Fragrant Venezuelaenes A and B with A 5–5–6–7 Tetracyclic Skeleton: Discovery, Biosynthesis, and Mechanisms of Central Catalysts
Li, Zhong; Jiang, Yuanyuan; Zhang, Xingwang; Chang, Yimin; Li, Shuai; Zhang, Xiaomin; Zheng, Shanmin; Geng, Ce; Men, Ping; Ma, Li; Yang, Ying; Gao, Zhengquan; Tang, Ya-Jie; Li, Shengying; ACS Catalysis 10 (2020) 5846–5851; doi:10.1021/acscatal.0c01575

data_4517639
_publ_section_title
;
 Fragrant Venezuelaenes A and B with A 5--5--6--7 Tetracyclic Skeleton:
 Discovery, Biosynthesis, and Mechanisms of Central Catalysts
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              5846
_journal_page_last               5851
_journal_paper_doi               10.1021/acscatal.0c01575
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_sum            'C20 H32'
_chemical_formula_weight         272.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5688(14)
_cell_length_b                   11.1801(10)
_cell_length_c                   11.1208(10)
_cell_measurement_reflns_used    2356
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.2590
_cell_measurement_theta_min      3.9990
_cell_volume                     1687.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12587
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.242
_diffrn_reflns_theta_max         67.242
_diffrn_reflns_theta_min         3.975
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.431
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.073
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 680 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(10)
_refine_ls_extinction_coef       0.034(2)
_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   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3021
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0530
_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^)+(0.0713P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1488
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2173
_reflns_number_total             3021
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c01575_si_002.cif
_cod_data_source_block           exp_10163
_cod_depositor_comments
;Adding full bibliography for 4517639.cif.

 Adding full bibliography for 4517639.cif.
;
_cod_database_code               4517639
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.950
_shelx_res_checksum              6368
_shelx_hkl_checksum              96325