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_1566552
_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         'C17 H31 N O3'
_chemical_formula_sum            'C17 H31 N O3'
_chemical_formula_weight         297.43
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-13
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.1891(16)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.37896(19)
_cell_length_b                   5.01515(14)
_cell_length_c                   13.9105(3)
_cell_measurement_reflns_used    8663
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.4550
_cell_measurement_theta_min      4.4090
_cell_volume                     852.51(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'SHELXD  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00-150.00  109
  2  \w    -69.00  32.00   1.00    1.00    --  -40.98  57.00   0.00  101
  3  \w   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00-120.00  109
  4  \w   -115.00 -16.00   1.00    1.00    --  -40.98 -38.00 -90.00   99
  5  \w   -113.00 -65.00   1.00    1.00    --  -40.98-137.00 -49.00   48
  6  \w     13.00 113.00   1.00    1.00    --   40.98  57.00   0.00  100
  7  \w     23.00  97.00   1.00    1.00    --   40.98-125.00  90.00   74
  8  \w     78.00 178.00   1.00    1.00    --  106.95  61.00 -60.00  100
  9  \w     74.00 178.00   1.00    1.00    --  106.95  77.00-180.00  104
 10  \w     81.00 178.00   1.00    1.00    --  106.95  45.00-180.00   97
 11  \w     81.00 178.00   1.00    1.00    --  106.95  45.00 -90.00   97
 12  \w     74.00 178.00   1.00    1.00    --  106.95  77.00-120.00  104
 13  \w     78.00 178.00   1.00    1.00    --  106.95  61.00-120.00  100
 14  \w     74.00 178.00   1.00    1.00    --  106.95  77.00-150.00  104
 15  \w     78.00 178.00   1.00    1.00    --  106.95  61.00-180.00  100
 16  \w     74.00 178.00   1.00    1.00    --  106.95  77.00 -60.00  104
 17  \w     78.00 178.00   1.00    1.00    --  106.95  61.00 -90.00  100
 18  \w     74.00 178.00   1.00    1.00    --  106.95  77.00 150.00  104
 19  \w     78.00 178.00   1.00    1.00    --  106.95  61.00-150.00  100
 20  \w     74.00 178.00   1.00    1.00    --  106.95  77.00 -90.00  104
 21  \w     94.00 178.00   1.00    1.00    --  106.95 125.00-150.00   84
 22  \w     81.00 178.00   1.00    1.00    --  106.95  45.00-150.00   97
 23  \w     94.00 178.00   1.00    1.00    --  106.95 125.00  60.00   84
 24  \w     81.00 108.00   1.00    1.00    --  106.95  45.00 -30.00   27
 25  \w     25.00 109.00   1.00    1.00    --  106.95 -95.00   0.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0186321000
_diffrn_orient_matrix_UB_12      0.0159016000
_diffrn_orient_matrix_UB_13      -0.1067534000
_diffrn_orient_matrix_UB_21      0.1231431000
_diffrn_orient_matrix_UB_22      0.0445086000
_diffrn_orient_matrix_UB_23      0.0345816000
_diffrn_orient_matrix_UB_31      0.0190359000
_diffrn_orient_matrix_UB_32      -0.3036479000
_diffrn_orient_matrix_UB_33      -0.0004549000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12214
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.694
_diffrn_reflns_theta_min         3.218
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60159
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1227 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3147
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0321
_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^)+(0.0566P)^2^+0.1439P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.665
_reflns_Friedel_fraction_full    0.866
_reflns_Friedel_fraction_max     0.826
_reflns_number_gt                3104
_reflns_number_total             3147
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00960_si_003.cif
_cod_data_source_block           microgrewiapine_F
_cod_database_code               1566552
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 100.00
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C3(H3A), C5'(H5'), C6(H6), C6'(H6')
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7'(H7'A,H7'B), C8'(H8'A,H8'B), C9'(H9'A,H9'B)
2.c Aromatic/amide H refined with riding coordinates:
 C1'(H1'), C2'(H2'), C3'(H3'), C4'(H4')
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10'(H10A,H10B,H10C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              71166
_shelx_hkl_checksum              93957
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.471
_oxdiff_exptl_absorpt_empirical_full_min 0.633