Chloroformate-mediated ring cleavage of indole alkaloids leads to re-engineered antiplasmodial agents.
Schultz, Daniel C.; Chávez-Riveros, Alejandra; Goertzen, 2nd, Michael G; Brummel, Beau R.; Paes, Raphaella A.; Santos, Natalia M.; Tenneti, Srinivasarao; Abboud, Khalil A.; Rocca, James R.; Seabra, Gustavo; Li, Chenglong; Chakrabarti, Debopam; Huigens, 3rd, Robert W; Organic & biomolecular chemistry 22 (2024) 8423–8436; doi:10.1039/d4ob00853g

data_7160011
_publ_section_title
;
 Chloroformate-mediated ring cleavage of indole alkaloids leads to
 re-engineered antiplasmodial agents.
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8423
_journal_page_last               8436
_journal_paper_doi               10.1039/d4ob00853g
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H30 N2 O5'
_chemical_formula_weight         426.50
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-03-08 deposited with the CCDC.	2024-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.69(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.382(3)
_cell_length_b                   7.3133(13)
_cell_length_c                   16.086(6)
_cell_measurement_reflns_used    9737
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.96
_cell_measurement_theta_min      2.84
_cell_volume                     1067.6(6)
_computing_cell_refinement       'Bruker APEX3 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX3 (Bruker, 2014)'
_computing_data_reduction        'Bruker Apex3 SAINT (Bruker, 2014)'
_computing_molecular_graphics    'XP in SHELXTL-plus, Bruker 2014'
_computing_publication_material  'SHELXL2015, Sheldrick, G. M. 2015'
_computing_structure_refinement  'SHELXL2015, Sheldrick G. M. 2015'
_computing_structure_solution    'SHELXL2015, Sheldrick G. M. 2015'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'D8 Venture with PHOTON III'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            36941
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.085
_diffrn_reflns_theta_min         2.840
_diffrn_source                   'micro source 3.0'
_exptl_absorpt_coefficient_mu    0.728
_exptl_absorpt_correction_T_max  0.9567
_exptl_absorpt_correction_T_min  0.8262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M., sadabs (2015). Acta Cryst. C71, 3-8.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       needles
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.066
_exptl_transmission_factor_max   0.6617
_exptl_transmission_factor_min   0.5500
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
; 
 Flack x determined using 1712 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.13(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3872
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0303
_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^)+(0.0596P)^2^+0.2024P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0856
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                3861
_reflns_number_total             3872
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00853g2.cif
_cod_data_source_block           V-27
_cod_depositor_comments
'Adding full bibliography for 7160009--7160014.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7160011
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.751
_shelx_estimated_absorpt_t_max   0.954
_shelx_res_checksum              66513
_publcif_funding_html
;
;