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#$Date: 2023-05-19 02:10:06 +0300 (Fri, 19 May 2023) $
#$Revision: 283882 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/30/7713099.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7713099
loop_
_publ_author_name
'Gomes, Pedro T.'
'Cruz, Tiago Carpinteiro'
'Lopes, Patrícia S.'
'Lemos, Maria Amélia N. D. A.'
'Veiros, Luis F.'
_publ_section_title
;
 New copper(I) complexes of bulky 5-substituted-2-iminopyrrolyl ligands as
 catalysts for azide-alkyne cycloaddition
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT00617D
_journal_year                    2023
_chemical_formula_moiety         'C50 H56 Cu2 N4 O4'
_chemical_formula_sum            'C50 H56 Cu2 N4 O4'
_chemical_formula_weight         904.06
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-02-21 deposited with the CCDC.	2023-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                83.347(6)
_cell_angle_beta                 80.624(6)
_cell_angle_gamma                80.833(5)
_cell_formula_units_Z            2
_cell_length_a                   10.5418(9)
_cell_length_b                   11.9349(11)
_cell_length_c                   21.971(2)
_cell_measurement_reflns_used    1588
_cell_measurement_temperature    150
_cell_measurement_theta_max      19.13
_cell_measurement_theta_min      2.93
_cell_volume                     2681.0(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    enCIFer
_computing_publication_material  ORTEP
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0
_diffrn_reflns_av_unetI/netI     0.1698
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9920
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.826
_diffrn_reflns_theta_min         1.736
_exptl_absorpt_coefficient_mu    0.834
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_description       prism
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.997
_refine_diff_density_min         -0.503
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       0.0122(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.864
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     554
_refine_ls_number_reflns         9920
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.864
_refine_ls_R_factor_all          0.1427
_refine_ls_R_factor_gt           0.0755
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1340P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1878
_refine_ls_wR_factor_ref         0.2177
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5305
_reflns_number_total             9920
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt00617d3.cif
_cod_data_source_block           1d
_cod_database_code               7713099
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.936
_shelx_estimated_absorpt_t_max   0.984
_platon_squeeze_void_probe_radius 1.20
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.27562(7) -0.07785(6) 0.23045(3) 0.0211(2) Uani 1 1 d . . . . .
Cu2 Cu 0.16790(6) 0.11118(6) 0.19183(3) 0.0215(2) Uani 1 1 d . . . . .
O1 O 0.2423(4) -0.4781(3) 0.2131(2) 0.0344(11) Uani 1 1 d . . . . .
O2 O 0.4065(4) -0.1473(3) 0.1184(2) 0.0286(10) Uani 1 1 d . . . . .
O3 O 0.3126(4) 0.4329(3) 0.0575(2) 0.0321(11) Uani 1 1 d . . . . .
O4 O 0.2303(4) 0.0590(4) 0.0598(2) 0.0322(11) Uani 1 1 d . . . . .
N1 N 0.1622(4) -0.1466(4) 0.1949(2) 0.0186(11) Uani 1 1 d . . . . .
N2 N -0.0028(4) 0.0821(4) 0.2234(2) 0.0232(12) Uani 1 1 d . . . . .
N3 N 0.3339(4) 0.1441(4) 0.1567(2) 0.0183(11) Uani 1 1 d . . . . .
N4 N 0.3922(5) -0.0163(4) 0.2691(2) 0.0239(12) Uani 1 1 d . . . . .
C1 C 0.3240(6) -0.3148(5) 0.1639(3) 0.0228(14) Uani 1 1 d . . . . .
C2 C 0.0304(6) -0.1134(5) 0.1949(3) 0.0263(15) Uani 1 1 d . . . . .
C3 C -0.0217(6) -0.2011(5) 0.1738(3) 0.0281(15) Uani 1 1 d . . . . .
H3 H -0.108490 -0.201120 0.170343 0.034 Uiso 1 1 calc R U . . .
C4 C 0.0797(6) -0.2871(5) 0.1592(3) 0.0305(16) Uani 1 1 d . . . . .
H4 H 0.074567 -0.355142 0.143571 0.037 Uiso 1 1 calc R U . . .
C5 C 0.1914(6) -0.2514(5) 0.1727(3) 0.0231(14) Uani 1 1 d . . . . .
C6 C -0.0450(5) -0.0104(5) 0.2138(3) 0.0222(14) Uani 1 1 d . . . . .
C7 C 0.4325(5) -0.2628(5) 0.1327(3) 0.0230(14) Uani 1 1 d . . . . .
C8 C 0.5520(6) -0.3253(6) 0.1185(3) 0.0307(16) Uani 1 1 d . . . . .
H8 H 0.621208 -0.289998 0.097523 0.037 Uiso 1 1 calc R U . . .
C9 C 0.5695(6) -0.4408(6) 0.1354(3) 0.0347(17) Uani 1 1 d . . . . .
H9 H 0.650907 -0.482809 0.125059 0.042 Uiso 1 1 calc R U . . .
C10 C 0.4712(6) -0.4954(5) 0.1667(3) 0.0305(16) Uani 1 1 d . . . . .
H10 H 0.485783 -0.573431 0.177770 0.037 Uiso 1 1 calc R U . . .
C11 C 0.3457(6) -0.4321(5) 0.1824(3) 0.0262(14) Uani 1 1 d . . . . .
C12 C 0.2610(8) -0.5967(6) 0.2337(4) 0.047(2) Uani 1 1 d . . . . .
H12A H 0.287033 -0.640258 0.198498 0.071 Uiso 1 1 calc R U . . .
H12B H 0.181260 -0.617773 0.256447 0.071 Uiso 1 1 calc R U . . .
H12C H 0.327351 -0.611791 0.259940 0.071 Uiso 1 1 calc R U . . .
C13 C 0.5085(6) -0.0922(6) 0.0832(3) 0.0393(18) Uani 1 1 d . . . . .
H13A H 0.580881 -0.102480 0.105807 0.059 Uiso 1 1 calc R U . . .
H13B H 0.478386 -0.012307 0.075796 0.059 Uiso 1 1 calc R U . . .
H13C H 0.535220 -0.124689 0.044395 0.059 Uiso 1 1 calc R U . . .
C14 C -0.1050(6) 0.1645(5) 0.2519(3) 0.0294(15) Uani 1 1 d . . . . .
C15 C -0.1715(7) 0.1351(6) 0.3107(3) 0.0375(18) Uani 1 1 d . . . . .
C16 C -0.2773(8) 0.2119(7) 0.3339(4) 0.063(3) Uani 1 1 d . . . . .
H16 H -0.325567 0.192051 0.371904 0.075 Uiso 1 1 calc R U . . .
C17 C -0.3133(9) 0.3169(7) 0.3025(4) 0.069(3) Uani 1 1 d . . . . .
H17 H -0.384789 0.366595 0.318600 0.083 Uiso 1 1 calc R U . . .
C18 C -0.2392(8) 0.3453(6) 0.2463(4) 0.052(2) Uani 1 1 d . . . . .
H18 H -0.261307 0.416087 0.225198 0.063 Uiso 1 1 calc R U . . .
C19 C -0.1337(6) 0.2727(5) 0.2204(3) 0.0322(16) Uani 1 1 d . . . . .
C20 C -0.0608(6) 0.3069(5) 0.1578(3) 0.0281(15) Uani 1 1 d . . . . .
H20 H 0.024306 0.259206 0.153618 0.034 Uiso 1 1 calc R U . . .
C21 C -0.1318(7) 0.2816(6) 0.1075(3) 0.0397(18) Uani 1 1 d . . . . .
H21A H -0.138347 0.201671 0.111381 0.060 Uiso 1 1 calc R U . . .
H21B H -0.084662 0.302307 0.067664 0.060 Uiso 1 1 calc R U . . .
H21C H -0.217263 0.324649 0.111584 0.060 Uiso 1 1 calc R U . . .
C22 C -0.0377(6) 0.4309(6) 0.1499(4) 0.0388(18) Uani 1 1 d . . . . .
H22A H -0.118162 0.479716 0.146005 0.058 Uiso 1 1 calc R U . . .
H22B H 0.023798 0.443446 0.113341 0.058 Uiso 1 1 calc R U . . .
H22C H -0.004110 0.447523 0.185409 0.058 Uiso 1 1 calc R U . . .
C23 C -0.1341(7) 0.0282(6) 0.3514(3) 0.0397(18) Uani 1 1 d . . . . .
H23 H -0.047331 -0.007505 0.334344 0.048 Uiso 1 1 calc R U . . .
C24 C -0.2258(8) -0.0561(7) 0.3569(4) 0.063(3) Uani 1 1 d . . . . .
H24A H -0.311404 -0.021809 0.373275 0.095 Uiso 1 1 calc R U . . .
H24B H -0.198371 -0.120973 0.384307 0.095 Uiso 1 1 calc R U . . .
H24C H -0.226890 -0.080061 0.316827 0.095 Uiso 1 1 calc R U . . .
C25 C -0.1316(9) 0.0550(8) 0.4195(4) 0.071(3) Uani 1 1 d . . . . .
H25A H -0.218591 0.064949 0.441376 0.107 Uiso 1 1 calc R U . . .
H25B H -0.094175 0.123559 0.418569 0.107 Uiso 1 1 calc R U . . .
H25C H -0.080350 -0.007120 0.440174 0.107 Uiso 1 1 calc R U . . .
C26 C 0.2691(5) 0.2464(5) 0.0572(3) 0.0223(14) Uani 1 1 d . . . . .
C27 C 0.4452(5) 0.1276(5) 0.1839(3) 0.0210(13) Uani 1 1 d . . . . .
C28 C 0.5409(5) 0.1817(5) 0.1476(3) 0.0277(15) Uani 1 1 d . . . . .
H28 H 0.623766 0.183603 0.156574 0.033 Uiso 1 1 calc R U . . .
C29 C 0.4898(6) 0.2329(5) 0.0951(3) 0.0285(15) Uani 1 1 d . . . . .
H29 H 0.531570 0.275437 0.061895 0.034 Uiso 1 1 calc R U . . .
C30 C 0.3634(5) 0.2078(5) 0.1023(3) 0.0213(13) Uani 1 1 d . . . . .
C31 C 0.4626(5) 0.0605(5) 0.2406(3) 0.0235(14) Uani 1 1 d . . . . .
C32 C 0.2068(5) 0.1688(5) 0.0341(3) 0.0237(14) Uani 1 1 d . . . . .
C33 C 0.1297(6) 0.2020(6) -0.0120(3) 0.0311(16) Uani 1 1 d . . . . .
H33 H 0.090128 0.149206 -0.027344 0.037 Uiso 1 1 calc R U . . .
C34 C 0.1126(6) 0.3170(6) -0.0349(3) 0.0299(15) Uani 1 1 d . . . . .
H34 H 0.061338 0.340473 -0.065969 0.036 Uiso 1 1 calc R U . . .
C35 C 0.1701(6) 0.3959(5) -0.0122(3) 0.0296(15) Uani 1 1 d . . . . .
H35 H 0.155488 0.472344 -0.026961 0.035 Uiso 1 1 calc R U . . .
C36 C 0.2499(5) 0.3611(5) 0.0328(3) 0.0200(13) Uani 1 1 d . . . . .
C37 C 0.3116(7) 0.5453(5) 0.0284(3) 0.0370(17) Uani 1 1 d . . . . .
H37A H 0.342115 0.542484 -0.015139 0.055 Uiso 1 1 calc R U . . .
H37B H 0.367236 0.584215 0.046348 0.055 Uiso 1 1 calc R U . . .
H37C H 0.224594 0.585344 0.034128 0.055 Uiso 1 1 calc R U . . .
C38 C 0.1701(8) -0.0256(6) 0.0383(3) 0.0437(19) Uani 1 1 d . . . . .
H38A H 0.077530 -0.003920 0.044316 0.066 Uiso 1 1 calc R U . . .
H38B H 0.191478 -0.097829 0.061254 0.066 Uiso 1 1 calc R U . . .
H38C H 0.200867 -0.031710 -0.004905 0.066 Uiso 1 1 calc R U . . .
C39 C 0.4147(5) -0.0578(5) 0.3309(3) 0.0222(14) Uani 1 1 d . . . . .
C40 C 0.3802(6) 0.0151(6) 0.3775(3) 0.0299(15) Uani 1 1 d . . . . .
C41 C 0.4025(7) -0.0279(6) 0.4367(3) 0.0387(17) Uani 1 1 d . . . . .
H41 H 0.379892 0.019921 0.468469 0.046 Uiso 1 1 calc R U . . .
C42 C 0.4567(7) -0.1384(6) 0.4501(3) 0.0390(18) Uani 1 1 d . . . . .
H42 H 0.471335 -0.164615 0.490275 0.047 Uiso 1 1 calc R U . . .
C43 C 0.4893(7) -0.2100(6) 0.4035(3) 0.0367(17) Uani 1 1 d . . . . .
H43 H 0.525274 -0.285224 0.412834 0.044 Uiso 1 1 calc R U . . .
C44 C 0.4702(6) -0.1734(5) 0.3431(3) 0.0280(15) Uani 1 1 d . . . . .
C45 C 0.5100(6) -0.2497(5) 0.2917(3) 0.0318(16) Uani 1 1 d . . . . .
H45 H 0.447935 -0.226760 0.262247 0.038 Uiso 1 1 calc R U . . .
C46 C 0.5068(8) -0.3754(6) 0.3117(3) 0.049(2) Uani 1 1 d . . . . .
H46A H 0.578792 -0.405023 0.333411 0.074 Uiso 1 1 calc R U . . .
H46B H 0.512655 -0.415947 0.275839 0.074 Uiso 1 1 calc R U . . .
H46C H 0.426951 -0.384823 0.338531 0.074 Uiso 1 1 calc R U . . .
C47 C 0.6442(7) -0.2345(7) 0.2564(4) 0.050(2) Uani 1 1 d . . . . .
H47A H 0.644692 -0.156273 0.240307 0.074 Uiso 1 1 calc R U . . .
H47B H 0.664539 -0.282224 0.222857 0.074 Uiso 1 1 calc R U . . .
H47C H 0.707791 -0.255456 0.283963 0.074 Uiso 1 1 calc R U . . .
C48 C 0.3106(7) 0.1349(6) 0.3664(4) 0.0420(19) Uani 1 1 d . . . . .
H48 H 0.344142 0.162609 0.324025 0.050 Uiso 1 1 calc R U . . .
C49 C 0.1698(10) 0.1346(10) 0.3680(6) 0.100(4) Uani 1 1 d . . . . .
H49A H 0.132992 0.104885 0.408392 0.150 Uiso 1 1 calc R U . . .
H49B H 0.156738 0.087732 0.337551 0.150 Uiso 1 1 calc R U . . .
H49C H 0.128188 0.211071 0.359179 0.150 Uiso 1 1 calc R U . . .
C50 C 0.3289(12) 0.2224(9) 0.4077(6) 0.109(5) Uani 1 1 d . . . . .
H50A H 0.300048 0.297459 0.389720 0.164 Uiso 1 1 calc R U . . .
H50B H 0.419227 0.215921 0.411688 0.164 Uiso 1 1 calc R U . . .
H50C H 0.279183 0.209312 0.447859 0.164 Uiso 1 1 calc R U . . .
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'
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'
Cu Cu 0.3201 1.2651 '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'
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 N4 176.7(2) . . ?
N1 Cu1 Cu2 89.07(14) . . ?
N4 Cu1 Cu2 94.04(15) . . ?
N3 Cu2 N2 176.9(2) . . ?
N3 Cu2 Cu1 87.19(14) . . ?
N2 Cu2 Cu1 95.20(14) . . ?
C11 O1 C12 117.8(5) . . ?
C7 O2 C13 117.2(4) . . ?
C36 O3 C37 117.2(5) . . ?
C32 O4 C38 117.9(5) . . ?
C5 N1 C2 106.6(5) . . ?
C5 N1 Cu1 124.8(4) . . ?
C2 N1 Cu1 127.8(4) . . ?
C6 N2 C14 112.7(5) . . ?
C6 N2 Cu2 122.0(4) . . ?
C14 N2 Cu2 124.6(4) . . ?
C30 N3 C27 105.0(5) . . ?
C30 N3 Cu2 125.9(4) . . ?
C27 N3 Cu2 128.2(4) . . ?
C31 N4 C39 116.3(5) . . ?
C31 N4 Cu1 122.7(4) . . ?
C39 N4 Cu1 120.9(4) . . ?
C11 C1 C7 117.6(5) . . ?
C11 C1 C5 120.2(5) . . ?
C7 C1 C5 122.0(5) . . ?
N1 C2 C3 108.8(5) . . ?
N1 C2 C6 127.5(6) . . ?
C3 C2 C6 123.7(5) . . ?
C4 C3 C2 107.6(5) . . ?
C4 C3 H3 126.2 . . ?
C2 C3 H3 126.2 . . ?
C3 C4 C5 106.4(5) . . ?
C3 C4 H4 126.8 . . ?
C5 C4 H4 126.8 . . ?
N1 C5 C4 110.7(5) . . ?
N1 C5 C1 123.2(5) . . ?
C4 C5 C1 126.1(5) . . ?
N2 C6 C2 127.4(5) . . ?
C8 C7 O2 123.7(6) . . ?
C8 C7 C1 121.5(6) . . ?
O2 C7 C1 114.8(5) . . ?
C7 C8 C9 119.7(6) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 121.9(6) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C9 C10 C11 119.6(6) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
O1 C11 C1 116.2(5) . . ?
O1 C11 C10 124.1(5) . . ?
C1 C11 C10 119.7(6) . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 121.4(6) . . ?
C15 C14 N2 119.3(5) . . ?
C19 C14 N2 119.3(6) . . ?
C16 C15 C14 117.5(6) . . ?
C16 C15 C23 117.7(6) . . ?
C14 C15 C23 124.7(6) . . ?
C15 C16 C17 122.4(7) . . ?
C15 C16 H16 118.8 . . ?
C17 C16 H16 118.8 . . ?
C18 C17 C16 117.9(7) . . ?
C18 C17 H17 121.1 . . ?
C16 C17 H17 121.1 . . ?
C19 C18 C17 122.7(7) . . ?
C19 C18 H18 118.7 . . ?
C17 C18 H18 118.7 . . ?
C18 C19 C14 117.7(6) . . ?
C18 C19 C20 119.9(6) . . ?
C14 C19 C20 122.1(5) . . ?
C19 C20 C21 109.5(5) . . ?
C19 C20 C22 113.2(5) . . ?
C21 C20 C22 111.2(5) . . ?
C19 C20 H20 107.6 . . ?
C21 C20 H20 107.6 . . ?
C22 C20 H20 107.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C15 113.4(6) . . ?
C24 C23 C25 105.6(7) . . ?
C15 C23 C25 111.5(6) . . ?
C24 C23 H23 108.8 . . ?
C15 C23 H23 108.8 . . ?
C25 C23 H23 108.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C32 C26 C36 117.9(5) . . ?
C32 C26 C30 121.4(5) . . ?
C36 C26 C30 120.4(5) . . ?
N3 C27 C28 110.9(5) . . ?
N3 C27 C31 125.4(5) . . ?
C28 C27 C31 123.7(5) . . ?
C27 C28 C29 106.7(5) . . ?
C27 C28 H28 126.6 . . ?
C29 C28 H28 126.6 . . ?
C28 C29 C30 106.1(5) . . ?
C28 C29 H29 126.9 . . ?
C30 C29 H29 126.9 . . ?
N3 C30 C29 111.2(5) . . ?
N3 C30 C26 123.3(5) . . ?
C29 C30 C26 125.5(6) . . ?
N4 C31 C27 127.1(5) . . ?
O4 C32 C33 123.6(6) . . ?
O4 C32 C26 114.7(5) . . ?
C33 C32 C26 121.8(6) . . ?
C32 C33 C34 118.5(6) . . ?
C32 C33 H33 120.7 . . ?
C34 C33 H33 120.7 . . ?
C35 C34 C33 121.2(6) . . ?
C35 C34 H34 119.4 . . ?
C33 C34 H34 119.4 . . ?
C34 C35 C36 119.8(6) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
O3 C36 C35 124.0(5) . . ?
O3 C36 C26 115.2(5) . . ?
C35 C36 C26 120.8(6) . . ?
O3 C37 H37A 109.5 . . ?
O3 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O3 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
O4 C38 H38A 109.5 . . ?
O4 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O4 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C40 C39 N4 119.3(5) . . ?
C40 C39 C44 121.5(6) . . ?
N4 C39 C44 119.2(5) . . ?
C39 C40 C41 117.8(6) . . ?
C39 C40 C48 122.1(6) . . ?
C41 C40 C48 120.0(6) . . ?
C42 C41 C40 122.4(7) . . ?
C42 C41 H41 118.8 . . ?
C40 C41 H41 118.8 . . ?
C43 C42 C41 119.2(7) . . ?
C43 C42 H42 120.4 . . ?
C41 C42 H42 120.4 . . ?
C42 C43 C44 121.9(6) . . ?
C42 C43 H43 119.1 . . ?
C44 C43 H43 119.1 . . ?
C43 C44 C39 117.2(6) . . ?
C43 C44 C45 122.2(6) . . ?
C39 C44 C45 120.6(6) . . ?
C44 C45 C46 114.6(6) . . ?
C44 C45 C47 112.0(6) . . ?
C46 C45 C47 108.9(6) . . ?
C44 C45 H45 107.0 . . ?
C46 C45 H45 107.0 . . ?
C47 C45 H45 107.0 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C45 C47 H47A 109.5 . . ?
C45 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C45 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C49 C48 C50 108.7(8) . . ?
C49 C48 C40 110.9(7) . . ?
C50 C48 C40 117.5(6) . . ?
C49 C48 H48 106.3 . . ?
C50 C48 H48 106.3 . . ?
C40 C48 H48 106.3 . . ?
C48 C49 H49A 109.5 . . ?
C48 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C48 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C48 C50 H50A 109.5 . . ?
C48 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C48 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
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 1.865(5) . ?
Cu1 N4 1.882(5) . ?
Cu1 Cu2 2.4806(10) . ?
Cu2 N3 1.877(5) . ?
Cu2 N2 1.891(5) . ?
O1 C11 1.345(7) . ?
O1 C12 1.428(7) . ?
O2 C7 1.371(7) . ?
O2 C13 1.423(7) . ?
O3 C36 1.369(7) . ?
O3 C37 1.417(7) . ?
O4 C32 1.367(7) . ?
O4 C38 1.435(7) . ?
N1 C5 1.367(7) . ?
N1 C2 1.383(7) . ?
N2 C6 1.305(7) . ?
N2 C14 1.451(7) . ?
N3 C30 1.359(7) . ?
N3 C27 1.378(7) . ?
N4 C31 1.311(8) . ?
N4 C39 1.433(7) . ?
C1 C11 1.405(8) . ?
C1 C7 1.427(8) . ?
C1 C5 1.474(8) . ?
C2 C3 1.412(8) . ?
C2 C6 1.419(8) . ?
C3 C4 1.383(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(8) . ?
C4 H4 0.9300 . ?
C7 C8 1.367(8) . ?
C8 C9 1.377(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.360(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.426(8) . ?
C10 H10 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.400(9) . ?
C14 C19 1.406(9) . ?
C15 C16 1.394(9) . ?
C15 C23 1.508(9) . ?
C16 C17 1.387(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.387(11) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.508(9) . ?
C20 C21 1.513(10) . ?
C20 C22 1.523(9) . ?
C20 H20 0.9800 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.484(10) . ?
C23 C25 1.571(12) . ?
C23 H23 0.9800 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C32 1.400(8) . ?
C26 C36 1.407(8) . ?
C26 C30 1.500(8) . ?
C27 C28 1.377(8) . ?
C27 C31 1.423(8) . ?
C28 C29 1.389(9) . ?
C28 H28 0.9300 . ?
C29 C30 1.392(8) . ?
C29 H29 0.9300 . ?
C32 C33 1.383(8) . ?
C33 C34 1.400(9) . ?
C33 H33 0.9300 . ?
C34 C35 1.375(9) . ?
C34 H34 0.9300 . ?
C35 C36 1.385(8) . ?
C35 H35 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 C40 1.387(9) . ?
C39 C44 1.424(8) . ?
C40 C41 1.384(9) . ?
C40 C48 1.511(9) . ?
C41 C42 1.370(10) . ?
C41 H41 0.9300 . ?
C42 C43 1.376(10) . ?
C42 H42 0.9300 . ?
C43 C44 1.385(9) . ?
C43 H43 0.9300 . ?
C44 C45 1.498(9) . ?
C45 C46 1.518(9) . ?
C45 C47 1.525(9) . ?
C45 H45 0.9800 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C48 C49 1.480(12) . ?
C48 C50 1.514(12) . ?
C48 H48 0.9800 . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
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
Cu2 Cu1 N1 C5 149.9(5) . . . . ?
Cu2 Cu1 N1 C2 -41.8(5) . . . . ?
Cu1 Cu2 N2 C6 -49.7(5) . . . . ?
Cu1 Cu2 N2 C14 140.0(5) . . . . ?
Cu1 Cu2 N3 C30 145.1(4) . . . . ?
Cu1 Cu2 N3 C27 -47.3(5) . . . . ?
Cu2 Cu1 N4 C31 -50.3(5) . . . . ?
Cu2 Cu1 N4 C39 134.0(4) . . . . ?
C5 N1 C2 C3 1.5(7) . . . . ?
Cu1 N1 C2 C3 -168.5(4) . . . . ?
C5 N1 C2 C6 -179.7(6) . . . . ?
Cu1 N1 C2 C6 10.3(9) . . . . ?
N1 C2 C3 C4 -1.6(7) . . . . ?
C6 C2 C3 C4 179.5(6) . . . . ?
C2 C3 C4 C5 1.0(8) . . . . ?
C2 N1 C5 C4 -0.9(7) . . . . ?
Cu1 N1 C5 C4 169.5(4) . . . . ?
C2 N1 C5 C1 178.4(6) . . . . ?
Cu1 N1 C5 C1 -11.3(8) . . . . ?
C3 C4 C5 N1 -0.1(7) . . . . ?
C3 C4 C5 C1 -179.3(6) . . . . ?
C11 C1 C5 N1 136.3(6) . . . . ?
C7 C1 C5 N1 -48.6(9) . . . . ?
C11 C1 C5 C4 -44.6(9) . . . . ?
C7 C1 C5 C4 130.5(7) . . . . ?
C14 N2 C6 C2 -170.5(6) . . . . ?
Cu2 N2 C6 C2 18.1(9) . . . . ?
N1 C2 C6 N2 14.3(11) . . . . ?
C3 C2 C6 N2 -167.0(6) . . . . ?
C13 O2 C7 C8 4.4(9) . . . . ?
C13 O2 C7 C1 -175.5(6) . . . . ?
C11 C1 C7 C8 3.0(9) . . . . ?
C5 C1 C7 C8 -172.3(6) . . . . ?
C11 C1 C7 O2 -177.1(5) . . . . ?
C5 C1 C7 O2 7.6(8) . . . . ?
O2 C7 C8 C9 179.1(6) . . . . ?
C1 C7 C8 C9 -1.0(10) . . . . ?
C7 C8 C9 C10 -0.8(10) . . . . ?
C8 C9 C10 C11 0.4(10) . . . . ?
C12 O1 C11 C1 -178.8(6) . . . . ?
C12 O1 C11 C10 3.0(9) . . . . ?
C7 C1 C11 O1 178.4(5) . . . . ?
C5 C1 C11 O1 -6.2(9) . . . . ?
C7 C1 C11 C10 -3.3(9) . . . . ?
C5 C1 C11 C10 172.1(5) . . . . ?
C9 C10 C11 O1 179.8(6) . . . . ?
C9 C10 C11 C1 1.7(9) . . . . ?
C6 N2 C14 C15 61.9(8) . . . . ?
Cu2 N2 C14 C15 -127.0(6) . . . . ?
C6 N2 C14 C19 -119.2(7) . . . . ?
Cu2 N2 C14 C19 51.9(8) . . . . ?
C19 C14 C15 C16 7.3(11) . . . . ?
N2 C14 C15 C16 -173.8(7) . . . . ?
C19 C14 C15 C23 -170.6(7) . . . . ?
N2 C14 C15 C23 8.2(11) . . . . ?
C14 C15 C16 C17 -3.5(14) . . . . ?
C23 C15 C16 C17 174.6(8) . . . . ?
C15 C16 C17 C18 -0.7(15) . . . . ?
C16 C17 C18 C19 1.2(15) . . . . ?
C17 C18 C19 C14 2.5(13) . . . . ?
C17 C18 C19 C20 177.3(8) . . . . ?
C15 C14 C19 C18 -6.9(11) . . . . ?
N2 C14 C19 C18 174.3(6) . . . . ?
C15 C14 C19 C20 178.4(6) . . . . ?
N2 C14 C19 C20 -0.4(10) . . . . ?
C18 C19 C20 C21 -81.9(8) . . . . ?
C14 C19 C20 C21 92.7(7) . . . . ?
C18 C19 C20 C22 42.8(9) . . . . ?
C14 C19 C20 C22 -142.6(6) . . . . ?
C16 C15 C23 C24 73.1(10) . . . . ?
C14 C15 C23 C24 -109.0(8) . . . . ?
C16 C15 C23 C25 -45.9(10) . . . . ?
C14 C15 C23 C25 132.1(8) . . . . ?
C30 N3 C27 C28 1.1(7) . . . . ?
Cu2 N3 C27 C28 -168.5(4) . . . . ?
C30 N3 C27 C31 -176.7(5) . . . . ?
Cu2 N3 C27 C31 13.7(8) . . . . ?
N3 C27 C28 C29 -0.9(7) . . . . ?
C31 C27 C28 C29 176.9(6) . . . . ?
C27 C28 C29 C30 0.4(7) . . . . ?
C27 N3 C30 C29 -0.8(6) . . . . ?
Cu2 N3 C30 C29 169.1(4) . . . . ?
C27 N3 C30 C26 -179.8(5) . . . . ?
Cu2 N3 C30 C26 -9.9(8) . . . . ?
C28 C29 C30 N3 0.3(7) . . . . ?
C28 C29 C30 C26 179.2(6) . . . . ?
C32 C26 C30 N3 -54.7(8) . . . . ?
C36 C26 C30 N3 131.2(6) . . . . ?
C32 C26 C30 C29 126.5(7) . . . . ?
C36 C26 C30 C29 -47.6(9) . . . . ?
C39 N4 C31 C27 -169.3(5) . . . . ?
Cu1 N4 C31 C27 14.8(8) . . . . ?
N3 C27 C31 N4 16.9(10) . . . . ?
C28 C27 C31 N4 -160.6(6) . . . . ?
C38 O4 C32 C33 -0.9(9) . . . . ?
C38 O4 C32 C26 -179.9(6) . . . . ?
C36 C26 C32 O4 179.8(5) . . . . ?
C30 C26 C32 O4 5.5(8) . . . . ?
C36 C26 C32 C33 0.7(9) . . . . ?
C30 C26 C32 C33 -173.5(6) . . . . ?
O4 C32 C33 C34 -180.0(6) . . . . ?
C26 C32 C33 C34 -1.1(9) . . . . ?
C32 C33 C34 C35 -0.4(9) . . . . ?
C33 C34 C35 C36 2.0(9) . . . . ?
C37 O3 C36 C35 -10.1(8) . . . . ?
C37 O3 C36 C26 171.2(5) . . . . ?
C34 C35 C36 O3 179.0(5) . . . . ?
C34 C35 C36 C26 -2.4(9) . . . . ?
C32 C26 C36 O3 179.7(5) . . . . ?
C30 C26 C36 O3 -6.0(8) . . . . ?
C32 C26 C36 C35 1.0(9) . . . . ?
C30 C26 C36 C35 175.3(5) . . . . ?
C31 N4 C39 C40 67.8(7) . . . . ?
Cu1 N4 C39 C40 -116.2(6) . . . . ?
C31 N4 C39 C44 -113.1(6) . . . . ?
Cu1 N4 C39 C44 62.8(7) . . . . ?
N4 C39 C40 C41 179.6(6) . . . . ?
C44 C39 C40 C41 0.6(9) . . . . ?
N4 C39 C40 C48 4.5(9) . . . . ?
C44 C39 C40 C48 -174.6(6) . . . . ?
C39 C40 C41 C42 0.0(10) . . . . ?
C48 C40 C41 C42 175.2(6) . . . . ?
C40 C41 C42 C43 -0.6(11) . . . . ?
C41 C42 C43 C44 0.7(11) . . . . ?
C42 C43 C44 C39 -0.1(10) . . . . ?
C42 C43 C44 C45 177.7(7) . . . . ?
C40 C39 C44 C43 -0.5(9) . . . . ?
N4 C39 C44 C43 -179.5(5) . . . . ?
C40 C39 C44 C45 -178.3(6) . . . . ?
N4 C39 C44 C45 2.6(9) . . . . ?
C43 C44 C45 C46 29.6(9) . . . . ?
C39 C44 C45 C46 -152.7(6) . . . . ?
C43 C44 C45 C47 -95.0(8) . . . . ?
C39 C44 C45 C47 82.7(7) . . . . ?
C39 C40 C48 C49 80.5(9) . . . . ?
C41 C40 C48 C49 -94.5(9) . . . . ?
C39 C40 C48 C50 -153.6(8) . . . . ?
C41 C40 C48 C50 31.4(11) . . . . ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.038 0.500 0.500 648 215 ' '
2 0.220 0.012 0.881 25 9 ' '
3 0.780 0.988 0.119 25 9 ' '
