#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/59/7155972.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_7155972
loop_
_publ_author_name
'Grellepois, Fabienne'
'Ben Jamaa, Abdelkhalek'
'Saraiva Rosa, Nathalie'
_publ_section_title
;
 α-Trifluoromethylated tertiary homoallylic amines: diastereoselective
 synthesis and conversion into β-aminoesters, γ- and δ-aminoalcohols,
 azetidines and pyrrolidines
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/C7OB02506H
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C12 H22 F3 N O3 S'
_chemical_formula_weight         317.37
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-10-03 deposited with the CCDC.
2017-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 99.961(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            2
_cell_length_a                   7.535(5)
_cell_length_b                   10.972(5)
_cell_length_c                   9.930(5)
_cell_measurement_reflns_used    9835
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.21
_cell_measurement_theta_min      4.03
_cell_volume                     808.6(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.001
_diffrn_measurement_device_type  CMOS
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            26501
_diffrn_reflns_theta_full        72.20
_diffrn_reflns_theta_max         72.20
_diffrn_reflns_theta_min         4.52
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.138
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.047(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3182
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0234
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0396P)²+0.0824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0626
_refine_ls_wR_factor_ref         0.0628
_reflns_number_gt                3128
_reflns_number_total             3182
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob02506h2.cif
_cod_data_source_block           cu_15fg012_0m
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7155972
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.17076(4) 0.10737(3) 0.26662(3) 0.02262(8) Uani 1 1 d .
F2 F 0.23829(12) 0.49985(8) 0.32489(9) 0.0319(2) Uani 1 1 d .
F3 F -0.04244(13) 0.53326(8) 0.24652(10) 0.0361(2) Uani 1 1 d .
F1 F 0.03489(14) 0.40597(9) 0.41153(9) 0.0375(2) Uani 1 1 d .
O2 O 0.44979(13) 0.38751(9) 0.11937(11) 0.0269(2) Uani 1 1 d .
O3 O 0.31832(13) 0.56302(9) 0.04147(10) 0.0246(2) Uani 1 1 d .
O1 O 0.19909(14) 0.04043(9) 0.14163(11) 0.0287(2) Uani 1 1 d .
N1 N 0.21454(16) 0.25518(10) 0.25391(12) 0.0214(2) Uani 1 1 d .
C2 C 0.12436(17) 0.39632(12) 0.05509(14) 0.0200(3) Uani 1 1 d .
C4 C 0.0760(2) 0.44551(13) 0.29319(15) 0.0263(3) Uani 1 1 d .
C3 C 0.31536(19) 0.44613(12) 0.07739(13) 0.0206(3) Uani 1 1 d .
C5 C -0.11339(19) 0.28715(13) 0.16263(17) 0.0282(3) Uani 1 1 d .
H5A H -0.1170 0.2195 0.1009 0.042 Uiso 1 1 calc R
H5B H -0.1981 0.3480 0.1230 0.042 Uiso 1 1 calc R
H5C H -0.1442 0.2597 0.2475 0.042 Uiso 1 1 calc R
C1 C 0.07658(18) 0.34170(12) 0.18892(14) 0.0207(3) Uani 1 1 d .
C8 C 0.49620(19) 0.61685(15) 0.05588(14) 0.0295(3) Uani 1 1 d .
H8A H 0.5522 0.6155 0.1504 0.044 Uiso 1 1 calc R
H8B H 0.4861 0.6996 0.0240 0.044 Uiso 1 1 calc R
H8C H 0.5682 0.5711 0.0029 0.044 Uiso 1 1 calc R
C9 C 0.3686(2) 0.07050(13) 0.39820(14) 0.0255(3) Uani 1 1 d .
C12 C 0.54249(17) 0.10826(17) 0.35169(13) 0.0275(3) Uani 1 1 d .
H12A H 0.5526 0.1955 0.3540 0.041 Uiso 1 1 calc R
H12B H 0.5414 0.0799 0.2601 0.041 Uiso 1 1 calc R
H12C H 0.6432 0.0732 0.4116 0.041 Uiso 1 1 calc R
C6 C 0.1049(2) 0.30177(14) -0.06194(14) 0.0253(3) Uani 1 1 d .
H6A H 0.1707 0.2287 -0.0289 0.030 Uiso 1 1 calc R
H6B H -0.0212 0.2799 -0.0876 0.030 Uiso 1 1 calc R
C11 C 0.3431(2) 0.13331(15) 0.53047(15) 0.0330(3) Uani 1 1 d .
H11A H 0.2283 0.1109 0.5525 0.050 Uiso 1 1 calc R
H11B H 0.3477 0.2201 0.5190 0.050 Uiso 1 1 calc R
H11C H 0.4372 0.1085 0.6032 0.050 Uiso 1 1 calc R
C7 C 0.1740(2) 0.34791(15) -0.18792(15) 0.0324(3) Uani 1 1 d .
H7A H 0.1157 0.4235 -0.2173 0.049 Uiso 1 1 calc R
H7B H 0.1481 0.2888 -0.2600 0.049 Uiso 1 1 calc R
H7C H 0.3018 0.3605 -0.1659 0.049 Uiso 1 1 calc R
C10 C 0.3595(2) -0.06781(15) 0.41224(18) 0.0372(4) Uani 1 1 d .
H10A H 0.4515 -0.0944 0.4856 0.056 Uiso 1 1 calc R
H10B H 0.3779 -0.1055 0.3285 0.056 Uiso 1 1 calc R
H10C H 0.2434 -0.0906 0.4314 0.056 Uiso 1 1 calc R
H1N H 0.320(3) 0.2687(19) 0.2304(18) 0.028(5) Uiso 1 1 d .
H2 H 0.044(2) 0.4610(15) 0.0264(16) 0.014(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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O1 S1 N1 111.02(6)
O1 S1 C9 105.48(7)
N1 S1 C9 96.93(6)
C3 O3 C8 115.08(11)
C1 N1 S1 121.84(10)
C3 C2 C6 108.38(11)
C3 C2 C1 111.55(10)
C6 C2 C1 112.19(12)
F3 C4 F1 107.17(12)
F3 C4 F2 106.62(12)
F1 C4 F2 106.07(12)
F3 C4 C1 112.22(12)
F1 C4 C1 112.26(12)
F2 C4 C1 112.10(11)
O2 C3 O3 123.47(13)
O2 C3 C2 125.01(13)
O3 C3 C2 111.50(11)
N1 C1 C5 113.02(12)
N1 C1 C4 105.44(11)
C5 C1 C4 107.00(12)
N1 C1 C2 111.89(11)
C5 C1 C2 110.64(11)
C4 C1 C2 108.51(11)
C12 C9 C11 112.47(13)
C12 C9 C10 110.69(14)
C11 C9 C10 110.88(13)
C12 C9 S1 110.95(10)
C11 C9 S1 107.67(11)
C10 C9 S1 103.81(11)
C7 C6 C2 113.15(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4889(12)
S1 N1 1.6642(14)
S1 C9 1.8490(17)
F2 C4 1.3479(19)
F3 C4 1.3398(18)
F1 C4 1.3383(18)
O2 C3 1.2114(18)
O3 C3 1.3324(18)
O3 C8 1.4489(18)
N1 C1 1.4718(18)
C2 C3 1.519(2)
C2 C6 1.546(2)
C2 C1 1.5558(19)
C4 C1 1.5398(19)
C5 C1 1.532(2)
C9 C12 1.520(2)
C9 C11 1.525(2)
C9 C10 1.527(2)
C6 C7 1.523(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139193294
