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#$Date: 2016-03-21 19:00:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178832 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/86/4108640.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_4108640
loop_
_publ_author_name
'Hien-Quang Do'
'Rana M. Kashif Khan'
'Olafs Daugulis'
_publ_section_title
;
 A General Method for Copper-Catalyzed Arylation of Arene C-H Bonds
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15185
_journal_page_last               15192
_journal_paper_doi               10.1021/ja805688p
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C38 H22 Cu2 F8 N4 O2'
_chemical_formula_weight         845.68
_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                 93.516(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.3839(6)
_cell_length_b                   17.3423(11)
_cell_length_c                   10.0786(6)
_cell_measurement_reflns_used    3841
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.09
_cell_measurement_theta_min      2.34
_cell_volume                     1637.09(18)
_computing_cell_refinement       'SAINT v7.12A (Bruker-Nonius, 2004)'
_computing_data_collection       'APEX2 v1.0-27 (Bruker-Nonius, 2005)'
_computing_data_reduction        'SAINT v7.12A (Bruker-Nonius, 2004)'
_computing_structure_refinement  'SHELXL v6.12 (G.M. Sheldrick, 2001)'
_computing_structure_solution    'SHELXS v6.12 (G.M. Sheldrick, 2001)'
_diffrn_ambient_temperature      223(2)
_diffrn_detector_area_resol_mean 4K
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker-Nonius APEX II CCD'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8401
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.34
_diffrn_standards_decay_%        0.0
_exptl_absorpt_coefficient_mu    1.389
_exptl_absorpt_correction_T_max  0.9856
_exptl_absorpt_correction_T_min  0.6505
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            'Bright red'
_exptl_crystal_density_diffrn    1.716
_exptl_crystal_description       column
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0282
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0551P)²+0.0356P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0834
_reflns_number_gt                2082
_reflns_number_total             3001
_reflns_threshold_expression     >4sigma(I)
_cod_data_source_file            ja805688p_si_001.cif
_cod_data_source_block           k1123
_cod_database_code               4108640
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
Cu Cu 0.62822(3) 0.514672(18) 0.46849(3) 0.04296(13) Uani 1 1 d .
F1 F 0.57859(14) 0.34126(8) 0.38302(14) 0.0505(4) Uani 1 1 d .
F2 F 0.42659(17) 0.28004(8) 0.17820(16) 0.0608(4) Uani 1 1 d .
F3 F 0.29647(17) 0.52863(9) 0.02418(14) 0.0587(4) Uani 1 1 d .
F4 F 0.44535(15) 0.59086(8) 0.23139(14) 0.0521(4) Uani 1 1 d .
O1 O 0.28348(19) 0.37135(11) -0.01177(16) 0.0570(5) Uani 1 1 d .
N1 N 0.80781(19) 0.48359(10) 0.58622(17) 0.0340(4) Uani 1 1 d .
N2 N 0.72232(19) 0.62321(11) 0.49994(18) 0.0375(4) Uani 1 1 d .
C1 C 0.8499(2) 0.41415(14) 0.6287(2) 0.0409(5) Uani 1 1 d .
H1 H 0.7916 0.3715 0.6060 0.049 Uiso 1 1 calc R
C2 C 0.9764(3) 0.40178(15) 0.7053(2) 0.0472(6) Uani 1 1 d .
H2 H 1.0014 0.3517 0.7341 0.057 Uiso 1 1 calc R
C3 C 1.0638(3) 0.46242(16) 0.7386(2) 0.0468(6) Uani 1 1 d .
H3 H 1.1499 0.4545 0.7893 0.056 Uiso 1 1 calc R
C4 C 1.0238(2) 0.53643(14) 0.6963(2) 0.0383(5) Uani 1 1 d .
C5 C 1.1100(2) 0.60359(16) 0.7226(2) 0.0461(6) Uani 1 1 d .
H5 H 1.1984 0.5986 0.7709 0.055 Uiso 1 1 calc R
C6 C 1.0664(3) 0.67378(16) 0.6794(2) 0.0463(6) Uani 1 1 d .
H6 H 1.1250 0.7168 0.6985 0.056 Uiso 1 1 calc R
C7 C 0.9327(2) 0.68438(14) 0.6050(2) 0.0391(5) Uani 1 1 d .
C8 C 0.8801(3) 0.75602(15) 0.5608(2) 0.0480(6) Uani 1 1 d .
H8 H 0.9326 0.8011 0.5808 0.058 Uiso 1 1 calc R
C9 C 0.7531(3) 0.76019(15) 0.4892(3) 0.0525(7) Uani 1 1 d .
H9 H 0.7164 0.8082 0.4604 0.063 Uiso 1 1 calc R
C10 C 0.6774(3) 0.69246(15) 0.4586(2) 0.0465(6) Uani 1 1 d .
H10 H 0.5911 0.6960 0.4065 0.056 Uiso 1 1 calc R
C11 C 0.8475(2) 0.61945(13) 0.5744(2) 0.0330(5) Uani 1 1 d .
C12 C 0.8940(2) 0.54410(14) 0.6201(2) 0.0336(5) Uani 1 1 d .
C13 C 0.5189(2) 0.46978(13) 0.3189(2) 0.0359(5) Uani 1 1 d .
C14 C 0.5093(2) 0.39125(13) 0.2956(2) 0.0361(5) Uani 1 1 d .
C15 C 0.4331(2) 0.35819(13) 0.1906(2) 0.0405(5) Uani 1 1 d .
C16 C 0.3588(2) 0.40299(14) 0.0960(2) 0.0411(6) Uani 1 1 d .
C17 C 0.3677(2) 0.48200(14) 0.1133(2) 0.0396(5) Uani 1 1 d .
C18 C 0.4461(2) 0.51212(13) 0.2211(2) 0.0365(5) Uani 1 1 d .
C19 C 0.1546(3) 0.3334(2) 0.0208(3) 0.0767(10) Uani 1 1 d .
H19A H 0.1142 0.3061 -0.0566 0.115 Uiso 1 1 calc R
H19B H 0.0868 0.3714 0.0488 0.115 Uiso 1 1 calc R
H19C H 0.1757 0.2970 0.0924 0.115 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'
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'
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
C13 Cu N1 135.68(9) .
C13 Cu N2 132.69(8) .
N1 Cu N2 80.02(7) .
C13 Cu Cu 69.76(7) 3_666
N1 Cu Cu 123.12(5) 3_666
N2 Cu Cu 122.10(5) 3_666
C16 O1 C19 113.74(19) .
C1 N1 C12 117.31(19) .
C1 N1 Cu 129.42(15) .
C12 N1 Cu 113.25(15) .
C10 N2 C11 117.6(2) .
C10 N2 Cu 129.86(16) .
C11 N2 Cu 112.54(14) .
N1 C1 C2 123.0(2) .
C3 C2 C1 119.8(2) .
C2 C3 C4 119.2(2) .
C3 C4 C12 117.5(2) .
C3 C4 C5 123.5(2) .
C12 C4 C5 119.0(2) .
C6 C5 C4 121.1(2) .
C5 C6 C7 121.6(2) .
C8 C7 C11 117.2(2) .
C8 C7 C6 124.1(2) .
C11 C7 C6 118.7(2) .
C9 C8 C7 119.8(2) .
C8 C9 C10 119.4(2) .
N2 C10 C9 122.9(2) .
N2 C11 C7 123.0(2) .
N2 C11 C12 117.04(19) .
C7 C11 C12 119.9(2) .
N1 C12 C4 123.2(2) .
N1 C12 C11 117.11(19) .
C4 C12 C11 119.7(2) .
C18 C13 C14 112.3(2) .
C18 C13 Cu 124.03(17) .
C14 C13 Cu 123.67(17) .
C15 C14 F1 115.9(2) .
C15 C14 C13 124.7(2) .
F1 C14 C13 119.3(2) .
F2 C15 C14 120.4(2) .
F2 C15 C16 118.6(2) .
C14 C15 C16 121.0(2) .
O1 C16 C15 122.2(2) .
O1 C16 C17 121.3(2) .
C15 C16 C17 116.4(2) .
F3 C17 C18 121.0(2) .
F3 C17 C16 118.9(2) .
C18 C17 C16 120.0(2) .
F4 C18 C17 115.6(2) .
F4 C18 C13 118.8(2) .
C17 C18 C13 125.5(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu C13 1.934(2) .
Cu N1 2.0720(18) .
Cu N2 2.0949(19) .
Cu Cu 2.5770(6) 3_666
F1 C14 1.371(2) .
F2 C15 1.362(3) .
F3 C17 1.355(3) .
F4 C18 1.369(3) .
O1 C16 1.374(3) .
O1 C19 1.432(3) .
N1 C1 1.330(3) .
N1 C12 1.356(3) .
N2 C10 1.331(3) .
N2 C11 1.356(3) .
C1 C2 1.393(3) .
C2 C3 1.363(4) .
C3 C4 1.397(4) .
C4 C12 1.405(3) .
C4 C5 1.434(3) .
C5 C6 1.348(4) .
C6 C7 1.433(3) .
C7 C8 1.399(3) .
C7 C11 1.404(3) .
C8 C9 1.357(4) .
C9 C10 1.397(4) .
C11 C12 1.444(3) .
C13 C18 1.376(3) .
C13 C14 1.384(3) .
C14 C15 1.367(3) .
C15 C16 1.384(3) .
C16 C17 1.383(3) .
C17 C18 1.377(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
C13 Cu N1 C1 -36.3(2) .
N2 Cu N1 C1 -179.9(2) .
Cu Cu N1 C1 58.1(2) 3_666
C13 Cu N1 C12 141.89(15) .
N2 Cu N1 C12 -1.72(14) .
Cu Cu N1 C12 -123.69(13) 3_666
C13 Cu N2 C10 35.7(3) .
N1 Cu N2 C10 -178.6(2) .
Cu Cu N2 C10 -55.6(2) 3_666
C13 Cu N2 C11 -144.38(15) .
N1 Cu N2 C11 1.29(15) .
Cu Cu N2 C11 124.29(13) 3_666
C12 N1 C1 C2 0.2(3) .
Cu N1 C1 C2 178.31(17) .
N1 C1 C2 C3 -0.7(4) .
C1 C2 C3 C4 0.8(4) .
C2 C3 C4 C12 -0.3(3) .
C2 C3 C4 C5 -178.1(2) .
C3 C4 C5 C6 180.0(2) .
C12 C4 C5 C6 2.2(3) .
C4 C5 C6 C7 -0.3(4) .
C5 C6 C7 C8 178.1(2) .
C5 C6 C7 C11 -1.4(3) .
C11 C7 C8 C9 -1.4(3) .
C6 C7 C8 C9 179.0(2) .
C7 C8 C9 C10 -1.0(4) .
C11 N2 C10 C9 -0.3(3) .
Cu N2 C10 C9 179.55(19) .
C8 C9 C10 N2 2.0(4) .
C10 N2 C11 C7 -2.3(3) .
Cu N2 C11 C7 177.80(16) .
C10 N2 C11 C12 179.2(2) .
Cu N2 C11 C12 -0.7(2) .
C8 C7 C11 N2 3.2(3) .
C6 C7 C11 N2 -177.2(2) .
C8 C7 C11 C12 -178.4(2) .
C6 C7 C11 C12 1.2(3) .
C1 N1 C12 C4 0.3(3) .
Cu N1 C12 C4 -178.12(16) .
C1 N1 C12 C11 -179.7(2) .
Cu N1 C12 C11 1.9(2) .
C3 C4 C12 N1 -0.2(3) .
C5 C4 C12 N1 177.7(2) .
C3 C4 C12 C11 179.7(2) .
C5 C4 C12 C11 -2.3(3) .
N2 C11 C12 N1 -0.8(3) .
C7 C11 C12 N1 -179.35(19) .
N2 C11 C12 C4 179.21(19) .
C7 C11 C12 C4 0.7(3) .
N1 Cu C13 C18 -149.51(17) .
N2 Cu C13 C18 -22.1(3) .
Cu Cu C13 C18 93.4(2) 3_666
N1 Cu C13 C14 28.1(2) .
N2 Cu C13 C14 155.45(16) .
Cu Cu C13 C14 -89.04(18) 3_666
C18 C13 C14 C15 -2.0(3) .
Cu C13 C14 C15 -179.86(18) .
C18 C13 C14 F1 178.77(19) .
Cu C13 C14 F1 0.9(3) .
F1 C14 C15 F2 1.2(3) .
C13 C14 C15 F2 -178.0(2) .
F1 C14 C15 C16 179.99(19) .
C13 C14 C15 C16 0.7(4) .
C19 O1 C16 C15 72.4(3) .
C19 O1 C16 C17 -109.6(3) .
F2 C15 C16 O1 -2.4(3) .
C14 C15 C16 O1 178.8(2) .
F2 C15 C16 C17 179.5(2) .
C14 C15 C16 C17 0.7(3) .
O1 C16 C17 F3 2.3(3) .
C15 C16 C17 F3 -179.62(19) .
O1 C16 C17 C18 -178.8(2) .
C15 C16 C17 C18 -0.7(3) .
F3 C17 C18 F4 0.5(3) .
C16 C17 C18 F4 -178.3(2) .
F3 C17 C18 C13 178.1(2) .
C16 C17 C18 C13 -0.7(4) .
C14 C13 C18 F4 179.53(19) .
Cu C13 C18 F4 -2.6(3) .
C14 C13 C18 C17 2.0(3) .
Cu C13 C18 C17 179.85(18) .
