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_1558623
_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_absolute_configuration ad
_chemical_formula_moiety         'C20 H20 N2 O3'
_chemical_formula_sum            'C20 H20 N2 O3'
_chemical_formula_weight         336.38
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-26
_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                   7.6535(3)
_cell_length_b                   13.7374(5)
_cell_length_c                   31.5932(15)
_cell_measurement_reflns_used    6630
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4480
_cell_measurement_theta_min      3.4710
_cell_volume                     3321.7(2)
_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 0.992
_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    -33.00  65.00   1.00    1.10    --   40.98 -37.00  30.00   98
  2  \w      0.00 121.00   1.00    1.10    --   40.98  19.00-150.00  121
  3  \w     94.00 178.00   1.00    4.39    --  106.95 125.00   0.00   84
  4  \w     24.00 109.00   1.00    4.39    --  106.95 -94.00 -60.00   85
  5  \w     24.00 109.00   1.00    4.39    --  106.95 -94.00   0.00   85
  6  \w     94.00 178.00   1.00    4.39    --  106.95 125.00 -30.00   84
  7  \w     81.00 178.00   1.00    4.39    --  106.95  45.00 -60.00   97
  8  \w     79.00 178.00   1.00    4.39    --  106.95  30.00  60.00   99
  9  \w     94.00 178.00   1.00    4.39    --  106.95 125.00  90.00   84
 10  \w   -117.00  -8.00   1.00    1.10    --  -40.98 -77.00  30.00  109
 11  \w      1.00  82.00   1.00    1.10    --   40.98 -99.00-120.00   81
 12  \w     79.00 134.00   1.00    4.39    --  106.95  30.00-150.00   55
;
_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      0.1131659000
_diffrn_orient_matrix_UB_12      0.0806102000
_diffrn_orient_matrix_UB_13      -0.0199570000
_diffrn_orient_matrix_UB_21      0.0591801000
_diffrn_orient_matrix_UB_22      0.0324036000
_diffrn_orient_matrix_UB_23      0.0444333000
_diffrn_orient_matrix_UB_31      0.1555924000
_diffrn_orient_matrix_UB_32      -0.0709061000
_diffrn_orient_matrix_UB_33      -0.0023907000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            20305
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.785
_diffrn_reflns_theta_min         2.797
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.739
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23379
_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    1.345
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details
;
 Flack x determined using 2090 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       0.00040(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         6612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.1013
_refine_ls_R_factor_gt           0.0951
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0492P)^2^+13.7136P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2315
_refine_ls_wR_factor_ref         0.2350
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                5963
_reflns_number_total             6612
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00925_si_002.cif
_cod_data_source_block           dnh-a-15
_cod_database_code               1558623
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.910
_reflns_odcompleteness_completeness 99.97
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00F(H00I), C00S(H00S), C00Z(H00Z), C014(H014)
2.b Secondary CH2 refined with riding coordinates:
 C00G(H00A,H00B), C00Q(H00C,H00D), C00V(H00E,H00F), C00W(H00G,H00H), C015(H01D,
 H01E), C017(H01F,H01G), C01B(H01I,H01J), C01D(H01L,H01M)
2.c Aromatic/amide H refined with riding coordinates:
 N007(H007), N008(H008), C00H(H00J), C00N(H00N), C00R(H00R), C00U(H00U),
 C00X(H00X), C00Y(H00Y), C010(H010), C013(H013), C016(H016), C018(H018),
 C01A(H01H), C01C(H01K)
2.d Idealised Me refined as rotating group:
 C012(H01A,H01B,H01C), C01E(H01N,H01O,H01P)
;
_shelx_res_checksum              85351
_shelx_hkl_checksum              95950
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.619
_oxdiff_exptl_absorpt_empirical_full_min 0.483