# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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 
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data_p-1
_database_code_depnum_ccdc_archive 'CCDC 1552123'
_audit_update_record             
;
2018-07-17 deposited with the CCDC.
2018-07-25 downloaded from the CCDC.
;
_audit_creation_date             2018-07-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H28 Cl4 Cu2 N6 O2, 4.75(H2 O)'
_chemical_formula_sum            'C36 H37.50 Cl4 Cu2 N6 O6.75'
_chemical_formula_weight         931.10
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.509(3)
_cell_length_b                   13.689(3)
_cell_length_c                   14.613(3)
_cell_angle_alpha                94.72(3)
_cell_angle_beta                 115.28(3)
_cell_angle_gamma                114.86(3)
_cell_volume                     1945.6(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12849
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.021
_cell_measurement_theta_min      1.626
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.423
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             951
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_Laue_measured_fraction_full 0.940
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12849
_diffrn_reflns_point_group_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         1.626
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.940
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_source                   synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.63000
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4817
_reflns_number_total             7197
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'PAL BL2D-SMDC Program'
_computing_cell_refinement       'HKL3000sm (Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.280
_refine_diff_density_min         -1.210
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         7197
_refine_ls_number_restraints     402
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0644
_refine_ls_restrained_S_all      1.149
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1700
_refine_ls_wR_factor_ref         0.1910
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Rigid bond restraints
 C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17,
 C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, C31, C32, C33,
  C34, C35, C36, N1, N2, N3, N4, N5, N6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25
\\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33
\\sim C34 \\sim C35 \\sim C36 \\sim N1 \\sim N2 \\sim N3 \\sim N4 \\sim N5
\\sim N6: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Others
 Fixed Sof: O3(0.75) H3A(0.75) H3B(0.75) O4(0.75) H4A(0.75) H4B(0.75) O5(0.75)
 H5A(0.75) H5B(0.75) O6(0.75) H6B(0.75) H6A(0.75) O8(0.75) H8A(0.75) H8B(0.75)
5.a Free rotating group:
 O7(H7B,H7A), O3(H3A,H3B), O4(H4A,H4B), O5(H5A,H5B), O6(H6B,H6A), O8(H8A,H8B)
5.b Rotating group:
 O1(H1A,H1B), O2(H2A,H2B)
5.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27),
  C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34),
 C35(H35), C36(H36)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.59292(7) 0.34566(6) 1.02258(5) 0.0313(2) Uani 1 1 d . . . . .
Cu2 Cu 0.15986(8) 0.18515(6) 0.45105(5) 0.0345(2) Uani 1 1 d . . . . .
Cl1 Cl 0.79343(15) 0.35297(12) 1.17807(11) 0.0357(3) Uani 1 1 d . . . . .
Cl2 Cl 0.13175(19) 0.20179(14) 0.27320(12) 0.0463(4) Uani 1 1 d . . . . .
Cl3 Cl 0.50723(18) 0.42049(15) 1.10182(13) 0.0505(4) Uani 1 1 d . . . . .
Cl4 Cl -0.0574(3) 0.06499(19) 0.40937(19) 0.0759(6) Uani 1 1 d . . . . .
O1 O 0.1869(5) 0.0536(4) 0.4380(3) 0.0463(11) Uani 1 1 d . . . . .
H1A H 0.152318 0.008087 0.471456 0.069 Uiso 1 1 d GR . . . .
H1B H 0.146120 0.012648 0.365727 0.069 Uiso 1 1 d GR . . . .
O2 O 0.7027(5) 0.5021(3) 1.0193(3) 0.0461(11) Uani 1 1 d . . . . .
H2A H 0.651657 0.533507 0.991788 0.069 Uiso 1 1 d GR . . . .
H2B H 0.763665 0.525160 1.091393 0.069 Uiso 1 1 d GR . . . .
N1 N 0.4518(5) 0.1855(4) 0.9928(3) 0.0290(10) Uani 1 1 d . U . . .
N2 N 0.6087(5) 0.2762(4) 0.9023(4) 0.0292(10) Uani 1 1 d . U . . .
N3 N 0.1427(5) 0.3179(4) 0.4928(3) 0.0305(10) Uani 1 1 d . U . . .
N4 N 0.3683(5) 0.2925(4) 0.5442(4) 0.0338(11) Uani 1 1 d . U . . .
N5 N -0.0358(5) 0.0824(4) 0.7716(4) 0.0356(11) Uani 1 1 d . U . . .
C1 C 0.1951(5) 0.3685(4) 0.5980(4) 0.0262(11) Uani 1 1 d . U . . .
C2 C 0.3317(6) 0.1297(5) 0.8994(4) 0.0274(11) Uani 1 1 d . U . . .
C3 C 0.3797(5) 0.2373(5) 0.7764(4) 0.0271(11) Uani 1 1 d . U . . .
C4 C 0.2299(5) 0.3040(4) 0.6733(4) 0.0249(11) Uani 1 1 d . U . . .
C5 C 0.3440(5) 0.2907(4) 0.7005(4) 0.0256(11) Uani 1 1 d . U . . .
C6 C 0.3008(6) 0.1962(4) 0.8245(4) 0.0259(11) Uani 1 1 d . U . . .
C7 C 0.4291(6) 0.3382(4) 0.6510(4) 0.0278(11) Uani 1 1 d . U . . .
C8 C 0.4988(6) 0.2214(4) 0.8016(4) 0.0268(11) Uani 1 1 d . U . . .
C9 C 0.1523(5) 0.2640(5) 0.7213(4) 0.0271(11) Uani 1 1 d . U . . .
C10 C 0.2092(6) 0.4725(5) 0.6339(4) 0.0296(12) Uani 1 1 d . U . . .
H10 H 0.247552 0.506868 0.706287 0.036 Uiso 1 1 calc R . . . .
C11 C 0.1862(6) 0.2079(5) 0.7966(4) 0.0289(11) Uani 1 1 d . U . . .
C12 C 0.7211(6) 0.2707(5) 0.9238(5) 0.0332(13) Uani 1 1 d . U . . .
H12 H 0.797104 0.309025 0.992443 0.040 Uiso 1 1 calc R . . . .
C13 C 0.0970(6) 0.1592(5) 0.8428(5) 0.0329(12) Uani 1 1 d . U . . .
C14 C 0.4986(6) 0.1550(5) 0.7247(5) 0.0338(13) Uani 1 1 d . U . . .
H14 H 0.420402 0.113847 0.657433 0.041 Uiso 1 1 calc R . . . .
N6 N 0.0476(7) 0.3499(5) 0.7794(6) 0.0597(16) Uani 1 1 d . U . . .
C15 C 0.7289(6) 0.2107(5) 0.8487(5) 0.0353(13) Uani 1 1 d . U . . .
H15 H 0.809670 0.211008 0.865475 0.042 Uiso 1 1 calc R . . . .
C16 C 0.4783(6) 0.1281(5) 1.0617(5) 0.0364(13) Uani 1 1 d . U . . .
H16 H 0.559991 0.166320 1.127064 0.044 Uiso 1 1 calc R . . . .
C17 C 0.0969(6) 0.3682(5) 0.4223(4) 0.0344(13) Uani 1 1 d . U . . .
H17 H 0.058199 0.333116 0.350051 0.041 Uiso 1 1 calc R . . . .
C18 C 0.2404(6) 0.0172(5) 0.8732(5) 0.0325(12) Uani 1 1 d . U . . .
H18 H 0.158346 -0.019542 0.808119 0.039 Uiso 1 1 calc R . . . .
C19 C 0.1056(6) 0.4697(5) 0.4539(5) 0.0344(13) Uani 1 1 d . U . . .
H19 H 0.070958 0.501371 0.403011 0.041 Uiso 1 1 calc R . . . .
C20 C 0.1648(6) 0.5244(5) 0.5597(5) 0.0339(13) Uani 1 1 d . U . . .
H20 H 0.175300 0.595204 0.581758 0.041 Uiso 1 1 calc R . . . .
C21 C 0.5650(6) 0.4261(5) 0.7122(5) 0.0349(13) Uani 1 1 d . U . . .
H21 H 0.605083 0.456607 0.785458 0.042 Uiso 1 1 calc R . . . .
C22 C 0.1482(7) 0.1940(5) 0.9513(5) 0.0377(14) Uani 1 1 d . U . . .
H22 H 0.240266 0.246955 0.998534 0.045 Uiso 1 1 calc R . . . .
C23 C 0.3907(6) 0.0165(5) 1.0401(5) 0.0365(13) Uani 1 1 d . U . . .
H23 H 0.412161 -0.020060 1.090254 0.044 Uiso 1 1 calc R . . . .
C24 C 0.2702(6) -0.0416(5) 0.9436(5) 0.0354(13) Uani 1 1 d . U . . .
H24 H 0.210272 -0.118590 0.926007 0.043 Uiso 1 1 calc R . . . .
C25 C 0.6151(7) 0.1506(5) 0.7488(5) 0.0365(13) Uani 1 1 d . U . . .
H25 H 0.616550 0.107051 0.697589 0.044 Uiso 1 1 calc R . . . .
C26 C 0.0322(7) 0.2795(5) 0.6947(5) 0.0394(14) Uani 1 1 d . U . . .
C27 C -0.0767(7) 0.0685(5) 0.9151(5) 0.0430(15) Uani 1 1 d . U . . .
H27 H -0.138408 0.034745 0.937912 0.052 Uiso 1 1 calc R . . . .
C28 C -0.1200(7) 0.0393(6) 0.8094(6) 0.0415(14) Uani 1 1 d . U . . .
H28 H -0.212077 -0.012884 0.761140 0.050 Uiso 1 1 calc R . . . .
C29 C 0.4433(7) 0.3320(6) 0.4974(5) 0.0413(14) Uani 1 1 d . U . . .
H29 H 0.403216 0.299193 0.424451 0.050 Uiso 1 1 calc R . . . .
C30 C 0.0569(7) 0.1472(6) 0.9884(5) 0.0422(15) Uani 1 1 d . U . . .
H30 H 0.086665 0.169078 1.060745 0.051 Uiso 1 1 calc R . . . .
C31 C 0.6395(6) 0.4673(6) 0.6628(5) 0.0438(15) Uani 1 1 d . U . . .
H31 H 0.730055 0.526447 0.702074 0.053 Uiso 1 1 calc R . . . .
C32 C 0.5771(7) 0.4191(6) 0.5545(6) 0.0466(16) Uani 1 1 d . U . . .
H32 H 0.625637 0.445641 0.519769 0.056 Uiso 1 1 calc R . . . .
C33 C -0.0792(7) 0.2264(7) 0.5932(7) 0.0598(19) Uani 1 1 d . U . . .
H33 H -0.085397 0.182388 0.537152 0.072 Uiso 1 1 calc R . . . .
C34 C -0.1649(9) 0.3172(7) 0.6760(7) 0.0589(18) Uani 1 1 d . U . . .
H34 H -0.234972 0.328263 0.672221 0.071 Uiso 1 1 calc R . . . .
C35 C -0.1940(8) 0.2501(7) 0.5849(6) 0.066(2) Uani 1 1 d . U . . .
H35 H -0.277267 0.220247 0.521534 0.079 Uiso 1 1 calc R . . . .
C36 C -0.0544(9) 0.3664(7) 0.7651(8) 0.066(2) Uani 1 1 d . U . . .
H36 H -0.044904 0.414102 0.820695 0.079 Uiso 1 1 calc R . . . .
O7 O 0.4371(3) 0.0695(3) 0.4621(3) 0.0259(8) Uani 1 1 d . . . . .
H7B H 0.473110 0.095257 0.416260 0.039 Uiso 1 1 d G . . A 1
H7A H 0.368660 0.064260 0.465180 0.039 Uiso 1 1 d G . . . .
O3 O 1.0153(7) 0.3316(7) 1.1447(5) 0.0579(18) Uani 0.75 1 d . . P . .
H3A H 1.051103 0.295261 1.196295 0.087 Uiso 0.75 1 d G . P . .
H3B H 0.945580 0.339758 1.141849 0.087 Uiso 0.75 1 d G . P . .
O4 O 0.7474(8) 0.1812(8) 1.3158(7) 0.073(2) Uani 0.75 1 d . . P . .
H4A H 0.808527 0.163359 1.345237 0.110 Uiso 0.75 1 d G . P . .
H4B H 0.769644 0.226143 1.282079 0.110 Uiso 0.75 1 d G . P . .
O5 O -0.4910(8) 0.1430(8) 0.3174(7) 0.072(2) Uani 0.75 1 d . . P . .
H5A H -0.521055 0.184905 0.276678 0.108 Uiso 0.75 1 d G . P . .
H5B H -0.418147 0.147923 0.323418 0.108 Uiso 0.75 1 d G . P . .
O6 O 0.9026(10) 0.5302(9) 0.9573(10) 0.099(3) Uani 0.75 1 d . . P . .
H6B H 0.827866 0.510322 0.970189 0.148 Uiso 0.75 1 d G . P B 1
H6A H 0.914050 0.577623 0.919443 0.148 Uiso 0.75 1 d G . P . .
O8 O 0.4027(12) 0.2745(13) 0.2395(10) 0.117(4) Uani 0.75 1 d . . P . .
H8A H 0.320624 0.259493 0.201932 0.175 Uiso 0.75 1 d G . P . .
H8B H 0.451194 0.316302 0.216432 0.175 Uiso 0.75 1 d G . P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 Cl1 2.5196(19) . ?
Cu1 Cl3 2.308(2) . ?
Cu1 O2 2.019(4) . ?
Cu1 N1 2.011(5) . ?
Cu1 N2 2.052(5) . ?
Cu2 Cl2 2.5128(17) . ?
Cu2 Cl4 2.264(3) . ?
Cu2 O1 1.976(4) . ?
Cu2 N3 1.994(5) . ?
Cu2 N4 2.057(5) . ?
O1 H1A 0.9043 . ?
O1 H1B 0.9443 . ?
O2 H2A 0.8913 . ?
O2 H2B 0.9202 . ?
N1 C2 1.348(7) . ?
N1 C16 1.344(7) . ?
N2 C8 1.357(7) . ?
N2 C12 1.340(7) . ?
N3 C1 1.362(7) . ?
N3 C17 1.344(7) . ?
N4 C7 1.353(7) . ?
N4 C29 1.349(8) . ?
N5 C13 1.350(8) . ?
N5 C28 1.337(8) . ?
C1 C4 1.501(7) . ?
C1 C10 1.386(7) . ?
C2 C6 1.509(7) . ?
C2 C18 1.368(8) . ?
C3 C5 1.396(8) . ?
C3 C6 1.406(8) . ?
C3 C8 1.489(8) . ?
C4 C5 1.406(7) . ?
C4 C9 1.390(8) . ?
C5 C7 1.494(8) . ?
C6 C11 1.396(8) . ?
C7 C21 1.393(8) . ?
C8 C14 1.384(8) . ?
C9 C11 1.413(8) . ?
C9 C26 1.496(8) . ?
C10 H10 0.9300 . ?
C10 C20 1.391(8) . ?
C11 C13 1.495(8) . ?
C12 H12 0.9300 . ?
C12 C15 1.378(8) . ?
C13 C22 1.380(8) . ?
C14 H14 0.9300 . ?
C14 C25 1.375(8) . ?
N6 C26 1.392(9) . ?
N6 C36 1.321(10) . ?
C15 H15 0.9300 . ?
C15 C25 1.370(9) . ?
C16 H16 0.9300 . ?
C16 C23 1.361(9) . ?
C17 H17 0.9300 . ?
C17 C19 1.371(8) . ?
C18 H18 0.9300 . ?
C18 C24 1.380(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.366(8) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C21 C31 1.380(9) . ?
C22 H22 0.9300 . ?
C22 C30 1.406(9) . ?
C23 H23 0.9300 . ?
C23 C24 1.373(8) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C33 1.370(10) . ?
C27 H27 0.9300 . ?
C27 C28 1.358(9) . ?
C27 C30 1.367(10) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C29 C32 1.373(10) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C31 C32 1.375(10) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C33 C35 1.560(12) . ?
C34 H34 0.9300 . ?
C34 C35 1.362(12) . ?
C34 C36 1.263(12) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
O7 H7B 0.9692 . ?
O7 H7A 0.8494 . ?
O3 H3A 0.9881 . ?
O3 H3B 0.9095 . ?
O4 H4A 0.8497 . ?
O4 H4B 0.8497 . ?
O5 H5A 0.9333 . ?
O5 H5B 0.8498 . ?
O6 H6B 0.9644 . ?
O6 H6A 0.8924 . ?
O8 H8A 0.8487 . ?
O8 H8B 0.8506 . ?

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
H7Ba O7 H7A 132.8 . . ?
H6Ba O6 H6A 117.5 . . ?
Cl3 Cu1 Cl1 103.84(6) . . ?
O2 Cu1 Cl1 95.04(16) . . ?
O2 Cu1 Cl3 88.29(14) . . ?
O2 Cu1 N2 89.57(18) . . ?
N1 Cu1 Cl1 97.45(14) . . ?
N1 Cu1 Cl3 92.05(14) . . ?
N1 Cu1 O2 167.05(19) . . ?
N1 Cu1 N2 85.31(19) . . ?
N2 Cu1 Cl1 97.97(13) . . ?
N2 Cu1 Cl3 158.19(14) . . ?
Cl4 Cu2 Cl2 102.87(9) . . ?
O1 Cu2 Cl2 94.24(14) . . ?
O1 Cu2 Cl4 88.89(16) . . ?
O1 Cu2 N3 169.03(18) . . ?
O1 Cu2 N4 90.2(2) . . ?
N3 Cu2 Cl2 96.60(14) . . ?
N3 Cu2 Cl4 90.28(15) . . ?
N3 Cu2 N4 86.54(19) . . ?
N4 Cu2 Cl2 98.52(14) . . ?
N4 Cu2 Cl4 158.60(15) . . ?
Cu2 O1 H1A 109.6 . . ?
Cu2 O1 H1B 111.3 . . ?
H1A O1 H1B 110.8 . . ?
Cu1 O2 H2A 112.4 . . ?
Cu1 O2 H2B 90.5 . . ?
H2A O2 H2B 122.2 . . ?
C2 N1 Cu1 120.8(4) . . ?
C16 N1 Cu1 121.1(4) . . ?
C16 N1 C2 117.9(5) . . ?
C8 N2 Cu1 120.4(4) . . ?
C12 N2 Cu1 120.8(4) . . ?
C12 N2 C8 118.3(5) . . ?
C1 N3 Cu2 119.1(4) . . ?
C17 N3 Cu2 122.0(4) . . ?
C17 N3 C1 118.3(5) . . ?
C7 N4 Cu2 121.0(4) . . ?
C29 N4 Cu2 119.7(4) . . ?
C29 N4 C7 118.5(5) . . ?
C28 N5 C13 117.8(5) . . ?
N3 C1 C4 117.3(5) . . ?
N3 C1 C10 121.7(5) . . ?
C10 C1 C4 120.9(5) . . ?
N1 C2 C6 117.4(5) . . ?
N1 C2 C18 121.6(5) . . ?
C18 C2 C6 121.0(5) . . ?
C5 C3 C6 119.9(5) . . ?
C5 C3 C8 118.7(5) . . ?
C6 C3 C8 121.3(5) . . ?
C5 C4 C1 120.9(5) . . ?
C9 C4 C1 118.6(5) . . ?
C9 C4 C5 120.4(5) . . ?
C3 C5 C4 119.7(5) . . ?
C3 C5 C7 120.7(5) . . ?
C4 C5 C7 119.5(5) . . ?
C3 C6 C2 120.0(5) . . ?
C11 C6 C2 119.2(5) . . ?
C11 C6 C3 120.5(5) . . ?
N4 C7 C5 117.1(5) . . ?
N4 C7 C21 121.5(5) . . ?
C21 C7 C5 121.4(5) . . ?
N2 C8 C3 117.5(5) . . ?
N2 C8 C14 121.1(5) . . ?
C14 C8 C3 121.3(5) . . ?
C4 C9 C11 120.2(5) . . ?
C4 C9 C26 121.0(5) . . ?
C11 C9 C26 118.8(5) . . ?
C1 C10 H10 120.6 . . ?
C1 C10 C20 118.8(5) . . ?
C20 C10 H10 120.6 . . ?
C6 C11 C9 119.2(5) . . ?
C6 C11 C13 121.1(5) . . ?
C9 C11 C13 119.6(5) . . ?
N2 C12 H12 118.5 . . ?
N2 C12 C15 122.9(5) . . ?
C15 C12 H12 118.5 . . ?
N5 C13 C11 115.8(5) . . ?
N5 C13 C22 122.8(6) . . ?
C22 C13 C11 121.3(6) . . ?
C8 C14 H14 120.3 . . ?
C25 C14 C8 119.3(5) . . ?
C25 C14 H14 120.3 . . ?
C36 N6 C26 119.2(7) . . ?
C12 C15 H15 120.8 . . ?
C25 C15 C12 118.5(6) . . ?
C25 C15 H15 120.8 . . ?
N1 C16 H16 118.6 . . ?
N1 C16 C23 122.9(6) . . ?
C23 C16 H16 118.6 . . ?
N3 C17 H17 119.0 . . ?
N3 C17 C19 122.0(5) . . ?
C19 C17 H17 119.0 . . ?
C2 C18 H18 120.0 . . ?
C2 C18 C24 119.9(5) . . ?
C24 C18 H18 120.0 . . ?
C17 C19 H19 119.8 . . ?
C20 C19 C17 120.3(6) . . ?
C20 C19 H19 119.8 . . ?
C10 C20 H20 120.6 . . ?
C19 C20 C10 118.8(5) . . ?
C19 C20 H20 120.6 . . ?
C7 C21 H21 120.4 . . ?
C31 C21 C7 119.3(6) . . ?
C31 C21 H21 120.4 . . ?
C13 C22 H22 121.0 . . ?
C13 C22 C30 118.0(6) . . ?
C30 C22 H22 121.0 . . ?
C16 C23 H23 120.3 . . ?
C16 C23 C24 119.4(6) . . ?
C24 C23 H23 120.3 . . ?
C18 C24 H24 120.9 . . ?
C23 C24 C18 118.2(6) . . ?
C23 C24 H24 120.9 . . ?
C14 C25 H25 120.1 . . ?
C15 C25 C14 119.7(6) . . ?
C15 C25 H25 120.1 . . ?
N6 C26 C9 114.4(6) . . ?
C33 C26 C9 119.2(7) . . ?
C33 C26 N6 126.4(7) . . ?
C28 C27 H27 119.8 . . ?
C28 C27 C30 120.5(6) . . ?
C30 C27 H27 119.8 . . ?
N5 C28 C27 122.7(6) . . ?
N5 C28 H28 118.6 . . ?
C27 C28 H28 118.6 . . ?
N4 C29 H29 119.1 . . ?
N4 C29 C32 121.9(6) . . ?
C32 C29 H29 119.1 . . ?
C22 C30 H30 120.9 . . ?
C27 C30 C22 118.2(6) . . ?
C27 C30 H30 120.9 . . ?
C21 C31 H31 120.7 . . ?
C32 C31 C21 118.6(6) . . ?
C32 C31 H31 120.7 . . ?
C29 C32 C31 120.1(6) . . ?
C29 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C26 C33 H33 124.8 . . ?
C26 C33 C35 110.4(8) . . ?
C35 C33 H33 124.8 . . ?
C35 C34 H34 116.0 . . ?
C36 C34 H34 116.0 . . ?
C36 C34 C35 128.0(9) . . ?
C33 C35 H35 122.0 . . ?
C34 C35 C33 115.9(7) . . ?
C34 C35 H35 122.0 . . ?
N6 C36 H36 120.0 . . ?
C34 C36 N6 120.0(9) . . ?
C34 C36 H36 120.0 . . ?
H3A O3 H3B 116.5 . . ?
H4A O4 H4B 109.5 . . ?
H5A O5 H5B 113.8 . . ?
H8A O8 H8B 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p-1865
_database_code_depnum_ccdc_archive 'CCDC 1846816'
_audit_update_record             
;
2018-07-17 deposited with the CCDC.
2018-07-25 downloaded from the CCDC.
;
_audit_creation_date             2018-07-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C19 H16 Cl2 Cu N3 O)'
_chemical_formula_sum            'C38 H32 Cl4 Cu2 N6 O2'
_chemical_formula_weight         873.57
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.263(3)
_cell_length_b                   11.838(4)
_cell_length_c                   17.404(6)
_cell_angle_alpha                85.270(12)
_cell_angle_beta                 89.651(12)
_cell_angle_gamma                86.120(12)
_cell_volume                     1897.7(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4853
_cell_measurement_temperature    100
_cell_measurement_theta_max      23.080
_cell_measurement_theta_min      2.349
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.445
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6244
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear green'
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19244
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        24.254
_diffrn_reflns_theta_max         24.254
_diffrn_reflns_theta_min         1.174
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4369
_reflns_number_total             5945
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         3.138
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.157
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.214
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     471
_refine_ls_number_reflns         5945
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0726
_refine_ls_restrained_S_all      1.214
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1798
_refine_ls_wR_factor_ref         0.1939
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1-H1
 0.85 with sigma of 0.01
 O2-H2
 0.85 with sigma of 0.01
 C37-H1
 1.911593 with sigma of 0.02
 Cu1-H1
 2.649897 with sigma of 0.02
 C38-H2
 1.922323 with sigma of 0.02
 Cu2-H2
 2.674255 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N1) = Uanis(N2)
4.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27),
  C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34),
 C35(H35), C36(H36)
4.b Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C38(H38A,H38B,H38C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 -0.20777(7) 0.73260(6) 0.88542(4) 0.0279(2) Uani 1 1 d D . . . .
Cu2 Cu 0.32354(8) 0.26844(6) 0.61059(4) 0.0297(2) Uani 1 1 d D . . . .
Cl1 Cl -0.36837(16) 0.62464(14) 0.95216(8) 0.0367(4) Uani 1 1 d . . . . .
Cl2 Cl 0.14741(16) 0.37944(13) 0.54610(8) 0.0369(4) Uani 1 1 d . . . . .
Cl3 Cl -0.33853(17) 0.86570(14) 0.79544(9) 0.0417(4) Uani 1 1 d . . . . .
Cl4 Cl 0.20772(18) 0.13781(14) 0.69984(10) 0.0439(4) Uani 1 1 d . . . . .
O1 O -0.1976(4) 0.8393(4) 0.9724(2) 0.0389(11) Uani 1 1 d D . . . .
H1 H -0.1189(17) 0.843(5) 0.998(2) 0.058 Uiso 1 1 d DR . . . .
O2 O 0.3506(4) 0.1650(4) 0.5206(2) 0.0403(11) Uani 1 1 d D . . . .
H2 H 0.4313(18) 0.157(5) 0.496(2) 0.060 Uiso 1 1 d DR . . . .
N1 N 0.0003(5) 0.7695(4) 0.8709(3) 0.0293(8) Uani 1 1 d . . . . .
N2 N 0.5348(5) 0.2263(4) 0.6253(3) 0.0293(8) Uani 1 1 d . . . . .
N3 N 0.3649(5) 0.3855(4) 0.6881(2) 0.0264(11) Uani 1 1 d . . . . .
N4 N -0.1492(5) 0.6114(4) 0.8112(3) 0.0270(11) Uani 1 1 d . . . . .
C1 C 0.0990(6) 0.6944(5) 0.9058(3) 0.0225(12) Uani 1 1 d . . . . .
N5 N -0.0525(5) 0.2155(4) 0.9420(3) 0.0345(12) Uani 1 1 d . . . . .
N6 N 0.5976(6) 0.2172(4) 0.4363(3) 0.0373(13) Uani 1 1 d . . . . .
C2 C 0.6258(6) 0.3022(5) 0.5920(3) 0.0237(13) Uani 1 1 d . . . . .
C3 C -0.0664(5) 0.4129(5) 0.9665(3) 0.0224(12) Uani 1 1 d . . . . .
C4 C 0.0394(6) 0.5956(5) 0.9527(3) 0.0245(13) Uani 1 1 d . . . . .
C5 C 0.4712(6) 0.4890(5) 0.5790(3) 0.0239(13) Uani 1 1 d . . . . .
C6 C -0.0636(6) 0.5197(5) 0.8370(3) 0.0243(13) Uani 1 1 d . . . . .
C7 C -0.0279(6) 0.5092(5) 0.9205(3) 0.0243(13) Uani 1 1 d . . . . .
C8 C 0.5524(6) 0.4036(5) 0.5452(3) 0.0250(13) Uani 1 1 d . . . . .
C9 C -0.1323(6) 0.3155(5) 0.9332(3) 0.0269(14) Uani 1 1 d . . . . .
C10 C 0.5809(6) 0.4128(5) 0.4656(3) 0.0273(13) Uani 1 1 d . . . . .
C11 C 0.4374(6) 0.4777(5) 0.6632(3) 0.0255(13) Uani 1 1 d . . . . .
C12 C 0.2463(6) 0.7084(5) 0.9018(3) 0.0305(14) Uani 1 1 d . . . . .
H12 H 0.311770 0.654123 0.926107 0.037 Uiso 1 1 calc R . . . .
C13 C 0.6627(6) 0.3165(5) 0.4305(3) 0.0295(14) Uani 1 1 d . . . . .
C14 C 0.5962(7) 0.1309(5) 0.6651(3) 0.0318(14) Uani 1 1 d . . . . .
H14 H 0.536870 0.077477 0.688177 0.038 Uiso 1 1 calc R . . . .
C15 C 0.7747(7) 0.2867(5) 0.5960(3) 0.0342(15) Uani 1 1 d . . . . .
H15 H 0.833225 0.340124 0.572224 0.041 Uiso 1 1 calc R . . . .
C16 C -0.1787(7) 0.6262(6) 0.7354(3) 0.0367(16) Uani 1 1 d . . . . .
H16 H -0.235879 0.690010 0.716704 0.044 Uiso 1 1 calc R . . . .
C17 C 0.4811(6) 0.5541(5) 0.7122(3) 0.0362(16) Uani 1 1 d . . . . .
H17 H 0.528613 0.617408 0.693367 0.043 Uiso 1 1 calc R . . . .
C18 C 0.3396(7) 0.3686(6) 0.7638(3) 0.0372(16) Uani 1 1 d . . . . .
H18 H 0.291919 0.304939 0.781708 0.045 Uiso 1 1 calc R . . . .
C19 C -0.0103(6) 0.4402(5) 0.7884(3) 0.0345(15) Uani 1 1 d . . . . .
H19 H 0.045898 0.376298 0.807887 0.041 Uiso 1 1 calc R . . . .
C20 C 0.0494(7) 0.8639(5) 0.8315(3) 0.0331(15) Uani 1 1 d . . . . .
H20 H -0.017278 0.917499 0.807492 0.040 Uiso 1 1 calc R . . . .
C21 C 0.2941(7) 0.8025(6) 0.8619(4) 0.0397(16) Uani 1 1 d . . . . .
H21 H 0.392603 0.813114 0.858686 0.048 Uiso 1 1 calc R . . . .
C22 C -0.2656(7) 0.3260(5) 0.8977(4) 0.0361(15) Uani 1 1 d . . . . .
H22 H -0.318464 0.395778 0.892114 0.043 Uiso 1 1 calc R . . . .
C23 C 0.7953(7) 0.3280(5) 0.3977(3) 0.0388(16) Uani 1 1 d . . . . .
H23 H 0.837303 0.397423 0.395046 0.047 Uiso 1 1 calc R . . . .
C24 C -0.1267(7) 0.5496(6) 0.6841(4) 0.0432(17) Uani 1 1 d . . . . .
H24 H -0.149704 0.561347 0.631967 0.052 Uiso 1 1 calc R . . . .
C25 C 0.3806(7) 0.4408(6) 0.8163(4) 0.0406(17) Uani 1 1 d . . . . .
H25 H 0.360006 0.426569 0.868453 0.049 Uiso 1 1 calc R . . . .
C26 C -0.0410(7) 0.4562(6) 0.7114(3) 0.0417(17) Uani 1 1 d . . . . .
H26 H -0.004004 0.404168 0.677865 0.050 Uiso 1 1 calc R . . . .
C27 C 0.7446(7) 0.1121(6) 0.6717(4) 0.0405(17) Uani 1 1 d . . . . .
H27 H 0.783974 0.047364 0.699998 0.049 Uiso 1 1 calc R . . . .
C28 C 0.8343(7) 0.1886(6) 0.6367(4) 0.0428(17) Uani 1 1 d . . . . .
H28 H 0.934176 0.175017 0.640211 0.051 Uiso 1 1 calc R . . . .
C29 C 0.1947(7) 0.8824(6) 0.8262(4) 0.0420(17) Uani 1 1 d . . . . .
H29 H 0.225459 0.947460 0.799078 0.050 Uiso 1 1 calc R . . . .
C30 C 0.6676(8) 0.1279(6) 0.4079(4) 0.0479(18) Uani 1 1 d . . . . .
H30 H 0.623404 0.059480 0.410637 0.057 Uiso 1 1 calc R . . . .
C31 C -0.1086(8) 0.1252(6) 0.9148(4) 0.0455(18) Uani 1 1 d . . . . .
H31 H -0.054637 0.055859 0.920657 0.055 Uiso 1 1 calc R . . . .
C32 C 0.4528(7) 0.5348(6) 0.7905(4) 0.0437(17) Uani 1 1 d . . . . .
H32 H 0.482150 0.584622 0.824999 0.052 Uiso 1 1 calc R . . . .
C33 C -0.2391(8) 0.1283(6) 0.8791(4) 0.0507(19) Uani 1 1 d . . . . .
H33 H -0.273324 0.063391 0.861028 0.061 Uiso 1 1 calc R . . . .
C34 C -0.3188(7) 0.2310(6) 0.8706(4) 0.0466(18) Uani 1 1 d . . . . .
H34 H -0.408646 0.236253 0.846627 0.056 Uiso 1 1 calc R . . . .
C35 C 0.8663(8) 0.2343(6) 0.3684(4) 0.051(2) Uani 1 1 d . . . . .
H35 H 0.956136 0.240146 0.344793 0.062 Uiso 1 1 calc R . . . .
C36 C 0.8023(8) 0.1324(6) 0.3746(4) 0.052(2) Uani 1 1 d . . . . .
H36 H 0.849294 0.067753 0.356679 0.063 Uiso 1 1 calc R . . . .
C37 C -0.3167(8) 0.8751(7) 1.0184(5) 0.065(2) Uani 1 1 d D . . . .
H37A H -0.402342 0.886521 0.987173 0.098 Uiso 1 1 calc GR . . . .
H37B H -0.297310 0.944996 1.039396 0.098 Uiso 1 1 calc GR . . . .
H37C H -0.330810 0.817930 1.059640 0.098 Uiso 1 1 calc GR . . . .
C38 C 0.2357(8) 0.1381(7) 0.4716(5) 0.065(2) Uani 1 1 d D . . . .
H38A H 0.211797 0.201566 0.434956 0.097 Uiso 1 1 calc GR . . . .
H38B H 0.152176 0.121744 0.502452 0.097 Uiso 1 1 calc GR . . . .
H38C H 0.266302 0.072921 0.444825 0.097 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 Cl1 2.2775(17) . ?
Cu1 Cl3 2.4000(17) . ?
Cu1 O1 2.057(4) . ?
Cu1 N1 2.014(5) . ?
Cu1 N4 2.053(5) . ?
Cu2 Cl2 2.2666(17) . ?
Cu2 Cl4 2.4007(18) . ?
Cu2 O2 2.070(4) . ?
Cu2 N2 1.999(5) . ?
Cu2 N3 2.066(5) . ?
O1 H1 0.860(10) . ?
O1 C37 1.420(7) . ?
O2 H2 0.859(10) . ?
O2 C38 1.436(8) . ?
N1 C1 1.343(7) . ?
N1 C20 1.366(7) . ?
N2 C2 1.366(7) . ?
N2 C14 1.367(7) . ?
N3 C11 1.360(7) . ?
N3 C18 1.338(7) . ?
N4 C6 1.348(7) . ?
N4 C16 1.344(7) . ?
C1 C4 1.505(8) . ?
C1 C12 1.386(8) . ?
N5 C9 1.351(7) . ?
N5 C31 1.341(8) . ?
N6 C13 1.354(8) . ?
N6 C30 1.331(8) . ?
C2 C8 1.518(8) . ?
C2 C15 1.380(8) . ?
C3 C4 1.424(7) 2_567 ?
C3 C7 1.403(7) . ?
C3 C9 1.499(8) . ?
C4 C3 1.424(7) 2_567 ?
C4 C7 1.391(8) . ?
C5 C8 1.387(7) . ?
C5 C10 1.401(8) 2_666 ?
C5 C11 1.494(7) . ?
C6 C7 1.486(8) . ?
C6 C19 1.382(7) . ?
C8 C10 1.406(8) . ?
C9 C22 1.378(8) . ?
C10 C5 1.401(8) 2_666 ?
C10 C13 1.496(8) . ?
C11 C17 1.375(8) . ?
C12 H12 0.9300 . ?
C12 C21 1.362(9) . ?
C13 C23 1.362(8) . ?
C14 H14 0.9300 . ?
C14 C27 1.382(9) . ?
C15 H15 0.9300 . ?
C15 C28 1.393(9) . ?
C16 H16 0.9300 . ?
C16 C24 1.386(9) . ?
C17 H17 0.9300 . ?
C17 C32 1.389(8) . ?
C18 H18 0.9300 . ?
C18 C25 1.375(9) . ?
C19 H19 0.9300 . ?
C19 C26 1.366(8) . ?
C20 H20 0.9300 . ?
C20 C29 1.380(9) . ?
C21 H21 0.9300 . ?
C21 C29 1.386(9) . ?
C22 H22 0.9300 . ?
C22 C34 1.376(9) . ?
C23 H23 0.9300 . ?
C23 C35 1.383(9) . ?
C24 H24 0.9300 . ?
C24 C26 1.371(9) . ?
C25 H25 0.9300 . ?
C25 C32 1.379(9) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C27 C28 1.373(9) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C30 C36 1.375(9) . ?
C31 H31 0.9300 . ?
C31 C33 1.359(10) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C33 C34 1.377(9) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C35 C36 1.376(10) . ?
C36 H36 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Cu1 Cl3 108.82(7) . . ?
O1 Cu1 Cl1 92.24(13) . . ?
O1 Cu1 Cl3 96.57(13) . . ?
N1 Cu1 Cl1 146.93(15) . . ?
N1 Cu1 Cl3 104.20(15) . . ?
N1 Cu1 O1 82.19(17) . . ?
N1 Cu1 N4 82.47(18) . . ?
N4 Cu1 Cl1 94.44(13) . . ?
N4 Cu1 Cl3 98.13(14) . . ?
N4 Cu1 O1 160.92(18) . . ?
Cl2 Cu2 Cl4 107.61(7) . . ?
O2 Cu2 Cl2 91.75(13) . . ?
O2 Cu2 Cl4 98.00(14) . . ?
N2 Cu2 Cl2 148.15(15) . . ?
N2 Cu2 Cl4 104.21(15) . . ?
N2 Cu2 O2 82.40(18) . . ?
N2 Cu2 N3 82.12(18) . . ?
N3 Cu2 Cl2 95.33(13) . . ?
N3 Cu2 Cl4 96.94(13) . . ?
N3 Cu2 O2 160.68(18) . . ?
Cu1 O1 H1 121.3(17) . . ?
C37 O1 Cu1 125.1(4) . . ?
C37 O1 H1 108.8(17) . . ?
Cu2 O2 H2 122.1(17) . . ?
C38 O2 Cu2 124.3(4) . . ?
C38 O2 H2 108.9(17) . . ?
C1 N1 Cu1 115.8(4) . . ?
C1 N1 C20 117.5(5) . . ?
C20 N1 Cu1 126.6(4) . . ?
C2 N2 Cu2 115.6(4) . . ?
C2 N2 C14 117.4(5) . . ?
C14 N2 Cu2 126.9(4) . . ?
C11 N3 Cu2 118.8(3) . . ?
C18 N3 Cu2 123.2(4) . . ?
C18 N3 C11 117.5(5) . . ?
C6 N4 Cu1 119.2(4) . . ?
C16 N4 Cu1 122.3(4) . . ?
C16 N4 C6 118.0(5) . . ?
N1 C1 C4 115.7(5) . . ?
N1 C1 C12 122.7(5) . . ?
C12 C1 C4 121.6(5) . . ?
C31 N5 C9 117.2(5) . . ?
C30 N6 C13 117.6(6) . . ?
N2 C2 C8 115.3(5) . . ?
N2 C2 C15 123.5(5) . . ?
C15 C2 C8 121.1(5) . . ?
C4 C3 C9 117.9(5) 2_567 . ?
C7 C3 C4 119.8(5) . 2_567 ?
C7 C3 C9 122.2(5) . . ?
C3 C4 C1 116.8(5) 2_567 . ?
C7 C4 C1 123.5(5) . . ?
C7 C4 C3 119.4(5) . 2_567 ?
C8 C5 C10 120.4(5) . 2_666 ?
C8 C5 C11 120.6(5) . . ?
C10 C5 C11 119.0(5) 2_666 . ?
N4 C6 C7 116.4(5) . . ?
N4 C6 C19 121.9(5) . . ?
C19 C6 C7 121.6(5) . . ?
C3 C7 C6 119.2(5) . . ?
C4 C7 C3 120.7(5) . . ?
C4 C7 C6 120.0(5) . . ?
C5 C8 C2 122.5(5) . . ?
C5 C8 C10 120.7(5) . . ?
C10 C8 C2 116.6(5) . . ?
N5 C9 C3 115.0(5) . . ?
N5 C9 C22 122.2(5) . . ?
C22 C9 C3 122.8(5) . . ?
C5 C10 C8 118.9(5) 2_666 . ?
C5 C10 C13 121.9(5) 2_666 . ?
C8 C10 C13 119.2(5) . . ?
N3 C11 C5 115.6(5) . . ?
N3 C11 C17 122.6(5) . . ?
C17 C11 C5 121.8(5) . . ?
C1 C12 H12 120.4 . . ?
C21 C12 C1 119.2(6) . . ?
C21 C12 H12 120.4 . . ?
N6 C13 C10 115.1(5) . . ?
N6 C13 C23 123.0(5) . . ?
C23 C13 C10 121.9(5) . . ?
N2 C14 H14 119.3 . . ?
N2 C14 C27 121.3(6) . . ?
C27 C14 H14 119.3 . . ?
C2 C15 H15 121.1 . . ?
C2 C15 C28 117.8(6) . . ?
C28 C15 H15 121.1 . . ?
N4 C16 H16 118.9 . . ?
N4 C16 C24 122.3(6) . . ?
C24 C16 H16 118.9 . . ?
C11 C17 H17 120.7 . . ?
C11 C17 C32 118.6(6) . . ?
C32 C17 H17 120.7 . . ?
N3 C18 H18 118.4 . . ?
N3 C18 C25 123.2(6) . . ?
C25 C18 H18 118.4 . . ?
C6 C19 H19 120.3 . . ?
C26 C19 C6 119.4(6) . . ?
C26 C19 H19 120.3 . . ?
N1 C20 H20 118.9 . . ?
N1 C20 C29 122.2(6) . . ?
C29 C20 H20 118.9 . . ?
C12 C21 H21 120.3 . . ?
C12 C21 C29 119.4(6) . . ?
C29 C21 H21 120.3 . . ?
C9 C22 H22 120.7 . . ?
C34 C22 C9 118.6(6) . . ?
C34 C22 H22 120.7 . . ?
C13 C23 H23 120.7 . . ?
C13 C23 C35 118.6(6) . . ?
C35 C23 H23 120.7 . . ?
C16 C24 H24 120.5 . . ?
C26 C24 C16 118.9(6) . . ?
C26 C24 H24 120.5 . . ?
C18 C25 H25 120.6 . . ?
C18 C25 C32 118.9(6) . . ?
C32 C25 H25 120.6 . . ?
C19 C26 C24 119.3(6) . . ?
C19 C26 H26 120.3 . . ?
C24 C26 H26 120.3 . . ?
C14 C27 H27 119.8 . . ?
C28 C27 C14 120.3(6) . . ?
C28 C27 H27 119.8 . . ?
C15 C28 H28 120.2 . . ?
C27 C28 C15 119.6(6) . . ?
C27 C28 H28 120.2 . . ?
C20 C29 C21 118.9(6) . . ?
C20 C29 H29 120.5 . . ?
C21 C29 H29 120.5 . . ?
N6 C30 H30 118.5 . . ?
N6 C30 C36 123.0(6) . . ?
C36 C30 H30 118.5 . . ?
N5 C31 H31 117.9 . . ?
N5 C31 C33 124.3(6) . . ?
C33 C31 H31 117.9 . . ?
C17 C32 H32 120.4 . . ?
C25 C32 C17 119.2(6) . . ?
C25 C32 H32 120.4 . . ?
C31 C33 H33 121.2 . . ?
C31 C33 C34 117.7(6) . . ?
C34 C33 H33 121.2 . . ?
C22 C34 C33 120.1(6) . . ?
C22 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C23 C35 H35 120.4 . . ?
C36 C35 C23 119.2(6) . . ?
C36 C35 H35 120.4 . . ?
C30 C36 C35 118.7(6) . . ?
C30 C36 H36 120.6 . . ?
C35 C36 H36 120.6 . . ?
O1 C37 H37A 109.5 . . ?
O1 C37 H37B 109.5 . . ?
O1 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
O2 C38 H38A 109.5 . . ?
O2 C38 H38B 109.5 . . ?
O2 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p-1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1552124'
_audit_update_record             
;
2018-07-17 deposited with the CCDC.
2018-07-25 downloaded from the CCDC.
;
_audit_creation_date             2018-07-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H28 Cl4 Cu2 N6 O2, 5.5(H2 O)'
_chemical_formula_sum            'C36 H39 Cl4 Cu2 N6 O7.50'
_chemical_formula_weight         944.61
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.081(5)
_cell_length_b                   10.926(6)
_cell_length_c                   12.055(7)
_cell_angle_alpha                113.957(18)
_cell_angle_beta                 111.576(17)
_cell_angle_gamma                91.514(16)
_cell_volume                     994.5(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4501
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.228
_cell_measurement_theta_min      2.031
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.395
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1537 before and 0.0926 after correction.
The Ratio of minimum to maximum transmission is 0.6473.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             483
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1043
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            27505
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.228
_diffrn_reflns_theta_max         25.228
_diffrn_reflns_theta_min         2.031
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2859
_reflns_number_total             3561
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.310
_refine_diff_density_min         -0.800
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3561
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0580
_refine_ls_restrained_S_all      1.179
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0557P)²+3.7812P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1506
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O1-H1A = O1-H1B
 0.84 with sigma of 0.01
 O4-H4A
 0.95 with sigma of 0.01
 O4-H4B
 0.95 with sigma of 0.01
 O2-H2A
 1 with sigma of 0.02
 H1A-H1B
 1.34 with sigma of 0.02
3. Others
 Fixed Sof: O4(0.75) H4A(0.75) H4B(0.75)
4.a Free rotating group:
 O2(H2A,H2B), O4(H4A,H4B), O3(H3A,H3B)
4.b Rotating group:
 O1(H1A,H1B)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C3(H3), C9(H9), C12(H12), C2(H2), C15(H15), C10(H10),
 C11(H11), C16(H16), C18(H18), C17(H17)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.22485(7) 0.60597(6) 0.34747(6) 0.0254(2) Uani 1 1 d . . . . .
Cl1 Cl 0.35923(17) 0.69896(15) 0.24979(16) 0.0418(4) Uani 1 1 d . . . . .
Cl2 Cl 0.18842(18) 0.37379(14) 0.23557(16) 0.0432(4) Uani 1 1 d . . . . .
N1 N -0.0099(4) 0.5985(4) 0.2390(4) 0.0198(8) Uani 1 1 d . . . . .
O1 O 0.4244(4) 0.6097(4) 0.4994(4) 0.0389(9) Uani 1 1 d D . . . .
H1A H 0.427046 0.671262 0.592274 0.058 Uiso 1 1 d DGR . . . .
H1B H 0.487971 0.632618 0.468239 0.058 Uiso 1 1 d DGR . . . .
N2 N 0.2132(4) 0.7864(4) 0.4880(4) 0.0215(9) Uani 1 1 d . . . . .
N3 N -0.3962(5) 0.2814(4) 0.2570(4) 0.0285(10) Uani 1 1 d . . . . .
O2 O 0.7140(6) 0.7723(5) 0.5699(5) 0.0589(13) Uani 1 1 d D . . . .
H2A H 0.728047 0.718751 0.628808 0.088 Uiso 1 1 d DG . . . .
H2B H 0.714722 0.836214 0.656096 0.088 Uiso 1 1 d G . . . .
C5 C -0.1183(5) 0.5813(4) 0.2873(4) 0.0179(10) Uani 1 1 d . . . . .
C6 C -0.0580(5) 0.5410(4) 0.3986(4) 0.0168(9) Uani 1 1 d . . . . .
C7 C 0.0636(5) 0.6306(4) 0.5239(4) 0.0177(9) Uani 1 1 d . . . . .
C13 C -0.1226(5) 0.4107(4) 0.3753(4) 0.0180(9) Uani 1 1 d . . . . .
C8 C 0.1241(5) 0.7732(4) 0.5518(5) 0.0200(10) Uani 1 1 d . . . . .
C1 C -0.0608(6) 0.6210(5) 0.1314(5) 0.0234(10) Uani 1 1 d . . . . .
H1 H 0.013306 0.632704 0.098125 0.028 Uiso 1 1 calc R . . . .
C4 C -0.2772(5) 0.5951(4) 0.2328(5) 0.0199(10) Uani 1 1 d . . . . .
H4 H -0.348077 0.588386 0.270436 0.024 Uiso 1 1 calc R . . . .
C3 C -0.3280(6) 0.6190(4) 0.1213(5) 0.0218(10) Uani 1 1 d . . . . .
H3 H -0.433597 0.629104 0.083459 0.026 Uiso 1 1 calc R . . . .
C14 C -0.2594(5) 0.3168(4) 0.2454(5) 0.0198(10) Uani 1 1 d . . . . .
C9 C 0.0949(6) 0.8868(5) 0.6421(5) 0.0255(11) Uani 1 1 d . . . . .
H9 H 0.033015 0.876019 0.685477 0.031 Uiso 1 1 calc R . . . .
C12 C 0.2771(6) 0.9119(5) 0.5144(5) 0.0290(11) Uani 1 1 d . . . . .
H12 H 0.339311 0.920701 0.470593 0.035 Uiso 1 1 calc R . . . .
C2 C -0.2208(6) 0.6276(5) 0.0671(5) 0.0244(11) Uani 1 1 d . . . . .
H2 H -0.254610 0.637684 -0.010947 0.029 Uiso 1 1 calc R . . . .
C15 C -0.2490(7) 0.2703(5) 0.1252(5) 0.0310(12) Uani 1 1 d . . . . .
H15 H -0.154062 0.294455 0.119396 0.037 Uiso 1 1 calc R . . . .
C10 C 0.1591(6) 1.0163(5) 0.6668(5) 0.0283(11) Uani 1 1 d . . . . .
H10 H 0.138099 1.093572 0.724802 0.034 Uiso 1 1 calc R . . . .
C11 C 0.2543(6) 1.0291(5) 0.6045(5) 0.0335(13) Uani 1 1 d . . . . .
H11 H 0.302594 1.115121 0.622582 0.040 Uiso 1 1 calc R . . . .
C16 C -0.3911(8) 0.1825(5) 0.0081(5) 0.0369(14) Uani 1 1 d . . . . .
H16 H -0.391223 0.147821 -0.076300 0.044 Uiso 1 1 calc R . . . .
O4 O 0.9476(7) 0.9113(6) 1.0369(6) 0.0535(15) Uani 0.75 1 d D . P . .
H4A H 0.944732 0.800472 0.986670 0.080 Uiso 0.75 1 d DG . P . .
H4B H 0.976323 0.974419 1.005749 0.080 Uiso 0.75 1 d DG . P . .
C18 C -0.5255(6) 0.1992(5) 0.1464(6) 0.0357(13) Uani 1 1 d . . . . .
H18 H -0.618563 0.174057 0.154135 0.043 Uiso 1 1 calc R . . . .
C17 C -0.5261(7) 0.1516(5) 0.0250(6) 0.0366(13) Uani 1 1 d . . . . .
H17 H -0.619983 0.096534 -0.049292 0.044 Uiso 1 1 calc R . . . .
O3 O 0.7777(12) 1.0383(6) 0.7583(6) 0.114(3) Uani 1 1 d . . . A 2
H3A H 0.728776 1.101145 0.749117 0.171 Uiso 1 1 d G . . A 2
H3B H 0.878414 1.055138 0.824173 0.171 Uiso 1 1 d G . . A 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 Cl1 2.4230(17) . ?
Cu1 Cl2 2.283(2) . ?
Cu1 N1 2.029(4) . ?
Cu1 O1 2.033(4) . ?
Cu1 N2 2.049(4) . ?
O3b H3A 0.8503 . ?
O3b H3B 0.9161 . ?
N1 C5 1.358(6) . ?
N1 C1 1.334(6) . ?
O1 H1A 1.0358 . ?
O1 H1B 0.8754 . ?
N2 C8 1.345(6) . ?
N2 C12 1.336(6) . ?
N3 C14 1.363(6) . ?
N3 C18 1.335(7) . ?
O2 H2A 1.0663 . ?
O2 H2B 0.9862 . ?
C5 C6 1.499(6) . ?
C5 C4 1.389(6) . ?
C6 C7 1.406(6) . ?
C6 C13 1.400(6) . ?
C7 C13 1.395(6) 2_566 ?
C7 C8 1.495(6) . ?
C13 C7 1.395(6) 2_566 ?
C13 C14 1.498(6) . ?
C8 C9 1.389(7) . ?
C1 H1 0.9300 . ?
C1 C2 1.393(7) . ?
C4 H4 0.9300 . ?
C4 C3 1.387(7) . ?
C3 H3 0.9300 . ?
C3 C2 1.377(7) . ?
C14 C15 1.368(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(7) . ?
C12 H12 0.9300 . ?
C12 C11 1.383(7) . ?
C2 H2 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.440(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.374(8) . ?
C11 H11 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.370(8) . ?
O4 H4A 1.1069 . ?
O4 H4B 0.9785 . ?
C18 H18 0.9300 . ?
C18 C17 1.337(8) . ?
C17 H17 0.9300 . ?

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
H3Ab O3b H3B 123.4 . . ?
Cl2 Cu1 Cl1 105.69(7) . . ?
N1 Cu1 Cl1 100.80(12) . . ?
N1 Cu1 Cl2 90.94(11) . . ?
N1 Cu1 O1 159.57(16) . . ?
N1 Cu1 N2 85.29(15) . . ?
O1 Cu1 Cl1 98.50(13) . . ?
O1 Cu1 Cl2 90.27(12) . . ?
O1 Cu1 N2 85.24(16) . . ?
N2 Cu1 Cl1 98.61(12) . . ?
N2 Cu1 Cl2 155.68(12) . . ?
C5 N1 Cu1 116.8(3) . . ?
C1 N1 Cu1 124.2(3) . . ?
C1 N1 C5 118.7(4) . . ?
Cu1 O1 H1A 112.6 . . ?
Cu1 O1 H1B 91.2 . . ?
H1A O1 H1B 123.0 . . ?
C8 N2 Cu1 114.9(3) . . ?
C12 N2 Cu1 126.0(3) . . ?
C12 N2 C8 119.0(4) . . ?
C18 N3 C14 118.6(5) . . ?
H2A O2 H2B 72.1 . . ?
N1 C5 C6 116.0(4) . . ?
N1 C5 C4 121.7(4) . . ?
C4 C5 C6 122.2(4) . . ?
C7 C6 C5 121.0(4) . . ?
C13 C6 C5 118.9(4) . . ?
C13 C6 C7 120.0(4) . . ?
C6 C7 C8 120.0(4) . . ?
C13 C7 C6 120.2(4) 2_566 . ?
C13 C7 C8 119.7(4) 2_566 . ?
C6 C13 C14 120.9(4) . . ?
C7 C13 C6 119.7(4) 2_566 . ?
C7 C13 C14 119.3(4) 2_566 . ?
N2 C8 C7 116.5(4) . . ?
N2 C8 C9 121.4(4) . . ?
C9 C8 C7 122.0(4) . . ?
N1 C1 H1 118.8 . . ?
N1 C1 C2 122.4(4) . . ?
C2 C1 H1 118.8 . . ?
C5 C4 H4 120.6 . . ?
C3 C4 C5 118.8(4) . . ?
C3 C4 H4 120.6 . . ?
C4 C3 H3 120.3 . . ?
C2 C3 C4 119.5(4) . . ?
C2 C3 H3 120.3 . . ?
N3 C14 C13 114.1(4) . . ?
N3 C14 C15 122.6(4) . . ?
C15 C14 C13 123.3(4) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.1(5) . . ?
C10 C9 H9 120.4 . . ?
N2 C12 H12 118.8 . . ?
N2 C12 C11 122.4(5) . . ?
C11 C12 H12 118.8 . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.7(4) . . ?
C3 C2 H2 120.6 . . ?
C14 C15 H15 121.4 . . ?
C14 C15 C16 117.2(5) . . ?
C16 C15 H15 121.4 . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 119.1(5) . . ?
C11 C10 H10 120.5 . . ?
C12 C11 H11 120.6 . . ?
C10 C11 C12 118.9(5) . . ?
C10 C11 H11 120.6 . . ?
C15 C16 H16 121.1 . . ?
C17 C16 C15 117.9(5) . . ?
C17 C16 H16 121.1 . . ?
H4A O4 H4B 121.5 . . ?
N3 C18 H18 118.8 . . ?
N3 C18 C17 122.5(5) . . ?
C17 C18 H18 118.8 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.2(5) . . ?
C18 C17 H17 119.4 . . ?

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
O1 H1A N3_$1 1.04 1.81 2.799(6) 158.9 2_566
O1 H1B O2 0.88 2.12 2.771(6) 130.3 .

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_khc
_database_code_depnum_ccdc_archive 'CCDC 1552125'
_audit_update_record             
;
2018-06-01 deposited with the CCDC.
2018-07-25 downloaded from the CCDC.
;
_audit_creation_date             2017-05-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H12 Cl2 Cu N3, 0.5(C3 H7 N O)'
_chemical_formula_sum            'C19.50 H15.50 Cl2 Cu N3.50 O0.50'
_chemical_formula_weight         441.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   8.9606(5)
_cell_length_b                   20.9052(13)
_cell_length_c                   20.0946(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.240(2)
_cell_angle_gamma                90
_cell_volume                     3763.3(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9863
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.52
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.457
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1071
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            44373
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.532
_diffrn_reflns_theta_min         1.948
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3162
_reflns_number_total             3906
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         3906
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0045P)²+16.6900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0659
_refine_ls_wR_factor_ref         0.0722
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C21-H21A = C21-H21B = C21-H21C
 0.96 with sigma of 0.02
 H21A-H21B = H21A-H21C = H21B-H21C
 1.56 with sigma of 0.02
 C20-H20A = C20-H20B = C20-H20C
 0.96 with sigma of 0.02
 H20A-H20B = H20A-H20C = H20B-H20C
 1.56 with sigma of 0.02
 C19-H19
 0.93 with sigma of 0.02
 O1-H19
 1.87 with sigma of 0.02
2. Others
 Fixed Sof: O1(0.5) C19(0.5) H19(0.5) C20(0.5) H20B(0.5) H20C(0.5) C21(0.5)
 H21B(0.5) H21C(0.5)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 -0.17016(4) 0.25517(2) 0.08601(2) 0.01019(9) Uani 1 1 d . . . . .
Cl1 Cl -0.30684(8) 0.17763(3) 0.03147(3) 0.01514(15) Uani 1 1 d . . . . .
Cl2 Cl -0.36078(8) 0.29327(4) 0.14414(3) 0.02072(17) Uani 1 1 d . . . . .
C1 C 0.0227(3) 0.24144(12) 0.21652(12) 0.0099(5) Uani 1 1 d . . . . .
C2 C 0.0426(3) 0.18323(13) 0.18366(13) 0.0098(5) Uani 1 1 d . . . . .
C3 C 0.0185(3) 0.12488(12) 0.21634(13) 0.0112(5) Uani 1 1 d . . . . .
C4 C 0.0543(3) 0.30393(13) 0.18374(12) 0.0114(6) Uani 1 1 d . . . . .
C5 C 0.1641(3) 0.34483(14) 0.20890(13) 0.0144(6) Uani 1 1 d . . . . .
H5 H 0.218(3) 0.3311(14) 0.2437(16) 0.017(8) Uiso 1 1 d . . . . .
C6 C 0.1814(4) 0.40455(15) 0.18074(14) 0.0190(6) Uani 1 1 d . . . . .
H6 H 0.255(4) 0.4330(15) 0.1966(15) 0.022(9) Uiso 1 1 d . . . . .
C7 C 0.0876(4) 0.42261(14) 0.12857(14) 0.0174(6) Uani 1 1 d . . . . .
H7 H 0.092(4) 0.4647(16) 0.1086(16) 0.029(9) Uiso 1 1 d . . . . .
C8 C -0.0161(3) 0.37911(13) 0.10458(13) 0.0142(6) Uani 1 1 d . . . . .
H8 H -0.078(3) 0.3882(14) 0.0697(15) 0.013(8) Uiso 1 1 d . . . . .
N1 N -0.0319(2) 0.32035(10) 0.13019(10) 0.0104(5) Uani 1 1 d . . . . .
C9 C 0.1015(3) 0.18119(12) 0.11469(12) 0.0097(5) Uani 1 1 d . . . . .
C10 C 0.2356(3) 0.15113(13) 0.10272(13) 0.0137(6) Uani 1 1 d . . . . .
H10 H 0.289(3) 0.1342(13) 0.1404(14) 0.009(7) Uiso 1 1 d . . . . .
C11 C 0.2850(3) 0.14617(14) 0.03798(14) 0.0157(6) Uani 1 1 d . . . . .
H11 H 0.377(4) 0.1266(16) 0.0284(16) 0.028(9) Uiso 1 1 d . . . . .
C12 C 0.1970(3) 0.17113(14) -0.01294(14) 0.0149(6) Uani 1 1 d . . . . .
H12 H 0.224(3) 0.1680(14) -0.0571(15) 0.016(8) Uiso 1 1 d . . . . .
C13 C 0.0662(3) 0.20181(13) 0.00214(13) 0.0122(6) Uani 1 1 d . . . . .
H13 H 0.003(3) 0.2184(14) -0.0295(14) 0.013(8) Uiso 1 1 d . . . . .
N2 N 0.0191(2) 0.20755(10) 0.06499(10) 0.0097(5) Uani 1 1 d . . . . .
C14 C 0.0300(3) 0.06378(13) 0.17789(13) 0.0116(6) Uani 1 1 d . . . . .
C15 C -0.0634(3) 0.05435(14) 0.12295(13) 0.0134(6) Uani 1 1 d . . . . .
H15 H -0.124(4) 0.0809(16) 0.1124(16) 0.019(9) Uiso 1 1 d . . . . .
C16 C -0.0484(3) -0.00084(15) 0.08604(14) 0.0193(6) Uani 1 1 d . . . . .
H16 H -0.113(4) -0.0077(15) 0.0481(16) 0.024(9) Uiso 1 1 d . . . . .
C17 C 0.0586(4) -0.04480(15) 0.10481(15) 0.0223(7) Uani 1 1 d . . . . .
H17 H 0.073(4) -0.0828(17) 0.0828(17) 0.030(9) Uiso 1 1 d . . . . .
C18 C 0.1461(4) -0.03228(15) 0.16092(15) 0.0215(7) Uani 1 1 d . . . . .
H18 H 0.222(4) -0.0628(15) 0.1744(15) 0.022(8) Uiso 1 1 d . . . . .
N3 N 0.1342(3) 0.02134(11) 0.19769(11) 0.0171(5) Uani 1 1 d . . . . .
O1 O 0.5988(7) 0.0641(2) 0.1586(3) 0.0538(17) Uani 0.5 1 d D . . . .
C19 C 0.5765(9) 0.1116(3) 0.1886(4) 0.0337(17) Uani 0.5 1 d D . . . .
H19 H 0.618(8) 0.1514(11) 0.177(3) 0.04(2) Uiso 0.5 1 d D . . . .
N4 N 0.500000 0.11406(17) 0.250000 0.0238(8) Uani 1 2 d S T P . .
C20 C 0.4464(8) 0.1740(3) 0.2721(3) 0.0272(15) Uani 0.5 1 d D . . . .
H20A H 0.500000 0.2065(13) 0.250000 0.032(14) Uiso 1 2 d DS T P . .
H20B H 0.467(6) 0.176(3) 0.3195(10) 0.06(3) Uiso 0.5 1 d D . . . .
H20C H 0.341(2) 0.179(3) 0.265(3) 0.06(3) Uiso 0.5 1 d D . . . .
C21 C 0.4702(9) 0.0576(4) 0.2828(4) 0.0377(18) Uani 0.5 1 d D . . . .
H21A H 0.500000 0.0246(14) 0.250000 0.07(2) Uiso 1 2 d DS T P . .
H21B H 0.522(7) 0.046(3) 0.3238(14) 0.12(4) Uiso 0.5 1 d D . . . .
H21C H 0.365(3) 0.049(3) 0.290(3) 0.04(2) Uiso 0.5 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 Cl1 2.2956(7) . ?
Cu1 Cl1 2.7509(7) 7_455 ?
Cu1 Cl2 2.2367(8) . ?
Cu1 N1 2.033(2) . ?
Cu1 N2 2.019(2) . ?
Cl1 Cu1 2.7508(7) 7_455 ?
C1 C1 1.414(5) 2 ?
C1 C2 1.398(4) . ?
C1 C4 1.493(4) . ?
C2 C3 1.404(4) . ?
C2 C9 1.494(4) . ?
C3 C3 1.400(5) 2 ?
C3 C14 1.497(4) . ?
C4 C5 1.391(4) . ?
C4 N1 1.355(3) . ?
C5 C6 1.381(4) . ?
C6 C7 1.382(4) . ?
C7 C8 1.379(4) . ?
C8 N1 1.341(3) . ?
C9 C10 1.382(4) . ?
C9 N2 1.347(3) . ?
C10 C11 1.387(4) . ?
C11 C12 1.381(4) . ?
C12 C13 1.376(4) . ?
C13 N2 1.346(3) . ?
C14 C15 1.385(4) . ?
C14 N3 1.342(4) . ?
C15 C16 1.380(4) . ?
C16 C17 1.375(4) . ?
C17 C18 1.384(4) . ?
C18 N3 1.348(4) . ?
O1 C19 1.181(8) . ?
O1 C21 1.349(9) 2_655 ?
C19 N4 1.425(7) . ?
C19 C20 1.539(9) 2_655 ?
C19 C21 1.338(10) 2_655 ?
N4 C19 1.425(7) 2_655 ?
N4 C20 1.416(7) . ?
N4 C20 1.416(7) 2_655 ?
N4 C21 1.380(7) 2_655 ?
N4 C21 1.380(7) . ?
C20 C19 1.539(9) 2_655 ?
C20 C20 1.322(14) 2_655 ?
C21 O1 1.349(9) 2_655 ?
C21 C19 1.338(10) 2_655 ?
C21 C21 1.432(16) 2_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Cu1 Cl1 85.50(2) . 7_455 ?
Cl2 Cu1 Cl1 95.46(3) . . ?
Cl2 Cu1 Cl1 102.85(3) . 7_455 ?
N1 Cu1 Cl1 93.79(6) . 7_455 ?
N1 Cu1 Cl1 174.62(7) . . ?
N1 Cu1 Cl2 89.89(6) . . ?
N2 Cu1 Cl1 96.89(6) . 7_455 ?
N2 Cu1 Cl1 89.65(6) . . ?
N2 Cu1 Cl2 159.92(6) . . ?
N2 Cu1 N1 85.14(9) . . ?
Cu1 Cl1 Cu1 94.50(2) . 7_455 ?
C1 C1 C4 118.76(14) 2 . ?
C2 C1 C1 119.46(15) . 2 ?
C2 C1 C4 121.7(2) . . ?
C1 C2 C3 120.9(2) . . ?
C1 C2 C9 121.0(2) . . ?
C3 C2 C9 118.0(2) . . ?
C2 C3 C14 119.1(2) . . ?
C3 C3 C2 119.60(15) 2 . ?
C3 C3 C14 121.26(14) 2 . ?
C5 C4 C1 121.1(2) . . ?
N1 C4 C1 117.5(2) . . ?
N1 C4 C5 121.3(2) . . ?
C6 C5 C4 119.4(3) . . ?
C5 C6 C7 119.1(3) . . ?
C8 C7 C6 118.6(3) . . ?
N1 C8 C7 123.1(3) . . ?
C4 N1 Cu1 120.57(18) . . ?
C8 N1 Cu1 121.02(18) . . ?
C8 N1 C4 118.3(2) . . ?
C10 C9 C2 120.0(2) . . ?
N2 C9 C2 118.5(2) . . ?
N2 C9 C10 121.5(2) . . ?
C9 C10 C11 119.6(3) . . ?
C12 C11 C10 118.6(3) . . ?
C13 C12 C11 119.3(3) . . ?
N2 C13 C12 122.3(3) . . ?
C9 N2 Cu1 119.75(17) . . ?
C13 N2 Cu1 121.49(18) . . ?
C13 N2 C9 118.8(2) . . ?
C15 C14 C3 119.1(2) . . ?
N3 C14 C3 117.8(2) . . ?
N3 C14 C15 123.1(3) . . ?
C16 C15 C14 118.9(3) . . ?
C17 C16 C15 119.2(3) . . ?
C16 C17 C18 118.4(3) . . ?
N3 C18 C17 123.6(3) . . ?
C14 N3 C18 116.7(2) . . ?
C19 O1 C21 63.4(5) . 2_655 ?
O1 C19 N4 124.2(6) . . ?
O1 C19 C20 177.9(8) . 2_655 ?
O1 C19 C21 64.4(5) . 2_655 ?
N4 C19 C20 56.9(4) . 2_655 ?
C21 C19 N4 59.8(4) 2_655 . ?
C21 C19 C20 116.6(6) 2_655 2_655 ?
C19 N4 C19 175.9(6) . 2_655 ?
C20 N4 C19 65.6(4) . 2_655 ?
C20 N4 C19 118.4(4) . . ?
C20 N4 C19 118.4(4) 2_655 2_655 ?
C20 N4 C19 65.6(4) 2_655 . ?
C20 N4 C20 55.7(6) 2_655 . ?
C21 N4 C19 119.0(5) . . ?
C21 N4 C19 57.0(4) 2_655 . ?
C21 N4 C19 57.0(4) . 2_655 ?
C21 N4 C19 119.0(5) 2_655 2_655 ?
C21 N4 C20 122.4(5) . . ?
C21 N4 C20 122.4(5) 2_655 2_655 ?
C21 N4 C20 167.4(5) 2_655 . ?
C21 N4 C20 167.4(5) . 2_655 ?
C21 N4 C21 62.5(7) 2_655 . ?
N4 C20 C19 57.5(4) . 2_655 ?
C20 C20 C19 116.8(4) 2_655 2_655 ?
C20 C20 N4 62.2(3) 2_655 . ?
O1 C21 N4 115.3(6) 2_655 . ?
O1 C21 C21 172.0(8) 2_655 2_655 ?
C19 C21 O1 52.2(5) 2_655 2_655 ?
C19 C21 N4 63.2(5) 2_655 . ?
C19 C21 C21 121.4(5) 2_655 2_655 ?
N4 C21 C21 58.7(4) . 2_655 ?

_olex2_submission_special_instructions 'No special instructions were received'
