# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_a21020a
_database_code_depnum_ccdc_archive 'CCDC 1045806'
_audit_update_record             
;
2015-01-27 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        a21020a
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H27 Cl2 Cu N5 O3'
_chemical_formula_weight         591.97

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.671(8)
_cell_length_b                   11.025(8)
_cell_length_c                   11.868(8)
_cell_angle_alpha                89.450(9)
_cell_angle_beta                 77.812(9)
_cell_angle_gamma                79.520(9)
_cell_volume                     1341.3(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    923
_cell_measurement_theta_min      2.465
_cell_measurement_theta_max      26.137

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             610
_exptl_absorpt_coefficient_mu    1.051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8583
_exptl_absorpt_correction_T_max  0.9022
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5542
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_av_sigmaI/netI    0.0704
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4609
_reflns_number_gt                3357
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1218P)²+0.0000P] 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         4609
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1815
_refine_ls_wR_factor_gt          0.1709
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.11292(6) 0.21517(5) 0.70219(5) 0.0461(2) Uani 1 1 d . . .
Cl1 Cl 0.33279(12) 0.34404(11) 0.54183(11) 0.0538(4) Uani 1 1 d . . .
Cl2 Cl -0.09402(11) 0.11875(11) 0.80585(10) 0.0456(3) Uani 1 1 d . . .
N1 N 0.2139(4) 0.0628(3) 0.6072(3) 0.0418(9) Uani 1 1 d . . .
N2 N -0.0023(3) 0.3842(3) 0.7404(3) 0.0356(8) Uani 1 1 d . . .
N3 N 0.2040(4) 0.1983(3) 0.8311(3) 0.0411(9) Uani 1 1 d . . .
N4 N 0.0402(3) 0.2376(3) 0.5664(3) 0.0314(8) Uani 1 1 d . . .
N5 N 0.4182(4) 0.1401(4) 1.0888(3) 0.0499(10) Uani 1 1 d . . .
O1 O -0.0872(4) 0.2075(4) 0.1830(3) 0.0712(11) Uani 1 1 d . . .
C1 C 0.3104(5) -0.0236(4) 0.6337(4) 0.0523(13) Uani 1 1 d . . .
H1A H 0.3352 -0.0154 0.7034 0.063 Uiso 1 1 calc R . .
C2 C 0.3720(5) -0.1216(5) 0.5621(5) 0.0616(15) Uani 1 1 d . . .
H2A H 0.4396 -0.1777 0.5820 0.074 Uiso 1 1 calc R . .
C3 C 0.3347(5) -0.1379(5) 0.4604(4) 0.0521(12) Uani 1 1 d . . .
H3A H 0.3754 -0.2054 0.4114 0.063 Uiso 1 1 calc R . .
C4 C 0.2356(4) -0.0524(4) 0.4324(4) 0.0409(10) Uani 1 1 d . . .
H4A H 0.2071 -0.0624 0.3649 0.049 Uiso 1 1 calc R . .
C5 C 0.1787(4) 0.0491(4) 0.5062(4) 0.0344(9) Uani 1 1 d . . .
C6 C 0.0764(4) 0.1506(4) 0.4828(4) 0.0325(9) Uani 1 1 d . . .
C7 C 0.0223(4) 0.1618(4) 0.3861(4) 0.0342(9) Uani 1 1 d . . .
H7A H 0.0477 0.1008 0.3279 0.041 Uiso 1 1 calc R . .
C8 C -0.0708(4) 0.2661(4) 0.3772(4) 0.0335(9) Uani 1 1 d . . .
C9 C -0.1068(4) 0.3566(4) 0.4667(3) 0.0340(9) Uani 1 1 d . . .
H9A H -0.1688 0.4269 0.4629 0.041 Uiso 1 1 calc R . .
C10 C -0.0487(4) 0.3392(4) 0.5597(3) 0.0310(9) Uani 1 1 d . . .
C11 C -0.1270(4) 0.2850(4) 0.2764(4) 0.0415(11) Uani 1 1 d . . .
C12 C -0.2163(4) 0.3782(4) 0.2583(4) 0.0419(11) Uani 1 1 d . . .
H12A H -0.2588 0.4429 0.3100 0.050 Uiso 1 1 calc R . .
C13 C -0.2355(6) 0.3616(6) 0.1464(5) 0.0712(17) Uani 1 1 d . . .
H13A H -0.2928 0.4138 0.1104 0.085 Uiso 1 1 calc R . .
C14 C -0.1596(6) 0.2612(6) 0.1023(5) 0.0673(16) Uani 1 1 d . . .
H14A H -0.1534 0.2289 0.0288 0.081 Uiso 1 1 calc R . .
C15 C -0.0730(4) 0.4235(4) 0.6606(3) 0.0321(9) Uani 1 1 d . . .
C16 C -0.1617(4) 0.5329(4) 0.6761(4) 0.0403(10) Uani 1 1 d . . .
H16A H -0.2083 0.5597 0.6197 0.048 Uiso 1 1 calc R . .
C17 C -0.1803(5) 0.6018(4) 0.7759(4) 0.0513(12) Uani 1 1 d . . .
H17A H -0.2401 0.6756 0.7878 0.062 Uiso 1 1 calc R . .
C18 C -0.1100(5) 0.5615(5) 0.8588(4) 0.0537(13) Uani 1 1 d . . .
H18A H -0.1225 0.6061 0.9277 0.064 Uiso 1 1 calc R . .
C19 C -0.0214(5) 0.4537(4) 0.8359(4) 0.0487(12) Uani 1 1 d . . .
H19A H 0.0284 0.4274 0.8901 0.058 Uiso 1 1 calc R . .
C20 C 0.1745(4) 0.1238(4) 0.9192(4) 0.0441(11) Uani 1 1 d . . .
H20A H 0.1036 0.0850 0.9218 0.053 Uiso 1 1 calc R . .
C21 C 0.2423(4) 0.1017(4) 1.0052(4) 0.0431(11) Uani 1 1 d . . .
H21A H 0.2175 0.0482 1.0634 0.052 Uiso 1 1 calc R . .
C22 C 0.3493(4) 0.1591(4) 1.0065(4) 0.0393(10) Uani 1 1 d . . .
C23 C 0.3786(5) 0.2371(5) 0.9138(4) 0.0470(12) Uani 1 1 d . . .
H23A H 0.4481 0.2785 0.9090 0.056 Uiso 1 1 calc R . .
C24 C 0.3069(5) 0.2527(5) 0.8316(4) 0.0464(11) Uani 1 1 d . . .
H24A H 0.3303 0.3044 0.7715 0.056 Uiso 1 1 calc R . .
C25 C 0.3826(5) 0.0622(5) 1.1859(4) 0.0614(15) Uani 1 1 d . . .
H25A H 0.3110 0.0249 1.1753 0.092 Uiso 1 1 calc R . .
H25B H 0.3572 0.1114 1.2560 0.092 Uiso 1 1 calc R . .
H25C H 0.4559 -0.0012 1.1902 0.092 Uiso 1 1 calc R . .
C26 C 0.5270(5) 0.2023(6) 1.0917(5) 0.0749(18) Uani 1 1 d . . .
H26A H 0.5428 0.2506 1.0242 0.112 Uiso 1 1 calc R . .
H26B H 0.6036 0.1419 1.0935 0.112 Uiso 1 1 calc R . .
H26C H 0.5061 0.2553 1.1593 0.112 Uiso 1 1 calc R . .
O2 O 0.5531(4) 0.4527(4) 0.6372(4) 0.0941(15) Uani 1 1 d . . .
H1O2 H 0.5567 0.4659 0.7068 0.113 Uiso 1 1 d R . .
H2O2 H 0.4871 0.5015 0.6233 0.113 Uiso 1 1 d R . .
O3 O 0.6498(4) 0.3430(6) 0.8289(5) 0.122(2) Uani 1 1 d . . .
H1O3 H 0.6639 0.3915 0.8782 0.146 Uiso 1 1 d R . .
H2O3 H 0.7156 0.2848 0.8132 0.146 Uiso 1 1 d R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N4 1.926(3) . ?
Cu1 N3 1.969(4) . ?
Cu1 N1 2.030(4) . ?
Cu1 N2 2.034(4) . ?
Cu1 Cl2 2.6835(19) . ?
Cu1 Cl1 3.228(2) . ?
N1 C5 1.347(5) . ?
N1 C1 1.356(6) . ?
N2 C19 1.333(5) . ?
N2 C15 1.351(5) . ?
N3 C20 1.344(6) . ?
N3 C24 1.344(6) . ?
N4 C6 1.333(5) . ?
N4 C10 1.344(5) . ?
N5 C22 1.335(5) . ?
N5 C25 1.458(6) . ?
N5 C26 1.459(6) . ?
O1 C11 1.352(6) . ?
O1 C14 1.413(7) . ?
C1 C2 1.359(7) . ?
C1 H1A 0.9300 . ?
C2 C3 1.371(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.377(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.391(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.482(6) . ?
C6 C7 1.385(6) . ?
C7 C8 1.395(6) . ?
C7 H7A 0.9300 . ?
C8 C9 1.408(6) . ?
C8 C11 1.445(6) . ?
C9 C10 1.371(5) . ?
C9 H9A 0.9300 . ?
C10 C15 1.472(6) . ?
C11 C12 1.318(6) . ?
C12 C13 1.404(7) . ?
C12 H12A 0.9300 . ?
C13 C14 1.289(8) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 C16 1.379(6) . ?
C16 C17 1.372(6) . ?
C16 H16A 0.9300 . ?
C17 C18 1.382(7) . ?
C17 H17A 0.9300 . ?
C18 C19 1.367(7) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C20 C21 1.367(6) . ?
C20 H20A 0.9300 . ?
C21 C22 1.405(6) . ?
C21 H21A 0.9300 . ?
C22 C23 1.408(6) . ?
C23 C24 1.353(6) . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
O2 H1O2 0.8500 . ?
O2 H2O2 0.8500 . ?
O3 H1O3 0.8499 . ?
O3 H2O3 0.8501 . ?

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
N4 Cu1 N3 173.77(15) . . ?
N4 Cu1 N1 79.80(14) . . ?
N3 Cu1 N1 98.69(15) . . ?
N4 Cu1 N2 79.97(14) . . ?
N3 Cu1 N2 100.87(14) . . ?
N1 Cu1 N2 159.12(15) . . ?
N4 Cu1 Cl2 89.03(11) . . ?
N3 Cu1 Cl2 97.17(13) . . ?
N1 Cu1 Cl2 97.57(12) . . ?
N2 Cu1 Cl2 87.18(11) . . ?
N4 Cu1 Cl1 80.84(11) . . ?
N3 Cu1 Cl1 92.98(13) . . ?
N1 Cu1 Cl1 82.34(12) . . ?
N2 Cu1 Cl1 89.41(11) . . ?
Cl2 Cu1 Cl1 169.73(4) . . ?
C5 N1 C1 118.1(4) . . ?
C5 N1 Cu1 114.2(3) . . ?
C1 N1 Cu1 127.7(3) . . ?
C19 N2 C15 118.1(4) . . ?
C19 N2 Cu1 127.8(3) . . ?
C15 N2 Cu1 113.9(3) . . ?
C20 N3 C24 115.6(4) . . ?
C20 N3 Cu1 122.2(3) . . ?
C24 N3 Cu1 121.9(3) . . ?
C6 N4 C10 121.5(3) . . ?
C6 N4 Cu1 119.4(3) . . ?
C10 N4 Cu1 119.1(3) . . ?
C22 N5 C25 121.5(4) . . ?
C22 N5 C26 122.4(4) . . ?
C25 N5 C26 116.0(4) . . ?
C11 O1 C14 104.9(4) . . ?
N1 C1 C2 122.3(5) . . ?
N1 C1 H1A 118.8 . . ?
C2 C1 H1A 118.8 . . ?
C1 C2 C3 120.0(5) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C2 C3 C4 118.7(5) . . ?
C2 C3 H3A 120.7 . . ?
C4 C3 H3A 120.7 . . ?
C3 C4 C5 119.3(4) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 H4A 120.3 . . ?
N1 C5 C4 121.5(4) . . ?
N1 C5 C6 114.0(4) . . ?
C4 C5 C6 124.5(4) . . ?
N4 C6 C7 120.8(4) . . ?
N4 C6 C5 112.4(4) . . ?
C7 C6 C5 126.8(4) . . ?
C6 C7 C8 118.9(4) . . ?
C6 C7 H7A 120.5 . . ?
C8 C7 H7A 120.5 . . ?
C7 C8 C9 119.1(4) . . ?
C7 C8 C11 121.4(4) . . ?
C9 C8 C11 119.5(4) . . ?
C10 C9 C8 118.7(4) . . ?
C10 C9 H9A 120.6 . . ?
C8 C9 H9A 120.6 . . ?
N4 C10 C9 121.0(4) . . ?
N4 C10 C15 112.4(3) . . ?
C9 C10 C15 126.5(4) . . ?
C12 C11 O1 110.4(4) . . ?
C12 C11 C8 127.2(4) . . ?
O1 C11 C8 122.3(4) . . ?
C11 C12 C13 107.3(4) . . ?
C11 C12 H12A 126.3 . . ?
C13 C12 H12A 126.3 . . ?
C14 C13 C12 107.8(5) . . ?
C14 C13 H13A 126.1 . . ?
C12 C13 H13A 126.1 . . ?
C13 C14 O1 109.5(5) . . ?
C13 C14 H14A 125.2 . . ?
O1 C14 H14A 125.2 . . ?
N2 C15 C16 121.5(4) . . ?
N2 C15 C10 114.5(3) . . ?
C16 C15 C10 124.0(4) . . ?
C17 C16 C15 119.0(4) . . ?
C17 C16 H16A 120.5 . . ?
C15 C16 H16A 120.5 . . ?
C16 C17 C18 120.0(4) . . ?
C16 C17 H17A 120.0 . . ?
C18 C17 H17A 120.0 . . ?
C19 C18 C17 117.6(4) . . ?
C19 C18 H18A 121.2 . . ?
C17 C18 H18A 121.2 . . ?
N2 C19 C18 123.8(4) . . ?
N2 C19 H19A 118.1 . . ?
C18 C19 H19A 118.1 . . ?
N3 C20 C21 124.0(4) . . ?
N3 C20 H20A 118.0 . . ?
C21 C20 H20A 118.0 . . ?
C20 C21 C22 120.4(4) . . ?
C20 C21 H21A 119.8 . . ?
C22 C21 H21A 119.8 . . ?
N5 C22 C21 122.4(4) . . ?
N5 C22 C23 122.8(4) . . ?
C21 C22 C23 114.8(4) . . ?
C24 C23 C22 120.7(4) . . ?
C24 C23 H23A 119.6 . . ?
C22 C23 H23A 119.6 . . ?
N3 C24 C23 124.3(4) . . ?
N3 C24 H24A 117.8 . . ?
C23 C24 H24A 117.8 . . ?
N5 C25 H25A 109.5 . . ?
N5 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N5 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N5 C26 H26A 109.5 . . ?
N5 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N5 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
H1O2 O2 H2O2 107.7 . . ?
H1O3 O3 H2O3 107.7 . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         1.330
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.110

_exptl_crystal_recrystallization_method 'Vapour Deposition'
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_a30701b
_database_code_depnum_ccdc_archive 'CCDC 1045807'
_audit_update_record             
;
2015-01-27 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        a30701b
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H13 Cl Cu F3 N3 O4 S'
_chemical_formula_weight         547.38

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   7.590(3)
_cell_length_b                   20.098(7)
_cell_length_c                   13.487(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.218(4)
_cell_angle_gamma                90
_cell_volume                     2051.9(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    839
_cell_measurement_theta_min      2.530
_cell_measurement_theta_max      24.558

_exptl_crystal_description       'dark blue'
_exptl_crystal_colour            block
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_F_000             1100
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.359
_shelx_estimated_absorpt_T_min   0.728
_shelx_estimated_absorpt_T_max   0.773
_exptl_absorpt_correction_type   multi=scan
_exptl_absorpt_correction_T_min  0.199
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9055
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.822
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3971
_reflns_number_gt                2815
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.0507P)²] 
 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         3971
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0935
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_restrained_S_all      0.914
_refine_ls_shift/su_max          0.006
_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
Cu1 Cu 1.05547(5) 0.53814(2) 0.38097(2) 0.03897(13) Uani 1 1 d . . . . .
Cl1 Cl 1.25943(12) 0.56074(4) 0.50039(6) 0.0537(2) Uani 1 1 d . . . . .
N1 N 1.1544(3) 0.45229(11) 0.33042(17) 0.0381(6) Uani 1 1 d . . . . .
N2 N 0.8584(3) 0.50935(11) 0.29349(16) 0.0343(5) Uani 1 1 d . . . . .
N3 N 0.8809(3) 0.61087(11) 0.40577(16) 0.0371(6) Uani 1 1 d . . . . .
S1 S 0.88156(11) 0.17792(4) 0.27632(6) 0.0459(2) Uani 1 1 d . . . . .
O1 O 0.4503(3) 0.39618(10) 0.04129(16) 0.0513(6) Uani 1 1 d . . . . .
O2 O 0.8348(3) 0.10881(10) 0.26321(17) 0.0554(6) Uani 1 1 d . . . . .
O3 O 0.8116(4) 0.22050(12) 0.19692(17) 0.0690(7) Uani 1 1 d . . . . .
O4 O 1.0614(3) 0.19001(11) 0.31164(17) 0.0592(6) Uani 1 1 d . . . . .
F1 F 0.7722(3) 0.26837(13) 0.3951(2) 0.1090(10) Uani 1 1 d . . . . .
F2 F 0.5839(3) 0.19242(14) 0.36001(19) 0.0969(8) Uani 1 1 d . . . . .
F3 F 0.8101(4) 0.17065(15) 0.46154(17) 0.1185(10) Uani 1 1 d . . . . .
C1 C 1.3132(4) 0.42613(15) 0.3560(2) 0.0436(7) Uani 1 1 d . . . . .
H1 H 1.3912 0.4498 0.3993 0.052 Uiso 1 1 calc R U . . .
C2 C 1.3657(5) 0.36557(16) 0.3208(2) 0.0524(9) Uani 1 1 d . . . . .
H2 H 1.4777 0.3489 0.3391 0.063 Uiso 1 1 calc R U . . .
C3 C 1.2495(5) 0.33010(15) 0.2578(2) 0.0518(8) Uani 1 1 d . . . . .
H3 H 1.2814 0.2888 0.2340 0.062 Uiso 1 1 calc R U . . .
C4 C 1.0855(4) 0.35637(15) 0.2305(2) 0.0467(8) Uani 1 1 d . . . . .
H4 H 1.0056 0.3328 0.1883 0.056 Uiso 1 1 calc R U . . .
C5 C 1.0408(4) 0.41805(13) 0.2665(2) 0.0371(7) Uani 1 1 d . . . . .
C6 C 0.8711(4) 0.45244(13) 0.2424(2) 0.0372(7) Uani 1 1 d . . . . .
C7 C 0.7312(4) 0.43125(14) 0.1786(2) 0.0408(7) Uani 1 1 d . . . . .
H7 H 0.7396 0.3919 0.1431 0.049 Uiso 1 1 calc R U . . .
C8 C 0.5776(4) 0.46937(14) 0.1680(2) 0.0387(7) Uani 1 1 d . . . . .
C9 C 0.5661(4) 0.52688(14) 0.2263(2) 0.0387(7) Uani 1 1 d . . . . .
H9 H 0.4629 0.5519 0.2231 0.046 Uiso 1 1 calc R U . . .
C10 C 0.7094(4) 0.54560(13) 0.28818(19) 0.0351(6) Uani 1 1 d . . . . .
C11 C 0.7217(4) 0.60396(13) 0.3550(2) 0.0355(7) Uani 1 1 d . . . . .
C12 C 0.5857(4) 0.64788(15) 0.3669(2) 0.0440(7) Uani 1 1 d . . . . .
H12 H 0.4756 0.6414 0.3334 0.053 Uiso 1 1 calc R U . . .
C13 C 0.6153(5) 0.70200(15) 0.4298(2) 0.0518(8) Uani 1 1 d . . . . .
H13 H 0.5258 0.7325 0.4389 0.062 Uiso 1 1 calc R U . . .
C14 C 0.7805(5) 0.70963(16) 0.4785(2) 0.0540(9) Uani 1 1 d . . . . .
H14 H 0.8043 0.7461 0.5199 0.065 Uiso 1 1 calc R U . . .
C15 C 0.9094(5) 0.66327(15) 0.4657(2) 0.0467(8) Uani 1 1 d . . . . .
H15 H 1.0196 0.6685 0.4997 0.056 Uiso 1 1 calc R U . . .
C16 C 0.4295(4) 0.45135(14) 0.0995(2) 0.0410(7) Uani 1 1 d . . . . .
C17 C 0.2697(4) 0.47830(16) 0.0772(2) 0.0489(8) Uani 1 1 d . . . . .
H17 H 0.2235 0.5159 0.1061 0.059 Uiso 1 1 calc R U . . .
C18 C 0.1848(5) 0.43843(17) 0.0012(2) 0.0545(9) Uani 1 1 d . . . . .
H18 H 0.0724 0.4448 -0.0295 0.065 Uiso 1 1 calc R U . . .
C19 C 0.2968(5) 0.39056(17) -0.0173(2) 0.0534(9) Uani 1 1 d . . . . .
H19 H 0.2740 0.3572 -0.0643 0.064 Uiso 1 1 calc R U . . .
C23 C 0.7555(5) 0.2030(2) 0.3790(3) 0.0693(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
Cu1 N2 1.925(2) . ?
Cu1 N3 2.017(2) . ?
Cu1 N1 2.020(2) . ?
Cu1 Cl1 2.1979(10) . ?
N1 C1 1.337(4) . ?
N1 C5 1.360(4) . ?
N2 C6 1.342(3) . ?
N2 C10 1.343(4) . ?
N3 C15 1.336(3) . ?
N3 C11 1.351(4) . ?
S1 O4 1.433(2) . ?
S1 O3 1.441(2) . ?
S1 O2 1.441(2) . ?
S1 C23 1.812(4) . ?
O1 C19 1.363(4) . ?
O1 C16 1.374(3) . ?
F1 C23 1.337(4) . ?
F2 C23 1.326(4) . ?
F3 C23 1.328(5) . ?
C1 C2 1.376(4) . ?
C2 C3 1.378(5) . ?
C3 C4 1.376(4) . ?
C4 C5 1.383(4) . ?
C5 C6 1.477(4) . ?
C6 C7 1.384(4) . ?
C7 C8 1.393(4) . ?
C8 C9 1.405(4) . ?
C8 C16 1.448(4) . ?
C9 C10 1.374(4) . ?
C10 C11 1.478(4) . ?
C11 C12 1.377(4) . ?
C12 C13 1.387(4) . ?
C13 C14 1.381(5) . ?
C14 C15 1.371(4) . ?
C16 C17 1.342(4) . ?
C17 C18 1.418(4) . ?
C18 C19 1.320(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
N2 Cu1 N3 80.17(10) . . ?
N2 Cu1 N1 80.07(10) . . ?
N3 Cu1 N1 160.02(10) . . ?
N2 Cu1 Cl1 170.11(7) . . ?
N3 Cu1 Cl1 99.47(7) . . ?
N1 Cu1 Cl1 99.48(7) . . ?
C1 N1 C5 118.8(3) . . ?
C1 N1 Cu1 126.8(2) . . ?
C5 N1 Cu1 114.3(2) . . ?
C6 N2 C10 121.8(2) . . ?
C6 N2 Cu1 119.27(19) . . ?
C10 N2 Cu1 118.89(19) . . ?
C15 N3 C11 119.1(3) . . ?
C15 N3 Cu1 126.4(2) . . ?
C11 N3 Cu1 114.53(18) . . ?
O4 S1 O3 115.87(15) . . ?
O4 S1 O2 115.08(14) . . ?
O3 S1 O2 114.03(14) . . ?
O4 S1 C23 104.02(16) . . ?
O3 S1 C23 102.51(19) . . ?
O2 S1 C23 102.86(17) . . ?
C19 O1 C16 105.6(2) . . ?
N1 C1 C2 122.5(3) . . ?
C3 C2 C1 118.8(3) . . ?
C4 C3 C2 119.5(3) . . ?
C3 C4 C5 119.4(3) . . ?
N1 C5 C4 121.0(3) . . ?
N1 C5 C6 113.8(2) . . ?
C4 C5 C6 125.1(3) . . ?
N2 C6 C7 120.0(3) . . ?
N2 C6 C5 112.4(2) . . ?
C7 C6 C5 127.6(3) . . ?
C6 C7 C8 119.5(3) . . ?
C7 C8 C9 118.7(3) . . ?
C7 C8 C16 122.2(3) . . ?
C9 C8 C16 119.1(3) . . ?
C10 C9 C8 119.1(3) . . ?
N2 C10 C9 120.7(3) . . ?
N2 C10 C11 112.5(2) . . ?
C9 C10 C11 126.8(3) . . ?
N3 C11 C12 121.7(3) . . ?
N3 C11 C10 113.9(2) . . ?
C12 C11 C10 124.5(3) . . ?
C11 C12 C13 119.0(3) . . ?
C14 C13 C12 118.6(3) . . ?
C15 C14 C13 119.7(3) . . ?
N3 C15 C14 121.8(3) . . ?
C17 C16 O1 109.7(3) . . ?
C17 C16 C8 133.5(3) . . ?
O1 C16 C8 116.8(3) . . ?
C16 C17 C18 106.8(3) . . ?
C19 C18 C17 106.5(3) . . ?
C18 C19 O1 111.4(3) . . ?
F2 C23 F3 109.0(4) . . ?
F2 C23 F1 105.6(3) . . ?
F3 C23 F1 109.0(3) . . ?
F2 C23 S1 112.0(3) . . ?
F3 C23 S1 110.8(3) . . ?
F1 C23 S1 110.4(3) . . ?

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
C5 N1 C1 C2 -0.5(4) . . . . ?
Cu1 N1 C1 C2 176.9(2) . . . . ?
N1 C1 C2 C3 -0.9(5) . . . . ?
C1 C2 C3 C4 1.0(5) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C1 N1 C5 C4 1.9(4) . . . . ?
Cu1 N1 C5 C4 -175.9(2) . . . . ?
C1 N1 C5 C6 -179.0(2) . . . . ?
Cu1 N1 C5 C6 3.3(3) . . . . ?
C3 C4 C5 N1 -1.8(4) . . . . ?
C3 C4 C5 C6 179.2(3) . . . . ?
C10 N2 C6 C7 3.1(4) . . . . ?
Cu1 N2 C6 C7 -179.5(2) . . . . ?
C10 N2 C6 C5 -174.8(2) . . . . ?
Cu1 N2 C6 C5 2.6(3) . . . . ?
N1 C5 C6 N2 -3.7(4) . . . . ?
C4 C5 C6 N2 175.4(3) . . . . ?
N1 C5 C6 C7 178.5(3) . . . . ?
C4 C5 C6 C7 -2.4(5) . . . . ?
N2 C6 C7 C8 -0.1(4) . . . . ?
C5 C6 C7 C8 177.5(3) . . . . ?
C6 C7 C8 C9 -3.1(4) . . . . ?
C6 C7 C8 C16 177.4(3) . . . . ?
C7 C8 C9 C10 3.3(4) . . . . ?
C16 C8 C9 C10 -177.2(3) . . . . ?
C6 N2 C10 C9 -2.8(4) . . . . ?
Cu1 N2 C10 C9 179.73(19) . . . . ?
C6 N2 C10 C11 176.5(2) . . . . ?
Cu1 N2 C10 C11 -0.9(3) . . . . ?
C8 C9 C10 N2 -0.4(4) . . . . ?
C8 C9 C10 C11 -179.7(3) . . . . ?
C15 N3 C11 C12 -3.0(4) . . . . ?
Cu1 N3 C11 C12 177.2(2) . . . . ?
C15 N3 C11 C10 177.6(2) . . . . ?
Cu1 N3 C11 C10 -2.2(3) . . . . ?
N2 C10 C11 N3 2.0(3) . . . . ?
C9 C10 C11 N3 -178.6(3) . . . . ?
N2 C10 C11 C12 -177.4(3) . . . . ?
C9 C10 C11 C12 1.9(5) . . . . ?
N3 C11 C12 C13 2.5(4) . . . . ?
C10 C11 C12 C13 -178.1(3) . . . . ?
C11 C12 C13 C14 -0.3(5) . . . . ?
C12 C13 C14 C15 -1.4(5) . . . . ?
C11 N3 C15 C14 1.2(4) . . . . ?
Cu1 N3 C15 C14 -179.1(2) . . . . ?
C13 C14 C15 N3 1.0(5) . . . . ?
C19 O1 C16 C17 0.0(3) . . . . ?
C19 O1 C16 C8 -178.8(3) . . . . ?
C7 C8 C16 C17 178.6(3) . . . . ?
C9 C8 C16 C17 -0.9(5) . . . . ?
C7 C8 C16 O1 -3.0(4) . . . . ?
C9 C8 C16 O1 177.5(2) . . . . ?
O1 C16 C17 C18 -0.1(4) . . . . ?
C8 C16 C17 C18 178.4(3) . . . . ?
C16 C17 C18 C19 0.1(4) . . . . ?
C17 C18 C19 O1 -0.1(4) . . . . ?
C16 O1 C19 C18 0.1(4) . . . . ?
O4 S1 C23 F2 -177.5(3) . . . . ?
O3 S1 C23 F2 61.4(3) . . . . ?
O2 S1 C23 F2 -57.2(3) . . . . ?
O4 S1 C23 F3 -55.6(3) . . . . ?
O3 S1 C23 F3 -176.7(3) . . . . ?
O2 S1 C23 F3 64.7(3) . . . . ?
O4 S1 C23 F1 65.2(3) . . . . ?
O3 S1 C23 F1 -55.9(3) . . . . ?
O2 S1 C23 F1 -174.5(3) . . . . ?

_refine_diff_density_max         0.503
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.073

_shelxl_version_number           2013-2


_exptl_crystal_recrystallization_method 'Vapour Deposition'
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_a40401a
_database_code_depnum_ccdc_archive 'CCDC 1045808'
_audit_update_record             
;
2015-01-27 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        a40401a
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H29 Cl2 Cu N5 O2'
_chemical_formula_weight         602.00

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

_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                   10.758(4)
_cell_length_b                   10.951(4)
_cell_length_c                   12.045(5)
_cell_angle_alpha                87.424(5)
_cell_angle_beta                 78.339(5)
_cell_angle_gamma                79.489(5)
_cell_volume                     1366.4(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    975
_cell_measurement_theta_min      2.776
_cell_measurement_theta_max      26.562

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_F_000             622
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.030
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.365
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5731
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.726
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.951
_reflns_number_total             4698
_reflns_number_gt                3445
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.1483P)²] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4698
_refine_ls_number_parameters     361
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.2032
_refine_ls_wR_factor_gt          0.1876
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.007
_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
Cu1 Cu 0.88397(6) 0.78821(5) 0.80204(5) 0.0420(3) Uani 1 1 d . . . . .
Cl1 Cl 1.08280(12) 0.89270(11) 0.70502(10) 0.0424(3) Uani 1 1 d . . . . .
Cl2 Cl 0.33761(13) 0.34080(12) 0.03809(12) 0.0517(4) Uani 1 1 d D . . . .
N1 N 0.9982(4) 0.6211(4) 0.7648(3) 0.0346(9) Uani 1 1 d . . . . .
N2 N 0.9582(3) 0.7599(3) 0.9349(3) 0.0282(8) Uani 1 1 d . . . . .
N3 N 0.7835(4) 0.9362(4) 0.8961(3) 0.0376(9) Uani 1 1 d . . . . .
N4 N 0.7926(4) 0.8099(4) 0.6753(3) 0.0391(9) Uani 1 1 d . . . . .
N5 N 0.5899(4) 0.8598(5) 0.4133(4) 0.0533(12) Uani 1 1 d . . . . .
C1 C 1.0175(5) 0.5550(5) 0.6696(4) 0.0457(13) Uani 1 1 d . . . . .
H1 H 0.9677 0.5827 0.6156 0.055 Uiso 1 1 calc R U . . .
C2 C 1.1075(5) 0.4484(5) 0.6488(4) 0.0499(13) Uani 1 1 d . . . . .
H2 H 1.1188 0.4047 0.5820 0.060 Uiso 1 1 calc R U . . .
C3 C 1.1791(5) 0.4083(5) 0.7272(5) 0.0462(13) Uani 1 1 d . . . . .
H3 H 1.2413 0.3367 0.7137 0.055 Uiso 1 1 calc R U . . .
C4 C 1.1617(5) 0.4715(5) 0.8273(4) 0.0392(11) Uani 1 1 d . . . . .
H4 H 1.2093 0.4426 0.8825 0.047 Uiso 1 1 calc R U . . .
C5 C 1.0717(4) 0.5785(4) 0.8420(4) 0.0304(10) Uani 1 1 d . . . . .
C6 C 1.0470(4) 0.6612(4) 0.9415(4) 0.0304(10) Uani 1 1 d . . . . .
C7 C 1.1065(4) 0.6418(4) 1.0330(4) 0.0327(10) Uani 1 1 d . . . . .
H7 H 1.1675 0.5706 1.0375 0.039 Uiso 1 1 calc R U . . .
C8 C 1.0748(4) 0.7298(4) 1.1193(4) 0.0323(10) Uani 1 1 d . . . . .
C9 C 0.9819(4) 0.8343(4) 1.1087(4) 0.0321(10) Uani 1 1 d . . . . .
H9 H 0.9593 0.8952 1.1641 0.039 Uiso 1 1 calc R U . . .
C10 C 0.9239(4) 0.8469(4) 1.0163(4) 0.0302(10) Uani 1 1 d . . . . .
C11 C 0.8222(4) 0.9485(4) 0.9931(4) 0.0316(10) Uani 1 1 d . . . . .
C12 C 0.7670(5) 1.0451(4) 1.0656(4) 0.0398(11) Uani 1 1 d . . . . .
H12 H 0.7973 1.0535 1.1315 0.048 Uiso 1 1 calc R U . . .
C13 C 0.6651(5) 1.1300(5) 1.0385(5) 0.0495(13) Uani 1 1 d . . . . .
H13 H 0.6243 1.1951 1.0872 0.059 Uiso 1 1 calc R U . . .
C14 C 0.6251(6) 1.1174(5) 0.9398(5) 0.0550(15) Uani 1 1 d . . . . .
H14 H 0.5573 1.1741 0.9201 0.066 Uiso 1 1 calc R U . . .
C15 C 0.6863(5) 1.0203(5) 0.8703(5) 0.0485(13) Uani 1 1 d . . . . .
H15 H 0.6594 1.0123 0.8027 0.058 Uiso 1 1 calc R U . . .
C16 C 1.1344(4) 0.7090(4) 1.2206(4) 0.0336(10) Uani 1 1 d . . . . .
C17 C 1.0821(6) 0.7776(5) 1.3180(4) 0.0509(14) Uani 1 1 d . . . . .
H17 H 1.0123 0.8418 1.3184 0.061 Uiso 1 1 calc R U . . .
C18 C 1.1331(6) 0.7512(6) 1.4152(4) 0.0570(15) Uani 1 1 d . . . . .
H18 H 1.0957 0.7967 1.4806 0.068 Uiso 1 1 calc R U . . .
C19 C 1.2371(5) 0.6597(5) 1.4160(5) 0.0503(14) Uani 1 1 d . . . . .
H19 H 1.2697 0.6413 1.4819 0.060 Uiso 1 1 calc R U . . .
C20 C 1.2931(6) 0.5951(5) 1.3189(5) 0.0586(15) Uani 1 1 d . . . . .
H20 H 1.3661 0.5344 1.3181 0.070 Uiso 1 1 calc R U . . .
C21 C 1.2428(5) 0.6186(5) 1.2224(5) 0.0508(14) Uani 1 1 d . . . . .
H21 H 1.2820 0.5733 1.1572 0.061 Uiso 1 1 calc R U . . .
C22 C 0.8191(5) 0.8884(5) 0.5904(4) 0.0433(12) Uani 1 1 d . . . . .
H22 H 0.8853 0.9323 0.5909 0.052 Uiso 1 1 calc R U . . .
C23 C 0.7553(5) 0.9089(5) 0.5023(4) 0.0406(11) Uani 1 1 d . . . . .
H23 H 0.7777 0.9658 0.4455 0.049 Uiso 1 1 calc R U . . .
C24 C 0.6559(5) 0.8435(5) 0.4982(4) 0.0405(12) Uani 1 1 d . . . . .
C25 C 0.6279(5) 0.7628(5) 0.5881(4) 0.0502(14) Uani 1 1 d . . . . .
H25 H 0.5613 0.7186 0.5910 0.060 Uiso 1 1 calc R U . . .
C26 C 0.6969(5) 0.7478(5) 0.6718(4) 0.0477(13) Uani 1 1 d . . . . .
H26 H 0.6769 0.6914 0.7298 0.057 Uiso 1 1 calc R U . . .
C27 C 0.4855(6) 0.7962(7) 0.4107(6) 0.0686(18) Uani 1 1 d . . . . .
H27A H 0.5132 0.7086 0.4202 0.103 Uiso 1 1 calc R U . . .
H27B H 0.4587 0.8116 0.3392 0.103 Uiso 1 1 calc R U . . .
H27C H 0.4145 0.8257 0.4710 0.103 Uiso 1 1 calc R U . . .
C28 C 0.6225(6) 0.9402(6) 0.3189(5) 0.0615(16) Uani 1 1 d . . . . .
H28A H 0.5758 1.0228 0.3357 0.092 Uiso 1 1 calc R U . . .
H28B H 0.6002 0.9106 0.2530 0.092 Uiso 1 1 calc R U . . .
H28C H 0.7135 0.9410 0.3047 0.092 Uiso 1 1 calc R U . . .
O1 O 0.5640(5) 0.4382(5) 0.1290(4) 0.0710(12) Uani 1 1 d D . . . .
H1A H 0.499(5) 0.418(6) 0.107(6) 0.09(3) Uiso 1 1 d D . . . .
H1B H 0.576(6) 0.508(5) 0.080(5) 0.08(2) Uiso 1 1 d D . . . .
O2 O 0.3449(5) 0.6783(6) 0.6766(5) 0.0906(17) Uani 1 1 d D . . . .
H2A H 0.266(4) 0.697(7) 0.699(6) 0.10(3) Uiso 1 1 d D . . . .
H2B H 0.378(7) 0.688(10) 0.735(6) 0.14(4) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.917(4) . ?
Cu1 N4 1.959(4) . ?
Cu1 N1 2.022(4) . ?
Cu1 N3 2.027(4) . ?
Cu1 Cl1 2.6482(15) . ?
N1 C1 1.343(6) . ?
N1 C5 1.354(6) . ?
N2 C6 1.316(6) . ?
N2 C10 1.347(5) . ?
N3 C11 1.338(6) . ?
N3 C15 1.339(6) . ?
N4 C22 1.326(6) . ?
N4 C26 1.343(7) . ?
N5 C24 1.347(6) . ?
N5 C27 1.432(7) . ?
N5 C28 1.432(7) . ?
C1 C2 1.371(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.345(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.486(6) . ?
C6 C7 1.373(6) . ?
C7 C8 1.398(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.395(6) . ?
C8 C16 1.480(6) . ?
C9 C10 1.372(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.471(6) . ?
C11 C12 1.371(6) . ?
C12 C13 1.385(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.365(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.366(7) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.384(6) . ?
C16 C21 1.389(7) . ?
C17 C18 1.388(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.361(8) . ?
C18 H18 0.9300 . ?
C19 C20 1.365(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.374(7) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.366(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.402(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.386(7) . ?
C25 C26 1.355(7) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
O1 H1A 0.86(4) . ?
O1 H1B 0.96(4) . ?
O2 H2A 0.82(4) . ?
O2 H2B 0.87(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N4 173.98(16) . . ?
N2 Cu1 N1 79.68(15) . . ?
N4 Cu1 N1 100.85(16) . . ?
N2 Cu1 N3 79.96(15) . . ?
N4 Cu1 N3 98.82(16) . . ?
N1 Cu1 N3 158.89(16) . . ?
N2 Cu1 Cl1 88.51(11) . . ?
N4 Cu1 Cl1 97.50(13) . . ?
N1 Cu1 Cl1 87.95(12) . . ?
N3 Cu1 Cl1 97.03(12) . . ?
C1 N1 C5 117.4(4) . . ?
C1 N1 Cu1 127.9(4) . . ?
C5 N1 Cu1 114.4(3) . . ?
C6 N2 C10 121.5(4) . . ?
C6 N2 Cu1 119.9(3) . . ?
C10 N2 Cu1 118.5(3) . . ?
C11 N3 C15 118.6(4) . . ?
C11 N3 Cu1 114.4(3) . . ?
C15 N3 Cu1 127.0(3) . . ?
C22 N4 C26 116.4(4) . . ?
C22 N4 Cu1 122.3(3) . . ?
C26 N4 Cu1 121.3(3) . . ?
C24 N5 C27 122.1(5) . . ?
C24 N5 C28 121.6(5) . . ?
C27 N5 C28 116.2(5) . . ?
N1 C1 C2 122.7(5) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C1 118.6(5) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 121.1(5) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 117.4(5) . . ?
C5 C4 H4 121.3 . . ?
C3 C4 H4 121.3 . . ?
N1 C5 C4 122.8(4) . . ?
N1 C5 C6 113.1(4) . . ?
C4 C5 C6 124.1(4) . . ?
N2 C6 C7 121.2(4) . . ?
N2 C6 C5 112.7(4) . . ?
C7 C6 C5 126.1(4) . . ?
C6 C7 C8 119.5(4) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C9 C8 C7 117.8(4) . . ?
C9 C8 C16 121.6(4) . . ?
C7 C8 C16 120.5(4) . . ?
C10 C9 C8 119.8(4) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
N2 C10 C9 120.2(4) . . ?
N2 C10 C11 112.8(4) . . ?
C9 C10 C11 127.1(4) . . ?
N3 C11 C12 122.2(4) . . ?
N3 C11 C10 114.0(4) . . ?
C12 C11 C10 123.8(4) . . ?
C11 C12 C13 118.4(5) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C14 C13 C12 119.6(5) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 118.9(5) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
N3 C15 C14 122.4(5) . . ?
N3 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C17 C16 C21 117.6(4) . . ?
C17 C16 C8 121.0(4) . . ?
C21 C16 C8 121.4(4) . . ?
C16 C17 C18 120.5(5) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 120.8(5) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 119.2(5) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C19 C20 C21 120.8(5) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C20 C21 C16 121.0(5) . . ?
C20 C21 H21 119.5 . . ?
C16 C21 H21 119.5 . . ?
N4 C22 C23 124.1(5) . . ?
N4 C22 H22 117.9 . . ?
C23 C22 H22 117.9 . . ?
C22 C23 C24 119.5(5) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
N5 C24 C25 122.1(5) . . ?
N5 C24 C23 122.0(5) . . ?
C25 C24 C23 115.9(4) . . ?
C26 C25 C24 120.6(5) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
N4 C26 C25 123.5(5) . . ?
N4 C26 H26 118.3 . . ?
C25 C26 H26 118.3 . . ?
N5 C27 H27A 109.5 . . ?
N5 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N5 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N5 C28 H28A 109.5 . . ?
N5 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N5 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
H1A O1 H1B 99(4) . . ?
H2A O2 H2B 104(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
C5 N1 C1 C2 -0.2(7) . . . . ?
Cu1 N1 C1 C2 173.1(4) . . . . ?
N1 C1 C2 C3 0.2(8) . . . . ?
C1 C2 C3 C4 0.9(8) . . . . ?
C2 C3 C4 C5 -2.0(8) . . . . ?
C1 N1 C5 C4 -1.0(7) . . . . ?
Cu1 N1 C5 C4 -175.2(3) . . . . ?
C1 N1 C5 C6 177.4(4) . . . . ?
Cu1 N1 C5 C6 3.2(5) . . . . ?
C3 C4 C5 N1 2.0(7) . . . . ?
C3 C4 C5 C6 -176.2(4) . . . . ?
C10 N2 C6 C7 1.2(6) . . . . ?
Cu1 N2 C6 C7 176.7(3) . . . . ?
C10 N2 C6 C5 -179.0(4) . . . . ?
Cu1 N2 C6 C5 -3.5(5) . . . . ?
N1 C5 C6 N2 0.0(5) . . . . ?
C4 C5 C6 N2 178.3(4) . . . . ?
N1 C5 C6 C7 179.8(4) . . . . ?
C4 C5 C6 C7 -1.9(7) . . . . ?
N2 C6 C7 C8 -1.6(7) . . . . ?
C5 C6 C7 C8 178.6(4) . . . . ?
C6 C7 C8 C9 0.6(6) . . . . ?
C6 C7 C8 C16 177.9(4) . . . . ?
C7 C8 C9 C10 0.8(6) . . . . ?
C16 C8 C9 C10 -176.5(4) . . . . ?
C6 N2 C10 C9 0.2(6) . . . . ?
Cu1 N2 C10 C9 -175.3(3) . . . . ?
C6 N2 C10 C11 -179.3(4) . . . . ?
Cu1 N2 C10 C11 5.2(5) . . . . ?
C8 C9 C10 N2 -1.2(6) . . . . ?
C8 C9 C10 C11 178.2(4) . . . . ?
C15 N3 C11 C12 -1.1(7) . . . . ?
Cu1 N3 C11 C12 178.3(3) . . . . ?
C15 N3 C11 C10 176.4(4) . . . . ?
Cu1 N3 C11 C10 -4.2(5) . . . . ?
N2 C10 C11 N3 -0.4(5) . . . . ?
C9 C10 C11 N3 -179.8(4) . . . . ?
N2 C10 C11 C12 177.0(4) . . . . ?
C9 C10 C11 C12 -2.4(7) . . . . ?
N3 C11 C12 C13 2.2(7) . . . . ?
C10 C11 C12 C13 -175.0(4) . . . . ?
C11 C12 C13 C14 -1.9(8) . . . . ?
C12 C13 C14 C15 0.5(9) . . . . ?
C11 N3 C15 C14 -0.3(8) . . . . ?
Cu1 N3 C15 C14 -179.7(4) . . . . ?
C13 C14 C15 N3 0.6(9) . . . . ?
C9 C8 C16 C17 13.5(7) . . . . ?
C7 C8 C16 C17 -163.7(5) . . . . ?
C9 C8 C16 C21 -167.8(5) . . . . ?
C7 C8 C16 C21 15.0(7) . . . . ?
C21 C16 C17 C18 -3.4(8) . . . . ?
C8 C16 C17 C18 175.3(5) . . . . ?
C16 C17 C18 C19 1.6(9) . . . . ?
C17 C18 C19 C20 1.4(9) . . . . ?
C18 C19 C20 C21 -2.3(9) . . . . ?
C19 C20 C21 C16 0.4(9) . . . . ?
C17 C16 C21 C20 2.5(8) . . . . ?
C8 C16 C21 C20 -176.2(5) . . . . ?
C26 N4 C22 C23 0.3(8) . . . . ?
Cu1 N4 C22 C23 -178.0(4) . . . . ?
N4 C22 C23 C24 -0.7(8) . . . . ?
C27 N5 C24 C25 0.7(9) . . . . ?
C28 N5 C24 C25 -177.8(5) . . . . ?
C27 N5 C24 C23 -177.9(5) . . . . ?
C28 N5 C24 C23 3.5(8) . . . . ?
C22 C23 C24 N5 -179.9(5) . . . . ?
C22 C23 C24 C25 1.4(7) . . . . ?
N5 C24 C25 C26 179.5(5) . . . . ?
C23 C24 C25 C26 -1.8(8) . . . . ?
C22 N4 C26 C25 -0.7(8) . . . . ?
Cu1 N4 C26 C25 177.6(4) . . . . ?
C24 C25 C26 N4 1.5(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2B O1 0.87(4) 2.21(8) 2.877(7) 133(9) 2_666
O2 H2A Cl1 0.82(4) 2.63(6) 3.293(6) 139(7) 1_455
O1 H1B Cl2 0.96(4) 2.33(4) 3.265(5) 165(5) 2_665
O1 H1A Cl2 0.86(4) 2.37(4) 3.225(5) 173(6) .
C25 H25 O2 0.93 2.46 3.300(8) 150.7 .
C23 H23 Cl1 0.93 2.73 3.623(5) 162.0 2_776
C12 H12 Cl1 0.93 2.70 3.616(5) 168.0 2_777
C9 H9 Cl1 0.93 2.78 3.697(5) 168.1 2_777
C7 H7 Cl2 0.93 2.83 3.755(5) 173.8 1_656
C4 H4 Cl2 0.93 2.64 3.565(5) 174.8 1_656

_refine_diff_density_max         1.323
_refine_diff_density_min         -1.631
_refine_diff_density_rms         0.117

_shelxl_version_number           2013-2


_exptl_crystal_recrystallization_method 'Vapour Deposition'
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_mo_30916b
_database_code_depnum_ccdc_archive 'CCDC 1045809'
_audit_update_record             
;
2015-01-27 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        mo_30916b
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H27 Cl2 Cu N5 O2 S'
_chemical_formula_weight         608.02

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'
S S 0.1246 0.1234 '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'
O O 0.0106 0.0060 '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                   10.634(3)
_cell_length_b                   10.982(3)
_cell_length_c                   11.926(3)
_cell_angle_alpha                89.311(4)
_cell_angle_beta                 77.918(4)
_cell_angle_gamma                79.929(4)
_cell_volume                     1340.6(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2423
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.00

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_F_000             626
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.126
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8686
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.747
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             5183
_reflns_number_gt                3877
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
; 
 w=1/[σ²(Fo²)+(0.1350P)²] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5183
_refine_ls_number_parameters     352
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.2024
_refine_ls_wR_factor_gt          0.1666
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.39043(6) 0.28319(5) 0.29703(5) 0.0252(2) Uani 1 1 d . . . . .
Cl1 Cl 0.59432(11) 0.38215(11) 0.19742(9) 0.0271(3) Uani 1 1 d D . . . .
Cl2 Cl 0.83840(12) 0.84035(11) 0.53612(10) 0.0307(3) Uani 1 1 d . . . . .
N1 N 0.2888(4) 0.4343(3) 0.3928(3) 0.0226(8) Uani 1 1 d . . . . .
N2 N 0.4623(3) 0.2585(3) 0.4328(3) 0.0191(8) Uani 1 1 d . . . . .
N3 N 0.5063(4) 0.1136(4) 0.2568(3) 0.0226(8) Uani 1 1 d . . . . .
N4 N 0.2963(4) 0.3015(4) 0.1706(3) 0.0232(8) Uani 1 1 d . . . . .
N5 N 0.0782(4) 0.3640(4) -0.0853(4) 0.0327(10) Uani 1 1 d . . . . .
C1 C 0.1909(5) 0.5189(5) 0.3670(4) 0.0316(11) Uani 1 1 d . . . . .
H1 H 0.1638 0.5088 0.2972 0.038 Uiso 1 1 calc R U . . .
C2 C 0.1287(5) 0.6195(5) 0.4384(4) 0.0341(12) Uani 1 1 d . . . . .
H2 H 0.0608 0.6782 0.4179 0.041 Uiso 1 1 calc R U . . .
C3 C 0.1681(5) 0.6325(5) 0.5405(4) 0.0333(11) Uani 1 1 d . . . . .
H3 H 0.1264 0.7000 0.5917 0.040 Uiso 1 1 calc R U . . .
C4 C 0.2675(4) 0.5474(4) 0.5676(4) 0.0254(10) Uani 1 1 d . . . . .
H4 H 0.2970 0.5569 0.6364 0.030 Uiso 1 1 calc R U . . .
C5 C 0.3241(4) 0.4478(4) 0.4936(4) 0.0201(9) Uani 1 1 d . . . . .
C6 C 0.4266(4) 0.3452(4) 0.5167(4) 0.0189(9) Uani 1 1 d . . . . .
C7 C 0.4825(4) 0.3323(4) 0.6126(4) 0.0206(9) Uani 1 1 d . . . . .
H7 H 0.4574 0.3942 0.6719 0.025 Uiso 1 1 calc R U . . .
C8 C 0.5755(4) 0.2281(4) 0.6213(4) 0.0202(9) Uani 1 1 d . . . . .
C9 C 0.6101(4) 0.1381(4) 0.5316(4) 0.0199(9) Uani 1 1 d . . . . .
H9 H 0.6728 0.0658 0.5353 0.024 Uiso 1 1 calc R U . . .
C10 C 0.5511(4) 0.1566(4) 0.4377(4) 0.0190(9) Uani 1 1 d . . . . .
C11 C 0.5768(4) 0.0736(4) 0.3363(4) 0.0183(9) Uani 1 1 d . . . . .
C12 C 0.6649(4) -0.0377(4) 0.3225(4) 0.0250(10) Uani 1 1 d . . . . .
H12 H 0.7101 -0.0672 0.3809 0.030 Uiso 1 1 calc R U . . .
C13 C 0.6840(5) -0.1039(4) 0.2203(4) 0.0279(10) Uani 1 1 d . . . . .
H13 H 0.7444 -0.1796 0.2069 0.033 Uiso 1 1 calc R U . . .
C14 C 0.6146(5) -0.0592(5) 0.1376(4) 0.0310(11) Uani 1 1 d . . . . .
H14 H 0.6289 -0.1022 0.0662 0.037 Uiso 1 1 calc R U . . .
C15 C 0.5263(5) 0.0465(4) 0.1601(4) 0.0278(10) Uani 1 1 d . . . . .
H15 H 0.4761 0.0744 0.1046 0.033 Uiso 1 1 calc R U . . .
C16 C 0.6335(4) 0.2079(4) 0.7224(4) 0.0234(10) Uani 1 1 d . . . . .
C17 C 0.7379(3) 0.1011(3) 0.7399(2) 0.0353(9) Uani 0.726(6) 1 d . . P A 1
H17 H 0.7845 0.0375 0.6860 0.042 Uiso 0.726(6) 1 calc R U P A 1
C18 C 0.7510(6) 0.1172(6) 0.8567(6) 0.0502(16) Uani 0.726(6) 1 d . . P A 1
H18 H 0.8086 0.0597 0.8908 0.060 Uiso 0.726(6) 1 calc R U P A 1
C19 C 0.6783(7) 0.2166(7) 0.9135(5) 0.0478(16) Uani 0.726(6) 1 d . . P A 1
H19 H 0.6804 0.2366 0.9903 0.057 Uiso 0.726(6) 1 calc R U P A 1
S1 S 0.58529(16) 0.30132(15) 0.83984(13) 0.0292(5) Uani 0.726(6) 1 d . . P A 1
S1' S 0.7379(3) 0.1011(3) 0.7399(2) 0.0353(9) Uani 0.274(6) 1 d . . P A 2
C19' C 0.7510(6) 0.1172(6) 0.8567(6) 0.0502(16) Uani 0.274(6) 1 d . . P A 2
H19' H 0.8086 0.0597 0.8908 0.060 Uiso 0.274(6) 1 calc R U P A 2
C18' C 0.6783(7) 0.2166(7) 0.9135(5) 0.0478(16) Uani 0.274(6) 1 d . . P A 2
H18' H 0.6804 0.2366 0.9903 0.057 Uiso 0.274(6) 1 calc R U P A 2
C17' C 0.58529(16) 0.30132(15) 0.83984(13) 0.0292(5) Uani 0.274(6) 1 d . . P A
2
H17' H 0.5250 0.3768 0.8570 0.035 Uiso 0.274(6) 1 calc R U P A 2
C20 C 0.1931(5) 0.2457(5) 0.1705(4) 0.0269(10) Uani 1 1 d . . . . .
H20 H 0.1707 0.1908 0.2306 0.032 Uiso 1 1 calc R U . . .
C21 C 0.1188(5) 0.2635(5) 0.0893(4) 0.0281(11) Uani 1 1 d . . . . .
H21 H 0.0471 0.2214 0.0941 0.034 Uiso 1 1 calc R U . . .
C22 C 0.1484(4) 0.3448(4) -0.0027(4) 0.0239(10) Uani 1 1 d . . . . .
C23 C 0.2565(5) 0.4022(5) -0.0011(4) 0.0258(10) Uani 1 1 d . . . . .
H23 H 0.2816 0.4580 -0.0596 0.031 Uiso 1 1 calc R U . . .
C24 C 0.3252(5) 0.3791(5) 0.0830(4) 0.0278(10) Uani 1 1 d . . . . .
H24 H 0.3977 0.4194 0.0806 0.033 Uiso 1 1 calc R U . . .
C25 C 0.1147(5) 0.4426(5) -0.1821(4) 0.0350(12) Uani 1 1 d . . . . .
H25A H 0.1466 0.5133 -0.1556 0.053 Uiso 1 1 calc R U . . .
H25B H 0.0383 0.4724 -0.2151 0.053 Uiso 1 1 calc R U . . .
H25C H 0.1837 0.3948 -0.2406 0.053 Uiso 1 1 calc R U . . .
C26 C -0.0298(5) 0.2993(6) -0.0878(5) 0.0466(15) Uani 1 1 d . . . . .
H26A H 0.0044 0.2175 -0.1245 0.070 Uiso 1 1 calc R U . . .
H26B H -0.0893 0.3471 -0.1314 0.070 Uiso 1 1 calc R U . . .
H26C H -0.0771 0.2900 -0.0092 0.070 Uiso 1 1 calc R U . . .
O1 O 0.0601(4) 0.9428(4) 0.6346(4) 0.0467(10) Uani 1 1 d D . . . .
H1A H 0.013(9) 0.916(7) 0.595(7) 0.14(4) Uiso 1 1 d D . . . .
H1B H 0.072(5) 1.012(3) 0.607(4) 0.023(13) Uiso 1 1 d D . . . .
O2 O 0.8472(4) 0.1541(5) 0.1695(4) 0.0618(14) Uani 1 1 d D . . . .
H2A H 0.875(4) 0.135(4) 0.230(3) 0.018(13) Uiso 1 1 d D . . . .
H2B H 0.801(4) 0.224(3) 0.180(4) 0.027 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.927(4) . ?
Cu1 N4 1.967(4) . ?
Cu1 N1 2.032(4) . ?
Cu1 N3 2.046(4) . ?
Cu1 Cl1 2.6474(13) . ?
N1 C5 1.350(6) . ?
N1 C1 1.353(6) . ?
N2 C6 1.338(5) . ?
N2 C10 1.342(6) . ?
N3 C15 1.334(6) . ?
N3 C11 1.352(6) . ?
N4 C20 1.348(6) . ?
N4 C24 1.358(6) . ?
N5 C22 1.349(6) . ?
N5 C26 1.457(7) . ?
N5 C25 1.461(6) . ?
C1 C2 1.384(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.491(6) . ?
C6 C7 1.390(6) . ?
C7 C8 1.394(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.411(6) . ?
C8 C16 1.463(6) . ?
C9 C10 1.390(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.472(6) . ?
C11 C12 1.393(6) . ?
C12 C13 1.387(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.349(7) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.512(6) . ?
C16 S1 1.681(5) . ?
C17 C18 1.445(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.323(10) . ?
C18 H18 0.9500 . ?
C19 S1 1.625(7) . ?
C19 H19 0.9500 . ?
C20 C21 1.364(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.425(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.408(6) . ?
C23 C24 1.357(7) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
O1 H1A 0.85(2) . ?
O1 H1B 0.840(19) . ?
O2 H2A 0.845(18) . ?
O2 H2B 0.830(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N4 172.42(15) . . ?
N2 Cu1 N1 79.82(15) . . ?
N4 Cu1 N1 98.06(15) . . ?
N2 Cu1 N3 80.25(15) . . ?
N4 Cu1 N3 101.03(15) . . ?
N1 Cu1 N3 159.43(15) . . ?
N2 Cu1 Cl1 89.43(11) . . ?
N4 Cu1 Cl1 98.08(12) . . ?
N1 Cu1 Cl1 97.43(11) . . ?
N3 Cu1 Cl1 87.44(11) . . ?
C5 N1 C1 118.2(4) . . ?
C5 N1 Cu1 114.5(3) . . ?
C1 N1 Cu1 127.3(3) . . ?
C6 N2 C10 122.1(4) . . ?
C6 N2 Cu1 119.4(3) . . ?
C10 N2 Cu1 118.5(3) . . ?
C15 N3 C11 118.6(4) . . ?
C15 N3 Cu1 127.7(3) . . ?
C11 N3 Cu1 113.4(3) . . ?
C20 N4 C24 116.2(4) . . ?
C20 N4 Cu1 122.0(3) . . ?
C24 N4 Cu1 121.7(3) . . ?
C22 N5 C26 121.8(4) . . ?
C22 N5 C25 121.1(4) . . ?
C26 N5 C25 116.8(4) . . ?
N1 C1 C2 122.5(5) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C1 118.2(5) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C4 C3 C2 119.9(5) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.1(4) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 122.1(4) . . ?
N1 C5 C6 113.7(4) . . ?
C4 C5 C6 124.3(4) . . ?
N2 C6 C7 120.3(4) . . ?
N2 C6 C5 112.3(4) . . ?
C7 C6 C5 127.3(4) . . ?
C6 C7 C8 119.7(4) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 118.5(4) . . ?
C7 C8 C16 121.8(4) . . ?
C9 C8 C16 119.7(4) . . ?
C10 C9 C8 119.0(4) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
N2 C10 C9 120.4(4) . . ?
N2 C10 C11 113.3(4) . . ?
C9 C10 C11 126.3(4) . . ?
N3 C11 C12 122.0(4) . . ?
N3 C11 C10 114.4(4) . . ?
C12 C11 C10 123.6(4) . . ?
C13 C12 C11 117.5(4) . . ?
C13 C12 H12 121.3 . . ?
C11 C12 H12 121.3 . . ?
C12 C13 C14 119.7(5) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 119.0(4) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
N3 C15 C14 123.0(5) . . ?
N3 C15 H15 118.5 . . ?
C14 C15 H15 118.5 . . ?
C8 C16 C17 126.5(4) . . ?
C8 C16 S1 123.0(4) . . ?
C17 C16 S1 110.5(3) . . ?
C18 C17 C16 104.7(4) . . ?
C18 C17 H17 127.7 . . ?
C16 C17 H17 127.7 . . ?
C19 C18 C17 116.3(5) . . ?
C19 C18 H18 121.9 . . ?
C17 C18 H18 121.9 . . ?
C18 C19 S1 113.8(4) . . ?
C18 C19 H19 123.1 . . ?
S1 C19 H19 123.1 . . ?
C19 S1 C16 94.7(3) . . ?
N4 C20 C21 123.9(4) . . ?
N4 C20 H20 118.0 . . ?
C21 C20 H20 118.0 . . ?
C20 C21 C22 120.3(4) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
N5 C22 C23 122.8(4) . . ?
N5 C22 C21 122.2(4) . . ?
C23 C22 C21 115.0(4) . . ?
C24 C23 C22 120.9(4) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 N4 123.8(4) . . ?
C23 C24 H24 118.1 . . ?
N4 C24 H24 118.1 . . ?
N5 C25 H25A 109.5 . . ?
N5 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N5 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N5 C26 H26A 109.5 . . ?
N5 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N5 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
H1A O1 H1B 105(3) . . ?
H2A O2 H2B 108(3) . . ?

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
C5 N1 C1 C2 1.7(7) . . . . ?
Cu1 N1 C1 C2 -179.4(4) . . . . ?
N1 C1 C2 C3 -0.7(8) . . . . ?
C1 C2 C3 C4 0.8(8) . . . . ?
C2 C3 C4 C5 -2.0(7) . . . . ?
C1 N1 C5 C4 -2.9(6) . . . . ?
Cu1 N1 C5 C4 178.1(3) . . . . ?
C1 N1 C5 C6 176.2(4) . . . . ?
Cu1 N1 C5 C6 -2.8(5) . . . . ?
C3 C4 C5 N1 3.1(7) . . . . ?
C3 C4 C5 C6 -175.9(4) . . . . ?
C10 N2 C6 C7 0.5(6) . . . . ?
Cu1 N2 C6 C7 -176.6(3) . . . . ?
C10 N2 C6 C5 -178.4(4) . . . . ?
Cu1 N2 C6 C5 4.5(5) . . . . ?
N1 C5 C6 N2 -0.8(5) . . . . ?
C4 C5 C6 N2 178.2(4) . . . . ?
N1 C5 C6 C7 -179.7(4) . . . . ?
C4 C5 C6 C7 -0.6(7) . . . . ?
N2 C6 C7 C8 -0.3(6) . . . . ?
C5 C6 C7 C8 178.4(4) . . . . ?
C6 C7 C8 C9 -0.1(6) . . . . ?
C6 C7 C8 C16 -177.7(4) . . . . ?
C7 C8 C9 C10 0.4(6) . . . . ?
C16 C8 C9 C10 178.0(4) . . . . ?
C6 N2 C10 C9 -0.3(6) . . . . ?
Cu1 N2 C10 C9 176.9(3) . . . . ?
C6 N2 C10 C11 -179.6(4) . . . . ?
Cu1 N2 C10 C11 -2.5(5) . . . . ?
C8 C9 C10 N2 -0.2(6) . . . . ?
C8 C9 C10 C11 179.0(4) . . . . ?
C15 N3 C11 C12 -2.9(6) . . . . ?
Cu1 N3 C11 C12 -177.7(3) . . . . ?
C15 N3 C11 C10 177.7(4) . . . . ?
Cu1 N3 C11 C10 2.9(4) . . . . ?
N2 C10 C11 N3 -0.5(5) . . . . ?
C9 C10 C11 N3 -179.8(4) . . . . ?
N2 C10 C11 C12 -179.8(4) . . . . ?
C9 C10 C11 C12 0.9(7) . . . . ?
N3 C11 C12 C13 3.7(6) . . . . ?
C10 C11 C12 C13 -177.0(4) . . . . ?
C11 C12 C13 C14 -1.1(7) . . . . ?
C12 C13 C14 C15 -2.1(7) . . . . ?
C11 N3 C15 C14 -0.5(7) . . . . ?
Cu1 N3 C15 C14 173.4(4) . . . . ?
C13 C14 C15 N3 3.0(8) . . . . ?
C7 C8 C16 C17 -177.9(4) . . . . ?
C9 C8 C16 C17 4.6(6) . . . . ?
C7 C8 C16 S1 5.0(6) . . . . ?
C9 C8 C16 S1 -172.5(3) . . . . ?
C8 C16 C17 C18 -174.2(4) . . . . ?
S1 C16 C17 C18 3.2(4) . . . . ?
C16 C17 C18 C19 -2.6(6) . . . . ?
C17 C18 C19 S1 0.9(7) . . . . ?
C18 C19 S1 C16 1.0(5) . . . . ?
C8 C16 S1 C19 174.9(4) . . . . ?
C17 C16 S1 C19 -2.5(3) . . . . ?
C24 N4 C20 C21 -0.2(7) . . . . ?
Cu1 N4 C20 C21 174.7(4) . . . . ?
N4 C20 C21 C22 0.1(8) . . . . ?
C26 N5 C22 C23 177.3(5) . . . . ?
C25 N5 C22 C23 2.8(8) . . . . ?
C26 N5 C22 C21 -2.1(8) . . . . ?
C25 N5 C22 C21 -176.7(5) . . . . ?
C20 C21 C22 N5 179.3(5) . . . . ?
C20 C21 C22 C23 -0.1(7) . . . . ?
N5 C22 C23 C24 -179.2(5) . . . . ?
C21 C22 C23 C24 0.3(7) . . . . ?
C22 C23 C24 N4 -0.4(8) . . . . ?
C20 N4 C24 C23 0.3(7) . . . . ?
Cu1 N4 C24 C23 -174.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 Cl1 0.95 2.64 3.575(5) 167.9 2_666
C7 H7 Cl1 0.95 2.83 3.760(5) 165.3 2_666
C9 H9 Cl2 0.95 2.78 3.723(5) 173.7 1_545
C12 H12 Cl2 0.95 2.62 3.565(5) 177.0 1_545
C21 H21 O2 0.95 2.37 3.275(7) 159.7 1_455
C23 H23 Cl1 0.95 2.71 3.638(5) 164.8 2_665
O1 H1A Cl2 0.85(2) 2.39(3) 3.213(5) 163(9) 1_455
O1 H1B Cl2 0.840(19) 2.50(3) 3.293(4) 157(5) 2_676
O2 H2A O1 0.845(18) 2.01(2) 2.846(7) 170(4) 2_666
O2 H2B Cl1 0.830(19) 2.53(3) 3.303(5) 156(5) .

_refine_diff_density_max         1.465
_refine_diff_density_min         -0.907
_refine_diff_density_rms         0.169

_shelxl_version_number           2013-2


_exptl_crystal_recrystallization_method 'Vapour Deposition'
