Concise gram-scale synthesis of Euphorikanin A skeleton through a domino ring-closing metathesis strategy.
Shi, Linlin; He, Yingdong; Gong, Jianxian; Yang, Zhen; Chemical communications (Cambridge, England) 56 (2020) 531–534; doi:10.1039/c9cc08830j

data_7125905
_publ_section_title
;
 Concise gram-scale synthesis of Euphorikanin A skeleton through a domino
 ring-closing metathesis strategy.
;
_journal_issue                   4
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              531
_journal_page_last               534
_journal_paper_doi               10.1039/c9cc08830j
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H26 O3'
_chemical_formula_sum            'C19 H26 O3'
_chemical_formula_weight         302.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-02 deposited with the CCDC.	2019-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.5910(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.2464(6)
_cell_length_b                   7.0762(2)
_cell_length_c                   28.1700(10)
_cell_measurement_reflns_used    9837
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.44
_cell_measurement_theta_min      4.85
_cell_volume                     3341.57(19)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      100
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            17171
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.469
_diffrn_reflns_theta_min         4.845
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0855 before and 0.0548 after correction. The Ratio of minimum to maximum transmission is 0.8769. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       0.0033(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         6095
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0513
_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^)+(0.0919P)^2^+2.0201P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1369
_refine_ls_wR_factor_ref         0.1384
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                5917
_reflns_number_total             6095
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc08830j2.cif
_cod_data_source_block           cxy0776_0m
_cod_database_code               7125905
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.838
_shelx_estimated_absorpt_t_min   0.786
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C9(H9), C11(H11), C23(H23), C25(H25), C34(H34), C36(H36)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C17(H17A,H17B), C24(H24A,H24B), C28(H28A,
 H28B), C33(H33A,H33B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C16(H16), C29(H29), C31(H31), C32(H32)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C),
 C20(H20A,H20B,H20C), C27(H27A,H27B,H27C), C37(H37A,H37B,H37C), C38(H38A,H38B,
 H38C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O5(H5A)
;
_olex2_submission_special_instructions 'No special instructions were received'