Synthesis of (+)-Pancratistatins via Catalytic Desymmetrization of Benzene.
Hernandez, Lucas W.; Pospech, Jola; Klöckner, Ulrich; Bingham, Tanner W.; Sarlah, David; Journal of the American Chemical Society 139 (2017) 15656–15659; doi:10.1021/jacs.7b10351

data_4131759
_publ_section_title
;
 Synthesis of (+)-Pancratistatins via Catalytic Desymmetrization of
 Benzene.
;
_journal_issue                   44
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15656
_journal_page_last               15659
_journal_paper_doi               10.1021/jacs.7b10351
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C16 H15 N3 O4'
_chemical_formula_sum            'C16 H15 N3 O4'
_chemical_formula_weight         313.31
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-21
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                72.6000(18)
_cell_angle_beta                 72.9177(19)
_cell_angle_gamma                86.0255(18)
_cell_formula_units_Z            2
_cell_length_a                   7.2463(5)
_cell_length_b                   9.5480(7)
_cell_length_c                   11.2269(8)
_cell_measurement_reflns_used    3404
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.326
_cell_measurement_theta_min      2.942
_cell_volume                     708.37(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker APEXII CCD area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'Bruker Kappa/ApexII CCD'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10076
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.040
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0425 before and 0.0360 after correction. The Ratio of minimum to maximum transmission is 0.9155. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_description       prism
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.252
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0073(19)
_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   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0304
_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^)+(0.0325P)^2^+0.2995P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0770
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2360
_reflns_number_total             2582
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b10351_si_002.cif
_cod_data_source_block           cm60y_0m
_cod_database_code               4131759
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.972
_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,H,H) groups, All N(H) groups
2. Others
 Sof(H9D)=Sof(H9E)=Sof(H9F)=1-FVAR(1)
 Sof(H9A)=Sof(H9B)=Sof(H9C)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2A)
3.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C15(H15), C16(H16)
3.d Disordered Me refined as rotating group:
 C9(H9A,H9B,H9C,H9D,H9E,H9F)
;
_olex2_submission_special_instructions 'No special instructions were received'