#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/35/1513512.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_1513512
loop_
_publ_author_name
'Gao, Bing'
'Zhao, Yanchuan'
'Ni, Chuanfa'
'Hu, Jinbo'
_publ_section_title
;
 AgF-mediated fluorinative homocoupling of gem-difluoroalkenes.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              102
_journal_page_last               105
_journal_paper_doi               10.1021/ol403083e
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C18 H8 F6 N2'
_chemical_formula_weight         366.26
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 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                 95.074(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.205(12)
_cell_length_b                   9.060(8)
_cell_length_c                   12.052(10)
_cell_measurement_reflns_used    896
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.545
_cell_measurement_theta_min      5.379
_cell_volume                     1654(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0995
_diffrn_reflns_av_sigmaI/netI    0.0781
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4283
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.0385
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.145
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1635
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.172
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.0751
_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)+(0.1448P)²+0.8651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2232
_refine_ls_wR_factor_ref         0.2530
_reflns_number_gt                1094
_reflns_number_total             1635
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol403083e_si_003.cif
_cod_data_source_block           cd21323
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      C2/m
_cod_database_code               1513512
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.1224(4) 0.0000 0.9304(5) 0.0895(17) Uani 1 2 d S . .
N2 N 0.3675(6) 0.0000 1.2059(5) 0.114(2) Uani 1 2 d S . .
F1 F 0.1057(3) 0.0000 0.4479(3) 0.199(4) Uani 1 2 d S . .
F2 F 0.2196(3) 0.1153(3) 0.4156(2) 0.1238(13) Uani 1 1 d . . .
F3 F 0.3732(7) 0.0000 0.4697(7) 0.098(4) Uani 0.50 2 d SPU A 1
F4 F 0.4294(3) 0.1177(5) 0.6012(5) 0.1358(18) Uani 0.80 1 d PU A 1
F3' F 0.3760(9) 0.0915(14) 0.4915(12) 0.096(3) Uani 0.25 1 d PU . 2
F4' F 0.4522(11) 0.0000 0.6413(16) 0.148(4) Uani 0.40 2 d SPU A 2
C1 C -0.0666(4) 0.0000 0.8730(5) 0.0680(14) Uani 1 2 d S . .
C2 C 0.0047(3) 0.0000 0.7998(4) 0.0536(12) Uani 1 2 d S . .
C3 C 0.0385(2) 0.1319(4) 0.7659(3) 0.0629(10) Uani 1 1 d . . .
H3 H 0.0154 0.2205 0.7894 0.075 Uiso 1 1 calc R . .
C4 C 0.1063(2) 0.1329(4) 0.6972(3) 0.0612(10) Uani 1 1 d . . .
H4 H 0.1291 0.2219 0.6740 0.073 Uiso 1 1 calc R . .
C5 C 0.1403(3) 0.0000 0.6631(3) 0.0503(11) Uani 1 2 d S . .
C6 C 0.2168(3) 0.0000 0.5907(4) 0.0528(12) Uani 1 2 d S . .
C7 C 0.2993(3) 0.0000 0.6379(4) 0.0517(11) Uani 1 2 d S A .
C8 C 0.3165(3) 0.0000 0.7621(3) 0.0487(11) Uani 1 2 d S . .
C9 C 0.3240(2) 0.1324(4) 0.8201(3) 0.0596(10) Uani 1 1 d . . .
H9 H 0.3197 0.2214 0.7815 0.071 Uiso 1 1 calc R . .
C10 C 0.3377(3) 0.1324(4) 0.9344(3) 0.0623(10) Uani 1 1 d . . .
H10 H 0.3425 0.2213 0.9731 0.075 Uiso 1 1 calc R . .
C11 C 0.3444(3) 0.0000 0.9919(4) 0.0569(12) Uani 1 2 d S . .
C12 C 0.3563(5) 0.0000 1.1111(4) 0.0744(16) Uani 1 2 d S . .
C13 C 0.1906(4) 0.0000 0.4673(4) 0.0743(16) Uani 1 2 d S . .
C14 C 0.3816(4) 0.0000 0.5763(5) 0.0672(14) Uani 1 2 d S . .
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
C14 F3' F3' 50.9(7) . 6
N1 C1 C2 180.0(6) . .
C3 C2 C3 120.5(4) 6 .
C3 C2 C1 119.8(2) 6 .
C3 C2 C1 119.8(2) . .
C2 C3 C4 120.1(3) . .
C2 C3 H3 119.9 . .
C4 C3 H3 119.9 . .
C3 C4 C5 119.4(3) . .
C3 C4 H4 120.3 . .
C5 C4 H4 120.3 . .
C4 C5 C4 120.5(4) . 6
C4 C5 C6 119.7(2) . .
C4 C5 C6 119.8(2) 6 .
C7 C6 C13 125.4(4) . .
C7 C6 C5 119.8(4) . .
C13 C6 C5 114.8(4) . .
C6 C7 C8 120.1(4) . .
C6 C7 C14 125.5(4) . .
C8 C7 C14 114.3(4) . .
C9 C8 C9 119.7(4) 6 .
C9 C8 C7 120.2(2) 6 .
C9 C8 C7 120.2(2) . .
C10 C9 C8 120.2(3) . .
C10 C9 H9 119.9 . .
C8 C9 H9 119.9 . .
C9 C10 C11 120.0(3) . .
C9 C10 H10 120.0 . .
C11 C10 H10 120.0 . .
C10 C11 C10 120.1(4) . 6
C10 C11 C12 120.0(2) . .
C10 C11 C12 120.0(2) 6 .
N2 C12 C11 178.6(8) . .
F1 C13 F2 106.6(4) . .
F1 C13 F2 106.6(4) . 6
F2 C13 F2 105.5(5) . 6
F1 C13 C6 110.6(5) . .
F2 C13 C6 113.5(3) . .
F2 C13 C6 113.5(3) 6 .
F4' C14 F3 128.5(9) . .
F4' C14 F4 55.8(4) . .
F3 C14 F4 103.5(5) . .
F4' C14 F4 55.8(4) . 6
F3 C14 F4 103.5(5) . 6
F4 C14 F4 108.9(7) . 6
F4' C14 F3' 118.2(8) . .
F3 C14 F3' 39.1(7) . .
F4 C14 F3' 70.2(7) . .
F4 C14 F3' 133.5(7) 6 .
F4' C14 F3' 118.2(8) . 6
F3 C14 F3' 39.1(7) . 6
F4 C14 F3' 133.4(7) . 6
F4 C14 F3' 70.2(7) 6 6
F3' C14 F3' 78.3(14) . 6
F4' C14 C7 112.8(8) . .
F3 C14 C7 118.7(6) . .
F4 C14 C7 110.8(3) . .
F4 C14 C7 110.8(3) 6 .
F3' C14 C7 112.6(6) . .
F3' C14 C7 112.6(6) 6 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.141(7) .
N2 C12 1.141(7) .
F1 C13 1.292(8) .
F2 C13 1.312(4) .
F3 C14 1.280(10) .
F4 C14 1.311(5) .
F3' C14 1.313(13) .
F3' F3' 1.66(3) 6
F4' C14 1.272(19) .
C1 C2 1.456(7) .
C2 C3 1.377(4) 6
C2 C3 1.377(4) .
C3 C4 1.379(5) .
C3 H3 0.9300 .
C4 C5 1.387(4) .
C4 H4 0.9300 .
C5 C4 1.387(4) 6
C5 C6 1.514(7) .
C6 C7 1.330(7) .
C6 C13 1.506(7) .
C7 C8 1.497(6) .
C7 C14 1.510(7) .
C8 C9 1.388(4) 6
C8 C9 1.388(4) .
C9 C10 1.376(5) .
C9 H9 0.9300 .
C10 C11 1.385(4) .
C10 H10 0.9300 .
C11 C10 1.385(4) 6
C11 C12 1.431(7) .
C13 F2 1.312(4) 6
C14 F4 1.311(5) 6
C14 F3' 1.313(13) 6
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
_geom_torsion_site_symmetry_4
N1 C1 C2 C3 90(100) . 6
N1 C1 C2 C3 -90(100) . .
C3 C2 C3 C4 0.2(7) 6 .
C1 C2 C3 C4 179.6(4) . .
C2 C3 C4 C5 -0.3(6) . .
C3 C4 C5 C4 0.3(7) . 6
C3 C4 C5 C6 -178.0(4) . .
C4 C5 C6 C7 89.2(3) . .
C4 C5 C6 C7 -89.2(3) 6 .
C4 C5 C6 C13 -90.8(3) . .
C4 C5 C6 C13 90.8(3) 6 .
C13 C6 C7 C8 180.0 . .
C5 C6 C7 C8 0.000(1) . .
C13 C6 C7 C14 0.000(1) . .
C5 C6 C7 C14 180.000(1) . .
C6 C7 C8 C9 89.6(4) . 6
C14 C7 C8 C9 -90.4(4) . 6
C6 C7 C8 C9 -89.6(4) . .
C14 C7 C8 C9 90.4(4) . .
C9 C8 C9 C10 -0.7(7) 6 .
C7 C8 C9 C10 178.4(4) . .
C8 C9 C10 C11 0.2(6) . .
C9 C10 C11 C10 0.3(8) . 6
C9 C10 C11 C12 -178.3(5) . .
C10 C11 C12 N2 -90.7(5) . .
C10 C11 C12 N2 90.7(5) 6 .
C7 C6 C13 F1 180.0 . .
C5 C6 C13 F1 0.0 . .
C7 C6 C13 F2 -60.2(4) . .
C5 C6 C13 F2 119.8(4) . .
C7 C6 C13 F2 60.2(4) . 6
C5 C6 C13 F2 -119.8(4) . 6
F3' F3' C14 F4' 115.8(9) 6 .
F3' F3' C14 F3 -1.5(16) 6 .
F3' F3' C14 F4 145.2(5) 6 .
F3' F3' C14 F4 47.6(7) 6 6
F3' F3' C14 C7 -109.8(8) 6 .
C6 C7 C14 F4' 180.000(4) . .
C8 C7 C14 F4' 0.000(3) . .
C6 C7 C14 F3 0.000(2) . .
C8 C7 C14 F3 180.000(1) . .
C6 C7 C14 F4 119.5(5) . .
C8 C7 C14 F4 -60.5(5) . .
C6 C7 C14 F4 -119.5(5) . 6
C8 C7 C14 F4 60.5(5) . 6
C6 C7 C14 F3' 43.1(8) . .
C8 C7 C14 F3' -136.9(8) . .
C6 C7 C14 F3' -43.1(8) . 6
C8 C7 C14 F3' 136.9(8) . 6
