#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:47:55 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180316 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/30/7153057.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_7153057
loop_
_publ_author_name
'Dou, Xiaowei'
'Lu, Yixin'
_publ_section_title
;
 Enantioselective conjugate addition of 3-fluoro-oxindoles to vinyl
 sulfone: an organocatalytic access to chiral 3-fluoro-3-substituted
 oxindoles.
;
_journal_issue                   32
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5217
_journal_page_last               5221
_journal_paper_doi               10.1039/c3ob41267a
_journal_volume                  11
_journal_year                    2013
_chemical_formula_sum            'C27 H25 F2 N O7 S2'
_chemical_formula_weight         577.60
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2718(7)
_cell_length_b                   13.6799(13)
_cell_length_c                   23.831(2)
_cell_measurement_reflns_used    4443
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.81
_cell_measurement_theta_min      2.27
_cell_volume                     2696.7(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0532
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            19152
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.12(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         6196
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0456P)²+0.0896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0910
_reflns_number_gt                5640
_reflns_number_total             6196
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ob41267a.txt
_cod_data_source_block           c009
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'MUlti-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'Not Measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7153057
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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 0.99965(6) 0.10550(4) 0.918504(18) 0.01472(11) Uani 1 1 d .
S2 S 1.01594(6) 0.25358(4) 0.821324(19) 0.01652(12) Uani 1 1 d .
F1 F 0.39050(16) -0.22249(10) 0.82686(5) 0.0258(3) Uani 1 1 d .
F2 F 0.91053(16) 0.01119(10) 0.74269(5) 0.0232(3) Uani 1 1 d .
O3 O 0.83741(18) -0.24460(11) 0.89542(6) 0.0212(3) Uani 1 1 d .
O5 O 0.95542(19) 0.19345(12) 0.94740(6) 0.0234(4) Uani 1 1 d .
O4 O 0.90906(18) 0.01817(11) 0.92935(6) 0.0201(3) Uani 1 1 d .
O6 O 1.03670(18) 0.24729(11) 0.76194(6) 0.0252(4) Uani 1 1 d .
O1 O 1.00175(19) -0.10432(10) 0.83436(6) 0.0200(3) Uani 1 1 d .
O7 O 0.88561(19) 0.31060(12) 0.84325(7) 0.0230(4) Uani 1 1 d .
O2 O 0.68185(19) -0.31155(11) 0.82655(6) 0.0234(4) Uani 1 1 d .
N1 N 0.7290(2) -0.14628(12) 0.83171(7) 0.0158(4) Uani 1 1 d .
C1 C 0.8641(3) -0.08707(16) 0.82208(8) 0.0161(4) Uani 1 1 d .
C2 C 0.8066(3) 0.00273(16) 0.78860(8) 0.0160(4) Uani 1 1 d .
C3 C 0.6376(3) -0.02457(16) 0.77223(9) 0.0176(5) Uani 1 1 d .
C4 C 0.5257(3) 0.02620(17) 0.74030(9) 0.0227(5) Uani 1 1 d .
H4 H 0.5548 0.0853 0.7220 0.027 Uiso 1 1 calc R
C5 C 0.3702(3) -0.01104(18) 0.73562(10) 0.0244(5) Uani 1 1 d .
H5 H 0.2931 0.0214 0.7127 0.029 Uiso 1 1 calc R
C6 C 0.3266(3) -0.09549(17) 0.76432(9) 0.0206(5) Uani 1 1 d .
H6 H 0.2192 -0.1197 0.7616 0.025 Uiso 1 1 calc R
C7 C 0.4387(3) -0.14408(16) 0.79663(8) 0.0166(4) Uani 1 1 d .
C8 C 0.5963(2) -0.11080(16) 0.79967(8) 0.0142(4) Uani 1 1 d .
C9 C 0.7449(3) -0.24461(16) 0.85022(8) 0.0176(4) Uani 1 1 d .
C10 C 0.9138(3) -0.33587(17) 0.91542(10) 0.0244(5) Uani 1 1 d .
C11 C 1.0176(3) -0.37701(19) 0.86895(10) 0.0345(6) Uani 1 1 d .
H11A H 0.9484 -0.3988 0.8380 0.052 Uiso 1 1 calc R
H11B H 1.0799 -0.4326 0.8833 0.052 Uiso 1 1 calc R
H11C H 1.0918 -0.3264 0.8554 0.052 Uiso 1 1 calc R
C12 C 0.7851(4) -0.40678(19) 0.93556(11) 0.0341(6) Uani 1 1 d .
H12A H 0.7176 -0.3749 0.9639 0.051 Uiso 1 1 calc R
H12B H 0.8371 -0.4645 0.9520 0.051 Uiso 1 1 calc R
H12C H 0.7177 -0.4268 0.9038 0.051 Uiso 1 1 calc R
C13 C 1.0173(4) -0.2981(2) 0.96357(10) 0.0382(7) Uani 1 1 d .
H13A H 1.0927 -0.2487 0.9494 0.057 Uiso 1 1 calc R
H13B H 1.0783 -0.3525 0.9800 0.057 Uiso 1 1 calc R
H13C H 0.9476 -0.2690 0.9923 0.057 Uiso 1 1 calc R
C14 C 0.8130(2) 0.09837(15) 0.82154(9) 0.0164(4) Uani 1 1 d .
H14A H 0.7393 0.0931 0.8541 0.020 Uiso 1 1 calc R
H14B H 0.7721 0.1517 0.7973 0.020 Uiso 1 1 calc R
C15 C 0.9829(3) 0.12675(14) 0.84301(8) 0.0139(4) Uani 1 1 d .
H15 H 1.0643 0.0847 0.8235 0.017 Uiso 1 1 calc R
C16 C 1.2065(3) 0.07960(15) 0.93088(8) 0.0145(4) Uani 1 1 d .
C17 C 1.2680(3) -0.00903(17) 0.91262(8) 0.0192(5) Uani 1 1 d .
H17 H 1.2015 -0.0548 0.8934 0.023 Uiso 1 1 calc R
C18 C 1.4295(3) -0.02898(19) 0.92318(8) 0.0242(5) Uani 1 1 d .
H18 H 1.4745 -0.0894 0.9112 0.029 Uiso 1 1 calc R
C19 C 1.5252(3) 0.03776(18) 0.95079(8) 0.0239(5) Uani 1 1 d .
H19 H 1.6361 0.0236 0.9572 0.029 Uiso 1 1 calc R
C20 C 1.4610(3) 0.12541(17) 0.96931(9) 0.0246(5) Uani 1 1 d .
H20 H 1.5274 0.1708 0.9888 0.030 Uiso 1 1 calc R
C21 C 1.2992(3) 0.14708(16) 0.95943(9) 0.0212(5) Uani 1 1 d .
H21 H 1.2537 0.2069 0.9720 0.025 Uiso 1 1 calc R
C22 C 1.1983(3) 0.29365(15) 0.85128(8) 0.0158(4) Uani 1 1 d .
C23 C 1.1928(3) 0.36051(16) 0.89486(9) 0.0198(5) Uani 1 1 d .
H23 H 1.0922 0.3825 0.9094 0.024 Uiso 1 1 calc R
C24 C 1.3374(3) 0.39478(18) 0.91688(10) 0.0264(5) Uani 1 1 d .
H24 H 1.3367 0.4406 0.9468 0.032 Uiso 1 1 calc R
C25 C 1.4828(3) 0.36197(17) 0.89500(10) 0.0288(5) Uani 1 1 d .
H25 H 1.5814 0.3855 0.9103 0.035 Uiso 1 1 calc R
C26 C 1.4869(3) 0.29609(17) 0.85152(9) 0.0267(5) Uani 1 1 d .
H26 H 1.5878 0.2744 0.8371 0.032 Uiso 1 1 calc R
C27 C 1.3433(3) 0.26111(17) 0.82850(9) 0.0214(5) Uani 1 1 d .
H27 H 1.3444 0.2162 0.7981 0.026 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
O5 S1 O4 118.64(9)
O5 S1 C16 109.53(10)
O4 S1 C16 107.94(10)
O5 S1 C15 108.66(9)
O4 S1 C15 105.69(9)
C16 S1 C15 105.59(9)
O6 S2 O7 119.06(10)
O6 S2 C22 108.56(9)
O7 S2 C22 109.19(10)
O6 S2 C15 103.92(9)
O7 S2 C15 107.54(10)
C22 S2 C15 108.01(9)
C9 O3 C10 120.68(17)
C1 N1 C9 121.63(17)
C1 N1 C8 109.31(17)
C9 N1 C8 124.13(17)
O1 C1 N1 127.2(2)
O1 C1 C2 125.24(19)
N1 C1 C2 107.43(17)
F2 C2 C3 113.02(16)
F2 C2 C14 108.09(16)
C3 C2 C14 112.32(18)
F2 C2 C1 106.36(17)
C3 C2 C1 102.97(17)
C14 C2 C1 113.98(16)
C4 C3 C8 121.3(2)
C4 C3 C2 129.9(2)
C8 C3 C2 108.51(18)
C3 C4 C5 118.6(2)
C3 C4 H4 120.7
C5 C4 H4 120.7
C4 C5 C6 120.4(2)
C4 C5 H5 119.8
C6 C5 H5 119.8
C7 C6 C5 120.1(2)
C7 C6 H6 119.9
C5 C6 H6 119.9
F1 C7 C6 118.85(19)
F1 C7 C8 120.74(19)
C6 C7 C8 120.4(2)
C7 C8 C3 119.0(2)
C7 C8 N1 130.0(2)
C3 C8 N1 110.67(18)
O2 C9 O3 129.6(2)
O2 C9 N1 122.55(18)
O3 C9 N1 107.85(18)
O3 C10 C11 108.74(18)
O3 C10 C12 110.0(2)
C11 C10 C12 113.1(2)
O3 C10 C13 101.36(18)
C11 C10 C13 111.1(2)
C12 C10 C13 111.9(2)
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C10 C12 H12A 109.5
C10 C12 H12B 109.5
H12A C12 H12B 109.5
C10 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C10 C13 H13A 109.5
C10 C13 H13B 109.5
H13A C13 H13B 109.5
C10 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C2 C14 C15 114.65(17)
C2 C14 H14A 108.6
C15 C14 H14A 108.6
C2 C14 H14B 108.6
C15 C14 H14B 108.6
H14A C14 H14B 107.6
C14 C15 S1 110.78(14)
C14 C15 S2 106.28(13)
S1 C15 S2 114.67(10)
C14 C15 H15 108.3
S1 C15 H15 108.3
S2 C15 H15 108.3
C21 C16 C17 122.4(2)
C21 C16 S1 119.03(17)
C17 C16 S1 118.51(16)
C16 C17 C18 118.0(2)
C16 C17 H17 121.0
C18 C17 H17 121.0
C19 C18 C17 120.7(2)
C19 C18 H18 119.7
C17 C18 H18 119.7
C18 C19 C20 120.5(2)
C18 C19 H19 119.8
C20 C19 H19 119.8
C19 C20 C21 120.0(2)
C19 C20 H20 120.0
C21 C20 H20 120.0
C16 C21 C20 118.4(2)
C16 C21 H21 120.8
C20 C21 H21 120.8
C23 C22 C27 122.2(2)
C23 C22 S2 118.87(17)
C27 C22 S2 118.84(16)
C22 C23 C24 118.6(2)
C22 C23 H23 120.7
C24 C23 H23 120.7
C25 C24 C23 119.8(2)
C25 C24 H24 120.1
C23 C24 H24 120.1
C26 C25 C24 121.2(2)
C26 C25 H25 119.4
C24 C25 H25 119.4
C25 C26 C27 120.1(2)
C25 C26 H26 120.0
C27 C26 H26 120.0
C22 C27 C26 118.2(2)
C22 C27 H27 120.9
C26 C27 H27 120.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O5 1.4337(16)
S1 O4 1.4337(16)
S1 C16 1.772(2)
S1 C15 1.8277(19)
S2 O6 1.4283(15)
S2 O7 1.4295(16)
S2 C22 1.756(2)
S2 C15 1.831(2)
F1 C7 1.352(2)
F2 C2 1.396(2)
O3 C9 1.322(2)
O3 C10 1.478(3)
O1 C1 1.199(3)
O2 C9 1.195(2)
N1 C1 1.400(3)
N1 C9 1.422(3)
N1 C8 1.422(3)
C1 C2 1.540(3)
C2 C3 1.499(3)
C2 C14 1.527(3)
C3 C4 1.385(3)
C3 C8 1.391(3)
C4 C5 1.388(3)
C4 H4 0.9500
C5 C6 1.390(3)
C5 H5 0.9500
C6 C7 1.376(3)
C6 H6 0.9500
C7 C8 1.383(3)
C10 C11 1.510(3)
C10 C12 1.518(3)
C10 C13 1.522(3)
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 C15 1.546(3)
C14 H14A 0.9900
C14 H14B 0.9900
C15 H15 1.0000
C16 C21 1.380(3)
C16 C17 1.385(3)
C17 C18 1.386(3)
C17 H17 0.9500
C18 C19 1.376(3)
C18 H18 0.9500
C19 C20 1.384(3)
C19 H19 0.9500
C20 C21 1.390(3)
C20 H20 0.9500
C21 H21 0.9500
C22 C23 1.385(3)
C22 C27 1.390(3)
C23 C24 1.388(3)
C23 H23 0.9500
C24 C25 1.386(4)
C24 H24 0.9500
C25 C26 1.374(3)
C25 H25 0.9500
C26 C27 1.393(3)
C26 H26 0.9500
C27 H27 0.9500
