Asymmetric Organocatalytic Wittig [2,3]-Rearrangement of Oxindoles.
Ošeka, Maksim; Kimm, Mariliis; Kaabel, Sandra; Järving, Ivar; Rissanen, Kari; Kanger, Tõnis; Organic letters 18 (2016) 1358–1361; doi:10.1021/acs.orglett.6b00291

data_1555496
_publ_section_title
;
 Asymmetric Organocatalytic Wittig [2,3]-Rearrangement of Oxindoles.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1358
_journal_page_last               1361
_journal_paper_doi               10.1021/acs.orglett.6b00291
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H22 F N O2'
_chemical_formula_sum            'C25 H22 F N O2'
_chemical_formula_weight         387.43
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-11-19
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.56524(7)
_cell_length_b                   18.64102(14)
_cell_length_c                   22.57118(18)
_cell_measurement_reflns_used    34152
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      67.2470
_cell_measurement_theta_min      1.9280
_cell_volume                     4024.57(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
HKL-2000
Rigaku Collection Strategy
(Daniels, L. M. (2011). Acta Cryst. A67, C143)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 22.17
_diffrn_detector_type            'Rigaku Saturn944+'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       AFC11
_diffrn_measurement_device_type  'Rigaku Saturn944+ (2x2 bin mode)'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            39394
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.330
_diffrn_reflns_theta_max         67.330
_diffrn_reflns_theta_min         3.075
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.6
_diffrn_source_power             0.03
_diffrn_source_target            CuK\a
_diffrn_source_type              'Rigaku MicroMax-003'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58319
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 3043 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     533
_refine_ls_number_reflns         7170
_refine_ls_number_restraints     476
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0281
_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/[\s^2^(Fo^2^)+(0.0414P)^2^+0.5978P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0744
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                7095
_reflns_number_total             7170
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b00291_si_003.cif
_cod_data_source_block           3i
_cod_database_code               1555496
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H2A-O2A
 0.84 with sigma of 0.02
 OBA-HBA
 0.84 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, CB0A, CB1A, CB2A,
  CB3A, CB4A, CB5A, CB6A, CB7A, CB8A, CB9A, CBA, C1A, C2A, C3A, C4A, C5A, C6A,
 C7A, C8A, C9A, C10A, C11A, C12A, C13A, C14A, C15A, C16A, C17A, C18A, C19A,
 C20A, C21A, C22A, C23A, C24A, C25A, NBA, N1A, O1, OBA, O1A, O2A, FBA, F1A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Ternary CH refined with riding coordinates:
 C9(H9), C9A(H9A)
4.b Secondary CH2 refined with riding coordinates:
 CB8A(HB8A,HB8B), C18A(H18A,H18B)
4.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), CB0A(HB0A), CB1A(HB1A),
 CB3A(HB3A), CB4A(HB4A), CB5A(HB5A), CB6A(HB6A), CB7A(HB7A), C6A(H6A), C7A(H7A),
  C8A(H8A), C10A(H10A), C13A(H13D), C14A(H14C), C15A(H15A), C16A(H16A),
 C17A(H17A), C20A(H20A), C21A(H21A), C23A(H23A), C24A(H24A)
4.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B), C11A(H11A,H11B)
4.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C25A(H25A,H25B,H25C)
;
_shelx_res_checksum              76892
_shelx_hkl_checksum              26421
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'