#------------------------------------------------------------------------------
#$Date: 2016-01-06 13:04:28 +0200 (Wed, 06 Jan 2016) $
#$Revision: 173607 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/06/1540649.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_1540649
loop_
_publ_author_name
'Shen, Tao'
'Huang, Xiaoqiang'
'Liang, Yu-Feng'
'Jiao, Ning'
_publ_section_title
;
 Cu-Catalyzed Transformation of Alkynes and Alkenes with Azide and
 Dimethyl Sulfoxide Reagents.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6186
_journal_page_last               6189
_journal_paper_doi               10.1021/acs.orglett.5b03179
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C11 H10 Br N2 S'
_chemical_formula_weight         282.18
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.533(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6870(12)
_cell_length_b                   5.6405(9)
_cell_length_c                   26.624(4)
_cell_measurement_reflns_used    2079
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.58
_cell_measurement_theta_min      2.91
_cell_volume                     1144.4(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_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  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            6000
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.91
_exptl_absorpt_coefficient_mu    3.741
_exptl_absorpt_correction_T_max  0.6623
_exptl_absorpt_correction_T_min  0.3543
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2009
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0312
_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)+(0.0290P)²+0.7930P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0768
_reflns_number_gt                1617
_reflns_number_total             2009
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b03179_si_002.cif
_cod_data_source_block           z
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1540649.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1540649
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.15775(5) 0.67880(8) 0.367687(14) 0.06739(17) Uani 1 1 d .
S1 S 0.20789(11) 0.09797(15) 0.00429(3) 0.0493(2) Uani 1 1 d .
N1 N 0.3454(4) 0.6862(4) 0.11836(10) 0.0461(6) Uani 1 1 d .
N2 N 0.3817(4) 0.5955(4) 0.07536(10) 0.0473(7) Uani 1 1 d .
N3 N 0.3832(3) 0.3577(4) 0.08087(9) 0.0368(6) Uani 1 1 d .
C1 C 0.3331(4) 0.3872(5) 0.24117(11) 0.0388(7) Uani 1 1 d .
H1A H 0.3916 0.2498 0.2337 0.047 Uiso 1 1 calc R
C2 C 0.2980(4) 0.4236(5) 0.29009(11) 0.0439(7) Uani 1 1 d .
H2A H 0.3324 0.3129 0.3153 0.053 Uiso 1 1 calc R
C3 C 0.2104(4) 0.6285(5) 0.30083(11) 0.0403(7) Uani 1 1 d .
C4 C 0.1613(4) 0.7944(5) 0.26372(13) 0.0434(7) Uani 1 1 d .
H4A H 0.1043 0.9325 0.2714 0.052 Uiso 1 1 calc R
C5 C 0.1972(4) 0.7543(5) 0.21523(12) 0.0409(7) Uani 1 1 d .
H5A H 0.1629 0.8662 0.1902 0.049 Uiso 1 1 calc R
C6 C 0.2838(4) 0.5500(4) 0.20255(11) 0.0340(6) Uani 1 1 d .
C7 C 0.3239(4) 0.5078(5) 0.15121(11) 0.0341(6) Uani 1 1 d .
C8 C 0.3486(4) 0.2982(5) 0.12712(11) 0.0381(7) Uani 1 1 d .
H8A H 0.3425 0.1460 0.1402 0.046 Uiso 1 1 calc R
C9 C 0.4097(4) 0.1998(5) 0.03916(12) 0.0429(7) Uani 1 1 d .
H9A H 0.4778 0.0638 0.0526 0.051 Uiso 1 1 calc R
H9B H 0.4771 0.2825 0.0162 0.051 Uiso 1 1 calc R
C10 C 0.1549(5) 0.3444(6) -0.03781(15) 0.0673(10) Uani 1 1 d .
H10B H 0.0469 0.3126 -0.0592 0.101 Uiso 1 1 calc R
H10C H 0.2473 0.3669 -0.0583 0.101 Uiso 1 1 calc R
H10D H 0.1421 0.4851 -0.0183 0.101 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'
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
C9 S1 C10 100.66(17)
N2 N1 C7 109.3(2)
N1 N2 N3 106.9(2)
C8 N3 N2 110.5(2)
C8 N3 C9 127.8(2)
N2 N3 C9 121.6(2)
C2 C1 C6 122.0(3)
C2 C1 H1A 119.0
C6 C1 H1A 119.0
C1 C2 C3 118.6(3)
C1 C2 H2A 120.7
C3 C2 H2A 120.7
C4 C3 C2 120.9(3)
C4 C3 Br1 119.9(2)
C2 C3 Br1 119.2(2)
C5 C4 C3 119.5(3)
C5 C4 H4A 120.3
C3 C4 H4A 120.3
C4 C5 C6 121.7(3)
C4 C5 H5A 119.2
C6 C5 H5A 119.2
C1 C6 C5 117.3(3)
C1 C6 C7 120.9(2)
C5 C6 C7 121.8(3)
N1 C7 C8 107.6(3)
N1 C7 C6 122.7(2)
C8 C7 C6 129.7(2)
N3 C8 C7 105.7(2)
N3 C8 H8A 127.2
C7 C8 H8A 127.2
N3 C9 S1 113.0(2)
N3 C9 H9A 109.0
S1 C9 H9A 109.0
N3 C9 H9B 109.0
S1 C9 H9B 109.0
H9A C9 H9B 107.8
S1 C10 H10B 109.5
S1 C10 H10C 109.5
H10B C10 H10C 109.5
S1 C10 H10D 109.5
H10B C10 H10D 109.5
H10C C10 H10D 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.898(3)
S1 C9 1.795(3)
S1 C10 1.798(4)
N1 N2 1.317(3)
N1 C7 1.357(4)
N2 N3 1.349(3)
N3 C8 1.336(4)
N3 C9 1.459(4)
C1 C2 1.380(4)
C1 C6 1.394(4)
C1 H1A 0.9300
C2 C3 1.386(4)
C2 H2A 0.9300
C3 C4 1.377(4)
C4 C5 1.374(4)
C4 H4A 0.9300
C5 C6 1.394(4)
C5 H5A 0.9300
C6 C7 1.460(4)
C7 C8 1.370(4)
C8 H8A 0.9300
C9 H9A 0.9700
C9 H9B 0.9700
C10 H10B 0.9600
C10 H10C 0.9600
C10 H10D 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
C7 N1 N2 N3 0.1(3)
N1 N2 N3 C8 -0.2(3)
N1 N2 N3 C9 176.6(3)
C6 C1 C2 C3 0.2(4)
C1 C2 C3 C4 -0.9(4)
C1 C2 C3 Br1 179.0(2)
C2 C3 C4 C5 1.0(4)
Br1 C3 C4 C5 -178.8(2)
C3 C4 C5 C6 -0.5(4)
C2 C1 C6 C5 0.3(4)
C2 C1 C6 C7 179.5(3)
C4 C5 C6 C1 -0.1(4)
C4 C5 C6 C7 -179.3(3)
N2 N1 C7 C8 0.1(3)
N2 N1 C7 C6 179.5(2)
C1 C6 C7 N1 -152.8(3)
C5 C6 C7 N1 26.4(4)
C1 C6 C7 C8 26.4(5)
C5 C6 C7 C8 -154.3(3)
N2 N3 C8 C7 0.2(3)
C9 N3 C8 C7 -176.2(3)
N1 C7 C8 N3 -0.2(3)
C6 C7 C8 N3 -179.5(3)
C8 N3 C9 S1 81.6(3)
N2 N3 C9 S1 -94.6(3)
C10 S1 C9 N3 82.8(2)
