#------------------------------------------------------------------------------
#$Date: 2022-11-09 03:51:36 +0200 (Wed, 09 Nov 2022) $
#$Revision: 279132 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/89/7158974.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_7158974
loop_
_publ_author_name
'Sunke, Rajnikanth'
'Ahmed Khan, Shabbir'
'Kumara Swamy, K. C.'
_publ_section_title
;
 Pd-catalysed intramolecular transformations of
 indolylbenzenesulfonamides: ortho-sulfonamido-bi(hetero)aryls via
 C2-arylation and polycyclic sultams via C3 arylation
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01610A
_journal_year                    2022
_chemical_formula_sum            'C17 H17 I N2 O2 S'
_chemical_formula_weight         440.29
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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_block_doi                 10.5517/ccdc.csd.cc2cxc8y
_audit_creation_method           'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_audit_update_record
;
2022-08-17 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 112.875(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2737(4)
_cell_length_b                   18.0774(6)
_cell_length_c                   16.6031(8)
_cell_measurement_reflns_used    6561
_cell_measurement_temperature    297.54(10)
_cell_measurement_theta_max      26.6990
_cell_measurement_theta_min      2.2520
_cell_volume                     1734.91(18)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      297.54(10)
_diffrn_measured_fraction_theta_full acta50
_diffrn_measured_fraction_theta_max 0.823
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_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  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8461
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    1.976
_exptl_absorpt_correction_T_max  0.8269
_exptl_absorpt_correction_T_min  0.6933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             872
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.883
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.078
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0405
_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)+(0.0631P)²+2.6845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1204
_reflns_number_gt                2177
_reflns_number_total             2513
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ob01610a2.cif
_cod_data_source_block           Compound5aa
_cod_original_cell_volume        1734.91(15)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7158974
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
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.09277(9) 0.49080(2) 0.40766(3) 0.0739(3) Uani 1 1 d . . .
S1 S -0.0645(2) 0.48002(8) 0.17041(10) 0.0487(4) Uani 1 1 d . . .
O1 O -0.2101(6) 0.4587(2) 0.2135(3) 0.0637(11) Uani 1 1 d . . .
N1 N 0.0997(7) 0.3089(2) 0.2682(3) 0.0414(10) Uani 1 1 d . . .
O2 O -0.1639(8) 0.5118(2) 0.0854(3) 0.0687(12) Uani 1 1 d . . .
N2 N 0.0709(7) 0.4036(2) 0.1611(3) 0.0456(10) Uani 1 1 d . . .
C1 C 0.2646(9) 0.2786(3) 0.3401(3) 0.0433(13) Uani 1 1 d . . .
C8 C 0.2004(9) 0.3661(2) 0.2400(3) 0.0388(12) Uani 1 1 d . . .
C6 C 0.4741(9) 0.3173(3) 0.3584(3) 0.0452(13) Uani 1 1 d . . .
C7 C 0.4247(9) 0.3729(3) 0.2933(3) 0.0440(12) Uani 1 1 d . . .
H7 H 0.5283 0.4076 0.2884 0.053 Uiso 1 1 calc R . .
C16 C 0.2316(9) 0.5471(3) 0.3282(4) 0.0447(13) Uani 1 1 d . . .
C2 C 0.2566(11) 0.2175(3) 0.3909(4) 0.0567(15) Uani 1 1 d . . .
H2 H 0.1185 0.1925 0.3798 0.068 Uiso 1 1 calc R . .
C13 C 0.4524(10) 0.6248(3) 0.2403(4) 0.0554(15) Uani 1 1 d . . .
H13 H 0.5271 0.6507 0.2104 0.067 Uiso 1 1 calc R . .
C11 C 0.1552(9) 0.5399(3) 0.2371(3) 0.0431(12) Uani 1 1 d . . .
C9 C -0.1365(10) 0.2825(3) 0.2257(4) 0.0582(15) Uani 1 1 d . . .
H9A H -0.2132 0.2859 0.2655 0.087 Uiso 1 1 calc R . .
H9B H -0.1352 0.2319 0.2083 0.087 Uiso 1 1 calc R . .
H9C H -0.2172 0.3122 0.1750 0.087 Uiso 1 1 calc R . .
C12 C 0.2729(10) 0.5798(3) 0.1952(4) 0.0489(13) Uani 1 1 d . . .
H12 H 0.2271 0.5753 0.1350 0.059 Uiso 1 1 calc R . .
C15 C 0.4110(10) 0.5946(3) 0.3723(4) 0.0532(14) Uani 1 1 d . . .
H15 H 0.4551 0.6008 0.4322 0.064 Uiso 1 1 calc R . .
C14 C 0.5270(10) 0.6332(3) 0.3301(4) 0.0537(15) Uani 1 1 d . . .
C3 C 0.4536(13) 0.1959(4) 0.4560(4) 0.0712(19) Uani 1 1 d . . .
H3 H 0.4508 0.1546 0.4890 0.085 Uiso 1 1 calc R . .
C10 C 0.1865(11) 0.4074(3) 0.0980(4) 0.0599(15) Uani 1 1 d . . .
H10A H 0.2194 0.3582 0.0842 0.090 Uiso 1 1 calc R . .
H10B H 0.3283 0.4347 0.1236 0.090 Uiso 1 1 calc R . .
H10C H 0.0864 0.4318 0.0455 0.090 Uiso 1 1 calc R . .
C5 C 0.6731(12) 0.2945(4) 0.4272(4) 0.0623(16) Uani 1 1 d . . .
H5 H 0.8113 0.3199 0.4402 0.075 Uiso 1 1 calc R . .
C4 C 0.6640(13) 0.2339(4) 0.4758(4) 0.0737(19) Uani 1 1 d . . .
H4 H 0.7968 0.2179 0.5218 0.088 Uiso 1 1 calc R . .
C17 C 0.7240(12) 0.6841(4) 0.3801(5) 0.081(2) Uani 1 1 d . . .
H17A H 0.7293 0.6910 0.4382 0.121 Uiso 1 1 calc R . .
H17B H 0.7014 0.7311 0.3509 0.121 Uiso 1 1 calc R . .
H17C H 0.8670 0.6628 0.3831 0.121 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'
I I -0.4742 1.8119 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 119.4(3) . . ?
O1 S1 N2 106.0(2) . . ?
O2 S1 N2 106.6(3) . . ?
O1 S1 C11 110.5(2) . . ?
O2 S1 C11 108.0(3) . . ?
N2 S1 C11 105.4(2) . . ?
C1 N1 C8 107.9(4) . . ?
C1 N1 C9 125.5(4) . . ?
C8 N1 C9 126.5(5) . . ?
C8 N2 C10 114.3(4) . . ?
C8 N2 S1 116.2(3) . . ?
C10 N2 S1 115.7(3) . . ?
N1 C1 C2 130.9(5) . . ?
N1 C1 C6 108.5(4) . . ?
C2 C1 C6 120.5(5) . . ?
C7 C8 N1 110.1(4) . . ?
C7 C8 N2 130.0(4) . . ?
N1 C8 N2 119.8(5) . . ?
C5 C6 C1 119.7(5) . . ?
C5 C6 C7 134.2(5) . . ?
C1 C6 C7 106.1(5) . . ?
C8 C7 C6 107.4(4) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
C15 C16 C11 119.8(4) . . ?
C15 C16 I1 114.8(4) . . ?
C11 C16 I1 125.4(4) . . ?
C3 C2 C1 118.4(6) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C12 C13 C14 121.3(5) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C12 C11 C16 117.6(5) . . ?
C12 C11 S1 116.1(4) . . ?
C16 C11 S1 126.1(4) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C13 C12 C11 121.5(5) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C16 C15 C14 121.9(5) . . ?
C16 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C15 C14 C13 117.8(5) . . ?
C15 C14 C17 120.8(6) . . ?
C13 C14 C17 121.4(5) . . ?
C2 C3 C4 122.1(6) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C5 C6 119.4(6) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C4 C3 120.0(6) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
I1 C16 2.104(4) . ?
S1 O1 1.416(4) . ?
S1 O2 1.423(4) . ?
S1 N2 1.661(4) . ?
S1 C11 1.764(6) . ?
N1 C1 1.354(6) . ?
N1 C8 1.385(5) . ?
N1 C9 1.452(7) . ?
N2 C8 1.417(6) . ?
N2 C10 1.490(6) . ?
C1 C2 1.402(7) . ?
C1 C6 1.413(7) . ?
C8 C7 1.345(7) . ?
C6 C5 1.387(8) . ?
C6 C7 1.420(7) . ?
C7 H7 0.9300 . ?
C16 C15 1.377(8) . ?
C16 C11 1.404(7) . ?
C2 C3 1.345(9) . ?
C2 H2 0.9300 . ?
C13 C12 1.355(8) . ?
C13 C14 1.387(8) . ?
C13 H13 0.9300 . ?
C11 C12 1.396(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C12 H12 0.9300 . ?
C15 C14 1.380(7) . ?
C15 H15 0.9300 . ?
C14 C17 1.506(8) . ?
C3 C4 1.408(10) . ?
C3 H3 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C5 C4 1.376(9) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
