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_4033953
_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_absolute_configuration 'CHOOSE rm ad rmad syn or unk'
_chemical_formula_moiety         'C18 H14 N2 O2'
_chemical_formula_sum            'C18 H14 N2 O2'
_chemical_formula_weight         290.32
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   9.0692(9)
_cell_length_b                   9.9319(8)
_cell_length_c                   15.9479(14)
_cell_measurement_reflns_used    3140
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.00
_cell_volume                     1436.5(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b30'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b30 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b30'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL Version 2018/1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2014 (Burla, et al., 2014)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17129
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.416
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608.00
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.21
_refine_ls_abs_structure_details
;
 Flack x determined using 1058 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0676P)^2^+0.0600P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1184
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2839
_reflns_number_total             3269
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo9b02038_si_006.cif
_cod_data_source_block           sengoku-LT-180425a
_cod_database_code               4033953
_shelx_res_checksum              69166
_shelx_hkl_checksum              71802