#------------------------------------------------------------------------------
#$Date: 2019-12-26 21:20:13 +0200 (Thu, 26 Dec 2019) $
#$Revision: 246096 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/17/2311734.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2311734
loop_
_publ_author_name
'Dey, Dhananjay'
'Chopra, Deepak'
_publ_section_title
;
 Quantitative analysis of solid-state diversity in trifluoromethylated
 phenylhydrazones.
;
_journal_issue                   'Pt 5'
_journal_name_full
'Acta crystallographica Section B, Structural science, crystal engineering and materials'
_journal_page_first              781
_journal_page_last               793
_journal_paper_doi               10.1107/S2052520617006643
_journal_volume                  73
_journal_year                    2017
_chemical_formula_sum            'C14 H11 F3 N2'
_chemical_formula_weight         264.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5823(6)
_cell_length_b                   13.8757(7)
_cell_length_c                   7.4479(3)
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.48
_cell_measurement_theta_min      2.94
_cell_volume                     1196.97(10)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            22984
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.525
_diffrn_reflns_theta_min         2.936
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.7343
_exptl_absorpt_correction_T_min  0.6452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3414
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0368
_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)+(0.0503P)²+0.1985P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0897
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3036
_reflns_number_total             3414
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao5033sup1.cif
_cod_data_source_block           HT20
_cod_database_code               2311734
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
F1 F 0.75926(15) 0.45385(9) 0.8262(2) 0.0393(4) Uani 1 1 d . .
F2 F 0.77569(12) 0.43847(8) 1.10965(18) 0.0292(3) Uani 1 1 d . .
F3 F 0.60943(10) 0.42710(8) 0.9882(3) 0.0367(3) Uani 1 1 d . .
N1 N 0.49483(13) -0.07978(10) 1.0378(2) 0.0183(3) Uani 1 1 d . .
H1 H 0.4401 -0.0569 1.1078 0.022 Uiso 1 1 calc R U
N2 N 0.58217(11) -0.02168(10) 0.9834(2) 0.0160(3) Uani 1 1 d . .
C4 C 0.48248(16) -0.37130(13) 0.8904(3) 0.0201(4) Uani 1 1 d . .
H4 H 0.4798 -0.4377 0.8598 0.024 Uiso 1 1 calc R U
C5 C 0.57785(15) -0.31531(12) 0.8440(3) 0.0187(3) Uani 1 1 d . .
H5 H 0.6402 -0.3440 0.7809 0.022 Uiso 1 1 calc R U
C6 C 0.58311(14) -0.21814(12) 0.8887(2) 0.0163(3) Uani 1 1 d . .
H6 H 0.6483 -0.1806 0.8556 0.020 Uiso 1 1 calc R U
C1 C 0.49170(13) -0.17618(11) 0.9827(3) 0.0142(3) Uani 1 1 d . .
C13 C 0.57933(15) 0.06664(11) 1.0366(2) 0.0153(3) Uani 1 1 d . .
H13 H 0.5183 0.0884 1.1115 0.018 Uiso 1 1 calc R U
C7 C 0.67070(13) 0.13348(11) 0.9811(2) 0.0144(3) Uani 1 1 d . .
C8 C 0.65452(14) 0.23272(11) 1.0061(2) 0.0147(3) Uani 1 1 d . .
H8 H 0.5873 0.2559 1.0648 0.018 Uiso 1 1 calc R U
C9 C 0.73760(14) 0.29681(12) 0.9442(2) 0.0153(3) Uani 1 1 d . .
C10 C 0.83839(14) 0.26481(12) 0.8620(2) 0.0179(3) Uani 1 1 d . .
H10 H 0.8945 0.3096 0.8207 0.021 Uiso 1 1 calc R U
C14 C 0.71941(15) 0.40342(12) 0.9658(3) 0.0185(3) Uani 1 1 d . .
C3 C 0.39164(15) -0.32866(12) 0.9818(3) 0.0191(3) Uani 1 1 d . .
H3 H 0.3263 -0.3664 1.0137 0.023 Uiso 1 1 calc R U
C2 C 0.39466(14) -0.23121(12) 1.0276(3) 0.0168(3) Uani 1 1 d . .
H2 H 0.3314 -0.2025 1.0887 0.020 Uiso 1 1 calc R U
C12 C 0.77315(15) 0.10110(13) 0.8998(3) 0.0167(3) Uani 1 1 d . .
H12 H 0.7859 0.0339 0.8850 0.020 Uiso 1 1 calc R U
C11 C 0.85590(15) 0.16615(13) 0.8410(3) 0.0185(3) Uani 1 1 d . .
H11 H 0.9247 0.1433 0.7862 0.022 Uiso 1 1 calc R U
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
N2 N1 C1 120.01(14)
N2 N1 H1 120.0
C1 N1 H1 120.0
C13 N2 N1 117.06(14)
C3 C4 C5 119.04(16)
C3 C4 H4 120.5
C5 C4 H4 120.5
C6 C5 C4 121.06(17)
C6 C5 H5 119.5
C4 C5 H5 119.5
C5 C6 C1 119.42(15)
C5 C6 H6 120.3
C1 C6 H6 120.3
C6 C1 C2 120.08(14)
C6 C1 N1 121.73(14)
C2 C1 N1 118.18(15)
N2 C13 C7 119.77(15)
N2 C13 H13 120.1
C7 C13 H13 120.1
C8 C7 C12 118.93(15)
C8 C7 C13 119.16(14)
C12 C7 C13 121.89(14)
C9 C8 C7 119.49(15)
C9 C8 H8 120.3
C7 C8 H8 120.3
C8 C9 C10 121.54(15)
C8 C9 C14 119.85(15)
C10 C9 C14 118.61(15)
C9 C10 C11 119.03(15)
C9 C10 H10 120.5
C11 C10 H10 120.5
F3 C14 F1 107.47(16)
F3 C14 F2 105.99(16)
F1 C14 F2 105.25(14)
F3 C14 C9 113.08(13)
F1 C14 C9 112.59(16)
F2 C14 C9 111.91(15)
C4 C3 C2 120.99(16)
C4 C3 H3 119.5
C2 C3 H3 119.5
C3 C2 C1 119.38(16)
C3 C2 H2 120.3
C1 C2 H2 120.3
C11 C12 C7 120.73(15)
C11 C12 H12 119.6
C7 C12 H12 119.6
C12 C11 C10 120.23(16)
C12 C11 H11 119.9
C10 C11 H11 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C14 1.335(2)
F2 C14 1.345(2)
F3 C14 1.326(2)
N1 N2 1.3555(19)
N1 C1 1.400(2)
N1 H1 0.8800
N2 C13 1.288(2)
C4 C3 1.386(3)
C4 C5 1.394(3)
C4 H4 0.9500
C5 C6 1.390(2)
C5 H5 0.9500
C6 C1 1.396(2)
C6 H6 0.9500
C1 C2 1.399(2)
C13 C7 1.467(2)
C13 H13 0.9500
C7 C8 1.402(2)
C7 C12 1.406(2)
C8 C9 1.389(2)
C8 H8 0.9500
C9 C10 1.391(2)
C9 C14 1.503(2)
C10 C11 1.393(2)
C10 H10 0.9500
C3 C2 1.395(2)
C3 H3 0.9500
C2 H2 0.9500
C12 C11 1.388(2)
C12 H12 0.9500
C11 H11 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
C1 N1 N2 C13 179.05(16)
C3 C4 C5 C6 0.3(3)
C4 C5 C6 C1 0.4(3)
C5 C6 C1 C2 -1.5(3)
C5 C6 C1 N1 177.18(17)
N2 N1 C1 C6 7.3(3)
N2 N1 C1 C2 -174.06(16)
N1 N2 C13 C7 -179.44(15)
N2 C13 C7 C8 166.32(16)
N2 C13 C7 C12 -12.2(3)
C12 C7 C8 C9 2.4(2)
C13 C7 C8 C9 -176.19(17)
C7 C8 C9 C10 -1.7(3)
C7 C8 C9 C14 178.30(16)
C8 C9 C10 C11 0.2(3)
C14 C9 C10 C11 -179.86(17)
C8 C9 C14 F3 -21.2(3)
C10 C9 C14 F3 158.81(18)
C8 C9 C14 F1 -143.29(17)
C10 C9 C14 F1 36.7(2)
C8 C9 C14 F2 98.38(18)
C10 C9 C14 F2 -81.6(2)
C5 C4 C3 C2 -0.1(3)
C4 C3 C2 C1 -0.9(3)
C6 C1 C2 C3 1.7(3)
N1 C1 C2 C3 -177.00(16)
C8 C7 C12 C11 -1.6(3)
C13 C7 C12 C11 176.98(17)
C7 C12 C11 C10 0.0(3)
C9 C10 C11 C12 0.7(3)
