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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/86/1508640.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_1508640
loop_
_publ_author_name
'Tolstoy, Päivi'
'Lee, Samantha X. Y.'
'Sparr, Christof'
'Ley, Steven V.'
_publ_section_title
;
 Synthesis of enantiomerically enriched 3-amino-2-oxindoles through a
 palladium-mediated asymmetric intramolecular arylation of α-ketimino
 amides.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4810
_journal_page_last               4813
_journal_paper_doi               10.1021/ol302119j
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration
;
 Flack parameter -0.03(4)
;
_chemical_formula_moiety         'C22 H17 F3 N2 O4 S'
_chemical_formula_sum            'C22 H17 F3 N2 O4 S'
_chemical_formula_weight         462.44
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.47(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.9853(1)
_cell_length_b                   16.2493(3)
_cell_length_c                   10.5283(2)
_cell_measurement_reflns_used    11042
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      33.14
_cell_measurement_theta_min      1.00
_cell_volume                     1023.92(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16669
_diffrn_reflns_theta_full        33.12
_diffrn_reflns_theta_max         33.12
_diffrn_reflns_theta_min         3.63
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         7028
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0331
_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)+(0.0370P)²+0.1939P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0837
_reflns_number_gt                6478
_reflns_number_total             7028
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302119j_si_001.cif
_cod_data_source_block           sl1240
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1508640
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 0.25415(5) 0.051981(19) 0.16713(3) 0.02464(7) Uani 1 1 d .
O1 O 0.28689(16) -0.00706(6) 0.04959(9) 0.02516(18) Uani 1 1 d .
O2 O 0.2042(2) 0.00581(8) 0.27743(10) 0.0391(3) Uani 1 1 d .
O3 O 0.1277(2) 0.12235(7) 0.13433(12) 0.0394(3) Uani 1 1 d .
O4 O 0.07094(18) -0.29735(6) 0.14294(10) 0.0302(2) Uani 1 1 d .
N1 N 0.21767(19) -0.16780(6) 0.11680(11) 0.0229(2) Uani 1 1 d .
H1N H 0.3361 -0.1382 0.1362 0.034 Uiso 1 1 calc R
N2 N 0.52214(18) -0.19884(7) 0.29171(10) 0.02074(19) Uani 1 1 d .
C1 C 0.0898(2) -0.04798(8) 0.00248(11) 0.0226(2) Uani 1 1 d .
C2 C 0.0597(2) -0.13031(8) 0.03704(11) 0.0213(2) Uani 1 1 d .
C3 C -0.1313(2) -0.16998(9) -0.01090(13) 0.0272(3) Uani 1 1 d .
H3 H -0.1595 -0.2259 0.0099 0.033 Uiso 1 1 calc R
C4 C -0.2792(3) -0.12711(10) -0.08892(14) 0.0320(3) Uani 1 1 d .
H4 H -0.4091 -0.1543 -0.1200 0.038 Uiso 1 1 calc R
C5 C -0.2421(3) -0.04583(10) -0.12258(13) 0.0326(3) Uani 1 1 d .
H5 H -0.3449 -0.0180 -0.1768 0.039 Uiso 1 1 calc R
C6 C -0.0536(2) -0.00510(9) -0.07661(13) 0.0289(3) Uani 1 1 d .
H6 H -0.0246 0.0505 -0.0990 0.035 Uiso 1 1 calc R
C7 C 0.5487(3) 0.08256(9) 0.17586(16) 0.0325(3) Uani 1 1 d .
F1 F 0.67697(17) 0.01798(7) 0.19497(12) 0.0471(3) Uani 1 1 d .
F2 F 0.57044(19) 0.13395(8) 0.27293(11) 0.0512(3) Uani 1 1 d .
F3 F 0.60810(19) 0.11976(7) 0.07052(11) 0.0504(3) Uani 1 1 d .
C8 C 0.2099(2) -0.24474(7) 0.16796(12) 0.0212(2) Uani 1 1 d .
C9 C 0.3941(2) -0.25997(7) 0.26580(11) 0.0196(2) Uani 1 1 d .
C10 C 0.4050(2) -0.34401(7) 0.32190(11) 0.0207(2) Uani 1 1 d .
C11 C 0.2259(2) -0.37474(8) 0.39166(13) 0.0250(2) Uani 1 1 d .
H11 H 0.0901 -0.3447 0.3962 0.030 Uiso 1 1 calc R
C12 C 0.2480(2) -0.44980(10) 0.45446(13) 0.0303(3) Uani 1 1 d .
H12 H 0.1272 -0.4708 0.5027 0.036 Uiso 1 1 calc R
C13 C 0.4461(3) -0.49409(9) 0.44668(15) 0.0330(3) Uani 1 1 d .
H13 H 0.4611 -0.5449 0.4905 0.040 Uiso 1 1 calc R
C14 C 0.6215(2) -0.46421(8) 0.37518(15) 0.0302(3) Uani 1 1 d .
H14 H 0.7555 -0.4952 0.3686 0.036 Uiso 1 1 calc R
C15 C 0.6022(2) -0.38898(8) 0.31292(13) 0.0244(2) Uani 1 1 d .
H15 H 0.7231 -0.3684 0.2644 0.029 Uiso 1 1 calc R
C16 C 0.6850(2) -0.19951(7) 0.39061(11) 0.0195(2) Uani 1 1 d .
C17 C 0.6569(2) -0.23928(8) 0.50756(12) 0.0245(2) Uani 1 1 d .
H17 H 0.5280 -0.2720 0.5219 0.029 Uiso 1 1 calc R
C18 C 0.8177(2) -0.23082(8) 0.60252(12) 0.0258(2) Uani 1 1 d .
H18 H 0.7954 -0.2572 0.6820 0.031 Uiso 1 1 calc R
C19 C 1.0116(2) -0.18455(8) 0.58411(12) 0.0225(2) Uani 1 1 d .
C20 C 1.0372(2) -0.14517(8) 0.46746(12) 0.0232(2) Uani 1 1 d .
H20 H 1.1681 -0.1137 0.4525 0.028 Uiso 1 1 calc R
C21 C 0.8752(2) -0.15110(7) 0.37263(11) 0.0216(2) Uani 1 1 d .
H21 H 0.8938 -0.1221 0.2951 0.026 Uiso 1 1 calc R
C22 C 1.1803(2) -0.17520(9) 0.69004(13) 0.0292(3) Uani 1 1 d .
H22A H 1.1827 -0.2254 0.7416 0.044 Uiso 1 1 calc R
H22B H 1.1393 -0.1282 0.7434 0.044 Uiso 1 1 calc R
H22C H 1.3286 -0.1659 0.6540 0.044 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
O3 S1 O2 120.87(8)
O3 S1 O1 111.71(6)
O2 S1 O1 110.43(6)
O3 S1 C7 107.81(7)
O2 S1 C7 108.16(8)
O1 S1 C7 94.50(7)
C1 O1 S1 116.38(8)
C8 N1 C2 127.72(11)
C8 N1 H1N 116.1
C2 N1 H1N 116.1
C9 N2 C16 123.72(10)
C6 C1 C2 124.01(12)
C6 C1 O1 118.61(12)
C2 C1 O1 117.35(11)
C1 C2 N1 119.01(11)
C1 C2 C3 116.89(11)
N1 C2 C3 124.10(11)
C4 C3 C2 119.70(13)
C4 C3 H3 120.1
C2 C3 H3 120.2
C5 C4 C3 121.76(14)
C5 C4 H4 119.1
C3 C4 H4 119.1
C4 C5 C6 119.71(13)
C4 C5 H5 120.1
C6 C5 H5 120.1
C1 C6 C5 117.92(13)
C1 C6 H6 121.0
C5 C6 H6 121.0
F1 C7 F3 109.53(14)
F1 C7 F2 109.35(14)
F3 C7 F2 109.59(13)
F1 C7 S1 110.59(10)
F3 C7 S1 110.43(11)
F2 C7 S1 107.33(11)
O4 C8 N1 125.69(11)
O4 C8 C9 121.38(11)
N1 C8 C9 112.92(10)
N2 C9 C10 126.99(11)
N2 C9 C8 116.49(10)
C10 C9 C8 116.51(10)
C15 C10 C11 120.19(12)
C15 C10 C9 119.28(11)
C11 C10 C9 120.33(11)
C12 C11 C10 119.49(12)
C12 C11 H11 120.3
C10 C11 H11 120.3
C13 C12 C11 120.19(13)
C13 C12 H12 119.9
C11 C12 H12 119.9
C14 C13 C12 120.10(13)
C14 C13 H13 119.9
C12 C13 H13 119.9
C13 C14 C15 120.23(13)
C13 C14 H14 119.9
C15 C14 H14 119.9
C14 C15 C10 119.78(13)
C14 C15 H15 120.1
C10 C15 H15 120.1
C21 C16 C17 118.82(11)
C21 C16 N2 116.81(11)
C17 C16 N2 124.12(11)
C18 C17 C16 119.94(11)
C18 C17 H17 120.0
C16 C17 H17 120.0
C17 C18 C19 121.65(12)
C17 C18 H18 119.2
C19 C18 H18 119.2
C20 C19 C18 117.81(12)
C20 C19 C22 121.87(12)
C18 C19 C22 120.26(12)
C21 C20 C19 121.32(12)
C21 C20 H20 119.3
C19 C20 H20 119.3
C20 C21 C16 120.40(11)
C20 C21 H21 119.8
C16 C21 H21 119.8
C19 C22 H22A 109.5
C19 C22 H22B 109.5
H22A C22 H22B 109.5
C19 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O3 1.4124(11)
S1 O2 1.4164(11)
S1 O1 1.5793(10)
S1 C7 1.8331(15)
O1 C1 1.4388(16)
O4 C8 1.2198(16)
N1 C8 1.3622(15)
N1 C2 1.3989(16)
N1 H1N 0.8800
N2 C9 1.2824(15)
N2 C16 1.4204(16)
C1 C6 1.3800(18)
C1 C2 1.3984(17)
C2 C3 1.4031(18)
C3 C4 1.390(2)
C3 H3 0.9500
C4 C5 1.386(2)
C4 H4 0.9500
C5 C6 1.391(2)
C5 H5 0.9500
C6 H6 0.9500
C7 F1 1.3147(19)
C7 F3 1.3147(19)
C7 F2 1.3253(18)
C8 C9 1.5232(17)
C9 C10 1.4891(16)
C10 C15 1.3916(18)
C10 C11 1.3969(18)
C11 C12 1.3932(19)
C11 H11 0.9500
C12 C13 1.390(2)
C12 H12 0.9500
C13 C14 1.385(2)
C13 H13 0.9500
C14 C15 1.3916(18)
C14 H14 0.9500
C15 H15 0.9500
C16 C21 1.3979(17)
C16 C17 1.4019(17)
C17 C18 1.3891(18)
C17 H17 0.9500
C18 C19 1.3974(19)
C18 H18 0.9500
C19 C20 1.3945(17)
C19 C22 1.5059(18)
C20 C21 1.3895(18)
C20 H20 0.9500
C21 H21 0.9500
C22 H22A 0.9800
C22 H22B 0.9800
C22 H22C 0.9800
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652030
2 PubChem 139040601
