Asymmetric Total Synthesis of (-)-Spirochensilide A.
Liang, Xin-Ting; Chen, Jia-Hua; Yang, Zhen; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c02522

data_4134754
_publ_section_title
;
 Asymmetric Total Synthesis of (-)-Spirochensilide A.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c02522
_journal_year                    2020
_chemical_formula_moiety         'C30 H42 O5'
_chemical_formula_sum            'C30 H42 O5'
_chemical_formula_weight         482.63
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.4159(7)
_cell_length_b                   12.8940(5)
_cell_length_c                   28.4623(12)
_cell_measurement_reflns_used    6789
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      22.5650
_cell_measurement_theta_min      2.2280
_cell_volume                     5290.5(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.29a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     22.00  48.00   0.50   15.00    --  -15.70  37.00-120.00   52
  2  \w    -79.00  14.00   0.50   15.00    --  -15.70  37.00-120.00  186
  3  \w    -49.00 -24.00   0.50   15.00    --  -15.70  77.00 120.00   50
  4  \w    -40.00  -9.00   0.50   15.00    --  -15.70  77.00   0.00   62
  5  \w    -56.00 -20.00   0.50   15.00    --  -15.70  77.00-150.00   72
  6  \w    -56.00 -13.00   0.50   15.00    --  -15.70  77.00 -30.00   86
  7  \w    -34.00  12.00   0.50   15.00    --  -15.70  57.00 -90.00   92
  8  \w     29.00  74.00   0.50   15.00    --  -15.70  57.00 -90.00   90
  9  \w    -31.00  20.00   0.50   15.00    --   15.80 -82.00  30.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0123641000
_diffrn_orient_matrix_UB_12      0.0047115000
_diffrn_orient_matrix_UB_13      -0.0240210000
_diffrn_orient_matrix_UB_21      0.0403797000
_diffrn_orient_matrix_UB_22      -0.0300960000
_diffrn_orient_matrix_UB_23      0.0041182000
_diffrn_orient_matrix_UB_31      -0.0252492000
_diffrn_orient_matrix_UB_32      -0.0458098000
_diffrn_orient_matrix_UB_33      -0.0051865000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            43469
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.580
_diffrn_reflns_theta_min         2.237
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_description       plate
_exptl_crystal_F_000             2096
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         6906
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1225
_refine_ls_R_factor_gt           0.0656
_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^)+(0.0567P)^2^+1.9466P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1282
_refine_ls_wR_factor_ref         0.1480
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4241
_reflns_number_total             6906
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02522_si_008.cif
_cod_data_source_block           exp_3214
_cod_database_code               4134754
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.997
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009), C00G(H00G), C00K(H00K), C00U(H00Z)
2.b Secondary CH2 refined with riding coordinates:
 C00E(H00A,H00B), C00J(H00C,H00D), C00L(H00E,H00F), C00M(H00H,H00J), C00O(H00L,
 H00M), C00S(H00U,H00V), C00V(H00,H)
2.c Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C00P(H00P)
2.d Idealised Me refined as rotating group:
 C00Q(H00N,H00O,H00Q), C00R(H00R,H00S,H00T), C00W(H0AA,HA,HB), C00Y(H2AA,HC,
 HD), C00Z(H3AA,HE,HF)
;
_shelx_res_checksum              12519
_shelx_hkl_checksum              98216
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.314
_oxdiff_exptl_absorpt_empirical_full_min 0.828