#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/32/1553225.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_1553225
loop_
_publ_author_name
'Yu, Jin-Sheng'
'Zhou, Jian'
_publ_section_title
;
 Organocatalytic enantioselective Mukaiyama--Mannich reaction of
 fluorinated enol silyl ethers and cyclic N-sulfonyl ketimines
;
_journal_issue                   3
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              298
_journal_paper_doi               10.1039/C5QO00407A
_journal_volume                  3
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C17 H14 F2 N2 O4 S'
_chemical_formula_weight         380.36
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_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
;
2015-11-28 deposited with the CCDC.
2015-12-28 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1956(3)
_cell_length_b                   9.6833(3)
_cell_length_c                   23.2873(8)
_cell_measurement_temperature    296(2)
_cell_volume                     1622.59(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Smart Apex II'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            18989
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.9590
_exptl_absorpt_correction_T_min  0.9049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2871
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0385P)²+0.6517P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0801
_reflns_number_gt                2733
_reflns_number_total             2871
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5qo00407a2.cif
_cod_data_source_block           z
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1553225
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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 0.19522(8) 0.54507(5) 0.03045(2) 0.03442(14) Uani 1 1 d .
F1 F 0.3297(2) 0.5852(2) -0.14053(7) 0.0713(5) Uani 1 1 d .
F2 F 0.3229(3) 0.7570(2) -0.08190(7) 0.0943(8) Uani 1 1 d .
O1 O 0.3828(2) 0.59641(17) 0.03530(7) 0.0484(4) Uani 1 1 d .
O2 O 0.0989(3) 0.5282(2) 0.08309(7) 0.0538(5) Uani 1 1 d .
O3 O 0.0719(3) 0.89242(16) -0.13911(8) 0.0505(5) Uani 1 1 d .
H3B H 0.0164 0.8961 -0.1084 0.076 Uiso 1 1 calc R
O4 O -0.2518(2) 0.5587(2) -0.08562(8) 0.0640(6) Uani 1 1 d .
N1 N 0.0738(3) 0.63677(19) -0.01434(7) 0.0415(5) Uani 1 1 d .
H1A H 0.0106 0.7080 -0.0041 0.050 Uiso 1 1 calc R
N2 N -0.0828(3) 0.68022(18) -0.15166(7) 0.0332(4) Uani 1 1 d .
C1 C 0.1914(3) 0.3997(2) -0.01403(9) 0.0337(5) Uani 1 1 d .
C2 C 0.2386(3) 0.2658(3) 0.00120(13) 0.0484(6) Uani 1 1 d .
H2A H 0.2774 0.2438 0.0382 0.058 Uiso 1 1 calc R
C3 C 0.2251(4) 0.1669(3) -0.04111(16) 0.0616(8) Uani 1 1 d .
H3A H 0.2534 0.0755 -0.0326 0.074 Uiso 1 1 calc R
C4 C 0.1703(4) 0.2017(3) -0.09578(15) 0.0618(8) Uani 1 1 d .
H4A H 0.1649 0.1335 -0.1238 0.074 Uiso 1 1 calc R
C5 C 0.1233(4) 0.3354(3) -0.10996(12) 0.0500(6) Uani 1 1 d .
H5A H 0.0855 0.3573 -0.1470 0.060 Uiso 1 1 calc R
C6 C 0.1331(3) 0.4360(2) -0.06816(9) 0.0342(5) Uani 1 1 d .
C7 C 0.0815(3) 0.5879(2) -0.07326(9) 0.0307(5) Uani 1 1 d .
C8 C -0.1079(3) 0.6062(2) -0.10296(9) 0.0368(5) Uani 1 1 d .
C9 C 0.0930(3) 0.7543(2) -0.15557(9) 0.0316(4) Uani 1 1 d .
C10 C 0.2142(3) 0.6717(3) -0.11216(9) 0.0400(5) Uani 1 1 d .
C11 C 0.1790(3) 0.7551(2) -0.21491(9) 0.0332(5) Uani 1 1 d .
C12 C 0.3041(4) 0.8583(3) -0.22907(10) 0.0472(6) Uani 1 1 d .
H12A H 0.3270 0.9301 -0.2035 0.057 Uiso 1 1 calc R
C13 C 0.3953(4) 0.8542(3) -0.28155(13) 0.0644(8) Uani 1 1 d .
H13A H 0.4788 0.9237 -0.2912 0.077 Uiso 1 1 calc R
C14 C 0.3626(5) 0.7477(4) -0.31942(12) 0.0679(9) Uani 1 1 d .
H14A H 0.4243 0.7450 -0.3545 0.081 Uiso 1 1 calc R
C15 C 0.2393(4) 0.6461(4) -0.30520(11) 0.0640(8) Uani 1 1 d .
H15A H 0.2167 0.5747 -0.3310 0.077 Uiso 1 1 calc R
C16 C 0.1481(4) 0.6480(3) -0.25335(10) 0.0481(6) Uani 1 1 d .
H16A H 0.0657 0.5775 -0.2440 0.058 Uiso 1 1 calc R
C17 C -0.2431(4) 0.7242(3) -0.18590(11) 0.0467(6) Uani 1 1 d .
H17A H -0.3465 0.6642 -0.1783 0.070 Uiso 1 1 calc R
H17B H -0.2122 0.7198 -0.2260 0.070 Uiso 1 1 calc R
H17C H -0.2757 0.8173 -0.1759 0.070 Uiso 1 1 calc R
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
O2 S1 O1 115.41(11)
O2 S1 N1 110.81(11)
O1 S1 N1 111.41(11)
O2 S1 C1 114.34(11)
O1 S1 C1 109.79(10)
N1 S1 C1 92.93(10)
C9 O3 H3B 109.5
C7 N1 S1 114.06(15)
C7 N1 H1A 123.0
S1 N1 H1A 123.0
C8 N2 C9 115.40(18)
C8 N2 C17 120.30(19)
C9 N2 C17 120.42(17)
C6 C1 C2 123.2(2)
C6 C1 S1 110.05(16)
C2 C1 S1 126.71(19)
C3 C2 C1 116.7(3)
C3 C2 H2A 121.6
C1 C2 H2A 121.6
C4 C3 C2 120.8(2)
C4 C3 H3A 119.6
C2 C3 H3A 119.6
C3 C4 C5 121.5(2)
C3 C4 H4A 119.2
C5 C4 H4A 119.2
C4 C5 C6 118.8(3)
C4 C5 H5A 120.6
C6 C5 H5A 120.6
C1 C6 C5 118.9(2)
C1 C6 C7 113.14(18)
C5 C6 C7 128.0(2)
N1 C7 C6 104.53(17)
N1 C7 C8 110.69(18)
C6 C7 C8 111.29(18)
N1 C7 C10 113.94(18)
C6 C7 C10 113.72(18)
C8 C7 C10 102.87(17)
O4 C8 N2 126.8(2)
O4 C8 C7 124.56(19)
N2 C8 C7 108.65(19)
O3 C9 N2 111.05(18)
O3 C9 C11 106.82(17)
N2 C9 C11 114.49(17)
O3 C9 C10 111.98(19)
N2 C9 C10 101.10(16)
C11 C9 C10 111.49(18)
F2 C10 F1 106.3(2)
F2 C10 C7 112.11(18)
F1 C10 C7 109.93(19)
F2 C10 C9 110.6(2)
F1 C10 C9 110.21(17)
C7 C10 C9 107.72(18)
C12 C11 C16 119.3(2)
C12 C11 C9 119.1(2)
C16 C11 C9 121.3(2)
C11 C12 C13 119.8(3)
C11 C12 H12A 120.1
C13 C12 H12A 120.1
C14 C13 C12 120.3(3)
C14 C13 H13A 119.8
C12 C13 H13A 119.8
C15 C14 C13 119.7(3)
C15 C14 H14A 120.2
C13 C14 H14A 120.2
C14 C15 C16 120.9(3)
C14 C15 H15A 119.5
C16 C15 H15A 119.5
C15 C16 C11 120.0(3)
C15 C16 H16A 120.0
C11 C16 H16A 120.0
N2 C17 H17A 109.5
N2 C17 H17B 109.5
H17A C17 H17B 109.5
N2 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4176(18)
S1 O1 1.4431(18)
S1 N1 1.6247(19)
S1 C1 1.748(2)
F1 C10 1.352(3)
F2 C10 1.338(3)
O3 C9 1.399(3)
O3 H3B 0.8200
O4 C8 1.203(3)
N1 C7 1.453(3)
N1 H1A 0.8600
N2 C8 1.353(3)
N2 C9 1.457(3)
N2 C17 1.466(3)
C1 C6 1.374(3)
C1 C2 1.387(3)
C2 C3 1.377(4)
C2 H2A 0.9300
C3 C4 1.375(4)
C3 H3A 0.9300
C4 C5 1.378(4)
C4 H4A 0.9300
C5 C6 1.379(3)
C5 H5A 0.9300
C6 C7 1.522(3)
C7 C8 1.539(3)
C7 C10 1.546(3)
C9 C11 1.514(3)
C9 C10 1.556(3)
C11 C12 1.384(3)
C11 C16 1.388(3)
C12 C13 1.388(4)
C12 H12A 0.9300
C13 C14 1.377(5)
C13 H13A 0.9300
C14 C15 1.366(5)
C14 H14A 0.9300
C15 C16 1.374(4)
C15 H15A 0.9300
C16 H16A 0.9300
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
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
O2 S1 N1 C7 -139.92(17)
O1 S1 N1 C7 90.13(18)
C1 S1 N1 C7 -22.47(18)
O2 S1 C1 C6 128.45(17)
O1 S1 C1 C6 -99.99(17)
N1 S1 C1 C6 14.02(17)
O2 S1 C1 C2 -51.4(2)
O1 S1 C1 C2 80.1(2)
N1 S1 C1 C2 -165.9(2)
C6 C1 C2 C3 0.1(4)
S1 C1 C2 C3 180.00(19)
C1 C2 C3 C4 1.1(4)
C2 C3 C4 C5 -1.4(5)
C3 C4 C5 C6 0.5(4)
C2 C1 C6 C5 -1.0(3)
S1 C1 C6 C5 179.09(18)
C2 C1 C6 C7 177.4(2)
S1 C1 C6 C7 -2.4(2)
C4 C5 C6 C1 0.7(4)
C4 C5 C6 C7 -177.5(2)
S1 N1 C7 C6 23.3(2)
S1 N1 C7 C8 143.21(17)
S1 N1 C7 C10 -101.4(2)
C1 C6 C7 N1 -12.2(2)
C5 C6 C7 N1 166.1(2)
C1 C6 C7 C8 -131.67(19)
C5 C6 C7 C8 46.6(3)
C1 C6 C7 C10 112.7(2)
C5 C6 C7 C10 -69.0(3)
C9 N2 C8 O4 165.3(2)
C17 N2 C8 O4 7.4(4)
C9 N2 C8 C7 -16.4(3)
C17 N2 C8 C7 -174.4(2)
N1 C7 C8 O4 -56.5(3)
C6 C7 C8 O4 59.3(3)
C10 C7 C8 O4 -178.6(2)
N1 C7 C8 N2 125.20(19)
C6 C7 C8 N2 -119.0(2)
C10 C7 C8 N2 3.1(2)
C8 N2 C9 O3 -97.3(2)
C17 N2 C9 O3 60.5(3)
C8 N2 C9 C11 141.59(19)
C17 N2 C9 C11 -60.5(3)
C8 N2 C9 C10 21.6(2)
C17 N2 C9 C10 179.50(19)
N1 C7 C10 F2 11.7(3)
C6 C7 C10 F2 -108.0(2)
C8 C7 C10 F2 131.6(2)
N1 C7 C10 F1 129.66(19)
C6 C7 C10 F1 10.0(3)
C8 C7 C10 F1 -110.5(2)
N1 C7 C10 C9 -110.2(2)
C6 C7 C10 C9 130.11(19)
C8 C7 C10 C9 9.6(2)
O3 C9 C10 F2 -22.4(3)
N2 C9 C10 F2 -140.7(2)
C11 C9 C10 F2 97.2(2)
O3 C9 C10 F1 -139.62(19)
N2 C9 C10 F1 102.09(19)
C11 C9 C10 F1 -20.0(2)
O3 C9 C10 C7 100.4(2)
N2 C9 C10 C7 -17.8(2)
C11 C9 C10 C7 -139.93(18)
O3 C9 C11 C12 33.8(3)
N2 C9 C11 C12 157.2(2)
C10 C9 C11 C12 -88.8(2)
O3 C9 C11 C16 -152.1(2)
N2 C9 C11 C16 -28.7(3)
C10 C9 C11 C16 85.3(3)
C16 C11 C12 C13 0.7(4)
C9 C11 C12 C13 174.9(2)
C11 C12 C13 C14 -0.4(4)
C12 C13 C14 C15 0.3(5)
C13 C14 C15 C16 -0.5(5)
C14 C15 C16 C11 0.8(4)
C12 C11 C16 C15 -0.9(4)
C9 C11 C16 C15 -175.0(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168303692
