Gelsecorydines A-E, Five Gelsedine-Corynanthe-Type Bisindole Alkaloids from the Fruits of Gelsemium elegans.
Li, Ni-Ping; Liu, Miao; Huang, Xiao-Jun; Gong, Xue-Ying; Zhang, Wei; Cheng, Min-Jing; Ye, Wen-Cai; Wang, Lei; The Journal of organic chemistry 83 (2018) 5707–5714; doi:10.1021/acs.joc.8b00736

data_4034813
_publ_section_title
;
 Gelsecorydines A-E, Five Gelsedine-Corynanthe-Type Bisindole Alkaloids
 from the Fruits of Gelsemium elegans.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5707
_journal_page_last               5714
_journal_paper_doi               10.1021/acs.joc.8b00736
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C40 H42 N4 O6, 3(C H4 O)'
_chemical_formula_sum            'C43 H54 N4 O9'
_chemical_formula_weight         770.90
_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     direct
_audit_creation_date             2017-05-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.07910(10)
_cell_length_b                   11.82320(10)
_cell_length_c                   31.0969(5)
_cell_measurement_reflns_used    20985
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3400
_cell_measurement_theta_min      3.9780
_cell_volume                     4073.40(8)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_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   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00  60.00  109
  2  \w   -115.00 -17.00   1.00    1.00    --  -40.98 -37.00 120.00   98
  3  \w      1.00  82.00   1.00    1.00    --   40.98 -99.00-120.00   81
  4  \w     34.00 121.00   1.00    2.50    --  106.95-125.00  30.00   87
  5  \w     94.00 178.00   1.00    2.50    --  106.95 125.00-150.00   84
  6  \w     94.00 178.00   1.00    2.50    --  106.95 125.00 150.00   84
  7  \w     94.00 178.00   1.00    2.50    --  106.95 125.00-180.00   84
  8  \w     54.00 178.00   1.00    2.50    --  106.95  15.00 -30.00  124
  9  \w     35.00 136.00   1.00    2.50    --  106.95 -61.00 120.00  101
 10  \w   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00 -90.00  109
 11  \w      1.00  82.00   1.00    1.00    --   40.98 -99.00 120.00   81
 12  \w     81.00 178.00   1.00    2.50    --  106.95  45.00  90.00   97
 13  \w     78.00 178.00   1.00    2.50    --  106.95  61.00  30.00  100
 14  \w     34.00 121.00   1.00    2.50    --  106.95-125.00 -30.00   87
 15  \w     54.00 178.00   1.00    2.50    --  106.95  15.00-150.00  124
 16  \w   -113.00 -13.00   1.00    1.00    --  -40.98 -57.00 -30.00  100
 17  \w      1.00  72.00   1.00    1.00    --   40.98 -99.00   0.00   71
;
_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      -0.0037687000
_diffrn_orient_matrix_UB_12      -0.0024620000
_diffrn_orient_matrix_UB_13      -0.0495151000
_diffrn_orient_matrix_UB_21      -0.0651509000
_diffrn_orient_matrix_UB_22      -0.1150601000
_diffrn_orient_matrix_UB_23      0.0014660000
_diffrn_orient_matrix_UB_31      -0.1228170000
_diffrn_orient_matrix_UB_32      0.0610542000
_diffrn_orient_matrix_UB_33      0.0007574000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            36572
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.893
_diffrn_reflns_theta_min         4.000
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.08904
_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            colorless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 2987 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         8146
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0485P)^2^+1.4315P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1074
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                7499
_reflns_number_total             8146
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00736_si_002.cif
_cod_data_source_block           674
_cod_database_code               4034813
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.919
_shelx_estimated_absorpt_t_min   0.864
_reflns_odcompleteness_completeness 99.95
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C00O(H00O), C00T(H00T), C00U(H00U), C00W(H00W), C012(H012), C013(H013),
 C017(H017)
2.b Secondary CH2 refined with riding coordinates:
 C00R(H00A,H00C), C00V(H00D,H00E), C00Z(H00J,H00K), C011(H01D,H01E), C01A(H01I,
 H01J)
2.c Aromatic/amide H refined with riding coordinates:
 N00B(H00B), C00H(H00H), C00M(H00M), C00Q(H00Q), C014(H014), C016(H016),
 C01B(H01K), C01C(H01L), C01E(H01P), C01F(H01Q), C01G(H01R), C01H(H01S)
2.d Idealised Me refined as rotating group:
 C00X(H00F,H00G,H00I), C010(H01A,H01B,H01C), C015(H01F,H01G,H01H), C01D(H01M,
 H01N,H01O), C01I(H01T,H01U,H01V), C01J(H01Z,H,HA), C01K(H01W,H01X,H01Y)
2.e Idealised tetrahedral OH refined as rotating group:
 O004(H004), O007(H007), O009(H009), O00D(H00L)
;
_shelx_res_checksum              30080
_shelx_hkl_checksum              63727
_shelx_fab_checksum              21403
_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 10.675
_oxdiff_exptl_absorpt_empirical_full_min 0.362