.5 . . ?
C00H C00M H00M 109.5 . . ?
C00H C00M H00N 109.5 . . ?
C00H C00M H00O 109.5 . . ?
H00M C00M H00N 109.5 . . ?
H00M C00M H00O 109.5 . . ?
H00N C00M H00O 109.5 . . ?
C00H C00O H00P 109.5 . . ?
C00H C00O H00Q 109.5 . . ?
C00H C00O H00R 109.5 . . ?
H00P C00O H00Q 109.5 . . ?
H00P C00O H00R 109.5 . . ?
H00Q C00O H00R 109.5 . . ?
F3 Sb3 F3 91.3(14) . 12_655 ?
F3 Sb3 F2 89.7(7) . . ?
F3 Sb3 F2 89.7(7) 12_655 . ?
F3 Sb3 F1 90.1(7) . . ?
F3 Sb3 F1 177.3(10) 12_655 . ?
F3 Sb3 F1 90.1(7) 12_655 12_655 ?
F3 Sb3 F1 177.3(10) . 12_655 ?
F3 Sb3 F4 91.4(7) 12_655 . ?
F3 Sb3 F4 91.4(7) . . ?
F1 Sb3 F2 88.0(8) 12_655 . ?
F1 Sb3 F2 88.0(8) . . ?
F1 Sb3 F1 88.5(14) 12_655 . ?
F1 Sb3 F4 90.9(7) . . ?
F1 Sb3 F4 90.9(7) 12_655 . ?
F4 Sb3 F2 178.4(13) . . ?
F5 Sb2 F6 179.6(13) . . ?
F5 Sb2 F7 90.8(8) . 12_655 ?
F5 Sb2 F7 90.8(8) . . ?
F5 Sb2 F8 91.0(10) . . ?
F5 Sb2 F9 90.4(10) . . ?
F7 Sb2 F6 89.2(8) 12_655 . ?
F7 Sb2 F6 89.2(8) . . ?
F7 Sb2 F7 178.2(16) . 12_655 ?
F7 Sb2 F9 89.5(8) . . ?
F7 Sb2 F9 89.5(8) 12_655 . ?
F8 Sb2 F6 89.4(10) . . ?
F8 Sb2 F7 90.5(8) . 12_655 ?
F8 Sb2 F7 90.5(8) . . ?
F8 Sb2 F9 178.6(12) . . ?
F9 Sb2 F6 89.2(10) . . ?
Cl1 C5 Cl1 115.0(18) . 4_566 ?
Cl1 C5 H5A 108.5 . . ?
Cl1 C5 H5A 108.5 4_566 . ?
Cl1 C5 H5B 108.5 . . ?
Cl1 C5 H5B 108.5 4_566 . ?
H5A C5 H5B 107.5 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 489.7 85.7 ?
2 0.000 0.500 0.500 489.7 85.7 ?
3 0.500 0.000 0.500 489.7 85.7 ?
4 0.500 0.500 0.000 489.7 85.7 ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sad_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2014604'
loop_
_audit_author_name
_audit_author_address
'Christian Philouze'
;CNRS
France
;
_audit_update_record             
;
2020-07-07 deposited with the CCDC.	2020-09-03 downloaded from the CCDC.
;
_audit_creation_date             2020-07-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H29 Cu0.5 N O'
_chemical_formula_sum            'C19 H29 Cu0.50 N O'
_chemical_formula_weight         319.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.661(4)
_cell_length_b                   16.537(3)
_cell_length_c                   13.206(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.07(3)
_cell_angle_gamma                90
_cell_volume                     3785.2(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    22919
_cell_measurement_temperature    200
_cell_measurement_theta_max      29.998
_cell_measurement_theta_min      2.463
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.608
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.801095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.1484 before and 0.0369 after correction.
The Ratio of minimum to maximum transmission is 0.8011.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1380
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            22919
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_min         2.463
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'APEX II'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'κ-geometry 4 circles diffractometer'
_diffrn_measurement_device_type  'Bruker-AXS-enraf-nonius KappaAPEXII'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_collimation    'Montel optic'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec ISG250'
_diffrn_source_target            Mo
_diffrn_source_type              'Microfocus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4467
_reflns_number_total             5485
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    ?
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         5485
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.155
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0271P)²+3.3252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0922
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C13A-C12
 1.5 with sigma of 0.02
3. Others
 Sof(C14B)=Sof(H14D)=Sof(H14E)=Sof(H14F)=Sof(C15B)=Sof(H15D)=Sof(H15E)=
 Sof(H15F)=Sof(C13B)=Sof(H13D)=Sof(H13E)=Sof(H13F)=1-FVAR(1)
 Sof(C13A)=Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(C14A)=Sof(H14A)=Sof(H14B)=
 Sof(H14C)=Sof(C15A)=Sof(H15A)=Sof(H15B)=Sof(H15C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
4.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C3(H3)
4.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C9(H9A,H9B,H9C), C17(H17A,H17B,H17C), C11(H11A,H11B,
 H11C), C10(H10A,H10B,H10C), C13A(H13A,H13B,H13C), C14A(H14A,H14B,H14C),
 C15A(H15A,H15B,H15C), C14B(H14D,H14E,H14F), C15B(H15D,H15E,H15F), C13B(H13D,
 H13E,H13F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.50266(2) 0.2500 0.02083(7) Uani 1 2 d S T P . .
O1 O 0.42493(6) 0.58246(6) 0.26115(9) 0.0273(2) Uani 1 1 d . . . . .
N1 N 0.46809(7) 0.42791(7) 0.34889(9) 0.0207(2) Uani 1 1 d . . . . .
C1 C 0.36270(8) 0.57332(8) 0.29895(11) 0.0224(3) Uani 1 1 d . . . . .
C16 C 0.51390(8) 0.35291(9) 0.38217(11) 0.0238(3) Uani 1 1 d . . . . .
C2 C 0.35046(8) 0.50474(8) 0.35803(11) 0.0227(3) Uani 1 1 d . . . . .
C8 C 0.31321(9) 0.70943(9) 0.21676(12) 0.0281(3) Uani 1 1 d . . . . .
C7 C 0.40513(8) 0.43971(8) 0.38251(11) 0.0228(3) Uani 1 1 d . . . . .
H7 H 0.3933 0.4004 0.4295 0.027 Uiso 1 1 calc R . . . .
C6 C 0.30389(9) 0.63477(9) 0.28255(11) 0.0247(3) Uani 1 1 d . . . . .
C4 C 0.22685(10) 0.55575(10) 0.38531(14) 0.0330(4) Uani 1 1 d . . . . .
C19 C 0.48695(9) 0.28606(9) 0.30175(11) 0.0251(3) Uani 1 1 d . . . . .
H19A H 0.5028 0.2336 0.3354 0.030 Uiso 1 1 calc R . . . .
H19B H 0.4298 0.2868 0.2869 0.030 Uiso 1 1 calc R . . . .
C5 C 0.23950(9) 0.62349(10) 0.32571(13) 0.0310(3) Uani 1 1 d . . . . .
H5 H 0.2009 0.6643 0.3145 0.037 Uiso 1 1 calc R . . . .
C3 C 0.28309(9) 0.49786(9) 0.40023(13) 0.0282(3) Uani 1 1 d . . . . .
H3 H 0.2767 0.4515 0.4403 0.034 Uiso 1 1 calc R . . . .
C18 C 0.59940(9) 0.37337(11) 0.39270(12) 0.0313(3) Uani 1 1 d . . . . .
H18A H 0.6088 0.3953 0.3273 0.047 Uiso 1 1 calc GR . . . .
H18B H 0.6303 0.3243 0.4101 0.047 Uiso 1 1 calc GR . . . .
H18C H 0.6140 0.4136 0.4474 0.047 Uiso 1 1 calc GR . . . .
C9 C 0.31904(12) 0.68276(13) 0.10731(13) 0.0415(4) Uani 1 1 d . . . . .
H9A H 0.3635 0.6467 0.1104 0.062 Uiso 1 1 calc GR . . . .
H9B H 0.3256 0.7304 0.0657 0.062 Uiso 1 1 calc GR . . . .
H9C H 0.2718 0.6541 0.0758 0.062 Uiso 1 1 calc GR . . . .
C12 C 0.15359(12) 0.54851(12) 0.4309(2) 0.0531(6) Uani 1 1 d D . . . .
C17 C 0.50125(11) 0.32148(12) 0.48699(12) 0.0369(4) Uani 1 1 d . . . . .
H17A H 0.5072 0.3661 0.5367 0.055 Uiso 1 1 calc GR . . . .
H17B H 0.5393 0.2793 0.5118 0.055 Uiso 1 1 calc GR . . . .
H17C H 0.4491 0.2990 0.4794 0.055 Uiso 1 1 calc GR . . . .
C11 C 0.38553(11) 0.75725(10) 0.26446(15) 0.0401(4) Uani 1 1 d . . . . .
H11A H 0.3809 0.7759 0.3334 0.060 Uiso 1 1 calc GR . . . .
H11B H 0.3910 0.8040 0.2208 0.060 Uiso 1 1 calc GR . . . .
H11C H 0.4310 0.7224 0.2697 0.060 Uiso 1 1 calc GR . . . .
C10 C 0.24393(12) 0.76705(12) 0.20643(16) 0.0442(5) Uani 1 1 d . . . . .
H10A H 0.1969 0.7385 0.1736 0.066 Uiso 1 1 calc GR . . . .
H10B H 0.2523 0.8136 0.1640 0.066 Uiso 1 1 calc GR . . . .
H10C H 0.2384 0.7857 0.2750 0.066 Uiso 1 1 calc GR . . . .
C13A C 0.08195(19) 0.5513(3) 0.3331(4) 0.0766(14) Uani 0.703(5) 1 d D . . A 1
H13A H 0.0849 0.6010 0.2936 0.115 Uiso 0.703(5) 1 calc GR . . A 1
H13B H 0.0331 0.5502 0.3580 0.115 Uiso 0.703(5) 1 calc GR . . A 1
H13C H 0.0846 0.5043 0.2887 0.115 Uiso 0.703(5) 1 calc GR . . A 1
C14A C 0.1447(3) 0.6225(2) 0.4925(4) 0.0704(13) Uani 0.703(5) 1 d . . . A 1
H14A H 0.1877 0.6258 0.5516 0.106 Uiso 0.703(5) 1 calc GR . . A 1
H14B H 0.0959 0.6197 0.5173 0.106 Uiso 0.703(5) 1 calc GR . . A 1
H14C H 0.1448 0.6705 0.4491 0.106 Uiso 0.703(5) 1 calc GR . . A 1
C15A C 0.1471(3) 0.4722(3) 0.4848(5) 0.0752(16) Uani 0.703(5) 1 d . . . A 1
H15A H 0.1513 0.4268 0.4384 0.113 Uiso 0.703(5) 1 calc GR . . A 1
H15B H 0.0970 0.4699 0.5063 0.113 Uiso 0.703(5) 1 calc GR . . A 1
H15C H 0.1886 0.4687 0.5457 0.113 Uiso 0.703(5) 1 calc GR . . A 1
C14B C 0.1032(6) 0.6135(5) 0.4221(10) 0.062(3) Uani 0.297(5) 1 d . . . A 2
H14D H 0.1312 0.6621 0.4506 0.092 Uiso 0.297(5) 1 calc GR . . A 2
H14E H 0.0620 0.6019 0.4603 0.092 Uiso 0.297(5) 1 calc GR . . A 2
H14F H 0.0806 0.6225 0.3492 0.092 Uiso 0.297(5) 1 calc GR . . A 2
C15B C 0.1188(5) 0.4671(6) 0.4155(11) 0.061(3) Uani 0.297(5) 1 d . . . A 2
H15D H 0.1029 0.4564 0.3415 0.092 Uiso 0.297(5) 1 calc GR . . A 2
H15E H 0.0737 0.4644 0.4485 0.092 Uiso 0.297(5) 1 calc GR . . A 2
H15F H 0.1568 0.4266 0.4464 0.092 Uiso 0.297(5) 1 calc GR . . A 2
C13B C 0.1886(5) 0.5443(6) 0.5668(6) 0.059(2) Uani 0.297(5) 1 d . . . A 2
H13D H 0.2245 0.4989 0.5829 0.088 Uiso 0.297(5) 1 calc GR . . A 2
H13E H 0.1452 0.5368 0.6022 0.088 Uiso 0.297(5) 1 calc GR . . A 2
H13F H 0.2154 0.5949 0.5899 0.088 Uiso 0.297(5) 1 calc GR . . A 2


_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 O1 1.8963(11) . ?
Cu1 O1 1.8963(11) 2_655 ?
Cu1 N1 1.9579(12) 2_655 ?
Cu1 N1 1.9579(12) . ?
O1 C1 1.3004(17) . ?
N1 C16 1.5000(18) . ?
N1 C7 1.2889(18) . ?
C1 C2 1.416(2) . ?
C1 C6 1.439(2) . ?
C16 C19 1.544(2) . ?
C16 C18 1.528(2) . ?
C16 C17 1.535(2) . ?
C2 C7 1.440(2) . ?
C2 C3 1.4121(19) . ?
C8 C6 1.537(2) . ?
C8 C9 1.533(2) . ?
C8 C11 1.531(3) . ?
C8 C10 1.536(2) . ?
C7 H7 0.9500 . ?
C6 C5 1.379(2) . ?
C4 C5 1.411(2) . ?
C4 C3 1.366(2) . ?
C4 C12 1.533(2) . ?
C19 C19 1.524(3) 2_655 ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C5 H5 0.9500 . ?
C3 H3 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C12 C13A 1.626(5) . ?
C12 C14A 1.494(4) . ?
C12 C15A 1.465(5) . ?
C12 C14B 1.387(8) . ?
C12 C15B 1.477(9) . ?
C12 C13B 1.783(8) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?

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
O1 Cu1 O1 91.80(7) . 2_655 ?
O1 Cu1 N1 95.31(5) . . ?
O1 Cu1 N1 141.83(5) . 2_655 ?
O1 Cu1 N1 141.83(5) 2_655 . ?
O1 Cu1 N1 95.31(5) 2_655 2_655 ?
N1 Cu1 N1 101.70(7) 2_655 . ?
C1 O1 Cu1 127.16(9) . . ?
C16 N1 Cu1 120.63(9) . . ?
C7 N1 Cu1 120.80(10) . . ?
C7 N1 C16 118.47(12) . . ?
O1 C1 C2 122.28(13) . . ?
O1 C1 C6 119.92(13) . . ?
C2 C1 C6 117.78(13) . . ?
N1 C16 C19 108.24(11) . . ?
N1 C16 C18 108.16(12) . . ?
N1 C16 C17 112.37(12) . . ?
C18 C16 C19 112.97(12) . . ?
C18 C16 C17 107.80(13) . . ?
C17 C16 C19 107.40(13) . . ?
C1 C2 C7 123.71(13) . . ?
C3 C2 C1 120.74(13) . . ?
C3 C2 C7 115.52(13) . . ?
C9 C8 C6 109.61(14) . . ?
C9 C8 C10 106.93(14) . . ?
C11 C8 C6 110.72(13) . . ?
C11 C8 C9 109.55(15) . . ?
C11 C8 C10 107.67(15) . . ?
C10 C8 C6 112.25(14) . . ?
N1 C7 C2 128.42(13) . . ?
N1 C7 H7 115.8 . . ?
C2 C7 H7 115.8 . . ?
C1 C6 C8 119.99(13) . . ?
C5 C6 C1 118.09(14) . . ?
C5 C6 C8 121.92(13) . . ?
C5 C4 C12 121.12(15) . . ?
C3 C4 C5 116.62(14) . . ?
C3 C4 C12 122.26(16) . . ?
C16 C19 H19A 107.1 . . ?
C16 C19 H19B 107.1 . . ?
C19 C19 C16 120.71(11) 2_655 . ?
C19 C19 H19A 107.1 2_655 . ?
C19 C19 H19B 107.1 2_655 . ?
H19A C19 H19B 106.8 . . ?
C6 C5 C4 124.69(14) . . ?
C6 C5 H5 117.7 . . ?
C4 C5 H5 117.7 . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 122.07(15) . . ?
C4 C3 H3 119.0 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C12 C13A 105.8(2) . . ?
C4 C12 C13B 104.0(3) . . ?
C14A C12 C4 109.5(2) . . ?
C14A C12 C13A 105.2(3) . . ?
C15A C12 C4 114.1(2) . . ?
C15A C12 C13A 106.8(3) . . ?
C15A C12 C14A 114.5(3) . . ?
C14B C12 C4 118.9(4) . . ?
C14B C12 C15B 116.8(6) . . ?
C14B C12 C13B 102.0(6) . . ?
C15B C12 C4 112.1(4) . . ?
C15B C12 C13B 99.1(7) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C13A H13A 109.5 . . ?
C12 C13A H13B 109.5 . . ?
C12 C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C12 C14A H14A 109.5 . . ?
C12 C14A H14B 109.5 . . ?
C12 C14A H14C 109.5 . . ?
H14A C14A H14B 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C12 C15A H15A 109.5 . . ?
C12 C15A H15B 109.5 . . ?
C12 C15A H15C 109.5 . . ?
H15A C15A H15B 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C12 C14B H14D 109.5 . . ?
C12 C14B H14E 109.5 . . ?
C12 C14B H14F 109.5 . . ?
H14D C14B H14E 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C12 C15B H15D 109.5 . . ?
C12 C15B H15E 109.5 . . ?
C12 C15B H15F 109.5 . . ?
H15D C15B H15E 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C12 C13B H13D 109.5 . . ?
C12 C13B H13E 109.5 . . ?
C12 C13B H13F 109.5 . . ?
H13D C13B H13E 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sad_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 2014607'
loop_
_audit_author_name
_audit_author_address
'Christian Philouze'
;CNRS
France
;
_audit_update_record             
;
2020-07-07 deposited with the CCDC.	2020-09-03 downloaded from the CCDC.
;
_audit_creation_date             2020-07-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'F6 Sb, C32 H46 Cu N2 O4, 0.98(C H2 Cl2)'
_chemical_formula_sum            'C32.98 H47.96 Cl1.96 Cu F6 N2 O4 Sb'
_chemical_formula_weight         905.01
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.027(2)
_cell_length_b                   13.071(3)
_cell_length_c                   14.287(3)
_cell_angle_alpha                108.75(3)
_cell_angle_beta                 92.22(3)
_cell_angle_gamma                91.99(3)
_cell_volume                     1946.1(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    39588
_cell_measurement_temperature    200
_cell_measurement_theta_max      30.000
_cell_measurement_theta_min      2.448
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.440
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.478624
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.2206 before and 0.0721 after correction.
The Ratio of minimum to maximum transmission is 0.4786.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             918
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            39588
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         2.448
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'APEX II'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'κ-geometry 4 circles diffractometer'
_diffrn_measurement_device_type  'Bruker-AXS-enraf-nonius KappaAPEXII'
_diffrn_measurement_method       'Phi and omega scans'
_diffrn_radiation_collimation    'Montel optic'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec ISG250'
_diffrn_source_target            Mo
_diffrn_source_type              'Microfocus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8611
_reflns_number_total             11332
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    ?
_refine_diff_density_max         0.920
_refine_diff_density_min         -1.054
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     492
_refine_ls_number_reflns         11332
_refine_ls_number_restraints     63
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0603
_refine_ls_restrained_S_all      1.152
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0270P)²+4.8368P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1362
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 Sb1, F6B, F3B, F5B, F5A, F3A, F4B, F4A, F1, F2, F6A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
F4A \\sim F4B \\sim F5A \\sim F5B \\sim F3A \\sim F3B \\sim F6A \\sim F1 \\sim
F2 \\sim F6B \\sim Sb1: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
4. Others
 Sof(Cl1)=Sof(Cl2)=Sof(C33)=Sof(H33A)=Sof(H33B)=FVAR(1)
 Sof(F6B)=Sof(F3B)=Sof(F4B)=Sof(F5B)=1-FVAR(2)
 Sof(F3A)=Sof(F4A)=Sof(F5A)=Sof(F6A)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C14(H14A,H14B), C33(H33A,H33B)
5.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C21(H21), C5(H5), C3(H3), C24(H24), C26(H26)
5.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C9(H9A,H9B,H9C), C30(H30A,H30B,H30C), C19(H19A,H19B,
 H19C), C10(H10A,H10B,H10C), C31(H31A,H31B,H31C), C20(H20A,H20B,H20C), C32(H32A,
 H32B,H32C), C11(H11A,H11B,H11C), C18(H18A,H18B,H18C), C12(H12A,H12B,H12C),
 C29(H29A,H29B,H29C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb1 Sb 0.17665(2) 0.84574(2) 0.07427(2) 0.03662(9) Uani 1 1 d . U . . .
Cu2 Cu 0.71531(4) 0.79567(4) 0.23648(3) 0.02667(11) Uani 1 1 d . . . . .
Cl1 Cl 0.1822(2) 0.2939(2) 0.2759(2) 0.1188(11) Uani 0.978(5) 1 d . . P . .
Cl2 Cl -0.06888(19) 0.2328(2) 0.2756(2) 0.1061(9) Uani 0.978(5) 1 d . . P . .
F1 F 0.0847(3) 0.8943(3) -0.0131(3) 0.0720(10) Uani 1 1 d . U . . .
F3A F 0.105(2) 0.7073(15) 0.0119(16) 0.101(4) Uani 0.63(4) 1 d . U P A 1
O1 O 0.8578(3) 0.7689(2) 0.3038(2) 0.0397(7) Uani 1 1 d . . . . .
O2 O 0.6552(3) 0.6574(2) 0.2365(2) 0.0407(7) Uani 1 1 d . . . . .
F2 F 0.2716(3) 0.7972(3) 0.1603(3) 0.0675(9) Uani 1 1 d . U . . .
F4A F 0.2529(14) 0.9805(12) 0.1278(17) 0.093(4) Uani 0.63(4) 1 d . U P A 1
F5A F 0.0598(15) 0.884(2) 0.1627(10) 0.099(5) Uani 0.63(4) 1 d . U P A 1
O4 O 0.2367(3) 0.4289(2) 0.0664(2) 0.0383(7) Uani 1 1 d . . . . .
F6A F 0.3015(14) 0.8077(17) -0.0183(12) 0.099(4) Uani 0.63(4) 1 d . U P A 1
O3 O 1.2631(3) 1.0317(3) 0.4413(3) 0.0470(8) Uani 1 1 d . . . . .
N2 N 0.6235(3) 0.7855(2) 0.1135(2) 0.0241(6) Uani 1 1 d . . . . .
N1 N 0.7309(3) 0.9514(3) 0.3056(2) 0.0281(6) Uani 1 1 d . . . . .
C16 C 0.6539(3) 0.8660(3) 0.0612(3) 0.0263(7) Uani 1 1 d . . . . .
C23 C 0.4926(3) 0.6306(3) 0.1155(3) 0.0262(7) Uani 1 1 d . . . . .
C2 C 0.9445(3) 0.9479(3) 0.3598(3) 0.0281(7) Uani 1 1 d . . . . .
C13 C 0.6248(4) 1.0200(3) 0.3024(3) 0.0347(9) Uani 1 1 d . . . . .
C1 C 0.9512(3) 0.8334(3) 0.3382(3) 0.0301(8) Uani 1 1 d . . . . .
C7 C 0.8324(3) 0.9978(3) 0.3491(3) 0.0296(8) Uani 1 1 d . . . . .
H7 H 0.8335 1.0743 0.3776 0.035 Uiso 1 1 calc R . . . .
C27 C 0.5103(4) 0.5171(3) 0.2241(3) 0.0295(8) Uani 1 1 d . . . . .
C21 C 0.5354(3) 0.7147(3) 0.0778(3) 0.0253(7) Uani 1 1 d . . . . .
H21 H 0.4935 0.7182 0.0197 0.030 Uiso 1 1 calc R . . . .
C28 C 0.5796(5) 0.4832(4) 0.3034(4) 0.0459(11) Uani 1 1 d . . . . .
C22 C 0.5564(3) 0.6041(3) 0.1929(3) 0.0292(8) Uani 1 1 d . . . . .
C17 C 0.6317(5) 1.1257(4) 0.3897(4) 0.0478(12) Uani 1 1 d . . . . .
H17A H 0.6470 1.1099 0.4516 0.072 Uiso 1 1 calc GR . . . .
H17B H 0.5547 1.1614 0.3921 0.072 Uiso 1 1 calc GR . . . .
H17C H 0.6979 1.1735 0.3814 0.072 Uiso 1 1 calc GR . . . .
C6 C 1.0649(4) 0.7903(3) 0.3580(3) 0.0348(9) Uani 1 1 d . . . . .
C9 C 1.0426(5) 0.6051(4) 0.2319(4) 0.0506(12) Uani 1 1 d . . . . .
H9A H 0.9569 0.6132 0.2164 0.076 Uiso 1 1 calc GR . . . .
H9B H 1.0567 0.5285 0.2204 0.076 Uiso 1 1 calc GR . . . .
H9C H 1.0935 0.6322 0.1894 0.076 Uiso 1 1 calc GR . . . .
C15 C 0.5853(4) 0.9688(3) 0.1077(3) 0.0311(8) Uani 1 1 d . . . . .
H15A H 0.5818 1.0081 0.0590 0.037 Uiso 1 1 calc R . . . .
H15B H 0.5006 0.9453 0.1144 0.037 Uiso 1 1 calc R . . . .
C14 C 0.6283(4) 1.0508(3) 0.2069(3) 0.0360(9) Uani 1 1 d . . . . .
H14A H 0.5793 1.1151 0.2167 0.043 Uiso 1 1 calc R . . . .
H14B H 0.7133 1.0737 0.2008 0.043 Uiso 1 1 calc R . . . .
C25 C 0.3398(3) 0.4908(3) 0.1033(3) 0.0297(8) Uani 1 1 d . . . . .
C5 C 1.1634(4) 0.8629(4) 0.3889(3) 0.0380(9) Uani 1 1 d . . . . .
H5 H 1.2404 0.8358 0.3977 0.046 Uiso 1 1 calc R . . . .
C30 C 0.5939(7) 0.5773(5) 0.4001(4) 0.0659(17) Uani 1 1 d . . . . .
H30A H 0.6438 0.6362 0.3903 0.099 Uiso 1 1 calc GR . . . .
H30B H 0.6334 0.5532 0.4514 0.099 Uiso 1 1 calc GR . . . .
H30C H 0.5137 0.6032 0.4207 0.099 Uiso 1 1 calc GR . . . .
C3 C 1.0471(3) 1.0171(3) 0.3948(3) 0.0320(8) Uani 1 1 d . . . . .
H3 H 1.0418 1.0929 0.4092 0.038 Uiso 1 1 calc R . . . .
C24 C 0.3851(3) 0.5724(3) 0.0707(3) 0.0278(7) Uani 1 1 d . . . . .
H24 H 0.3436 0.5890 0.0183 0.033 Uiso 1 1 calc R . . . .
C8 C 1.0752(4) 0.6696(4) 0.3404(3) 0.0418(10) Uani 1 1 d . . . . .
C26 C 0.4022(4) 0.4651(3) 0.1799(3) 0.0341(9) Uani 1 1 d . . . . .
H26 H 0.3683 0.4097 0.2020 0.041 Uiso 1 1 calc R . . . .
C4 C 1.1560(3) 0.9743(4) 0.4081(3) 0.0354(9) Uani 1 1 d . . . . .
C19 C 0.6135(4) 0.8236(3) -0.0486(3) 0.0331(8) Uani 1 1 d . . . . .
H19A H 0.6429 0.7510 -0.0784 0.050 Uiso 1 1 calc GR . . . .
H19B H 0.6470 0.8722 -0.0820 0.050 Uiso 1 1 calc GR . . . .
H19C H 0.5245 0.8205 -0.0557 0.050 Uiso 1 1 calc GR . . . .
C10 C 1.2052(5) 0.6428(5) 0.3646(5) 0.0677(18) Uani 1 1 d . . . . .
H10A H 1.2619 0.6660 0.3234 0.102 Uiso 1 1 calc GR . . . .
H10B H 1.2088 0.5647 0.3513 0.102 Uiso 1 1 calc GR . . . .
H10C H 1.2276 0.6808 0.4346 0.102 Uiso 1 1 calc GR . . . .
C31 C 0.5110(7) 0.3892(5) 0.3257(5) 0.071(2) Uani 1 1 d . . . . .
H31A H 0.4324 0.4131 0.3523 0.106 Uiso 1 1 calc GR . . . .
H31B H 0.5593 0.3672 0.3743 0.106 Uiso 1 1 calc GR . . . .
H31C H 0.4977 0.3278 0.2645 0.106 Uiso 1 1 calc GR . . . .
C20 C 0.7913(3) 0.8838(4) 0.0680(3) 0.0359(9) Uani 1 1 d . . . . .
H20A H 0.8207 0.9067 0.1376 0.054 Uiso 1 1 calc GR . . . .
H20B H 0.8137 0.9400 0.0392 0.054 Uiso 1 1 calc GR . . . .
H20C H 0.8280 0.8162 0.0316 0.054 Uiso 1 1 calc GR . . . .
C32 C 0.1694(4) 0.4463(4) -0.0138(4) 0.0431(10) Uani 1 1 d . . . . .
H32A H 0.2214 0.4361 -0.0699 0.065 Uiso 1 1 calc GR . . . .
H32B H 0.1412 0.5202 0.0070 0.065 Uiso 1 1 calc GR . . . .
H32C H 0.0991 0.3946 -0.0337 0.065 Uiso 1 1 calc GR . . . .
C11 C 0.9900(6) 0.6342(4) 0.4083(4) 0.0561(14) Uani 1 1 d . . . . .
H11A H 1.0125 0.6755 0.4775 0.084 Uiso 1 1 calc GR . . . .
H11B H 0.9972 0.5568 0.3979 0.084 Uiso 1 1 calc GR . . . .
H11C H 0.9059 0.6476 0.3926 0.084 Uiso 1 1 calc GR . . . .
C18 C 0.5092(4) 0.9569(4) 0.3094(4) 0.0443(10) Uani 1 1 d . . . . .
H18A H 0.5058 0.8859 0.2579 0.066 Uiso 1 1 calc GR . . . .
H18B H 0.4385 0.9967 0.3001 0.066 Uiso 1 1 calc GR . . . .
H18C H 0.5086 0.9473 0.3746 0.066 Uiso 1 1 calc GR . . . .
C12 C 1.2656(5) 1.1440(4) 0.4562(5) 0.0613(15) Uani 1 1 d . . . . .
H12A H 1.2425 1.1561 0.3938 0.092 Uiso 1 1 calc GR . . . .
H12B H 1.3478 1.1754 0.4788 0.092 Uiso 1 1 calc GR . . . .
H12C H 1.2084 1.1784 0.5063 0.092 Uiso 1 1 calc GR . . . .
C29 C 0.7018(6) 0.4447(5) 0.2669(5) 0.0656(16) Uani 1 1 d . . . . .
H29A H 0.6904 0.3854 0.2040 0.098 Uiso 1 1 calc GR . . . .
H29B H 0.7445 0.4189 0.3159 0.098 Uiso 1 1 calc GR . . . .
H29C H 0.7500 0.5045 0.2572 0.098 Uiso 1 1 calc GR . . . .
C33 C 0.0594(8) 0.2193(10) 0.2081(6) 0.114(4) Uani 0.978(5) 1 d . . P . .
H33A H 0.0789 0.1421 0.1840 0.137 Uiso 0.978(5) 1 calc R . P . .
H33B H 0.0426 0.2426 0.1496 0.137 Uiso 0.978(5) 1 calc R . P . .
F6B F 0.305(2) 0.859(4) 0.008(3) 0.113(9) Uani 0.37(4) 1 d . U P A 2
F3B F 0.139(4) 0.713(3) 0.002(2) 0.091(7) Uani 0.37(4) 1 d . U P A 2
F4B F 0.208(5) 0.988(2) 0.162(3) 0.120(9) Uani 0.37(4) 1 d . U P A 2
F5B F 0.039(2) 0.831(4) 0.146(2) 0.088(7) Uani 0.37(4) 1 d . U P A 2


_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
Sb1 F1 1.856(3) . ?
Sb1 F3A 1.874(13) . ?
Sb1 F2 1.860(3) . ?
Sb1 F4A 1.838(11) . ?
Sb1 F5A 1.809(13) . ?
Sb1 F6A 1.912(10) . ?
Sb1 F6B 1.77(2) . ?
Sb1 F3B 1.74(3) . ?
Sb1 F4B 1.89(2) . ?
Sb1 F5B 1.899(17) . ?
Cu2 O1 1.911(3) . ?
Cu2 O2 1.904(3) . ?
Cu2 N2 1.957(3) . ?
Cu2 N1 1.954(3) . ?
Cl1 C33 1.710(9) . ?
Cl2 C33 1.726(10) . ?
O1 C1 1.283(5) . ?
O2 C22 1.295(4) . ?
O4 C25 1.356(4) . ?
O4 C32 1.425(5) . ?
O3 C4 1.360(5) . ?
O3 C12 1.414(7) . ?
N2 C16 1.510(4) . ?
N2 C21 1.286(4) . ?
N1 C13 1.506(5) . ?
N1 C7 1.290(5) . ?
C16 C15 1.534(5) . ?
C16 C19 1.528(5) . ?
C16 C20 1.519(5) . ?
C23 C21 1.444(5) . ?
C23 C22 1.427(5) . ?
C23 C24 1.400(5) . ?
C2 C1 1.433(6) . ?
C2 C7 1.444(5) . ?
C2 C3 1.394(5) . ?
C13 C17 1.533(6) . ?
C13 C14 1.543(6) . ?
C13 C18 1.518(6) . ?
C1 C6 1.446(5) . ?
C7 H7 0.9500 . ?
C27 C28 1.531(6) . ?
C27 C22 1.433(5) . ?
C27 C26 1.375(6) . ?
C21 H21 0.9500 . ?
C28 C30 1.524(7) . ?
C28 C31 1.545(7) . ?
C28 C29 1.508(9) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C6 C5 1.377(6) . ?
C6 C8 1.525(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C9 C8 1.529(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C14 1.522(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C25 C24 1.380(5) . ?
C25 C26 1.407(6) . ?
C5 H5 0.9500 . ?
C5 C4 1.399(6) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C3 H3 0.9500 . ?
C3 C4 1.374(6) . ?
C24 H24 0.9500 . ?
C8 C10 1.540(6) . ?
C8 C11 1.539(8) . ?
C26 H26 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?

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
F1 Sb1 F3A 88.3(8) . . ?
F1 Sb1 F2 178.83(17) . . ?
F1 Sb1 F6A 90.4(6) . . ?
F1 Sb1 F4B 92.0(12) . . ?
F1 Sb1 F5B 92.6(8) . . ?
F3A Sb1 F6A 87.6(7) . . ?
F2 Sb1 F3A 92.0(8) . . ?
F2 Sb1 F6A 88.5(6) . . ?
F2 Sb1 F4B 88.0(13) . . ?
F2 Sb1 F5B 88.6(8) . . ?
F4A Sb1 F1 90.4(7) . . ?
F4A Sb1 F3A 176.1(8) . . ?
F4A Sb1 F2 89.2(7) . . ?
F4A Sb1 F6A 88.8(5) . . ?
F5A Sb1 F1 89.6(6) . . ?
F5A Sb1 F3A 93.4(8) . . ?
F5A Sb1 F2 91.5(6) . . ?
F5A Sb1 F4A 90.3(6) . . ?
F5A Sb1 F6A 179.1(6) . . ?
F6B Sb1 F1 88.0(11) . . ?
F6B Sb1 F2 90.9(11) . . ?
F6B Sb1 F4B 90.6(11) . . ?
F6B Sb1 F5B 179.4(14) . . ?
F3B Sb1 F1 89.7(12) . . ?
F3B Sb1 F2 90.3(12) . . ?
F3B Sb1 F6B 94.6(13) . . ?
F3B Sb1 F4B 174.6(14) . . ?
F3B Sb1 F5B 85.2(11) . . ?
F4B Sb1 F5B 89.6(10) . . ?
O1 Cu2 N2 150.31(14) . . ?
O1 Cu2 N1 92.87(13) . . ?
O2 Cu2 O1 85.83(12) . . ?
O2 Cu2 N2 93.42(12) . . ?
O2 Cu2 N1 147.47(15) . . ?
N1 Cu2 N2 103.06(13) . . ?
C1 O1 Cu2 127.5(3) . . ?
C22 O2 Cu2 128.0(2) . . ?
C25 O4 C32 118.7(3) . . ?
C4 O3 C12 117.5(4) . . ?
C16 N2 Cu2 118.9(2) . . ?
C21 N2 Cu2 122.0(3) . . ?
C21 N2 C16 119.1(3) . . ?
C13 N1 Cu2 119.5(2) . . ?
C7 N1 Cu2 121.3(3) . . ?
C7 N1 C13 119.1(3) . . ?
N2 C16 C15 108.7(3) . . ?
N2 C16 C19 112.1(3) . . ?
N2 C16 C20 107.4(3) . . ?
C19 C16 C15 106.9(3) . . ?
C20 C16 C15 114.4(3) . . ?
C20 C16 C19 107.4(3) . . ?
C22 C23 C21 122.9(3) . . ?
C24 C23 C21 116.8(3) . . ?
C24 C23 C22 120.3(3) . . ?
C1 C2 C7 122.5(3) . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 C7 116.6(4) . . ?
N1 C13 C17 112.0(3) . . ?
N1 C13 C14 108.3(3) . . ?
N1 C13 C18 108.2(3) . . ?
C17 C13 C14 107.2(4) . . ?
C18 C13 C17 107.6(4) . . ?
C18 C13 C14 113.6(3) . . ?
O1 C1 C2 121.2(3) . . ?
O1 C1 C6 119.6(4) . . ?
C2 C1 C6 119.2(3) . . ?
N1 C7 C2 128.0(4) . . ?
N1 C7 H7 116.0 . . ?
C2 C7 H7 116.0 . . ?
C22 C27 C28 121.0(4) . . ?
C26 C27 C28 121.4(3) . . ?
C26 C27 C22 117.6(3) . . ?
N2 C21 C23 127.8(3) . . ?
N2 C21 H21 116.1 . . ?
C23 C21 H21 116.1 . . ?
C27 C28 C31 111.4(4) . . ?
C30 C28 C27 110.3(4) . . ?
C30 C28 C31 107.2(5) . . ?
C29 C28 C27 109.3(4) . . ?
C29 C28 C30 110.9(5) . . ?
C29 C28 C31 107.7(5) . . ?
O2 C22 C23 121.6(3) . . ?
O2 C22 C27 118.7(3) . . ?
C23 C22 C27 119.7(3) . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 C6 C8 121.1(4) . . ?
C5 C6 C1 116.6(4) . . ?
C5 C6 C8 122.2(4) . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
C16 C15 H15A 107.0 . . ?
C16 C15 H15B 107.0 . . ?
H15A C15 H15B 106.7 . . ?
C14 C15 C16 121.4(3) . . ?
C14 C15 H15A 107.0 . . ?
C14 C15 H15B 107.0 . . ?
C13 C14 H14A 107.3 . . ?
C13 C14 H14B 107.3 . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14A 107.3 . . ?
C15 C14 H14B 107.3 . . ?
H14A C14 H14B 106.9 . . ?
O4 C25 C24 125.2(4) . . ?
O4 C25 C26 114.5(3) . . ?
C24 C25 C26 120.2(3) . . ?
C6 C5 H5 118.3 . . ?
C6 C5 C4 123.4(4) . . ?
C4 C5 H5 118.3 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.2(4) . . ?
C4 C3 H3 120.4 . . ?
C23 C24 H24 120.3 . . ?
C25 C24 C23 119.5(4) . . ?
C25 C24 H24 120.3 . . ?
C6 C8 C9 110.4(4) . . ?
C6 C8 C10 111.7(4) . . ?
C6 C8 C11 109.2(4) . . ?
C9 C8 C10 107.5(4) . . ?
C9 C8 C11 110.4(4) . . ?
C11 C8 C10 107.7(4) . . ?
C27 C26 C25 122.6(3) . . ?
C27 C26 H26 118.7 . . ?
C25 C26 H26 118.7 . . ?
O3 C4 C5 113.8(4) . . ?
O3 C4 C3 125.7(4) . . ?
C3 C4 C5 120.5(4) . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C32 H32A 109.5 . . ?
O4 C32 H32B 109.5 . . ?
O4 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
Cl1 C33 Cl2 112.4(5) . . ?
Cl1 C33 H33A 109.1 . . ?
Cl1 C33 H33B 109.1 . . ?
Cl2 C33 H33A 109.1 . . ?
Cl2 C33 H33B 109.1 . . ?
H33A C33 H33B 107.9 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sad3
_database_code_depnum_ccdc_archive 'CCDC 2014610'
loop_
_audit_author_name
_audit_author_address
'Christian Philouze'
;CNRS
France
;
_audit_update_record             
;
2020-07-07 deposited with the CCDC.	2020-09-03 downloaded from the CCDC.
;
_audit_creation_date             2020-07-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H38 Cu N2 O4, C0.16 H0.32 Cl0.32'
_chemical_formula_sum            'C36.16 H38.32 Cl0.32 Cu N2 O4'
_chemical_formula_weight         639.60
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      rhombohedral
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3:r'
_space_group_name_Hall           '-P 3*'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'z, x, y'
'y, z, x'
'-x, -y, -z'
'-z, -x, -y'
'-y, -z, -x'

_cell_length_a                   21.012(2)
_cell_length_b                   21.012(2)
_cell_length_c                   21.012(2)
_cell_angle_alpha                115.759(17)
_cell_angle_beta                 115.759(17)
_cell_angle_gamma                115.759(17)
_cell_volume                     4814(2)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    29196
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.497
_cell_measurement_theta_min      2.841
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.500579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.1998 before and 0.0597 after correction.
The Ratio of minimum to maximum transmission is 0.5006.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2014
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            29196
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.841
_diffrn_ambient_temperature      200.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'APEX II'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'κ-geometry 4 circles diffractometer'
_diffrn_measurement_device_type  'Bruker-AXS-enraf-nonius KappaAPEXII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    'Montel optic'
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Multilayer mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec ISG250'
_diffrn_source_target            Mo
_diffrn_source_type              'Microfocus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4660
_reflns_number_total             7300
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       EvalCCD
_computing_data_collection       Collect
_computing_data_reduction        EvalCCD
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    ?
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         7300
_refine_ls_number_restraints     59
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0562
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0349P)²+4.6650P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1343
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl1-C37
 1.8 with sigma of 0.02
 H37A-C37
 0.95 with sigma of 0.02
 H37B-C37
 0.95 with sigma of 0.02
 H37B-H37A
 1.6 with sigma of 0.02
 Cl1-H37B
 2.65 with sigma of 0.02
3. Rigid bond restraints
 O4A, O4B, C36A, C36B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C29, O4B, O4A, C36A, C36B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O4B \\sim O4A \\sim C36B \\sim C36A: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
O4B \\sim O4A \\sim C36A \\sim C36B \\sim C29: within 1.7A with sigma of 0.04
and sigma for terminal atoms of 0.08
5. Others
 Sof(C36B)=Sof(H36D)=Sof(H36E)=Sof(H36F)=Sof(O4B)=1-FVAR(1)
 Sof(O4A)=Sof(C36A)=Sof(H36A)=Sof(H36B)=Sof(H36C)=FVAR(1)
 Sof(C37)=Sof(H37A)=Sof(H37B)=0.33333*FVAR(3)
 Sof(Cl1)=0.66666*FVAR(3)
6.a Riding coordinates:
 C37(H37A,H37B)
6.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C25(H25), C28(H28), C7(H7), C14(H14), C24(H24), C30(H30),
 C22(H22), C17(H17), C15(H15), C21(H21), C16(H16), C23(H23)
6.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C34(H34A,H34B,
 H34C), C33(H33A,H33B,H33C), C35(H35A,H35B,H35C), C12(H12A,H12B,H12C),
 C36A(H36A,H36B,H36C), C36B(H36D,H36E,H36F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.68479(3) 0.81694(3) 0.15142(3) 0.03371(13) Uani 1 1 d . . . . .
O1 O 0.84069(17) 0.94562(18) 0.27384(17) 0.0358(5) Uani 1 1 d . . . . .
N1 N 0.6842(2) 0.7882(2) 0.2277(2) 0.0336(6) Uani 1 1 d . . . . .
N2 N 0.5345(2) 0.7389(2) 0.0503(2) 0.0380(6) Uani 1 1 d . . . . .
O3 O 1.12748(18) 1.22010(18) 0.71481(18) 0.0393(5) Uani 1 1 d . . . . .
O2 O 0.68581(18) 0.8014(2) 0.05684(19) 0.0456(6) Uani 1 1 d . . . . .
O4A O 0.3729(6) 0.5717(5) -0.3675(5) 0.0585(17) Uani 0.712(12) 1 d . U . A 1
C4 C 1.0491(3) 1.1430(3) 0.6021(3) 0.0316(7) Uani 1 1 d . . . . .
C6 C 1.0189(2) 1.1149(2) 0.4619(3) 0.0296(6) Uani 1 1 d . . . . .
C5 C 1.0840(2) 1.1785(2) 0.5697(3) 0.0309(7) Uani 1 1 d . . . . .
H5 H 1.1573 1.2510 0.6258 0.037 Uiso 1 1 calc R . . . .
C3 C 0.9460(2) 1.0389(2) 0.5241(2) 0.0301(6) Uani 1 1 d . . . . .
H3 H 0.9229 1.0125 0.5451 0.036 Uiso 1 1 calc R . . . .
C1 C 0.9064(2) 1.0064(2) 0.3773(2) 0.0285(6) Uani 1 1 d . . . . .
C26 C 0.6072(3) 0.7459(3) -0.0434(3) 0.0369(7) Uani 1 1 d . . . . .
C8 C 1.0610(3) 1.1575(3) 0.4308(3) 0.0353(7) Uani 1 1 d . . . . .
C11 C 1.0528(3) 1.0827(3) 0.3566(3) 0.0449(9) Uani 1 1 d . . . . .
H11A H 1.1000 1.0829 0.3967 0.067 Uiso 1 1 calc GR . . . .
H11B H 1.0771 1.1099 0.3352 0.067 Uiso 1 1 calc GR . . . .
H11C H 0.9760 1.0073 0.2903 0.067 Uiso 1 1 calc GR . . . .
C2 C 0.8732(2) 0.9698(2) 0.4108(2) 0.0282(6) Uani 1 1 d . . . . .
C13 C 0.5915(3) 0.6769(3) 0.1624(3) 0.0367(7) Uani 1 1 d . . . . .
C27 C 0.5008(3) 0.6904(3) -0.0980(3) 0.0391(8) Uani 1 1 d . . . . .
C9 C 0.9939(4) 1.1639(3) 0.3722(4) 0.0506(9) Uani 1 1 d . . . . .
H9A H 0.9166 1.0895 0.3029 0.076 Uiso 1 1 calc GR . . . .
H9B H 1.0235 1.1955 0.3562 0.076 Uiso 1 1 calc GR . . . .
H9C H 0.9983 1.2107 0.4198 0.076 Uiso 1 1 calc GR . . . .
C10 C 1.1839(3) 1.2738(3) 0.5339(3) 0.0557(10) Uani 1 1 d . . . . .
H10A H 1.1932 1.3250 0.5841 0.084 Uiso 1 1 calc GR . . . .
H10B H 1.2080 1.2993 0.5114 0.084 Uiso 1 1 calc GR . . . .
H10C H 1.2285 1.2708 0.5717 0.084 Uiso 1 1 calc GR . . . .
C25 C 0.4745(3) 0.6959(3) -0.0456(3) 0.0406(8) Uani 1 1 d . . . . .
H25 H 0.4045 0.6643 -0.0854 0.049 Uiso 1 1 calc R . . . .
C34 C 0.7728(4) 0.7607(4) -0.0124(4) 0.0649(12) Uani 1 1 d . . . . .
H34A H 0.8442 0.7973 0.0198 0.097 Uiso 1 1 calc GR . . . .
H34B H 0.7157 0.6808 -0.0785 0.097 Uiso 1 1 calc GR . . . .
H34C H 0.7776 0.7758 0.0417 0.097 Uiso 1 1 calc GR . . . .
C33 C 0.8279(3) 0.9270(3) 0.0582(3) 0.0514(9) Uani 1 1 d . . . . .
H33A H 0.8294 0.9399 0.1099 0.077 Uiso 1 1 calc GR . . . .
H33B H 0.8078 0.9537 0.0366 0.077 Uiso 1 1 calc GR . . . .
H33C H 0.9011 0.9668 0.0940 0.077 Uiso 1 1 calc GR . . . .
C20 C 0.4948(3) 0.7467(3) 0.0906(3) 0.0415(8) Uani 1 1 d . . . . .
C19 C 0.4732(3) 0.6960(3) 0.1165(3) 0.0425(8) Uani 1 1 d . . . . .
C28 C 0.4169(3) 0.6297(3) -0.2086(3) 0.0496(10) Uani 1 1 d . . . . .
H28 H 0.3458 0.5928 -0.2451 0.059 Uiso 1 1 calc R . . . .
C18 C 0.4887(3) 0.6302(3) 0.1043(3) 0.0410(8) Uani 1 1 d . . . . .
C7 C 0.7681(2) 0.8596(3) 0.3327(3) 0.0307(7) Uani 1 1 d . . . . .
H7 H 0.7588 0.8361 0.3609 0.037 Uiso 1 1 calc R . . . .
C35 C 0.7480(5) 0.7896(5) -0.1190(4) 0.0830(16) Uani 1 1 d . . . . .
H35A H 0.8232 0.8329 -0.0788 0.125 Uiso 1 1 calc GR . . . .
H35B H 0.7273 0.8153 -0.1420 0.125 Uiso 1 1 calc GR . . . .
H35C H 0.6966 0.7114 -0.1844 0.125 Uiso 1 1 calc GR . . . .
C31 C 0.6285(3) 0.7419(3) -0.1006(3) 0.0399(8) Uani 1 1 d . . . . .
C32 C 0.7433(3) 0.8042(3) -0.0436(3) 0.0461(9) Uani 1 1 d . . . . .
C14 C 0.6061(3) 0.6173(3) 0.1574(3) 0.0467(9) Uani 1 1 d . . . . .
H14 H 0.6768 0.6504 0.1974 0.056 Uiso 1 1 calc R . . . .
C29 C 0.4388(3) 0.6247(3) -0.2618(3) 0.0533(10) Uani 1 1 d . U . . .
C24 C 0.4330(3) 0.7056(3) 0.1532(4) 0.0531(10) Uani 1 1 d . . . . .
H24 H 0.4162 0.6703 0.1698 0.064 Uiso 1 1 calc R . . . .
C30 C 0.5438(3) 0.6810(3) -0.2070(3) 0.0503(9) Uani 1 1 d . . . . .
H30 H 0.5575 0.6770 -0.2454 0.060 Uiso 1 1 calc R . . . .
C12 C 1.0932(3) 1.1914(3) 0.7519(3) 0.0506(9) Uani 1 1 d . . . . .
H12A H 1.0273 1.1703 0.7196 0.076 Uiso 1 1 calc GR . . . .
H12B H 1.1527 1.2548 0.8326 0.076 Uiso 1 1 calc GR . . . .
H12C H 1.0758 1.1292 0.7290 0.076 Uiso 1 1 calc GR . . . .
C22 C 0.4401(4) 0.8159(4) 0.1423(4) 0.0673(12) Uani 1 1 d . . . . .
H22 H 0.4299 0.8575 0.1519 0.081 Uiso 1 1 calc R . . . .
C17 C 0.4019(3) 0.5216(3) 0.0406(3) 0.0555(11) Uani 1 1 d . . . . .
H17 H 0.3306 0.4871 -0.0011 0.067 Uiso 1 1 calc R . . . .
C15 C 0.5184(3) 0.5097(3) 0.0944(4) 0.0623(12) Uani 1 1 d . . . . .
H15 H 0.5289 0.4694 0.0917 0.075 Uiso 1 1 calc R . . . .
C21 C 0.4788(3) 0.8065(4) 0.1039(4) 0.0541(10) Uani 1 1 d . . . . .
H21 H 0.4944 0.8414 0.0867 0.065 Uiso 1 1 calc R . . . .
C16 C 0.4166(3) 0.4618(3) 0.0360(4) 0.0661(13) Uani 1 1 d . . . . .
H16 H 0.3560 0.3879 -0.0076 0.079 Uiso 1 1 calc R . . . .
C23 C 0.4169(4) 0.7648(4) 0.1661(4) 0.0650(12) Uani 1 1 d . . . . .
H23 H 0.3896 0.7702 0.1917 0.078 Uiso 1 1 calc R . . . .
C36A C 0.2666(6) 0.5175(6) -0.4269(5) 0.059(2) Uani 0.712(12) 1 d . U . A 1
H36A H 0.2246 0.4838 -0.4997 0.088 Uiso 0.712(12) 1 calc GR . . A 1
H36B H 0.2724 0.5710 -0.3864 0.088 Uiso 0.712(12) 1 calc GR . . A 1
H36C H 0.2287 0.4600 -0.4361 0.088 Uiso 0.712(12) 1 calc GR . . A 1
C36B C 0.3397(15) 0.5315(16) -0.4359(16) 0.071(6) Uani 0.288(12) 1 d . U . A 2
H36D H 0.2703 0.4872 -0.5080 0.107 Uiso 0.288(12) 1 calc GR . . A 2
H36E H 0.3506 0.4888 -0.4454 0.107 Uiso 0.288(12) 1 calc GR . . A 2
H36F H 0.4013 0.5993 -0.4038 0.107 Uiso 0.288(12) 1 calc GR . . A 2
O4B O 0.3351(13) 0.5587(13) -0.3660(12) 0.068(5) Uani 0.288(12) 1 d . U . A 2
Cl1 Cl 0.461(3) 0.4696(11) -0.465(2) 0.270(13) Uani 0.315(8) 1 d D . . . .
C37 C 0.579(3) 0.579(3) -0.421(3) 0.23(2) Uani 0.473(11) 3 d DS T P . .
H37A H 0.5651 0.6131 -0.4019 0.277 Uiso 0.158(4) 1 d DR . . . .
H37B H 0.6534 0.6187 -0.3698 0.277 Uiso 0.158(4) 1 d DR . . . .


_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 O1 1.895(4) . ?
Cu1 N1 1.945(3) . ?
Cu1 N2 1.952(3) . ?
Cu1 O2 1.880(2) . ?
O1 C1 1.307(4) . ?
N1 C13 1.441(4) . ?
N1 C7 1.293(4) . ?
N2 C25 1.299(5) . ?
N2 C20 1.432(5) . ?
O3 C4 1.379(4) . ?
O3 C12 1.417(5) . ?
O2 C26 1.300(4) . ?
O4A C29 1.388(7) . ?
O4A C36A 1.405(10) . ?
C4 C5 1.400(5) . ?
C4 C3 1.357(5) . ?
C6 C5 1.369(5) . ?
C6 C1 1.443(5) . ?
C6 C8 1.529(4) . ?
C5 H5 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.419(5) . ?
C1 C2 1.417(4) . ?
C26 C27 1.420(5) . ?
C26 C31 1.439(5) . ?
C8 C11 1.526(5) . ?
C8 C9 1.524(5) . ?
C8 C10 1.544(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C2 C7 1.426(5) . ?
C13 C18 1.395(5) . ?
C13 C14 1.387(5) . ?
C27 C25 1.415(5) . ?
C27 C28 1.431(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C25 H25 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C34 C32 1.521(6) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C33 C32 1.519(6) . ?
C20 C19 1.392(5) . ?
C20 C21 1.383(5) . ?
C19 C18 1.497(5) . ?
C19 C24 1.387(6) . ?
C28 H28 0.9500 . ?
C28 C29 1.363(6) . ?
C18 C17 1.389(5) . ?
C7 H7 0.9500 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C35 C32 1.535(6) . ?
C31 C32 1.532(6) . ?
C31 C30 1.371(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.384(6) . ?
C29 C30 1.390(6) . ?
C29 O4B 1.433(16) . ?
C24 H24 0.9500 . ?
C24 C23 1.374(6) . ?
C30 H30 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C22 H22 0.9500 . ?
C22 C21 1.385(6) . ?
C22 C23 1.365(7) . ?
C17 H17 0.9500 . ?
C17 C16 1.392(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.368(6) . ?
C21 H21 0.9500 . ?
C16 H16 0.9500 . ?
C23 H23 0.9500 . ?
C36A H36A 0.9800 . ?
C36A H36B 0.9800 . ?
C36A H36C 0.9800 . ?
C36B H36D 0.9800 . ?
C36B H36E 0.9800 . ?
C36B H36F 0.9800 . ?
C36B O4B 1.39(3) . ?
Cl1 Cl1 1.478(16) 6_655 ?
Cl1 Cl1 1.478(17) 5_565 ?
Cl1 C37 1.70(3) 4_664 ?
Cl1 C37 1.869(13) . ?
C37 Cl1 1.869(13) 2_654 ?
C37 Cl1 1.869(13) 3_564 ?
C37 Cl1 1.70(3) 4_664 ?
C37 Cl1 1.70(3) 6_655 ?
C37 Cl1 1.70(3) 5_565 ?
C37 H37A 0.8910 . ?
C37 H37B 0.9647 . ?

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
O1 Cu1 N1 92.36(10) . . ?
O1 Cu1 N2 153.60(12) . . ?
N1 Cu1 N2 96.66(11) . . ?
O2 Cu1 O1 89.68(11) . . ?
O2 Cu1 N1 154.53(12) . . ?
O2 Cu1 N2 92.64(12) . . ?
C1 O1 Cu1 127.5(2) . . ?
C13 N1 Cu1 118.4(2) . . ?
C7 N1 Cu1 123.8(2) . . ?
C7 N1 C13 117.2(3) . . ?
C25 N2 Cu1 123.7(3) . . ?
C25 N2 C20 116.5(3) . . ?
C20 N2 Cu1 118.7(2) . . ?
C4 O3 C12 116.6(3) . . ?
C26 O2 Cu1 130.6(2) . . ?
C29 O4A C36A 112.9(6) . . ?
O3 C4 C5 114.5(3) . . ?
C3 C4 O3 125.8(3) . . ?
C3 C4 C5 119.6(3) . . ?
C5 C6 C1 117.8(3) . . ?
C5 C6 C8 121.8(3) . . ?
C1 C6 C8 120.4(3) . . ?
C4 C5 H5 118.1 . . ?
C6 C5 C4 123.8(3) . . ?
C6 C5 H5 118.1 . . ?
C4 C3 H3 120.3 . . ?
C4 C3 C2 119.4(3) . . ?
C2 C3 H3 120.3 . . ?
O1 C1 C6 119.2(3) . . ?
O1 C1 C2 122.9(3) . . ?
C2 C1 C6 117.9(3) . . ?
O2 C26 C27 122.1(3) . . ?
O2 C26 C31 119.4(3) . . ?
C27 C26 C31 118.5(3) . . ?
C6 C8 C10 111.4(3) . . ?
C11 C8 C6 111.2(3) . . ?
C11 C8 C10 106.5(3) . . ?
C9 C8 C6 109.1(3) . . ?
C9 C8 C11 110.1(3) . . ?
C9 C8 C10 108.4(3) . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 C2 C7 116.7(3) . . ?
C1 C2 C3 121.4(3) . . ?
C1 C2 C7 121.8(3) . . ?
C18 C13 N1 120.0(3) . . ?
C14 C13 N1 118.9(3) . . ?
C14 C13 C18 121.0(3) . . ?
C26 C27 C28 119.9(3) . . ?
C25 C27 C26 122.5(3) . . ?
C25 C27 C28 117.6(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C25 C27 127.8(3) . . ?
N2 C25 H25 116.1 . . ?
C27 C25 H25 116.1 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
C19 C20 N2 121.1(3) . . ?
C21 C20 N2 118.6(3) . . ?
C21 C20 C19 120.3(4) . . ?
C20 C19 C18 123.3(3) . . ?
C24 C19 C20 117.8(3) . . ?
C24 C19 C18 118.9(3) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 C27 120.1(4) . . ?
C29 C28 H28 119.9 . . ?
C13 C18 C19 121.9(3) . . ?
C17 C18 C13 117.2(3) . . ?
C17 C18 C19 120.7(3) . . ?
N1 C7 C2 126.9(3) . . ?
N1 C7 H7 116.5 . . ?
C2 C7 H7 116.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C32 C35 H35A 109.5 . . ?
C32 C35 H35B 109.5 . . ?
C32 C35 H35C 109.5 . . ?
C26 C31 C32 120.5(3) . . ?
C30 C31 C26 118.4(3) . . ?
C30 C31 C32 121.1(3) . . ?
C34 C32 C35 108.0(4) . . ?
C34 C32 C31 109.6(3) . . ?
C33 C32 C34 110.6(3) . . ?
C33 C32 C35 107.2(4) . . ?
C33 C32 C31 109.6(3) . . ?
C31 C32 C35 111.8(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
O4A C29 C30 109.0(5) . . ?
C28 C29 O4A 131.3(5) . . ?
C28 C29 C30 119.7(3) . . ?
C28 C29 O4B 101.0(8) . . ?
C30 C29 O4B 139.3(8) . . ?
C19 C24 H24 119.1 . . ?
C23 C24 C19 121.7(4) . . ?
C23 C24 H24 119.1 . . ?
C31 C30 C29 123.4(4) . . ?
C31 C30 H30 118.3 . . ?
C29 C30 H30 118.3 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C23 C22 C21 119.5(4) . . ?
C18 C17 H17 119.1 . . ?
C18 C17 C16 121.8(4) . . ?
C16 C17 H17 119.1 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.7(4) . . ?
C16 C15 H15 120.1 . . ?
C20 C21 C22 120.5(4) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C17 C16 H16 120.1 . . ?
C15 C16 C17 119.8(4) . . ?
C15 C16 H16 120.1 . . ?
C24 C23 H23 119.9 . . ?
C22 C23 C24 120.1(4) . . ?
C22 C23 H23 119.9 . . ?
O4A C36A H36A 109.5 . . ?
O4A C36A H36B 109.5 . . ?
O4A C36A H36C 109.5 . . ?
H36A C36A H36B 109.5 . . ?
H36A C36A H36C 109.5 . . ?
H36B C36A H36C 109.5 . . ?
H36D C36B H36E 109.5 . . ?
H36D C36B H36F 109.5 . . ?
H36E C36B H36F 109.5 . . ?
O4B C36B H36D 109.5 . . ?
O4B C36B H36E 109.5 . . ?
O4B C36B H36F 109.5 . . ?
C36B O4B C29 107.2(15) . . ?
Cl1 Cl1 Cl1 116.0(12) 6_655 5_565 ?
Cl1 Cl1 C37 71.8(7) 5_565 4_664 ?
Cl1 Cl1 C37 59.5(12) 6_655 . ?
Cl1 Cl1 C37 59.5(12) 5_565 . ?
Cl1 Cl1 C37 71.8(7) 6_655 4_664 ?
C37 Cl1 C37 71(2) 4_664 . ?
Cl1 C37 Cl1 95(2) 6_655 5_565 ?
Cl1 C37 Cl1 95(2) 6_655 4_664 ?
Cl1 C37 Cl1 109(2) 4_664 . ?
Cl1 C37 Cl1 109(2) 6_655 3_564 ?
Cl1 C37 Cl1 84.2(12) 2_654 . ?
Cl1 C37 Cl1 48.7(8) 4_664 3_564 ?
Cl1 C37 Cl1 48.7(8) 5_565 3_564 ?
Cl1 C37 Cl1 109(2) 5_565 2_654 ?
Cl1 C37 Cl1 48.7(8) 6_655 2_654 ?
Cl1 C37 Cl1 84.2(12) 3_564 2_654 ?
Cl1 C37 Cl1 48.7(8) 6_655 . ?
Cl1 C37 Cl1 48.7(8) 5_565 . ?
Cl1 C37 Cl1 48.7(8) 4_664 2_654 ?
Cl1 C37 Cl1 84.2(12) 3_564 . ?
Cl1 C37 Cl1 95(2) 5_565 4_664 ?
Cl1 C37 H37A 131.3 6_655 . ?
Cl1 C37 H37A 44.4 5_565 . ?
Cl1 C37 H37A 111.6 4_664 . ?
Cl1 C37 H37A 67.8 3_564 . ?
Cl1 C37 H37A 150.4 2_654 . ?
Cl1 C37 H37A 83.6 . . ?
Cl1 C37 H37B 159.6 5_565 . ?
Cl1 C37 H37B 128.8 . . ?
Cl1 C37 H37B 89.3 2_654 . ?
Cl1 C37 H37B 103.5 4_664 . ?
Cl1 C37 H37B 145.5 3_564 . ?
Cl1 C37 H37B 90.9 6_655 . ?
H37A C37 H37B 119.1 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
