Total synthesis of malagashanine: a chloroquine potentiating indole alkaloid with unusual stereochemistry.
Kong, A.; Mancheno, D. E.; Boudet, N.; Delgado, R.; Andreansky, E. S.; Blakey, S. B.; Chemical science 8 (2017) 697–700; doi:10.1039/c6sc03578g

data_1544162
_publ_section_title
;
 Total synthesis of malagashanine: a chloroquine potentiating indole
 alkaloid with unusual stereochemistry.
;
_journal_issue                   1
_journal_name_full               'Chemical science'
_journal_page_first              697
_journal_page_last               700
_journal_paper_doi               10.1039/c6sc03578g
_journal_volume                  8
_journal_year                    2017
_chemical_formula_moiety         'C29 H34 N2 O6 S'
_chemical_formula_sum            'C29 H34 N2 O6 S'
_chemical_formula_weight         538.64
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a'
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-06-23
_audit_creation_method
;
Olex2 1.2-dev
(compiled 2016.05.11 svn.r3296 for OlexSys, GUI svn.r5177)
;
_audit_update_record
;
2016-07-01 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   29.2891(19)
_cell_length_b                   29.2891(19)
_cell_length_c                   18.1917(13)
_cell_measurement_reflns_used    2671
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      58.755
_cell_measurement_theta_min      2.860
_cell_volume                     15605.8(18)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'APEX2 v2014.11 (Bruker, 2014)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1158
_diffrn_reflns_av_unetI/netI     0.0828
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            37725
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        65.078
_diffrn_reflns_theta_max         65.078
_diffrn_reflns_theta_min         2.859
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.002
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0998 before and 0.0519 after correction.
The Ratio of minimum to maximum transmission is 0.7477.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.917
_exptl_crystal_description       irreg
_exptl_crystal_F_000             4576
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         6404
_refine_ls_number_restraints     249
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1707
_refine_ls_R_factor_gt           0.0690
_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^)+(0.0824P)^2^+3.5296P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1637
_refine_ls_wR_factor_ref         0.2190
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2484
_reflns_number_total             6404
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6sc03578g2.cif
_cod_data_source_block           dm-ii-253_sq
_cod_depositor_comments
;Adding full bibliography for 1544162.cif.

 Adding full bibliography for 1544162.cif.
;
_cod_original_cell_volume        15606(2)
_cod_database_code               1544162
_shelx_estimated_absorpt_t_max   0.898
_shelx_estimated_absorpt_t_min   0.714
_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. Rigid body (RIGU) restrains
 C3, C10, C4, C17, C2, C1, N2
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C3, C4, C9, N1, C10
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N1, C25, O3, C26, C9
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C9, C8, C7, C6, C5, C4, C3
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C11, C12, O4, C13, C14, C15, C27, C28
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C28, O5, O6, C29, C14
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C18, C23, C22, C21, C20, C19, C24
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3.a Ternary CH refined with riding coordinates:
 C10(H10), C15(H15), C14(H14), C11(H11), C13(H13), C17(H17)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C16(H16A,H16B), C12(H12A,H12B), C1(H1A,H1B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C7(H7), C6(H6), C23(H23), C22(H22), C19(H19), C20(H20)
3.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C24(H24A,H24B,
 H24C)
;
_shelx_fab_checksum              1905
_shelx_shelxl_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id DM-II-253
_olex2_submission_special_instructions 'No special instructions were received'