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_7160012
_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            'C30 H35 I N2 O6'
_chemical_formula_weight         646.50
_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   mixed
_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                 111.9770(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.0831(6)
_cell_length_b                   9.8234(5)
_cell_length_c                   13.0300(6)
_cell_measurement_reflns_used    9687
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.93
_cell_measurement_theta_min      2.67
_cell_volume                     1434.24(12)
_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  'SHELXL2014/7, Sheldrick, G. M. 2014'
_computing_structure_refinement  'SHELXL2014/7, Sheldrick G. M. 2014'
_computing_structure_solution    'SHELXL2014/7, Sheldrick G. M. 2014'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            45405
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         33.356
_diffrn_reflns_theta_min         2.672
_diffrn_source                   'I\mS microsource 3.0'
_exptl_absorpt_coefficient_mu    1.162
_exptl_absorpt_correction_T_max  0.9539
_exptl_absorpt_correction_T_min  0.8514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M., sadabs (2014). Acta Cryst. C71, 3--8.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_description       needle
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.058
_exptl_transmission_factor_max   0.5659
_exptl_transmission_factor_min   0.5264
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.987
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
; 
 Flack x determined using 4234 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.017(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         9830
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0206
_refine_ls_R_factor_gt           0.0198
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0226P)^2^+0.3774P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0477
_refine_ls_wR_factor_ref         0.0481
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.839
_reflns_number_gt                9642
_reflns_number_total             9830
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00853g2.cif
_cod_data_source_block           Y-20
_cod_depositor_comments
'Adding full bibliography for 7160009--7160014.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7160012
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.755
_shelx_estimated_absorpt_t_max   0.936
_shelx_res_checksum              47785
_publcif_funding_html
;
;