Microbial Transformations of two Beyerane-type Diterpenes by Cunninghamella echinulata.
Gao, Yu-Qi; Li, Ruoxin; Wang, Weiwei; Lee, Shoei-Sheng; Gao, Jin-Ming; Journal of agricultural and food chemistry  (2020) –; doi:10.1021/acs.jafc.0c00592

data_1557786
_publ_section_title
;
 Microbial Transformations of two Beyerane-type Diterpenes by
 Cunninghamella echinulata.
;
_journal_name_full               'Journal of agricultural and food chemistry'
_journal_paper_doi               10.1021/acs.jafc.0c00592
_journal_year                    2020
_chemical_formula_moiety         'C20 H32 O4, C H4 O'
_chemical_formula_sum            'C21 H36 O5'
_chemical_formula_weight         368.50
_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             2018-10-08
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7541(8)
_cell_length_b                   13.6991(17)
_cell_length_c                   21.781(3)
_cell_measurement_reflns_used    4643
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.39
_cell_volume                     2015.3(4)
_computing_cell_refinement       'SAINT v7.56A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.56A (Bruker, 2009)'
_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      296.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10615
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.727
_diffrn_reflns_theta_min         1.756
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9767
_exptl_absorpt_correction_T_min  0.9702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1295 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3824
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0775P)^2^+0.1805P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1238
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3411
_reflns_number_total             3824
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jf0c00592_si_003.cif
_cod_data_source_block           xb4269_0m
_cod_database_code               1557786
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.970
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C5(H5), C12(H12), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C6(H6A,H6B), C7(H7A,H7B), C16(H16A,H16B), C1(H1A,H1B),
 C14(H14A,H14B), C2(H2A,H2B), C3(H3A,H3B)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C18(H18A,H18B,H18C), C00Q(H00A,H00B,
 H00C)
2.d Idealised tetrahedral OH refined as rotating group:
 O23(H23), O24(H24), O003(H003), O22(H22)
;
_shelx_res_checksum              14922
_shelx_hkl_checksum              20966
_shelx_shelxl_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'