#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/39/1513947.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_1513947
loop_
_publ_author_name
'Xie, Jin'
'Yuan, Xiangai'
'Abdukader, Ablimit'
'Zhu, Chengjian'
'Ma, Jing'
_publ_section_title
;
 Visible-light-promoted radical C-h trifluoromethylation of free anilines.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1768
_journal_page_last               1771
_journal_paper_doi               10.1021/ol500469a
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C9 H8 F3 N O2'
_chemical_formula_sum            'C9 H8 F3 N O2'
_chemical_formula_weight         219.16
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 106.010(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.293(3)
_cell_length_b                   8.606(2)
_cell_length_c                   14.701(3)
_cell_measurement_reflns_used    1906
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.73
_cell_measurement_theta_min      2.74
_cell_volume                     1859.8(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5047
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_correction_T_min  0.9636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1638
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0372
_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)+(0.0620P)²+0.7730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1119
_reflns_number_gt                1373
_reflns_number_total             1638
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol500469a_si_002.cif
_cod_data_source_block           20130828dd_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/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_cell_volume        1859.9(7)
_cod_original_sg_symbol_H-M      'C2/c  '
_cod_database_code               1513947
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C1 C 0.76848(10) 0.45681(18) 0.87805(11) 0.0405(4) Uani 1 1 d .
C2 C 0.80820(11) 0.44062(19) 0.80338(11) 0.0426(4) Uani 1 1 d .
C3 C 0.89013(11) 0.5204(2) 0.81086(12) 0.0474(4) Uani 1 1 d .
H3 H 0.9180 0.5115 0.7623 0.057 Uiso 1 1 calc R
C4 C 0.92999(11) 0.6108(2) 0.88781(12) 0.0450(4) Uani 1 1 d .
H4 H 0.9842 0.6620 0.8906 0.054 Uiso 1 1 calc R
C5 C 0.89011(10) 0.62694(19) 0.96202(11) 0.0410(4) Uani 1 1 d .
C6 C 0.80930(11) 0.54847(19) 0.95596(12) 0.0417(4) Uani 1 1 d .
H6 H 0.7820 0.5575 1.0050 0.050 Uiso 1 1 calc R
C7 C 0.93101(11) 0.72018(19) 1.04780(12) 0.0431(4) Uani 1 1 d .
C8 C 1.05135(13) 0.8884(2) 1.12288(13) 0.0565(5) Uani 1 1 d .
H8A H 1.0214 0.9872 1.1190 0.085 Uiso 1 1 calc R
H8B H 1.1135 0.9038 1.1227 0.085 Uiso 1 1 calc R
H8C H 1.0497 0.8368 1.1803 0.085 Uiso 1 1 calc R
C9 C 0.68378(12) 0.3703(2) 0.87681(12) 0.0492(4) Uani 1 1 d .
F1 F 0.61550(7) 0.39613(15) 0.79859(8) 0.0656(4) Uani 1 1 d .
F2 F 0.69669(8) 0.21522(13) 0.87872(9) 0.0726(4) Uani 1 1 d .
F3 F 0.65171(7) 0.40348(16) 0.95012(8) 0.0707(4) Uani 1 1 d .
N1 N 0.77091(11) 0.3534(2) 0.72409(11) 0.0564(4) Uani 1 1 d .
H1A H 0.8041 0.3260 0.6811 0.068 Uiso 1 1 d R
H1B H 0.7219 0.2863 0.7210 0.068 Uiso 1 1 d R
O1 O 1.00570(8) 0.79446(15) 1.04301(8) 0.0528(3) Uani 1 1 d .
O2 O 0.90085(9) 0.72864(17) 1.11516(9) 0.0622(4) 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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 120.63(15)
C6 C1 C9 119.03(14)
C2 C1 C9 120.29(15)
N1 C2 C1 123.52(15)
N1 C2 C3 119.09(15)
C1 C2 C3 117.38(15)
C4 C3 C2 121.73(15)
C4 C3 H3 119.1
C2 C3 H3 119.1
C3 C4 C5 120.74(15)
C3 C4 H4 119.6
C5 C4 H4 119.6
C6 C5 C4 118.30(15)
C6 C5 C7 118.53(14)
C4 C5 C7 123.15(15)
C1 C6 C5 121.22(15)
C1 C6 H6 119.4
C5 C6 H6 119.4
O2 C7 O1 123.00(16)
O2 C7 C5 124.45(15)
O1 C7 C5 112.55(14)
O1 C8 H8A 109.5
O1 C8 H8B 109.5
H8A C8 H8B 109.5
O1 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
F3 C9 F1 106.55(14)
F3 C9 F2 106.24(14)
F1 C9 F2 104.87(15)
F3 C9 C1 113.32(15)
F1 C9 C1 113.34(14)
F2 C9 C1 111.87(15)
C2 N1 H1A 122.2
C2 N1 H1B 121.2
H1A N1 H1B 112.6
C7 O1 C8 117.29(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.389(2)
C1 C2 1.400(2)
C1 C9 1.490(2)
C2 N1 1.371(2)
C2 C3 1.406(2)
C3 C4 1.370(2)
C3 H3 0.9300
C4 C5 1.396(2)
C4 H4 0.9300
C5 C6 1.389(2)
C5 C7 1.480(2)
C6 H6 0.9300
C7 O2 1.204(2)
C7 O1 1.328(2)
C8 O1 1.438(2)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 F3 1.332(2)
C9 F1 1.342(2)
C9 F2 1.349(2)
N1 H1A 0.9434
N1 H1B 0.9374
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
C6 C1 C2 N1 -179.24(16)
C9 C1 C2 N1 3.4(2)
C6 C1 C2 C3 0.0(2)
C9 C1 C2 C3 -177.39(15)
N1 C2 C3 C4 179.16(16)
C1 C2 C3 C4 -0.1(2)
C2 C3 C4 C5 0.0(3)
C3 C4 C5 C6 0.3(2)
C3 C4 C5 C7 178.62(16)
C2 C1 C6 C5 0.3(2)
C9 C1 C6 C5 177.66(15)
C4 C5 C6 C1 -0.4(2)
C7 C5 C6 C1 -178.81(14)
C6 C5 C7 O2 2.9(3)
C4 C5 C7 O2 -175.45(17)
C6 C5 C7 O1 -177.27(14)
C4 C5 C7 O1 4.4(2)
C6 C1 C9 F3 5.8(2)
C2 C1 C9 F3 -176.83(14)
C6 C1 C9 F1 127.35(16)
C2 C1 C9 F1 -55.2(2)
C6 C1 C9 F2 -114.33(17)
C2 C1 C9 F2 63.1(2)
O2 C7 O1 C8 0.0(3)
C5 C7 O1 C8 -179.79(14)
