Angiogenesis-Inhibitory Piperidine Alkaloids from the Leaves of <i>Microcos paniculata</i>.
Wu, Zhen-Long; Zhang, Wei-Yan; Zhong, Jin-Cheng; Huang, Xiao-Jun; Xu, Wei; Chen, Min-Feng; Weng, Shao-Quan; Zhang, Dong-Mei; Che, Chun-Tao; Ye, Wen-Cai; Wang, Ying; Journal of natural products 85 (2022) 375–383; doi:10.1021/acs.jnatprod.1c00960

data_1566554
_publ_section_title
;
 Angiogenesis-Inhibitory Piperidine Alkaloids from the Leaves of
 <i>Microcos paniculata</i>.
;
_journal_issue                   2
_journal_name_full               'Journal of natural products'
_journal_page_first              375
_journal_page_last               383
_journal_paper_doi               10.1021/acs.jnatprod.1c00960
_journal_volume                  85
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H25 N O'
_chemical_formula_sum            'C16 H25 N O'
_chemical_formula_weight         247.37
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-01-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.08090(10)
_cell_length_b                   9.5095(2)
_cell_length_c                   31.1268(6)
_cell_measurement_reflns_used    6683
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.1300
_cell_measurement_theta_min      2.7960
_cell_volume                     1503.95(5)
_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      99.99(10)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            14387
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.857
_diffrn_reflns_theta_min         2.839
_exptl_absorpt_coefficient_mu    0.514
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.092
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1100 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         3009
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0409
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1318
_reflns_Friedel_coverage         0.670
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                2856
_reflns_number_total             3009
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00960_si_004.cif
_cod_data_source_block           microgrewiapine_G
_cod_database_code               1566554
_shelx_shelxl_version_number     2017/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C9'(H9'A,H9'B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C8'(H8'), C1'(H1'), C7'(H7'), C2'(H2'), C5'(H5'), C3'(H3'), C6'(H6'), C4'(H4')
2.d Idealised Me refined as rotating group:
 C4BA(H4BA,H4BB,H4BC), C10'(H10A,H10B,H10C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1AA(H1AA)
;
_shelx_res_checksum              93862
_shelx_hkl_checksum              87952
_olex2_submission_special_instructions 'No special instructions were received'