Evolution of a Strategy for the Enantioselective Total Synthesis of (+)-Psiguadial B.
Chapman, Lauren M.; Beck, Jordan C.; Lacker, Caitlin R.; Wu, Linglin; Reisman, Sarah E.; The Journal of organic chemistry 83 (2018) 6066–6085; doi:10.1021/acs.joc.8b00728

data_4035775
_publ_section_title
;
 Evolution of a Strategy for the Enantioselective Total Synthesis of
 (+)-Psiguadial B.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6066
_journal_page_last               6085
_journal_paper_doi               10.1021/acs.joc.8b00728
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H28 N2 O2'
_chemical_formula_sum            'C23 H28 N2 O2'
_chemical_formula_weight         364.47
_chemical_name_common            LMC-04-038
_chemical_name_systematic        LMC-04-038
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-05-02
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5496(4)
_cell_length_b                   10.8428(6)
_cell_length_c                   27.6666(15)
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    100
_cell_measurement_theta_max      79.33
_cell_measurement_theta_min      3.19
_cell_volume                     1964.77(19)
_computing_cell_refinement       'SAINT v8.34A (Bruker-AXS, 2007)'
_computing_data_collection       'APEX2 v2014.11-0 (Bruker-AXS, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker-AXS, 2007)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (She ldrick, 2013)'
_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 0.992
_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  0.0414
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            24424
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.392
_diffrn_reflns_theta_min         3.195
_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    0.619
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_correction_T_min  0.7017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2014/5 (Sheldrick, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1579 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(9)
_refine_ls_extinction_coef       0.0031(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         4179
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0272
_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^)+(0.0314P)^2^+0.3640P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0655
_refine_ls_wR_factor_ref         0.0672
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                3953
_reflns_number_total             4179
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00728_si_002.cif
_cod_data_source_block           p16026_a
_cod_database_code               4035775
_shelx_estimated_absorpt_t_max   0.941
_shelx_estimated_absorpt_t_min   0.861
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H11A,H11B,H1} of C11, All C(H,H) groups
 At 1.5 times of:
  {H14A,H14B,H14C} of C14, {H5A,H5B,H5C} of C5, {H4A,H4B,H4C} of C4
2.a Ternary CH refined with riding coordinates:
 C7(H7), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C6(H6A,H6B), C13(H13A,H13B), C12(H12A,H12B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C16(H16), C22(H22), C21(H21), C20(H20)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C4(H4A,H4B,H4C), C5(H5A,H5B,H5C)
;
_shelx_res_checksum              84014
_shelx_hkl_checksum              17979
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'