Asymmetric total syntheses of sarglamides A, C, D, E, and F.
Kim, Ryungwoo; Wu, Yanting; Tong, Rongbiao; Chemical science 15 (2024) 12856–12860; doi:10.1039/d4sc03553d

data_1572120
_publ_section_title
;
 Asymmetric total syntheses of sarglamides A, C, D, E, and F.
;
_journal_issue                   32
_journal_name_full               'Chemical science'
_journal_page_first              12856
_journal_page_last               12860
_journal_paper_doi               10.1039/d4sc03553d
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H24 O4'
_chemical_formula_sum            'C18 H24 O4'
_chemical_formula_weight         304.37
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-03-01
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-27 deposited with the CCDC.	2024-07-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.29909(12)
_cell_length_b                   10.79136(13)
_cell_length_c                   27.3078(3)
_cell_measurement_reflns_used    5911
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.9100
_cell_measurement_theta_min      3.2320
_cell_volume                     3035.02(6)
_computing_cell_refinement       'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.90 (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.984
_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   -113.00 -10.00   1.00    1.00    --  -41.01 -19.00   0.00  103
  2  \w     27.00  95.00   1.00    1.00    --   41.01-125.00 -30.00   68
  3  \w    104.00 178.00   1.00    2.00    --  112.00 111.00-150.00   74
  4  \w     44.00 140.00   1.00    2.00    --  112.00 -61.00 150.00   96
  5  \w    104.00 175.00   1.00    2.00    --  112.00 111.00-180.00   71
  6  \w    104.00 159.00   1.00    2.00    --  112.00  77.00 150.00   55
  7  \w     38.00 107.00   1.00    2.00    --  112.00 -94.00  30.00   69
  8  \w    105.00 175.00   1.00    2.00    --  112.00  77.00 -60.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1350611000
_diffrn_orient_matrix_UB_12      0.0066603000
_diffrn_orient_matrix_UB_13      -0.0241599000
_diffrn_orient_matrix_UB_21      -0.0172199000
_diffrn_orient_matrix_UB_22      0.1404926000
_diffrn_orient_matrix_UB_23      -0.0077886000
_diffrn_orient_matrix_UB_31      0.0619531000
_diffrn_orient_matrix_UB_32      0.0247295000
_diffrn_orient_matrix_UB_33      0.0503578000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11494
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.064
_diffrn_reflns_theta_min         3.237
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.90 (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 2268 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         6230
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0421P)^2^+0.1911P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0869
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                5743
_reflns_number_total             6230
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc03553d2.cif
_cod_data_source_block           rkim10_cu100k_auto
_cod_depositor_comments          'Adding full bibliography for 1572120.cif.'
_cod_database_code               1572120
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.877
_shelx_estimated_absorpt_t_min   0.864
_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:
 C4(H4), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C16(H16), C4A(H4A),
 C7A(H7A), C8A(H8A), C10A(H10A), C11A(H11A), C12A(H12A), C16A(H16A)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C9(H9A,H9B), C13(H13A,H13B), C2A(H2AA,H2AB),
 C5A(H5AA,H5AB), C9A(H9AA,H9AB), C13A(H13C,H13D)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C15A(H15D,H15E,
 H15F), C17A(H17D,H17E,H17F), C18A(H18D,H18E,H18F)
;
_shelx_res_checksum              54450
_shelx_hkl_checksum              82135
_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 1.274
_oxdiff_exptl_absorpt_empirical_full_min 0.845