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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1532091'
_audit_update_record             
;
2017-02-10 deposited with the CCDC.
2017-12-28 downloaded from the CCDC.
;
_audit_creation_date             2015-08-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H14 Cl Cu N4 S, C H4 O'
_chemical_formula_sum            'C21 H18 Cl Cu N4 O S'
_chemical_formula_weight         473.44
_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'
S S 0.3331 0.5567 '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                   9.4142(8)
_cell_length_b                   10.2389(8)
_cell_length_c                   11.9095(10)
_cell_angle_alpha                87.064(7)
_cell_angle_beta                 67.901(8)
_cell_angle_gamma                71.422(7)
_cell_volume                     1005.13(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2939
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.4080
_cell_measurement_theta_min      4.0070
_shelx_estimated_absorpt_T_max   0.721
_shelx_estimated_absorpt_T_min   0.593
_exptl_absorpt_coefficient_mu    3.895
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7630
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.432
_diffrn_reflns_theta_min         4.019
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 10.5281
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -43.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2335   37.0000 -180.0000 79

#__ type_ start__ end____ width___ exp.time_
  2 omega -119.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2335  -77.0000   60.0000 109

#__ type_ start__ end____ width___ exp.time_
  3 omega  -95.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2335  125.0000 -180.0000 79

#__ type_ start__ end____ width___ exp.time_
  4 omega   59.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2335 -125.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega -115.00  -39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -60.0000 76

#__ type_ start__ end____ width___ exp.time_
  6 omega  -51.00   -3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000   45.0000   30.0000 48

#__ type_ start__ end____ width___ exp.time_
  7 omega   40.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 47

#__ type_ start__ end____ width___ exp.time_
  8 omega   53.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000   60.0000 123

#__ type_ start__ end____ width___ exp.time_
  9 omega   46.00  143.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -60.0000 97

#__ type_ start__ end____ width___ exp.time_
 10 omega  135.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000  -90.0000 40

#__ type_ start__ end____ width___ exp.time_
 11 omega   79.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   30.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  -30.0000 40

#__ type_ start__ end____ width___ exp.time_
 13 omega   82.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 14 omega  106.00  171.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  111.0000 -120.0000 65

#__ type_ start__ end____ width___ exp.time_
 15 omega   79.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
 16 omega   48.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 17 omega   59.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -150.0000 57

#__ type_ start__ end____ width___ exp.time_
 18 omega  114.00  139.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 19 omega   43.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 20 omega   36.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  -60.0000 80

#__ type_ start__ end____ width___ exp.time_
 21 omega   71.00  132.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -30.0000 61

#__ type_ start__ end____ width___ exp.time_
 22 omega   87.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -60.0000 89
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0665400000
_diffrn_orient_matrix_UB_12      -0.1552147000
_diffrn_orient_matrix_UB_13      0.0153222000
_diffrn_orient_matrix_UB_21      0.0675478000
_diffrn_orient_matrix_UB_22      0.0340835000
_diffrn_orient_matrix_UB_23      0.0901809000
_diffrn_orient_matrix_UB_31      -0.1607760000
_diffrn_orient_matrix_UB_32      0.0098755000
_diffrn_orient_matrix_UB_33      0.1060384000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3310
_reflns_number_total             4103
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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         0.523
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.074
_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     264
_refine_ls_number_reflns         4103
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.042
_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)+(0.0428P)²+0.5202P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0964
_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.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C16(H16), C1(H1), C8(H8), C10(H10), C17(H17), C3(H3), C4(H4),
 C2(H2), C20(H20), C19(H19), C9(H9)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_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
Cu1 Cu 0.26163(4) 1.02713(4) 0.23065(3) 0.01805(11) Uani 1 1 d . . . . .
Cl1 Cl 0.42085(7) 1.04053(7) 0.32920(6) 0.02333(15) Uani 1 1 d . . . . .
S1 S 0.58145(7) 1.22549(7) -0.08643(6) 0.02267(15) Uani 1 1 d . . . . .
N2 N 0.1426(2) 0.9190(2) 0.34997(19) 0.0171(4) Uani 1 1 d . . . . .
N3 N -0.0548(2) 0.8248(2) 0.40857(19) 0.0177(4) Uani 1 1 d . . . . .
N4 N 0.3598(3) 1.1347(3) 0.1030(2) 0.0241(5) Uani 1 1 d . . . . .
N1 N 0.0643(2) 1.0663(2) 0.18456(19) 0.0190(4) Uani 1 1 d . . . . .
O1 O 0.3630(4) 0.3678(3) 0.3397(2) 0.0541(8) Uani 1 1 d . . . . .
H1A H 0.3983 0.2862 0.3145 0.081 Uiso 1 1 calc GR . . . .
C13 C 0.4513(3) 1.1719(3) 0.0250(2) 0.0202(5) Uani 1 1 d . . . . .
C6 C 0.0114(3) 0.9131(3) 0.3350(2) 0.0159(5) Uani 1 1 d . . . . .
C12 C 0.1662(3) 0.8282(3) 0.4360(2) 0.0187(5) Uani 1 1 d . . . . .
C15 C -0.1254(3) 0.6906(3) 0.2825(2) 0.0184(5) Uani 1 1 d . . . . .
C14 C -0.1800(3) 0.7716(3) 0.4031(2) 0.0204(5) Uani 1 1 d . . . . .
H14A H -0.2779 0.8484 0.4143 0.024 Uiso 1 1 calc R . . . .
H14B H -0.2055 0.7123 0.4687 0.024 Uiso 1 1 calc R . . . .
C5 C -0.0412(3) 0.9988(3) 0.2469(2) 0.0171(5) Uani 1 1 d . . . . .
C18 C -0.0259(3) 0.5377(2) 0.0602(2) 0.0160(5) Uani 1 1 d . . . . .
C11 C 0.2875(3) 0.7902(3) 0.4846(2) 0.0233(6) Uani 1 1 d . . . . .
H11 H 0.3703 0.8290 0.4605 0.028 Uiso 1 1 calc R . . . .
C7 C 0.0416(3) 0.7685(3) 0.4747(2) 0.0195(5) Uani 1 1 d . . . . .
C16 C -0.2367(3) 0.6914(3) 0.2323(2) 0.0215(5) Uani 1 1 d . . . . .
H16 H -0.3451 0.7433 0.2721 0.026 Uiso 1 1 calc R . . . .
C1 C 0.0326(3) 1.1503(3) 0.1024(2) 0.0234(5) Uani 1 1 d . . . . .
H1 H 0.1053 1.1965 0.0607 0.028 Uiso 1 1 calc R . . . .
C8 C 0.0307(4) 0.6725(3) 0.5618(3) 0.0272(6) Uani 1 1 d . . . . .
H8 H -0.0527 0.6344 0.5873 0.033 Uiso 1 1 calc R . . . .
C10 C 0.2785(4) 0.6932(3) 0.5693(3) 0.0298(6) Uani 1 1 d . . . . .
H10 H 0.3585 0.6642 0.6015 0.036 Uiso 1 1 calc R . . . .
C17 C -0.1884(3) 0.6158(3) 0.1235(2) 0.0213(5) Uani 1 1 d . . . . .
H17 H -0.2653 0.6169 0.0919 0.026 Uiso 1 1 calc R . . . .
C3 C -0.2125(3) 1.1033(3) 0.1389(3) 0.0248(6) Uani 1 1 d . . . . .
H3 H -0.3054 1.1155 0.1232 0.030 Uiso 1 1 calc R . . . .
C4 C -0.1806(3) 1.0162(3) 0.2251(2) 0.0222(5) Uani 1 1 d . . . . .
H4 H -0.2521 0.9696 0.2683 0.027 Uiso 1 1 calc R . . . .
C2 C -0.1044(3) 1.1724(3) 0.0758(3) 0.0262(6) Uani 1 1 d . . . . .
H2 H -0.1233 1.2318 0.0175 0.031 Uiso 1 1 calc R . . . .
C20 C 0.0358(3) 0.6104(3) 0.2225(3) 0.0264(6) Uani 1 1 d . . . . .
H20 H 0.1116 0.6067 0.2560 0.032 Uiso 1 1 calc R . . . .
C19 C 0.0840(3) 0.5358(3) 0.1130(3) 0.0260(6) Uani 1 1 d . . . . .
H19 H 0.1923 0.4832 0.0740 0.031 Uiso 1 1 calc R . . . .
C9 C 0.1512(4) 0.6371(3) 0.6083(3) 0.0325(7) Uani 1 1 d . . . . .
H9 H 0.1479 0.5739 0.6674 0.039 Uiso 1 1 calc R . . . .
C21 C 0.4385(4) 0.4441(4) 0.2497(3) 0.0359(7) Uani 1 1 d . . . . .
H21A H 0.4135 0.4380 0.1795 0.054 Uiso 1 1 calc GR . . . .
H21B H 0.5537 0.4076 0.2277 0.054 Uiso 1 1 calc GR . . . .
H21C H 0.4002 0.5391 0.2803 0.054 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 Cl1 2.2615(7) . ?
Cu1 N2 1.983(2) . ?
Cu1 N4 1.949(2) . ?
Cu1 N1 2.045(2) . ?
S1 C13 1.641(3) . ?
N2 C6 1.332(3) . ?
N2 C12 1.380(3) . ?
N3 C6 1.357(3) . ?
N3 C14 1.470(3) . ?
N3 C7 1.391(3) . ?
N4 C13 1.149(4) . ?
N1 C5 1.359(3) . ?
N1 C1 1.325(4) . ?
O1 C21 1.400(4) . ?
C6 C5 1.461(3) . ?
C12 C11 1.408(4) . ?
C12 C7 1.408(4) . ?
C15 C14 1.519(3) . ?
C15 C16 1.386(4) . ?
C15 C20 1.392(4) . ?
C5 C4 1.387(4) . ?
C18 C18 1.496(5) 2_565 ?
C18 C17 1.401(3) . ?
C18 C19 1.393(4) . ?
C11 C10 1.378(4) . ?
C7 C8 1.390(4) . ?
C16 C17 1.386(4) . ?
C1 C2 1.389(4) . ?
C8 C9 1.384(4) . ?
C10 C9 1.405(4) . ?
C3 C4 1.381(4) . ?
C3 C2 1.389(4) . ?
C20 C19 1.388(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 Cl1 96.29(7) . . ?
N2 Cu1 N1 80.52(9) . . ?
N4 Cu1 Cl1 90.99(7) . . ?
N4 Cu1 N2 172.69(10) . . ?
N4 Cu1 N1 92.36(9) . . ?
N1 Cu1 Cl1 160.98(6) . . ?
C6 N2 Cu1 114.03(17) . . ?
C6 N2 C12 106.5(2) . . ?
C12 N2 Cu1 138.55(18) . . ?
C6 N3 C14 127.8(2) . . ?
C6 N3 C7 106.9(2) . . ?
C7 N3 C14 123.9(2) . . ?
C13 N4 Cu1 163.2(2) . . ?
C5 N1 Cu1 114.74(17) . . ?
C1 N1 Cu1 125.93(18) . . ?
C1 N1 C5 119.3(2) . . ?
N4 C13 S1 179.8(3) . . ?
N2 C6 N3 112.0(2) . . ?
N2 C6 C5 118.4(2) . . ?
N3 C6 C5 129.6(2) . . ?
N2 C12 C11 131.3(3) . . ?
N2 C12 C7 108.5(2) . . ?
C7 C12 C11 120.2(2) . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 C20 118.7(2) . . ?
C20 C15 C14 120.9(2) . . ?
N3 C14 C15 111.8(2) . . ?
N1 C5 C6 111.8(2) . . ?
N1 C5 C4 120.9(2) . . ?
C4 C5 C6 127.3(2) . . ?
C17 C18 C18 120.6(3) . 2_565 ?
C19 C18 C18 122.1(3) . 2_565 ?
C19 C18 C17 117.3(2) . . ?
C10 C11 C12 117.2(3) . . ?
N3 C7 C12 106.0(2) . . ?
C8 C7 N3 131.4(3) . . ?
C8 C7 C12 122.6(3) . . ?
C15 C16 C17 120.8(2) . . ?
N1 C1 C2 122.9(3) . . ?
C9 C8 C7 116.1(3) . . ?
C11 C10 C9 121.5(3) . . ?
C16 C17 C18 121.2(2) . . ?
C4 C3 C2 119.2(3) . . ?
C3 C4 C5 119.6(2) . . ?
C3 C2 C1 118.1(3) . . ?
C19 C20 C15 120.3(3) . . ?
C20 C19 C18 121.6(2) . . ?
C8 C9 C10 122.3(3) . . ?

_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_2
_database_code_depnum_ccdc_archive 'CCDC 1532092'
_audit_update_record             
;
2017-02-10 deposited with the CCDC.
2017-12-28 downloaded from the CCDC.
;
_audit_creation_date             2015-08-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '0.5(C76 H56 Br6 Cu4 N12 O2)'
_chemical_formula_sum            'C38 H28 Br3 Cu2 N6 O'
_chemical_formula_weight         951.47
_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      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   9.7938(3)
_cell_length_b                   19.0133(15)
_cell_length_c                   14.1848(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.517(4)
_cell_angle_gamma                90
_cell_volume                     2568.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1969
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      68.3410
_cell_measurement_theta_min      3.9460
_shelx_estimated_absorpt_T_max   0.741
_shelx_estimated_absorpt_T_min   0.587
_exptl_absorpt_coefficient_mu    3.981
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             938
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0830
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            ?
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.319
_diffrn_reflns_theta_min         3.204
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 10.5281
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -103.00  -14.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2335  -37.0000    0.0000 89

#__ type_ start__ end____ width___ exp.time_
  2 omega  -96.00   -4.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.2335  125.0000  150.0000 92

#__ type_ start__ end____ width___ exp.time_
  3 omega -116.00  -89.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000 -111.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega  -31.00   16.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000   30.0000  -60.0000 47

#__ type_ start__ end____ width___ exp.time_
  5 omega  117.00  144.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   39.00  105.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000 -120.0000 66

#__ type_ start__ end____ width___ exp.time_
  7 omega   51.00  143.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   60.0000 92

#__ type_ start__ end____ width___ exp.time_
  8 omega   35.00   90.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 55

#__ type_ start__ end____ width___ exp.time_
  9 omega   52.00   99.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -30.0000 47

#__ type_ start__ end____ width___ exp.time_
 10 omega   64.00   92.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
 11 omega   41.00   80.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 39

#__ type_ start__ end____ width___ exp.time_
 12 omega   87.00  114.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 13 omega  139.00  174.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 35

#__ type_ start__ end____ width___ exp.time_
 14 omega   40.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 51

#__ type_ start__ end____ width___ exp.time_
 15 omega   79.00  178.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 99
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1599487000
_diffrn_orient_matrix_UB_12      -0.0090575000
_diffrn_orient_matrix_UB_13      -0.0154472000
_diffrn_orient_matrix_UB_21      -0.0234167000
_diffrn_orient_matrix_UB_22      0.0694085000
_diffrn_orient_matrix_UB_23      -0.0576265000
_diffrn_orient_matrix_UB_31      -0.0043020000
_diffrn_orient_matrix_UB_32      -0.0409595000
_diffrn_orient_matrix_UB_33      -0.0943795000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2583
_reflns_number_total             5450
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         1.842
_refine_diff_density_min         -1.500
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         5450
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1282
_refine_ls_R_factor_gt           0.0794
_refine_ls_restrained_S_all      0.981
_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)+(0.1176P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2185
_refine_ls_wR_factor_ref         0.2373
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C1(H1), C11(H11), C4(H4), C2(H2), C3(H3), C9(H9), C18(H18),
 C16(H16), C8(H8), C10(H10), C19(H19)
;
_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
Br1 Br 0.37726(7) 0.63043(6) 0.56989(7) 0.0768(3) Uani 1 1 d . . . . .
Cu1 Cu 0.14848(10) 0.66639(7) 0.46443(9) 0.0691(4) Uani 1 1 d . . . . .
Br2 Br 0.1386(3) 0.7500 0.31855(15) 0.1218(7) Uani 1 2 d S T P . .
N3 N 0.0081(6) 0.4887(4) 0.3172(6) 0.0704(19) Uani 1 1 d . . . . .
N1 N -0.0460(5) 0.6262(4) 0.4807(5) 0.0616(17) Uani 1 1 d . . . . .
C7 C 0.1332(8) 0.4882(6) 0.2866(7) 0.077(3) Uani 1 1 d . . . . .
C17 C -0.4416(8) 0.4908(6) 0.0421(6) 0.070(2) Uani 1 1 d . . . . .
C15 C -0.3174(10) 0.4070(6) 0.1614(7) 0.086(3) Uani 1 1 d . . . . .
H15 H -0.3124 0.3619 0.1875 0.104 Uiso 1 1 calc R . . . .
C14 C -0.2200(7) 0.4565(5) 0.1999(6) 0.068(2) Uani 1 1 d . . . . .
C1 C -0.1231(7) 0.6552(5) 0.5354(7) 0.070(2) Uani 1 1 d . . . . .
H1 H -0.0878 0.6937 0.5738 0.084 Uiso 1 1 calc R . . . .
C11 C 0.3419(8) 0.5585(7) 0.3156(7) 0.096(4) Uani 1 1 d . . . . .
H11 H 0.3936 0.5967 0.3458 0.115 Uiso 1 1 calc R . . . .
C4 C -0.2259(8) 0.5406(5) 0.4224(7) 0.077(3) Uani 1 1 d . . . . .
H4 H -0.2577 0.5024 0.3825 0.093 Uiso 1 1 calc R . . . .
N2 N 0.1271(6) 0.5831(5) 0.3821(5) 0.075(2) Uani 1 1 d . . . . .
C2 C -0.2567(7) 0.6293(6) 0.5372(7) 0.078(3) Uani 1 1 d . . . . .
H2 H -0.3107 0.6507 0.5750 0.093 Uiso 1 1 calc R . . . .
C5 C -0.0943(7) 0.5713(6) 0.4270(6) 0.073(3) Uani 1 1 d . . . . .
C12 C 0.2056(7) 0.5452(6) 0.3279(6) 0.073(3) Uani 1 1 d . . . . .
C13 C -0.1039(8) 0.4350(5) 0.2885(7) 0.077(3) Uani 1 1 d . . . . .
H13A H -0.1461 0.4264 0.3429 0.093 Uiso 1 1 calc R . . . .
H13B H -0.0618 0.3914 0.2741 0.093 Uiso 1 1 calc R . . . .
C3 C -0.3060(7) 0.5705(6) 0.4805(7) 0.076(3) Uani 1 1 d . . . . .
H3 H -0.3929 0.5513 0.4818 0.091 Uiso 1 1 calc R . . . .
C6 C 0.0095(7) 0.5447(5) 0.3739(6) 0.067(2) Uani 1 1 d . . . . .
C9 C 0.3173(12) 0.4605(8) 0.2156(9) 0.112(4) Uani 1 1 d . . . . .
H9 H 0.3525 0.4340 0.1715 0.134 Uiso 1 1 calc R . . . .
C18 C -0.3411(11) 0.5396(6) 0.0819(9) 0.115(5) Uani 1 1 d . . . . .
H18 H -0.3458 0.5848 0.0562 0.138 Uiso 1 1 calc R . . . .
C16 C -0.4268(9) 0.4255(7) 0.0806(7) 0.089(3) Uani 1 1 d . . . . .
H16 H -0.4913 0.3912 0.0529 0.107 Uiso 1 1 calc R . . . .
C8 C 0.1834(10) 0.4404(7) 0.2314(8) 0.099(4) Uani 1 1 d . . . . .
H8 H 0.1363 0.3995 0.2068 0.119 Uiso 1 1 calc R . . . .
C10 C 0.3958(9) 0.5139(6) 0.2584(8) 0.089(3) Uani 1 1 d . . . . .
H10 H 0.4860 0.5207 0.2493 0.107 Uiso 1 1 calc R . . . .
C19 C -0.2295(10) 0.5213(6) 0.1628(9) 0.099(4) Uani 1 1 d . . . . .
H19 H -0.1628 0.5549 0.1898 0.118 Uiso 1 1 calc R . . . .
O1 O 0.1347(7) 0.7500 0.5368(6) 0.0619(19) Uani 1 2 d S T P . .


_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
Br1 Cu1 2.4816(13) . ?
Cu1 Br2 2.593(2) . ?
Cu1 N1 2.114(5) . ?
Cu1 N2 1.950(9) . ?
Cu1 O1 1.914(5) . ?
Br2 Cu1 2.593(2) 4_575 ?
N3 C7 1.392(10) . ?
N3 C13 1.484(10) . ?
N3 C6 1.332(11) . ?
N1 C1 1.324(11) . ?
N1 C5 1.313(12) . ?
C7 C12 1.351(14) . ?
C7 C8 1.365(15) . ?
C17 C17 1.490(16) 3_465 ?
C17 C18 1.375(12) . ?
C17 C16 1.350(14) . ?
C15 C14 1.361(12) . ?
C15 C16 1.418(13) . ?
C14 C13 1.540(12) . ?
C14 C19 1.335(13) . ?
C1 C2 1.403(10) . ?
C11 C12 1.409(10) . ?
C11 C10 1.363(14) . ?
C4 C5 1.402(11) . ?
C4 C3 1.385(13) . ?
N2 C12 1.407(11) . ?
N2 C6 1.346(10) . ?
C2 C3 1.396(14) . ?
C5 C6 1.487(11) . ?
C9 C8 1.433(15) . ?
C9 C10 1.331(16) . ?
C18 C19 1.430(13) . ?
O1 Cu1 1.914(5) 4_575 ?

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
Br1 Cu1 Br2 120.67(8) . . ?
N1 Cu1 Br1 123.0(2) . . ?
N1 Cu1 Br2 116.2(2) . . ?
N2 Cu1 Br1 95.33(19) . . ?
N2 Cu1 Br2 92.4(2) . . ?
N2 Cu1 N1 78.3(3) . . ?
O1 Cu1 Br1 94.2(2) . . ?
O1 Cu1 Br2 85.7(2) . . ?
O1 Cu1 N1 93.7(3) . . ?
O1 Cu1 N2 169.9(3) . . ?
Cu1 Br2 Cu1 75.62(8) . 4_575 ?
C7 N3 C13 123.9(8) . . ?
C6 N3 C7 108.0(7) . . ?
C6 N3 C13 128.1(7) . . ?
C1 N1 Cu1 124.4(6) . . ?
C5 N1 Cu1 115.8(5) . . ?
C5 N1 C1 119.6(7) . . ?
C12 C7 N3 105.7(8) . . ?
C12 C7 C8 124.0(9) . . ?
C8 C7 N3 130.2(10) . . ?
C18 C17 C17 120.8(12) . 3_465 ?
C16 C17 C17 122.0(10) . 3_465 ?
C16 C17 C18 117.1(9) . . ?
C14 C15 C16 118.6(10) . . ?
C15 C14 C13 117.3(9) . . ?
C19 C14 C15 120.2(9) . . ?
C19 C14 C13 122.5(8) . . ?
N1 C1 C2 121.8(9) . . ?
C10 C11 C12 118.2(10) . . ?
C3 C4 C5 116.4(9) . . ?
C12 N2 Cu1 138.4(6) . . ?
C6 N2 Cu1 117.5(6) . . ?
C6 N2 C12 104.0(8) . . ?
C3 C2 C1 118.0(8) . . ?
N1 C5 C4 124.0(8) . . ?
N1 C5 C6 111.6(7) . . ?
C4 C5 C6 124.4(10) . . ?
C7 C12 C11 120.5(9) . . ?
C7 C12 N2 110.4(7) . . ?
N2 C12 C11 129.1(10) . . ?
N3 C13 C14 113.5(8) . . ?
C4 C3 C2 120.2(8) . . ?
N3 C6 N2 111.9(7) . . ?
N3 C6 C5 131.7(8) . . ?
N2 C6 C5 116.4(9) . . ?
C10 C9 C8 125.8(11) . . ?
C17 C18 C19 120.3(10) . . ?
C17 C16 C15 123.0(9) . . ?
C7 C8 C9 112.2(11) . . ?
C9 C10 C11 118.9(9) . . ?
C14 C19 C18 120.7(9) . . ?
Cu1 O1 Cu1 112.3(4) 4_575 . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.020 0.000 0.000 1060 330 ' '

#===END
