(9βH)- and 17-Nor-Pimaranes from Icacina oliviformis
Sun, Meng; Guo, Brian; Xu, Mingming; Zhao, Ming; Onakpa, Monday M.; Wu, Zhenlong; Burdette, Joanna E.; Che, Chun-Tao; Journal of Natural Products  (2021) –; doi:10.1021/acs.jnatprod.9b01131

data_1561308
_publ_section_title
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 (9\bH)- and 17-Nor-Pimaranes from Icacina oliviformis
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.9b01131
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H30 O12, 3(H2 O)'
_chemical_formula_sum            'C26 H36 O15'
_chemical_formula_weight         588.55
_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   mixed
_audit_creation_date             2020-10-20
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.880(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.6480(12)
_cell_length_b                   6.3182(7)
_cell_length_c                   20.729(2)
_cell_measurement_reflns_used    6805
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      53.74
_cell_measurement_theta_min      3.63
_cell_volume                     1387.2(3)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      193.0
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0773
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9960
_diffrn_reflns_point_group_measured_fraction_full 0.934
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.529
_diffrn_reflns_theta_min         1.864
_exptl_absorpt_coefficient_mu    0.639
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.757
_refine_diff_density_min         -0.731
_refine_diff_density_rms         0.111
_refine_ls_abs_structure_details
;
 Flack x determined using 1304 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     387
_refine_ls_number_reflns         4753
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0746
_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^)+(0.1560P)^2^+0.3705P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2174
_refine_ls_wR_factor_ref         0.2327
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.874
_reflns_Friedel_fraction_max     0.851
_reflns_number_gt                3843
_reflns_number_total             4753
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b01131_si_002.cif
_cod_data_source_block           20201017lin_nzy_xmm_0m_a_sq
_cod_database_code               1561308
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.927
_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, All O(H,H) groups
2. Restrained distances
 H2A-H5_$2
 2.1 with sigma of 0.01
 H3A-H4A_$1
 2.1 with sigma of 0.01
 H2A-H3A_$1
 2.1 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
O16 \\sim O15: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
4. Others
 Sof(O16)=Sof(H16C)=Sof(H16D)=1-FVAR(1)
 Sof(O15)=Sof(H15C)=Sof(H15D)=FVAR(1)
5.a Riding coordinates:
 C3(H3), C13(H13), C26(H26A,H26B,H26C), O1(H1), O4(H4A), O13(H13A,H13B),
 O14(H14A,H14B), O15(H15C,H15D)
5.b Free rotating group:
 O16(H16C,H16D)
5.c Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C12(H12)
5.d Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C15(H15A,H15B), C16(H16A,H16B), C19(H19A,H19B)
5.e Aromatic/amide H refined with riding coordinates:
 C22(H22), C23(H23), C25(H25)
5.f Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
5.g Idealised tetrahedral OH refined as rotating group:
 O3(H3A), O8(H8), O2(H2A)
;
_shelx_res_checksum              78493
_shelx_hkl_checksum              7057
_shelx_shelxl_version_number     2018/3
_olex2_submission_special_instructions 'No special instructions were received'