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_4034290
_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_formula_moiety         'C18 H21 N3 O3, 0.5(C4 H8 O)'
_chemical_formula_sum            'C20 H25 N3 O3.5'
_chemical_formula_weight         363.43
_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
_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                 99.8206(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.65608(8)
_cell_length_b                   16.50980(14)
_cell_length_c                   10.94821(9)
_cell_measurement_reflns_used    30294
_cell_measurement_temperature    298.01(19)
_cell_measurement_theta_max      75.0270
_cell_measurement_theta_min      2.7250
_cell_volume                     1897.89(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)'
_diffrn_ambient_temperature      298.01(19)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.971
_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  0.0241
_diffrn_reflns_av_unetI/netI     0.0083
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            41156
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.480
_diffrn_reflns_theta_min         4.897
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65034
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourles
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       chunk
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.509
_exptl_crystal_size_min          0.349
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3824
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0625P)^2^+0.3886P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1205
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3568
_reflns_number_total             3824
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00242_si_002.cif
_cod_data_source_block           sio101
_cod_original_formula_sum        'C20 H25 N3 O3.50'
_cod_database_code               4034290
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. 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
2. Restrained distances
 O30-C32 \\sim O30-C33
 with sigma of 0.04
 O30-C31 \\sim O30-C34
 with sigma of 0.02
 C31-C32 \\sim C33-C34 \\sim C32-C33
 with sigma of 0.04
3. Others
 Fixed Sof: O30(0.5) C31(0.5) H31A(0.5) H31B(0.5) C32(0.5) H32A(0.5) H32B(0.5)
 C33(0.5) H33A(0.5) H33B(0.5) C34(0.5) H34A(0.5) H34B(0.5)
4.a Ternary CH refined with riding coordinates:
 C11(H11), C10(H10)
4.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C17(H17A,H17B), C16(H16A,H16B), C15(H15A,H15B), C31(H31A,
 H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C1(H1A), C3(H3), C2(H2)
4.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              78385
_shelx_hkl_checksum              52919
_olex2_submission_special_instructions 'No special instructions were received'