# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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#######################################################################

data_s68
_database_code_depnum_ccdc_archive 'CCDC 1568987'
_audit_update_record             
;
2017-08-14 deposited with the CCDC.
2018-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 Cl3 Cu N2 O3'
_chemical_formula_weight         517.27

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.4882(4)
_cell_length_b                   10.6650(3)
_cell_length_c                   24.9547(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4388.19(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14802
_cell_measurement_theta_min      2.416
_cell_measurement_theta_max      28.497

_exptl_crystal_description       plane
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_F_000             2104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.913
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.092
_exptl_absorpt_coefficient_mu    1.386
_shelx_estimated_absorpt_T_min   0.364
_shelx_estimated_absorpt_T_max   0.883
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.428
_exptl_absorpt_correction_T_max  0.885
_exptl_absorpt_process_details   'Oxford Diffraction CrysAlis'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Sapphire CCD'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean 8.2564
_diffrn_reflns_number            30275
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.416
_diffrn_reflns_theta_max         28.497
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5187
_reflns_number_gt                3828
_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       'Oxford Diffraction CrysAlis'
_computing_cell_refinement       'Oxford Diffraction CrysAlis'
_computing_data_reduction        'Oxford Diffraction CrysAlis'
_computing_structure_solution    'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'

_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)+(0.0394P)²+2.2486P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5187
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_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 0.08222(2) 0.64311(2) 0.31849(2) 0.03627(9) Uani 1 1 d . . . . .
O1 O 0.16374(9) 0.55254(15) 0.28140(6) 0.0449(4) Uani 1 1 d . . . . .
C2 C 0.19001(12) 0.56876(19) 0.23258(9) 0.0391(5) Uani 1 1 d . . . . .
C3 C 0.26098(14) 0.4990(2) 0.21751(10) 0.0476(5) Uani 1 1 d . . . . .
H3A H 0.2850 0.4457 0.2423 0.057 Uiso 1 1 calc R U . . .
C4 C 0.29315(14) 0.5092(2) 0.16845(10) 0.0499(6) Uani 1 1 d . . . . .
H4A H 0.3402 0.4648 0.1605 0.060 Uiso 1 1 calc R U . . .
C5 C 0.25767(14) 0.5855(2) 0.12831(10) 0.0460(5) Uani 1 1 d . . . . .
C6 C 0.29057(17) 0.5911(3) 0.07604(11) 0.0610(7) Uani 1 1 d . . . . .
H6A H 0.3370 0.5453 0.0680 0.073 Uiso 1 1 calc R U . . .
C7 C 0.2555(2) 0.6621(3) 0.03747(11) 0.0668(8) Uani 1 1 d . . . . .
H7A H 0.2773 0.6640 0.0031 0.080 Uiso 1 1 calc R U . . .
C8 C 0.18677(18) 0.7320(3) 0.04945(10) 0.0624(7) Uani 1 1 d . . . . .
H8A H 0.1632 0.7813 0.0230 0.075 Uiso 1 1 calc R U . . .
C9 C 0.15321(16) 0.7294(2) 0.09975(9) 0.0506(6) Uani 1 1 d . . . . .
H9A H 0.1073 0.7774 0.1069 0.061 Uiso 1 1 calc R U . . .
C10 C 0.18706(13) 0.65537(19) 0.14079(9) 0.0403(5) Uani 1 1 d . . . . .
C11 C 0.15352(13) 0.64751(19) 0.19477(8) 0.0367(4) Uani 1 1 d . . . . .
C12 C 0.08311(12) 0.7195(2) 0.20760(8) 0.0372(4) Uani 1 1 d . . . . .
H12A H 0.0599 0.7645 0.1796 0.045 Uiso 1 1 calc R U . . .
N13 N 0.04806(10) 0.72903(16) 0.25371(7) 0.0375(4) Uani 1 1 d . . . . .
C14 C -0.02366(14) 0.8119(2) 0.25553(9) 0.0456(5) Uani 1 1 d . . . . .
H14A H -0.0494 0.8135 0.2206 0.055 Uiso 1 1 calc R U . . .
H14B H -0.0068 0.8965 0.2642 0.055 Uiso 1 1 calc R U . . .
C15 C -0.08396(13) 0.7663(2) 0.29707(10) 0.0484(5) Uani 1 1 d . . . . .
H15A H -0.1361 0.8055 0.2906 0.058 Uiso 1 1 calc R U . . .
H15B H -0.0908 0.6763 0.2934 0.058 Uiso 1 1 calc R U . . .
C16 C -0.05704(15) 0.7956(2) 0.35273(9) 0.0442(5) Uani 1 1 d . . . . .
N17 N 0.01768(11) 0.75682(17) 0.36687(7) 0.0420(4) Uani 1 1 d . . . . .
C18 C 0.04605(18) 0.7856(2) 0.41573(10) 0.0549(6) Uani 1 1 d . . . . .
H18A H 0.0978 0.7591 0.4253 0.066 Uiso 1 1 calc R U . . .
C19 C 0.0011(2) 0.8528(3) 0.45217(11) 0.0689(8) Uani 1 1 d . . . . .
H19A H 0.0220 0.8718 0.4858 0.083 Uiso 1 1 calc R U . . .
C20 C -0.0756(2) 0.8915(3) 0.43791(13) 0.0751(9) Uani 1 1 d . . . . .
H20A H -0.1072 0.9371 0.4618 0.090 Uiso 1 1 calc R U . . .
C21 C -0.10477(19) 0.8620(2) 0.38817(11) 0.0624(7) Uani 1 1 d . . . . .
H21A H -0.1567 0.8868 0.3782 0.075 Uiso 1 1 calc R U . . .
C30 C 0.0558(2) 0.3953(3) 0.44228(11) 0.0725(8) Uani 1 1 d . . . . .
H30A H 0.1060 0.4137 0.4602 0.109 Uiso 1 1 calc R U . . .
H30B H 0.0112 0.4162 0.4653 0.109 Uiso 1 1 calc R U . . .
H30C H 0.0538 0.3076 0.4337 0.109 Uiso 1 1 calc R U . . .
C31 C 0.05035(13) 0.4712(2) 0.39144(8) 0.0396(5) Uani 1 1 d . . . . .
O32 O -0.00878(11) 0.46249(16) 0.36220(7) 0.0560(4) Uani 1 1 d . . . . .
O33 O 0.10949(9) 0.54406(15) 0.38191(6) 0.0454(4) Uani 1 1 d . . . . .
C40 C 0.20225(16) 1.1054(2) 0.36723(10) 0.0552(6) Uani 1 1 d . . . . .
H40A H 0.2470 1.0598 0.3502 0.066 Uiso 1 1 calc R U . A 1
Cl1A Cl 0.2126(4) 1.2643(6) 0.3454(2) 0.0819(10) Uani 0.5474 1 d . . P B 1
Cl2A Cl 0.2047(3) 1.0612(6) 0.4356(2) 0.0791(11) Uani 0.5474 1 d . . P B 1
Cl3A Cl 0.1139(3) 1.0450(6) 0.3385(3) 0.0783(11) Uani 0.5474 1 d . . P B 1
Cl1B Cl 0.2291(5) 1.2598(8) 0.3629(3) 0.0953(17) Uani 0.4526 1 d . . P B 2
Cl2B Cl 0.2000(4) 1.0967(8) 0.4356(3) 0.100(2) Uani 0.4526 1 d . . P B 2
Cl3B Cl 0.1043(5) 1.0777(8) 0.3416(4) 0.096(2) Uani 0.4526 1 d . . P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.8965(15) . ?
Cu1 N13 1.9416(17) . ?
Cu1 O33 1.9553(15) . ?
Cu1 N17 2.0151(18) . ?
O1 C2 1.304(3) . ?
C2 C11 1.399(3) . ?
C2 C3 1.437(3) . ?
C3 C4 1.339(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.417(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.414(3) . ?
C5 C10 1.417(3) . ?
C6 C7 1.354(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.389(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.372(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.409(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.458(3) . ?
C11 C12 1.428(3) . ?
C12 N13 1.292(3) . ?
C12 H12A 0.9300 . ?
N13 C14 1.477(3) . ?
C14 C15 1.516(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.491(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N17 1.347(3) . ?
C16 C21 1.380(3) . ?
N17 C18 1.341(3) . ?
C18 C19 1.375(4) . ?
C18 H18A 0.9300 . ?
C19 C20 1.376(5) . ?
C19 H19A 0.9300 . ?
C20 C21 1.368(4) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
C30 C31 1.508(3) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 O32 1.221(3) . ?
C31 O33 1.269(3) . ?
C40 Cl1B 1.708(9) . ?
C40 Cl2B 1.710(8) . ?
C40 Cl3A 1.747(7) . ?
C40 Cl3B 1.762(9) . ?
C40 Cl2A 1.770(6) . ?
C40 Cl1A 1.788(7) . ?
C40 H40A 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N13 92.27(7) . . ?
O1 Cu1 O33 87.53(6) . . ?
N13 Cu1 O33 174.62(7) . . ?
O1 Cu1 N17 166.71(7) . . ?
N13 Cu1 N17 93.54(7) . . ?
O33 Cu1 N17 87.80(7) . . ?
C2 O1 Cu1 128.58(13) . . ?
O1 C2 C11 124.52(19) . . ?
O1 C2 C3 116.5(2) . . ?
C11 C2 C3 119.0(2) . . ?
C4 C3 C2 121.3(2) . . ?
C4 C3 H3A 119.3 . . ?
C2 C3 H3A 119.3 . . ?
C3 C4 C5 122.0(2) . . ?
C3 C4 H4A 119.0 . . ?
C5 C4 H4A 119.0 . . ?
C6 C5 C10 119.7(2) . . ?
C6 C5 C4 121.2(2) . . ?
C10 C5 C4 119.1(2) . . ?
C7 C6 C5 121.0(3) . . ?
C7 C6 H6A 119.5 . . ?
C5 C6 H6A 119.5 . . ?
C6 C7 C8 119.7(2) . . ?
C6 C7 H7A 120.1 . . ?
C8 C7 H7A 120.1 . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 H8A 119.5 . . ?
C7 C8 H8A 119.5 . . ?
C8 C9 C10 121.1(2) . . ?
C8 C9 H9A 119.4 . . ?
C10 C9 H9A 119.4 . . ?
C9 C10 C5 117.4(2) . . ?
C9 C10 C11 123.6(2) . . ?
C5 C10 C11 119.0(2) . . ?
C2 C11 C12 121.39(19) . . ?
C2 C11 C10 119.63(19) . . ?
C12 C11 C10 119.0(2) . . ?
N13 C12 C11 127.3(2) . . ?
N13 C12 H12A 116.4 . . ?
C11 C12 H12A 116.4 . . ?
C12 N13 C14 115.64(18) . . ?
C12 N13 Cu1 125.08(14) . . ?
C14 N13 Cu1 119.27(13) . . ?
N13 C14 C15 110.75(18) . . ?
N13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
N13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 112.0(2) . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
N17 C16 C21 120.8(2) . . ?
N17 C16 C15 116.89(19) . . ?
C21 C16 C15 122.3(2) . . ?
C18 N17 C16 119.2(2) . . ?
C18 N17 Cu1 119.87(17) . . ?
C16 N17 Cu1 120.71(15) . . ?
N17 C18 C19 122.1(3) . . ?
N17 C18 H18A 118.9 . . ?
C19 C18 H18A 118.9 . . ?
C18 C19 C20 118.7(3) . . ?
C18 C19 H19A 120.6 . . ?
C20 C19 H19A 120.6 . . ?
C21 C20 C19 119.3(3) . . ?
C21 C20 H20A 120.4 . . ?
C19 C20 H20A 120.4 . . ?
C20 C21 C16 119.9(3) . . ?
C20 C21 H21A 120.0 . . ?
C16 C21 H21A 120.0 . . ?
C31 C30 H30A 109.5 . . ?
C31 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C31 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O32 C31 O33 123.2(2) . . ?
O32 C31 C30 120.7(2) . . ?
O33 C31 C30 116.1(2) . . ?
C31 O33 Cu1 107.80(13) . . ?
Cl1B C40 Cl2B 97.0(4) . . ?
Cl1B C40 Cl3B 112.1(4) . . ?
Cl2B C40 Cl3B 109.5(4) . . ?
Cl3A C40 Cl2A 108.5(3) . . ?
Cl3A C40 Cl1A 107.7(3) . . ?
Cl2A C40 Cl1A 122.9(3) . . ?
Cl3A C40 H40A 105.5 . . ?
Cl2A C40 H40A 105.5 . . ?
Cl1A C40 H40A 105.5 . . ?

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
N13 Cu1 O1 C2 10.31(19) . . . . ?
O33 Cu1 O1 C2 -175.07(18) . . . . ?
N17 Cu1 O1 C2 -105.6(3) . . . . ?
Cu1 O1 C2 C11 -9.8(3) . . . . ?
Cu1 O1 C2 C3 170.77(15) . . . . ?
O1 C2 C3 C4 -179.7(2) . . . . ?
C11 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 -2.2(4) . . . . ?
C3 C4 C5 C6 -177.3(2) . . . . ?
C3 C4 C5 C10 1.4(3) . . . . ?
C10 C5 C6 C7 -0.2(4) . . . . ?
C4 C5 C6 C7 178.6(2) . . . . ?
C5 C6 C7 C8 0.9(4) . . . . ?
C6 C7 C8 C9 -0.7(4) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C8 C9 C10 C5 1.0(3) . . . . ?
C8 C9 C10 C11 -179.2(2) . . . . ?
C6 C5 C10 C9 -0.8(3) . . . . ?
C4 C5 C10 C9 -179.5(2) . . . . ?
C6 C5 C10 C11 179.4(2) . . . . ?
C4 C5 C10 C11 0.6(3) . . . . ?
O1 C2 C11 C12 0.9(3) . . . . ?
C3 C2 C11 C12 -179.7(2) . . . . ?
O1 C2 C11 C10 -178.23(19) . . . . ?
C3 C2 C11 C10 1.2(3) . . . . ?
C9 C10 C11 C2 178.3(2) . . . . ?
C5 C10 C11 C2 -1.9(3) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C5 C10 C11 C12 179.00(19) . . . . ?
C2 C11 C12 N13 4.8(3) . . . . ?
C10 C11 C12 N13 -176.1(2) . . . . ?
C11 C12 N13 C14 179.3(2) . . . . ?
C11 C12 N13 Cu1 -1.2(3) . . . . ?
C12 N13 C14 C15 149.1(2) . . . . ?
Cu1 N13 C14 C15 -30.4(3) . . . . ?
N13 C14 C15 C16 75.5(3) . . . . ?
C14 C15 C16 N17 -53.5(3) . . . . ?
C14 C15 C16 C21 124.8(2) . . . . ?
C21 C16 N17 C18 -1.2(3) . . . . ?
C15 C16 N17 C18 177.2(2) . . . . ?
C21 C16 N17 Cu1 172.92(18) . . . . ?
C15 C16 N17 Cu1 -8.7(3) . . . . ?
C16 N17 C18 C19 0.4(4) . . . . ?
Cu1 N17 C18 C19 -173.7(2) . . . . ?
N17 C18 C19 C20 0.1(4) . . . . ?
C18 C19 C20 C21 0.0(4) . . . . ?
C19 C20 C21 C16 -0.8(4) . . . . ?
N17 C16 C21 C20 1.3(4) . . . . ?
C15 C16 C21 C20 -176.9(3) . . . . ?
O32 C31 O33 Cu1 4.9(3) . . . . ?
C30 C31 O33 Cu1 -174.17(18) . . . . ?

_refine_diff_density_max         0.327
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.054

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
####################################################################### 
# 
# 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_mb40
_database_code_depnum_ccdc_archive 'CCDC 1834036'
_audit_update_record             
;
2018-04-01 deposited with the CCDC.
2018-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H15 Cu N3 O4'
_chemical_formula_sum            'C18 H15 Cu N3 O4'
_chemical_formula_weight         400.87

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   30.800(2)
_cell_length_b                   7.1636(4)
_cell_length_c                   14.9571(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.322(6)
_cell_angle_gamma                90
_cell_volume                     3280.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    24945
_cell_measurement_theta_min      2.661
_cell_measurement_theta_max      28.475

_exptl_crystal_description       rod
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_F_000             1640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    1.362
_shelx_estimated_absorpt_T_min   0.532
_shelx_estimated_absorpt_T_max   0.865
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.532
_exptl_absorpt_correction_T_max  0.865
_exptl_absorpt_process_details   'Oxford Diffraction CrysAlis'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Sapphire CCD'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean 8.2564
_diffrn_reflns_number            11646
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.661
_diffrn_reflns_theta_max         28.475
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3788
_reflns_number_gt                3080
_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       'Oxford Diffraction CrysAlis'
_computing_cell_refinement       'Oxford Diffraction CrysAlis'
_computing_data_reduction        'Oxford Diffraction CrysAlis'
_computing_structure_solution    'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'

_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)+(0.0410P)²+0.9789P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3788
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0838
_refine_ls_wR_factor_gt          0.0769
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
Cu1 Cu 0.12113(2) 0.23629(3) 0.56027(2) 0.04490(10) Uani 1 1 d . . . . .
O1 O 0.16416(4) 0.06116(17) 0.59838(9) 0.0512(3) Uani 1 1 d . . . . .
C2 C 0.20583(6) 0.0881(2) 0.61699(11) 0.0421(4) Uani 1 1 d . . . . .
C3 C 0.23093(7) -0.0664(3) 0.65537(12) 0.0505(5) Uani 1 1 d . . . . .
H3A H 0.2170 -0.1798 0.6627 0.061 Uiso 1 1 calc R U . . .
C4 C 0.27390(7) -0.0519(3) 0.68105(12) 0.0523(5) Uani 1 1 d . . . . .
H4A H 0.2890 -0.1554 0.7058 0.063 Uiso 1 1 calc R U . . .
C5 C 0.29714(6) 0.1174(3) 0.67150(11) 0.0462(4) Uani 1 1 d . . . . .
C6 C 0.34189(7) 0.1321(3) 0.70304(13) 0.0587(5) Uani 1 1 d . . . . .
H6A H 0.3563 0.0295 0.7303 0.070 Uiso 1 1 calc R U . . .
C7 C 0.36430(8) 0.2935(4) 0.69427(16) 0.0654(6) Uani 1 1 d . . . . .
H7A H 0.3937 0.3016 0.7158 0.078 Uiso 1 1 calc R U . . .
C8 C 0.34265(7) 0.4466(3) 0.65273(15) 0.0615(5) Uani 1 1 d . . . . .
H8A H 0.3579 0.5569 0.6459 0.074 Uiso 1 1 calc R U . . .
C9 C 0.29899(7) 0.4364(3) 0.62175(13) 0.0516(5) Uani 1 1 d . . . . .
H9A H 0.2853 0.5404 0.5941 0.062 Uiso 1 1 calc R U . . .
C10 C 0.27436(6) 0.2729(2) 0.63058(11) 0.0411(4) Uani 1 1 d . . . . .
C11 C 0.22775(6) 0.2569(2) 0.60332(11) 0.0383(4) Uani 1 1 d . . . . .
C12 C 0.20425(6) 0.4155(2) 0.56443(11) 0.0403(4) Uani 1 1 d . . . . .
H12A H 0.2210 0.5190 0.5532 0.048 Uiso 1 1 calc R U . . .
N13 N 0.16275(5) 0.43208(19) 0.54320(10) 0.0410(3) Uani 1 1 d . . . . .
C14 C 0.14730(6) 0.6114(2) 0.50199(14) 0.0482(4) Uani 1 1 d . . . . .
H14A H 0.1488 0.6059 0.4376 0.058 Uiso 1 1 calc R U . . .
H14B H 0.1664 0.7112 0.5262 0.058 Uiso 1 1 calc R U . . .
C15 C 0.10066(7) 0.6544(3) 0.51970(15) 0.0525(5) Uani 1 1 d . . . . .
H15A H 0.0983 0.6397 0.5835 0.063 Uiso 1 1 calc R U . . .
H15B H 0.0942 0.7837 0.5041 0.063 Uiso 1 1 calc R U . . .
C16 C 0.06736(6) 0.5324(3) 0.46800(12) 0.0455(4) Uani 1 1 d . . . . .
N17 N 0.07176(5) 0.3466(2) 0.48083(11) 0.0463(4) Uani 1 1 d . . . . .
C18 C 0.04272(7) 0.2315(3) 0.43547(16) 0.0558(5) Uani 1 1 d . . . . .
H18A H 0.0461 0.1036 0.4443 0.067 Uiso 1 1 calc R U . . .
C19 C 0.00845(8) 0.2932(4) 0.37706(16) 0.0618(6) Uani 1 1 d . . . . .
H19A H -0.0111 0.2097 0.3469 0.074 Uiso 1 1 calc R U . . .
C20 C 0.00388(7) 0.4818(4) 0.36442(14) 0.0630(6) Uani 1 1 d . . . . .
H20A H -0.0192 0.5284 0.3255 0.076 Uiso 1 1 calc R U . . .
C21 C 0.03340(7) 0.6018(3) 0.40917(14) 0.0573(5) Uani 1 1 d . . . . .
H21A H 0.0306 0.7299 0.4000 0.069 Uiso 1 1 calc R U . . .
N30 N 0.07279(5) 0.1413(2) 0.68892(13) 0.0533(4) Uani 1 1 d . . . . .
O31 O 0.07718(5) 0.06596(19) 0.61321(10) 0.0583(4) Uani 1 1 d . . . . .
O32 O 0.09281(6) 0.2890(2) 0.70706(13) 0.0697(5) Uani 1 1 d . . . . .
O33 O 0.04925(6) 0.0677(3) 0.73927(13) 0.0846(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.8681(13) . ?
Cu1 N13 1.9361(15) . ?
Cu1 N17 1.9874(16) . ?
Cu1 O31 2.0455(14) . ?
O1 C2 1.297(2) . ?
C2 C11 1.411(2) . ?
C2 C3 1.433(2) . ?
C3 C4 1.341(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.424(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.411(3) . ?
C5 C10 1.419(2) . ?
C6 C7 1.360(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.394(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.375(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.410(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.453(3) . ?
C11 C12 1.435(2) . ?
C12 N13 1.288(2) . ?
C12 H12A 0.9300 . ?
N13 C14 1.480(2) . ?
C14 C15 1.521(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.497(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N17 1.349(2) . ?
C16 C21 1.383(3) . ?
N17 C18 1.344(3) . ?
C18 C19 1.367(3) . ?
C18 H18A 0.9300 . ?
C19 C20 1.369(3) . ?
C19 H19A 0.9300 . ?
C20 C21 1.371(3) . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9300 . ?
N30 O33 1.221(2) . ?
N30 O32 1.240(2) . ?
N30 O31 1.275(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N13 93.94(6) . . ?
O1 Cu1 N17 156.91(6) . . ?
N13 Cu1 N17 96.16(6) . . ?
O1 Cu1 O31 87.64(6) . . ?
N13 Cu1 O31 163.58(6) . . ?
N17 Cu1 O31 88.47(6) . . ?
C2 O1 Cu1 128.15(11) . . ?
O1 C2 C11 125.03(16) . . ?
O1 C2 C3 116.64(17) . . ?
C11 C2 C3 118.32(18) . . ?
C4 C3 C2 121.78(19) . . ?
C4 C3 H3A 119.1 . . ?
C2 C3 H3A 119.1 . . ?
C3 C4 C5 121.92(17) . . ?
C3 C4 H4A 119.0 . . ?
C5 C4 H4A 119.0 . . ?
C6 C5 C10 120.30(19) . . ?
C6 C5 C4 120.90(18) . . ?
C10 C5 C4 118.80(18) . . ?
C7 C6 C5 121.2(2) . . ?
C7 C6 H6A 119.4 . . ?
C5 C6 H6A 119.4 . . ?
C6 C7 C8 119.3(2) . . ?
C6 C7 H7A 120.4 . . ?
C8 C7 H7A 120.4 . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 H8A 119.7 . . ?
C7 C8 H8A 119.7 . . ?
C8 C9 C10 121.95(19) . . ?
C8 C9 H9A 119.0 . . ?
C10 C9 H9A 119.0 . . ?
C9 C10 C5 116.54(18) . . ?
C9 C10 C11 124.37(16) . . ?
C5 C10 C11 119.06(17) . . ?
C2 C11 C12 120.62(17) . . ?
C2 C11 C10 120.03(15) . . ?
C12 C11 C10 119.34(16) . . ?
N13 C12 C11 127.97(17) . . ?
N13 C12 H12A 116.0 . . ?
C11 C12 H12A 116.0 . . ?
C12 N13 C14 116.57(15) . . ?
C12 N13 Cu1 123.67(12) . . ?
C14 N13 Cu1 119.75(12) . . ?
N13 C14 C15 111.70(16) . . ?
N13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
N13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 113.48(15) . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
N17 C16 C21 120.17(18) . . ?
N17 C16 C15 116.75(16) . . ?
C21 C16 C15 123.08(18) . . ?
C18 N17 C16 118.83(17) . . ?
C18 N17 Cu1 118.75(14) . . ?
C16 N17 Cu1 122.37(13) . . ?
N17 C18 C19 123.3(2) . . ?
N17 C18 H18A 118.4 . . ?
C19 C18 H18A 118.4 . . ?
C18 C19 C20 117.9(2) . . ?
C18 C19 H19A 121.1 . . ?
C20 C19 H19A 121.1 . . ?
C19 C20 C21 119.9(2) . . ?
C19 C20 H20A 120.0 . . ?
C21 C20 H20A 120.0 . . ?
C20 C21 C16 119.9(2) . . ?
C20 C21 H21A 120.0 . . ?
C16 C21 H21A 120.0 . . ?
O33 N30 O32 123.27(19) . . ?
O33 N30 O31 119.56(17) . . ?
O32 N30 O31 117.17(17) . . ?
N30 O31 Cu1 103.35(11) . . ?

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
N13 Cu1 O1 C2 8.63(15) . . . . ?
N17 Cu1 O1 C2 124.49(18) . . . . ?
O31 Cu1 O1 C2 -155.00(15) . . . . ?
Cu1 O1 C2 C11 -6.5(3) . . . . ?
Cu1 O1 C2 C3 172.64(12) . . . . ?
O1 C2 C3 C4 -176.90(18) . . . . ?
C11 C2 C3 C4 2.3(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 176.85(18) . . . . ?
C3 C4 C5 C10 -2.3(3) . . . . ?
C10 C5 C6 C7 -0.7(3) . . . . ?
C4 C5 C6 C7 -179.90(19) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C9 C10 C5 -1.3(3) . . . . ?
C8 C9 C10 C11 176.73(19) . . . . ?
C6 C5 C10 C9 1.6(3) . . . . ?
C4 C5 C10 C9 -179.24(17) . . . . ?
C6 C5 C10 C11 -176.57(16) . . . . ?
C4 C5 C10 C11 2.6(2) . . . . ?
O1 C2 C11 C12 -1.3(3) . . . . ?
C3 C2 C11 C12 179.49(16) . . . . ?
O1 C2 C11 C10 177.23(16) . . . . ?
C3 C2 C11 C10 -1.9(2) . . . . ?
C9 C10 C11 C2 -178.49(17) . . . . ?
C5 C10 C11 C2 -0.5(2) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C5 C10 C11 C12 178.09(15) . . . . ?
C2 C11 C12 N13 4.7(3) . . . . ?
C10 C11 C12 N13 -173.91(17) . . . . ?
C11 C12 N13 C14 -178.71(17) . . . . ?
C11 C12 N13 Cu1 0.1(3) . . . . ?
C12 N13 C14 C15 -153.10(16) . . . . ?
Cu1 N13 C14 C15 28.1(2) . . . . ?
N13 C14 C15 C16 -71.6(2) . . . . ?
C14 C15 C16 N17 57.8(2) . . . . ?
C14 C15 C16 C21 -122.0(2) . . . . ?
C21 C16 N17 C18 0.1(3) . . . . ?
C15 C16 N17 C18 -179.68(18) . . . . ?
C21 C16 N17 Cu1 177.34(14) . . . . ?
C15 C16 N17 Cu1 -2.4(2) . . . . ?
C16 N17 C18 C19 -0.5(3) . . . . ?
Cu1 N17 C18 C19 -177.88(18) . . . . ?
N17 C18 C19 C20 0.2(4) . . . . ?
C18 C19 C20 C21 0.5(3) . . . . ?
C19 C20 C21 C16 -1.0(3) . . . . ?
N17 C16 C21 C20 0.6(3) . . . . ?
C15 C16 C21 C20 -179.59(19) . . . . ?
O33 N30 O31 Cu1 -177.58(16) . . . . ?
O32 N30 O31 Cu1 3.1(2) . . . . ?

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.056

_shelxl_version_number           2014-3


_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_445
_database_code_depnum_ccdc_archive 'CCDC 1824509'
_audit_update_record             
;
2018-02-17 deposited with the CCDC.
2018-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 Cl Cu N2 O'
_chemical_formula_weight         374.31

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   12.1310(4)
_cell_length_b                   8.8134(3)
_cell_length_c                   29.6697(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3172.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    21872
_cell_measurement_theta_min      2.311
_cell_measurement_theta_max      28.510

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_F_000             1528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.283
_exptl_crystal_size_min          0.151
_exptl_absorpt_coefficient_mu    1.550
_shelx_estimated_absorpt_T_min   0.659
_shelx_estimated_absorpt_T_max   0.800
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_T_max  0.816
_exptl_absorpt_process_details   'Oxford Diffraction CrysAlis'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Oxford Sapphire CCD'
_diffrn_measurement_method       θ/2θ
_diffrn_detector_area_resol_mean 8.2564
_diffrn_reflns_number            20459
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.311
_diffrn_reflns_theta_max         28.510
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.797
_diffrn_reflns_point_group_measured_fraction_full 0.881
_reflns_number_total             6418
_reflns_number_gt                5500
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.674
_reflns_Friedel_fraction_max     0.655
_reflns_Friedel_fraction_full    0.757

_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       'Oxford Diffraction CrysAlis'
_computing_cell_refinement       'Oxford Diffraction CrysAlis'
_computing_data_reduction        'Oxford Diffraction CrysAlis'
_computing_structure_solution    'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'

_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)+(0.0433P)²+0.8036P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2005 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.232(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6418
_refine_ls_number_parameters     415
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0880
_refine_ls_wR_factor_gt          0.0804
_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
Cu1 Cu 0.41933(5) 0.09369(7) 0.38357(2) 0.03385(16) Uani 1 1 d . . . . .
Cl1 Cl 0.33577(11) 0.28864(18) 0.34736(6) 0.0554(4) Uani 1 1 d . . . . .
N1 N 0.5641(3) 0.1572(6) 0.35825(18) 0.0318(11) Uani 1 1 d . . . . .
C2 C 0.5991(4) 0.2990(6) 0.36541(19) 0.0402(12) Uani 1 1 d . . . . .
H2A H 0.5574 0.3615 0.3840 0.048 Uiso 1 1 calc R U . . .
C3 C 0.6940(5) 0.3572(7) 0.3465(2) 0.0508(15) Uani 1 1 d . . . . .
H3A H 0.7160 0.4563 0.3523 0.061 Uiso 1 1 calc R U . . .
C4 C 0.7555(5) 0.2637(8) 0.3187(2) 0.0520(15) Uani 1 1 d . . . . .
H4A H 0.8197 0.2993 0.3052 0.062 Uiso 1 1 calc R U . . .
C5 C 0.7208(4) 0.1188(7) 0.3115(2) 0.0456(14) Uani 1 1 d . . . . .
H5A H 0.7615 0.0551 0.2928 0.055 Uiso 1 1 calc R U . . .
C6 C 0.6242(4) 0.0649(7) 0.33183(19) 0.0366(13) Uani 1 1 d . . . . .
C7 C 0.5827(4) -0.0928(6) 0.3247(2) 0.0410(13) Uani 1 1 d . . . . .
H7A H 0.6369 -0.1490 0.3075 0.049 Uiso 1 1 calc R U . . .
H7B H 0.5156 -0.0883 0.3070 0.049 Uiso 1 1 calc R U . . .
C8 C 0.5591(5) -0.1783(7) 0.3681(2) 0.0390(15) Uani 1 1 d . . . . .
H8A H 0.5494 -0.2851 0.3612 0.047 Uiso 1 1 calc R U . . .
H8B H 0.6218 -0.1687 0.3881 0.047 Uiso 1 1 calc R U . . .
N9 N 0.4603(3) -0.1217(5) 0.39086(17) 0.0361(11) Uani 1 1 d . . . . .
C10 C 0.4050(4) -0.2158(6) 0.41484(19) 0.0359(12) Uani 1 1 d . . . . .
H10A H 0.4330 -0.3139 0.4162 0.043 Uiso 1 1 calc R U . . .
C11 C 0.3059(4) -0.1897(6) 0.43977(17) 0.0312(10) Uani 1 1 d . . . . .
C12 C 0.2479(5) -0.3175(6) 0.45960(18) 0.0381(12) Uani 1 1 d . . . . .
C13 C 0.2862(6) -0.4686(8) 0.4575(3) 0.0531(17) Uani 1 1 d . . . . .
H13A H 0.3525 -0.4892 0.4429 0.064 Uiso 1 1 calc R U . . .
C14 C 0.2272(7) -0.5870(7) 0.4766(3) 0.068(2) Uani 1 1 d . . . . .
H14A H 0.2549 -0.6852 0.4752 0.081 Uiso 1 1 calc R U . . .
C15 C 0.1263(7) -0.5599(10) 0.4979(3) 0.076(3) Uani 1 1 d . . . . .
H15A H 0.0870 -0.6393 0.5109 0.091 Uiso 1 1 calc R U . . .
C16 C 0.0866(6) -0.4165(9) 0.4994(3) 0.0607(19) Uani 1 1 d . . . . .
H16A H 0.0187 -0.3992 0.5130 0.073 Uiso 1 1 calc R U . . .
C17 C 0.1448(4) -0.2921(7) 0.48105(18) 0.0425(13) Uani 1 1 d . . . . .
C18 C 0.1023(4) -0.1433(7) 0.48334(19) 0.0432(13) Uani 1 1 d . . . . .
H18A H 0.0343 -0.1270 0.4970 0.052 Uiso 1 1 calc R U . . .
C19 C 0.1579(5) -0.0245(8) 0.4663(3) 0.0425(16) Uani 1 1 d . . . . .
H19A H 0.1292 0.0727 0.4697 0.051 Uiso 1 1 calc R U . . .
C20 C 0.2609(4) -0.0447(7) 0.44297(19) 0.0346(11) Uani 1 1 d . . . . .
O21 O 0.3043(3) 0.0786(4) 0.42611(16) 0.0454(10) Uani 1 1 d . . . . .
Cu2 Cu 0.82472(4) 0.40750(7) 0.17734(2) 0.03212(16) Uani 1 1 d . . . . .
Cl2 Cl 0.90875(11) 0.21335(17) 0.21369(6) 0.0504(4) Uani 1 1 d . . . . .
N31 N 0.6803(3) 0.3447(6) 0.20295(19) 0.0333(12) Uani 1 1 d . . . . .
C32 C 0.6461(4) 0.2005(6) 0.19576(19) 0.0385(11) Uani 1 1 d . . . . .
H32A H 0.6876 0.1382 0.1770 0.046 Uiso 1 1 calc R U . . .
C33 C 0.5523(5) 0.1430(7) 0.21523(19) 0.0446(13) Uani 1 1 d . . . . .
H33A H 0.5306 0.0435 0.2097 0.054 Uiso 1 1 calc R U . . .
C34 C 0.4914(4) 0.2346(8) 0.2428(2) 0.0507(15) Uani 1 1 d . . . . .
H34A H 0.4282 0.1975 0.2567 0.061 Uiso 1 1 calc R U . . .
C35 C 0.5244(4) 0.3819(7) 0.2499(2) 0.0431(13) Uani 1 1 d . . . . .
H35A H 0.4830 0.4456 0.2683 0.052 Uiso 1 1 calc R U . . .
C36 C 0.6197(4) 0.4352(6) 0.22949(18) 0.0335(12) Uani 1 1 d . . . . .
C37 C 0.6617(5) 0.5936(7) 0.2367(2) 0.0414(14) Uani 1 1 d . . . . .
H37A H 0.7293 0.5892 0.2540 0.050 Uiso 1 1 calc R U . . .
H37B H 0.6079 0.6502 0.2540 0.050 Uiso 1 1 calc R U . . .
C38 C 0.6839(4) 0.6771(8) 0.1926(3) 0.0418(17) Uani 1 1 d . . . . .
H38A H 0.6208 0.6658 0.1728 0.050 Uiso 1 1 calc R U . . .
H38B H 0.6934 0.7844 0.1988 0.050 Uiso 1 1 calc R U . . .
N39 N 0.7834(3) 0.6184(4) 0.16971(16) 0.0314(10) Uani 1 1 d . . . . .
C40 C 0.8402(4) 0.7178(6) 0.14694(18) 0.0314(11) Uani 1 1 d . . . . .
H40A H 0.8133 0.8166 0.1470 0.038 Uiso 1 1 calc R U . . .
C41 C 0.9391(4) 0.6926(6) 0.12183(17) 0.0303(10) Uani 1 1 d . . . . .
C42 C 0.9981(4) 0.8212(6) 0.10304(16) 0.0314(10) Uani 1 1 d . . . . .
C43 C 0.9642(5) 0.9751(7) 0.1075(3) 0.0433(15) Uani 1 1 d . . . . .
H43A H 0.8966 0.9955 0.1211 0.052 Uiso 1 1 calc R U . . .
C44 C 1.0258(6) 1.0925(7) 0.0930(2) 0.0541(16) Uani 1 1 d . . . . .
H44A H 1.0019 1.1915 0.0977 0.065 Uiso 1 1 calc R U . . .
C45 C 1.1268(6) 1.0654(7) 0.0707(2) 0.0554(17) Uani 1 1 d . . . . .
H45A H 1.1685 1.1461 0.0599 0.066 Uiso 1 1 calc R U . . .
C46 C 1.1625(5) 0.9199(7) 0.0651(2) 0.0484(16) Uani 1 1 d . . . . .
H46A H 1.2295 0.9021 0.0507 0.058 Uiso 1 1 calc R U . . .
C47 C 1.1000(4) 0.7970(6) 0.08056(17) 0.0363(11) Uani 1 1 d . . . . .
C48 C 1.1404(4) 0.6458(6) 0.07667(18) 0.0377(11) Uani 1 1 d . . . . .
H48A H 1.2070 0.6293 0.0619 0.045 Uiso 1 1 calc R U . . .
C49 C 1.0850(5) 0.5249(7) 0.0937(3) 0.0374(15) Uani 1 1 d . . . . .
H49A H 1.1135 0.4277 0.0899 0.045 Uiso 1 1 calc R U . . .
C50 C 0.9832(4) 0.5447(6) 0.1176(2) 0.0329(11) Uani 1 1 d . . . . .
O51 O 0.9389(3) 0.4242(4) 0.13483(15) 0.0421(10) 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 O21 1.887(4) . ?
Cu1 N9 1.974(4) . ?
Cu1 N1 1.990(5) . ?
Cu1 Cl1 2.2658(16) . ?
N1 C2 1.337(7) . ?
N1 C6 1.345(8) . ?
C2 C3 1.379(8) . ?
C2 H2A 0.9300 . ?
C3 C4 1.384(10) . ?
C3 H3A 0.9300 . ?
C4 C5 1.362(9) . ?
C4 H4A 0.9300 . ?
C5 C6 1.401(8) . ?
C5 H5A 0.9300 . ?
C6 C7 1.493(8) . ?
C7 C8 1.517(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N9 1.463(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
N9 C10 1.283(7) . ?
C10 C11 1.429(7) . ?
C10 H10A 0.9300 . ?
C11 C20 1.393(8) . ?
C11 C12 1.453(7) . ?
C12 C13 1.412(9) . ?
C12 C17 1.421(8) . ?
C13 C14 1.387(9) . ?
C13 H13A 0.9300 . ?
C14 C15 1.398(11) . ?
C14 H14A 0.9300 . ?
C15 C16 1.353(12) . ?
C15 H15A 0.9300 . ?
C16 C17 1.413(8) . ?
C16 H16A 0.9300 . ?
C17 C18 1.411(8) . ?
C18 C19 1.344(9) . ?
C18 H18A 0.9300 . ?
C19 C20 1.440(9) . ?
C19 H19A 0.9300 . ?
C20 O21 1.307(7) . ?
Cu2 O51 1.879(4) . ?
Cu2 N39 1.938(4) . ?
Cu2 N31 1.989(4) . ?
Cu2 Cl2 2.2650(15) . ?
N31 C36 1.340(7) . ?
N31 C32 1.353(7) . ?
C32 C33 1.373(7) . ?
C32 H32A 0.9300 . ?
C33 C34 1.366(9) . ?
C33 H33A 0.9300 . ?
C34 C35 1.375(9) . ?
C34 H34A 0.9300 . ?
C35 C36 1.386(7) . ?
C35 H35A 0.9300 . ?
C36 C37 1.501(8) . ?
C37 C38 1.523(9) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 N39 1.480(7) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
N39 C40 1.304(6) . ?
C40 C41 1.429(7) . ?
C40 H40A 0.9300 . ?
C41 C50 1.415(7) . ?
C41 C42 1.452(7) . ?
C42 C47 1.420(7) . ?
C42 C43 1.424(8) . ?
C43 C44 1.347(8) . ?
C43 H43A 0.9300 . ?
C44 C45 1.413(9) . ?
C44 H44A 0.9300 . ?
C45 C46 1.364(10) . ?
C45 H45A 0.9300 . ?
C46 C47 1.400(7) . ?
C46 H46A 0.9300 . ?
C47 C48 1.425(7) . ?
C48 C49 1.358(8) . ?
C48 H48A 0.9300 . ?
C49 C50 1.434(9) . ?
C49 H49A 0.9300 . ?
C50 O51 1.296(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
O21 Cu1 N9 92.59(18) . . ?
O21 Cu1 N1 157.7(2) . . ?
N9 Cu1 N1 95.1(2) . . ?
O21 Cu1 Cl1 92.28(13) . . ?
N9 Cu1 Cl1 153.35(16) . . ?
N1 Cu1 Cl1 90.13(15) . . ?
C2 N1 C6 119.1(5) . . ?
C2 N1 Cu1 118.9(4) . . ?
C6 N1 Cu1 121.9(4) . . ?
N1 C2 C3 123.2(6) . . ?
N1 C2 H2A 118.4 . . ?
C3 C2 H2A 118.4 . . ?
C2 C3 C4 118.1(6) . . ?
C2 C3 H3A 120.9 . . ?
C4 C3 H3A 120.9 . . ?
C5 C4 C3 119.0(5) . . ?
C5 C4 H4A 120.5 . . ?
C3 C4 H4A 120.5 . . ?
C4 C5 C6 120.6(6) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
N1 C6 C5 120.0(6) . . ?
N1 C6 C7 117.6(5) . . ?
C5 C6 C7 122.5(5) . . ?
C6 C7 C8 114.0(5) . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
N9 C8 C7 112.1(5) . . ?
N9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
N9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C10 N9 C8 117.7(5) . . ?
C10 N9 Cu1 123.4(4) . . ?
C8 N9 Cu1 118.9(4) . . ?
N9 C10 C11 128.5(5) . . ?
N9 C10 H10A 115.7 . . ?
C11 C10 H10A 115.7 . . ?
C20 C11 C10 120.9(5) . . ?
C20 C11 C12 119.5(4) . . ?
C10 C11 C12 119.5(5) . . ?
C13 C12 C17 117.3(5) . . ?
C13 C12 C11 123.6(5) . . ?
C17 C12 C11 119.1(5) . . ?
C14 C13 C12 121.4(7) . . ?
C14 C13 H13A 119.3 . . ?
C12 C13 H13A 119.3 . . ?
C13 C14 C15 120.6(7) . . ?
C13 C14 H14A 119.7 . . ?
C15 C14 H14A 119.7 . . ?
C16 C15 C14 119.0(7) . . ?
C16 C15 H15A 120.5 . . ?
C14 C15 H15A 120.5 . . ?
C15 C16 C17 122.3(7) . . ?
C15 C16 H16A 118.8 . . ?
C17 C16 H16A 118.8 . . ?
C18 C17 C16 121.4(5) . . ?
C18 C17 C12 119.3(5) . . ?
C16 C17 C12 119.3(6) . . ?
C19 C18 C17 121.5(5) . . ?
C19 C18 H18A 119.2 . . ?
C17 C18 H18A 119.2 . . ?
C18 C19 C20 121.3(6) . . ?
C18 C19 H19A 119.3 . . ?
C20 C19 H19A 119.3 . . ?
O21 C20 C11 125.4(5) . . ?
O21 C20 C19 115.5(5) . . ?
C11 C20 C19 119.1(5) . . ?
C20 O21 Cu1 127.8(4) . . ?
O51 Cu2 N39 92.11(17) . . ?
O51 Cu2 N31 158.1(2) . . ?
N39 Cu2 N31 94.82(19) . . ?
O51 Cu2 Cl2 92.71(13) . . ?
N39 Cu2 Cl2 153.67(15) . . ?
N31 Cu2 Cl2 90.24(16) . . ?
C36 N31 C32 118.9(5) . . ?
C36 N31 Cu2 122.8(4) . . ?
C32 N31 Cu2 118.1(4) . . ?
N31 C32 C33 122.3(5) . . ?
N31 C32 H32A 118.9 . . ?
C33 C32 H32A 118.9 . . ?
C34 C33 C32 118.8(5) . . ?
C34 C33 H33A 120.6 . . ?
C32 C33 H33A 120.6 . . ?
C33 C34 C35 119.5(5) . . ?
C33 C34 H34A 120.3 . . ?
C35 C34 H34A 120.3 . . ?
C34 C35 C36 119.7(6) . . ?
C34 C35 H35A 120.1 . . ?
C36 C35 H35A 120.1 . . ?
N31 C36 C35 120.8(5) . . ?
N31 C36 C37 116.8(4) . . ?
C35 C36 C37 122.4(5) . . ?
C36 C37 C38 112.8(5) . . ?
C36 C37 H37A 109.0 . . ?
C38 C37 H37A 109.0 . . ?
C36 C37 H37B 109.0 . . ?
C38 C37 H37B 109.0 . . ?
H37A C37 H37B 107.8 . . ?
N39 C38 C37 111.7(5) . . ?
N39 C38 H38A 109.3 . . ?
C37 C38 H38A 109.3 . . ?
N39 C38 H38B 109.3 . . ?
C37 C38 H38B 109.3 . . ?
H38A C38 H38B 107.9 . . ?
C40 N39 C38 115.8(4) . . ?
C40 N39 Cu2 124.7(3) . . ?
C38 N39 Cu2 119.5(4) . . ?
N39 C40 C41 127.5(4) . . ?
N39 C40 H40A 116.2 . . ?
C41 C40 H40A 116.2 . . ?
C50 C41 C40 120.5(5) . . ?
C50 C41 C42 119.9(4) . . ?
C40 C41 C42 119.5(4) . . ?
C47 C42 C43 116.0(5) . . ?
C47 C42 C41 119.5(4) . . ?
C43 C42 C41 124.4(5) . . ?
C44 C43 C42 122.7(6) . . ?
C44 C43 H43A 118.6 . . ?
C42 C43 H43A 118.6 . . ?
C43 C44 C45 120.1(6) . . ?
C43 C44 H44A 119.9 . . ?
C45 C44 H44A 119.9 . . ?
C46 C45 C44 119.5(6) . . ?
C46 C45 H45A 120.3 . . ?
C44 C45 H45A 120.3 . . ?
C45 C46 C47 121.0(6) . . ?
C45 C46 H46A 119.5 . . ?
C47 C46 H46A 119.5 . . ?
C46 C47 C42 120.7(5) . . ?
C46 C47 C48 120.7(5) . . ?
C42 C47 C48 118.5(4) . . ?
C49 C48 C47 122.3(5) . . ?
C49 C48 H48A 118.9 . . ?
C47 C48 H48A 118.9 . . ?
C48 C49 C50 121.0(5) . . ?
C48 C49 H49A 119.5 . . ?
C50 C49 H49A 119.5 . . ?
O51 C50 C41 124.3(5) . . ?
O51 C50 C49 116.9(5) . . ?
C41 C50 C49 118.8(5) . . ?
C50 O51 Cu2 129.4(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 0.8(8) . . . . ?
Cu1 N1 C2 C3 -175.0(4) . . . . ?
N1 C2 C3 C4 0.2(9) . . . . ?
C2 C3 C4 C5 -0.5(9) . . . . ?
C3 C4 C5 C6 -0.1(9) . . . . ?
C2 N1 C6 C5 -1.4(8) . . . . ?
Cu1 N1 C6 C5 174.3(4) . . . . ?
C2 N1 C6 C7 179.8(5) . . . . ?
Cu1 N1 C6 C7 -4.5(7) . . . . ?
C4 C5 C6 N1 1.1(9) . . . . ?
C4 C5 C6 C7 179.8(6) . . . . ?
N1 C6 C7 C8 -53.3(7) . . . . ?
C5 C6 C7 C8 127.9(6) . . . . ?
C6 C7 C8 N9 72.1(6) . . . . ?
C7 C8 N9 C10 150.7(5) . . . . ?
C7 C8 N9 Cu1 -29.6(7) . . . . ?
C8 N9 C10 C11 -179.2(5) . . . . ?
Cu1 N9 C10 C11 1.1(8) . . . . ?
N9 C10 C11 C20 -4.8(9) . . . . ?
N9 C10 C11 C12 171.3(5) . . . . ?
C20 C11 C12 C13 179.0(6) . . . . ?
C10 C11 C12 C13 2.9(8) . . . . ?
C20 C11 C12 C17 1.4(7) . . . . ?
C10 C11 C12 C17 -174.8(5) . . . . ?
C17 C12 C13 C14 -1.7(10) . . . . ?
C11 C12 C13 C14 -179.4(7) . . . . ?
C12 C13 C14 C15 1.2(13) . . . . ?
C13 C14 C15 C16 0.4(13) . . . . ?
C14 C15 C16 C17 -1.5(12) . . . . ?
C15 C16 C17 C18 -179.4(7) . . . . ?
C15 C16 C17 C12 1.0(10) . . . . ?
C13 C12 C17 C18 -179.0(6) . . . . ?
C11 C12 C17 C18 -1.2(8) . . . . ?
C13 C12 C17 C16 0.6(9) . . . . ?
C11 C12 C17 C16 178.4(5) . . . . ?
C16 C17 C18 C19 179.4(7) . . . . ?
C12 C17 C18 C19 -1.0(9) . . . . ?
C17 C18 C19 C20 3.1(11) . . . . ?
C10 C11 C20 O21 -3.0(8) . . . . ?
C12 C11 C20 O21 -179.1(5) . . . . ?
C10 C11 C20 C19 176.6(6) . . . . ?
C12 C11 C20 C19 0.6(8) . . . . ?
C18 C19 C20 O21 176.9(6) . . . . ?
C18 C19 C20 C11 -2.8(10) . . . . ?
C11 C20 O21 Cu1 13.9(8) . . . . ?
C19 C20 O21 Cu1 -165.8(5) . . . . ?
N9 Cu1 O21 C20 -13.5(5) . . . . ?
N1 Cu1 O21 C20 -123.8(6) . . . . ?
Cl1 Cu1 O21 C20 140.3(5) . . . . ?
C36 N31 C32 C33 -1.0(8) . . . . ?
Cu2 N31 C32 C33 174.4(4) . . . . ?
N31 C32 C33 C34 0.0(8) . . . . ?
C32 C33 C34 C35 0.9(8) . . . . ?
C33 C34 C35 C36 -0.9(9) . . . . ?
C32 N31 C36 C35 1.0(8) . . . . ?
Cu2 N31 C36 C35 -174.1(4) . . . . ?
C32 N31 C36 C37 179.5(5) . . . . ?
Cu2 N31 C36 C37 4.4(7) . . . . ?
C34 C35 C36 N31 -0.1(8) . . . . ?
C34 C35 C36 C37 -178.5(5) . . . . ?
N31 C36 C37 C38 53.7(7) . . . . ?
C35 C36 C37 C38 -127.8(5) . . . . ?
C36 C37 C38 N39 -72.6(6) . . . . ?
C37 C38 N39 C40 -147.0(5) . . . . ?
C37 C38 N39 Cu2 30.1(7) . . . . ?
C38 N39 C40 C41 179.9(5) . . . . ?
Cu2 N39 C40 C41 3.0(8) . . . . ?
N39 C40 C41 C50 3.4(8) . . . . ?
N39 C40 C41 C42 -172.6(5) . . . . ?
C50 C41 C42 C47 0.0(7) . . . . ?
C40 C41 C42 C47 176.0(4) . . . . ?
C50 C41 C42 C43 -176.4(6) . . . . ?
C40 C41 C42 C43 -0.4(8) . . . . ?
C47 C42 C43 C44 -2.3(10) . . . . ?
C41 C42 C43 C44 174.2(6) . . . . ?
C42 C43 C44 C45 2.6(11) . . . . ?
C43 C44 C45 C46 -1.8(11) . . . . ?
C44 C45 C46 C47 0.9(10) . . . . ?
C45 C46 C47 C42 -0.8(9) . . . . ?
C45 C46 C47 C48 -176.8(6) . . . . ?
C43 C42 C47 C46 1.4(8) . . . . ?
C41 C42 C47 C46 -175.3(5) . . . . ?
C43 C42 C47 C48 177.5(5) . . . . ?
C41 C42 C47 C48 0.8(7) . . . . ?
C46 C47 C48 C49 176.0(6) . . . . ?
C42 C47 C48 C49 -0.1(9) . . . . ?
C47 C48 C49 C50 -1.4(11) . . . . ?
C40 C41 C50 O51 1.1(8) . . . . ?
C42 C41 C50 O51 177.0(5) . . . . ?
C40 C41 C50 C49 -177.4(5) . . . . ?
C42 C41 C50 C49 -1.4(8) . . . . ?
C48 C49 C50 O51 -176.4(6) . . . . ?
C48 C49 C50 C41 2.2(10) . . . . ?
C41 C50 O51 Cu2 -12.2(8) . . . . ?
C49 C50 O51 Cu2 166.3(5) . . . . ?
N39 Cu2 O51 C50 14.2(5) . . . . ?
N31 Cu2 O51 C50 122.7(6) . . . . ?
Cl2 Cu2 O51 C50 -139.9(5) . . . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.051

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
