Biomimetic kinetic resolution: highly enantio- and diastereoselective transfer hydrogenation of aglain ketones to access flavagline natural products.
Stone, Steven D.; Lajkiewicz, Neil J.; Whitesell, Luke; Hilmy, Ahmed; Porco, Jr, John A; Journal of the American Chemical Society 137 (2015) 525–530; doi:10.1021/ja511728b

data_4123192
_publ_section_title
;
 Biomimetic kinetic resolution: highly enantio- and diastereoselective
 transfer hydrogenation of aglain ketones to access flavagline natural
 products.
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              525
_journal_page_last               530
_journal_paper_doi               10.1021/ja511728b
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety         'C31 H29 N O7'
_chemical_formula_sum            'C31 H29 N O7'
_chemical_formula_weight         527.55
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-09-30
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2014-09-30 # Formatted by publCIF

;
_cell_angle_alpha                72.571(3)
_cell_angle_beta                 74.463(2)
_cell_angle_gamma                62.139(2)
_cell_formula_units_Z            8
_cell_length_a                   16.4623(7)
_cell_length_b                   16.6870(7)
_cell_length_c                   21.9358(10)
_cell_measurement_temperature    100(2)
_cell_volume                     5024.1(4)
_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    'XT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            17631
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        66.749
_diffrn_reflns_theta_max         66.749
_diffrn_reflns_theta_min         3.060
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       prism
_exptl_crystal_F_000             2224
_exptl_crystal_size_max          0.167
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1432
_refine_ls_number_reflns         17631
_refine_ls_number_restraints     1392
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0552
_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^)+(0.0670P)^2^+2.8860P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1484
_refine_ls_wR_factor_ref         0.1537
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15808
_reflns_number_total             17631
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {efb2ef41-edfe-4d22-a516-8aadd98b58e2}
_cod_data_source_file            ja511728b_si_002.cif
_cod_data_source_block           lajkiewicz7b_0m
_cod_depositor_comments          'Adding full bibliography for 4123192.cif.'
_cod_database_code               4123192
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(H20C)=Sof(H20D)=Sof(H18C)=Sof(H18D)=Sof(C19E)=Sof(H19C)=Sof(H19D)=1-FVAR(1)
 Sof(H20A)=Sof(H20B)=Sof(H18A)=Sof(H18B)=Sof(C19D)=Sof(H19A)=Sof(H19B)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C9B(H9B), C21B(H21B), C21A(H21A), C9A(H9A), C9C(H9C), C21C(H21C), C21D(H21D),
 C9D(H9D)
4.b Secondary CH2 refined with riding coordinates:
 C19B(H19E,H19F), C18B(H18E,H18F), C20B(H20E,H20F), C20C(H20G,H20H), C20A(H20I,
 H20J), C18C(H18G,H18H), C19A(H19I,H19J), C19C(H19G,H19H), C18A(H18I,H18J),
 C20D(H20A,H20B), C20D(H20C,H20D), C18D(H18A,H18B), C18D(H18C,H18D), C19D(H19A,
 H19B), C19E(H19C,H19D)
4.c Aromatic/amide H refined with riding coordinates:
 C29B(H29B), C15B(H15B), C26B(H26B), C15A(H15A), C7A(H7A), C26C(H26C),
 C14B(H14B), C29C(H29C), C6A(H6A), C4A(H4A), C6C(H6C), C11B(H11B), C3A(H3A),
 C6D(H6D), C4B(H4B), C3B(H3B), C7C(H7C), C11A(H11A), C29A(H29A), C14C(H14C),
 C3C(H3C), C7D(H7D), C12B(H12B), C29D(H29D), C12C(H12C), C11C(H11C), C15C(H15C),
  C13A(H13A), C14A(H14A), C26A(H26A), C12A(H12A), C15D(H15D), C6B(H6B),
 C4C(H4C), C7B(H7B), C13B(H13B), C12D(H12D), C13C(H13C), C13D(H13D), C14D(H14D),
  C4D(H4D), C11D(H11D), C26D(H26D), C3D(H3D)
4.d Idealised Me refined as rotating group:
 C28B(H28D,H28E,H28F), C28C(H28G,H28H,H28I), C31B(H31D,H31E,H31F), C31A(H31J,
 H31K,H31L), C31C(H31G,H31H,H31I), C31D(H31A,H31B,H31C), C1C(H1CA,H1CB,H1CC),
 C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC), C28D(H28A,H28B,H28C), C28A(H28J,H28K,
 H28L), C1D(H1DA,H1DB,H1DC)
4.e Idealised tetrahedral OH refined as rotating group:
 O5B(H5B), O5A(H5A), O5C(H5C), O00D(H00D)
;
_shelx_res_checksum              66183
_shelx_hkl_checksum              52385
_olex2_submission_special_instructions 'No special instructions were received'