# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_CuCl
_database_code_depnum_ccdc_archive 'CCDC 1560294'
_audit_update_record             
;
2017-10-21 deposited with the CCDC.
2017-11-10 downloaded from the CCDC.
;
_audit_creation_date             2017-10-21
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H20 Cl Cu2 N6 O5'
_chemical_formula_sum            'C32 H20 Cl Cu2 N6 O5'
_chemical_formula_weight         731.09
_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      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                   22.7003(12)
_cell_length_b                   16.1285(7)
_cell_length_c                   11.5653(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.890(3)
_cell_angle_gamma                90
_cell_volume                     3776.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1552
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.87
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.395
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1396
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7153
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.059
_diffrn_reflns_theta_min         3.503
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2981
_reflns_number_total             3593
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3593
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0509
_refine_ls_restrained_S_all      1.085
_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)+(0.0768P)²+5.0855P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1475
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C9(H9), C15(H15), C13(H13), C7(H7), C12(H12), C1(H1), C4(H4),
 C2(H2), C5(H5)
;
_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 -0.42252(2) 0.36711(3) 0.30973(4) 0.01806(17) Uani 1 1 d . . . . .
Cl1 Cl -0.5000 0.49073(7) 0.2500 0.0259(3) Uani 1 2 d S T P . .
O2 O -0.08570(11) 0.84109(15) 0.3557(2) 0.0216(5) Uani 1 1 d . . . . .
O3 O -0.5000 0.2961(2) 0.2500 0.0209(6) Uani 1 2 d S T P . .
O1 O -0.14669(13) 0.74599(17) 0.2124(2) 0.0310(6) Uani 1 1 d . . . . .
N2 N -0.09962(14) 0.83814(17) 1.0021(2) 0.0202(6) Uani 1 1 d . . . . .
N1 N -0.34490(14) 0.44672(18) 0.3705(3) 0.0217(6) Uani 1 1 d . . . . .
N3 N -0.18349(14) 0.67516(18) 0.5935(3) 0.0225(6) Uani 1 1 d . . . . .
C14 C -0.07710(17) 0.8339(2) 0.8193(3) 0.0224(7) Uani 1 1 d . . . . .
H14 H -0.0523 0.8532 0.7793 0.027 Uiso 1 1 calc R . . . .
C8 C -0.13990(17) 0.7403(2) 0.4233(3) 0.0226(7) Uani 1 1 d . . . . .
C3 C -0.24928(17) 0.5710(2) 0.4420(3) 0.0236(7) Uani 1 1 d . . . . .
C6 C -0.20270(17) 0.6412(2) 0.4762(3) 0.0230(7) Uani 1 1 d . . . . .
C9 C -0.11902(17) 0.7739(2) 0.5454(3) 0.0235(7) Uani 1 1 d . . . . .
H9 H -0.0897 0.8183 0.5723 0.028 Uiso 1 1 calc R . . . .
C15 C -0.06509(17) 0.8632(2) 0.9400(3) 0.0218(7) Uani 1 1 d . . . . .
H15 H -0.0316 0.9021 0.9801 0.026 Uiso 1 1 calc R . . . .
C16 C -0.12196(16) 0.7780(2) 0.3231(3) 0.0228(7) Uani 1 1 d . . . . .
C13 C -0.14779(18) 0.7825(2) 0.9425(3) 0.0289(8) Uani 1 1 d . . . . .
H13 H -0.1724 0.7651 0.9841 0.035 Uiso 1 1 calc R . . . .
C7 C -0.18197(18) 0.6728(2) 0.3880(3) 0.0252(7) Uani 1 1 d . . . . .
H7 H -0.1963 0.6487 0.3066 0.030 Uiso 1 1 calc R . . . .
C10 C -0.14268(17) 0.7399(2) 0.6284(3) 0.0226(7) Uani 1 1 d . . . . .
C11 C -0.12648(17) 0.7755(2) 0.7578(3) 0.0225(7) Uani 1 1 d . . . . .
C12 C -0.16239(19) 0.7500(2) 0.8235(3) 0.0295(8) Uani 1 1 d . . . . .
H12 H -0.1960 0.7111 0.7861 0.035 Uiso 1 1 calc R . . . .
C1 C -0.3351(2) 0.4991(2) 0.4667(3) 0.0317(8) Uani 1 1 d . . . . .
H1 H -0.3612 0.4940 0.5092 0.038 Uiso 1 1 calc R . . . .
C4 C -0.2610(2) 0.5176(3) 0.3414(4) 0.0408(10) Uani 1 1 d . . . . .
H4 H -0.2370 0.5227 0.2946 0.049 Uiso 1 1 calc R . . . .
C2 C -0.2878(2) 0.5604(2) 0.5057(3) 0.0308(8) Uani 1 1 d . . . . .
H2 H -0.2818 0.5947 0.5749 0.037 Uiso 1 1 calc R . . . .
C5 C -0.3079(2) 0.4568(3) 0.3096(4) 0.0377(10) Uani 1 1 d . . . . .
H5 H -0.3142 0.4209 0.2420 0.045 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
Cu1 Cl1 2.5389(10) . ?
Cu1 O2 2.049(2) 4_445 ?
Cu1 O3 1.9453(19) . ?
Cu1 N2 2.054(3) 4_446 ?
Cu1 N1 2.032(3) . ?
Cl1 Cu1 2.5389(10) 2_455 ?
O2 Cu1 2.049(2) 4_455 ?
O2 C16 1.254(4) . ?
O3 Cu1 1.9452(19) 2_455 ?
O1 C16 1.254(4) . ?
N2 Cu1 2.054(3) 4_456 ?
N2 C15 1.342(4) . ?
N2 C13 1.340(5) . ?
N1 C1 1.332(4) . ?
N1 C5 1.328(4) . ?
N3 C6 1.340(4) . ?
N3 C10 1.332(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(4) . ?
C14 C11 1.389(5) . ?
C8 C9 1.380(5) . ?
C8 C16 1.519(4) . ?
C8 C7 1.383(5) . ?
C3 C6 1.475(5) . ?
C3 C4 1.374(5) . ?
C3 C2 1.386(5) . ?
C6 C7 1.399(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.405(4) . ?
C15 H15 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.366(5) . ?
C7 H7 0.9300 . ?
C10 C11 1.486(4) . ?
C11 C12 1.404(5) . ?
C12 H12 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.376(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.369(6) . ?
C2 H2 0.9300 . ?
C5 H5 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
O2 Cu1 Cl1 104.56(7) 4_445 . ?
O2 Cu1 N2 149.47(11) 4_445 4_446 ?
O3 Cu1 Cl1 87.83(8) . . ?
O3 Cu1 O2 89.85(7) . 4_445 ?
O3 Cu1 N2 89.48(8) . 4_446 ?
O3 Cu1 N1 176.87(11) . . ?
N2 Cu1 Cl1 105.92(8) 4_446 . ?
N1 Cu1 Cl1 89.05(8) . . ?
N1 Cu1 O2 91.24(10) . 4_445 ?
N1 Cu1 N2 91.08(11) . 4_446 ?
Cu1 Cl1 Cu1 76.51(4) 2_455 . ?
C16 O2 Cu1 102.11(19) . 4_455 ?
Cu1 O3 Cu1 107.83(15) 2_455 . ?
C15 N2 Cu1 125.1(2) . 4_456 ?
C13 N2 Cu1 116.7(2) . 4_456 ?
C13 N2 C15 117.7(3) . . ?
C1 N1 Cu1 118.8(2) . . ?
C5 N1 Cu1 123.5(2) . . ?
C5 N1 C1 117.3(3) . . ?
C10 N3 C6 119.4(3) . . ?
C15 C14 H14 120.1 . . ?
C15 C14 C11 119.7(3) . . ?
C11 C14 H14 120.1 . . ?
C9 C8 C16 122.5(3) . . ?
C9 C8 C7 118.9(3) . . ?
C7 C8 C16 118.5(3) . . ?
C4 C3 C6 123.3(3) . . ?
C4 C3 C2 116.4(3) . . ?
C2 C3 C6 120.1(3) . . ?
N3 C6 C3 116.8(3) . . ?
N3 C6 C7 121.8(3) . . ?
C7 C6 C3 121.4(3) . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 119.0(3) . . ?
C10 C9 H9 120.5 . . ?
N2 C15 C14 122.8(3) . . ?
N2 C15 H15 118.6 . . ?
C14 C15 H15 118.6 . . ?
O2 C16 C8 117.5(3) . . ?
O1 C16 O2 124.8(3) . . ?
O1 C16 C8 117.6(3) . . ?
N2 C13 H13 118.5 . . ?
N2 C13 C12 123.0(3) . . ?
C12 C13 H13 118.5 . . ?
C8 C7 C6 119.1(3) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
N3 C10 C9 121.8(3) . . ?
N3 C10 C11 115.4(3) . . ?
C9 C10 C11 122.7(3) . . ?
C14 C11 C10 123.5(3) . . ?
C14 C11 C12 117.0(3) . . ?
C12 C11 C10 119.5(3) . . ?
C13 C12 C11 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
N1 C1 H1 118.6 . . ?
N1 C1 C2 122.7(3) . . ?
C2 C1 H1 118.6 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 C3 120.1(3) . . ?
C1 C2 H2 120.0 . . ?
N1 C5 C4 123.1(3) . . ?
N1 C5 H5 118.4 . . ?
C4 C5 H5 118.4 . . ?

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 O2 C16 O1 -2.6(4) 4_455 . . . ?
Cu1 O2 C16 C8 -179.5(2) 4_455 . . . ?
Cu1 N2 C15 C14 171.8(3) 4_456 . . . ?
Cu1 N2 C13 C12 -172.0(3) 4_456 . . . ?
Cu1 N1 C1 C2 -173.6(3) . . . . ?
Cu1 N1 C5 C4 171.7(4) . . . . ?
N2 C13 C12 C11 -0.6(6) . . . . ?
N1 C1 C2 C3 1.7(6) . . . . ?
N3 C6 C7 C8 0.8(6) . . . . ?
N3 C10 C11 C14 169.3(3) . . . . ?
N3 C10 C11 C12 -10.9(5) . . . . ?
C14 C11 C12 C13 -0.2(6) . . . . ?
C8 C9 C10 N3 1.5(5) . . . . ?
C8 C9 C10 C11 -175.8(3) . . . . ?
C3 C6 C7 C8 177.9(3) . . . . ?
C3 C4 C5 N1 1.2(8) . . . . ?
C6 N3 C10 C9 0.0(5) . . . . ?
C6 N3 C10 C11 177.5(3) . . . . ?
C6 C3 C4 C5 -175.9(4) . . . . ?
C6 C3 C2 C1 174.7(4) . . . . ?
C9 C8 C16 O2 1.4(5) . . . . ?
C9 C8 C16 O1 -175.7(3) . . . . ?
C9 C8 C7 C6 0.8(5) . . . . ?
C9 C10 C11 C14 -13.3(5) . . . . ?
C9 C10 C11 C12 166.5(4) . . . . ?
C15 N2 C13 C12 0.8(6) . . . . ?
C15 C14 C11 C10 -179.6(3) . . . . ?
C15 C14 C11 C12 0.6(5) . . . . ?
C16 C8 C9 C10 174.2(3) . . . . ?
C16 C8 C7 C6 -175.4(3) . . . . ?
C13 N2 C15 C14 -0.3(5) . . . . ?
C7 C8 C9 C10 -1.8(5) . . . . ?
C7 C8 C16 O2 177.5(3) . . . . ?
C7 C8 C16 O1 0.4(5) . . . . ?
C10 N3 C6 C3 -178.4(3) . . . . ?
C10 N3 C6 C7 -1.2(5) . . . . ?
C10 C11 C12 C13 -180.0(3) . . . . ?
C11 C14 C15 N2 -0.4(5) . . . . ?
C1 N1 C5 C4 0.1(7) . . . . ?
C4 C3 C6 N3 -163.7(4) . . . . ?
C4 C3 C6 C7 19.0(6) . . . . ?
C4 C3 C2 C1 -0.4(6) . . . . ?
C2 C3 C6 N3 21.5(5) . . . . ?
C2 C3 C6 C7 -155.7(4) . . . . ?
C2 C3 C4 C5 -1.0(7) . . . . ?
C5 N1 C1 C2 -1.6(6) . . . . ?

_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 0.500 0.000 0.061 569 179 ' '
2 0.000 0.500 -0.016 569 179 ' '
_platon_squeeze_details          ?

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

data_Cu
_database_code_depnum_ccdc_archive 'CCDC 1581237'
_audit_update_record             
;
2017-10-21 deposited with the CCDC.
2017-11-10 downloaded from the CCDC.
;
_audit_creation_date             2017-10-04
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H22 Cu N6 O5'
_chemical_formula_sum            'C32 H22 Cu N6 O5'
_chemical_formula_weight         634.11
_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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.249(3)
_cell_length_b                   14.078(3)
_cell_length_c                   16.178(3)
_cell_angle_alpha                90
_cell_angle_beta                 117.20(3)
_cell_angle_gamma                90
_cell_volume                     3089.0(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1300
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.87
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.756
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2808
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_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            8260
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.127
_diffrn_reflns_theta_min         2.024
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7536
_reflns_number_total             8260
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.845
_refine_diff_density_min         -0.662
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       0.0122(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         8260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.043
_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)+(0.0786P)²+2.5878P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1421
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C27(H27), C3(H3), C19(H19), C8(H8), C11(H11), C22(H22), C6(H6), C9(H9),
 C10(H10), C26(H26), C29(H29), C24(H24), C23(H23), C13(H13), C31(H31), C28(H28),
  C15(H15), C32(H32), C12(H12), C16(H16)
;
_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 0.37276(2) 0.49528(2) 0.56741(2) 0.01882(10) Uani 1 1 d . . . . .
O1 O 0.44764(10) 0.46703(10) 0.69900(8) 0.0229(3) Uani 1 1 d . . . . .
O3 O 0.31025(10) 0.52967(9) 0.43598(8) 0.0218(3) Uani 1 1 d . . . . .
O5 O 0.24868(11) 0.40059(11) 0.56249(10) 0.0301(3) Uani 1 1 d . . . . .
H5A H 0.1893 0.4193 0.5483 0.045 Uiso 1 1 d GR . . . .
H5B H 0.2536 0.3403 0.5743 0.045 Uiso 1 1 d GR . . . .
N3 N 0.44167(11) 0.11612(11) 1.03942(10) 0.0197(3) Uani 1 1 d . . . . .
O2 O 0.55857(12) 0.58460(12) 0.74497(10) 0.0340(3) Uani 1 1 d . . . . .
N4 N 0.31940(11) 0.88307(11) 0.09416(10) 0.0205(3) Uani 1 1 d . . . . .
N2 N 0.61103(11) 0.42278(11) 1.04086(10) 0.0202(3) Uani 1 1 d . . . . .
N5 N 0.18437(11) 0.55796(11) 0.09360(10) 0.0215(3) Uani 1 1 d . . . . .
O4 O 0.19940(14) 0.41235(13) 0.38137(11) 0.0443(5) Uani 1 1 d . . . . .
C5 C 0.54580(12) 0.37169(12) 0.96936(11) 0.0187(3) Uani 1 1 d . . . . .
C27 C 0.29444(13) 0.80789(12) 0.03660(12) 0.0211(3) Uani 1 1 d . . . . .
H27 H 0.2969 0.8141 -0.0195 0.025 Uiso 1 1 calc R . . . .
C4 C 0.64884(14) 0.50179(11) 1.02271(13) 0.0194(3) Uani 1 1 d . . . . .
C3 C 0.62299(12) 0.53126(13) 0.93206(11) 0.0202(3) Uani 1 1 d . . . . .
H3 H 0.6526 0.5844 0.9213 0.024 Uiso 1 1 calc R . . . .
C19 C 0.25486(13) 0.59575(13) 0.25642(12) 0.0212(3) Uani 1 1 d . . . . .
H19 H 0.2902 0.6379 0.3045 0.025 Uiso 1 1 calc R . . . .
C20 C 0.23208(12) 0.61819(12) 0.16477(11) 0.0198(3) Uani 1 1 d . . . . .
C2 C 0.55245(13) 0.48008(13) 0.85821(12) 0.0194(3) Uani 1 1 d . . . . .
C8 C 0.50809(13) 0.27350(12) 1.07823(11) 0.0195(3) Uani 1 1 d . . . . .
H8 H 0.5302 0.3227 1.1213 0.023 Uiso 1 1 calc R . . . .
C11 C 0.47968(13) 0.20522(12) 0.93362(11) 0.0197(3) Uani 1 1 d . . . . .
H11 H 0.4810 0.2081 0.8767 0.024 Uiso 1 1 calc R . . . .
N6 N -0.01278(14) 0.30174(15) -0.12950(13) 0.0370(4) Uani 1 1 d . . . . .
C22 C 0.17230(14) 0.44718(13) 0.20056(12) 0.0234(3) Uani 1 1 d . . . . .
H22 H 0.1500 0.3891 0.2109 0.028 Uiso 1 1 calc R . . . .
C6 C 0.51255(13) 0.39894(12) 0.87678(11) 0.0195(3) Uani 1 1 d . . . . .
H6 H 0.4648 0.3636 0.8287 0.023 Uiso 1 1 calc R . . . .
C7 C 0.51035(12) 0.28312(13) 0.99354(11) 0.0185(3) Uani 1 1 d . . . . .
C9 C 0.47284(13) 0.19040(12) 1.09821(11) 0.0202(3) Uani 1 1 d . . . . .
H9 H 0.4706 0.1858 1.1546 0.024 Uiso 1 1 calc R . . . .
C10 C 0.44744(13) 0.12396(13) 0.95895(12) 0.0206(3) Uani 1 1 d . . . . .
H10 H 0.4288 0.0722 0.9187 0.025 Uiso 1 1 calc R . . . .
C26 C 0.26536(13) 0.72195(12) 0.05708(12) 0.0213(3) Uani 1 1 d . . . . .
H26 H 0.2495 0.6715 0.0156 0.026 Uiso 1 1 calc R . . . .
C18 C 0.22351(14) 0.50912(13) 0.27391(13) 0.0218(3) Uani 1 1 d . . . . .
C29 C 0.07029(15) 0.44640(15) -0.05914(12) 0.0265(4) Uani 1 1 d . . . . .
H29 H 0.0878 0.5077 -0.0673 0.032 Uiso 1 1 calc R . . . .
C17 C 0.24446(15) 0.48080(14) 0.37144(13) 0.0236(3) Uani 1 1 d . . . . .
C1 C 0.51889(14) 0.51460(13) 0.75969(12) 0.0216(3) Uani 1 1 d . . . . .
C25 C 0.25994(12) 0.71106(13) 0.14016(12) 0.0201(3) Uani 1 1 d . . . . .
C21 C 0.15494(13) 0.47350(13) 0.11128(12) 0.0212(3) Uani 1 1 d . . . . .
C30 C 0.09946(14) 0.41122(13) 0.02927(12) 0.0235(3) Uani 1 1 d . . . . .
C14 C 0.71961(14) 0.55624(15) 1.10408(13) 0.0258(4) Uani 1 1 d . . . . .
C24 C 0.28168(14) 0.79020(13) 0.19827(12) 0.0236(3) Uani 1 1 d . . . . .
H24 H 0.2765 0.7868 0.2533 0.028 Uiso 1 1 calc R . . . .
C23 C 0.31109(14) 0.87386(13) 0.17314(12) 0.0239(3) Uani 1 1 d . . . . .
H23 H 0.3257 0.9260 0.2126 0.029 Uiso 1 1 calc R . . . .
C13 C 0.73859(15) 0.65062(15) 1.09783(16) 0.0312(4) Uani 1 1 d . . . . .
H13 H 0.7078 0.6829 1.0416 0.037 Uiso 1 1 calc R . . . .
C31 C 0.07349(19) 0.31921(16) 0.03733(14) 0.0365(5) Uani 1 1 d . . . . .
H31 H 0.0930 0.2921 0.0956 0.044 Uiso 1 1 calc R . . . .
C28 C 0.01480(16) 0.38995(17) -0.13568(14) 0.0339(4) Uani 1 1 d . . . . .
H28 H -0.0042 0.4152 -0.1945 0.041 Uiso 1 1 calc R . . . .
C15 C 0.7675(3) 0.5133(2) 1.18852(17) 0.0625(11) Uani 1 1 d . . . . .
H15 H 0.7537 0.4502 1.1952 0.075 Uiso 1 1 calc R . . . .
C32 C 0.0173(2) 0.26734(19) -0.04338(17) 0.0431(6) Uani 1 1 d . . . . .
H32 H -0.0002 0.2055 -0.0371 0.052 Uiso 1 1 calc R . . . .
N1 N 0.8555(3) 0.6546(3) 1.26114(17) 0.0956(15) Uani 1 1 d . . . . .
C12 C 0.8067(2) 0.6972(2) 1.1799(2) 0.0496(7) Uani 1 1 d . . . . .
H12 H 0.8177 0.7617 1.1763 0.059 Uiso 1 1 calc R . . . .
C16 C 0.8362(4) 0.5622(4) 1.2641(2) 0.111(2) Uani 1 1 d . . . . .
H16 H 0.8708 0.5296 1.3197 0.134 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
Cu1 O1 1.9422(14) . ?
Cu1 O3 1.9522(14) . ?
Cu1 O5 2.2860(15) . ?
Cu1 N3 2.0504(15) 4_565 ?
Cu1 N4 2.0257(16) 4_576 ?
O1 C1 1.272(2) . ?
O3 C17 1.270(2) . ?
O5 H5A 0.8666 . ?
O5 H5B 0.8665 . ?
N3 Cu1 2.0504(15) 4_566 ?
N3 C9 1.346(2) . ?
N3 C10 1.349(2) . ?
O2 C1 1.235(2) . ?
N4 Cu1 2.0257(16) 4_575 ?
N4 C27 1.345(2) . ?
N4 C23 1.347(2) . ?
N2 C5 1.339(2) . ?
N2 C4 1.346(2) . ?
N5 C20 1.345(2) . ?
N5 C21 1.347(2) . ?
O4 C17 1.236(2) . ?
C5 C6 1.398(2) . ?
C5 C7 1.481(2) . ?
C27 H27 0.9300 . ?
C27 C26 1.380(2) . ?
C4 C3 1.396(2) . ?
C4 C14 1.479(2) . ?
C3 H3 0.9300 . ?
C3 C2 1.389(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.396(2) . ?
C19 C18 1.386(2) . ?
C20 C25 1.484(2) . ?
C2 C6 1.390(2) . ?
C2 C1 1.514(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.393(2) . ?
C8 C9 1.386(2) . ?
C11 H11 0.9300 . ?
C11 C7 1.395(2) . ?
C11 C10 1.379(2) . ?
N6 C28 1.329(3) . ?
N6 C32 1.342(3) . ?
C22 H22 0.9300 . ?
C22 C18 1.390(2) . ?
C22 C21 1.394(2) . ?
C6 H6 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C26 H26 0.9300 . ?
C26 C25 1.392(2) . ?
C18 C17 1.513(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.381(3) . ?
C29 C28 1.387(3) . ?
C25 C24 1.396(2) . ?
C21 C30 1.490(2) . ?
C30 C31 1.378(3) . ?
C14 C13 1.373(3) . ?
C14 C15 1.361(3) . ?
C24 H24 0.9300 . ?
C24 C23 1.386(3) . ?
C23 H23 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.418(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.396(3) . ?
C28 H28 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.377(4) . ?
C32 H32 0.9300 . ?
N1 C12 1.322(5) . ?
N1 C16 1.339(5) . ?
C12 H12 0.9300 . ?
C16 H16 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
O1 Cu1 O3 173.93(6) . . ?
O1 Cu1 O5 88.93(6) . . ?
O1 Cu1 N3 88.94(6) . 4_565 ?
O1 Cu1 N4 91.79(6) . 4_576 ?
O3 Cu1 O5 97.03(6) . . ?
O3 Cu1 N3 89.62(6) . 4_565 ?
O3 Cu1 N4 88.81(6) . 4_576 ?
N3 Cu1 O5 92.63(6) 4_565 . ?
N4 Cu1 O5 95.37(6) 4_576 . ?
N4 Cu1 N3 171.98(6) 4_576 4_565 ?
C1 O1 Cu1 127.24(12) . . ?
C17 O3 Cu1 124.77(12) . . ?
Cu1 O5 H5A 125.4 . . ?
Cu1 O5 H5B 125.3 . . ?
H5A O5 H5B 109.3 . . ?
C9 N3 Cu1 119.30(12) . 4_566 ?
C9 N3 C10 117.44(15) . . ?
C10 N3 Cu1 122.81(12) . 4_566 ?
C27 N4 Cu1 122.12(12) . 4_575 ?
C27 N4 C23 117.49(16) . . ?
C23 N4 Cu1 120.34(12) . 4_575 ?
C5 N2 C4 118.60(15) . . ?
C20 N5 C21 118.50(15) . . ?
N2 C5 C6 122.73(16) . . ?
N2 C5 C7 116.15(14) . . ?
C6 C5 C7 121.11(15) . . ?
N4 C27 H27 118.5 . . ?
N4 C27 C26 122.97(16) . . ?
C26 C27 H27 118.5 . . ?
N2 C4 C3 122.10(16) . . ?
N2 C4 C14 116.45(16) . . ?
C3 C4 C14 121.45(16) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 C4 119.02(17) . . ?
C2 C3 H3 120.5 . . ?
C20 C19 H19 120.8 . . ?
C18 C19 H19 120.8 . . ?
C18 C19 C20 118.34(16) . . ?
N5 C20 C19 122.78(16) . . ?
N5 C20 C25 115.78(15) . . ?
C19 C20 C25 121.44(15) . . ?
C3 C2 C6 118.93(16) . . ?
C3 C2 C1 119.69(16) . . ?
C6 C2 C1 121.36(16) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C9 C8 C7 119.88(15) . . ?
C7 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C7 119.82(15) . . ?
C28 N6 C32 116.44(19) . . ?
C18 C22 H22 120.5 . . ?
C18 C22 C21 118.97(17) . . ?
C21 C22 H22 120.5 . . ?
C5 C6 H6 120.8 . . ?
C2 C6 C5 118.49(16) . . ?
C2 C6 H6 120.8 . . ?
C8 C7 C5 121.19(15) . . ?
C8 C7 C11 117.12(16) . . ?
C11 C7 C5 121.68(15) . . ?
N3 C9 C8 122.72(15) . . ?
N3 C9 H9 118.6 . . ?
C8 C9 H9 118.6 . . ?
N3 C10 C11 122.95(16) . . ?
N3 C10 H10 118.5 . . ?
C11 C10 H10 118.5 . . ?
C27 C26 H26 120.1 . . ?
C27 C26 C25 119.71(16) . . ?
C25 C26 H26 120.1 . . ?
C19 C18 C22 119.31(17) . . ?
C19 C18 C17 121.12(16) . . ?
C22 C18 C17 119.57(16) . . ?
C30 C29 H29 120.2 . . ?
C30 C29 C28 119.7(2) . . ?
C28 C29 H29 120.2 . . ?
O3 C17 C18 115.19(16) . . ?
O4 C17 O3 126.35(17) . . ?
O4 C17 C18 118.43(17) . . ?
O1 C1 C2 113.71(16) . . ?
O2 C1 O1 126.31(17) . . ?
O2 C1 C2 119.96(17) . . ?
C26 C25 C20 120.43(16) . . ?
C26 C25 C24 117.49(16) . . ?
C24 C25 C20 122.08(16) . . ?
N5 C21 C22 122.05(16) . . ?
N5 C21 C30 116.05(15) . . ?
C22 C21 C30 121.87(17) . . ?
C29 C30 C21 119.63(17) . . ?
C31 C30 C29 117.69(17) . . ?
C31 C30 C21 122.67(17) . . ?
C13 C14 C4 121.92(18) . . ?
C15 C14 C4 120.1(2) . . ?
C15 C14 C13 118.0(2) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 C25 119.31(16) . . ?
C23 C24 H24 120.3 . . ?
N4 C23 C24 122.93(17) . . ?
N4 C23 H23 118.5 . . ?
C24 C23 H23 118.5 . . ?
C14 C13 H13 121.1 . . ?
C14 C13 C12 117.9(2) . . ?
C12 C13 H13 121.1 . . ?
C30 C31 H31 120.6 . . ?
C30 C31 C32 118.9(2) . . ?
C32 C31 H31 120.6 . . ?
N6 C28 C29 123.6(2) . . ?
N6 C28 H28 118.2 . . ?
C29 C28 H28 118.2 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
N6 C32 C31 123.7(2) . . ?
N6 C32 H32 118.2 . . ?
C31 C32 H32 118.2 . . ?
C12 N1 C16 116.3(3) . . ?
C13 C12 H12 118.0 . . ?
N1 C12 C13 124.0(3) . . ?
N1 C12 H12 118.0 . . ?
C15 C16 H16 118.5 . . ?
N1 C16 C15 123.1(3) . . ?
N1 C16 H16 118.5 . . ?

_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 0.000 -0.008 -0.004 501 92 ' '
2 0.315 0.245 0.684 28 7 ' '
3 0.315 0.255 0.184 28 7 ' '
4 0.685 0.755 0.316 28 7 ' '
5 0.685 0.745 0.816 28 7 ' '
_platon_squeeze_details          ?

####################################################################### 
# 
# 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_CuBr
_database_code_depnum_ccdc_archive 'CCDC 1560295'
_audit_update_record             
;
2017-10-21 deposited with the CCDC.
2017-11-10 downloaded from the CCDC.
;
_audit_creation_date             2017-10-12
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H20 Br Cu2 N6 O5'
_chemical_formula_sum            'C32 H20 Br Cu2 N6 O5'
_chemical_formula_weight         775.54
_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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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                   22.6373(15)
_cell_length_b                   16.3743(12)
_cell_length_c                   11.5237(7)
_cell_angle_alpha                90
_cell_angle_beta                 116.401(2)
_cell_angle_gamma                90
_cell_volume                     3826.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1552
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.87
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.198
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6638
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14383
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         2.866
_diffrn_ambient_temperature      301.8
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3060
_reflns_number_total             3756
_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       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         3.846
_refine_diff_density_min         -0.864
_refine_diff_density_rms         0.166
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3756
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0616
_refine_ls_restrained_S_all      1.116
_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)+(0.1278P)²+20.6442P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2013
_refine_ls_wR_factor_ref         0.2108
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C5(H5), C4(H4), C12(H12), C2(H2), C1(H1), C9(H9), C7(H7), C10(H10),
 C6(H6)
;
_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 0.42088(3) 0.13471(4) 0.18833(5) 0.0239(2) Uani 1 1 d . . . . .
Br1 Br 0.5000 0.00497(6) 0.2500 0.0538(3) Uani 1 2 d S T P . .
O1W O 0.5000 0.2000(3) 0.2500 0.0277(11) Uani 1 2 d S T P . .
O1 O 0.40998(18) 0.1620(2) -0.6492(3) 0.0309(8) Uani 1 1 d . . . . .
N2 N 0.1568(2) 0.5571(3) -0.6260(4) 0.0309(10) Uani 1 1 d . . . . .
C15 C 0.3543(3) 0.2629(3) -0.3737(5) 0.0279(11) Uani 1 1 d . . . . .
N1 N 0.3986(2) 0.1661(3) 0.0001(4) 0.0271(9) Uani 1 1 d . . . . .
N3 N 0.3138(2) 0.3276(3) -0.4082(4) 0.0307(10) Uani 1 1 d . . . . .
C14 C 0.3775(3) 0.2281(4) -0.4578(5) 0.0298(11) Uani 1 1 d . . . . .
H14 H 0.4057 0.1834 -0.4320 0.036 Uiso 1 1 calc R . . . .
C16 C 0.3745(3) 0.2246(4) -0.6810(5) 0.0298(11) Uani 1 1 d . . . . .
C3 C 0.3710(3) 0.2289(3) -0.2439(5) 0.0268(11) Uani 1 1 d . . . . .
C5 C 0.4336(3) 0.1437(4) -0.0613(5) 0.0332(12) Uani 1 1 d . . . . .
H5 H 0.4686 0.1077 -0.0202 0.040 Uiso 1 1 calc R . . . .
C11 C 0.2964(3) 0.3607(3) -0.5239(5) 0.0287(11) Uani 1 1 d . . . . .
C8 C 0.2496(3) 0.4313(4) -0.5575(5) 0.0313(12) Uani 1 1 d . . . . .
O2 O 0.3515(3) 0.2560(3) -0.7886(4) 0.0587(15) Uani 1 1 d . . . . .
C13 C 0.3571(3) 0.2620(3) -0.5794(5) 0.0283(11) Uani 1 1 d . . . . .
C4 C 0.4205(3) 0.1717(4) -0.1838(5) 0.0345(13) Uani 1 1 d . . . . .
H4 H 0.4447 0.1522 -0.2254 0.041 Uiso 1 1 calc R . . . .
C12 C 0.3165(3) 0.3297(4) -0.6120(5) 0.0316(12) Uani 1 1 d . . . . .
H12 H 0.3027 0.3542 -0.6927 0.038 Uiso 1 1 calc R . . . .
C2 C 0.3348(3) 0.2512(4) -0.1787(5) 0.0417(15) Uani 1 1 d . . . . .
H2 H 0.3004 0.2883 -0.2163 0.050 Uiso 1 1 calc R . . . .
C1 C 0.3493(3) 0.2190(4) -0.0596(5) 0.0397(14) Uani 1 1 d . . . . .
H1 H 0.3238 0.2345 -0.0185 0.048 Uiso 1 1 calc R . . . .
C9 C 0.2130(3) 0.4440(4) -0.4911(6) 0.0438(16) Uani 1 1 d . . . . .
H9 H 0.2187 0.4105 -0.4217 0.053 Uiso 1 1 calc R . . . .
C7 C 0.2377(4) 0.4826(5) -0.6587(8) 0.068(3) Uani 1 1 d . . . . .
H7 H 0.2613 0.4764 -0.7067 0.082 Uiso 1 1 calc R . . . .
C10 C 0.1678(3) 0.5061(4) -0.5274(6) 0.0450(16) Uani 1 1 d . . . . .
H10 H 0.1435 0.5134 -0.4811 0.054 Uiso 1 1 calc R . . . .
C6 C 0.1913(4) 0.5432(5) -0.6903(7) 0.062(2) Uani 1 1 d . . . . .
H6 H 0.1839 0.5763 -0.7611 0.074 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
Cu1 Br1 2.6635(10) . ?
Cu1 O1W 1.930(3) . ?
Cu1 O1 2.043(4) 1_556 ?
Cu1 N2 2.025(4) 4_544 ?
Cu1 N1 2.062(4) . ?
Br1 Cu1 2.6635(10) 2_655 ?
O1W Cu1 1.930(3) 2_655 ?
O1 Cu1 2.043(4) 1_554 ?
O1 C16 1.252(7) . ?
N2 Cu1 2.025(4) 4_554 ?
N2 C10 1.341(7) . ?
N2 C6 1.315(7) . ?
C15 N3 1.340(7) . ?
C15 C14 1.412(7) . ?
C15 C3 1.479(7) . ?
N1 C5 1.327(7) . ?
N1 C1 1.337(7) . ?
N3 C11 1.326(7) . ?
C14 H14 0.9300 . ?
C14 C13 1.382(7) . ?
C16 O2 1.224(7) . ?
C16 C13 1.520(7) . ?
C3 C4 1.387(8) . ?
C3 C2 1.384(7) . ?
C5 H5 0.9300 . ?
C5 C4 1.384(8) . ?
C11 C8 1.497(7) . ?
C11 C12 1.381(7) . ?
C8 C9 1.371(8) . ?
C8 C7 1.363(8) . ?
C13 C12 1.381(8) . ?
C4 H4 0.9300 . ?
C12 H12 0.9300 . ?
C2 H2 0.9300 . ?
C2 C1 1.368(8) . ?
C1 H1 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.369(8) . ?
C7 H7 0.9300 . ?
C7 C6 1.371(9) . ?
C10 H10 0.9300 . ?
C6 H6 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
O1W Cu1 Br1 86.56(13) . . ?
O1W Cu1 O1 90.67(12) . 1_556 ?
O1W Cu1 N2 174.75(19) . 4_544 ?
O1W Cu1 N1 90.11(13) . . ?
O1 Cu1 Br1 105.71(11) 1_556 . ?
O1 Cu1 N1 146.81(18) 1_556 . ?
N2 Cu1 Br1 88.22(14) 4_544 . ?
N2 Cu1 O1 91.30(16) 4_544 1_556 ?
N2 Cu1 N1 90.89(17) 4_544 . ?
N1 Cu1 Br1 107.46(13) . . ?
Cu1 Br1 Cu1 74.19(4) 2_655 . ?
Cu1 O1W Cu1 112.7(3) 2_655 . ?
C16 O1 Cu1 103.6(3) . 1_554 ?
C10 N2 Cu1 119.8(4) . 4_554 ?
C6 N2 Cu1 123.3(4) . 4_554 ?
C6 N2 C10 115.9(5) . . ?
N3 C15 C14 121.9(5) . . ?
N3 C15 C3 115.6(4) . . ?
C14 C15 C3 122.4(5) . . ?
C5 N1 Cu1 124.6(4) . . ?
C5 N1 C1 117.7(5) . . ?
C1 N1 Cu1 117.4(3) . . ?
C11 N3 C15 118.7(4) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 C15 118.5(5) . . ?
C13 C14 H14 120.8 . . ?
O1 C16 C13 117.2(5) . . ?
O2 C16 O1 124.7(5) . . ?
O2 C16 C13 118.1(5) . . ?
C4 C3 C15 123.1(5) . . ?
C2 C3 C15 120.1(5) . . ?
C2 C3 C4 116.7(5) . . ?
N1 C5 H5 118.5 . . ?
N1 C5 C4 123.0(5) . . ?
C4 C5 H5 118.5 . . ?
N3 C11 C8 115.9(5) . . ?
N3 C11 C12 122.7(5) . . ?
C12 C11 C8 121.3(5) . . ?
C9 C8 C11 120.4(5) . . ?
C7 C8 C11 123.0(5) . . ?
C7 C8 C9 116.5(5) . . ?
C14 C13 C16 122.4(5) . . ?
C12 C13 C14 118.6(5) . . ?
C12 C13 C16 118.9(5) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.5(5) . . ?
C5 C4 H4 120.3 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.5(5) . . ?
C13 C12 H12 120.2 . . ?
C3 C2 H2 119.7 . . ?
C1 C2 C3 120.5(5) . . ?
C1 C2 H2 119.7 . . ?
N1 C1 C2 122.6(5) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.8(5) . . ?
C10 C9 H9 120.1 . . ?
C8 C7 H7 119.7 . . ?
C8 C7 C6 120.7(6) . . ?
C6 C7 H7 119.7 . . ?
N2 C10 C9 123.7(5) . . ?
N2 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
N2 C6 C7 123.5(6) . . ?
N2 C6 H6 118.2 . . ?
C7 C6 H6 118.2 . . ?

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 O1 C16 O2 2.7(7) 1_554 . . . ?
Cu1 O1 C16 C13 -179.4(4) 1_554 . . . ?
Cu1 N2 C10 C9 170.2(6) 4_554 . . . ?
Cu1 N2 C6 C7 -170.4(8) 4_554 . . . ?
Cu1 N1 C5 C4 -174.3(5) . . . . ?
Cu1 N1 C1 C2 172.6(6) . . . . ?
O1 C16 C13 C14 -1.9(8) . . . . ?
O1 C16 C13 C12 -178.1(5) . . . . ?
C15 N3 C11 C8 178.4(5) . . . . ?
C15 N3 C11 C12 2.2(9) . . . . ?
C15 C14 C13 C16 -174.5(5) . . . . ?
C15 C14 C13 C12 1.7(8) . . . . ?
C15 C3 C4 C5 179.1(5) . . . . ?
C15 C3 C2 C1 178.9(6) . . . . ?
N1 C5 C4 C3 3.5(10) . . . . ?
N3 C15 C14 C13 -0.4(9) . . . . ?
N3 C15 C3 C4 -168.6(6) . . . . ?
N3 C15 C3 C2 14.3(8) . . . . ?
N3 C11 C8 C9 -18.6(9) . . . . ?
N3 C11 C8 C7 165.8(7) . . . . ?
N3 C11 C12 C13 -0.9(9) . . . . ?
C14 C15 N3 C11 -1.5(8) . . . . ?
C14 C15 C3 C4 13.5(9) . . . . ?
C14 C15 C3 C2 -163.7(6) . . . . ?
C14 C13 C12 C11 -1.1(9) . . . . ?
C16 C13 C12 C11 175.2(5) . . . . ?
C3 C15 N3 C11 -179.5(5) . . . . ?
C3 C15 C14 C13 177.4(5) . . . . ?
C3 C2 C1 N1 0.8(11) . . . . ?
C5 N1 C1 C2 -1.1(10) . . . . ?
C11 C8 C9 C10 -176.5(6) . . . . ?
C11 C8 C7 C6 175.9(8) . . . . ?
C8 C11 C12 C13 -176.9(5) . . . . ?
C8 C9 C10 N2 -0.2(12) . . . . ?
C8 C7 C6 N2 1.3(16) . . . . ?
O2 C16 C13 C14 176.1(6) . . . . ?
O2 C16 C13 C12 -0.1(9) . . . . ?
C4 C3 C2 C1 1.6(10) . . . . ?
C12 C11 C8 C9 157.7(6) . . . . ?
C12 C11 C8 C7 -17.9(10) . . . . ?
C2 C3 C4 C5 -3.6(9) . . . . ?
C1 N1 C5 C4 -1.1(9) . . . . ?
C9 C8 C7 C6 0.1(13) . . . . ?
C7 C8 C9 C10 -0.6(11) . . . . ?
C10 N2 C6 C7 -2.0(13) . . . . ?
C6 N2 C10 C9 1.5(11) . . . . ?

_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 0.000 0.000 -0.010 458 65 ' '
2 0.500 0.500 0.102 458 65 ' '
_platon_squeeze_details          
;
two methanol molecules had been squeezed
;
