#------------------------------------------------------------------------------
#$Date: 2021-07-05 21:14:42 +0300 (Mon, 05 Jul 2021) $
#$Revision: 267249 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/80/7158084.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_7158084
loop_
_publ_author_name
'Lee, Kyu Ree'
'Jung, Da Jung'
'Ahn, Subin'
'Kim, Ji Won'
'Lee, Sang-Gi'
_publ_section_title
;
 Catalyst-controlled divergent transformations of
 N-sulfonyl-1,2,3-triazoles into isoquinolin-3-ones and
 2-aminoindanones.
;
_journal_issue                   23
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5093
_journal_page_last               5097
_journal_paper_doi               10.1039/d1ob00708d
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C18 H17 N O3 S'
_chemical_formula_sum            'C18 H17 N O3 S'
_chemical_formula_weight         327.39
_chemical_name_common            160628No1
_chemical_name_systematic        160628No1
_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_Hall  '-P 1'
_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           SHELXTL
_audit_update_record
;
2018-09-27 deposited with the CCDC.	2021-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                106.868(2)
_cell_angle_beta                 106.256(2)
_cell_angle_gamma                99.042(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3301(5)
_cell_length_b                   10.1313(5)
_cell_length_c                   10.5314(6)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.64
_cell_volume                     788.58(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'PHOTON 100 CMOS'
_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  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0133
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            33101
_diffrn_reflns_theta_full        28.34
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3937
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0389
_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)+(0.0582P)²+0.3016P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1112
_reflns_number_gt                3438
_reflns_number_total             3937
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ob00708d2.cif
_cod_data_source_block           No1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' 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.

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 7158083--7158084.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7158084
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
O1 O -0.08088(14) 0.37594(12) 0.55578(12) 0.0392(2) Uani 1 1 d . . .
C1 C 0.03022(17) 0.33007(14) 0.51786(15) 0.0296(3) Uani 1 1 d . . .
C2 C 0.01549(18) 0.27507(16) 0.36401(15) 0.0331(3) Uani 1 1 d . . .
H2A H -0.0429 0.1728 0.3231 0.040 Uiso 1 1 calc R . .
H2B H -0.0568 0.3237 0.3130 0.040 Uiso 1 1 calc R . .
C3 C 0.18727(18) 0.29680(14) 0.34214(14) 0.0289(3) Uani 1 1 d . . .
C4 C 0.2071(2) 0.32709(16) 0.22566(15) 0.0365(3) Uani 1 1 d . . .
H4 H 0.1111 0.3330 0.1569 0.044 Uiso 1 1 calc R . .
C5 C 0.3688(2) 0.34842(17) 0.21129(17) 0.0428(4) Uani 1 1 d . . .
H5 H 0.3817 0.3675 0.1320 0.051 Uiso 1 1 calc R . .
C6 C 0.5111(2) 0.34176(17) 0.31294(18) 0.0415(4) Uani 1 1 d . . .
H6 H 0.6205 0.3574 0.3032 0.050 Uiso 1 1 calc R . .
C7 C 0.49227(19) 0.31197(16) 0.42946(16) 0.0349(3) Uani 1 1 d . . .
H7 H 0.5889 0.3077 0.4989 0.042 Uiso 1 1 calc R . .
C8 C 0.32972(18) 0.28840(14) 0.44294(14) 0.0285(3) Uani 1 1 d . . .
C9 C 0.30518(18) 0.24998(15) 0.56594(14) 0.0297(3) Uani 1 1 d . . .
H9 H 0.4176 0.2855 0.6447 0.036 Uiso 1 1 calc R . .
C10 C 0.2437(2) 0.08953(17) 0.52631(17) 0.0393(3) Uani 1 1 d . . .
H10 H 0.1321 0.0429 0.4597 0.047 Uiso 1 1 calc R . .
C11 C 0.3339(3) 0.0126(2) 0.5776(3) 0.0605(5) Uani 1 1 d . . .
H11A H 0.4460 0.0556 0.6445 0.073 Uiso 1 1 calc R . .
H11B H 0.2875 -0.0865 0.5482 0.073 Uiso 1 1 calc R . .
N1 N 0.17859(15) 0.32175(13) 0.61348(12) 0.0294(2) Uani 1 1 d . . .
S1 S 0.21046(4) 0.38704(4) 0.78804(3) 0.03171(11) Uani 1 1 d . . .
O2 O 0.20001(15) 0.53143(11) 0.82348(12) 0.0420(3) Uani 1 1 d . . .
O3 O 0.36667(14) 0.35490(14) 0.85401(11) 0.0442(3) Uani 1 1 d . . .
C12 C 0.03985(19) 0.28661(15) 0.81576(14) 0.0312(3) Uani 1 1 d . . .
C13 C -0.0975(2) 0.34267(17) 0.83209(17) 0.0377(3) Uani 1 1 d . . .
H13 H -0.1066 0.4292 0.8183 0.045 Uiso 1 1 calc R . .
C14 C -0.2216(2) 0.26933(18) 0.86914(17) 0.0422(4) Uani 1 1 d . . .
H14 H -0.3143 0.3074 0.8818 0.051 Uiso 1 1 calc R . .
C15 C -0.2108(2) 0.14072(18) 0.88774(16) 0.0440(4) Uani 1 1 d . . .
C16 C -0.0746(2) 0.08468(17) 0.86618(17) 0.0451(4) Uani 1 1 d . . .
H16 H -0.0689 -0.0043 0.8749 0.054 Uiso 1 1 calc R . .
C17 C 0.0527(2) 0.15727(16) 0.83206(16) 0.0385(3) Uani 1 1 d . . .
H17 H 0.1459 0.1197 0.8202 0.046 Uiso 1 1 calc R . .
C18 C -0.3415(3) 0.0654(3) 0.9349(2) 0.0684(6) Uani 1 1 d . . .
H18A H -0.4270 0.1189 0.9440 0.103 Uiso 1 1 calc R . .
H18B H -0.2831 0.0585 1.0255 0.103 Uiso 1 1 calc R . .
H18C H -0.3984 -0.0297 0.8656 0.103 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
O1 C1 N1 121.77(13) . . ?
O1 C1 C2 122.58(13) . . ?
N1 C1 C2 115.64(11) . . ?
C3 C2 C1 113.58(11) . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C8 C3 C4 119.57(13) . . ?
C8 C3 C2 118.36(12) . . ?
C4 C3 C2 122.06(13) . . ?
C5 C4 C3 119.91(14) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 120.37(14) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.02(14) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C8 119.68(14) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C3 C8 C7 120.43(13) . . ?
C3 C8 C9 119.05(12) . . ?
C7 C8 C9 120.50(13) . . ?
N1 C9 C8 109.03(11) . . ?
N1 C9 C10 110.43(12) . . ?
C8 C9 C10 111.44(12) . . ?
N1 C9 H9 108.6 . . ?
C8 C9 H9 108.6 . . ?
C10 C9 H9 108.6 . . ?
C11 C10 C9 124.58(17) . . ?
C11 C10 H10 117.7 . . ?
C9 C10 H10 117.7 . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
C1 N1 C9 121.82(11) . . ?
C1 N1 S1 119.02(9) . . ?
C9 N1 S1 119.08(9) . . ?
O2 S1 O3 119.86(8) . . ?
O2 S1 N1 108.01(6) . . ?
O3 S1 N1 104.51(6) . . ?
O2 S1 C12 108.66(7) . . ?
O3 S1 C12 108.02(7) . . ?
N1 S1 C12 107.09(6) . . ?
C13 C12 C17 121.21(14) . . ?
C13 C12 S1 119.71(11) . . ?
C17 C12 S1 118.88(12) . . ?
C12 C13 C14 119.07(14) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 120.88(15) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 118.81(14) . . ?
C14 C15 C18 120.46(18) . . ?
C16 C15 C18 120.70(18) . . ?
C17 C16 C15 121.35(15) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C12 118.62(15) . . ?
C16 C17 H17 120.7 . . ?
C12 C17 H17 120.7 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
O1 C1 1.2109(17) . ?
C1 N1 1.3907(17) . ?
C1 C2 1.5146(19) . ?
C2 C3 1.5046(19) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 C8 1.3861(19) . ?
C3 C4 1.3937(19) . ?
C4 C5 1.388(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.382(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.389(2) . ?
C6 H6 0.9400 . ?
C7 C8 1.3916(19) . ?
C7 H7 0.9400 . ?
C8 C9 1.5124(18) . ?
C9 N1 1.4888(17) . ?
C9 C10 1.518(2) . ?
C9 H9 0.9900 . ?
C10 C11 1.290(2) . ?
C10 H10 0.9400 . ?
C11 H11A 0.9400 . ?
C11 H11B 0.9400 . ?
N1 S1 1.6892(12) . ?
S1 O2 1.4241(12) . ?
S1 O3 1.4284(12) . ?
S1 C12 1.7580(14) . ?
C12 C13 1.386(2) . ?
C12 C17 1.386(2) . ?
C13 C14 1.388(2) . ?
C13 H13 0.9400 . ?
C14 C15 1.385(2) . ?
C14 H14 0.9400 . ?
C15 C16 1.390(3) . ?
C15 C18 1.509(2) . ?
C16 C17 1.384(2) . ?
C16 H16 0.9400 . ?
C17 H17 0.9400 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
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 C1 C2 C3 149.15(14) . . . . ?
N1 C1 C2 C3 -32.21(17) . . . . ?
C1 C2 C3 C8 33.70(18) . . . . ?
C1 C2 C3 C4 -145.26(13) . . . . ?
C8 C3 C4 C5 0.1(2) . . . . ?
C2 C3 C4 C5 179.01(14) . . . . ?
C3 C4 C5 C6 -0.9(2) . . . . ?
C4 C5 C6 C7 0.7(2) . . . . ?
C5 C6 C7 C8 0.2(2) . . . . ?
C4 C3 C8 C7 0.9(2) . . . . ?
C2 C3 C8 C7 -178.07(13) . . . . ?
C4 C3 C8 C9 -177.71(13) . . . . ?
C2 C3 C8 C9 3.30(18) . . . . ?
C6 C7 C8 C3 -1.1(2) . . . . ?
C6 C7 C8 C9 177.54(13) . . . . ?
C3 C8 C9 N1 -39.14(16) . . . . ?
C7 C8 C9 N1 142.24(13) . . . . ?
C3 C8 C9 C10 83.01(15) . . . . ?
C7 C8 C9 C10 -95.61(16) . . . . ?
N1 C9 C10 C11 -125.90(18) . . . . ?
C8 C9 C10 C11 112.76(19) . . . . ?
O1 C1 N1 C9 172.71(13) . . . . ?
C2 C1 N1 C9 -5.95(18) . . . . ?
O1 C1 N1 S1 -3.94(19) . . . . ?
C2 C1 N1 S1 177.40(9) . . . . ?
C8 C9 N1 C1 41.04(17) . . . . ?
C10 C9 N1 C1 -81.71(15) . . . . ?
C8 C9 N1 S1 -142.31(10) . . . . ?
C10 C9 N1 S1 94.94(13) . . . . ?
C1 N1 S1 O2 -54.33(12) . . . . ?
C9 N1 S1 O2 128.92(10) . . . . ?
C1 N1 S1 O3 177.00(11) . . . . ?
C9 N1 S1 O3 0.25(12) . . . . ?
C1 N1 S1 C12 62.54(12) . . . . ?
C9 N1 S1 C12 -114.20(11) . . . . ?
O2 S1 C12 C13 15.09(14) . . . . ?
O3 S1 C12 C13 146.58(12) . . . . ?
N1 S1 C12 C13 -101.35(13) . . . . ?
O2 S1 C12 C17 -159.81(12) . . . . ?
O3 S1 C12 C17 -28.32(14) . . . . ?
N1 S1 C12 C17 83.75(13) . . . . ?
C17 C12 C13 C14 1.7(2) . . . . ?
S1 C12 C13 C14 -173.04(12) . . . . ?
C12 C13 C14 C15 -0.9(2) . . . . ?
C13 C14 C15 C16 -1.1(2) . . . . ?
C13 C14 C15 C18 177.02(17) . . . . ?
C14 C15 C16 C17 2.5(2) . . . . ?
C18 C15 C16 C17 -175.65(16) . . . . ?
C15 C16 C17 C12 -1.7(2) . . . . ?
C13 C12 C17 C16 -0.4(2) . . . . ?
S1 C12 C17 C16 174.40(12) . . . . ?
