# 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_20171018_1a_0m
_database_code_depnum_ccdc_archive 'CCDC 1918759'
loop_
_audit_author_name
_audit_author_address
'Li hai-tao'
;LiaoNingUniversity
China
;
_audit_update_record             
;
2019-05-27 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;
_audit_creation_date             2017-10-18
_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                   6.9780(6)
_cell_length_b                   14.7620(13)
_cell_length_c                   12.3395(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.140(3)
_cell_angle_gamma                90
_cell_volume                     1251.23(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9875
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.328
_cell_measurement_theta_min      3.139
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.532
_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            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             610
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18666
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         28.348
_diffrn_reflns_theta_min         3.140
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_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         0.884
_reflns_Friedel_fraction_full    0.937
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                5750
_reflns_number_total             6027
_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         0.483
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 2579 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.053(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         6027
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0303
_refine_ls_restrained_S_all      1.066
_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)+(0.0286P)²+0.6235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0749
_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(H1C,H1D)
2.b Ternary CH refined with riding coordinates:
 C6(H6), C1(H1)
2.c Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), C5(H5A,H5B), C7(H7A,H7B), C13(H13A,H13B), C2(H2C,
 H2D), C4(H4A,H4B), C3(H3A,H3B)
2.d Aromatic/amide H refined with riding coordinates:
 C8(H8), N3(H3), C9(H9), N4(H4), C11(H11), C14(H14), C15(H15), C12(H12),
 C17(H17), C18(H18)
;
_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 0.99156(6) 0.50564(3) 0.10625(3) 0.03019(10) Uani 1 1 d . . . . .
Cl5 Cl 0.24983(12) 0.35596(6) 0.42778(7) 0.03781(19) Uani 1 1 d . . . . .
Cl4 Cl 0.50716(15) 0.50333(8) 0.12392(6) 0.0425(2) Uani 1 1 d . . . . .
Cl6 Cl 1.10078(12) 0.65221(7) 0.43946(8) 0.0420(2) Uani 1 1 d . . . . .
Cl1 Cl 1.00618(15) 0.35476(7) 0.10886(9) 0.0479(3) Uani 1 1 d . . . . .
Cl2 Cl 0.91886(15) 0.51001(9) -0.07751(6) 0.0467(2) Uani 1 1 d . . . . .
Cl3 Cl 0.95050(19) 0.65456(7) 0.12194(10) 0.0555(3) Uani 1 1 d . . . . .
N1 N 0.6624(4) 0.61073(18) 0.3528(2) 0.0236(5) Uani 1 1 d . . . . .
H1A H 0.7895 0.6223 0.3649 0.028 Uiso 1 1 calc R . . . .
H1B H 0.6322 0.5843 0.2872 0.028 Uiso 1 1 calc R . . . .
N2 N 0.6355(4) 0.39641(17) 0.3493(2) 0.0201(5) Uani 1 1 d . . . . .
H2A H 0.5184 0.3828 0.3638 0.024 Uiso 1 1 calc R . . . .
H2B H 0.6183 0.4262 0.2856 0.024 Uiso 1 1 calc R . . . .
O1 O 1.0664(6) 0.5027(3) 0.26677(19) 0.0677(10) Uani 1 1 d . . . . .
H1C H 1.0734 0.5565 0.2920 0.102 Uiso 1 1 d GR . . . .
H1D H 1.1768 0.4770 0.2844 0.102 Uiso 1 1 d GR . . . .
C6 C 0.7383(4) 0.4584(2) 0.4392(2) 0.0236(6) Uani 1 1 d . . . . .
H6 H 0.8674 0.4740 0.4238 0.028 Uiso 1 1 calc R . . . .
C1 C 0.6169(5) 0.5457(2) 0.4409(2) 0.0236(5) Uani 1 1 d . . . . .
H1 H 0.4786 0.5297 0.4237 0.028 Uiso 1 1 calc R . . . .
C10 C 0.6419(5) 0.2527(2) 0.2434(3) 0.0255(6) Uani 1 1 d . . . . .
C8 C 0.3664(6) 0.2033(3) 0.1132(3) 0.0367(8) Uani 1 1 d . . . . .
H8 H 0.2345 0.2071 0.0837 0.044 Uiso 1 1 calc R . . . .
N3 N 0.4789(5) 0.1445(2) 0.0732(3) 0.0413(7) Uani 1 1 d . . . . .
H3 H 0.4277 0.1107 0.0190 0.050 Uiso 1 1 calc R . . . .
C9 C 0.4469(5) 0.2591(2) 0.1993(3) 0.0319(7) Uani 1 1 d . . . . .
H9 H 0.3691 0.3011 0.2274 0.038 Uiso 1 1 calc R . . . .
N4 N 0.5946(9) 0.8680(3) 0.0818(3) 0.0664(13) Uani 1 1 d . . . . .
H4 H 0.6039 0.9030 0.0272 0.080 Uiso 1 1 calc R . . . .
C11 C 0.7535(6) 0.1886(3) 0.1991(4) 0.0414(9) Uani 1 1 d . . . . .
H11 H 0.8852 0.1822 0.2277 0.050 Uiso 1 1 calc R . . . .
C5 C 0.7614(7) 0.4036(3) 0.5470(3) 0.0431(9) Uani 1 1 d . . . . .
H5A H 0.6411 0.3712 0.5489 0.052 Uiso 1 1 calc R . . . .
H5B H 0.8634 0.3590 0.5470 0.052 Uiso 1 1 calc R . . . .
C16 C 0.5674(5) 0.7567(2) 0.2530(3) 0.0272(6) Uani 1 1 d . . . . .
C7 C 0.7423(5) 0.3105(2) 0.3368(3) 0.0290(6) Uani 1 1 d . . . . .
H7A H 0.7550 0.2762 0.4048 0.035 Uiso 1 1 calc R . . . .
H7B H 0.8722 0.3250 0.3244 0.035 Uiso 1 1 calc R . . . .
C13 C 0.5527(6) 0.6985(2) 0.3511(3) 0.0374(8) Uani 1 1 d . . . . .
H13A H 0.6025 0.7321 0.4176 0.045 Uiso 1 1 calc R . . . .
H13B H 0.4166 0.6853 0.3514 0.045 Uiso 1 1 calc R . . . .
C14 C 0.7469(9) 0.8582(4) 0.1597(5) 0.0656(14) Uani 1 1 d . . . . .
H14 H 0.8624 0.8881 0.1550 0.079 Uiso 1 1 calc R . . . .
C15 C 0.7356(6) 0.8038(3) 0.2478(4) 0.0468(10) Uani 1 1 d . . . . .
H15 H 0.8420 0.7986 0.3046 0.056 Uiso 1 1 calc R . . . .
C2 C 0.6550(7) 0.5949(3) 0.5518(3) 0.0388(8) Uani 1 1 d . . . . .
H2C H 0.7805 0.6249 0.5605 0.047 Uiso 1 1 calc R . . . .
H2D H 0.5565 0.6413 0.5520 0.047 Uiso 1 1 calc R . . . .
C12 C 0.6672(7) 0.1353(3) 0.1130(4) 0.0495(11) Uani 1 1 d . . . . .
H12 H 0.7407 0.0927 0.0827 0.059 Uiso 1 1 calc R . . . .
C17 C 0.4111(6) 0.7686(3) 0.1685(4) 0.0510(11) Uani 1 1 d . . . . .
H17 H 0.2950 0.7378 0.1689 0.061 Uiso 1 1 calc R . . . .
C4 C 0.8100(9) 0.4604(3) 0.6500(3) 0.0615(14) Uani 1 1 d . . . . .
H4A H 0.9356 0.4893 0.6528 0.074 Uiso 1 1 calc R . . . .
H4B H 0.8165 0.4224 0.7147 0.074 Uiso 1 1 calc R . . . .
C3 C 0.6530(10) 0.5319(3) 0.6487(4) 0.0675(16) Uani 1 1 d . . . . .
H3A H 0.5267 0.5030 0.6423 0.081 Uiso 1 1 calc R . . . .
H3B H 0.6768 0.5661 0.7169 0.081 Uiso 1 1 calc R . . . .
C18 C 0.4292(10) 0.8270(4) 0.0833(4) 0.0674(17) Uani 1 1 d . . . . .
H18 H 0.3238 0.8371 0.0271 0.081 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 2.2296(11) . ?
Cu1 Cl2 2.2356(8) . ?
Cu1 Cl3 2.2297(11) . ?
Cu1 O1 1.958(2) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C1 1.525(4) . ?
N1 C13 1.503(4) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 C6 1.518(4) . ?
N2 C7 1.493(4) . ?
O1 H1C 0.8515 . ?
O1 H1D 0.8516 . ?
C6 H6 0.9800 . ?
C6 C1 1.545(4) . ?
C6 C5 1.541(5) . ?
C1 H1 0.9800 . ?
C1 C2 1.531(4) . ?
C10 C9 1.377(5) . ?
C10 C11 1.396(5) . ?
C10 C7 1.504(4) . ?
C8 H8 0.9300 . ?
C8 N3 1.323(5) . ?
C8 C9 1.383(5) . ?
N3 H3 0.8600 . ?
N3 C12 1.326(6) . ?
C9 H9 0.9300 . ?
N4 H4 0.8600 . ?
N4 C14 1.309(8) . ?
N4 C18 1.306(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.511(6) . ?
C16 C13 1.503(5) . ?
C16 C15 1.375(5) . ?
C16 C17 1.381(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14 0.9300 . ?
C14 C15 1.365(6) . ?
C15 H15 0.9300 . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C2 C3 1.517(6) . ?
C12 H12 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.382(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.518(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C18 H18 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
Cl1 Cu1 Cl2 92.58(5) . . ?
Cl1 Cu1 Cl3 171.85(5) . . ?
Cl3 Cu1 Cl2 92.86(5) . . ?
O1 Cu1 Cl1 87.68(12) . . ?
O1 Cu1 Cl2 177.65(14) . . ?
O1 Cu1 Cl3 87.12(12) . . ?
H1A N1 H1B 107.8 . . ?
C1 N1 H1A 109.1 . . ?
C1 N1 H1B 109.1 . . ?
C13 N1 H1A 109.1 . . ?
C13 N1 H1B 109.1 . . ?
C13 N1 C1 112.5(2) . . ?
H2A N2 H2B 107.6 . . ?
C6 N2 H2A 108.7 . . ?
C6 N2 H2B 108.7 . . ?
C7 N2 H2A 108.7 . . ?
C7 N2 H2B 108.7 . . ?
C7 N2 C6 114.0(2) . . ?
Cu1 O1 H1C 109.7 . . ?
Cu1 O1 H1D 109.7 . . ?
H1C O1 H1D 109.4 . . ?
N2 C6 H6 109.4 . . ?
N2 C6 C1 108.9(2) . . ?
N2 C6 C5 106.2(2) . . ?
C1 C6 H6 109.4 . . ?
C5 C6 H6 109.4 . . ?
C5 C6 C1 113.6(3) . . ?
N1 C1 C6 109.4(2) . . ?
N1 C1 H1 108.5 . . ?
N1 C1 C2 108.3(2) . . ?
C6 C1 H1 108.5 . . ?
C2 C1 C6 113.5(3) . . ?
C2 C1 H1 108.5 . . ?
C9 C10 C11 118.2(3) . . ?
C9 C10 C7 123.9(3) . . ?
C11 C10 C7 117.9(3) . . ?
N3 C8 H8 120.3 . . ?
N3 C8 C9 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C8 N3 H3 118.5 . . ?
C8 N3 C12 122.9(3) . . ?
C12 N3 H3 118.5 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C14 N4 H4 118.5 . . ?
C18 N4 H4 118.5 . . ?
C18 N4 C14 122.9(4) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.5(4) . . ?
C12 C11 H11 120.2 . . ?
C6 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C4 C5 C6 114.1(3) . . ?
C4 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
C15 C16 C13 120.4(3) . . ?
C15 C16 C17 117.9(4) . . ?
C17 C16 C13 121.6(4) . . ?
N2 C7 C10 112.8(3) . . ?
N2 C7 H7A 109.0 . . ?
N2 C7 H7B 109.0 . . ?
C10 C7 H7A 109.0 . . ?
C10 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
N1 C13 C16 113.4(3) . . ?
N1 C13 H13A 108.9 . . ?
N1 C13 H13B 108.9 . . ?
C16 C13 H13A 108.9 . . ?
C16 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
N4 C14 H14 120.1 . . ?
N4 C14 C15 119.8(5) . . ?
C15 C14 H14 120.1 . . ?
C16 C15 H15 119.9 . . ?
C14 C15 C16 120.3(4) . . ?
C14 C15 H15 119.9 . . ?
C1 C2 H2C 109.0 . . ?
C1 C2 H2D 109.0 . . ?
H2C C2 H2D 107.8 . . ?
C3 C2 C1 112.9(3) . . ?
C3 C2 H2C 109.0 . . ?
C3 C2 H2D 109.0 . . ?
N3 C12 C11 119.9(4) . . ?
N3 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.2(5) . . ?
C18 C17 H17 120.4 . . ?
C5 C4 H4A 109.9 . . ?
C5 C4 H4B 109.9 . . ?
C5 C4 C3 108.8(4) . . ?
H4A C4 H4B 108.3 . . ?
C3 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
C2 C3 C4 109.2(4) . . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
C4 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
H3A C3 H3B 108.3 . . ?
N4 C18 C17 119.9(4) . . ?
N4 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?

_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_20171211_1a_0m
_database_code_depnum_ccdc_archive 'CCDC 1918797'
loop_
_audit_author_name
_audit_author_address
'Li hai-tao'
;liaoningUniversity
China
;
_audit_update_record             
;
2019-05-27 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;
_audit_creation_date             2017-12-11
_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           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   15.872(3)
_cell_length_b                   7.3428(12)
_cell_length_c                   9.2728(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1080.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.308
_cell_measurement_theta_min      3.379
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.920
_exptl_absorpt_coefficient_mu    0.564
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1021 before and 0.0389 after correction.
The Ratio of minimum to maximum transmission is 0.8336.
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    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18659
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         28.308
_diffrn_reflns_theta_min         3.379
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.969
_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         0.726
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                2604
_reflns_number_total             2634
_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         0.278
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 1089 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2634
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0257
_refine_ls_restrained_S_all      1.093
_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)+(0.0338P)²+0.2978P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0688
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C1(H1), C4(H4), C5(H5)
;
_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
Cl0A Cl 0.50852(3) 0.75065(6) 0.11354(6) 0.03553(14) Uani 1 1 d . . . . .
Cl2 Cl 0.66945(3) 0.09426(8) 0.38019(5) 0.03824(14) Uani 1 1 d . . . . .
N1 N 0.59457(8) 0.4955(2) 0.33368(14) 0.0203(3) Uani 1 1 d . . . . .
H1A H 0.6005 0.3750 0.3324 0.024 Uiso 1 1 calc R . . . .
H1B H 0.5672 0.5279 0.2539 0.024 Uiso 1 1 calc R . . . .
N2 N 0.83490(12) 0.5255(3) -0.03165(19) 0.0384(4) Uani 1 1 d . . . . .
H2 H 0.8677 0.5220 -0.1054 0.046 Uiso 1 1 calc R . . . .
O1 O 1.0000 0.5000 0.4479(4) 0.0673(8) Uani 1 2 d S T P . .
C7 C 0.54247(10) 0.5491(2) 0.46387(17) 0.0216(3) Uani 1 1 d . . . . .
H7 H 0.5324 0.6807 0.4607 0.026 Uiso 1 1 calc R . . . .
C6 C 0.67893(11) 0.5814(3) 0.33364(18) 0.0299(4) Uani 1 1 d . . . . .
H6A H 0.7099 0.5376 0.4169 0.036 Uiso 1 1 calc R . . . .
H6B H 0.6720 0.7119 0.3447 0.036 Uiso 1 1 calc R . . . .
C3 C 0.73064(10) 0.5466(2) 0.20133(19) 0.0222(3) Uani 1 1 d . . . . .
C2 C 0.69822(12) 0.5285(4) 0.0636(2) 0.0347(5) Uani 1 1 d . . . . .
H2A H 0.6403 0.5220 0.0492 0.042 Uiso 1 1 calc R . . . .
C1 C 0.75288(14) 0.5203(4) -0.0523(2) 0.0381(5) Uani 1 1 d . . . . .
H1 H 0.7316 0.5109 -0.1455 0.046 Uiso 1 1 calc R . . . .
C4 C 0.81743(12) 0.5448(3) 0.2183(2) 0.0375(5) Uani 1 1 d . . . . .
H4 H 0.8410 0.5495 0.3101 0.045 Uiso 1 1 calc R . . . .
C8 C 0.59118(12) 0.5040(4) 0.6019(2) 0.0424(5) Uani 1 1 d . . . . .
H8A H 0.6051 0.3753 0.6023 0.051 Uiso 1 1 calc R . . . .
H8B H 0.6435 0.5722 0.6029 0.051 Uiso 1 1 calc R . . . .
C5 C 0.86854(13) 0.5361(4) 0.0986(3) 0.0490(6) Uani 1 1 d . . . . .
H5 H 0.9268 0.5377 0.1094 0.059 Uiso 1 1 calc R . . . .
C9 C 0.54110(14) 0.5490(5) 0.7363(2) 0.0553(9) Uani 1 1 d . . . . .
H9A H 0.5732 0.5144 0.8210 0.066 Uiso 1 1 calc R . . . .
H9B H 0.5312 0.6792 0.7405 0.066 Uiso 1 1 calc R . . . .
H1C H 0.959(2) 0.514(6) 0.506(4) 0.080(13) 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
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 C7 1.5152(19) . ?
N1 C6 1.480(2) . ?
N2 H2 0.8600 . ?
N2 C1 1.316(3) . ?
N2 C5 1.323(3) . ?
O1 H1C 0.85(4) . ?
C7 C7 1.529(3) 2_665 ?
C7 H7 0.9800 . ?
C7 C8 1.532(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C3 1.498(2) . ?
C3 C2 1.383(2) . ?
C3 C4 1.387(2) . ?
C2 H2A 0.9300 . ?
C2 C1 1.383(3) . ?
C1 H1 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.376(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.515(3) . ?
C5 H5 0.9300 . ?
C9 C9 1.490(5) 2_665 ?
C9 H9A 0.9700 . ?
C9 H9B 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
H1A N1 H1B 107.8 . . ?
C7 N1 H1A 109.1 . . ?
C7 N1 H1B 109.1 . . ?
C6 N1 H1A 109.1 . . ?
C6 N1 H1B 109.1 . . ?
C6 N1 C7 112.55(13) . . ?
C1 N2 H2 118.9 . . ?
C1 N2 C5 122.26(17) . . ?
C5 N2 H2 118.9 . . ?
N1 C7 C7 111.04(12) . 2_665 ?
N1 C7 H7 108.7 . . ?
N1 C7 C8 109.52(14) . . ?
C7 C7 H7 108.7 2_665 . ?
C7 C7 C8 110.08(13) 2_665 . ?
C8 C7 H7 108.7 . . ?
N1 C6 H6A 108.5 . . ?
N1 C6 H6B 108.5 . . ?
N1 C6 C3 115.04(14) . . ?
H6A C6 H6B 107.5 . . ?
C3 C6 H6A 108.5 . . ?
C3 C6 H6B 108.5 . . ?
C2 C3 C6 124.66(15) . . ?
C2 C3 C4 118.26(16) . . ?
C4 C3 C6 116.93(16) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 C3 119.25(18) . . ?
C1 C2 H2A 120.4 . . ?
N2 C1 C2 120.39(19) . . ?
N2 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.65(19) . . ?
C5 C4 H4 120.2 . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 C7 112.05(17) . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
N2 C5 C4 120.07(19) . . ?
N2 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C9 C9 C8 110.8(2) 2_665 . ?
C9 C9 H9A 109.5 2_665 . ?
C9 C9 H9B 109.5 2_665 . ?
H9A C9 H9B 108.1 . . ?

_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_20180523_4b_0m
_database_code_depnum_ccdc_archive 'CCDC 1918760'
loop_
_audit_author_name
_audit_author_address
'Li hai-tao'
;liaoning University
China
;
_audit_update_record             
;
2019-05-30 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;
_audit_creation_date             2019-05-30
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl8 Cu2, H2 O, C18 H28 N4'
_chemical_formula_sum            'C18 H30 Cl8 Cu2 N4 O'
_chemical_formula_weight         729.14
_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      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                   9.6563(5)
_cell_length_b                   11.4146(7)
_cell_length_c                   24.6751(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2719.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9314
_cell_measurement_temperature    173.01
_cell_measurement_theta_max      28.311
_cell_measurement_theta_min      3.053
_shelx_estimated_absorpt_T_max   0.815
_shelx_estimated_absorpt_T_min   0.589
_exptl_absorpt_coefficient_mu    2.371
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1099 before and 0.0617 after correction.
The Ratio of minimum to maximum transmission is 0.6189.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            36360
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.884
_diffrn_ambient_temperature      173.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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         0.736
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                4663
_reflns_number_total             4700
_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         0.518
_refine_diff_density_min         -1.071
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details 
;
 Flack x determined using 1956 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.028(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.243
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4700
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0213
_refine_ls_R_factor_gt           0.0211
_refine_ls_restrained_S_all      1.243
_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)+(0.0292P)²+1.1085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0543
_refine_ls_wR_factor_ref         0.0544
_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 Free rotating group:
 O1(H,HA)
2.b Ternary CH refined with riding coordinates:
 C7(H7), C12(H12)
2.c Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), N3(H3A,H3B), C10(H10A,H10B), C9(H9A,H9B), C8(H8A,H8B), C6(H6A,
 H6B), C11(H11A,H11B), C13(H13A,H13B)
2.d Aromatic/amide H refined with riding coordinates:
 N4(H4), N1(H1), C4(H4A), C2(H2), C15(H15), C18(H18), C1(H1A), C17(H17),
 C14(H14), C5(H5)
;
_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 0.27735(4) 0.45591(3) 0.61754(2) 0.01116(10) Uani 1 1 d . . . . .
Cu2 Cu 0.26599(4) 0.77491(3) 0.62262(2) 0.01155(10) Uani 1 1 d . . . . .
Cl8 Cl 0.22797(8) 0.59035(6) 0.68422(3) 0.01308(16) Uani 1 1 d . . . . .
Cl7 Cl 0.28850(8) 0.63894(6) 0.55319(3) 0.01320(16) Uani 1 1 d . . . . .
Cl5 Cl 0.50360(8) 0.81372(7) 0.62177(3) 0.01535(16) Uani 1 1 d . . . . .
Cl3 Cl 0.05958(8) 0.38097(8) 0.62327(3) 0.02050(18) Uani 1 1 d . . . . .
Cl1 Cl 0.50450(8) 0.44563(7) 0.65090(3) 0.01505(17) Uani 1 1 d . . . . .
Cl6 Cl 0.24231(9) 0.88771(7) 0.70002(3) 0.01823(17) Uani 1 1 d . . . . .
Cl2 Cl 0.33496(9) 0.32457(7) 0.55129(3) 0.01808(18) Uani 1 1 d . . . . .
Cl4 Cl 0.05963(9) 0.84100(7) 0.59183(3) 0.01967(19) Uani 1 1 d . . . . .
O1 O 0.2314(2) 0.1185(2) 0.62887(10) 0.0180(5) Uani 1 1 d . . . . .
H H 0.1828 0.0617 0.6427 0.027 Uiso 1 1 d G . . . .
HA H 0.1702 0.1708 0.6195 0.027 Uiso 1 1 d G . . . .
N2 N 0.4769(3) 0.1841(2) 0.68041(10) 0.0103(5) Uani 1 1 d . . . . .
H2A H 0.4795 0.2611 0.6710 0.012 Uiso 1 1 calc R . . . .
H2B H 0.4004 0.1519 0.6648 0.012 Uiso 1 1 calc R . . . .
N4 N 0.1341(3) -0.1177(3) 0.45262(11) 0.0172(6) Uani 1 1 d . . . . .
H4 H 0.0615 -0.1564 0.4407 0.021 Uiso 1 1 calc R . . . .
N3 N 0.4847(3) 0.0647(2) 0.57124(10) 0.0101(5) Uani 1 1 d . . . . .
H3A H 0.4063 0.1011 0.5829 0.012 Uiso 1 1 calc R . . . .
H3B H 0.4817 -0.0108 0.5831 0.012 Uiso 1 1 calc R . . . .
N1 N 0.0530(3) 0.2508(3) 0.78931(11) 0.0191(6) Uani 1 1 d . . . . .
H1 H -0.0332 0.2656 0.7986 0.023 Uiso 1 1 calc R . . . .
C4 C 0.2573(4) 0.3100(3) 0.74582(13) 0.0175(7) Uani 1 1 d . . . . .
H4A H 0.3087 0.3677 0.7267 0.021 Uiso 1 1 calc R . . . .
C3 C 0.3178(3) 0.2026(3) 0.75906(13) 0.0137(7) Uani 1 1 d . . . . .
C7 C 0.6044(3) 0.1238(3) 0.65822(12) 0.0098(6) Uani 1 1 d . . . . .
H7 H 0.6051 0.0407 0.6710 0.012 Uiso 1 1 calc R . . . .
C12 C 0.6091(3) 0.1249(3) 0.59615(12) 0.0094(6) Uani 1 1 d . . . . .
H12 H 0.6120 0.2080 0.5833 0.011 Uiso 1 1 calc R . . . .
C10 C 0.8713(3) 0.1213(3) 0.59954(13) 0.0149(7) Uani 1 1 d . . . . .
H10A H 0.8781 0.2017 0.5847 0.018 Uiso 1 1 calc R . . . .
H10B H 0.9544 0.0771 0.5880 0.018 Uiso 1 1 calc R . . . .
C2 C 0.2426(3) 0.1220(3) 0.78880(13) 0.0164(7) Uani 1 1 d . . . . .
H2 H 0.2827 0.0489 0.7985 0.020 Uiso 1 1 calc R . . . .
C15 C 0.2278(4) 0.0502(3) 0.49339(13) 0.0165(7) Uani 1 1 d . . . . .
H15 H 0.2157 0.1258 0.5087 0.020 Uiso 1 1 calc R . . . .
C9 C 0.8659(3) 0.1265(3) 0.66124(13) 0.0154(7) Uani 1 1 d . . . . .
H9A H 0.8701 0.0461 0.6762 0.018 Uiso 1 1 calc R . . . .
H9B H 0.9470 0.1705 0.6750 0.018 Uiso 1 1 calc R . . . .
C16 C 0.3597(3) 0.0017(3) 0.48944(13) 0.0120(7) Uani 1 1 d . . . . .
C18 C 0.2587(4) -0.1665(3) 0.44781(14) 0.0206(7) Uani 1 1 d . . . . .
H18 H 0.2675 -0.2416 0.4316 0.025 Uiso 1 1 calc R . . . .
C8 C 0.7335(3) 0.1859(3) 0.68010(12) 0.0140(6) Uani 1 1 d . . . . .
H8A H 0.7335 0.2684 0.6677 0.017 Uiso 1 1 calc R . . . .
H8B H 0.7307 0.1861 0.7202 0.017 Uiso 1 1 calc R . . . .
C1 C 0.1096(4) 0.1483(3) 0.80429(15) 0.0222(8) Uani 1 1 d . . . . .
H1A H 0.0580 0.0944 0.8255 0.027 Uiso 1 1 calc R . . . .
C17 C 0.3746(4) -0.1093(3) 0.46610(14) 0.0187(7) Uani 1 1 d . . . . .
H17 H 0.4635 -0.1444 0.4630 0.022 Uiso 1 1 calc R . . . .
C14 C 0.1150(4) -0.0118(3) 0.47498(14) 0.0186(7) Uani 1 1 d . . . . .
H14 H 0.0245 0.0201 0.4781 0.022 Uiso 1 1 calc R . . . .
C6 C 0.4639(4) 0.1749(4) 0.74136(13) 0.0187(7) Uani 1 1 d . . . . .
H6A H 0.4886 0.0946 0.7531 0.022 Uiso 1 1 calc R . . . .
H6B H 0.5290 0.2303 0.7588 0.022 Uiso 1 1 calc R . . . .
C11 C 0.7421(3) 0.0619(3) 0.57756(13) 0.0135(6) Uani 1 1 d . . . . .
H11A H 0.7397 -0.0204 0.5902 0.016 Uiso 1 1 calc R . . . .
H11B H 0.7458 0.0613 0.5375 0.016 Uiso 1 1 calc R . . . .
C13 C 0.4860(3) 0.0647(3) 0.50973(13) 0.0141(7) Uani 1 1 d . . . . .
H13A H 0.4863 0.1463 0.4961 0.017 Uiso 1 1 calc R . . . .
H13B H 0.5705 0.0250 0.4964 0.017 Uiso 1 1 calc R . . . .
C5 C 0.1222(4) 0.3311(3) 0.76084(14) 0.0187(7) Uani 1 1 d . . . . .
H5 H 0.0785 0.4025 0.7510 0.022 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 Cl8 2.2998(8) . ?
Cu1 Cl7 2.6263(8) . ?
Cu1 Cl3 2.2746(9) . ?
Cu1 Cl1 2.3457(9) . ?
Cu1 Cl2 2.2869(9) . ?
Cu2 Cl8 2.6236(8) . ?
Cu2 Cl7 2.3219(8) . ?
Cu2 Cl5 2.3370(9) . ?
Cu2 Cl6 2.3146(8) . ?
Cu2 Cl4 2.2620(9) . ?
O1 H 0.8698 . ?
O1 HA 0.8710 . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 C7 1.513(4) . ?
N2 C6 1.513(4) . ?
N4 H4 0.8800 . ?
N4 C18 1.331(5) . ?
N4 C14 1.342(5) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 C12 1.515(4) . ?
N3 C13 1.518(4) . ?
N1 H1 0.8800 . ?
N1 C1 1.343(5) . ?
N1 C5 1.334(5) . ?
C4 H4A 0.9500 . ?
C4 C3 1.397(5) . ?
C4 C5 1.378(5) . ?
C3 C2 1.383(5) . ?
C3 C6 1.510(4) . ?
C7 H7 1.0000 . ?
C7 C12 1.532(4) . ?
C7 C8 1.533(4) . ?
C12 H12 1.0000 . ?
C12 C11 1.542(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C9 1.525(5) . ?
C10 C11 1.520(4) . ?
C2 H2 0.9500 . ?
C2 C1 1.373(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(5) . ?
C15 C14 1.376(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.520(4) . ?
C16 C17 1.399(5) . ?
C16 C13 1.502(5) . ?
C18 H18 0.9500 . ?
C18 C17 1.373(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C1 H1A 0.9500 . ?
C17 H17 0.9500 . ?
C14 H14 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C5 H5 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
Cl8 Cu1 Cl7 84.85(3) . . ?
Cl8 Cu1 Cl1 88.64(3) . . ?
Cl3 Cu1 Cl8 90.85(3) . . ?
Cl3 Cu1 Cl7 112.00(3) . . ?
Cl3 Cu1 Cl1 145.47(3) . . ?
Cl3 Cu1 Cl2 91.30(3) . . ?
Cl1 Cu1 Cl7 102.33(3) . . ?
Cl2 Cu1 Cl8 177.83(4) . . ?
Cl2 Cu1 Cl7 94.55(3) . . ?
Cl2 Cu1 Cl1 89.46(3) . . ?
Cl7 Cu2 Cl8 84.48(3) . . ?
Cl7 Cu2 Cl5 91.61(3) . . ?
Cl5 Cu2 Cl8 107.14(3) . . ?
Cl6 Cu2 Cl8 87.41(3) . . ?
Cl6 Cu2 Cl7 171.84(3) . . ?
Cl6 Cu2 Cl5 89.94(3) . . ?
Cl4 Cu2 Cl8 109.82(3) . . ?
Cl4 Cu2 Cl7 93.30(3) . . ?
Cl4 Cu2 Cl5 143.00(4) . . ?
Cl4 Cu2 Cl6 90.27(3) . . ?
Cu1 Cl8 Cu2 95.30(3) . . ?
Cu2 Cl7 Cu1 94.69(3) . . ?
H O1 HA 104.4 . . ?
H2A N2 H2B 107.7 . . ?
C7 N2 H2A 108.9 . . ?
C7 N2 H2B 108.9 . . ?
C6 N2 H2A 108.9 . . ?
C6 N2 H2B 108.9 . . ?
C6 N2 C7 113.3(2) . . ?
C18 N4 H4 118.7 . . ?
C18 N4 C14 122.5(3) . . ?
C14 N4 H4 118.7 . . ?
H3A N3 H3B 107.7 . . ?
C12 N3 H3A 108.9 . . ?
C12 N3 H3B 108.9 . . ?
C12 N3 C13 113.5(2) . . ?
C13 N3 H3A 108.9 . . ?
C13 N3 H3B 108.9 . . ?
C1 N1 H1 118.7 . . ?
C5 N1 H1 118.7 . . ?
C5 N1 C1 122.6(3) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
C5 C4 C3 119.1(3) . . ?
C4 C3 C6 120.4(3) . . ?
C2 C3 C4 119.2(3) . . ?
C2 C3 C6 120.3(3) . . ?
N2 C7 H7 108.8 . . ?
N2 C7 C12 112.4(2) . . ?
N2 C7 C8 108.9(2) . . ?
C12 C7 H7 108.8 . . ?
C12 C7 C8 108.9(3) . . ?
C8 C7 H7 108.8 . . ?
N3 C12 C7 112.3(2) . . ?
N3 C12 H12 109.0 . . ?
N3 C12 C11 109.1(2) . . ?
C7 C12 H12 109.0 . . ?
C7 C12 C11 108.5(3) . . ?
C11 C12 H12 109.0 . . ?
H10A C10 H10B 108.1 . . ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
C11 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C11 C10 C9 110.2(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 C3 119.5(3) . . ?
C1 C2 H2 120.2 . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.8(3) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C8 C9 C10 110.6(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C15 C16 C17 118.9(3) . . ?
C15 C16 C13 122.0(3) . . ?
C17 C16 C13 119.1(3) . . ?
N4 C18 H18 119.7 . . ?
N4 C18 C17 120.6(3) . . ?
C17 C18 H18 119.7 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C9 C8 C7 111.7(3) . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
N1 C1 C2 119.7(3) . . ?
N1 C1 H1A 120.2 . . ?
C2 C1 H1A 120.2 . . ?
C16 C17 H17 120.6 . . ?
C18 C17 C16 118.8(3) . . ?
C18 C17 H17 120.6 . . ?
N4 C14 C15 119.4(3) . . ?
N4 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
C3 C6 N2 110.5(3) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 C12 111.7(3) . . ?
C10 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
N3 C13 H13A 109.9 . . ?
N3 C13 H13B 109.9 . . ?
C16 C13 N3 109.1(3) . . ?
C16 C13 H13A 109.9 . . ?
C16 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
N1 C5 C4 119.8(3) . . ?
N1 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
