Preparation of spiro[indole-3,5′-isoxazoles] via Grignard conjugate addition/spirocyclization sequence
Aksenov, Alexander V.; Aksenov, Dmitrii A.; Aksenov, Nicolai A.; Skomorokhov, Anton A.; Aleksandrova, Elena V.; Rubin, Michael; RSC Advances 11 (2021) 1783–1793; doi:10.1039/D0RA10219A

data_7242037
_publ_section_title
;
 Preparation of spiro[indole-3,5&#x2032;-isoxazoles] via Grignard
 conjugate addition/spirocyclization sequence
;
_journal_issue                   3
_journal_name_full               'RSC Advances'
_journal_page_first              1783
_journal_page_last               1793
_journal_paper_doi               10.1039/D0RA10219A
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C22 H14 F2 N2 O'
_chemical_formula_sum            'C22 H14 F2 N2 O'
_chemical_formula_weight         360.35
_chemical_name_systematic
4'-(3,5-difluorophenyl)-2-phenyl-4'H-spiro[indole-3,5'-isoxazole]
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-08-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-22 deposited with the CCDC.	2020-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.3576(18)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.4243(4)
_cell_length_b                   15.3838(2)
_cell_length_c                   11.4158(2)
_cell_measurement_reflns_used    15198
_cell_measurement_temperature    104(6)
_cell_measurement_theta_max      75.8320
_cell_measurement_theta_min      3.5680
_cell_volume                     3489.85(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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      104(6)
_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 0.996
_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    -66.00  33.00   1.00    1.75    --  -41.35  38.00 150.00   99
  2  \w   -121.00   0.00   1.00    1.75    --  -41.35 -19.00 -30.00  121
  3  \w      7.00  34.00   1.00    1.75    --   41.35  83.00 -16.72   27
  4  \w      7.00  34.00   1.00    1.75    --   41.35  83.00  58.07   27
  5  \w    -31.00  69.00   1.00    1.75    --   41.35 -57.00-180.00  100
  6  \w      7.00  33.00   1.00    1.75    --   41.35  84.00-110.50   26
  7  \w     30.00 106.00   1.00    7.01    --  112.00 -95.00-120.00   76
  8  \w     46.00 178.00   1.00    7.01    --  112.00  13.00 158.67  132
  9  \w     40.00 141.00   1.00    7.01    --  112.00 -61.00 120.00  101
 10  \w     30.00 106.00   1.00    7.01    --  112.00 -95.00  30.00   76
 11  \w     40.00 141.00   1.00    7.01    --  112.00 -61.00-120.00  101
 12  \w     30.00 106.00   1.00    7.01    --  112.00 -95.00 150.00   76
 13  \w     39.00 138.00   1.00    7.01    --  112.00 -45.00 120.00   99
 14  \w     30.00  96.00   1.00    7.01    --  112.00 -95.00 -90.00   66
 15  \w    116.00 141.00   1.00    7.01    --  112.00  30.00  30.00   25
 16  \w     80.00 107.00   1.00    7.01    --  112.00 -22.00 -69.16   27
 17  \w     89.00 128.00   1.00    7.01    --  112.00  45.00  90.00   39
 18  \w     41.00  99.00   1.00    7.01    --  112.00-111.00 150.00   58
 19  \w     37.00  78.00   1.00    7.01    --  112.00-111.00   0.00   41
 20  \w     77.00 106.00   1.00    7.01    --  112.00 -45.00-120.00   29
 21  \w    121.00 148.00   1.00    7.01    --  112.00  45.00  60.00   27
 22  \w     76.00 106.00   1.00    7.01    --  112.00 178.00  30.00   30
 23  \w     54.00  82.00   1.00    7.01    --  112.00 -84.00 173.91   28
 24  \w    103.00 130.00   1.00    7.01    --  112.00 -84.00 173.91   27
 25  \w    133.00 158.00   1.00    7.01    --  112.00  77.00  90.00   25
 26  \w    145.00 178.00   1.00    7.01    --  112.00  77.00 120.00   33
 27  \w     38.00  66.00   1.00    7.01    --  112.00 -95.00 -30.00   28
 28  \w    118.00 178.00   1.00    7.01    --  112.00 111.00  60.00   60
 29  \w     38.00 103.00   1.00    7.01    --  112.00 -30.00 150.00   65
 30  \w    128.00 160.00   1.00    7.01    --  112.00  31.00-110.00   32
 31  \w     54.00 108.00   1.00    7.01    --  112.00-111.00  30.00   54
 32  \w     37.00  74.00   1.00    7.01    --  112.00 -30.00-150.00   37
 33  \w    115.00 140.00   1.00    7.01    --  112.00 -30.00-150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0114263000
_diffrn_orient_matrix_UB_12      0.0395538000
_diffrn_orient_matrix_UB_13      0.1269988000
_diffrn_orient_matrix_UB_21      0.0766495000
_diffrn_orient_matrix_UB_22      -0.0072700000
_diffrn_orient_matrix_UB_23      0.0141993000
_diffrn_orient_matrix_UB_31      0.0011662000
_diffrn_orient_matrix_UB_32      0.0917594000
_diffrn_orient_matrix_UB_33      -0.0538115000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            37744
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.611
_diffrn_reflns_theta_min         2.223
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.801
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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 light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_preparation
'Prepared by Michael additon of Gringard reagent to niitroalkene'
_exptl_crystal_recrystallization_method
'Crystal was prepared by evaporation of saturated solution'
_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.266
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     542
_refine_ls_number_reflns         7322
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0624P)^2^+0.6232P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1230
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6246
_reflns_number_total             7322
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra10219a2.cif
_cod_data_source_block           anna_ros534_11
_cod_original_cell_volume        3489.86(10)
_cod_database_code               7242037
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C22H14F2N2O
_reflns_odcompleteness_completeness 98.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Sof(C50)=Sof(H50)=Sof(C49)=Sof(H49)=Sof(C48)=Sof(H48)=Sof(C47)=Sof(H47)=
 Sof(C46)=Sof(H46)=Sof(C45)=1-FVAR(1)
 Sof(C39)=Sof(C40)=Sof(H40)=Sof(C41)=Sof(H41)=Sof(C42)=Sof(H42)=Sof(C43)=
 Sof(H43)=Sof(C44)=Sof(H44)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C9(H9), C31(H31)
3.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C16(H16), C34(H34),
 C38(H38), C12(H12), C10(H10), C32(H32), C36(H36), C14(H14), C27(H27), C40(H40),
  C41(H41), C42(H42), C43(H43), C44(H44), C30(H30), C8(H8), C28(H28), C29(H29),
 C5(H5), C7(H7), C6(H6), C50(H50), C49(H49), C48(H48), C47(H47), C46(H46)
;
_shelx_res_checksum              76033
_olex2_date_sample_data_collection 2020-07-22
_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 1.435
_oxdiff_exptl_absorpt_empirical_full_min 0.727