Jatrophane Diterpenoids from Euphorbia glomerulans.
Hasan, Aobulikasimu; Liu, Ge-Yu; Hu, Rui; Aisa, H. A.; Journal of natural products 82 (2019) 724–734; doi:10.1021/acs.jnatprod.8b00507

data_1552630
_publ_section_title
;
 Jatrophane Diterpenoids from Euphorbia glomerulans.
;
_journal_issue                   4
_journal_name_full               'Journal of natural products'
_journal_page_first              724
_journal_page_last               734
_journal_paper_doi               10.1021/acs.jnatprod.8b00507
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C35 H42 O12, C2 H3 N'
_chemical_formula_sum            'C37 H45 N O12'
_chemical_formula_weight         695.74
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-26
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.213(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.7453(5)
_cell_length_b                   8.9804(4)
_cell_length_c                   18.5229(8)
_cell_measurement_reflns_used    6103
_cell_measurement_temperature    296
_cell_measurement_theta_max      72.139
_cell_measurement_theta_min      4.055
_cell_volume                     1893.94(14)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      296.15
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0412
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16159
_diffrn_reflns_point_group_measured_fraction_full 0.861
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        66.593
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_min         4.055
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1254 before and 0.0592 after correction. The Ratio of minimum to maximum transmission is 0.7241. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       block
_exptl_crystal_F_000             740
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1998 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(10)
_refine_ls_extinction_coef       0.0148(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         5754
_refine_ls_number_restraints     383
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0680P)^2^+0.1050P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1129
_reflns_Friedel_coverage         0.633
_reflns_Friedel_fraction_full    0.717
_reflns_Friedel_fraction_max     0.717
_reflns_number_gt                5506
_reflns_number_total             5754
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00507_si_002.cif
_cod_data_source_block           cu_20171028-c11b-9_0m
_cod_database_code               1552630
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.915
_shelx_estimated_absorpt_t_min   0.816
_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
2. Rigid bond restraints
 C32, C33
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
C32 \\sim C33: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Ternary CH refined with riding coordinates:
 C5(H5), C4(H4), C3(H3), C8(H8), C2(H2), C7(H7), C13(H13)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
5.c Aromatic/amide H refined with riding coordinates:
 C30(H30), C12(H12), C11(H11), C34(H34), C32(H32), C31(H31), C33(H33)
5.d X=CH2 refined with riding coordinates:
 C25(H25A,H25B)
5.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C27(H27A,H27B,H27C), C18(H18A,H18B,H18C), C23(H23A,H23B,
 H23C), C016(H01A,H01B,H01C), C20(H20A,H20B,H20C), C17(H17A,H17B,H17C),
 C22(H22A,H22B,H22C), C36(H36A,H36B,H36C)
;
_olex2_submission_special_instructions 'No special instructions were received'