#------------------------------------------------------------------------------
#$Date: 2019-11-24 14:47:06 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238227 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/49/1554942.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_1554942
loop_
_publ_author_name
'Liu, He'
'Shen, Qilong'
_publ_section_title
;
 Bistrifluoromethylated organocuprate [Ph4P]+[Cu(CF3)2]−:
 synthesis, characterization and its application for trifluoromethylation
 of activated heteroaryl bromides, chlorides and iodides
;
_journal_issue                   14
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2324
_journal_paper_doi               10.1039/C9QO00527G
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C2 Cu F6, C24 H20 P'
_chemical_formula_sum            'C26 H20 Cu F6 P'
_chemical_formula_weight         540.93
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-04-18 deposited with the CCDC.	2019-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.5529(6)
_cell_length_b                   7.3629(3)
_cell_length_c                   19.8862(6)
_cell_measurement_reflns_used    5195
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.62
_cell_volume                     2277.26(15)
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.01
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12640
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_min         2.431
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.091
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0735 before and 0.0504 after correction. The Ratio of minimum to maximum transmission is 0.8576. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.959
_refine_diff_density_min         -0.799
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0459
_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)+(0.0873P)²+1.7865P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1394
_refine_ls_wR_factor_ref         0.1500
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2132
_reflns_number_total             2612
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9qo00527g2.cif
_cod_data_source_block           d8v18488
_cod_database_code               1554942
_shelxl_version_number           2013-4
_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   0.918
_shelx_estimated_absorpt_t_min   0.853
_olex2_refinement_description
;
1. Others
 Fixed U12: P1(0)
 Fixed U23: P1(0)
 Fixed Uiso: H3(0.035) H4(0.04) H5(0.04) H6(0.04) H7(0.035) H9(0.036)
 H10(0.043) H11(0.046) H12(0.046) H13(0.037)
 Fixed X: Cu1(0.5) P1(0.5) H3(0.5471) H4(0.4752) H5(0.3273) H6(0.2517)
 H7(0.3234) H9(0.4049) H10(0.313) H11(0.2797) H12(0.3376) H13(0.4295)
 Fixed Y: Cu1(0.5) H3(0.7626) H4(0.9528) H5(0.9177) H6(0.6933) H7(0.4979)
 H9(0.1529) H10(-0.0467) H11(-0.0005) H12(0.2473) H13(0.4479)
 Fixed Z: Cu1(0.5) P1(0.75) H3(0.6675) H4(0.5921) H5(0.575) H6(0.6326)
 H7(0.7057) H9(0.7132) H10(0.7694) H11(0.8824) H12(0.9399) H13(0.8848)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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 0.0333(2) Uani 1 2 d S T P
F1 F 0.39141(12) 0.2817(3) 0.57907(9) 0.0473(5) Uani 1 1 d . . .
F2 F 0.39207(17) 0.1978(4) 0.47650(14) 0.0853(10) Uani 1 1 d . . .
F3 F 0.32093(14) 0.4333(4) 0.50585(11) 0.0634(6) Uani 1 1 d . . .
C1 C 0.40013(19) 0.3496(4) 0.51462(14) 0.0370(6) Uani 1 1 d . . .
P1 P 0.5000 0.46619(13) 0.7500 0.0206(2) Uani 1 2 d S T P
C2 C 0.44238(15) 0.6109(3) 0.69328(11) 0.0224(5) Uani 1 1 d . . .
C3 C 0.48723(16) 0.7473(4) 0.65985(14) 0.0293(6) Uani 1 1 d . . .
H3 H 0.5471 0.7626 0.6675 0.035 Uiso 1 1 calc R . .
C4 C 0.44452(19) 0.8608(4) 0.61548(13) 0.0330(6) Uani 1 1 d . . .
H4 H 0.4752 0.9528 0.5921 0.040 Uiso 1 1 calc R . .
C5 C 0.35667(18) 0.8398(4) 0.60534(14) 0.0336(6) Uani 1 1 d . . .
H5 H 0.3273 0.9177 0.5750 0.040 Uiso 1 1 calc R . .
C6 C 0.31192(17) 0.7060(4) 0.63927(14) 0.0333(6) Uani 1 1 d . . .
H6 H 0.2517 0.6933 0.6326 0.040 Uiso 1 1 calc R . .
C7 C 0.35424(16) 0.5907(4) 0.68288(13) 0.0288(5) Uani 1 1 d . . .
H7 H 0.3234 0.4979 0.7057 0.035 Uiso 1 1 calc R . .
C8 C 0.42681(15) 0.3196(3) 0.79418(12) 0.0234(5) Uani 1 1 d . . .
C9 C 0.39149(18) 0.1719(4) 0.75927(14) 0.0301(6) Uani 1 1 d . . .
H9 H 0.4049 0.1529 0.7132 0.036 Uiso 1 1 calc R . .
C10 C 0.33699(17) 0.0540(4) 0.79271(16) 0.0358(6) Uani 1 1 d . . .
H10 H 0.3130 -0.0467 0.7694 0.043 Uiso 1 1 calc R . .
C11 C 0.31706(18) 0.0815(4) 0.85979(16) 0.0382(7) Uani 1 1 d . . .
H11 H 0.2797 -0.0005 0.8824 0.046 Uiso 1 1 calc R . .
C12 C 0.35149(19) 0.2283(4) 0.89396(15) 0.0384(7) Uani 1 1 d . . .
H12 H 0.3376 0.2473 0.9399 0.046 Uiso 1 1 calc R . .
C13 C 0.40607(17) 0.3471(4) 0.86127(14) 0.0311(6) Uani 1 1 d . . .
H13 H 0.4295 0.4479 0.8848 0.037 Uiso 1 1 calc R . .
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'
P P 0.1023 0.0942 '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
C1 Cu1 C1 180.0 5_666 .
F1 C1 Cu1 115.2(2) . .
F1 C1 F3 100.9(2) . .
F2 C1 Cu1 117.6(2) . .
F2 C1 F1 102.2(3) . .
F2 C1 F3 102.3(3) . .
F3 C1 Cu1 116.1(2) . .
C2 P1 C2 107.03(15) 3_656 .
C2 P1 C8 111.47(10) . 3_656
C2 P1 C8 110.36(11) . .
C2 P1 C8 110.36(11) 3_656 3_656
C2 P1 C8 111.47(10) 3_656 .
C8 P1 C8 106.22(16) 3_656 .
C3 C2 P1 118.63(18) . .
C3 C2 C7 119.9(2) . .
C7 C2 P1 121.44(19) . .
C2 C3 H3 120.0 . .
C4 C3 C2 120.0(2) . .
C4 C3 H3 120.0 . .
C3 C4 H4 120.1 . .
C3 C4 C5 119.8(3) . .
C5 C4 H4 120.1 . .
C4 C5 H5 119.9 . .
C6 C5 C4 120.2(2) . .
C6 C5 H5 119.9 . .
C5 C6 H6 119.8 . .
C7 C6 C5 120.3(2) . .
C7 C6 H6 119.8 . .
C2 C7 H7 120.1 . .
C6 C7 C2 119.7(2) . .
C6 C7 H7 120.1 . .
C9 C8 P1 118.14(19) . .
C13 C8 P1 121.98(19) . .
C13 C8 C9 119.9(2) . .
C8 C9 H9 120.4 . .
C10 C9 C8 119.2(3) . .
C10 C9 H9 120.4 . .
C9 C10 H10 119.7 . .
C9 C10 C11 120.6(3) . .
C11 C10 H10 119.7 . .
C10 C11 H11 120.0 . .
C10 C11 C12 120.0(3) . .
C12 C11 H11 120.0 . .
C11 C12 H12 120.0 . .
C13 C12 C11 120.1(3) . .
C13 C12 H12 120.0 . .
C8 C13 H13 119.9 . .
C12 C13 C8 120.2(3) . .
C12 C13 H13 119.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 C1 1.930(3) 5_666
Cu1 C1 1.930(3) .
F1 C1 1.382(3) .
F2 C1 1.356(4) .
F3 C1 1.388(4) .
P1 C2 1.792(2) .
P1 C2 1.792(2) 3_656
P1 C8 1.798(2) .
P1 C8 1.798(2) 3_656
C2 C3 1.392(4) .
C2 C7 1.394(3) .
C3 H3 0.9500 .
C3 C4 1.385(4) .
C4 H4 0.9500 .
C4 C5 1.390(4) .
C5 H5 0.9500 .
C5 C6 1.382(4) .
C6 H6 0.9500 .
C6 C7 1.381(4) .
C7 H7 0.9500 .
C8 C9 1.403(3) .
C8 C13 1.387(4) .
C9 H9 0.9500 .
C9 C10 1.384(4) .
C10 H10 0.9500 .
C10 C11 1.384(4) .
C11 H11 0.9500 .
C11 C12 1.385(4) .
C12 H12 0.9500 .
C12 C13 1.381(4) .
C13 H13 0.9500 .
