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#$Date: 2025-08-23 01:57:28 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301878 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/10/7701042.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_7701042
loop_
_publ_author_name
'Parasar, Devaborniny'
'Ponduru, Tharun T.'
'Noonikara-Poyil, Anurag'
'Jayaratna, Naleen B.'
'Dias, H. V. Rasika'
_publ_section_title
;
 Acetylene and terminal alkyne complexes of copper(i) supported by
 fluorinated pyrazolates: syntheses, structures, and transformations.
;
_journal_issue                   42
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              15782
_journal_page_last               15794
_journal_paper_doi               10.1039/c9dt03350e
_journal_volume                  48
_journal_year                    2019
_chemical_formula_moiety         'C22 H20 Cu2 F12 N4'
_chemical_formula_sum            'C22 H20 Cu2 F12 N4'
_chemical_formula_weight         695.50
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-06-18 deposited with the CCDC.    2019-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                97.7580(10)
_cell_angle_beta                 90.3530(10)
_cell_angle_gamma                107.1170(10)
_cell_formula_units_Z            2
_cell_length_a                   8.4602(3)
_cell_length_b                   9.2660(4)
_cell_length_c                   17.3777(7)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.41
_cell_measurement_theta_min      3.03
_cell_volume                     1288.50(9)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
'Bruker D8 Quest with a Photon 100 CMOS detector'
_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  0.0196
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17811
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.414
_diffrn_reflns_theta_min         2.755
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.757
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6680
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0499 before and 0.0366 after correction. The Ratio of minimum to maximum transmission is 0.8953. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.793
_exptl_crystal_description       plates
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.642
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         7741
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0274
_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)+(0.0308P)²+0.8429P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0685
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6796
_reflns_number_total             7741
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt03350e2.cif
_cod_data_source_block           rad517_0m_a
_cod_depositor_comments
'Adding full bibliography for 7701037--7701042.cif.'
_cod_database_code               7701042
_shelx_shelxl_version_number     2014/7
_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   0.957
_shelx_estimated_absorpt_t_min   0.678
_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:
 C15(H15A,H15B), C18(H18A,H18B), C16(H16A,H16B), C17(H17A,H17B), C21(H21A,
 H21B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C2(H2)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C11(H11A,H11B,H11C)
;
_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
Cu1 Cu 0.35783(2) 0.70080(2) 0.76353(2) 0.01147(5) Uani 1 1 d .
Cu2 Cu 0.61981(2) 0.62642(2) 0.27280(2) 0.01143(5) Uani 1 1 d .
F8 F 0.73593(15) 0.87928(11) 0.16241(6) 0.0293(2) Uani 1 1 d .
F12 F 0.66445(14) 0.14009(11) 0.04844(7) 0.0306(2) Uani 1 1 d .
F2 F 0.08435(15) 0.81730(12) 0.70497(6) 0.0308(2) Uani 1 1 d .
F9 F 0.53253(14) 0.78022(13) 0.07907(7) 0.0323(2) Uani 1 1 d .
F7 F 0.78018(15) 0.84925(12) 0.03978(6) 0.0294(2) Uani 1 1 d .
F10 F 0.83334(16) 0.27045(13) -0.02503(6) 0.0335(3) Uani 1 1 d .
F6 F -0.12302(13) 0.10175(12) 0.57562(7) 0.0319(2) Uani 1 1 d .
F1 F 0.08475(18) 0.78392(13) 0.58120(7) 0.0381(3) Uani 1 1 d .
F11 F 0.91479(17) 0.25300(15) 0.08907(8) 0.0457(4) Uani 1 1 d .
F4 F 0.12941(15) 0.13161(14) 0.55308(9) 0.0487(4) Uani 1 1 d .
N3 N 0.66478(16) 0.56368(14) 0.16410(7) 0.0134(2) Uani 1 1 d .
N1 N 0.18767(15) 0.56315(13) 0.68664(7) 0.0120(2) Uani 1 1 d .
N2 N 0.19076(15) 0.41639(13) 0.67611(7) 0.0123(2) Uani 1 1 d .
N4 N 0.68796(16) 0.42404(13) 0.15056(7) 0.0133(2) Uani 1 1 d .
F3 F -0.14056(15) 0.69604(15) 0.63818(11) 0.0552(4) Uani 1 1 d .
F5 F 0.0452(3) 0.10124(14) 0.66730(8) 0.0662(6) Uani 1 1 d .
C19 C 0.47458(18) 0.66889(16) 0.35547(8) 0.0139(2) Uani 1 1 d .
C14 C 0.51243(18) 0.87183(16) 0.71922(8) 0.0150(3) Uani 1 1 d .
C8 C 0.74326(18) 0.40738(16) 0.07864(8) 0.0144(3) Uani 1 1 d .
C15 C 0.49886(19) 0.90333(16) 0.63851(8) 0.0146(3) Uani 1 1 d .
H15A H 0.5900 0.9949 0.6308 0.018 Uiso 1 1 calc R
H15B H 0.3929 0.9255 0.6303 0.018 Uiso 1 1 calc R
C18 C 0.49551(18) 0.65513(16) 0.43863(8) 0.0136(2) Uani 1 1 d .
H18A H 0.6037 0.6376 0.4474 0.016 Uiso 1 1 calc R
H18B H 0.4080 0.5647 0.4508 0.016 Uiso 1 1 calc R
C6 C 0.70621(18) 0.63110(16) 0.10025(8) 0.0144(3) Uani 1 1 d .
C3 C 0.06279(18) 0.33487(16) 0.62699(8) 0.0139(3) Uani 1 1 d .
C13 C 0.56319(19) 0.87299(17) 0.78600(9) 0.0172(3) Uani 1 1 d .
C1 C 0.05806(18) 0.56951(16) 0.64383(8) 0.0141(3) Uani 1 1 d .
C20 C 0.41315(18) 0.68336(17) 0.29343(8) 0.0150(3) Uani 1 1 d .
C16 C 0.50652(19) 0.76897(16) 0.57843(8) 0.0143(3) Uani 1 1 d .
H16A H 0.6139 0.7491 0.5860 0.017 Uiso 1 1 calc R
H16B H 0.4177 0.6768 0.5877 0.017 Uiso 1 1 calc R
C9 C 0.6895(2) 0.78479(18) 0.09570(9) 0.0193(3) Uani 1 1 d .
C7 C 0.75770(19) 0.53658(17) 0.04359(8) 0.0164(3) Uani 1 1 d .
H7 H 0.7939 0.5555 -0.0067 0.020 Uiso 1 1 calc R
C17 C 0.48758(18) 0.79529(16) 0.49469(8) 0.0126(2) Uani 1 1 d .
H17A H 0.5771 0.8860 0.4844 0.015 Uiso 1 1 calc R
H17B H 0.3802 0.8147 0.4863 0.015 Uiso 1 1 calc R
C10 C 0.7881(2) 0.26747(17) 0.04822(9) 0.0178(3) Uani 1 1 d .
C2 C -0.02632(18) 0.42707(17) 0.60428(9) 0.0164(3) Uani 1 1 d .
H2 H -0.1217 0.3994 0.5700 0.020 Uiso 1 1 calc R
C4 C 0.0209(2) 0.71626(18) 0.64240(10) 0.0209(3) Uani 1 1 d .
C21 C 0.2979(2) 0.7061(2) 0.23523(9) 0.0208(3) Uani 1 1 d .
H21A H 0.3610 0.7790 0.2017 0.025 Uiso 1 1 calc R
H21B H 0.2173 0.7513 0.2624 0.025 Uiso 1 1 calc R
C5 C 0.0298(2) 0.16761(18) 0.60614(10) 0.0204(3) Uani 1 1 d .
C12 C 0.6657(2) 0.9110(2) 0.85985(9) 0.0246(3) Uani 1 1 d .
H12A H 0.6448 0.8184 0.8855 0.029 Uiso 1 1 calc R
H12B H 0.6316 0.9885 0.8951 0.029 Uiso 1 1 calc R
C22 C 0.2043(2) 0.5575(2) 0.18462(11) 0.0326(4) Uani 1 1 d .
H22A H 0.1279 0.5775 0.1478 0.049 Uiso 1 1 calc GR
H22B H 0.1416 0.4848 0.2176 0.049 Uiso 1 1 calc GR
H22C H 0.2833 0.5145 0.1559 0.049 Uiso 1 1 calc GR
C11 C 0.8480(2) 0.9709(3) 0.84768(11) 0.0321(4) Uani 1 1 d .
H11A H 0.8830 0.8939 0.8136 0.048 Uiso 1 1 calc GR
H11B H 0.9099 0.9936 0.8979 0.048 Uiso 1 1 calc GR
H11C H 0.8700 1.0642 0.8236 0.048 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 N4 97.89(5) . 2_666
N1 Cu1 C14 113.33(5) . .
N4 Cu1 C14 147.53(6) 2_666 .
C13 Cu1 N1 149.06(6) . .
C13 Cu1 N4 111.53(6) . 2_666
C13 Cu1 C14 36.26(6) . .
N3 Cu2 N2 97.80(5) . 2_666
N3 Cu2 C20 118.36(6) . .
C19 Cu2 N3 153.16(6) . .
C19 Cu2 N2 107.14(6) . 2_666
C19 Cu2 C20 36.31(6) . .
C20 Cu2 N2 143.43(5) . 2_666
N4 N3 Cu2 114.39(9) . .
C6 N3 Cu2 136.84(10) . .
C6 N3 N4 107.68(11) . .
N2 N1 Cu1 114.13(9) . .
C1 N1 Cu1 138.13(10) . .
C1 N1 N2 107.55(11) . .
N1 N2 Cu2 116.83(9) . 2_666
C3 N2 Cu2 135.38(10) . 2_666
C3 N2 N1 107.62(11) . .
N3 N4 Cu1 116.79(9) . 2_666
C8 N4 Cu1 135.53(10) . 2_666
C8 N4 N3 107.65(11) . .
C18 C19 Cu2 125.59(10) . .
C20 C19 Cu2 72.75(9) . .
C20 C19 C18 161.30(15) . .
C15 C14 Cu1 124.74(10) . .
C13 C14 Cu1 71.56(10) . .
C13 C14 C15 163.40(15) . .
N4 C8 C7 110.93(13) . .
N4 C8 C10 120.35(13) . .
C7 C8 C10 128.63(13) . .
C14 C15 H15A 109.2 . .
C14 C15 H15B 109.2 . .
C14 C15 C16 112.06(12) . .
H15A C15 H15B 107.9 . .
C16 C15 H15A 109.2 . .
C16 C15 H15B 109.2 . .
C19 C18 H18A 108.8 . .
C19 C18 H18B 108.8 . .
C19 C18 C17 113.97(11) . .
H18A C18 H18B 107.7 . .
C17 C18 H18A 108.8 . .
C17 C18 H18B 108.8 . .
N3 C6 C9 120.94(13) . .
N3 C6 C7 110.90(13) . .
C7 C6 C9 128.13(13) . .
N2 C3 C2 110.89(13) . .
N2 C3 C5 120.34(13) . .
C2 C3 C5 128.73(14) . .
C14 C13 Cu1 72.18(10) . .
C14 C13 C12 163.06(16) . .
C12 C13 Cu1 124.68(12) . .
N1 C1 C2 111.07(12) . .
N1 C1 C4 120.87(13) . .
C2 C1 C4 128.06(13) . .
C19 C20 Cu2 70.94(9) . .
C19 C20 C21 162.03(15) . .
C21 C20 Cu2 126.90(11) . .
C15 C16 H16A 108.9 . .
C15 C16 H16B 108.9 . .
H16A C16 H16B 107.7 . .
C17 C16 C15 113.56(12) . .
C17 C16 H16A 108.9 . .
C17 C16 H16B 108.9 . .
F8 C9 F9 106.04(13) . .
F8 C9 F7 107.97(14) . .
F8 C9 C6 112.52(13) . .
F9 C9 C6 112.37(13) . .
F7 C9 F9 106.47(13) . .
F7 C9 C6 111.12(13) . .
C8 C7 H7 128.6 . .
C6 C7 C8 102.83(13) . .
C6 C7 H7 128.6 . .
C18 C17 H17A 109.6 . .
C18 C17 H17B 109.6 . .
C16 C17 C18 110.06(11) . .
C16 C17 H17A 109.6 . .
C16 C17 H17B 109.6 . .
H17A C17 H17B 108.2 . .
F12 C10 F10 106.66(13) . .
F12 C10 F11 106.83(14) . .
F12 C10 C8 113.18(13) . .
F10 C10 C8 110.95(13) . .
F11 C10 F10 106.69(14) . .
F11 C10 C8 112.14(13) . .
C3 C2 H2 128.6 . .
C1 C2 C3 102.86(13) . .
C1 C2 H2 128.6 . .
F2 C4 F1 105.75(14) . .
F2 C4 C1 112.45(13) . .
F1 C4 C1 111.95(14) . .
F3 C4 F2 107.74(15) . .
F3 C4 F1 107.18(15) . .
F3 C4 C1 111.43(14) . .
C20 C21 H21A 109.2 . .
C20 C21 H21B 109.2 . .
C20 C21 C22 112.23(15) . .
H21A C21 H21B 107.9 . .
C22 C21 H21A 109.2 . .
C22 C21 H21B 109.2 . .
F6 C5 F4 105.68(13) . .
F6 C5 C3 111.26(13) . .
F4 C5 C3 112.79(14) . .
F5 C5 F6 107.07(15) . .
F5 C5 F4 107.67(16) . .
F5 C5 C3 112.00(13) . .
C13 C12 H12A 109.1 . .
C13 C12 H12B 109.1 . .
C13 C12 C11 112.71(15) . .
H12A C12 H12B 107.8 . .
C11 C12 H12A 109.1 . .
C11 C12 H12B 109.1 . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22B 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C12 C11 H11A 109.5 . .
C12 C11 H11B 109.5 . .
C12 C11 H11C 109.5 . .
H11A C11 H11B 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 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 1.9799(12) .
Cu1 N4 1.9816(12) 2_666
Cu1 C14 1.9841(15) .
Cu1 C13 1.9770(15) .
Cu2 N3 1.9731(12) .
Cu2 N2 1.9915(12) 2_666
Cu2 C19 1.9704(14) .
Cu2 C20 1.9908(14) .
F8 C9 1.3351(18) .
F12 C10 1.3274(19) .
F2 C4 1.330(2) .
F9 C9 1.344(2) .
F7 C9 1.3363(18) .
F10 C10 1.3330(18) .
F6 C5 1.3282(19) .
F1 C4 1.343(2) .
F11 C10 1.3310(19) .
F4 C5 1.328(2) .
N3 N4 1.3549(16) .
N3 C6 1.3445(18) .
N1 N2 1.3554(16) .
N1 C1 1.3413(18) .
N2 Cu2 1.9915(12) 2_666
N2 C3 1.3433(18) .
N4 Cu1 1.9816(12) 2_666
N4 C8 1.3425(18) .
F3 C4 1.323(2) .
F5 C5 1.322(2) .
C19 C18 1.4819(19) .
C19 C20 1.234(2) .
C14 C15 1.481(2) .
C14 C13 1.233(2) .
C8 C7 1.390(2) .
C8 C10 1.487(2) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C15 C16 1.5303(19) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C18 C17 1.5332(19) .
C6 C9 1.484(2) .
C6 C7 1.387(2) .
C3 C2 1.386(2) .
C3 C5 1.484(2) .
C13 C12 1.486(2) .
C1 C2 1.385(2) .
C1 C4 1.486(2) .
C20 C21 1.478(2) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C16 C17 1.5227(19) .
C7 H7 0.9500 .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C2 H2 0.9500 .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C21 C22 1.523(3) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C12 C11 1.505(3) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168342487
