#------------------------------------------------------------------------------
#$Date: 2016-03-25 14:07:06 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179880 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/76/7017643.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_7017643
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 H14 F26 N2'
_chemical_formula_sum            'C26 H14 F26 N2'
_chemical_formula_weight         848.39
_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                83.270(4)
_cell_angle_beta                 80.137(4)
_cell_angle_gamma                86.720(4)
_cell_formula_units_Z            1
_cell_length_a                   5.4351(3)
_cell_length_b                   9.9164(4)
_cell_length_c                   14.5715(6)
_cell_measurement_reflns_used    4268
_cell_measurement_temperature    198(2)
_cell_measurement_theta_max      25.40
_cell_measurement_theta_min      3.72
_cell_volume                     767.86(6)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0130
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15277
_diffrn_reflns_theta_full        25.40
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         3.34
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.9533
_exptl_absorpt_correction_T_min  0.9193
_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    1.835
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             418
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2814
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0582P)²+0.3148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1089
_reflns_number_gt                2358
_reflns_number_total             2814
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1dt11299f.txt
_cod_data_source_block           bud3
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7017643
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
C1 C 0.4898(3) 0.06408(16) 0.02634(12) 0.0312(4) Uani 1 1 d .
H1A H 0.3098 0.0820 0.0521 0.037 Uiso 1 1 calc R
C2 C 0.6352(3) 0.03709(17) 0.10911(12) 0.0332(4) Uani 1 1 d .
H2A H 0.5653 -0.0424 0.1510 0.040 Uiso 1 1 calc R
H2B H 0.8118 0.0136 0.0846 0.040 Uiso 1 1 calc R
C3 C 0.6266(3) 0.15592(17) 0.16555(12) 0.0329(4) Uani 1 1 d .
C4 C 0.6985(3) 0.11705(16) 0.26344(12) 0.0339(4) Uani 1 1 d .
C5 C 0.7201(3) 0.23686(17) 0.32126(12) 0.0330(4) Uani 1 1 d .
C6 C 0.7326(3) 0.19494(17) 0.42620(13) 0.0374(4) Uani 1 1 d .
C7 C 0.8125(4) 0.30827(19) 0.47798(14) 0.0417(4) Uani 1 1 d .
C8 C 0.7633(5) 0.2845(2) 0.58513(15) 0.0552(6) Uani 1 1 d .
C9 C 0.5830(3) 0.18736(17) -0.03951(12) 0.0332(4) Uani 1 1 d .
N10 N 0.8134(3) 0.17449(16) -0.08895(11) 0.0409(4) Uani 1 1 d .
C11 C 0.8984(4) 0.2819(2) -0.14746(15) 0.0532(5) Uani 1 1 d .
H11A H 1.0605 0.2743 -0.1837 0.064 Uiso 1 1 calc R
C12 C 0.7645(5) 0.4029(2) -0.15823(16) 0.0616(7) Uani 1 1 d .
H12A H 0.8338 0.4770 -0.2002 0.074 Uiso 1 1 calc R
C13 C 0.5295(5) 0.4149(2) -0.10733(16) 0.0589(6) Uani 1 1 d .
H13A H 0.4330 0.4975 -0.1134 0.071 Uiso 1 1 calc R
C14 C 0.4347(4) 0.30492(18) -0.04690(14) 0.0445(5) Uani 1 1 d .
H14A H 0.2715 0.3100 -0.0113 0.053 Uiso 1 1 calc R
F15 F 0.3951(2) 0.21721(12) 0.17753(8) 0.0473(3) Uani 1 1 d .
F16 F 0.7854(2) 0.25374(10) 0.12132(7) 0.0441(3) Uani 1 1 d .
F17 F 0.9197(2) 0.04800(11) 0.25222(8) 0.0506(3) Uani 1 1 d .
F18 F 0.5253(3) 0.03416(12) 0.31330(8) 0.0556(3) Uani 1 1 d .
F19 F 0.9290(2) 0.30271(12) 0.28351(8) 0.0500(3) Uani 1 1 d .
F20 F 0.5250(2) 0.32394(11) 0.31572(8) 0.0489(3) Uani 1 1 d .
F21 F 0.5030(2) 0.15750(14) 0.46966(8) 0.0589(4) Uani 1 1 d .
F22 F 0.8889(3) 0.08829(12) 0.43451(9) 0.0622(4) Uani 1 1 d .
F23 F 0.6972(3) 0.42552(11) 0.45203(8) 0.0545(3) Uani 1 1 d .
F24 F 1.0587(2) 0.32308(15) 0.45248(9) 0.0614(4) Uani 1 1 d .
F25 F 0.5192(3) 0.28997(18) 0.61804(10) 0.0833(5) Uani 1 1 d .
F26 F 0.8636(4) 0.38106(15) 0.61952(10) 0.0848(5) Uani 1 1 d .
F27 F 0.8546(3) 0.16614(14) 0.61547(10) 0.0746(5) Uani 1 1 d .
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 111.56(14) . .
C9 C1 C1 111.00(18) . 2_655
C2 C1 C1 109.42(16) . 2_655
C9 C1 H1A 108.3 . .
C2 C1 H1A 108.3 . .
C1 C1 H1A 108.3 2_655 .
C3 C2 C1 113.74(14) . .
C3 C2 H2A 108.8 . .
C1 C2 H2A 108.8 . .
C3 C2 H2B 108.8 . .
C1 C2 H2B 108.8 . .
H2A C2 H2B 107.7 . .
F15 C3 F16 105.99(13) . .
F15 C3 C2 111.05(14) . .
F16 C3 C2 111.67(14) . .
F15 C3 C4 107.71(14) . .
F16 C3 C4 106.40(14) . .
C2 C3 C4 113.60(14) . .
F18 C4 F17 108.55(14) . .
F18 C4 C3 107.88(14) . .
F17 C4 C3 107.82(14) . .
F18 C4 C5 108.00(14) . .
F17 C4 C5 108.20(14) . .
C3 C4 C5 116.19(14) . .
F20 C5 F19 108.07(14) . .
F20 C5 C6 108.19(14) . .
F19 C5 C6 107.49(14) . .
F20 C5 C4 109.29(14) . .
F19 C5 C4 108.64(14) . .
C6 C5 C4 114.96(14) . .
F22 C6 F21 107.92(15) . .
F22 C6 C7 108.75(15) . .
F21 C6 C7 107.70(15) . .
F22 C6 C5 109.54(15) . .
F21 C6 C5 108.10(15) . .
C7 C6 C5 114.63(14) . .
F23 C7 F24 107.85(16) . .
F23 C7 C8 108.06(16) . .
F24 C7 C8 106.49(17) . .
F23 C7 C6 109.29(16) . .
F24 C7 C6 108.76(15) . .
C8 C7 C6 116.09(16) . .
F27 C8 F26 109.6(2) . .
F27 C8 F25 108.2(2) . .
F26 C8 F25 107.1(2) . .
F27 C8 C7 111.45(18) . .
F26 C8 C7 109.52(18) . .
F25 C8 C7 110.93(19) . .
N10 C9 C14 123.05(17) . .
N10 C9 C1 116.14(15) . .
C14 C9 C1 120.81(17) . .
C11 N10 C9 117.00(18) . .
N10 C11 C12 123.7(2) . .
N10 C11 H11A 118.2 . .
C12 C11 H11A 118.2 . .
C13 C12 C11 118.81(19) . .
C13 C12 H12A 120.6 . .
C11 C12 H12A 120.6 . .
C12 C13 C14 118.9(2) . .
C12 C13 H13A 120.5 . .
C14 C13 H13A 120.5 . .
C9 C14 C13 118.5(2) . .
C9 C14 H14A 120.7 . .
C13 C14 H14A 120.7 . .
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(2) .
C1 C2 1.542(2) .
C1 C1 1.549(3) 2_655
C1 H1A 1.0000 .
C2 C3 1.508(2) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 F15 1.359(2) .
C3 F16 1.3639(19) .
C3 C4 1.543(3) .
C4 F18 1.343(2) .
C4 F17 1.344(2) .
C4 C5 1.556(2) .
C5 F20 1.336(2) .
C5 F19 1.343(2) .
C5 C6 1.549(3) .
C6 F22 1.326(2) .
C6 F21 1.350(2) .
C6 C7 1.545(3) .
C7 F23 1.335(2) .
C7 F24 1.338(2) .
C7 C8 1.531(3) .
C8 F27 1.306(3) .
C8 F26 1.316(3) .
C8 F25 1.331(3) .
C9 N10 1.341(2) .
C9 C14 1.383(3) .
N10 C11 1.335(2) .
C11 C12 1.375(4) .
C11 H11A 0.9500 .
C12 C13 1.369(4) .
C12 H12A 0.9500 .
C13 C14 1.384(3) .
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 57.0(2) .
C1 C1 C2 C3 -179.80(16) 2_655
C1 C2 C3 F15 40.6(2) .
C1 C2 C3 F16 -77.45(18) .
C1 C2 C3 C4 162.21(14) .
F15 C3 C4 F18 58.72(17) .
F16 C3 C4 F18 172.02(13) .
C2 C3 C4 F18 -64.71(19) .
F15 C3 C4 F17 175.77(13) .
F16 C3 C4 F17 -70.93(16) .
C2 C3 C4 F17 52.34(19) .
F15 C3 C4 C5 -62.65(19) .
F16 C3 C4 C5 50.65(19) .
C2 C3 C4 C5 173.92(14) .
F18 C4 C5 F20 -76.41(17) .
F17 C4 C5 F20 166.28(13) .
C3 C4 C5 F20 44.9(2) .
F18 C4 C5 F19 165.89(14) .
F17 C4 C5 F19 48.58(18) .
C3 C4 C5 F19 -72.81(19) .
F18 C4 C5 C6 45.4(2) .
F17 C4 C5 C6 -71.87(18) .
C3 C4 C5 C6 166.74(14) .
F20 C5 C6 F22 166.90(14) .
F19 C5 C6 F22 -76.62(18) .
C4 C5 C6 F22 44.5(2) .
F20 C5 C6 F21 49.55(18) .
F19 C5 C6 F21 166.03(13) .
C4 C5 C6 F21 -72.89(19) .
F20 C5 C6 C7 -70.56(19) .
F19 C5 C6 C7 45.9(2) .
C4 C5 C6 C7 167.00(15) .
F22 C6 C7 F23 165.32(15) .
F21 C6 C7 F23 -77.98(18) .
C5 C6 C7 F23 42.4(2) .
F22 C6 C7 F24 47.8(2) .
F21 C6 C7 F24 164.52(14) .
C5 C6 C7 F24 -75.2(2) .
F22 C6 C7 C8 -72.2(2) .
F21 C6 C7 C8 44.5(2) .
C5 C6 C7 C8 164.84(17) .
F23 C7 C8 F27 175.09(18) .
F24 C7 C8 F27 -69.3(2) .
C6 C7 C8 F27 52.0(3) .
F23 C7 C8 F26 -63.5(2) .
F24 C7 C8 F26 52.2(2) .
C6 C7 C8 F26 173.39(18) .
F23 C7 C8 F25 54.5(2) .
F24 C7 C8 F25 170.11(17) .
C6 C7 C8 F25 -68.7(2) .
C2 C1 C9 N10 68.6(2) .
C1 C1 C9 N10 -53.7(2) 2_655
C2 C1 C9 C14 -111.53(18) .
C1 C1 C9 C14 126.2(2) 2_655
C14 C9 N10 C11 0.0(3) .
C1 C9 N10 C11 179.86(16) .
C9 N10 C11 C12 0.8(3) .
N10 C11 C12 C13 -0.8(3) .
C11 C12 C13 C14 -0.1(3) .
N10 C9 C14 C13 -0.7(3) .
C1 C9 C14 C13 179.38(17) .
C12 C13 C14 C9 0.8(3) .
