A one-pot multicomponent coupling/cyclization for natural product herbicide (±)-thaxtomin A.
Bourgault, Jean Paul; Maddirala, Amarendar Reddy; Andreana, Peter R.; Organic & biomolecular chemistry 12 (2014) 8125–8127; doi:10.1039/c4ob01148a

data_7153957
_publ_section_title
;
 A one-pot multicomponent coupling/cyclization for natural product
 herbicide (+-)-thaxtomin A.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8125
_journal_page_last               8127
_journal_paper_doi               10.1039/c4ob01148a
_journal_volume                  12
_journal_year                    2014
_chemical_formula_moiety         'C22 H22 N4 O6, 0.2 CH3OH'
_chemical_formula_sum            'C22.2 H22.8 N4 O6.2'
_chemical_formula_weight         444.84
_chemical_name_systematic        '()-Thaxtomin A '
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 111.2467(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4151(3)
_cell_length_b                   11.3424(3)
_cell_length_c                   14.8403(3)
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      60.0
_cell_measurement_theta_min      3.8
_cell_volume                     2104.61(9)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Apex CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_source         'ImuS microfocus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21585
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        61.000
_diffrn_reflns_theta_max         59.842
_diffrn_reflns_theta_min         3.811
_exptl_absorpt_coefficient_mu    0.872
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_correction_T_min  0.682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_description       plate
_exptl_crystal_F_000             934
_exptl_crystal_size_max          0.137
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         3100
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0417
_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^)+(0.0523P)^2^+2.1110P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1106
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2963
_reflns_number_total             3100
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ob01148a2.cif
_cod_data_source_block           redo100
_cod_depositor_comments
'Adding full bibliography for 7153956--7153957.cif.'
_cod_original_formula_sum        'C22.20 H22.80 N4 O6.20'
_cod_database_code               7153957
_shelx_estimated_absorpt_t_min   0.682
_shelx_estimated_absorpt_t_max   0.752
_shelxl_version_number           2014-3