# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1418882'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2016-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H38 Br2 Cl2 Cu2 N6 O4'
_chemical_formula_weight         976.52

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.9700(6)
_cell_length_b                   16.1782(14)
_cell_length_c                   17.0252(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.1440(10)
_cell_angle_gamma                90.00
_cell_volume                     1904.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5239
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      28.8

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             980
_exptl_absorpt_coefficient_mu    3.402
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4603
_exptl_absorpt_correction_T_max  0.5084
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9904
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         25.49
_reflns_number_total             3552
_reflns_number_gt                3075
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0369P)²+1.8615P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3552
_refine_ls_number_parameters     240
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0771
_refine_ls_wR_factor_gt          0.0727
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.63949(5) 0.44663(2) 1.051817(18) 0.03454(11) Uani 1 1 d . . .
Br1 Br 0.42678(4) 0.31025(2) 1.058112(19) 0.04739(11) Uani 1 1 d . . .
Cl1 Cl 0.72202(14) 0.29117(7) 1.26769(7) 0.0807(3) Uani 1 1 d . . .
N1 N 0.8890(3) 0.40657(13) 1.02924(12) 0.0316(5) Uani 1 1 d . . .
N2 N 1.0098(3) 0.38833(15) 1.09826(13) 0.0337(5) Uani 1 1 d D . .
N3 N 0.4565(4) 0.37523(19) 0.67351(15) 0.0522(7) Uani 1 1 d . . .
O1 O 0.5634(3) 0.46997(13) 0.94062(10) 0.0411(5) Uani 1 1 d . . .
O2 O 0.7691(3) 0.43571(12) 1.16131(11) 0.0386(4) Uani 1 1 d . . .
C1 C 0.8199(4) 0.39654(16) 0.88903(15) 0.0336(6) Uani 1 1 d . . .
C2 C 0.6300(4) 0.43021(16) 0.88005(15) 0.0333(6) Uani 1 1 d . . .
C3 C 0.5142(4) 0.42342(18) 0.80879(16) 0.0378(6) Uani 1 1 d . . .
H3 H 0.3896 0.4449 0.8045 0.045 Uiso 1 1 calc R . .
C4 C 0.5766(4) 0.38520(18) 0.74193(16) 0.0391(6) Uani 1 1 d . . .
C5 C 0.7707(4) 0.35634(19) 0.74980(16) 0.0424(7) Uani 1 1 d . . .
H5 H 0.8206 0.3337 0.7064 0.051 Uiso 1 1 calc R . .
C6 C 0.8832(4) 0.36188(19) 0.82068(16) 0.0413(7) Uani 1 1 d . . .
H6 H 1.0089 0.3417 0.8244 0.050 Uiso 1 1 calc R . .
C7 C 0.9422(4) 0.38834(17) 0.96147(16) 0.0347(6) Uani 1 1 d . . .
H7 H 1.0672 0.3688 0.9601 0.042 Uiso 1 1 calc R . .
C8 C 0.9325(4) 0.40253(16) 1.16436(15) 0.0319(6) Uani 1 1 d . . .
C9 C 1.0407(4) 0.37664(17) 1.24103(15) 0.0338(6) Uani 1 1 d . . .
C10 C 0.9536(4) 0.32855(19) 1.29363(18) 0.0428(7) Uani 1 1 d . . .
C11 C 1.0480(6) 0.3066(2) 1.3662(2) 0.0619(10) Uani 1 1 d . . .
H11 H 0.9874 0.2736 1.4005 0.074 Uiso 1 1 calc R . .
C12 C 1.2319(7) 0.3341(3) 1.3871(2) 0.0753(12) Uani 1 1 d . . .
H12 H 1.2970 0.3200 1.4363 0.090 Uiso 1 1 calc R . .
C13 C 1.3226(6) 0.3822(3) 1.3365(3) 0.0768(12) Uani 1 1 d . . .
H13 H 1.4478 0.4010 1.3518 0.092 Uiso 1 1 calc R . .
C14 C 1.2285(5) 0.4027(2) 1.2630(2) 0.0539(8) Uani 1 1 d . . .
H14 H 1.2914 0.4341 1.2282 0.065 Uiso 1 1 calc R . .
C15 C 0.5211(5) 0.3343(2) 0.60546(18) 0.0527(8) Uani 1 1 d . . .
H15A H 0.4095 0.3107 0.5736 0.063 Uiso 1 1 calc R . .
H15B H 0.6062 0.2891 0.6242 0.063 Uiso 1 1 calc R . .
C16 C 0.6256(6) 0.3896(3) 0.5538(2) 0.0706(11) Uani 1 1 d . . .
H16A H 0.5385 0.4313 0.5304 0.106 Uiso 1 1 calc R . .
H16B H 0.6720 0.3573 0.5128 0.106 Uiso 1 1 calc R . .
H16C H 0.7328 0.4155 0.5852 0.106 Uiso 1 1 calc R . .
C17 C 0.2478(5) 0.3973(3) 0.6653(2) 0.0692(11) Uani 1 1 d . . .
H17A H 0.1750 0.3546 0.6346 0.083 Uiso 1 1 calc R . .
H17B H 0.2057 0.3978 0.7175 0.083 Uiso 1 1 calc R . .
C18 C 0.2026(8) 0.4746(4) 0.6287(4) 0.123(2) Uani 1 1 d . . .
H18A H 0.2909 0.5158 0.6523 0.184 Uiso 1 1 calc R . .
H18B H 0.0728 0.4899 0.6359 0.184 Uiso 1 1 calc R . .
H18C H 0.2133 0.4706 0.5732 0.184 Uiso 1 1 calc R . .
H2 H 1.126(3) 0.364(2) 1.095(2) 0.080 Uiso 1 1 d D . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9385(18) . ?
Cu1 N1 1.939(2) . ?
Cu1 O1 1.9703(18) 3_667 ?
Cu1 O2 1.9756(18) . ?
Cu1 Br1 2.6678(5) . ?
Cu1 Cu1 3.0038(6) 3_667 ?
Cl1 C10 1.729(3) . ?
N1 C7 1.289(3) . ?
N1 N2 1.389(3) . ?
N2 C8 1.327(3) . ?
N2 H2 0.906(10) . ?
N3 C4 1.357(4) . ?
N3 C15 1.454(4) . ?
N3 C17 1.488(4) . ?
O1 C2 1.346(3) . ?
O1 Cu1 1.9703(18) 3_667 ?
O2 C8 1.254(3) . ?
C1 C6 1.411(4) . ?
C1 C7 1.416(4) . ?
C1 C2 1.422(4) . ?
C2 C3 1.375(4) . ?
C3 C4 1.411(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.422(4) . ?
C5 C6 1.358(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.484(4) . ?
C9 C14 1.382(4) . ?
C9 C10 1.382(4) . ?
C10 C11 1.373(5) . ?
C11 C12 1.361(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.372(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.505(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.415(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N1 90.85(8) . . ?
O1 Cu1 O1 79.57(8) . 3_667 ?
N1 Cu1 O1 155.60(9) . 3_667 ?
O1 Cu1 O2 167.51(9) . . ?
N1 Cu1 O2 80.86(8) . . ?
O1 Cu1 O2 104.31(7) 3_667 . ?
O1 Cu1 Br1 96.57(7) . . ?
N1 Cu1 Br1 104.37(7) . . ?
O1 Cu1 Br1 99.02(7) 3_667 . ?
O2 Cu1 Br1 94.55(6) . . ?
O1 Cu1 Cu1 40.17(5) . 3_667 ?
N1 Cu1 Cu1 127.36(6) . 3_667 ?
O1 Cu1 Cu1 39.40(5) 3_667 3_667 ?
O2 Cu1 Cu1 142.39(6) . 3_667 ?
Br1 Cu1 Cu1 100.175(19) . 3_667 ?
C7 N1 N2 119.8(2) . . ?
C7 N1 Cu1 128.23(19) . . ?
N2 N1 Cu1 111.56(16) . . ?
C8 N2 N1 114.4(2) . . ?
C8 N2 H2 126(3) . . ?
N1 N2 H2 119(3) . . ?
C4 N3 C15 121.3(3) . . ?
C4 N3 C17 122.9(3) . . ?
C15 N3 C17 115.5(3) . . ?
C2 O1 Cu1 125.21(16) . . ?
C2 O1 Cu1 134.10(16) . 3_667 ?
Cu1 O1 Cu1 100.43(8) . 3_667 ?
C8 O2 Cu1 112.55(16) . . ?
C6 C1 C7 117.7(2) . . ?
C6 C1 C2 116.5(2) . . ?
C7 C1 C2 125.5(2) . . ?
O1 C2 C3 119.6(2) . . ?
O1 C2 C1 120.4(2) . . ?
C3 C2 C1 120.0(2) . . ?
C2 C3 C4 122.7(3) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
N3 C4 C3 121.7(3) . . ?
N3 C4 C5 121.3(3) . . ?
C3 C4 C5 116.9(3) . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 123.6(3) . . ?
C5 C6 H6 118.2 . . ?
C1 C6 H6 118.2 . . ?
N1 C7 C1 123.3(2) . . ?
N1 C7 H7 118.3 . . ?
C1 C7 H7 118.3 . . ?
O2 C8 N2 120.1(2) . . ?
O2 C8 C9 121.1(2) . . ?
N2 C8 C9 118.8(2) . . ?
C14 C9 C10 118.3(3) . . ?
C14 C9 C8 120.8(3) . . ?
C10 C9 C8 120.8(3) . . ?
C11 C10 C9 122.0(3) . . ?
C11 C10 Cl1 117.8(3) . . ?
C9 C10 Cl1 120.2(2) . . ?
C12 C11 C10 118.7(4) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C11 C12 C13 120.9(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C12 C13 C14 120.1(4) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 120.0(4) . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?
N3 C15 C16 114.5(3) . . ?
N3 C15 H15A 108.6 . . ?
C16 C15 H15A 108.6 . . ?
N3 C15 H15B 108.6 . . ?
C16 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 N3 114.5(4) . . ?
C18 C17 H17A 108.6 . . ?
N3 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
N3 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 Br1 0.906(10) 2.426(13) 3.317(2) 168(4) 1_655

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.820
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.064
####################################################################### 
# 
# 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 1418883'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2016-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H52 Cu N6 O12'
_chemical_formula_weight         776.34

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.7015(4)
_cell_length_b                   15.2568(9)
_cell_length_c                   17.9245(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.912(2)
_cell_angle_gamma                90.00
_cell_volume                     1825.93(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7853
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.1

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             822
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8457
_exptl_absorpt_correction_T_max  0.8672
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15050
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.64
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3384
_reflns_number_gt                2678
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0498P)²+1.3910P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3384
_refine_ls_number_parameters     240
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1161
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.0000 0.0000 0.03899(16) Uani 1 2 d S . .
N1 N 0.1812(3) 0.01251(13) 0.09434(11) 0.0396(5) Uani 1 1 d . . .
N2 N 0.0541(3) -0.05585(14) 0.33059(12) 0.0410(5) Uani 1 1 d D . .
N3 N 0.4005(6) 0.7951(3) 0.27876(17) 0.0799(10) Uani 1 1 d . . .
O1 O 0.1667(3) 0.07300(13) -0.05357(10) 0.0499(5) Uani 1 1 d . . .
O2 O 0.2102(4) -0.05013(19) 0.48459(12) 0.0749(7) Uani 1 1 d . . .
O3 O 0.2177(5) 0.7841(2) 0.27899(18) 0.0981(9) Uani 1 1 d . . .
O4 O 0.4606(5) 0.8685(2) 0.29781(18) 0.0955(9) Uani 1 1 d . . .
O5 O 0.5077(6) 0.7374(3) 0.2600(2) 0.1540(19) Uani 1 1 d . . .
O6 O 1.0222(7) 0.6324(2) 0.2194(2) 0.1365(14) Uani 1 1 d D . .
C1 C 0.4285(4) 0.10618(17) 0.04153(14) 0.0405(6) Uani 1 1 d . . .
C2 C 0.3371(4) 0.11044(16) -0.03232(14) 0.0396(6) Uani 1 1 d . . .
C3 C 0.4380(4) 0.15824(19) -0.08465(15) 0.0478(7) Uani 1 1 d . . .
H3 H 0.3818 0.1623 -0.1338 0.057 Uiso 1 1 calc R . .
C4 C 0.6176(4) 0.19904(18) -0.06505(16) 0.0492(7) Uani 1 1 d . . .
H4 H 0.6796 0.2299 -0.1014 0.059 Uiso 1 1 calc R . .
C5 C 0.7097(4) 0.19555(17) 0.00776(16) 0.0465(6) Uani 1 1 d . . .
C6 C 0.6133(4) 0.14931(18) 0.05938(16) 0.0466(6) Uani 1 1 d . . .
H6A H 0.6718 0.1461 0.1083 0.056 Uiso 1 1 calc R . .
C7 C 0.9086(4) 0.2414(2) 0.02813(19) 0.0618(8) Uani 1 1 d . . .
H7A H 0.8873 0.3036 0.0302 0.093 Uiso 1 1 calc R . .
H7B H 0.9992 0.2286 -0.0091 0.093 Uiso 1 1 calc R . .
H7C H 0.9647 0.2210 0.0761 0.093 Uiso 1 1 calc R . .
C8 C 0.3450(4) 0.05667(17) 0.09930(14) 0.0428(6) Uani 1 1 d . . .
H8 H 0.4180 0.0565 0.1458 0.051 Uiso 1 1 calc R . .
C9 C 0.1369(4) -0.03374(18) 0.16359(14) 0.0431(6) Uani 1 1 d . . .
H9A H 0.2576 -0.0368 0.1975 0.052 Uiso 1 1 calc R . .
H9B H 0.0948 -0.0932 0.1513 0.052 Uiso 1 1 calc R . .
C10 C -0.0260(4) 0.01230(18) 0.20222(15) 0.0469(7) Uani 1 1 d . . .
H10A H 0.0248 0.0685 0.2207 0.056 Uiso 1 1 calc R . .
H10B H -0.1381 0.0236 0.1656 0.056 Uiso 1 1 calc R . .
C11 C -0.1006(4) -0.0384(2) 0.26663(15) 0.0483(7) Uani 1 1 d . . .
H11A H -0.2103 -0.0061 0.2855 0.058 Uiso 1 1 calc R . .
H11B H -0.1535 -0.0941 0.2478 0.058 Uiso 1 1 calc R . .
C12 C -0.0318(5) -0.1085(2) 0.39034(16) 0.0567(8) Uani 1 1 d . . .
H12A H -0.0851 -0.1631 0.3694 0.068 Uiso 1 1 calc R . .
H12B H -0.1406 -0.0764 0.4100 0.068 Uiso 1 1 calc R . .
C13 C 0.1274(5) -0.1275(3) 0.45244(18) 0.0683(9) Uani 1 1 d . . .
H13A H 0.0699 -0.1618 0.4908 0.082 Uiso 1 1 calc R . .
H13B H 0.2327 -0.1620 0.4329 0.082 Uiso 1 1 calc R . .
C14 C 0.2961(6) -0.0001(3) 0.4296(2) 0.0787(11) Uani 1 1 d . . .
H14A H 0.4040 -0.0333 0.4103 0.094 Uiso 1 1 calc R . .
H14B H 0.3531 0.0530 0.4523 0.094 Uiso 1 1 calc R . .
C15 C 0.1449(6) 0.0242(2) 0.36531(19) 0.0660(9) Uani 1 1 d . . .
H15A H 0.0412 0.0608 0.3836 0.079 Uiso 1 1 calc R . .
H15B H 0.2104 0.0574 0.3282 0.079 Uiso 1 1 calc R . .
C16 C 0.8907(7) 0.6710(4) 0.1695(3) 0.1132(16) Uani 1 1 d . . .
H16A H 0.7779 0.6913 0.1942 0.170 Uiso 1 1 calc R . .
H16B H 0.8463 0.6295 0.1313 0.170 Uiso 1 1 calc R . .
H16C H 0.9536 0.7197 0.1471 0.170 Uiso 1 1 calc R . .
H2 H 0.152(4) -0.089(2) 0.3138(19) 0.080 Uiso 1 1 d D . .
H6 H 1.108(5) 0.6772(18) 0.233(2) 0.080 Uiso 1 1 d D . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.8961(18) . ?
Cu1 O1 1.8961(18) 3 ?
Cu1 N1 2.005(2) 3 ?
Cu1 N1 2.005(2) . ?
N1 C8 1.285(3) . ?
N1 C9 1.480(3) . ?
N2 C15 1.478(4) . ?
N2 C12 1.493(3) . ?
N2 C11 1.502(3) . ?
N2 H2 0.899(10) . ?
N3 O5 1.202(4) . ?
N3 O4 1.228(4) . ?
N3 O3 1.237(4) . ?
O1 C2 1.304(3) . ?
O2 C13 1.407(4) . ?
O2 C14 1.409(4) . ?
O6 C16 1.337(6) . ?
O6 H6 0.910(10) . ?
C1 C2 1.412(3) . ?
C1 C6 1.414(4) . ?
C1 C8 1.434(4) . ?
C2 C3 1.406(4) . ?
C3 C4 1.373(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(4) . ?
C5 C7 1.522(4) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8 0.9300 . ?
C9 C10 1.514(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.510(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.502(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.514(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.00(14) . 3 ?
O1 Cu1 N1 88.25(8) . 3 ?
O1 Cu1 N1 91.75(8) 3 3 ?
O1 Cu1 N1 91.75(8) . . ?
O1 Cu1 N1 88.25(8) 3 . ?
N1 Cu1 N1 180.00(13) 3 . ?
C8 N1 C9 115.1(2) . . ?
C8 N1 Cu1 124.10(17) . . ?
C9 N1 Cu1 120.76(16) . . ?
C15 N2 C12 108.2(2) . . ?
C15 N2 C11 114.0(2) . . ?
C12 N2 C11 111.1(2) . . ?
C15 N2 H2 109(2) . . ?
C12 N2 H2 106(2) . . ?
C11 N2 H2 109(2) . . ?
O5 N3 O4 123.8(5) . . ?
O5 N3 O3 121.1(5) . . ?
O4 N3 O3 115.1(3) . . ?
C2 O1 Cu1 130.44(16) . . ?
C13 O2 C14 109.8(2) . . ?
C16 O6 H6 102(3) . . ?
C2 C1 C6 119.5(2) . . ?
C2 C1 C8 122.5(2) . . ?
C6 C1 C8 118.0(2) . . ?
O1 C2 C3 119.4(2) . . ?
O1 C2 C1 123.5(2) . . ?
C3 C2 C1 117.0(2) . . ?
C4 C3 C2 121.7(3) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 122.0(3) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 117.1(2) . . ?
C6 C5 C7 121.9(3) . . ?
C4 C5 C7 121.0(3) . . ?
C5 C6 C1 122.8(3) . . ?
C5 C6 H6A 118.6 . . ?
C1 C6 H6A 118.6 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C1 127.6(2) . . ?
N1 C8 H8 116.2 . . ?
C1 C8 H8 116.2 . . ?
N1 C9 C10 111.5(2) . . ?
N1 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 114.3(2) . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
N2 C11 C10 115.0(2) . . ?
N2 C11 H11A 108.5 . . ?
C10 C11 H11A 108.5 . . ?
N2 C11 H11B 108.5 . . ?
C10 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
N2 C12 C13 110.0(2) . . ?
N2 C12 H12A 109.7 . . ?
C13 C12 H12A 109.7 . . ?
N2 C12 H12B 109.7 . . ?
C13 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
O2 C13 C12 111.8(3) . . ?
O2 C13 H13A 109.2 . . ?
C12 C13 H13A 109.2 . . ?
O2 C13 H13B 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
O2 C14 C15 112.2(3) . . ?
O2 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
O2 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
N2 C15 C14 110.0(3) . . ?
N2 C15 H15A 109.7 . . ?
C14 C15 H15A 109.7 . . ?
N2 C15 H15B 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
O6 C16 H16A 109.5 . . ?
O6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O3 0.899(10) 2.09(2) 2.862(4) 143(3) 1_545
N2 H2 O4 0.899(10) 2.211(17) 3.061(4) 158(3) 1_545
N2 H2 N3 0.899(10) 2.545(12) 3.434(4) 170(3) 1_545
O6 H6 O3 0.910(10) 1.947(17) 2.824(5) 161(4) 1_655

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1418888'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2016-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 Cl2 Cu2 N2 O2'
_chemical_formula_weight         546.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.840(2)
_cell_length_b                   10.704(3)
_cell_length_c                   13.449(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.458(3)
_cell_angle_gamma                90.00
_cell_volume                     1126.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5556
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      27.4

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             556
_exptl_absorpt_coefficient_mu    2.146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7118
_exptl_absorpt_correction_T_max  0.7678
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7719
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_sigmaI/netI    0.0547
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         25.50
_reflns_number_total             1922
_reflns_number_gt                1599
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1257P)²+7.9853P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1922
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0759
_refine_ls_wR_factor_ref         0.2235
_refine_ls_wR_factor_gt          0.2137
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.1536(3) 0.7977(2) 0.4722(2) 0.0603(8) Uani 1 1 d . . .
Cu1 Cu 0.97769(11) 0.64224(9) 0.49661(8) 0.0324(4) Uani 1 1 d . . .
N1 N 0.7659(8) 0.7370(6) 0.4988(5) 0.0312(15) Uani 1 1 d . . .
O1 O 0.8658(7) 0.4894(5) 0.4524(5) 0.0384(14) Uani 1 1 d . . .
C1 C 0.5907(9) 0.5818(7) 0.4065(5) 0.0278(15) Uani 1 1 d . . .
C2 C 0.7106(9) 0.4849(7) 0.4001(6) 0.0282(16) Uani 1 1 d . . .
C3 C 0.6706(11) 0.3833(8) 0.3376(7) 0.039(2) Uani 1 1 d . . .
H3 H 0.7495 0.3193 0.3313 0.047 Uiso 1 1 calc R . .
C4 C 0.5143(11) 0.3781(8) 0.2854(7) 0.041(2) Uani 1 1 d . . .
H4 H 0.4903 0.3101 0.2438 0.049 Uiso 1 1 calc R . .
C5 C 0.3921(11) 0.4694(8) 0.2923(6) 0.0391(19) Uani 1 1 d . . .
C6 C 0.4329(9) 0.5702(8) 0.3535(6) 0.0332(17) Uani 1 1 d . . .
H6 H 0.3518 0.6327 0.3597 0.040 Uiso 1 1 calc R . .
C7 C 0.2197(14) 0.4640(12) 0.2343(8) 0.064(3) Uani 1 1 d . . .
H7A H 0.1301 0.4725 0.2794 0.096 Uiso 1 1 calc R . .
H7B H 0.2081 0.3854 0.2002 0.096 Uiso 1 1 calc R . .
H7C H 0.2119 0.5307 0.1865 0.096 Uiso 1 1 calc R . .
C8 C 0.6244(9) 0.6949(7) 0.4607(5) 0.0276(15) Uani 1 1 d . . .
H8 H 0.5295 0.7450 0.4694 0.033 Uiso 1 1 calc R . .
C9 C 0.7721(10) 0.8608(8) 0.5422(7) 0.0361(18) Uani 1 1 d . . .
H9 H 0.8342 0.9228 0.5047 0.043 Uiso 1 1 calc R . .
C10 C 0.6285(12) 0.9124(9) 0.5968(7) 0.050(2) Uani 1 1 d . . .
H10A H 0.6034 1.0008 0.5892 0.060 Uiso 1 1 calc R . .
H10B H 0.5295 0.8596 0.6037 0.060 Uiso 1 1 calc R . .
C11 C 0.7879(13) 0.8774(9) 0.6521(8) 0.053(2) Uani 1 1 d . . .
H11A H 0.7870 0.8029 0.6932 0.063 Uiso 1 1 calc R . .
H11B H 0.8610 0.9441 0.6786 0.063 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
Cl1 Cu1 2.198(2) . ?
Cu1 O1 1.933(5) . ?
Cu1 N1 1.947(6) . ?
Cu1 O1 1.964(5) 3_766 ?
N1 C8 1.275(10) . ?
N1 C9 1.449(10) . ?
O1 C2 1.370(9) . ?
O1 Cu1 1.964(5) 3_766 ?
C1 C6 1.396(10) . ?
C1 C2 1.406(11) . ?
C1 C8 1.430(11) . ?
C2 C3 1.399(11) . ?
C3 C4 1.376(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(12) . ?
C5 C7 1.520(12) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8 0.9300 . ?
C9 C11 1.486(13) . ?
C9 C10 1.487(12) . ?
C9 H9 0.9800 . ?
C10 C11 1.464(14) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N1 94.2(2) . . ?
O1 Cu1 O1 76.3(2) . 3_766 ?
N1 Cu1 O1 152.1(3) . 3_766 ?
O1 Cu1 Cl1 150.7(2) . . ?
N1 Cu1 Cl1 98.7(2) . . ?
O1 Cu1 Cl1 102.16(18) 3_766 . ?
C8 N1 C9 119.5(6) . . ?
C8 N1 Cu1 122.1(5) . . ?
C9 N1 Cu1 118.3(5) . . ?
C2 O1 Cu1 124.1(5) . . ?
C2 O1 Cu1 132.2(5) . 3_766 ?
Cu1 O1 Cu1 103.7(2) . 3_766 ?
C6 C1 C2 118.6(7) . . ?
C6 C1 C8 117.8(7) . . ?
C2 C1 C8 123.6(7) . . ?
O1 C2 C3 119.7(7) . . ?
O1 C2 C1 121.3(7) . . ?
C3 C2 C1 119.0(7) . . ?
C4 C3 C2 119.9(7) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 122.6(8) . . ?
C5 C4 H4 118.7 . . ?
C3 C4 H4 118.7 . . ?
C4 C5 C6 117.2(8) . . ?
C4 C5 C7 122.7(9) . . ?
C6 C5 C7 120.1(9) . . ?
C5 C6 C1 122.7(8) . . ?
C5 C6 H6 118.7 . . ?
C1 C6 H6 118.7 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C1 129.3(7) . . ?
N1 C8 H8 115.4 . . ?
C1 C8 H8 115.4 . . ?
N1 C9 C11 120.6(7) . . ?
N1 C9 C10 122.1(7) . . ?
C11 C9 C10 59.0(6) . . ?
N1 C9 H9 114.6 . . ?
C11 C9 H9 114.6 . . ?
C10 C9 H9 114.6 . . ?
C11 C10 C9 60.5(6) . . ?
C11 C10 H10A 117.7 . . ?
C9 C10 H10A 117.7 . . ?
C11 C10 H10B 117.7 . . ?
C9 C10 H10B 117.7 . . ?
H10A C10 H10B 114.8 . . ?
C10 C11 C9 60.5(6) . . ?
C10 C11 H11A 117.7 . . ?
C9 C11 H11A 117.7 . . ?
C10 C11 H11B 117.7 . . ?
C9 C11 H11B 117.7 . . ?
H11A C11 H11B 114.8 . . ?

_diffrn_measured_fraction_theta_max 0.915
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.915
_refine_diff_density_max         1.757
_refine_diff_density_min         -0.729
_refine_diff_density_rms         0.165
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1418889'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2016-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H44 Cl4 Cu2 N4 O4'
_chemical_formula_weight         793.57

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.188(2)
_cell_length_b                   16.085(3)
_cell_length_c                   10.0808(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.675(2)
_cell_angle_gamma                90.00
_cell_volume                     1635.1(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2619
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      27.0

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             820
_exptl_absorpt_coefficient_mu    1.670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6087
_exptl_absorpt_correction_T_max  0.6613
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8519
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3043
_reflns_number_gt                2406
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0366P)²+1.1549P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3043
_refine_ls_number_parameters     204
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0778
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.94171(4) 0.07007(2) 0.56563(4) 0.02537(12) Uani 1 1 d . . .
N1 N 1.0172(2) 0.17814(14) 0.6537(3) 0.0253(6) Uani 1 1 d . . .
N2 N 0.7829(3) 0.42167(17) 0.5099(3) 0.0364(7) Uani 1 1 d D . .
O1 O 1.0963(2) 0.04474(12) 0.5210(2) 0.0281(5) Uani 1 1 d . . .
O2 O 0.5797(3) 0.54630(17) 0.4145(3) 0.0516(7) Uani 1 1 d . . .
Cl1 Cl 0.73243(8) 0.12439(5) 0.43245(9) 0.0393(2) Uani 1 1 d . . .
Cl2 Cl 0.95787(8) 0.02736(5) 0.81205(9) 0.0354(2) Uani 1 1 d . . .
C1 C 1.2121(3) 0.17389(18) 0.6031(3) 0.0286(7) Uani 1 1 d . . .
C2 C 1.1954(3) 0.09567(18) 0.5339(3) 0.0249(7) Uani 1 1 d . . .
C3 C 1.2872(3) 0.0734(2) 0.4813(4) 0.0347(8) Uani 1 1 d . . .
H3 H 1.2781 0.0226 0.4338 0.042 Uiso 1 1 calc R . .
C4 C 1.3911(3) 0.1248(2) 0.4979(4) 0.0375(8) Uani 1 1 d . . .
H4 H 1.4507 0.1074 0.4618 0.045 Uiso 1 1 calc R . .
C5 C 1.4098(3) 0.2018(2) 0.5669(4) 0.0366(8) Uani 1 1 d . . .
C6 C 1.3203(3) 0.2246(2) 0.6180(4) 0.0388(8) Uani 1 1 d . . .
H6 H 1.3308 0.2757 0.6648 0.047 Uiso 1 1 calc R . .
C7 C 1.1265(3) 0.20775(19) 0.6626(3) 0.0314(7) Uani 1 1 d . . .
H7 H 1.1542 0.2575 0.7141 0.038 Uiso 1 1 calc R . .
C8 C 0.9518(3) 0.22501(19) 0.7313(4) 0.0356(8) Uani 1 1 d . . .
H8A H 1.0061 0.2191 0.8362 0.043 Uiso 1 1 calc R . .
H8B H 0.8675 0.1984 0.7091 0.043 Uiso 1 1 calc R . .
C9 C 0.9260(4) 0.3165(2) 0.6981(4) 0.0431(9) Uani 1 1 d . . .
H9A H 0.8925 0.3406 0.7637 0.052 Uiso 1 1 calc R . .
H9B H 1.0086 0.3443 0.7160 0.052 Uiso 1 1 calc R . .
C10 C 0.8293(4) 0.3306(2) 0.5443(4) 0.0425(9) Uani 1 1 d . . .
H10A H 0.7525 0.2956 0.5227 0.051 Uiso 1 1 calc R . .
H10B H 0.8688 0.3137 0.4798 0.051 Uiso 1 1 calc R . .
C11 C 0.6782(4) 0.4272(2) 0.3563(4) 0.0423(9) Uani 1 1 d . . .
H11A H 0.6049 0.3911 0.3449 0.051 Uiso 1 1 calc R . .
H11B H 0.7136 0.4082 0.2892 0.051 Uiso 1 1 calc R . .
C12 C 0.6289(4) 0.5144(2) 0.3182(4) 0.0460(9) Uani 1 1 d . . .
H12A H 0.7008 0.5495 0.3218 0.055 Uiso 1 1 calc R . .
H12B H 0.5592 0.5157 0.2184 0.055 Uiso 1 1 calc R . .
C13 C 0.6820(4) 0.5444(3) 0.5623(5) 0.0537(11) Uani 1 1 d . . .
H13A H 0.6475 0.5666 0.6282 0.064 Uiso 1 1 calc R . .
H13B H 0.7548 0.5796 0.5691 0.064 Uiso 1 1 calc R . .
C14 C 0.7326(4) 0.4581(2) 0.6099(4) 0.0429(9) Uani 1 1 d . . .
H14A H 0.8032 0.4596 0.7092 0.052 Uiso 1 1 calc R . .
H14B H 0.6616 0.4237 0.6105 0.052 Uiso 1 1 calc R . .
C15 C 1.5247(4) 0.2563(2) 0.5811(5) 0.0535(11) Uani 1 1 d . . .
H15A H 1.5039 0.2835 0.4889 0.080 Uiso 1 1 calc R . .
H15B H 1.6026 0.2228 0.6073 0.080 Uiso 1 1 calc R . .
H15C H 1.5406 0.2973 0.6561 0.080 Uiso 1 1 calc R . .
H2 H 0.854(2) 0.4522(18) 0.520(4) 0.041(10) Uiso 1 1 d D . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.968(2) . ?
Cu1 O1 2.008(2) 3_756 ?
Cu1 O1 2.008(2) . ?
Cu1 Cl1 2.3075(9) . ?
Cu1 Cl2 2.5072(9) . ?
N1 C7 1.279(4) . ?
N1 C8 1.486(4) . ?
N2 C14 1.472(5) . ?
N2 C11 1.485(4) . ?
N2 C10 1.543(4) . ?
N2 H2 0.903(10) . ?
O1 C2 1.339(3) . ?
O1 Cu1 2.008(2) 3_756 ?
O2 C12 1.405(4) . ?
O2 C13 1.432(5) . ?
C1 C2 1.411(4) . ?
C1 C6 1.413(4) . ?
C1 C7 1.440(4) . ?
C2 C3 1.391(4) . ?
C3 C4 1.376(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.360(5) . ?
C5 C15 1.511(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.510(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.474(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.495(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.498(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
N1 Cu1 O1 167.73(9) . 3_756 ?
N1 Cu1 O1 92.16(9) . . ?
O1 Cu1 O1 75.91(9) 3_756 . ?
N1 Cu1 Cl1 93.26(8) . . ?
O1 Cu1 Cl1 97.18(6) 3_756 . ?
O1 Cu1 Cl1 134.56(7) . . ?
N1 Cu1 Cl2 87.83(8) . . ?
O1 Cu1 Cl2 95.15(7) 3_756 . ?
O1 Cu1 Cl2 117.83(7) . . ?
Cl1 Cu1 Cl2 107.43(3) . . ?
C7 N1 C8 116.6(3) . . ?
C7 N1 Cu1 124.8(2) . . ?
C8 N1 Cu1 118.2(2) . . ?
C14 N2 C11 109.1(3) . . ?
C14 N2 C10 114.5(3) . . ?
C11 N2 C10 109.1(3) . . ?
C14 N2 H2 106(2) . . ?
C11 N2 H2 110(2) . . ?
C10 N2 H2 107(2) . . ?
C2 O1 Cu1 127.96(19) . 3_756 ?
C2 O1 Cu1 127.70(18) . . ?
Cu1 O1 Cu1 104.09(9) 3_756 . ?
C12 O2 C13 109.6(3) . . ?
C2 C1 C6 119.4(3) . . ?
C2 C1 C7 125.0(3) . . ?
C6 C1 C7 115.6(3) . . ?
O1 C2 C3 121.5(3) . . ?
O1 C2 C1 121.3(3) . . ?
C3 C2 C1 117.2(3) . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 122.1(3) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C6 C5 C4 116.9(3) . . ?
C6 C5 C15 122.9(3) . . ?
C4 C5 C15 120.1(3) . . ?
C5 C6 C1 122.8(3) . . ?
C5 C6 H6 118.6 . . ?
C1 C6 H6 118.6 . . ?
N1 C7 C1 128.2(3) . . ?
N1 C7 H7 115.9 . . ?
C1 C7 H7 115.9 . . ?
N1 C8 C9 118.0(3) . . ?
N1 C8 H8A 107.8 . . ?
C9 C8 H8A 107.8 . . ?
N1 C8 H8B 107.8 . . ?
C9 C8 H8B 107.8 . . ?
H8A C8 H8B 107.1 . . ?
C10 C9 C8 111.4(3) . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 N2 113.8(3) . . ?
C9 C10 H10A 108.8 . . ?
N2 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
N2 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
N2 C11 C12 111.1(3) . . ?
N2 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N2 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
O2 C12 C11 112.1(3) . . ?
O2 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
O2 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
O2 C13 C14 112.0(3) . . ?
O2 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
O2 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
N2 C14 C13 110.7(3) . . ?
N2 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 Cl2 0.903(10) 2.38(2) 3.164(3) 145(3) 2_756
N2 H2 Cl2 0.903(10) 2.82(3) 3.445(3) 127(3) 4_565

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1418890'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2016-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 Cl Cu N2 O2'
_chemical_formula_weight         356.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2905(8)
_cell_length_b                   9.0921(10)
_cell_length_c                   11.8121(13)
_cell_angle_alpha                100.605(3)
_cell_angle_beta                 98.485(3)
_cell_angle_gamma                91.807(3)
_cell_volume                     759.79(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5779
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             366
_exptl_absorpt_coefficient_mu    1.618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6879
_exptl_absorpt_correction_T_max  0.7073
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6463
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         25.49
_reflns_number_total             2760
_reflns_number_gt                2490
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0289P)²+1.2979P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2760
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1061
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.67648(6) 1.02504(4) 0.16909(3) 0.03483(16) Uani 1 1 d . . .
N1 N 0.6994(4) 0.8639(3) 0.0393(2) 0.0333(6) Uani 1 1 d . . .
N2 N 0.6190(4) 0.8529(3) 0.2456(2) 0.0365(6) Uani 1 1 d . . .
O1 O 0.7511(4) 1.1754(3) 0.0901(2) 0.0412(6) Uani 1 1 d . . .
O2 O 0.0397(5) 0.3790(4) 0.2371(3) 0.0746(9) Uani 1 1 d . . .
H2 H -0.0554 0.3240 0.2182 0.112 Uiso 1 1 calc R . .
C1 C 0.7914(5) 1.0169(4) -0.0909(3) 0.0374(8) Uani 1 1 d . . .
C2 C 0.7918(4) 1.1581(4) -0.0158(3) 0.0357(7) Uani 1 1 d . . .
C3 C 0.8381(5) 1.2853(4) -0.0595(3) 0.0428(8) Uani 1 1 d . . .
H3 H 0.8425 1.3793 -0.0118 0.051 Uiso 1 1 calc R . .
C4 C 0.8772(5) 1.2745(5) -0.1713(3) 0.0474(9) Uani 1 1 d . . .
H4 H 0.9044 1.3619 -0.1975 0.057 Uiso 1 1 calc R . .
C5 C 0.8773(5) 1.1379(5) -0.2458(3) 0.0464(9) Uani 1 1 d . . .
C6 C 0.8364(5) 1.0118(5) -0.2043(3) 0.0442(8) Uani 1 1 d . . .
H6 H 0.8381 0.9188 -0.2525 0.053 Uiso 1 1 calc R . .
C7 C 0.7488(5) 0.8790(4) -0.0582(3) 0.0369(7) Uani 1 1 d . . .
H7 H 0.7572 0.7918 -0.1120 0.044 Uiso 1 1 calc R . .
C8 C 0.6318(4) 0.7166(4) 0.1816(3) 0.0364(7) Uani 1 1 d . . .
C9 C 0.6165(5) 0.5875(4) 0.2267(4) 0.0497(9) Uani 1 1 d . . .
H9 H 0.6282 0.4941 0.1814 0.060 Uiso 1 1 calc R . .
C10 C 0.5837(6) 0.5996(5) 0.3397(4) 0.0552(10) Uani 1 1 d . . .
H10 H 0.5738 0.5143 0.3719 0.066 Uiso 1 1 calc R . .
C11 C 0.5657(6) 0.7379(5) 0.4043(4) 0.0535(10) Uani 1 1 d . . .
H11 H 0.5409 0.7476 0.4803 0.064 Uiso 1 1 calc R . .
C12 C 0.5850(5) 0.8634(4) 0.3553(3) 0.0439(8) Uani 1 1 d . . .
H12 H 0.5740 0.9576 0.3996 0.053 Uiso 1 1 calc R . .
C13 C 0.9171(6) 1.1297(6) -0.3696(3) 0.0621(12) Uani 1 1 d . . .
H13A H 0.9459 1.0294 -0.4007 0.093 Uiso 1 1 calc R . .
H13B H 1.0208 1.1978 -0.3689 0.093 Uiso 1 1 calc R . .
H13C H 0.8098 1.1566 -0.4172 0.093 Uiso 1 1 calc R . .
C14 C 0.0852(9) 0.4101(7) 0.3571(5) 0.0889(17) Uani 1 1 d . . .
H14A H 0.2114 0.4506 0.3786 0.133 Uiso 1 1 calc R . .
H14B H 0.0719 0.3196 0.3868 0.133 Uiso 1 1 calc R . .
H14C H 0.0038 0.4818 0.3894 0.133 Uiso 1 1 calc R . .
C22 C 0.6578(5) 0.7130(4) 0.0573(3) 0.0401(8) Uani 1 1 d . . .
H22A H 0.7587 0.6503 0.0390 0.048 Uiso 1 1 calc R . .
H22B H 0.5455 0.6701 0.0054 0.048 Uiso 1 1 calc R . .
Cl1 Cl 0.6386(2) 1.20419(11) 0.31927(9) 0.0688(4) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.900(2) . ?
Cu1 N1 1.947(3) . ?
Cu1 N2 2.008(3) . ?
Cu1 Cl1 2.2328(10) . ?
N1 C7 1.285(4) . ?
N1 C22 1.456(4) . ?
N2 C8 1.342(4) . ?
N2 C12 1.342(4) . ?
O1 C2 1.311(4) . ?
O2 C14 1.381(6) . ?
O2 H2 0.8200 . ?
C1 C7 1.417(5) . ?
C1 C6 1.418(5) . ?
C1 C2 1.419(5) . ?
C2 C3 1.401(5) . ?
C3 C4 1.378(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.368(6) . ?
C5 C13 1.521(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.383(5) . ?
C8 C22 1.503(5) . ?
C9 C10 1.377(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.367(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N1 92.84(11) . . ?
O1 Cu1 N2 173.82(11) . . ?
N1 Cu1 N2 82.49(11) . . ?
O1 Cu1 Cl1 89.21(8) . . ?
N1 Cu1 Cl1 177.38(9) . . ?
N2 Cu1 Cl1 95.58(9) . . ?
C7 N1 C22 118.2(3) . . ?
C7 N1 Cu1 126.2(2) . . ?
C22 N1 Cu1 115.6(2) . . ?
C8 N2 C12 118.8(3) . . ?
C8 N2 Cu1 114.9(2) . . ?
C12 N2 Cu1 126.0(2) . . ?
C2 O1 Cu1 128.0(2) . . ?
C14 O2 H2 109.5 . . ?
C7 C1 C6 117.7(3) . . ?
C7 C1 C2 123.2(3) . . ?
C6 C1 C2 119.1(3) . . ?
O1 C2 C3 119.0(3) . . ?
O1 C2 C1 124.0(3) . . ?
C3 C2 C1 117.0(3) . . ?
C4 C3 C2 121.7(4) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 122.1(4) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C6 C5 C4 117.3(3) . . ?
C6 C5 C13 121.8(4) . . ?
C4 C5 C13 120.9(4) . . ?
C5 C6 C1 122.8(4) . . ?
C5 C6 H6 118.6 . . ?
C1 C6 H6 118.6 . . ?
N1 C7 C1 125.7(3) . . ?
N1 C7 H7 117.2 . . ?
C1 C7 H7 117.2 . . ?
N2 C8 C9 121.9(3) . . ?
N2 C8 C22 115.8(3) . . ?
C9 C8 C22 122.3(3) . . ?
C10 C9 C8 118.8(4) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C11 C10 C9 119.5(4) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 119.1(4) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
N2 C12 C11 121.8(4) . . ?
N2 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C22 C8 110.3(3) . . ?
N1 C22 H22A 109.6 . . ?
C8 C22 H22A 109.6 . . ?
N1 C22 H22B 109.6 . . ?
C8 C22 H22B 109.6 . . ?
H22A C22 H22B 108.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 Cl1 0.82 2.95 3.624(4) 141.1 1_445
O2 H2 O1 0.82 2.15 2.892(4) 151.3 1_445

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.714
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.076
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1418891'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2016-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H44 Cu2 N4 O4'
_chemical_formula_weight         771.87

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   24.219(3)
_cell_length_b                   10.2396(13)
_cell_length_c                   15.6794(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.360(2)
_cell_angle_gamma                90.00
_cell_volume                     3711.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4666
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1608
_exptl_absorpt_coefficient_mu    1.192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7163
_exptl_absorpt_correction_T_max  0.7391
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19090
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         0.88
_diffrn_reflns_theta_max         25.50
_reflns_number_total             6919
_reflns_number_gt                4647
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0387P)²+1.1557P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6919
_refine_ls_number_parameters     454
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0933
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.259675(15) -0.21793(3) 0.36803(2) 0.05259(11) Uani 1 1 d . . .
Cu2 Cu 0.237622(18) 0.23067(3) 0.57886(2) 0.06631(13) Uani 1 1 d . . .
N1 N 0.20919(10) -0.1017(2) 0.27751(14) 0.0518(5) Uani 1 1 d . . .
N2 N 0.26157(12) 0.3081(2) 0.48064(15) 0.0600(6) Uani 1 1 d . . .
N3 N 0.30618(11) -0.2603(2) 0.49122(15) 0.0548(6) Uani 1 1 d . . .
N4 N 0.21209(14) 0.0859(2) 0.64095(16) 0.0716(8) Uani 1 1 d . . .
O1 O 0.19918(9) -0.33143(18) 0.37220(14) 0.0670(5) Uani 1 1 d . . .
O2 O 0.31283(11) 0.2321(2) 0.65927(14) 0.0831(7) Uani 1 1 d . . .
O3 O 0.32405(8) -0.18457(19) 0.32701(12) 0.0621(5) Uani 1 1 d . . .
O4 O 0.16420(10) 0.3114(2) 0.54144(14) 0.0742(6) Uani 1 1 d . . .
C1 C 0.12027(12) -0.2265(3) 0.26213(18) 0.0532(7) Uani 1 1 d . . .
C2 C 0.14420(13) -0.3237(3) 0.3270(2) 0.0556(7) Uani 1 1 d . . .
C3 C 0.10552(14) -0.4160(3) 0.3439(2) 0.0682(8) Uani 1 1 d . . .
H3 H 0.1199 -0.4816 0.3856 0.082 Uiso 1 1 calc R . .
C4 C 0.04749(14) -0.4118(3) 0.3005(2) 0.0730(9) Uani 1 1 d . . .
H4 H 0.0236 -0.4752 0.3133 0.088 Uiso 1 1 calc R . .
C5 C 0.02272(13) -0.3151(3) 0.2373(2) 0.0685(8) Uani 1 1 d . . .
C6 C 0.06013(13) -0.2262(3) 0.2191(2) 0.0650(8) Uani 1 1 d . . .
H6 H 0.0450 -0.1624 0.1762 0.078 Uiso 1 1 calc R . .
C7 C 0.15482(13) -0.1221(3) 0.24207(18) 0.0570(7) Uani 1 1 d . . .
H7 H 0.1353 -0.0630 0.1984 0.068 Uiso 1 1 calc R . .
C8 C 0.23518(13) 0.0136(3) 0.24761(19) 0.0605(7) Uani 1 1 d . . .
H8A H 0.2072 0.0515 0.1959 0.073 Uiso 1 1 calc R . .
H8B H 0.2683 -0.0141 0.2296 0.073 Uiso 1 1 calc R . .
C9 C 0.25456(13) 0.1184(3) 0.3212(2) 0.0646(8) Uani 1 1 d . . .
H9A H 0.2807 0.0786 0.3741 0.078 Uiso 1 1 calc R . .
H9B H 0.2758 0.1858 0.3009 0.078 Uiso 1 1 calc R . .
C10 C 0.20548(13) 0.1805(3) 0.3458(2) 0.0679(8) Uani 1 1 d . . .
H10A H 0.1934 0.1220 0.3855 0.081 Uiso 1 1 calc R . .
H10B H 0.1731 0.1902 0.2920 0.081 Uiso 1 1 calc R . .
C11 C 0.21899(14) 0.3136(3) 0.39097(19) 0.0659(8) Uani 1 1 d . . .
H11A H 0.2337 0.3707 0.3534 0.079 Uiso 1 1 calc R . .
H11B H 0.1834 0.3516 0.3960 0.079 Uiso 1 1 calc R . .
C12 C 0.31071(15) 0.3645(3) 0.4927(2) 0.0637(8) Uani 1 1 d . . .
H12 H 0.3160 0.4079 0.4436 0.076 Uiso 1 1 calc R . .
C13 C 0.35855(15) 0.3682(3) 0.5735(2) 0.0642(8) Uani 1 1 d . . .
C14 C 0.35744(17) 0.2993(3) 0.6516(2) 0.0718(9) Uani 1 1 d . . .
C15 C 0.40850(19) 0.3026(4) 0.7244(2) 0.0869(11) Uani 1 1 d . . .
H15 H 0.4091 0.2599 0.7770 0.104 Uiso 1 1 calc R . .
C16 C 0.45693(18) 0.3665(4) 0.7200(3) 0.0893(11) Uani 1 1 d . . .
H16 H 0.4897 0.3650 0.7695 0.107 Uiso 1 1 calc R . .
C17 C 0.45908(17) 0.4343(3) 0.6434(3) 0.0794(10) Uani 1 1 d . . .
C18 C 0.40943(16) 0.4337(3) 0.5726(2) 0.0729(9) Uani 1 1 d . . .
H18 H 0.4094 0.4792 0.5212 0.088 Uiso 1 1 calc R . .
C19 C -0.04244(14) -0.3074(4) 0.1965(3) 0.0985(12) Uani 1 1 d . . .
H19A H -0.0526 -0.2249 0.1668 0.148 Uiso 1 1 calc R . .
H19B H -0.0607 -0.3156 0.2427 0.148 Uiso 1 1 calc R . .
H19C H -0.0552 -0.3769 0.1540 0.148 Uiso 1 1 calc R . .
C20 C 0.51488(16) 0.4973(4) 0.6394(3) 0.1050(13) Uani 1 1 d . . .
H20A H 0.5078 0.5455 0.5847 0.157 Uiso 1 1 calc R . .
H20B H 0.5433 0.4308 0.6418 0.157 Uiso 1 1 calc R . .
H20C H 0.5289 0.5555 0.6892 0.157 Uiso 1 1 calc R . .
C21 C 0.39925(12) -0.2100(2) 0.46700(18) 0.0528(7) Uani 1 1 d . . .
C22 C 0.37860(13) -0.1804(3) 0.37417(19) 0.0534(7) Uani 1 1 d . . .
C23 C 0.42066(13) -0.1465(3) 0.3324(2) 0.0615(8) Uani 1 1 d . . .
H23 H 0.4090 -0.1293 0.2714 0.074 Uiso 1 1 calc R . .
C24 C 0.47834(14) -0.1383(3) 0.3789(2) 0.0648(8) Uani 1 1 d . . .
H24 H 0.5044 -0.1147 0.3485 0.078 Uiso 1 1 calc R . .
C25 C 0.49923(13) -0.1641(3) 0.4706(2) 0.0638(8) Uani 1 1 d . . .
C26 C 0.45914(13) -0.1996(3) 0.5120(2) 0.0624(8) Uani 1 1 d . . .
H26 H 0.4719 -0.2179 0.5728 0.075 Uiso 1 1 calc R . .
C27 C 0.36177(14) -0.2493(3) 0.51794(19) 0.0587(8) Uani 1 1 d . . .
H27 H 0.3798 -0.2693 0.5776 0.070 Uiso 1 1 calc R . .
C28 C 0.27696(14) -0.3053(3) 0.5563(2) 0.0640(8) Uani 1 1 d . . .
H28A H 0.3054 -0.3423 0.6079 0.077 Uiso 1 1 calc R . .
H28B H 0.2495 -0.3734 0.5292 0.077 Uiso 1 1 calc R . .
C29 C 0.24519(14) -0.1935(3) 0.5867(2) 0.0739(9) Uani 1 1 d . . .
H29A H 0.2193 -0.1520 0.5343 0.089 Uiso 1 1 calc R . .
H29B H 0.2217 -0.2296 0.6214 0.089 Uiso 1 1 calc R . .
C30 C 0.28440(15) -0.0921(3) 0.6414(2) 0.0783(10) Uani 1 1 d . . .
H30A H 0.2985 -0.0373 0.6019 0.094 Uiso 1 1 calc R . .
H30B H 0.3176 -0.1353 0.6820 0.094 Uiso 1 1 calc R . .
C31 C 0.25612(16) -0.0053(3) 0.6958(2) 0.0842(11) Uani 1 1 d . . .
H31A H 0.2380 -0.0605 0.7299 0.101 Uiso 1 1 calc R . .
H31B H 0.2860 0.0450 0.7379 0.101 Uiso 1 1 calc R . .
C32 C 0.15904(18) 0.0703(3) 0.6392(2) 0.0787(10) Uani 1 1 d . . .
H32 H 0.1515 -0.0025 0.6693 0.094 Uiso 1 1 calc R . .
C33 C 0.11004(16) 0.1508(3) 0.5965(2) 0.0707(9) Uani 1 1 d . . .
C34 C 0.11558(16) 0.2697(3) 0.5532(2) 0.0690(9) Uani 1 1 d . . .
C35 C 0.06567(16) 0.3469(4) 0.5220(2) 0.0844(10) Uani 1 1 d . . .
H35 H 0.0685 0.4291 0.4984 0.101 Uiso 1 1 calc R . .
C36 C 0.01248(17) 0.3032(4) 0.5255(2) 0.0908(11) Uani 1 1 d . . .
H36 H -0.0197 0.3563 0.5029 0.109 Uiso 1 1 calc R . .
C37 C 0.00539(18) 0.1829(4) 0.5617(3) 0.0873(11) Uani 1 1 d . . .
C38 C 0.05470(18) 0.1117(3) 0.5984(2) 0.0857(11) Uani 1 1 d . . .
H38 H 0.0514 0.0331 0.6262 0.103 Uiso 1 1 calc R . .
C39 C 0.56323(13) -0.1511(3) 0.5208(2) 0.0796(10) Uani 1 1 d . . .
H39A H 0.5685 -0.0854 0.5662 0.119 Uiso 1 1 calc R . .
H39B H 0.5840 -0.1265 0.4798 0.119 Uiso 1 1 calc R . .
H39C H 0.5777 -0.2331 0.5481 0.119 Uiso 1 1 calc R . .
C40 C -0.05423(17) 0.1342(4) 0.5590(3) 0.1219(16) Uani 1 1 d . . .
H40A H -0.0570 0.0424 0.5460 0.183 Uiso 1 1 calc R . .
H40B H -0.0830 0.1802 0.5134 0.183 Uiso 1 1 calc R . .
H40C H -0.0604 0.1493 0.6159 0.183 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 1.887(2) . ?
Cu1 O3 1.8867(19) . ?
Cu1 N3 1.972(2) . ?
Cu1 N1 1.972(2) . ?
Cu2 O2 1.881(3) . ?
Cu2 O4 1.888(2) . ?
Cu2 N2 1.967(2) . ?
Cu2 N4 1.971(3) . ?
N1 C7 1.285(3) . ?
N1 C8 1.478(3) . ?
N2 C12 1.285(4) . ?
N2 C11 1.476(4) . ?
N3 C27 1.290(4) . ?
N3 C28 1.477(3) . ?
N4 C32 1.287(4) . ?
N4 C31 1.484(4) . ?
O1 C2 1.311(3) . ?
O2 C14 1.316(4) . ?
O3 C22 1.308(3) . ?
O4 C34 1.317(4) . ?
C1 C6 1.411(4) . ?
C1 C2 1.417(4) . ?
C1 C7 1.449(4) . ?
C2 C3 1.410(4) . ?
C3 C4 1.367(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.403(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(4) . ?
C5 C19 1.518(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.542(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.497(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.526(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.440(4) . ?
C12 H12 0.9300 . ?
C13 C18 1.406(4) . ?
C13 C14 1.421(4) . ?
C14 C15 1.411(5) . ?
C15 C16 1.362(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.401(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(4) . ?
C17 C20 1.516(5) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C26 1.415(4) . ?
C21 C22 1.424(4) . ?
C21 C27 1.434(4) . ?
C22 C23 1.409(4) . ?
C23 C24 1.372(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.400(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.367(4) . ?
C25 C39 1.520(4) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.533(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.493(4) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.528(4) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.436(5) . ?
C32 H32 0.9300 . ?
C33 C38 1.408(5) . ?
C33 C34 1.419(4) . ?
C34 C35 1.405(4) . ?
C35 C36 1.381(5) . ?
C35 H35 0.9300 . ?
C36 C37 1.388(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.371(5) . ?
C37 C40 1.516(5) . ?
C38 H38 0.9300 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?

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 148.51(9) . . ?
O1 Cu1 N3 93.03(10) . . ?
O3 Cu1 N3 94.89(9) . . ?
O1 Cu1 N1 94.34(9) . . ?
O3 Cu1 N1 92.48(9) . . ?
N3 Cu1 N1 152.60(9) . . ?
O2 Cu2 O4 146.99(10) . . ?
O2 Cu2 N2 93.94(11) . . ?
O4 Cu2 N2 92.90(10) . . ?
O2 Cu2 N4 93.36(11) . . ?
O4 Cu2 N4 94.43(11) . . ?
N2 Cu2 N4 154.02(10) . . ?
C7 N1 C8 118.1(2) . . ?
C7 N1 Cu1 123.25(18) . . ?
C8 N1 Cu1 118.61(18) . . ?
C12 N2 C11 118.4(2) . . ?
C12 N2 Cu2 122.9(2) . . ?
C11 N2 Cu2 118.4(2) . . ?
C27 N3 C28 118.1(2) . . ?
C27 N3 Cu1 122.30(19) . . ?
C28 N3 Cu1 119.6(2) . . ?
C32 N4 C31 118.3(3) . . ?
C32 N4 Cu2 122.8(2) . . ?
C31 N4 Cu2 118.8(2) . . ?
C2 O1 Cu1 128.18(17) . . ?
C14 O2 Cu2 126.9(2) . . ?
C22 O3 Cu1 127.68(17) . . ?
C34 O4 Cu2 127.8(2) . . ?
C6 C1 C2 119.2(3) . . ?
C6 C1 C7 118.3(3) . . ?
C2 C1 C7 122.3(3) . . ?
O1 C2 C3 118.9(3) . . ?
O1 C2 C1 124.2(3) . . ?
C3 C2 C1 116.9(3) . . ?
C4 C3 C2 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 122.2(3) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C6 C5 C4 116.4(3) . . ?
C6 C5 C19 123.1(3) . . ?
C4 C5 C19 120.4(3) . . ?
C5 C6 C1 123.3(3) . . ?
C5 C6 H6 118.3 . . ?
C1 C6 H6 118.3 . . ?
N1 C7 C1 127.6(3) . . ?
N1 C7 H7 116.2 . . ?
C1 C7 H7 116.2 . . ?
N1 C8 C9 112.4(2) . . ?
N1 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 113.6(2) . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 C11 115.0(3) . . ?
C9 C10 H10A 108.5 . . ?
C11 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
C11 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
N2 C11 C10 113.6(2) . . ?
N2 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
N2 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
N2 C12 C13 127.4(3) . . ?
N2 C12 H12 116.3 . . ?
C13 C12 H12 116.3 . . ?
C18 C13 C14 119.2(3) . . ?
C18 C13 C12 118.8(3) . . ?
C14 C13 C12 121.9(3) . . ?
O2 C14 C15 118.9(3) . . ?
O2 C14 C13 124.4(3) . . ?
C15 C14 C13 116.6(4) . . ?
C16 C15 C14 122.0(4) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C16 C17 122.3(4) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
C18 C17 C16 116.3(4) . . ?
C18 C17 C20 123.0(4) . . ?
C16 C17 C20 120.5(4) . . ?
C17 C18 C13 123.6(3) . . ?
C17 C18 H18 118.2 . . ?
C13 C18 H18 118.2 . . ?
C5 C19 H19A 109.5 . . ?
C5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 119.2(3) . . ?
C26 C21 C27 118.0(3) . . ?
C22 C21 C27 122.8(3) . . ?
O3 C22 C23 119.6(3) . . ?
O3 C22 C21 123.9(3) . . ?
C23 C22 C21 116.5(3) . . ?
C24 C23 C22 122.1(3) . . ?
C24 C23 H23 119.0 . . ?
C22 C23 H23 119.0 . . ?
C23 C24 C25 122.2(3) . . ?
C23 C24 H24 118.9 . . ?
C25 C24 H24 118.9 . . ?
C26 C25 C24 116.5(3) . . ?
C26 C25 C39 122.5(3) . . ?
C24 C25 C39 121.0(3) . . ?
C25 C26 C21 123.5(3) . . ?
C25 C26 H26 118.3 . . ?
C21 C26 H26 118.3 . . ?
N3 C27 C21 128.1(3) . . ?
N3 C27 H27 116.0 . . ?
C21 C27 H27 116.0 . . ?
N3 C28 C29 111.7(2) . . ?
N3 C28 H28A 109.3 . . ?
C29 C28 H28A 109.3 . . ?
N3 C28 H28B 109.3 . . ?
C29 C28 H28B 109.3 . . ?
H28A C28 H28B 107.9 . . ?
C30 C29 C28 113.9(3) . . ?
C30 C29 H29A 108.8 . . ?
C28 C29 H29A 108.8 . . ?
C30 C29 H29B 108.8 . . ?
C28 C29 H29B 108.8 . . ?
H29A C29 H29B 107.7 . . ?
C29 C30 C31 114.3(3) . . ?
C29 C30 H30A 108.7 . . ?
C31 C30 H30A 108.7 . . ?
C29 C30 H30B 108.7 . . ?
C31 C30 H30B 108.7 . . ?
H30A C30 H30B 107.6 . . ?
N4 C31 C30 114.1(2) . . ?
N4 C31 H31A 108.7 . . ?
C30 C31 H31A 108.7 . . ?
N4 C31 H31B 108.7 . . ?
C30 C31 H31B 108.7 . . ?
H31A C31 H31B 107.6 . . ?
N4 C32 C33 128.3(3) . . ?
N4 C32 H32 115.9 . . ?
C33 C32 H32 115.9 . . ?
C38 C33 C34 118.7(3) . . ?
C38 C33 C32 119.1(3) . . ?
C34 C33 C32 122.2(3) . . ?
O4 C34 C35 118.7(3) . . ?
O4 C34 C33 124.1(3) . . ?
C35 C34 C33 117.1(3) . . ?
C36 C35 C34 121.3(3) . . ?
C36 C35 H35 119.4 . . ?
C34 C35 H35 119.4 . . ?
C35 C36 C37 122.3(4) . . ?
C35 C36 H36 118.8 . . ?
C37 C36 H36 118.8 . . ?
C38 C37 C36 116.4(4) . . ?
C38 C37 C40 122.7(4) . . ?
C36 C37 C40 120.9(4) . . ?
C37 C38 C33 123.8(3) . . ?
C37 C38 H38 118.1 . . ?
C33 C38 H38 118.1 . . ?
C25 C39 H39A 109.5 . . ?
C25 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C25 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C37 C40 H40A 109.5 . . ?
C37 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C37 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1418892'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2016-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H28 Br4 Cl2 Cu N4 O4'
_chemical_formula_weight         866.56

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.7486(8)
_cell_length_b                   23.271(3)
_cell_length_c                   8.1150(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.353(11)
_cell_angle_gamma                90.00
_cell_volume                     1459.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2235
_cell_measurement_theta_min      3.6
_cell_measurement_theta_max      27.9

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.972
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             846
_exptl_absorpt_coefficient_mu    6.445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3740
_exptl_absorpt_correction_T_max  0.3900
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6417
_diffrn_reflns_av_R_equivalents  0.0810
_diffrn_reflns_av_sigmaI/netI    0.0972
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2642
_reflns_number_gt                1832
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1224P)²+7.9781P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2642
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0905
_refine_ls_wR_factor_ref         0.2417
_refine_ls_wR_factor_gt          0.2155
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.5000 0.0000 0.0255(5) Uani 1 2 d S . .
N1 N 0.2403(9) 0.5093(3) 0.1085(10) 0.0239(17) Uani 1 1 d . . .
N2 N 0.1235(10) 0.5915(4) 0.3407(10) 0.0290(18) Uani 1 1 d . . .
H2A H 0.1001 0.5571 0.3845 0.035 Uiso 1 1 calc R . .
H2B H 0.0533 0.5960 0.2481 0.035 Uiso 1 1 calc R . .
O1 O 0.0295(8) 0.4177(3) -0.0152(8) 0.0290(15) Uani 1 1 d . . .
O2 O -0.2187(13) 0.6353(5) 0.3603(12) 0.068(3) Uani 1 1 d . . .
H2 H -0.2523 0.6027 0.3360 0.102 Uiso 1 1 calc R . .
Br1 Br -0.07553(16) 0.29295(5) -0.04076(18) 0.0588(5) Uani 1 1 d . . .
Br2 Br 0.20427(15) 0.50701(6) 0.67593(15) 0.0468(4) Uani 1 1 d . . .
Cl1 Cl 0.5553(4) 0.26454(15) 0.3054(5) 0.0683(11) Uani 1 1 d . . .
C1 C 0.3019(11) 0.4069(4) 0.1407(11) 0.024(2) Uani 1 1 d . . .
C2 C 0.1494(11) 0.3860(4) 0.0574(11) 0.025(2) Uani 1 1 d . . .
C3 C 0.1288(12) 0.3244(5) 0.0586(12) 0.030(2) Uani 1 1 d . . .
C4 C 0.2539(14) 0.2883(4) 0.1332(13) 0.035(2) Uani 1 1 d . . .
H4 H 0.2372 0.2487 0.1318 0.042 Uiso 1 1 calc R . .
C5 C 0.4029(13) 0.3113(5) 0.2093(14) 0.038(3) Uani 1 1 d . . .
C6 C 0.4315(13) 0.3690(5) 0.2119(14) 0.037(3) Uani 1 1 d . . .
H6 H 0.5351 0.3836 0.2599 0.045 Uiso 1 1 calc R . .
C7 C 0.3420(12) 0.4662(5) 0.1526(12) 0.030(2) Uani 1 1 d . . .
H7 H 0.4528 0.4756 0.1965 0.036 Uiso 1 1 calc R . .
C8 C 0.3239(12) 0.5665(5) 0.1274(12) 0.030(2) Uani 1 1 d . . .
H8A H 0.2715 0.5923 0.0442 0.035 Uiso 1 1 calc R . .
H8B H 0.4457 0.5629 0.1089 0.035 Uiso 1 1 calc R . .
C9 C 0.3067(12) 0.5918(5) 0.2963(12) 0.032(2) Uani 1 1 d . . .
H9A H 0.3772 0.5699 0.3778 0.038 Uiso 1 1 calc R . .
H9B H 0.3494 0.6310 0.2984 0.038 Uiso 1 1 calc R . .
C10 C 0.0846(15) 0.6379(5) 0.4617(13) 0.040(3) Uani 1 1 d . . .
H10A H 0.1030 0.6754 0.4132 0.048 Uiso 1 1 calc R . .
H10B H 0.1622 0.6344 0.5607 0.048 Uiso 1 1 calc R . .
C11 C -0.1007(17) 0.6330(6) 0.5060(16) 0.057(4) Uani 1 1 d . . .
H11A H -0.1159 0.5969 0.5633 0.068 Uiso 1 1 calc R . .
H11B H -0.1263 0.6640 0.5799 0.068 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 1.935(7) 3_565 ?
Cu1 O1 1.935(7) . ?
Cu1 N1 2.010(7) . ?
Cu1 N1 2.010(7) 3_565 ?
N1 C7 1.308(13) . ?
N1 C8 1.483(13) . ?
N2 C9 1.490(13) . ?
N2 C10 1.505(12) . ?
N2 H2A 0.9000 . ?
N2 H2B 0.9000 . ?
O1 C2 1.293(11) . ?
O2 C11 1.440(16) . ?
O2 H2 0.8200 . ?
Br1 C3 1.870(10) . ?
Cl1 C5 1.746(10) . ?
C1 C2 1.403(13) . ?
C1 C7 1.418(14) . ?
C1 C6 1.425(14) . ?
C2 C3 1.442(14) . ?
C3 C4 1.386(14) . ?
C4 C5 1.376(15) . ?
C4 H4 0.9300 . ?
C5 C6 1.359(16) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.508(14) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.511(18) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.000(1) 3_565 . ?
O1 Cu1 N1 88.6(3) 3_565 . ?
O1 Cu1 N1 91.4(3) . . ?
O1 Cu1 N1 91.4(3) 3_565 3_565 ?
O1 Cu1 N1 88.6(3) . 3_565 ?
N1 Cu1 N1 180.000(1) . 3_565 ?
C7 N1 C8 114.2(7) . . ?
C7 N1 Cu1 123.8(6) . . ?
C8 N1 Cu1 121.7(6) . . ?
C9 N2 C10 113.3(8) . . ?
C9 N2 H2A 108.9 . . ?
C10 N2 H2A 108.9 . . ?
C9 N2 H2B 108.9 . . ?
C10 N2 H2B 108.9 . . ?
H2A N2 H2B 107.7 . . ?
C2 O1 Cu1 128.4(6) . . ?
C11 O2 H2 109.5 . . ?
C2 C1 C7 122.9(8) . . ?
C2 C1 C6 121.5(9) . . ?
C7 C1 C6 115.5(8) . . ?
O1 C2 C1 124.8(9) . . ?
O1 C2 C3 119.6(8) . . ?
C1 C2 C3 115.6(8) . . ?
C4 C3 C2 122.0(9) . . ?
C4 C3 Br1 119.5(8) . . ?
C2 C3 Br1 118.5(7) . . ?
C5 C4 C3 119.7(9) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C6 C5 C4 121.4(9) . . ?
C6 C5 Cl1 120.3(8) . . ?
C4 C5 Cl1 118.3(9) . . ?
C5 C6 C1 119.7(10) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
N1 C7 C1 127.1(8) . . ?
N1 C7 H7 116.4 . . ?
C1 C7 H7 116.4 . . ?
N1 C8 C9 112.1(8) . . ?
N1 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N2 C9 C8 111.7(7) . . ?
N2 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
N2 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
N2 C10 C11 109.9(9) . . ?
N2 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
N2 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
O2 C11 C10 111.0(11) . . ?
O2 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
O2 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2B Br1 0.90 3.10 3.626(9) 119.7 3_565
N2 H2B O1 0.90 1.97 2.821(10) 155.9 3_565
O2 H2 Br2 0.82 2.58 3.326(11) 151.4 3_566
N2 H2A Br2 0.90 2.80 3.417(8) 126.7 3_566
N2 H2A Br2 0.90 2.70 3.377(8) 132.3 .

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         2.163
_refine_diff_density_min         -1.333
_refine_diff_density_rms         0.244
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1418897'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2016-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 Cu N3 O S'
_chemical_formula_weight         346.88

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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.9863(4)
_cell_length_b                   15.3790(8)
_cell_length_c                   13.3498(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.874(2)
_cell_angle_gamma                90.00
_cell_volume                     1433.57(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8867
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             708
_exptl_absorpt_coefficient_mu    1.670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7312
_exptl_absorpt_correction_T_max  0.7312
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14017
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         27.56
_reflns_number_total             3268
_reflns_number_gt                2700
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0330P)²+0.9648P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3268
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0860
_refine_ls_wR_factor_gt          0.0797
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.16246(4) 0.106720(17) 0.92973(2) 0.03313(11) Uani 1 1 d . . .
N1 N 0.1989(3) -0.01094(12) 0.88472(14) 0.0317(4) Uani 1 1 d . . .
N2 N 0.0794(3) 0.12552(12) 0.78488(14) 0.0327(4) Uani 1 1 d . . .
N3 N 0.1205(4) 0.22653(14) 0.96561(18) 0.0576(6) Uani 1 1 d . . .
O1 O 0.2404(2) 0.08137(10) 1.06453(12) 0.0381(4) Uani 1 1 d . . .
S1 S -0.00103(17) 0.39680(5) 0.95474(7) 0.0762(3) Uani 1 1 d . . .
C1 C 0.3030(3) -0.07164(15) 1.04449(17) 0.0345(5) Uani 1 1 d . . .
C2 C 0.2948(3) 0.00600(15) 1.10086(17) 0.0329(5) Uani 1 1 d . . .
C3 C 0.3481(3) 0.00017(18) 1.20406(18) 0.0409(6) Uani 1 1 d . . .
H3 H 0.3431 0.0498 1.2437 0.049 Uiso 1 1 calc R . .
C4 C 0.4069(3) -0.07679(19) 1.24675(19) 0.0464(6) Uani 1 1 d . . .
H4 H 0.4403 -0.0778 1.3147 0.056 Uiso 1 1 calc R . .
C5 C 0.4185(3) -0.15401(18) 1.1915(2) 0.0447(6) Uani 1 1 d . . .
C6 C 0.3666(3) -0.14980(17) 1.0917(2) 0.0431(6) Uani 1 1 d . . .
H6 H 0.3732 -0.2001 1.0533 0.052 Uiso 1 1 calc R . .
C7 C 0.2542(3) -0.07507(15) 0.93982(18) 0.0361(5) Uani 1 1 d . . .
H7 H 0.2636 -0.1289 0.9087 0.043 Uiso 1 1 calc R . .
C8 C 0.1531(4) -0.02754(16) 0.77867(17) 0.0391(5) Uani 1 1 d . . .
H8A H 0.0483 -0.0688 0.7725 0.047 Uiso 1 1 calc R . .
H8B H 0.2635 -0.0526 0.7472 0.047 Uiso 1 1 calc R . .
C9 C 0.0976(3) 0.05553(16) 0.72687(17) 0.0374(5) Uani 1 1 d . . .
C10 C 0.0639(5) 0.0593(2) 0.6243(2) 0.0575(7) Uani 1 1 d . . .
H10 H 0.0835 0.0106 0.5847 0.069 Uiso 1 1 calc R . .
C11 C 0.0012(5) 0.1359(2) 0.5815(2) 0.0599(8) Uani 1 1 d . . .
H11 H -0.0228 0.1394 0.5127 0.072 Uiso 1 1 calc R . .
C12 C -0.0258(4) 0.20727(19) 0.64112(19) 0.0473(6) Uani 1 1 d . . .
H12 H -0.0721 0.2592 0.6141 0.057 Uiso 1 1 calc R . .
C13 C 0.0175(3) 0.19989(16) 0.74182(18) 0.0396(5) Uani 1 1 d . . .
H13 H 0.0033 0.2486 0.7822 0.048 Uiso 1 1 calc R . .
C14 C 0.4810(4) -0.2389(2) 1.2395(2) 0.0635(9) Uani 1 1 d . . .
H14A H 0.3710 -0.2752 1.2484 0.095 Uiso 1 1 calc R . .
H14B H 0.5424 -0.2274 1.3036 0.095 Uiso 1 1 calc R . .
H14C H 0.5691 -0.2679 1.1972 0.095 Uiso 1 1 calc R . .
C15 C 0.0677(4) 0.29695(16) 0.96174(18) 0.0445(6) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9033(16) . ?
Cu1 N1 1.9262(18) . ?
Cu1 N3 1.929(2) . ?
Cu1 N2 2.0215(18) . ?
N1 C7 1.283(3) . ?
N1 C8 1.464(3) . ?
N2 C9 1.334(3) . ?
N2 C13 1.345(3) . ?
N3 C15 1.145(3) . ?
O1 C2 1.308(3) . ?
S1 C15 1.611(3) . ?
C1 C2 1.414(3) . ?
C1 C6 1.422(3) . ?
C1 C7 1.428(3) . ?
C2 C3 1.418(3) . ?
C3 C4 1.371(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.402(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(4) . ?
C5 C14 1.513(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.498(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.383(3) . ?
C10 C11 1.375(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N1 93.78(7) . . ?
O1 Cu1 N3 90.12(8) . . ?
N1 Cu1 N3 176.10(9) . . ?
O1 Cu1 N2 176.40(7) . . ?
N1 Cu1 N2 82.68(8) . . ?
N3 Cu1 N2 93.42(9) . . ?
C7 N1 C8 118.2(2) . . ?
C7 N1 Cu1 125.73(16) . . ?
C8 N1 Cu1 116.02(14) . . ?
C9 N2 C13 118.3(2) . . ?
C9 N2 Cu1 114.19(15) . . ?
C13 N2 Cu1 127.49(16) . . ?
C15 N3 Cu1 160.7(2) . . ?
C2 O1 Cu1 127.07(15) . . ?
C2 C1 C6 119.7(2) . . ?
C2 C1 C7 122.7(2) . . ?
C6 C1 C7 117.6(2) . . ?
O1 C2 C1 124.6(2) . . ?
O1 C2 C3 118.7(2) . . ?
C1 C2 C3 116.7(2) . . ?
C4 C3 C2 121.6(2) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 122.3(2) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C6 C5 C4 117.0(2) . . ?
C6 C5 C14 121.1(3) . . ?
C4 C5 C14 121.9(3) . . ?
C5 C6 C1 122.7(3) . . ?
C5 C6 H6 118.7 . . ?
C1 C6 H6 118.7 . . ?
N1 C7 C1 126.2(2) . . ?
N1 C7 H7 116.9 . . ?
C1 C7 H7 116.9 . . ?
N1 C8 C9 110.05(19) . . ?
N1 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
N1 C8 H8B 109.6 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N2 C9 C10 121.6(2) . . ?
N2 C9 C8 116.6(2) . . ?
C10 C9 C8 121.7(2) . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C12 C11 C10 119.5(2) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 118.1(3) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
N2 C13 C12 123.1(2) . . ?
N2 C13 H13 118.4 . . ?
C12 C13 H13 118.4 . . ?
C5 C14 H14A 109.5 . . ?
C5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 S1 178.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.56
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.062
####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1418904'
_audit_update_record             
;
2015-08-15 deposited with the CCDC.
2016-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 Br2 Cl2 Cu N2 O2'
_chemical_formula_weight         666.71

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           multi-scan
_symmetry_space_group_name_H-M   SADABS

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.2353(8)
_cell_length_b                   12.4758(6)
_cell_length_c                   11.1404(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.349(3)
_cell_angle_gamma                90.00
_cell_volume                     1211.07(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2066
_cell_measurement_theta_min      4.0
_cell_measurement_theta_max      28.8

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.828
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             662
_exptl_absorpt_coefficient_mu    4.447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4027
_exptl_absorpt_correction_T_max  0.4412
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5409
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         25.49
_reflns_number_total             2255
_reflns_number_gt                1672
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0333P)²+0.9807P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2255
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0824
_refine_ls_wR_factor_gt          0.0733
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.0000 0.0000 1.0000 0.02767(16) Uani 1 2 d S . .
N1 N 0.9220(3) 0.15117(19) 0.9994(3) 0.0273(6) Uani 1 1 d . . .
O1 O 1.0712(3) 0.03365(17) 0.8623(2) 0.0357(6) Uani 1 1 d . . .
Br1 Br 1.24073(6) 0.00837(3) 0.67261(4) 0.05414(17) Uani 1 1 d . . .
C1 C 1.0845(4) 0.2238(2) 0.8852(3) 0.0269(7) Uani 1 1 d . . .
C2 C 1.1172(4) 0.1255(3) 0.8361(3) 0.0279(7) Uani 1 1 d . . .
C3 C 1.2036(4) 0.1342(3) 0.7523(3) 0.0297(8) Uani 1 1 d . . .
C4 C 1.2610(4) 0.2294(3) 0.7265(3) 0.0361(8) Uani 1 1 d . . .
H4 H 1.3195 0.2310 0.6727 0.043 Uiso 1 1 calc R . .
C5 C 1.2317(4) 0.3230(3) 0.7808(3) 0.0346(8) Uani 1 1 d . . .
C6 C 1.1417(4) 0.3216(3) 0.8567(3) 0.0329(8) Uani 1 1 d . . .
H6 H 1.1183 0.3853 0.8895 0.039 Uiso 1 1 calc R . .
C7 C 0.9800(4) 0.2299(2) 0.9572(3) 0.0301(8) Uani 1 1 d . . .
H7 H 0.9519 0.2982 0.9746 0.036 Uiso 1 1 calc R . .
C8 C 0.8056(4) 0.1756(2) 1.0615(3) 0.0307(8) Uani 1 1 d . . .
H8 H 0.8446 0.1474 1.1485 0.037 Uiso 1 1 calc R . .
C9 C 0.7590(4) 0.2916(3) 1.0697(4) 0.0411(9) Uani 1 1 d . . .
H9A H 0.8398 0.3315 1.1319 0.049 Uiso 1 1 calc R . .
H9B H 0.7330 0.3271 0.9878 0.049 Uiso 1 1 calc R . .
C10 C 0.6194(5) 0.2794(3) 1.1115(4) 0.0538(11) Uani 1 1 d . . .
H10A H 0.5510 0.3402 1.0834 0.065 Uiso 1 1 calc R . .
H10B H 0.6500 0.2746 1.2035 0.065 Uiso 1 1 calc R . .
C11 C 0.5404(4) 0.1766(3) 1.0503(4) 0.0445(9) Uani 1 1 d . . .
H11A H 0.4444 0.1926 0.9836 0.053 Uiso 1 1 calc R . .
H11B H 0.5190 0.1312 1.1131 0.053 Uiso 1 1 calc R . .
C12 C 0.6522(4) 0.1208(3) 0.9948(4) 0.0376(8) Uani 1 1 d . . .
H12A H 0.6581 0.0446 1.0131 0.045 Uiso 1 1 calc R . .
H12B H 0.6210 0.1310 0.9034 0.045 Uiso 1 1 calc R . .
Cl1 Cl 1.30551(14) 0.44325(8) 0.74750(12) 0.0628(3) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.905(2) . ?
Cu1 O1 1.905(2) 3_757 ?
Cu1 N1 2.018(2) 3_757 ?
Cu1 N1 2.018(2) . ?
N1 C7 1.280(4) . ?
N1 C8 1.490(4) . ?
O1 C2 1.289(4) . ?
Br1 C3 1.890(3) . ?
C1 C6 1.406(4) . ?
C1 C2 1.415(4) . ?
C1 C7 1.447(4) . ?
C2 C3 1.420(4) . ?
C3 C4 1.369(4) . ?
C4 C5 1.383(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(4) . ?
C5 Cl1 1.738(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.522(4) . ?
C8 C12 1.526(5) . ?
C8 H8 0.9800 . ?
C9 C10 1.517(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.521(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.535(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.000(1) . 3_757 ?
O1 Cu1 N1 89.45(10) . 3_757 ?
O1 Cu1 N1 90.55(10) 3_757 3_757 ?
O1 Cu1 N1 90.55(10) . . ?
O1 Cu1 N1 89.45(10) 3_757 . ?
N1 Cu1 N1 180.00(16) 3_757 . ?
C7 N1 C8 117.9(3) . . ?
C7 N1 Cu1 121.7(2) . . ?
C8 N1 Cu1 120.07(18) . . ?
C2 O1 Cu1 127.3(2) . . ?
C6 C1 C2 121.4(3) . . ?
C6 C1 C7 116.7(3) . . ?
C2 C1 C7 121.7(3) . . ?
O1 C2 C1 123.7(3) . . ?
O1 C2 C3 121.1(3) . . ?
C1 C2 C3 115.2(3) . . ?
C4 C3 C2 123.1(3) . . ?
C4 C3 Br1 118.6(2) . . ?
C2 C3 Br1 118.3(2) . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 Cl1 120.3(3) . . ?
C4 C5 Cl1 119.2(3) . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
N1 C7 C1 126.9(3) . . ?
N1 C7 H7 116.5 . . ?
C1 C7 H7 116.5 . . ?
N1 C8 C9 119.0(3) . . ?
N1 C8 C12 112.3(3) . . ?
C9 C8 C12 102.7(3) . . ?
N1 C8 H8 107.4 . . ?
C9 C8 H8 107.4 . . ?
C12 C8 H8 107.4 . . ?
C10 C9 C8 102.1(3) . . ?
C10 C9 H9A 111.4 . . ?
C8 C9 H9A 111.4 . . ?
C10 C9 H9B 111.4 . . ?
C8 C9 H9B 111.4 . . ?
H9A C9 H9B 109.2 . . ?
C9 C10 C11 106.1(3) . . ?
C9 C10 H10A 110.5 . . ?
C11 C10 H10A 110.5 . . ?
C9 C10 H10B 110.5 . . ?
C11 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
C10 C11 C12 106.0(3) . . ?
C10 C11 H11A 110.5 . . ?
C12 C11 H11A 110.5 . . ?
C10 C11 H11B 110.5 . . ?
C12 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
C8 C12 C11 103.9(3) . . ?
C8 C12 H12A 111.0 . . ?
C11 C12 H12A 111.0 . . ?
C8 C12 H12B 111.0 . . ?
C11 C12 H12B 111.0 . . ?
H12A C12 H12B 109.0 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.49
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.647
_refine_diff_density_rms         0.075
