#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:37:41 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268958 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/82/7158203.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_7158203
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            'C22 H18 Cl N O2 S'
_chemical_formula_weight         395.88
_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                104.997(3)
_cell_angle_beta                 112.432(3)
_cell_angle_gamma                95.785(4)
_cell_formula_units_Z            2
_cell_length_a                   10.0494(11)
_cell_length_b                   10.1081(10)
_cell_length_c                   10.9713(10)
_cell_measurement_reflns_used    9862
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.25
_cell_volume                     969.89(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0140
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            35324
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.036(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3388
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0422P)²+0.4096P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0918
_reflns_number_gt                2977
_reflns_number_total             3388
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob00925g2.cif
_cod_data_source_block           Compound3ad
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7158201--7158205.cif.
;
_cod_original_cell_volume        969.88(17)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7158203
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 0.25917(6) 0.64120(5) 0.63997(5) 0.04661(17) Uani 1 1 d . . .
Cl1 Cl 0.16421(6) -0.17941(6) 0.00008(5) 0.06087(19) Uani 1 1 d . . .
O2 O 0.13624(19) 0.69702(15) 0.64872(17) 0.0680(4) Uani 1 1 d . . .
N1 N 0.24202(17) 0.48060(15) 0.64946(14) 0.0422(4) Uani 1 1 d . . .
O1 O 0.40287(19) 0.72526(16) 0.73470(15) 0.0716(5) Uani 1 1 d . . .
C10 C 0.24597(18) 0.13749(16) 0.40984(17) 0.0342(4) Uani 1 1 d . . .
C9 C 0.27237(18) 0.25057(17) 0.54053(17) 0.0351(4) Uani 1 1 d . . .
C8 C 0.25107(18) 0.37967(17) 0.53644(16) 0.0360(4) Uani 1 1 d . . .
C6 C 0.24151(18) 0.44408(17) 0.42735(17) 0.0367(4) Uani 1 1 d . . .
C16 C 0.32054(18) 0.21290(17) 0.67043(17) 0.0358(4) Uani 1 1 d . . .
C13 C 0.1960(2) -0.06075(18) 0.16095(17) 0.0406(4) Uani 1 1 d . . .
C17 C 0.43167(19) 0.30549(19) 0.79451(18) 0.0434(4) Uani 1 1 d . . .
H17 H 0.4762 0.3912 0.7954 0.052 Uiso 1 1 calc R . .
C11 C 0.10423(19) 0.08012(19) 0.30668(18) 0.0427(4) Uani 1 1 d . . .
H11 H 0.0250 0.1091 0.3211 0.051 Uiso 1 1 calc R . .
C21 C 0.2593(2) 0.08419(18) 0.67263(19) 0.0429(4) Uani 1 1 d . . .
H21 H 0.1872 0.0194 0.5907 0.051 Uiso 1 1 calc R . .
C12 C 0.0784(2) -0.01983(19) 0.18220(19) 0.0456(4) Uani 1 1 d . . .
H12 H -0.0175 -0.0587 0.1139 0.055 Uiso 1 1 calc R . .
C1 C 0.24536(19) 0.58680(18) 0.47152(18) 0.0395(4) Uani 1 1 d . . .
C18 C 0.4764(2) 0.2715(2) 0.91595(19) 0.0504(5) Uani 1 1 d . . .
H18 H 0.5507 0.3344 0.9978 0.060 Uiso 1 1 calc R . .
C15 C 0.3615(2) 0.0889(2) 0.38752(19) 0.0483(5) Uani 1 1 d . . .
H15 H 0.4570 0.1228 0.4578 0.058 Uiso 1 1 calc R . .
C5 C 0.2360(2) 0.38643(19) 0.29498(18) 0.0457(4) Uani 1 1 d . . .
H5 H 0.2375 0.2921 0.2634 0.055 Uiso 1 1 calc R . .
C20 C 0.3041(2) 0.0510(2) 0.7950(2) 0.0493(5) Uani 1 1 d . . .
H20 H 0.2612 -0.0350 0.7947 0.059 Uiso 1 1 calc R . .
C14 C 0.3376(2) -0.0089(2) 0.2628(2) 0.0507(5) Uani 1 1 d . . .
H14 H 0.4163 -0.0391 0.2481 0.061 Uiso 1 1 calc R . .
C22 C 0.1516(2) 0.4420(2) 0.7174(2) 0.0537(5) Uani 1 1 d . . .
H22A H 0.0797 0.3564 0.6570 0.080 Uiso 1 1 calc R . .
H22B H 0.1021 0.5156 0.7372 0.080 Uiso 1 1 calc R . .
H22C H 0.2135 0.4286 0.8028 0.080 Uiso 1 1 calc R . .
C19 C 0.4118(2) 0.1448(2) 0.9168(2) 0.0512(5) Uani 1 1 d . . .
H19 H 0.4409 0.1231 0.9992 0.061 Uiso 1 1 calc R . .
C4 C 0.2283(2) 0.4684(2) 0.21023(19) 0.0504(5) Uani 1 1 d . . .
C2 C 0.2418(2) 0.6723(2) 0.3907(2) 0.0495(5) Uani 1 1 d . . .
H2 H 0.2464 0.7678 0.4241 0.059 Uiso 1 1 calc R . .
C3 C 0.2313(2) 0.6107(2) 0.2592(2) 0.0534(5) Uani 1 1 d . . .
H3 H 0.2260 0.6652 0.2017 0.064 Uiso 1 1 calc R . .
C7 C 0.2149(3) 0.4034(3) 0.0652(2) 0.0776(7) Uani 1 1 d . . .
H7A H 0.2627 0.3257 0.0625 0.116 Uiso 1 1 calc R . .
H7B H 0.2611 0.4722 0.0391 0.116 Uiso 1 1 calc R . .
H7C H 0.1124 0.3706 0.0013 0.116 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'
Cl Cl 0.1484 0.1585 '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 116.61(10) . . ?
O1 S1 N1 111.01(9) . . ?
O2 S1 N1 109.89(9) . . ?
O1 S1 C1 110.57(9) . . ?
O2 S1 C1 112.72(9) . . ?
N1 S1 C1 93.73(7) . . ?
C8 N1 C22 121.34(15) . . ?
C8 N1 S1 113.27(11) . . ?
C22 N1 S1 117.76(12) . . ?
C11 C10 C15 118.28(15) . . ?
C11 C10 C9 120.24(15) . . ?
C15 C10 C9 121.47(15) . . ?
C8 C9 C16 123.14(14) . . ?
C8 C9 C10 120.00(14) . . ?
C16 C9 C10 116.86(13) . . ?
C9 C8 N1 121.96(14) . . ?
C9 C8 C6 129.08(14) . . ?
N1 C8 C6 108.89(13) . . ?
C1 C6 C5 117.32(15) . . ?
C1 C6 C8 111.90(14) . . ?
C5 C6 C8 130.71(15) . . ?
C21 C16 C17 117.80(16) . . ?
C21 C16 C9 121.65(15) . . ?
C17 C16 C9 120.53(15) . . ?
C14 C13 C12 121.23(16) . . ?
C14 C13 Cl1 119.67(14) . . ?
C12 C13 Cl1 119.09(14) . . ?
C18 C17 C16 120.84(17) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C10 C11 C12 121.04(16) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C20 C21 C16 121.04(17) . . ?
C20 C21 H21 119.5 . . ?
C16 C21 H21 119.5 . . ?
C13 C12 C11 119.13(16) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C2 C1 C6 123.45(16) . . ?
C2 C1 S1 125.59(14) . . ?
C6 C1 S1 110.94(13) . . ?
C19 C18 C17 120.50(18) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C14 C15 C10 121.26(17) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
C4 C5 C6 120.53(17) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C19 C20 C21 120.28(18) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C13 C14 C15 118.95(17) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C19 C18 119.50(17) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C5 C4 C3 119.77(17) . . ?
C5 C4 C7 119.98(19) . . ?
C3 C4 C7 120.25(18) . . ?
C3 C2 C1 117.49(17) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 121.37(17) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
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 O1 1.4275(16) . ?
S1 O2 1.4341(15) . ?
S1 N1 1.6494(15) . ?
S1 C1 1.7321(17) . ?
Cl1 C13 1.7471(17) . ?
N1 C8 1.427(2) . ?
N1 C22 1.460(2) . ?
C10 C11 1.382(2) . ?
C10 C15 1.385(2) . ?
C10 C9 1.494(2) . ?
C9 C8 1.353(2) . ?
C9 C16 1.484(2) . ?
C8 C6 1.481(2) . ?
C6 C1 1.389(2) . ?
C6 C5 1.395(2) . ?
C16 C21 1.392(2) . ?
C16 C17 1.395(2) . ?
C13 C14 1.372(3) . ?
C13 C12 1.372(3) . ?
C17 C18 1.381(3) . ?
C17 H17 0.9300 . ?
C11 C12 1.384(2) . ?
C11 H11 0.9300 . ?
C21 C20 1.385(3) . ?
C21 H21 0.9300 . ?
C12 H12 0.9300 . ?
C1 C2 1.383(2) . ?
C18 C19 1.380(3) . ?
C18 H18 0.9300 . ?
C15 C14 1.382(3) . ?
C15 H15 0.9300 . ?
C5 C4 1.384(3) . ?
C5 H5 0.9300 . ?
C20 C19 1.374(3) . ?
C20 H20 0.9300 . ?
C14 H14 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C19 H19 0.9300 . ?
C4 C3 1.392(3) . ?
C4 C7 1.503(3) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
