Eupulcherol A, a triterpenoid with a new carbon skeleton from Euphorbia pulcherrima, and its anti-Alzheimer's disease bioactivity.
Yu, Chun-Xue; Wang, Ru-Yue; Qi, Feng-Ming; Su, Pan-Jie; Yu, Yi-Fan; Li, Bing; Zhao, Ye; Zhi, De-Juan; Zhang, Zhan-Xin; Fei, Dong-Qing; Organic & biomolecular chemistry 18 (2019) 76–80; doi:10.1039/c9ob02334h

data_7157211
_publ_section_title
;
 Eupulcherol A, a triterpenoid with a new carbon skeleton from Euphorbia
 pulcherrima, and its anti-Alzheimer's disease bioactivity.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              76
_journal_page_last               80
_journal_paper_doi               10.1039/c9ob02334h
_journal_volume                  18
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         '0.5(C60 H96 O4)'
_chemical_formula_sum            'C30 H48 O2'
_chemical_formula_weight         440.68
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-03-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-24 deposited with the CCDC.	2019-11-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.44427(8)
_cell_length_b                   25.7480(3)
_cell_length_c                   31.5946(4)
_cell_measurement_reflns_used    7419
_cell_measurement_temperature    292.2(4)
_cell_measurement_theta_max      69.8650
_cell_measurement_theta_min      6.8600
_cell_volume                     5242.40(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      292.2(4)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
  1 omega   19.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -120.0000 36

  2 omega  -26.00   43.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   57.0000   30.0000 69

  3 omega   38.00  101.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   30.0000 63

  4 omega  -16.00   83.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000  -60.0000 99

  5 omega   53.00   79.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 26

  6 omega   42.00   83.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 41

  7 omega   35.00   61.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 26

  8 omega  105.00  167.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000   90.0000 62

  9 omega   36.00  105.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 69

 10 omega   78.00  177.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 99

 11 omega  110.00  136.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 26

 12 omega   63.00   89.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   90.0000 26

 13 omega  100.00  153.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 53

 14 omega   69.00   94.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 25

 15 omega   44.00   69.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   60.0000 25

 16 omega   38.00   63.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   30.0000 25

 17 omega   54.00   79.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 25

 18 omega   60.00  100.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  150.0000 40

 19 omega   47.00  131.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  120.0000 84
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0318913000
_diffrn_orient_matrix_UB_12      -0.0476222000
_diffrn_orient_matrix_UB_13      -0.0287895000
_diffrn_orient_matrix_UB_21      -0.0047407000
_diffrn_orient_matrix_UB_22      0.0357727000
_diffrn_orient_matrix_UB_23      -0.0390578000
_diffrn_orient_matrix_UB_31      0.2369493000
_diffrn_orient_matrix_UB_32      -0.0057016000
_diffrn_orient_matrix_UB_33      -0.0046484000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            21164
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.719
_diffrn_reflns_theta_min         3.707
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.509
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_description       block
_exptl_crystal_F_000             1952
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 3235 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     684
_refine_ls_number_reflns         9517
_refine_ls_number_restraints     109
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0430
_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^)+(0.0545P)^2^+0.4921P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1105
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    0.954
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                8490
_reflns_number_total             9517
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02334h2.cif
_cod_data_source_block           yuchx_0109
_cod_depositor_comments          'Adding full bibliography for 7157211.cif.'
_cod_original_cell_volume        5242.40(10)
_cod_database_code               7157211
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 98.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C2-C3 \\sim C46A_$1-C3
 with sigma of 0.02
 C2-C1 \\sim C46A_$1-C1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C24) \\sim Ueq, Uanis(C24B) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C23B)
\\sim Ueq, Uanis(O1B) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq,
Uanis(O1) \\sim Ueq, Uanis(C3B) \\sim Ueq, Uanis(C46A) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(C54) \\sim Ueq, Uanis(C54B) \\sim Ueq, Uanis(C53) \\sim Ueq, Uanis(C53B)
\\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C33B) \\sim Ueq,
Uanis(O3B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: C2(0.6) H2A(0.6) H2B(0.6) C3(0.6) H3(0.6) H1A(0.6) H1B(0.6)
 H54C(0.4) H54D(0.4) C23(0.6) H23A(0.6) H23B(0.6) H23C(0.6) O1(0.6) H1(0.6)
 H32A(0.65) H32B(0.65) H48C(0.35) H48D(0.35) O3(0.65) H3A(0.65) C33(0.65)
 H33(0.65) C54(0.65) H54A(0.65) H54B(0.65) H54E(0.65) C23B(0.4) H4A(0.4)
 H4B(0.4) H4C(0.4) C53(0.65) H53A(0.65) H53B(0.65) H53C(0.65) O1B(0.4)
 H0AA(0.4) C33B(0.35) H6AA(0.35) C54B(0.35) H8AA(0.35) H8AB(0.35) H8AC(0.35)
 C53B(0.35) H7AA(0.35) H7AB(0.35) H7AC(0.35) O3B(0.35) H59A(0.35) C24(0.6)
 H24A(0.6) H24B(0.6) H24C(0.6) C24B(0.4) H3AA(0.4) H3AB(0.4) H3AC(0.4) C3B(0.4)
 H0BA(0.4) C46A(0.4) H46C(0.4) H46D(0.4)
5.a Ternary CH refined with riding coordinates:
 C21(H21), C18(H18), C7(H7), C3(H3), C22(H22), C37(H37), C48(H48), C52(H52),
 C51(H51), C33(H33), C33B(H6AA), C3B(H0BA)
5.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C6(H6A,H6B), C19(H19A,H19B), C11(H11A,H11B), C12(H12A,H12B),
 C20(H20A,H20B), C2(H2A,H2B), C1(H1A,H1B), C1(H54C,H54D), C31(H31A,H31B),
 C41(H41A,H41B), C42(H42A,H42B), C36(H36A,H36B), C46(H46A,H46B), C32(H32A,H32B),
  C32(H48C,H48D), C49(H49A,H49B), C50(H50A,H50B), C46A(H46C,H46D)
5.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C45(H45)
5.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C25(H25A,H25B,
 H25C), C30(H30A,H30B,H30C), C23(H23A,H23B,H23C), C29(H29A,H29B,H29C), C56(H56A,
 H56B,H56C), C55(H55A,H55B,H55C), C58(H58A,H58B,H58C), C57(H57A,H57B,H57C),
 C59(H59B,H59C,H59D), C60(H60A,H60B,H60C), C54(H54A,H54B,H54E), C23B(H4A,H4B,
 H4C), C53(H53A,H53B,H53C), C54B(H8AA,H8AB,H8AC), C53B(H7AA,H7AB,H7AC),
 C24(H24A,H24B,H24C), C24B(H3AA,H3AB,H3AC)
5.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1), O4(H4), O3(H3A), O1B(H0AA), O3B(H59A)
;
_shelx_res_checksum              51076
_olex2_date_sample_data_collection 2019-01-09
_olex2_submission_special_instructions 'No special instructions were received'