Structurally Diverse Indole Alkaloids with Vasorelaxant Activity from Melodinus hemsleyanus
Zhang, Jian; Liu, Zhi-Wen; Li, Yong; Wei, Cui-Jie; Xie, Jing; Yuan, Meng-Fei; Zhang, Dong-Mei; Ye, Wen-Cai; Zhang, Xiao-Qi; Journal of Natural Products  (2020) –; doi:10.1021/acs.jnatprod.9b00925

data_1558624
_publ_section_title
;
 Structurally Diverse Indole Alkaloids with Vasorelaxant Activity from
 Melodinus hemsleyanus
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.9b00925
_journal_year                    2020
_chemical_formula_moiety         'C20 H25 N3 O5, 4(O)'
_chemical_formula_sum            'C20 H25 N3 O9'
_chemical_formula_weight         451.43
_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     dual
_audit_creation_date             2018-07-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.70090(10)
_cell_length_b                   11.6468(2)
_cell_length_c                   42.6723(7)
_cell_measurement_reflns_used    25578
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5960
_cell_measurement_theta_min      3.9240
_cell_volume                     4324.31(11)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_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    -70.00  34.00   1.00    1.00    --  -40.46  57.00 -60.00  104
  2  \w     23.00  98.00   1.00    1.00    --   40.46-125.00 120.00   75
  3  \w      1.00  82.00   1.00    1.00    --   40.46 -99.00 150.00   81
  4  \w     29.00 115.00   1.00    1.06    --  107.48-111.00 -90.00   86
  5  \w     77.00 178.00   1.00    1.06    --  107.48  61.00  30.00  101
  6  \w    100.00 178.00   1.00    1.06    --  107.48 111.00 -60.00   78
  7  \w     46.00 178.00   1.00    1.06    --  107.48  15.00-180.00  132
  8  \w     23.00 109.00   1.00    1.06    --  107.48 -94.00 -30.00   86
  9  \w    100.00 178.00   1.00    1.06    --  107.48 111.00  60.00   78
 10  \w   -114.00 -11.00   1.00    1.00    --  -40.46 -57.00 -90.00  103
 11  \w   -114.00 -11.00   1.00    1.00    --  -40.46 -57.00 150.00  103
 12  \w     77.00 178.00   1.00    1.06    --  107.48  30.00 -90.00  101
 13  \w     77.00 178.00   1.00    1.06    --  107.48  61.00 -30.00  101
 14  \w     80.00 178.00   1.00    1.06    --  107.48  45.00-150.00   98
 15  \w     33.00 138.00   1.00    1.06    --  107.48 -61.00   0.00  105
 16  \w   -114.00 -11.00   1.00    1.00    --  -40.46 -57.00  30.00  103
 17  \w    -67.00  36.00   1.00    1.00    --  -40.46  37.00  60.00  103
 18  \w     74.00 178.00   1.00    1.06    --  107.48  77.00  60.00  104
;
_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      -0.1537969000
_diffrn_orient_matrix_UB_12      -0.0652304000
_diffrn_orient_matrix_UB_13      0.0018017000
_diffrn_orient_matrix_UB_21      0.0092320000
_diffrn_orient_matrix_UB_22      -0.0253294000
_diffrn_orient_matrix_UB_23      -0.0353909000
_diffrn_orient_matrix_UB_31      0.0872016000
_diffrn_orient_matrix_UB_32      -0.1122536000
_diffrn_orient_matrix_UB_33      0.0069253000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            43899
_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         73.748
_diffrn_reflns_theta_min         3.934
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.938
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87773
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.662
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Flack x determined using 3549 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     596
_refine_ls_number_reflns         8633
_refine_ls_number_restraints     16
_refine_ls_restrained_S_all      3.061
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0468
_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^)+(0.0809P)^2^+3.8099P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1344
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                8475
_reflns_number_total             8633
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00925_si_003.cif
_cod_data_source_block           dmh-21
_cod_database_code               1558624
_shelx_shelxl_version_number     2016/4
_reflns_odcompleteness_completeness 99.93
_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 N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H00B-H00G
 2.15 with sigma of 0.02
 H2A-H10A
 2.15 with sigma of 0.02
3. Rigid bond restraints
 N2, C12
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 N002, C00R
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
N2 \\sim C12: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
N002 \\sim C00R: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004
5.a Ternary CH refined with riding coordinates:
 C00Y(H00Y), C17(H17), C014(H014), C19(H19), C18(H18), C01D(H01F), C01J(H01K)
5.b Secondary CH2 refined with riding coordinates:
 C00Z(H00D,H00E), C016(H01A,H01B), C017(H01C,H01D), C01F(H01H,H01I), C13(H13A,
 H13B), C16(H16A,H16B), C9(H9A,H9B), C10(H10A,H10B)
5.c Aromatic/amide H refined with riding coordinates:
 N00G(H00G), C013(H013), C01C(H01E), C01E(H01G), C01I(H01J), C8(H8), C5(H5A),
 C6(H6), C7(H7)
5.d X=CH2 refined with riding coordinates:
 N002(H00A,H00B), N2(H2A,H2B)
5.e Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C01R(H01L,H01M,H01N)
5.f Idealised tetrahedral OH refined as rotating group:
 O5(H5), O003(H003), O4(H4), O008(H008), O3(H3)
;
_shelx_res_checksum              21288
_shelx_hkl_checksum              2496
_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 1.212
_oxdiff_exptl_absorpt_empirical_full_min 0.886