Chemoenzymatic synthesis of (+)-isoagatholactone, (+)-spongian-16-one, and 3-deoxychavalone A <i>via</i> biocatalytic polyene cyclization.
Xiao, Wen; Wang, Su-Jing; Yu, Ming-Zhu; Zhang, Xue-Jie; Xiang, Zheng; Organic & biomolecular chemistry 21 (2023) 5527–5531; doi:10.1039/d3ob00206c

data_7159417
_publ_section_title
;
 Chemoenzymatic synthesis of (+)-isoagatholactone, (+)-spongian-16-one,
 and 3-deoxychavalone A <i>via</i> biocatalytic polyene cyclization.
;
_journal_issue                   27
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5527
_journal_page_last               5531
_journal_paper_doi               10.1039/d3ob00206c
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration s
_chemical_formula_sum            'C27 H38 N2 O7'
_chemical_formula_weight         502.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-03-17 deposited with the CCDC.	2023-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.001(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.16740(10)
_cell_length_b                   28.3059(4)
_cell_length_c                   7.81700(10)
_cell_measurement_reflns_used    6687
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      76.0320
_cell_measurement_theta_min      3.1040
_cell_volume                     1274.00(4)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8063
_diffrn_reflns_point_group_measured_fraction_full 0.788
_diffrn_reflns_point_group_measured_fraction_max 0.740
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.658
_diffrn_reflns_theta_min         3.122
_exptl_absorpt_coefficient_mu    0.773
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_description       bolck
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 1202 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(15)
_refine_ls_extinction_coef       0.0136(13)
_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   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         3959
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0653P)^2^+0.0765P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1111
_reflns_Friedel_coverage         0.516
_reflns_Friedel_fraction_full    0.567
_reflns_Friedel_fraction_max     0.514
_reflns_number_gt                3723
_reflns_number_total             3959
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00206c2.cif
_cod_data_source_block           wsj-peake-2no2-ag
_cod_depositor_comments          'Adding full bibliography for 7159417.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7159417
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              84461