Catalytic Enantioselective Synthesis of Carbocyclic and Heterocyclic Spiranes via a Decarboxylative Aldol Cyclization
Inanaga, Kazato; Wollenburg, Marco; Bachman, Shoshana; Hafeman, Nicholas; Stoltz, Brian M.; Chemical Science  (2020) –; doi:10.1039/D0SC02366C

data_1558398
_publ_section_title
;
 Catalytic Enantioselective Synthesis of Carbocyclic and Heterocyclic
 Spiranes via a Decarboxylative Aldol Cyclization
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02366C
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H19 N O3'
_chemical_formula_sum            'C16 H19 N O3'
_chemical_formula_weight         273.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2017-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227),
 SHELXL-2014,
 and manual edit
;
_audit_update_record
;
2020-04-26 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.925(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.0356(4)
_cell_length_b                   10.8751(9)
_cell_length_c                   10.5262(7)
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    100
_cell_measurement_theta_max      78.21
_cell_measurement_theta_min      4.24
_cell_volume                     684.32(9)
_computing_cell_refinement       'SAINT V8.37A (Bruker-AXS, 2007)'
_computing_data_collection
'APEX3 BIS V6.2.1/2016-03-01 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT V8.37A (Bruker-AXS, 2007)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT-2014/4 (Sheldrick, 2012)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Area Detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            34337
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         78.780
_diffrn_reflns_theta_min         4.240
_diffrn_source                   'I\mS HB micro-focus sealed tube'
_diffrn_source_current           1
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_source_voltage           50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.8741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0930 before and 0.0689 after correction.
The Ratio of minimum to maximum transmission is 0.8876.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1311 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         2909
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0287
_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^)+(0.0452P)^2^+0.1077P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0736
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                2867
_reflns_number_total             2909
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc02366c2.cif
_cod_data_source_block           p16478
_cod_original_cell_volume        684.32(8)
_cod_database_code               1558398
_shelx_estimated_absorpt_t_max   0.910
_shelx_estimated_absorpt_t_min   0.848
_refine_ls_abs_structure_hooft   0.15(4)
_olex2_refinement_description
;
;
_shelx_res_checksum              31644
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'