# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2009

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Shengming Ma'
_publ_contact_author_email       MASM@MAIL.SIOC.AC.CN

_publ_section_title              
;
An Efficient Synthesis of Carbazoles
from PtCl2-Catalyzed Cyclization of 1-(Indol-2-yl)-2,3-allenols
;
loop_
_publ_author_name
'Shengming Ma.'
'Chunling Fu.'
'Wangqing Kong.'

data_z
_database_code_depnum_ccdc_archive 'CCDC 713481'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 N'
_chemical_formula_weight         271.35

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.4171(5)
_cell_length_b                   7.7041(2)
_cell_length_c                   17.2037(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.5740(10)
_cell_angle_gamma                90.00
_cell_volume                     2875.54(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.781
_exptl_crystal_size_mid          0.728
_exptl_crystal_size_min          0.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.767185
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13510
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2540
_reflns_number_gt                2242
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0449P)^2^+1.1537P] 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         2540
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0891
_refine_ls_wR_factor_gt          0.0850
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_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 0.25904(4) 0.32059(11) 0.09141(5) 0.0294(2) Uani 1 1 d . . .
C1 C 0.31327(5) 0.24358(13) 0.13404(6) 0.0297(2) Uani 1 1 d . . .
C2 C 0.37384(5) 0.28665(15) 0.13580(7) 0.0363(3) Uani 1 1 d . . .
H2A H 0.3830 0.3795 0.1044 0.044 Uiso 1 1 calc R . .
C3 C 0.42015(6) 0.18968(17) 0.18478(7) 0.0433(3) Uani 1 1 d . . .
H3A H 0.4619 0.2164 0.1869 0.052 Uiso 1 1 calc R . .
C4 C 0.40693(6) 0.05289(18) 0.23137(7) 0.0460(3) Uani 1 1 d . . .
H4A H 0.4398 -0.0103 0.2653 0.055 Uiso 1 1 calc R . .
C5 C 0.34699(6) 0.00882(15) 0.22866(7) 0.0405(3) Uani 1 1 d . . .
H5A H 0.3383 -0.0853 0.2598 0.049 Uiso 1 1 calc R . .
C6 C 0.29896(5) 0.10415(14) 0.17958(6) 0.0322(3) Uani 1 1 d . . .
C7 C 0.23279(5) 0.09893(13) 0.16377(6) 0.0317(3) Uani 1 1 d . . .
C8 C 0.20988(5) 0.23518(13) 0.10957(6) 0.0291(2) Uani 1 1 d . . .
C9 C 0.14714(5) 0.26822(14) 0.08206(6) 0.0315(3) Uani 1 1 d . . .
H9A H 0.1326 0.3601 0.0453 0.038 Uiso 1 1 calc R . .
C10 C 0.10595(5) 0.16354(15) 0.10955(6) 0.0347(3) Uani 1 1 d . . .
C11 C 0.12896(6) 0.02721(15) 0.16375(7) 0.0399(3) Uani 1 1 d . . .
H11A H 0.1008 -0.0437 0.1823 0.048 Uiso 1 1 calc R . .
C12 C 0.19098(6) -0.00551(14) 0.19027(6) 0.0378(3) Uani 1 1 d . . .
H12A H 0.2053 -0.0985 0.2264 0.045 Uiso 1 1 calc R . .
C13 C 0.03876(6) 0.19667(15) 0.08288(7) 0.0388(3) Uani 1 1 d . . .
C14 C 0.01118(6) 0.25311(17) 0.00538(8) 0.0445(3) Uani 1 1 d . . .
H14A H 0.0358 0.2699 -0.0316 0.053 Uiso 1 1 calc R . .
C15 C -0.05145(7) 0.28515(18) -0.01874(10) 0.0562(4) Uani 1 1 d . . .
H15A H -0.0696 0.3226 -0.0721 0.067 Uiso 1 1 calc R . .
C16 C -0.08773(7) 0.26270(19) 0.03479(11) 0.0620(4) Uani 1 1 d . . .
H16A H -0.1308 0.2848 0.0184 0.074 Uiso 1 1 calc R . .
C17 C -0.06114(7) 0.2083(2) 0.11185(11) 0.0604(4) Uani 1 1 d . . .
H17A H -0.0859 0.1939 0.1488 0.072 Uiso 1 1 calc R . .
C18 C 0.00115(6) 0.17455(18) 0.13580(8) 0.0498(3) Uani 1 1 d . . .
H18A H 0.0188 0.1357 0.1890 0.060 Uiso 1 1 calc R . .
C19 C 0.25503(5) 0.48488(13) 0.04858(6) 0.0303(2) Uani 1 1 d . . .
H19A H 0.2172 0.4858 0.0041 0.036 Uiso 1 1 calc R . .
H19B H 0.2908 0.4960 0.0250 0.036 Uiso 1 1 calc R . .
C20 C 0.25389(6) 0.63806(15) 0.10331(7) 0.0391(3) Uani 1 1 d . . .
H20A H 0.2512 0.7460 0.0725 0.059 Uiso 1 1 calc R . .
H20B H 0.2917 0.6387 0.1469 0.059 Uiso 1 1 calc R . .
H20C H 0.2180 0.6286 0.1259 0.059 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 0.0388(5) 0.0235(5) 0.0265(4) 0.0035(3) 0.0097(4) 0.0017(4)
C1 0.0422(6) 0.0244(5) 0.0227(5) -0.0031(4) 0.0083(4) 0.0040(4)
C2 0.0456(7) 0.0325(6) 0.0313(6) -0.0022(5) 0.0109(5) 0.0024(5)
C3 0.0434(7) 0.0471(7) 0.0378(6) -0.0035(5) 0.0068(5) 0.0075(6)
C4 0.0536(8) 0.0450(7) 0.0351(6) 0.0010(5) 0.0029(5) 0.0155(6)
C5 0.0625(8) 0.0296(6) 0.0278(6) 0.0017(5) 0.0086(5) 0.0091(5)
C6 0.0510(7) 0.0236(5) 0.0223(5) -0.0029(4) 0.0098(4) 0.0038(5)
C7 0.0526(7) 0.0218(5) 0.0219(5) -0.0026(4) 0.0115(4) 0.0001(5)
C8 0.0434(6) 0.0228(5) 0.0230(5) -0.0035(4) 0.0118(4) -0.0018(4)
C9 0.0439(7) 0.0262(6) 0.0252(5) -0.0026(4) 0.0101(5) -0.0012(5)
C10 0.0474(7) 0.0308(6) 0.0283(5) -0.0085(5) 0.0142(5) -0.0076(5)
C11 0.0576(8) 0.0336(6) 0.0323(6) -0.0037(5) 0.0184(5) -0.0130(5)
C12 0.0626(8) 0.0256(6) 0.0267(5) 0.0011(4) 0.0139(5) -0.0040(5)
C13 0.0466(7) 0.0300(6) 0.0427(7) -0.0121(5) 0.0164(5) -0.0105(5)
C14 0.0459(8) 0.0403(7) 0.0481(7) -0.0061(5) 0.0134(6) -0.0047(6)
C15 0.0490(8) 0.0445(8) 0.0704(9) -0.0053(7) 0.0066(7) -0.0040(6)
C16 0.0427(8) 0.0447(8) 0.0997(13) -0.0135(8) 0.0203(8) -0.0072(6)
C17 0.0548(9) 0.0515(9) 0.0855(11) -0.0201(8) 0.0374(8) -0.0172(7)
C18 0.0550(8) 0.0471(8) 0.0534(8) -0.0142(6) 0.0250(6) -0.0171(6)
C19 0.0406(6) 0.0244(5) 0.0269(5) 0.0044(4) 0.0104(4) 0.0006(4)
C20 0.0602(8) 0.0251(6) 0.0323(6) 0.0021(5) 0.0122(5) 0.0005(5)

_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 C8 1.3851(14) . ?
N1 C1 1.3853(14) . ?
N1 C19 1.4559(13) . ?
C1 C2 1.3907(16) . ?
C1 C6 1.4132(15) . ?
C2 C3 1.3805(17) . ?
C2 H2A 0.9500 . ?
C3 C4 1.4000(19) . ?
C3 H3A 0.9500 . ?
C4 C5 1.3753(19) . ?
C4 H4A 0.9500 . ?
C5 C6 1.3978(16) . ?
C5 H5A 0.9500 . ?
C6 C7 1.4398(17) . ?
C7 C12 1.3960(16) . ?
C7 C8 1.4121(15) . ?
C8 C9 1.3898(16) . ?
C9 C10 1.3952(15) . ?
C9 H9A 0.9500 . ?
C10 C11 1.4130(17) . ?
C10 C13 1.4820(17) . ?
C11 C12 1.3731(18) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C14 1.3907(18) . ?
C13 C18 1.3982(17) . ?
C14 C15 1.3825(19) . ?
C14 H14A 0.9500 . ?
C15 C16 1.384(2) . ?
C15 H15A 0.9500 . ?
C16 C17 1.375(2) . ?
C16 H16A 0.9500 . ?
C17 C18 1.378(2) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 C20 1.5139(15) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C8 N1 C1 108.61(9) . . ?
C8 N1 C19 125.16(9) . . ?
C1 N1 C19 125.06(9) . . ?
N1 C1 C2 129.14(10) . . ?
N1 C1 C6 109.13(10) . . ?
C2 C1 C6 121.73(10) . . ?
C3 C2 C1 117.66(11) . . ?
C3 C2 H2A 121.2 . . ?
C1 C2 H2A 121.2 . . ?
C2 C3 C4 121.46(12) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C5 C4 C3 120.81(11) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 119.22(11) . . ?
C4 C5 H5A 120.4 . . ?
C6 C5 H5A 120.4 . . ?
C5 C6 C1 119.11(11) . . ?
C5 C6 C7 134.41(11) . . ?
C1 C6 C7 106.45(9) . . ?
C12 C7 C8 118.79(11) . . ?
C12 C7 C6 134.33(10) . . ?
C8 C7 C6 106.87(9) . . ?
N1 C8 C9 129.09(10) . . ?
N1 C8 C7 108.92(10) . . ?
C9 C8 C7 121.99(10) . . ?
C8 C9 C10 118.56(10) . . ?
C8 C9 H9A 120.7 . . ?
C10 C9 H9A 120.7 . . ?
C9 C10 C11 119.37(11) . . ?
C9 C10 C13 120.22(11) . . ?
C11 C10 C13 120.41(10) . . ?
C12 C11 C10 121.79(11) . . ?
C12 C11 H11A 119.1 . . ?
C10 C11 H11A 119.1 . . ?
C11 C12 C7 119.51(11) . . ?
C11 C12 H12A 120.2 . . ?
C7 C12 H12A 120.2 . . ?
C14 C13 C18 117.84(12) . . ?
C14 C13 C10 121.51(11) . . ?
C18 C13 C10 120.65(12) . . ?
C15 C14 C13 121.10(13) . . ?
C15 C14 H14A 119.5 . . ?
C13 C14 H14A 119.5 . . ?
C14 C15 C16 120.02(15) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C17 C16 C15 119.65(14) . . ?
C17 C16 H16A 120.2 . . ?
C15 C16 H16A 120.2 . . ?
C16 C17 C18 120.45(14) . . ?
C16 C17 H17A 119.8 . . ?
C18 C17 H17A 119.8 . . ?
C17 C18 C13 120.94(14) . . ?
C17 C18 H18A 119.5 . . ?
C13 C18 H18A 119.5 . . ?
N1 C19 C20 111.81(8) . . ?
N1 C19 H19A 109.3 . . ?
C20 C19 H19A 109.3 . . ?
N1 C19 H19B 109.3 . . ?
C20 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
C8 N1 C1 C2 -179.02(10) . . . . ?
C19 N1 C1 C2 -10.85(16) . . . . ?
C8 N1 C1 C6 0.95(11) . . . . ?
C19 N1 C1 C6 169.12(9) . . . . ?
N1 C1 C2 C3 179.05(10) . . . . ?
C6 C1 C2 C3 -0.92(16) . . . . ?
C1 C2 C3 C4 -0.15(17) . . . . ?
C2 C3 C4 C5 1.13(19) . . . . ?
C3 C4 C5 C6 -0.99(18) . . . . ?
C4 C5 C6 C1 -0.06(16) . . . . ?
C4 C5 C6 C7 -177.92(11) . . . . ?
N1 C1 C6 C5 -178.94(9) . . . . ?
C2 C1 C6 C5 1.04(15) . . . . ?
N1 C1 C6 C7 -0.53(11) . . . . ?
C2 C1 C6 C7 179.45(9) . . . . ?
C5 C6 C7 C12 -1.4(2) . . . . ?
C1 C6 C7 C12 -179.47(11) . . . . ?
C5 C6 C7 C8 177.97(11) . . . . ?
C1 C6 C7 C8 -0.08(11) . . . . ?
C1 N1 C8 C9 179.09(10) . . . . ?
C19 N1 C8 C9 10.94(16) . . . . ?
C1 N1 C8 C7 -1.01(11) . . . . ?
C19 N1 C8 C7 -169.16(9) . . . . ?
C12 C7 C8 N1 -179.83(9) . . . . ?
C6 C7 C8 N1 0.67(11) . . . . ?
C12 C7 C8 C9 0.08(15) . . . . ?
C6 C7 C8 C9 -179.42(9) . . . . ?
N1 C8 C9 C10 -179.72(10) . . . . ?
C7 C8 C9 C10 0.39(15) . . . . ?
C8 C9 C10 C11 -0.41(15) . . . . ?
C8 C9 C10 C13 178.81(9) . . . . ?
C9 C10 C11 C12 -0.03(16) . . . . ?
C13 C10 C11 C12 -179.26(10) . . . . ?
C10 C11 C12 C7 0.51(17) . . . . ?
C8 C7 C12 C11 -0.53(15) . . . . ?
C6 C7 C12 C11 178.81(11) . . . . ?
C9 C10 C13 C14 35.97(16) . . . . ?
C11 C10 C13 C14 -144.81(12) . . . . ?
C9 C10 C13 C18 -142.98(11) . . . . ?
C11 C10 C13 C18 36.23(16) . . . . ?
C18 C13 C14 C15 -0.44(18) . . . . ?
C10 C13 C14 C15 -179.43(12) . . . . ?
C13 C14 C15 C16 0.6(2) . . . . ?
C14 C15 C16 C17 -0.1(2) . . . . ?
C15 C16 C17 C18 -0.6(2) . . . . ?
C16 C17 C18 C13 0.8(2) . . . . ?
C14 C13 C18 C17 -0.24(18) . . . . ?
C10 C13 C18 C17 178.76(11) . . . . ?
C8 N1 C19 C20 80.69(13) . . . . ?
C1 N1 C19 C20 -85.56(12) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.036