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_4033960
_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         'C23 H18 N2 O'
_chemical_formula_sum            'C23 H18 N2 O'
_chemical_formula_weight         338.39
_chemical_name_systematic
2-(1-methyl-3-oxo-2-phenylindolin-2-yl)-2-phenylacetonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_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                 99.986(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3188(3)
_cell_length_b                   7.4995(2)
_cell_length_c                   25.0534(6)
_cell_measurement_reflns_used    6604
_cell_measurement_temperature    150.1(3)
_cell_measurement_theta_max      75.5690
_cell_measurement_theta_min      4.8190
_cell_volume                     1724.36(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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      150.1(3)
_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 0.998
_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    -83.00  20.00   1.00    2.00    --  -42.10  99.00 -35.00  103
  2  \w      1.00  83.00   1.00    2.00    --   42.10 -99.00-141.00   82
  3  \w    113.00 139.00   1.00   12.00    --  112.00  99.00 -35.00   26
  4  \w     32.00  92.00   1.00   12.00    --  112.00 -99.00-141.00   60
  5  \w   -104.00 -35.00   1.00    2.00    --  -42.10 -57.00-120.00   69
  6  \w    -27.00  15.00   1.00    2.00    --   42.10 -38.00  90.00   42
  7  \w     20.00  67.00   1.00    2.00    --   42.10 -38.00  90.00   47
  8  \w    128.00 177.00   1.00   12.00    --  112.00 111.00  60.00   49
  9  \w     65.00  97.00   1.00   12.00    --  112.00 -94.00 -90.00   32
 10  \w     59.00 151.00   1.00   12.00    --  112.00 178.00  90.00   92
 11  \w    100.00 177.00   1.00   12.00    --  112.00 111.00 -60.00   77
 12  \w     56.00 115.00   1.00   12.00    --  112.00-111.00 -90.00   59
 13  \w     93.00 145.00   1.00   12.00    --  112.00  30.00 120.00   52
 14  \w     87.00 151.00   1.00   12.00    --  112.00  61.00-120.00   64
 15  \w     58.00 138.00   1.00   12.00    --  112.00 -45.00-150.00   80
 16  \w     92.00 151.00   1.00   12.00    --  112.00  30.00 -30.00   59
 17  \w     87.00 178.00   1.00   12.00    --  112.00  45.00  60.00   91
;
_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      -0.1496914000
_diffrn_orient_matrix_UB_12      0.0057539000
_diffrn_orient_matrix_UB_13      0.0181058000
_diffrn_orient_matrix_UB_21      -0.0281329000
_diffrn_orient_matrix_UB_22      -0.1946670000
_diffrn_orient_matrix_UB_23      -0.0184880000
_diffrn_orient_matrix_UB_31      0.0704901000
_diffrn_orient_matrix_UB_32      -0.0652186000
_diffrn_orient_matrix_UB_33      0.0568458000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10464
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.497
_diffrn_reflns_theta_min         4.841
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.303
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.315
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0611P)^2^+0.7210P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1217
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3098
_reflns_number_total             3524
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01874_si_002.cif
_cod_data_source_block           anna_11112017_da_nme_nitrile_8_cr
_cod_original_cell_volume        1724.37(9)
_cod_database_code               4033960
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.825
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C005(H005)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C00E(H00E), C00D(H00D), C00F(H00F), C00B(H00B), C00H(H00H),
 C00I(H00I), C00J(H00J), C00O(H00O), C00L(H00L), C00M(H00M), C00N(H00N),
 C00P(H00P), C00Q(H00Q)
2.c Fitted hexagon refined as free rotating group:
 C004(C006,C00E,C00D,C00F,C00B), C008(C00H,C00I,C00J,C00O,C00L)
2.d Idealised Me refined as rotating group:
 C00K(H00A,H00C,H00G)
;
_shelx_res_checksum              63784
_shelx_hkl_checksum              98548
_olex2_exptl_crystal_mounting_method
'Mounted on the glass stick by acrylic glue'
_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 1.958
_oxdiff_exptl_absorpt_empirical_full_min 0.618