Divergent Synthesis of Methylene Lactone- and Methylene Lactam-Based Spiro Compounds: Utility of Amido-Functionalized γ-Hydroxylactam as a Precursor for Cytotoxic <i>N</i>,<i>O</i>- and <i>N</i>,<i>N</i>-Spiro Compounds.
Sengoku, Tetsuya; Shirai, Anna; Takano, Ayaka; Inuzuka, Toshiyasu; Sakamoto, Masami; Takahashi, Masaki; Yoda, Hidemi; The Journal of organic chemistry 84 (2019) 12532–12541; doi:10.1021/acs.joc.9b02038

data_4033954
_publ_section_title
;
 Divergent Synthesis of Methylene Lactone- and Methylene Lactam-Based
 Spiro Compounds: Utility of Amido-Functionalized \g-Hydroxylactam as a
 Precursor for Cytotoxic <i>N</i>,<i>O</i>- and <i>N</i>,<i>N</i>-Spiro
 Compounds.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12532
_journal_page_last               12541
_journal_paper_doi               10.1021/acs.joc.9b02038
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C19 H22 B N O3'
_chemical_formula_weight         323.18
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 113.778(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.756(4)
_cell_length_b                   17.147(5)
_cell_length_c                   9.519(3)
_cell_measurement_reflns_used    6191
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.2439
_cell_measurement_theta_min      2.3756
_cell_volume                     1756.0(10)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19583
_diffrn_reflns_theta_full        27.461
_diffrn_reflns_theta_max         27.461
_diffrn_reflns_theta_min         2.235
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.421
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         3967
_refine_ls_number_restraints     180
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0667
_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^)+(0.1221P)^2^+0.6660P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1850
_refine_ls_wR_factor_ref         0.2005
_reflns_number_gt                3137
_reflns_number_total             3967
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02038_si_005.cif
_cod_data_source_block           I
_cod_database_code               4033954