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#$Date: 2025-04-05 06:57:38 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299068 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160201.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_7160201
loop_
_publ_author_name
'Ajitrao Kisan, Devadkar'
'Paul, Ishita'
'Dey, Soumyadip'
'Sau, Abhijit'
'Panda, Tarun K.'
_publ_section_title
;
 Facile access to trifluoromethyl propargyl alcohol by metal-free transfer
 hydrogenation and cyanation of alkynyl ketones.
;
_journal_issue                   1
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              197
_journal_page_last               201
_journal_paper_doi               10.1039/d4ob00844h
_journal_volume                  23
_journal_year                    2024
_chemical_formula_moiety         'C18 H14 F3 N3'
_chemical_formula_sum            'C18 H14 F3 N3'
_chemical_formula_weight         329.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-04-21 deposited with the CCDC.	2024-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                105.651(2)
_cell_angle_beta                 105.770(2)
_cell_angle_gamma                101.840(2)
_cell_formula_units_Z            2
_cell_length_a                   7.0003(5)
_cell_length_b                   10.2027(7)
_cell_length_c                   12.3065(8)
_cell_measurement_reflns_used    23404
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.188
_cell_measurement_theta_min      2.173
_cell_volume                     776.85(9)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'ORTEP III and WINGX'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23404
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.188
_diffrn_reflns_theta_min         2.173
_diffrn_source                   'Bruker APEX-II CCD'
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       plates
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3427
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0370
_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)+(0.0464P)²+0.2291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.0990
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3087
_reflns_number_total             3427
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00844h2.cif
_cod_data_source_block           shelx_6b
_cod_depositor_comments
'Adding full bibliography for 7160200--7160202.cif.'
_cod_database_code               7160201
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.52774(15) 0.67046(10) 0.21203(9) 0.0282(2) Uani 1 1 d . . . . .
N2 N 0.2029(2) -0.04460(12) -0.06899(12) 0.0459(3) Uani 1 1 d . . . . .
N3 N 0.38800(15) 0.74657(10) 0.20897(8) 0.0260(2) Uani 1 1 d . . . . .
F1 F 0.17254(12) 0.93283(8) 0.21547(8) 0.0469(2) Uani 1 1 d . . . . .
F2 F 0.39503(13) 1.04381(8) 0.39384(7) 0.0430(2) Uani 1 1 d . . . . .
F3 F 0.45123(13) 1.09524(8) 0.24532(7) 0.0423(2) Uani 1 1 d . . . . .
C1 C 0.7797(3) 0.65442(19) 0.65443(14) 0.0550(4) Uani 1 1 d . . . . .
H1A H 0.808600 0.572328 0.674787 0.083 Uiso 1 1 calc R U . . .
H1B H 0.628890 0.635567 0.619935 0.083 Uiso 1 1 calc R U . . .
H1C H 0.837346 0.739501 0.727324 0.083 Uiso 1 1 calc R U . . .
C2 C 0.8781(2) 0.67874(13) 0.56431(11) 0.0342(3) Uani 1 1 d . . . . .
C3 C 0.76996(19) 0.70349(12) 0.46259(11) 0.0294(2) Uani 1 1 d . . . . .
H3 H 0.630653 0.705477 0.449744 0.035 Uiso 1 1 calc R U . . .
C4 C 0.86185(17) 0.72537(11) 0.37943(10) 0.0246(2) Uani 1 1 d . . . . .
C5 C 0.74733(17) 0.76124(12) 0.27332(10) 0.0263(2) Uani 1 1 d . . . . .
H5 H 0.822122 0.752400 0.214328 0.032 Uiso 1 1 calc R U . . .
C6 C 0.45945(18) 0.52489(11) 0.15044(9) 0.0250(2) Uani 1 1 d . . . . .
C7 C 0.60415(19) 0.44864(13) 0.14428(10) 0.0299(2) Uani 1 1 d . . . . .
H7 H 0.749009 0.497619 0.179996 0.036 Uiso 1 1 calc R U . . .
C8 C 0.5363(2) 0.30246(13) 0.08635(11) 0.0318(3) Uani 1 1 d . . . . .
H8 H 0.634812 0.251285 0.082461 0.038 Uiso 1 1 calc R U . . .
C9 C 0.3242(2) 0.22978(12) 0.03364(10) 0.0302(3) Uani 1 1 d . . . . .
C10 C 0.2553(2) 0.07682(13) -0.02328(11) 0.0355(3) Uani 1 1 d . . . . .
C11 C 0.48994(18) 0.87908(12) 0.26229(10) 0.0260(2) Uani 1 1 d . . . . .
C12 C 0.72144(18) 0.91285(12) 0.31041(11) 0.0302(3) Uani 1 1 d . . . . .
H12A H 0.778115 0.960810 0.398870 0.036 Uiso 1 1 calc R U . . .
H12B H 0.789475 0.973356 0.272560 0.036 Uiso 1 1 calc R U . . .
C13 C 1.0815(2) 0.67591(13) 0.58071(12) 0.0386(3) Uani 1 1 d . . . . .
H13 H 1.158383 0.659871 0.649843 0.046 Uiso 1 1 calc R U . . .
C14 C 1.17294(19) 0.69593(14) 0.49859(13) 0.0388(3) Uani 1 1 d . . . . .
H14 H 1.311871 0.693141 0.511205 0.047 Uiso 1 1 calc R U . . .
C15 C 1.06392(18) 0.72028(12) 0.39707(12) 0.0318(3) Uani 1 1 d . . . . .
H15 H 1.127537 0.733337 0.340137 0.038 Uiso 1 1 calc R U . . .
C16 C 0.37590(19) 0.98679(12) 0.27804(11) 0.0309(3) Uani 1 1 d . . . . .
C17 C 0.24619(18) 0.45160(12) 0.09516(10) 0.0278(2) Uani 1 1 d . . . . .
H17 H 0.147304 0.502735 0.097189 0.033 Uiso 1 1 calc R U . . .
C18 C 0.17931(19) 0.30562(12) 0.03785(10) 0.0306(3) Uani 1 1 d . . . . .
H18 H 0.034587 0.256435 0.001167 0.037 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
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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 N1 C6 119.87(9) . . ?
N3 N1 C5 113.38(9) . . ?
C6 N1 C5 126.39(9) . . ?
C11 N3 N1 108.07(9) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C13 C2 C3 118.18(12) . . ?
C13 C2 C1 120.19(12) . . ?
C3 C2 C1 121.63(13) . . ?
C4 C3 C2 121.28(11) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C15 C4 C3 119.42(11) . . ?
C15 C4 C5 119.78(10) . . ?
C3 C4 C5 120.74(10) . . ?
N1 C5 C4 113.08(9) . . ?
N1 C5 C12 101.58(9) . . ?
C4 C5 C12 112.99(9) . . ?
N1 C5 H5 109.6 . . ?
C4 C5 H5 109.6 . . ?
C12 C5 H5 109.6 . . ?
N1 C6 C17 120.70(10) . . ?
N1 C6 C7 119.99(10) . . ?
C17 C6 C7 119.31(10) . . ?
C8 C7 C6 120.13(11) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.33(11) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C18 119.77(11) . . ?
C8 C9 C10 119.82(11) . . ?
C18 C9 C10 120.41(12) . . ?
N2 C10 C9 179.06(15) . . ?
N3 C11 C16 119.70(10) . . ?
N3 C11 C12 115.70(10) . . ?
C16 C11 C12 124.52(10) . . ?
C11 C12 C5 101.26(9) . . ?
C11 C12 H12A 111.5 . . ?
C5 C12 H12A 111.5 . . ?
C11 C12 H12B 111.5 . . ?
C5 C12 H12B 111.5 . . ?
H12A C12 H12B 109.3 . . ?
C14 C13 C2 121.00(12) . . ?
C14 C13 H13 119.5 . . ?
C2 C13 H13 119.5 . . ?
C13 C14 C15 120.53(12) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C4 C15 C14 119.57(12) . . ?
C4 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
F1 C16 F3 107.76(10) . . ?
F1 C16 F2 106.60(10) . . ?
F3 C16 F2 106.35(9) . . ?
F1 C16 C11 113.11(10) . . ?
F3 C16 C11 111.45(10) . . ?
F2 C16 C11 111.22(10) . . ?
C18 C17 C6 120.31(11) . . ?
C18 C17 H17 119.8 . . ?
C6 C17 H17 119.8 . . ?
C17 C18 C9 120.14(11) . . ?
C17 C18 H18 119.9 . . ?
C9 C18 H18 119.9 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N3 1.3670(13) . ?
N1 C6 1.3832(14) . ?
N1 C5 1.4827(14) . ?
N2 C10 1.1449(17) . ?
N3 C11 1.2801(14) . ?
F1 C16 1.3328(14) . ?
F2 C16 1.3432(15) . ?
F3 C16 1.3345(14) . ?
C1 C2 1.5035(19) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C13 1.390(2) . ?
C2 C3 1.3921(17) . ?
C3 C4 1.3903(16) . ?
C3 H3 0.9500 . ?
C4 C15 1.3857(16) . ?
C4 C5 1.5136(15) . ?
C5 C12 1.5533(16) . ?
C5 H5 1.0000 . ?
C6 C17 1.4021(16) . ?
C6 C7 1.4037(16) . ?
C7 C8 1.3819(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.3928(18) . ?
C8 H8 0.9500 . ?
C9 C18 1.3999(18) . ?
C9 C10 1.4410(16) . ?
C11 C16 1.4872(16) . ?
C11 C12 1.4949(16) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.372(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.3899(19) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C17 C18 1.3794(16) . ?
C17 H17 0.9500 . ?
C18 H18 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 N3 C11 -173.87(10) . . . . ?
C5 N1 N3 C11 -0.34(13) . . . . ?
C13 C2 C3 C4 -0.21(18) . . . . ?
C1 C2 C3 C4 -179.76(12) . . . . ?
C2 C3 C4 C15 1.01(17) . . . . ?
C2 C3 C4 C5 -176.18(10) . . . . ?
N3 N1 C5 C4 121.72(10) . . . . ?
C6 N1 C5 C4 -65.25(14) . . . . ?
N3 N1 C5 C12 0.34(12) . . . . ?
C6 N1 C5 C12 173.37(10) . . . . ?
C15 C4 C5 N1 137.70(11) . . . . ?
C3 C4 C5 N1 -45.13(14) . . . . ?
C15 C4 C5 C12 -107.60(12) . . . . ?
C3 C4 C5 C12 69.58(13) . . . . ?
N3 N1 C6 C17 -6.72(16) . . . . ?
C5 N1 C6 C17 -179.34(10) . . . . ?
N3 N1 C6 C7 174.19(10) . . . . ?
C5 N1 C6 C7 1.57(17) . . . . ?
N1 C6 C7 C8 177.79(10) . . . . ?
C17 C6 C7 C8 -1.31(17) . . . . ?
C6 C7 C8 C9 0.05(18) . . . . ?
C7 C8 C9 C18 0.97(17) . . . . ?
C7 C8 C9 C10 -178.09(11) . . . . ?
N1 N3 C11 C16 -176.81(10) . . . . ?
N1 N3 C11 C12 0.19(13) . . . . ?
N3 C11 C12 C5 0.02(13) . . . . ?
C16 C11 C12 C5 176.86(10) . . . . ?
N1 C5 C12 C11 -0.20(11) . . . . ?
C4 C5 C12 C11 -121.64(10) . . . . ?
C3 C2 C13 C14 -0.45(19) . . . . ?
C1 C2 C13 C14 179.10(13) . . . . ?
C2 C13 C14 C15 0.3(2) . . . . ?
C3 C4 C15 C14 -1.14(17) . . . . ?
C5 C4 C15 C14 176.07(10) . . . . ?
C13 C14 C15 C4 0.49(19) . . . . ?
N3 C11 C16 F1 -10.48(16) . . . . ?
C12 C11 C16 F1 172.80(10) . . . . ?
N3 C11 C16 F3 -132.07(11) . . . . ?
C12 C11 C16 F3 51.21(15) . . . . ?
N3 C11 C16 F2 109.45(12) . . . . ?
C12 C11 C16 F2 -67.27(14) . . . . ?
N1 C6 C17 C18 -177.53(10) . . . . ?
C7 C6 C17 C18 1.56(16) . . . . ?
C6 C17 C18 C9 -0.55(17) . . . . ?
C8 C9 C18 C17 -0.72(17) . . . . ?
C10 C9 C18 C17 178.33(11) . . . . ?
