# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_20160908q
_database_code_depnum_ccdc_archive 'CCDC 1527274'
_audit_update_record             
;
2017-01-13 deposited with the CCDC.
2017-10-20 downloaded from the CCDC.
;
_audit_creation_date             2016-11-09
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C32 H22 Cl4 Cu2 N6'
_chemical_formula_sum            'C32 H22 Cl4 Cu2 N6'
_chemical_formula_weight         759.44
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   11.2017(3)
_cell_length_b                   17.1297(4)
_cell_length_c                   9.4880(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.712(3)
_cell_angle_gamma                90.00
_cell_volume                     1679.41(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4072
_cell_measurement_temperature    293
_cell_measurement_theta_max      74.9240
_cell_measurement_theta_min      4.9920
_exptl_absorpt_coefficient_mu    4.743
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.00019
_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_colour            'dull brownish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             764
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7107
_diffrn_reflns_theta_full        76.47
_diffrn_reflns_theta_max         76.47
_diffrn_reflns_theta_min         5.00
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 10.5281
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3020
_reflns_number_total             3452
_reflns_threshold_expression     >2sigma(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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       Fsqd
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3452
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0809P)²+0.1709P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1266
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
Details about the Squeezed Material
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  0.500  0.000       115        25 ' '
   2  0.500  1.000  0.500       115        25 ' '
_platon_squeeze_details
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C15(H15), C12(H12), C3(H3A), C8(H8), C14(H14), C7(H7),
 C13(H13), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cu1 Cu 0.93008(3) 0.424648(19) 0.06705(4) 0.04589(15) Uani 1 d . . .
Cl1 Cl 1.14503(6) 0.46288(3) 0.06038(6) 0.04982(17) Uani 1 d . . .
Cl2 Cl 0.85641(8) 0.45112(4) 0.25972(7) 0.0614(2) Uani 1 d . . .
N2 N 0.8333(2) 0.35110(12) -0.1104(2) 0.0490(4) Uani 1 d . . .
N1 N 1.01449(19) 0.32304(12) 0.1626(2) 0.0458(4) Uani 1 d . . .
C10 C 0.8676(2) 0.27810(15) -0.0730(3) 0.0501(5) Uani 1 d . . .
N3 N 0.8046(2) 0.22750(14) -0.1871(3) 0.0600(6) Uani 1 d . . .
H3 H 0.8144 0.1777 -0.1852 0.072 Uiso 1 calc . . R
C9 C 0.9670(3) 0.26016(14) 0.0770(3) 0.0506(5) Uani 1 d . . .
C2 C 1.1670(3) 0.38129(17) 0.3932(3) 0.0553(6) Uani 1 d . . .
H2 H 1.1343 0.4307 0.3590 0.066 Uiso 1 calc . . R
C1 C 1.1130(2) 0.31510(15) 0.3028(3) 0.0489(5) Uani 1 d . . .
C16 C 0.7400(2) 0.34980(17) -0.2590(3) 0.0535(6) Uani 1 d . . .
C15 C 0.6735(3) 0.4101(2) -0.3552(4) 0.0672(8) Uani 1 d . . .
H15 H 0.6858 0.4618 -0.3231 0.081 Uiso 1 calc . . R
C12 C 0.6343(3) 0.2521(2) -0.4547(4) 0.0780(10) Uani 1 d . . .
H12 H 0.6210 0.2005 -0.4878 0.094 Uiso 1 calc . . R
C3 C 1.2684(3) 0.3724(2) 0.5323(3) 0.0681(7) Uani 1 d . . .
H3A H 1.3054 0.4162 0.5910 0.082 Uiso 1 calc . . R
C8 C 1.0095(3) 0.18399(16) 0.1272(4) 0.0618(7) Uani 1 d . . .
H8 H 0.9723 0.1411 0.0657 0.074 Uiso 1 calc . . R
C11 C 0.7211(3) 0.27164(18) -0.3078(3) 0.0595(7) Uani 1 d . . .
C6 C 1.1608(3) 0.23881(17) 0.3583(3) 0.0599(7) Uani 1 d . . .
C14 C 0.5887(3) 0.3904(3) -0.4998(4) 0.0823(10) Uani 1 d . . .
H14 H 0.5430 0.4295 -0.5671 0.099 Uiso 1 calc . . R
C7 C 1.1056(4) 0.17413(17) 0.2668(4) 0.0691(8) Uani 1 d . . .
H7 H 1.1348 0.1242 0.3016 0.083 Uiso 1 calc . . R
C13 C 0.5702(3) 0.3119(3) -0.5472(4) 0.0866(12) Uani 1 d . . .
H13 H 0.5120 0.3005 -0.6456 0.104 Uiso 1 calc . . R
C4 C 1.3160(3) 0.2980(2) 0.5857(4) 0.0777(9) Uani 1 d . . .
H4 H 1.3844 0.2931 0.6799 0.093 Uiso 1 calc . . R
C5 C 1.2653(3) 0.2335(2) 0.5043(4) 0.0743(9) Uani 1 d . . .
H5 H 1.2986 0.1848 0.5432 0.089 Uiso 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 2.5195(7) . ?
Cu1 Cl1 2.2574(6) 3_765 ?
Cu1 Cl2 2.3223(7) . ?
Cu1 N2 2.046(2) . ?
Cu1 N1 2.021(2) . ?
Cl1 Cu1 2.2574(6) 3_765 ?
N2 C10 1.316(3) . ?
N2 C16 1.394(3) . ?
N1 C9 1.330(3) . ?
N1 C1 1.368(3) . ?
C10 N3 1.353(3) . ?
C10 C9 1.462(4) . ?
N3 C11 1.390(4) . ?
C9 C8 1.407(4) . ?
C2 C1 1.409(4) . ?
C2 C3 1.377(4) . ?
C1 C6 1.433(3) . ?
C16 C15 1.389(5) . ?
C16 C11 1.406(4) . ?
C15 C14 1.375(4) . ?
C12 C11 1.398(4) . ?
C12 C13 1.359(6) . ?
C3 C4 1.399(5) . ?
C8 C7 1.357(5) . ?
C6 C7 1.396(5) . ?
C6 C5 1.430(5) . ?
C14 C13 1.408(6) . ?
C4 C5 1.341(6) . ?

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
Cl1 Cu1 Cl1 85.81(2) 3_765 . ?
Cl1 Cu1 Cl2 94.75(3) 3_765 . ?
Cl2 Cu1 Cl1 127.05(3) . . ?
N2 Cu1 Cl1 96.62(6) . 3_765 ?
N2 Cu1 Cl1 110.32(6) . . ?
N2 Cu1 Cl2 122.10(7) . . ?
N1 Cu1 Cl1 87.08(6) . . ?
N1 Cu1 Cl1 171.30(6) . 3_765 ?
N1 Cu1 Cl2 93.54(6) . . ?
N1 Cu1 N2 81.16(8) . . ?
Cu1 Cl1 Cu1 94.19(2) 3_765 . ?
C10 N2 Cu1 110.91(17) . . ?
C10 N2 C16 106.5(2) . . ?
C16 N2 Cu1 142.57(18) . . ?
C9 N1 Cu1 114.56(17) . . ?
C9 N1 C1 119.7(2) . . ?
C1 N1 Cu1 125.73(17) . . ?
N2 C10 N3 112.7(2) . . ?
N2 C10 C9 119.7(2) . . ?
N3 C10 C9 127.6(2) . . ?
C10 N3 C11 106.7(2) . . ?
N1 C9 C10 113.5(2) . . ?
N1 C9 C8 122.7(3) . . ?
C8 C9 C10 123.7(3) . . ?
C3 C2 C1 119.7(3) . . ?
N1 C1 C2 120.5(2) . . ?
N1 C1 C6 119.7(3) . . ?
C2 C1 C6 119.9(2) . . ?
N2 C16 C11 107.9(3) . . ?
C15 C16 N2 131.0(3) . . ?
C15 C16 C11 121.1(3) . . ?
C14 C15 C16 117.6(3) . . ?
C13 C12 C11 117.0(3) . . ?
C2 C3 C4 120.4(3) . . ?
C7 C8 C9 118.9(3) . . ?
N3 C11 C16 106.2(2) . . ?
N3 C11 C12 132.8(3) . . ?
C12 C11 C16 121.0(3) . . ?
C7 C6 C1 118.8(3) . . ?
C7 C6 C5 123.6(3) . . ?
C5 C6 C1 117.6(3) . . ?
C15 C14 C13 120.8(4) . . ?
C8 C7 C6 120.2(3) . . ?
C12 C13 C14 122.5(3) . . ?
C5 C4 C3 121.6(3) . . ?
C4 C5 C6 120.8(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_20161011a
_database_code_depnum_ccdc_archive 'CCDC 1527275'
_audit_update_record             
;
2017-01-13 deposited with the CCDC.
2017-10-20 downloaded from the CCDC.
;
_audit_creation_date             2017-01-05
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C34 H26 Br Cu N3 P'
_chemical_formula_sum            'C34 H26 Br Cu N3 P'
_chemical_formula_weight         651.00
_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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.81614(17)
_cell_length_b                   15.9919(3)
_cell_length_c                   18.4289(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.1399(17)
_cell_angle_gamma                90.00
_cell_volume                     2876.36(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6892
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.9900
_cell_measurement_theta_min      4.5400
_exptl_absorpt_coefficient_mu    3.441
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63394
_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_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13100
_diffrn_reflns_theta_full        76.49
_diffrn_reflns_theta_max         76.49
_diffrn_reflns_theta_min         3.67
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.5281
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -61.00   30.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3585   77.0000   30.0000 91

#__ type_ start__ end____ width___ exp.time_
  2 omega -113.00  -21.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3585  -57.0000  -90.0000 92

#__ type_ start__ end____ width___ exp.time_
  3 omega  -61.00   21.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3585   57.0000  150.0000 82

#__ type_ start__ end____ width___ exp.time_
  4 omega   95.00  127.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  120.0000 32

#__ type_ start__ end____ width___ exp.time_
  5 omega   43.00   94.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   30.0000 51

#__ type_ start__ end____ width___ exp.time_
  6 omega   75.00  112.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   90.0000 37

#__ type_ start__ end____ width___ exp.time_
  7 omega   57.00  110.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
  8 omega  142.00  176.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 34

#__ type_ start__ end____ width___ exp.time_
  9 omega   93.00  134.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 41

#__ type_ start__ end____ width___ exp.time_
 10 omega   35.00   73.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -120.0000 38

#__ type_ start__ end____ width___ exp.time_
 11 omega  149.00  176.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 12 omega   38.00   99.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -30.0000 61

#__ type_ start__ end____ width___ exp.time_
 13 omega   40.00  116.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -180.0000 76

#__ type_ start__ end____ width___ exp.time_
 14 omega   55.00   96.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -90.0000 41

#__ type_ start__ end____ width___ exp.time_
 15 omega   88.00  155.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   60.0000 67
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0909446000
_diffrn_orient_matrix_UB_12      0.0547099000
_diffrn_orient_matrix_UB_13      -0.0543882000
_diffrn_orient_matrix_UB_21      0.0887630000
_diffrn_orient_matrix_UB_22      0.0768344000
_diffrn_orient_matrix_UB_23      0.0234233000
_diffrn_orient_matrix_UB_31      0.0937924000
_diffrn_orient_matrix_UB_32      -0.0195263000
_diffrn_orient_matrix_UB_33      -0.0596367000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                5049
_reflns_number_total             5915
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_threshold_expression     >2sigma(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  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5915
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0469P)²+1.4135P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1008
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C21(H21), C27(H27), C17(H17), C33(H33), C23(H23), C18(H18), C6(H6),
 C5(H5), C7(H7), C19(H19), C14(H14), C11(H11), C32(H32), C13(H13), C20(H20),
 C30(H30), C29(H29), C26(H26), C12(H12), C24(H24), C31(H31), C3(H3A), C4(H4),
 C25(H25)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 0.44715(3) 0.316745(19) 0.356943(17) 0.06299(11) Uani 1 d . . .
Cu1 Cu 0.31898(4) 0.30524(2) 0.46515(2) 0.04792(11) Uani 1 d . . .
P1 P 0.21631(5) 0.18342(3) 0.47002(3) 0.04076(13) Uani 1 d . . .
N2 N 0.4332(2) 0.36373(13) 0.55209(11) 0.0480(4) Uani 1 d . . .
N1 N 0.2255(2) 0.42751(12) 0.46242(11) 0.0464(4) Uani 1 d . . .
N3 N 0.4834(2) 0.48424(15) 0.61011(12) 0.0550(5) Uani 1 d . . .
C16 C 0.0420(2) 0.18105(14) 0.42330(14) 0.0448(5) Uani 1 d . . .
C9 C 0.4005(2) 0.44336(15) 0.55765(13) 0.0468(5) Uani 1 d . . .
C1 C 0.1180(3) 0.45668(16) 0.41578(14) 0.0495(5) Uani 1 d . . .
C2 C 0.0549(3) 0.40267(19) 0.36208(16) 0.0612(7) Uani 1 d . . .
H2 H 0.0870 0.3483 0.3585 0.073 Uiso 1 calc . . R
C28 C 0.1876(2) 0.14706(15) 0.56112(13) 0.0442(5) Uani 1 d . . .
C21 C -0.0730(3) 0.18409(18) 0.46119(17) 0.0576(6) Uani 1 d . . .
H21 H -0.0631 0.1815 0.5119 0.069 Uiso 1 calc . . R
C22 C 0.2982(2) 0.09519(15) 0.42974(13) 0.0458(5) Uani 1 d . . .
C27 C 0.2286(3) 0.02380(18) 0.40361(18) 0.0635(7) Uani 1 d . . .
H27 H 0.1346 0.0198 0.4058 0.076 Uiso 1 calc . . R
C17 C 0.0244(3) 0.18487(17) 0.34773(16) 0.0563(6) Uani 1 d . . .
H17 H 0.1005 0.1839 0.3217 0.068 Uiso 1 calc . . R
C8 C 0.2865(3) 0.48013(15) 0.51117(14) 0.0490(5) Uani 1 d . . .
C0AA C 0.0702(3) 0.53970(17) 0.42011(17) 0.0575(6) Uani 1 d . . .
C33 C 0.1606(3) 0.06438(17) 0.57747(16) 0.0563(6) Uani 1 d . . .
H33 H 0.1653 0.0234 0.5420 0.068 Uiso 1 calc . . R
C23 C 0.4375(3) 0.09913(19) 0.4258(2) 0.0692(8) Uani 1 d . . .
H23 H 0.4864 0.1462 0.4429 0.083 Uiso 1 calc . . R
C18 C -0.1062(3) 0.1902(2) 0.31056(19) 0.0698(8) Uani 1 d . . .
H18 H -0.1174 0.1915 0.2598 0.084 Uiso 1 calc . . R
C6 C 0.1371(3) 0.59281(18) 0.47256(19) 0.0673(8) Uani 1 d . . .
H6 H 0.1074 0.6477 0.4766 0.081 Uiso 1 calc . . R
C5 C -0.0427(3) 0.5652(2) 0.3695(2) 0.0758(9) Uani 1 d . . .
H5 H -0.0759 0.6195 0.3714 0.091 Uiso 1 calc . . R
C7 C 0.2456(3) 0.56412(17) 0.51774(17) 0.0596(7) Uani 1 d . . .
H7 H 0.2920 0.5992 0.5523 0.072 Uiso 1 calc . . R
C19 C -0.2189(3) 0.1936(2) 0.3489(2) 0.0763(9) Uani 1 d . . .
H19 H -0.3063 0.1976 0.3241 0.092 Uiso 1 calc . . R
C15 C 0.5436(3) 0.35030(17) 0.60429(14) 0.0517(6) Uani 1 d . . .
C10 C 0.5774(3) 0.42581(19) 0.64102(14) 0.0558(6) Uani 1 d . . .
C14 C 0.6186(3) 0.2781(2) 0.62253(18) 0.0678(8) Uani 1 d . . .
H14 H 0.5980 0.2277 0.5986 0.081 Uiso 1 calc . . R
C11 C 0.6855(3) 0.4323(2) 0.69575(15) 0.0680(8) Uani 1 d . . .
H11 H 0.7079 0.4826 0.7193 0.082 Uiso 1 calc . . R
C32 C 0.1267(3) 0.0421(2) 0.64580(18) 0.0656(8) Uani 1 d . . .
H32 H 0.1113 -0.0137 0.6565 0.079 Uiso 1 calc . . R
C13 C 0.7258(4) 0.2846(2) 0.67815(19) 0.0771(9) Uani 1 d . . .
H13 H 0.7775 0.2374 0.6922 0.092 Uiso 1 calc . . R
C20 C -0.2024(3) 0.1911(2) 0.4234(2) 0.0740(9) Uani 1 d . . .
H20 H -0.2789 0.1940 0.4490 0.089 Uiso 1 calc . . R
C30 C 0.1426(5) 0.1838(3) 0.6823(2) 0.0880(11) Uani 1 d . . .
H30 H 0.1338 0.2247 0.7174 0.106 Uiso 1 calc . . R
C29 C 0.1822(3) 0.2059(2) 0.61549(17) 0.0663(7) Uani 1 d . . .
H29 H 0.2057 0.2611 0.6069 0.080 Uiso 1 calc . . R
C26 C 0.2978(4) -0.0412(2) 0.3744(2) 0.0821(10) Uani 1 d . . .
H26 H 0.2504 -0.0886 0.3567 0.098 Uiso 1 calc . . R
C12 C 0.7571(4) 0.3604(2) 0.71312(18) 0.0755(9) Uani 1 d . . .
H12 H 0.8298 0.3623 0.7498 0.091 Uiso 1 calc . . R
C24 C 0.5047(4) 0.0332(2) 0.3964(3) 0.0987(15) Uani 1 d . . .
H24 H 0.5986 0.0368 0.3938 0.118 Uiso 1 calc . . R
C31 C 0.1159(3) 0.1017(3) 0.69725(18) 0.0765(9) Uani 1 d . . .
H31 H 0.0904 0.0870 0.7427 0.092 Uiso 1 calc . . R
C3 C -0.0529(4) 0.4297(2) 0.31526(19) 0.0753(8) Uani 1 d . . .
H3A H -0.0943 0.3933 0.2802 0.090 Uiso 1 calc . . R
C4 C -0.1019(4) 0.5115(2) 0.3192(2) 0.0806(10) Uani 1 d . . .
H4 H -0.1758 0.5289 0.2870 0.097 Uiso 1 calc . . R
C25 C 0.4369(5) -0.0357(2) 0.3717(2) 0.0941(13) Uani 1 d . . .
H25 H 0.4839 -0.0797 0.3527 0.113 Uiso 1 calc . . R
H3 H 0.491(3) 0.541(2) 0.6149(19) 0.077(10) Uiso 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
Br1 Cu1 2.4759(5) . ?
Cu1 P1 2.1996(6) . ?
Cu1 N2 2.077(2) . ?
Cu1 N1 2.158(2) . ?
P1 C16 1.832(2) . ?
P1 C28 1.827(3) . ?
P1 C22 1.821(2) . ?
N2 C9 1.320(3) . ?
N2 C15 1.387(3) . ?
N1 C1 1.370(3) . ?
N1 C8 1.326(3) . ?
N3 C9 1.362(3) . ?
N3 C10 1.392(4) . ?
C16 C21 1.390(4) . ?
C16 C17 1.386(4) . ?
C9 C8 1.459(4) . ?
C1 C2 1.406(4) . ?
C1 C0AA 1.413(4) . ?
C2 C3 1.362(4) . ?
C28 C33 1.388(4) . ?
C28 C29 1.379(4) . ?
C21 C20 1.386(4) . ?
C22 C27 1.390(4) . ?
C22 C23 1.379(4) . ?
C27 C26 1.382(4) . ?
C17 C18 1.390(4) . ?
C8 C7 1.411(4) . ?
C0AA C6 1.397(4) . ?
C0AA C5 1.429(5) . ?
C33 C32 1.383(4) . ?
C23 C24 1.384(5) . ?
C18 C19 1.376(5) . ?
C6 C7 1.360(4) . ?
C5 C4 1.349(5) . ?
C19 C20 1.365(5) . ?
C15 C10 1.407(4) . ?
C15 C14 1.392(4) . ?
C10 C11 1.387(4) . ?
C14 C13 1.392(4) . ?
C11 C12 1.368(5) . ?
C32 C31 1.357(5) . ?
C13 C12 1.392(5) . ?
C30 C29 1.376(5) . ?
C30 C31 1.372(5) . ?
C26 C25 1.374(6) . ?
C24 C25 1.342(6) . ?
C3 C4 1.398(5) . ?

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
P1 Cu1 Br1 111.91(2) . . ?
N2 Cu1 Br1 108.00(6) . . ?
N2 Cu1 P1 125.40(6) . . ?
N2 Cu1 N1 78.64(8) . . ?
N1 Cu1 Br1 99.51(5) . . ?
N1 Cu1 P1 127.44(6) . . ?
C16 P1 Cu1 114.09(8) . . ?
C28 P1 Cu1 115.84(8) . . ?
C28 P1 C16 101.37(11) . . ?
C22 P1 Cu1 116.46(8) . . ?
C22 P1 C16 102.90(11) . . ?
C22 P1 C28 104.25(11) . . ?
C9 N2 Cu1 112.27(17) . . ?
C9 N2 C15 105.9(2) . . ?
C15 N2 Cu1 141.49(18) . . ?
C1 N1 Cu1 128.34(17) . . ?
C8 N1 Cu1 113.52(17) . . ?
C8 N1 C1 118.1(2) . . ?
C9 N3 C10 106.7(2) . . ?
C21 C16 P1 122.1(2) . . ?
C17 C16 P1 118.74(19) . . ?
C17 C16 C21 118.9(2) . . ?
N2 C9 N3 112.7(2) . . ?
N2 C9 C8 121.4(2) . . ?
N3 C9 C8 125.9(2) . . ?
N1 C1 C2 118.9(2) . . ?
N1 C1 C0AA 121.5(3) . . ?
C2 C1 C0AA 119.5(3) . . ?
C3 C2 C1 120.3(3) . . ?
C33 C28 P1 123.7(2) . . ?
C29 C28 P1 118.2(2) . . ?
C29 C28 C33 118.0(3) . . ?
C20 C21 C16 120.0(3) . . ?
C27 C22 P1 123.78(19) . . ?
C23 C22 P1 118.0(2) . . ?
C23 C22 C27 118.2(2) . . ?
C26 C27 C22 120.6(3) . . ?
C16 C17 C18 120.5(3) . . ?
N1 C8 C9 113.9(2) . . ?
N1 C8 C7 123.4(3) . . ?
C7 C8 C9 122.7(2) . . ?
C1 C0AA C5 118.0(3) . . ?
C6 C0AA C1 118.4(3) . . ?
C6 C0AA C5 123.5(3) . . ?
C32 C33 C28 120.9(3) . . ?
C22 C23 C24 120.2(3) . . ?
C19 C18 C17 119.9(3) . . ?
C7 C6 C0AA 119.9(3) . . ?
C4 C5 C0AA 120.9(3) . . ?
C6 C7 C8 118.7(3) . . ?
C20 C19 C18 120.0(3) . . ?
N2 C15 C10 109.1(2) . . ?
N2 C15 C14 130.6(3) . . ?
C14 C15 C10 120.3(3) . . ?
N3 C10 C15 105.5(2) . . ?
C11 C10 N3 132.0(3) . . ?
C11 C10 C15 122.5(3) . . ?
C15 C14 C13 117.0(3) . . ?
C12 C11 C10 116.2(3) . . ?
C31 C32 C33 120.0(3) . . ?
C12 C13 C14 121.2(3) . . ?
C19 C20 C21 120.8(3) . . ?
C31 C30 C29 120.2(3) . . ?
C30 C29 C28 120.7(3) . . ?
C25 C26 C27 119.8(4) . . ?
C11 C12 C13 122.8(3) . . ?
C25 C24 C23 121.2(3) . . ?
C32 C31 C30 120.1(3) . . ?
C2 C3 C4 120.8(3) . . ?
C5 C4 C3 120.4(3) . . ?
C24 C25 C26 119.9(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
