P(NMe2)3-Mediated Reductive (1 + 4) Annulation Reaction of Isatins with Nitroalkenes: An Access to Spirooxindolyl Isoxazoline N-Oxides and Their Corresponding Isoxazolines.
Liu, Yiyi; Li, Hengyu; Zhou, Xun; He, Zhengjie; The Journal of organic chemistry 82 (2017) 10997–11007; doi:10.1021/acs.joc.7b01962

data_4032950
_publ_section_title
;
 P(NMe2)3-Mediated Reductive (1 + 4) Annulation Reaction of Isatins with
 Nitroalkenes: An Access to Spirooxindolyl Isoxazoline N-Oxides and Their
 Corresponding Isoxazolines.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10997
_journal_page_last               11007
_journal_paper_doi               10.1021/acs.joc.7b01962
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C23 H23 Cl N2 O6'
_chemical_formula_sum            'C23 H23 Cl N2 O6'
_chemical_formula_weight         458.88
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-26
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.430(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3699(3)
_cell_length_b                   17.3809(5)
_cell_length_c                   12.7667(3)
_cell_measurement_reflns_used    13189
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      29.5150
_cell_measurement_theta_min      1.9840
_cell_volume                     2286.57(11)
_computing_cell_refinement
;
CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 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, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      294.15
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.814
_diffrn_detector_type            'Rigaku Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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   -105.00  75.00   0.50    5.00    --  -15.00  45.00   0.00  360
  2  \w   -105.00  75.00   0.50    5.00    --  -15.00  45.00  90.00  360
  3  \w   -105.00  75.00   0.50    5.00    --  -15.00  45.00 180.00  360
;
_diffrn_measurement_device       'AFC10: Fixed Chi 2 circle'
_diffrn_measurement_device_type  'Rigaku Xtalab P200'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0022287000
_diffrn_orient_matrix_UB_12      0.0171422000
_diffrn_orient_matrix_UB_13      -0.0501874000
_diffrn_orient_matrix_UB_21      -0.0532192000
_diffrn_orient_matrix_UB_22      0.0238777000
_diffrn_orient_matrix_UB_23      0.0087014000
_diffrn_orient_matrix_UB_31      0.0435869000
_diffrn_orient_matrix_UB_32      0.0283006000
_diffrn_orient_matrix_UB_33      0.0230849000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29712
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.700
_diffrn_reflns_theta_min         1.987
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0770P)^2^+0.4840P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.1643
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4572
_reflns_number_total             5895
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01962_si_002.cif
_cod_data_source_block           m20160527d
_cod_depositor_comments
'Adding full bibliography for 4032950--4032951.cif.'
_cod_original_cell_volume        2286.59(10)
_cod_database_code               4032950
_chemical_oxdiff_formula         C20H20N2O6Cl
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.944
_reflns_odcompleteness_completeness 88.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.94
_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.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C23(H23A,H23B,
 H23C)
;
_shelx_res_checksum              77162
_shelx_hkl_checksum              69919
_shelx_shelxl_version_number     2014/8
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.112
_oxdiff_exptl_absorpt_empirical_full_min 0.539