First total synthesis of the biologically active 2,7-dioxygenated tricyclic carbazole alkaloids 7-methoxy-O-methylmukonal, clausine H (clauszoline-C), clausine K (clauszoline-J) and clausine O.
Kataeva, Olga; Krahl, Micha P.; Knölker, Hans-Joachim; Organic & biomolecular chemistry 3 (2005) 3099–3101; doi:10.1039/b507660a

data_7151347
_publ_section_title
;
 First total synthesis of the biologically active 2,7-dioxygenated
 tricyclic carbazole alkaloids 7-methoxy-O-methylmukonal, clausine H
 (clauszoline-C), clausine K (clauszoline-J) and clausine O.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3099
_journal_page_last               3101
_journal_paper_doi               10.1039/b507660a
_journal_volume                  3
_journal_year                    2005
_chemical_formula_sum            'C16 H15 N O4'
_chemical_formula_weight         285.29
_chemical_melting_point          464.6(5)
_chemical_name_common            'clausine H'
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.051(1)
_cell_length_b                   7.509(1)
_cell_length_c                   7.739(1)
_cell_measurement_reflns_used    34
_cell_measurement_temperature    198(2)
_cell_measurement_theta_max      19.52
_cell_measurement_theta_min      4.17
_cell_volume                     1339.5(3)
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'Schakal-99 (E.Keller 1999)'
_computing_publication_material  'XCIF 6.12 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      198(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_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  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15467
_diffrn_reflns_theta_full        25.40
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_correction_T_min  0.9506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2.03.(Sheldrick,Bruker AXS Inc.,2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    'refined as riding atoms'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2198
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0475P)^2^+0.0043P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0740
_reflns_number_gt                1835
_reflns_number_total             2198
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b507660a.txt
_cod_data_source_block           compound2
_cod_depositor_comments
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The following automatic conversions were performed:

'_chemical_melting_point' value '191-192 C' was changed to '464.6(5)'
- it was converted from degrees Celsius(C) to Kelvins(K), the average
value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
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_cod_original_sg_symbol_H-M      Pca2(1)
_cod_database_code               7151347