Stereo- and Regioselective 1,3-Dipolar Cycloaddition of the Stable Ninhydrin-Derived Azomethine Ylide to Cyclopropenes: Trapping of Unstable Cyclopropene Dipolarophiles.
Filatov, Alexander S.; Wang, Siqi; Khoroshilova, Olesya V.; Lozovskiy, Stanislav V.; Larina, Anna G.; Boitsov, Vitali M.; Stepakov, Alexander V.; The Journal of organic chemistry 84 (2019) 7017–7036; doi:10.1021/acs.joc.9b00753

data_4034592
_publ_section_title
;
 Stereo- and Regioselective 1,3-Dipolar Cycloaddition of the Stable
 Ninhydrin-Derived Azomethine Ylide to Cyclopropenes: Trapping of Unstable
 Cyclopropene Dipolarophiles.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7017
_journal_page_last               7036
_journal_paper_doi               10.1021/acs.joc.9b00753
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C17 H17 N O2'
_chemical_formula_sum            'C17 H17 N O2'
_chemical_formula_weight         267.31
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-12-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                88.483(3)
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_cell_angle_gamma                89.643(3)
_cell_formula_units_Z            4
_cell_length_a                   9.7016(4)
_cell_length_b                   11.6604(4)
_cell_length_c                   11.7270(5)
_cell_measurement_reflns_used    7877
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.7740
_cell_measurement_theta_min      3.1440
_cell_volume                     1324.17(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -44.00   35.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178  -57.0000   90.0000 79

  2 omega   46.00   72.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178 -178.0000   60.0000 26

  3 omega   21.00   65.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178  -99.0000 -120.0000 44

  4 omega  -21.00   63.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178  -99.0000  -30.0000 84

  5 omega   39.00   65.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178  -99.0000  120.0000 26

  6 omega    2.00   46.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178   77.0000   60.0000 44

  7 omega  -21.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178   19.0000  -90.0000 117

  8 omega  -91.00   -1.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -57.0000   90.0000 90

  9 omega   56.00   98.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178  178.0000  150.0000 42

 10 omega   -7.00   73.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178   77.0000 -120.0000 80

 11 omega  -45.00   62.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178  -19.0000  150.0000 107

 12 omega    6.00   92.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178   69.0000  -22.0000 86
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0145956000
_diffrn_orient_matrix_UB_12      0.0596530000
_diffrn_orient_matrix_UB_13      0.0011196000
_diffrn_orient_matrix_UB_21      0.0472791000
_diffrn_orient_matrix_UB_22      0.0093696000
_diffrn_orient_matrix_UB_23      -0.0475724000
_diffrn_orient_matrix_UB_31      -0.0539718000
_diffrn_orient_matrix_UB_32      -0.0075278000
_diffrn_orient_matrix_UB_33      -0.0375150000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21722
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.728
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.341
_exptl_crystal_description       prism
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.716
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         6082
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0721
_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^)+(0.0908P)^2^+2.3485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1929
_refine_ls_wR_factor_ref         0.1984
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_reflns_number_gt                5325
_reflns_number_total             6082
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00753_si_003.cif
_cod_data_source_block           8296-11045_step-73
_cod_original_cell_volume        1324.16(9)
_cod_database_code               4034592
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C17 H17 N O2'
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.961
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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:
 C6BB(H6BB), C6AB(H6AB), C6A(H6A), C1AA(H1AA)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C4B(H4BA,H4BB), C1B(H1BA,H1BB), C6B(H6BA,H6BC), C5(H5A,H5B),
 C1(H1A,H1B), C5B(H5BA,H5BB), C6(H6B,H6C)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C12B(H12B), C10(H10), C9B(H9B), C11B(H11B), C10B(H10B),
 C11(H11)
2.d Idealised Me refined as rotating group:
 C7B(H7BA,H7BB,H7BC), C7(H7A,H7B,H7C)
;
_shelx_res_checksum              75504
_shelx_hkl_checksum              18740
_olex2_submission_special_instructions 'No special instructions were received'