#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/25/7122534.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_7122534
loop_
_publ_author_name
'Titov, Aleksei'
'Larionov, Vladimir A.'
'Smol’yakov, Alexander F.'
'Godovikova, Maria I.'
'Titova, Ekaterina M.'
'Maleev, Victor I.'
'Shubina, Elena'
_publ_section_title
;
 Interaction of the trinuclear copper(I) pyrazolate with alkynes and
 carbon-carbon triple bond activation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC08592G
_journal_year                    2018
_chemical_formula_moiety         'C36 H32 Cu3 F24 N8'
_chemical_formula_sum            'C36 H32 Cu3 F24 N8'
_chemical_formula_weight         1223.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc20t5kl
_audit_creation_date             2018-10-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-03 deposited with the CCDC.
2018-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                107.62(3)
_cell_angle_beta                 100.88(2)
_cell_angle_gamma                95.18(2)
_cell_formula_units_Z            1
_cell_length_a                   8.550(9)
_cell_length_b                   10.660(12)
_cell_length_c                   13.468(14)
_cell_measurement_reflns_used    7996
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.691
_cell_measurement_theta_min      2.466
_cell_volume                     1135(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15153
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.571
_diffrn_reflns_theta_min         1.629
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.531
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0668 before and 0.0281 after correction. The Ratio of minimum to maximum transmission is 0.7654. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_description       plate
_exptl_crystal_F_000             607
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.630
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         6937
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0263
_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)+(0.0382P)²+0.2851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0717
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6032
_reflns_number_total             6937
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc08592g2.cif
_cod_data_source_block           a_CCDC1
_cod_database_code               7122534
_shelxl_version_number           2014/6
_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_max   0.927
_shelx_estimated_absorpt_t_min   0.739
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b), C14(H14a,H14b), C15(H15a,H15b), C16(H16a,H16b), C17(H17a,H17b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7)
2.c Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
Cu1 Cu 0.5000 0.5000 0.5000 0.01442(5) Uani 1 2 d S T P
Cu2 Cu 0.43469(2) 0.44466(2) 0.72231(2) 0.01892(5) Uani 1 1 d . . .
F1 F 0.32780(10) 0.32533(8) 0.28596(7) 0.02552(17) Uani 1 1 d . . .
F2 F 0.46474(12) 0.16235(10) 0.26403(7) 0.0329(2) Uani 1 1 d . . .
F3 F 0.20456(13) 0.12165(9) 0.22835(7) 0.0367(2) Uani 1 1 d . . .
F4 F 0.24084(15) 0.20060(10) 0.72197(8) 0.0437(3) Uani 1 1 d . . .
F5 F 0.38029(13) 0.04559(11) 0.67022(9) 0.0409(2) Uani 1 1 d . . .
F6 F 0.12977(12) 0.01730(10) 0.59415(8) 0.0389(2) Uani 1 1 d . . .
F7 F 0.14048(14) 0.52674(11) 0.81759(8) 0.0425(2) Uani 1 1 d . . .
F8 F 0.27247(14) 0.72556(11) 0.88412(8) 0.0421(2) Uani 1 1 d . . .
F9 F 0.01980(14) 0.69440(15) 0.81008(10) 0.0576(4) Uani 1 1 d . . .
F10 F 0.28572(13) 0.79541(9) 0.44723(8) 0.0348(2) Uani 1 1 d . . .
F11 F 0.03975(12) 0.69626(12) 0.40355(9) 0.0427(3) Uani 1 1 d . . .
F12 F 0.23098(12) 0.58440(9) 0.36037(7) 0.0319(2) Uani 1 1 d . . .
N1 N 0.40182(13) 0.31961(10) 0.49390(9) 0.0175(2) Uani 1 1 d . . .
N2 N 0.38258(13) 0.29439(11) 0.58441(9) 0.0185(2) Uani 1 1 d . . .
N3 N 0.32360(13) 0.57719(11) 0.56775(9) 0.0181(2) Uani 1 1 d . . .
N4 N 0.31147(13) 0.56625(11) 0.66400(9) 0.0192(2) Uani 1 1 d . . .
C1 C 0.33563(16) 0.20889(12) 0.40934(10) 0.0188(2) Uani 1 1 d . . .
C2 C 0.27125(17) 0.10924(13) 0.44368(11) 0.0229(3) Uani 1 1 d . . .
H2 H 0.2175 0.0219 0.4018 0.027 Uiso 1 1 calc R . .
C3 C 0.30463(16) 0.16856(13) 0.55440(11) 0.0201(2) Uani 1 1 d . . .
C4 C 0.33379(17) 0.20413(13) 0.29728(11) 0.0222(3) Uani 1 1 d . . .
C5 C 0.26412(18) 0.10854(14) 0.63523(12) 0.0259(3) Uani 1 1 d . . .
C6 C 0.19458(16) 0.63465(14) 0.69565(11) 0.0225(3) Uani 1 1 d . . .
C7 C 0.12695(17) 0.69072(15) 0.62022(12) 0.0259(3) Uani 1 1 d . . .
H7 H 0.0427 0.7431 0.6223 0.031 Uiso 1 1 calc R . .
C8 C 0.21287(16) 0.65143(13) 0.54085(11) 0.0203(2) Uani 1 1 d . . .
C9 C 0.19254(18) 0.68192(15) 0.43861(12) 0.0254(3) Uani 1 1 d . . .
C10 C 0.15600(18) 0.64539(17) 0.80139(13) 0.0299(3) Uani 1 1 d . . .
C11 C 0.5503(2) 0.52216(17) 0.87363(12) 0.0320(3) Uani 1 1 d . . .
H11 H 0.545(3) 0.600(3) 0.9135(19) 0.053(7) Uiso 1 1 d . . .
C12 C 0.58848(18) 0.41196(15) 0.84027(11) 0.0262(3) Uani 1 1 d . . .
C13 C 0.66647(18) 0.29118(15) 0.83206(13) 0.0276(3) Uani 1 1 d . . .
H13A H 0.6570 0.2410 0.7556 0.033 Uiso 1 1 calc R . .
H13B H 0.6085 0.2330 0.8629 0.033 Uiso 1 1 calc R . .
C14 C 0.84507(17) 0.32441(15) 0.89009(12) 0.0254(3) Uani 1 1 d . . .
H14A H 0.9049 0.3802 0.8583 0.030 Uiso 1 1 calc R . .
H14B H 0.8560 0.3754 0.9665 0.030 Uiso 1 1 calc R . .
C15 C 0.91586(18) 0.19548(15) 0.88018(13) 0.0289(3) Uani 1 1 d . . .
H15A H 0.8529 0.1402 0.9108 0.035 Uiso 1 1 calc R . .
H15B H 0.9023 0.1453 0.8033 0.035 Uiso 1 1 calc R . .
C16 C 1.09390(18) 0.21484(16) 0.93525(12) 0.0286(3) Uani 1 1 d . . .
H16A H 1.1079 0.2583 1.0132 0.034 Uiso 1 1 calc R . .
H16B H 1.1576 0.2741 0.9083 0.034 Uiso 1 1 calc R . .
C17 C 1.15693(19) 0.08081(18) 0.91446(15) 0.0341(3) Uani 1 1 d . . .
H17A H 1.0957 0.0235 0.9443 0.041 Uiso 1 1 calc R . .
H17B H 1.1369 0.0356 0.8363 0.041 Uiso 1 1 calc R . .
C18 C 1.3359(2) 0.0953(2) 0.96321(17) 0.0458(4) Uani 1 1 d . . .
H18A H 1.3973 0.1538 0.9355 0.069 Uiso 1 1 calc GR . .
H18B H 1.3701 0.0074 0.9444 0.069 Uiso 1 1 calc GR . .
H18C H 1.3557 0.1339 1.0412 0.069 Uiso 1 1 calc GR . .
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'
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'
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
N1 Cu1 N1 180.0 2_666 .
N1 Cu1 N3 88.84(7) . .
N1 Cu1 N3 88.84(7) 2_666 2_666
N1 Cu1 N3 91.16(7) . 2_666
N1 Cu1 N3 91.16(7) 2_666 .
N3 Cu1 N3 180.0 2_666 .
N2 Cu2 C12 114.17(9) . .
N4 Cu2 N2 94.87(9) . .
N4 Cu2 C12 150.58(6) . .
C11 Cu2 N2 149.99(7) . .
C11 Cu2 N4 115.04(8) . .
C11 Cu2 C12 35.82(8) . .
N2 N1 Cu1 120.96(9) . .
C1 N1 Cu1 130.83(11) . .
C1 N1 N2 108.07(13) . .
N1 N2 Cu2 118.88(11) . .
C3 N2 Cu2 132.92(10) . .
C3 N2 N1 107.27(12) . .
N4 N3 Cu1 119.05(9) . .
C8 N3 Cu1 132.84(10) . .
C8 N3 N4 107.90(11) . .
N3 N4 Cu2 120.04(9) . .
C6 N4 Cu2 131.95(11) . .
C6 N4 N3 107.46(11) . .
N1 C1 C2 110.39(14) . .
N1 C1 C4 121.73(13) . .
C2 C1 C4 127.87(12) . .
C1 C2 H2 128.4 . .
C1 C2 C3 103.15(13) . .
C3 C2 H2 128.4 . .
N2 C3 C2 111.12(12) . .
N2 C3 C5 121.15(13) . .
C2 C3 C5 127.73(14) . .
F1 C4 C1 111.55(11) . .
F2 C4 F1 106.45(11) . .
F2 C4 C1 113.25(12) . .
F3 C4 F1 107.06(12) . .
F3 C4 F2 106.97(14) . .
F3 C4 C1 111.20(12) . .
F4 C5 F6 107.69(14) . .
F4 C5 C3 112.03(14) . .
F5 C5 F4 106.50(14) . .
F5 C5 F6 106.11(14) . .
F5 C5 C3 112.71(14) . .
F6 C5 C3 111.43(13) . .
N4 C6 C7 111.11(13) . .
N4 C6 C10 120.36(13) . .
C7 C6 C10 128.51(14) . .
C6 C7 H7 128.5 . .
C6 C7 C8 103.09(14) . .
C8 C7 H7 128.5 . .
N3 C8 C7 110.45(13) . .
N3 C8 C9 121.95(12) . .
C7 C8 C9 127.60(13) . .
F10 C9 F12 106.10(13) . .
F10 C9 C8 113.27(13) . .
F11 C9 F10 106.43(13) . .
F11 C9 F12 107.59(13) . .
F11 C9 C8 111.18(12) . .
F12 C9 C8 111.88(13) . .
F7 C10 F8 105.64(14) . .
F7 C10 C6 112.19(13) . .
F8 C10 C6 112.36(14) . .
F9 C10 F7 107.77(14) . .
F9 C10 F8 107.00(15) . .
F9 C10 C6 111.53(13) . .
Cu2 C11 H11 123.7(16) . .
C12 C11 Cu2 73.41(11) . .
C12 C11 H11 162.8(16) . .
C11 C12 Cu2 70.76(11) . .
C11 C12 C13 162.95(15) . .
C13 C12 Cu2 126.24(11) . .
C12 C13 H13A 109.0 . .
C12 C13 H13B 109.0 . .
C12 C13 C14 112.75(13) . .
H13A C13 H13B 107.8 . .
C14 C13 H13A 109.0 . .
C14 C13 H13B 109.0 . .
C13 C14 H14A 109.7 . .
C13 C14 H14B 109.7 . .
H14A C14 H14B 108.2 . .
C15 C14 C13 109.71(13) . .
C15 C14 H14A 109.7 . .
C15 C14 H14B 109.7 . .
C14 C15 H15A 108.5 . .
C14 C15 H15B 108.5 . .
H15A C15 H15B 107.5 . .
C16 C15 C14 114.96(13) . .
C16 C15 H15A 108.5 . .
C16 C15 H15B 108.5 . .
C15 C16 H16A 109.4 . .
C15 C16 H16B 109.4 . .
C15 C16 C17 111.15(14) . .
H16A C16 H16B 108.0 . .
C17 C16 H16A 109.4 . .
C17 C16 H16B 109.4 . .
C16 C17 H17A 108.9 . .
C16 C17 H17B 108.9 . .
H17A C17 H17B 107.7 . .
C18 C17 C16 113.22(16) . .
C18 C17 H17A 108.9 . .
C18 C17 H17B 108.9 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 1.999(2) 2_666
Cu1 N1 1.999(2) .
Cu1 N3 2.0184(18) .
Cu1 N3 2.0184(18) 2_666
Cu2 N2 1.993(2) .
Cu2 N4 1.9893(18) .
Cu2 C11 1.971(2) .
Cu2 C12 2.001(2) .
F1 C4 1.350(2) .
F2 C4 1.346(2) .
F3 C4 1.3413(19) .
F4 C5 1.340(2) .
F5 C5 1.340(2) .
F6 C5 1.343(2) .
F7 C10 1.346(2) .
F8 C10 1.347(2) .
F9 C10 1.329(2) .
F10 C9 1.348(2) .
F11 C9 1.342(2) .
F12 C9 1.352(2) .
N1 N2 1.361(2) .
N1 C1 1.354(2) .
N2 C3 1.347(2) .
N3 N4 1.358(2) .
N3 C8 1.3540(19) .
N4 C6 1.348(2) .
C1 C2 1.390(2) .
C1 C4 1.492(2) .
C2 H2 0.9500 .
C2 C3 1.393(2) .
C3 C5 1.496(2) .
C6 C7 1.390(2) .
C6 C10 1.495(2) .
C7 H7 0.9500 .
C7 C8 1.392(2) .
C8 C9 1.491(2) .
C11 H11 0.86(3) .
C11 C12 1.222(3) .
C12 C13 1.487(2) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C13 C14 1.534(2) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C14 C15 1.531(3) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C15 C16 1.528(3) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C16 C17 1.538(3) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C17 C18 1.521(3) .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139189265
