A complex stereochemical relay approach to the antimalarial alkaloid ocimicide A1. Evidence for a structural revision.
Nikolayevskiy, Herman; Tun, Kyaw Moe; Rablen, Paul R.; Ben Mamoun, Choukri; Herzon, Seth; Chem. Sci.  (2017) –; doi:10.1039/C7SC01127J

data_1545985
_publ_section_title
;
 A complex stereochemical relay approach to the antimalarial alkaloid
 ocimicide A1. Evidence for a structural revision.
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC01127J
_journal_year                    2017
_chemical_formula_moiety         'C24 H28 N4 O6'
_chemical_formula_sum            'C24 H28 N4 O6'
_chemical_formula_weight         468.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-03-11 deposited with the CCDC.
2017-05-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.159(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.7641(7)
_cell_length_b                   11.6113(4)
_cell_length_c                   14.8749(7)
_cell_measurement_reflns_used    10663
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      65.5880
_cell_measurement_theta_min      2.8330
_cell_volume                     2681.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_molecular_graphics
; 
Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., 
OLEX2: A complete structure solution, refinement and analysis program 
(2009). J. Appl. Cryst., 42, 339-341. 
;
_computing_publication_material  'CIFTAB-2014/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1919
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            81113
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.847
_diffrn_reflns_theta_max         66.847
_diffrn_reflns_theta_min         2.846
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.700
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.39.16b (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_description       Needle
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4754
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0604
_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^)+(0.0925P)^2^+0.3334P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1691
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3161
_reflns_number_total             4754
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc01127j2.cif
_cod_data_source_block           007-14186
_cod_database_code               1545985
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.884
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_checksum              85266
_shelx_hkl_checksum              30860
_shelx_fab_checksum              79821