Asymmetric synthesis of venezuelaene's core with a <i>trans</i>-fused [5-5] ring system.
Chen, Louxi; Zhang, Chao-Han; Liu, Junyang; Li, Chuang-Chuang; Chemical communications (Cambridge, England) 61 (2025) 10823–10826; doi:10.1039/d5cc02504d

data_7134684
_publ_section_title
;
 Asymmetric synthesis of venezuelaene's core with a <i>trans</i>-fused
 [5-5] ring system.
;
_journal_issue                   58
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10823
_journal_page_last               10826
_journal_paper_doi               10.1039/d5cc02504d
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H44 O3 Si'
_chemical_formula_sum            'C26 H44 O3 Si'
_chemical_formula_weight         432.70
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-14
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-02-08 deposited with the CCDC.	2025-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                75.509(3)
_cell_angle_beta                 65.961(3)
_cell_angle_gamma                67.425(3)
_cell_formula_units_Z            2
_cell_length_a                   11.0269(10)
_cell_length_b                   11.0409(10)
_cell_length_c                   12.3804(11)
_cell_measurement_reflns_used    9568
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      56.99
_cell_measurement_theta_min      4.03
_cell_volume                     1263.2(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Apex3 (Bruker 2018)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2014'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Bruker PHOTON III area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            50323
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.082
_diffrn_reflns_theta_min         3.422
_diffrn_source                   'microfocus Metaljet'
_diffrn_source_current           3.0
_diffrn_source_power             0.20958
_diffrn_source_type              'Incoatec Metaljet'
_diffrn_source_voltage           69.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1003 before and 0.0633 after correction.
The Ratio of minimum to maximum transmission is 0.8223.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 4769 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         10149
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0711P)^2^+0.2811P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1021
_reflns_Friedel_coverage         0.962
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                9971
_reflns_number_total             10149
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc02504d2.cif
_cod_data_source_block           cxy5025_0m
_cod_depositor_comments
'Adding full bibliography for 7134683--7134684.cif.'
_cod_database_code               7134684
_shelx_shelxl_version_number     2019/2
_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:
 C2(H2), C3(H3), C5(H5), C6(H6), C13(H13), C19(H19), C25(H25), C28(H28),
 C30(H30), C31(H31), C37(H37), C38(H38), C40(H40), C49(H49)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C24(H24A,H24B),
 C27(H27A,H27B), C36(H36A,H36B), C39(H39A,H39B), C46(H46A,H46B), C48(H48A,H48B)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C11(H11A,H11B,H11C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C26(H26A,H26B,H26C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C), C35(H35A,
 H35B,H35C), C42(H42A,H42B,H42C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C),
 C50(H50A,H50B,H50C), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C)
;
_shelx_res_checksum              38748
_shelx_hkl_checksum              31945
_olex2_submission_special_instructions 'No special instructions were received'