# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2009
data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Wim Dehaen'
_publ_contact_author_email       WIM.DEHAEN@CHEM.KULEUVEN.BE

_publ_section_title              
;
A facile and general method for the synthesis of
6,12-diaryl-5,11-dihydroindolo[3,2-b]carbazoles
;
loop_
_publ_author_name
'Wim Dehaen'
'Rong Gu.'
'L.Van Meervelt'
'Koen Robeyns'
'S.Van Snick'

# Attachment 'x-ray of compound 1a.cif'

data_wim84
_database_code_depnum_ccdc_archive 'CCDC 701159'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H22 N2, C4 H8 O, 2(C2 H6 O S)'
_chemical_formula_sum            'C38 H42 N2 O3 S2'
_chemical_formula_weight         638.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6191(3)
_cell_length_b                   9.4722(4)
_cell_length_c                   10.8125(5)
_cell_angle_alpha                87.925(2)
_cell_angle_beta                 80.702(2)
_cell_angle_gamma                70.015(2)
_cell_volume                     818.52(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1086
_cell_measurement_theta_min      33.5
_cell_measurement_theta_max      70.57

_exptl_crystal_description       ?
_exptl_crystal_colour            translucent
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    1.789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.431
_exptl_absorpt_correction_T_max  0.699
_exptl_absorpt_process_details   'Bruker SADABS (SADABS, 1997)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'crossed Goebel mirrors'
_diffrn_measurement_device_type  'SMART 6000'
_diffrn_measurement_method       'omega and phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12506
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.14
_diffrn_reflns_theta_max         70.96
_reflns_number_total             3082
_reflns_number_gt                2811
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (SMART, 1997)'
_computing_cell_refinement       'Bruker SAINT (SAINT, 1997)'
_computing_data_reduction        'Bruker SAINT (SAINT, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLUTON (Spek, 1998)'
_computing_publication_material  'PLATON (Spek, 1998)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0830P)^2^+0.3912P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3082
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1356
_refine_ls_wR_factor_gt          0.1317
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
N1 N 0.89113(18) 0.44782(16) 0.24549(13) 0.0174(3) Uani 1 1 d . . .
H1 H 0.9343 0.3725 0.2937 0.021 Uiso 1 1 calc R . .
C2 C 0.7470(2) 0.56806(18) 0.27961(16) 0.0172(4) Uani 1 1 d . . .
C3 C 0.6325(2) 0.59727(19) 0.39100(16) 0.0194(4) Uani 1 1 d . . .
H3 H 0.6524 0.5335 0.4608 0.023 Uiso 1 1 calc R . .
C4 C 0.4894(2) 0.7221(2) 0.39598(16) 0.0216(4) Uani 1 1 d . . .
H4 H 0.4087 0.7436 0.4701 0.026 Uiso 1 1 calc R . .
C5 C 0.4608(2) 0.81817(19) 0.29319(17) 0.0217(4) Uani 1 1 d . . .
H5 H 0.3605 0.9025 0.2990 0.026 Uiso 1 1 calc R . .
C6 C 0.5761(2) 0.79197(18) 0.18385(16) 0.0189(4) Uani 1 1 d . . .
H6 H 0.5568 0.8586 0.1157 0.023 Uiso 1 1 calc R . .
C7 C 0.7221(2) 0.66493(18) 0.17561(15) 0.0167(4) Uani 1 1 d . . .
C8 C 0.8587(2) 0.59672(18) 0.07730(16) 0.0158(3) Uani 1 1 d . . .
C9 C 0.9570(2) 0.46497(18) 0.12293(16) 0.0160(3) Uani 1 1 d . . .
C10 C 0.8858(2) 0.64803(18) -0.05546(15) 0.0161(4) Uani 1 1 d . . .
H10 H 0.9019 0.7475 -0.0540 0.019 Uiso 1 1 calc R . .
C11 C 0.7373(2) 0.66440(18) -0.12240(15) 0.0166(4) Uani 1 1 d . . .
C12 C 0.6612(2) 0.5560(2) -0.11130(17) 0.0231(4) Uani 1 1 d . . .
H12 H 0.6996 0.4723 -0.0593 0.028 Uiso 1 1 calc R . .
C13 C 0.5301(2) 0.5680(2) -0.17480(18) 0.0253(4) Uani 1 1 d . . .
H13 H 0.4796 0.4926 -0.1661 0.030 Uiso 1 1 calc R . .
C14 C 0.4723(2) 0.6897(2) -0.25107(17) 0.0234(4) Uani 1 1 d . . .
H14 H 0.3828 0.6978 -0.2951 0.028 Uiso 1 1 calc R . .
C15 C 0.5465(3) 0.7989(2) -0.26220(19) 0.0283(4) Uani 1 1 d . . .
H15 H 0.5074 0.8828 -0.3139 0.034 Uiso 1 1 calc R . .
C16 C 0.6783(2) 0.7870(2) -0.19818(18) 0.0238(4) Uani 1 1 d . . .
H16 H 0.7281 0.8628 -0.2063 0.029 Uiso 1 1 calc R . .
O21 O 0.8980(4) 0.0245(3) 0.8814(3) 0.0334(7) Uani 0.50 1 d P . .
C22 C 1.081(2) -0.0278(17) 0.884(2) 0.036(3) Uani 0.50 1 d P . .
H22A H 1.1271 0.0541 0.8630 0.043 Uiso 0.50 1 calc PR . .
H22B H 1.1418 -0.1138 0.8252 0.043 Uiso 0.50 1 calc PR . .
C23 C 1.0908(9) -0.0745(7) 1.0190(7) 0.0412(15) Uani 0.50 1 d P . .
H23A H 1.1050 -0.1825 1.0279 0.049 Uiso 0.50 1 calc PR . .
H23B H 1.1860 -0.0566 1.0477 0.049 Uiso 0.50 1 calc PR . .
C24 C 0.935(2) 0.017(2) 1.090(2) 0.050(5) Uani 0.50 1 d P . .
H24A H 0.9544 0.0844 1.1492 0.060 Uiso 0.50 1 calc PR . .
H24B H 0.8781 -0.0470 1.1389 0.060 Uiso 0.50 1 calc PR . .
C25 C 0.8289(8) 0.1085(7) 0.9944(6) 0.0389(14) Uani 0.50 1 d P . .
H25A H 0.7099 0.1184 1.0193 0.047 Uiso 0.50 1 calc PR . .
H25B H 0.8375 0.2101 0.9861 0.047 Uiso 0.50 1 calc PR . .
S31 S 0.05721(6) 0.26411(5) 0.51489(4) 0.02492(18) Uani 1 1 d . . .
O32 O -0.03564(19) 0.22084(16) 0.42314(13) 0.0306(3) Uani 1 1 d . . .
C33 C 0.2005(3) 0.0920(2) 0.5605(2) 0.0325(5) Uani 1 1 d . . .
H33A H 0.1411 0.0215 0.5862 0.049 Uiso 1 1 calc R . .
H33B H 0.2499 0.1116 0.6307 0.049 Uiso 1 1 calc R . .
H33C H 0.2892 0.0486 0.4895 0.049 Uiso 1 1 calc R . .
C34 C -0.0831(3) 0.3080(3) 0.6597(2) 0.0356(5) Uani 1 1 d . . .
H34A H -0.1782 0.3989 0.6506 0.053 Uiso 1 1 calc R . .
H34B H -0.0248 0.3249 0.7253 0.053 Uiso 1 1 calc R . .
H34C H -0.1235 0.2241 0.6827 0.053 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0207(7) 0.0158(7) 0.0139(7) 0.0066(5) -0.0046(5) -0.0038(5)
C2 0.0215(8) 0.0158(8) 0.0157(8) 0.0034(6) -0.0060(7) -0.0070(6)
C3 0.0248(9) 0.0196(8) 0.0148(8) 0.0043(6) -0.0048(7) -0.0084(7)
C4 0.0245(9) 0.0224(9) 0.0162(8) 0.0005(7) -0.0009(7) -0.0066(7)
C5 0.0232(9) 0.0163(8) 0.0219(9) 0.0016(6) -0.0039(7) -0.0022(7)
C6 0.0249(9) 0.0146(8) 0.0168(8) 0.0038(6) -0.0060(7) -0.0052(7)
C7 0.0210(8) 0.0159(8) 0.0143(8) 0.0026(6) -0.0052(6) -0.0071(7)
C8 0.0196(8) 0.0142(8) 0.0139(8) 0.0036(6) -0.0052(6) -0.0053(6)
C9 0.0196(8) 0.0151(8) 0.0136(8) 0.0039(6) -0.0047(6) -0.0057(6)
C10 0.0207(8) 0.0127(7) 0.0144(8) 0.0044(6) -0.0041(6) -0.0047(6)
C11 0.0188(8) 0.0153(8) 0.0130(8) 0.0013(6) -0.0028(6) -0.0023(6)
C12 0.0305(9) 0.0205(8) 0.0201(9) 0.0074(7) -0.0091(7) -0.0095(7)
C13 0.0314(10) 0.0260(9) 0.0235(9) 0.0041(7) -0.0076(8) -0.0151(8)
C14 0.0224(9) 0.0278(9) 0.0196(9) 0.0024(7) -0.0074(7) -0.0063(7)
C15 0.0318(10) 0.0242(9) 0.0302(10) 0.0127(8) -0.0160(8) -0.0075(8)
C16 0.0285(9) 0.0189(8) 0.0266(10) 0.0094(7) -0.0111(8) -0.0094(7)
O21 0.0378(16) 0.0308(15) 0.0324(16) 0.0042(12) -0.0085(13) -0.0117(12)
C22 0.027(3) 0.035(4) 0.030(7) 0.014(4) 0.009(4) 0.001(3)
C23 0.046(4) 0.030(3) 0.053(4) 0.008(3) -0.024(4) -0.014(3)
C24 0.061(9) 0.066(7) 0.032(8) 0.005(4) 0.006(5) -0.037(7)
C25 0.040(3) 0.035(3) 0.039(3) -0.002(2) -0.008(3) -0.008(3)
S31 0.0316(3) 0.0219(3) 0.0214(3) 0.00620(17) -0.00742(19) -0.00834(19)
O32 0.0435(8) 0.0282(7) 0.0234(7) 0.0122(5) -0.0151(6) -0.0133(6)
C33 0.0384(11) 0.0269(10) 0.0274(10) 0.0032(8) -0.0118(9) -0.0023(8)
C34 0.0298(10) 0.0459(13) 0.0284(11) -0.0033(9) -0.0051(8) -0.0088(9)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
N1 C2 1.375(2) . ?
N1 C9 1.382(2) . ?
N1 H1 0.8800 . ?
C2 C3 1.398(3) . ?
C2 C7 1.422(2) . ?
C3 C4 1.381(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.409(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.406(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.435(2) . ?
C8 C9 1.373(2) . ?
C8 C10 1.507(2) . ?
C9 C10 1.503(2) 2_765 ?
C10 C9 1.503(2) 2_765 ?
C10 C11 1.530(2) . ?
C10 H10 1.0000 . ?
C11 C12 1.387(3) . ?
C11 C16 1.393(2) . ?
C12 C13 1.385(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
O21 C25 1.412(7) . ?
O21 C22 1.489(17) . ?
C22 C23 1.52(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.44(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.54(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
S31 O32 1.5175(15) . ?
S31 C34 1.783(2) . ?
S31 C33 1.785(2) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?

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 N1 C9 108.71(13) . . ?
C2 N1 H1 125.6 . . ?
C9 N1 H1 125.6 . . ?
N1 C2 C3 130.03(15) . . ?
N1 C2 C7 107.94(14) . . ?
C3 C2 C7 121.96(16) . . ?
C4 C3 C2 117.68(16) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C5 121.27(16) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 121.24(16) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 118.75(15) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C6 C7 C2 119.06(15) . . ?
C6 C7 C8 134.24(16) . . ?
C2 C7 C8 106.53(14) . . ?
C9 C8 C7 106.96(14) . . ?
C9 C8 C10 124.78(15) . . ?
C7 C8 C10 128.04(15) . . ?
C8 C9 N1 109.85(15) . . ?
C8 C9 C10 127.54(15) . 2_765 ?
N1 C9 C10 122.62(14) . 2_765 ?
C9 C10 C8 107.57(13) 2_765 . ?
C9 C10 C11 110.79(14) 2_765 . ?
C8 C10 C11 112.03(14) . . ?
C9 C10 H10 108.8 2_765 . ?
C8 C10 H10 108.8 . . ?
C11 C10 H10 108.8 . . ?
C12 C11 C16 118.65(17) . . ?
C12 C11 C10 120.80(15) . . ?
C16 C11 C10 120.54(16) . . ?
C13 C12 C11 121.03(16) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 120.24(18) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C15 C14 C13 119.23(18) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 120.51(17) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 120.33(17) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C25 O21 C22 103.2(9) . . ?
O21 C22 C23 102.4(13) . . ?
O21 C22 H22A 111.3 . . ?
C23 C22 H22A 111.3 . . ?
O21 C22 H22B 111.3 . . ?
C23 C22 H22B 111.3 . . ?
H22A C22 H22B 109.2 . . ?
C24 C23 C22 105.6(11) . . ?
C24 C23 H23A 110.6 . . ?
C22 C23 H23A 110.6 . . ?
C24 C23 H23B 110.6 . . ?
C22 C23 H23B 110.6 . . ?
H23A C23 H23B 108.8 . . ?
C23 C24 C25 106.2(14) . . ?
C23 C24 H24A 110.5 . . ?
C25 C24 H24A 110.5 . . ?
C23 C24 H24B 110.5 . . ?
C25 C24 H24B 110.5 . . ?
H24A C24 H24B 108.7 . . ?
O21 C25 C24 104.1(8) . . ?
O21 C25 H25A 110.9 . . ?
C24 C25 H25A 110.9 . . ?
O21 C25 H25B 110.9 . . ?
C24 C25 H25B 110.9 . . ?
H25A C25 H25B 109.0 . . ?
O32 S31 C34 106.01(10) . . ?
O32 S31 C33 106.00(9) . . ?
C34 S31 C33 97.57(11) . . ?
S31 C33 H33A 109.5 . . ?
S31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
S31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
S31 C34 H34A 109.5 . . ?
S31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
S31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        67.70
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.898
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.076