#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/76/7017645.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_7017645
loop_
_publ_author_name
'Mikhaylov, Dmitry'
'Gryaznova, Tatyana'
'Dudkina, Yulia'
'Khrizanphorov, Mikhail'
'Latypov, Shamil'
'Kataeva, Olga'
'Vicic, David A.'
'Sinyashin, Oleg G.'
'Budnikova, Yulia'
_publ_section_title
;
 Electrochemical nickel-induced fluoroalkylation: synthetic, structural
 and mechanistic study.
;
_journal_issue                   1
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              165
_journal_page_last               172
_journal_paper_doi               10.1039/c1dt11299f
_journal_volume                  41
_journal_year                    2012
_chemical_formula_moiety         'C26 H16 F24 N2'
_chemical_formula_sum            'C26 H16 F24 N2'
_chemical_formula_weight         812.41
_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                 110.047(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   16.091(1)
_cell_length_b                   5.905(1)
_cell_length_c                   16.645(1)
_cell_measurement_reflns_used    26400
_cell_measurement_temperature    198(2)
_cell_measurement_theta_max      25.40
_cell_measurement_theta_min      3.04
_cell_volume                     1485.7(3)
_computing_cell_refinement       'Dirax/lsq (Duisenberg, 1992)'
_computing_data_collection       'Collect (Nonius BV, 1999)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX (Farrugia 1999), enCIFer (Allen et al. 2004)'
_computing_structure_refinement
'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia 1999), PLATON (Spek 2005)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      198(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       φ
_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  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24975
_diffrn_reflns_theta_full        25.40
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.9769
_exptl_absorpt_correction_T_min  0.8954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS version 2.10 (Sheldrick,Bruker AXS Inc.,2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.816
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         2732
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0390
_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)+(0.0488P)²+1.0517P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1058
_reflns_number_gt                2070
_reflns_number_total             2732
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1dt11299f.txt
_cod_data_source_block           bud4
_cod_original_sg_symbol_Hall     '-P 2yn '
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7017645
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.55118(12) -0.0171(4) 0.01648(13) 0.0285(5) Uani 1 1 d . . .
H1A H 0.5794 0.1237 0.0043 0.034 Uiso 1 1 calc R . .
C2 C 0.57545(13) -0.2167(4) -0.03124(13) 0.0312(5) Uani 1 1 d . . .
H2A H 0.5676 -0.3606 -0.0042 0.037 Uiso 1 1 calc R . .
H2B H 0.5345 -0.2182 -0.0912 0.037 Uiso 1 1 calc R . .
C3 C 0.66862(13) -0.2030(4) -0.03062(13) 0.0314(5) Uani 1 1 d . . .
C4 C 0.70019(13) -0.4133(4) -0.06613(12) 0.0289(5) Uani 1 1 d . . .
C5 C 0.78844(13) -0.3932(4) -0.08373(13) 0.0306(5) Uani 1 1 d . . .
C6 C 0.82774(13) -0.6167(4) -0.10222(13) 0.0305(5) Uani 1 1 d . A .
C7 C 0.90444(13) -0.5953(4) -0.13743(13) 0.0337(5) Uani 1 1 d D . .
C8A C 0.9607(5) -0.8079(13) -0.1275(6) 0.0438(19) Uani 0.530(5) 1 d PD A 1
H8A H 0.9874 -0.8512 -0.0659 0.053 Uiso 0.530(5) 1 calc PR A 1
F25A F 0.9091(2) -0.9750(5) -0.1726(2) 0.0603(11) Uani 0.530(5) 1 d PD A 1
F26A F 1.0243(5) -0.7701(19) -0.1613(4) 0.0543(15) Uani 0.530(5) 1 d PD A 1
C8B C 0.9403(7) -0.8282(16) -0.1531(6) 0.0438(19) Uani 0.470(5) 1 d PD A 2
H8B H 0.8912 -0.9277 -0.1888 0.053 Uiso 0.470(5) 1 calc PR A 2
F25B F 0.9827(2) -0.9234(6) -0.0761(2) 0.0584(12) Uani 0.470(5) 1 d PD A 2
F26B F 0.9993(6) -0.789(2) -0.1925(5) 0.068(2) Uani 0.470(5) 1 d PD A 2
C9 C 0.58535(13) -0.0580(4) 0.11225(13) 0.0323(5) Uani 1 1 d . . .
N10 N 0.55930(13) -0.2518(4) 0.13778(13) 0.0458(5) Uani 1 1 d . . .
C11 C 0.5862(2) -0.2888(6) 0.22265(18) 0.0627(8) Uani 1 1 d . . .
H11A H 0.5684 -0.4255 0.2421 0.075 Uiso 1 1 calc R . .
C12 C 0.6379(2) -0.1415(7) 0.28283(17) 0.0673(9) Uani 1 1 d . . .
H12A H 0.6548 -0.1754 0.3421 0.081 Uiso 1 1 calc R . .
C13 C 0.66456(18) 0.0554(6) 0.25566(16) 0.0596(8) Uani 1 1 d . . .
H13A H 0.7007 0.1607 0.2957 0.071 Uiso 1 1 calc R . .
C14 C 0.63800(15) 0.0981(4) 0.16903(15) 0.0438(6) Uani 1 1 d . . .
H14A H 0.6557 0.2335 0.1486 0.053 Uiso 1 1 calc R . .
F15 F 0.72697(8) -0.1622(3) 0.04804(9) 0.0582(5) Uani 1 1 d . . .
F16 F 0.67641(11) -0.0250(2) -0.07949(11) 0.0600(5) Uani 1 1 d . . .
F17 F 0.63699(8) -0.4774(3) -0.13850(9) 0.0509(4) Uani 1 1 d . . .
F18 F 0.70955(9) -0.5821(2) -0.00841(9) 0.0503(4) Uani 1 1 d . . .
F19 F 0.77403(10) -0.2587(2) -0.15255(9) 0.0524(4) Uani 1 1 d . . .
F20 F 0.84836(8) -0.2922(2) -0.01684(9) 0.0495(4) Uani 1 1 d . . .
F21 F 0.85928(9) -0.7345(2) -0.02782(8) 0.0461(4) Uani 1 1 d . . .
F22 F 0.76384(8) -0.7399(2) -0.15806(8) 0.0414(3) Uani 1 1 d . . .
F23 F 0.87218(9) -0.5150(3) -0.21810(8) 0.0498(4) Uani 1 1 d . A .
F24 F 0.96424(8) -0.4471(2) -0.09052(9) 0.0473(4) Uani 1 1 d . A .
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'
F F 0.0171 0.0103 '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
C9 C1 C2 110.77(17) . .
C9 C1 C1 110.42(19) . 3_655
C2 C1 C1 109.9(2) . 3_655
C9 C1 H1A 108.6 . .
C2 C1 H1A 108.6 . .
C1 C1 H1A 108.6 3_655 .
C3 C2 C1 112.58(17) . .
C3 C2 H2A 109.1 . .
C1 C2 H2A 109.1 . .
C3 C2 H2B 109.1 . .
C1 C2 H2B 109.1 . .
H2A C2 H2B 107.8 . .
F15 C3 F16 105.48(18) . .
F15 C3 C2 112.29(17) . .
F16 C3 C2 109.56(18) . .
F15 C3 C4 107.87(17) . .
F16 C3 C4 106.51(16) . .
C2 C3 C4 114.59(17) . .
F17 C4 F18 107.20(17) . .
F17 C4 C3 109.01(16) . .
F18 C4 C3 107.03(16) . .
F17 C4 C5 108.33(16) . .
F18 C4 C5 107.68(16) . .
C3 C4 C5 117.15(17) . .
F20 C5 F19 108.03(18) . .
F20 C5 C6 108.70(16) . .
F19 C5 C6 107.36(16) . .
F20 C5 C4 108.82(16) . .
F19 C5 C4 107.71(16) . .
C6 C5 C4 115.97(17) . .
F22 C6 F21 108.21(17) . .
F22 C6 C5 109.51(16) . .
F21 C6 C5 107.91(16) . .
F22 C6 C7 107.75(16) . .
F21 C6 C7 106.91(16) . .
C5 C6 C7 116.28(18) . .
F24 C7 F23 107.80(18) . .
F24 C7 C8A 101.2(3) . .
F23 C7 C8A 114.2(4) . .
F24 C7 C8B 116.4(4) . .
F23 C7 C8B 100.5(3) . .
C8A C7 C8B 17.1(6) . .
F24 C7 C6 109.96(17) . .
F23 C7 C6 108.78(17) . .
C8A C7 C6 114.5(4) . .
C8B C7 C6 112.6(4) . .
F26A C8A F25A 107.6(7) . .
F26A C8A C7 109.1(7) . .
F25A C8A C7 108.3(6) . .
F26A C8A H8A 110.6 . .
F25A C8A H8A 110.6 . .
C7 C8A H8A 110.6 . .
F26B C8B F25B 108.9(9) . .
F26B C8B C7 107.1(8) . .
F25B C8B C7 107.8(6) . .
F26B C8B H8B 111.0 . .
F25B C8B H8B 111.0 . .
C7 C8B H8B 111.0 . .
N10 C9 C14 122.6(2) . .
N10 C9 C1 115.46(19) . .
C14 C9 C1 121.9(2) . .
C9 N10 C11 116.7(2) . .
N10 C11 C12 124.1(3) . .
N10 C11 H11A 118.0 . .
C12 C11 H11A 118.0 . .
C13 C12 C11 118.5(3) . .
C13 C12 H12A 120.7 . .
C11 C12 H12A 120.7 . .
C12 C13 C14 118.7(3) . .
C12 C13 H13A 120.6 . .
C14 C13 H13A 120.6 . .
C13 C14 C9 119.4(3) . .
C13 C14 H14A 120.3 . .
C9 C14 H14A 120.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C9 1.517(3) .
C1 C2 1.545(3) .
C1 C1 1.560(4) 3_655
C1 H1A 1.0000 .
C2 C3 1.498(3) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 F15 1.346(2) .
C3 F16 1.361(3) .
C3 C4 1.535(3) .
C4 F17 1.337(2) .
C4 F18 1.356(2) .
C4 C5 1.550(3) .
C5 F20 1.338(2) .
C5 F19 1.347(2) .
C5 C6 1.539(3) .
C6 F22 1.340(2) .
C6 F21 1.358(2) .
C6 C7 1.542(3) .
C7 F24 1.337(2) .
C7 F23 1.349(3) .
C7 C8A 1.523(8) .
C7 C8B 1.548(10) .
C8A F26A 1.345(6) .
C8A F25A 1.342(7) .
C8A H8A 1.0000 .
C8B F26B 1.347(6) .
C8B F25B 1.351(7) .
C8B H8B 1.0000 .
C9 N10 1.337(3) .
C9 C14 1.383(3) .
N10 C11 1.346(3) .
C11 C12 1.371(4) .
C11 H11A 0.9500 .
C12 C13 1.369(5) .
C12 H12A 0.9500 .
C13 C14 1.379(4) .
C13 H13A 0.9500 .
C14 H14A 0.9500 .
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
C9 C1 C2 C3 -80.9(2) .
C1 C1 C2 C3 156.8(2) 3_655
C1 C2 C3 F15 48.4(2) .
C1 C2 C3 F16 -68.5(2) .
C1 C2 C3 C4 171.89(17) .
F15 C3 C4 F17 170.91(16) .
F16 C3 C4 F17 -76.3(2) .
C2 C3 C4 F17 45.1(2) .
F15 C3 C4 F18 55.3(2) .
F16 C3 C4 F18 168.10(16) .
C2 C3 C4 F18 -70.6(2) .
F15 C3 C4 C5 -65.7(2) .
F16 C3 C4 C5 47.2(2) .
C2 C3 C4 C5 168.46(17) .
F17 C4 C5 F20 169.34(17) .
F18 C4 C5 F20 -75.0(2) .
C3 C4 C5 F20 45.6(2) .
F17 C4 C5 F19 52.5(2) .
F18 C4 C5 F19 168.10(16) .
C3 C4 C5 F19 -71.3(2) .
F17 C4 C5 C6 -67.8(2) .
F18 C4 C5 C6 47.8(2) .
C3 C4 C5 C6 168.45(17) .
F20 C5 C6 F22 168.63(16) .
F19 C5 C6 F22 -74.7(2) .
C4 C5 C6 F22 45.7(2) .
F20 C5 C6 F21 51.1(2) .
F19 C5 C6 F21 167.68(15) .
C4 C5 C6 F21 -71.9(2) .
F20 C5 C6 C7 -69.0(2) .
F19 C5 C6 C7 47.6(2) .
C4 C5 C6 C7 168.09(17) .
F22 C6 C7 F24 171.06(17) .
F21 C6 C7 F24 -72.8(2) .
C5 C6 C7 F24 47.8(2) .
F22 C6 C7 F23 53.2(2) .
F21 C6 C7 F23 169.34(17) .
C5 C6 C7 F23 -70.1(2) .
F22 C6 C7 C8A -75.8(4) .
F21 C6 C7 C8A 40.3(4) .
C5 C6 C7 C8A 160.9(4) .
F22 C6 C7 C8B -57.3(4) .
F21 C6 C7 C8B 58.8(4) .
C5 C6 C7 C8B 179.4(4) .
F24 C7 C8A F26A -62.6(6) .
F23 C7 C8A F26A 52.9(6) .
C8B C7 C8A F26A 92(2) .
C6 C7 C8A F26A 179.2(4) .
F24 C7 C8A F25A -179.4(5) .
F23 C7 C8A F25A -63.9(6) .
C8B C7 C8A F25A -25.0(19) .
C6 C7 C8A F25A 62.4(7) .
F24 C7 C8B F26B -58.6(7) .
F23 C7 C8B F26B 57.5(7) .
C8A C7 C8B F26B -87(2) .
C6 C7 C8B F26B 173.1(5) .
F24 C7 C8B F25B 58.4(8) .
F23 C7 C8B F25B 174.5(6) .
C8A C7 C8B F25B 30.1(18) .
C6 C7 C8B F25B -69.9(8) .
C2 C1 C9 N10 -55.3(2) .
C1 C1 C9 N10 66.6(3) 3_655
C2 C1 C9 C14 126.2(2) .
C1 C1 C9 C14 -111.8(2) 3_655
C14 C9 N10 C11 0.6(3) .
C1 C9 N10 C11 -177.8(2) .
C9 N10 C11 C12 -0.1(4) .
N10 C11 C12 C13 -0.4(4) .
C11 C12 C13 C14 0.4(4) .
C12 C13 C14 C9 0.1(4) .
N10 C9 C14 C13 -0.6(3) .
C1 C9 C14 C13 177.7(2) .
