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#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/16/7151688.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_7151688
loop_
_publ_author_name
'Grellepois, Fabienne'
'Nonnenmacher, Jean'
'Lachaud, Fabien'
'Portella, Charles'
_publ_section_title
;
 Enantiomerically pure 2-aryl(alkyl)-2-trifluoromethylaziridines:
 synthesis and ring opening with selected O- and N-nucleophiles.
;
_journal_issue                   4
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1160
_journal_page_last               1168
_journal_paper_doi               10.1039/C0OB00690D
_journal_volume                  9
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H25 F3 N2 O2 S'
_chemical_formula_weight         462.52
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6263(13)
_cell_length_b                   14.1765(14)
_cell_length_c                   16.473(2)
_cell_measurement_reflns_used    4405
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.38
_cell_measurement_theta_min      2.45
_cell_volume                     2248.0(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.955
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0583
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18019
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_min         1.90
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'KAPPA APEXII ICMMO'
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         6529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0559P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1031
_reflns_number_gt                5364
_reflns_number_total             6529
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0OB00690D.TXT
_cod_data_source_block           publication_text
_cod_original_cell_volume        2248.1(5)
_cod_database_code               7151688
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5544(2) 0.58148(12) 0.78958(10) 0.0168(4) Uani 1 1 d . . .
C2 C 0.5585(2) 0.56971(12) 0.69582(10) 0.0136(3) Uani 1 1 d . . .
C3 C 0.5296(2) 0.66803(12) 0.65653(11) 0.0157(4) Uani 1 1 d . . .
H3A H 0.5898 0.7147 0.6813 0.019 Uiso 1 1 calc R . .
H3B H 0.5517 0.6652 0.5991 0.019 Uiso 1 1 calc R . .
C4 C 0.3377(2) 0.76240(12) 0.60164(10) 0.0147(4) Uani 1 1 d . . .
H4 H 0.4127 0.8067 0.5888 0.018 Uiso 1 1 calc R . .
C5 C 0.2137(2) 0.81720(13) 0.63369(11) 0.0202(4) Uani 1 1 d . . .
H5A H 0.1401 0.7741 0.6468 0.030 Uiso 1 1 calc R . .
H5B H 0.1823 0.8607 0.5930 0.030 Uiso 1 1 calc R . .
H5C H 0.2404 0.8514 0.6815 0.030 Uiso 1 1 calc R . .
C10 C 0.3008(2) 0.70697(12) 0.52556(10) 0.0148(4) Uani 1 1 d . . .
C11 C 0.1989(2) 0.63681(12) 0.52794(10) 0.0155(4) Uani 1 1 d . . .
H11 H 0.1556 0.6224 0.5769 0.019 Uiso 1 1 calc R . .
C12 C 0.1615(2) 0.58833(13) 0.45802(11) 0.0182(4) Uani 1 1 d . . .
H12 H 0.0921 0.5427 0.4601 0.022 Uiso 1 1 calc R . .
C13 C 0.2275(2) 0.60785(15) 0.38493(11) 0.0207(4) Uani 1 1 d . . .
H13 H 0.2034 0.5750 0.3382 0.025 Uiso 1 1 calc R . .
C14 C 0.3292(2) 0.67630(15) 0.38219(11) 0.0232(4) Uani 1 1 d . . .
H14 H 0.3735 0.6895 0.3333 0.028 Uiso 1 1 calc R . .
C15 C 0.3660(2) 0.72597(14) 0.45203(11) 0.0207(4) Uani 1 1 d . . .
H15 H 0.4346 0.7721 0.4494 0.025 Uiso 1 1 calc R . .
C20 C 0.6993(2) 0.53297(11) 0.66613(11) 0.0147(3) Uani 1 1 d . . .
C21 C 0.7122(2) 0.51340(13) 0.58317(11) 0.0191(4) Uani 1 1 d . . .
H21 H 0.6373 0.5241 0.5487 0.023 Uiso 1 1 calc R . .
C23 C 0.8356(2) 0.47818(14) 0.55171(13) 0.0247(5) Uani 1 1 d . . .
H23 H 0.8424 0.4649 0.4966 0.030 Uiso 1 1 calc R . .
C24 C 0.9483(2) 0.46280(14) 0.60193(13) 0.0264(5) Uani 1 1 d . . .
H24 H 1.0304 0.4385 0.5808 0.032 Uiso 1 1 calc R . .
C25 C 0.9382(2) 0.48384(13) 0.68409(13) 0.0253(4) Uani 1 1 d . . .
H25 H 1.0143 0.4747 0.7180 0.030 Uiso 1 1 calc R . .
C26 C 0.8141(2) 0.51867(13) 0.71570(12) 0.0195(4) Uani 1 1 d . . .
H26 H 0.8080 0.5325 0.7708 0.023 Uiso 1 1 calc R . .
C30 C 0.4592(2) 0.36455(12) 0.56334(10) 0.0149(4) Uani 1 1 d . . .
C31 C 0.3712(2) 0.40036(14) 0.50442(11) 0.0201(4) Uani 1 1 d . . .
H31 H 0.3006 0.4420 0.5185 0.024 Uiso 1 1 calc R . .
C32 C 0.3897(2) 0.37341(14) 0.42422(11) 0.0213(4) Uani 1 1 d . . .
H32 H 0.3311 0.3975 0.3844 0.026 Uiso 1 1 calc R . .
C33 C 0.4948(2) 0.31080(13) 0.40238(11) 0.0184(4) Uani 1 1 d . . .
C34 C 0.5835(2) 0.27677(13) 0.46297(11) 0.0207(4) Uani 1 1 d . . .
H34 H 0.6549 0.2356 0.4491 0.025 Uiso 1 1 calc R . .
C35 C 0.5664(2) 0.30360(12) 0.54367(10) 0.0188(4) Uani 1 1 d . . .
H35 H 0.6259 0.2809 0.5836 0.023 Uiso 1 1 calc R . .
C36 C 0.5098(3) 0.27832(14) 0.31542(11) 0.0248(5) Uani 1 1 d . . .
H36A H 0.6033 0.2573 0.3062 0.037 Uiso 1 1 calc R . .
H36B H 0.4890 0.3297 0.2795 0.037 Uiso 1 1 calc R . .
H36C H 0.4466 0.2273 0.3053 0.037 Uiso 1 1 calc R . .
N1 N 0.44149(17) 0.51044(10) 0.67286(9) 0.0147(3) Uani 1 1 d . . .
H1 H 0.3670 0.5410 0.6611 0.018 Uiso 1 1 calc R . .
N2 N 0.38548(16) 0.69735(11) 0.66628(9) 0.0151(3) Uani 1 1 d . . .
H2 H 0.3334 0.6788 0.7056 0.018 Uiso 1 1 calc R . .
O1 O 0.53165(17) 0.35309(9) 0.71505(7) 0.0207(3) Uani 1 1 d . . .
O2 O 0.28250(16) 0.37877(9) 0.67976(8) 0.0214(3) Uani 1 1 d . . .
F1 F 0.64380(14) 0.64733(8) 0.81585(6) 0.0237(3) Uani 1 1 d . . .
F2 F 0.58219(13) 0.50212(7) 0.82982(6) 0.0204(2) Uani 1 1 d . . .
F3 F 0.42747(14) 0.60911(8) 0.81460(6) 0.0226(2) Uani 1 1 d . . .
S1 S 0.42722(5) 0.39679(3) 0.66557(2) 0.01456(10) 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'
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'
S S 0.1246 0.1234 '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
F2 C1 F1 107.37(15) . . ?
F2 C1 F3 105.95(15) . . ?
F1 C1 F3 106.30(14) . . ?
F2 C1 C2 113.49(14) . . ?
F1 C1 C2 112.28(15) . . ?
F3 C1 C2 110.98(16) . . ?
N1 C2 C20 113.91(14) . . ?
N1 C2 C1 107.50(15) . . ?
C20 C2 C1 112.10(16) . . ?
N1 C2 C3 105.63(15) . . ?
C20 C2 C3 109.21(14) . . ?
C1 C2 C3 108.15(14) . . ?
N2 C3 C2 112.26(15) . . ?
N2 C4 C5 108.20(14) . . ?
N2 C4 C10 110.06(14) . . ?
C5 C4 C10 111.51(16) . . ?
C15 C10 C11 118.64(17) . . ?
C15 C10 C4 120.78(17) . . ?
C11 C10 C4 120.58(16) . . ?
C12 C11 C10 120.72(17) . . ?
C11 C12 C13 120.10(18) . . ?
C14 C13 C12 119.56(17) . . ?
C13 C14 C15 120.58(18) . . ?
C10 C15 C14 120.38(19) . . ?
C26 C20 C21 118.31(19) . . ?
C26 C20 C2 124.44(17) . . ?
C21 C20 C2 117.25(17) . . ?
C23 C21 C20 120.8(2) . . ?
C24 C23 C21 120.32(19) . . ?
C23 C24 C25 119.7(2) . . ?
C24 C25 C26 120.0(2) . . ?
C20 C26 C25 120.94(19) . . ?
C35 C30 C31 121.38(16) . . ?
C35 C30 S1 120.87(14) . . ?
C31 C30 S1 117.73(15) . . ?
C30 C31 C32 119.23(19) . . ?
C31 C32 C33 120.97(18) . . ?
C32 C33 C34 118.58(17) . . ?
C32 C33 C36 120.53(18) . . ?
C34 C33 C36 120.86(19) . . ?
C35 C34 C33 120.98(19) . . ?
C30 C35 C34 118.83(17) . . ?
C2 N1 S1 131.18(13) . . ?
C3 N2 C4 113.18(14) . . ?
O1 S1 O2 120.71(9) . . ?
O1 S1 N1 109.12(8) . . ?
O2 S1 N1 104.29(9) . . ?
O1 S1 C30 107.86(9) . . ?
O2 S1 C30 106.12(9) . . ?
N1 S1 C30 108.18(8) . . ?
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
C1 F2 1.333(2) . ?
C1 F1 1.341(2) . ?
C1 F3 1.348(2) . ?
C1 C2 1.554(2) . ?
C2 N1 1.455(2) . ?
C2 C20 1.532(3) . ?
C2 C3 1.562(2) . ?
C3 N2 1.457(3) . ?
C4 N2 1.482(2) . ?
C4 C5 1.519(3) . ?
C4 C10 1.521(2) . ?
C10 C15 1.391(2) . ?
C10 C11 1.397(3) . ?
C11 C12 1.389(2) . ?
C12 C13 1.390(3) . ?
C13 C14 1.379(3) . ?
C14 C15 1.395(3) . ?
C20 C26 1.389(3) . ?
C20 C21 1.400(3) . ?
C21 C23 1.389(3) . ?
C23 C24 1.381(3) . ?
C24 C25 1.389(3) . ?
C25 C26 1.394(3) . ?
C30 C35 1.384(3) . ?
C30 C31 1.385(3) . ?
C30 S1 1.7720(17) . ?
C31 C32 1.387(2) . ?
C32 C33 1.393(3) . ?
C33 C34 1.399(3) . ?
C33 C36 1.512(2) . ?
C34 C35 1.393(2) . ?
N1 S1 1.6215(14) . ?
O1 S1 1.4348(14) . ?
O2 S1 1.4355(15) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653464
2 PubChem 53309152
