#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/12/7151285.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_7151285
loop_
_publ_author_name
'Krahl, Micha P.'
'Jäger, Anne'
'Krause, Tilo'
'Knölker, Hans-Joachim'
_publ_section_title
;
 First total synthesis of the 7-oxygenated carbazole alkaloids
 clauszoline-K, 3-formyl-7-hydroxycarbazole, clausine M, clausine N and
 the anti-HIV active siamenol using a highly efficient
 palladium-catalyzed approach.
;
_journal_issue                   17
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3215
_journal_page_last               3219
_journal_paper_doi               10.1039/b607792g
_journal_volume                  4
_journal_year                    2006
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C15 H13 N O3'
_chemical_formula_sum            'C15 H13 N O3'
_chemical_formula_weight         255.26
_chemical_melting_point          468
_chemical_name_common            'Clausine C (Clauszoline L)'
_chemical_name_systematic        'methyl 7-methoxy-9H-carbazole-3-carboxylate'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.10(2)
_cell_angle_beta                 102.27(3)
_cell_angle_gamma                104.33(3)
_cell_formula_units_Z            2
_cell_length_a                   8.118(3)
_cell_length_b                   9.020(2)
_cell_length_c                   9.143(3)
_cell_measurement_reflns_used    21
_cell_measurement_temperature    198(2)
_cell_measurement_theta_max      18.58
_cell_measurement_theta_min      4.80
_cell_volume                     612.2(4)
_computing_cell_refinement       'Dirax/lsq (Duisenberg, 1992)'
_computing_data_collection       'Collect (Nonius BV, 1999)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2003)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997), SCHAKAL99 (Keller & Pierrard, 1999)'
_computing_publication_material
'WinGX (Farrugia, 1999), enCIFer (Allen et al., 2004)'
_computing_structure_refinement
'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia, 1999), PLATON (Spek, 2005)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_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       φ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14687
_diffrn_reflns_theta_full        25.40
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         3.03
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_correction_T_min  0.7754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS version 2.10 (Sheldrick, Bruker AXS Inc.,2002)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0450
_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)+(0.0596P)²+0.2620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1255
_reflns_number_gt                1792
_reflns_number_total             2242
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b607792g.txt
_cod_data_source_block           an7
_cod_database_code               7151285
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.6818(3) 0.6549(2) 0.4197(2) 0.0341(5) Uani 1 1 d . . .
H1 H 0.6182 0.5549 0.3489 0.041 Uiso 1 1 calc R . .
C2 C 0.6505(3) 0.7917(2) 0.3917(2) 0.0316(4) Uani 1 1 d . . .
H2 H 0.5639 0.7859 0.3009 0.038 Uiso 1 1 calc R . .
C3 C 0.7456(2) 0.9400(2) 0.4965(2) 0.0275(4) Uani 1 1 d . . .
C4 C 0.8708(2) 0.9519(2) 0.6309(2) 0.0265(4) Uani 1 1 d . . .
H4 H 0.9336 1.0523 0.7013 0.032 Uiso 1 1 calc R . .
C4A C 0.9038(2) 0.8149(2) 0.6621(2) 0.0260(4) Uani 1 1 d . . .
C4B C 1.0225(2) 0.7818(2) 0.7847(2) 0.0274(4) Uani 1 1 d . . .
C5 C 1.1462(3) 0.8709(2) 0.9261(2) 0.0353(5) Uani 1 1 d . . .
H5 H 1.1678 0.9823 0.9579 0.042 Uiso 1 1 calc R . .
C6 C 1.2353(3) 0.7965(2) 1.0176(2) 0.0387(5) Uani 1 1 d . . .
H6 H 1.3174 0.8569 1.1140 0.046 Uiso 1 1 calc R . .
C7 C 1.2075(3) 0.6319(2) 0.9715(2) 0.0325(4) Uani 1 1 d . . .
C8 C 1.0861(2) 0.5393(2) 0.8342(2) 0.0288(4) Uani 1 1 d . . .
H8 H 1.0661 0.4282 0.8026 0.035 Uiso 1 1 calc R . .
C8A C 0.9944(2) 0.6168(2) 0.7444(2) 0.0265(4) Uani 1 1 d . . .
C9A C 0.8086(2) 0.6669(2) 0.5537(2) 0.0278(4) Uani 1 1 d . . .
N9 N 0.8644(2) 0.55052(19) 0.60570(19) 0.0306(4) Uani 1 1 d . . .
C10 C 0.7143(2) 1.0863(2) 0.4648(2) 0.0288(4) Uani 1 1 d . . .
O11 O 0.79121(19) 1.21814(15) 0.54742(17) 0.0397(4) Uani 1 1 d . . .
O12 O 0.58899(18) 1.05863(16) 0.33187(17) 0.0389(4) Uani 1 1 d . . .
C13 C 0.5510(3) 1.1954(2) 0.2908(3) 0.0409(5) Uani 1 1 d . . .
H13A H 0.5115 1.2522 0.3726 0.061 Uiso 1 1 calc R . .
H13B H 0.4577 1.1614 0.1929 0.061 Uiso 1 1 calc R . .
H13C H 0.6579 1.2656 0.2790 0.061 Uiso 1 1 calc R . .
O14 O 1.30837(19) 0.57363(17) 1.07185(17) 0.0415(4) Uani 1 1 d . . .
C15 C 1.2891(3) 0.4081(3) 1.0284(3) 0.0415(5) Uani 1 1 d . . .
H15A H 1.1658 0.3475 1.0131 0.062 Uiso 1 1 calc R . .
H15B H 1.3659 0.3809 1.1105 0.062 Uiso 1 1 calc R . .
H15C H 1.3224 0.3825 0.9318 0.062 Uiso 1 1 calc R . .
H9N H 0.826(3) 0.456(3) 0.565(3) 0.045(7) Uiso 1 1 d . . .
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
C2 C1 C9A 118.47(18) . . ?
C2 C1 H1 120.8 . . ?
C9A C1 H1 120.8 . . ?
C1 C2 C3 120.64(18) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 120.93(17) . . ?
C4 C3 C10 118.55(17) . . ?
C2 C3 C10 120.51(17) . . ?
C3 C4 C4A 119.40(16) . . ?
C3 C4 H4 120.3 . . ?
C4A C4 H4 120.3 . . ?
C4 C4A C9A 118.77(17) . . ?
C4 C4A C4B 134.86(17) . . ?
C9A C4A C4B 106.35(15) . . ?
C5 C4B C8A 117.61(17) . . ?
C5 C4B C4A 135.83(17) . . ?
C8A C4B C4A 106.53(16) . . ?
C6 C5 C4B 119.64(18) . . ?
C6 C5 H5 120.2 . . ?
C4B C5 H5 120.2 . . ?
C5 C6 C7 121.14(19) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
O14 C7 C8 123.70(18) . . ?
O14 C7 C6 115.08(18) . . ?
C8 C7 C6 121.22(18) . . ?
C7 C8 C8A 116.69(17) . . ?
C7 C8 H8 121.7 . . ?
C8A C8 H8 121.7 . . ?
N9 C8A C8 127.62(17) . . ?
N9 C8A C4B 108.73(16) . . ?
C8 C8A C4B 123.65(17) . . ?
N9 C9A C1 129.44(17) . . ?
N9 C9A C4A 108.78(17) . . ?
C1 C9A C4A 121.77(17) . . ?
C9A N9 C8A 109.60(16) . . ?
C9A N9 H9N 126.5(17) . . ?
C8A N9 H9N 123.9(17) . . ?
O11 C10 O12 122.52(17) . . ?
O11 C10 C3 124.79(18) . . ?
O12 C10 C3 112.69(16) . . ?
C10 O12 C13 116.48(16) . . ?
O12 C13 H13A 109.5 . . ?
O12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 O14 C15 117.37(16) . . ?
O14 C15 H15A 109.5 . . ?
O14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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 C2 1.379(3) . ?
C1 C9A 1.390(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.408(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(3) . ?
C3 C10 1.474(3) . ?
C4 C4A 1.395(2) . ?
C4 H4 0.9500 . ?
C4A C9A 1.420(2) . ?
C4A C4B 1.444(3) . ?
C4B C5 1.405(3) . ?
C4B C8A 1.410(2) . ?
C5 C6 1.370(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.409(3) . ?
C6 H6 0.9500 . ?
C7 O14 1.367(2) . ?
C7 C8 1.381(3) . ?
C8 C8A 1.391(3) . ?
C8 H8 0.9500 . ?
C8A N9 1.381(3) . ?
C9A N9 1.367(2) . ?
N9 H9N 0.81(3) . ?
C10 O11 1.209(2) . ?
C10 O12 1.344(2) . ?
O12 C13 1.440(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
O14 C15 1.429(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
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
C9A C1 C2 C3 0.3(3) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C1 C2 C3 C10 178.81(18) . . . . ?
C2 C3 C4 C4A 0.5(3) . . . . ?
C10 C3 C4 C4A -179.25(16) . . . . ?
C3 C4 C4A C9A 0.5(3) . . . . ?
C3 C4 C4A C4B 178.80(19) . . . . ?
C4 C4A C4B C5 4.0(4) . . . . ?
C9A C4A C4B C5 -177.5(2) . . . . ?
C4 C4A C4B C8A -178.0(2) . . . . ?
C9A C4A C4B C8A 0.4(2) . . . . ?
C8A C4B C5 C6 0.8(3) . . . . ?
C4A C4B C5 C6 178.5(2) . . . . ?
C4B C5 C6 C7 1.1(3) . . . . ?
C5 C6 C7 O14 178.40(19) . . . . ?
C5 C6 C7 C8 -1.7(3) . . . . ?
O14 C7 C8 C8A -179.71(17) . . . . ?
C6 C7 C8 C8A 0.4(3) . . . . ?
C7 C8 C8A N9 -178.29(18) . . . . ?
C7 C8 C8A C4B 1.5(3) . . . . ?
C5 C4B C8A N9 177.73(17) . . . . ?
C4A C4B C8A N9 -0.7(2) . . . . ?
C5 C4B C8A C8 -2.1(3) . . . . ?
C4A C4B C8A C8 179.49(16) . . . . ?
C2 C1 C9A N9 -179.1(2) . . . . ?
C2 C1 C9A C4A 0.8(3) . . . . ?
C4 C4A C9A N9 178.72(16) . . . . ?
C4B C4A C9A N9 0.0(2) . . . . ?
C4 C4A C9A C1 -1.2(3) . . . . ?
C4B C4A C9A C1 -179.91(18) . . . . ?
C1 C9A N9 C8A 179.5(2) . . . . ?
C4A C9A N9 C8A -0.4(2) . . . . ?
C8 C8A N9 C9A -179.47(18) . . . . ?
C4B C8A N9 C9A 0.7(2) . . . . ?
C4 C3 C10 O11 0.6(3) . . . . ?
C2 C3 C10 O11 -179.16(19) . . . . ?
C4 C3 C10 O12 -179.47(16) . . . . ?
C2 C3 C10 O12 0.8(2) . . . . ?
O11 C10 O12 C13 0.6(3) . . . . ?
C3 C10 O12 C13 -179.37(16) . . . . ?
C8 C7 O14 C15 1.9(3) . . . . ?
C6 C7 O14 C15 -178.22(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9992336
