# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_1-cu-bpprd-c2h4-clo4
_database_code_depnum_ccdc_archive 'CCDC 2267404'
loop_
_audit_author_name
_audit_author_address
'Kunihisa Sugimoto'
;Kindai University
Japan
;
_audit_update_record             
;
2023-06-04 deposited with the CCDC.	2023-09-22 downloaded from the CCDC.
;
_audit_creation_date             2023-03-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 Cu2 N4, 2(Cl O4)'
_chemical_formula_sum            'C18 H18 Cl2 Cu2 N4 O8'
_chemical_formula_weight         616.34
_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.3225(3)
_cell_length_b                   13.0447(4)
_cell_length_c                   15.7577(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.276(3)
_cell_angle_gamma                90
_cell_volume                     2196.91(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11404
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      31.64
_cell_measurement_theta_min      3.79
_shelx_estimated_absorpt_T_max   0.554
_shelx_estimated_absorpt_T_min   0.554
_exptl_absorpt_coefficient_mu    2.235
_exptl_absorpt_correction_T_max  0.512
_exptl_absorpt_correction_T_min  0.406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.863
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1240
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            26013
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.433
_diffrn_reflns_theta_min         3.110
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5613
_reflns_number_total             6603
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.382
_refine_diff_density_min         -1.076
_refine_diff_density_rms         0.136
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6603
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0591P)²+0.8142P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1080
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.53324(2) 0.41026(2) 0.73864(2) 0.01518(8) Uani 1 1 d . . . . .
Cu2 Cu 1.05833(2) 0.51443(2) 0.87514(2) 0.01518(8) Uani 1 1 d . . . . .
Cl1 Cl 0.44305(5) 0.16840(4) 0.60951(4) 0.02088(12) Uani 1 1 d . . . . .
Cl2 Cl 1.06089(4) 0.38564(4) 0.67230(3) 0.01471(11) Uani 1 1 d . . . . .
O1 O 0.53345(19) 0.24903(16) 0.64465(12) 0.0297(4) Uani 1 1 d . . . . .
O2 O 0.4972(2) 0.08780(18) 0.57474(18) 0.0445(6) Uani 1 1 d . . . . .
O3 O 0.3917(3) 0.1340(2) 0.67460(16) 0.0528(7) Uani 1 1 d . . . . .
O4 O 0.34327(19) 0.21126(18) 0.53402(15) 0.0401(5) Uani 1 1 d . . . . .
O5 O 0.94216(16) 0.34295(15) 0.66913(12) 0.0242(4) Uani 1 1 d . . . . .
O6 O 1.13353(16) 0.31047(14) 0.64456(11) 0.0237(3) Uani 1 1 d . . . . .
O7 O 1.12898(17) 0.4172(2) 0.76328(13) 0.0416(6) Uani 1 1 d . . . . .
O8 O 1.03956(18) 0.47191(15) 0.61262(15) 0.0342(5) Uani 1 1 d . . . . .
N1 N 0.44769(16) 0.49154(15) 0.63034(11) 0.0148(3) Uani 1 1 d . . . . .
N2 N 0.68921(15) 0.47629(13) 0.72218(11) 0.0114(3) Uani 1 1 d . . . . .
N3 N 0.97059(16) 0.38665(14) 0.89093(11) 0.0139(3) Uani 1 1 d . . . . .
N4 N 0.89460(15) 0.54453(14) 0.78017(11) 0.0125(3) Uani 1 1 d . . . . .
C1 C 0.52122(18) 0.56058(16) 0.60868(13) 0.0120(3) Uani 1 1 d . . . . .
C2 C 0.47550(19) 0.62727(17) 0.53664(13) 0.0136(4) Uani 1 1 d . . . . .
C3 C 0.3487(2) 0.62142(17) 0.48534(14) 0.0157(4) Uani 1 1 d . . . . .
C4 C 0.27316(19) 0.55004(19) 0.50689(14) 0.0175(4) Uani 1 1 d . . . . .
C5 C 0.32602(19) 0.48559(18) 0.58013(14) 0.0166(4) Uani 1 1 d . . . . .
C6 C 0.85777(18) 0.37608(16) 0.82661(13) 0.0119(3) Uani 1 1 d . . . . .
C7 C 0.79766(19) 0.28247(16) 0.80680(14) 0.0145(4) Uani 1 1 d . . . . .
C8 C 0.8546(2) 0.19756(18) 0.85662(15) 0.0179(4) Uani 1 1 d . . . . .
C9 C 0.9680(2) 0.20832(18) 0.92561(15) 0.0195(4) Uani 1 1 d . . . . .
C10 C 1.0234(2) 0.30467(18) 0.94041(14) 0.0178(4) Uani 1 1 d . . . . .
C11 C 0.80929(17) 0.47062(15) 0.77357(13) 0.0113(3) Uani 1 1 d . . . . .
C12 C 0.85878(19) 0.62641(17) 0.72647(14) 0.0144(4) Uani 1 1 d . . . . .
C13 C 0.73908(19) 0.63461(16) 0.66542(14) 0.0134(4) Uani 1 1 d . . . . .
C14 C 0.65407(17) 0.55843(16) 0.66667(12) 0.0113(3) Uani 1 1 d . . . . .
C15 C 0.4168(2) 0.3588(2) 0.80168(16) 0.0219(5) Uani 1 1 d . . . . .
C16 C 0.5363(2) 0.3343(2) 0.85139(16) 0.0258(5) Uani 1 1 d . . . . .
C17 C 1.2268(2) 0.5394(2) 0.96608(16) 0.0221(5) Uani 1 1 d . . . . .
C18 C 1.1902(2) 0.6240(2) 0.91241(19) 0.0261(5) Uani 1 1 d . . . . .
H2 H 0.525(3) 0.673(3) 0.526(2) 0.026(8) Uiso 1 1 d . . . . .
H3 H 0.314(3) 0.670(3) 0.438(2) 0.031(8) Uiso 1 1 d . . . . .
H4 H 0.183(3) 0.545(3) 0.471(2) 0.025(8) Uiso 1 1 d . . . . .
H5 H 0.276(3) 0.432(2) 0.5926(19) 0.015(6) Uiso 1 1 d . . . . .
H7 H 0.726(3) 0.279(2) 0.763(2) 0.023(7) Uiso 1 1 d . . . . .
H8 H 0.823(3) 0.145(3) 0.846(2) 0.023(8) Uiso 1 1 d . . . . .
H9 H 1.002(3) 0.144(3) 0.966(2) 0.033(9) Uiso 1 1 d . . . . .
H10 H 1.106(3) 0.309(2) 0.9855(19) 0.018(7) Uiso 1 1 d . . . . .
H12 H 0.911(3) 0.676(2) 0.731(2) 0.022(7) Uiso 1 1 d . . . . .
H13 H 0.711(3) 0.686(2) 0.6320(19) 0.014(6) Uiso 1 1 d . . . . .
H15A H 0.381(3) 0.416(3) 0.812(2) 0.026(8) Uiso 1 1 d . . . . .
H15B H 0.363(3) 0.308(3) 0.766(2) 0.038(9) Uiso 1 1 d . . . . .
H16A H 0.569(4) 0.272(3) 0.853(3) 0.046(11) Uiso 1 1 d . . . . .
H16B H 0.582(3) 0.373(3) 0.899(2) 0.038(9) Uiso 1 1 d . . . . .
H17A H 1.226(3) 0.541(3) 1.033(2) 0.035(9) Uiso 1 1 d . . . . .
H17B H 1.292(4) 0.494(3) 0.960(2) 0.041(10) Uiso 1 1 d . . . . .
H18A H 1.214(3) 0.638(3) 0.865(2) 0.031(8) Uiso 1 1 d . . . . .
H18B H 1.160(4) 0.687(4) 0.925(3) 0.069(14) 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
Cu1 N1 1.9705(18) . ?
Cu1 N2 2.0568(17) . ?
Cu1 C15 2.010(2) . ?
Cu1 C16 2.025(2) . ?
Cu2 N3 1.9976(19) . ?
Cu2 N4 1.9996(17) . ?
Cu2 C17 1.998(2) . ?
Cu2 C18 2.009(2) . ?
Cl1 O1 1.4445(19) . ?
Cl1 O2 1.415(2) . ?
Cl1 O3 1.409(2) . ?
Cl1 O4 1.455(2) . ?
Cl2 O5 1.4406(17) . ?
Cl2 O6 1.4375(17) . ?
Cl2 O7 1.4453(18) . ?
Cl2 O8 1.4349(19) . ?
N1 C1 1.345(3) . ?
N1 C5 1.345(3) . ?
N2 C11 1.335(2) . ?
N2 C14 1.357(3) . ?
N3 C6 1.350(2) . ?
N3 C10 1.342(3) . ?
N4 C11 1.344(3) . ?
N4 C12 1.340(3) . ?
C1 C2 1.388(3) . ?
C1 C14 1.480(3) . ?
C2 C3 1.398(3) . ?
C2 H2 0.88(3) . ?
C3 C4 1.380(3) . ?
C3 H3 0.95(3) . ?
C4 C5 1.393(3) . ?
C4 H4 0.99(3) . ?
C5 H5 0.96(3) . ?
C6 C7 1.383(3) . ?
C6 C11 1.489(3) . ?
C7 C8 1.387(3) . ?
C7 H7 0.87(3) . ?
C8 C9 1.389(3) . ?
C8 H8 0.76(3) . ?
C9 C10 1.389(3) . ?
C9 H9 1.04(4) . ?
C10 H10 0.97(3) . ?
C12 C13 1.383(3) . ?
C12 H12 0.86(3) . ?
C13 C14 1.388(3) . ?
C13 H13 0.84(3) . ?
C15 C16 1.358(3) . ?
C15 H15A 0.88(3) . ?
C15 H15B 0.94(4) . ?
C16 H16A 0.88(4) . ?
C16 H16B 0.91(4) . ?
C17 C18 1.369(4) . ?
C17 H17A 1.07(3) . ?
C17 H17B 0.97(4) . ?
C18 H18A 0.90(4) . ?
C18 H18B 0.94(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N2 82.10(7) . . ?
N1 Cu1 C15 113.12(9) . . ?
N1 Cu1 C16 152.17(9) . . ?
C15 Cu1 N2 158.87(8) . . ?
C15 Cu1 C16 39.34(10) . . ?
C16 Cu1 N2 123.31(8) . . ?
N3 Cu2 N4 83.15(7) . . ?
N3 Cu2 C17 116.27(9) . . ?
N3 Cu2 C18 155.39(9) . . ?
N4 Cu2 C18 119.65(9) . . ?
C17 Cu2 N4 159.13(10) . . ?
C17 Cu2 C18 39.96(11) . . ?
O1 Cl1 O4 107.12(13) . . ?
O2 Cl1 O1 110.29(13) . . ?
O2 Cl1 O4 106.72(15) . . ?
O3 Cl1 O1 111.31(14) . . ?
O3 Cl1 O2 112.37(17) . . ?
O3 Cl1 O4 108.78(16) . . ?
O5 Cl2 O7 109.30(12) . . ?
O6 Cl2 O5 110.29(11) . . ?
O6 Cl2 O7 108.92(11) . . ?
O8 Cl2 O5 109.09(11) . . ?
O8 Cl2 O6 108.97(12) . . ?
O8 Cl2 O7 110.25(15) . . ?
C1 N1 Cu1 114.31(13) . . ?
C1 N1 C5 119.26(18) . . ?
C5 N1 Cu1 126.40(15) . . ?
C11 N2 Cu1 130.18(14) . . ?
C11 N2 C14 117.24(17) . . ?
C14 N2 Cu1 109.31(12) . . ?
C6 N3 Cu2 112.20(14) . . ?
C10 N3 Cu2 126.36(15) . . ?
C10 N3 C6 118.97(19) . . ?
C11 N4 Cu2 112.46(14) . . ?
C12 N4 Cu2 129.93(14) . . ?
C12 N4 C11 117.58(17) . . ?
N1 C1 C2 122.18(18) . . ?
N1 C1 C14 114.75(17) . . ?
C2 C1 C14 123.07(19) . . ?
C1 C2 C3 118.2(2) . . ?
C1 C2 H2 120(2) . . ?
C3 C2 H2 122(2) . . ?
C2 C3 H3 119(2) . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 121(2) . . ?
C3 C4 C5 118.64(19) . . ?
C3 C4 H4 120.9(19) . . ?
C5 C4 H4 120.4(19) . . ?
N1 C5 C4 121.9(2) . . ?
N1 C5 H5 118.9(17) . . ?
C4 C5 H5 119.1(17) . . ?
N3 C6 C7 122.20(19) . . ?
N3 C6 C11 114.76(18) . . ?
C7 C6 C11 122.82(18) . . ?
C6 C7 C8 118.38(19) . . ?
C6 C7 H7 119(2) . . ?
C8 C7 H7 123(2) . . ?
C7 C8 C9 119.9(2) . . ?
C7 C8 H8 119(2) . . ?
C9 C8 H8 121(2) . . ?
C8 C9 C10 118.2(2) . . ?
C8 C9 H9 117.1(19) . . ?
C10 C9 H9 124.6(19) . . ?
N3 C10 C9 122.2(2) . . ?
N3 C10 H10 121.2(18) . . ?
C9 C10 H10 116.4(18) . . ?
N2 C11 N4 124.68(19) . . ?
N2 C11 C6 119.94(18) . . ?
N4 C11 C6 115.35(17) . . ?
N4 C12 C13 121.59(19) . . ?
N4 C12 H12 119(2) . . ?
C13 C12 H12 119(2) . . ?
C12 C13 C14 117.37(19) . . ?
C12 C13 H13 125(2) . . ?
C14 C13 H13 117.2(19) . . ?
N2 C14 C1 115.78(17) . . ?
N2 C14 C13 121.15(18) . . ?
C13 C14 C1 123.08(18) . . ?
Cu1 C15 H15A 103(2) . . ?
Cu1 C15 H15B 109(2) . . ?
C16 C15 Cu1 70.91(14) . . ?
C16 C15 H15A 121(2) . . ?
C16 C15 H15B 120(2) . . ?
H15A C15 H15B 117(3) . . ?
Cu1 C16 H16A 111(3) . . ?
Cu1 C16 H16B 107(2) . . ?
C15 C16 Cu1 69.74(14) . . ?
C15 C16 H16A 124(3) . . ?
C15 C16 H16B 123(2) . . ?
H16A C16 H16B 111(3) . . ?
Cu2 C17 H17A 113.4(19) . . ?
Cu2 C17 H17B 114(2) . . ?
C18 C17 Cu2 70.45(14) . . ?
C18 C17 H17A 120(2) . . ?
C18 C17 H17B 121(2) . . ?
H17A C17 H17B 111(3) . . ?
Cu2 C18 H18A 107(2) . . ?
Cu2 C18 H18B 114(3) . . ?
C17 C18 Cu2 69.59(14) . . ?
C17 C18 H18A 124(2) . . ?
C17 C18 H18B 130(3) . . ?
H18A C18 H18B 103(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 N1 C1 C2 -177.34(15) . . . . ?
Cu1 N1 C1 C14 3.5(2) . . . . ?
Cu1 N1 C5 C4 176.97(16) . . . . ?
Cu1 N2 C11 N4 -150.80(16) . . . . ?
Cu1 N2 C11 C6 31.1(3) . . . . ?
Cu1 N2 C14 C1 -20.1(2) . . . . ?
Cu1 N2 C14 C13 159.96(15) . . . . ?
Cu2 N3 C6 C7 159.85(16) . . . . ?
Cu2 N3 C6 C11 -14.8(2) . . . . ?
Cu2 N3 C10 C9 -158.34(17) . . . . ?
Cu2 N4 C11 N2 172.93(16) . . . . ?
Cu2 N4 C11 C6 -8.9(2) . . . . ?
Cu2 N4 C12 C13 -178.49(15) . . . . ?
N1 C1 C2 C3 -0.2(3) . . . . ?
N1 C1 C14 N2 11.9(3) . . . . ?
N1 C1 C14 C13 -168.18(19) . . . . ?
N3 C6 C7 C8 1.6(3) . . . . ?
N3 C6 C11 N2 -165.59(18) . . . . ?
N3 C6 C11 N4 16.2(3) . . . . ?
N4 C12 C13 C14 4.9(3) . . . . ?
C1 N1 C5 C4 -1.0(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C1 C14 N2 -167.18(18) . . . . ?
C2 C1 C14 C13 12.7(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 N1 0.4(3) . . . . ?
C5 N1 C1 C2 0.9(3) . . . . ?
C5 N1 C1 C14 -178.25(18) . . . . ?
C6 N3 C10 C9 2.4(3) . . . . ?
C6 C7 C8 C9 1.3(3) . . . . ?
C7 C6 C11 N2 19.8(3) . . . . ?
C7 C6 C11 N4 -158.47(19) . . . . ?
C7 C8 C9 C10 -2.3(3) . . . . ?
C8 C9 C10 N3 0.5(3) . . . . ?
C10 N3 C6 C7 -3.4(3) . . . . ?
C10 N3 C6 C11 -178.10(18) . . . . ?
C11 N2 C14 C1 178.18(17) . . . . ?
C11 N2 C14 C13 -1.7(3) . . . . ?
C11 N4 C12 C13 -0.8(3) . . . . ?
C11 C6 C7 C8 175.87(19) . . . . ?
C12 N4 C11 N2 -5.1(3) . . . . ?
C12 N4 C11 C6 173.03(17) . . . . ?
C12 C13 C14 N2 -3.6(3) . . . . ?
C12 C13 C14 C1 176.51(19) . . . . ?
C14 N2 C11 N4 6.4(3) . . . . ?
C14 N2 C11 C6 -171.72(17) . . . . ?
C14 C1 C2 C3 178.87(18) . . . . ?

_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_2-cu-bpprd-c2h4-no3
_database_code_depnum_ccdc_archive 'CCDC 2267405'
loop_
_audit_author_name
_audit_author_address
'Kunihisa Sugimoto'
;Kindai University
Japan
;
_audit_update_record             
;
2023-06-04 deposited with the CCDC.	2023-09-22 downloaded from the CCDC.
;
_audit_creation_date             2023-03-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 Cu2 N5 O3, N O3'
_chemical_formula_sum            'C18 H18 Cu2 N6 O6'
_chemical_formula_weight         541.46
_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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.3576(3)
_cell_length_b                   10.9852(6)
_cell_length_c                   11.9635(7)
_cell_angle_alpha                64.609(5)
_cell_angle_beta                 67.153(4)
_cell_angle_gamma                84.922(4)
_cell_volume                     1019.33(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7836
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      31.36
_cell_measurement_theta_min      2.98
_shelx_estimated_absorpt_T_max   0.675
_shelx_estimated_absorpt_T_min   0.567
_exptl_absorpt_coefficient_mu    2.137
_exptl_absorpt_correction_T_max  0.652
_exptl_absorpt_correction_T_min  0.476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19629
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.362
_diffrn_reflns_theta_min         2.994
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5130
_reflns_number_total             6011
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         6011
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0325
_refine_ls_restrained_S_all      1.048
_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)+(0.0307P)²+0.2815P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0855
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12),
 C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.11065(2) 0.45346(2) 0.76723(2) 0.01116(6) Uani 1 1 d . . . . .
Cu2 Cu 0.69675(2) 0.79896(2) 0.54834(2) 0.01310(7) Uani 1 1 d . . . . .
O1 O 0.15204(14) 0.37531(13) 0.62983(13) 0.0156(2) Uani 1 1 d . . . . .
O2 O 0.04677(16) 0.24154(14) 0.58614(14) 0.0191(3) Uani 1 1 d . . . . .
O3 O -0.09334(15) 0.30243(16) 0.74386(14) 0.0220(3) Uani 1 1 d . . . . .
O4 O 0.32812(19) 0.80359(15) 0.74343(14) 0.0262(3) Uani 1 1 d . . . . .
O5 O 0.30423(17) 0.63214(13) 0.93135(14) 0.0212(3) Uani 1 1 d . . . . .
O6 O 0.4047(2) 0.82725(14) 0.88346(16) 0.0280(3) Uani 1 1 d . . . . .
N1 N 0.12673(17) 0.28595(14) 0.91911(14) 0.0113(3) Uani 1 1 d . . . . .
N2 N 0.36710(15) 0.47655(13) 0.73350(13) 0.0097(2) Uani 1 1 d . . . . .
N3 N 0.56946(16) 0.78948(14) 0.45230(14) 0.0113(3) Uani 1 1 d . . . . .
N4 N 0.59272(16) 0.61089(14) 0.67800(14) 0.0126(3) Uani 1 1 d . . . . .
N5 N 0.03229(17) 0.30562(14) 0.65360(15) 0.0130(3) Uani 1 1 d . . . . .
N6 N 0.34611(17) 0.75430(15) 0.85198(15) 0.0145(3) Uani 1 1 d . . . . .
C1 C 0.26012(19) 0.27344(16) 0.93980(16) 0.0110(3) Uani 1 1 d . . . . .
C2 C 0.2825(2) 0.15878(18) 1.04156(17) 0.0158(3) Uani 1 1 d . . . . .
H2 H 0.377407 0.152071 1.054363 0.019 Uiso 1 1 calc R U . . .
C3 C 0.1630(2) 0.05448(18) 1.12387(18) 0.0174(3) Uani 1 1 d . . . . .
H3 H 0.175523 -0.025087 1.193310 0.021 Uiso 1 1 calc R U . . .
C4 C 0.0257(2) 0.06830(18) 1.10316(17) 0.0166(3) Uani 1 1 d . . . . .
H4 H -0.057777 -0.001227 1.158902 0.020 Uiso 1 1 calc R U . . .
C5 C 0.0115(2) 0.18515(17) 0.99980(17) 0.0137(3) Uani 1 1 d . . . . .
H5 H -0.082795 0.194110 0.985679 0.016 Uiso 1 1 calc R U . . .
C6 C 0.47049(18) 0.67592(16) 0.51917(16) 0.0100(3) Uani 1 1 d . . . . .
C7 C 0.37477(19) 0.64928(17) 0.46723(16) 0.0117(3) Uani 1 1 d . . . . .
H7 H 0.308604 0.567345 0.515188 0.014 Uiso 1 1 calc R U . . .
C8 C 0.3768(2) 0.74475(17) 0.34305(17) 0.0134(3) Uani 1 1 d . . . . .
H8 H 0.310951 0.729700 0.305660 0.016 Uiso 1 1 calc R U . . .
C9 C 0.4773(2) 0.86221(17) 0.27541(17) 0.0138(3) Uani 1 1 d . . . . .
H9 H 0.480932 0.929102 0.190976 0.017 Uiso 1 1 calc R U . . .
C10 C 0.5720(2) 0.88039(17) 0.33287(17) 0.0136(3) Uani 1 1 d . . . . .
H10 H 0.641401 0.960333 0.285775 0.016 Uiso 1 1 calc R U . . .
C11 C 0.47523(18) 0.58186(16) 0.65165(16) 0.0105(3) Uani 1 1 d . . . . .
C12 C 0.6059(2) 0.52239(18) 0.79198(17) 0.0153(3) Uani 1 1 d . . . . .
H12 H 0.686744 0.540161 0.813807 0.018 Uiso 1 1 calc R U . . .
C13 C 0.5055(2) 0.40588(17) 0.87908(17) 0.0144(3) Uani 1 1 d . . . . .
H13 H 0.520113 0.340756 0.956589 0.017 Uiso 1 1 calc R U . . .
C14 C 0.38275(19) 0.38838(16) 0.84825(16) 0.0109(3) Uani 1 1 d . . . . .
C15 C 0.0244(2) 0.63576(18) 0.70137(18) 0.0177(3) Uani 1 1 d . . . . .
H15A H 0.101692 0.715280 0.637446 0.021 Uiso 1 1 calc R U . . .
H15B H -0.067526 0.637580 0.679251 0.021 Uiso 1 1 calc R U . . .
C16 C -0.0033(2) 0.59080(18) 0.83429(19) 0.0171(3) Uani 1 1 d . . . . .
H16A H -0.113132 0.563407 0.898339 0.021 Uiso 1 1 calc R U . . .
H16B H 0.056108 0.641116 0.856529 0.021 Uiso 1 1 calc R U . . .
C17 C 0.7755(2) 0.98932(18) 0.49240(18) 0.0172(3) Uani 1 1 d . . . . .
H17A H 0.875758 1.025994 0.414149 0.021 Uiso 1 1 calc R U . . .
H17B H 0.697195 1.055994 0.493989 0.021 Uiso 1 1 calc R U . . .
C18 C 0.7838(2) 0.90465(18) 0.61337(19) 0.0183(3) Uani 1 1 d . . . . .
H18A H 0.710778 0.916618 0.693141 0.022 Uiso 1 1 calc R U . . .
H18B H 0.889332 0.886620 0.613306 0.022 Uiso 1 1 calc R U . . .


_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 2.0606(13) . ?
Cu1 N1 2.0015(15) . ?
Cu1 N2 2.2921(14) . ?
Cu1 C15 2.0339(17) . ?
Cu1 C16 2.0360(18) . ?
Cu2 N3 1.9843(15) . ?
Cu2 N4 2.0143(14) . ?
Cu2 C17 2.0134(17) . ?
Cu2 C18 2.0124(18) . ?
O1 N5 1.2808(18) . ?
O2 N5 1.2453(19) . ?
O3 N5 1.240(2) . ?
O4 N6 1.248(2) . ?
O5 N6 1.2520(19) . ?
O6 N6 1.258(2) . ?
N1 C1 1.349(2) . ?
N1 C5 1.344(2) . ?
N2 C11 1.3370(19) . ?
N2 C14 1.355(2) . ?
N3 C6 1.352(2) . ?
N3 C10 1.339(2) . ?
N4 C11 1.352(2) . ?
N4 C12 1.339(2) . ?
C1 C2 1.396(2) . ?
C1 C14 1.485(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.392(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(2) . ?
C6 C11 1.491(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.398(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.390(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(2) . ?
C10 H10 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.384(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.367(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.373(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N2 95.11(5) . . ?
N1 Cu1 O1 98.62(6) . . ?
N1 Cu1 N2 77.93(5) . . ?
N1 Cu1 C15 149.66(7) . . ?
N1 Cu1 C16 110.81(7) . . ?
C15 Cu1 O1 108.53(7) . . ?
C15 Cu1 N2 111.95(6) . . ?
C15 Cu1 C16 39.25(7) . . ?
C16 Cu1 O1 145.37(7) . . ?
C16 Cu1 N2 108.25(6) . . ?
N3 Cu2 N4 83.03(6) . . ?
N3 Cu2 C17 113.20(7) . . ?
N3 Cu2 C18 149.60(7) . . ?
C17 Cu2 N4 156.19(7) . . ?
C18 Cu2 N4 118.82(7) . . ?
C18 Cu2 C17 39.88(7) . . ?
N5 O1 Cu1 112.44(10) . . ?
C1 N1 Cu1 118.26(11) . . ?
C5 N1 Cu1 122.89(12) . . ?
C5 N1 C1 118.84(15) . . ?
C11 N2 Cu1 130.93(11) . . ?
C11 N2 C14 116.81(14) . . ?
C14 N2 Cu1 107.29(10) . . ?
C6 N3 Cu2 113.65(11) . . ?
C10 N3 Cu2 127.71(11) . . ?
C10 N3 C6 118.64(14) . . ?
C11 N4 Cu2 111.39(11) . . ?
C12 N4 Cu2 131.01(12) . . ?
C12 N4 C11 116.81(14) . . ?
O2 N5 O1 118.59(14) . . ?
O3 N5 O1 119.24(14) . . ?
O3 N5 O2 122.15(15) . . ?
O4 N6 O5 120.34(15) . . ?
O4 N6 O6 120.34(15) . . ?
O5 N6 O6 119.32(15) . . ?
N1 C1 C2 122.04(15) . . ?
N1 C1 C14 116.43(14) . . ?
C2 C1 C14 121.54(15) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.72(16) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.07(17) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.16(16) . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 122.17(16) . . ?
N1 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
N3 C6 C7 122.29(15) . . ?
N3 C6 C11 114.54(14) . . ?
C7 C6 C11 123.16(14) . . ?
C6 C7 H7 120.5 . . ?
C6 C7 C8 118.95(15) . . ?
C8 C7 H7 120.5 . . ?
C7 C8 H8 120.7 . . ?
C9 C8 C7 118.56(16) . . ?
C9 C8 H8 120.7 . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 119.08(16) . . ?
C10 C9 H9 120.5 . . ?
N3 C10 C9 122.45(15) . . ?
N3 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
N2 C11 N4 125.22(15) . . ?
N2 C11 C6 118.93(14) . . ?
N4 C11 C6 115.84(14) . . ?
N4 C12 H12 118.9 . . ?
N4 C12 C13 122.18(16) . . ?
C13 C12 H12 118.9 . . ?
C12 C13 H13 121.5 . . ?
C12 C13 C14 117.06(16) . . ?
C14 C13 H13 121.5 . . ?
N2 C14 C1 116.35(14) . . ?
N2 C14 C13 121.67(14) . . ?
C13 C14 C1 121.97(15) . . ?
Cu1 C15 H15A 116.6 . . ?
Cu1 C15 H15B 116.6 . . ?
H15A C15 H15B 113.6 . . ?
C16 C15 Cu1 70.46(10) . . ?
C16 C15 H15A 116.6 . . ?
C16 C15 H15B 116.6 . . ?
Cu1 C16 H16A 116.6 . . ?
Cu1 C16 H16B 116.6 . . ?
C15 C16 Cu1 70.29(11) . . ?
C15 C16 H16A 116.6 . . ?
C15 C16 H16B 116.6 . . ?
H16A C16 H16B 113.6 . . ?
Cu2 C17 H17A 116.6 . . ?
Cu2 C17 H17B 116.6 . . ?
H17A C17 H17B 113.6 . . ?
C18 C17 Cu2 70.02(10) . . ?
C18 C17 H17A 116.6 . . ?
C18 C17 H17B 116.6 . . ?
Cu2 C18 H18A 116.6 . . ?
Cu2 C18 H18B 116.6 . . ?
C17 C18 Cu2 70.10(10) . . ?
C17 C18 H18A 116.6 . . ?
C17 C18 H18B 116.6 . . ?
H18A C18 H18B 113.6 . . ?

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 O1 N5 O2 -172.73(12) . . . . ?
Cu1 O1 N5 O3 6.3(2) . . . . ?
Cu1 N1 C1 C2 -178.61(13) . . . . ?
Cu1 N1 C1 C14 1.32(19) . . . . ?
Cu1 N1 C5 C4 178.69(13) . . . . ?
Cu1 N2 C11 N4 147.58(14) . . . . ?
Cu1 N2 C11 C6 -33.2(2) . . . . ?
Cu1 N2 C14 C1 20.89(16) . . . . ?
Cu1 N2 C14 C13 -158.24(14) . . . . ?
Cu2 N3 C6 C7 -178.43(13) . . . . ?
Cu2 N3 C6 C11 0.73(17) . . . . ?
Cu2 N3 C10 C9 179.77(13) . . . . ?
Cu2 N4 C11 N2 -167.00(13) . . . . ?
Cu2 N4 C11 C6 13.78(18) . . . . ?
Cu2 N4 C12 C13 169.23(13) . . . . ?
N1 C1 C2 C3 0.0(3) . . . . ?
N1 C1 C14 N2 -16.8(2) . . . . ?
N1 C1 C14 C13 162.36(16) . . . . ?
N3 C6 C7 C8 -1.9(2) . . . . ?
N3 C6 C11 N2 170.74(14) . . . . ?
N3 C6 C11 N4 -10.0(2) . . . . ?
N4 C12 C13 C14 -4.3(3) . . . . ?
C1 N1 C5 C4 -0.4(2) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C1 C14 N2 163.17(16) . . . . ?
C2 C1 C14 C13 -17.7(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 N1 -0.2(3) . . . . ?
C5 N1 C1 C2 0.5(2) . . . . ?
C5 N1 C1 C14 -179.55(15) . . . . ?
C6 N3 C10 C9 -0.1(3) . . . . ?
C6 C7 C8 C9 1.0(2) . . . . ?
C7 C6 C11 N2 -10.1(2) . . . . ?
C7 C6 C11 N4 169.16(16) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C8 C9 C10 N3 -0.7(3) . . . . ?
C10 N3 C6 C7 1.4(2) . . . . ?
C10 N3 C6 C11 -179.40(15) . . . . ?
C11 N2 C14 C1 178.72(14) . . . . ?
C11 N2 C14 C13 -0.4(2) . . . . ?
C11 N4 C12 C13 0.5(3) . . . . ?
C11 C6 C7 C8 178.99(15) . . . . ?
C12 N4 C11 N2 3.9(2) . . . . ?
C12 N4 C11 C6 -175.30(15) . . . . ?
C12 C13 C14 N2 4.3(3) . . . . ?
C12 C13 C14 C1 -174.79(16) . . . . ?
C14 N2 C11 N4 -3.9(2) . . . . ?
C14 N2 C11 C6 175.27(14) . . . . ?
C14 C1 C2 C3 -179.92(16) . . . . ?

_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_3-cu-bpprd-c2h4-bf4
_database_code_depnum_ccdc_archive 'CCDC 2267406'
loop_
_audit_author_name
_audit_author_address
'Kunihisa Sugimoto'
;Kindai University
Japan
;
_audit_update_record             
;
2023-06-04 deposited with the CCDC.	2023-09-22 downloaded from the CCDC.
;
_audit_creation_date             2023-03-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 Cu2 N4, 2(B F4)'
_chemical_formula_sum            'C18 H18 B2 Cu2 F8 N4'
_chemical_formula_weight         591.06
_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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.1296(4)
_cell_length_b                   12.9401(4)
_cell_length_c                   15.7337(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.055(4)
_cell_angle_gamma                90
_cell_volume                     2141.78(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15116
_cell_measurement_temperature    97.15
_cell_measurement_theta_max      31.77
_cell_measurement_theta_min      3.17
_shelx_estimated_absorpt_T_max   0.820
_shelx_estimated_absorpt_T_min   0.576
_exptl_absorpt_coefficient_mu    2.070
_exptl_absorpt_correction_T_max  0.813
_exptl_absorpt_correction_T_min  0.280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.833
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.919
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            31668
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.421
_diffrn_reflns_theta_min         2.791
_diffrn_ambient_temperature      97.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5816
_reflns_number_total             6502
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.732
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6502
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.031
_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)+(0.0279P)²+1.8088P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0776
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.96771(2) 0.58451(2) 0.26066(2) 0.01218(6) Uani 1 1 d . . . . .
Cu2 Cu 0.43603(2) 0.48441(2) 0.11883(2) 0.01342(6) Uani 1 1 d . . . . .
F1 F 1.15165(13) 0.79524(12) 0.46524(10) 0.0425(4) Uani 1 1 d . . . . .
F2 F 0.99700(15) 0.91318(12) 0.41500(14) 0.0535(5) Uani 1 1 d . . . . .
F3 F 0.97126(12) 0.75281(9) 0.35352(8) 0.0281(3) Uani 1 1 d . . . . .
F4 F 1.11372(17) 0.86541(13) 0.32826(11) 0.0508(4) Uani 1 1 d . . . . .
F5 F 0.56218(10) 0.65672(9) 0.33527(8) 0.0248(2) Uani 1 1 d . . . . .
F6 F 0.37354(11) 0.68627(9) 0.35884(8) 0.0268(2) Uani 1 1 d . . . . .
F7 F 0.46306(13) 0.52824(10) 0.38394(11) 0.0396(3) Uani 1 1 d . . . . .
F8 F 0.37949(12) 0.58954(13) 0.24040(9) 0.0426(4) Uani 1 1 d . . . . .
N1 N 1.05240(13) 0.50358(10) 0.36964(9) 0.0125(2) Uani 1 1 d . . . . .
N2 N 0.80737(12) 0.52105(9) 0.27695(8) 0.0093(2) Uani 1 1 d . . . . .
N3 N 0.52551(12) 0.61383(10) 0.10658(9) 0.0128(2) Uani 1 1 d . . . . .
N4 N 0.59926(12) 0.45277(10) 0.21575(9) 0.0121(2) Uani 1 1 d . . . . .
C1 C 0.97586(14) 0.43533(11) 0.39156(10) 0.0105(3) Uani 1 1 d . . . . .
C2 C 1.01953(15) 0.36994(12) 0.46508(10) 0.0127(3) Uani 1 1 d . . . . .
C3 C 1.14753(16) 0.37559(12) 0.51747(10) 0.0154(3) Uani 1 1 d . . . . .
C4 C 1.22616(16) 0.44609(14) 0.49533(11) 0.0166(3) Uani 1 1 d . . . . .
C5 C 1.17508(15) 0.50904(13) 0.42066(11) 0.0156(3) Uani 1 1 d . . . . .
C6 C 0.63891(14) 0.62374(12) 0.17228(10) 0.0106(3) Uani 1 1 d . . . . .
C7 C 0.70013(15) 0.71788(12) 0.19435(10) 0.0131(3) Uani 1 1 d . . . . .
C8 C 0.64418(16) 0.80471(12) 0.14463(11) 0.0159(3) Uani 1 1 d . . . . .
C9 C 0.53113(16) 0.79393(13) 0.07401(11) 0.0171(3) Uani 1 1 d . . . . .
C10 C 0.47376(16) 0.69717(13) 0.05745(11) 0.0162(3) Uani 1 1 d . . . . .
C11 C 0.68618(14) 0.52774(11) 0.22434(10) 0.0102(3) Uani 1 1 d . . . . .
C12 C 0.63361(15) 0.36944(12) 0.26862(11) 0.0135(3) Uani 1 1 d . . . . .
C13 C 0.75368(15) 0.36112(12) 0.33157(10) 0.0127(3) Uani 1 1 d . . . . .
C14 C 0.84127(14) 0.43799(11) 0.33234(10) 0.0099(2) Uani 1 1 d . . . . .
C15 C 1.09104(17) 0.64124(15) 0.20404(12) 0.0206(3) Uani 1 1 d . . . . .
C16 C 0.97039(17) 0.66740(16) 0.15248(12) 0.0233(4) Uani 1 1 d . . . . .
C17 C 0.26450(16) 0.46114(15) 0.02854(12) 0.0210(3) Uani 1 1 d . . . . .
C18 C 0.30094(17) 0.37592(15) 0.08216(14) 0.0240(4) Uani 1 1 d . . . . .
B1 B 1.05761(19) 0.83365(16) 0.38946(13) 0.0197(4) Uani 1 1 d . . . . .
B2 B 0.44447(17) 0.61495(15) 0.32975(12) 0.0153(3) Uani 1 1 d . . . . .
H2 H 0.969(2) 0.3261(17) 0.4814(15) 0.015(5) Uiso 1 1 d . . . . .
H3 H 1.179(2) 0.3331(17) 0.5680(16) 0.019(5) Uiso 1 1 d . . . . .
H4 H 1.311(2) 0.4492(18) 0.5312(16) 0.017(5) Uiso 1 1 d . . . . .
H5 H 1.225(2) 0.5587(18) 0.4036(17) 0.022(6) Uiso 1 1 d . . . . .
H7 H 0.773(2) 0.7242(17) 0.2431(15) 0.015(5) Uiso 1 1 d . . . . .
H8 H 0.682(2) 0.8694(19) 0.1604(16) 0.022(6) Uiso 1 1 d . . . . .
H9 H 0.497(2) 0.8525(18) 0.0386(17) 0.022(6) Uiso 1 1 d . . . . .
H10 H 0.398(2) 0.6889(18) 0.0142(17) 0.021(6) Uiso 1 1 d . . . . .
H12 H 0.572(2) 0.3171(17) 0.2597(15) 0.015(5) Uiso 1 1 d . . . . .
H13 H 0.778(2) 0.3052(18) 0.3695(16) 0.021(6) Uiso 1 1 d . . . . .
H15A H 1.143(3) 0.685(2) 0.2498(18) 0.031(7) Uiso 1 1 d . . . . .
H15B H 1.132(3) 0.586(2) 0.1915(19) 0.032(7) Uiso 1 1 d . . . . .
H16A H 0.928(3) 0.631(2) 0.100(2) 0.042(8) Uiso 1 1 d . . . . .
H16B H 0.936(3) 0.734(2) 0.1606(19) 0.034(7) Uiso 1 1 d . . . . .
H17A H 0.214(3) 0.510(2) 0.0398(19) 0.028(6) Uiso 1 1 d . . . . .
H17B H 0.277(2) 0.4668(19) -0.0309(18) 0.028(6) Uiso 1 1 d . . . . .
H18A H 0.338(3) 0.321(2) 0.066(2) 0.043(8) Uiso 1 1 d . . . . .
H18B H 0.270(3) 0.364(2) 0.1298(18) 0.029(6) 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
Cu1 N1 1.9672(13) . ?
Cu1 N2 2.0550(13) . ?
Cu1 C15 2.0037(17) . ?
Cu1 C16 2.0203(17) . ?
Cu2 N3 1.9897(14) . ?
Cu2 N4 1.9960(13) . ?
Cu2 C17 1.9957(17) . ?
Cu2 C18 1.9994(17) . ?
F1 B1 1.396(2) . ?
F2 B1 1.361(2) . ?
F3 B1 1.408(2) . ?
F4 B1 1.371(2) . ?
F5 B2 1.393(2) . ?
F6 B2 1.386(2) . ?
F7 B2 1.383(2) . ?
F8 B2 1.394(2) . ?
N1 C1 1.348(2) . ?
N1 C5 1.341(2) . ?
N2 C11 1.3353(19) . ?
N2 C14 1.3573(18) . ?
N3 C6 1.3513(19) . ?
N3 C10 1.342(2) . ?
N4 C11 1.3453(19) . ?
N4 C12 1.339(2) . ?
C1 C2 1.387(2) . ?
C1 C14 1.484(2) . ?
C2 C3 1.396(2) . ?
C2 H2 0.89(2) . ?
C3 C4 1.385(2) . ?
C3 H3 0.94(2) . ?
C4 C5 1.390(2) . ?
C4 H4 0.93(2) . ?
C5 H5 0.94(2) . ?
C6 C7 1.384(2) . ?
C6 C11 1.486(2) . ?
C7 C8 1.394(2) . ?
C7 H7 0.92(2) . ?
C8 C9 1.387(2) . ?
C8 H8 0.93(2) . ?
C9 C10 1.391(2) . ?
C9 H9 0.94(2) . ?
C10 H10 0.90(2) . ?
C12 C13 1.384(2) . ?
C12 H12 0.94(2) . ?
C13 C14 1.390(2) . ?
C13 H13 0.92(2) . ?
C15 C16 1.366(3) . ?
C15 H15A 0.95(3) . ?
C15 H15B 0.91(3) . ?
C16 H16A 0.94(3) . ?
C16 H16B 0.97(3) . ?
C17 C18 1.367(3) . ?
C17 H17A 0.90(3) . ?
C17 H17B 0.99(3) . ?
C18 H18A 0.90(3) . ?
C18 H18B 0.94(3) . ?

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 N2 82.36(5) . . ?
N1 Cu1 C15 112.32(7) . . ?
N1 Cu1 C16 151.92(7) . . ?
C15 Cu1 N2 161.92(6) . . ?
C15 Cu1 C16 39.67(7) . . ?
C16 Cu1 N2 124.71(6) . . ?
N3 Cu2 N4 83.52(5) . . ?
N3 Cu2 C17 116.79(7) . . ?
N3 Cu2 C18 156.35(7) . . ?
N4 Cu2 C18 119.18(7) . . ?
C17 Cu2 N4 158.97(7) . . ?
C17 Cu2 C18 40.02(8) . . ?
C1 N1 Cu1 114.14(10) . . ?
C5 N1 Cu1 126.74(11) . . ?
C5 N1 C1 119.11(14) . . ?
C11 N2 Cu1 129.74(10) . . ?
C11 N2 C14 117.52(13) . . ?
C14 N2 Cu1 109.02(9) . . ?
C6 N3 Cu2 112.19(10) . . ?
C10 N3 Cu2 126.72(11) . . ?
C10 N3 C6 118.83(14) . . ?
C11 N4 Cu2 111.97(10) . . ?
C12 N4 Cu2 130.07(11) . . ?
C12 N4 C11 117.92(13) . . ?
N1 C1 C2 122.32(14) . . ?
N1 C1 C14 114.64(13) . . ?
C2 C1 C14 123.02(14) . . ?
C1 C2 C3 118.22(15) . . ?
C1 C2 H2 123.1(15) . . ?
C3 C2 H2 118.7(15) . . ?
C2 C3 H3 120.1(14) . . ?
C4 C3 C2 119.53(15) . . ?
C4 C3 H3 120.4(14) . . ?
C3 C4 C5 118.76(15) . . ?
C3 C4 H4 118.4(14) . . ?
C5 C4 H4 122.8(14) . . ?
N1 C5 C4 122.06(15) . . ?
N1 C5 H5 116.2(15) . . ?
C4 C5 H5 121.7(15) . . ?
N3 C6 C7 122.41(14) . . ?
N3 C6 C11 114.60(13) . . ?
C7 C6 C11 122.74(13) . . ?
C6 C7 C8 118.40(14) . . ?
C6 C7 H7 121.0(14) . . ?
C8 C7 H7 120.5(14) . . ?
C7 C8 H8 119.5(15) . . ?
C9 C8 C7 119.37(15) . . ?
C9 C8 H8 121.1(15) . . ?
C8 C9 C10 118.78(15) . . ?
C8 C9 H9 118.4(15) . . ?
C10 C9 H9 122.8(15) . . ?
N3 C10 C9 122.07(15) . . ?
N3 C10 H10 117.4(15) . . ?
C9 C10 H10 120.5(15) . . ?
N2 C11 N4 124.28(14) . . ?
N2 C11 C6 119.99(13) . . ?
N4 C11 C6 115.71(13) . . ?
N4 C12 C13 121.36(14) . . ?
N4 C12 H12 116.2(14) . . ?
C13 C12 H12 122.4(14) . . ?
C12 C13 C14 117.48(14) . . ?
C12 C13 H13 122.4(15) . . ?
C14 C13 H13 120.0(15) . . ?
N2 C14 C1 115.69(13) . . ?
N2 C14 C13 120.93(14) . . ?
C13 C14 C1 123.38(13) . . ?
Cu1 C15 H15A 102.8(16) . . ?
Cu1 C15 H15B 106.1(17) . . ?
C16 C15 Cu1 70.82(10) . . ?
C16 C15 H15A 122.9(16) . . ?
C16 C15 H15B 122.5(18) . . ?
H15A C15 H15B 114(2) . . ?
Cu1 C16 H16A 109.9(18) . . ?
Cu1 C16 H16B 104.5(17) . . ?
C15 C16 Cu1 69.51(10) . . ?
C15 C16 H16A 121.3(18) . . ?
C15 C16 H16B 119.5(17) . . ?
H16A C16 H16B 117(2) . . ?
Cu2 C17 H17A 105.6(17) . . ?
Cu2 C17 H17B 105.1(15) . . ?
C18 C17 Cu2 70.14(10) . . ?
C18 C17 H17A 121.4(17) . . ?
C18 C17 H17B 122.4(15) . . ?
H17A C17 H17B 115(2) . . ?
Cu2 C18 H18A 105.7(19) . . ?
Cu2 C18 H18B 109.0(16) . . ?
C17 C18 Cu2 69.84(10) . . ?
C17 C18 H18A 122(2) . . ?
C17 C18 H18B 120.9(16) . . ?
H18A C18 H18B 115(2) . . ?
F1 B1 F3 107.55(15) . . ?
F2 B1 F1 108.82(18) . . ?
F2 B1 F3 109.95(16) . . ?
F2 B1 F4 111.35(18) . . ?
F4 B1 F1 108.67(17) . . ?
F4 B1 F3 110.39(16) . . ?
F5 B2 F8 108.79(15) . . ?
F6 B2 F5 110.27(15) . . ?
F6 B2 F8 109.04(14) . . ?
F7 B2 F5 109.14(14) . . ?
F7 B2 F6 108.86(15) . . ?
F7 B2 F8 110.74(16) . . ?

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 178.54(11) . . . . ?
Cu1 N1 C1 C14 -3.02(16) . . . . ?
Cu1 N1 C5 C4 -178.28(12) . . . . ?
Cu1 N2 C11 N4 148.32(12) . . . . ?
Cu1 N2 C11 C6 -33.3(2) . . . . ?
Cu1 N2 C14 C1 21.38(15) . . . . ?
Cu1 N2 C14 C13 -158.09(12) . . . . ?
Cu2 N3 C6 C7 -160.18(12) . . . . ?
Cu2 N3 C6 C11 14.29(16) . . . . ?
Cu2 N3 C10 C9 159.38(13) . . . . ?
Cu2 N4 C11 N2 -172.30(12) . . . . ?
Cu2 N4 C11 C6 9.24(16) . . . . ?
Cu2 N4 C12 C13 178.72(11) . . . . ?
N1 C1 C2 C3 -0.2(2) . . . . ?
N1 C1 C14 N2 -13.17(18) . . . . ?
N1 C1 C14 C13 166.28(14) . . . . ?
N3 C6 C7 C8 -2.2(2) . . . . ?
N3 C6 C11 N2 165.42(13) . . . . ?
N3 C6 C11 N4 -16.05(19) . . . . ?
N4 C12 C13 C14 -5.8(2) . . . . ?
C1 N1 C5 C4 0.3(2) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
C2 C1 C14 N2 165.26(14) . . . . ?
C2 C1 C14 C13 -15.3(2) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C4 C5 N1 0.0(2) . . . . ?
C5 N1 C1 C2 -0.2(2) . . . . ?
C5 N1 C1 C14 178.20(13) . . . . ?
C6 N3 C10 C9 -2.2(2) . . . . ?
C6 C7 C8 C9 -1.3(2) . . . . ?
C7 C6 C11 N2 -20.1(2) . . . . ?
C7 C6 C11 N4 158.39(14) . . . . ?
C7 C8 C9 C10 2.9(2) . . . . ?
C8 C9 C10 N3 -1.2(3) . . . . ?
C10 N3 C6 C7 3.9(2) . . . . ?
C10 N3 C6 C11 178.38(13) . . . . ?
C11 N2 C14 C1 -178.21(12) . . . . ?
C11 N2 C14 C13 2.3(2) . . . . ?
C11 N4 C12 C13 1.3(2) . . . . ?
C11 C6 C7 C8 -176.21(14) . . . . ?
C12 N4 C11 N2 5.6(2) . . . . ?
C12 N4 C11 C6 -172.90(13) . . . . ?
C12 C13 C14 N2 3.9(2) . . . . ?
C12 C13 C14 C1 -175.54(14) . . . . ?
C14 N2 C11 N4 -7.3(2) . . . . ?
C14 N2 C11 C6 171.07(13) . . . . ?
C14 C1 C2 C3 -178.52(13) . . . . ?

_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_4-cu-bpprd-u-c2h4-bf4
_database_code_depnum_ccdc_archive 'CCDC 2267407'
loop_
_audit_author_name
_audit_author_address
'Kunihisa Sugimoto'
;Kindai University
Japan
;
_audit_update_record             
;
2023-06-04 deposited with the CCDC.	2023-09-22 downloaded from the CCDC.
;
_audit_creation_date             2023-06-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 Cu3 N8, C32 H28 Cu3 N8, 6(B F4)'
_chemical_formula_sum            'C62 H52 B6 Cu6 F24 N16'
_chemical_formula_weight         1923.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.7929(6)
_cell_length_b                   11.3730(2)
_cell_length_c                   29.0946(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.594(3)
_cell_angle_gamma                90
_cell_volume                     7105.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21077
_cell_measurement_temperature    97.15
_cell_measurement_theta_max      31.73
_cell_measurement_theta_min      2.76
_shelx_estimated_absorpt_T_max   0.864
_shelx_estimated_absorpt_T_min   0.766
_exptl_absorpt_coefficient_mu    1.881
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_correction_T_min  0.766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.798
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             3824
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            50700
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.411
_diffrn_reflns_theta_min         2.768
_diffrn_ambient_temperature      97.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9477
_reflns_number_total             10738
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         2.683
_refine_diff_density_min         -1.635
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     535
_refine_ls_number_reflns         10738
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²+19.7521P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0944
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C31-H31a = C31-H31b
 0.99 with sigma of 0.02
 C30-H30b = C30-H30a
 0.99 with sigma of 0.02
 C29-H29b = C29-H29a
 0.99 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uiso(H29b) = Uiso(H29a)
Uiso(H31a) = Uiso(H31b) = Uiso(H30b) = Uiso(H30a)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12),
 C13(H13), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23),
  C24(H24), C26(H26), C27(H27)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.61119(3) 0.750000 0.01456(7) Uani 1 2 d S T P . .
Cu2 Cu 0.49907(2) 0.46857(2) 0.56318(2) 0.01507(6) Uani 1 1 d . . . . .
Cu3 Cu 0.500000 0.92926(3) 0.750000 0.01912(7) Uani 1 2 d S T P . .
Cu4 Cu 0.33922(2) 1.01649(2) 0.54341(2) 0.02521(7) Uani 1 1 d . . . . .
F1 F 0.40319(7) 0.82645(12) 0.57352(5) 0.0297(3) Uani 1 1 d . . . . .
F2 F 0.47104(6) 0.67775(11) 0.57883(5) 0.0275(3) Uani 1 1 d . . . . .
F3 F 0.46002(13) 0.8236(2) 0.52399(9) 0.0877(10) Uani 1 1 d . . . . .
F4 F 0.38235(12) 0.6932(3) 0.51379(11) 0.1107(13) Uani 1 1 d . . . . .
F5 F 0.20957(7) 1.23764(15) 0.53125(5) 0.0376(3) Uani 1 1 d . . . . .
F6 F 0.12300(6) 1.25398(13) 0.55316(6) 0.0322(3) Uani 1 1 d . . . . .
F7 F 0.21666(6) 1.21250(14) 0.61050(5) 0.0325(3) Uani 1 1 d . . . . .
F8 F 0.16808(6) 1.07490(12) 0.55374(5) 0.0253(3) Uani 1 1 d . . . . .
F9 F 0.28949(7) 1.17405(12) 0.73922(5) 0.0320(3) Uani 1 1 d . . . . .
F10 F 0.31884(7) 1.28547(15) 0.80811(5) 0.0378(3) Uani 1 1 d . . . . .
F11 F 0.38605(6) 1.25641(17) 0.76588(5) 0.0391(4) Uani 1 1 d . . . . .
F12 F 0.30086(7) 1.37112(12) 0.73413(6) 0.0341(3) Uani 1 1 d . . . . .
N1 N 0.58577(7) 0.64638(13) 0.79225(5) 0.0137(3) Uani 1 1 d . . . . .
N2 N 0.54993(7) 0.52692(13) 0.70830(5) 0.0123(3) Uani 1 1 d . . . . .
N3 N 0.44115(7) 0.41482(14) 0.59643(5) 0.0146(3) Uani 1 1 d . . . . .
N4 N 0.55840(7) 0.48778(14) 0.63074(5) 0.0139(3) Uani 1 1 d . . . . .
N5 N 0.44094(8) 0.90110(14) 0.78298(6) 0.0173(3) Uani 1 1 d . . . . .
N6 N 0.40988(8) 1.00855(14) 0.69278(6) 0.0178(3) Uani 1 1 d . . . . .
N7 N 0.42394(9) 1.08111(15) 0.57564(6) 0.0230(3) Uani 1 1 d . . . . .
N8 N 0.33734(8) 1.01717(16) 0.61172(6) 0.0233(3) Uani 1 1 d . . . . .
C1 C 0.63075(8) 0.61796(15) 0.77342(6) 0.0132(3) Uani 1 1 d . . . . .
C2 C 0.69393(9) 0.62417(17) 0.80058(7) 0.0186(3) Uani 1 1 d . . . . .
H2 H 0.724463 0.607171 0.785930 0.022 Uiso 1 1 calc R U . . .
C3 C 0.71150(9) 0.65565(19) 0.84945(7) 0.0223(4) Uani 1 1 d . . . . .
H3 H 0.754261 0.659669 0.868905 0.027 Uiso 1 1 calc R U . . .
C4 C 0.66567(9) 0.68107(18) 0.86936(7) 0.0213(4) Uani 1 1 d . . . . .
H4 H 0.676503 0.700854 0.902904 0.026 Uiso 1 1 calc R U . . .
C5 C 0.60359(9) 0.67727(16) 0.83962(6) 0.0169(3) Uani 1 1 d . . . . .
H5 H 0.572454 0.697283 0.853273 0.020 Uiso 1 1 calc R U . . .
C6 C 0.46513(8) 0.42771(15) 0.64555(6) 0.0123(3) Uani 1 1 d . . . . .
C7 C 0.43303(9) 0.39050(16) 0.67587(6) 0.0154(3) Uani 1 1 d . . . . .
H7 H 0.451135 0.397473 0.710290 0.019 Uiso 1 1 calc R U . . .
C8 C 0.37379(9) 0.34277(17) 0.65489(7) 0.0189(3) Uani 1 1 d . . . . .
H8 H 0.350786 0.317141 0.674880 0.023 Uiso 1 1 calc R U . . .
C9 C 0.34867(9) 0.33296(17) 0.60459(7) 0.0199(3) Uani 1 1 d . . . . .
H9 H 0.307909 0.302431 0.589533 0.024 Uiso 1 1 calc R U . . .
C10 C 0.38437(8) 0.36876(17) 0.57657(7) 0.0178(3) Uani 1 1 d . . . . .
H10 H 0.367758 0.360116 0.542129 0.021 Uiso 1 1 calc R U . . .
C11 C 0.52790(8) 0.48311(15) 0.66312(6) 0.0124(3) Uani 1 1 d . . . . .
C12 C 0.61564(8) 0.53507(16) 0.64523(6) 0.0157(3) Uani 1 1 d . . . . .
H12 H 0.637743 0.539478 0.622806 0.019 Uiso 1 1 calc R U . . .
C13 C 0.64315(8) 0.57751(17) 0.69209(6) 0.0153(3) Uani 1 1 d . . . . .
H13 H 0.684242 0.608449 0.702699 0.018 Uiso 1 1 calc R U . . .
C14 C 0.60814(8) 0.57299(15) 0.72298(6) 0.0127(3) Uani 1 1 d . . . . .
C15 C 0.38086(9) 0.93025(16) 0.75997(7) 0.0187(3) Uani 1 1 d . . . . .
C16 C 0.33613(10) 0.92188(19) 0.78287(9) 0.0259(4) Uani 1 1 d . . . . .
H16 H 0.294116 0.943471 0.766038 0.031 Uiso 1 1 calc R U . . .
C17 C 0.35403(11) 0.8814(2) 0.83075(9) 0.0289(4) Uani 1 1 d . . . . .
H17 H 0.324212 0.874252 0.846876 0.035 Uiso 1 1 calc R U . . .
C18 C 0.41551(11) 0.85178(19) 0.85458(8) 0.0257(4) Uani 1 1 d . . . . .
H18 H 0.428759 0.824298 0.887306 0.031 Uiso 1 1 calc R U . . .
C19 C 0.45759(10) 0.86312(17) 0.82955(7) 0.0208(4) Uani 1 1 d . . . . .
H19 H 0.499956 0.843223 0.845978 0.025 Uiso 1 1 calc R U . . .
C20 C 0.44151(10) 1.08291(16) 0.62511(7) 0.0196(3) Uani 1 1 d . . . . .
C21 C 0.49835(10) 1.12790(17) 0.65375(7) 0.0204(4) Uani 1 1 d . . . . .
H21 H 0.508973 1.131870 0.688201 0.024 Uiso 1 1 calc R U . . .
C22 C 0.53993(11) 1.16745(18) 0.63107(8) 0.0238(4) Uani 1 1 d . . . . .
H22 H 0.579486 1.197944 0.649939 0.029 Uiso 1 1 calc R U . . .
C23 C 0.52270(12) 1.1616(2) 0.58076(8) 0.0278(4) Uani 1 1 d . . . . .
H23 H 0.550603 1.186275 0.564668 0.033 Uiso 1 1 calc R U . . .
C24 C 0.46408(12) 1.11913(19) 0.55421(8) 0.0273(4) Uani 1 1 d . . . . .
H24 H 0.451963 1.116918 0.519636 0.033 Uiso 1 1 calc R U . . .
C25 C 0.39436(9) 1.03424(16) 0.64520(7) 0.0189(3) Uani 1 1 d . . . . .
C26 C 0.29214(10) 0.9792(2) 0.62763(8) 0.0267(4) Uani 1 1 d . . . . .
H26 H 0.251344 0.969252 0.604893 0.032 Uiso 1 1 calc R U . . .
C27 C 0.30306(10) 0.9541(2) 0.67624(8) 0.0252(4) Uani 1 1 d . . . . .
H27 H 0.270467 0.928705 0.687404 0.030 Uiso 1 1 calc R U . . .
C28 C 0.36379(9) 0.96739(17) 0.70824(7) 0.0191(3) Uani 1 1 d . . . . .
C29 C 0.46852(8) 0.47926(18) 0.48989(6) 0.0163(3) Uani 1 1 d D . . . .
C30 C 0.26389(14) 0.9531(3) 0.49190(10) 0.0448(7) Uani 1 1 d D . . . .
C31 C 0.30911(13) 0.9766(2) 0.47214(8) 0.0353(5) Uani 1 1 d D . . . .
B1 B 0.42877(13) 0.7549(2) 0.54651(9) 0.0292(5) Uani 1 1 d . . . . .
B2 B 0.17943(10) 1.1958(2) 0.56217(8) 0.0210(4) Uani 1 1 d . . . . .
B3 B 0.32389(10) 1.2711(2) 0.76206(8) 0.0217(4) Uani 1 1 d . . . . .
H29A H 0.4590(12) 0.3982(16) 0.4808(9) 0.020(4) Uiso 1 1 d D . . . .
H29B H 0.4338(10) 0.530(2) 0.4874(10) 0.020(4) Uiso 1 1 d D . . . .
H31A H 0.3343(14) 0.910(2) 0.4683(13) 0.048(5) Uiso 1 1 d D . . . .
H30A H 0.2601(16) 0.8717(19) 0.5030(12) 0.048(5) Uiso 1 1 d D . . . .
H31B H 0.3123(16) 1.048(2) 0.4551(12) 0.048(5) Uiso 1 1 d D . . . .
H30B H 0.2300(13) 1.008(3) 0.4895(13) 0.048(5) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.9701(15) . ?
Cu1 N1 1.9701(15) 2_656 ?
Cu1 N2 2.1476(14) 2_656 ?
Cu1 N2 2.1476(14) . ?
Cu2 N3 1.9770(15) . ?
Cu2 N4 1.9892(15) . ?
Cu2 C29 2.0118(17) 5_666 ?
Cu2 C29 2.0126(17) . ?
Cu3 N5 1.9240(16) 2_656 ?
Cu3 N5 1.9239(16) . ?
Cu3 N6 2.3475(16) . ?
Cu3 N6 2.3475(16) 2_656 ?
Cu4 N7 1.9833(19) . ?
Cu4 N8 2.0022(19) . ?
Cu4 C30 1.997(3) . ?
Cu4 C31 2.006(2) . ?
F1 B1 1.388(3) . ?
F2 B1 1.405(3) . ?
F3 B1 1.364(4) . ?
F4 B1 1.357(4) . ?
F5 B2 1.386(3) . ?
F6 B2 1.391(3) . ?
F7 B2 1.390(2) . ?
F8 B2 1.406(3) . ?
F9 B3 1.388(3) . ?
F10 B3 1.392(3) . ?
F11 B3 1.394(3) . ?
F12 B3 1.394(3) . ?
N1 C1 1.353(2) . ?
N1 C5 1.346(2) . ?
N2 C11 1.336(2) . ?
N2 C14 1.355(2) . ?
N3 C6 1.356(2) . ?
N3 C10 1.335(2) . ?
N4 C11 1.347(2) . ?
N4 C12 1.342(2) . ?
N5 C15 1.349(2) . ?
N5 C19 1.350(2) . ?
N6 C25 1.341(2) . ?
N6 C28 1.357(3) . ?
N7 C20 1.359(2) . ?
N7 C24 1.340(3) . ?
N8 C25 1.352(3) . ?
N8 C26 1.335(3) . ?
C1 C2 1.393(2) . ?
C1 C14 1.474(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(2) . ?
C6 C11 1.488(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.392(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.386(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.392(3) . ?
C10 H10 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.383(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.389(2) . ?
C15 C16 1.396(3) . ?
C15 C28 1.484(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.392(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.391(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(3) . ?
C20 C25 1.491(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.398(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.384(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.387(3) . ?
C24 H24 0.9500 . ?
C26 H26 0.9500 . ?
C26 C27 1.381(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.393(3) . ?
C29 C29 1.436(3) 5_666 ?
C29 H29A 0.963(16) . ?
C29 H29B 0.966(16) . ?
C30 C31 1.364(5) . ?
C30 H30A 0.993(18) . ?
C30 H30B 0.979(18) . ?
C31 H31A 0.979(18) . ?
C31 H31B 0.965(18) . ?

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 N1 156.56(9) . 2_656 ?
N1 Cu1 N2 80.80(6) . . ?
N1 Cu1 N2 109.95(6) 2_656 . ?
N1 Cu1 N2 109.95(6) . 2_656 ?
N1 Cu1 N2 80.80(6) 2_656 2_656 ?
N2 Cu1 N2 126.99(8) . 2_656 ?
N3 Cu2 N4 83.96(6) . . ?
N3 Cu2 C29 119.11(7) . . ?
N3 Cu2 C29 160.75(7) . 5_666 ?
N4 Cu2 C29 115.03(7) . 5_666 ?
N4 Cu2 C29 156.82(7) . . ?
C29 Cu2 C29 41.81(9) 5_666 . ?
N5 Cu3 N5 160.84(10) . 2_656 ?
N5 Cu3 N6 107.60(6) . 2_656 ?
N5 Cu3 N6 79.95(6) 2_656 2_656 ?
N5 Cu3 N6 107.60(6) 2_656 . ?
N5 Cu3 N6 79.95(6) . . ?
N6 Cu3 N6 134.81(8) 2_656 . ?
N7 Cu4 N8 82.57(7) . . ?
N7 Cu4 C30 160.80(11) . . ?
N7 Cu4 C31 120.94(10) . . ?
N8 Cu4 C31 155.97(11) . . ?
C30 Cu4 N8 116.56(11) . . ?
C30 Cu4 C31 39.86(13) . . ?
C1 N1 Cu1 115.27(11) . . ?
C5 N1 Cu1 125.96(13) . . ?
C5 N1 C1 117.85(16) . . ?
C11 N2 Cu1 128.81(12) . . ?
C11 N2 C14 117.35(14) . . ?
C14 N2 Cu1 107.31(11) . . ?
C6 N3 Cu2 112.52(12) . . ?
C10 N3 Cu2 128.25(12) . . ?
C10 N3 C6 119.23(15) . . ?
C11 N4 Cu2 110.35(11) . . ?
C12 N4 Cu2 128.44(12) . . ?
C12 N4 C11 118.14(15) . . ?
C15 N5 Cu3 118.38(13) . . ?
C15 N5 C19 118.29(17) . . ?
C19 N5 Cu3 123.08(14) . . ?
C25 N6 Cu3 132.91(13) . . ?
C25 N6 C28 116.85(17) . . ?
C28 N6 Cu3 102.88(12) . . ?
C20 N7 Cu4 113.64(15) . . ?
C24 N7 Cu4 127.44(15) . . ?
C24 N7 C20 118.91(19) . . ?
C25 N8 Cu4 112.37(14) . . ?
C26 N8 Cu4 128.23(15) . . ?
C26 N8 C25 117.64(19) . . ?
N1 C1 C2 122.52(16) . . ?
N1 C1 C14 115.23(15) . . ?
C2 C1 C14 122.15(16) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.83(17) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 118.90(18) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.12(17) . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 122.69(17) . . ?
N1 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
N3 C6 C7 121.66(16) . . ?
N3 C6 C11 114.15(14) . . ?
C7 C6 C11 124.19(15) . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C8 118.75(16) . . ?
C8 C7 H7 120.6 . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.40(17) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 120.7 . . ?
C8 C9 C10 118.65(17) . . ?
C10 C9 H9 120.7 . . ?
N3 C10 C9 122.25(17) . . ?
N3 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
N2 C11 N4 124.18(16) . . ?
N2 C11 C6 119.78(15) . . ?
N4 C11 C6 116.02(15) . . ?
N4 C12 H12 119.3 . . ?
N4 C12 C13 121.43(16) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 H13 121.4 . . ?
C12 C13 C14 117.15(16) . . ?
C14 C13 H13 121.4 . . ?
N2 C14 C1 115.24(14) . . ?
N2 C14 C13 121.63(15) . . ?
C13 C14 C1 123.13(16) . . ?
N5 C15 C16 121.94(19) . . ?
N5 C15 C28 116.78(17) . . ?
C16 C15 C28 121.24(18) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.0(2) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.39(19) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 120.8 . . ?
C17 C18 C19 118.4(2) . . ?
C19 C18 H18 120.8 . . ?
N5 C19 C18 122.96(19) . . ?
N5 C19 H19 118.5 . . ?
C18 C19 H19 118.5 . . ?
N7 C20 C21 121.87(19) . . ?
N7 C20 C25 114.48(18) . . ?
C21 C20 C25 123.65(17) . . ?
C20 C21 H21 120.6 . . ?
C20 C21 C22 118.76(18) . . ?
C22 C21 H21 120.6 . . ?
C21 C22 H22 120.4 . . ?
C23 C22 C21 119.1(2) . . ?
C23 C22 H22 120.4 . . ?
C22 C23 H23 120.5 . . ?
C22 C23 C24 119.0(2) . . ?
C24 C23 H23 120.5 . . ?
N7 C24 C23 122.26(19) . . ?
N7 C24 H24 118.9 . . ?
C23 C24 H24 118.9 . . ?
N6 C25 N8 124.73(19) . . ?
N6 C25 C20 120.67(17) . . ?
N8 C25 C20 114.58(17) . . ?
N8 C26 H26 119.1 . . ?
N8 C26 C27 121.8(2) . . ?
C27 C26 H26 119.1 . . ?
C26 C27 H27 121.3 . . ?
C26 C27 C28 117.3(2) . . ?
C28 C27 H27 121.3 . . ?
N6 C28 C15 117.74(17) . . ?
N6 C28 C27 121.47(19) . . ?
C27 C28 C15 120.70(19) . . ?
Cu2 C29 Cu2 138.19(9) 5_666 . ?
Cu2 C29 H29A 101.6(16) . . ?
Cu2 C29 H29A 100.2(15) 5_666 . ?
Cu2 C29 H29B 105.5(16) 5_666 . ?
Cu2 C29 H29B 95.7(16) . . ?
C29 C29 Cu2 69.12(13) 5_666 5_666 ?
C29 C29 Cu2 69.07(13) 5_666 . ?
C29 C29 H29A 121.9(16) 5_666 . ?
C29 C29 H29B 121.0(16) 5_666 . ?
H29A C29 H29B 117(2) . . ?
Cu4 C30 H30A 104(2) . . ?
Cu4 C30 H30B 106(2) . . ?
C31 C30 Cu4 70.41(16) . . ?
C31 C30 H30A 119(2) . . ?
C31 C30 H30B 122(2) . . ?
H30A C30 H30B 118(3) . . ?
Cu4 C31 H31A 106(2) . . ?
Cu4 C31 H31B 106(2) . . ?
C30 C31 Cu4 69.73(15) . . ?
C30 C31 H31A 117(2) . . ?
C30 C31 H31B 125(2) . . ?
H31A C31 H31B 116(3) . . ?
F1 B1 F2 108.13(18) . . ?
F3 B1 F1 108.8(2) . . ?
F3 B1 F2 109.1(2) . . ?
F4 B1 F1 108.9(2) . . ?
F4 B1 F2 110.2(2) . . ?
F4 B1 F3 111.6(3) . . ?
F5 B2 F6 110.05(19) . . ?
F5 B2 F7 110.02(17) . . ?
F5 B2 F8 108.94(17) . . ?
F6 B2 F8 109.15(16) . . ?
F7 B2 F6 109.75(17) . . ?
F7 B2 F8 108.91(18) . . ?
F9 B3 F10 109.77(18) . . ?
F9 B3 F11 109.78(19) . . ?
F9 B3 F12 109.15(18) . . ?
F10 B3 F11 110.31(18) . . ?
F10 B3 F12 109.22(19) . . ?
F11 B3 F12 108.58(18) . . ?

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 -172.31(14) . . . . ?
Cu1 N1 C1 C14 4.13(19) . . . . ?
Cu1 N1 C5 C4 168.57(15) . . . . ?
Cu1 N2 C11 N4 143.98(14) . . . . ?
Cu1 N2 C11 C6 -34.3(2) . . . . ?
Cu1 N2 C14 C1 27.00(17) . . . . ?
Cu1 N2 C14 C13 -152.58(14) . . . . ?
Cu2 N3 C6 C7 -177.14(14) . . . . ?
Cu2 N3 C6 C11 2.27(19) . . . . ?
Cu2 N3 C10 C9 179.13(14) . . . . ?
Cu2 N4 C11 N2 -159.03(14) . . . . ?
Cu2 N4 C11 C6 19.30(19) . . . . ?
Cu2 N4 C12 C13 158.48(14) . . . . ?
Cu3 N5 C15 C16 -174.54(16) . . . . ?
Cu3 N5 C15 C28 7.8(2) . . . . ?
Cu3 N5 C19 C18 174.71(16) . . . . ?
Cu3 N6 C25 N8 141.23(16) . . . . ?
Cu3 N6 C25 C20 -37.3(3) . . . . ?
Cu3 N6 C28 C15 21.67(19) . . . . ?
Cu3 N6 C28 C27 -154.86(16) . . . . ?
Cu4 N7 C20 C21 -178.20(15) . . . . ?
Cu4 N7 C20 C25 1.1(2) . . . . ?
Cu4 N7 C24 C23 -179.28(16) . . . . ?
Cu4 N8 C25 N6 -161.56(15) . . . . ?
Cu4 N8 C25 C20 17.1(2) . . . . ?
Cu4 N8 C26 C27 161.46(16) . . . . ?
N1 C1 C2 C3 3.0(3) . . . . ?
N1 C1 C14 N2 -22.5(2) . . . . ?
N1 C1 C14 C13 157.07(17) . . . . ?
N3 C6 C7 C8 -2.4(3) . . . . ?
N3 C6 C11 N2 163.54(15) . . . . ?
N3 C6 C11 N4 -14.9(2) . . . . ?
N4 C12 C13 C14 -2.3(3) . . . . ?
N5 C15 C16 C17 -0.5(3) . . . . ?
N5 C15 C28 N6 -22.4(3) . . . . ?
N5 C15 C28 C27 154.16(18) . . . . ?
N7 C20 C21 C22 -3.1(3) . . . . ?
N7 C20 C25 N6 166.43(17) . . . . ?
N7 C20 C25 N8 -12.3(2) . . . . ?
N8 C26 C27 C28 -1.4(3) . . . . ?
C1 N1 C5 C4 0.1(3) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C1 C14 N2 153.96(17) . . . . ?
C2 C1 C14 C13 -26.5(3) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
C3 C4 C5 N1 2.0(3) . . . . ?
C5 N1 C1 C2 -2.6(3) . . . . ?
C5 N1 C1 C14 173.82(15) . . . . ?
C6 N3 C10 C9 -0.2(3) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C7 C6 C11 N2 -17.1(3) . . . . ?
C7 C6 C11 N4 164.52(17) . . . . ?
C7 C8 C9 C10 1.6(3) . . . . ?
C8 C9 C10 N3 -1.7(3) . . . . ?
C10 N3 C6 C7 2.3(3) . . . . ?
C10 N3 C6 C11 -178.34(16) . . . . ?
C11 N2 C14 C1 -178.81(15) . . . . ?
C11 N2 C14 C13 1.6(2) . . . . ?
C11 N4 C12 C13 0.3(3) . . . . ?
C11 C6 C7 C8 178.28(17) . . . . ?
C12 N4 C11 N2 2.8(3) . . . . ?
C12 N4 C11 C6 -178.82(16) . . . . ?
C12 C13 C14 N2 1.3(3) . . . . ?
C12 C13 C14 C1 -178.29(17) . . . . ?
C14 N2 C11 N4 -3.8(3) . . . . ?
C14 N2 C11 C6 177.94(15) . . . . ?
C14 C1 C2 C3 -173.24(18) . . . . ?
C15 N5 C19 C18 0.6(3) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C16 C15 C28 N6 159.94(19) . . . . ?
C16 C15 C28 C27 -23.5(3) . . . . ?
C16 C17 C18 C19 -0.3(3) . . . . ?
C17 C18 C19 N5 -0.4(3) . . . . ?
C19 N5 C15 C16 -0.1(3) . . . . ?
C19 N5 C15 C28 -177.79(17) . . . . ?
C20 N7 C24 C23 -0.8(3) . . . . ?
C20 C21 C22 C23 0.7(3) . . . . ?
C21 C20 C25 N6 -14.3(3) . . . . ?
C21 C20 C25 N8 166.99(18) . . . . ?
C21 C22 C23 C24 1.5(3) . . . . ?
C22 C23 C24 N7 -1.5(3) . . . . ?
C24 N7 C20 C21 3.1(3) . . . . ?
C24 N7 C20 C25 -177.64(17) . . . . ?
C25 N6 C28 C15 175.66(16) . . . . ?
C25 N6 C28 C27 -0.9(3) . . . . ?
C25 N8 C26 C27 -2.2(3) . . . . ?
C25 C20 C21 C22 177.76(18) . . . . ?
C26 N8 C25 N6 4.6(3) . . . . ?
C26 N8 C25 C20 -176.78(17) . . . . ?
C26 C27 C28 N6 3.0(3) . . . . ?
C26 C27 C28 C15 -173.48(19) . . . . ?
C28 N6 C25 N8 -3.1(3) . . . . ?
C28 N6 C25 C20 178.40(16) . . . . ?
C28 C15 C16 C17 177.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
