Muhenrins A–C, pimarane-type diterpenoids from Munronia henryi
Su, Wan-Bai; Hou, Xiao-Meng; Zhang, Ling; Yan, Li; Tang, Zhi-Yang; Yu, Yang; Liu, Jin-Song; Sun, Yun-Peng; Wang, Guo-Kai; RSC Advances 15 (2025) 25542–25547; doi:10.1039/D5RA04525H

data_7250698
_publ_section_title
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 Muhenrins A--C, pimarane-type diterpenoids from Munronia henryi
;
_journal_issue                   31
_journal_name_full               'RSC Advances'
_journal_page_first              25542
_journal_page_last               25547
_journal_paper_doi               10.1039/D5RA04525H
_journal_volume                  15
_journal_year                    2025
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C20 H30 O4'
_chemical_formula_sum            'C20 H30 O4'
_chemical_formula_weight         334.44
_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             2025-04-28
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2025.02.13 svn.rdd3e1f77 for OlexSys, GUI svn.r7147)
;
_audit_update_record
;
2025-05-18 deposited with the CCDC.	2025-07-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0825(8)
_cell_length_b                   12.7004(8)
_cell_length_c                   12.9052(8)
_cell_measurement_reflns_used    8370
_cell_measurement_temperature    170
_cell_measurement_theta_max      74.68
_cell_measurement_theta_min      3.42
_cell_volume                     1980.3(2)
_computing_cell_refinement       'SAINT V8.41 (?, 2016)'
_computing_data_reduction        'SAINT V8.41 (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17312
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.740
_diffrn_reflns_theta_min         4.885
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6014
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1304 before and 0.0965 after correction.
The Ratio of minimum to maximum transmission is 0.7978.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 1477 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0582
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0966P)^2^+0.6038P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1559
_refine_ls_wR_factor_ref         0.1622
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                3702
_reflns_number_total             3988
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra04525h2.cif
_cod_data_source_block           cu_2025427_0m
_cod_database_code               7250698
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.930
_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:
 C5(H5), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1(H1A,H1B), C3(H3A,H3B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15)
2.d X=CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.e Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C17(H17A,H17B,
 H17C)
2.f Idealised tetrahedral OH refined as rotating group:
 O4(H4), O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'