Forging the tricyclic core framework of euphordraculoate B <i>via</i> a Barbier-type allyl addition.
Meng, Lingduan; Liu, Jingjing; Sun, Zeying; Hou, Yangdong; Huang, Qingyun; Tang, Pingping; Organic & biomolecular chemistry 23 (2025) 589–592; doi:10.1039/d4ob01743a

data_7160264
_publ_section_title
;
 Forging the tricyclic core framework of euphordraculoate B <i>via</i> a
 Barbier-type allyl addition.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              589
_journal_page_last               592
_journal_paper_doi               10.1039/d4ob01743a
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C37 H50 O4 Si'
_chemical_formula_sum            'C37 H50 O4 Si'
_chemical_formula_weight         586.86
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-05-09 deposited with the CCDC.	2024-11-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.6459(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.62167(13)
_cell_length_b                   10.50225(11)
_cell_length_c                   15.14865(15)
_cell_measurement_reflns_used    19166
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      31.7270
_cell_measurement_theta_min      1.9090
_cell_volume                     1686.43(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_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    -41.00  73.00   1.00    5.00    --  -16.40  34.00  32.00  114
  2  \w   -106.00   8.00   1.00    5.00    --  -16.40 -34.00-125.00  114
  3  \w   -106.00   8.00   1.00    5.00    --  -16.40 -38.00 120.00  114
  4  \w    -30.00  40.00   1.00    5.00    --  -16.40  38.00 150.00   70
  5  \w    -42.00  73.00   1.00    5.00    --  -16.40  57.00  90.00  115
  6  \w    -93.00   7.00   1.00    5.00    --  -16.40 -38.00  30.00  100
  7  \w    -41.00  72.00   1.00    5.00    --  -16.40  38.00-180.00  113
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0618470000
_diffrn_orient_matrix_UB_12      -0.0204714000
_diffrn_orient_matrix_UB_13      0.0136344000
_diffrn_orient_matrix_UB_21      0.0219818000
_diffrn_orient_matrix_UB_22      0.0216123000
_diffrn_orient_matrix_UB_23      -0.0406215000
_diffrn_orient_matrix_UB_31      0.0130517000
_diffrn_orient_matrix_UB_32      0.0606294000
_diffrn_orient_matrix_UB_33      0.0190876000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            38186
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.575
_diffrn_reflns_theta_min         1.921
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.156
_exptl_crystal_description       plate
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 3929 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     395
_refine_ls_number_reflns         9443
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0447
_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^)+(0.0625P)^2^+0.1546P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1097
_reflns_Friedel_coverage         0.903
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                9105
_reflns_number_total             9443
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01743a2.cif
_cod_data_source_block           r20231011b
_cod_depositor_comments          'Adding full bibliography for 7160264.cif.'
_cod_database_code               7160264
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C37H50O4Si1
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.971
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51
_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. Restrained distances
 O3-H3 = O2-H2
 0.85 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3A), C4(H4), C5(H5), C6(H6), C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C10(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C33(H33), C34(H34),
 C35(H35), C36(H36), C37(H37)
3.d X=CH2 refined with riding coordinates:
 C15(H15A,H15B), C18(H18A,H18B)
3.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,
 H25B,H25C)
;
_shelx_res_checksum              11476
_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 1.471
_oxdiff_exptl_absorpt_empirical_full_min 0.569