Total Synthesis of (-)-Rhodomollanol A.
Gao, Jianhong; Rao, Peirong; Xu, Kaixiang; Wang, Shuaifeng; Wu, Yufei; Ding, Hanfeng; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c00308

data_4134265
_publ_section_title
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 Total Synthesis of (-)-Rhodomollanol A.
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_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c00308
_journal_year                    2020
_chemical_formula_moiety         'C20 H28 O5'
_chemical_formula_sum            'C20 H28 O5'
_chemical_formula_weight         348.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                99.192(19)
_cell_angle_beta                 101.842(19)
_cell_angle_gamma                99.459(17)
_cell_formula_units_Z            2
_cell_length_a                   8.585(3)
_cell_length_b                   9.649(3)
_cell_length_c                   10.848(4)
_cell_measurement_reflns_used    7208
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.11
_cell_measurement_theta_min      2.48
_cell_volume                     849.9(5)
_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      170.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10429
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.072
_diffrn_reflns_theta_min         2.476
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1176 before and 0.0329 after correction.
The Ratio of minimum to maximum transmission is 0.9569.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0476P)^2^+0.3634P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.0978
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3450
_reflns_number_total             3709
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c00308_si_005.cif
_cod_data_source_block           191210_gjh_rhodomollanol_0m
_cod_database_code               4134265
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.954
_olex2_refinement_description
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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 C(H,H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2A), C5(H5A), C7(H7), C10(H10), C11(H11), C14(H14), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O5(H5)
;
_shelx_res_checksum              70275
_shelx_hkl_checksum              82392
_olex2_submission_special_instructions 'No special instructions were received'