#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:20:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178466 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/87/4028740.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_4028740
loop_
_publ_author_name
'Anton Lishchynskyi'
'Maxim A. Novikov'
'Eddy Martin'
'Eduardo C. Escudero-Adán'
'Petr Novák'
'Vladimir V. Grushin'
_publ_section_title
;
 Trifluoromethylation of Aryl and Heteroaryl Halides with
 Fluoroform-Derived CuCF3: Scope, Limitations, and Mechanistic Features
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11126
_journal_page_last               11146
_journal_paper_doi               10.1021/jo401423h
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C38 H30 Cu2 F12 N2 O10'
_chemical_formula_weight         1029.72
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                71.799(2)
_cell_angle_beta                 75.062(2)
_cell_angle_gamma                80.007(2)
_cell_formula_units_Z            1
_cell_length_a                   8.0701(6)
_cell_length_b                   10.4214(8)
_cell_length_c                   12.9523(9)
_cell_measurement_reflns_used    3214
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.48
_cell_measurement_theta_min      2.28
_cell_volume                     994.69(13)
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10123
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.39
_diffrn_reflns_theta_min         1.70
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_current           0.6
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Bruker APEX DUO'
_exptl_absorpt_coefficient_mu    1.186
_exptl_absorpt_correction_T_max  0.9653
_exptl_absorpt_correction_T_min  0.8421
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_description       block
_exptl_crystal_F_000             518
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0210P)²+0.7980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0725
_reflns_number_gt                4265
_reflns_number_total             5117
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401423h_si_004.cif
_cod_data_source_block           mo_al420_0m
_cod_database_code               4028740
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cu1 Cu 0.57590(3) 0.60332(2) -0.00386(2) 0.01024(6) Uani 1 1 d .
O1 O 0.74494(18) 0.54671(15) -0.12377(12) 0.0176(3) Uani 1 1 d .
O2 O 0.61937(17) 0.36952(14) -0.11936(11) 0.0164(3) Uani 1 1 d .
O3 O 0.69610(18) 0.47100(14) 0.10623(12) 0.0167(3) Uani 1 1 d .
O4 O 0.56493(17) 0.29460(14) 0.11184(11) 0.0152(3) Uani 1 1 d .
O5 O 0.68484(17) 0.77607(14) -0.00697(11) 0.0146(3) Uani 1 1 d .
F1 F 0.58286(16) 0.38539(13) -0.32782(11) 0.0250(3) Uani 1 1 d .
F2 F 0.74520(18) 0.25745(15) -0.42265(11) 0.0320(3) Uani 1 1 d .
F3 F 0.68423(17) 0.18445(13) -0.24467(11) 0.0258(3) Uani 1 1 d .
F4 F 0.42004(15) 0.12212(13) 0.34537(10) 0.0233(3) Uani 1 1 d .
F5 F 0.47468(16) 0.15934(13) 0.48648(10) 0.0227(3) Uani 1 1 d .
F6 F 0.44344(16) 0.32619(13) 0.34225(10) 0.0232(3) Uani 1 1 d .
N1 N 0.7247(2) 0.90948(18) 0.09130(15) 0.0194(4) Uani 1 1 d .
C1 C 0.7360(2) 0.4481(2) -0.15790(16) 0.0130(4) Uani 1 1 d .
C2 C 0.8841(2) 0.4232(2) -0.25065(16) 0.0145(4) Uani 1 1 d .
C3 C 1.0363(3) 0.4757(2) -0.25947(18) 0.0198(4) Uani 1 1 d .
H3 H 1.0406 0.5222 -0.2079 0.024 Uiso 1 1 calc R
C4 C 1.1817(3) 0.4618(2) -0.3416(2) 0.0250(5) Uani 1 1 d .
H4 H 1.2836 0.4993 -0.3466 0.030 Uiso 1 1 calc R
C5 C 1.1775(3) 0.3934(2) -0.41575(19) 0.0262(5) Uani 1 1 d .
H5 H 1.2768 0.3833 -0.4720 0.031 Uiso 1 1 calc R
C6 C 1.0286(3) 0.3391(2) -0.40860(18) 0.0227(5) Uani 1 1 d .
H6 H 1.0270 0.2916 -0.4601 0.027 Uiso 1 1 calc R
C7 C 0.8813(3) 0.3531(2) -0.32711(17) 0.0162(4) Uani 1 1 d .
C8 C 0.7233(3) 0.2959(2) -0.32926(18) 0.0201(4) Uani 1 1 d .
C9 C 0.6676(2) 0.3483(2) 0.14020(16) 0.0121(4) Uani 1 1 d .
C10 C 0.7736(2) 0.25359(19) 0.21867(16) 0.0123(4) Uani 1 1 d .
C11 C 0.9511(2) 0.2365(2) 0.17924(17) 0.0155(4) Uani 1 1 d .
H11 H 1.0014 0.2882 0.1066 0.019 Uiso 1 1 calc R
C12 C 1.0553(3) 0.1452(2) 0.24456(18) 0.0182(4) Uani 1 1 d .
H12 H 1.1763 0.1341 0.2167 0.022 Uiso 1 1 calc R
C13 C 0.9827(3) 0.0700(2) 0.35070(18) 0.0187(4) Uani 1 1 d .
H13 H 1.0536 0.0060 0.3952 0.022 Uiso 1 1 calc R
C14 C 0.8064(3) 0.0880(2) 0.39202(17) 0.0163(4) Uani 1 1 d .
H14 H 0.7574 0.0378 0.4655 0.020 Uiso 1 1 calc R
C15 C 0.7012(2) 0.1793(2) 0.32653(16) 0.0129(4) Uani 1 1 d .
C16 C 0.5115(3) 0.1967(2) 0.37436(17) 0.0169(4) Uani 1 1 d .
C17 C 0.6925(3) 0.7939(2) 0.08175(17) 0.0161(4) Uani 1 1 d .
H17 H 0.6742 0.7199 0.1472 0.019 Uiso 1 1 calc R
C18 C 0.7477(3) 1.0291(2) -0.0036(2) 0.0271(5) Uani 1 1 d .
H18A H 0.7578 1.0040 -0.0720 0.041 Uiso 1 1 calc R
H18B H 0.8528 1.0674 -0.0078 0.041 Uiso 1 1 calc R
H18C H 0.6482 1.0967 0.0050 0.041 Uiso 1 1 calc R
C19 C 0.7209(4) 0.9257(3) 0.1998(2) 0.0378(7) Uani 1 1 d .
H19A H 0.6987 0.8397 0.2573 0.057 Uiso 1 1 calc R
H19B H 0.6292 0.9964 0.2157 0.057 Uiso 1 1 calc R
H19C H 0.8321 0.9519 0.1992 0.057 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'
O O 0.0106 0.0060 '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'
Cu Cu 0.3201 1.2651 '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
O1 Cu1 O4 88.99(6) . 2_665
O1 Cu1 O3 89.77(6) . .
O4 Cu1 O3 169.16(5) 2_665 .
O1 Cu1 O2 168.74(6) . 2_665
O4 Cu1 O2 89.70(6) 2_665 2_665
O3 Cu1 O2 89.42(6) . 2_665
O1 Cu1 O5 99.66(5) . .
O4 Cu1 O5 94.48(6) 2_665 .
O3 Cu1 O5 96.34(6) . .
O2 Cu1 O5 91.60(5) 2_665 .
O1 Cu1 Cu1 83.14(4) . 2_665
O4 Cu1 Cu1 83.90(4) 2_665 2_665
O3 Cu1 Cu1 85.27(4) . 2_665
O2 Cu1 Cu1 85.59(4) 2_665 2_665
O5 Cu1 Cu1 176.76(4) . 2_665
C1 O1 Cu1 125.05(13) . .
C1 O2 Cu1 120.69(12) . 2_665
C9 O3 Cu1 120.88(13) . .
C9 O4 Cu1 123.07(13) . 2_665
C17 O5 Cu1 119.52(13) . .
C17 N1 C18 121.47(18) . .
C17 N1 C19 121.16(19) . .
C18 N1 C19 117.08(18) . .
O2 C1 O1 125.52(18) . .
O2 C1 C2 119.25(17) . .
O1 C1 C2 115.19(17) . .
C3 C2 C7 118.19(18) . .
C3 C2 C1 115.57(17) . .
C7 C2 C1 126.24(17) . .
C4 C3 C2 121.7(2) . .
C5 C4 C3 119.6(2) . .
C4 C5 C6 120.1(2) . .
C5 C6 C7 120.9(2) . .
C6 C7 C2 119.49(19) . .
C6 C7 C8 116.99(18) . .
C2 C7 C8 123.47(18) . .
F1 C8 F3 107.40(17) . .
F1 C8 F2 105.73(17) . .
F3 C8 F2 105.33(17) . .
F1 C8 C7 113.07(17) . .
F3 C8 C7 113.33(18) . .
F2 C8 C7 111.40(17) . .
O4 C9 O3 126.89(19) . .
O4 C9 C10 116.13(17) . .
O3 C9 C10 116.90(16) . .
C11 C10 C15 119.21(18) . .
C11 C10 C9 117.71(17) . .
C15 C10 C9 123.03(17) . .
C12 C11 C10 120.78(19) . .
C11 C12 C13 119.84(19) . .
C12 C13 C14 120.0(2) . .
C13 C14 C15 120.33(19) . .
C14 C15 C10 119.79(18) . .
C14 C15 C16 118.78(18) . .
C10 C15 C16 121.43(18) . .
F6 C16 F5 106.35(16) . .
F6 C16 F4 106.41(16) . .
F5 C16 F4 105.62(16) . .
F6 C16 C15 112.35(16) . .
F5 C16 C15 112.26(17) . .
F4 C16 C15 113.31(16) . .
O5 C17 N1 124.24(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.9550(14) .
Cu1 O4 1.9621(14) 2_665
Cu1 O3 1.9739(14) .
Cu1 O2 1.9852(14) 2_665
Cu1 O5 2.1216(13) .
Cu1 Cu1 2.6203(5) 2_665
O1 C1 1.258(2) .
O2 C1 1.255(2) .
O2 Cu1 1.9852(14) 2_665
O3 C9 1.257(2) .
O4 C9 1.257(2) .
O4 Cu1 1.9622(14) 2_665
O5 C17 1.238(2) .
F1 C8 1.337(2) .
F2 C8 1.350(2) .
F3 C8 1.343(2) .
F4 C16 1.347(2) .
F5 C16 1.347(2) .
F6 C16 1.344(2) .
N1 C17 1.323(2) .
N1 C18 1.450(3) .
N1 C19 1.459(3) .
C1 C2 1.512(3) .
C2 C3 1.394(3) .
C2 C7 1.408(3) .
C3 C4 1.387(3) .
C4 C5 1.372(3) .
C5 C6 1.385(3) .
C6 C7 1.392(3) .
C7 C8 1.508(3) .
C9 C10 1.506(3) .
C10 C11 1.391(3) .
C10 C15 1.398(3) .
C11 C12 1.384(3) .
C12 C13 1.385(3) .
C13 C14 1.386(3) .
C14 C15 1.390(3) .
C15 C16 1.498(3) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
O4 Cu1 O1 C1 -83.50(16) 2_665
O3 Cu1 O1 C1 85.73(16) .
O2 Cu1 O1 C1 -0.1(4) 2_665
O5 Cu1 O1 C1 -177.88(16) .
Cu1 Cu1 O1 C1 0.47(16) 2_665
O1 Cu1 O3 C9 -82.96(15) .
O4 Cu1 O3 C9 0.5(4) 2_665
O2 Cu1 O3 C9 85.81(15) 2_665
O5 Cu1 O3 C9 177.35(14) .
Cu1 Cu1 O3 C9 0.18(14) 2_665
O1 Cu1 O5 C17 -136.04(15) .
O4 Cu1 O5 C17 134.22(15) 2_665
O3 Cu1 O5 C17 -45.19(15) .
O2 Cu1 O5 C17 44.40(15) 2_665
Cu1 Cu1 O5 C17 74.3(8) 2_665
Cu1 O2 C1 O1 1.4(3) 2_665
Cu1 O2 C1 C2 179.16(13) 2_665
Cu1 O1 C1 O2 -1.2(3) .
Cu1 O1 C1 C2 -179.13(13) .
O2 C1 C2 C3 -155.78(19) .
O1 C1 C2 C3 22.3(3) .
O2 C1 C2 C7 24.2(3) .
O1 C1 C2 C7 -157.8(2) .
C7 C2 C3 C4 0.8(3) .
C1 C2 C3 C4 -179.2(2) .
C2 C3 C4 C5 -0.8(4) .
C3 C4 C5 C6 0.2(4) .
C4 C5 C6 C7 0.3(4) .
C5 C6 C7 C2 -0.2(3) .
C5 C6 C7 C8 177.4(2) .
C3 C2 C7 C6 -0.3(3) .
C1 C2 C7 C6 179.7(2) .
C3 C2 C7 C8 -177.7(2) .
C1 C2 C7 C8 2.3(3) .
C6 C7 C8 F1 -128.3(2) .
C2 C7 C8 F1 49.2(3) .
C6 C7 C8 F3 109.2(2) .
C2 C7 C8 F3 -73.4(3) .
C6 C7 C8 F2 -9.4(3) .
C2 C7 C8 F2 168.07(19) .
Cu1 O4 C9 O3 0.2(3) 2_665
Cu1 O4 C9 C10 -176.37(12) 2_665
Cu1 O3 C9 O4 -0.3(3) .
Cu1 O3 C9 C10 176.28(12) .
O4 C9 C10 C11 114.3(2) .
O3 C9 C10 C11 -62.7(2) .
O4 C9 C10 C15 -63.2(2) .
O3 C9 C10 C15 119.8(2) .
C15 C10 C11 C12 1.4(3) .
C9 C10 C11 C12 -176.21(17) .
C10 C11 C12 C13 -0.3(3) .
C11 C12 C13 C14 -1.1(3) .
C12 C13 C14 C15 1.4(3) .
C13 C14 C15 C10 -0.3(3) .
C13 C14 C15 C16 -179.62(18) .
C11 C10 C15 C14 -1.1(3) .
C9 C10 C15 C14 176.34(17) .
C11 C10 C15 C16 178.22(17) .
C9 C10 C15 C16 -4.3(3) .
C14 C15 C16 F6 142.50(18) .
C10 C15 C16 F6 -36.9(3) .
C14 C15 C16 F5 22.7(3) .
C10 C15 C16 F5 -156.67(17) .
C14 C15 C16 F4 -96.9(2) .
C10 C15 C16 F4 83.8(2) .
Cu1 O5 C17 N1 -165.75(16) .
C18 N1 C17 O5 2.4(3) .
C19 N1 C17 O5 176.0(2) .
