POCl3-mediated Cyclization of (+)-S-Mahanimbine Led to the Divergent Synthesis of Natural Product Derivatives with Antiplasmodial Activity.
Yedukondalu, Nalli; Thakur, Vandana; Mohmmed, Asif; Gupta, Vivek; Ali, Asif; New J. Chem. 41 (2017) 4923–4930; doi:10.1039/C7NJ00487G

data_7056167
_publ_section_title
;
 POCl3-mediated Cyclization of (+)-S-Mahanimbine Led to the Divergent
 Synthesis of Natural Product Derivatives with Antiplasmodial Activity.
;
_journal_issue                   12
_journal_name_full               'New J. Chem.'
_journal_page_first              4923
_journal_page_last               4930
_journal_paper_doi               10.1039/C7NJ00487G
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         'C23 H25 N O'
_chemical_formula_sum            'C23 H25 N O'
_chemical_formula_weight         331.44
_chemical_name_common            MK-POCL3-R
_chemical_name_systematic
; 
 5,7-dimethyl-2-(propan-2-ylidene)-1,2,3,4,5,13-hexahydro-1,5-
 methanooxocino[3,2-a]carbazole 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc14hz2p
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-04-06 deposited with the CCDC.
2017-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.851(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.4284(6)
_cell_length_b                   18.5039(14)
_cell_length_c                   23.3119(16)
_cell_measurement_reflns_used    3356
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6210
_cell_measurement_theta_min      3.7750
_cell_volume                     3627.5(5)
_computing_cell_refinement       'CrysAlis Pro  (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis Pro  (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis Pro  (Oxford Diffraction, 2010)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1049
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Xcalibur, sapphire3'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_av_sigmaI/netI    0.1404
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14007
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.43
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Crysalis PRO (Oxford Diffraction, 2010)'
_exptl_crystal_colour            'color less'
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0023(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         7064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.1760
_refine_ls_R_factor_gt           0.0791
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0758P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1726
_refine_ls_wR_factor_ref         0.2269
_reflns_number_gt                2884
_reflns_number_total             7064
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7nj00487g2.cif
_cod_data_source_block           5
_cod_depositor_comments
;

2017-11-13
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      P21/c
_cod_original_formula_moiety     'C46 H50 N2 O2'
_cod_original_formula_sum        'C46 H50 N2 O2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     662.88
_cod_database_code               7056167