Gelsekoumidines A and B: Two Pairs of Atropisomeric Bisindole Alkaloids from the Roots of Gelsemium elegans.
Zhang, Wei; Xu, Wei; Wang, Gui-Yang; Gong, Xue-Ying; Li, Ni-Ping; Wang, Lei; Ye, Wen-Cai; Organic letters 19 (2017) 5194–5197; doi:10.1021/acs.orglett.7b02463

data_1547159
_publ_section_title
;
 Gelsekoumidines A and B: Two Pairs of Atropisomeric Bisindole Alkaloids
 from the Roots of Gelsemium elegans.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5194
_journal_page_last               5197
_journal_paper_doi               10.1021/acs.orglett.7b02463
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C39 H40 N4 O6, 4(O)'
_chemical_formula_sum            'C39 H40 N4 O10'
_chemical_formula_weight         724.75
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.5813(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6396(3)
_cell_length_b                   20.1301(4)
_cell_length_c                   14.1840(3)
_cell_measurement_reflns_used    11113
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.8410
_cell_measurement_theta_min      3.8020
_cell_volume                     3607.55(14)
_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, 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 0.993
_diffrn_measured_fraction_theta_max 0.971
_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   -115.00 -16.00   1.00    1.37    --  -40.48 -37.00 120.00   99
  2  \w    -65.00  34.00   1.00    1.37    --  -40.48  37.00 150.00   99
  3  \w    -69.00  33.00   1.00    1.37    --  -40.48  57.00   0.00  102
  4  \w   -115.00 -16.00   1.00    1.37    --  -40.48 -37.00-150.00   99
  5  \w     23.00  97.00   1.00    1.37    --   40.48-125.00  60.00   74
  6  \w      1.00  81.00   1.00    1.37    --   40.48 -99.00-180.00   80
  7  \w     75.00 178.00   1.00    5.48    --  107.58  77.00 120.00  103
  8  \w     82.00 178.00   1.00    5.48    --  107.58  45.00-180.00   96
  9  \w     82.00 178.00   1.00    5.48    --  107.58  45.00  90.00   96
 10  \w     82.00 178.00   1.00    5.48    --  107.58  45.00 -90.00   96
 11  \w     94.00 178.00   1.00    5.48    --  107.58 125.00-120.00   84
 12  \w     25.00 109.00   1.00    5.48    --  107.58 -94.00  90.00   84
 13  \w     25.00 109.00   1.00    5.48    --  107.58 -94.00 -90.00   84
 14  \w     75.00 175.00   1.00    5.48    --  107.58  77.00 -90.00  100
;
_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      -0.1045317000
_diffrn_orient_matrix_UB_12      0.0096809000
_diffrn_orient_matrix_UB_13      0.0520075000
_diffrn_orient_matrix_UB_21      0.0225469000
_diffrn_orient_matrix_UB_22      -0.0637034000
_diffrn_orient_matrix_UB_23      0.0573826000
_diffrn_orient_matrix_UB_31      0.0587892000
_diffrn_orient_matrix_UB_32      0.0412767000
_diffrn_orient_matrix_UB_33      0.0762285000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26285
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.899
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.020
_diffrn_reflns_theta_min         3.813
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.805
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34621
_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    1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details
;
 Flack x determined using 4646 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     963
_refine_ls_number_reflns         13180
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0759
_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^)+(0.1479P)^2^+2.0319P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2056
_refine_ls_wR_factor_ref         0.2176
_reflns_Friedel_coverage         0.799
_reflns_Friedel_fraction_full    0.877
_reflns_Friedel_fraction_max     0.823
_reflns_number_gt                11944
_reflns_number_total             13180
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02463_si_002.cif
_cod_data_source_block           ga
_cod_depositor_comments          'Adding full bibliography for 1547159.cif.'
_cod_original_cell_volume        3607.54(12)
_cod_database_code               1547159
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.37
_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:
 C3'(H3'), C010(H010), C15'(H15'), C012(H012), C018(H018), C16'(H16'),
 C5'(H5'), C01G(H01G), C01H(H01H), C01O(H01O), C5(H5), C01S(H01S), C14'(H14'),
 C16(H16), C3(H3A), C15(H15), C02I(H02I), C02Q(H02Q)
2.b Secondary CH2 refined with riding coordinates:
 C017(H01A,H01B), C01A(H01C,H01D), C17'(H17A,H17B), C6'(H6'A,H6'B), C17(H17C,
 H17D), C029(H02A,H02B), C6(H6A,H6B), C02C(H02C,H02D), C14(H14A,H14B),
 C02L(H02H,H02L)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C00W(H00W), C00X(H00X), C015(H015), C016(H016),
 C01I(H01I), C9(H9), C10(H10), C11'(H11'), C12'(H12'), C01Z(H01Z), C022(H022),
 C22(H22), C9'(H9'), C10'(H10'), C11(H11), C02J(H02J), C02K(H02K), C02M(H02M),
 C02O(H02O), C12(H12)
2.d Idealised Me refined as rotating group:
 C18'(H18A,H18B,H18C), C02F(H02E,H02F,H02G), C21(H21A,H21B,H21C), C21'(H21D,
 H21E,H21F), C02T(H02N,H02P,H02R), C02U(H02S,H02T,H02U)
2.e Idealised tetrahedral OH refined as rotating group:
 O006(H006), O3(H3)
;
_olex2_date_sample_data_collection 2017-03-08
_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 2.006
_oxdiff_exptl_absorpt_empirical_full_min 0.493