Sublyratins A-O, Labdane-Type Diterpenoids from <i>Croton sublyratus</i>.
Qi, Jing-Jing; Zhou, Jun-Su; Zhang, Yan; Fan, Yao-Yue; Zhou, Bin; Liu, Hong-Chun; Zhao, Jin-Xin; Yue, Jian-Min; Journal of natural products 84 (2021) 2971–2980; doi:10.1021/acs.jnatprod.1c00804

data_1565508
_publ_section_title
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 Sublyratins A-O, Labdane-Type Diterpenoids from <i>Croton sublyratus</i>.
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_journal_issue                   11
_journal_name_full               'Journal of natural products'
_journal_page_first              2971
_journal_page_last               2980
_journal_paper_doi               10.1021/acs.jnatprod.1c00804
_journal_volume                  84
_journal_year                    2021
_chemical_formula_moiety         '2(C20 H30 O4), H2 O'
_chemical_formula_sum            'C40 H62 O9'
_chemical_formula_weight         686.89
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.336(2)
_cell_length_b                   25.356(3)
_cell_length_c                   6.3309(7)
_cell_measurement_reflns_used    2679
_cell_measurement_temperature    170
_cell_measurement_theta_max      75.064
_cell_measurement_theta_min      3.486
_cell_volume                     3746.0(7)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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      170.0
_diffrn_measured_fraction_theta_full 0.924
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1010
_diffrn_reflns_av_unetI/netI     0.1258
_diffrn_reflns_Laue_measured_fraction_full 0.924
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_number            18421
_diffrn_reflns_point_group_measured_fraction_full 0.897
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.243
_diffrn_reflns_theta_min         2.573
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1399 before and 0.0928 after correction. The Ratio of minimum to maximum transmission is 0.7714. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_description       needle
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 917 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     466
_refine_ls_number_reflns         6779
_refine_ls_number_restraints     467
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.1413
_refine_ls_R_factor_gt           0.0842
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1040P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1982
_refine_ls_wR_factor_ref         0.2301
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    0.862
_reflns_Friedel_fraction_max     0.838
_reflns_number_gt                3801
_reflns_number_total             6779
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00804_si_005.cif
_cod_data_source_block           cu_2021202_0m
_cod_database_code               1565508
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.948
_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, All O(H,H) groups
2. Restrained distances
 C1-C01C \\sim C0AA-C01C \\sim C01B-C016
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
5. Others
 Fixed Sof: H01K(0.5) H01L(0.5) C1(0.5) H1A(0.5) H1B(0.5) C0AA(0.5) H0AA(0.5)
 H0AB(0.5)
6.a Free rotating group:
 O009(H00,H)
6.b Ternary CH refined with riding coordinates:
 C00B(H00D), C00E(H00N), C00H(H00H), C00L(H00U), C00O(H00W), C00R(H00X),
 C00S(H00S), C00T(H00T)
6.c Secondary CH2 refined with riding coordinates:
 C00Q(H00F,H00G), C00W(H00Y,HA), C00X(H00Z,HB), C00Z(H00L,H00M), C010(H01M,
 H01N), C011(H01A,H01B), C012(H01C,H01D), C018(H01U,H01V)
6.d Aromatic/amide H refined with riding coordinates:
 C00C(H00E), C00M(H00V), C016(H016), C01C(H01K), C01C(H01L)
6.e X=CH2 refined with riding coordinates:
 C01B(H01Z,HC), C1(H1A,H1B), C0AA(H0AA,H0AB)
6.f Idealised Me refined as rotating group:
 C008(H00A,H00B,H00C), C00G(H00O,H00Q,H00R), C00Y(H00I,H00J,H00K), C013(H01O,
 H01P,H01Q), C015(H01E,H01F,H01G), C017(H01R,H01S,H01T), C019(H01H,H01I,H01J),
 C01A(H01W,H01X,H01Y)
6.g Idealised tetrahedral OH refined as rotating group:
 O004(H004), O005(H005), O006(H006), O00P(H00P)
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_olex2_submission_special_instructions 'No special instructions were received'