#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:00:49 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180327 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/41/7154146.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_7154146
loop_
_publ_author_name
'Zhu, Yu'
'Shen, Xin-Rui'
'Tang, Hai-Tao'
'Lin, Min'
'Zhan, Zhuang-Ping'
_publ_section_title
;
 Silver(i)-catalyzed annulation for the regioselective synthesis of
 N-imino-γ-carbolinium ylides from hydrazones of indole-3-carbonyl
 derivatives and propargylic alcohols.
;
_journal_issue                   47
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9514
_journal_page_last               9518
_journal_paper_doi               10.1039/c4ob02020k
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C35 H27 N3 O2 S'
_chemical_formula_weight         553.66
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 105.211(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2471(5)
_cell_length_b                   15.4948(8)
_cell_length_c                   17.7996(9)
_cell_measurement_reflns_used    5973
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3240
_cell_measurement_theta_min      3.7350
_cell_volume                     2727.2(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14289
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.34
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77392
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1160
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         5273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0616
_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)+(0.0494P)²+1.6302P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1175
_reflns_number_gt                4207
_reflns_number_total             5273
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ob02020k2.cif
_cod_data_source_block           z0509
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to 'constr'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 7154145--7154146.cif.
;
_cod_original_cell_volume        2727.1(2)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7154146
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
S1 S 0.41091(4) 0.12958(3) 0.21750(3) 0.01712(14) Uani 1 1 d .
O1 O 0.53003(12) 0.16690(9) 0.20121(8) 0.0220(3) Uani 1 1 d .
N1 N -0.22344(15) 0.10019(11) 0.18067(9) 0.0190(4) Uani 1 1 d .
H1A H -0.2840 0.1223 0.2022 0.023 Uiso 1 1 calc R
N2 N 0.16476(14) 0.16618(11) 0.18883(9) 0.0156(3) Uani 1 1 d .
O2 O 0.38283(13) 0.03989(9) 0.19637(8) 0.0229(3) Uani 1 1 d .
N3 N 0.29183(14) 0.19465(11) 0.17867(9) 0.0170(4) Uani 1 1 d .
C3 C -0.35872(19) -0.08091(14) 0.04735(12) 0.0223(4) Uani 1 1 d .
H3B H -0.4381 -0.1137 0.0257 0.027 Uiso 1 1 calc R
C10 C -0.02921(18) 0.19951(13) 0.23501(11) 0.0168(4) Uani 1 1 d .
C20 C -0.28246(19) 0.36019(13) 0.27521(12) 0.0219(4) Uani 1 1 d .
H20A H -0.3515 0.3967 0.2456 0.026 Uiso 1 1 calc R
C19 C -0.25391(19) 0.35993(13) 0.35432(12) 0.0232(5) Uani 1 1 d .
H19A H -0.3016 0.3977 0.3797 0.028 Uiso 1 1 calc R
C7 C -0.02681(17) 0.07614(13) 0.14895(10) 0.0152(4) Uani 1 1 d .
C8 C 0.10301(17) 0.09741(13) 0.14782(10) 0.0158(4) Uani 1 1 d .
H8A H 0.1492 0.0638 0.1183 0.019 Uiso 1 1 calc R
C22 C 0.17914(18) 0.29567(13) 0.27216(11) 0.0190(4) Uani 1 1 d .
H22A H 0.2737 0.2783 0.2967 0.023 Uiso 1 1 calc R
H22B H 0.1387 0.3148 0.3141 0.023 Uiso 1 1 calc R
C29 C 0.43301(18) 0.13395(13) 0.31974(11) 0.0186(4) Uani 1 1 d .
C4 C -0.24018(19) -0.09990(14) 0.02497(11) 0.0208(4) Uani 1 1 d .
H4A H -0.2406 -0.1451 -0.0112 0.025 Uiso 1 1 calc R
C23 C 0.18018(19) 0.37140(13) 0.21812(12) 0.0203(4) Uani 1 1 d .
C5 C -0.12265(18) -0.05330(13) 0.05518(10) 0.0180(4) Uani 1 1 d .
H5B H -0.0424 -0.0661 0.0402 0.022 Uiso 1 1 calc R
C18 C -0.15362(18) 0.30385(13) 0.39952(11) 0.0199(4) Uani 1 1 d .
C13 C -0.07632(18) 0.25201(13) 0.36123(11) 0.0178(4) Uani 1 1 d .
C21 C -0.20901(18) 0.30581(13) 0.23714(11) 0.0196(4) Uani 1 1 d .
H21A H -0.2320 0.3047 0.1819 0.023 Uiso 1 1 calc R
C11 C -0.09402(17) 0.12861(13) 0.19223(11) 0.0158(4) Uani 1 1 d .
C30 C 0.35404(19) 0.08404(14) 0.35559(12) 0.0232(5) Uani 1 1 d .
H30A H 0.2917 0.0434 0.3262 0.028 Uiso 1 1 calc R
C34 C 0.52544(19) 0.19239(15) 0.36285(12) 0.0261(5) Uani 1 1 d .
H34A H 0.5799 0.2262 0.3384 0.031 Uiso 1 1 calc R
C27 C 0.0612(2) 0.48209(16) 0.13061(15) 0.0367(6) Uani 1 1 d .
H27A H -0.0217 0.5077 0.1031 0.044 Uiso 1 1 calc R
C6 C -0.12447(17) 0.01283(13) 0.10806(10) 0.0160(4) Uani 1 1 d .
C9 C 0.10243(18) 0.21815(13) 0.23261(10) 0.0170(4) Uani 1 1 d .
C17 C -0.1291(2) 0.29815(14) 0.48143(12) 0.0247(5) Uani 1 1 d .
H17A H -0.1806 0.3324 0.5074 0.030 Uiso 1 1 calc R
C12 C -0.10549(17) 0.25480(13) 0.27815(11) 0.0175(4) Uani 1 1 d .
C1 C -0.24498(18) 0.03070(13) 0.12954(11) 0.0168(4) Uani 1 1 d .
C2 C -0.36330(19) -0.01608(13) 0.09980(11) 0.0209(4) Uani 1 1 d .
H2B H -0.4437 -0.0039 0.1149 0.025 Uiso 1 1 calc R
C15 C 0.0486(2) 0.19492(14) 0.48668(12) 0.0243(5) Uani 1 1 d .
H15A H 0.1178 0.1590 0.5169 0.029 Uiso 1 1 calc R
C14 C 0.02796(19) 0.19865(14) 0.40769(11) 0.0217(4) Uani 1 1 d .
H14A H 0.0834 0.1655 0.3834 0.026 Uiso 1 1 calc R
C32 C 0.4581(2) 0.15299(16) 0.47929(12) 0.0304(5) Uani 1 1 d .
C28 C 0.0604(2) 0.41188(15) 0.17853(14) 0.0305(5) Uani 1 1 d .
H28A H -0.0233 0.3909 0.1846 0.037 Uiso 1 1 calc R
C33 C 0.5376(2) 0.20102(16) 0.44209(13) 0.0305(5) Uani 1 1 d .
H33A H 0.6017 0.2406 0.4716 0.037 Uiso 1 1 calc R
C26 C 0.1822(2) 0.51510(16) 0.12263(15) 0.0359(6) Uani 1 1 d .
H26A H 0.1833 0.5639 0.0905 0.043 Uiso 1 1 calc R
C16 C -0.0326(2) 0.24415(15) 0.52330(12) 0.0268(5) Uani 1 1 d .
H16A H -0.0197 0.2396 0.5780 0.032 Uiso 1 1 calc R
C24 C 0.3005(2) 0.40451(15) 0.20892(14) 0.0288(5) Uani 1 1 d .
H24A H 0.3836 0.3780 0.2350 0.035 Uiso 1 1 calc R
C35 C 0.4718(3) 0.1652(2) 0.56482(14) 0.0462(7) Uani 1 1 d .
H35A H 0.5406 0.2092 0.5854 0.069 Uiso 1 1 calc R
H35B H 0.4988 0.1106 0.5922 0.069 Uiso 1 1 calc R
H35C H 0.3849 0.1839 0.5726 0.069 Uiso 1 1 calc R
C31 C 0.3672(2) 0.09415(15) 0.43489(13) 0.0292(5) Uani 1 1 d .
H31A H 0.3130 0.0601 0.4593 0.035 Uiso 1 1 calc R
C25 C 0.3011(2) 0.47589(16) 0.16209(15) 0.0368(6) Uani 1 1 d .
H25A H 0.3848 0.4981 0.1571 0.044 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'
S S 0.1246 0.1234 '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
O1 S1 O2 116.86(8)
O1 S1 N3 104.51(8)
O2 S1 N3 114.64(8)
O1 S1 C29 107.62(8)
O2 S1 C29 105.42(9)
N3 S1 C29 107.31(9)
C11 N1 C1 109.33(15)
C8 N2 C9 122.80(15)
C8 N2 N3 119.19(15)
C9 N2 N3 117.42(15)
N2 N3 S1 111.64(12)
C2 C3 C4 121.96(18)
C9 C10 C11 118.12(17)
C9 C10 C12 122.48(17)
C11 C10 C12 119.33(16)
C19 C20 C21 119.78(18)
C20 C19 C18 120.94(18)
C8 C7 C11 118.70(17)
C8 C7 C6 134.11(17)
C11 C7 C6 106.89(15)
N2 C8 C7 119.91(17)
C9 C22 C23 114.20(15)
C34 C29 C30 120.31(19)
C34 C29 S1 118.48(15)
C30 C29 S1 121.10(15)
C5 C4 C3 120.58(19)
C24 C23 C28 117.8(2)
C24 C23 C22 121.04(18)
C28 C23 C22 121.09(17)
C4 C5 C6 118.70(17)
C17 C18 C13 119.20(18)
C17 C18 C19 121.81(18)
C13 C18 C19 118.99(18)
C18 C13 C14 118.37(17)
C18 C13 C12 119.15(17)
C14 C13 C12 122.48(17)
C12 C21 C20 121.54(18)
N1 C11 C10 129.81(17)
N1 C11 C7 109.00(16)
C10 C11 C7 121.12(16)
C29 C30 C31 119.34(19)
C29 C34 C33 119.4(2)
C26 C27 C28 120.3(2)
C5 C6 C1 119.61(17)
C5 C6 C7 134.79(17)
C1 C6 C7 105.56(16)
N2 C9 C10 119.33(17)
N2 C9 C22 117.70(16)
C10 C9 C22 122.88(17)
C16 C17 C18 120.68(19)
C21 C12 C13 119.40(17)
C21 C12 C10 119.44(17)
C13 C12 C10 121.09(16)
N1 C1 C2 128.71(17)
N1 C1 C6 109.22(16)
C2 C1 C6 122.06(18)
C3 C2 C1 117.08(18)
C14 C15 C16 120.17(19)
C15 C14 C13 120.63(19)
C31 C32 C33 117.9(2)
C31 C32 C35 121.9(2)
C33 C32 C35 120.2(2)
C27 C28 C23 121.2(2)
C34 C33 C32 121.6(2)
C25 C26 C27 118.8(2)
C17 C16 C15 120.86(19)
C23 C24 C25 120.8(2)
C30 C31 C32 121.5(2)
C26 C25 C24 121.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4471(13)
S1 O2 1.4488(15)
S1 N3 1.5938(16)
S1 C29 1.775(2)
N1 C11 1.361(2)
N1 C1 1.389(2)
N2 C8 1.351(2)
N2 C9 1.387(2)
N2 N3 1.430(2)
C3 C2 1.380(3)
C3 C4 1.405(3)
C10 C9 1.391(3)
C10 C11 1.401(3)
C10 C12 1.500(3)
C20 C19 1.361(3)
C20 C21 1.415(3)
C19 C18 1.423(3)
C7 C8 1.376(3)
C7 C11 1.417(3)
C7 C6 1.453(3)
C22 C9 1.505(3)
C22 C23 1.519(3)
C29 C34 1.387(3)
C29 C30 1.390(3)
C4 C5 1.386(3)
C23 C24 1.384(3)
C23 C28 1.394(3)
C5 C6 1.395(3)
C18 C17 1.416(3)
C18 C13 1.421(3)
C13 C14 1.430(3)
C13 C12 1.430(3)
C21 C12 1.370(3)
C30 C31 1.391(3)
C34 C33 1.389(3)
C27 C26 1.382(3)
C27 C28 1.384(3)
C6 C1 1.413(3)
C17 C16 1.359(3)
C1 C2 1.392(3)
C15 C14 1.367(3)
C15 C16 1.408(3)
C32 C31 1.392(3)
C32 C33 1.393(3)
C32 C35 1.504(3)
C26 C25 1.378(3)
C24 C25 1.386(3)
