1,3-Dipolar Cycloaddition of Isatin-Derived Azomethine Ylides with 2 H-Azirines: Stereoselective Synthesis of 1,3-Diazaspiro[bicyclo[3.1.0]hexane]oxindoles.
Angyal, Anikó; Demjén, András; Harmat, Veronika; Wölfling, János; Puskás, László G; Kanizsai, Iván; The Journal of organic chemistry 84 (2019) 4273–4281; doi:10.1021/acs.joc.9b00242

data_4034289
_publ_contact_author             'Veronika Harmat'
_publ_section_title
;
 1,3-Dipolar Cycloaddition of Isatin-Derived Azomethine Ylides with 2
 H-Azirines: Stereoselective Synthesis of
 1,3-Diazaspiro[bicyclo[3.1.0]hexane]oxindoles.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4273
_journal_page_last               4281
_journal_paper_doi               10.1021/acs.joc.9b00242
_journal_volume                  84
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H21 N3 O3'
_chemical_formula_sum            'C21 H21 N3 O3'
_chemical_formula_weight         363.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-01-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.75667(10)
_cell_length_b                   13.67134(11)
_cell_length_c                   14.32506(12)
_cell_measurement_reflns_used    17886
_cell_measurement_temperature    299.18(10)
_cell_measurement_theta_max      74.6410
_cell_measurement_theta_min      3.0290
_cell_volume                     1910.77(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      299.18(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0098
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21399
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.450
_diffrn_reflns_theta_min         6.476
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.180
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
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            colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.821
_exptl_crystal_size_mid          0.573
_exptl_crystal_size_min          0.306
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3820
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0311
_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^)+(0.0492P)^2^+0.2068P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0833
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                3763
_reflns_number_total             3820
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00242_si_001.cif
_cod_data_source_block           sio201
_cod_database_code               4034289
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8(2)
 0.2(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C2(H2), N1(H1), C6(H6), C19(H19), C15(H15), C1(H1A), C16(H16),
 C18(H18), C17(H17)
3.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              81910
_shelx_hkl_checksum              40140
_olex2_submission_special_instructions 'No special instructions were received'