#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/45/7154599.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_7154599
loop_
_publ_author_name
'Liu, Shan'
'Xi, Hailing'
'Zhang, Jingjing'
'Wu, Xia'
'Gao, Qinghe'
'Wu, Anxin'
_publ_section_title
;
 Organopromoted direct synthesis of
 6-iodo-3-methylthioimidazo[1,2-a]pyridines via convergent integration of
 three self-sorting domino sequences.
;
_journal_issue                   33
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8807
_journal_page_last               8811
_journal_paper_doi               10.1039/c5ob01313e
_journal_volume                  13
_journal_year                    2015
_chemical_formula_sum            'C14 H11 I N2 S'
_chemical_formula_weight         366.21
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_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           SHELXL-97
_audit_update_record
;
2015-06-24 deposited with the CCDC.
2015-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                91.830(2)
_cell_angle_beta                 96.597(3)
_cell_angle_gamma                110.961(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9798(13)
_cell_length_b                   8.2157(14)
_cell_length_c                   11.2639(18)
_cell_measurement_reflns_used    4843
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      31.75
_cell_measurement_theta_min      2.66
_cell_volume                     682.90(19)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5028
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    2.480
_exptl_absorpt_correction_T_max  0.7895
_exptl_absorpt_correction_T_min  0.7551
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.908
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.100
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2952
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0296
_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)+(0.0494P)²+0.4867P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0967
_reflns_number_gt                2757
_reflns_number_total             2952
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01313e2.cif
_cod_data_source_block           g:\150325b_1\mo_150325b_1_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7154599.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7154599
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
N2 N 0.3931(3) 0.6080(3) 0.1675(2) 0.0305(5) Uani 1 1 d .
C1 C 0.1765(4) 0.4440(4) -0.1383(3) 0.0346(6) Uani 1 1 d .
C2 C 0.0219(4) 0.2919(5) -0.1477(3) 0.0450(7) Uani 1 1 d .
H2 H -0.0173 0.2394 -0.0789 0.054 Uiso 1 1 calc R
C3 C -0.0732(5) 0.2191(5) -0.2594(4) 0.0537(9) Uani 1 1 d .
H3 H -0.1752 0.1172 -0.2652 0.064 Uiso 1 1 calc R
C4 C -0.0176(5) 0.2969(6) -0.3623(4) 0.0570(9) Uani 1 1 d .
H4 H -0.0826 0.2482 -0.4368 0.068 Uiso 1 1 calc R
C5 C 0.1344(6) 0.4468(6) -0.3539(3) 0.0528(8) Uani 1 1 d .
H5 H 0.1730 0.4987 -0.4230 0.063 Uiso 1 1 calc R
N1 N 0.3636(3) 0.7102(3) -0.0120(2) 0.0355(5) Uani 1 1 d .
C6 C 0.2305(4) 0.5210(5) -0.2421(3) 0.0415(7) Uani 1 1 d .
H6 H 0.3319 0.6234 -0.2371 0.050 Uiso 1 1 calc R
C7 C 0.2746(4) 0.5322(4) -0.0212(3) 0.0323(5) Uani 1 1 d .
C8 C 0.4349(4) 0.7532(4) 0.1010(3) 0.0327(5) Uani 1 1 d .
C9 C 0.2908(4) 0.4640(3) 0.0885(3) 0.0312(5) Uani 1 1 d .
C10 C 0.4440(4) 0.6201(4) 0.2884(3) 0.0351(6) Uani 1 1 d .
H10 H 0.4113 0.5209 0.3311 0.042 Uiso 1 1 calc R
C11 C 0.5428(4) 0.7793(4) 0.3450(3) 0.0355(6) Uani 1 1 d .
C12 C 0.5933(4) 0.9319(4) 0.2812(3) 0.0398(6) Uani 1 1 d .
H12 H 0.6632 1.0400 0.3212 0.048 Uiso 1 1 calc R
C13 C 0.5386(4) 0.9193(4) 0.1611(3) 0.0403(7) Uani 1 1 d .
H13 H 0.5692 1.0189 0.1188 0.048 Uiso 1 1 calc R
C14 C 0.0231(5) 0.2176(6) 0.1931(5) 0.0613(11) Uani 1 1 d .
H14A H 0.0433 0.3080 0.2552 0.092 Uiso 1 1 calc R
H14B H -0.0170 0.1057 0.2258 0.092 Uiso 1 1 calc R
H14C H -0.0678 0.2215 0.1307 0.092 Uiso 1 1 calc R
I1 I 0.61752(3) 0.80021(3) 0.529713(18) 0.05295(15) Uani 1 1 d .
S1 S 0.23341(10) 0.25123(9) 0.13142(8) 0.03740(19) Uani 1 1 d .
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'
I I -0.4742 1.8119 '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
C10 N2 C8 122.5(2)
C10 N2 C9 130.6(2)
C8 N2 C9 106.8(2)
C6 C1 C2 118.8(3)
C6 C1 C7 119.1(3)
C2 C1 C7 121.9(3)
C3 C2 C1 120.1(3)
C3 C2 H2 119.9
C1 C2 H2 119.9
C4 C3 C2 120.5(4)
C4 C3 H3 119.7
C2 C3 H3 119.7
C5 C4 C3 119.8(3)
C5 C4 H4 120.1
C3 C4 H4 120.1
C4 C5 C6 120.1(4)
C4 C5 H5 119.9
C6 C5 H5 119.9
C8 N1 C7 105.9(2)
C1 C6 C5 120.7(3)
C1 C6 H6 119.7
C5 C6 H6 119.7
N1 C7 C9 111.1(2)
N1 C7 C1 118.8(3)
C9 C7 C1 130.0(3)
N1 C8 N2 111.4(2)
N1 C8 C13 130.3(3)
N2 C8 C13 118.3(3)
C7 C9 N2 104.8(2)
C7 C9 S1 132.9(2)
N2 C9 S1 121.8(2)
C11 C10 N2 118.7(3)
C11 C10 H10 120.6
N2 C10 H10 120.6
C10 C11 C12 121.3(3)
C10 C11 I1 119.1(2)
C12 C11 I1 119.6(2)
C13 C12 C11 119.6(3)
C13 C12 H12 120.2
C11 C12 H12 120.2
C12 C13 C8 119.5(3)
C12 C13 H13 120.2
C8 C13 H13 120.2
S1 C14 H14A 109.5
S1 C14 H14B 109.5
H14A C14 H14B 109.5
S1 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C9 S1 C14 102.09(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N2 C10 1.366(4)
N2 C8 1.388(3)
N2 C9 1.390(4)
C1 C6 1.386(5)
C1 C2 1.398(4)
C1 C7 1.475(4)
C2 C3 1.387(5)
C2 H2 0.9300
C3 C4 1.382(6)
C3 H3 0.9300
C4 C5 1.376(6)
C4 H4 0.9300
C5 C6 1.392(5)
C5 H5 0.9300
N1 C8 1.315(4)
N1 C7 1.373(4)
C6 H6 0.9300
C7 C9 1.384(4)
C8 C13 1.417(4)
C9 S1 1.741(3)
C10 C11 1.353(4)
C10 H10 0.9300
C11 C12 1.419(4)
C11 I1 2.081(3)
C12 C13 1.362(5)
C12 H12 0.9300
C13 H13 0.9300
C14 S1 1.823(4)
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 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
C6 C1 C2 C3 0.9(5)
C7 C1 C2 C3 175.9(3)
C1 C2 C3 C4 -0.7(6)
C2 C3 C4 C5 0.7(6)
C3 C4 C5 C6 -0.8(6)
C2 C1 C6 C5 -1.0(5)
C7 C1 C6 C5 -176.2(3)
C4 C5 C6 C1 1.0(6)
C8 N1 C7 C9 0.2(3)
C8 N1 C7 C1 178.8(2)
C6 C1 C7 N1 25.4(4)
C2 C1 C7 N1 -149.6(3)
C6 C1 C7 C9 -156.3(3)
C2 C1 C7 C9 28.7(5)
C7 N1 C8 N2 -0.9(3)
C7 N1 C8 C13 -179.0(3)
C10 N2 C8 N1 -176.6(3)
C9 N2 C8 N1 1.2(3)
C10 N2 C8 C13 1.7(4)
C9 N2 C8 C13 179.6(3)
N1 C7 C9 N2 0.5(3)
C1 C7 C9 N2 -177.9(3)
N1 C7 C9 S1 -171.2(2)
C1 C7 C9 S1 10.4(5)
C10 N2 C9 C7 176.6(3)
C8 N2 C9 C7 -1.0(3)
C10 N2 C9 S1 -10.5(4)
C8 N2 C9 S1 171.9(2)
C8 N2 C10 C11 -1.7(4)
C9 N2 C10 C11 -178.9(3)
N2 C10 C11 C12 0.1(5)
N2 C10 C11 I1 179.0(2)
C10 C11 C12 C13 1.3(5)
I1 C11 C12 C13 -177.5(3)
C11 C12 C13 C8 -1.2(5)
N1 C8 C13 C12 177.8(3)
N2 C8 C13 C12 -0.3(5)
C7 C9 S1 C14 -101.6(3)
N2 C9 S1 C14 87.8(3)
