# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# 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_llbr
_database_code_depnum_ccdc_archive 'CCDC 1402142'
_audit_update_record             
;
2015-05-21 deposited with the CCDC.
2016-10-13 downloaded from the CCDC.
;
_audit_creation_date             2014-06-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'Br, C28 H32 Cu N12 O4'
_chemical_formula_sum            'C28 H32 Br Cu N12 O4'
_chemical_formula_weight         744.10
_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'
Br Br -0.6763 1.2805 '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'
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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P c m n'
_space_group_name_Hall           '-P 2n 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   6.06932(11)
_cell_length_b                   25.5373(6)
_cell_length_c                   27.9983(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4339.57(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11265
_cell_measurement_temperature    292.2(6)
_cell_measurement_theta_max      72.6310
_cell_measurement_theta_min      4.6360
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.129
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60512
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0800
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            34401
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         4.687
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.2(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -31.00   53.00   1.0000    4.8950
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000  150.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega   10.00  104.00   1.0000    4.8950
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   75.00   1.0000    4.8950
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000    0.0000 74

#__ type_ start__ end____ width___ exp.time_
  4 omega   10.00  104.00   1.0000    4.8950
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000    0.0000 94

#__ type_ start__ end____ width___ exp.time_
  5 omega   20.00  104.00   1.0000    4.8950
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
  6 omega   20.00  104.00   1.0000    4.8950
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
  7 omega   91.00  176.00   1.0000   19.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -150.0000 85

#__ type_ start__ end____ width___ exp.time_
  8 omega   39.00  109.00   1.0000   19.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 70

#__ type_ start__ end____ width___ exp.time_
  9 omega   40.00   98.00   1.0000   19.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

#__ type_ start__ end____ width___ exp.time_
 10 omega   90.00  175.00   1.0000   19.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 85

#__ type_ start__ end____ width___ exp.time_
 11 omega   39.00  109.00   1.0000   19.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

#__ type_ start__ end____ width___ exp.time_
 12 omega   38.00   91.00   1.0000   19.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
 13 omega   70.00  178.00   1.0000   19.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  150.0000 108

#__ type_ start__ end____ width___ exp.time_
 14 omega   40.00   98.00   1.0000   19.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

#__ type_ start__ end____ width___ exp.time_
 15 omega   10.00  104.00   1.0000    4.8950
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000 -150.0000 94

#__ type_ start__ end____ width___ exp.time_
 16 omega   18.00  106.00   1.0000    4.8950
omega____ theta____ kappa____ phi______ frames
    -       36.5421   38.0000 -150.0000 88

#__ type_ start__ end____ width___ exp.time_
 17 omega  -31.00   53.00   1.0000    4.8950
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000   60.0000 84

#__ type_ start__ end____ width___ exp.time_
 18 omega   20.00  104.00   1.0000    4.8950
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
 19 omega    1.00   75.00   1.0000    4.8950
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000 -180.0000 74

#__ type_ start__ end____ width___ exp.time_
 20 omega  -31.00   53.00   1.0000    4.8950
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000 -120.0000 84

#__ type_ start__ end____ width___ exp.time_
 21 omega   37.00  146.00   1.0000   19.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   60.0000 109

#__ type_ start__ end____ width___ exp.time_
 22 omega   40.00  116.00   1.0000   19.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   90.0000 76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0231665000
_diffrn_orient_matrix_UB_12      0.0444830000
_diffrn_orient_matrix_UB_13      0.0368454000
_diffrn_orient_matrix_UB_21      -0.1081890000
_diffrn_orient_matrix_UB_22      -0.0348881000
_diffrn_orient_matrix_UB_23      0.0382504000
_diffrn_orient_matrix_UB_31      0.2284561000
_diffrn_orient_matrix_UB_32      -0.0210325000
_diffrn_orient_matrix_UB_33      0.0143989000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3374
_reflns_number_total             3967
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.636
_refine_diff_density_min         -1.804
_refine_diff_density_rms         0.147
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3967
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0980
_refine_ls_restrained_S_all      1.107
_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)+(0.1655P)²+16.2752P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3076
_refine_ls_wR_factor_ref         0.3134
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C19(H19A,H19B), C32(H32A,H32B), C90(H90A,H90B)
2.b Aromatic/amide H refined with riding coordinates:
 N9(H9), N11(H11), N10(H10), C68(H68), C85(H85), C93(H93), C91(H91), C92(H92)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Br4 Br 0.39123(14) 0.2500 0.43829(3) 0.0475(4) Uani 1 2 d S T P . .
Cu1 Cu 0.8953(2) 0.2500 0.43855(4) 0.0503(5) Uani 1 2 d S T P . .
N9 N 0.8091(12) 0.3784(3) 0.3479(3) 0.078(2) Uani 1 1 d . . . . .
H9 H 0.7350 0.4044 0.3368 0.093 Uiso 1 1 calc R . . . .
N8 N 0.7667(9) 0.3630(2) 0.54189(19) 0.0523(13) Uani 1 1 d . . . . .
N11 N 0.6355(8) 0.3139(3) 0.6321(2) 0.0620(18) Uani 1 1 d . . . . .
H11 H 0.5021 0.3036 0.6365 0.074 Uiso 1 1 calc R . . . .
C14 C 0.6266(13) 0.3884(3) 0.5780(3) 0.071(2) Uani 1 1 d . . . . .
H14A H 0.4730 0.3816 0.5706 0.085 Uiso 1 1 calc R . . . .
H14B H 0.6498 0.4259 0.5770 0.085 Uiso 1 1 calc R . . . .
C19 C 1.1521(13) 0.3883(3) 0.2985(3) 0.067(2) Uani 1 1 d . . . . .
H19A H 1.3048 0.3799 0.3053 0.081 Uiso 1 1 calc R . . . .
H19B H 1.1369 0.4261 0.2994 0.081 Uiso 1 1 calc R . . . .
C32 C 1.0962(13) 0.3695(4) 0.2498(3) 0.076(3) Uani 1 1 d . . . . .
H32A H 0.9419 0.3762 0.2433 0.092 Uiso 1 1 calc R . . . .
H32B H 1.1832 0.3884 0.2264 0.092 Uiso 1 1 calc R . . . .
N6 N 0.8980(9) 0.3076(2) 0.38852(18) 0.0473(12) Uani 1 1 d . . . . .
N10 N 1.1396(9) 0.3135(4) 0.2455(2) 0.072(2) Uani 1 1 d . . . . .
H10 H 1.2737 0.3033 0.2420 0.087 Uiso 1 1 calc R . . . .
N7 N 0.8879(9) 0.3073(2) 0.48839(18) 0.0502(13) Uani 1 1 d . . . . .
C61 C 1.0115(10) 0.3651(2) 0.3359(2) 0.0431(13) Uani 1 1 d . . . . .
C68 C 0.7401(12) 0.3433(3) 0.3809(3) 0.0596(17) Uani 1 1 d . . . . .
H68 H 0.6037 0.3439 0.3960 0.071 Uiso 1 1 calc R . . . .
C83 C 0.7924(10) 0.2782(3) 0.6307(2) 0.063(2) Uani 1 1 d . . . . .
C85 C 0.7187(11) 0.3215(3) 0.5161(2) 0.0502(15) Uani 1 1 d . . . . .
H85 H 0.5839 0.3042 0.5171 0.060 Uiso 1 1 calc R . . . .
C90 C 0.6760(13) 0.3689(4) 0.6266(3) 0.074(2) Uani 1 1 d . . . . .
H90A H 0.8293 0.3760 0.6339 0.088 Uiso 1 1 calc R . . . .
H90B H 0.5865 0.3880 0.6494 0.088 Uiso 1 1 calc R . . . .
C93 C 1.0634(11) 0.3202(3) 0.3603(2) 0.0500(14) Uani 1 1 d . . . . .
H93 H 1.1944 0.3015 0.3574 0.060 Uiso 1 1 calc R . . . .
C91 C 1.0451(12) 0.3441(3) 0.4968(3) 0.0612(18) Uani 1 1 d . . . . .
H91 H 1.1801 0.3458 0.4811 0.073 Uiso 1 1 calc R . . . .
C92 C 0.9794(13) 0.3770(3) 0.5302(3) 0.073(2) Uani 1 1 d . . . . .
H92 H 1.0608 0.4043 0.5434 0.087 Uiso 1 1 calc R . . . .
O1 O 1.1723(8) 0.3132(3) 0.6316(2) 0.088(2) Uani 1 1 d . . . . .
C95 C 0.7393(10) 0.2790(4) 0.2484(2) 0.076(3) Uani 1 1 d . . . . .
C94 C 0.9817(9) 0.2777(3) 0.2467(2) 0.0593(19) Uani 1 1 d . . . . .
C96 C 1.0348(11) 0.2813(4) 0.6308(3) 0.076(3) Uani 1 1 d . . . . .
O2 O 0.5988(8) 0.3128(3) 0.2473(2) 0.089(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N6 2.031(5) . ?
Cu1 N6 2.031(5) 8_565 ?
Cu1 N7 2.022(5) . ?
Cu1 N7 2.022(5) 8_565 ?
N9 H9 0.8600 . ?
N9 C61 1.317(9) . ?
N9 C68 1.355(9) . ?
N8 C14 1.472(9) . ?
N8 C85 1.315(8) . ?
N8 C92 1.379(10) . ?
N11 H11 0.8600 . ?
N11 C83 1.318(10) . ?
N11 C90 1.434(12) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C90 1.479(13) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C32 1.485(13) . ?
C19 C61 1.475(9) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 N10 1.458(13) . ?
N6 C68 1.339(9) . ?
N6 C93 1.317(8) . ?
N10 H10 0.8600 . ?
N10 C94 1.325(10) . ?
N7 C85 1.338(8) . ?
N7 C91 1.360(9) . ?
C61 C93 1.372(8) . ?
C68 H68 0.9300 . ?
C83 C83 1.442(18) 8_565 ?
C83 C96 1.473(8) . ?
C85 H85 0.9300 . ?
C90 H90A 0.9700 . ?
C90 H90B 0.9700 . ?
C93 H93 0.9300 . ?
C91 H91 0.9300 . ?
C91 C92 1.319(10) . ?
C92 H92 0.9300 . ?
O1 C96 1.166(11) . ?
C95 C95 1.48(2) 8_565 ?
C95 C94 1.472(8) . ?
C95 O2 1.215(11) . ?
C94 C94 1.414(17) 8_565 ?
C96 C96 1.60(2) 8_565 ?

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
N6 Cu1 N6 92.8(3) 8_565 . ?
N7 Cu1 N6 179.2(2) . 8_565 ?
N7 Cu1 N6 179.2(2) 8_565 . ?
N7 Cu1 N6 87.3(2) . . ?
N7 Cu1 N6 87.3(2) 8_565 8_565 ?
N7 Cu1 N7 92.7(3) 8_565 . ?
C61 N9 H9 126.5 . . ?
C61 N9 C68 106.9(6) . . ?
C68 N9 H9 126.5 . . ?
C85 N8 C14 127.2(6) . . ?
C85 N8 C92 106.6(5) . . ?
C92 N8 C14 126.1(6) . . ?
C83 N11 H11 118.3 . . ?
C83 N11 C90 123.4(6) . . ?
C90 N11 H11 118.3 . . ?
N8 C14 H14A 109.3 . . ?
N8 C14 H14B 109.3 . . ?
N8 C14 C90 111.5(7) . . ?
H14A C14 H14B 108.0 . . ?
C90 C14 H14A 109.3 . . ?
C90 C14 H14B 109.3 . . ?
H19A C19 H19B 107.8 . . ?
C32 C19 H19A 109.0 . . ?
C32 C19 H19B 109.0 . . ?
C61 C19 H19A 109.0 . . ?
C61 C19 H19B 109.0 . . ?
C61 C19 C32 113.0(6) . . ?
C19 C32 H32A 109.5 . . ?
C19 C32 H32B 109.5 . . ?
H32A C32 H32B 108.1 . . ?
N10 C32 C19 110.7(6) . . ?
N10 C32 H32A 109.5 . . ?
N10 C32 H32B 109.5 . . ?
C68 N6 Cu1 126.6(4) . . ?
C93 N6 Cu1 126.6(4) . . ?
C93 N6 C68 106.5(5) . . ?
C32 N10 H10 118.5 . . ?
C94 N10 C32 122.9(6) . . ?
C94 N10 H10 118.5 . . ?
C85 N7 Cu1 127.9(4) . . ?
C85 N7 C91 104.5(6) . . ?
C91 N7 Cu1 127.1(4) . . ?
N9 C61 C19 128.0(6) . . ?
N9 C61 C93 107.7(6) . . ?
C93 C61 C19 123.8(6) . . ?
N9 C68 H68 125.1 . . ?
N6 C68 N9 109.7(6) . . ?
N6 C68 H68 125.1 . . ?
N11 C83 C83 133.7(4) . 8_565 ?
N11 C83 C96 133.2(8) . . ?
C83 C83 C96 93.0(5) 8_565 . ?
N8 C85 N7 111.5(6) . . ?
N8 C85 H85 124.2 . . ?
N7 C85 H85 124.2 . . ?
N11 C90 C14 113.1(6) . . ?
N11 C90 H90A 109.0 . . ?
N11 C90 H90B 109.0 . . ?
C14 C90 H90A 109.0 . . ?
C14 C90 H90B 109.0 . . ?
H90A C90 H90B 107.8 . . ?
N6 C93 C61 109.1(6) . . ?
N6 C93 H93 125.5 . . ?
C61 C93 H93 125.5 . . ?
N7 C91 H91 124.7 . . ?
C92 C91 N7 110.5(6) . . ?
C92 C91 H91 124.7 . . ?
N8 C92 H92 126.7 . . ?
C91 C92 N8 106.6(6) . . ?
C91 C92 H92 126.7 . . ?
C94 C95 C95 88.7(5) . 8_565 ?
O2 C95 C95 135.4(5) . 8_565 ?
O2 C95 C94 135.8(9) . . ?
N10 C94 C95 135.1(8) . . ?
N10 C94 C94 133.6(4) . 8_565 ?
C94 C94 C95 91.3(5) 8_565 . ?
C83 C96 C96 87.0(5) . 8_565 ?
O1 C96 C83 138.7(9) . . ?
O1 C96 C96 134.3(6) . 8_565 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 N6 C68 N9 174.0(5) . . . . ?
Cu1 N6 C93 C61 -172.4(4) . . . . ?
Cu1 N7 C85 N8 -175.0(4) . . . . ?
Cu1 N7 C91 C92 176.5(6) . . . . ?
N9 C61 C93 N6 -2.9(8) . . . . ?
N8 C14 C90 N11 -61.9(8) . . . . ?
N11 C83 C96 O1 -0.6(14) . . . . ?
N11 C83 C96 C96 177.7(7) . . . 8_565 ?
C14 N8 C85 N7 -176.9(7) . . . . ?
C14 N8 C92 C91 179.4(8) . . . . ?
C19 C32 N10 C94 102.8(8) . . . . ?
C19 C61 C93 N6 -175.2(6) . . . . ?
C32 C19 C61 N9 -79.1(10) . . . . ?
C32 C19 C61 C93 91.6(9) . . . . ?
C32 N10 C94 C95 5.4(12) . . . . ?
C32 N10 C94 C94 -174.7(5) . . . 8_565 ?
N7 C91 C92 N8 -3.7(10) . . . . ?
C61 N9 C68 N6 -1.5(9) . . . . ?
C61 C19 C32 N10 -64.8(9) . . . . ?
C68 N9 C61 C19 174.5(7) . . . . ?
C68 N9 C61 C93 2.7(8) . . . . ?
C68 N6 C93 C61 2.0(7) . . . . ?
C83 N11 C90 C14 100.2(8) . . . . ?
C83 C83 C96 O1 -178.2(10) 8_565 . . . ?
C83 C83 C96 C96 0.0 8_565 . . 8_565 ?
C85 N8 C14 C90 94.4(9) . . . . ?
C85 N8 C92 C91 2.1(10) . . . . ?
C85 N7 C91 C92 3.9(9) . . . . ?
C90 N11 C83 C83 -173.1(4) . . . 8_565 ?
C90 N11 C83 C96 10.1(11) . . . . ?
C93 N6 C68 N9 -0.3(8) . . . . ?
C91 N7 C85 N8 -2.5(8) . . . . ?
C92 N8 C14 C90 -82.3(10) . . . . ?
C92 N8 C85 N7 0.3(8) . . . . ?
C95 C95 C94 N10 179.9(7) 8_565 . . . ?
C95 C95 C94 C94 -0.003(0) 8_565 . . 8_565 ?
O2 C95 C94 N10 4.0(13) . . . . ?
O2 C95 C94 C94 -175.9(9) . . . 8_565 ?

_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 -0.333 0.000 -0.446 780.8 23.1 ?
2 0.188 0.250 0.049 7.2 0.0 ?
3 -0.049 0.500 -0.144 780.8 23.1 ?
4 -0.188 0.750 0.951 7.2 0.0 ?
5 0.313 0.250 0.549 7.2 0.0 ?
6 0.687 0.750 0.451 7.2 0.0 ?

_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_llclrr
_database_code_depnum_ccdc_archive 'CCDC 1402219'
_audit_update_record             
;
2015-05-21 deposited with the CCDC.
2016-10-13 downloaded from the CCDC.
;
_audit_creation_date             2014-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C28 H32 Cu N12 O4, Cl'
_chemical_formula_sum            'C28 H32 Cl Cu N12 O4'
_chemical_formula_weight         699.64
_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'
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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   27.9361(13)
_cell_length_b                   25.4180(14)
_cell_length_c                   6.0524(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4297.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7143
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      72.3260
_cell_measurement_theta_min      4.6850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.633
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.081
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            21536
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.048
_diffrn_reflns_theta_min         4.704
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    1.00   75.00   1.0000    7.3950
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000   90.0000 74

#__ type_ start__ end____ width___ exp.time_
  2 omega  -31.00   63.00   1.0000    7.3950
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -77.0000    0.0000 94

#__ type_ start__ end____ width___ exp.time_
  3 omega   20.00  104.00   1.0000    7.3950
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega    1.00   75.00   1.0000    7.3950
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000    0.0000 74

#__ type_ start__ end____ width___ exp.time_
  5 omega    1.00   75.00   1.0000    7.3950
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000  -60.0000 74

#__ type_ start__ end____ width___ exp.time_
  6 omega   20.00  104.00   1.0000    7.3950
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
  7 omega   39.00  109.00   1.0000   29.5750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 70

#__ type_ start__ end____ width___ exp.time_
  8 omega   87.00  178.00   1.0000   29.5750
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -180.0000 91

#__ type_ start__ end____ width___ exp.time_
  9 omega   39.00  109.00   1.0000   29.5750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 70

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   91.00   1.0000   29.5750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -31.0000  -19.0000 53

#__ type_ start__ end____ width___ exp.time_
 11 omega   39.00  109.00   1.0000   29.5750
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

#__ type_ start__ end____ width___ exp.time_
 12 omega   81.00  176.00   1.0000   29.5750
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 95

#__ type_ start__ end____ width___ exp.time_
 13 omega  -31.00   53.00   1.0000    7.3950
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -57.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
 14 omega   10.00  104.00   1.0000    7.3950
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
 15 omega   10.00  104.00   1.0000    7.3950
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000 -150.0000 94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0181758000
_diffrn_orient_matrix_UB_12      0.0541797000
_diffrn_orient_matrix_UB_13      -0.0775409000
_diffrn_orient_matrix_UB_21      -0.0434253000
_diffrn_orient_matrix_UB_22      -0.0266162000
_diffrn_orient_matrix_UB_23      -0.1094857000
_diffrn_orient_matrix_UB_31      -0.0287546000
_diffrn_orient_matrix_UB_32      0.0059183000
_diffrn_orient_matrix_UB_33      0.2160405000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3221
_reflns_number_total             3922
_reflns_odcompleteness_completeness 99.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.982
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3922
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0924
_refine_ls_restrained_S_all      1.055
_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)+(0.1410P)²+5.7200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2630
_refine_ls_wR_factor_ref         0.2698
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C17(H17A,H17B), C1(H1A,H1B), C63(H63A,H63B)
2.b Aromatic/amide H refined with riding coordinates:
 C46(H46), N4(H4), N15(H15), C34(H34), C50(H50), C58(H58), C81(H81), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Cu3 Cu 0.56316(3) 0.2500 0.6024(2) 0.0874(5) Uani 1 2 d S T P . .
Cl4 Cl 0.56306(5) 0.2500 0.1097(2) 0.0531(4) Uani 1 2 d S T P . .
N8 N 0.66587(13) 0.36414(14) 0.4825(7) 0.0618(9) Uani 1 1 d . . . . .
N9 N 0.46076(12) 0.36377(14) 0.7370(6) 0.0611(9) Uani 1 1 d . . . . .
C18 C 0.37140(13) 0.2778(2) 0.7142(6) 0.0668(13) Uani 1 1 d . . . . .
O27 O 0.75500(15) 0.3143(2) 0.8950(5) 0.0962(14) Uani 1 1 d . . . . .
C46 C 0.64048(14) 0.32126(18) 0.4316(8) 0.0618(11) Uani 1 1 d . . . . .
H46 H 0.6422 0.3037 0.2971 0.074 Uiso 1 1 calc R . . . .
N47 N 0.51331(11) 0.30760(14) 0.6132(7) 0.0667(11) Uani 1 1 d . . . . .
O54 O 0.37067(15) 0.1865(2) 0.3289(5) 0.1054(16) Uani 1 1 d . . . . .
C60 C 0.75463(13) 0.2775(2) 0.5111(6) 0.0657(13) Uani 1 1 d . . . . .
N4 N 0.37064(13) 0.3137(2) 0.8745(5) 0.0690(12) Uani 1 1 d . . . . .
H4 H 0.3674 0.3033 1.0090 0.083 Uiso 1 1 calc R . . . .
N15 N 0.75646(13) 0.3141(2) 0.3557(5) 0.0708(12) Uani 1 1 d . . . . .
H15 H 0.7607 0.3041 0.2214 0.085 Uiso 1 1 calc R . . . .
C23 C 0.7027(2) 0.3892(2) 0.3437(8) 0.0769(15) Uani 1 1 d . . . . .
H23A H 0.7018 0.4269 0.3659 0.092 Uiso 1 1 calc R . . . .
H23B H 0.6957 0.3822 0.1894 0.092 Uiso 1 1 calc R . . . .
C34 C 0.48654(15) 0.32146(17) 0.7845(8) 0.0615(11) Uani 1 1 d . . . . .
H34 H 0.4859 0.3039 0.9193 0.074 Uiso 1 1 calc R . . . .
C12 C 0.75415(14) 0.2797(2) 0.7543(6) 0.0797(17) Uani 1 1 d . . . . .
C14 C 0.37144(16) 0.2207(3) 0.4719(7) 0.0837(17) Uani 1 1 d . . . . .
N1 N 0.61294(12) 0.30731(14) 0.5963(6) 0.0584(9) Uani 1 1 d . . . . .
C17 C 0.4247(2) 0.3889(2) 0.8777(8) 0.0767(14) Uani 1 1 d . . . . .
H17A H 0.4257 0.4267 0.8548 0.092 Uiso 1 1 calc R . . . .
H17B H 0.4323 0.3821 1.0314 0.092 Uiso 1 1 calc R . . . .
C1 C 0.75187(19) 0.3691(3) 0.3971(8) 0.0834(17) Uani 1 1 d . . . . .
H1A H 0.7752 0.3880 0.3088 0.100 Uiso 1 1 calc R . . . .
H1B H 0.7588 0.3760 0.5514 0.100 Uiso 1 1 calc R . . . .
C50 C 0.65415(19) 0.3776(2) 0.6929(8) 0.0743(13) Uani 1 1 d . . . . .
H50 H 0.6668 0.4054 0.7738 0.089 Uiso 1 1 calc R . . . .
C58 C 0.47176(17) 0.3779(2) 0.5221(8) 0.0735(13) Uani 1 1 d . . . . .
H58 H 0.4595 0.4062 0.4424 0.088 Uiso 1 1 calc R . . . .
C63 C 0.37500(18) 0.3694(2) 0.8304(9) 0.0816(16) Uani 1 1 d . . . . .
H63A H 0.3523 0.3885 0.9212 0.098 Uiso 1 1 calc R . . . .
H63B H 0.3672 0.3762 0.6768 0.098 Uiso 1 1 calc R . . . .
C81 C 0.50429(18) 0.3417(2) 0.4521(8) 0.0751(13) Uani 1 1 d . . . . .
H81 H 0.5182 0.3410 0.3125 0.090 Uiso 1 1 calc R . . . .
C3 C 0.62092(17) 0.3434(2) 0.7621(9) 0.0740(13) Uani 1 1 d . . . . .
H3 H 0.6058 0.3439 0.8989 0.089 Uiso 1 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
Cu3 N47 2.022(3) . ?
Cu3 N47 2.022(3) 8_565 ?
Cu3 N1 2.014(3) 8_565 ?
Cu3 N1 2.014(3) . ?
N8 C46 1.336(5) . ?
N8 C23 1.473(6) . ?
N8 C50 1.359(6) . ?
N9 C34 1.326(5) . ?
N9 C17 1.466(6) . ?
N9 C58 1.384(6) . ?
C18 C18 1.414(11) 8_565 ?
C18 N4 1.331(6) . ?
C18 C14 1.466(6) 8_565 ?
O27 C12 1.225(6) . ?
C46 H46 0.9300 . ?
C46 N1 1.308(6) . ?
N47 C34 1.326(6) . ?
N47 C81 1.329(6) . ?
O54 C14 1.226(7) . ?
C60 C60 1.397(10) 8_565 ?
C60 N15 1.325(6) . ?
C60 C12 1.473(5) . ?
N4 H4 0.8600 . ?
N4 C63 1.447(7) . ?
N15 H15 0.8600 . ?
N15 C1 1.426(8) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C1 1.500(8) . ?
C34 H34 0.9300 . ?
C12 C12 1.510(12) 8_565 ?
C14 C18 1.466(6) 8_565 ?
C14 C14 1.491(13) 8_565 ?
N1 C3 1.377(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C63 1.501(8) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C50 H50 0.9300 . ?
C50 C3 1.339(7) . ?
C58 H58 0.9300 . ?
C58 C81 1.361(7) . ?
C63 H63A 0.9700 . ?
C63 H63B 0.9700 . ?
C81 H81 0.9300 . ?
C3 H3 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N47 Cu3 N47 92.8(2) 8_565 . ?
N1 Cu3 N47 87.27(14) 8_565 8_565 ?
N1 Cu3 N47 179.21(18) . 8_565 ?
N1 Cu3 N47 87.27(14) . . ?
N1 Cu3 N47 179.21(18) 8_565 . ?
N1 Cu3 N1 92.6(2) 8_565 . ?
C46 N8 C23 126.3(4) . . ?
C46 N8 C50 107.1(4) . . ?
C50 N8 C23 126.4(4) . . ?
C34 N9 C17 127.0(4) . . ?
C34 N9 C58 107.1(4) . . ?
C58 N9 C17 125.8(4) . . ?
C18 C18 C14 91.5(3) 8_565 8_565 ?
N4 C18 C18 133.2(3) . 8_565 ?
N4 C18 C14 135.3(5) . 8_565 ?
N8 C46 H46 124.5 . . ?
N1 C46 N8 111.0(4) . . ?
N1 C46 H46 124.5 . . ?
C34 N47 Cu3 127.3(3) . . ?
C34 N47 C81 107.0(4) . . ?
C81 N47 Cu3 125.4(3) . . ?
C60 C60 C12 92.2(3) 8_565 . ?
N15 C60 C60 134.7(3) . 8_565 ?
N15 C60 C12 133.0(5) . . ?
C18 N4 H4 118.8 . . ?
C18 N4 C63 122.3(4) . . ?
C63 N4 H4 118.8 . . ?
C60 N15 H15 117.9 . . ?
C60 N15 C1 124.2(4) . . ?
C1 N15 H15 117.9 . . ?
N8 C23 H23A 109.3 . . ?
N8 C23 H23B 109.3 . . ?
N8 C23 C1 111.7(4) . . ?
H23A C23 H23B 107.9 . . ?
C1 C23 H23A 109.3 . . ?
C1 C23 H23B 109.3 . . ?
N9 C34 H34 124.7 . . ?
N47 C34 N9 110.6(4) . . ?
N47 C34 H34 124.7 . . ?
O27 C12 C60 136.3(5) . . ?
O27 C12 C12 135.9(3) . 8_565 ?
C60 C12 C12 87.8(3) . 8_565 ?
C18 C14 C14 88.5(3) 8_565 8_565 ?
O54 C14 C18 136.4(6) . 8_565 ?
O54 C14 C14 135.1(4) . 8_565 ?
C46 N1 Cu3 128.0(3) . . ?
C46 N1 C3 106.2(4) . . ?
C3 N1 Cu3 125.4(3) . . ?
N9 C17 H17A 109.1 . . ?
N9 C17 H17B 109.1 . . ?
N9 C17 C63 112.4(4) . . ?
H17A C17 H17B 107.9 . . ?
C63 C17 H17A 109.1 . . ?
C63 C17 H17B 109.1 . . ?
N15 C1 C23 112.2(4) . . ?
N15 C1 H1A 109.2 . . ?
N15 C1 H1B 109.2 . . ?
C23 C1 H1A 109.2 . . ?
C23 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
N8 C50 H50 126.4 . . ?
C3 C50 N8 107.2(4) . . ?
C3 C50 H50 126.4 . . ?
N9 C58 H58 127.3 . . ?
C81 C58 N9 105.3(4) . . ?
C81 C58 H58 127.3 . . ?
N4 C63 C17 111.5(4) . . ?
N4 C63 H63A 109.3 . . ?
N4 C63 H63B 109.3 . . ?
C17 C63 H63A 109.3 . . ?
C17 C63 H63B 109.3 . . ?
H63A C63 H63B 108.0 . . ?
N47 C81 C58 109.9(4) . . ?
N47 C81 H81 125.1 . . ?
C58 C81 H81 125.1 . . ?
N1 C3 H3 125.8 . . ?
C50 C3 N1 108.5(4) . . ?
C50 C3 H3 125.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu3 N47 C34 N9 174.6(3) . . . . ?
Cu3 N47 C81 C58 -174.4(4) . . . . ?
Cu3 N1 C3 C50 -175.4(3) . . . . ?
N8 C46 N1 Cu3 174.1(3) . . . . ?
N8 C46 N1 C3 0.2(5) . . . . ?
N8 C23 C1 N15 62.3(5) . . . . ?
N8 C50 C3 N1 1.9(6) . . . . ?
N9 C17 C63 N4 62.2(5) . . . . ?
N9 C58 C81 N47 -0.5(6) . . . . ?
C18 C18 N4 C63 174.6(3) 8_565 . . . ?
C18 N4 C63 C17 -101.3(5) . . . . ?
C46 N8 C23 C1 -93.0(6) . . . . ?
C46 N8 C50 C3 -1.7(6) . . . . ?
C46 N1 C3 C50 -1.3(6) . . . . ?
C60 C60 N15 C1 174.4(3) 8_565 . . . ?
C60 C60 C12 O27 177.9(5) 8_565 . . . ?
C60 C60 C12 C12 -0.001(1) 8_565 . . 8_565 ?
C60 N15 C1 C23 -100.9(5) . . . . ?
N15 C60 C12 O27 0.4(8) . . . . ?
N15 C60 C12 C12 -177.5(4) . . . 8_565 ?
C23 N8 C46 N1 175.9(4) . . . . ?
C23 N8 C50 C3 -176.7(5) . . . . ?
C34 N9 C17 C63 -93.6(6) . . . . ?
C34 N9 C58 C81 0.4(6) . . . . ?
C34 N47 C81 C58 0.5(6) . . . . ?
C12 C60 N15 C1 -9.1(7) . . . . ?
C14 C18 N4 C63 -7.2(7) 8_565 . . . ?
C17 N9 C34 N47 175.8(4) . . . . ?
C17 N9 C58 C81 -175.5(5) . . . . ?
C50 N8 C46 N1 0.9(5) . . . . ?
C50 N8 C23 C1 81.1(6) . . . . ?
C58 N9 C34 N47 -0.1(5) . . . . ?
C58 N9 C17 C63 81.5(6) . . . . ?
C81 N47 C34 N9 -0.2(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 -0.542 0.000 -0.070 766.7 37.1 ?
2 -0.042 0.250 0.283 8.2 0.0 ?
3 -0.484 0.500 -0.381 766.7 37.1 ?
4 0.042 0.750 0.717 8.2 0.0 ?
5 0.167 0.250 0.500 7.3 0.9 ?
6 0.333 0.750 0.000 7.3 1.1 ?
7 0.458 0.250 0.217 8.2 0.0 ?
8 0.542 0.750 0.783 8.2 0.0 ?
9 0.667 0.250 0.000 7.3 0.9 ?
10 0.833 0.750 0.500 7.3 1.1 ?

_olex2_submission_special_instructions 'No special instructions were received'
