Preparation of Stereodefined 2-(3-Oxoindolin-2-yl)-2-Arylacetonitriles via One-Pot Reaction of Indoles with Nitroalkenes.
Aksenov, Alexander V.; Aksenov, Dmitrii A.; Aksenov, Nicolai A.; Aleksandrova, Elena V.; Rubin, Michael; The Journal of organic chemistry 84 (2019) 12420–12429; doi:10.1021/acs.joc.9b01874

data_4033959
_publ_section_title
;
 Preparation of Stereodefined 2-(3-Oxoindolin-2-yl)-2-Arylacetonitriles
 via One-Pot Reaction of Indoles with Nitroalkenes.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12420
_journal_page_last               12429
_journal_paper_doi               10.1021/acs.joc.9b01874
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C22 H16 N2 O'
_chemical_formula_sum            'C22 H16 N2 O'
_chemical_formula_weight         324.37
_chemical_name_systematic
2-(3-oxo-2-phenylindolin-2-yl)-2-phenylacetonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-03
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.841(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8092(3)
_cell_length_b                   11.4234(4)
_cell_length_c                   17.0959(5)
_cell_measurement_reflns_used    6203
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.0720
_cell_measurement_theta_min      4.5990
_cell_volume                     1683.77(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -91.00  -6.00   1.00    1.00    --  -41.35 125.00  60.00   85
  2  \w   -105.00 -17.00   1.00    1.00    --  -41.35 -38.00 -90.00   88
  3  \w     -8.00  26.00   1.00    1.00    --  -41.35  77.00-180.00   34
  4  \w     55.00  80.00   1.00    1.00    --   41.35-125.00  90.00   25
  5  \w     37.00 102.00   1.00    4.00    --  112.00-111.00  30.00   65
  6  \w     65.00 106.00   1.00    4.00    --  112.00 -95.00  60.00   41
  7  \w     88.00 113.00   1.00    4.00    --  112.00 -45.00  30.00   25
  8  \w     82.00 108.00   1.00    4.00    --  112.00 -95.00 -55.00   26
  9  \w     66.00 109.00   1.00    4.00    --  112.00 -95.00-120.00   43
 10  \w     97.00 165.00   1.00    4.00    --  112.00 -15.00-180.00   68
 11  \w     82.00 173.00   1.00    4.00    --  112.00  77.00-180.00   91
 12  \w    109.00 176.00   1.00    4.00    --  112.00  95.00  54.00   67
 13  \w    109.00 164.00   1.00    4.00    --  112.00 111.00 150.00   55
 14  \w     79.00 128.00   1.00    4.00    --  112.00  77.00  90.00   49
 15  \w     39.00  66.00   1.00    4.00    --  112.00 -45.00  30.00   27
 16  \w     41.00  80.00   1.00    4.00    --  112.00 -95.00 -90.00   39
 17  \w     30.00  55.00   1.00    4.00    --  112.00 -95.00-120.00   25
 18  \w     37.00  65.00   1.00    4.00    --  112.00 -15.00-180.00   28
 19  \w   -114.00 -14.00   1.00    1.00    --  -41.85 -57.00-180.00  100
 20  \w   -114.00 -14.00   1.00    1.00    --  -41.85 -57.00  60.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0633796000
_diffrn_orient_matrix_UB_12      0.1258002000
_diffrn_orient_matrix_UB_13      0.0123942000
_diffrn_orient_matrix_UB_21      -0.0359510000
_diffrn_orient_matrix_UB_22      0.0015313000
_diffrn_orient_matrix_UB_23      0.0844436000
_diffrn_orient_matrix_UB_31      0.1631227000
_diffrn_orient_matrix_UB_32      -0.0485307000
_diffrn_orient_matrix_UB_33      0.0347105000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9845
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.168
_diffrn_reflns_theta_min         4.687
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_correction_T_min  0.813
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_preparation
'Prepared by Michael addition of nitrostyrene to 2-phenylindole'
_exptl_crystal_recrystallization_method 'Crystallized by evaporation of EtOH'
_exptl_crystal_size_max          0.538
_exptl_crystal_size_mid          0.356
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0675P)^2^+0.4516P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1248
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3191
_reflns_number_total             3468
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01874_si_003.cif
_cod_data_source_block           anna_18092017_nu_nitrile_2_2
_cod_database_code               4033959
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         C22H16N2O
_shelx_estimated_absorpt_t_max   0.834
_shelx_estimated_absorpt_t_min   0.729
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C6(H6), C22(H22), C9(H9), C15(H15), C12(H12), C18(H18), C8(H8),
 C7(H7), C21(H21), C14(H14), C20(H20), C13(H13), C19(H19)
;
_shelx_res_checksum              81241
_shelx_hkl_checksum              35246
_shelx_fab_checksum              85083
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.871
_oxdiff_exptl_absorpt_empirical_full_min 0.629