Hitoyol A and B, Two Norsesquiterpenoids from the Basidiomycete Coprinopsis cinerea
Otaka, Junnosuke; Hashizume, Daisuke; Masumoto, Yui; Muranaka, Atsuya; Uchiyama, Masanobu; Koshino, Hiroyuki; Futamura, Yushi; Osada, Hiroyuki; Organic Letters  (2017) –; doi:10.1021/acs.orglett.7b01784

data_1546562
_publ_section_title
;
 Hitoyol A and B, Two Norsesquiterpenoids from the Basidiomycete
 Coprinopsis cinerea
;
_journal_name_full               'Organic Letters'
_journal_paper_doi               10.1021/acs.orglett.7b01784
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H20 O4'
_chemical_formula_sum            'C14 H20 O4'
_chemical_formula_weight         252.30
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.69085(14)
_cell_length_b                   7.90495(14)
_cell_length_c                   21.4299(4)
_cell_measurement_reflns_used    26018
_cell_measurement_temperature    150
_cell_measurement_theta_max      68.295
_cell_measurement_theta_min      4.125
_cell_volume                     1302.85(4)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       RAPID-AUTO
_computing_data_reduction        RAPID-AUTO
_computing_molecular_graphics    SHELXLE
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    SIR-2004
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku RAXIS RAPID'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            26278
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.224
_diffrn_reflns_theta_min         4.126
_diffrn_source                   'Fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.764
_exptl_absorpt_correction_T_max  0.8333
_exptl_absorpt_correction_T_min  0.7352
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   numabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.467
_exptl_crystal_size_mid          0.386
_exptl_crystal_size_min          0.258
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 875 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         2388
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0538P)^2^+0.1385P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0861
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2251
_reflns_number_total             2388
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01784_si_001.cif
_cod_data_source_block           Cc-8
_cod_database_code               1546562
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.717
_shelx_estimated_absorpt_t_max   0.827
_shelx_res_checksum              60447
_shelx_hkl_checksum              83510