#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:56:51 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180405 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/74/7207431.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_7207431
loop_
_publ_author_name
'Panini, Piyush'
'Chopra, Deepak'
_publ_section_title
;
 Role of intermolecular interactions involving organic fluorine in
 trifluoromethylated benzanilides
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              1972
_journal_paper_doi               10.1039/c2ce06254b
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C15 H9 F6 N O'
_chemical_formula_sum            'C15 H9 F6 N O'
_chemical_formula_weight         333.23
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
_cell_angle_beta                 108.350(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8346(8)
_cell_length_b                   8.061(5)
_cell_length_c                   14.155(5)
_cell_measurement_reflns_used    719
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.7
_cell_measurement_theta_min      1.6
_cell_volume                     1390.0(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.923
_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  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0535
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23224
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.81
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  0.9678
_exptl_absorpt_correction_T_min  0.9189
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4769
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.976
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0445
_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)+(0.0536P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1157
_reflns_number_gt                2610
_reflns_number_total             4769
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce06254b.txt
_cod_data_source_block           T-3-1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1390.0(11)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7207431
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 0.75155(10) 0.18601(16) 0.35774(9) 0.0272(3) Uani 1 1 d . . .
C2 C 0.68328(10) 0.25049(16) 0.40870(9) 0.0293(3) Uani 1 1 d . . .
C3 C 0.72291(12) 0.27092(19) 0.51154(10) 0.0359(3) Uani 1 1 d . . .
C4 C 0.83050(12) 0.22610(19) 0.56389(11) 0.0388(4) Uani 1 1 d . . .
C5 C 0.89858(12) 0.16591(19) 0.51362(10) 0.0379(4) Uani 1 1 d . . .
C6 C 0.86007(11) 0.14691(17) 0.41078(10) 0.0326(3) Uani 1 1 d . . .
C7 C 0.73111(10) 0.21794(15) 0.08562(9) 0.0244(3) Uani 1 1 d . . .
C8 C 0.63973(11) 0.13413(18) 0.02431(10) 0.0315(3) Uani 1 1 d . . .
C9 C 0.61585(12) 0.14270(18) -0.07816(10) 0.0324(3) Uani 1 1 d . . .
C10 C 0.68251(11) 0.23230(16) -0.11969(9) 0.0299(3) Uani 1 1 d . A .
C11 C 0.77557(12) 0.31195(18) -0.05851(10) 0.0339(3) Uani 1 1 d . . .
C12 C 0.79979(11) 0.30393(18) 0.04399(10) 0.0306(3) Uani 1 1 d . . .
C13 C 0.70872(10) 0.14273(16) 0.24826(9) 0.0267(3) Uani 1 1 d . . .
C14 C 0.65321(14) 0.2443(2) -0.23007(10) 0.0426(4) Uani 1 1 d . . .
C15 C 0.56715(12) 0.3007(2) 0.35483(10) 0.0376(3) Uani 1 1 d . . .
N1 N 0.75662(9) 0.22649(14) 0.19044(8) 0.0266(2) Uani 1 1 d . . .
O1 O 0.63810(7) 0.03483(11) 0.21885(6) 0.0321(2) Uani 1 1 d . . .
F1A F 0.6054(7) 0.3719(7) -0.2636(3) 0.129(4) Uani 0.426(5) 1 d P A 1
F2A F 0.6073(5) 0.1143(7) -0.2746(3) 0.086(2) Uani 0.426(5) 1 d P A 1
F3A F 0.7501(3) 0.2483(8) -0.25604(19) 0.0850(19) Uani 0.426(5) 1 d P A 1
F1B F 0.6735(4) 0.1157(5) -0.2744(2) 0.0906(18) Uani 0.574(5) 1 d P A 2
F2B F 0.6860(3) 0.3765(4) -0.26459(15) 0.0694(14) Uani 0.574(5) 1 d P A 2
F3B F 0.53757(16) 0.2570(5) -0.27488(14) 0.0670(10) Uani 0.574(5) 1 d P A 2
F4 F 0.55711(6) 0.37184(11) 0.26583(6) 0.0452(2) Uani 1 1 d . . .
F5 F 0.52862(7) 0.41090(13) 0.40627(6) 0.0562(3) Uani 1 1 d . . .
F6 F 0.49707(7) 0.17247(13) 0.33567(7) 0.0550(3) Uani 1 1 d . . .
H1 H 0.8040(12) 0.3064(17) 0.2198(11) 0.033(4) Uiso 1 1 d . . .
H3 H 0.6742(12) 0.3212(18) 0.5429(12) 0.046(5) Uiso 1 1 d . . .
H4 H 0.8543(12) 0.2420(18) 0.6312(12) 0.043(4) Uiso 1 1 d . . .
H5 H 0.9721(13) 0.1361(18) 0.5513(12) 0.045(4) Uiso 1 1 d . . .
H6 H 0.9093(12) 0.1047(17) 0.3751(10) 0.034(4) Uiso 1 1 d . . .
H8 H 0.5950(12) 0.0734(17) 0.0526(11) 0.040(4) Uiso 1 1 d . . .
H9 H 0.5481(12) 0.0876(18) -0.1219(12) 0.044(4) Uiso 1 1 d . . .
H11 H 0.8240(12) 0.3743(17) -0.0860(11) 0.038(4) Uiso 1 1 d . . .
H12 H 0.8615(11) 0.3613(17) 0.0863(10) 0.030(4) Uiso 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 119.21(12)
C6 C1 C13 118.59(12)
C2 C1 C13 121.97(11)
C3 C2 C1 120.08(12)
C3 C2 C15 118.49(12)
C1 C2 C15 121.43(11)
C2 C3 C4 120.00(14)
C2 C3 H3 117.1(9)
C4 C3 H3 122.9(9)
C5 C4 C3 120.01(13)
C5 C4 H4 122.0(9)
C3 C4 H4 117.9(9)
C4 C5 C6 120.37(13)
C4 C5 H5 118.4(10)
C6 C5 H5 121.3(10)
C5 C6 C1 120.28(14)
C5 C6 H6 120.0(8)
C1 C6 H6 119.7(8)
C12 C7 C8 119.95(12)
C12 C7 N1 116.83(11)
C8 C7 N1 123.17(12)
C9 C8 C7 119.50(13)
C9 C8 H8 120.7(9)
C7 C8 H8 119.8(9)
C10 C9 C8 120.51(13)
C10 C9 H9 120.2(9)
C8 C9 H9 119.3(9)
C9 C10 C11 120.04(12)
C9 C10 C14 119.56(12)
C11 C10 C14 120.40(13)
C12 C11 C10 119.69(13)
C12 C11 H11 118.9(8)
C10 C11 H11 121.4(8)
C11 C12 C7 120.25(12)
C11 C12 H12 120.3(9)
C7 C12 H12 119.3(9)
O1 C13 N1 125.20(12)
O1 C13 C1 120.06(11)
N1 C13 C1 114.70(11)
F1A C14 F2A 114.0(4)
F1A C14 F1B 130.5(3)
F2A C14 F2B 130.3(2)
F1B C14 F2B 109.9(2)
F1A C14 F3A 105.0(4)
F2A C14 F3A 101.5(3)
F1B C14 F3B 100.6(2)
F2B C14 F3B 100.9(2)
F3A C14 F3B 140.15(18)
F1A C14 C10 113.2(2)
F2A C14 C10 113.1(2)
F1B C14 C10 115.98(19)
F2B C14 C10 116.34(15)
F3A C14 C10 108.91(16)
F3B C14 C10 110.83(14)
F5 C15 F6 106.41(12)
F5 C15 F4 106.40(12)
F6 C15 F4 106.10(11)
F5 C15 C2 112.38(12)
F6 C15 C2 112.99(13)
F4 C15 C2 112.07(11)
C13 N1 C7 127.71(11)
C13 N1 H1 116.9(9)
C7 N1 H1 114.9(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.3946(18)
C1 C2 1.3987(19)
C1 C13 1.5130(17)
C2 C3 1.3923(18)
C2 C15 1.5005(19)
C3 C4 1.394(2)
C3 H3 0.963(16)
C4 C5 1.377(2)
C4 H4 0.913(15)
C5 C6 1.3906(19)
C5 H5 0.957(16)
C6 H6 0.986(15)
C7 C12 1.3899(18)
C7 C8 1.3943(18)
C7 N1 1.4169(16)
C8 C9 1.3867(19)
C8 H8 0.935(15)
C9 C10 1.3841(19)
C9 H9 0.999(15)
C10 C11 1.3920(19)
C10 C14 1.4907(19)
C11 C12 1.3864(19)
C11 H11 0.972(15)
C12 H12 0.950(13)
C13 O1 1.2304(15)
C13 N1 1.3492(17)
C14 F1A 1.215(3)
C14 F2A 1.269(5)
C14 F1B 1.280(3)
C14 F2B 1.297(3)
C14 F3A 1.404(3)
C14 F3B 1.422(3)
C15 F5 1.3381(17)
C15 F6 1.3408(19)
C15 F4 1.3528(16)
N1 H1 0.894(15)
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 C3 -1.69(19)
C13 C1 C2 C3 172.68(12)
C6 C1 C2 C15 177.65(13)
C13 C1 C2 C15 -7.97(19)
C1 C2 C3 C4 -0.4(2)
C15 C2 C3 C4 -179.78(13)
C2 C3 C4 C5 1.8(2)
C3 C4 C5 C6 -1.1(2)
C4 C5 C6 C1 -1.1(2)
C2 C1 C6 C5 2.4(2)
C13 C1 C6 C5 -172.12(12)
C12 C7 C8 C9 -2.5(2)
N1 C7 C8 C9 174.93(12)
C7 C8 C9 C10 0.6(2)
C8 C9 C10 C11 1.3(2)
C8 C9 C10 C14 -178.02(13)
C9 C10 C11 C12 -1.3(2)
C14 C10 C11 C12 177.97(13)
C10 C11 C12 C7 -0.5(2)
C8 C7 C12 C11 2.4(2)
N1 C7 C12 C11 -175.12(12)
C6 C1 C13 O1 112.21(15)
C2 C1 C13 O1 -62.20(17)
C6 C1 C13 N1 -65.65(16)
C2 C1 C13 N1 119.94(14)
C9 C10 C14 F1A 97.9(5)
C11 C10 C14 F1A -81.4(5)
C9 C10 C14 F2A -33.7(4)
C11 C10 C14 F2A 147.0(4)
C9 C10 C14 F1B -76.5(3)
C11 C10 C14 F1B 104.2(3)
C9 C10 C14 F2B 151.9(3)
C11 C10 C14 F2B -27.5(3)
C9 C10 C14 F3A -145.8(3)
C11 C10 C14 F3A 34.9(3)
C9 C10 C14 F3B 37.3(3)
C11 C10 C14 F3B -142.0(2)
C3 C2 C15 F5 22.10(19)
C1 C2 C15 F5 -157.26(12)
C3 C2 C15 F6 -98.34(15)
C1 C2 C15 F6 82.30(15)
C3 C2 C15 F4 141.85(13)
C1 C2 C15 F4 -37.50(19)
O1 C13 N1 C7 5.1(2)
C1 C13 N1 C7 -177.20(11)
C12 C7 N1 C13 -173.60(12)
C8 C7 N1 C13 8.9(2)
