Toward the total synthesis of grayanane diterpene mollanol A by a Prins [3 + 2] strategy.
Miao, Jianzhuang; Zheng, Yi-Xuan; Wang, Linna; Lu, Shi-Chao; Zhang, Shi-Peng; Gong, Ya-Ling; Xu, Shu; Organic & biomolecular chemistry 18 (2020) 1877–1880; doi:10.1039/d0ob00160k

data_7157351
_publ_section_title
;
 Toward the total synthesis of grayanane diterpene mollanol A by a Prins
 [3 + 2] strategy.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1877
_journal_page_last               1880
_journal_paper_doi               10.1039/d0ob00160k
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C25 H31 Br O4'
_chemical_formula_sum            'C25 H31 Br O4'
_chemical_formula_weight         475.41
_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     dual
_audit_creation_date             2017-07-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-08-13 deposited with the CCDC.	2020-02-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7572(4)
_cell_length_b                   14.2840(7)
_cell_length_c                   23.8212(14)
_cell_measurement_reflns_used    7124
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      30.521
_cell_measurement_theta_min      2.978
_cell_volume                     2299.2(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.994
_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  0.0670
_diffrn_reflns_av_unetI/netI     0.0852
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            25510
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.561
_diffrn_reflns_theta_min         1.662
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.816
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1359 before and 0.0797 after correction. The Ratio of minimum to maximum transmission is 0.5698. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 1469 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.038(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         6978
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0514
_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^)+(0.0322P)^2^+0.1459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.1015
_reflns_Friedel_coverage         0.757
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                4702
_reflns_number_total             6978
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00160k2.cif
_cod_data_source_block           mo_d8v17203_0m
_cod_depositor_comments
'Adding full bibliography for 7157350--7157351.cif.'
_cod_database_code               7157351
_shelx_shelxl_version_number     2014/8
_shelx_estimated_absorpt_t_max   0.915
_shelx_estimated_absorpt_t_min   0.713
_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:
 C6(H6), C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C10(H10A,H10B), C12(H12A,H12B),
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C22(H22), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C)
;
_shelx_res_checksum              89884
_olex2_submission_special_instructions 'No special instructions were received'