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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/7/70/10/7701038.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_7701038
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         'C18 H12 Cu2 F12 N4'
_chemical_formula_sum            'C18 H12 Cu2 F12 N4'
_chemical_formula_weight         639.40
_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     dual
_audit_creation_date             2018-06-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-18 deposited with the CCDC.    2019-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                92.068(2)
_cell_angle_beta                 110.195(2)
_cell_angle_gamma                115.740(2)
_cell_formula_units_Z            2
_cell_length_a                   10.4189(5)
_cell_length_b                   10.4808(5)
_cell_length_c                   12.2860(6)
_cell_measurement_reflns_used    8933
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.72
_cell_measurement_theta_min      3.15
_cell_volume                     1106.40(10)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 0.986
_diffrn_measured_fraction_theta_max 0.971
_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  0.0224
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14149
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.722
_diffrn_reflns_theta_min         3.152
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.037
_exptl_absorpt_correction_T_max  0.3394
_exptl_absorpt_correction_T_min  0.2702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0675 before and 0.0445 after correction. The Ratio of minimum to maximum transmission is 0.7961. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.919
_exptl_crystal_description       rhomboid
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.901
_refine_diff_density_min         -0.716
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         7904
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0362
_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)+(0.0426P)²+1.0689P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0963
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6165
_reflns_number_total             7904
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt03350e2.cif
_cod_data_source_block           rad640_0m_a
_cod_depositor_comments
'Adding full bibliography for 7701037--7701042.cif.'
_cod_original_cell_volume        1106.40(9)
_cod_database_code               7701038
_shelx_shelxl_version_number     2017/1
_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   0.854
_shelx_estimated_absorpt_t_min   0.630
_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:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C15(H15)
;
_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 0.72525(3) 0.25016(3) 0.61042(2) 0.01629(6) Uani 1 1 d .
Cu2 Cu 0.40464(3) 0.79359(3) 0.19142(2) 0.01640(6) Uani 1 1 d .
F1 F 0.9680(2) 0.15096(18) 0.60228(15) 0.0388(4) Uani 1 1 d .
F2 F 0.7840(2) -0.0653(2) 0.51888(15) 0.0442(4) Uani 1 1 d .
F3 F 0.9941(2) -0.0292(2) 0.66317(18) 0.0513(5) Uani 1 1 d .
F4 F 0.6901(2) 0.06077(16) 1.01216(13) 0.0366(4) Uani 1 1 d .
F5 F 0.5434(2) -0.15606(18) 0.91083(17) 0.0525(5) Uani 1 1 d .
F6 F 0.7810(3) -0.0884(3) 1.02328(19) 0.0618(6) Uani 1 1 d .
F7 F 0.30299(19) 0.40016(19) 0.01624(14) 0.0377(4) Uani 1 1 d .
F8 F 0.2607(2) 0.57383(17) -0.04235(14) 0.0351(3) Uani 1 1 d .
F9 F 0.07310(18) 0.35415(17) -0.10087(13) 0.0360(3) Uani 1 1 d .
F10 F 0.0657(2) 0.3361(2) 0.40164(17) 0.0500(5) Uani 1 1 d .
F11 F -0.0165(2) 0.49055(17) 0.37173(17) 0.0416(4) Uani 1 1 d .
F12 F -0.1506(2) 0.27970(18) 0.25518(16) 0.0488(5) Uani 1 1 d .
N1 N 0.7601(2) 0.11416(18) 0.70851(15) 0.0185(3) Uani 1 1 d .
N2 N 0.7046(2) 0.09572(18) 0.79483(15) 0.0184(3) Uani 1 1 d .
N3 N 0.24389(19) 0.59587(18) 0.17644(15) 0.0164(3) Uani 1 1 d .
N4 N 0.19042(19) 0.57745(18) 0.26398(15) 0.0168(3) Uani 1 1 d .
C1 C 0.8251(2) 0.0274(2) 0.71151(19) 0.0207(4) Uani 1 1 d .
C2 C 0.8130(3) -0.0499(2) 0.8001(2) 0.0257(4) Uani 1 1 d .
H2 H 0.848460 -0.118700 0.821391 0.031 Uiso 1 1 calc R
C3 C 0.7362(3) -0.0019(2) 0.84978(19) 0.0217(4) Uani 1 1 d .
C4 C 0.8930(3) 0.0210(3) 0.6249(2) 0.0288(5) Uani 1 1 d .
C5 C 0.6869(3) -0.0472(2) 0.9482(2) 0.0264(4) Uani 1 1 d .
C6 C 0.6136(3) 0.1585(3) 0.4408(2) 0.0257(4) Uani 1 1 d .
H6 H 0.596(4) 0.071(4) 0.407(3) 0.038(9) Uiso 1 1 d .
C7 C 0.6109(3) 0.2733(2) 0.45179(19) 0.0228(4) Uani 1 1 d .
C8 C 0.5754(3) 0.3945(3) 0.4289(2) 0.0262(4) Uani 1 1 d .
H8A H 0.628638 0.468351 0.503965 0.031 Uiso 1 1 calc R
H8B H 0.462058 0.357264 0.403302 0.031 Uiso 1 1 calc R
C9 C 0.6249(3) 0.4673(2) 0.33409(19) 0.0227(4) Uani 1 1 d .
H9A H 0.736858 0.499530 0.356148 0.027 Uiso 1 1 calc R
H9B H 0.565435 0.396640 0.256686 0.027 Uiso 1 1 calc R
C10 C 0.5955(3) 0.5972(2) 0.32297(19) 0.0219(4) Uani 1 1 d .
H10A H 0.659224 0.669057 0.399743 0.026 Uiso 1 1 calc R
H10B H 0.484786 0.564842 0.306314 0.026 Uiso 1 1 calc R
C11 C 0.6339(2) 0.6704(2) 0.22495(19) 0.0217(4) Uani 1 1 d .
H11A H 0.744454 0.702438 0.241224 0.026 Uiso 1 1 calc R
H11B H 0.569590 0.598948 0.147955 0.026 Uiso 1 1 calc R
C12 C 0.6057(2) 0.7971(2) 0.21574(18) 0.0207(4) Uani 1 1 d .
C13 C 0.6221(3) 0.9200(2) 0.2187(2) 0.0240(4) Uani 1 1 d .
H13 H 0.668(4) 1.020(4) 0.224(3) 0.045(9) Uiso 1 1 d .
C14 C 0.1624(2) 0.4688(2) 0.09656(18) 0.0181(3) Uani 1 1 d .
C15 C 0.0540(2) 0.3656(2) 0.1300(2) 0.0218(4) Uani 1 1 d .
H15 H -0.018825 0.267606 0.089782 0.026 Uiso 1 1 calc R
C16 C 0.0771(2) 0.4399(2) 0.23693(19) 0.0192(4) Uani 1 1 d .
C17 C 0.1993(3) 0.4503(2) -0.00744(19) 0.0236(4) Uani 1 1 d .
C18 C -0.0060(3) 0.3865(2) 0.3159(2) 0.0268(4) Uani 1 1 d .
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 100.29(7) . 2_666
N1 Cu1 C7 146.56(8) . .
N4 Cu1 C7 111.41(8) 2_666 .
C6 Cu1 N1 112.13(9) . .
C6 Cu1 N4 147.31(9) . 2_666
C6 Cu1 C7 35.98(9) . .
N2 Cu2 C12 147.72(8) 2_666 .
N3 Cu2 N2 99.78(7) . 2_666
N3 Cu2 C12 110.87(8) . .
C13 Cu2 N2 112.63(9) . 2_666
C13 Cu2 N3 146.77(9) . .
C13 Cu2 C12 35.94(9) . .
N2 N1 Cu1 116.37(13) . .
C1 N1 Cu1 135.92(15) . .
C1 N1 N2 107.70(17) . .
N1 N2 Cu2 116.88(13) . 2_666
C3 N2 Cu2 135.42(15) . 2_666
C3 N2 N1 107.66(17) . .
N4 N3 Cu2 115.71(12) . .
C14 N3 Cu2 136.71(14) . .
C14 N3 N4 107.48(16) . .
N3 N4 Cu1 117.65(12) . 2_666
C16 N4 Cu1 134.19(14) . 2_666
C16 N4 N3 107.90(16) . .
N1 C1 C2 110.87(19) . .
N1 C1 C4 120.3(2) . .
C2 C1 C4 128.8(2) . .
C1 C2 H2 128.6 . .
C1 C2 C3 102.83(19) . .
C3 C2 H2 128.6 . .
N2 C3 C2 110.9(2) . .
N2 C3 C5 120.44(19) . .
C2 C3 C5 128.6(2) . .
F1 C4 F2 105.5(2) . .
F1 C4 C1 112.76(19) . .
F2 C4 C1 112.2(2) . .
F3 C4 F1 107.1(2) . .
F3 C4 F2 107.2(2) . .
F3 C4 C1 111.7(2) . .
F4 C5 C3 112.03(18) . .
F5 C5 F4 106.0(2) . .
F5 C5 F6 107.5(2) . .
F5 C5 C3 113.2(2) . .
F6 C5 F4 106.6(2) . .
F6 C5 C3 111.1(2) . .
Cu1 C6 H6 126(2) . .
C7 C6 Cu1 73.47(14) . .
C7 C6 H6 161(2) . .
C6 C7 Cu1 70.55(14) . .
C6 C7 C8 163.4(2) . .
C8 C7 Cu1 125.75(16) . .
C7 C8 H8A 108.9 . .
C7 C8 H8B 108.9 . .
C7 C8 C9 113.57(18) . .
H8A C8 H8B 107.7 . .
C9 C8 H8A 108.9 . .
C9 C8 H8B 108.9 . .
C8 C9 H9A 109.7 . .
C8 C9 H9B 109.7 . .
H9A C9 H9B 108.2 . .
C10 C9 C8 110.03(17) . .
C10 C9 H9A 109.7 . .
C10 C9 H9B 109.7 . .
C9 C10 H10A 109.0 . .
C9 C10 H10B 109.0 . .
C9 C10 C11 113.00(17) . .
H10A C10 H10B 107.8 . .
C11 C10 H10A 109.0 . .
C11 C10 H10B 109.0 . .
C10 C11 H11A 109.1 . .
C10 C11 H11B 109.1 . .
H11A C11 H11B 107.9 . .
C12 C11 C10 112.37(17) . .
C12 C11 H11A 109.1 . .
C12 C11 H11B 109.1 . .
C11 C12 Cu2 125.30(15) . .
C13 C12 Cu2 70.45(14) . .
C13 C12 C11 163.9(2) . .
Cu2 C13 H13 125(2) . .
C12 C13 Cu2 73.61(14) . .
C12 C13 H13 161(2) . .
N3 C14 C15 110.93(18) . .
N3 C14 C17 120.88(18) . .
C15 C14 C17 128.09(18) . .
C14 C15 H15 128.4 . .
C14 C15 C16 103.20(17) . .
C16 C15 H15 128.4 . .
N4 C16 C15 110.49(18) . .
N4 C16 C18 120.75(18) . .
C15 C16 C18 128.75(19) . .
F7 C17 C14 111.70(19) . .
F8 C17 F7 106.18(19) . .
F8 C17 F9 107.55(19) . .
F8 C17 C14 113.09(18) . .
F9 C17 F7 106.23(18) . .
F9 C17 C14 111.67(18) . .
F10 C18 C16 112.5(2) . .
F11 C18 F10 105.7(2) . .
F11 C18 F12 107.1(2) . .
F11 C18 C16 112.30(18) . .
F12 C18 F10 107.4(2) . .
F12 C18 C16 111.5(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 1.9716(17) .
Cu1 N4 1.9752(16) 2_666
Cu1 C6 1.957(2) .
Cu1 C7 1.990(2) .
Cu2 N2 1.9838(17) 2_666
Cu2 N3 1.9693(17) .
Cu2 C12 1.994(2) .
Cu2 C13 1.959(2) .
F1 C4 1.340(3) .
F2 C4 1.344(3) .
F3 C4 1.329(3) .
F4 C5 1.336(3) .
F5 C5 1.324(3) .
F6 C5 1.330(3) .
F7 C17 1.347(3) .
F8 C17 1.334(3) .
F9 C17 1.336(2) .
F10 C18 1.336(3) .
F11 C18 1.332(3) .
F12 C18 1.334(3) .
N1 N2 1.355(2) .
N1 C1 1.344(3) .
N2 C3 1.342(3) .
N3 N4 1.356(2) .
N3 C14 1.344(2) .
N4 C16 1.341(2) .
C1 C2 1.388(3) .
C1 C4 1.481(3) .
C2 H2 0.9500 .
C2 C3 1.390(3) .
C3 C5 1.487(3) .
C6 H6 0.91(3) .
C6 C7 1.219(3) .
C7 C8 1.481(3) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C8 C9 1.530(3) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C9 C10 1.521(3) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C10 C11 1.527(3) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C11 C12 1.480(3) .
C12 C13 1.220(3) .
C13 H13 0.93(3) .
C14 C15 1.381(3) .
C14 C17 1.484(3) .
C15 H15 0.9500 .
C15 C16 1.391(3) .
C16 C18 1.484(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168342485
