Synthesis of Alstoscholarisines A-E, Monoterpene Indole Alkaloids with Modulating Effects on Neural Stem Cells.
Mason, Jeremy D.; Weinreb, Steven M.; The Journal of organic chemistry 83 (2018) 5877–5896; doi:10.1021/acs.joc.8b00889

data_4035778
_publ_section_title
;
 Synthesis of Alstoscholarisines A-E, Monoterpene Indole Alkaloids with
 Modulating Effects on Neural Stem Cells.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5877
_journal_page_last               5896
_journal_paper_doi               10.1021/acs.joc.8b00889
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C27 H30 N2 O4 S'
_chemical_formula_sum            'C27 H30 N2 O4 S'
_chemical_formula_weight         478.59
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-07-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_cell_angle_alpha                90.378(7)
_cell_angle_beta                 104.548(7)
_cell_angle_gamma                109.881(7)
_cell_formula_units_Z            2
_cell_length_a                   10.578(4)
_cell_length_b                   10.734(4)
_cell_length_c                   12.077(5)
_cell_measurement_reflns_used    6465
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.337
_cell_measurement_theta_min      2.361
_cell_volume                     1241.8(8)
_computing_cell_refinement       'SAINT V6.36A (BRUKER, 2016)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT V6.36A (BRUKER, 2016)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0875
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18915
_diffrn_reflns_theta_full        28.60
_diffrn_reflns_theta_max         28.60
_diffrn_reflns_theta_min         1.75
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           32.0
_diffrn_source_power             1.6
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_T_max  0.9
_exptl_absorpt_correction_T_min  0.072150
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS V2.05 (BRUKER, 2001) was used for absorption correction.
R(int) was 0.1171 before and 0.0919 after correction.
The Ratio of minimum to maximum transmission is 0.0722.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.19(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     619
_refine_ls_number_reflns         9814
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0744
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1114P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1872
_refine_ls_wR_factor_ref         0.2090
_reflns_number_gt                6223
_reflns_number_total             9814
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b00889_si_002.cif
_cod_data_source_block           jdm3s
_cod_original_cell_volume        1241.8(9)
_cod_database_code               4035778
_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
2. Uiso/Uaniso restraints and constraints
Uanis(O4) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
3.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C17(H17), C30(H30), C31(H31), C32(H32), C45(H45)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C28(H28A,H28B), C29(H29A,H29B),
 C33(H33A,H33B)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C13(H13), C14(H14), C15(H15), C16(H16), C22(H22), C23(H23), C25(H25),
 C26(H26), C34(H34), C40(H40), C41(H41), C42(H42), C43(H43), C49(H49), C50(H50),
  C52(H52), C53(H53)
3.d X=CH2 refined with riding coordinates:
 C8(H8A,H8B), C35(H35A,H35B)
3.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C27(H27A,H27B,H27C), C44(H44A,H44B,
 H44C), C47(H47A,H47B,H47C), C54(H54A,H54B,H54C)
;
_olex2_submission_special_instructions 'No special instructions were received'