#------------------------------------------------------------------------------
#$Date: 2016-03-21 08:48:38 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178612 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/23/4072352.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_4072352
loop_
_publ_author_name
'Dubinina, Galyna G.'
'Ogikubo, Junichi'
'Vicic, David A.'
_publ_section_title
;
 Structure of Bis(trifluoromethyl)cuprate and Its Role in
 Trifluoromethylation Reactions
;
_journal_issue                   23
_journal_name_full               Organometallics
_journal_page_first              6233
_journal_paper_doi               10.1021/om800794m
_journal_volume                  27
_journal_year                    2008
_chemical_formula_sum            'C44 H52 Cu2 F6 N4'
_chemical_formula_weight         877.98
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.43(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.23(2)
_cell_length_b                   8.460(15)
_cell_length_c                   23.49(4)
_cell_measurement_reflns_used    3567
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      31.606
_cell_measurement_theta_min      1.6985
_cell_volume                     2382(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.925
_diffrn_measured_fraction_theta_max 0.925
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1119
_diffrn_reflns_av_sigmaI/netI    0.1195
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            25014
_diffrn_reflns_theta_full        31.89
_diffrn_reflns_theta_max         31.89
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.947
_exptl_absorpt_correction_T_max  0.8331
_exptl_absorpt_correction_T_min  0.7031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Rigaku
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.892
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         7588
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.2065
_refine_ls_R_factor_gt           0.0946
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1128P)²+0.7661P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2139
_refine_ls_wR_factor_ref         0.2684
_reflns_number_gt                3365
_reflns_number_total             7588
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om800794m_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2/c
_cod_database_code               4072352
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
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 0.5000 1.0000 0.0000 0.0531(3) Uani 1 2 d S
Cu2 Cu 1.0000 0.40544(10) 0.2500 0.0401(2) Uani 1 2 d S
F1 F 0.5957(4) 0.6872(5) 0.00972(18) 0.0957(13) Uani 1 1 d .
F2 F 0.6252(3) 0.8120(5) 0.09421(15) 0.0946(13) Uani 1 1 d .
F3 F 0.7231(3) 0.8743(6) 0.0277(2) 0.1068(15) Uani 1 1 d .
N1 N 0.9131(3) 0.4376(5) 0.12172(16) 0.0458(10) Uani 1 1 d .
N2 N 0.7825(3) 0.3666(5) 0.17064(16) 0.0453(10) Uani 1 1 d .
C1 C 0.6134(5) 0.8433(8) 0.0339(3) 0.0673(17) Uani 1 1 d .
C2 C 0.8937(4) 0.4040(6) 0.17569(19) 0.0414(10) Uani 1 1 d .
C3 C 0.8093(4) 0.4305(8) 0.0739(2) 0.0587(15) Uani 1 1 d .
H3A H 0.8191 0.3565 0.0427 0.070 Uiso 1 1 calc R
H3B H 0.7893 0.5363 0.0570 0.070 Uiso 1 1 calc R
C4 C 0.7187(5) 0.3678(8) 0.1083(2) 0.0618(15) Uani 1 1 d .
H4A H 0.6537 0.4397 0.1035 0.074 Uiso 1 1 calc R
H4B H 0.6929 0.2604 0.0953 0.074 Uiso 1 1 calc R
C5 C 1.0218(4) 0.4951(6) 0.10940(19) 0.0438(11) Uani 1 1 d .
C6 C 1.0525(5) 0.6579(6) 0.1204(2) 0.0516(12) Uani 1 1 d .
C7 C 1.1566(4) 0.7099(6) 0.1078(2) 0.0534(13) Uani 1 1 d .
H7A H 1.1779 0.8171 0.1151 0.064 Uiso 1 1 calc R
C8 C 1.2293(4) 0.6074(6) 0.0849(2) 0.0471(12) Uani 1 1 d .
C9 C 1.1957(4) 0.4451(6) 0.0741(2) 0.0470(12) Uani 1 1 d .
H9A H 1.2432 0.3748 0.0588 0.056 Uiso 1 1 calc R
C10 C 1.0916(4) 0.3871(6) 0.0860(2) 0.0451(11) Uani 1 1 d .
C11 C 0.9755(6) 0.7742(7) 0.1455(3) 0.0722(18) Uani 1 1 d .
H11A H 0.8993 0.7665 0.1228 0.108 Uiso 1 1 calc R
H11B H 1.0029 0.8825 0.1435 0.108 Uiso 1 1 calc R
H11C H 0.9757 0.7468 0.1861 0.108 Uiso 1 1 calc R
C12 C 1.3430(4) 0.6656(8) 0.0724(2) 0.0623(15) Uani 1 1 d .
H12A H 1.3306 0.7571 0.0463 0.093 Uiso 1 1 calc R
H12B H 1.3779 0.5804 0.0540 0.093 Uiso 1 1 calc R
H12C H 1.3922 0.6960 0.1090 0.093 Uiso 1 1 calc R
C13 C 1.0593(5) 0.2110(7) 0.0738(3) 0.0720(17) Uani 1 1 d .
H13A H 1.0297 0.1679 0.1064 0.108 Uiso 1 1 calc R
H13B H 1.1254 0.1507 0.0692 0.108 Uiso 1 1 calc R
H13C H 1.0023 0.2032 0.0382 0.108 Uiso 1 1 calc R
C14 C 0.7320(4) 0.3102(6) 0.21922(18) 0.0393(10) Uani 1 1 d .
C15 C 0.6763(4) 0.4204(6) 0.2501(2) 0.0454(11) Uani 1 1 d .
C16 C 0.6242(4) 0.3591(6) 0.2959(2) 0.0483(12) Uani 1 1 d .
H16A H 0.5852 0.4298 0.3161 0.058 Uiso 1 1 calc R
C17 C 0.6298(4) 0.1969(6) 0.3113(2) 0.0474(12) Uani 1 1 d .
C18 C 0.6882(4) 0.0919(6) 0.2806(2) 0.0535(13) Uani 1 1 d .
H18A H 0.6917 -0.0170 0.2906 0.064 Uiso 1 1 calc R
C19 C 0.7415(4) 0.1446(6) 0.2353(2) 0.0492(12) Uani 1 1 d .
C20 C 0.6704(6) 0.5983(7) 0.2350(3) 0.0704(17) Uani 1 1 d .
H20A H 0.7462 0.6403 0.2387 0.106 Uiso 1 1 calc R
H20B H 0.6319 0.6545 0.2617 0.106 Uiso 1 1 calc R
H20C H 0.6296 0.6128 0.1950 0.106 Uiso 1 1 calc R
C21 C 0.5693(5) 0.1357(8) 0.3597(3) 0.0704(17) Uani 1 1 d .
H21A H 0.5430 0.2259 0.3794 0.106 Uiso 1 1 calc R
H21B H 0.6214 0.0728 0.3879 0.106 Uiso 1 1 calc R
H21C H 0.5056 0.0700 0.3421 0.106 Uiso 1 1 calc R
C22 C 0.8069(6) 0.0258(7) 0.2031(3) 0.0751(19) Uani 1 1 d .
H22A H 0.7971 -0.0819 0.2166 0.113 Uiso 1 1 calc R
H22B H 0.8864 0.0530 0.2114 0.113 Uiso 1 1 calc R
H22C H 0.7781 0.0322 0.1611 0.113 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'
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
C1 Cu1 C1 180.0(3) 3_675 .
C2 Cu2 C2 179.3(3) . 2_755
C2 N1 C5 124.9(4) . .
C2 N1 C3 113.8(4) . .
C5 N1 C3 120.9(4) . .
C2 N2 C14 124.3(4) . .
C2 N2 C4 113.1(4) . .
C14 N2 C4 122.2(4) . .
F3 C1 F2 103.2(5) . .
F3 C1 F1 101.7(5) . .
F2 C1 F1 101.6(5) . .
F3 C1 Cu1 116.3(4) . .
F2 C1 Cu1 117.0(4) . .
F1 C1 Cu1 114.8(4) . .
N1 C2 N2 108.5(4) . .
N1 C2 Cu2 128.3(4) . .
N2 C2 Cu2 123.2(3) . .
N1 C3 C4 101.7(4) . .
N1 C3 H3A 111.4 . .
C4 C3 H3A 111.4 . .
N1 C3 H3B 111.4 . .
C4 C3 H3B 111.4 . .
H3A C3 H3B 109.3 . .
N2 C4 C3 102.5(4) . .
N2 C4 H4A 111.3 . .
C3 C4 H4A 111.3 . .
N2 C4 H4B 111.3 . .
C3 C4 H4B 111.3 . .
H4A C4 H4B 109.2 . .
C10 C5 C6 121.7(5) . .
C10 C5 N1 119.2(4) . .
C6 C5 N1 119.1(4) . .
C7 C6 C5 118.0(5) . .
C7 C6 C11 120.9(5) . .
C5 C6 C11 121.1(5) . .
C8 C7 C6 122.6(5) . .
C8 C7 H7A 118.7 . .
C6 C7 H7A 118.7 . .
C7 C8 C9 118.0(4) . .
C7 C8 C12 121.8(5) . .
C9 C8 C12 120.1(5) . .
C8 C9 C10 121.5(5) . .
C8 C9 H9A 119.3 . .
C10 C9 H9A 119.3 . .
C5 C10 C9 118.3(5) . .
C5 C10 C13 122.2(5) . .
C9 C10 C13 119.6(5) . .
C6 C11 H11A 109.5 . .
C6 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C6 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C8 C12 H12A 109.5 . .
C8 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C8 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C10 C13 H13A 109.5 . .
C10 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C10 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C15 C14 C19 121.3(4) . .
C15 C14 N2 119.5(4) . .
C19 C14 N2 119.2(4) . .
C14 C15 C16 117.7(5) . .
C14 C15 C20 121.6(4) . .
C16 C15 C20 120.7(5) . .
C17 C16 C15 122.0(4) . .
C17 C16 H16A 119.0 . .
C15 C16 H16A 119.0 . .
C16 C17 C18 118.6(4) . .
C16 C17 C21 120.1(5) . .
C18 C17 C21 121.3(5) . .
C17 C18 C19 122.3(5) . .
C17 C18 H18A 118.9 . .
C19 C18 H18A 118.9 . .
C18 C19 C14 118.1(4) . .
C18 C19 C22 120.8(5) . .
C14 C19 C22 121.1(5) . .
C15 C20 H20A 109.5 . .
C15 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C15 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C17 C21 H21A 109.5 . .
C17 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C17 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C19 C22 H22A 109.5 . .
C19 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C19 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 C1 1.970(6) 3_675
Cu1 C1 1.970(6) .
Cu2 C2 1.959(5) .
Cu2 C2 1.959(5) 2_755
F1 C1 1.437(8) .
F2 C1 1.419(7) .
F3 C1 1.403(7) .
N1 C2 1.365(6) .
N1 C5 1.497(6) .
N1 C3 1.520(7) .
N2 C2 1.379(6) .
N2 C14 1.480(6) .
N2 C4 1.516(6) .
C3 C4 1.586(7) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C10 1.433(7) .
C5 C6 1.438(8) .
C6 C7 1.431(7) .
C6 C11 1.557(7) .
C7 C8 1.422(7) .
C7 H7A 0.9500 .
C8 C9 1.441(7) .
C8 C12 1.558(7) .
C9 C10 1.442(7) .
C9 H9A 0.9500 .
C10 C13 1.553(8) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 C15 1.433(7) .
C14 C19 1.449(7) .
C15 C16 1.451(7) .
C15 C20 1.544(8) .
C16 C17 1.418(8) .
C16 H16A 0.9500 .
C17 C18 1.422(7) .
C17 C21 1.562(7) .
C18 C19 1.426(7) .
C18 H18A 0.9500 .
C19 C22 1.569(8) .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
