Synthesis of Spiro[indole-3,5'-isoxazoles] with Anticancer Activity via a Formal [4 + 1]-Spirocyclization of Nitroalkenes to Indoles.
Aksenov, Alexander V.; Aksenov, Dmitrii A.; Arutiunov, Nikolai A.; Aksenov, Nicolai A.; Aleksandrova, Elena V.; Zhao, Zhenze; Du, Liqin; Kornienko, Alexander; Rubin, Michael; The Journal of organic chemistry 84 (2019) 7123–7137; doi:10.1021/acs.joc.9b00808

data_4034626
_publ_section_title
;
 Synthesis of Spiro[indole-3,5'-isoxazoles] with Anticancer Activity via a
 Formal [4 + 1]-Spirocyclization of Nitroalkenes to Indoles.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7123
_journal_page_last               7137
_journal_paper_doi               10.1021/acs.joc.9b00808
_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
_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                 90.0450(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1571(2)
_cell_length_b                   12.4540(2)
_cell_length_c                   11.9000(2)
_cell_measurement_reflns_used    11640
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      75.6950
_cell_measurement_theta_min      5.1000
_cell_volume                     1653.51(5)
_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      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_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    1.00    --  -41.72  99.00 -96.00  103
  2  \w      1.00  83.00   1.00    1.00    --   41.72 -99.00 157.00   82
  3  \w    101.00 141.00   1.00    4.00    --  112.00  99.00 -96.00   40
  4  \w     35.00 103.00   1.00    4.00    --  112.00 -99.00 157.00   68
  5  \w   -112.00 -22.00   1.00    1.00    --  -41.72 -57.00 150.00   90
  6  \w    -20.00  21.00   1.00    1.00    --  -41.72  57.00  60.00   41
  7  \w    -67.00 -27.00   1.00    1.00    --  -41.72  57.00  60.00   40
  8  \w     58.00 106.00   1.00    4.00    --  112.00 178.00  60.00   48
  9  \w     38.00 100.00   1.00    4.00    --  112.00-111.00-120.00   62
 10  \w     43.00  90.00   1.00    4.00    --  112.00 -30.00 -60.00   47
 11  \w     42.00  68.00   1.00    4.00    --  112.00 -30.00-150.00   26
 12  \w     39.00  98.00   1.00    4.00    --  112.00 -45.00  30.00   59
 13  \w     52.00 108.00   1.00    4.00    --  112.00 -95.00  90.00   56
 14  \w     56.00  97.00   1.00    4.00    --  112.00 -45.00-180.00   41
 15  \w    123.00 150.00   1.00    4.00    --  112.00 178.00  60.00   27
 16  \w     52.00  82.00   1.00    4.00    --  112.00 -30.00   0.00   30
 17  \w    101.00 175.00   1.00    4.00    --  112.00 111.00  60.00   74
 18  \w     70.00  96.00   1.00    4.00    --  112.00 -45.00 -60.00   26
 19  \w     52.00  84.00   1.00    4.00    --  112.00 -95.00-180.00   32
 20  \w     44.00 133.00   1.00    4.00    --  112.00 -61.00 -60.00   89
 21  \w     50.00  76.00   1.00    4.00    --  112.00-111.00  60.00   26
 22  \w     85.00 113.00   1.00    4.00    --  112.00-111.00  60.00   28
 23  \w    139.00 167.00   1.00    4.00    --  112.00 111.00-120.00   28
 24  \w     82.00 108.00   1.00    4.00    --  112.00 -95.00-180.00   26
 25  \w     99.00 125.00   1.00    4.00    --  112.00  30.00 120.00   26
 26  \w   -114.00 -14.00   1.00    1.00    --  -41.85 -57.00  30.00  100
 27  \w    -50.00  32.00   1.00    1.00    --  -41.85  38.00-150.00   82
 28  \w   -118.00  -9.00   1.00    1.00    --  -41.85 -77.00-150.00  109
 29  \w   -118.00  -9.00   1.00    1.00    --  -41.85 -77.00  90.00  109
 30  \w   -118.00  -9.00   1.00    1.00    --  -41.85 -77.00 -30.00  109
 31  \w    -50.00  32.00   1.00    1.00    --  -41.85  38.00-120.00   82
 32  \w   -114.00 -89.00   1.00    1.00    --  -41.85 -57.00 -90.00   25
;
_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      -0.0016136000
_diffrn_orient_matrix_UB_12      0.1005962000
_diffrn_orient_matrix_UB_13      -0.0752948000
_diffrn_orient_matrix_UB_21      -0.0746773000
_diffrn_orient_matrix_UB_22      0.0598163000
_diffrn_orient_matrix_UB_23      0.0889558000
_diffrn_orient_matrix_UB_31      0.1160678000
_diffrn_orient_matrix_UB_32      0.0401255000
_diffrn_orient_matrix_UB_33      0.0564264000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16080
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.841
_diffrn_reflns_theta_min         5.141
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.638
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.248
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (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    1.303
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.525
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.347
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0623P)^2^+0.5996P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1221
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3217
_reflns_number_total             3424
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00808_si_001.cif
_cod_data_source_block           anna_spoira_nu_11
_cod_database_code               4034626
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.809
_shelx_estimated_absorpt_t_min   0.731
_reflns_odcompleteness_completeness 99.97
_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:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C5(H5), C8(H8), C18(H18), C6(H6), C16(H16), C12(H12), C19(H19),
 C14(H14), C7(H7), C15(H15), C22(H22), C20(H20), C13(H13), C21(H21)
;
_shelx_res_checksum              19188
_shelx_hkl_checksum              64902
_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 3.835
_oxdiff_exptl_absorpt_empirical_full_min 0.558