#------------------------------------------------------------------------------
#$Date: 2017-11-07 03:10:59 +0200 (Tue, 07 Nov 2017) $
#$Revision: 202777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/73/1547394.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_1547394
loop_
_publ_author_name
'Paladhi, Sushovan'
'Park, Sang Yeon'
'Yang, Jung Woon'
'Song, Choong Eui'
_publ_section_title
;
 Asymmetric Synthesis of α-Fluoro-β-Amino-oxindoles with
 Tetrasubstituted C-F Stereogenic Centers via Cooperative Cation-Binding
 Catalysis.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5336
_journal_page_last               5339
_journal_paper_doi               10.1021/acs.orglett.7b02628
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H27 F N2 O3'
_chemical_formula_sum            'C23 H27 F N2 O3'
_chemical_formula_weight         398.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1934(9)
_cell_length_b                   11.1437(10)
_cell_length_c                   19.3947(18)
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      21.79
_cell_measurement_theta_min      2.26
_cell_volume                     2203.1(3)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1441
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            68177
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.086
_diffrn_reflns_theta_min         2.100
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_description       Block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
; 
 Flack x determined using 984 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         4382
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0382P)²+0.5568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2895
_reflns_number_total             4382
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol7b02628_si_002.cif
_cod_data_source_block           195K-chiral
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 1547394.cif.
;
_cod_database_code               1547394
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N1 N 0.8477(3) 0.9464(3) 0.79198(15) 0.0462(8) Uani 1 1 d . .
C1 C 0.8838(4) 0.8324(3) 0.80410(19) 0.0457(9) Uani 1 1 d . .
C2 C 0.7663(4) 0.7671(3) 0.8371(2) 0.0439(9) Uani 1 1 d . .
C3 C 0.6604(4) 0.8596(3) 0.8348(2) 0.0447(9) Uani 1 1 d . .
C4 C 0.5301(4) 0.8528(4) 0.8511(2) 0.0522(10) Uani 1 1 d . .
H4 H 0.4950 0.7815 0.8693 0.063 Uiso 1 1 calc R U
C5 C 0.4491(4) 0.9530(4) 0.8404(2) 0.0600(11) Uani 1 1 d . .
C6 C 0.5057(5) 1.0563(4) 0.8158(2) 0.0623(11) Uani 1 1 d . .
H6 H 0.4523 1.1242 0.8097 0.075 Uiso 1 1 calc R U
C7 C 0.6378(4) 1.0651(4) 0.7996(2) 0.0567(11) Uani 1 1 d . .
H7 H 0.6741 1.1371 0.7830 0.068 Uiso 1 1 calc R U
C8 C 0.7132(4) 0.9646(3) 0.80876(18) 0.0437(9) Uani 1 1 d . .
C9 C 0.9332(5) 1.0341(4) 0.7603(2) 0.0647(12) Uani 1 1 d . .
H9A H 1.0049 0.9933 0.7373 0.097 Uiso 1 1 calc R U
H9B H 0.9681 1.0870 0.7955 0.097 Uiso 1 1 calc R U
H9C H 0.8840 1.0807 0.7269 0.097 Uiso 1 1 calc R U
O1 O 0.9916(3) 0.7880(2) 0.79299(14) 0.0596(7) Uani 1 1 d . .
F1 F 0.7354(2) 0.67020(18) 0.79368(12) 0.0655(7) Uani 1 1 d . .
C10 C 0.3041(4) 0.9453(5) 0.8558(3) 0.0846(15) Uani 1 1 d . .
H10A H 0.2902 0.9518 0.9051 0.127 Uiso 1 1 calc R U
H10B H 0.2703 0.8690 0.8396 0.127 Uiso 1 1 calc R U
H10C H 0.2586 1.0102 0.8325 0.127 Uiso 1 1 calc R U
C11 C 0.7976(3) 0.7153(3) 0.9081(2) 0.0429(9) Uani 1 1 d . .
H11 H 0.7177 0.6746 0.9252 0.051 Uiso 1 1 calc R U
C12 C 0.8356(3) 0.8097(3) 0.96067(18) 0.0385(8) Uani 1 1 d . .
C13 C 0.9577(3) 0.8653(3) 0.9601(2) 0.0462(10) Uani 1 1 d . .
H13 H 1.0165 0.8493 0.9239 0.055 Uiso 1 1 calc R U
C14 C 0.9940(4) 0.9433(3) 1.0119(2) 0.0472(9) Uani 1 1 d . .
H14 H 1.0768 0.9802 1.0099 0.057 Uiso 1 1 calc R U
C15 C 0.9118(4) 0.9688(3) 1.0665(2) 0.0497(10) Uani 1 1 d . .
C16 C 0.7886(4) 0.9161(4) 1.0654(2) 0.0586(11) Uani 1 1 d . .
H16 H 0.7290 0.9336 1.1010 0.070 Uiso 1 1 calc R U
C17 C 0.7509(4) 0.8389(3) 1.0137(2) 0.0519(10) Uani 1 1 d . .
H17 H 0.6663 0.8055 1.0145 0.062 Uiso 1 1 calc R U
C18 C 0.9572(5) 1.0483(4) 1.1250(2) 0.0738(13) Uani 1 1 d . .
H18A H 1.0515 1.0585 1.1223 0.111 Uiso 1 1 calc R U
H18B H 0.9344 1.0114 1.1686 0.111 Uiso 1 1 calc R U
H18C H 0.9147 1.1259 1.1214 0.111 Uiso 1 1 calc R U
N2 N 0.8993(3) 0.6245(2) 0.90013(19) 0.0517(9) Uani 1 1 d . .
H2 H 0.9686 0.6409 0.8758 0.062 Uiso 1 1 calc R U
C19 C 0.8883(3) 0.5157(3) 0.9296(2) 0.0409(9) Uani 1 1 d . .
O2 O 0.9869(2) 0.4453(2) 0.90764(12) 0.0433(6) Uani 1 1 d . .
O3 O 0.8026(3) 0.4880(2) 0.96839(16) 0.0649(9) Uani 1 1 d . .
C20 C 0.9990(4) 0.3221(3) 0.9350(2) 0.0493(9) Uani 1 1 d . .
C21 C 1.1204(4) 0.2764(3) 0.8983(3) 0.0670(13) Uani 1 1 d . .
H21A H 1.1071 0.2809 0.8488 0.101 Uiso 1 1 calc R U
H21B H 1.1365 0.1938 0.9115 0.101 Uiso 1 1 calc R U
H21C H 1.1952 0.3254 0.9110 0.101 Uiso 1 1 calc R U
C22 C 1.0227(5) 0.3278(4) 1.0113(2) 0.0847(16) Uani 1 1 d . .
H22A H 1.0902 0.3869 1.0209 0.127 Uiso 1 1 calc R U
H22B H 1.0511 0.2498 1.0277 0.127 Uiso 1 1 calc R U
H22C H 0.9422 0.3505 1.0345 0.127 Uiso 1 1 calc R U
C23 C 0.8807(5) 0.2497(4) 0.9155(3) 0.0890(18) Uani 1 1 d . .
H23A H 0.8053 0.2776 0.9414 0.133 Uiso 1 1 calc R U
H23B H 0.8964 0.1657 0.9258 0.133 Uiso 1 1 calc R U
H23C H 0.8637 0.2588 0.8665 0.133 Uiso 1 1 calc R U
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'
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
C1 N1 C8 111.0(3) .
C1 N1 C9 123.2(3) .
C8 N1 C9 125.5(3) .
O1 C1 N1 126.7(3) 1
O1 C1 N1 126.7(3) .
O1 C1 C2 125.4(3) 1
O1 C1 C2 125.4(3) .
N1 C1 C2 107.9(3) .
F1 C2 C3 110.6(3) .
F1 C2 C11 107.3(3) .
C3 C2 C11 116.0(3) .
F1 C2 C1 106.8(3) .
C3 C2 C1 102.9(3) .
C11 C2 C1 113.0(3) .
C4 C3 C8 120.6(3) .
C4 C3 C2 131.0(3) .
C8 C3 C2 108.3(3) .
C3 C4 C5 119.5(4) .
C3 C4 H4 120.2 .
C5 C4 H4 120.2 .
C6 C5 C4 118.1(4) .
C6 C5 C10 121.8(4) .
C4 C5 C10 120.1(5) .
C5 C6 C7 123.1(4) .
C5 C6 H6 118.4 .
C7 C6 H6 118.4 .
C8 C7 C6 117.2(4) .
C8 C7 H7 121.4 .
C6 C7 H7 121.4 .
C7 C8 C3 121.4(4) .
C7 C8 N1 128.9(4) .
C3 C8 N1 109.7(3) .
N1 C9 H9A 109.5 .
N1 C9 H9B 109.5 .
H9A C9 H9B 109.5 .
N1 C9 H9C 109.5 .
H9A C9 H9C 109.5 .
H9B C9 H9C 109.5 .
C5 C10 H10A 109.5 .
C5 C10 H10B 109.5 .
H10A C10 H10B 109.5 .
C5 C10 H10C 109.5 .
H10A C10 H10C 109.5 .
H10B C10 H10C 109.5 .
N2 C11 C12 111.9(3) .
N2 C11 C2 108.4(3) .
C12 C11 C2 113.5(3) .
N2 C11 H11 107.6 .
C12 C11 H11 107.6 .
C2 C11 H11 107.6 .
C17 C12 C13 117.4(4) .
C17 C12 C11 120.3(3) .
C13 C12 C11 122.2(3) .
C14 C13 C12 121.0(4) .
C14 C13 H13 119.5 .
C12 C13 H13 119.5 .
C13 C14 C15 121.7(4) .
C13 C14 H14 119.1 .
C15 C14 H14 119.1 .
C14 C15 C16 116.8(4) .
C14 C15 C18 120.7(4) .
C16 C15 C18 122.5(4) .
C17 C16 C15 121.9(4) .
C17 C16 H16 119.0 .
C15 C16 H16 119.0 .
C16 C17 C12 121.0(4) .
C16 C17 H17 119.5 .
C12 C17 H17 119.5 .
C15 C18 H18A 109.5 .
C15 C18 H18B 109.5 .
H18A C18 H18B 109.5 .
C15 C18 H18C 109.5 .
H18A C18 H18C 109.5 .
H18B C18 H18C 109.5 .
C19 N2 C11 121.5(3) .
C19 N2 H2 119.3 .
C11 N2 H2 119.3 .
O3 C19 O2 126.6(3) .
O3 C19 N2 124.2(3) .
O2 C19 N2 109.2(3) .
C19 O2 C20 119.4(3) .
O2 C20 C23 110.1(3) .
O2 C20 C22 109.1(3) .
C23 C20 C22 113.6(4) .
O2 C20 C21 102.2(3) .
C23 C20 C21 110.9(3) .
C22 C20 C21 110.2(4) .
C20 C21 H21A 109.5 .
C20 C21 H21B 109.5 .
H21A C21 H21B 109.5 .
C20 C21 H21C 109.5 .
H21A C21 H21C 109.5 .
H21B C21 H21C 109.5 .
C20 C22 H22A 109.5 .
C20 C22 H22B 109.5 .
H22A C22 H22B 109.5 .
C20 C22 H22C 109.5 .
H22A C22 H22C 109.5 .
H22B C22 H22C 109.5 .
C20 C23 H23A 109.5 .
C20 C23 H23B 109.5 .
H23A C23 H23B 109.5 .
C20 C23 H23C 109.5 .
H23A C23 H23C 109.5 .
H23B C23 H23C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.343(4) .
N1 C8 1.423(5) .
N1 C9 1.446(5) .
C1 O1 1.225(4) 1
C1 O1 1.225(4) .
C1 C2 1.541(5) .
C2 F1 1.405(4) .
C2 C3 1.494(5) .
C2 C11 1.528(5) .
C3 C4 1.368(5) .
C3 C8 1.383(5) .
C4 C5 1.404(6) .
C4 H4 0.9400 .
C5 C6 1.373(6) .
C5 C10 1.511(6) .
C6 C7 1.387(6) .
C6 H6 0.9400 .
C7 C8 1.370(5) .
C7 H7 0.9400 .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C9 H9C 0.9700 .
O1 O1 0.000(10) 1
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C10 H10C 0.9700 .
C11 N2 1.457(4) .
C11 C12 1.515(5) .
C11 H11 0.9900 .
C12 C17 1.382(5) .
C12 C13 1.390(5) .
C13 C14 1.379(5) .
C13 H13 0.9400 .
C14 C15 1.380(5) .
C14 H14 0.9400 .
C15 C16 1.387(5) .
C15 C18 1.511(6) .
C16 C17 1.375(5) .
C16 H16 0.9400 .
C17 H17 0.9400 .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C18 H18C 0.9700 .
N2 C19 1.345(4) .
N2 H2 0.8700 .
C19 O3 1.194(4) .
C19 O2 1.344(4) .
O2 C20 1.477(4) .
C20 C23 1.500(6) .
C20 C22 1.500(6) .
C20 C21 1.516(5) .
C21 H21A 0.9700 .
C21 H21B 0.9700 .
C21 H21C 0.9700 .
C22 H22A 0.9700 .
C22 H22B 0.9700 .
C22 H22C 0.9700 .
C23 H23A 0.9700 .
C23 H23B 0.9700 .
C23 H23C 0.9700 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 O1 0.87 2.31 2.920(4) 127.6 1
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C8 N1 C1 O1 177.7(4) . 1
C9 N1 C1 O1 2.7(6) . 1
C8 N1 C1 O1 177.7(4) . .
C9 N1 C1 O1 2.7(6) . .
C8 N1 C1 C2 -4.2(4) . .
C9 N1 C1 C2 -179.2(3) . .
O1 C1 C2 F1 -60.7(5) 1 .
O1 C1 C2 F1 -60.7(5) . .
N1 C1 C2 F1 121.2(3) . .
O1 C1 C2 C3 -177.1(4) 1 .
O1 C1 C2 C3 -177.1(4) . .
N1 C1 C2 C3 4.8(4) . .
O1 C1 C2 C11 57.1(5) 1 .
O1 C1 C2 C11 57.1(5) . .
N1 C1 C2 C11 -121.1(3) . .
F1 C2 C3 C4 60.0(5) . .
C11 C2 C3 C4 -62.4(5) . .
C1 C2 C3 C4 173.7(4) . .
F1 C2 C3 C8 -117.3(3) . .
C11 C2 C3 C8 120.2(3) . .
C1 C2 C3 C8 -3.6(4) . .
C8 C3 C4 C5 0.8(6) . .
C2 C3 C4 C5 -176.3(4) . .
C3 C4 C5 C6 -2.1(6) . .
C3 C4 C5 C10 177.8(4) . .
C4 C5 C6 C7 1.6(6) . .
C10 C5 C6 C7 -178.3(4) . .
C5 C6 C7 C8 0.2(6) . .
C6 C7 C8 C3 -1.6(5) . .
C6 C7 C8 N1 175.3(3) . .
C4 C3 C8 C7 1.1(6) . .
C2 C3 C8 C7 178.8(3) . .
C4 C3 C8 N1 -176.3(4) . .
C2 C3 C8 N1 1.4(4) . .
C1 N1 C8 C7 -175.3(4) . .
C9 N1 C8 C7 -0.5(6) . .
C1 N1 C8 C3 1.9(4) . .
C9 N1 C8 C3 176.7(4) . .
N1 C1 O1 O1 0.0(4) . 1
C2 C1 O1 O1 0.0(3) . 1
F1 C2 C11 N2 54.0(4) . .
C3 C2 C11 N2 178.2(3) . .
C1 C2 C11 N2 -63.4(4) . .
F1 C2 C11 C12 178.9(3) . .
C3 C2 C11 C12 -56.9(4) . .
C1 C2 C11 C12 61.5(4) . .
N2 C11 C12 C17 -128.5(3) . .
C2 C11 C12 C17 108.5(4) . .
N2 C11 C12 C13 47.9(4) . .
C2 C11 C12 C13 -75.1(4) . .
C17 C12 C13 C14 2.0(5) . .
C11 C12 C13 C14 -174.5(3) . .
C12 C13 C14 C15 0.7(5) . .
C13 C14 C15 C16 -2.7(5) . .
C13 C14 C15 C18 175.9(4) . .
C14 C15 C16 C17 2.1(6) . .
C18 C15 C16 C17 -176.5(4) . .
C15 C16 C17 C12 0.6(6) . .
C13 C12 C17 C16 -2.6(5) . .
C11 C12 C17 C16 173.9(3) . .
C12 C11 N2 C19 102.2(4) . .
C2 C11 N2 C19 -132.0(4) . .
C11 N2 C19 O3 -6.4(6) . .
C11 N2 C19 O2 172.9(3) . .
O3 C19 O2 C20 -3.0(6) . .
N2 C19 O2 C20 177.7(3) . .
C19 O2 C20 C23 62.6(4) . .
C19 O2 C20 C22 -62.7(4) . .
C19 O2 C20 C21 -179.5(3) . .
