#------------------------------------------------------------------------------
#$Date: 2019-12-26 21:20:13 +0200 (Thu, 26 Dec 2019) $
#$Revision: 246096 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/17/2311732.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_2311732
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            'C15 H10 F6 N2'
_chemical_formula_weight         332.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 103.740(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.2831(9)
_cell_length_b                   4.8177(3)
_cell_length_c                   19.0386(11)
_cell_measurement_reflns_used    3889
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.29
_cell_measurement_theta_min      2.74
_cell_volume                     1361.69(14)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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  0.0261
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9984
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.202
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6777
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2939
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0312
_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)+(0.0328P)²+0.2219P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0680
_refine_ls_wR_factor_ref         0.0693
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2757
_reflns_number_total             2939
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao5033sup1.cif
_cod_data_source_block           HT11
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2311732
_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   0.992
loop_
_space_group_symop_operation_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'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 0.2455(13) 0.913(2) 0.1997(6) 0.0173(5) Uani 0.530(16) 1 d . . P A 1
H1A H 0.3041 0.9178 0.2174 0.021 Uiso 0.530(16) 1 calc R U P A 1
N2A N 0.1982(8) 0.740(5) 0.2269(16) 0.0173(5) Uani 0.530(16) 1 d . . P A 1
C13A C 0.2373(16) 0.564(3) 0.2747(6) 0.0173(5) Uani 0.530(16) 1 d . . P A 1
H13A H 0.3011 0.5503 0.2858 0.021 Uiso 0.530(16) 1 calc R U P A 1
N1B N 0.2376(15) 0.581(3) 0.2818(5) 0.0173(5) Uani 0.470(16) 1 d . . P A 2
H1B H 0.2964 0.5954 0.2977 0.021 Uiso 0.470(16) 1 calc R U P A 2
N2B N 0.1915(9) 0.742(6) 0.2271(18) 0.0173(5) Uani 0.470(16) 1 d . . P A 2
C13B C 0.2477(19) 0.893(3) 0.1946(8) 0.0173(5) Uani 0.470(16) 1 d . . P A 2
H13B H 0.3110 0.8646 0.2067 0.021 Uiso 0.470(16) 1 calc R U P A 2
F1 F 0.39523(9) 1.3340(3) 0.19583(7) 0.0342(4) Uani 1 1 d . . . . .
F2 F 0.39901(9) 1.3893(3) 0.08448(8) 0.0324(4) Uani 1 1 d . . . . .
F3 F 0.39014(10) 0.9814(3) 0.12653(9) 0.0312(4) Uani 1 1 d . . . . .
F5 F 0.35928(10) 0.0578(3) 0.45536(8) 0.0335(4) Uani 1 1 d . . . . .
F4 F 0.36261(9) 0.4746(3) 0.41749(8) 0.0298(4) Uani 1 1 d . . . . .
F6 F 0.37466(9) 0.1345(3) 0.34775(7) 0.0319(4) Uani 1 1 d . . . . .
C1 C 0.20646(15) 1.0945(5) 0.14188(12) 0.0171(5) Uani 1 1 d . . . . .
C2 C 0.25917(15) 1.2605(5) 0.10773(11) 0.0175(5) Uani 1 1 d . . . . .
C3 C 0.21822(17) 1.4507(5) 0.05472(12) 0.0213(5) Uani 1 1 d . . . . .
H3 H 0.2544 1.5655 0.0324 0.026 Uiso 1 1 calc R U . . .
C4 C 0.12533(17) 1.4730(5) 0.03444(12) 0.0234(6) Uani 1 1 d . . . . .
H4 H 0.0977 1.6018 -0.0019 0.028 Uiso 1 1 calc R U . . .
C5 C 0.07297(16) 1.3063(5) 0.06741(13) 0.0227(5) Uani 1 1 d . . . . .
H5 H 0.0092 1.3209 0.0534 0.027 Uiso 1 1 calc R U . . .
C6 C 0.11246(16) 1.1186(5) 0.12061(12) 0.0203(5) Uani 1 1 d . . . . .
H6 H 0.0757 1.0057 0.1428 0.024 Uiso 1 1 calc R U . . .
C7 C 0.18740(15) 0.3871(5) 0.31236(11) 0.0177(5) Uani 1 1 d . . . . .
C8 C 0.23037(15) 0.2138(5) 0.36963(12) 0.0188(5) Uani 1 1 d . . . . .
C9 C 0.18003(16) 0.0311(5) 0.40094(12) 0.0229(5) Uani 1 1 d . . . . .
H9 H 0.2096 -0.0858 0.4395 0.027 Uiso 1 1 calc R U . . .
C10 C 0.08752(17) 0.0184(5) 0.37649(14) 0.0256(6) Uani 1 1 d . . . . .
H10 H 0.0535 -0.1072 0.3979 0.031 Uiso 1 1 calc R U . . .
C11 C 0.04469(17) 0.1905(5) 0.32051(13) 0.0243(6) Uani 1 1 d . . . . .
H11 H -0.0190 0.1831 0.3038 0.029 Uiso 1 1 calc R U . . .
C12 C 0.09348(16) 0.3724(5) 0.28873(12) 0.0211(5) Uani 1 1 d . . . . .
H12 H 0.0630 0.4889 0.2504 0.025 Uiso 1 1 calc R U . . .
C14 C 0.35948(17) 1.2428(5) 0.12792(13) 0.0221(5) Uani 1 1 d . . . . .
C15 C 0.33020(16) 0.2192(5) 0.39745(12) 0.0216(5) 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'
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
N2A N1A C1 122.4(15)
N2A N1A H1A 118.8
C1 N1A H1A 118.8
C13A N2A N1A 120.0(13)
N2A C13A C7 122.1(17)
N2A C13A H13A 118.9
C7 C13A H13A 118.9
N2B N1B C7 117.4(17)
N2B N1B H1B 121.3
C7 N1B H1B 121.3
N1B N2B C13B 112.5(14)
N2B C13B C1 117(2)
N2B C13B H13B 121.4
C1 C13B H13B 121.4
C2 C1 C6 118.8(2)
C2 C1 N1A 122.0(8)
C6 C1 N1A 119.2(8)
C2 C1 C13B 120.5(11)
C6 C1 C13B 120.6(11)
C3 C2 C1 120.1(2)
C3 C2 C14 118.7(2)
C1 C2 C14 121.1(2)
C4 C3 C2 120.4(2)
C4 C3 H3 119.8
C2 C3 H3 119.8
C3 C4 C5 119.6(2)
C3 C4 H4 120.2
C5 C4 H4 120.2
C6 C5 C4 120.8(2)
C6 C5 H5 119.6
C4 C5 H5 119.6
C5 C6 C1 120.3(2)
C5 C6 H6 119.9
C1 C6 H6 119.9
C12 C7 C8 118.3(2)
C12 C7 N1B 121.0(8)
C8 C7 N1B 120.7(8)
C12 C7 C13A 119.5(8)
C8 C7 C13A 122.1(8)
C9 C8 C7 120.2(2)
C9 C8 C15 118.8(2)
C7 C8 C15 121.0(2)
C10 C9 C8 120.6(2)
C10 C9 H9 119.7
C8 C9 H9 119.7
C9 C10 C11 119.4(2)
C9 C10 H10 120.3
C11 C10 H10 120.3
C12 C11 C10 120.8(2)
C12 C11 H11 119.6
C10 C11 H11 119.6
C11 C12 C7 120.7(2)
C11 C12 H12 119.6
C7 C12 H12 119.6
F2 C14 F3 105.75(19)
F2 C14 F1 106.30(19)
F3 C14 F1 105.04(19)
F2 C14 C2 113.47(19)
F3 C14 C2 112.9(2)
F1 C14 C2 112.65(19)
F5 C15 F4 105.67(19)
F5 C15 F6 106.13(19)
F4 C15 F6 105.2(2)
F5 C15 C8 113.2(2)
F4 C15 C8 113.1(2)
F6 C15 C8 112.83(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1A N2A 1.29(3)
N1A C1 1.422(13)
N1A H1A 0.8800
N2A C13A 1.28(2)
C13A C7 1.443(19)
C13A H13A 0.9500
N1B N2B 1.36(3)
N1B C7 1.418(18)
N1B H1B 0.8800
N2B C13B 1.38(4)
C13B C1 1.430(18)
C13B H13B 0.9500
F1 C14 1.352(3)
F2 C14 1.336(3)
F3 C14 1.346(3)
F5 C15 1.336(3)
F4 C15 1.347(3)
F6 C15 1.352(3)
C1 C2 1.400(3)
C1 C6 1.402(3)
C2 C3 1.396(3)
C2 C14 1.492(3)
C3 C4 1.384(3)
C3 H3 0.9500
C4 C5 1.385(3)
C4 H4 0.9500
C5 C6 1.385(3)
C5 H5 0.9500
C6 H6 0.9500
C7 C12 1.400(3)
C7 C8 1.406(3)
C8 C9 1.393(3)
C8 C15 1.492(3)
C9 C10 1.381(3)
C9 H9 0.9500
C10 C11 1.386(4)
C10 H10 0.9500
C11 C12 1.380(3)
C11 H11 0.9500
C12 H12 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 N1A N2A C13A 174.1(13)
N1A N2A C13A C7 173(2)
C7 N1B N2B C13B -171(2)
N1B N2B C13B C1 -172.9(14)
N2A N1A C1 C2 -173(2)
N2A N1A C1 C6 10(2)
N2B C13B C1 C2 178(2)
N2B C13B C1 C6 -5(2)
C6 C1 C2 C3 1.5(3)
N1A C1 C2 C3 -175.4(5)
C13B C1 C2 C3 178.0(6)
C6 C1 C2 C14 -179.7(2)
N1A C1 C2 C14 3.3(5)
C13B C1 C2 C14 -3.2(7)
C1 C2 C3 C4 -1.3(3)
C14 C2 C3 C4 179.9(2)
C2 C3 C4 C5 0.4(3)
C3 C4 C5 C6 0.3(4)
C4 C5 C6 C1 0.0(4)
C2 C1 C6 C5 -0.9(3)
N1A C1 C6 C5 176.2(4)
C13B C1 C6 C5 -177.4(7)
N2B N1B C7 C12 -2.5(14)
N2B N1B C7 C8 -179.5(15)
N2A C13A C7 C12 10.4(16)
N2A C13A C7 C8 -173.7(17)
C12 C7 C8 C9 0.7(3)
N1B C7 C8 C9 177.8(6)
C13A C7 C8 C9 -175.3(6)
C12 C7 C8 C15 -180.0(2)
N1B C7 C8 C15 -2.9(6)
C13A C7 C8 C15 4.0(6)
C7 C8 C9 C10 -0.3(3)
C15 C8 C9 C10 -179.6(2)
C8 C9 C10 C11 -0.3(3)
C9 C10 C11 C12 0.4(4)
C10 C11 C12 C7 0.0(3)
C8 C7 C12 C11 -0.6(3)
N1B C7 C12 C11 -177.6(6)
C13A C7 C12 C11 175.5(6)
C3 C2 C14 F2 -8.9(3)
C1 C2 C14 F2 172.35(19)
C3 C2 C14 F3 -129.2(2)
C1 C2 C14 F3 52.0(3)
C3 C2 C14 F1 112.0(2)
C1 C2 C14 F1 -66.8(3)
C9 C8 C15 F5 -5.5(3)
C7 C8 C15 F5 175.2(2)
C9 C8 C15 F4 -125.7(2)
C7 C8 C15 F4 55.0(3)
C9 C8 C15 F6 115.1(2)
C7 C8 C15 F6 -64.2(3)
