#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:37:41 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268958 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/82/7158202.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_7158202
loop_
_publ_author_name
'Sandeep, K.'
'Siva Reddy, Alla'
'Kumara Swamy, K. C.'
_publ_section_title
;
 Palladium-catalysed cyclisation of ynamides and propargyl tethered
 iodosulfonamides with boronic acids leading to benzosultams.
;
_journal_issue                   31
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6871
_journal_page_last               6882
_journal_paper_doi               10.1039/d1ob00925g
_journal_volume                  19
_journal_year                    2021
_chemical_formula_sum            'C21 H19 N O2 S2'
_chemical_formula_weight         381.49
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2021-05-08 deposited with the CCDC.	2021-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.477(2)
_cell_angle_beta                 106.658(2)
_cell_angle_gamma                116.051(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8974(2)
_cell_length_b                   9.9589(3)
_cell_length_c                   11.7524(3)
_cell_measurement_reflns_used    7197
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.6920
_cell_measurement_theta_min      2.2890
_cell_volume                     984.84(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13154
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.285
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             400
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3470
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0632P)²+0.3450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1339
_reflns_number_gt                2779
_reflns_number_total             3470
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob00925g2.cif
_cod_data_source_block           Compound3jb
_cod_depositor_comments
'Adding full bibliography for 7158201--7158205.cif.'
_cod_original_cell_volume        984.84(4)
_cod_database_code               7158202
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
S1 S 0.32341(7) 0.24920(7) 0.78440(5) 0.0526(2) Uani 1 1 d . . .
S2 S 1.00225(9) 0.20307(10) 0.94401(6) 0.0735(3) Uani 1 1 d . . .
O2 O 0.3084(2) 0.3681(2) 0.83914(17) 0.0746(6) Uani 1 1 d . . .
O1 O 0.2456(2) 0.1023(2) 0.81522(17) 0.0741(6) Uani 1 1 d . . .
N1 N 0.5114(2) 0.2977(2) 0.80597(16) 0.0494(5) Uani 1 1 d . . .
C10 C 0.7152(2) 0.2753(2) 0.58406(19) 0.0402(5) Uani 1 1 d . . .
C8 C 0.5438(3) 0.2811(3) 0.69651(18) 0.0419(5) Uani 1 1 d . . .
C9 C 0.6726(2) 0.2660(2) 0.69625(19) 0.0418(5) Uani 1 1 d . . .
C6 C 0.4052(3) 0.2605(2) 0.59353(18) 0.0399(5) Uani 1 1 d . . .
C15 C 0.6973(3) 0.1482(3) 0.5196(2) 0.0449(5) Uani 1 1 d . . .
H15 H 0.6705 0.0584 0.5516 0.054 Uiso 1 1 calc R . .
C17 C 0.7688(3) 0.2289(3) 0.79939(19) 0.0456(5) Uani 1 1 d . . .
C5 C 0.3804(3) 0.2454(3) 0.4701(2) 0.0484(6) Uani 1 1 d . . .
H5 H 0.4644 0.2610 0.4423 0.058 Uiso 1 1 calc R . .
C1 C 0.2751(3) 0.2367(3) 0.6296(2) 0.0446(5) Uani 1 1 d . . .
C14 C 0.7187(3) 0.1531(3) 0.4089(2) 0.0507(6) Uani 1 1 d . . .
H14 H 0.7034 0.0656 0.3664 0.061 Uiso 1 1 calc R . .
C11 C 0.7648(3) 0.4086(3) 0.5366(2) 0.0564(6) Uani 1 1 d . . .
H11 H 0.7826 0.4969 0.5796 0.068 Uiso 1 1 calc R . .
C13 C 0.7623(3) 0.2842(3) 0.3592(2) 0.0537(6) Uani 1 1 d . . .
C2 C 0.1255(3) 0.1970(3) 0.5500(2) 0.0544(6) Uani 1 1 d . . .
H2 H 0.0409 0.1805 0.5774 0.065 Uiso 1 1 calc R . .
C4 C 0.2316(3) 0.2073(3) 0.3884(2) 0.0562(7) Uani 1 1 d . . .
C3 C 0.1059(3) 0.1828(3) 0.4299(2) 0.0586(7) Uani 1 1 d . . .
H3 H 0.0063 0.1562 0.3747 0.070 Uiso 1 1 calc R . .
C20 C 0.9269(3) 0.2728(3) 0.8240(2) 0.0569(7) Uani 1 1 d . . .
H20 H 0.9872 0.3345 0.7797 0.068 Uiso 1 1 calc R . .
C12 C 0.7882(4) 0.4122(3) 0.4260(2) 0.0637(7) Uani 1 1 d . . .
H12 H 0.8222 0.5033 0.3961 0.076 Uiso 1 1 calc R . .
C18 C 0.7095(3) 0.1335(3) 0.8816(2) 0.0598(7) Uani 1 1 d . . .
H18 H 0.6041 0.0905 0.8792 0.072 Uiso 1 1 calc R . .
C19 C 0.8258(3) 0.1121(3) 0.9649(2) 0.0642(7) Uani 1 1 d . . .
H19 H 0.8080 0.0539 1.0256 0.077 Uiso 1 1 calc R . .
C21 C 0.6325(3) 0.4125(4) 0.9087(2) 0.0726(8) Uani 1 1 d . . .
H21A H 0.7289 0.4662 0.8897 0.109 Uiso 1 1 calc R . .
H21B H 0.6524 0.3643 0.9775 0.109 Uiso 1 1 calc R . .
H21C H 0.5955 0.4822 0.9262 0.109 Uiso 1 1 calc R . .
C16 C 0.7819(5) 0.2880(4) 0.2362(3) 0.0862(10) Uani 1 1 d . . .
H16A H 0.7255 0.3370 0.1891 0.129 Uiso 1 1 calc R . .
H16B H 0.7399 0.1865 0.1969 0.129 Uiso 1 1 calc R . .
H16C H 0.8926 0.3430 0.2445 0.129 Uiso 1 1 calc R . .
C7 C 0.2085(4) 0.1932(5) 0.2556(2) 0.0928(11) Uani 1 1 d . . .
H7A H 0.3046 0.2049 0.2431 0.139 Uiso 1 1 calc R . .
H7B H 0.1830 0.2703 0.2229 0.139 Uiso 1 1 calc R . .
H7C H 0.1234 0.0954 0.2161 0.139 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 116.75(13) . . ?
O2 S1 N1 110.38(11) . . ?
O1 S1 N1 110.55(12) . . ?
O2 S1 C1 113.31(12) . . ?
O1 S1 C1 109.62(12) . . ?
N1 S1 C1 93.92(10) . . ?
C19 S2 C20 92.06(13) . . ?
C8 N1 C21 121.1(2) . . ?
C8 N1 S1 113.10(15) . . ?
C21 N1 S1 118.86(17) . . ?
C11 C10 C15 117.6(2) . . ?
C11 C10 C9 121.3(2) . . ?
C15 C10 C9 121.0(2) . . ?
C9 C8 N1 121.75(19) . . ?
C9 C8 C6 128.9(2) . . ?
N1 C8 C6 108.72(18) . . ?
C8 C9 C17 123.5(2) . . ?
C8 C9 C10 119.40(19) . . ?
C17 C9 C10 116.95(19) . . ?
C1 C6 C5 117.0(2) . . ?
C1 C6 C8 111.69(19) . . ?
C5 C6 C8 130.9(2) . . ?
C14 C15 C10 120.8(2) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C20 C17 C18 110.3(2) . . ?
C20 C17 C9 124.0(2) . . ?
C18 C17 C9 125.5(2) . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C2 C1 C6 123.4(2) . . ?
C2 C1 S1 125.42(19) . . ?
C6 C1 S1 110.99(17) . . ?
C15 C14 C13 121.7(2) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C10 C11 C12 120.8(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C12 C13 C14 117.5(2) . . ?
C12 C13 C16 121.1(2) . . ?
C14 C13 C16 121.5(2) . . ?
C3 C2 C1 117.8(2) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 C7 119.6(3) . . ?
C3 C4 C7 120.8(2) . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C17 C20 S2 112.98(19) . . ?
C17 C20 H20 123.5 . . ?
S2 C20 H20 123.5 . . ?
C13 C12 C11 121.5(2) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C19 C18 C17 112.6(2) . . ?
C19 C18 H18 123.7 . . ?
C17 C18 H18 123.7 . . ?
C18 C19 S2 112.0(2) . . ?
C18 C19 H19 124.0 . . ?
S2 C19 H19 124.0 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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
S1 O2 1.4266(19) . ?
S1 O1 1.430(2) . ?
S1 N1 1.6428(19) . ?
S1 C1 1.732(2) . ?
S2 C19 1.671(3) . ?
S2 C20 1.702(3) . ?
N1 C8 1.437(3) . ?
N1 C21 1.464(3) . ?
C10 C11 1.382(3) . ?
C10 C15 1.386(3) . ?
C10 C9 1.487(3) . ?
C8 C9 1.348(3) . ?
C8 C6 1.479(3) . ?
C9 C17 1.472(3) . ?
C6 C1 1.392(3) . ?
C6 C5 1.395(3) . ?
C15 C14 1.375(3) . ?
C15 H15 0.9300 . ?
C17 C20 1.364(3) . ?
C17 C18 1.424(3) . ?
C5 C4 1.388(3) . ?
C5 H5 0.9300 . ?
C1 C2 1.382(3) . ?
C14 C13 1.376(3) . ?
C14 H14 0.9300 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9300 . ?
C13 C12 1.374(4) . ?
C13 C16 1.511(3) . ?
C2 C3 1.367(4) . ?
C2 H2 0.9300 . ?
C4 C3 1.389(4) . ?
C4 C7 1.507(4) . ?
C3 H3 0.9300 . ?
C20 H20 0.9300 . ?
C12 H12 0.9300 . ?
C18 C19 1.379(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
