Asymmetric total synthesis of humulane sesquiterpenoids alashanoids B, C, E, and F and 2,9-humuladien-6-ol-8-one.
Barik, Rasmita; Nanda, Samik; Organic & biomolecular chemistry 22 (2024) 4478–4487; doi:10.1039/d4ob00393d

data_7159890
_publ_section_title
;
 Asymmetric total synthesis of humulane sesquiterpenoids alashanoids B, C,
 E, and F and 2,9-humuladien-6-ol-8-one.
;
_journal_issue                   22
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4478
_journal_page_last               4487
_journal_paper_doi               10.1039/d4ob00393d
_journal_volume                  22
_journal_year                    2024
_chemical_formula_sum            'C15 H24 O2'
_chemical_formula_weight         236.4
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_update_record
;
2023-10-16 deposited with the CCDC.	2024-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0794(2)
_cell_length_b                   13.0587(4)
_cell_length_c                   17.7262(6)
_cell_measurement_reflns_used    6094
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.78
_cell_measurement_theta_min      2.78
_cell_volume                     1407.27(8)
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Photon III'
_diffrn_measurement_method       'Bruker Photon III'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17469
_diffrn_reflns_theta_full        27.1
_diffrn_reflns_theta_max         27.1
_diffrn_reflns_theta_min         2.78
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7066
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            White
_exptl_crystal_density_diffrn    1.1156
_exptl_crystal_description       Cuboid
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.25
_refine_ls_abs_structure_details
'  1293 of Friedel pairs used in the refinement'
_refine_ls_extinction_coef       27000(6000)
_refine_ls_extinction_method
'B-C type 1 Gaussian isotropic (Becker & Coppens, 1974)'
_refine_ls_goodness_of_fit_gt    2.68
_refine_ls_goodness_of_fit_ref   2.51
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_constraints    92
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3092
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.0489
_refine_ls_shift/su_mean         0.0102
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     w=1/(\s^2^(F)+0.0001F^2^)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0543
_refine_ls_wR_factor_ref         0.0552
_reflns_number_gt                2640
_reflns_number_total             3092
_reflns_threshold_expression     I>3\s(I)
_cod_data_source_file            d4ob00393d2.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7159890--7159891.cif.
;
_cod_original_sg_symbol_Hall     'P 2xab;2ybc;2zac'
_cod_database_code               7159890