Catalytic asymmetric total syntheses of myrtucommuacetalone, myrtucommuacetalone B, and callistrilones A, C, D and E.
Cheng, Min-Jing; Cao, Jia-Qing; Yang, Xin-Yi; Zhong, Li-Ping; Hu, Li-Jun; Lu, Xi; Hou, Bao-Long; Hu, Ya-Jian; Wang, Ying; You, Xue-Fu; Wang, Lei; Ye, Wen-Cai; Li, Chuang-Chuang; Chemical science 9 (2018) 1488–1495; doi:10.1039/c7sc04672c

data_1548238
_publ_section_title
;
 Catalytic asymmetric total syntheses of myrtucommuacetalone,
 myrtucommuacetalone B, and callistrilones A, C, D and E.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              1488
_journal_page_last               1495
_journal_paper_doi               10.1039/c7sc04672c
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C34 H44 O6'
_chemical_formula_sum            'C34 H44 O6'
_chemical_formula_weight         548.69
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-11-15
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_audit_update_record
;
2017-10-28 deposited with the CCDC.
2017-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.7200(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.5410(2)
_cell_length_b                   16.4653(3)
_cell_length_c                   32.9338(5)
_cell_measurement_reflns_used    22536
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.4930
_cell_measurement_theta_min      3.8360
_cell_volume                     6227.12(18)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            20250
_diffrn_reflns_point_group_measured_fraction_full 0.907
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.236
_diffrn_reflns_theta_min         3.806
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_description       block
_exptl_crystal_F_000             2368
_refine_diff_density_max         0.921
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 7501 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1511
_refine_ls_number_reflns         20250
_refine_ls_number_restraints     81
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0714
_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^)+(0.0827P)^2^+11.2360P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1899
_refine_ls_wR_factor_ref         0.1914
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    0.817
_reflns_Friedel_fraction_max     0.813
_reflns_number_gt                19521
_reflns_number_total             20250
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc04672c2.cif
_cod_data_source_block           3+2_1f_tw_sq
_cod_depositor_comments
'Adding full bibliography for 1548236--1548240.cif.'
_cod_database_code               1548238
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.887(4) 0.113(4)
2. 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) groups, All O(H) groups
3. Restrained distances
 C51-C45
 1.5 with sigma of 0.001
 C45-C50A
 1.5 with sigma of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(C50A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C30) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C29) \\sim Ueq: with sigma of
0.001 and sigma for terminal atoms of 0.002
Uanis(C50) \\sim Ueq, Uanis(C51A) \\sim Ueq, Uanis(C51) \\sim Ueq: with sigma
of 0.001 and sigma for terminal atoms of 0.002
5. Rigid body (RIGU) restrains
 C45, C50, C51, C51A, C50A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C25, C28, C29, C30
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C51A)=Sof(H51D)=Sof(H51E)=Sof(H51F)=Sof(C50A)=Sof(H50D)=Sof(H50E)=
 Sof(H50F)=1-FVAR(1)
 Sof(C50)=Sof(H50A)=Sof(H50B)=Sof(H50C)=Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(H51C)=
 FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C4(H4), C18(H18), C22(H22), C25(H25), C28(H28), C32(H32), C38(H38), C52(H52),
 C56(H56), C59(H59), C62(H62), C66(H66), C72(H72), C86(H86), C90(H90), C93(H93),
  C96(H96), C100(H100), C106(H106), C120(H120), C124(H124), C127(H127),
 C130(H130), C134(H134)
7.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C58(H58A,H58B), C92(H92A,H92B), C126(H12A,H12B)
7.c Aromatic/amide H refined with riding coordinates:
 C26(H26), C27(H27), C60(H60), C61(H61), C94(H94), C95(H95), C128(H128),
 C129(H129)
7.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C),
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C), C31(H31A,H31B,H31C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C39(H39A,
 H39B,H39C), C40(H40A,H40B,H40C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C),
 C50(H50A,H50B,H50C), C51(H51A,H51B,H51C), C63(H63A,H63B,H63C), C64(H64A,H64B,
 H64C), C65(H65A,H65B,H65C), C67(H67A,H67B,H67C), C68(H68A,H68B,H68C), C73(H73A,
 H73B,H73C), C74(H74A,H74B,H74C), C82(H82A,H82B,H82C), C83(H83A,H83B,H83C),
 C84(H84A,H84B,H84C), C85(H85A,H85B,H85C), C97(H97A,H97B,H97C), C98(H98A,H98B,
 H98C), C99(H99A,H99B,H99C), C101(H10A,H10B,H10C), C102(H10D,H10E,H10F),
 C107(H10G,H10H,H10I), C108(H10J,H10K,H10L), C116(H11A,H11B,H11C), C117(H11D,
 H11E,H11F), C118(H11G,H11H,H11I), C119(H11J,H11K,H11L), C131(H13A,H13B,H13C),
 C132(H13D,H13E,H13F), C133(H13G,H13H,H13I), C135(H13J,H13K,H13L), C136(H13M,
 H13N,H13O), C51A(H51D,H51E,H51F), C50A(H50D,H50E,H50F)
7.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O7(H7), O13(H13), O19(H19)
;
_shelx_res_checksum              79272
_shelx_fab_checksum              56811
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'