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_1566551
_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 unk
_chemical_formula_moiety         'C17 H29 N O'
_chemical_formula_sum            'C17 H29 N O'
_chemical_formula_weight         263.41
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-12
_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                 92.55(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.180(2)
_cell_length_b                   4.6280(11)
_cell_length_c                   48.944(12)
_cell_measurement_reflns_used    395
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      52.6450
_cell_measurement_theta_min      6.1510
_cell_volume                     1624.8(7)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5368
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.963
_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      7.00  35.00   1.00    3.00    --  -40.98  77.00  60.00   28
  2  \w    -70.00   5.00   1.00    3.00    --  -40.98  77.00  60.00   75
  3  \w     61.00 106.00   1.00    3.00    --   40.98  38.00-150.00   45
  4  \w    117.00 170.00   1.00    5.00    --  106.95  45.00-150.00   53
  5  \w    127.00 178.00   1.00    5.00    --  106.95 125.00-150.00   51
  6  \w     45.00 118.00   1.00    5.00    --  106.95 -45.00 120.00   73
  7  \w     32.00 105.00   1.00    5.00    --  106.95 -95.00 150.00   73
  8  \w     25.00 159.00   1.00    5.00    --  106.95 -15.00  30.00  134
  9  \w   -113.00 -31.00   1.00    3.00    --  -40.98 -57.00 120.00   82
;
_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      -0.2145681000
_diffrn_orient_matrix_UB_12      0.0168251000
_diffrn_orient_matrix_UB_13      -0.0016716000
_diffrn_orient_matrix_UB_21      0.0019505000
_diffrn_orient_matrix_UB_22      -0.0046062000
_diffrn_orient_matrix_UB_23      -0.0314381000
_diffrn_orient_matrix_UB_31      -0.0102932000
_diffrn_orient_matrix_UB_32      -0.3325709000
_diffrn_orient_matrix_UB_33      0.0003938000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_unetI/netI     0.1418
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -60
_diffrn_reflns_number            5885
_diffrn_reflns_point_group_measured_fraction_full 0.692
_diffrn_reflns_point_group_measured_fraction_max 0.658
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.847
_diffrn_reflns_theta_min         2.711
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44413
_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    0.538
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.3(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         4339
_refine_ls_number_restraints     33
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1288
_refine_ls_R_factor_gt           0.0987
_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^)+(0.1609P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2885
_refine_ls_wR_factor_ref         0.3282
_reflns_Friedel_coverage         0.211
_reflns_Friedel_fraction_full    0.294
_reflns_Friedel_fraction_max     0.264
_reflns_number_gt                2403
_reflns_number_total             4339
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00960_si_008.cif
_cod_data_source_block           microgrewiapine_A
_cod_original_cell_volume        1624.7(8)
_cod_database_code               1566551
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.976
_reflns_odcompleteness_completeness 99.76
_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. Restrained distances
 C1-C16
 1.35 with sigma of 0.02
3. Rigid bond restraints
 C12, C13
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C12 \\sim C13: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
Uanis(C4) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.004
Uanis(N1) = Uanis(C17)
Uanis(C5) = Uanis(C6)
Uanis(C1) = Uanis(C2)
Uanis(C1) = Uanis(C16)
Uanis(C3) = Uanis(C4)
Uanis(C9) = Uanis(C10)
5.a Ternary CH refined with riding coordinates:
 C5(H5), C1(H1A), C2(H2)
5.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C13(H13A,H13B), C14(H14A,H14B), C12(H12A,H12B)
5.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C11(H11), C8(H8), C10(H10), C9(H9)
5.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C16(H16A,H16B,H16C), C15(H15A,H15B,H15C)
5.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              7981
_shelx_hkl_checksum              59456
_shelx_fab_checksum              805
_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 1.606
_oxdiff_exptl_absorpt_empirical_full_min 0.570