#------------------------------------------------------------------------------
#$Date: 2018-02-18 11:45:15 +0200 (Sun, 18 Feb 2018) $
#$Revision: 206489 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/59/7155975.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_7155975
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            'C11 H20 F3 N O2 S'
_chemical_formula_weight         287.35
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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
_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                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            8
_cell_length_a                   11.039(5)
_cell_length_b                   12.316(5)
_cell_length_c                   21.359(5)
_cell_measurement_reflns_used    9866
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      65.16
_cell_measurement_theta_min      4.14
_cell_volume                     2903.9(19)
_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      101(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            26534
_diffrn_reflns_theta_full        65.16
_diffrn_reflns_theta_max         65.16
_diffrn_reflns_theta_min         4.14
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.272
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.077(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         4953
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0680P)²+1.0886P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1171
_reflns_number_gt                4509
_reflns_number_total             4953
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob02506h2.cif
_cod_data_source_block           cu_14fg009_0m
_cod_depositor_comments
;

2018-02-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C22 H40 F6 N2 O4 S2'
_cod_original_formula_weight         574.68
_cod_original_formula_units_Z            4
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7155975
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
S1 S -0.08507(6) -0.07846(6) 0.04738(4) 0.02256(18) Uani 1 1 d .
S1' S 0.24408(7) 0.20066(7) 0.18976(4) 0.02805(19) Uani 1 1 d .
F2 F -0.09904(18) 0.20114(16) 0.09489(9) 0.0363(5) Uani 1 1 d .
F3 F -0.28034(19) 0.26515(15) 0.09135(10) 0.0404(5) Uani 1 1 d .
O2 O -0.3259(2) 0.0726(2) -0.07809(11) 0.0314(5) Uani 1 1 d .
F1 F -0.17924(19) 0.24036(15) 0.00625(10) 0.0362(5) Uani 1 1 d .
F1' F 0.29217(18) -0.03453(17) 0.32240(10) 0.0407(5) Uani 1 1 d .
O1 O -0.1427(2) -0.18552(18) 0.03299(11) 0.0323(5) Uani 1 1 d .
F3' F 0.1536(2) -0.14392(15) 0.28956(11) 0.0436(5) Uani 1 1 d .
O1' O 0.1661(2) 0.2987(2) 0.18226(12) 0.0398(6) Uani 1 1 d .
F2' F 0.2876(2) -0.07982(18) 0.22631(11) 0.0505(6) Uani 1 1 d .
N1 N -0.1683(2) 0.0208(2) 0.01970(14) 0.0241(6) Uani 1 1 d .
O2' O 0.1795(3) 0.1688(3) 0.37759(13) 0.0457(7) Uani 1 1 d .
N1' N 0.2124(2) 0.1375(2) 0.25456(13) 0.0253(6) Uani 1 1 d .
C7 C -0.2031(3) 0.1975(3) 0.06332(15) 0.0297(7) Uani 1 1 d .
C1 C -0.2533(3) 0.0820(3) 0.05927(14) 0.0230(6) Uani 1 1 d .
C5 C -0.3975(3) 0.1296(3) -0.03361(16) 0.0305(8) Uani 1 1 d .
H5A H -0.4819 0.1269 -0.0461 0.037 Uiso 1 1 calc R
H5B H -0.3728 0.2052 -0.0325 0.037 Uiso 1 1 calc R
C3 C -0.4354(3) -0.0332(3) 0.03273(16) 0.0287(7) Uani 1 1 d .
C2 C -0.3837(3) 0.0802(3) 0.03122(16) 0.0269(7) Uani 1 1 d .
C1' C 0.1331(3) 0.0425(3) 0.26012(15) 0.0266(7) Uani 1 1 d .
C6 C -0.2582(3) 0.0379(3) 0.12634(14) 0.0297(7) Uani 1 1 d .
H6A H -0.2858 -0.0360 0.1257 0.045 Uiso 1 1 calc R
H6B H -0.3131 0.0811 0.1507 0.045 Uiso 1 1 calc R
H6C H -0.1788 0.0410 0.1446 0.045 Uiso 1 1 calc R
C9' C 0.3816(3) 0.3286(3) 0.26915(18) 0.0403(9) Uani 1 1 d .
H9D H 0.3578 0.2866 0.3049 0.061 Uiso 1 1 calc R
H9E H 0.3211 0.3827 0.2607 0.061 Uiso 1 1 calc R
H9F H 0.4577 0.3636 0.2775 0.061 Uiso 1 1 calc R
C9 C 0.0048(4) -0.0964(3) -0.07280(16) 0.0366(8) Uani 1 1 d .
H9A H 0.0748 -0.1021 -0.0993 0.055 Uiso 1 1 calc R
H9B H -0.0469 -0.0394 -0.0879 0.055 Uiso 1 1 calc R
H9C H -0.0387 -0.1639 -0.0732 0.055 Uiso 1 1 calc R
C5' C 0.0947(4) 0.0811(3) 0.37832(16) 0.0369(8) Uani 1 1 d .
H5'A H 0.0301 0.0977 0.4076 0.044 Uiso 1 1 calc R
H5'B H 0.1351 0.0158 0.3929 0.044 Uiso 1 1 calc R
C8 C 0.0443(3) -0.0709(3) -0.00658(16) 0.0292(7) Uani 1 1 d .
C7' C 0.2170(3) -0.0541(3) 0.27474(17) 0.0328(8) Uani 1 1 d .
C3' C -0.0475(3) 0.1474(3) 0.2966(2) 0.0429(10) Uani 1 1 d .
C6' C 0.0682(4) 0.0163(3) 0.19882(17) 0.0416(9) Uani 1 1 d .
H6'A H 0.0209 0.0779 0.1860 0.062 Uiso 1 1 calc R
H6'B H 0.0159 -0.0451 0.2049 0.062 Uiso 1 1 calc R
H6'C H 0.1269 -0.0003 0.1671 0.062 Uiso 1 1 calc R
C2' C 0.0404(3) 0.0598(3) 0.31384(17) 0.0286(7) Uani 1 1 d .
C10 C 0.1294(3) -0.1582(3) 0.0185(2) 0.0416(9) Uani 1 1 d .
H10A H 0.0912 -0.2279 0.0151 0.062 Uiso 1 1 calc R
H10B H 0.1477 -0.1435 0.0616 0.062 Uiso 1 1 calc R
H10C H 0.2031 -0.1581 -0.0054 0.062 Uiso 1 1 calc R
C11 C 0.1018(3) 0.0406(3) -0.0005(2) 0.0395(9) Uani 1 1 d .
H11A H 0.1790 0.0408 -0.0212 0.059 Uiso 1 1 calc R
H11B H 0.1128 0.0576 0.0430 0.059 Uiso 1 1 calc R
H11C H 0.0500 0.0939 -0.0194 0.059 Uiso 1 1 calc R
C8' C 0.3947(3) 0.2545(3) 0.21277(16) 0.0312(8) Uani 1 1 d .
C10' C 0.4361(3) 0.3169(3) 0.15538(19) 0.0440(10) Uani 1 1 d .
H10D H 0.5188 0.3391 0.1608 0.066 Uiso 1 1 calc R
H10E H 0.3859 0.3798 0.1499 0.066 Uiso 1 1 calc R
H10F H 0.4299 0.2711 0.1191 0.066 Uiso 1 1 calc R
C11' C 0.4759(3) 0.1581(3) 0.22597(19) 0.0412(9) Uani 1 1 d .
H11D H 0.5581 0.1825 0.2305 0.062 Uiso 1 1 calc R
H11E H 0.4709 0.1075 0.1919 0.062 Uiso 1 1 calc R
H11F H 0.4503 0.1233 0.2639 0.062 Uiso 1 1 calc R
C4 C -0.5413(3) -0.0586(3) 0.0553(2) 0.0424(9) Uani 1 1 d .
C4' C -0.1647(4) 0.1399(4) 0.3037(3) 0.085(2) Uani 1 1 d .
H4'B H -0.1983 0.0771 0.3205 0.102 Uiso 1 1 calc R
H4'A H -0.2145 0.1973 0.2920 0.102 Uiso 1 1 calc R
H2N H 0.213(3) 0.168(3) 0.2914(18) 0.031(10) Uiso 1 1 d .
H1N H -0.186(4) 0.019(3) -0.015(2) 0.044(13) Uiso 1 1 d .
H3 H -0.387(3) -0.087(3) 0.0128(17) 0.031(9) Uiso 1 1 d .
H4B H -0.568(4) -0.134(3) 0.0523(19) 0.042(11) Uiso 1 1 d .
H3' H -0.010(4) 0.206(4) 0.285(2) 0.063(14) Uiso 1 1 d .
H2' H -0.008(3) -0.004(3) 0.3147(17) 0.032(10) Uiso 1 1 d .
H2 H -0.433(3) 0.122(3) 0.0577(17) 0.026(9) Uiso 1 1 d .
H4A H -0.592(4) -0.006(3) 0.0770(18) 0.036(10) Uiso 1 1 d .
H2O H 0.162(4) 0.212(4) 0.397(2) 0.040(14) Uiso 1 1 d .
H1O H -0.321(5) 0.111(4) -0.106(3) 0.072(18) 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 110.17(14)
O1 S1 C8 104.27(15)
N1 S1 C8 99.87(15)
O1' S1' N1' 110.77(14)
O1' S1' C8' 104.85(15)
N1' S1' C8' 97.94(15)
C1 N1 S1 122.2(2)
C1' N1' S1' 125.4(2)
F2 C7 F3 107.6(3)
F2 C7 F1 105.9(3)
F3 C7 F1 106.5(3)
F2 C7 C1 111.9(3)
F3 C7 C1 112.0(3)
F1 C7 C1 112.5(3)
N1 C1 C7 106.1(2)
N1 C1 C6 112.2(3)
C7 C1 C6 106.8(3)
N1 C1 C2 111.2(3)
C7 C1 C2 111.7(3)
C6 C1 C2 108.8(3)
O2 C5 C2 110.8(3)
C4 C3 C2 124.7(4)
C3 C2 C5 110.6(3)
C3 C2 C1 110.7(3)
C5 C2 C1 115.9(3)
N1' C1' C6' 112.3(3)
N1' C1' C7' 105.9(2)
C6' C1' C7' 107.0(3)
N1' C1' C2' 110.1(3)
C6' C1' C2' 110.7(3)
C7' C1' C2' 110.7(3)
O2' C5' C2' 112.2(3)
C9 C8 C11 112.9(3)
C9 C8 C10 111.1(3)
C11 C8 C10 110.5(3)
C9 C8 S1 110.6(2)
C11 C8 S1 108.5(2)
C10 C8 S1 102.9(2)
F2' C7' F1' 105.8(3)
F2' C7' F3' 107.0(3)
F1' C7' F3' 107.0(3)
F2' C7' C1' 112.2(3)
F1' C7' C1' 112.9(3)
F3' C7' C1' 111.7(3)
C4' C3' C2' 124.2(4)
C3' C2' C5' 110.7(3)
C3' C2' C1' 110.1(3)
C5' C2' C1' 115.6(3)
C11' C8' C10' 111.7(3)
C11' C8' C9' 112.3(3)
C10' C8' C9' 111.4(3)
C11' C8' S1' 107.4(2)
C10' C8' S1' 103.7(2)
C9' C8' S1' 109.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.496(2)
S1 N1 1.640(3)
S1 C8 1.838(3)
S1' O1' 1.491(3)
S1' N1' 1.626(3)
S1' C8' 1.856(3)
F2 C7 1.333(4)
F3 C7 1.334(4)
O2 C5 1.422(4)
F1 C7 1.354(4)
F1' C7' 1.335(4)
F3' C7' 1.347(4)
F2' C7' 1.333(4)
N1 C1 1.471(4)
O2' C5' 1.430(5)
N1' C1' 1.466(4)
C7 C1 1.529(5)
C1 C6 1.533(4)
C1 C2 1.559(4)
C5 C2 1.520(5)
C3 C4 1.303(5)
C3 C2 1.509(5)
C1' C6' 1.527(5)
C1' C7' 1.540(5)
C1' C2' 1.553(5)
C9' C8' 1.518(5)
C9 C8 1.513(5)
C5' C2' 1.525(5)
C8 C11 1.518(5)
C8 C10 1.525(5)
C3' C4' 1.306(6)
C3' C2' 1.497(5)
C8' C11' 1.514(5)
C8' C10' 1.517(5)
