#------------------------------------------------------------------------------
#$Date: 2019-11-03 12:43:47 +0200 (Sun, 03 Nov 2019) $
#$Revision: 221424 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/83/4128301.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_4128301
loop_
_publ_author_name
'Belligund, Kavita'
'Mathew, Thomas'
'Hunt, Jonathan R.'
'Nirmalchandar, Archith'
'Haiges, Ralf'
'Dawlaty, Jahan'
'Prakash, G. K. Surya'
_publ_section_title
;
 Photochemistry of 2-Nitroarenes: 2-Nitrophenyl-α-trifluoromethyl
 Carbinols as Synthons for Fluoroorganics.
;
_journal_issue                   40
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15921
_journal_page_last               15931
_journal_paper_doi               10.1021/jacs.9b07241
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C8 H4 F3 N O3'
_chemical_formula_sum            'C8 H4 F3 N O3'
_chemical_formula_weight         219.12
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 105.719(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4041(11)
_cell_length_b                   16.548(3)
_cell_length_c                   8.0820(14)
_cell_measurement_reflns_used    98
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      26.5277
_cell_measurement_theta_min      2.9051
_cell_volume                     824.5(3)
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS, 2014)'
_computing_data_collection
'Bruker Instrument Service v2012.12.0.3 (Bruker AXS, 2012)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_publication_material  'SHELXTL XT 2014/4 (Bruker AXS, 2014)'
_computing_structure_refinement  'SHELXTL XL 2014/7 (Bruker AXS, 2014)'
_computing_structure_solution    'SHELXTL XT 2014/4 (Bruker AXS, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'
_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19479
_diffrn_reflns_theta_full        30.65
_diffrn_reflns_theta_max         30.65
_diffrn_reflns_theta_min         2.46
_diffrn_source                   'fine-focus tube'
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5 (Bruker AXS, 2014)'
_exptl_crystal_colour            'clear orange'
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.338
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.127
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.248
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0579P)²+0.3014P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1035
_reflns_number_gt                2114
_reflns_number_total             2527
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b07241_si_006.cif
_cod_data_source_block           I
_cod_original_cell_volume        824.5(2)
_cod_database_code               4128301
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
C C1 0.64806(17) 0.39665(6) 0.67385(13) 0.0128(2) Uani d . . 1
C C2 0.76050(18) 0.43304(7) 0.57684(13) 0.0148(2) Uani d . . 1
H H2 0.8919 0.4609 0.6279 0.018 Uiso calc U R 1
C C3 0.67309(18) 0.42840(6) 0.38784(13) 0.0136(2) Uani d . . 1
C C4 0.47192(18) 0.38204(7) 0.31506(14) 0.0158(2) Uani d . . 1
H H4 0.4183 0.3774 0.1938 0.019 Uiso calc U R 1
C C5 0.36228(18) 0.34617(7) 0.41579(14) 0.0161(2) Uani d . . 1
H H5 0.2326 0.3169 0.3672 0.019 Uiso calc U R 1
C C6 0.44796(17) 0.35367(6) 0.59971(14) 0.0139(2) Uani d . . 1
C C7 0.68106(17) 0.39086(6) 0.86513(13) 0.0130(2) Uani d . . 1
C C8 0.87494(19) 0.33676(7) 0.95286(14) 0.0175(2) Uani d . . 1
N N1 0.35822(16) 0.32520(6) 0.71450(13) 0.0178(2) Uani d . . 1
O O1 0.48890(13) 0.34569(5) 0.87856(10) 0.01791(18) Uani d . . 1
O O2 0.69447(14) 0.46519(5) 0.94113(10) 0.01714(18) Uani d . . 1
H H2O 0.709(3) 0.4604(10) 1.045(2) 0.021 Uiso d U . 1
O O3 0.76742(14) 0.46356(5) 0.29363(10) 0.01853(18) Uani d . . 1
F F1 0.88861(13) 0.32745(5) 1.11992(9) 0.0272(2) Uani d . . 1
F F2 1.06001(12) 0.36928(5) 0.94041(10) 0.02771(19) Uani d . . 1
F F3 0.85718(14) 0.26327(5) 0.88176(10) 0.0282(2) Uani d . . 1
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
C2 C1 C6 122.28(10)
C2 C1 C7 132.84(10)
C6 C1 C7 104.85(9)
C1 C2 C3 117.84(10)
C1 C2 H2 121.1
C3 C2 H2 121.1
O3 C3 C4 121.15(10)
O3 C3 C2 119.96(10)
C4 C3 C2 118.89(9)
C5 C4 C3 121.92(10)
C5 C4 H4 119.0
C3 C4 H4 119.0
C4 C5 C6 117.97(10)
C4 C5 H5 121.0
C6 C5 H5 121.0
N1 C6 C5 125.69(10)
N1 C6 C1 113.24(10)
C5 C6 C1 121.06(10)
O2 C7 O1 112.12(9)
O2 C7 C1 112.23(9)
O1 C7 C1 102.76(8)
O2 C7 C8 111.82(9)
O1 C7 C8 104.92(9)
C1 C7 C8 112.42(9)
F2 C8 F3 108.02(10)
F2 C8 F1 107.88(10)
F3 C8 F1 107.68(10)
F2 C8 C7 110.73(10)
F3 C8 C7 111.54(9)
F1 C8 C7 110.85(9)
C6 N1 O1 108.64(9)
N1 O1 C7 110.49(8)
C7 O2 H2O 110.3(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.3422(15)
C1 C6 1.4460(15)
C1 C7 1.5056(14)
C2 C3 1.4796(14)
C2 H2 0.95
C3 O3 1.2380(13)
C3 C4 1.4777(15)
C4 C5 1.3483(16)
C4 H4 0.95
C5 C6 1.4436(15)
C5 H5 0.95
C6 N1 1.3046(15)
C7 O2 1.3671(13)
C7 O1 1.4688(13)
C7 C8 1.5391(16)
C8 F2 1.3300(14)
C8 F3 1.3367(14)
C8 F1 1.3381(13)
N1 O1 1.4043(12)
O2 H2O 0.822(18)
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 0.19(16)
C7 C1 C2 C3 -177.69(11)
C1 C2 C3 O3 177.40(11)
C1 C2 C3 C4 -2.03(15)
O3 C3 C4 C5 -177.22(11)
C2 C3 C4 C5 2.20(16)
C3 C4 C5 C6 -0.43(17)
C4 C5 C6 N1 177.45(11)
C4 C5 C6 C1 -1.48(16)
C2 C1 C6 N1 -177.42(11)
C7 C1 C6 N1 0.97(12)
C2 C1 C6 C5 1.64(17)
C7 C1 C6 C5 -179.97(10)
C2 C1 C7 O2 56.28(16)
C6 C1 C7 O2 -121.87(10)
C2 C1 C7 O1 176.92(12)
C6 C1 C7 O1 -1.23(10)
C2 C1 C7 C8 -70.81(16)
C6 C1 C7 C8 111.04(10)
O2 C7 C8 F2 -61.79(12)
O1 C7 C8 F2 176.44(8)
C1 C7 C8 F2 65.51(12)
O2 C7 C8 F3 177.87(9)
O1 C7 C8 F3 56.11(11)
C1 C7 C8 F3 -54.82(13)
O2 C7 C8 F1 57.90(12)
O1 C7 C8 F1 -63.86(11)
C1 C7 C8 F1 -174.79(9)
C5 C6 N1 O1 -179.24(10)
C1 C6 N1 O1 -0.24(13)
C6 N1 O1 C7 -0.64(12)
O2 C7 O1 N1 121.89(9)
C1 C7 O1 N1 1.17(11)
C8 C7 O1 N1 -116.54(9)
