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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_pl5
_database_code_depnum_ccdc_archive 'CCDC 1543792'
_audit_update_record             
;
2017-04-13 deposited with the CCDC.
2018-10-18 downloaded from the CCDC.
;
_audit_creation_date             2017-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H42 Cl2 Cu2 N8 O8, 2(Cl O4)'
_chemical_formula_sum            'C44 H42 Cl4 Cu2 N8 O16'
_chemical_formula_weight         1207.73
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4013(6)
_cell_length_b                   9.4328(6)
_cell_length_c                   16.0385(11)
_cell_angle_alpha                84.045(2)
_cell_angle_beta                 84.266(2)
_cell_angle_gamma                78.661(2)
_cell_volume                     1235.36(15)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4468
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.212
_cell_measurement_theta_min      2.997
_shelx_estimated_absorpt_T_max   0.837
_shelx_estimated_absorpt_T_min   0.769
_exptl_absorpt_coefficient_mu    1.156
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0747 before and 0.0575 after correction.
The Ratio of minimum to maximum transmission is 0.9161.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark green'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1042
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            29505
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.423
_diffrn_reflns_theta_max         25.423
_diffrn_reflns_theta_min         2.884
_diffrn_ambient_temperature      296.0
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3059
_reflns_number_total             4537
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         4537
_refine_ls_number_restraints     88
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0596
_refine_ls_restrained_S_all      1.082
_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)+(0.0715P)²+2.0243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1562
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl2-O5A \\sim Cl2-O6B \\sim Cl2-O5B \\sim Cl2-O8B \\sim Cl2-O6A \\sim Cl2-O8A
\\sim Cl2-O7A \\sim Cl2-O7B
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 Cl2, O8B, O5B, O7B, O6B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Cl2, O8A, O6A, O7A, O5A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(O5A)=Sof(O6A)=Sof(O7A)=Sof(O8A)=1-FVAR(1)
 Sof(O5B)=Sof(O6B)=Sof(O7B)=Sof(O8B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B), C13(H13A,H13B)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C10(H10), C9(H9), C4(H4), C3(H3), C2(H2), C1(H1),
 C16(H16), C17(H17), C18(H18), C19(H19)
5.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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 0.53527(7) 0.63231(6) 0.22479(4) 0.0374(2) Uani 1 1 d . . . . .
Cl1 Cl 0.87128(18) 0.76944(16) 0.11328(9) 0.0533(4) Uani 1 1 d . . . . .
O1 O 0.7664(5) 0.6648(5) 0.1244(2) 0.0603(11) Uani 1 1 d . . . . .
O2 O 0.7773(8) 0.9059(6) 0.1039(4) 0.119(2) Uani 1 1 d . . . . .
O3 O 0.9638(7) 0.7507(7) 0.1833(3) 0.101(2) Uani 1 1 d . . . . .
O4 O 0.9776(6) 0.7457(6) 0.0406(3) 0.0928(16) Uani 1 1 d . . . . .
N3 N 0.4787(5) 0.4939(5) 0.1532(2) 0.0405(10) Uani 1 1 d . . . . .
N2 N 0.6703(5) 0.4495(4) 0.2788(2) 0.0350(9) Uani 1 1 d . . . . .
N1 N 0.6189(5) 0.7303(4) 0.3086(2) 0.0377(10) Uani 1 1 d . . . . .
N4 N 0.3860(5) 0.8032(5) 0.1758(3) 0.0475(11) Uani 1 1 d . . . . .
C12 C 0.3515(7) 0.5107(6) 0.1063(3) 0.0494(14) Uani 1 1 d . . . . .
H12 H 0.2732 0.5953 0.1079 0.059 Uiso 1 1 calc R . . . .
C11 C 0.3339(8) 0.4076(8) 0.0565(4) 0.0618(17) Uani 1 1 d . . . . .
H11 H 0.2439 0.4215 0.0251 0.074 Uiso 1 1 calc R . . . .
C10 C 0.4483(9) 0.2840(8) 0.0526(4) 0.0666(18) Uani 1 1 d . . . . .
H10 H 0.4393 0.2143 0.0173 0.080 Uiso 1 1 calc R . . . .
C9 C 0.5775(9) 0.2635(7) 0.1018(4) 0.0621(17) Uani 1 1 d . . . . .
H9 H 0.6553 0.1784 0.1012 0.075 Uiso 1 1 calc R . . . .
C8 C 0.5906(7) 0.3706(6) 0.1519(3) 0.0444(13) Uani 1 1 d . . . . .
C7 C 0.7279(7) 0.3625(6) 0.2058(3) 0.0468(13) Uani 1 1 d . . . . .
H7A H 0.7678 0.2623 0.2255 0.056 Uiso 1 1 calc R . . . .
H7B H 0.8168 0.3997 0.1732 0.056 Uiso 1 1 calc R . . . .
C6 C 0.8013(6) 0.5007(5) 0.3162(3) 0.0389(12) Uani 1 1 d . . . . .
H6A H 0.8896 0.5108 0.2735 0.047 Uiso 1 1 calc R . . . .
H6B H 0.8440 0.4300 0.3607 0.047 Uiso 1 1 calc R . . . .
C5 C 0.7362(6) 0.6430(5) 0.3510(3) 0.0359(11) Uani 1 1 d . . . . .
C4 C 0.7911(7) 0.6876(6) 0.4199(3) 0.0474(13) Uani 1 1 d . . . . .
H4 H 0.8705 0.6264 0.4498 0.057 Uiso 1 1 calc R . . . .
C3 C 0.7260(8) 0.8255(7) 0.4441(4) 0.0572(16) Uani 1 1 d . . . . .
H3 H 0.7622 0.8578 0.4904 0.069 Uiso 1 1 calc R . . . .
C2 C 0.6097(7) 0.9130(6) 0.4001(4) 0.0563(15) Uani 1 1 d . . . . .
H2 H 0.5660 1.0060 0.4154 0.068 Uiso 1 1 calc R . . . .
C1 C 0.5575(7) 0.8621(6) 0.3328(3) 0.0466(13) Uani 1 1 d . . . . .
H1 H 0.4765 0.9215 0.3030 0.056 Uiso 1 1 calc R . . . .
C13 C 0.5767(7) 0.3610(6) 0.3428(3) 0.0455(13) Uani 1 1 d . . . . .
H13A H 0.4773 0.3507 0.3199 0.055 Uiso 1 1 calc R . . . .
H13B H 0.6416 0.2646 0.3527 0.055 Uiso 1 1 calc R . . . .
C14 C 0.5334(6) 0.4280(6) 0.4254(3) 0.0398(12) Uani 1 1 d . . . . .
C15 C 0.4032(6) 0.5465(6) 0.4315(3) 0.0397(12) Uani 1 1 d . . . . .
C16 C 0.2991(6) 0.5958(7) 0.3651(3) 0.0494(14) Uani 1 1 d . . . . .
H16 H 0.3111 0.5424 0.3185 0.059 Uiso 1 1 calc R . . . .
C17 C 0.1843(7) 0.7169(7) 0.3678(4) 0.0610(17) Uani 1 1 d . . . . .
H17 H 0.1199 0.7473 0.3230 0.073 Uiso 1 1 calc R . . . .
C18 C 0.1620(7) 0.7967(7) 0.4375(4) 0.0590(16) Uani 1 1 d . . . . .
H18 H 0.0862 0.8830 0.4376 0.071 Uiso 1 1 calc R . . . .
C19 C 0.2491(7) 0.7508(6) 0.5056(4) 0.0510(14) Uani 1 1 d . . . . .
H19 H 0.2276 0.8029 0.5529 0.061 Uiso 1 1 calc R . . . .
C20 C 0.3724(6) 0.6242(6) 0.5050(3) 0.0391(12) Uani 1 1 d . . . . .
C21 C 0.2933(7) 0.8958(6) 0.1495(4) 0.0491(14) Uani 1 1 d . . . . .
C22 C 0.1745(9) 1.0152(7) 0.1160(5) 0.086(2) Uani 1 1 d . . . . .
H22A H 0.2101 1.1050 0.1194 0.129 Uiso 1 1 calc GR . . . .
H22B H 0.0715 1.0166 0.1481 0.129 Uiso 1 1 calc GR . . . .
H22C H 0.1629 1.0033 0.0583 0.129 Uiso 1 1 calc GR . . . .
Cl2 Cl 0.1632(2) 1.21465(18) 0.30849(12) 0.0728(5) Uani 1 1 d D U . . .
O5B O 0.0137(10) 1.1653(10) 0.3163(7) 0.0820(19) Uani 0.593(9) 1 d D U P A 1
O6B O 0.3165(10) 1.1437(11) 0.2777(8) 0.106(2) Uani 0.593(9) 1 d D U P A 1
O7B O 0.1617(13) 1.3150(11) 0.3721(6) 0.091(2) Uani 0.593(9) 1 d D U P A 1
O8B O 0.1212(13) 1.3091(10) 0.2343(6) 0.0869(19) Uani 0.593(9) 1 d D U P A 1
O5A O 0.0764(19) 1.1075(15) 0.3063(11) 0.093(2) Uani 0.407(9) 1 d D U P A 2
O6A O 0.2970(14) 1.1268(13) 0.3432(10) 0.088(2) Uani 0.407(9) 1 d D U P A 2
O7A O 0.1074(19) 1.2718(16) 0.3892(8) 0.087(2) Uani 0.407(9) 1 d D U P A 2
O8A O 0.1824(18) 1.3338(13) 0.2505(8) 0.081(2) Uani 0.407(9) 1 d D U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 2.442(4) . ?
Cu1 N3 1.978(4) . ?
Cu1 N2 2.032(4) . ?
Cu1 N1 1.963(4) . ?
Cu1 N4 1.982(5) . ?
Cl1 O1 1.434(4) . ?
Cl1 O2 1.373(5) . ?
Cl1 O3 1.406(4) . ?
Cl1 O4 1.406(5) . ?
N3 C12 1.343(6) . ?
N3 C8 1.345(7) . ?
N2 C7 1.486(6) . ?
N2 C6 1.485(6) . ?
N2 C13 1.513(6) . ?
N1 C5 1.346(6) . ?
N1 C1 1.330(6) . ?
N4 C21 1.127(6) . ?
C12 H12 0.9300 . ?
C12 C11 1.359(8) . ?
C11 H11 0.9300 . ?
C11 C10 1.359(9) . ?
C10 H10 0.9300 . ?
C10 C9 1.376(9) . ?
C9 H9 0.9300 . ?
C9 C8 1.382(8) . ?
C8 C7 1.495(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C5 1.490(7) . ?
C5 C4 1.372(7) . ?
C4 H4 0.9300 . ?
C4 C3 1.387(8) . ?
C3 H3 0.9300 . ?
C3 C2 1.353(8) . ?
C2 H2 0.9300 . ?
C2 C1 1.370(7) . ?
C1 H1 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.509(7) . ?
C14 C15 1.405(7) . ?
C14 C20 1.422(7) 2_666 ?
C15 C16 1.429(7) . ?
C15 C20 1.428(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.344(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(9) . ?
C18 H18 0.9300 . ?
C18 C19 1.362(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.419(7) . ?
C20 C14 1.422(7) 2_666 ?
C21 C22 1.447(8) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
Cl2 O5B 1.413(8) . ?
Cl2 O6B 1.397(8) . ?
Cl2 O7B 1.459(8) . ?
Cl2 O8B 1.440(8) . ?
Cl2 O5A 1.362(10) . ?
Cl2 O6A 1.386(10) . ?
Cl2 O7A 1.453(11) . ?
Cl2 O8A 1.407(10) . ?

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
N3 Cu1 O1 89.64(15) . . ?
N3 Cu1 N2 82.78(16) . . ?
N3 Cu1 N4 94.98(18) . . ?
N2 Cu1 O1 90.09(15) . . ?
N1 Cu1 O1 91.00(15) . . ?
N1 Cu1 N3 167.14(17) . . ?
N1 Cu1 N2 84.38(16) . . ?
N1 Cu1 N4 97.78(17) . . ?
N4 Cu1 O1 94.51(17) . . ?
N4 Cu1 N2 174.87(17) . . ?
O2 Cl1 O1 108.7(3) . . ?
O2 Cl1 O3 112.3(4) . . ?
O2 Cl1 O4 109.1(4) . . ?
O3 Cl1 O1 108.3(3) . . ?
O4 Cl1 O1 109.6(3) . . ?
O4 Cl1 O3 108.8(3) . . ?
Cl1 O1 Cu1 132.9(2) . . ?
C12 N3 Cu1 128.8(4) . . ?
C12 N3 C8 119.1(5) . . ?
C8 N3 Cu1 112.0(3) . . ?
C7 N2 Cu1 102.4(3) . . ?
C7 N2 C13 108.0(4) . . ?
C6 N2 Cu1 104.8(3) . . ?
C6 N2 C7 114.3(4) . . ?
C6 N2 C13 112.1(4) . . ?
C13 N2 Cu1 115.2(3) . . ?
C5 N1 Cu1 113.3(3) . . ?
C1 N1 Cu1 126.5(3) . . ?
C1 N1 C5 119.6(4) . . ?
C21 N4 Cu1 175.6(5) . . ?
N3 C12 H12 119.1 . . ?
N3 C12 C11 121.9(6) . . ?
C11 C12 H12 119.1 . . ?
C12 C11 H11 120.1 . . ?
C12 C11 C10 119.8(6) . . ?
C10 C11 H11 120.1 . . ?
C11 C10 H10 120.5 . . ?
C11 C10 C9 119.1(6) . . ?
C9 C10 H10 120.5 . . ?
C10 C9 H9 120.3 . . ?
C10 C9 C8 119.3(6) . . ?
C8 C9 H9 120.3 . . ?
N3 C8 C9 120.8(5) . . ?
N3 C8 C7 115.1(4) . . ?
C9 C8 C7 124.1(5) . . ?
N2 C7 C8 109.5(4) . . ?
N2 C7 H7A 109.8 . . ?
N2 C7 H7B 109.8 . . ?
C8 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
N2 C6 H6A 109.6 . . ?
N2 C6 H6B 109.6 . . ?
N2 C6 C5 110.1(4) . . ?
H6A C6 H6B 108.2 . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
N1 C5 C6 115.1(4) . . ?
N1 C5 C4 120.7(5) . . ?
C4 C5 C6 124.2(4) . . ?
C5 C4 H4 120.6 . . ?
C5 C4 C3 118.9(5) . . ?
C3 C4 H4 120.6 . . ?
C4 C3 H3 120.1 . . ?
C2 C3 C4 119.8(5) . . ?
C2 C3 H3 120.1 . . ?
C3 C2 H2 120.6 . . ?
C3 C2 C1 118.8(5) . . ?
C1 C2 H2 120.6 . . ?
N1 C1 C2 122.1(5) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
N2 C13 H13A 109.0 . . ?
N2 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 N2 113.0(4) . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C15 C14 C13 119.1(4) . . ?
C15 C14 C20 120.5(5) . 2_666 ?
C20 C14 C13 120.3(5) 2_666 . ?
C14 C15 C16 122.2(5) . . ?
C14 C15 C20 120.4(4) . . ?
C20 C15 C16 117.4(5) . . ?
C15 C16 H16 119.0 . . ?
C17 C16 C15 122.1(6) . . ?
C17 C16 H16 119.0 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 119.9(5) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.4 . . ?
C19 C18 C17 121.2(6) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.6(6) . . ?
C20 C19 H19 119.7 . . ?
C14 C20 C15 118.8(5) 2_666 . ?
C19 C20 C14 122.6(5) . 2_666 ?
C19 C20 C15 118.6(5) . . ?
N4 C21 C22 179.7(7) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O5B Cl2 O7B 109.7(6) . . ?
O5B Cl2 O8B 92.7(6) . . ?
O6B Cl2 O5B 128.4(6) . . ?
O6B Cl2 O7B 116.2(6) . . ?
O6B Cl2 O8B 98.3(7) . . ?
O8B Cl2 O7B 103.5(6) . . ?
O5A Cl2 O6A 96.3(9) . . ?
O5A Cl2 O7A 103.5(9) . . ?
O5A Cl2 O8A 130.8(9) . . ?
O6A Cl2 O7A 90.5(9) . . ?
O6A Cl2 O8A 120.7(8) . . ?
O8A Cl2 O7A 107.0(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6A O8B 0.97 2.52 3.176(11) 125.0 1_645
C6 H6B O7A 0.97 2.47 3.247(15) 137.0 1_645
C3 H3 O7B 0.93 2.66 3.255(12) 122.7 2_676
C3 H3 O7A 0.93 2.41 3.112(15) 131.7 2_676
C1 H1 O6B 0.93 2.28 3.113(11) 149.2 .
C1 H1 O6A 0.93 2.31 2.986(12) 128.8 .

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 N3 C12 C11 176.3(4) . . . . ?
Cu1 N3 C8 C9 -176.4(4) . . . . ?
Cu1 N3 C8 C7 1.9(5) . . . . ?
Cu1 N2 C7 C8 -43.3(4) . . . . ?
Cu1 N2 C6 C5 37.0(4) . . . . ?
Cu1 N2 C13 C14 -75.0(5) . . . . ?
Cu1 N1 C5 C6 11.0(5) . . . . ?
Cu1 N1 C5 C4 -170.4(4) . . . . ?
Cu1 N1 C1 C2 170.4(4) . . . . ?
O2 Cl1 O1 Cu1 -55.8(5) . . . . ?
O3 Cl1 O1 Cu1 66.6(4) . . . . ?
O4 Cl1 O1 Cu1 -174.9(3) . . . . ?
N3 C12 C11 C10 -0.8(9) . . . . ?
N3 C8 C7 N2 29.3(6) . . . . ?
N2 C6 C5 N1 -33.4(6) . . . . ?
N2 C6 C5 C4 148.2(5) . . . . ?
N2 C13 C14 C15 77.3(6) . . . . ?
N2 C13 C14 C20 -100.1(5) . . . 2_666 ?
N1 C5 C4 C3 -1.4(8) . . . . ?
C12 N3 C8 C9 1.3(8) . . . . ?
C12 N3 C8 C7 179.7(4) . . . . ?
C12 C11 C10 C9 2.2(9) . . . . ?
C11 C10 C9 C8 -1.9(9) . . . . ?
C10 C9 C8 N3 0.1(8) . . . . ?
C10 C9 C8 C7 -178.1(5) . . . . ?
C9 C8 C7 N2 -152.4(5) . . . . ?
C8 N3 C12 C11 -1.0(8) . . . . ?
C7 N2 C6 C5 148.3(4) . . . . ?
C7 N2 C13 C14 171.3(4) . . . . ?
C6 N2 C7 C8 -156.0(4) . . . . ?
C6 N2 C13 C14 44.6(6) . . . . ?
C6 C5 C4 C3 177.0(5) . . . . ?
C5 N1 C1 C2 -0.1(8) . . . . ?
C5 C4 C3 C2 0.4(9) . . . . ?
C4 C3 C2 C1 0.7(9) . . . . ?
C3 C2 C1 N1 -0.9(9) . . . . ?
C1 N1 C5 C6 -177.3(4) . . . . ?
C1 N1 C5 C4 1.2(7) . . . . ?
C13 N2 C7 C8 78.6(5) . . . . ?
C13 N2 C6 C5 -88.5(5) . . . . ?
C13 C14 C15 C16 6.9(7) . . . . ?
C13 C14 C15 C20 -171.9(4) . . . . ?
C14 C15 C16 C17 -173.7(5) . . . . ?
C14 C15 C20 C14 -5.4(8) . . . 2_666 ?
C14 C15 C20 C19 174.4(5) . . . . ?
C15 C16 C17 C18 -1.3(9) . . . . ?
C16 C15 C20 C14 175.7(4) . . . 2_666 ?
C16 C15 C20 C19 -4.5(7) . . . . ?
C16 C17 C18 C19 -3.3(9) . . . . ?
C17 C18 C19 C20 3.8(9) . . . . ?
C18 C19 C20 C14 180.0(5) . . . 2_666 ?
C18 C19 C20 C15 0.2(8) . . . . ?
C20 C14 C15 C16 -175.7(5) 2_666 . . . ?
C20 C14 C15 C20 5.5(8) 2_666 . . . ?
C20 C15 C16 C17 5.1(8) . . . . ?

_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_pl7
_database_code_depnum_ccdc_archive 'CCDC 1543794'
_audit_update_record             
;
2017-04-13 deposited with the CCDC.
2018-10-18 downloaded from the CCDC.
;
_audit_creation_date             2017-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H46 Cu2 N8 O2, 4(Cl1 O4)'
_chemical_formula_sum            'C44 H46 Cl4 Cu2 N8 O18'
_chemical_formula_weight         1243.77
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0380(3)
_cell_length_b                   10.6269(3)
_cell_length_c                   12.7725(4)
_cell_angle_alpha                109.7640(10)
_cell_angle_beta                 95.8450(10)
_cell_angle_gamma                97.6530(10)
_cell_volume                     1254.94(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9863
_cell_measurement_temperature    296
_cell_measurement_theta_max      27.816
_cell_measurement_theta_min      2.929
_shelx_estimated_absorpt_T_max   0.804
_shelx_estimated_absorpt_T_min   0.755
_exptl_absorpt_coefficient_mu    1.143
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6831
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0602 before and 0.0499 after correction.
The Ratio of minimum to maximum transmission is 0.9162.
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    1.646
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            42084
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.921
_diffrn_reflns_theta_min         2.929
_diffrn_ambient_temperature      296.0
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 D8 QUEST CMOS'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4727
_reflns_number_total             5996
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         5996
_refine_ls_number_restraints     195
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.185
_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)+(0.0590P)²+1.0051P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1175
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 O6A-O8A \\sim O6A-O7A \\sim O6A-O9A \\sim O8A-O7A \\sim O8A-O9A \\sim O7A-O9A
 with sigma of 0.04
 Cl2A-O6A \\sim Cl2A-O8A \\sim Cl2A-O7A \\sim Cl2A-O9A
 with sigma of 0.02
 O6B-O8B \\sim O6B-O7B \\sim O6B-O9B \\sim O8B-O7B \\sim O8B-O9B \\sim O7B-O9B
 with sigma of 0.04
 Cl2B-O6B \\sim Cl2B-O8B \\sim Cl2B-O7B \\sim Cl2B-O9B
 with sigma of 0.02
 O4A-O2A \\sim O4A-O5A \\sim O2A-O5A \\sim O2B-O4B \\sim O2B-O5B \\sim O4B-O5B
 with sigma of 0.04
 Cl1-O3 \\sim Cl1-O4A \\sim Cl1-O2A \\sim Cl1-O5A \\sim Cl1-O2B \\sim Cl1-O4B
\\sim Cl1-O5B
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 Cl1, O3, O4A, O2A, O5A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Cl2A, O6A, O8A, O7A, O9A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Cl1, O3, O2B, O4B, O5B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Cl2B, O6B, O8B, O7B, O9B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(Cl2B)=Sof(O6B)=Sof(O8B)=Sof(O7B)=Sof(O9B)=1-FVAR(1)
 Sof(Cl2A)=Sof(O6A)=Sof(O8A)=Sof(O7A)=Sof(O9A)=FVAR(1)
 Sof(O2B)=Sof(O4B)=Sof(O5B)=1-FVAR(2)
 Sof(O4A)=Sof(O2A)=Sof(O5A)=FVAR(2)
5.a Rotating group:
 O1(H1A,H1B)
5.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C13(H13A,H13B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C16(H16), C17(H17), C18(H18), C19(H19)
5.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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 0.30480(3) 0.67380(3) 0.74031(2) 0.03565(11) Uani 1 1 d . . . . .
O1 O 0.5112(2) 0.8179(2) 0.80153(19) 0.0580(6) Uani 1 1 d . . . . .
H1A H 0.5675 0.8031 0.7476 0.087 Uiso 1 1 d GR . . . .
H1B H 0.5592 0.8091 0.8633 0.087 Uiso 1 1 d GR . . . .
N1 N 0.3185(2) 0.6293(2) 0.57855(17) 0.0337(4) Uani 1 1 d . . . . .
N2 N 0.2028(2) 0.8169(2) 0.71522(18) 0.0341(4) Uani 1 1 d . . . . .
N3 N 0.2623(2) 0.7511(2) 0.89595(18) 0.0430(5) Uani 1 1 d . . . . .
N4 N 0.3658(2) 0.5085(2) 0.7548(2) 0.0448(5) Uani 1 1 d . . . . .
C1 C 0.3358(3) 0.5103(3) 0.5041(2) 0.0382(5) Uani 1 1 d . . . . .
H1 H 0.3483 0.4395 0.5291 0.046 Uiso 1 1 calc R . . . .
C2 C 0.3354(3) 0.4907(3) 0.3922(2) 0.0420(6) Uani 1 1 d . . . . .
H2 H 0.3458 0.4071 0.3420 0.050 Uiso 1 1 calc R . . . .
C3 C 0.3195(3) 0.5960(3) 0.3551(2) 0.0440(6) Uani 1 1 d . . . . .
H3 H 0.3201 0.5846 0.2797 0.053 Uiso 1 1 calc R . . . .
C4 C 0.3025(3) 0.7188(3) 0.4309(2) 0.0418(6) Uani 1 1 d . . . . .
H4 H 0.2935 0.7917 0.4078 0.050 Uiso 1 1 calc R . . . .
C5 C 0.2991(2) 0.7311(2) 0.5418(2) 0.0352(5) Uani 1 1 d . . . . .
C6 C 0.2703(3) 0.8560(3) 0.6292(2) 0.0404(6) Uani 1 1 d . . . . .
H6A H 0.3547 0.9192 0.6652 0.048 Uiso 1 1 calc R . . . .
H6B H 0.2116 0.9005 0.5938 0.048 Uiso 1 1 calc R . . . .
C7 C 0.2270(3) 0.9300(3) 0.8261(2) 0.0457(6) Uani 1 1 d . . . . .
H7A H 0.1589 0.9873 0.8284 0.055 Uiso 1 1 calc R . . . .
H7B H 0.3160 0.9852 0.8373 0.055 Uiso 1 1 calc R . . . .
C8 C 0.2191(3) 0.8705(3) 0.9173(2) 0.0440(6) Uani 1 1 d . . . . .
C9 C 0.1738(3) 0.9334(3) 1.0169(3) 0.0561(8) Uani 1 1 d . . . . .
H9 H 0.1439 1.0158 1.0303 0.067 Uiso 1 1 calc R . . . .
C10 C 0.1736(4) 0.8722(4) 1.0967(3) 0.0662(10) Uani 1 1 d . . . . .
H10 H 0.1434 0.9130 1.1645 0.079 Uiso 1 1 calc R . . . .
C11 C 0.2179(4) 0.7514(4) 1.0752(3) 0.0637(9) Uani 1 1 d . . . . .
H11 H 0.2180 0.7089 1.1280 0.076 Uiso 1 1 calc R . . . .
C12 C 0.2624(3) 0.6933(3) 0.9744(2) 0.0526(7) Uani 1 1 d . . . . .
H12 H 0.2936 0.6114 0.9602 0.063 Uiso 1 1 calc R . . . .
C13 C 0.0503(3) 0.7692(3) 0.6781(2) 0.0376(5) Uani 1 1 d . . . . .
H13A H 0.0083 0.7657 0.7424 0.045 Uiso 1 1 calc R . . . .
H13B H 0.0129 0.8345 0.6515 0.045 Uiso 1 1 calc R . . . .
C14 C 0.0154(2) 0.6305(2) 0.5855(2) 0.0321(5) Uani 1 1 d . . . . .
C15 C -0.0069(2) 0.6175(2) 0.4719(2) 0.0326(5) Uani 1 1 d . . . . .
C16 C -0.0200(3) 0.7301(3) 0.4363(2) 0.0428(6) Uani 1 1 d . . . . .
H16 H -0.0197 0.8147 0.4904 0.051 Uiso 1 1 calc R . . . .
C17 C -0.0328(3) 0.7174(3) 0.3265(3) 0.0494(7) Uani 1 1 d . . . . .
H17 H -0.0442 0.7919 0.3061 0.059 Uiso 1 1 calc R . . . .
C18 C -0.0289(3) 0.5923(3) 0.2434(2) 0.0485(7) Uani 1 1 d . . . . .
H18 H -0.0312 0.5856 0.1688 0.058 Uiso 1 1 calc R . . . .
C19 C -0.0219(3) 0.4808(3) 0.2714(2) 0.0405(6) Uani 1 1 d . . . . .
H19 H -0.0210 0.3983 0.2149 0.049 Uiso 1 1 calc R . . . .
C20 C -0.0159(2) 0.4864(2) 0.3854(2) 0.0318(5) Uani 1 1 d . . . . .
C21 C 0.3898(3) 0.4112(3) 0.7623(2) 0.0446(6) Uani 1 1 d . . . . .
C22 C 0.4196(4) 0.2864(4) 0.7736(3) 0.0645(9) Uani 1 1 d . . . . .
H22A H 0.4476 0.2317 0.7057 0.097 Uiso 1 1 calc GR . . . .
H22B H 0.3395 0.2373 0.7868 0.097 Uiso 1 1 calc GR . . . .
H22C H 0.4913 0.3074 0.8359 0.097 Uiso 1 1 calc GR . . . .
Cl2A Cl 0.7461(3) 0.6875(3) 0.9677(2) 0.0550(5) Uani 0.778(8) 1 d D U P A 1
O6A O 0.6385(4) 0.7693(4) 0.9866(3) 0.0693(10) Uani 0.778(8) 1 d D U P A 1
O8A O 0.8346(7) 0.7342(5) 1.0720(4) 0.0823(14) Uani 0.778(8) 1 d D U P A 1
O7A O 0.8027(6) 0.7079(5) 0.8760(4) 0.0830(13) Uani 0.778(8) 1 d D U P A 1
O9A O 0.6850(6) 0.5502(4) 0.9368(4) 0.0932(14) Uani 0.778(8) 1 d D U P A 1
Cl2B Cl 0.7727(14) 0.6821(14) 0.9678(11) 0.079(3) Uani 0.222(8) 1 d D U P A 2
O6B O 0.6327(16) 0.6916(19) 0.9566(13) 0.090(3) Uani 0.222(8) 1 d D U P A 2
O8B O 0.837(2) 0.7741(17) 1.0755(15) 0.078(3) Uani 0.222(8) 1 d D U P A 2
O7B O 0.8487(19) 0.7421(17) 0.9041(13) 0.076(3) Uani 0.222(8) 1 d D U P A 2
O9B O 0.795(2) 0.5506(12) 0.9424(11) 0.089(3) Uani 0.222(8) 1 d D U P A 2
Cl1 Cl 0.69714(8) 0.91227(7) 0.59443(6) 0.05069(18) Uani 1 1 d D U . . .
O3 O 0.6051(3) 0.9952(3) 0.6446(3) 0.0915(8) Uani 1 1 d D U . . .
O4A O 0.8150(5) 0.9947(5) 0.5888(5) 0.0796(13) Uani 0.716(7) 1 d D U P B 1
O2A O 0.7367(6) 0.8400(5) 0.6683(4) 0.0825(12) Uani 0.716(7) 1 d D U P B 1
O5A O 0.6432(5) 0.8089(5) 0.4889(4) 0.0979(14) Uani 0.716(7) 1 d D U P B 1
O2B O 0.6716(13) 0.8000(10) 0.6201(11) 0.075(2) Uani 0.284(7) 1 d D U P B 2
O4B O 0.8337(10) 0.9869(13) 0.6300(10) 0.064(2) Uani 0.284(7) 1 d D U P B 2
O5B O 0.6618(11) 0.8929(13) 0.4781(7) 0.079(2) Uani 0.284(7) 1 d D U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 2.295(2) . ?
Cu1 N1 1.981(2) . ?
Cu1 N2 2.035(2) . ?
Cu1 N3 1.993(2) . ?
Cu1 N4 1.994(2) . ?
O1 H1A 0.9212 . ?
O1 H1B 0.9205 . ?
N1 C1 1.345(3) . ?
N1 C5 1.346(3) . ?
N2 C6 1.491(3) . ?
N2 C7 1.486(3) . ?
N2 C13 1.519(3) . ?
N3 C8 1.345(4) . ?
N3 C12 1.341(4) . ?
N4 C21 1.125(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.372(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(4) . ?
C5 C6 1.503(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.505(4) . ?
C8 C9 1.377(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.363(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(5) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.514(3) . ?
C14 C15 1.401(3) . ?
C14 C20 1.412(3) 2_566 ?
C15 C16 1.434(3) . ?
C15 C20 1.440(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.354(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.401(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.357(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.432(3) . ?
C20 C14 1.412(3) 2_566 ?
C21 C22 1.448(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
Cl2A O6A 1.464(4) . ?
Cl2A O8A 1.416(5) . ?
Cl2A O7A 1.420(4) . ?
Cl2A O9A 1.408(5) . ?
Cl2B O6B 1.418(14) . ?
Cl2B O8B 1.417(15) . ?
Cl2B O7B 1.413(14) . ?
Cl2B O9B 1.378(14) . ?
Cl1 O3 1.413(3) . ?
Cl1 O4A 1.398(4) . ?
Cl1 O2A 1.460(4) . ?
Cl1 O5A 1.418(4) . ?
Cl1 O2B 1.341(8) . ?
Cl1 O4B 1.433(9) . ?
Cl1 O5B 1.429(8) . ?

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
N1 Cu1 O1 94.19(8) . . ?
N1 Cu1 N2 82.75(8) . . ?
N1 Cu1 N3 165.50(9) . . ?
N1 Cu1 N4 96.78(9) . . ?
N2 Cu1 O1 94.18(8) . . ?
N3 Cu1 O1 88.04(9) . . ?
N3 Cu1 N2 82.80(9) . . ?
N3 Cu1 N4 97.09(10) . . ?
N4 Cu1 O1 97.99(9) . . ?
N4 Cu1 N2 167.82(9) . . ?
Cu1 O1 H1A 112.8 . . ?
Cu1 O1 H1B 112.6 . . ?
H1A O1 H1B 105.8 . . ?
C1 N1 Cu1 127.84(18) . . ?
C1 N1 C5 118.9(2) . . ?
C5 N1 Cu1 113.06(17) . . ?
C6 N2 Cu1 103.87(15) . . ?
C6 N2 C13 112.2(2) . . ?
C7 N2 Cu1 105.30(16) . . ?
C7 N2 C6 112.16(19) . . ?
C7 N2 C13 108.7(2) . . ?
C13 N2 Cu1 114.42(15) . . ?
C8 N3 Cu1 113.28(18) . . ?
C12 N3 Cu1 127.6(2) . . ?
C12 N3 C8 118.9(3) . . ?
C21 N4 Cu1 174.6(2) . . ?
N1 C1 H1 119.1 . . ?
N1 C1 C2 121.8(2) . . ?
C2 C1 H1 119.1 . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.3(3) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.7(2) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 121.8(2) . . ?
N1 C5 C6 115.0(2) . . ?
C4 C5 C6 123.2(2) . . ?
N2 C6 C5 109.48(19) . . ?
N2 C6 H6A 109.8 . . ?
N2 C6 H6B 109.8 . . ?
C5 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 H7A 110.0 . . ?
N2 C7 H7B 110.0 . . ?
N2 C7 C8 108.6(2) . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 H7A 110.0 . . ?
C8 C7 H7B 110.0 . . ?
N3 C8 C7 115.2(2) . . ?
N3 C8 C9 121.5(3) . . ?
C9 C8 C7 123.3(3) . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 118.9(3) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.5(3) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.2(3) . . ?
C12 C11 H11 120.4 . . ?
N3 C12 C11 122.0(3) . . ?
N3 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
N2 C13 H13A 109.1 . . ?
N2 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 N2 112.50(19) . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 C20 119.9(2) . 2_566 ?
C20 C14 C13 118.9(2) 2_566 . ?
C14 C15 C16 123.0(2) . . ?
C14 C15 C20 119.7(2) . . ?
C16 C15 C20 117.3(2) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 C15 122.2(3) . . ?
C17 C16 H16 118.9 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.1(3) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.3(3) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.0 . . ?
C18 C19 C20 121.9(3) . . ?
C20 C19 H19 119.0 . . ?
C14 C20 C15 120.1(2) 2_566 . ?
C14 C20 C19 122.2(2) 2_566 . ?
C19 C20 C15 117.6(2) . . ?
N4 C21 C22 179.0(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O8A Cl2A O6A 105.2(3) . . ?
O8A Cl2A O7A 116.0(4) . . ?
O7A Cl2A O6A 105.6(3) . . ?
O9A Cl2A O6A 107.8(3) . . ?
O9A Cl2A O8A 111.8(3) . . ?
O9A Cl2A O7A 109.7(3) . . ?
O8B Cl2B O6B 108.3(14) . . ?
O7B Cl2B O6B 114.4(12) . . ?
O7B Cl2B O8B 96.8(12) . . ?
O9B Cl2B O6B 113.3(12) . . ?
O9B Cl2B O8B 115.1(13) . . ?
O9B Cl2B O7B 108.1(12) . . ?
O3 Cl1 O2A 107.8(2) . . ?
O3 Cl1 O5A 115.3(3) . . ?
O3 Cl1 O4B 110.0(6) . . ?
O3 Cl1 O5B 102.0(5) . . ?
O4A Cl1 O3 109.2(3) . . ?
O4A Cl1 O2A 107.2(3) . . ?
O4A Cl1 O5A 111.9(3) . . ?
O5A Cl1 O2A 104.9(3) . . ?
O2B Cl1 O3 105.7(5) . . ?
O2B Cl1 O4B 116.0(7) . . ?
O2B Cl1 O5B 115.3(7) . . ?
O5B Cl1 O4B 106.9(6) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O2A 0.92 2.12 2.998(5) 158.3 .
O1 H1A O2B 0.92 2.02 2.922(11) 167.8 .
O1 H1B O6A 0.92 1.89 2.806(4) 171.9 .
O1 H1B O6B 0.92 2.14 2.992(16) 152.7 .
C2 H2 O2B 0.93 2.40 3.031(9) 125.3 2_666
C7 H7A O8B 0.97 2.41 3.15(2) 132.9 2_677
C12 H12 O9A 0.93 2.51 3.239(5) 135.5 2_667
C22 H22A O5A 0.96 2.43 3.125(6) 129.1 2_666
C22 H22A O5B 0.96 2.34 3.089(10) 134.9 2_666

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 N1 C1 C2 175.97(19) . . . . ?
Cu1 N1 C5 C4 -178.94(19) . . . . ?
Cu1 N1 C5 C6 -0.4(3) . . . . ?
Cu1 N2 C6 C5 40.8(2) . . . . ?
Cu1 N2 C7 C8 -40.5(2) . . . . ?
Cu1 N2 C13 C14 -45.8(2) . . . . ?
Cu1 N3 C8 C7 -6.9(3) . . . . ?
Cu1 N3 C8 C9 174.3(2) . . . . ?
Cu1 N3 C12 C11 -173.3(2) . . . . ?
N1 C1 C2 C3 1.2(4) . . . . ?
N1 C5 C6 N2 -28.4(3) . . . . ?
N2 C7 C8 N3 32.7(3) . . . . ?
N2 C7 C8 C9 -148.6(3) . . . . ?
N2 C13 C14 C15 -94.5(3) . . . . ?
N2 C13 C14 C20 80.7(3) . . . 2_566 ?
N3 C8 C9 C10 0.3(5) . . . . ?
C1 N1 C5 C4 -3.0(4) . . . . ?
C1 N1 C5 C6 175.6(2) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C3 C4 C5 N1 3.3(4) . . . . ?
C3 C4 C5 C6 -175.1(2) . . . . ?
C4 C5 C6 N2 150.1(2) . . . . ?
C5 N1 C1 C2 0.7(4) . . . . ?
C6 N2 C7 C8 -152.8(2) . . . . ?
C6 N2 C13 C14 72.2(3) . . . . ?
C7 N2 C6 C5 154.0(2) . . . . ?
C7 N2 C13 C14 -163.2(2) . . . . ?
C7 C8 C9 C10 -178.4(3) . . . . ?
C8 N3 C12 C11 1.0(4) . . . . ?
C8 C9 C10 C11 0.0(5) . . . . ?
C9 C10 C11 C12 0.2(5) . . . . ?
C10 C11 C12 N3 -0.7(5) . . . . ?
C12 N3 C8 C7 178.0(3) . . . . ?
C12 N3 C8 C9 -0.7(4) . . . . ?
C13 N2 C6 C5 -83.3(2) . . . . ?
C13 N2 C7 C8 82.5(3) . . . . ?
C13 C14 C15 C16 -10.2(4) . . . . ?
C13 C14 C15 C20 169.0(2) . . . . ?
C14 C15 C16 C17 175.6(2) . . . . ?
C14 C15 C20 C14 6.1(4) . . . 2_566 ?
C14 C15 C20 C19 -172.5(2) . . . . ?
C15 C16 C17 C18 -2.2(4) . . . . ?
C16 C15 C20 C14 -174.6(2) . . . 2_566 ?
C16 C15 C20 C19 6.8(3) . . . . ?
C16 C17 C18 C19 4.6(4) . . . . ?
C17 C18 C19 C20 -1.1(4) . . . . ?
C18 C19 C20 C14 176.8(2) . . . 2_566 ?
C18 C19 C20 C15 -4.7(4) . . . . ?
C20 C14 C15 C16 174.7(2) 2_566 . . . ?
C20 C14 C15 C20 -6.1(4) 2_566 . . . ?
C20 C15 C16 C17 -3.6(4) . . . . ?

_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_pl8
_database_code_depnum_ccdc_archive 'CCDC 1543793'
_audit_update_record             
;
2017-04-13 deposited with the CCDC.
2018-10-18 downloaded from the CCDC.
;
_audit_creation_date             2017-04-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C27 H23 Cl Cu N3), 2(Cl O4)'
_chemical_formula_sum            'C54 H46 Cl4 Cu2 N6 O8'
_chemical_formula_weight         1175.85
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.5432(11)
_cell_length_b                   12.0648(12)
_cell_length_c                   20.0110(18)
_cell_angle_alpha                90
_cell_angle_beta                 94.684(3)
_cell_angle_gamma                90
_cell_volume                     2777.6(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    296
_cell_measurement_theta_max      24.875
_cell_measurement_theta_min      3.094
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.015
_exptl_absorpt_correction_T_max  0.7369
_exptl_absorpt_correction_T_min  0.6721
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0987 before and 0.0849 after correction. The Ratio of minimum to maximum transmission is 0.9121. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1204
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            51374
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.436
_diffrn_reflns_theta_min         3.093
_diffrn_ambient_temperature      296.0
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'PHOTON area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4146
_reflns_number_total             5692
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         5692
_refine_ls_number_restraints     202
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.125
_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)+(0.0587P)²+1.7608P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1240
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 O1A-O2A \\sim O1A-O4A \\sim O1A-O3A \\sim O2A-O4A \\sim O2A-O3A \\sim O3B-O1B
\\sim O3B-O4B \\sim O3B-O2B
 \\sim O4A-O3A \\sim O1B-O4B \\sim O1B-O2B \\sim O4B-O2B
 with sigma of 0.04
 Cl2-O1A \\sim Cl2-O2A \\sim Cl2-O3B \\sim Cl2-O4A \\sim Cl2-O1B \\sim Cl2-O3A
\\sim Cl2-O4B \\sim Cl2-O2B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl2 \\sim O1A \\sim O2A \\sim O4A \\sim O3A: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
Cl2 \\sim O3B \\sim O1B \\sim O4B \\sim O2B: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 Cl2, O1A, O2A, O3B, O4A, O1B, O3A, O4B, O2B
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(O1B)=Sof(O3A)=Sof(O4B)=Sof(O2B)=1-FVAR(1)
 Sof(O1A)=Sof(O2A)=Sof(O3B)=Sof(O4A)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C13(H13A,H13B)
6.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C23(H23), C24(H24), C25(H25),
  C26(H26)
;
_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 0.46401(3) 0.10489(3) 0.43937(2) 0.03965(13) Uani 1 1 d . . . . .
Cl1 Cl 0.44013(7) 0.11171(6) 0.54941(4) 0.0511(2) Uani 1 1 d . . . . .
Cl2 Cl 0.71400(8) 0.44095(8) 0.29810(5) 0.0666(2) Uani 1 1 d D U . . .
O1A O 0.6433(6) 0.4339(9) 0.3538(3) 0.0835(17) Uani 0.540(5) 1 d D U P A 1
O2A O 0.8332(4) 0.4617(6) 0.3198(4) 0.0946(16) Uani 0.540(5) 1 d D U P A 1
O3B O 0.7030(6) 0.5568(5) 0.2776(4) 0.1014(16) Uani 0.540(5) 1 d D U P A 2
O4A O 0.7155(6) 0.3279(5) 0.2708(3) 0.0992(16) Uani 0.540(5) 1 d D U P A 1
N1 N 0.3064(2) 0.0493(2) 0.40878(12) 0.0445(6) Uani 1 1 d . . . . .
N2 N 0.4833(2) 0.10936(19) 0.33942(11) 0.0407(5) Uani 1 1 d . . . . .
N3 N 0.6250(2) 0.1628(2) 0.44501(12) 0.0463(6) Uani 1 1 d . . . . .
C1 C 0.2115(3) 0.0490(3) 0.44281(19) 0.0612(9) Uani 1 1 d . . . . .
H1 H 0.2170 0.0731 0.4871 0.073 Uiso 1 1 calc R . . . .
C2 C 0.1048(3) 0.0135(3) 0.4135(2) 0.0774(12) Uani 1 1 d . . . . .
H2 H 0.0396 0.0141 0.4379 0.093 Uiso 1 1 calc R . . . .
C3 C 0.0962(3) -0.0225(3) 0.3487(2) 0.0775(12) Uani 1 1 d . . . . .
H3 H 0.0252 -0.0462 0.3284 0.093 Uiso 1 1 calc R . . . .
C4 C 0.1929(3) -0.0231(3) 0.3141(2) 0.0638(10) Uani 1 1 d . . . . .
H4 H 0.1890 -0.0484 0.2701 0.077 Uiso 1 1 calc R . . . .
C5 C 0.2974(3) 0.0142(2) 0.34527(15) 0.0455(7) Uani 1 1 d . . . . .
C6 C 0.4088(3) 0.0167(3) 0.31188(15) 0.0513(8) Uani 1 1 d . . . . .
H6A H 0.4495 -0.0531 0.3194 0.062 Uiso 1 1 calc R . . . .
H6B H 0.3922 0.0264 0.2639 0.062 Uiso 1 1 calc R . . . .
C7 C 0.6087(3) 0.0882(3) 0.33337(16) 0.0542(8) Uani 1 1 d . . . . .
H7A H 0.6304 0.1162 0.2907 0.065 Uiso 1 1 calc R . . . .
H7B H 0.6234 0.0091 0.3348 0.065 Uiso 1 1 calc R . . . .
C8 C 0.6805(3) 0.1441(3) 0.38950(16) 0.0508(8) Uani 1 1 d . . . . .
C9 C 0.7960(3) 0.1707(3) 0.3870(2) 0.0710(11) Uani 1 1 d . . . . .
H9 H 0.8338 0.1558 0.3487 0.085 Uiso 1 1 calc R . . . .
C10 C 0.8548(3) 0.2198(4) 0.4422(2) 0.0806(12) Uani 1 1 d . . . . .
H10 H 0.9328 0.2386 0.4413 0.097 Uiso 1 1 calc R . . . .
C11 C 0.7977(3) 0.2406(3) 0.4979(2) 0.0726(11) Uani 1 1 d . . . . .
H11 H 0.8360 0.2741 0.5352 0.087 Uiso 1 1 calc R . . . .
C12 C 0.6837(3) 0.2115(3) 0.49811(17) 0.0574(8) Uani 1 1 d . . . . .
H12 H 0.6450 0.2257 0.5362 0.069 Uiso 1 1 calc R . . . .
C13 C 0.4516(3) 0.2197(3) 0.30676(14) 0.0455(7) Uani 1 1 d . . . . .
H13A H 0.5050 0.2755 0.3259 0.055 Uiso 1 1 calc R . . . .
H13B H 0.4630 0.2143 0.2594 0.055 Uiso 1 1 calc R . . . .
C14 C 0.3297(3) 0.2584(2) 0.31388(13) 0.0410(6) Uani 1 1 d . . . . .
C15 C 0.3056(3) 0.3205(2) 0.37075(14) 0.0436(7) Uani 1 1 d . . . . .
C16 C 0.3919(3) 0.3526(3) 0.42241(15) 0.0533(8) Uani 1 1 d . . . . .
H16 H 0.4692 0.3338 0.4185 0.064 Uiso 1 1 calc R . . . .
C17 C 0.3632(4) 0.4103(3) 0.47732(18) 0.0682(10) Uani 1 1 d . . . . .
H17 H 0.4211 0.4288 0.5106 0.082 Uiso 1 1 calc R . . . .
C18 C 0.2486(4) 0.4420(3) 0.4845(2) 0.0768(12) Uani 1 1 d . . . . .
H18 H 0.2308 0.4812 0.5223 0.092 Uiso 1 1 calc R . . . .
C19 C 0.1638(4) 0.4161(3) 0.4369(2) 0.0678(10) Uani 1 1 d . . . . .
H19 H 0.0883 0.4397 0.4417 0.081 Uiso 1 1 calc R . . . .
C20 C 0.1875(3) 0.3533(3) 0.37918(16) 0.0505(8) Uani 1 1 d . . . . .
C21 C 0.0997(3) 0.3220(3) 0.33188(18) 0.0557(8) Uani 1 1 d . . . . .
H21 H 0.0236 0.3420 0.3382 0.067 Uiso 1 1 calc R . . . .
C22 C 0.1211(3) 0.2619(3) 0.27556(16) 0.0493(7) Uani 1 1 d . . . . .
C23 C 0.0281(3) 0.2261(3) 0.2288(2) 0.0661(10) Uani 1 1 d . . . . .
H23 H -0.0481 0.2435 0.2366 0.079 Uiso 1 1 calc R . . . .
C24 C 0.0489(4) 0.1681(3) 0.1740(2) 0.0725(11) Uani 1 1 d . . . . .
H24 H -0.0128 0.1433 0.1450 0.087 Uiso 1 1 calc R . . . .
C25 C 0.1631(4) 0.1446(3) 0.16021(17) 0.0670(10) Uani 1 1 d . . . . .
H25 H 0.1764 0.1066 0.1211 0.080 Uiso 1 1 calc R . . . .
C26 C 0.2559(3) 0.1765(3) 0.20307(15) 0.0558(8) Uani 1 1 d . . . . .
H26 H 0.3311 0.1615 0.1921 0.067 Uiso 1 1 calc R . . . .
C27 C 0.2382(3) 0.2325(2) 0.26441(14) 0.0437(7) Uani 1 1 d . . . . .
O1B O 0.6810(8) 0.4307(11) 0.3641(4) 0.087(2) Uani 0.460(5) 1 d D U P A 2
O3A O 0.6686(6) 0.5077(6) 0.2464(3) 0.0812(15) Uani 0.460(5) 1 d D U P A 1
O4B O 0.6317(7) 0.3872(7) 0.2524(4) 0.1089(19) Uani 0.460(5) 1 d D U P A 2
O2B O 0.8225(6) 0.4038(7) 0.2890(4) 0.0933(17) Uani 0.460(5) 1 d D U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 Cl1 2.2429(8) . ?
Cu1 N1 1.988(2) . ?
Cu1 N2 2.031(2) . ?
Cu1 N3 1.980(2) . ?
Cl2 O1A 1.436(6) . ?
Cl2 O2A 1.431(5) . ?
Cl2 O3B 1.459(6) . ?
Cl2 O4A 1.470(5) . ?
Cl2 O1B 1.409(7) . ?
Cl2 O3A 1.380(6) . ?
Cl2 O4B 1.420(7) . ?
Cl2 O2B 1.356(6) . ?
N1 C1 1.337(4) . ?
N1 C5 1.335(4) . ?
N2 C6 1.489(4) . ?
N2 C7 1.484(4) . ?
N2 C13 1.514(4) . ?
N3 C8 1.346(4) . ?
N3 C12 1.347(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.388(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.363(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.360(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(4) . ?
C5 C6 1.497(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.500(5) . ?
C8 C9 1.376(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.365(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.362(5) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.501(4) . ?
C14 C15 1.409(4) . ?
C14 C27 1.422(4) . ?
C15 C16 1.430(4) . ?
C15 C20 1.443(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.364(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.396(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.345(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.426(5) . ?
C20 C21 1.382(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.379(5) . ?
C22 C23 1.432(4) . ?
C22 C27 1.432(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.339(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.397(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.372(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.431(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 Cl1 97.58(8) . . ?
N1 Cu1 N2 82.93(10) . . ?
N2 Cu1 Cl1 176.30(7) . . ?
N3 Cu1 Cl1 96.96(8) . . ?
N3 Cu1 N1 165.38(10) . . ?
N3 Cu1 N2 82.46(10) . . ?
O1A Cl2 O4A 104.9(5) . . ?
O2A Cl2 O1A 111.7(4) . . ?
O2A Cl2 O4A 103.6(4) . . ?
O1B Cl2 O3B 108.9(6) . . ?
O1B Cl2 O4B 110.2(5) . . ?
O3A Cl2 O1A 114.2(5) . . ?
O3A Cl2 O2A 115.0(4) . . ?
O3A Cl2 O4A 106.2(5) . . ?
O4B Cl2 O3B 102.6(5) . . ?
O2B Cl2 O3B 109.8(4) . . ?
O2B Cl2 O1B 114.8(5) . . ?
O2B Cl2 O4B 109.8(5) . . ?
C1 N1 Cu1 127.7(2) . . ?
C5 N1 Cu1 113.5(2) . . ?
C5 N1 C1 118.7(3) . . ?
C6 N2 Cu1 103.77(18) . . ?
C6 N2 C13 112.8(2) . . ?
C7 N2 Cu1 105.18(17) . . ?
C7 N2 C6 112.2(2) . . ?
C7 N2 C13 108.6(2) . . ?
C13 N2 Cu1 113.96(17) . . ?
C8 N3 Cu1 113.7(2) . . ?
C8 N3 C12 118.8(3) . . ?
C12 N3 Cu1 127.4(2) . . ?
N1 C1 H1 119.3 . . ?
N1 C1 C2 121.4(4) . . ?
C2 C1 H1 119.3 . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.1(4) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.3(4) . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 121.9(3) . . ?
N1 C5 C6 114.5(2) . . ?
C4 C5 C6 123.6(3) . . ?
N2 C6 C5 109.9(2) . . ?
N2 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
N2 C7 H7A 109.6 . . ?
N2 C7 H7B 109.6 . . ?
N2 C7 C8 110.1(2) . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
N3 C8 C7 115.0(3) . . ?
N3 C8 C9 121.3(3) . . ?
C9 C8 C7 123.7(3) . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 119.0(4) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.5(4) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.1(4) . . ?
C12 C11 H11 120.4 . . ?
N3 C12 C11 122.2(4) . . ?
N3 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
N2 C13 H13A 108.4 . . ?
N2 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
C14 C13 N2 115.4(2) . . ?
C14 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
C15 C14 C13 119.4(3) . . ?
C15 C14 C27 119.6(3) . . ?
C27 C14 C13 121.0(3) . . ?
C14 C15 C16 123.8(3) . . ?
C14 C15 C20 119.4(3) . . ?
C16 C15 C20 116.8(3) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.4(3) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.1(4) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.3(4) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.4(4) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C15 119.0(3) . . ?
C21 C20 C15 119.5(3) . . ?
C21 C20 C19 121.5(3) . . ?
C20 C21 H21 118.9 . . ?
C22 C21 C20 122.2(3) . . ?
C22 C21 H21 118.9 . . ?
C21 C22 C23 121.2(3) . . ?
C21 C22 C27 119.5(3) . . ?
C27 C22 C23 119.3(3) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.2(4) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.2(3) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 119.3 . . ?
C26 C25 C24 121.4(4) . . ?
C26 C25 H25 119.3 . . ?
C25 C26 H26 119.7 . . ?
C25 C26 C27 120.6(3) . . ?
C27 C26 H26 119.7 . . ?
C14 C27 C22 119.6(3) . . ?
C14 C27 C26 123.4(3) . . ?
C26 C27 C22 117.0(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7A O3B 0.97 2.55 3.254(7) 129.4 2_645
C13 H13A O4B 0.97 2.54 3.156(8) 121.0 .

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 N1 C1 C2 176.0(3) . . . . ?
Cu1 N1 C5 C4 -177.2(2) . . . . ?
Cu1 N1 C5 C6 3.9(3) . . . . ?
Cu1 N2 C6 C5 41.0(3) . . . . ?
Cu1 N2 C7 C8 -37.7(3) . . . . ?
Cu1 N2 C13 C14 -57.9(3) . . . . ?
Cu1 N3 C8 C7 2.7(3) . . . . ?
Cu1 N3 C8 C9 -174.6(3) . . . . ?
Cu1 N3 C12 C11 174.8(3) . . . . ?
N1 C1 C2 C3 0.3(6) . . . . ?
N1 C5 C6 N2 -31.4(3) . . . . ?
N2 C7 C8 N3 24.4(4) . . . . ?
N2 C7 C8 C9 -158.3(3) . . . . ?
N2 C13 C14 C15 87.5(3) . . . . ?
N2 C13 C14 C27 -92.0(3) . . . . ?
N3 C8 C9 C10 -1.4(5) . . . . ?
C1 N1 C5 C4 -0.6(4) . . . . ?
C1 N1 C5 C6 -179.4(3) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C2 C3 C4 C5 -1.0(6) . . . . ?
C3 C4 C5 N1 1.1(5) . . . . ?
C3 C4 C5 C6 179.8(3) . . . . ?
C4 C5 C6 N2 149.8(3) . . . . ?
C5 N1 C1 C2 -0.1(5) . . . . ?
C6 N2 C7 C8 -149.8(3) . . . . ?
C6 N2 C13 C14 60.1(3) . . . . ?
C7 N2 C6 C5 154.1(2) . . . . ?
C7 N2 C13 C14 -174.8(2) . . . . ?
C7 C8 C9 C10 -178.5(3) . . . . ?
C8 N3 C12 C11 -1.1(5) . . . . ?
C8 C9 C10 C11 0.2(6) . . . . ?
C9 C10 C11 C12 0.5(6) . . . . ?
C10 C11 C12 N3 -0.1(6) . . . . ?
C12 N3 C8 C7 179.2(3) . . . . ?
C12 N3 C8 C9 1.9(5) . . . . ?
C13 N2 C6 C5 -82.8(3) . . . . ?
C13 N2 C7 C8 84.7(3) . . . . ?
C13 C14 C15 C16 1.9(4) . . . . ?
C13 C14 C15 C20 -177.1(3) . . . . ?
C13 C14 C27 C22 174.3(3) . . . . ?
C13 C14 C27 C26 -4.9(4) . . . . ?
C14 C15 C16 C17 -178.3(3) . . . . ?
C14 C15 C20 C19 180.0(3) . . . . ?
C14 C15 C20 C21 0.9(4) . . . . ?
C15 C14 C27 C22 -5.1(4) . . . . ?
C15 C14 C27 C26 175.7(3) . . . . ?
C15 C16 C17 C18 -1.3(5) . . . . ?
C15 C20 C21 C22 -1.5(5) . . . . ?
C16 C15 C20 C19 0.9(4) . . . . ?
C16 C15 C20 C21 -178.2(3) . . . . ?
C16 C17 C18 C19 -0.1(6) . . . . ?
C17 C18 C19 C20 1.9(6) . . . . ?
C18 C19 C20 C15 -2.2(5) . . . . ?
C18 C19 C20 C21 176.8(3) . . . . ?
C19 C20 C21 C22 179.5(3) . . . . ?
C20 C15 C16 C17 0.8(4) . . . . ?
C20 C21 C22 C23 177.2(3) . . . . ?
C20 C21 C22 C27 -1.3(5) . . . . ?
C21 C22 C23 C24 179.8(3) . . . . ?
C21 C22 C27 C14 4.6(4) . . . . ?
C21 C22 C27 C26 -176.1(3) . . . . ?
C22 C23 C24 C25 -2.3(6) . . . . ?
C23 C22 C27 C14 -173.9(3) . . . . ?
C23 C22 C27 C26 5.4(4) . . . . ?
C23 C24 C25 C26 2.3(6) . . . . ?
C24 C25 C26 C27 1.6(5) . . . . ?
C25 C26 C27 C14 173.8(3) . . . . ?
C25 C26 C27 C22 -5.4(4) . . . . ?
C27 C14 C15 C16 -178.6(3) . . . . ?
C27 C14 C15 C20 2.3(4) . . . . ?
C27 C22 C23 C24 -1.7(5) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.118 0.256 0.602 92.7 20.5 '1 acetonitrile'
2 -0.118 0.744 0.398 92.7 20.0 '1 acetonitrile'
3 0.382 0.756 0.898 92.7 20.1 '1 acetonitrile'
4 0.618 0.244 0.102 92.7 20.5 '1 acetonitrile'

_olex2_submission_special_instructions 'No special instructions were received'
