Abietane Diterpenoids from the Roots of Clerodendrum trichotomum and Their Nitric Oxide Inhibitory Activities.
Hu, Hai-Jun; Zhou, Yue; Han, Zhu-Zhen; Shi, Yan-Hong; Zhang, Shu-Sheng; Wang, Zheng-Tao; Yang, Li; Journal of natural products 81 (2018) 1508–1516; doi:10.1021/acs.jnatprod.7b00814

data_1553319
_publ_section_title
;
 Abietane Diterpenoids from the Roots of Clerodendrum trichotomum and
 Their Nitric Oxide Inhibitory Activities.
;
_journal_issue                   7
_journal_name_full               'Journal of natural products'
_journal_page_first              1508
_journal_page_last               1516
_journal_paper_doi               10.1021/acs.jnatprod.7b00814
_journal_volume                  81
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C20 H24 O5'
_chemical_formula_sum            'C20 H24 O5'
_chemical_formula_weight         344.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-30
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.092(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.3772(7)
_cell_length_b                   8.3180(3)
_cell_length_c                   11.8120(6)
_cell_measurement_reflns_used    4017
_cell_measurement_temperature    296
_cell_measurement_theta_max      69.181
_cell_measurement_theta_min      3.96
_cell_volume                     1799.13(13)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (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
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6930
_diffrn_reflns_point_group_measured_fraction_full 0.765
_diffrn_reflns_point_group_measured_fraction_max 0.743
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.687
_diffrn_reflns_theta_min         3.960
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1013 before and 0.0420 after correction. The Ratio of minimum to maximum transmission is 0.8650. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 698 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2523
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0809P)^2^+0.4760P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1312
_refine_ls_wR_factor_ref         0.1337
_reflns_Friedel_coverage         0.443
_reflns_Friedel_fraction_full    0.514
_reflns_Friedel_fraction_max     0.493
_reflns_number_gt                2432
_reflns_number_total             2523
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00814_si_004.cif
_cod_data_source_block           dm17326
_cod_database_code               1553319
_shelx_shelxl_version_number     2014/8
_shelx_estimated_absorpt_t_max   0.866
_shelx_estimated_absorpt_t_min   0.808
_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:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C15(H15A,H15B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4), O5(H5)
;
_shelx_res_checksum              78614
_shelx_hkl_checksum              12925
_shelx_fab_checksum              52518
_olex2_submission_special_instructions 'No special instructions were received'