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#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/18/7151830.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_7151830
loop_
_publ_author_name
'Rao, R. Mohan'
'Reddy, Upendar C. H.'
Alinakhi,
'Mulakayala, Naveen'
'Alvala, Mallika'
'Arunasree, M. K.'
'Poondra, Rajamohan R.'
'Iqbal, Javed'
'Pal, Manojit'
_publ_section_title
;
 Sequential coupling/desilylation-coupling/cyclization in a single pot
 under Pd/C-Cu catalysis: synthesis of 2-(hetero)aryl indoles.
;
_journal_issue                   10
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3808
_journal_page_last               3816
_journal_paper_doi               10.1039/c0ob01161d
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C17 H17 N O2 S '
_chemical_formula_sum            'C17 H17 N O2 S'
_chemical_formula_weight         299.39
_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'
_audit_creation_date             2010-05-20
_audit_creation_method           'by CrystalStructure 3.8'
_cell_angle_alpha                69.524(7)
_cell_angle_beta                 88.465(14)
_cell_angle_gamma                89.340(13)
_cell_formula_units_Z            2
_cell_length_a                   5.805(4)
_cell_length_b                   10.234(6)
_cell_length_c                   13.495(8)
_cell_measurement_reflns_used    4183
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     750.8(8)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8318
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         27.44
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             316.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.41
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2971
_refine_ls_R_factor_gt           0.0574
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979)
19207.1000 26572.0000 7561.1600
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0603
_reflns_number_gt                2515
_reflns_number_total             2988
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            c0ob01161d.txt
_cod_data_source_block           '__SX_100519_001'
_cod_original_formula_sum        'C17 H17 N O2 S '
_cod_database_code               7151830
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S Uani 0.54499(7) 0.06291(4) 0.66217(3) 1.000 0.0438(1) . .
O1 O Uani 0.6700(2) 0.00189(14) 0.75668(10) 1.000 0.0691(4) . .
O2 O Uani 0.6656(2) 0.10046(12) 0.56306(9) 1.000 0.0569(4) . .
N1 N Uani 0.4160(2) 0.20891(12) 0.66932(8) 1.000 0.0384(3) . .
C1 C Uani 0.2550(2) 0.28159(14) 0.58979(10) 1.000 0.0376(4) . .
C2 C Uani 0.0697(2) 0.31972(17) 0.63645(11) 1.000 0.0434(4) . .
C3 C Uani -0.0324(2) 0.28390(17) 0.83296(12) 1.000 0.0485(5) . .
C4 C Uani 0.0466(3) 0.22619(18) 0.93514(12) 1.000 0.0529(5) . .
C5 C Uani 0.2620(3) 0.16086(19) 0.95134(12) 1.000 0.0552(5) . .
C6 C Uani 0.3998(2) 0.14855(18) 0.86996(12) 1.000 0.0508(5) . .
C7 C Uani 0.3134(2) 0.20292(14) 0.76841(10) 1.000 0.0392(4) . .
C8 C Uani 0.1011(2) 0.27109(15) 0.74892(11) 1.000 0.0402(4) . .
C9 C Uani -0.0964(3) 0.2331(2) 1.02870(14) 1.000 0.0739(7) . .
C10 C Uani 0.3121(3) -0.04581(18) 0.66161(15) 1.000 0.0622(6) . .
C11 C Uani 0.3016(2) 0.31461(14) 0.47617(10) 1.000 0.0383(4) . .
C12 C Uani 0.1364(2) 0.28464(18) 0.41409(11) 1.000 0.0469(4) . .
C13 C Uani 0.1753(2) 0.3187(2) 0.30657(12) 1.000 0.0547(5) . .
C14 C Uani 0.3770(2) 0.38597(17) 0.25698(11) 1.000 0.0487(5) . .
C15 C Uani 0.5384(2) 0.41712(16) 0.31888(12) 1.000 0.0476(4) . .
C16 C Uani 0.5038(2) 0.38224(16) 0.42695(11) 1.000 0.0439(4) . .
C17 C Uani 0.4213(4) 0.4185(2) 0.14063(14) 1.000 0.0767(8) . .
H2 H Uiso -0.05990 0.37040 0.60080 1.000 0.0520 calc R
H3 H Uiso -0.17590 0.33160 0.81990 1.000 0.0590 calc R
H5 H Uiso 0.31680 0.12270 1.02140 1.000 0.0660 calc R
H6 H Uiso 0.54740 0.10560 0.88240 1.000 0.0610 calc R
H12 H Uiso -0.00340 0.24020 0.44580 1.000 0.0560 calc R
H13 H Uiso 0.06170 0.29660 0.26560 1.000 0.0670 calc R
H15 H Uiso 0.67630 0.46350 0.28640 1.000 0.0560 calc R
H16 H Uiso 0.61820 0.40450 0.46750 1.000 0.0520 calc R
H71 H Uiso 0.58200 0.41460 0.12670 1.000 0.0910 calc R
H72 H Uiso 0.36520 0.50960 0.10300 1.000 0.0920 calc R
H73 H Uiso 0.34360 0.35260 0.11860 1.000 0.0910 calc R
H91 H Uiso -0.19250 0.15310 1.05400 1.000 0.0910 calc R
H92 H Uiso -0.18910 0.31480 1.00840 1.000 0.0910 calc R
H93 H Uiso 0.00360 0.23390 1.08310 1.000 0.0910 calc R
H101 H Uiso 0.19050 0.01060 0.62300 1.000 0.0760 calc R
H102 H Uiso 0.35820 -0.11100 0.62920 1.000 0.0760 calc R
H103 H Uiso 0.26040 -0.09440 0.73220 1.000 0.0760 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 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.125 0.123
;
International Tables for Crystallography
(1992, 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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 118.89(7) . . . yes
O1 S1 N1 107.21(7) . . . yes
O1 S1 C10 109.48(9) . . . yes
O2 S1 N1 107.57(7) . . . yes
O2 S1 C10 108.88(8) . . . yes
N1 S1 C10 103.73(8) . . . yes
S1 N1 C1 118.72(10) . . . yes
S1 N1 C7 118.09(9) . . . yes
C1 N1 C7 106.24(10) . . . yes
N1 C1 C2 109.21(11) . . . yes
N1 C1 C11 123.02(11) . . . yes
C2 C1 C11 127.65(12) . . . no
C1 C2 C8 108.86(12) . . . no
C4 C3 C8 119.39(13) . . . no
C3 C4 C5 119.03(14) . . . no
C3 C4 C9 121.08(15) . . . no
C5 C4 C9 119.89(14) . . . no
C4 C5 C6 123.01(14) . . . no
C5 C6 C7 116.96(13) . . . no
N1 C7 C6 129.93(12) . . . yes
N1 C7 C8 108.34(11) . . . yes
C6 C7 C8 121.65(12) . . . no
C2 C8 C3 132.73(12) . . . no
C2 C8 C7 107.34(12) . . . no
C3 C8 C7 119.91(12) . . . no
C1 C11 C12 119.73(11) . . . no
C1 C11 C16 121.55(12) . . . no
C12 C11 C16 118.63(12) . . . no
C11 C12 C13 120.34(12) . . . no
C12 C13 C14 121.30(14) . . . no
C13 C14 C15 117.98(13) . . . no
C13 C14 C17 120.94(15) . . . no
C15 C14 C17 121.05(14) . . . no
C14 C15 C16 121.57(12) . . . no
C11 C16 C15 120.17(12) . . . no
C1 C2 H2 126.00 . . . no
C8 C2 H2 126.00 . . . no
C4 C3 H3 120.00 . . . no
C8 C3 H3 120.00 . . . no
C4 C5 H5 119.00 . . . no
C6 C5 H5 118.00 . . . no
C5 C6 H6 122.00 . . . no
C7 C6 H6 121.00 . . . no
C4 C9 H91 109.00 . . . no
C4 C9 H92 110.00 . . . no
C4 C9 H93 109.00 . . . no
H91 C9 H92 109.00 . . . no
H91 C9 H93 109.00 . . . no
H92 C9 H93 110.00 . . . no
S1 C10 H101 109.00 . . . no
S1 C10 H102 110.00 . . . no
S1 C10 H103 110.00 . . . no
H101 C10 H102 109.00 . . . no
H101 C10 H103 109.00 . . . no
H102 C10 H103 109.00 . . . no
C11 C12 H12 120.00 . . . no
C13 C12 H12 120.00 . . . no
C12 C13 H13 119.00 . . . no
C14 C13 H13 119.00 . . . no
C14 C15 H15 119.00 . . . no
C16 C15 H15 119.00 . . . no
C11 C16 H16 120.00 . . . no
C15 C16 H16 120.00 . . . no
C14 C17 H71 110.00 . . . no
C14 C17 H72 109.00 . . . no
C14 C17 H73 109.00 . . . no
H71 C17 H72 109.00 . . . no
H71 C17 H73 110.00 . . . no
H72 C17 H73 110.00 . . . no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4231(16) . . yes
S1 O2 1.4224(16) . . yes
S1 N1 1.6952(18) . . yes
S1 C10 1.763(2) . . yes
N1 C1 1.4345(19) . . yes
N1 C7 1.4309(19) . . yes
C1 C2 1.353(2) . . no
C1 C11 1.468(2) . . no
C2 C8 1.438(2) . . no
C3 C4 1.385(2) . . no
C3 C8 1.400(2) . . no
C4 C5 1.397(3) . . no
C4 C9 1.514(3) . . no
C5 C6 1.382(2) . . no
C6 C7 1.391(2) . . no
C7 C8 1.394(2) . . no
C11 C12 1.395(2) . . no
C11 C16 1.398(2) . . no
C12 C13 1.381(2) . . no
C13 C14 1.395(2) . . no
C14 C15 1.383(2) . . no
C14 C17 1.502(2) . . no
C15 C16 1.384(2) . . no
C2 H2 0.9500 . . no
C3 H3 0.9500 . . no
C5 H5 0.9500 . . no
C6 H6 0.9500 . . no
C9 H91 0.9500 . . no
C9 H92 0.9500 . . no
C9 H93 0.9500 . . no
C10 H101 0.9500 . . no
C10 H102 0.9500 . . no
C10 H103 0.9500 . . no
C12 H12 0.9500 . . no
C13 H13 0.9500 . . no
C15 H15 0.9500 . . no
C16 H16 0.9500 . . no
C17 H71 0.9500 . . no
C17 H72 0.9500 . . no
C17 H73 0.9500 . . no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C12 H12 O2 0.9500 2.5600 3.498(3) 169.00 1_455 yes
C10 H102 O2 0.9500 2.5700 3.269(3) 131.00 2_656 yes
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
O1 S1 N1 C1 -172.33(10) . . . . no
O1 S1 N1 C7 -41.50(12) . . . . no
O2 S1 N1 C1 58.72(11) . . . . no
O2 S1 N1 C7 -170.45(10) . . . . no
C10 S1 N1 C1 -56.54(12) . . . . no
C10 S1 N1 C7 74.29(12) . . . . no
S1 N1 C1 C2 137.08(12) . . . . no
S1 N1 C1 C11 -46.76(17) . . . . no
C7 N1 C1 C2 1.13(16) . . . . no
C7 N1 C1 C11 177.29(13) . . . . no
S1 N1 C7 C6 46.3(2) . . . . no
S1 N1 C7 C8 -137.13(11) . . . . no
C1 N1 C7 C6 -177.44(16) . . . . no
C1 N1 C7 C8 -0.86(16) . . . . no
N1 C1 C2 C8 -0.97(18) . . . . no
C11 C1 C2 C8 -176.90(14) . . . . no
N1 C1 C11 C12 131.61(15) . . . . no
N1 C1 C11 C16 -51.7(2) . . . . no
C2 C1 C11 C12 -53.0(2) . . . . no
C2 C1 C11 C16 123.73(17) . . . . no
C1 C2 C8 C3 178.48(17) . . . . no
C1 C2 C8 C7 0.42(18) . . . . no
C8 C3 C4 C5 2.3(3) . . . . no
C8 C3 C4 C9 -177.75(16) . . . . no
C4 C3 C8 C2 -179.03(18) . . . . no
C4 C3 C8 C7 -1.2(2) . . . . no
C3 C4 C5 C6 -1.2(3) . . . . no
C9 C4 C5 C6 178.83(18) . . . . no
C4 C5 C6 C7 -1.0(3) . . . . no
C5 C6 C7 N1 178.37(16) . . . . no
C5 C6 C7 C8 2.2(2) . . . . no
N1 C7 C8 C2 0.30(17) . . . . no
N1 C7 C8 C3 -178.06(14) . . . . no
C6 C7 C8 C2 177.22(15) . . . . no
C6 C7 C8 C3 -1.1(2) . . . . no
C1 C11 C12 C13 178.19(16) . . . . no
C16 C11 C12 C13 1.4(2) . . . . no
C1 C11 C16 C15 -177.31(14) . . . . no
C12 C11 C16 C15 -0.6(2) . . . . no
C11 C12 C13 C14 -1.3(3) . . . . no
C12 C13 C14 C15 0.3(3) . . . . no
C12 C13 C14 C17 178.02(18) . . . . no
C13 C14 C15 C16 0.5(3) . . . . no
C17 C14 C15 C16 -177.19(17) . . . . no
C14 C15 C16 C11 -0.4(2) . . . . no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26996042
2 PubChem 53388442
