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

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

data_20180102_1a_0m
_database_code_depnum_ccdc_archive 'CCDC 1888681'
loop_
_audit_author_name
_audit_author_address
'Li hai-tao'
;Liaoning University, Shenyang, 110036, China.
China
;
_audit_update_record             
;
2019-01-04 deposited with the CCDC.	2019-06-19 downloaded from the CCDC.
;
_audit_creation_date             2018-01-02
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(Cl), C18 H28 N4, H2 O'
_chemical_formula_sum            'C18 H30 Cl4 N4 O'
_chemical_formula_weight         460.26
_chemical_absolute_configuration ad
_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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   7.7024(11)
_cell_length_b                   15.716(2)
_cell_length_c                   18.368(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2223.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9281
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.262
_cell_measurement_theta_min      2.946
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.908
_exptl_absorpt_coefficient_mu    0.548
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0780 before and 0.0556 after correction.
The Ratio of minimum to maximum transmission is 0.7877.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            28774
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         28.262
_diffrn_reflns_theta_min         2.945
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                5189
_reflns_number_total             5401
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.398
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 2204 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.062(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         5401
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.120
_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)+(0.0265P)²+0.9214P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0789
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), N3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C3(H3C,H3D),
 C13(H13A,H13B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N4(H4), C14(H14), C8(H8), C16(H16), C18(H18), C11(H11), C10(H10),
 C12(H12), 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
Cl1 Cl 0.51789(8) 0.99655(4) 0.41366(4) 0.03940(15) Uani 1 1 d . . . . .
Cl4 Cl 0.23209(9) 0.32651(4) 0.42514(4) 0.04136(16) Uani 1 1 d . . . . .
Cl2 Cl 0.17332(10) 0.68673(4) 0.42743(4) 0.04291(17) Uani 1 1 d . . . . .
Cl3 Cl 0.53381(10) 0.49608(4) 0.29722(3) 0.04101(17) Uani 1 1 d . . . . .
N2 N 0.5178(3) 0.59294(11) 0.44532(10) 0.0238(4) Uani 1 1 d . . . . .
H2A H 0.5110 0.5606 0.4056 0.029 Uiso 1 1 calc R . . . .
H2B H 0.4310 0.6302 0.4433 0.029 Uiso 1 1 calc R . . . .
N1 N 0.6074(3) 0.83509(13) 0.32915(12) 0.0317(4) Uani 1 1 d . . . . .
H1 H 0.5612 0.8844 0.3351 0.038 Uiso 1 1 calc R . . . .
N3 N 0.5966(3) 0.40455(11) 0.44661(10) 0.0235(4) Uani 1 1 d . . . . .
H3A H 0.4951 0.3775 0.4468 0.028 Uiso 1 1 calc R . . . .
H3B H 0.5999 0.4376 0.4073 0.028 Uiso 1 1 calc R . . . .
C15 C 0.6838(3) 0.70177(14) 0.37821(13) 0.0264(4) Uani 1 1 d . . . . .
N4 N 0.6362(3) 0.15312(14) 0.32636(14) 0.0395(5) Uani 1 1 d . . . . .
H4 H 0.5873 0.1043 0.3317 0.047 Uiso 1 1 calc R . . . .
C2 C 0.4891(3) 0.53646(13) 0.51107(11) 0.0225(4) Uani 1 1 d . . . . .
H2 H 0.3694 0.5154 0.5092 0.027 Uiso 1 1 calc R . . . .
C1 C 0.6102(3) 0.45944(13) 0.51400(11) 0.0218(4) Uani 1 1 d . . . . .
H1A H 0.7301 0.4794 0.5190 0.026 Uiso 1 1 calc R . . . .
C14 C 0.6098(3) 0.78148(15) 0.38549(14) 0.0297(5) Uani 1 1 d . . . . .
H14 H 0.5615 0.7978 0.4298 0.036 Uiso 1 1 calc R . . . .
C9 C 0.7223(3) 0.28412(14) 0.37675(13) 0.0291(5) Uani 1 1 d . . . . .
C8 C 0.6456(4) 0.20534(15) 0.38399(15) 0.0337(5) Uani 1 1 d . . . . .
H8 H 0.6006 0.1884 0.4287 0.040 Uiso 1 1 calc R . . . .
C16 C 0.7561(4) 0.68013(15) 0.31144(13) 0.0313(5) Uani 1 1 d . . . . .
H16 H 0.8085 0.6273 0.3053 0.038 Uiso 1 1 calc R . . . .
C4 C 0.4642(4) 0.53579(16) 0.64841(12) 0.0316(5) Uani 1 1 d . . . . .
H4A H 0.4831 0.5696 0.6919 0.038 Uiso 1 1 calc R . . . .
H4B H 0.3424 0.5201 0.6467 0.038 Uiso 1 1 calc R . . . .
C5 C 0.5745(3) 0.45624(17) 0.65181(12) 0.0324(5) Uani 1 1 d . . . . .
H5A H 0.5358 0.4209 0.6919 0.039 Uiso 1 1 calc R . . . .
H5B H 0.6944 0.4719 0.6608 0.039 Uiso 1 1 calc R . . . .
C7 C 0.7406(4) 0.34063(17) 0.44270(13) 0.0358(6) Uani 1 1 d . . . . .
H7A H 0.7396 0.3059 0.4863 0.043 Uiso 1 1 calc R . . . .
H7B H 0.8511 0.3701 0.4406 0.043 Uiso 1 1 calc R . . . .
C18 C 0.6738(4) 0.81562(16) 0.26352(14) 0.0330(5) Uani 1 1 d . . . . .
H18 H 0.6682 0.8544 0.2254 0.040 Uiso 1 1 calc R . . . .
C3 C 0.5099(3) 0.58845(14) 0.58103(13) 0.0309(5) Uani 1 1 d . . . . .
H3C H 0.6289 0.6082 0.5849 0.037 Uiso 1 1 calc R . . . .
H3D H 0.4350 0.6380 0.5788 0.037 Uiso 1 1 calc R . . . .
C13 C 0.6858(3) 0.64165(16) 0.44219(13) 0.0320(5) Uani 1 1 d . . . . .
H13A H 0.7822 0.6023 0.4374 0.038 Uiso 1 1 calc R . . . .
H13B H 0.7014 0.6736 0.4869 0.038 Uiso 1 1 calc R . . . .
C11 C 0.7760(4) 0.25124(18) 0.25067(14) 0.0434(7) Uani 1 1 d . . . . .
H11 H 0.8191 0.2666 0.2052 0.052 Uiso 1 1 calc R . . . .
C10 C 0.7884(4) 0.30680(17) 0.30926(15) 0.0369(6) Uani 1 1 d . . . . .
H10 H 0.8413 0.3595 0.3032 0.044 Uiso 1 1 calc R . . . .
C12 C 0.6995(4) 0.17368(19) 0.26092(16) 0.0419(6) Uani 1 1 d . . . . .
H12 H 0.6914 0.1354 0.2225 0.050 Uiso 1 1 calc R . . . .
C6 C 0.5630(4) 0.40561(15) 0.58072(13) 0.0345(5) Uani 1 1 d . . . . .
H6A H 0.4458 0.3840 0.5750 0.041 Uiso 1 1 calc R . . . .
H6B H 0.6409 0.3572 0.5834 0.041 Uiso 1 1 calc R . . . .
C17 C 0.7502(4) 0.73738(17) 0.25383(13) 0.0353(5) Uani 1 1 d . . . . .
H17 H 0.7977 0.7228 0.2090 0.042 Uiso 1 1 calc R . . . .
O1 O 0.0164(6) 0.4995(3) 0.3696(3) 0.123(2) Uani 1 1 d . . . . .
H1B H 0.057(7) 0.536(3) 0.379(3) 0.075(17) Uiso 1 1 d . . . . .
H1C H 0.069(7) 0.464(3) 0.366(3) 0.076(17) Uiso 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
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 C2 1.515(3) . ?
N2 C13 1.505(3) . ?
N1 H1 0.8600 . ?
N1 C14 1.335(3) . ?
N1 C18 1.345(3) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 C1 1.512(3) . ?
N3 C7 1.499(3) . ?
C15 C14 1.383(3) . ?
C15 C16 1.389(3) . ?
C15 C13 1.508(3) . ?
N4 H4 0.8600 . ?
N4 C8 1.341(3) . ?
N4 C12 1.337(4) . ?
C2 H2 0.9800 . ?
C2 C1 1.529(3) . ?
C2 C3 1.531(3) . ?
C1 H1A 0.9800 . ?
C1 C6 1.533(3) . ?
C14 H14 0.9300 . ?
C9 C8 1.378(3) . ?
C9 C7 1.509(3) . ?
C9 C10 1.387(4) . ?
C8 H8 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.390(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.513(4) . ?
C4 C3 1.530(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.532(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C18 H18 0.9300 . ?
C18 C17 1.375(4) . ?
C3 H3C 0.9700 . ?
C3 H3D 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C11 H11 0.9300 . ?
C11 C10 1.389(3) . ?
C11 C12 1.367(4) . ?
C10 H10 0.9300 . ?
C12 H12 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C17 H17 0.9300 . ?
O1 H1B 0.68(5) . ?
O1 H1C 0.69(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H2A N2 H2B 107.3 . . ?
C2 N2 H2A 108.0 . . ?
C2 N2 H2B 108.0 . . ?
C13 N2 H2A 108.0 . . ?
C13 N2 H2B 108.0 . . ?
C13 N2 C2 117.00(17) . . ?
C14 N1 H1 118.4 . . ?
C14 N1 C18 123.1(2) . . ?
C18 N1 H1 118.4 . . ?
H3A N3 H3B 107.9 . . ?
C1 N3 H3A 109.3 . . ?
C1 N3 H3B 109.3 . . ?
C7 N3 H3A 109.3 . . ?
C7 N3 H3B 109.3 . . ?
C7 N3 C1 111.73(17) . . ?
C14 C15 C16 118.2(2) . . ?
C14 C15 C13 119.8(2) . . ?
C16 C15 C13 122.0(2) . . ?
C8 N4 H4 118.6 . . ?
C12 N4 H4 118.6 . . ?
C12 N4 C8 122.8(2) . . ?
N2 C2 H2 107.9 . . ?
N2 C2 C1 113.78(17) . . ?
N2 C2 C3 109.94(17) . . ?
C1 C2 H2 107.9 . . ?
C1 C2 C3 109.21(17) . . ?
C3 C2 H2 107.9 . . ?
N3 C1 C2 112.36(17) . . ?
N3 C1 H1A 109.0 . . ?
N3 C1 C6 108.85(17) . . ?
C2 C1 H1A 109.0 . . ?
C2 C1 C6 108.70(18) . . ?
C6 C1 H1A 109.0 . . ?
N1 C14 C15 120.2(2) . . ?
N1 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C8 C9 C7 119.4(2) . . ?
C8 C9 C10 118.3(2) . . ?
C10 C9 C7 122.2(2) . . ?
N4 C8 C9 119.8(2) . . ?
N4 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0(2) . . ?
C17 C16 H16 120.0 . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C5 C4 C3 110.5(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C4 C5 C6 111.19(19) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
N3 C7 C9 111.3(2) . . ?
N3 C7 H7A 109.4 . . ?
N3 C7 H7B 109.4 . . ?
C9 C7 H7A 109.4 . . ?
C9 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N1 C18 H18 120.6 . . ?
N1 C18 C17 118.8(2) . . ?
C17 C18 H18 120.6 . . ?
C2 C3 H3C 109.3 . . ?
C2 C3 H3D 109.3 . . ?
C4 C3 C2 111.47(18) . . ?
C4 C3 H3C 109.3 . . ?
C4 C3 H3D 109.3 . . ?
H3C C3 H3D 108.0 . . ?
N2 C13 C15 109.86(19) . . ?
N2 C13 H13A 109.7 . . ?
N2 C13 H13B 109.7 . . ?
C15 C13 H13A 109.7 . . ?
C15 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C12 C11 C10 118.9(3) . . ?
C9 C10 C11 120.4(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
N4 C12 C11 119.8(2) . . ?
N4 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C1 C6 H6A 109.1 . . ?
C1 C6 H6B 109.1 . . ?
C5 C6 C1 112.40(18) . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.6(2) . . ?
C18 C17 H17 120.2 . . ?
H1B O1 H1C 116(6) . . ?

_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_20171128_3a_0m
_database_code_depnum_ccdc_archive 'CCDC 1888684'
loop_
_audit_author_name
_audit_author_address
'Li hai-tao'
;Liaoning University, Shenyang, 110036, China.
China
;
_audit_update_record             
;
2019-01-04 deposited with the CCDC.	2019-06-19 downloaded from the CCDC.
;
_audit_creation_date             2017-11-28
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl3 Cu H2 O, 3(Cl), C18 H28 N4'
_chemical_formula_sum            'C18 H30 Cl6 Cu N4 O'
_chemical_formula_weight         594.70
_chemical_absolute_configuration ad
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.9923(5)
_cell_length_b                   14.3694(10)
_cell_length_c                   12.7878(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.514(2)
_cell_angle_gamma                90
_cell_volume                     1259.00(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9853
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.364
_cell_measurement_theta_min      2.973
_shelx_estimated_absorpt_T_max   0.914
_shelx_estimated_absorpt_T_min   0.815
_exptl_absorpt_coefficient_mu    1.523
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1048 before and 0.0656 after correction.
The Ratio of minimum to maximum transmission is 0.7354.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             610
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21527
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         28.370
_diffrn_reflns_theta_min         2.973
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_full    0.945
_reflns_Friedel_fraction_max     0.947
_reflns_number_gt                5938
_reflns_number_total             6090
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.998
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details 
;
 Flack x determined using 2680 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.072(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         6090
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.074
_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)+(0.0402P)²+1.4134P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.0979
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O1(H1B,H1C)
2.b Ternary CH refined with riding coordinates:
 C7(H7), C12(H12)
2.c Secondary CH2 refined with riding coordinates:
 N4(H4A,H4B), N3(H3A,H3B), C8(H8A,H8B), C13(H13A,H13B), C6(H6A,H6B), C10(H10A,
 H10B), C11(H11A,H11B), C9(H9A,H9B)
2.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C15(H15), C1(H1A), C16(H16), C18(H18), C3(H3), C2(H2),
 N2(H2A), 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
Cu01 Cu 1.01007(8) 0.50706(4) 0.90125(3) 0.02890(13) Uani 1 1 d . . . . .
Cl3 Cl 0.76608(16) 0.35973(9) 0.58685(10) 0.0397(3) Uani 1 1 d . . . . .
Cl6 Cl 1.01889(18) 0.34783(8) 0.89796(10) 0.0376(3) Uani 1 1 d . . . . .
Cl2 Cl 0.5540(2) 0.51428(10) 0.85145(8) 0.0421(3) Uani 1 1 d . . . . .
Cl5 Cl 1.08017(18) 0.50861(13) 1.07907(8) 0.0430(2) Uani 1 1 d . . . . .
Cl4 Cl 1.0555(2) 0.66253(8) 0.89229(12) 0.0434(3) Uani 1 1 d . . . . .
Cl1 Cl 0.89723(18) 0.65927(10) 0.58020(12) 0.0460(3) Uani 1 1 d . . . . .
O1 O 0.9844(5) 0.5028(3) 0.7455(2) 0.0325(6) Uani 1 1 d . . . . .
H1B H 0.9492 0.5568 0.7173 0.049 Uiso 1 1 d GR . . . .
H1C H 0.8888 0.4665 0.7165 0.049 Uiso 1 1 d GR . . . .
N4 N 0.3715(5) 0.4016(2) 0.6450(3) 0.0217(7) Uani 1 1 d . . . . .
H4A H 0.4920 0.3908 0.6351 0.026 Uiso 1 1 calc R . . . .
H4B H 0.3810 0.4330 0.7058 0.026 Uiso 1 1 calc R . . . .
N3 N 0.3418(5) 0.6160(2) 0.6414(3) 0.0218(7) Uani 1 1 d . . . . .
H3A H 0.2138 0.6227 0.6368 0.026 Uiso 1 1 calc R . . . .
H3B H 0.3903 0.5886 0.7035 0.026 Uiso 1 1 calc R . . . .
N1 N 0.6285(6) 0.2134(3) 0.8910(4) 0.0335(9) Uani 1 1 d . . . . .
H1 H 0.7482 0.2206 0.9226 0.040 Uiso 1 1 calc R . . . .
C7 C 0.2649(6) 0.4614(3) 0.5537(3) 0.0229(7) Uani 1 1 d . . . . .
H7 H 0.1333 0.4751 0.5652 0.028 Uiso 1 1 calc R . . . .
C14 C 0.4458(6) 0.7630(3) 0.7421(3) 0.0227(7) Uani 1 1 d . . . . .
C12 C 0.3769(6) 0.5535(3) 0.5510(3) 0.0233(7) Uani 1 1 d . . . . .
H12 H 0.5168 0.5399 0.5612 0.028 Uiso 1 1 calc R . . . .
C4 C 0.3670(6) 0.2560(3) 0.7521(3) 0.0243(8) Uani 1 1 d . . . . .
C5 C 0.5578(6) 0.2663(3) 0.8046(4) 0.0280(9) Uani 1 1 d . . . . .
H5 H 0.6380 0.3096 0.7805 0.034 Uiso 1 1 calc R . . . .
C15 C 0.6205(7) 0.7646(4) 0.8132(4) 0.0372(11) Uani 1 1 d . . . . .
H15 H 0.7261 0.7305 0.7998 0.045 Uiso 1 1 calc R . . . .
C8 C 0.2495(9) 0.4054(3) 0.4499(4) 0.0385(12) Uani 1 1 d . . . . .
H8A H 0.3768 0.3800 0.4468 0.046 Uiso 1 1 calc R . . . .
H8B H 0.1609 0.3536 0.4508 0.046 Uiso 1 1 calc R . . . .
C13 C 0.4332(7) 0.7104(3) 0.6392(4) 0.0306(9) Uani 1 1 d . . . . .
H13A H 0.3572 0.7464 0.5814 0.037 Uiso 1 1 calc R . . . .
H13B H 0.5635 0.7031 0.6249 0.037 Uiso 1 1 calc R . . . .
C1 C 0.5196(8) 0.1500(4) 0.9297(5) 0.0429(12) Uani 1 1 d . . . . .
H1A H 0.5724 0.1157 0.9903 0.051 Uiso 1 1 calc R . . . .
C16 C 0.6382(9) 0.8156(4) 0.9021(4) 0.0434(13) Uani 1 1 d . . . . .
H16 H 0.7577 0.8158 0.9496 0.052 Uiso 1 1 calc R . . . .
C18 C 0.2924(8) 0.8129(4) 0.7643(5) 0.0431(12) Uani 1 1 d . . . . .
H18 H 0.1729 0.8120 0.7168 0.052 Uiso 1 1 calc R . . . .
C3 C 0.2537(8) 0.1898(4) 0.7897(5) 0.0386(11) Uani 1 1 d . . . . .
H3 H 0.1250 0.1808 0.7549 0.046 Uiso 1 1 calc R . . . .
C6 C 0.2742(6) 0.3111(3) 0.6552(4) 0.0301(9) Uani 1 1 d . . . . .
H6A H 0.2765 0.2741 0.5920 0.036 Uiso 1 1 calc R . . . .
H6B H 0.1387 0.3226 0.6581 0.036 Uiso 1 1 calc R . . . .
C10 C 0.3116(13) 0.5447(4) 0.3491(4) 0.0551(17) Uani 1 1 d . . . . .
H10A H 0.2671 0.5803 0.2844 0.066 Uiso 1 1 calc R . . . .
H10B H 0.4428 0.5229 0.3490 0.066 Uiso 1 1 calc R . . . .
C11 C 0.3134(10) 0.6067(3) 0.4464(4) 0.0392(12) Uani 1 1 d . . . . .
H11A H 0.4018 0.6584 0.4446 0.047 Uiso 1 1 calc R . . . .
H11B H 0.1837 0.6319 0.4433 0.047 Uiso 1 1 calc R . . . .
C2 C 0.3307(9) 0.1365(4) 0.8792(5) 0.0473(14) Uani 1 1 d . . . . .
H2 H 0.2540 0.0921 0.9042 0.057 Uiso 1 1 calc R . . . .
N2 N 0.3136(12) 0.8645(5) 0.8569(7) 0.080(2) Uani 1 1 d . . . . .
H2A H 0.2179 0.8956 0.8724 0.097 Uiso 1 1 calc R . . . .
C9 C 0.1784(12) 0.4627(4) 0.3515(4) 0.0543(17) Uani 1 1 d . . . . .
H9A H 0.0470 0.4846 0.3512 0.065 Uiso 1 1 calc R . . . .
H9B H 0.1749 0.4247 0.2885 0.065 Uiso 1 1 calc R . . . .
C17 C 0.4985(13) 0.8642(6) 0.9249(6) 0.066(2) Uani 1 1 d . . . . .
H17 H 0.5195 0.8995 0.9871 0.079 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu01 Cl6 2.2896(13) . ?
Cu01 Cl5 2.2285(10) . ?
Cu01 Cl4 2.2626(14) . ?
Cu01 O1 1.964(3) . ?
O1 H1B 0.8704 . ?
O1 H1C 0.8707 . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N4 C7 1.520(5) . ?
N4 C6 1.486(5) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 C12 1.522(5) . ?
N3 C13 1.502(5) . ?
N1 H1 0.8600 . ?
N1 C5 1.352(6) . ?
N1 C1 1.344(7) . ?
C7 H7 0.9800 . ?
C7 C12 1.542(5) . ?
C7 C8 1.538(6) . ?
C14 C15 1.370(6) . ?
C14 C13 1.504(6) . ?
C14 C18 1.367(6) . ?
C12 H12 0.9800 . ?
C12 C11 1.527(6) . ?
C4 C5 1.376(6) . ?
C4 C3 1.385(6) . ?
C4 C6 1.503(6) . ?
C5 H5 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.337(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.503(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C1 H1A 0.9300 . ?
C1 C2 1.364(9) . ?
C16 H16 0.9300 . ?
C16 C17 1.281(11) . ?
C18 H18 0.9300 . ?
C18 N2 1.380(9) . ?
C3 H3 0.9300 . ?
C3 C2 1.393(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.528(7) . ?
C10 C9 1.506(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C2 H2 0.9300 . ?
N2 H2A 0.8600 . ?
N2 C17 1.407(12) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
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
Cl5 Cu01 Cl6 91.57(6) . . ?
Cl5 Cu01 Cl4 92.14(6) . . ?
Cl4 Cu01 Cl6 168.88(6) . . ?
O1 Cu01 Cl6 87.01(12) . . ?
O1 Cu01 Cl5 172.60(10) . . ?
O1 Cu01 Cl4 87.97(12) . . ?
Cu01 O1 H1B 110.7 . . ?
Cu01 O1 H1C 111.0 . . ?
H1B O1 H1C 103.2 . . ?
H4A N4 H4B 107.7 . . ?
C7 N4 H4A 108.9 . . ?
C7 N4 H4B 108.9 . . ?
C6 N4 H4A 108.9 . . ?
C6 N4 H4B 108.9 . . ?
C6 N4 C7 113.6(3) . . ?
H3A N3 H3B 107.8 . . ?
C12 N3 H3A 109.1 . . ?
C12 N3 H3B 109.1 . . ?
C13 N3 H3A 109.1 . . ?
C13 N3 H3B 109.1 . . ?
C13 N3 C12 112.6(3) . . ?
C5 N1 H1 118.6 . . ?
C1 N1 H1 118.6 . . ?
C1 N1 C5 122.7(4) . . ?
N4 C7 H7 109.2 . . ?
N4 C7 C12 109.2(3) . . ?
N4 C7 C8 107.8(3) . . ?
C12 C7 H7 109.2 . . ?
C8 C7 H7 109.2 . . ?
C8 C7 C12 112.2(4) . . ?
C15 C14 C13 118.6(4) . . ?
C18 C14 C15 119.0(5) . . ?
C18 C14 C13 122.3(4) . . ?
N3 C12 C7 109.2(3) . . ?
N3 C12 H12 108.9 . . ?
N3 C12 C11 107.9(3) . . ?
C7 C12 H12 108.9 . . ?
C11 C12 C7 112.9(4) . . ?
C11 C12 H12 108.9 . . ?
C5 C4 C3 118.0(4) . . ?
C5 C4 C6 124.2(4) . . ?
C3 C4 C6 117.7(4) . . ?
N1 C5 C4 120.0(4) . . ?
N1 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.6(5) . . ?
C16 C15 H15 120.2 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C7 112.9(4) . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
N3 C13 C14 112.9(3) . . ?
N3 C13 H13A 109.0 . . ?
N3 C13 H13B 109.0 . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
N1 C1 H1A 120.4 . . ?
N1 C1 C2 119.3(5) . . ?
C2 C1 H1A 120.4 . . ?
C15 C16 H16 118.4 . . ?
C17 C16 C15 123.1(6) . . ?
C17 C16 H16 118.4 . . ?
C14 C18 H18 119.8 . . ?
C14 C18 N2 120.4(6) . . ?
N2 C18 H18 119.8 . . ?
C4 C3 H3 119.7 . . ?
C4 C3 C2 120.6(5) . . ?
C2 C3 H3 119.7 . . ?
N4 C6 C4 113.8(3) . . ?
N4 C6 H6A 108.8 . . ?
N4 C6 H6B 108.8 . . ?
C4 C6 H6A 108.8 . . ?
C4 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
H10A C10 H10B 108.2 . . ?
C11 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
C9 C10 C11 110.1(5) . . ?
C12 C11 C10 112.0(4) . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C1 C2 C3 119.3(5) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C18 N2 H2A 121.4 . . ?
C18 N2 C17 117.2(6) . . ?
C17 N2 H2A 121.4 . . ?
C8 C9 C10 110.1(5) . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.2 . . ?
C16 C17 N2 120.6(6) . . ?
C16 C17 H17 119.7 . . ?
N2 C17 H17 119.7 . . ?

_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_20171221_3a_0m
_database_code_depnum_ccdc_archive 'CCDC 1888685'
loop_
_audit_author_name
_audit_author_address
'Li hai-tao'
;Liaoning University, Shenyang, 110036, China.
China
;
_audit_update_record             
;
2019-01-04 deposited with the CCDC.	2019-06-19 downloaded from the CCDC.
;
_audit_creation_date             2017-12-22
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H24 Cl2 Cu N4'
_chemical_formula_sum            'C18 H24 Cl2 Cu N4'
_chemical_formula_weight         430.85
_chemical_absolute_configuration ad
_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'

_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      hexagonal
_space_group_IT_number           178
_space_group_name_H-M_alt        'P 61 2 2'
_space_group_name_Hall           'P 61 2 (0 0 -1)'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+1/6'
'-y, x-y, z+1/3'
'-x, -y, z+1/2'
'-x+y, -x, z+2/3'
'y, -x+y, z+5/6'
'-y, -x, -z+5/6'
'x-y, -y, -z'
'x, x-y, -z+1/6'
'y, x, -z+1/3'
'-x+y, y, -z+1/2'
'-x, -x+y, -z+2/3'

_cell_length_a                   9.8247(4)
_cell_length_b                   9.8247(4)
_cell_length_c                   32.973(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2756.3(3)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    9782
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.232
_cell_measurement_theta_min      3.089
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.488
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1072 before and 0.0738 after correction.
The Ratio of minimum to maximum transmission is 0.6997.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1338
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0395
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            51693
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_min         3.441
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.576
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2223
_reflns_number_total             2269
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.224
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.10(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         2269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.174
_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)+(0.0194P)²+3.1456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0789
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.90(3)
 0.10(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
3.a Ternary CH refined with riding coordinates:
 N2(H2), C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C008(H00A,H00B), C7(H7A,H7B), C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C9(H9), C3(H3), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_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 -0.77001(7) -0.38500(3) -0.4167 0.02740(15) Uani 1 2 d S T P . .
Cl1 Cl -0.94199(12) -0.63833(11) -0.43125(3) 0.0448(3) Uani 1 1 d . . . . .
N4 N -0.5935(4) -0.0691(4) -0.55482(9) 0.0419(8) Uani 1 1 d . . . . .
N2 N -0.5939(3) -0.3822(3) -0.44926(7) 0.0254(5) Uani 1 1 d . . . . .
H2 H -0.5821 -0.4698 -0.4394 0.031 Uiso 1 1 calc R . . . .
C1 C -0.7304(5) -0.0771(5) -0.54654(12) 0.0424(9) Uani 1 1 d . . . . .
H1 H -0.7500 -0.0017 -0.5577 0.051 Uiso 1 1 calc R . . . .
C008 C -0.6306(5) -0.4100(4) -0.49375(10) 0.0344(7) Uani 1 1 d . . . . .
H00A H -0.5404 -0.4024 -0.5078 0.041 Uiso 1 1 calc R . . . .
H00B H -0.7180 -0.5157 -0.4976 0.041 Uiso 1 1 calc R . . . .
C9 C -0.8450(5) -0.1930(5) -0.52202(12) 0.0438(10) Uani 1 1 d . . . . .
H9 H -0.9397 -0.1958 -0.5172 0.053 Uiso 1 1 calc R . . . .
C3 C -0.8148(4) -0.3036(5) -0.50501(11) 0.0372(8) Uani 1 1 d . . . . .
H3 H -0.8901 -0.3834 -0.4889 0.045 Uiso 1 1 calc R . . . .
C4 C -0.6713(4) -0.2952(4) -0.51210(9) 0.0295(7) Uani 1 1 d . . . . .
C5 C -0.5674(4) -0.1767(5) -0.53759(11) 0.0383(8) Uani 1 1 d . . . . .
H5 H -0.4722 -0.1718 -0.5431 0.046 Uiso 1 1 calc R . . . .
C6 C -0.4451(3) -0.2358(4) -0.43950(9) 0.0250(6) Uani 1 1 d . . . . .
H6 H -0.4460 -0.1482 -0.4534 0.030 Uiso 1 1 calc R . . . .
C7 C -0.2973(4) -0.2386(5) -0.45240(11) 0.0342(7) Uani 1 1 d . . . . .
H7A H -0.2974 -0.3283 -0.4401 0.041 Uiso 1 1 calc R . . . .
H7B H -0.2976 -0.2502 -0.4816 0.041 Uiso 1 1 calc R . . . .
C8 C -0.1497(4) -0.0890(5) -0.43977(12) 0.0438(9) Uani 1 1 d . . . . .
H8A H -0.1436 -0.0004 -0.4544 0.053 Uiso 1 1 calc R . . . .
H8B H -0.0580 -0.0968 -0.4468 0.053 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 Cl1 2.2528(10) 9_554 ?
Cu1 Cl1 2.2528(10) . ?
Cu1 N2 2.025(3) . ?
Cu1 N2 2.025(3) 9_554 ?
N4 C1 1.335(5) . ?
N4 C5 1.334(5) . ?
N2 H2 0.9800 . ?
N2 C008 1.503(4) . ?
N2 C6 1.486(4) . ?
C1 H1 0.9300 . ?
C1 C9 1.391(6) . ?
C008 H00A 0.9700 . ?
C008 H00B 0.9700 . ?
C008 C4 1.500(5) . ?
C9 H9 0.9300 . ?
C9 C3 1.381(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(5) . ?
C4 C5 1.384(5) . ?
C5 H5 0.9300 . ?
C6 C6 1.528(6) 9_554 ?
C6 H6 0.9800 . ?
C6 C7 1.526(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.518(5) . ?
C8 C8 1.549(8) 9_554 ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Cu1 Cl1 98.98(6) 9_554 . ?
N2 Cu1 Cl1 153.59(8) 9_554 . ?
N2 Cu1 Cl1 153.59(8) . 9_554 ?
N2 Cu1 Cl1 93.76(8) 9_554 9_554 ?
N2 Cu1 Cl1 93.76(8) . . ?
N2 Cu1 N2 84.56(15) . 9_554 ?
C5 N4 C1 116.9(3) . . ?
Cu1 N2 H2 106.7 . . ?
C008 N2 Cu1 112.9(2) . . ?
C008 N2 H2 106.7 . . ?
C6 N2 Cu1 108.60(19) . . ?
C6 N2 H2 106.7 . . ?
C6 N2 C008 114.7(2) . . ?
N4 C1 H1 118.4 . . ?
N4 C1 C9 123.2(4) . . ?
C9 C1 H1 118.4 . . ?
N2 C008 H00A 109.0 . . ?
N2 C008 H00B 109.0 . . ?
H00A C008 H00B 107.8 . . ?
C4 C008 N2 112.8(3) . . ?
C4 C008 H00A 109.0 . . ?
C4 C008 H00B 109.0 . . ?
C1 C9 H9 120.8 . . ?
C3 C9 C1 118.3(4) . . ?
C3 C9 H9 120.8 . . ?
C9 C3 H3 120.1 . . ?
C9 C3 C4 119.7(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C008 122.1(3) . . ?
C5 C4 C008 121.1(3) . . ?
C5 C4 C3 116.8(3) . . ?
N4 C5 C4 124.9(4) . . ?
N4 C5 H5 117.5 . . ?
C4 C5 H5 117.5 . . ?
N2 C6 C6 107.14(19) . 9_554 ?
N2 C6 H6 108.2 . . ?
N2 C6 C7 114.0(3) . . ?
C6 C6 H6 108.2 9_554 . ?
C7 C6 C6 111.0(2) . 9_554 ?
C7 C6 H6 108.2 . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 C6 111.3(3) . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C7 C8 C8 111.0(3) . 9_554 ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C8 C8 H8A 109.4 9_554 . ?
C8 C8 H8B 109.4 9_554 . ?
H8A C8 H8B 108.0 . . ?

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
Cu1 N2 C008 C4 56.1(3) . . . . ?
Cu1 N2 C6 C6 40.6(3) . . . 9_554 ?
Cu1 N2 C6 C7 163.9(2) . . . . ?
N4 C1 C9 C3 0.9(7) . . . . ?
N2 C008 C4 C3 -74.0(4) . . . . ?
N2 C008 C4 C5 107.0(4) . . . . ?
N2 C6 C7 C8 -177.3(3) . . . . ?
C1 N4 C5 C4 0.2(6) . . . . ?
C1 C9 C3 C4 1.1(6) . . . . ?
C008 N2 C6 C6 168.0(3) . . . 9_554 ?
C008 N2 C6 C7 -68.7(3) . . . . ?
C008 C4 C5 N4 -179.3(3) . . . . ?
C9 C3 C4 C008 178.7(3) . . . . ?
C9 C3 C4 C5 -2.3(5) . . . . ?
C3 C4 C5 N4 1.7(6) . . . . ?
C5 N4 C1 C9 -1.5(6) . . . . ?
C6 N2 C008 C4 -69.1(4) . . . . ?
C6 C6 C7 C8 -56.2(4) 9_554 . . . ?
C6 C7 C8 C8 55.5(5) . . . 9_554 ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.90(3)
2 0.10(3)

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

data_gf01_a
_database_code_depnum_ccdc_archive 'CCDC 1888682'
loop_
_audit_author_name
_audit_author_address
'Li hai-tao'
;liaoning University
China
;
_audit_update_record             
;
2019-06-12 deposited with the CCDC.	2019-06-19 downloaded from the CCDC.
;
_audit_creation_date             2019-06-12
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'Cl4 Cu, 2(Cl), C18 H28 N4'
_chemical_formula_sum            'C18 H28 Cl6 Cu N4'
_chemical_formula_weight         576.68
_chemical_absolute_configuration ad
_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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z'
3 '-x+1/2, y+1/2, -z'
4 'x+1/2, -y+1/2, -z'

_cell_length_a                   13.7107(8)
_cell_length_b                   23.0021(14)
_cell_length_c                   7.9717(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2514.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6595
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.20
_cell_measurement_theta_min      2.31
_exptl_absorpt_coefficient_mu    1.520
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0929 before and 0.0628 after correction.
The Ratio of minimum to maximum transmission is 0.9356.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1180
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11177
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         2.97
_diffrn_ambient_temperature      149.65
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                3553
_reflns_number_total             4428
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.939
_refine_diff_density_min         -0.962
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         4428
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0646
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0797P)²+7.0874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.1669
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2. Uiso/Uaniso restraints and constraints
C18 \\sim C17 \\sim C16: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.01
N4 \\sim C6 \\sim C7: within 2A with sigma of 0.01 and sigma for terminal atoms
of 0.01
Uanis(N3) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(Cl4')=1-FVAR(1)
 Sof(Cl4)=FVAR(1)
 Sof(Cl1')=1-FVAR(2)
 Sof(Cl1)=FVAR(2)
 Fixed Sof: Cl5(0.5)
4.a Ternary CH refined with riding coordinates:
 C2(H2), C1(H1)
4.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), C3(H3A,H3B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,
 H11B), C12(H12A,H12B), C13(H13A,H13B)
4.c Aromatic/amide H refined with riding coordinates:
 N4(H4), N3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C18(H18), C17(H17), C16(H16),
 C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cu1 Cu 0.36460(7) 0.24527(4) 0.01111(12) 0.0414(3) Uani 1 d . . 1 . . .
Cl7 Cl 0.65537(12) 0.53167(8) 0.5663(2) 0.0368(4) Uani 1 d . . 1 . . .
Cl6 Cl 0.0000 0.5000 0.6941(3) 0.0380(6) Uani 1 d . . 2 S T P
Cl1 Cl 0.4001(3) 0.26318(12) 0.2881(3) 0.0651(11) Uani 0.798(6) d A 1 1 . . .
Cl1' Cl 0.3639(7) 0.3314(4) 0.1709(12) 0.041(3) Uani 0.202(6) d A 2 1 . . .
Cl3 Cl 0.42431(16) 0.15627(8) -0.0026(3) 0.0500(5) Uani 1 d A . 1 . . .
Cl2 Cl 0.20169(16) 0.24131(9) -0.0172(4) 0.0699(8) Uani 1 d A . 1 . . .
Cl4 Cl 0.4209(3) 0.3238(2) -0.1114(6) 0.0419(19) Uani 0.435(8) d A 1 1 . . .
Cl4' Cl 0.4079(5) 0.2890(2) -0.2314(7) 0.096(3) Uani 0.565(8) d A 2 1 . . .
Cl5 Cl 0.4953(3) 0.4752(2) 0.0608(7) 0.0676(14) Uani 0.50 d . . 1 . . .
N1 N 0.6851(4) 0.4597(3) 0.8873(8) 0.0342(15) Uani 1 d . . 1 . . .
H1A H 0.6305 0.4748 0.9384 0.041 Uiso 1 calc . . 1 R . .
H1B H 0.6908 0.4769 0.7836 0.041 Uiso 1 calc . . 1 R . .
N2 N 0.8184(4) 0.5625(2) 0.8185(7) 0.0231(12) Uani 1 d . . 1 . . .
H2A H 0.8768 0.5463 0.7856 0.028 Uiso 1 calc . . 1 R . .
H2B H 0.7713 0.5504 0.7440 0.028 Uiso 1 calc . . 1 R . .
N4 N 0.5400(6) 0.3817(4) 0.4601(11) 0.074(3) Uani 1 d . . 1 . U .
H4 H 0.4859 0.3940 0.4126 0.089 Uiso 1 calc . . 1 R . .
N3 N 0.8149(8) 0.6884(3) 0.3791(11) 0.070(3) Uani 1 d . . 1 . U .
H3 H 0.7700 0.7003 0.3082 0.085 Uiso 1 calc . . 1 R . .
C4 C 0.8553(6) 0.6485(3) 0.6407(9) 0.0308(16) Uani 1 d . . 1 . . .
C5 C 0.7851(7) 0.6675(3) 0.5312(11) 0.055(2) Uani 1 d . . 1 . . .
H5 H 0.7179 0.6661 0.5600 0.066 Uiso 1 calc . . 1 R . .
C6 C 0.9082(12) 0.6919(4) 0.3317(12) 0.078(3) Uani 1 d . . 1 . U .
H6 H 0.9250 0.7081 0.2260 0.094 Uiso 1 calc . . 1 R . .
C7 C 0.9766(11) 0.6725(5) 0.4333(12) 0.081(3) Uani 1 d . . 1 . U .
H7 H 1.0432 0.6734 0.4003 0.097 Uiso 1 calc . . 1 R . .
C8 C 0.9502(7) 0.6507(4) 0.5900(11) 0.052(2) Uani 1 d . . 1 . . .
H8 H 0.9996 0.6369 0.6634 0.063 Uiso 1 calc . . 1 R . .
C3 C 0.8267(6) 0.6278(3) 0.8107(9) 0.0343(18) Uani 1 d . . 1 . . .
H3A H 0.7633 0.6453 0.8418 0.041 Uiso 1 calc . . 1 R . .
H3B H 0.8759 0.6409 0.8934 0.041 Uiso 1 calc . . 1 R . .
C2 C 0.7929(4) 0.5404(3) 0.9913(9) 0.0263(14) Uani 1 d . . 1 . . .
H2 H 0.7333 0.5610 1.0325 0.032 Uiso 1 calc . . 1 R . .
C9 C 0.8791(5) 0.5541(3) 1.1089(8) 0.0322(16) Uani 1 d . . 1 . . .
H9A H 0.9393 0.5368 1.0621 0.039 Uiso 1 calc . . 1 R . .
H9B H 0.8884 0.5968 1.1144 0.039 Uiso 1 calc . . 1 R . .
C10 C 0.8628(5) 0.5308(3) 1.2847(8) 0.0348(17) Uani 1 d . . 1 . . .
H10A H 0.8058 0.5505 1.3356 0.042 Uiso 1 calc . . 1 R . .
H10B H 0.9206 0.5394 1.3547 0.042 Uiso 1 calc . . 1 R . .
C11 C 0.8450(5) 0.4653(3) 1.2826(9) 0.0333(16) Uani 1 d . . 1 . . .
H11A H 0.8311 0.4514 1.3977 0.040 Uiso 1 calc . . 1 R . .
H11B H 0.9039 0.4450 1.2411 0.040 Uiso 1 calc . . 1 R . .
C12 C 0.7577(5) 0.4520(3) 1.1672(9) 0.0326(17) Uani 1 d . . 1 . . .
H12A H 0.7474 0.4094 1.1620 0.039 Uiso 1 calc . . 1 R . .
H12B H 0.6980 0.4699 1.2145 0.039 Uiso 1 calc . . 1 R . .
C1 C 0.7744(4) 0.4752(3) 0.9920(9) 0.0266(13) Uani 1 d . . 1 . . .
H1 H 0.8326 0.4552 0.9431 0.032 Uiso 1 calc . . 1 R . .
C13 C 0.6709(8) 0.3962(4) 0.8637(11) 0.062(3) Uani 1 d . . 1 . . .
H13A H 0.7313 0.3758 0.8979 0.074 Uiso 1 calc . . 1 R . .
H13B H 0.6177 0.3830 0.9384 0.074 Uiso 1 calc . . 1 R . .
C14 C 0.6470(5) 0.3796(3) 0.6890(9) 0.0308(16) Uani 1 d . . 1 . . .
C18 C 0.7074(9) 0.3461(4) 0.5979(14) 0.068(3) Uani 1 d . . 1 . U .
H18 H 0.7682 0.3345 0.6439 0.082 Uiso 1 calc . . 1 R . .
C17 C 0.6817(12) 0.3283(5) 0.4358(17) 0.086(3) Uani 1 d . . 1 . U .
H17 H 0.7230 0.3029 0.3742 0.103 Uiso 1 calc . . 1 R . .
C16 C 0.6032(13) 0.3463(5) 0.3729(14) 0.089(4) Uani 1 d . . 1 . U .
H16 H 0.5870 0.3351 0.2617 0.107 Uiso 1 calc . . 1 R . .
C15 C 0.5616(6) 0.3973(4) 0.6184(10) 0.0404(19) Uani 1 d . . 1 . . .
H15 H 0.5174 0.4206 0.6808 0.048 Uiso 1 calc . . 1 R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 Cl1 2.298(3) . ?
Cu1 Cl1' 2.356(8) . ?
Cu1 Cl3 2.207(2) . ?
Cu1 Cl2 2.247(2) . ?
Cu1 Cl4 2.193(4) . ?
Cu1 Cl4' 2.259(5) . ?
Cl5 Cl5 1.150(10) 2_665 ?
N1 H1A 0.9200 . ?
N1 H1B 0.9200 . ?
N1 C1 1.525(8) . ?
N1 C13 1.484(10) . ?
N2 H2A 0.9200 . ?
N2 H2B 0.9200 . ?
N2 C3 1.508(8) . ?
N2 C2 1.510(9) . ?
N4 H4 0.8800 . ?
N4 C16 1.377(16) . ?
N4 C15 1.344(12) . ?
N3 H3 0.8800 . ?
N3 C5 1.367(13) . ?
N3 C6 1.336(16) . ?
C4 C5 1.371(11) . ?
C4 C8 1.364(12) . ?
C4 C3 1.489(10) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.317(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.394(13) . ?
C8 H8 0.9500 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C2 H2 1.0000 . ?
C2 C9 1.540(9) . ?
C2 C1 1.521(8) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.518(10) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.524(10) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.541(10) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C1 1.512(10) . ?
C1 H1 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.481(11) . ?
C14 C18 1.343(12) . ?
C14 C15 1.361(10) . ?
C18 H18 0.9500 . ?
C18 C17 1.401(17) . ?
C17 H17 0.9500 . ?
C17 C16 1.257(19) . ?
C16 H16 0.9500 . ?
C15 H15 0.9500 . ?

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' 48.0(3) . . ?
Cl3 Cu1 Cl1 97.77(10) . . ?
Cl3 Cu1 Cl1' 143.9(3) . . ?
Cl3 Cu1 Cl2 109.03(9) . . ?
Cl3 Cu1 Cl4' 105.86(14) . . ?
Cl2 Cu1 Cl1 108.31(12) . . ?
Cl2 Cu1 Cl1' 94.8(2) . . ?
Cl2 Cu1 Cl4' 101.1(2) . . ?
Cl4 Cu1 Cl1 101.88(15) . . ?
Cl4 Cu1 Cl1' 63.2(3) . . ?
Cl4 Cu1 Cl3 127.67(16) . . ?
Cl4 Cu1 Cl2 109.77(14) . . ?
Cl4 Cu1 Cl4' 32.82(19) . . ?
Cl4' Cu1 Cl1 133.4(2) . . ?
Cl4' Cu1 Cl1' 95.1(3) . . ?
H1A N1 H1B 107.7 . . ?
C1 N1 H1A 108.8 . . ?
C1 N1 H1B 108.8 . . ?
C13 N1 H1A 108.8 . . ?
C13 N1 H1B 108.8 . . ?
C13 N1 C1 113.9(6) . . ?
H2A N2 H2B 107.8 . . ?
C3 N2 H2A 109.0 . . ?
C3 N2 H2B 109.0 . . ?
C3 N2 C2 112.9(5) . . ?
C2 N2 H2A 109.0 . . ?
C2 N2 H2B 109.0 . . ?
C16 N4 H4 120.3 . . ?
C15 N4 H4 120.3 . . ?
C15 N4 C16 119.5(10) . . ?
C5 N3 H3 118.0 . . ?
C6 N3 H3 118.0 . . ?
C6 N3 C5 123.9(9) . . ?
C5 C4 C3 119.8(8) . . ?
C8 C4 C5 118.0(8) . . ?
C8 C4 C3 122.2(7) . . ?
N3 C5 C4 117.8(10) . . ?
N3 C5 H5 121.1 . . ?
C4 C5 H5 121.1 . . ?
N3 C6 H6 120.4 . . ?
C7 C6 N3 119.2(10) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C8 119.2(13) . . ?
C8 C7 H7 120.4 . . ?
C4 C8 C7 121.8(11) . . ?
C4 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
N2 C3 H3A 109.2 . . ?
N2 C3 H3B 109.2 . . ?
C4 C3 N2 112.1(6) . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
N2 C2 H2 109.3 . . ?
N2 C2 C9 108.0(5) . . ?
N2 C2 C1 111.9(6) . . ?
C9 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
C1 C2 C9 109.1(5) . . ?
C2 C9 H9A 109.2 . . ?
C2 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 C2 112.1(6) . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C9 C10 C11 111.3(6) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C10 C11 H11A 109.9 . . ?
C10 C11 H11B 109.9 . . ?
C10 C11 C12 109.1(6) . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C1 C12 C11 111.3(5) . . ?
C1 C12 H12A 109.4 . . ?
C1 C12 H12B 109.4 . . ?
N1 C1 H1 108.6 . . ?
C2 C1 N1 111.3(5) . . ?
C2 C1 H1 108.6 . . ?
C12 C1 N1 107.5(5) . . ?
C12 C1 C2 112.1(6) . . ?
C12 C1 H1 108.6 . . ?
N1 C13 H13A 108.8 . . ?
N1 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 N1 113.7(6) . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C18 C14 C13 121.3(9) . . ?
C18 C14 C15 118.6(8) . . ?
C15 C14 C13 120.2(8) . . ?
C14 C18 H18 119.6 . . ?
C14 C18 C17 120.7(12) . . ?
C17 C18 H18 119.6 . . ?
C18 C17 H17 120.4 . . ?
C16 C17 C18 119.1(13) . . ?
C16 C17 H17 120.4 . . ?
N4 C16 H16 118.9 . . ?
C17 C16 N4 122.1(12) . . ?
C17 C16 H16 118.9 . . ?
N4 C15 C14 119.9(8) . . ?
N4 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
