#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:49:09 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178825 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/79/4107992.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_4107992
loop_
_publ_author_name
'Galyna G. Dubinina'
'Hideki Furutachi'
'David A. Vicic'
_publ_section_title
;
 Active Trifluoromethylating Agents from Well-Defined Copper(I)-CF3
 Complexes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8600
_journal_page_last               8601
_journal_paper_doi               10.1021/ja802946s
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C13 H27 Cu N2 O'
_chemical_formula_weight         290.91
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 94.423(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.170(4)
_cell_length_b                   8.528(3)
_cell_length_c                   16.418(6)
_cell_measurement_reflns_used    3565
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3
_cell_volume                     1559.3(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0883
_diffrn_reflns_av_sigmaI/netI    0.0695
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15433
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    1.390
_exptl_absorpt_correction_T_max  0.8186
_exptl_absorpt_correction_T_min  0.6273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Rigaku
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.001
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.209
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         3565
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.209
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0659
_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)+(0.0406P)²+3.0157P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1616
_reflns_number_gt                2848
_reflns_number_total             3565
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja802946s-file001_1.cif
_cod_data_source_block           comp5
_cod_original_cell_volume        1559.3(9)
_cod_database_code               4107992
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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 0.89077(5) 0.57954(6) 0.02741(3) 0.03048(19) Uani 1 1 d .
O1 O 1.0576(3) 0.5355(4) 0.06799(17) 0.0355(7) Uani 1 1 d .
N1 N 0.6697(3) 0.6209(4) 0.1041(2) 0.0337(9) Uani 1 1 d .
N2 N 0.7327(3) 0.8366(4) 0.0521(2) 0.0327(8) Uani 1 1 d .
C1 C 0.7581(4) 0.6828(5) 0.0632(2) 0.0272(8) Uani 1 1 d .
C2 C 0.5820(4) 0.7361(6) 0.1278(3) 0.0399(11) Uani 1 1 d .
H1 H 0.5906 0.7563 0.1873 0.048 Uiso 1 1 calc R
H2 H 0.4989 0.7016 0.1118 0.048 Uiso 1 1 calc R
C3 C 0.6154(4) 0.8799(5) 0.0796(3) 0.0412(11) Uani 1 1 d .
H3 H 0.5561 0.8992 0.0326 0.049 Uiso 1 1 calc R
H4 H 0.6214 0.9745 0.1146 0.049 Uiso 1 1 calc R
C4 C 0.6711(4) 0.4601(5) 0.1341(3) 0.0424(12) Uani 1 1 d .
H5 H 0.7443 0.4082 0.1152 0.051 Uiso 1 1 calc R
C5 C 0.6813(7) 0.4550(8) 0.2264(4) 0.078(2) Uani 1 1 d .
H6 H 0.7465 0.5242 0.2475 0.094 Uiso 1 1 calc R
H7 H 0.6984 0.3474 0.2447 0.094 Uiso 1 1 calc R
H8 H 0.6055 0.4900 0.2468 0.094 Uiso 1 1 calc R
C6 C 0.5645(6) 0.3696(7) 0.0991(4) 0.0625(16) Uani 1 1 d .
H9 H 0.4908 0.4215 0.1135 0.075 Uiso 1 1 calc R
H10 H 0.5674 0.2629 0.1214 0.075 Uiso 1 1 calc R
H11 H 0.5656 0.3652 0.0395 0.075 Uiso 1 1 calc R
C7 C 0.7989(4) 0.9391(5) 0.0006(3) 0.0389(11) Uani 1 1 d .
H12 H 0.8709 0.8792 -0.0145 0.047 Uiso 1 1 calc R
C8 C 0.8446(6) 1.0828(7) 0.0460(4) 0.0687(18) Uani 1 1 d .
H22 H 0.7767 1.1415 0.0651 0.082 Uiso 1 1 calc R
H23 H 0.8882 1.1492 0.0096 0.082 Uiso 1 1 calc R
H24 H 0.8987 1.0514 0.0930 0.082 Uiso 1 1 calc R
C9 C 0.7259(6) 0.9782(8) -0.0783(4) 0.0686(18) Uani 1 1 d .
H25 H 0.6874 0.8827 -0.1010 0.082 Uiso 1 1 calc R
H26 H 0.7788 1.0216 -0.1176 0.082 Uiso 1 1 calc R
H27 H 0.6641 1.0555 -0.0675 0.082 Uiso 1 1 calc R
C10 C 1.1083(4) 0.5309(6) 0.1484(3) 0.0357(10) Uani 1 1 d .
C11 C 1.0752(6) 0.3769(8) 0.1877(4) 0.0651(17) Uani 1 1 d .
H13 H 0.9876 0.3678 0.1864 0.078 Uiso 1 1 calc R
H14 H 1.1094 0.3743 0.2445 0.078 Uiso 1 1 calc R
H15 H 1.1074 0.2892 0.1575 0.078 Uiso 1 1 calc R
C12 C 1.0583(5) 0.6682(8) 0.1961(3) 0.0646(18) Uani 1 1 d .
H16 H 1.0761 0.7673 0.1693 0.077 Uiso 1 1 calc R
H17 H 1.0958 0.6683 0.2521 0.077 Uiso 1 1 calc R
H18 H 0.9712 0.6564 0.1974 0.077 Uiso 1 1 calc R
C13 C 1.2429(4) 0.5439(7) 0.1499(3) 0.0525(14) Uani 1 1 d .
H19 H 1.2744 0.4566 0.1192 0.063 Uiso 1 1 calc R
H20 H 1.2775 0.5402 0.2066 0.063 Uiso 1 1 calc R
H21 H 1.2644 0.6434 0.1249 0.063 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'
N N 0.0061 0.0033 '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'
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_1
_geom_angle_site_symmetry_3
C1 Cu1 O1 137.85(15) . .
C1 Cu1 O1 140.97(15) . 3_765
O1 Cu1 O1 81.16(13) . 3_765
C1 Cu1 Cu1 178.22(14) . 3_765
O1 Cu1 Cu1 40.65(9) . 3_765
O1 Cu1 Cu1 40.51(8) 3_765 3_765
C10 O1 Cu1 129.1(3) . .
C10 O1 Cu1 127.9(3) . 3_765
Cu1 O1 Cu1 98.84(13) . 3_765
C1 N1 C4 123.4(4) . .
C1 N1 C2 113.7(4) . .
C4 N1 C2 122.2(4) . .
C1 N2 C7 123.4(3) . .
C1 N2 C3 112.8(4) . .
C7 N2 C3 122.2(3) . .
N1 C1 N2 107.1(3) . .
N1 C1 Cu1 127.3(3) . .
N2 C1 Cu1 125.6(3) . .
N1 C2 C3 102.0(3) . .
N1 C2 H1 111.4 . .
C3 C2 H1 111.4 . .
N1 C2 H2 111.4 . .
C3 C2 H2 111.4 . .
H1 C2 H2 109.2 . .
N2 C3 C2 102.6(3) . .
N2 C3 H3 111.3 . .
C2 C3 H3 111.3 . .
N2 C3 H4 111.3 . .
C2 C3 H4 111.3 . .
H3 C3 H4 109.2 . .
N1 C4 C6 111.6(4) . .
N1 C4 C5 111.4(5) . .
C6 C4 C5 111.5(5) . .
N1 C4 H5 107.4 . .
C6 C4 H5 107.4 . .
C5 C4 H5 107.4 . .
C4 C5 H6 109.5 . .
C4 C5 H7 109.5 . .
H6 C5 H7 109.5 . .
C4 C5 H8 109.5 . .
H6 C5 H8 109.5 . .
H7 C5 H8 109.5 . .
C4 C6 H9 109.5 . .
C4 C6 H10 109.5 . .
H9 C6 H10 109.5 . .
C4 C6 H11 109.5 . .
H9 C6 H11 109.5 . .
H10 C6 H11 109.5 . .
N2 C7 C8 111.7(4) . .
N2 C7 C9 111.4(4) . .
C8 C7 C9 112.7(5) . .
N2 C7 H12 106.9 . .
C8 C7 H12 106.9 . .
C9 C7 H12 106.9 . .
C7 C8 H22 109.5 . .
C7 C8 H23 109.5 . .
H22 C8 H23 109.5 . .
C7 C8 H24 109.5 . .
H22 C8 H24 109.5 . .
H23 C8 H24 109.5 . .
C7 C9 H25 109.5 . .
C7 C9 H26 109.5 . .
H25 C9 H26 109.5 . .
C7 C9 H27 109.5 . .
H25 C9 H27 109.5 . .
H26 C9 H27 109.5 . .
O1 C10 C13 110.2(4) . .
O1 C10 C11 109.3(4) . .
C13 C10 C11 109.3(5) . .
O1 C10 C12 108.9(4) . .
C13 C10 C12 109.7(4) . .
C11 C10 C12 109.3(5) . .
C10 C11 H13 109.5 . .
C10 C11 H14 109.5 . .
H13 C11 H14 109.5 . .
C10 C11 H15 109.5 . .
H13 C11 H15 109.5 . .
H14 C11 H15 109.5 . .
C10 C12 H16 109.5 . .
C10 C12 H17 109.5 . .
H16 C12 H17 109.5 . .
C10 C12 H18 109.5 . .
H16 C12 H18 109.5 . .
H17 C12 H18 109.5 . .
C10 C13 H19 109.5 . .
C10 C13 H20 109.5 . .
H19 C13 H20 109.5 . .
C10 C13 H21 109.5 . .
H19 C13 H21 109.5 . .
H20 C13 H21 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 1.858(4) .
Cu1 O1 1.966(3) .
Cu1 O1 1.972(3) 3_765
Cu1 Cu1 2.9906(12) 3_765
O1 C10 1.396(5) .
O1 Cu1 1.972(3) 3_765
N1 C1 1.344(5) .
N1 C4 1.457(6) .
N1 C2 1.461(5) .
N2 C1 1.351(5) .
N2 C7 1.457(6) .
N2 C3 1.466(5) .
C2 C3 1.522(6) .
C2 H1 0.9900 .
C2 H2 0.9900 .
C3 H3 0.9900 .
C3 H4 0.9900 .
C4 C6 1.495(8) .
C4 C5 1.511(8) .
C4 H5 1.0000 .
C5 H6 0.9800 .
C5 H7 0.9800 .
C5 H8 0.9800 .
C6 H9 0.9800 .
C6 H10 0.9800 .
C6 H11 0.9800 .
C7 C8 1.503(7) .
C7 C9 1.514(7) .
C7 H12 1.0000 .
C8 H22 0.9800 .
C8 H23 0.9800 .
C8 H24 0.9800 .
C9 H25 0.9800 .
C9 H26 0.9800 .
C9 H27 0.9800 .
C10 C13 1.506(6) .
C10 C11 1.522(7) .
C10 C12 1.538(7) .
C11 H13 0.9800 .
C11 H14 0.9800 .
C11 H15 0.9800 .
C12 H16 0.9800 .
C12 H17 0.9800 .
C12 H18 0.9800 .
C13 H19 0.9800 .
C13 H20 0.9800 .
C13 H21 0.9800 .
