Labdane-Type Diterpenoids from Croton laevigatus
Huang, Hong-Li; Qi, Feng-Ming; Yuan, Ji-Cheng; Zhao, Cai-Gui; Yang, Jing-Wei; Fang, Fu-Hu; Wu, Quan-xiang; Gao, Kun; Yuan, Cheng-Shan; RSC Advances  (2014) –; doi:10.1039/C4RA04863F

data_7217673
_publ_section_title
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 Labdane-Type Diterpenoids from Croton laevigatus
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_journal_name_full               'RSC Advances'
_journal_paper_doi               10.1039/C4RA04863F
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C22 H36 O5,0.5(C H2 Cl2)'
_chemical_formula_sum            'C22.5 H37 Cl O5'
_chemical_formula_weight         422.97
_chemical_melting_point          415.7
_chemical_name_systematic
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 ?
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_chemical_optical_rotation       '[\a]^26^~D~=+9.09 (c 0.11, in CHCl3)'
_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'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-07-28
_audit_creation_method
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Olex2 1.2-beta
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 129.100(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.328(15)
_cell_length_b                   11.042(7)
_cell_length_c                   19.217(19)
_cell_measurement_reflns_used    2123
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.47
_cell_measurement_theta_min      2.73
_cell_volume                     4335(6)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.1320
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14626
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         2.131
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             1832
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1256 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.30(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     538
_refine_ls_number_reflns         7875
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1511
_refine_ls_R_factor_gt           0.0782
_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^)+(0.0440P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1362
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_full    0.951
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                4290
_reflns_number_total             7875
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ra04863f2.cif
_cod_data_source_block           compound_8
_cod_original_cell_volume        4336(6)
_cod_original_formula_sum        'C22.50 H37 Cl O5'
_cod_database_code               7217673
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.954
_olex2_refinement_description
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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. Restrained distances
 C37-C36A \\sim C36B-C37B
 with sigma of 0.02
 C36A-C35 \\sim C36B-C35
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uiso(C36A) = Uiso(C36B)
4. Others
 Fixed Sof: C36A(0.83) H36A(0.83) C37(0.83) H37A(0.83) H37B(0.83) C36B(0.17)
 H36B(0.17) C37B(0.17) H37C(0.17) H37D(0.17) Cl1(0.5) C45(0.25) H45(0.5)
 Cl2(0.125) Cl3(0.25) Cl4(0.125)
5.a Riding coordinates:
 C45(H45)
5.b Ternary CH refined with riding coordinates:
 C27(H27), C31(H31), C34(H34), C5(H5), C9(H9), C12(H12)
5.c Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C28(H28A,H28B), C29(H29A,
 H29B), C33(H33A,H33B), C39(H39A,H39B), C40(H40A,H40B), C1(H1A,H1B), C2(H2A,
 H2B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C17(H17A,H17B),
 C18(H18A,H18B)
5.d Aromatic/amide H refined with riding coordinates:
 C36A(H36A), C36B(H36B), C14(H14)
5.e X=CH2 refined with riding coordinates:
 C37(H37A,H37B), C37B(H37C,H37D), C15(H15A,H15B)
5.f Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C), C44(H44A,H44B,
 H44C), C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,
 H22B,H22C)
5.g Idealised tetrahedral OH refined as rotating group:
 O6(H6), O7(H7), O1(H1), O2(H2)
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_olex2_submission_special_instructions 'No special instructions were received'