#------------------------------------------------------------------------------
#$Date: 2019-11-08 00:03:35 +0200 (Fri, 08 Nov 2019) $
#$Revision: 224175 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/94/7049448.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_7049448
loop_
_publ_author_name
'Parasar, Devaborniny'
'Jayaratna, Naleen B.'
'Muñoz-Castro, Alvaro'
'Conway, Allison E.'
'Mykhailiuk, Pavel K.'
'Dias, H. V. Rasika'
_publ_section_title
;
 Carbonyl complexes of copper(i) stabilized by bridging fluorinated
 pyrazolates and halide ions.
;
_journal_issue                   19
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              6358
_journal_page_last               6371
_journal_paper_doi               10.1039/c9dt00486f
_journal_volume                  48
_journal_year                    2019
_chemical_formula_moiety         'C12 H2 Cu2 F12 N4 O2'
_chemical_formula_sum            'C12 H2 Cu2 F12 N4 O2'
_chemical_formula_weight         589.26
_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             2019-02-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-02-01 deposited with the CCDC.    2019-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                68.669(3)
_cell_angle_beta                 87.811(4)
_cell_angle_gamma                62.226(3)
_cell_formula_units_Z            3
_cell_length_a                   11.4684(14)
_cell_length_b                   11.5000(14)
_cell_length_c                   12.1867(15)
_cell_measurement_reflns_used    9900
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.96
_cell_measurement_theta_min      2.94
_cell_volume                     1307.8(3)
_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 0.989
_diffrn_measured_fraction_theta_max 0.988
_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  0.0251
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_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       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16195
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_min         2.935
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.583
_exptl_absorpt_correction_T_max  0.2251
_exptl_absorpt_correction_T_min  0.1137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0932 before and 0.0576 after correction. The Ratio of minimum to maximum transmission is 0.5051. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.245
_exptl_crystal_description       block
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.992
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.152
_refine_ls_extinction_coef       0.0310(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         7250
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0366
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0111P)²+3.5977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0877
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6890
_reflns_number_total             7250
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt00486f2.cif
_cod_data_source_block           rad667_0m_a
_cod_depositor_comments
'Adding full bibliography for 7049446--7049452.cif.'
_cod_database_code               7049448
_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   0.358
_shelx_estimated_absorpt_t_min   0.331
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C14(H14)
;
_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 0.43842(3) 0.58021(3) 0.14918(3) 0.01375(8) Uani 1 1 d .
Cu2 Cu 0.22510(3) 0.43704(3) 0.15923(3) 0.01370(8) Uani 1 1 d .
F1 F 0.13229(16) 1.04428(16) 0.12721(18) 0.0297(4) Uani 1 1 d .
F2 F 0.32431(15) 0.86576(17) 0.22172(14) 0.0231(3) Uani 1 1 d .
F3 F 0.27983(17) 0.94049(17) 0.03166(14) 0.0266(3) Uani 1 1 d .
F4 F -0.17548(14) 0.79669(16) 0.20754(16) 0.0253(3) Uani 1 1 d .
F5 F -0.04064(15) 0.56892(16) 0.28265(14) 0.0217(3) Uani 1 1 d .
F6 F -0.11042(15) 0.67876(17) 0.09405(14) 0.0232(3) Uani 1 1 d .
F7 F 0.73502(15) 0.41436(16) 0.07872(14) 0.0219(3) Uani 1 1 d .
F8 F 0.76507(17) 0.32413(19) 0.26922(14) 0.0286(3) Uani 1 1 d .
F9 F 0.85633(15) 0.18678(18) 0.1744(2) 0.0383(5) Uani 1 1 d .
F10 F 0.53250(16) -0.03630(16) 0.20543(18) 0.0299(4) Uani 1 1 d .
F11 F 0.35669(15) 0.09260(16) 0.26317(13) 0.0215(3) Uani 1 1 d .
F12 F 0.36144(17) 0.14316(18) 0.07683(14) 0.0253(3) Uani 1 1 d .
O1 O 0.6270(2) 0.6838(2) 0.1679(2) 0.0326(5) Uani 1 1 d .
O2 O 0.0338(2) 0.3356(2) 0.1425(2) 0.0299(4) Uani 1 1 d .
N1 N 0.24554(18) 0.6863(2) 0.14842(17) 0.0135(3) Uani 1 1 d .
N2 N 0.16521(18) 0.6256(2) 0.16414(17) 0.0139(3) Uani 1 1 d .
N3 N 0.50190(18) 0.3842(2) 0.15846(17) 0.0139(3) Uani 1 1 d .
N4 N 0.41851(18) 0.32844(19) 0.16286(17) 0.0128(3) Uani 1 1 d .
C1 C 0.1710(2) 0.8188(2) 0.1470(2) 0.0143(4) Uani 1 1 d .
C2 C 0.0416(2) 0.8474(2) 0.1620(2) 0.0166(4) Uani 1 1 d .
H2 H -0.030757 0.931930 0.164479 0.020 Uiso 1 1 calc R
C3 C 0.0433(2) 0.7221(2) 0.1724(2) 0.0141(4) Uani 1 1 d .
C4 C 0.2272(2) 0.9170(2) 0.1320(2) 0.0169(4) Uani 1 1 d .
C5 C -0.0700(2) 0.6913(2) 0.1890(2) 0.0161(4) Uani 1 1 d .
C6 C 0.6273(2) 0.2793(2) 0.1700(2) 0.0150(4) Uani 1 1 d .
C7 C 0.6291(2) 0.1536(2) 0.1825(2) 0.0167(4) Uani 1 1 d .
H7 H 0.703690 0.064062 0.192564 0.020 Uiso 1 1 calc R
C8 C 0.4951(2) 0.1910(2) 0.17660(19) 0.0138(4) Uani 1 1 d .
C9 C 0.7455(2) 0.3014(2) 0.1731(2) 0.0184(4) Uani 1 1 d .
C10 C 0.4368(2) 0.0980(2) 0.1801(2) 0.0160(4) Uani 1 1 d .
C11 C 0.5545(2) 0.6474(3) 0.1568(2) 0.0220(5) Uani 1 1 d .
C12 C 0.1080(2) 0.3719(3) 0.1500(2) 0.0205(4) Uani 1 1 d .
Cu3 Cu 0.39058(3) -0.06839(3) 0.50026(3) 0.01466(8) Uani 1 1 d .
F13 F 0.69486(16) -0.53980(16) 0.54200(18) 0.0315(4) Uani 1 1 d .
F14 F 0.52348(16) -0.41212(16) 0.60523(14) 0.0234(3) Uani 1 1 d .
F15 F 0.52030(16) -0.35971(18) 0.41763(14) 0.0250(3) Uani 1 1 d .
F16 F 1.01459(15) -0.30612(18) 0.47540(19) 0.0328(4) Uani 1 1 d .
F17 F 0.94217(16) -0.18474(19) 0.58593(15) 0.0281(3) Uani 1 1 d .
F18 F 0.88652(15) -0.07752(17) 0.39587(14) 0.0241(3) Uani 1 1 d .
O3 O 0.1973(2) -0.1582(2) 0.4607(2) 0.0320(4) Uani 1 1 d .
N5 N 0.58465(18) -0.1782(2) 0.50664(17) 0.0142(3) Uani 1 1 d .
N6 N 0.66757(19) -0.1213(2) 0.49687(18) 0.0149(3) Uani 1 1 d .
C13 C 0.6592(2) -0.3129(2) 0.5128(2) 0.0155(4) Uani 1 1 d .
C14 C 0.7909(2) -0.3467(2) 0.5066(2) 0.0177(4) Uani 1 1 d .
H14 H 0.863813 -0.433612 0.508613 0.021 Uiso 1 1 calc R
C15 C 0.7907(2) -0.2223(2) 0.4966(2) 0.0158(4) Uani 1 1 d .
C16 C 0.5998(2) -0.4061(2) 0.5192(2) 0.0172(4) Uani 1 1 d .
C17 C 0.9082(2) -0.1976(3) 0.4886(2) 0.0193(4) Uani 1 1 d .
C18 C 0.2712(2) -0.1269(3) 0.4788(2) 0.0214(5) 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'
O O 0.0106 0.0060 '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_3
N1 Cu1 N3 113.92(8) .
C11 Cu1 N1 123.74(9) .
C11 Cu1 N3 122.04(9) .
N4 Cu2 N2 114.00(7) .
C12 Cu2 N2 122.19(9) .
C12 Cu2 N4 123.80(9) .
N2 N1 Cu1 122.79(14) .
C1 N1 Cu1 129.40(15) .
C1 N1 N2 107.40(17) .
N1 N2 Cu2 122.60(14) .
C3 N2 Cu2 129.78(15) .
C3 N2 N1 107.40(18) .
N4 N3 Cu1 122.87(14) .
C6 N3 Cu1 129.74(15) .
C6 N3 N4 107.23(17) .
N3 N4 Cu2 122.78(14) .
C8 N4 Cu2 129.76(15) .
C8 N4 N3 107.34(17) .
N1 C1 C2 111.22(19) .
N1 C1 C4 122.23(19) .
C2 C1 C4 126.5(2) .
C1 C2 H2 128.5 .
C1 C2 C3 103.02(19) .
C3 C2 H2 128.5 .
N2 C3 C2 110.96(19) .
N2 C3 C5 121.8(2) .
C2 C3 C5 127.2(2) .
F1 C4 F2 107.30(19) .
F1 C4 C1 110.89(19) .
F2 C4 C1 112.51(19) .
F3 C4 F1 107.00(19) .
F3 C4 F2 106.40(19) .
F3 C4 C1 112.39(19) .
F4 C5 F5 107.16(18) .
F4 C5 F6 107.09(18) .
F4 C5 C3 110.40(19) .
F5 C5 C3 113.03(18) .
F6 C5 F5 105.87(19) .
F6 C5 C3 112.92(19) .
N3 C6 C7 111.32(19) .
N3 C6 C9 121.8(2) .
C7 C6 C9 126.8(2) .
C6 C7 H7 128.6 .
C8 C7 C6 102.89(19) .
C8 C7 H7 128.6 .
N4 C8 C7 111.21(19) .
N4 C8 C10 122.21(19) .
C7 C8 C10 126.5(2) .
F7 C9 C6 112.95(19) .
F8 C9 F7 105.66(19) .
F8 C9 C6 112.9(2) .
F9 C9 F7 107.5(2) .
F9 C9 F8 107.2(2) .
F9 C9 C6 110.33(19) .
F10 C10 F11 106.62(19) .
F10 C10 F12 107.91(19) .
F10 C10 C8 111.04(18) .
F11 C10 C8 112.84(19) .
F12 C10 F11 105.44(18) .
F12 C10 C8 112.61(19) .
O1 C11 Cu1 176.2(3) .
O2 C12 Cu2 178.2(2) .
N5 Cu3 N6 113.23(8) 2_656
C18 Cu3 N5 124.03(10) .
C18 Cu3 N6 122.48(10) 2_656
N6 N5 Cu3 123.09(14) .
C13 N5 Cu3 129.34(15) .
C13 N5 N6 107.44(18) .
N5 N6 Cu3 123.06(14) 2_656
C15 N6 Cu3 129.50(16) 2_656
C15 N6 N5 107.17(18) .
N5 C13 C14 111.3(2) .
N5 C13 C16 122.2(2) .
C14 C13 C16 126.4(2) .
C13 C14 H14 128.6 .
C13 C14 C15 102.9(2) .
C15 C14 H14 128.6 .
N6 C15 C14 111.2(2) .
N6 C15 C17 122.0(2) .
C14 C15 C17 126.8(2) .
F13 C16 F14 107.03(19) .
F13 C16 F15 107.8(2) .
F13 C16 C13 110.97(19) .
F14 C16 C13 112.60(19) .
F15 C16 F14 105.66(19) .
F15 C16 C13 112.40(19) .
F16 C17 F17 107.4(2) .
F16 C17 F18 107.3(2) .
F16 C17 C15 110.5(2) .
F17 C17 F18 105.8(2) .
F17 C17 C15 112.7(2) .
F18 C17 C15 112.8(2) .
O3 C18 Cu3 176.9(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 1.9647(19) .
Cu1 N3 1.9791(19) .
Cu1 C11 1.844(2) .
Cu2 N2 1.9704(19) .
Cu2 N4 1.9665(18) .
Cu2 C12 1.840(2) .
F1 C4 1.337(3) .
F2 C4 1.340(3) .
F3 C4 1.337(3) .
F4 C5 1.340(3) .
F5 C5 1.348(3) .
F6 C5 1.341(3) .
F7 C9 1.342(3) .
F8 C9 1.338(3) .
F9 C9 1.334(3) .
F10 C10 1.336(3) .
F11 C10 1.345(3) .
F12 C10 1.337(3) .
O1 C11 1.122(3) .
O2 C12 1.128(3) .
N1 N2 1.364(2) .
N1 C1 1.349(3) .
N2 C3 1.349(3) .
N3 N4 1.368(2) .
N3 C6 1.348(3) .
N4 C8 1.350(3) .
C1 C2 1.383(3) .
C1 C4 1.497(3) .
C2 H2 0.9500 .
C2 C3 1.391(3) .
C3 C5 1.486(3) .
C6 C7 1.388(3) .
C6 C9 1.495(3) .
C7 H7 0.9500 .
C7 C8 1.386(3) .
C8 C10 1.490(3) .
Cu3 N5 1.9690(19) .
Cu3 N6 1.9760(19) 2_656
Cu3 C18 1.846(3) .
F13 C16 1.334(3) .
F14 C16 1.342(3) .
F15 C16 1.342(3) .
F16 C17 1.336(3) .
F17 C17 1.340(3) .
F18 C17 1.346(3) .
O3 C18 1.119(3) .
N5 N6 1.364(3) .
N5 C13 1.350(3) .
N6 C15 1.348(3) .
C13 C14 1.380(3) .
C13 C16 1.495(3) .
C14 H14 0.9500 .
C14 C15 1.390(3) .
C15 C17 1.494(3) .
