# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_cl095
_database_code_depnum_ccdc_archive 'CCDC 1566628'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL30aBr]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H30 Br2 Cu2 N4 O6'
_chemical_formula_sum            'C26 H30 Br2 Cu2 N4 O6'
_chemical_formula_weight         781.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7302(4)
_cell_length_b                   9.2879(5)
_cell_length_c                   10.2517(5)
_cell_angle_alpha                94.782(4)
_cell_angle_beta                 94.310(4)
_cell_angle_gamma                108.849(4)
_cell_volume                     690.07(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    7578
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      28.5

_exptl_crystal_description       block
_exptl_crystal_colour            'blue green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.880
_exptl_crystal_F_000             390
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.065
_exptl_absorpt_coefficient_mu    4.485
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            8291
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.005
_diffrn_reflns_theta_max         28.451
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.929
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3242
_reflns_number_gt                2709
_reflns_threshold_expression     'I > 2σ(I)'

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_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     
'w=1/[σ²(Fo²)+(0.0408P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3242
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0658
_refine_ls_wR_factor_gt          0.0628
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0652(3) 0.2210(3) -0.1636(2) 0.0210(5) Uani 1 1 d . . . . .
H1 H 0.0072 0.2844 -0.2040 0.025 Uiso 1 1 calc R U . . .
C2 C 0.0309(4) 0.0737(3) -0.2221(2) 0.0221(5) Uani 1 1 d . . . . .
H2 H -0.0484 0.0367 -0.3017 0.026 Uiso 1 1 calc R U . . .
C3 C 0.1143(4) -0.0192(3) -0.1625(3) 0.0219(5) Uani 1 1 d . . . . .
H3 H 0.0926 -0.1210 -0.2008 0.026 Uiso 1 1 calc R U . . .
C4 C 0.2292(3) 0.0378(3) -0.0471(2) 0.0199(5) Uani 1 1 d . . . . .
H4 H 0.2881 -0.0240 -0.0051 0.024 Uiso 1 1 calc R U . . .
C5 C 0.2572(3) 0.1868(3) 0.0068(2) 0.0162(4) Uani 1 1 d . . . . .
C6 C 0.3765(3) 0.2544(3) 0.1335(2) 0.0197(5) Uani 1 1 d . . . . .
H6A H 0.3248 0.1948 0.2055 0.024 Uiso 1 1 calc R U . . .
H6B H 0.5013 0.2491 0.1260 0.024 Uiso 1 1 calc R U . . .
C7 C 0.4969(3) 0.4906(3) 0.2667(2) 0.0182(4) Uani 1 1 d . . . . .
H7 H 0.5652 0.4383 0.3126 0.022 Uiso 1 1 calc R U . . .
C8 C 0.5259(3) 0.6450(3) 0.3178(2) 0.0190(5) Uani 1 1 d . . . . .
C9 C 0.4329(3) 0.7341(3) 0.2573(2) 0.0199(5) Uani 1 1 d . . . . .
C10 C 0.4583(4) 0.8966(3) 0.3112(3) 0.0260(5) Uani 1 1 d . . . . .
H10A H 0.3881 0.9400 0.2518 0.039 Uiso 1 1 calc R U . . .
H10B H 0.5890 0.9580 0.3185 0.039 Uiso 1 1 calc R U . . .
H10C H 0.4144 0.8975 0.3984 0.039 Uiso 1 1 calc R U . . .
C11 C 0.6597(3) 0.7085(3) 0.4351(2) 0.0216(5) Uani 1 1 d . . . . .
C12 C 0.8967(4) 0.6597(3) 0.5705(3) 0.0252(5) Uani 1 1 d . . . . .
H12A H 0.9070 0.5685 0.6096 0.030 Uiso 1 1 calc R U . . .
H12B H 0.8633 0.7247 0.6389 0.030 Uiso 1 1 calc R U . . .
C13 C 1.0792(4) 0.7482(4) 0.5265(3) 0.0305(6) Uani 1 1 d . . . . .
H13A H 1.0993 0.6935 0.4462 0.046 Uiso 1 1 calc R U . . .
H13B H 1.1780 0.7584 0.5961 0.046 Uiso 1 1 calc R U . . .
H13C H 1.0789 0.8502 0.5087 0.046 Uiso 1 1 calc R U . . .
N1 N 0.1779(3) 0.2779(2) -0.0515(2) 0.0172(4) Uani 1 1 d . . . . .
N2 N 0.3877(3) 0.4141(2) 0.1645(2) 0.0178(4) Uani 1 1 d . . . . .
O1 O 0.3219(2) 0.6852(2) 0.15245(19) 0.0236(4) Uani 1 1 d . . . . .
O2 O 0.6885(3) 0.8278(2) 0.5029(2) 0.0352(5) Uani 1 1 d . . . . .
O3 O 0.7546(3) 0.6121(2) 0.46079(19) 0.0283(4) Uani 1 1 d . . . . .
Cu1 Cu 0.23834(4) 0.48817(3) 0.04627(3) 0.01711(8) Uani 1 1 d . . . . .
Br1 Br 0.12448(3) 0.59922(3) -0.13397(2) 0.01872(7) 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
C1 N1 1.346(3) . ?
C1 C2 1.381(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.386(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.347(3) . ?
C5 C6 1.497(3) . ?
C6 N2 1.464(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.292(3) . ?
C7 C8 1.425(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.411(3) . ?
C8 C11 1.471(3) . ?
C9 O1 1.275(3) . ?
C9 C10 1.509(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O2 1.205(3) . ?
C11 O3 1.358(3) . ?
C12 O3 1.444(3) . ?
C12 C13 1.509(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N1 Cu1 2.013(2) . ?
N2 Cu1 1.928(2) . ?
O1 Cu1 1.9364(18) . ?
Cu1 Br1 2.4317(4) . ?
Cu1 Br1 2.8919(4) 2_565 ?
Br1 Cu1 2.8919(4) 2_565 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.3(2) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C1 C2 C3 118.8(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 119.3(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 118.9(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.9(2) . . ?
N1 C5 C6 116.4(2) . . ?
C4 C5 C6 121.7(2) . . ?
N2 C6 C5 110.21(19) . . ?
N2 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
N2 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
N2 C7 C8 127.0(2) . . ?
N2 C7 H7 116.5 . . ?
C8 C7 H7 116.5 . . ?
C9 C8 C7 121.5(2) . . ?
C9 C8 C11 121.4(2) . . ?
C7 C8 C11 117.1(2) . . ?
O1 C9 C8 123.2(2) . . ?
O1 C9 C10 114.4(2) . . ?
C8 C9 C10 122.4(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 O3 121.7(2) . . ?
O2 C11 C8 127.8(2) . . ?
O3 C11 C8 110.4(2) . . ?
O3 C12 C13 110.7(2) . . ?
O3 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 N1 C5 118.7(2) . . ?
C1 N1 Cu1 126.85(16) . . ?
C5 N1 Cu1 114.42(16) . . ?
C7 N2 C6 117.0(2) . . ?
C7 N2 Cu1 126.97(17) . . ?
C6 N2 Cu1 115.98(15) . . ?
C9 O1 Cu1 131.20(16) . . ?
C11 O3 C12 117.6(2) . . ?
N2 Cu1 O1 90.13(8) . . ?
N2 Cu1 N1 82.84(8) . . ?
O1 Cu1 N1 172.74(8) . . ?
N2 Cu1 Br1 164.41(6) . . ?
O1 Cu1 Br1 90.46(6) . . ?
N1 Cu1 Br1 95.83(6) . . ?
N2 Cu1 Br1 106.66(6) . 2_565 ?
O1 Cu1 Br1 93.78(6) . 2_565 ?
N1 Cu1 Br1 89.97(6) . 2_565 ?
Br1 Cu1 Br1 88.847(12) . 2_565 ?
Cu1 Br1 Cu1 91.153(12) . 2_565 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.5(4) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 N1 -1.1(4) . . . . ?
C3 C4 C5 C6 178.5(2) . . . . ?
N1 C5 C6 N2 -2.6(3) . . . . ?
C4 C5 C6 N2 177.8(2) . . . . ?
N2 C7 C8 C9 -0.4(4) . . . . ?
N2 C7 C8 C11 -179.3(2) . . . . ?
C7 C8 C9 O1 -1.9(4) . . . . ?
C11 C8 C9 O1 177.0(2) . . . . ?
C7 C8 C9 C10 178.7(2) . . . . ?
C11 C8 C9 C10 -2.5(4) . . . . ?
C9 C8 C11 O2 10.9(4) . . . . ?
C7 C8 C11 O2 -170.2(3) . . . . ?
C9 C8 C11 O3 -168.9(2) . . . . ?
C7 C8 C11 O3 10.0(3) . . . . ?
C2 C1 N1 C5 -1.2(4) . . . . ?
C2 C1 N1 Cu1 -179.12(18) . . . . ?
C4 C5 N1 C1 1.5(3) . . . . ?
C6 C5 N1 C1 -178.1(2) . . . . ?
C4 C5 N1 Cu1 179.63(18) . . . . ?
C6 C5 N1 Cu1 0.0(3) . . . . ?
C8 C7 N2 C6 -178.0(2) . . . . ?
C8 C7 N2 Cu1 2.7(4) . . . . ?
C5 C6 N2 C7 -175.2(2) . . . . ?
C5 C6 N2 Cu1 4.2(3) . . . . ?
C8 C9 O1 Cu1 1.7(4) . . . . ?
C10 C9 O1 Cu1 -178.84(17) . . . . ?
O2 C11 O3 C12 -2.0(4) . . . . ?
C8 C11 O3 C12 177.9(2) . . . . ?
C13 C12 O3 C11 -90.1(3) . . . . ?

_refine_diff_density_max         0.796
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.095

####################################################################### 
# 
# 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_cl115
_database_code_depnum_ccdc_archive 'CCDC 1566630'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7

_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL30dBr]'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 Br Cu N3 O2'
_chemical_formula_weight         373.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.6905(4)
_cell_length_b                   24.3476(14)
_cell_length_c                   7.7833(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.207(4)
_cell_angle_gamma                90
_cell_volume                     1339.46(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    5553
_cell_measurement_theta_min      1.68
_cell_measurement_theta_max      28.67

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.853
_exptl_crystal_F_000             740
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.093
_exptl_absorpt_coefficient_mu    4.614
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            8129
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.673
_diffrn_reflns_theta_max         28.523
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3151
_reflns_number_gt                2226
_reflns_threshold_expression     'I > 2σ(I)'

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_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     
'w=1/[σ²(Fo²)+(0.0630P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3151
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_restrained_S_all      0.960
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.2351(6) 0.62999(16) 0.4949(6) 0.0216(8) Uani 1 1 d . . . . .
H1 H 1.1164 0.6395 0.3997 0.026 Uiso 1 1 calc R U . . .
C2 C 1.2829(6) 0.57529(17) 0.5265(6) 0.0271(10) Uani 1 1 d . . . . .
H2 H 1.1993 0.5475 0.4540 0.033 Uiso 1 1 calc R U . . .
C3 C 1.4558(6) 0.56166(16) 0.6663(6) 0.0283(10) Uani 1 1 d . . . . .
H3 H 1.4930 0.5243 0.6908 0.034 Uiso 1 1 calc R U . . .
C4 C 1.5728(6) 0.60291(16) 0.7693(6) 0.0242(9) Uani 1 1 d . . . . .
H4 H 1.6915 0.5943 0.8660 0.029 Uiso 1 1 calc R U . . .
C5 C 1.5160(5) 0.65745(14) 0.7306(5) 0.0164(8) Uani 1 1 d . . . . .
C6 C 1.6399(5) 0.70342(14) 0.8408(5) 0.0165(7) Uani 1 1 d . . . . .
H6A H 1.6594 0.7001 0.9740 0.020 Uiso 1 1 calc R U . . .
H6B H 1.7649 0.7013 0.8325 0.020 Uiso 1 1 calc R U . . .
C7 C 1.6441(5) 0.80018(15) 0.8409(5) 0.0160(7) Uani 1 1 d . . . . .
H7 H 1.7644 0.7956 0.9402 0.019 Uiso 1 1 calc R U . . .
C8 C 1.5826(5) 0.85461(15) 0.7867(5) 0.0161(7) Uani 1 1 d . . . . .
C9 C 1.4081(5) 0.86627(15) 0.6363(5) 0.0163(8) Uani 1 1 d . . . . .
C10 C 1.1875(6) 0.93075(17) 0.4445(6) 0.0243(9) Uani 1 1 d . . . . .
H10A H 1.0804 0.9187 0.4756 0.029 Uiso 1 1 calc R U . . .
H10B H 1.1806 0.9111 0.3306 0.029 Uiso 1 1 calc R U . . .
C11 C 1.1799(6) 0.99167(18) 0.4136(7) 0.0336(12) Uani 1 1 d . . . . .
H11A H 1.1805 1.0105 0.5252 0.050 Uiso 1 1 calc R U . . .
H11B H 1.0640 1.0011 0.3060 0.050 Uiso 1 1 calc R U . . .
H11C H 1.2902 1.0033 0.3895 0.050 Uiso 1 1 calc R U . . .
C12 C 1.7020(5) 0.89865(16) 0.8865(6) 0.0196(8) Uani 1 1 d . . . . .
N1 N 1.3507(5) 0.67066(13) 0.5941(4) 0.0176(7) Uani 1 1 d . . . . .
N2 N 1.5504(4) 0.75601(12) 0.7666(4) 0.0163(6) Uani 1 1 d . . . . .
N3 N 1.7990(5) 0.93355(15) 0.9688(6) 0.0309(9) Uani 1 1 d . . . . .
O1 O 1.2925(4) 0.83112(11) 0.5381(4) 0.0198(6) Uani 1 1 d . . . . .
O2 O 1.3675(4) 0.91936(11) 0.5999(4) 0.0193(6) Uani 1 1 d . . . . .
Cu1 Cu 1.30338(6) 0.75127(2) 0.56019(6) 0.01451(13) Uani 1 1 d . . . . .
Br1 Br 1.05817(5) 0.74588(2) 0.24926(5) 0.01691(12) 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
C1 N1 1.351(5) . ?
C1 C2 1.378(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.376(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(5) . ?
C4 H4 0.9500 . ?
C5 N1 1.335(5) . ?
C5 C6 1.501(5) . ?
C6 N2 1.461(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.297(5) . ?
C7 C8 1.414(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.419(5) . ?
C8 C12 1.426(5) . ?
C9 O1 1.254(4) . ?
C9 O2 1.334(4) . ?
C10 O2 1.462(5) . ?
C10 C11 1.500(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N3 1.145(5) . ?
N1 Cu1 1.995(3) . ?
N2 Cu1 1.949(3) . ?
O1 Cu1 1.951(3) . ?
Cu1 Br1 2.4152(6) . ?
Cu1 Br1 2.8132(6) 4_576 ?
Br1 Cu1 2.8131(6) 4_575 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.5(4) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 118.5(4) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 119.2(4) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 119.5(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 121.4(4) . . ?
N1 C5 C6 117.8(3) . . ?
C4 C5 C6 120.9(3) . . ?
N2 C6 C5 109.5(3) . . ?
N2 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
N2 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 125.6(3) . . ?
N2 C7 H7 117.2 . . ?
C8 C7 H7 117.2 . . ?
C7 C8 C9 122.0(3) . . ?
C7 C8 C12 118.3(3) . . ?
C9 C8 C12 119.7(3) . . ?
O1 C9 O2 118.8(3) . . ?
O1 C9 C8 125.4(3) . . ?
O2 C9 C8 115.8(3) . . ?
O2 C10 C11 106.5(3) . . ?
O2 C10 H10A 110.4 . . ?
C11 C10 H10A 110.4 . . ?
O2 C10 H10B 110.4 . . ?
C11 C10 H10B 110.4 . . ?
H10A C10 H10B 108.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C8 179.1(4) . . ?
C5 N1 C1 118.9(3) . . ?
C5 N1 Cu1 114.1(2) . . ?
C1 N1 Cu1 126.9(3) . . ?
C7 N2 C6 117.3(3) . . ?
C7 N2 Cu1 127.3(3) . . ?
C6 N2 Cu1 115.4(2) . . ?
C9 O1 Cu1 129.1(2) . . ?
C9 O2 C10 115.2(3) . . ?
N2 Cu1 O1 90.44(12) . . ?
N2 Cu1 N1 83.19(13) . . ?
O1 Cu1 N1 172.57(13) . . ?
N2 Cu1 Br1 162.14(10) . . ?
O1 Cu1 Br1 88.65(8) . . ?
N1 Cu1 Br1 96.24(9) . . ?
N2 Cu1 Br1 101.77(10) . 4_576 ?
O1 Cu1 Br1 90.43(9) . 4_576 ?
N1 Cu1 Br1 94.60(10) . 4_576 ?
Br1 Cu1 Br1 96.074(19) . 4_576 ?
Cu1 Br1 Cu1 95.920(19) . 4_575 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.4(7) . . . . ?
C1 C2 C3 C4 0.4(7) . . . . ?
C2 C3 C4 C5 -0.3(7) . . . . ?
C3 C4 C5 N1 -0.8(7) . . . . ?
C3 C4 C5 C6 179.7(4) . . . . ?
N1 C5 C6 N2 -1.9(5) . . . . ?
C4 C5 C6 N2 177.6(4) . . . . ?
N2 C7 C8 C9 -2.0(6) . . . . ?
N2 C7 C8 C12 178.6(4) . . . . ?
C7 C8 C9 O1 0.1(6) . . . . ?
C12 C8 C9 O1 179.5(4) . . . . ?
C7 C8 C9 O2 -179.9(4) . . . . ?
C12 C8 C9 O2 -0.5(6) . . . . ?
C4 C5 N1 C1 1.6(6) . . . . ?
C6 C5 N1 C1 -178.9(4) . . . . ?
C4 C5 N1 Cu1 -178.3(3) . . . . ?
C6 C5 N1 Cu1 1.2(4) . . . . ?
C2 C1 N1 C5 -1.4(6) . . . . ?
C2 C1 N1 Cu1 178.5(3) . . . . ?
C8 C7 N2 C6 179.1(4) . . . . ?
C8 C7 N2 Cu1 0.9(6) . . . . ?
C5 C6 N2 C7 -176.7(3) . . . . ?
C5 C6 N2 Cu1 1.8(4) . . . . ?
O2 C9 O1 Cu1 -177.3(3) . . . . ?
C8 C9 O1 Cu1 2.7(6) . . . . ?
O1 C9 O2 C10 -0.1(5) . . . . ?
C8 C9 O2 C10 179.9(3) . . . . ?
C11 C10 O2 C9 -173.8(4) . . . . ?

_refine_diff_density_max         0.918
_refine_diff_density_min         -0.844
_refine_diff_density_rms         0.146

####################################################################### 
# 
# 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_cl113
_database_code_depnum_ccdc_archive 'CCDC 1566631'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_cl113               
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: Cracked crystal, crystal of bad quality
;
_vrf_PLAT020_cl113               
;
PROBLEM: The value of Rint is greater than 0.12 .........      0.186 Report
RESPONSE: Cracked crystal, crystal of bad quality
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL30fBr]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H34 Br2 Cu2 N4 O6'
_chemical_formula_sum            'C36 H34 Br2 Cu2 N4 O6'
_chemical_formula_weight         905.57

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   10.5383(6)
_cell_length_b                   9.5476(5)
_cell_length_c                   17.4636(12)
_cell_angle_alpha                90
_cell_angle_beta                 100.791(5)
_cell_angle_gamma                90
_cell_volume                     1726.04(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    13861
_cell_measurement_theta_min      2.11
_cell_measurement_theta_max      28.47

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_F_000             908
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.104
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.093
_exptl_absorpt_coefficient_mu    3.600
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            16911
_diffrn_reflns_av_unetI/netI     0.1080
_diffrn_reflns_av_R_equivalents  0.1860
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.099
_diffrn_reflns_theta_max         28.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4145
_reflns_number_gt                2693
_reflns_threshold_expression     'I > 2σ(I)'


_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_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     
'w=1/[σ²(Fo²)+(0.1351P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4145
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1115
_refine_ls_R_factor_gt           0.0733
_refine_ls_wR_factor_ref         0.2261
_refine_ls_wR_factor_gt          0.1886
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3570(7) 0.2284(7) 0.5345(5) 0.0504(18) Uani 1 1 d . . . . .
H1 H 0.3090 0.2992 0.5036 0.061 Uiso 1 1 calc R U . . .
C2 C 0.2950(7) 0.1384(7) 0.5768(5) 0.0515(18) Uani 1 1 d . . . . .
H2 H 0.2044 0.1463 0.5743 0.062 Uiso 1 1 calc R U . . .
C3 C 0.3639(8) 0.0367(8) 0.6229(6) 0.059(2) Uani 1 1 d . . . . .
H3 H 0.3217 -0.0240 0.6532 0.070 Uiso 1 1 calc R U . . .
C4 C 0.4951(8) 0.0238(7) 0.6245(5) 0.0480(16) Uani 1 1 d . . . . .
H4 H 0.5441 -0.0465 0.6552 0.058 Uiso 1 1 calc R U . . .
C5 C 0.5526(7) 0.1143(6) 0.5809(4) 0.0405(14) Uani 1 1 d . . . . .
C6 C 0.6960(7) 0.1121(7) 0.5814(5) 0.0480(17) Uani 1 1 d . . . . .
H6A H 0.7438 0.1410 0.6333 0.058 Uiso 1 1 calc R U . . .
H6B H 0.7233 0.0159 0.5708 0.058 Uiso 1 1 calc R U . . .
C7 C 0.8271(6) 0.1830(7) 0.4910(5) 0.0433(16) Uani 1 1 d . . . . .
H7 H 0.8776 0.1028 0.5085 0.052 Uiso 1 1 calc R U . . .
C8 C 0.8679(6) 0.2644(6) 0.4346(5) 0.0419(15) Uani 1 1 d . . . . .
C9 C 0.8163(6) 0.4006(6) 0.4140(4) 0.0362(13) Uani 1 1 d . . . . .
C10 C 0.8807(6) 0.5031(6) 0.3706(4) 0.0397(14) Uani 1 1 d . . . . .
C11 C 1.0160(6) 0.5158(7) 0.3834(5) 0.0421(15) Uani 1 1 d . . . . .
H11 H 1.0688 0.4561 0.4196 0.051 Uiso 1 1 calc R U . . .
C12 C 1.0722(6) 0.6168(7) 0.3425(5) 0.0448(16) Uani 1 1 d . . . . .
H12 H 1.1636 0.6233 0.3492 0.054 Uiso 1 1 calc R U . . .
C13 C 0.9958(7) 0.7069(7) 0.2925(5) 0.0494(17) Uani 1 1 d . . . . .
H13 H 1.0348 0.7760 0.2654 0.059 Uiso 1 1 calc R U . . .
C14 C 0.8616(7) 0.6979(7) 0.2811(5) 0.0502(17) Uani 1 1 d . . . . .
H14 H 0.8091 0.7614 0.2472 0.060 Uiso 1 1 calc R U . . .
C15 C 0.8056(6) 0.5949(7) 0.3200(4) 0.0442(16) Uani 1 1 d . . . . .
H15 H 0.7142 0.5873 0.3117 0.053 Uiso 1 1 calc R U . . .
C16 C 0.9614(6) 0.1957(6) 0.3934(5) 0.0447(17) Uani 1 1 d . . . . .
C17 C 1.0341(7) 0.1632(7) 0.2732(6) 0.054(2) Uani 1 1 d . . . . .
H17A H 0.9971 0.1745 0.2171 0.065 Uiso 1 1 calc R U . . .
H17B H 1.0384 0.0618 0.2852 0.065 Uiso 1 1 calc R U . . .
C18 C 1.1681(7) 0.2241(8) 0.2901(6) 0.0557(19) Uani 1 1 d . . . . .
H18A H 1.1643 0.3237 0.2763 0.084 Uiso 1 1 calc R U . . .
H18B H 1.2228 0.1746 0.2593 0.084 Uiso 1 1 calc R U . . .
H18C H 1.2045 0.2136 0.3457 0.084 Uiso 1 1 calc R U . . .
Br1 Br 0.41674(6) 0.45429(7) 0.39350(5) 0.0487(3) Uani 1 1 d . . . . .
Cu1 Cu 0.59287(7) 0.34315(7) 0.48281(6) 0.0410(3) Uani 1 1 d . . . . .
N1 N 0.4861(5) 0.2174(5) 0.5364(4) 0.0416(13) Uani 1 1 d . . . . .
N2 N 0.7251(5) 0.2059(5) 0.5229(4) 0.0420(13) Uani 1 1 d . . . . .
O1 O 0.7158(4) 0.4469(4) 0.4372(3) 0.0440(11) Uani 1 1 d . . . . .
O2 O 1.0362(5) 0.1043(5) 0.4239(4) 0.0625(16) Uani 1 1 d . . . . .
O3 O 0.9509(4) 0.2321(5) 0.3195(3) 0.0441(11) 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
C1 N1 1.358(8) . ?
C1 C2 1.376(10) . ?
C1 H1 0.9500 . ?
C2 C3 1.377(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.366(10) . ?
C4 H4 0.9500 . ?
C5 N1 1.364(9) . ?
C5 C6 1.509(9) . ?
C6 N2 1.433(9) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.319(8) . ?
C7 C8 1.385(10) . ?
C7 H7 0.9500 . ?
C8 C9 1.430(8) . ?
C8 C16 1.478(9) . ?
C9 O1 1.282(7) . ?
C9 C10 1.479(9) . ?
C10 C15 1.383(10) . ?
C10 C11 1.407(8) . ?
C11 C12 1.397(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(11) . ?
C12 H12 0.9500 . ?
C13 C14 1.393(10) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(10) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 O2 1.229(8) . ?
C16 O3 1.321(9) . ?
C17 O3 1.456(8) . ?
C17 C18 1.504(10) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
Br1 Cu1 2.4330(11) . ?
Br1 Cu1 2.9150(12) 3_666 ?
Cu1 O1 1.918(5) . ?
Cu1 N2 1.945(5) . ?
Cu1 N1 1.995(5) . ?
Cu1 Br1 2.9151(12) 3_666 ?

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 C1 C2 120.9(7) . . ?
N1 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C1 C2 C3 120.1(7) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 119.4(7) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 118.6(7) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C4 122.6(6) . . ?
N1 C5 C6 114.9(6) . . ?
C4 C5 C6 122.5(6) . . ?
N2 C6 C5 109.6(6) . . ?
N2 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
N2 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 126.5(6) . . ?
N2 C7 H7 116.8 . . ?
C8 C7 H7 116.8 . . ?
C7 C8 C9 122.3(5) . . ?
C7 C8 C16 114.9(5) . . ?
C9 C8 C16 122.6(6) . . ?
O1 C9 C8 122.1(6) . . ?
O1 C9 C10 114.9(5) . . ?
C8 C9 C10 122.8(5) . . ?
C15 C10 C11 119.3(6) . . ?
C15 C10 C9 118.9(6) . . ?
C11 C10 C9 121.6(6) . . ?
C12 C11 C10 119.5(6) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C13 C12 C11 120.2(6) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.7(6) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 119.1(7) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C10 C15 C14 121.1(6) . . ?
C10 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
O2 C16 O3 122.7(6) . . ?
O2 C16 C8 122.4(7) . . ?
O3 C16 C8 114.7(6) . . ?
O3 C17 C18 110.9(6) . . ?
O3 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
O3 C17 H17B 109.5 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
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 . . ?
Cu1 Br1 Cu1 86.70(3) . 3_666 ?
O1 Cu1 N2 90.2(2) . . ?
O1 Cu1 N1 171.8(2) . . ?
N2 Cu1 N1 81.6(2) . . ?
O1 Cu1 Br1 90.13(15) . . ?
N2 Cu1 Br1 159.02(19) . . ?
N1 Cu1 Br1 97.67(17) . . ?
O1 Cu1 Br1 94.87(15) . 3_666 ?
N2 Cu1 Br1 107.57(19) . 3_666 ?
N1 Cu1 Br1 87.17(16) . 3_666 ?
Br1 Cu1 Br1 93.30(3) . 3_666 ?
C1 N1 C5 118.4(6) . . ?
C1 N1 Cu1 126.3(5) . . ?
C5 N1 Cu1 115.2(4) . . ?
C7 N2 C6 119.9(5) . . ?
C7 N2 Cu1 123.0(5) . . ?
C6 N2 Cu1 116.3(4) . . ?
C9 O1 Cu1 128.0(4) . . ?
C16 O3 C17 118.3(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 1.1(12) . . . . ?
C1 C2 C3 C4 -1.7(12) . . . . ?
C2 C3 C4 C5 0.9(12) . . . . ?
C3 C4 C5 N1 0.5(11) . . . . ?
C3 C4 C5 C6 177.5(7) . . . . ?
N1 C5 C6 N2 -10.2(9) . . . . ?
C4 C5 C6 N2 172.6(7) . . . . ?
N2 C7 C8 C9 12.2(12) . . . . ?
N2 C7 C8 C16 -163.5(7) . . . . ?
C7 C8 C9 O1 -11.3(11) . . . . ?
C16 C8 C9 O1 164.2(7) . . . . ?
C7 C8 C9 C10 163.2(7) . . . . ?
C16 C8 C9 C10 -21.4(10) . . . . ?
O1 C9 C10 C15 -37.7(9) . . . . ?
C8 C9 C10 C15 147.5(7) . . . . ?
O1 C9 C10 C11 137.8(7) . . . . ?
C8 C9 C10 C11 -37.0(10) . . . . ?
C15 C10 C11 C12 -2.7(10) . . . . ?
C9 C10 C11 C12 -178.2(7) . . . . ?
C10 C11 C12 C13 2.7(11) . . . . ?
C11 C12 C13 C14 -0.8(12) . . . . ?
C12 C13 C14 C15 -1.1(12) . . . . ?
C11 C10 C15 C14 0.8(11) . . . . ?
C9 C10 C15 C14 176.5(7) . . . . ?
C13 C14 C15 C10 1.1(12) . . . . ?
C7 C8 C16 O2 -28.3(10) . . . . ?
C9 C8 C16 O2 155.9(7) . . . . ?
C7 C8 C16 O3 146.4(6) . . . . ?
C9 C8 C16 O3 -29.3(9) . . . . ?
C2 C1 N1 C5 0.4(11) . . . . ?
C2 C1 N1 Cu1 -177.2(6) . . . . ?
C4 C5 N1 C1 -1.2(10) . . . . ?
C6 C5 N1 C1 -178.4(6) . . . . ?
C4 C5 N1 Cu1 176.7(6) . . . . ?
C6 C5 N1 Cu1 -0.6(8) . . . . ?
C8 C7 N2 C6 -179.5(7) . . . . ?
C8 C7 N2 Cu1 11.3(11) . . . . ?
C5 C6 N2 C7 -153.0(6) . . . . ?
C5 C6 N2 Cu1 16.9(8) . . . . ?
C8 C9 O1 Cu1 -14.0(10) . . . . ?
C10 C9 O1 Cu1 171.1(5) . . . . ?
O2 C16 O3 C17 -1.7(9) . . . . ?
C8 C16 O3 C17 -176.4(5) . . . . ?
C18 C17 O3 C16 -78.6(8) . . . . ?

_refine_diff_density_max         1.153
_refine_diff_density_min         -1.340
_refine_diff_density_rms         0.178

####################################################################### 
# 
# 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_kd037
_database_code_depnum_ccdc_archive 'CCDC 1915614'
loop_
_audit_author_name
_audit_author_address
'Katja Dankhoff'
;University of Bayreuth, Inorganic Chemistry IV
Germany
;
_audit_update_record             
;
2019-05-13 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;
_audit_creation_date             2019-01-09
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;

_chemical_name_common            '[CuL37dBr]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H14 Br Cu N3 O2'
_chemical_formula_sum            'C13 H14 Br Cu N3 O2'
_chemical_formula_weight         387.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8986(4)
_cell_length_b                   8.2689(3)
_cell_length_c                   11.3892(4)
_cell_angle_alpha                85.890(3)
_cell_angle_beta                 78.823(3)
_cell_angle_gamma                81.476(3)
_cell_volume                     720.98(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    8410
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      29.1

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_F_000             386
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.119
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.098
_exptl_absorpt_coefficient_mu    4.289
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            8912
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -10
_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       15
_diffrn_reflns_theta_min         1.824
_diffrn_reflns_theta_max         29.131
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3350
_reflns_number_gt                2709
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON

_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     
'w=1/[σ²(Fo²)+(0.0415P)²+0.1860P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3350
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.0741
_refine_ls_wR_factor_gt          0.0694
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3504(4) 0.4379(3) -0.1245(2) 0.0251(6) Uani 1 1 d . . . . .
H1 H 0.2291 0.4483 -0.0924 0.030 Uiso 1 1 calc R U . . .
C2 C 0.4123(4) 0.5313(3) -0.2279(3) 0.0284(6) Uani 1 1 d . . . . .
H2 H 0.3295 0.6040 -0.2634 0.034 Uiso 1 1 calc R U . . .
C3 C 0.5950(4) 0.5236(3) -0.2838(2) 0.0258(6) Uani 1 1 d . . . . .
C4 C 0.7067(4) 0.4192(3) -0.2294(2) 0.0236(6) Uani 1 1 d . . . . .
H4 H 0.8285 0.4076 -0.2596 0.028 Uiso 1 1 calc R U . . .
C5 C 0.6373(4) 0.3266(3) -0.1252(2) 0.0204(5) Uani 1 1 d . . . . .
C6 C 0.7567(4) 0.2093(3) -0.0665(2) 0.0229(6) Uani 1 1 d . . . . .
H6A H 0.8447 0.2663 -0.0414 0.027 Uiso 1 1 calc R U . . .
H6B H 0.8181 0.1243 -0.1225 0.027 Uiso 1 1 calc R U . . .
C7 C 0.7334(4) 0.0377(3) 0.1112(2) 0.0211(5) Uani 1 1 d . . . . .
H7 H 0.8568 0.0198 0.0890 0.025 Uiso 1 1 calc R U . . .
C8 C 0.6551(4) -0.0436(3) 0.2209(2) 0.0205(5) Uani 1 1 d . . . . .
C9 C 0.4693(4) -0.0297(3) 0.2713(2) 0.0213(5) Uani 1 1 d . . . . .
C10 C 0.2243(4) -0.0924(3) 0.4358(2) 0.0243(6) Uani 1 1 d . . . . .
H10A H 0.1547 -0.1238 0.3798 0.029 Uiso 1 1 calc R U . . .
H10B H 0.1834 0.0236 0.4546 0.029 Uiso 1 1 calc R U . . .
C11 C 0.1976(4) -0.1994(3) 0.5503(2) 0.0276(6) Uani 1 1 d . . . . .
H11A H 0.2390 -0.3141 0.5317 0.041 Uiso 1 1 calc R U . . .
H11B H 0.0734 -0.1877 0.5861 0.041 Uiso 1 1 calc R U . . .
H11C H 0.2632 -0.1656 0.6069 0.041 Uiso 1 1 calc R U . . .
C12 C 0.7701(4) -0.1420(3) 0.2827(2) 0.0240(6) Uani 1 1 d . . . . .
C13 C 0.6657(4) 0.6236(4) -0.3969(3) 0.0341(7) Uani 1 1 d . . . . .
H13A H 0.7932 0.6085 -0.4102 0.051 Uiso 1 1 calc R U . . .
H13B H 0.6212 0.7398 -0.3866 0.051 Uiso 1 1 calc R U . . .
H13C H 0.6276 0.5863 -0.4661 0.051 Uiso 1 1 calc R U . . .
N1 N 0.4615(3) 0.3355(3) -0.07218(19) 0.0212(5) Uani 1 1 d . . . . .
N2 N 0.6494(3) 0.1312(3) 0.04233(19) 0.0209(5) Uani 1 1 d . . . . .
N3 N 0.8660(3) -0.2194(3) 0.3308(2) 0.0330(6) Uani 1 1 d . . . . .
O1 O 0.3559(2) 0.0520(2) 0.22424(16) 0.0226(4) Uani 1 1 d . . . . .
O2 O 0.4149(2) -0.1114(2) 0.37727(16) 0.0232(4) Uani 1 1 d . . . . .
Cu1 Cu 0.39404(4) 0.19408(4) 0.07749(3) 0.01905(9) Uani 1 1 d . . . . .
Br1 Br 0.08136(3) 0.26866(3) 0.12121(2) 0.02380(9) 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
C1 N1 1.324(3) . ?
C1 C2 1.407(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.454(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.348(4) . ?
C3 C13 1.537(4) . ?
C4 C5 1.427(4) . ?
C4 H4 0.9500 . ?
C5 N1 1.396(4) . ?
C5 C6 1.469(3) . ?
C6 N2 1.520(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.271(3) . ?
C7 C8 1.449(4) . ?
C7 H7 0.9500 . ?
C8 C12 1.389(3) . ?
C8 C9 1.459(4) . ?
C9 O1 1.225(3) . ?
C9 O2 1.366(3) . ?
C10 O2 1.514(3) . ?
C10 C11 1.520(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N3 1.119(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N1 Cu1 2.026(2) . ?
N2 Cu1 1.976(2) . ?
O1 Cu1 1.9732(18) . ?
Cu1 Br1 2.4173(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 119.8(3) . . ?
N1 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C1 C2 C3 124.1(3) . . ?
C1 C2 H2 117.9 . . ?
C3 C2 H2 117.9 . . ?
C4 C3 C2 115.4(2) . . ?
C4 C3 C13 119.5(3) . . ?
C2 C3 C13 125.1(3) . . ?
C3 C4 C5 118.3(3) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 125.7(2) . . ?
N1 C5 C6 115.3(2) . . ?
C4 C5 C6 119.0(2) . . ?
C5 C6 N2 107.9(2) . . ?
C5 C6 H6A 110.1 . . ?
N2 C6 H6A 110.1 . . ?
C5 C6 H6B 110.1 . . ?
N2 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
N2 C7 C8 124.9(3) . . ?
N2 C7 H7 117.6 . . ?
C8 C7 H7 117.6 . . ?
C12 C8 C7 115.9(2) . . ?
C12 C8 C9 118.2(2) . . ?
C7 C8 C9 126.0(2) . . ?
O1 C9 O2 116.7(2) . . ?
O1 C9 C8 124.0(2) . . ?
O2 C9 C8 119.4(2) . . ?
O2 C10 C11 110.5(2) . . ?
O2 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
O2 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C8 178.2(3) . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 N1 C5 116.6(2) . . ?
C1 N1 Cu1 124.74(19) . . ?
C5 N1 Cu1 118.64(17) . . ?
C7 N2 C6 116.7(2) . . ?
C7 N2 Cu1 123.66(19) . . ?
C6 N2 Cu1 119.43(15) . . ?
C9 O1 Cu1 126.16(18) . . ?
C9 O2 C10 120.9(2) . . ?
O1 Cu1 N2 95.10(8) . . ?
O1 Cu1 N1 173.68(8) . . ?
N2 Cu1 N1 78.76(9) . . ?
O1 Cu1 Br1 84.50(5) . . ?
N2 Cu1 Br1 179.52(7) . . ?
N1 Cu1 Br1 101.65(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.2(4) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C1 C2 C3 C13 179.7(3) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C13 C3 C4 C5 -179.4(2) . . . . ?
C3 C4 C5 N1 -0.9(4) . . . . ?
C3 C4 C5 C6 178.5(2) . . . . ?
N1 C5 C6 N2 -1.6(3) . . . . ?
C4 C5 C6 N2 178.9(2) . . . . ?
N2 C7 C8 C12 179.4(3) . . . . ?
N2 C7 C8 C9 -1.1(4) . . . . ?
C12 C8 C9 O1 -179.2(2) . . . . ?
C7 C8 C9 O1 1.3(4) . . . . ?
C12 C8 C9 O2 0.8(4) . . . . ?
C7 C8 C9 O2 -178.6(2) . . . . ?
C2 C1 N1 C5 -0.3(4) . . . . ?
C2 C1 N1 Cu1 179.4(2) . . . . ?
C4 C5 N1 C1 0.7(4) . . . . ?
C6 C5 N1 C1 -178.7(2) . . . . ?
C4 C5 N1 Cu1 -179.1(2) . . . . ?
C6 C5 N1 Cu1 1.5(3) . . . . ?
C8 C7 N2 C6 178.0(2) . . . . ?
C8 C7 N2 Cu1 3.8(4) . . . . ?
C5 C6 N2 C7 -173.3(2) . . . . ?
C5 C6 N2 Cu1 1.2(3) . . . . ?
O2 C9 O1 Cu1 175.75(15) . . . . ?
C8 C9 O1 Cu1 -4.2(4) . . . . ?
O1 C9 O2 C10 -3.5(3) . . . . ?
C8 C9 O2 C10 176.5(2) . . . . ?
C11 C10 O2 C9 178.3(2) . . . . ?

_refine_diff_density_max         0.610
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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_cl093
_database_code_depnum_ccdc_archive 'CCDC 1566632'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '[CuL30iBr]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H26 Br2 Cu2 N4 O6'
_chemical_formula_sum            'C24 H26 Br2 Cu2 N4 O6'
_chemical_formula_weight         753.38
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0566(4)
_cell_length_b                   8.4259(4)
_cell_length_c                   11.1094(5)
_cell_angle_alpha                75.675(4)
_cell_angle_beta                 86.846(4)
_cell_angle_gamma                68.045(4)
_cell_volume                     677.12(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    7582
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      28.4

_exptl_crystal_description       prism
_exptl_crystal_colour            'blue green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.848
_exptl_crystal_F_000             374
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.099
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    4.567
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            8251
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.893
_diffrn_reflns_theta_max         28.421
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.937
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             3198
_reflns_number_gt                2677
_reflns_threshold_expression     'I > 2σ(I)'

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON

_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     
'w=1/[σ²(Fo²)+(0.0312P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3198
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0560
_refine_ls_wR_factor_gt          0.0534
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2913(3) 0.2901(3) 1.1377(2) 0.0174(4) Uani 1 1 d . . . . .
H1 H 0.3503 0.1683 1.1763 0.021 Uiso 1 1 calc R U . . .
C2 C 0.1602(3) 0.3946(3) 1.2000(2) 0.0187(4) Uani 1 1 d . . . . .
H2 H 0.1290 0.3457 1.2805 0.022 Uiso 1 1 calc R U . . .
C3 C 0.0743(3) 0.5727(3) 1.1434(2) 0.0196(4) Uani 1 1 d . . . . .
H3 H -0.0154 0.6473 1.1854 0.024 Uiso 1 1 calc R U . . .
C4 C 0.1201(3) 0.6401(3) 1.0261(2) 0.0184(4) Uani 1 1 d . . . . .
H4 H 0.0620 0.7613 0.9858 0.022 Uiso 1 1 calc R U . . .
C5 C 0.2530(3) 0.5277(3) 0.96778(19) 0.0151(4) Uani 1 1 d . . . . .
C6 C 0.3032(3) 0.5906(3) 0.8376(2) 0.0179(4) Uani 1 1 d . . . . .
H6A H 0.2002 0.6257 0.7791 0.021 Uiso 1 1 calc R U . . .
H6B H 0.3349 0.6949 0.8318 0.021 Uiso 1 1 calc R U . . .
C7 C 0.5323(3) 0.4903(3) 0.70219(19) 0.0174(4) Uani 1 1 d . . . . .
H7 H 0.4901 0.6113 0.6590 0.021 Uiso 1 1 calc R U . . .
C8 C 0.6737(3) 0.3713(3) 0.6483(2) 0.0197(4) Uani 1 1 d . . . . .
C9 C 0.7405(3) 0.1884(3) 0.7020(2) 0.0229(5) Uani 1 1 d . . . . .
C10 C 0.8826(4) 0.0587(4) 0.6438(3) 0.0387(7) Uani 1 1 d . . . . .
H10A H 0.9192 -0.0592 0.7002 0.058 Uiso 1 1 calc R U . . .
H10B H 0.9863 0.0938 0.6280 0.058 Uiso 1 1 calc R U . . .
H10C H 0.8349 0.0569 0.5650 0.058 Uiso 1 1 calc R U . . .
C11 C 0.7429(3) 0.4504(3) 0.5333(2) 0.0229(5) Uani 1 1 d . . . . .
C12 C 0.7382(4) 0.7218(4) 0.4021(2) 0.0369(6) Uani 1 1 d . . . . .
H12A H 0.8688 0.6852 0.4023 0.055 Uiso 1 1 calc R U . . .
H12B H 0.6835 0.8490 0.3956 0.055 Uiso 1 1 calc R U . . .
H12C H 0.6966 0.6950 0.3310 0.055 Uiso 1 1 calc R U . . .
N1 N 0.3385(2) 0.3559(2) 1.02309(16) 0.0149(3) Uani 1 1 d . . . . .
N2 N 0.4557(2) 0.4491(2) 0.80464(16) 0.0164(3) Uani 1 1 d . . . . .
O1 O 0.6887(2) 0.1176(2) 0.80421(15) 0.0236(3) Uani 1 1 d . . . . .
O2 O 0.8376(3) 0.3754(3) 0.46047(16) 0.0342(4) Uani 1 1 d . . . . .
O3 O 0.6876(3) 0.6281(2) 0.51572(15) 0.0293(4) Uani 1 1 d . . . . .
Cu1 Cu 0.52682(3) 0.22149(3) 0.92209(2) 0.01574(7) Uani 1 1 d . . . . .
Br1 Br 0.69653(3) -0.01491(3) 1.09529(2) 0.01807(7) 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
C1 N1 1.352(3) . ?
C1 C2 1.377(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.344(3) . ?
C5 C6 1.501(3) . ?
C6 N2 1.462(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.298(3) . ?
C7 C8 1.424(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.407(3) . ?
C8 C11 1.472(3) . ?
C9 O1 1.273(3) . ?
C9 C10 1.502(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O2 1.209(3) . ?
C11 O3 1.358(3) . ?
C12 O3 1.440(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N1 Cu1 2.0004(17) . ?
N2 Cu1 1.9319(18) . ?
O1 Cu1 1.9259(15) . ?
Cu1 Br1 2.4281(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 121.8(2) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C1 C2 C3 119.0(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 119.46(19) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 118.8(2) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 121.85(19) . . ?
N1 C5 C6 116.57(17) . . ?
C4 C5 C6 121.54(19) . . ?
N2 C6 C5 109.47(17) . . ?
N2 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
N2 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 126.2(2) . . ?
N2 C7 H7 116.9 . . ?
C8 C7 H7 116.9 . . ?
C9 C8 C7 121.40(19) . . ?
C9 C8 C11 122.4(2) . . ?
C7 C8 C11 116.2(2) . . ?
O1 C9 C8 123.6(2) . . ?
O1 C9 C10 113.8(2) . . ?
C8 C9 C10 122.6(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 O3 121.3(2) . . ?
O2 C11 C8 127.5(2) . . ?
O3 C11 C8 111.12(19) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 N1 C1 119.01(18) . . ?
C5 N1 Cu1 114.63(14) . . ?
C1 N1 Cu1 126.36(14) . . ?
C7 N2 C6 117.00(18) . . ?
C7 N2 Cu1 126.89(16) . . ?
C6 N2 Cu1 116.07(13) . . ?
C9 O1 Cu1 130.92(15) . . ?
C11 O3 C12 116.2(2) . . ?
O1 Cu1 N2 89.78(7) . . ?
O1 Cu1 N1 171.70(7) . . ?
N2 Cu1 N1 82.75(7) . . ?
O1 Cu1 Br1 91.75(5) . . ?
N2 Cu1 Br1 156.75(6) . . ?
N1 Cu1 Br1 96.54(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.1(3) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 N1 -0.5(3) . . . . ?
C3 C4 C5 C6 177.0(2) . . . . ?
N1 C5 C6 N2 -7.0(3) . . . . ?
C4 C5 C6 N2 175.28(18) . . . . ?
N2 C7 C8 C9 2.8(4) . . . . ?
N2 C7 C8 C11 -178.0(2) . . . . ?
C7 C8 C9 O1 -4.2(4) . . . . ?
C11 C8 C9 O1 176.7(2) . . . . ?
C7 C8 C9 C10 176.7(2) . . . . ?
C11 C8 C9 C10 -2.4(4) . . . . ?
C9 C8 C11 O2 13.4(4) . . . . ?
C7 C8 C11 O2 -165.7(2) . . . . ?
C9 C8 C11 O3 -166.2(2) . . . . ?
C7 C8 C11 O3 14.7(3) . . . . ?
C4 C5 N1 C1 1.3(3) . . . . ?
C6 C5 N1 C1 -176.36(19) . . . . ?
C4 C5 N1 Cu1 -179.11(16) . . . . ?
C6 C5 N1 Cu1 3.2(2) . . . . ?
C2 C1 N1 C5 -1.0(3) . . . . ?
C2 C1 N1 Cu1 179.47(16) . . . . ?
C8 C7 N2 C6 -175.2(2) . . . . ?
C8 C7 N2 Cu1 7.1(3) . . . . ?
C5 C6 N2 C7 -170.10(19) . . . . ?
C5 C6 N2 Cu1 7.8(2) . . . . ?
C8 C9 O1 Cu1 -4.7(4) . . . . ?
C10 C9 O1 Cu1 174.52(19) . . . . ?
O2 C11 O3 C12 4.0(3) . . . . ?
C8 C11 O3 C12 -176.4(2) . . . . ?

_refine_diff_density_max         0.509
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.083

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_kd066
_database_code_depnum_ccdc_archive 'CCDC 1915617'
loop_
_audit_author_name
_audit_author_address
'Katja Dankhoff'
;University of Bayreuth, Inorganic Chemistry IV
Germany
;
_audit_update_record             
;
2019-05-13 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;
_audit_creation_date             2019-01-09
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;

_chemical_name_common            '[CuL40cBr]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H19 Br Cu N2 O4'
_chemical_formula_sum            'C15 H19 Br Cu N2 O4'
_chemical_formula_weight         434.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/a'
_space_group_name_Hall           '-P 2yab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.9002(3)
_cell_length_b                   18.0037(6)
_cell_length_c                   11.3870(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.962(4)
_cell_angle_gamma                90
_cell_volume                     1613.54(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    10363
_cell_measurement_theta_min      1.6
_cell_measurement_theta_max      28.4

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_F_000             876
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.079
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.037
_exptl_absorpt_coefficient_mu    3.851
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;??
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            12531
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.795
_diffrn_reflns_theta_max         28.445
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3900
_reflns_number_gt                2978
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON

_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     
'w=1/[σ²(Fo²)+(0.0611P)²+1.1213P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3900
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2050(4) 0.3655(2) 0.4174(3) 0.0237(7) Uani 1 1 d . . . . .
H1 H 0.2650 0.3273 0.4609 0.028 Uiso 1 1 calc R U . . .
C2 C 0.2234(5) 0.4384(2) 0.4578(3) 0.0272(8) Uani 1 1 d . . . . .
C3 C 0.1359(5) 0.4932(2) 0.3906(3) 0.0280(8) Uani 1 1 d . . . . .
H3 H 0.1450 0.5438 0.4142 0.034 Uiso 1 1 calc R U . . .
C4 C 0.0360(5) 0.4737(2) 0.2897(3) 0.0271(8) Uani 1 1 d . . . . .
H4 H -0.0231 0.5109 0.2432 0.033 Uiso 1 1 calc R U . . .
C5 C 0.0226(4) 0.40013(19) 0.2570(3) 0.0206(7) Uani 1 1 d . . . . .
C6 C -0.0889(5) 0.37572(19) 0.1497(3) 0.0249(8) Uani 1 1 d . . . . .
H6A H -0.2062 0.3938 0.1554 0.030 Uiso 1 1 calc R U . . .
H6B H -0.0462 0.3974 0.0780 0.030 Uiso 1 1 calc R U . . .
C7 C -0.1794(4) 0.2644(2) 0.0527(3) 0.0225(7) Uani 1 1 d . . . . .
H7 H -0.2376 0.2977 -0.0016 0.027 Uiso 1 1 calc R U . . .
C8 C -0.2008(5) 0.18771(18) 0.0279(3) 0.0216(7) Uani 1 1 d . . . . .
C9 C -0.1153(4) 0.1345(2) 0.1052(3) 0.0227(7) Uani 1 1 d . . . . .
C10 C -0.0631(5) 0.0086(2) 0.1606(4) 0.0290(8) Uani 1 1 d . . . . .
H10A H -0.0797 0.0209 0.2435 0.035 Uiso 1 1 calc R U . . .
H10B H 0.0602 0.0070 0.1512 0.035 Uiso 1 1 calc R U . . .
C11 C -0.1453(5) -0.0645(2) 0.1264(4) 0.0318(9) Uani 1 1 d . . . . .
H11A H -0.2691 -0.0587 0.1191 0.048 Uiso 1 1 calc R U . . .
H11B H -0.1125 -0.1017 0.1870 0.048 Uiso 1 1 calc R U . . .
H11C H -0.1078 -0.0808 0.0507 0.048 Uiso 1 1 calc R U . . .
C12 C -0.3109(5) 0.1633(2) -0.0749(3) 0.0262(8) Uani 1 1 d . . . . .
C13 C -0.4881(5) 0.2020(2) -0.2416(3) 0.0302(8) Uani 1 1 d . . . . .
H13A H -0.5907 0.1765 -0.2175 0.036 Uiso 1 1 calc R U . . .
H13B H -0.4284 0.1678 -0.2921 0.036 Uiso 1 1 calc R U . . .
C14 C -0.5382(5) 0.2716(2) -0.3085(4) 0.0303(8) Uani 1 1 d . . . . .
H14A H -0.6000 0.3045 -0.2587 0.045 Uiso 1 1 calc R U . . .
H14B H -0.6112 0.2588 -0.3796 0.045 Uiso 1 1 calc R U . . .
H14C H -0.4360 0.2968 -0.3310 0.045 Uiso 1 1 calc R U . . .
C15 C 0.3326(5) 0.4546(2) 0.5691(3) 0.0304(9) Uani 1 1 d . . . . .
H15A H 0.3433 0.5085 0.5796 0.046 Uiso 1 1 calc R U . . .
H15B H 0.4455 0.4329 0.5642 0.046 Uiso 1 1 calc R U . . .
H15C H 0.2805 0.4331 0.6364 0.046 Uiso 1 1 calc R U . . .
N1 N 0.1063(4) 0.34667(17) 0.3198(3) 0.0222(6) Uani 1 1 d . . . . .
N2 N -0.0894(4) 0.29443(16) 0.1409(3) 0.0222(6) Uani 1 1 d . . . . .
O1 O -0.0148(3) 0.14956(14) 0.1923(2) 0.0261(6) Uani 1 1 d . . . . .
O2 O -0.1468(3) 0.06305(14) 0.0811(2) 0.0261(6) Uani 1 1 d . . . . .
O3 O -0.3436(4) 0.10046(16) -0.1057(3) 0.0456(8) Uani 1 1 d . . . . .
O4 O -0.3780(3) 0.22187(14) -0.1388(2) 0.0256(5) Uani 1 1 d . . . . .
Cu1 Cu 0.04715(5) 0.24402(2) 0.26590(4) 0.02179(13) Uani 1 1 d . . . . .
Br1 Br 0.20249(5) 0.17819(2) 0.42087(3) 0.02798(13) 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
C1 N1 1.344(4) . ?
C1 C2 1.393(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.395(6) . ?
C2 C15 1.500(5) . ?
C3 C4 1.382(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(5) . ?
C4 H4 0.9500 . ?
C5 N1 1.339(4) . ?
C5 C6 1.508(5) . ?
C6 N2 1.467(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.298(5) . ?
C7 C8 1.416(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.431(5) . ?
C8 C12 1.464(5) . ?
C9 O1 1.245(4) . ?
C9 O2 1.334(4) . ?
C10 O2 1.454(4) . ?
C10 C11 1.504(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O3 1.205(5) . ?
C12 O4 1.363(4) . ?
C13 O4 1.442(5) . ?
C13 C14 1.501(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 Cu1 1.990(3) . ?
N2 Cu1 1.936(3) . ?
O1 Cu1 1.940(3) . ?
Cu1 Br1 2.3769(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 123.1(3) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 116.9(4) . . ?
C1 C2 C15 119.9(3) . . ?
C3 C2 C15 123.2(3) . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 121.6(3) . . ?
N1 C5 C6 116.7(3) . . ?
C4 C5 C6 121.7(3) . . ?
N2 C6 C5 110.1(3) . . ?
N2 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
N2 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 127.5(3) . . ?
N2 C7 H7 116.3 . . ?
C8 C7 H7 116.3 . . ?
C7 C8 C9 119.2(3) . . ?
C7 C8 C12 120.3(3) . . ?
C9 C8 C12 120.5(3) . . ?
O1 C9 O2 117.9(3) . . ?
O1 C9 C8 125.4(3) . . ?
O2 C9 C8 116.7(3) . . ?
O2 C10 C11 105.4(3) . . ?
O2 C10 H10A 110.7 . . ?
C11 C10 H10A 110.7 . . ?
O2 C10 H10B 110.7 . . ?
C11 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 O4 120.5(3) . . ?
O3 C12 C8 127.7(3) . . ?
O4 C12 C8 111.8(3) . . ?
O4 C13 C14 108.6(3) . . ?
O4 C13 H13A 110.0 . . ?
C14 C13 H13A 110.0 . . ?
O4 C13 H13B 110.0 . . ?
C14 C13 H13B 110.0 . . ?
H13A C13 H13B 108.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C15 H15A 109.5 . . ?
C2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 N1 C1 119.0(3) . . ?
C5 N1 Cu1 114.2(2) . . ?
C1 N1 Cu1 126.4(3) . . ?
C7 N2 C6 117.8(3) . . ?
C7 N2 Cu1 127.4(3) . . ?
C6 N2 Cu1 114.8(2) . . ?
C9 O1 Cu1 130.9(2) . . ?
C9 O2 C10 117.1(3) . . ?
C12 O4 C13 114.9(3) . . ?
N2 Cu1 O1 89.41(12) . . ?
N2 Cu1 N1 83.82(12) . . ?
O1 Cu1 N1 172.33(12) . . ?
N2 Cu1 Br1 177.05(9) . . ?
O1 Cu1 Br1 88.77(8) . . ?
N1 Cu1 Br1 98.14(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -1.2(5) . . . . ?
N1 C1 C2 C15 178.5(3) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C15 C2 C3 C4 -179.2(3) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C3 C4 C5 N1 -1.0(5) . . . . ?
C3 C4 C5 C6 178.1(3) . . . . ?
N1 C5 C6 N2 3.5(4) . . . . ?
C4 C5 C6 N2 -175.7(3) . . . . ?
N2 C7 C8 C9 -0.6(6) . . . . ?
N2 C7 C8 C12 178.6(3) . . . . ?
C7 C8 C9 O1 -3.4(5) . . . . ?
C12 C8 C9 O1 177.4(3) . . . . ?
C7 C8 C9 O2 176.7(3) . . . . ?
C12 C8 C9 O2 -2.5(5) . . . . ?
C7 C8 C12 O3 -178.5(4) . . . . ?
C9 C8 C12 O3 0.7(6) . . . . ?
C7 C8 C12 O4 2.0(5) . . . . ?
C9 C8 C12 O4 -178.8(3) . . . . ?
C4 C5 N1 C1 0.3(5) . . . . ?
C6 C5 N1 C1 -178.8(3) . . . . ?
C4 C5 N1 Cu1 173.5(3) . . . . ?
C6 C5 N1 Cu1 -5.7(4) . . . . ?
C2 C1 N1 C5 0.8(5) . . . . ?
C2 C1 N1 Cu1 -171.5(3) . . . . ?
C8 C7 N2 C6 -178.8(3) . . . . ?
C8 C7 N2 Cu1 0.9(5) . . . . ?
C5 C6 N2 C7 -179.8(3) . . . . ?
C5 C6 N2 Cu1 0.4(3) . . . . ?
O2 C9 O1 Cu1 -173.1(2) . . . . ?
C8 C9 O1 Cu1 7.0(5) . . . . ?
O1 C9 O2 C10 1.2(5) . . . . ?
C8 C9 O2 C10 -178.8(3) . . . . ?
C11 C10 O2 C9 169.8(3) . . . . ?
O3 C12 O4 C13 0.6(5) . . . . ?
C8 C12 O4 C13 -180.0(3) . . . . ?
C14 C13 O4 C12 -174.7(3) . . . . ?

_refine_diff_density_max         0.923
_refine_diff_density_min         -0.882
_refine_diff_density_rms         0.119

####################################################################### 
# 
# 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_kd046
_database_code_depnum_ccdc_archive 'CCDC 1915615'
loop_
_audit_author_name
_audit_author_address
'Katja Dankhoff'
;University of Bayreuth, Inorganic Chemistry IV
Germany
;
_audit_update_record             
;
2019-05-13 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;
_audit_creation_date             2019-01-09
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL38cBr]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H16 Br Cl Cu N2 O4'
_chemical_formula_sum            'C14 H16 Br Cl Cu N2 O4'
_chemical_formula_weight         455.19

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0351(3)
_cell_length_b                   9.6830(3)
_cell_length_c                   11.4547(4)
_cell_angle_alpha                98.869(3)
_cell_angle_beta                 102.321(3)
_cell_angle_gamma                104.864(3)
_cell_volume                     820.70(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    12430
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      28.5

_exptl_crystal_description       cube
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_F_000             454
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.095
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.065
_exptl_absorpt_coefficient_mu    3.947
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;??
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            12083
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.866
_diffrn_reflns_theta_max         28.491
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3966
_reflns_number_gt                3236
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON

_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     
'w=1/[σ²(Fo²)+(0.0547P)²+0.8234P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3966
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0995
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2677(4) 0.1223(3) 1.0268(3) 0.0262(7) Uani 1 1 d . . . . .
H1 H 0.1462 0.1102 0.9884 0.031 Uiso 1 1 calc R U . . .
C2 C 0.3060(4) 0.0458(3) 1.1155(3) 0.0260(7) Uani 1 1 d . . . . .
H2 H 0.2135 -0.0176 1.1388 0.031 Uiso 1 1 calc R U . . .
C3 C 0.4844(4) 0.0643(3) 1.1697(3) 0.0245(6) Uani 1 1 d . . . . .
C4 C 0.6182(4) 0.1580(3) 1.1360(3) 0.0238(6) Uani 1 1 d . . . . .
H4 H 0.7405 0.1710 1.1729 0.029 Uiso 1 1 calc R U . . .
C5 C 0.5691(4) 0.2324(3) 1.0466(3) 0.0214(6) Uani 1 1 d . . . . .
C6 C 0.7063(4) 0.3358(3) 1.0050(3) 0.0234(6) Uani 1 1 d . . . . .
H6A H 0.7857 0.4139 1.0759 0.028 Uiso 1 1 calc R U . . .
H6B H 0.7803 0.2822 0.9699 0.028 Uiso 1 1 calc R U . . .
C7 C 0.7197(4) 0.4934(3) 0.8657(3) 0.0227(6) Uani 1 1 d . . . . .
H7 H 0.8449 0.5144 0.8975 0.027 Uiso 1 1 calc R U . . .
C8 C 0.6646(4) 0.5652(3) 0.7737(3) 0.0222(6) Uani 1 1 d . . . . .
C9 C 0.4796(4) 0.5349(3) 0.7160(3) 0.0235(6) Uani 1 1 d . . . . .
C10 C 0.2448(4) 0.5717(4) 0.5696(3) 0.0297(7) Uani 1 1 d . . . . .
H10A H 0.1796 0.5946 0.6305 0.036 Uiso 1 1 calc R U . . .
H10B H 0.1926 0.4669 0.5280 0.036 Uiso 1 1 calc R U . . .
C11 C 0.2345(5) 0.6673(4) 0.4779(3) 0.0322(7) Uani 1 1 d . . . . .
H11A H 0.2815 0.7705 0.5210 0.048 Uiso 1 1 calc R U . . .
H11B H 0.1098 0.6464 0.4318 0.048 Uiso 1 1 calc R U . . .
H11C H 0.3054 0.6472 0.4212 0.048 Uiso 1 1 calc R U . . .
C12 C 0.8103(4) 0.6708(4) 0.7462(3) 0.0257(6) Uani 1 1 d . . . . .
C13 C 0.8908(5) 0.8465(4) 0.6287(3) 0.0331(8) Uani 1 1 d . . . . .
H13A H 0.9806 0.8081 0.5987 0.040 Uiso 1 1 calc R U . . .
H13B H 0.9528 0.9246 0.7036 0.040 Uiso 1 1 calc R U . . .
C14 C 0.7873(5) 0.9044(5) 0.5313(4) 0.0472(10) Uani 1 1 d . . . . .
H14A H 0.7461 0.8319 0.4534 0.071 Uiso 1 1 calc R U . . .
H14B H 0.8646 0.9959 0.5215 0.071 Uiso 1 1 calc R U . . .
H14C H 0.6840 0.9230 0.5558 0.071 Uiso 1 1 calc R U . . .
N1 N 0.3965(3) 0.2143(3) 0.9921(2) 0.0228(5) Uani 1 1 d . . . . .
N2 N 0.6182(3) 0.4008(3) 0.9130(2) 0.0228(5) Uani 1 1 d . . . . .
O1 O 0.3549(3) 0.4465(3) 0.7427(2) 0.0280(5) Uani 1 1 d . . . . .
O2 O 0.4347(3) 0.6044(2) 0.6288(2) 0.0262(5) Uani 1 1 d . . . . .
O3 O 0.9660(3) 0.7030(3) 0.8032(3) 0.0427(7) Uani 1 1 d . . . . .
O4 O 0.7579(3) 0.7303(3) 0.6534(2) 0.0316(5) Uani 1 1 d . . . . .
Cl1 Cl 0.53861(11) -0.03380(9) 1.27820(7) 0.03100(19) Uani 1 1 d . . . . .
Cu1 Cu 0.36054(5) 0.33245(4) 0.86601(3) 0.02318(11) Uani 1 1 d . . . . .
Br1 Br 0.04319(4) 0.26187(4) 0.81549(3) 0.02987(11) 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
C1 N1 1.354(4) . ?
C1 C2 1.375(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.388(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(4) . ?
C3 Cl1 1.727(3) . ?
C4 C5 1.387(4) . ?
C4 H4 0.9500 . ?
C5 N1 1.348(4) . ?
C5 C6 1.500(4) . ?
C6 N2 1.457(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.313(4) . ?
C7 C8 1.405(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.425(4) . ?
C8 C12 1.469(4) . ?
C9 O1 1.266(4) . ?
C9 O2 1.327(4) . ?
C10 O2 1.460(4) . ?
C10 C11 1.506(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O3 1.216(4) . ?
C12 O4 1.326(4) . ?
C13 O4 1.448(4) . ?
C13 C14 1.513(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N1 Cu1 1.995(3) . ?
N2 Cu1 1.930(3) . ?
O1 Cu1 1.922(2) . ?
Cu1 Br1 2.3787(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.5(3) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C1 C2 C3 117.8(3) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 Cl1 120.0(3) . . ?
C2 C3 Cl1 119.4(2) . . ?
C3 C4 C5 118.2(3) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
N1 C5 C4 121.8(3) . . ?
N1 C5 C6 116.8(3) . . ?
C4 C5 C6 121.4(3) . . ?
N2 C6 C5 109.8(2) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 127.6(3) . . ?
N2 C7 H7 116.2 . . ?
C8 C7 H7 116.2 . . ?
C7 C8 C9 120.3(3) . . ?
C7 C8 C12 114.8(3) . . ?
C9 C8 C12 124.9(3) . . ?
O1 C9 O2 117.7(3) . . ?
O1 C9 C8 124.4(3) . . ?
O2 C9 C8 117.9(3) . . ?
O2 C10 C11 105.7(3) . . ?
O2 C10 H10A 110.6 . . ?
C11 C10 H10A 110.6 . . ?
O2 C10 H10B 110.6 . . ?
C11 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 O4 122.1(3) . . ?
O3 C12 C8 123.6(3) . . ?
O4 C12 C8 114.3(3) . . ?
O4 C13 C14 105.0(3) . . ?
O4 C13 H13A 110.7 . . ?
C14 C13 H13A 110.7 . . ?
O4 C13 H13B 110.7 . . ?
C14 C13 H13B 110.7 . . ?
H13A C13 H13B 108.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 N1 C1 119.0(3) . . ?
C5 N1 Cu1 114.19(19) . . ?
C1 N1 Cu1 126.8(2) . . ?
C7 N2 C6 117.7(3) . . ?
C7 N2 Cu1 126.3(2) . . ?
C6 N2 Cu1 115.89(18) . . ?
C9 O1 Cu1 131.0(2) . . ?
C9 O2 C10 117.5(2) . . ?
C12 O4 C13 117.6(3) . . ?
O1 Cu1 N2 90.31(10) . . ?
O1 Cu1 N1 172.91(10) . . ?
N2 Cu1 N1 83.24(10) . . ?
O1 Cu1 Br1 89.15(7) . . ?
N2 Cu1 Br1 176.52(8) . . ?
N1 Cu1 Br1 97.46(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.5(5) . . . . ?
C1 C2 C3 C4 0.6(5) . . . . ?
C1 C2 C3 Cl1 -178.1(2) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
Cl1 C3 C4 C5 178.6(2) . . . . ?
C3 C4 C5 N1 -0.7(5) . . . . ?
C3 C4 C5 C6 -180.0(3) . . . . ?
N1 C5 C6 N2 2.0(4) . . . . ?
C4 C5 C6 N2 -178.8(3) . . . . ?
N2 C7 C8 C9 -3.3(5) . . . . ?
N2 C7 C8 C12 175.9(3) . . . . ?
C7 C8 C9 O1 1.0(5) . . . . ?
C12 C8 C9 O1 -178.0(3) . . . . ?
C7 C8 C9 O2 -179.3(3) . . . . ?
C12 C8 C9 O2 1.6(5) . . . . ?
C7 C8 C12 O3 -5.0(5) . . . . ?
C9 C8 C12 O3 174.1(3) . . . . ?
C7 C8 C12 O4 175.5(3) . . . . ?
C9 C8 C12 O4 -5.4(5) . . . . ?
C4 C5 N1 C1 0.9(5) . . . . ?
C6 C5 N1 C1 -179.8(3) . . . . ?
C4 C5 N1 Cu1 -179.6(2) . . . . ?
C6 C5 N1 Cu1 -0.4(4) . . . . ?
C2 C1 N1 C5 -0.3(5) . . . . ?
C2 C1 N1 Cu1 -179.7(2) . . . . ?
C8 C7 N2 C6 177.8(3) . . . . ?
C8 C7 N2 Cu1 1.5(5) . . . . ?
C5 C6 N2 C7 -179.3(3) . . . . ?
C5 C6 N2 Cu1 -2.7(3) . . . . ?
O2 C9 O1 Cu1 -176.8(2) . . . . ?
C8 C9 O1 Cu1 2.9(5) . . . . ?
O1 C9 O2 C10 -0.8(4) . . . . ?
C8 C9 O2 C10 179.5(3) . . . . ?
C11 C10 O2 C9 178.9(3) . . . . ?
O3 C12 O4 C13 -5.8(5) . . . . ?
C8 C12 O4 C13 173.7(3) . . . . ?
C14 C13 O4 C12 -172.6(3) . . . . ?

_refine_diff_density_max         0.550
_refine_diff_density_min         -0.842
_refine_diff_density_rms         0.108

####################################################################### 
# 
# 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_kd057
_database_code_depnum_ccdc_archive 'CCDC 1915616'
loop_
_audit_author_name
_audit_author_address
'Katja Dankhoff'
;University of Bayreuth, Inorganic Chemistry IV
Germany
;
_audit_update_record             
;
2019-05-13 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;
_audit_creation_date             2019-01-09
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL40dBr]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H14 Br Cu N3 O2'
_chemical_formula_sum            'C13 H14 Br Cu N3 O2'
_chemical_formula_weight         387.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5494(2)
_cell_length_b                   8.2358(3)
_cell_length_c                   12.3671(4)
_cell_angle_alpha                107.000(3)
_cell_angle_beta                 96.398(3)
_cell_angle_gamma                102.191(3)
_cell_volume                     706.30(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    10057
_cell_measurement_theta_min      1.8
_cell_measurement_theta_max      28.5

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_F_000             386
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.085
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.032
_exptl_absorpt_coefficient_mu    4.378
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            10623
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.752
_diffrn_reflns_theta_max         28.458
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3406
_reflns_number_gt                2770
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON

_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     
'w=1/[σ²(Fo²)+(0.0340P)²+0.2645P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3406
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0659
_refine_ls_wR_factor_gt          0.0623
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8754(3) 0.1274(3) 0.3349(2) 0.0217(5) Uani 1 1 d . . . . .
H1 H 0.8813 0.2492 0.3627 0.026 Uiso 1 1 calc R U . . .
C2 C 0.9284(3) 0.0616(3) 0.2306(2) 0.0217(5) Uani 1 1 d . . . . .
C3 C 0.9271(3) -0.1148(3) 0.1951(2) 0.0237(5) Uani 1 1 d . . . . .
H3 H 0.9677 -0.1639 0.1257 0.028 Uiso 1 1 calc R U . . .
C4 C 0.8674(3) -0.2199(3) 0.2599(2) 0.0234(5) Uani 1 1 d . . . . .
H4 H 0.8670 -0.3407 0.2356 0.028 Uiso 1 1 calc R U . . .
C5 C 0.8082(3) -0.1460(3) 0.3608(2) 0.0202(5) Uani 1 1 d . . . . .
C6 C 0.7245(4) -0.2552(3) 0.4290(2) 0.0217(5) Uani 1 1 d . . . . .
H6A H 0.6085 -0.3401 0.3826 0.026 Uiso 1 1 calc R U . . .
H6B H 0.8104 -0.3223 0.4487 0.026 Uiso 1 1 calc R U . . .
C7 C 0.6209(3) -0.2164(3) 0.6061(2) 0.0201(5) Uani 1 1 d . . . . .
H7 H 0.6016 -0.3403 0.5849 0.024 Uiso 1 1 calc R U . . .
C8 C 0.5759(3) -0.1316(3) 0.7117(2) 0.0206(5) Uani 1 1 d . . . . .
C12 C 0.5040(4) -0.2381(3) 0.7777(2) 0.0261(5) Uani 1 1 d . . . . .
C9 C 0.5926(3) 0.0520(3) 0.7506(2) 0.0208(5) Uani 1 1 d . . . . .
C10 C 0.5666(4) 0.3045(3) 0.8960(2) 0.0249(5) Uani 1 1 d . . . . .
H11A H 0.4938 0.3293 0.9579 0.030 Uiso 1 1 calc R U . . .
H11B H 0.5132 0.3401 0.8324 0.030 Uiso 1 1 calc R U . . .
C11 C 0.7636(4) 0.4112(3) 0.9414(2) 0.0297(6) Uani 1 1 d . . . . .
H12A H 0.8193 0.3713 1.0011 0.045 Uiso 1 1 calc R U . . .
H12B H 0.7664 0.5356 0.9743 0.045 Uiso 1 1 calc R U . . .
H12C H 0.8332 0.3961 0.8784 0.045 Uiso 1 1 calc R U . . .
C13 C 0.9805(4) 0.1772(4) 0.1585(2) 0.0296(6) Uani 1 1 d . . . . .
H13A H 0.8723 0.1648 0.1021 0.044 Uiso 1 1 calc R U . . .
H13B H 1.0779 0.1420 0.1182 0.044 Uiso 1 1 calc R U . . .
H13C H 1.0253 0.2999 0.2083 0.044 Uiso 1 1 calc R U . . .
N1 N 0.8156(3) 0.0269(3) 0.39911(17) 0.0192(4) Uani 1 1 d . . . . .
N2 N 0.6865(3) -0.1418(3) 0.53449(17) 0.0191(4) Uani 1 1 d . . . . .
N3 N 0.4453(4) -0.3314(3) 0.8259(2) 0.0366(6) Uani 1 1 d . . . . .
O1 O 0.6405(2) 0.1532(2) 0.69414(14) 0.0220(4) Uani 1 1 d . . . . .
O2 O 0.5529(2) 0.1165(2) 0.85421(15) 0.0241(4) Uani 1 1 d . . . . .
Cu1 Cu 0.73514(4) 0.10448(3) 0.55095(2) 0.01851(8) Uani 1 1 d . . . . .
Br1 Br 0.81228(3) 0.40897(3) 0.58026(2) 0.02365(8) 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
C1 N1 1.351(3) . ?
C1 C2 1.384(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.387(4) . ?
C2 C13 1.507(3) . ?
C3 C4 1.384(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.349(3) . ?
C5 C6 1.498(3) . ?
C6 N2 1.463(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.302(3) . ?
C7 C8 1.404(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.419(3) . ?
C8 C12 1.431(3) . ?
C12 N3 1.151(3) . ?
C9 O1 1.258(3) . ?
C9 O2 1.330(3) . ?
C10 O2 1.458(3) . ?
C10 C11 1.508(4) . ?
C10 H11A 0.9900 . ?
C10 H11B 0.9900 . ?
C11 H12A 0.9800 . ?
C11 H12B 0.9800 . ?
C11 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N1 Cu1 2.005(2) . ?
N2 Cu1 1.9280(19) . ?
O1 Cu1 1.9481(17) . ?
Cu1 Br1 2.3587(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 123.2(2) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 117.0(2) . . ?
C1 C2 C13 120.9(2) . . ?
C3 C2 C13 122.1(2) . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 118.8(2) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 121.3(2) . . ?
N1 C5 C6 116.9(2) . . ?
C4 C5 C6 121.7(2) . . ?
N2 C6 C5 109.82(19) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 126.3(2) . . ?
N2 C7 H7 116.8 . . ?
C8 C7 H7 116.8 . . ?
C7 C8 C9 122.0(2) . . ?
C7 C8 C12 117.7(2) . . ?
C9 C8 C12 120.3(2) . . ?
N3 C12 C8 176.4(3) . . ?
O1 C9 O2 119.6(2) . . ?
O1 C9 C8 124.6(2) . . ?
O2 C9 C8 115.8(2) . . ?
O2 C10 C11 111.9(2) . . ?
O2 C10 H11A 109.2 . . ?
C11 C10 H11A 109.2 . . ?
O2 C10 H11B 109.2 . . ?
C11 C10 H11B 109.2 . . ?
H11A C10 H11B 107.9 . . ?
C10 C11 H12A 109.5 . . ?
C10 C11 H12B 109.5 . . ?
H12A C11 H12B 109.5 . . ?
C10 C11 H12C 109.5 . . ?
H12A C11 H12C 109.5 . . ?
H12B C11 H12C 109.5 . . ?
C2 C13 H13A 109.5 . . ?
C2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 N1 C1 118.8(2) . . ?
C5 N1 Cu1 113.80(16) . . ?
C1 N1 Cu1 127.39(16) . . ?
C7 N2 C6 117.4(2) . . ?
C7 N2 Cu1 126.75(17) . . ?
C6 N2 Cu1 115.85(15) . . ?
C9 O1 Cu1 128.97(16) . . ?
C9 O2 C10 117.05(19) . . ?
N2 Cu1 O1 90.87(8) . . ?
N2 Cu1 N1 83.29(8) . . ?
O1 Cu1 N1 173.65(8) . . ?
N2 Cu1 Br1 176.18(6) . . ?
O1 Cu1 Br1 88.32(5) . . ?
N1 Cu1 Br1 97.66(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -3.2(4) . . . . ?
N1 C1 C2 C13 175.5(2) . . . . ?
C1 C2 C3 C4 2.7(4) . . . . ?
C13 C2 C3 C4 -175.9(2) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 N1 -3.0(4) . . . . ?
C3 C4 C5 C6 173.9(2) . . . . ?
N1 C5 C6 N2 -6.7(3) . . . . ?
C4 C5 C6 N2 176.2(2) . . . . ?
N2 C7 C8 C9 2.3(4) . . . . ?
N2 C7 C8 C12 179.6(2) . . . . ?
C7 C8 C9 O1 3.1(4) . . . . ?
C12 C8 C9 O1 -174.2(2) . . . . ?
C7 C8 C9 O2 -177.2(2) . . . . ?
C12 C8 C9 O2 5.6(3) . . . . ?
C4 C5 N1 C1 2.6(4) . . . . ?
C6 C5 N1 C1 -174.4(2) . . . . ?
C4 C5 N1 Cu1 -176.84(18) . . . . ?
C6 C5 N1 Cu1 6.1(3) . . . . ?
C2 C1 N1 C5 0.5(4) . . . . ?
C2 C1 N1 Cu1 179.96(18) . . . . ?
C8 C7 N2 C6 179.8(2) . . . . ?
C8 C7 N2 Cu1 -1.5(4) . . . . ?
C5 C6 N2 C7 -177.0(2) . . . . ?
C5 C6 N2 Cu1 4.2(3) . . . . ?
O2 C9 O1 Cu1 171.64(15) . . . . ?
C8 C9 O1 Cu1 -8.7(4) . . . . ?
O1 C9 O2 C10 0.5(3) . . . . ?
C8 C9 O2 C10 -179.3(2) . . . . ?
C11 C10 O2 C9 -78.9(3) . . . . ?

_refine_diff_density_max         0.422
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.081

####################################################################### 
# 
# 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_cl102
_database_code_depnum_ccdc_archive 'CCDC 1566629'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
?
;
_chemical_name_common            '[CuL30bBr]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H26 Br2 Cu2 N4 O4'
_chemical_formula_sum            'C24 H26 Br2 Cu2 N4 O4'
_chemical_formula_weight         721.39

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'
Br Br -0.2901 2.4595 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9933(7)
_cell_length_b                   9.2785(11)
_cell_length_c                   9.4396(10)
_cell_angle_alpha                90.031(9)
_cell_angle_beta                 98.575(7)
_cell_angle_gamma                111.440(8)
_cell_volume                     643.21(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    6173
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      28.6

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.862
_exptl_crystal_F_000             358
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.097
_exptl_absorpt_coefficient_mu    4.798
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            7822
_diffrn_reflns_av_unetI/netI     0.1159
_diffrn_reflns_av_R_equivalents  0.1611
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.186
_diffrn_reflns_theta_max         28.579
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             3021
_reflns_number_gt                2078
_reflns_threshold_expression     'I > 2σ(I)'


_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       X-AREA-STOE
_computing_cell_refinement       X-AREA-STOE
_computing_data_reduction        X-AREA-STOE
_computing_structure_solution    SIR97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  PLATON
_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     
'w=1/[σ²(Fo²)+(0.1865P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3021
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0814
_refine_ls_wR_factor_ref         0.2878
_refine_ls_wR_factor_gt          0.2254
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -1.0284(12) 0.2721(10) 0.6771(10) 0.0368(18) Uani 1 1 d . . . . .
H1 H -0.9621 0.2090 0.7110 0.044 Uiso 1 1 calc R U . . .
C2 C -0.9886(13) 0.4120(11) 0.7501(10) 0.042(2) Uani 1 1 d . . . . .
H2 H -0.9013 0.4432 0.8353 0.050 Uiso 1 1 calc R U . . .
C3 C -1.0801(13) 0.5052(10) 0.6951(10) 0.042(2) Uani 1 1 d . . . . .
H3 H -1.0531 0.6039 0.7414 0.051 Uiso 1 1 calc R U . . .
C4 C -1.2110(13) 0.4566(10) 0.5731(11) 0.0398(19) Uani 1 1 d . . . . .
H4 H -1.2746 0.5205 0.5355 0.048 Uiso 1 1 calc R U . . .
C5 C -1.2470(11) 0.3129(9) 0.5073(9) 0.0323(16) Uani 1 1 d . . . . .
C6 C -1.3787(11) 0.2534(9) 0.3733(9) 0.0344(17) Uani 1 1 d . . . . .
H6A H -1.4985 0.2554 0.3864 0.041 Uiso 1 1 calc R U . . .
H6B H -1.3358 0.3205 0.2944 0.041 Uiso 1 1 calc R U . . .
C7 C -1.5219(13) 0.0211(10) 0.2252(10) 0.041(2) Uani 1 1 d . . . . .
H7 H -1.5941 0.0750 0.1800 0.049 Uiso 1 1 calc R U . . .
C8 C -1.5575(12) -0.1315(10) 0.1672(9) 0.0375(19) Uani 1 1 d . . . . .
C9 C -1.4556(12) -0.2208(9) 0.2250(10) 0.0365(18) Uani 1 1 d . . . . .
C10 C -1.4831(13) -0.3768(11) 0.1612(11) 0.045(2) Uani 1 1 d . . . . .
H10A H -1.4403 -0.3652 0.0682 0.067 Uiso 1 1 calc R U . . .
H10B H -1.6128 -0.4422 0.1476 0.067 Uiso 1 1 calc R U . . .
H10C H -1.4141 -0.4253 0.2258 0.067 Uiso 1 1 calc R U . . .
C11 C -1.7018(12) -0.1880(10) 0.0416(10) 0.040(2) Uani 1 1 d . . . . .
C12 C -1.8313(13) -0.1030(12) 0.0003(10) 0.046(2) Uani 1 1 d . . . . .
H12A H -1.7725 -0.0133 -0.0538 0.069 Uiso 1 1 calc R U . . .
H12B H -1.8619 -0.0676 0.0873 0.069 Uiso 1 1 calc R U . . .
H12C H -1.9427 -0.1733 -0.0592 0.069 Uiso 1 1 calc R U . . .
Br1 Br -1.11740(11) -0.11525(9) 0.64537(9) 0.0354(3) Uani 1 1 d . . . . .
Cu1 Cu -1.23562(13) 0.01497(11) 0.45340(11) 0.0339(4) Uani 1 1 d . . . . .
N1 N -1.1572(10) 0.2204(8) 0.5598(8) 0.0348(15) Uani 1 1 d . . . . .
N2 N -1.3979(9) 0.0931(8) 0.3357(8) 0.0339(15) Uani 1 1 d . . . . .
O1 O -1.3323(9) -0.1755(7) 0.3352(7) 0.0432(16) Uani 1 1 d . . . . .
O2 O -1.7202(10) -0.3014(8) -0.0367(8) 0.0515(18) 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
C1 N1 1.347(11) . ?
C1 C2 1.376(12) . ?
C1 H1 0.9500 . ?
C2 C3 1.380(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(11) . ?
C4 H4 0.9500 . ?
C5 N1 1.358(11) . ?
C5 C6 1.481(11) . ?
C6 N2 1.476(10) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.313(11) . ?
C7 C8 1.430(12) . ?
C7 H7 0.9500 . ?
C8 C9 1.417(13) . ?
C8 C11 1.470(12) . ?
C9 O1 1.273(10) . ?
C9 C10 1.495(11) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O2 1.237(11) . ?
C11 C12 1.524(14) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
Br1 Cu1 2.4419(13) . ?
Cu1 N2 1.924(7) . ?
Cu1 O1 1.925(6) . ?
Cu1 N1 1.993(7) . ?

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 C1 C2 123.0(8) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C1 C2 C3 117.6(8) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C2 C3 C4 120.7(8) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 118.5(9) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
N1 C5 C4 121.4(8) . . ?
N1 C5 C6 116.0(7) . . ?
C4 C5 C6 122.5(8) . . ?
N2 C6 C5 109.9(7) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 C8 125.5(9) . . ?
N2 C7 H7 117.3 . . ?
C8 C7 H7 117.3 . . ?
C9 C8 C7 121.8(8) . . ?
C9 C8 C11 122.1(8) . . ?
C7 C8 C11 116.0(9) . . ?
O1 C9 C8 123.2(7) . . ?
O1 C9 C10 114.0(8) . . ?
C8 C9 C10 122.8(8) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 C8 122.3(9) . . ?
O2 C11 C12 117.4(8) . . ?
C8 C11 C12 120.2(8) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 Cu1 O1 90.3(3) . . ?
N2 Cu1 N1 82.7(3) . . ?
O1 Cu1 N1 172.9(3) . . ?
N2 Cu1 Br1 160.7(2) . . ?
O1 Cu1 Br1 89.8(2) . . ?
N1 Cu1 Br1 96.9(2) . . ?
C1 N1 C5 118.7(7) . . ?
C1 N1 Cu1 126.2(6) . . ?
C5 N1 Cu1 115.1(5) . . ?
C7 N2 C6 116.4(7) . . ?
C7 N2 Cu1 127.6(6) . . ?
C6 N2 Cu1 116.0(5) . . ?
C9 O1 Cu1 131.5(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -3.2(15) . . . . ?
C1 C2 C3 C4 1.9(15) . . . . ?
C2 C3 C4 C5 -0.4(15) . . . . ?
C3 C4 C5 N1 0.0(14) . . . . ?
C3 C4 C5 C6 -177.4(9) . . . . ?
N1 C5 C6 N2 6.8(11) . . . . ?
C4 C5 C6 N2 -175.7(8) . . . . ?
N2 C7 C8 C9 -1.1(16) . . . . ?
N2 C7 C8 C11 -179.2(9) . . . . ?
C7 C8 C9 O1 3.3(15) . . . . ?
C11 C8 C9 O1 -178.7(9) . . . . ?
C7 C8 C9 C10 -176.4(9) . . . . ?
C11 C8 C9 C10 1.6(14) . . . . ?
C9 C8 C11 O2 -13.8(15) . . . . ?
C7 C8 C11 O2 164.3(9) . . . . ?
C9 C8 C11 C12 168.4(9) . . . . ?
C7 C8 C11 C12 -13.5(13) . . . . ?
C2 C1 N1 C5 2.8(14) . . . . ?
C2 C1 N1 Cu1 -176.1(7) . . . . ?
C4 C5 N1 C1 -1.2(13) . . . . ?
C6 C5 N1 C1 176.4(8) . . . . ?
C4 C5 N1 Cu1 177.9(7) . . . . ?
C6 C5 N1 Cu1 -4.6(10) . . . . ?
C8 C7 N2 C6 177.3(9) . . . . ?
C8 C7 N2 Cu1 -2.0(15) . . . . ?
C5 C6 N2 C7 174.6(8) . . . . ?
C5 C6 N2 Cu1 -6.1(9) . . . . ?
C8 C9 O1 Cu1 -2.4(14) . . . . ?
C10 C9 O1 Cu1 177.4(7) . . . . ?

_refine_diff_density_max         1.413
_refine_diff_density_min         -1.940
_refine_diff_density_rms         0.280

