Euphorbesulins A-P, Structurally Diverse Diterpenoids from Euphorbia esula.
Zhou, Bin; Wu, Yan; Dalal, Seema; Cassera, Maria B.; Yue, Jian-Min; Journal of natural products 79 (2016) 1952–1961; doi:10.1021/acs.jnatprod.6b00205

data_1543725
_publ_section_title
;
 Euphorbesulins A-P, Structurally Diverse Diterpenoids from Euphorbia
 esula.
;
_journal_issue                   8
_journal_name_full               'Journal of natural products'
_journal_page_first              1952
_journal_page_last               1961
_journal_paper_doi               10.1021/acs.jnatprod.6b00205
_journal_volume                  79
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C33 H44 O9'
_chemical_formula_sum            'C33 H44 O9'
_chemical_formula_weight         584.68
_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     direct
_audit_creation_date             2014-11-19
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.1400(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2223(3)
_cell_length_b                   19.4300(4)
_cell_length_c                   13.7491(3)
_cell_measurement_reflns_used    5553
_cell_measurement_temperature    130
_cell_measurement_theta_max      68.82
_cell_measurement_theta_min      3.301
_cell_volume                     3439.79(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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.971
_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  0.0584
_diffrn_reflns_av_unetI/netI     0.0954
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17584
_diffrn_reflns_point_group_measured_fraction_full 0.823
_diffrn_reflns_point_group_measured_fraction_max 0.806
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.482
_diffrn_reflns_theta_min         3.301
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.4558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1405 before and 0.0798 after correction. The Ratio of minimum to maximum transmission is 0.6052. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_description       plate
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
;
 Flack x determined using 3370 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     777
_refine_ls_number_reflns         10417
_refine_ls_number_restraints     43
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0747
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1436P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1902
_refine_ls_wR_factor_ref         0.1939
_reflns_Friedel_coverage         0.609
_reflns_Friedel_fraction_full    0.650
_reflns_Friedel_fraction_max     0.630
_reflns_number_gt                9674
_reflns_number_total             10417
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np6b00205_si_002.cif
_cod_data_source_block           cu_dm14667_0m
_cod_depositor_comments          'Adding full bibliography for 1543725.cif.'
_cod_database_code               1543725
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.825
_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. Uiso/Uaniso restraints and constraints
Uanis(C4A) \\sim Ueq, Uanis(C6A) \\sim Ueq, Uanis(C21A) \\sim Ueq, Uanis(C13)
\\sim Ueq, Uanis(O2A) \\sim Ueq, Uanis(C27A) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
Uanis(C4) \\sim Ueq, Uanis(C4A) \\sim Ueq, Uanis(C6A) \\sim Ueq, Uanis(O2A)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C4) \\sim Ueq, Uanis(C4A) \\sim Ueq, Uanis(C6A) \\sim Ueq, Uanis(O2A)
\\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
3.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5A), C12(H12), C29(H29), C31(H31), C2A(H2A),
 C3A(H3A), C4A(H4A), C5A(H5AB), C12A(H12A), C29A(H29A), C31A(H31A)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7A,H7B), C11(H11A,H11B), C1A(H1AA,H1AB), C7A(H7AB,H7AC),
 C11A(H11C,H11D)
3.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C23A(H23A), C24A(H24A),
 C25A(H25A), C26A(H26A), C27A(H27A)
3.d X=CH2 refined with riding coordinates:
 C17(H17A,H17B), C17A(H17C,H17D)
3.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C),
 C16A(H16D,H16E,H16F), C18A(H18D,H18E,H18F), C19A(H19D,H19E,H19F), C20A(H20D,
 H20E,H20F), C30A(H30D,H30E,H30F), C32A(H32D,H32E,H32F), C33A(H33D,H33E,H33F)
3.f Idealised tetrahedral OH refined as rotating group:
 O5(H5), O7(H7), O9(H9), O5A(H5AA), O7A(H7AA), O9A(H9A)
;
_shelx_res_checksum              28387
_shelx_hkl_checksum              60442
_olex2_submission_special_instructions 'No special instructions were received'