#------------------------------------------------------------------------------
#$Date: 2015-12-03 15:12:24 +0200 (Thu, 03 Dec 2015) $
#$Revision: 170694 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/81/7118105.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_7118105
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_sum            'C22 H20 Br2 N2 S2'
_chemical_formula_weight         536.34
_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
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-12-04 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.120(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.883(3)
_cell_length_b                   5.8646(8)
_cell_length_c                   17.600(2)
_cell_measurement_reflns_used    1491
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      49.730
_cell_measurement_theta_min      4.899
_cell_volume                     2134.1(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5836
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.492
_diffrn_reflns_theta_min         1.970
_exptl_absorpt_coefficient_mu    4.005
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.145
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.045
_refine_diff_density_max         1.057
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0485
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0612P)²+4.1731P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1252
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                1558
_reflns_number_total             1987
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc07511d2.cif
_cod_data_source_block           cd214695
_cod_original_cell_volume        2134.0(5)
_cod_database_code               7118105
_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. 
;
_shelxl_version_number           2013-4
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
Br1 Br 0.08782(3) 0.83107(11) 0.15187(3) 0.0696(3) Uani 1 1 d . . . . .
S1 S 0.41624(5) 0.7830(2) 0.52820(7) 0.0431(3) Uani 1 1 d . . . . .
N1 N 0.30344(15) 1.0011(5) 0.48866(19) 0.0311(7) Uani 1 1 d . . . . .
C1 C 0.21124(19) 0.8321(6) 0.3858(2) 0.0303(8) Uani 1 1 d . . . . .
C2 C 0.16441(19) 0.8903(7) 0.3143(2) 0.0351(9) Uani 1 1 d . . . . .
H2 H 0.1420 1.0272 0.3095 0.042 Uiso 1 1 calc R U . . .
C3 C 0.1514(2) 0.7422(8) 0.2500(2) 0.0396(10) Uani 1 1 d . . . . .
C4 C 0.1835(2) 0.5391(8) 0.2549(2) 0.0429(10) Uani 1 1 d . . . . .
H4 H 0.1740 0.4417 0.2108 0.051 Uiso 1 1 calc R U . . .
C5 C 0.2305(2) 0.4820(7) 0.3266(2) 0.0372(9) Uani 1 1 d . . . . .
H5 H 0.2529 0.3452 0.3309 0.045 Uiso 1 1 calc R U . . .
C6 C 0.24433(19) 0.6273(6) 0.3921(2) 0.0311(8) Uani 1 1 d . . . . .
C7 C 0.29588(18) 0.5868(6) 0.4724(2) 0.0314(8) Uani 1 1 d . . . . .
H7 H 0.3257 0.4689 0.4664 0.038 Uiso 1 1 calc R U . . .
C8 C 0.33181(18) 0.8109(7) 0.4938(2) 0.0309(8) Uani 1 1 d . . . . .
C9 C 0.23197(18) 0.9860(6) 0.4584(2) 0.0294(8) Uani 1 1 d . . . . .
H9 H 0.2154 1.1389 0.4404 0.035 Uiso 1 1 calc R U . . .
C10 C 0.4429(2) 1.0699(8) 0.5601(3) 0.0455(11) Uani 1 1 d . . . . .
H10A H 0.4868 1.0890 0.5599 0.055 Uiso 1 1 calc R U . . .
H10B H 0.4157 1.1771 0.5218 0.055 Uiso 1 1 calc R U . . .
C11 C 0.4408(3) 1.1246(10) 0.6412(3) 0.0698(16) Uani 1 1 d . . . . .
H11A H 0.3975 1.1041 0.6422 0.105 Uiso 1 1 calc R U . . .
H11B H 0.4538 1.2800 0.6541 0.105 Uiso 1 1 calc R U . . .
H11C H 0.4696 1.0252 0.6800 0.105 Uiso 1 1 calc R U . . .
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C8 S1 C10 102.5(2) . .
C8 N1 C9 114.1(3) . .
C2 C1 C6 119.9(3) . .
C2 C1 C9 123.5(3) . .
C6 C1 C9 116.5(3) . .
C3 C2 C1 119.0(4) . .
C3 C2 H2 120.5 . .
C1 C2 H2 120.5 . .
C4 C3 C2 122.1(4) . .
C4 C3 Br1 120.2(3) . .
C2 C3 Br1 117.7(3) . .
C3 C4 C5 118.7(4) . .
C3 C4 H4 120.6 . .
C5 C4 H4 120.6 . .
C4 C5 C6 120.4(4) . .
C4 C5 H5 119.8 . .
C6 C5 H5 119.8 . .
C5 C6 C1 120.0(4) . .
C5 C6 C7 125.1(4) . .
C1 C6 C7 114.9(3) . .
C6 C7 C8 105.3(3) . .
C6 C7 C9 113.8(3) . 7_566
C8 C7 C9 109.9(3) . 7_566
C6 C7 H7 109.2 . .
C8 C7 H7 109.2 . .
C9 C7 H7 109.2 7_566 .
N1 C8 C7 123.0(3) . .
N1 C8 S1 122.9(3) . .
C7 C8 S1 114.0(3) . .
N1 C9 C1 109.3(3) . .
N1 C9 C7 111.4(3) . 7_566
C1 C9 C7 113.8(3) . 7_566
N1 C9 H9 107.3 . .
C1 C9 H9 107.3 . .
C7 C9 H9 107.3 7_566 .
C11 C10 S1 113.2(4) . .
C11 C10 H10A 108.9 . .
S1 C10 H10A 108.9 . .
C11 C10 H10B 108.9 . .
S1 C10 H10B 108.9 . .
H10A C10 H10B 107.8 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C3 1.901(4) .
S1 C8 1.753(4) .
S1 C10 1.809(5) .
N1 C8 1.265(5) .
N1 C9 1.480(5) .
C1 C2 1.381(6) .
C1 C6 1.388(5) .
C1 C9 1.507(5) .
C2 C3 1.380(6) .
C2 H2 0.9300 .
C3 C4 1.372(6) .
C4 C5 1.382(6) .
C4 H4 0.9300 .
C5 C6 1.385(5) .
C5 H5 0.9300 .
C6 C7 1.510(5) .
C7 C8 1.514(5) .
C7 C9 1.589(5) 7_566
C7 H7 0.9800 .
C9 C7 1.589(5) 7_566
C9 H9 0.9800 .
C10 C11 1.477(7) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9 N1 0.98 2.55 3.315(5) 134.5 7_576
C9 H9 N1 0.98 2.55 3.315(5) 134.5 7_576
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
C6 C1 C2 C3 0.0(6) . . . .
C9 C1 C2 C3 176.6(4) . . . .
C1 C2 C3 C4 -0.1(6) . . . .
C1 C2 C3 Br1 -178.7(3) . . . .
C2 C3 C4 C5 0.0(6) . . . .
Br1 C3 C4 C5 178.6(3) . . . .
C3 C4 C5 C6 0.3(6) . . . .
C4 C5 C6 C1 -0.4(6) . . . .
C4 C5 C6 C7 -177.9(4) . . . .
C2 C1 C6 C5 0.2(6) . . . .
C9 C1 C6 C5 -176.6(3) . . . .
C2 C1 C6 C7 178.0(3) . . . .
C9 C1 C6 C7 1.2(5) . . . .
C5 C6 C7 C8 133.5(4) . . . .
C1 C6 C7 C8 -44.1(4) . . . .
C5 C6 C7 C9 -106.1(4) . . . 7_566
C1 C6 C7 C9 76.3(4) . . . 7_566
C9 N1 C8 C7 -1.1(5) . . . .
C9 N1 C8 S1 -179.9(3) . . . .
C6 C7 C8 N1 47.3(5) . . . .
C9 C7 C8 N1 -75.6(5) 7_566 . . .
C6 C7 C8 S1 -133.8(3) . . . .
C9 C7 C8 S1 103.3(3) 7_566 . . .
C10 S1 C8 N1 6.0(4) . . . .
C10 S1 C8 C7 -172.8(3) . . . .
C8 N1 C9 C1 -46.1(4) . . . .
C8 N1 C9 C7 80.6(4) . . . 7_566
C2 C1 C9 N1 -130.6(4) . . . .
C6 C1 C9 N1 46.1(4) . . . .
C2 C1 C9 C7 104.1(4) . . . 7_566
C6 C1 C9 C7 -79.2(4) . . . 7_566
C8 S1 C10 C11 81.4(4) . . . .
