Camellianols A-G, Barrigenol-like Triterpenoids with PTP1B Inhibitory Effects from the Endangered Ornamental Plant Camellia crapnelliana.
Xiong, Juan; Wan, Jiang; Ding, Jie; Wang, Pei-Pei; Ma, Guang-Lei; Li, Jia; Hu, Jin-Feng; Journal of natural products 80 (2017) 2874–2882; doi:10.1021/acs.jnatprod.7b00241

data_1547776
_publ_section_title
;
 Camellianols A-G, Barrigenol-like Triterpenoids with PTP1B Inhibitory
 Effects from the Endangered Ornamental Plant Camellia crapnelliana.
;
_journal_issue                   11
_journal_name_full               'Journal of natural products'
_journal_page_first              2874
_journal_page_last               2882
_journal_paper_doi               10.1021/acs.jnatprod.7b00241
_journal_volume                  80
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C30 H48 O5, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C30.5 H49 Cl O5'
_chemical_formula_weight         531.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.819(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.8304(3)
_cell_length_b                   7.6333(2)
_cell_length_c                   20.2122(6)
_cell_measurement_reflns_used    4604
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      70.138
_cell_measurement_theta_min      4.613
_cell_volume                     1478.89(7)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      298.83
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11099
_diffrn_reflns_point_group_measured_fraction_full 0.924
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.109
_diffrn_reflns_theta_min         5.680
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.425
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1511 before and 0.0765 after correction. The Ratio of minimum to maximum transmission is 0.7041. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_description       block
_exptl_crystal_F_000             578
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1384 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         5139
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0604
_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^)+(0.0967P)^2^+0.0859P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1535
_refine_ls_wR_factor_ref         0.1706
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    0.858
_reflns_Friedel_fraction_max     0.842
_reflns_number_gt                4188
_reflns_number_total             5139
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00241_si_002.cif
_cod_data_source_block           cu_d8v17138_0m
_cod_depositor_comments          'Adding full bibliography for 1547776.cif.'
_cod_original_formula_sum        'C30.50 H49 Cl O5'
_cod_database_code               1547776
_shelx_shelxl_version_number     2014/8
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.932
_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. Restrained distances
 Cl1-C31 = C32-C31
 1.8 with sigma of 0.02
 Cl1-C31 = Cl3-C32 = Cl4-C32
 1.8 with sigma of 0.02
 Cl2-C31 = Cl1-C31
 1.8 with sigma of 0.02
 H1A-H31A_$3
 2 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl3 \\sim Cl4 \\sim C32 \\sim Cl1 \\sim C31: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02
Cl1 \\sim Cl2 \\sim C31: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
4. Others
 Fixed Sof: Cl3(0.25) Cl4(0.25) C32(0.25) H32A(0.25) H32B(0.25) Cl1(0.25)
 Cl2(0.25) C31(0.25) H31A(0.25) H31B(0.25)
5.a Ternary CH refined with riding coordinates:
 C5(H5A), C9(H9), C15(H15), C16(H16), C18(H18), C22(H22)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C11(H11A,H11B), C19(H19A,
 H19B), C21(H21A,H21B), C28(H28A,H28B), C32(H32A,H32B), C31(H31A,H31B)
5.c Aromatic/amide H refined with riding coordinates:
 C12(H12)
5.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
5.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O4(H4), O5(H5)
;
_shelx_res_checksum              26987
_shelx_hkl_checksum              21750
_olex2_submission_special_instructions 'No special instructions were received'