Total Synthesis of Bruceolline I.
Scarpi, Dina; Faggi, Cristina; Occhiato, Ernesto G.; Journal of natural products 80 (2017) 2384–2388; doi:10.1021/acs.jnatprod.7b00311

data_1546590
_publ_section_title
;
 Total Synthesis of Bruceolline I.
;
_journal_issue                   8
_journal_name_full               'Journal of natural products'
_journal_page_first              2384
_journal_page_last               2388
_journal_paper_doi               10.1021/acs.jnatprod.7b00311
_journal_volume                  80
_journal_year                    2017
_chemical_formula_moiety         'C13 H11 N1 O3, H2 O1'
_chemical_formula_sum            'C13 H13 N O4'
_chemical_formula_weight         247.24
_chemical_name_common            'Bruceollina H'
_chemical_name_systematic
6-hydroxy-3,3-dimethylcyclopenta[b]indole-1,2(3H,4H)-dione
_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
_audit_creation_date
;
'Tue Jul 12 09:17:44 2016'
;
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 96.194(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.3080(2)
_cell_length_b                   30.6110(8)
_cell_length_c                   8.3800(2)
_cell_measurement_reflns_used    4158
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.4770
_cell_measurement_theta_min      4.8090
_cell_volume                     2373.75(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2004 J.Appl.Cryst.38,381-388'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.1241
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details
;
  1 omega -126.00  -79.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.2824  -99.0000    0.0000 47

  2 omega -126.00  -79.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.2824  -99.0000 -180.0000 47

  3 omega  -25.00   69.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       46.2824  -37.0000  -90.0000 94

  4 omega   73.00  118.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       46.2824  125.0000    0.0000 45

  5 omega -120.00  -18.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000   77.0000  -60.0000 102

  6 omega -159.00  -65.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -61.0000 -180.0000 94

  7 omega   24.00   69.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -30.0000   60.0000 45

  8 omega   24.00   69.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -30.0000   90.0000 45

  9 omega   24.00   69.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -30.0000   30.0000 45

 10 omega   24.00   54.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -30.0000 -150.0000 30

 11 omega   24.00   57.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -30.0000  -60.0000 33

 12 omega   36.00   76.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919  -45.0000  -30.0000 40

 13 omega  102.00  160.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       96.6919   45.0000   30.0000 58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12107
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.616
_diffrn_reflns_theta_min         4.779
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.865
_exptl_absorpt_correction_T_max  0.9744
_exptl_absorpt_correction_T_min  0.9372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         4335
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0512
_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^)+(0.0475P)^2^+0.4505P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1406
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3255
_reflns_number_total             4335
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np7b00311_si_001.cif
_cod_data_source_block           120
_cod_depositor_comments
;
        Adding full bibliography for 1546590.cif.

2019-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C13 H11 N1 O3, H2 O1)'
_cod_original_formula_sum        'C26 H26 N2 O8'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     494.49
_cod_database_code               1546590
_shelxl_version_number           2014/6
_shelx_res_checksum              29013
_shelx_hkl_checksum              29588