#------------------------------------------------------------------------------
#$Date: 2025-08-22 13:33:34 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301861 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/13/7151347.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7151347
loop_
_publ_author_name
'Kataeva, Olga'
'Krahl, Micha P.'
'Knölker, Hans-Joachim'
_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 & 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/[σ²(Fo²)+(0.0475P)²+0.0043P] where P=(Fo²+2Fc²)/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
;
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 
;
_cod_original_sg_symbol_H-M      Pca2(1)
_cod_database_code               7151347
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.30212(8) 0.5939(3) -0.0101(2) 0.0251(4) Uani 1 1 d . . .
C2 C 0.25146(9) 0.6863(3) -0.0649(3) 0.0268(4) Uani 1 1 d . . .
C3 C 0.25505(8) 0.8520(3) -0.1428(3) 0.0295(5) Uani 1 1 d . . .
H3 H 0.2211 0.9127 -0.1800 0.035 Uiso 1 1 calc R . .
C4 C 0.30985(8) 0.9270(2) -0.1649(2) 0.0243(4) Uani 1 1 d . . .
C5 C 0.36056(8) 0.8402(3) -0.1110(2) 0.0236(4) Uani 1 1 d . . .
C6 C 0.35613(8) 0.6738(3) -0.0346(2) 0.0234(4) Uani 1 1 d . . .
H6 H 0.3903 0.6134 0.0014 0.028 Uiso 1 1 calc R . .
N7 N 0.32435(6) 1.0889(2) -0.2363(2) 0.0286(4) Uani 1 1 d . . .
H7 H 0.2997 1.1659 -0.2807 0.034 Uiso 1 1 calc R . .
C8 C 0.38408(8) 1.1110(3) -0.2270(2) 0.0244(4) Uani 1 1 d . . .
C9 C 0.41709(7) 1.2576(2) -0.2778(3) 0.0251(4) Uani 1 1 d . . .
H9 H 0.3999 1.3598 -0.3287 0.030 Uiso 1 1 calc R . .
C10 C 0.47642(7) 1.2459(3) -0.2498(3) 0.0254(4) Uani 1 1 d . . .
C11 C 0.50172(8) 1.0964(3) -0.1733(3) 0.0268(5) Uani 1 1 d . . .
H11 H 0.5425 1.0934 -0.1554 0.032 Uiso 1 1 calc R . .
C12 C 0.46830(8) 0.9533(3) -0.1236(2) 0.0251(4) Uani 1 1 d . . .
H12 H 0.4858 0.8520 -0.0717 0.030 Uiso 1 1 calc R . .
C13 C 0.40844(8) 0.9590(2) -0.1503(2) 0.0220(4) Uani 1 1 d . . .
C14 C 0.29881(9) 0.4204(3) 0.0802(3) 0.0265(5) Uani 1 1 d . . .
O14 O 0.25659(6) 0.3279(2) 0.0977(2) 0.0412(4) Uani 1 1 d . . .
O15 O 0.35081(6) 0.37435(17) 0.14595(19) 0.0356(4) Uani 1 1 d . . .
C16 C 0.35169(10) 0.2123(3) 0.2444(3) 0.0454(6) Uani 1 1 d . . .
H16A H 0.3242 0.2216 0.3405 0.068 Uiso 1 1 calc R . .
H16B H 0.3908 0.1924 0.2899 0.068 Uiso 1 1 calc R . .
H16C H 0.3407 0.1124 0.1699 0.068 Uiso 1 1 calc R . .
O17 O 0.19953(6) 0.60460(19) -0.0355(2) 0.0370(4) Uani 1 1 d . . .
C18 C 0.14816(8) 0.7065(3) -0.0671(3) 0.0383(6) Uani 1 1 d . . .
H18A H 0.1484 0.8131 0.0059 0.057 Uiso 1 1 calc R . .
H18B H 0.1139 0.6342 -0.0400 0.057 Uiso 1 1 calc R . .
H18C H 0.1469 0.7418 -0.1890 0.057 Uiso 1 1 calc R . .
O19 O 0.51544(5) 1.37760(16) -0.29237(19) 0.0314(3) Uani 1 1 d . . .
C20 C 0.49325(9) 1.5356(3) -0.3682(3) 0.0369(5) Uani 1 1 d . . .
H20A H 0.4739 1.5064 -0.4773 0.055 Uiso 1 1 calc R . .
H20B H 0.5252 1.6186 -0.3905 0.055 Uiso 1 1 calc R . .
H20C H 0.4653 1.5910 -0.2892 0.055 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.81(18) . . ?
C6 C1 C14 119.26(17) . . ?
C2 C1 C14 121.85(17) . . ?
O17 C2 C3 121.94(18) . . ?
O17 C2 C1 116.81(17) . . ?
C3 C2 C1 121.25(18) . . ?
C2 C3 C4 118.09(18) . . ?
N7 C4 C3 128.78(17) . . ?
N7 C4 C5 109.14(15) . . ?
C3 C4 C5 122.07(17) . . ?
C6 C5 C4 119.00(17) . . ?
C6 C5 C13 134.40(17) . . ?
C4 C5 C13 106.59(16) . . ?
C5 C6 C1 120.77(17) . . ?
C4 N7 C8 109.00(15) . . ?
N7 C8 C9 128.38(17) . . ?
N7 C8 C13 108.72(16) . . ?
C9 C8 C13 122.87(16) . . ?
C10 C9 C8 116.37(17) . . ?
O19 C10 C9 124.14(17) . . ?
O19 C10 C11 113.96(15) . . ?
C9 C10 C11 121.90(17) . . ?
C12 C11 C10 120.81(17) . . ?
C11 C12 C13 119.18(17) . . ?
C12 C13 C8 118.88(17) . . ?
C12 C13 C5 134.56(17) . . ?
C8 C13 C5 106.53(15) . . ?
O14 C14 O15 121.93(18) . . ?
O14 C14 C1 127.07(19) . . ?
O15 C14 C1 111.00(16) . . ?
C14 O15 C16 115.50(15) . . ?
C2 O17 C18 117.21(16) . . ?
C10 O19 C20 117.65(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.395(3) . ?
C1 C2 1.423(3) . ?
C1 C14 1.480(3) . ?
C2 O17 1.364(2) . ?
C2 C3 1.385(3) . ?
C3 C4 1.394(3) . ?
C4 N7 1.376(2) . ?
C4 C5 1.402(3) . ?
C5 C6 1.386(3) . ?
C5 C13 1.452(3) . ?
N7 C8 1.389(2) . ?
C8 C9 1.394(3) . ?
C8 C13 1.404(3) . ?
C9 C10 1.387(2) . ?
C10 O19 1.377(2) . ?
C10 C11 1.397(3) . ?
C11 C12 1.377(3) . ?
C12 C13 1.396(3) . ?
C14 O14 1.203(2) . ?
C14 O15 1.347(2) . ?
O15 C16 1.436(2) . ?
O17 C18 1.431(3) . ?
O19 C20 1.419(2) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O17 -178.85(17) . . . . ?
C14 C1 C2 O17 -2.1(3) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C14 C1 C2 C3 177.28(19) . . . . ?
O17 C2 C3 C4 178.84(18) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 N7 -179.26(19) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
N7 C4 C5 C6 179.95(17) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
N7 C4 C5 C13 0.9(2) . . . . ?
C3 C4 C5 C13 -178.45(19) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C13 C5 C6 C1 178.2(2) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C14 C1 C6 C5 -176.80(17) . . . . ?
C3 C4 N7 C8 178.2(2) . . . . ?
C5 C4 N7 C8 -1.1(2) . . . . ?
C4 N7 C8 C9 -177.4(2) . . . . ?
C4 N7 C8 C13 0.9(2) . . . . ?
N7 C8 C9 C10 178.47(19) . . . . ?
C13 C8 C9 C10 0.5(3) . . . . ?
C8 C9 C10 O19 179.8(2) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
O19 C10 C11 C12 -179.95(17) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 C8 -0.1(3) . . . . ?
C11 C12 C13 C5 -177.6(2) . . . . ?
N7 C8 C13 C12 -178.44(16) . . . . ?
C9 C8 C13 C12 -0.1(3) . . . . ?
N7 C8 C13 C5 -0.3(2) . . . . ?
C9 C8 C13 C5 178.04(18) . . . . ?
C6 C5 C13 C12 -1.5(4) . . . . ?
C4 C5 C13 C12 177.3(2) . . . . ?
C6 C5 C13 C8 -179.2(2) . . . . ?
C4 C5 C13 C8 -0.3(2) . . . . ?
C6 C1 C14 O14 -172.9(2) . . . . ?
C2 C1 C14 O14 10.4(3) . . . . ?
C6 C1 C14 O15 7.6(2) . . . . ?
C2 C1 C14 O15 -169.07(17) . . . . ?
O14 C14 O15 C16 -2.7(3) . . . . ?
C1 C14 O15 C16 176.79(17) . . . . ?
C3 C2 O17 C18 -8.1(3) . . . . ?
C1 C2 O17 C18 171.29(17) . . . . ?
C9 C10 O19 C20 0.6(3) . . . . ?
C11 C10 O19 C20 -178.99(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4475130
2 PubChem 5315952
