#------------------------------------------------------------------------------
#$Date: 2015-12-03 15:12:24 +0200 (Thu, 03 Dec 2015) $
#$Revision: 170694 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/81/7118107.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_7118107
loop_
_publ_author_name
'Yu Jiang'
'Run Sun'
'Qiang Wang'
'Xiang-Ying Tang'
'Min Shi'
_publ_section_title
;
 Cyclization of sulfide, ether or tertiary amine-tethered
 N-sulfonyl-1,2,3-triazoles: a facile synthetic protocol for 3-substituted
 isoquinolines or dihydroisoquinolines
;
_journal_name_full               Chem.Commun.
_journal_page_first              16968
_journal_paper_doi               10.1039/C5cc07511D
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C23 H21 N O2 S2'
_chemical_formula_sum            'C23 H21 N O2 S2'
_chemical_formula_weight         407.53
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-05-11
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-05-14 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.3470(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   32.732(2)
_cell_length_b                   9.3213(7)
_cell_length_c                   12.9047(9)
_cell_measurement_reflns_used    7320
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.577
_cell_measurement_theta_min      2.27
_cell_volume                     3934.0(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 1.000
_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_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19513
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.602
_diffrn_reflns_theta_min         1.245
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0599 before and 0.0370 after correction.
The Ratio of minimum to maximum transmission is 0.8866.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      .
_exptl_crystal_description       Block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         6047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0609P)²+2.1976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1104
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                5022
_reflns_number_total             6047
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc07511d2.cif
_cod_data_source_block           mo_dm15371_0m
_cod_database_code               7118107
_shelxl_version_number           2014-3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.931
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C18(H18), C19(H19), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.18153(2) 0.12793(4) 0.49452(2) 0.02153(9) Uani 1 1 d . . . . .
S2 S 0.11023(2) -0.00778(3) 0.65022(2) 0.01729(8) Uani 1 1 d . . . . .
O1 O 0.12637(3) -0.10912(10) 0.57922(8) 0.0237(2) Uani 1 1 d . . . . .
O2 O 0.09639(3) -0.05755(11) 0.74777(7) 0.0246(2) Uani 1 1 d . . . . .
N1 N 0.14642(3) 0.11219(11) 0.67809(8) 0.0162(2) Uani 1 1 d . . . . .
C1 C 0.15755(4) 0.20977(14) 0.59802(9) 0.0167(2) Uani 1 1 d . . . . .
C2 C 0.15085(4) 0.35077(14) 0.61156(10) 0.0184(2) Uani 1 1 d . . . . .
H2 H 0.1591 0.4156 0.5618 0.022 Uiso 1 1 calc R . . . .
C3 C 0.13086(4) 0.40378(14) 0.70270(10) 0.0176(2) Uani 1 1 d . . . . .
C4 C 0.11425(4) 0.54192(15) 0.70728(11) 0.0220(3) Uani 1 1 d . . . . .
H4 H 0.1159 0.6032 0.6507 0.026 Uiso 1 1 calc R . . . .
C5 C 0.09539(4) 0.58786(15) 0.79569(12) 0.0254(3) Uani 1 1 d . . . . .
H5 H 0.0846 0.6800 0.7983 0.030 Uiso 1 1 calc R . . . .
C6 C 0.09262(4) 0.49709(15) 0.88023(12) 0.0249(3) Uani 1 1 d . . . . .
H6 H 0.0796 0.5279 0.9389 0.030 Uiso 1 1 calc R . . . .
C7 C 0.10936(4) 0.35969(15) 0.87728(11) 0.0213(3) Uani 1 1 d . . . . .
H7 H 0.1075 0.2988 0.9340 0.026 Uiso 1 1 calc R . . . .
C8 C 0.12879(4) 0.31406(13) 0.78956(10) 0.0168(2) Uani 1 1 d . . . . .
C9 C 0.15086(4) 0.17286(13) 0.78466(9) 0.0156(2) Uani 1 1 d . . . . .
H9 H 0.1385 0.1060 0.8329 0.019 Uiso 1 1 calc R . . . .
C10 C 0.19649(4) 0.18449(13) 0.81293(9) 0.0161(2) Uani 1 1 d . . . . .
C11 C 0.21333(4) 0.30560(15) 0.86097(10) 0.0217(3) Uani 1 1 d . . . . .
H11 H 0.1966 0.3830 0.8760 0.026 Uiso 1 1 calc R . . . .
C12 C 0.25506(4) 0.31179(17) 0.88674(11) 0.0255(3) Uani 1 1 d . . . . .
H12 H 0.2661 0.3936 0.9183 0.031 Uiso 1 1 calc R . . . .
C13 C 0.28006(4) 0.19776(18) 0.86577(11) 0.0266(3) Uani 1 1 d . . . . .
H13 H 0.3079 0.2024 0.8828 0.032 Uiso 1 1 calc R . . . .
C14 C 0.26346(4) 0.07578(18) 0.81914(11) 0.0276(3) Uani 1 1 d . . . . .
H14 H 0.2802 -0.0021 0.8056 0.033 Uiso 1 1 calc R . . . .
C15 C 0.22202(4) 0.06957(15) 0.79271(10) 0.0222(3) Uani 1 1 d . . . . .
H15 H 0.2112 -0.0124 0.7611 0.027 Uiso 1 1 calc R . . . .
C16 C 0.19704(5) 0.28158(18) 0.42191(12) 0.0309(3) Uani 1 1 d . . . . .
H16A H 0.1733 0.3335 0.3972 0.046 Uiso 1 1 calc GR . . . .
H16B H 0.2123 0.2506 0.3640 0.046 Uiso 1 1 calc GR . . . .
H16C H 0.2138 0.3427 0.4657 0.046 Uiso 1 1 calc GR . . . .
C17 C 0.07018(4) 0.08450(14) 0.58422(10) 0.0181(2) Uani 1 1 d . . . . .
C18 C 0.06469(4) 0.06749(15) 0.47786(10) 0.0221(3) Uani 1 1 d . . . . .
H18 H 0.0818 0.0073 0.4419 0.026 Uiso 1 1 calc R . . . .
C19 C 0.03333(4) 0.14152(16) 0.42588(11) 0.0241(3) Uani 1 1 d . . . . .
H19 H 0.0294 0.1300 0.3546 0.029 Uiso 1 1 calc R . . . .
C20 C 0.00767(4) 0.23238(16) 0.47810(11) 0.0242(3) Uani 1 1 d . . . . .
C21 C 0.01377(4) 0.24708(17) 0.58541(12) 0.0282(3) Uani 1 1 d . . . . .
H21 H -0.0033 0.3074 0.6215 0.034 Uiso 1 1 calc R . . . .
C22 C 0.04461(4) 0.17369(17) 0.63884(11) 0.0251(3) Uani 1 1 d . . . . .
H22 H 0.0482 0.1837 0.7103 0.030 Uiso 1 1 calc R . . . .
C23 C -0.02570(5) 0.3135(2) 0.41981(14) 0.0351(4) Uani 1 1 d . . . . .
H23A H -0.0213 0.3088 0.3468 0.053 Uiso 1 1 calc GR . . . .
H23B H -0.0254 0.4119 0.4418 0.053 Uiso 1 1 calc GR . . . .
H23C H -0.0517 0.2715 0.4336 0.053 Uiso 1 1 calc GR . . . .
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
C1 S1 C16 101.28(7) . .
O1 S2 O2 119.14(6) . .
O1 S2 N1 107.74(6) . .
O1 S2 C17 107.45(6) . .
O2 S2 N1 106.06(6) . .
O2 S2 C17 109.14(6) . .
N1 S2 C17 106.68(6) . .
C1 N1 S2 118.14(8) . .
C1 N1 C9 113.98(10) . .
C9 N1 S2 119.90(8) . .
N1 C1 S1 114.07(9) . .
C2 C1 S1 127.24(10) . .
C2 C1 N1 118.58(11) . .
C1 C2 H2 119.4 . .
C1 C2 C3 121.18(12) . .
C3 C2 H2 119.4 . .
C4 C3 C2 122.31(12) . .
C4 C3 C8 118.90(12) . .
C8 C3 C2 118.78(11) . .
C3 C4 H4 119.8 . .
C5 C4 C3 120.36(13) . .
C5 C4 H4 119.8 . .
C4 C5 H5 119.9 . .
C6 C5 C4 120.30(13) . .
C6 C5 H5 119.9 . .
C5 C6 H6 120.0 . .
C5 C6 C7 120.04(13) . .
C7 C6 H6 120.0 . .
C6 C7 H7 120.1 . .
C8 C7 C6 119.85(13) . .
C8 C7 H7 120.1 . .
C3 C8 C9 116.69(11) . .
C7 C8 C3 120.52(12) . .
C7 C8 C9 122.66(11) . .
N1 C9 C8 110.03(10) . .
N1 C9 H9 108.6 . .
N1 C9 C10 107.78(10) . .
C8 C9 H9 108.6 . .
C8 C9 C10 113.24(10) . .
C10 C9 H9 108.6 . .
C11 C10 C9 122.02(11) . .
C15 C10 C9 119.35(11) . .
C15 C10 C11 118.60(12) . .
C10 C11 H11 119.8 . .
C10 C11 C12 120.44(13) . .
C12 C11 H11 119.8 . .
C11 C12 H12 119.8 . .
C13 C12 C11 120.42(13) . .
C13 C12 H12 119.8 . .
C12 C13 H13 120.2 . .
C12 C13 C14 119.58(13) . .
C14 C13 H13 120.2 . .
C13 C14 H14 119.9 . .
C15 C14 C13 120.19(14) . .
C15 C14 H14 119.9 . .
C10 C15 H15 119.6 . .
C14 C15 C10 120.76(13) . .
C14 C15 H15 119.6 . .
S1 C16 H16A 109.5 . .
S1 C16 H16B 109.5 . .
S1 C16 H16C 109.5 . .
H16A C16 H16B 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C18 C17 S2 119.18(10) . .
C18 C17 C22 120.91(12) . .
C22 C17 S2 119.91(10) . .
C17 C18 H18 120.5 . .
C17 C18 C19 119.04(13) . .
C19 C18 H18 120.5 . .
C18 C19 H19 119.3 . .
C20 C19 C18 121.32(13) . .
C20 C19 H19 119.3 . .
C19 C20 C21 118.46(13) . .
C19 C20 C23 120.38(14) . .
C21 C20 C23 121.17(14) . .
C20 C21 H21 119.4 . .
C22 C21 C20 121.21(13) . .
C22 C21 H21 119.4 . .
C17 C22 H22 120.5 . .
C21 C22 C17 119.06(13) . .
C21 C22 H22 120.5 . .
C20 C23 H23A 109.5 . .
C20 C23 H23B 109.5 . .
C20 C23 H23C 109.5 . .
H23A C23 H23B 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.7515(13) .
S1 C16 1.7960(15) .
S2 O1 1.4320(10) .
S2 O2 1.4324(10) .
S2 N1 1.6579(11) .
S2 C17 1.7585(13) .
N1 C1 1.4347(15) .
N1 C9 1.4885(16) .
C1 C2 1.3450(18) .
C2 H2 0.9300 .
C2 C3 1.4554(18) .
C3 C4 1.4000(18) .
C3 C8 1.4024(17) .
C4 H4 0.9300 .
C4 C5 1.387(2) .
C5 H5 0.9300 .
C5 C6 1.387(2) .
C6 H6 0.9300 .
C6 C7 1.3941(19) .
C7 H7 0.9300 .
C7 C8 1.3878(18) .
C8 C9 1.5039(17) .
C9 H9 0.9800 .
C9 C10 1.5265(17) .
C10 C11 1.3910(18) .
C10 C15 1.3898(18) .
C11 H11 0.9300 .
C11 C12 1.3936(19) .
C12 H12 0.9300 .
C12 C13 1.375(2) .
C13 H13 0.9300 .
C13 C14 1.387(2) .
C14 H14 0.9300 .
C14 C15 1.3865(19) .
C15 H15 0.9300 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
C17 C18 1.3860(18) .
C17 C22 1.3918(18) .
C18 H18 0.9300 .
C18 C19 1.3868(19) .
C19 H19 0.9300 .
C19 C20 1.387(2) .
C20 C21 1.398(2) .
C20 C23 1.504(2) .
C21 H21 0.9300 .
C21 C22 1.380(2) .
C22 H22 0.9300 .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
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
S1 C1 C2 C3 -179.20(9) . . . .
S2 N1 C1 S1 -67.13(11) . . . .
S2 N1 C1 C2 116.28(12) . . . .
S2 N1 C9 C8 -96.24(11) . . . .
S2 N1 C9 C10 139.85(9) . . . .
S2 C17 C18 C19 -179.37(11) . . . .
S2 C17 C22 C21 178.92(12) . . . .
O1 S2 N1 C1 69.26(11) . . . .
O1 S2 N1 C9 -143.68(9) . . . .
O1 S2 C17 C18 -10.46(13) . . . .
O1 S2 C17 C22 169.81(11) . . . .
O2 S2 N1 C1 -162.13(9) . . . .
O2 S2 N1 C9 -15.07(11) . . . .
O2 S2 C17 C18 -140.95(11) . . . .
O2 S2 C17 C22 39.32(13) . . . .
N1 S2 C17 C18 104.86(11) . . . .
N1 S2 C17 C22 -74.87(12) . . . .
N1 C1 C2 C3 -3.10(18) . . . .
N1 C9 C10 C11 135.93(12) . . . .
N1 C9 C10 C15 -45.75(15) . . . .
C1 N1 C9 C8 52.11(13) . . . .
C1 N1 C9 C10 -71.81(12) . . . .
C1 C2 C3 C4 -163.47(13) . . . .
C1 C2 C3 C8 17.61(19) . . . .
C2 C3 C4 C5 179.86(13) . . . .
C2 C3 C8 C7 -178.85(12) . . . .
C2 C3 C8 C9 5.10(17) . . . .
C3 C4 C5 C6 -0.3(2) . . . .
C3 C8 C9 N1 -38.20(15) . . . .
C3 C8 C9 C10 82.48(13) . . . .
C4 C3 C8 C7 2.20(19) . . . .
C4 C3 C8 C9 -173.86(11) . . . .
C4 C5 C6 C7 1.0(2) . . . .
C5 C6 C7 C8 0.0(2) . . . .
C6 C7 C8 C3 -1.6(2) . . . .
C6 C7 C8 C9 174.22(12) . . . .
C7 C8 C9 N1 145.84(12) . . . .
C7 C8 C9 C10 -93.48(14) . . . .
C8 C3 C4 C5 -1.2(2) . . . .
C8 C9 C10 C11 13.98(16) . . . .
C8 C9 C10 C15 -167.69(11) . . . .
C9 N1 C1 S1 143.93(9) . . . .
C9 N1 C1 C2 -32.67(16) . . . .
C9 C10 C11 C12 179.25(12) . . . .
C9 C10 C15 C14 -178.85(12) . . . .
C10 C11 C12 C13 -0.5(2) . . . .
C11 C10 C15 C14 -0.5(2) . . . .
C11 C12 C13 C14 -0.3(2) . . . .
C12 C13 C14 C15 0.8(2) . . . .
C13 C14 C15 C10 -0.4(2) . . . .
C15 C10 C11 C12 0.91(19) . . . .
C16 S1 C1 N1 -172.14(10) . . . .
C16 S1 C1 C2 4.10(14) . . . .
C17 S2 N1 C1 -45.87(11) . . . .
C17 S2 N1 C9 101.20(10) . . . .
C17 C18 C19 C20 0.4(2) . . . .
C18 C17 C22 C21 -0.8(2) . . . .
C18 C19 C20 C21 -0.7(2) . . . .
C18 C19 C20 C23 178.97(14) . . . .
C19 C20 C21 C22 0.2(2) . . . .
C20 C21 C22 C17 0.5(2) . . . .
C22 C17 C18 C19 0.4(2) . . . .
C23 C20 C21 C22 -179.42(15) . . . .
