#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/22/2222243.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222243
loop_
_publ_author_name
'Bibila Mayaya Bisseyou, Yvon'
'Sissouma, Drissa'
'Goulizan Bi, Severin D.'
'Ouattara, Mahama'
'Yao-Kakou, R. C. A.'
_publ_section_title
;1-(2-Methylimidazo[1,2-a]pyridin-3-yl)-3,3-bis(methylsulfanyl)prop-2-enone
 monohydrate
;
_journal_coeditor_code           BQ2145
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1698
_journal_page_last               o1699
_journal_paper_doi               10.1107/S1600536809023514
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H14 N2 O S2, H2 O'
_chemical_formula_moiety         'C13 H14 N2 O S2, H2 O'
_chemical_formula_sum            'C13 H16 N2 O2 S2'
_chemical_formula_weight         296.41
_chemical_melting_point          430
_chemical_name_systematic
;
1-(2-Methylimidazo[1,2-a]pyridin-3-yl)-3,3-bis(methylsulfanyl)prop-
2-enone monohydrate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           CRYSTALS_ver_12.85
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.14050(10)
_cell_length_b                   17.7653(3)
_cell_length_c                   31.3919(6)
_cell_measurement_reflns_used    11253
_cell_measurement_temperature    295
_cell_measurement_theta_max      30
_cell_measurement_theta_min      4
_cell_volume                     2866.79(9)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009)
;
_computing_publication_material  'CRYSTALS (Betteridge et al.,  2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al.,  2003)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       φ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.05
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            11253
_diffrn_reflns_theta_full        28.056
_diffrn_reflns_theta_max         30.496
_diffrn_reflns_theta_min         1.297
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.371
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.25
_refine_ls_extinction_coef       1.055(5)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9899
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2066
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.000155
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[σ²(F²) + (0.04P)² + 3.2P], where P=[max(Fo²,0) + 2Fc²]/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1375
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.0973
_reflns_number_gt                2344
_reflns_number_total             4202
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            bq2145.cif
_cod_data_source_block           I
_cod_database_code               2222243
_cod_database_fobs_code          2222243
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,z
x+1/2,-y+1/2,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
x+1/2,y,-z+1/2
loop_
_atom_site_type_symbol
_atom_site_label
_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_disorder_assembly
_atom_site_disorder_group
S S1 0.01264(14) 0.40723(4) 0.05322(3) 0.0552 Uani 1.0000 . .
S S2 -0.11568(16) 0.46016(4) 0.14025(3) 0.0696 Uani 1.0000 . .
O O1 0.3999(4) 0.30577(10) 0.05889(6) 0.0542 Uani 1.0000 . .
N N1 0.7820(4) 0.21236(11) 0.09663(7) 0.0394 Uani 1.0000 . .
O O2w 0.9388(4) 0.07731(12) 0.22997(7) 0.0739 Uani 1.0000 . .
N N2 0.8459(5) 0.18741(13) 0.16574(8) 0.0559 Uani 1.0000 . .
C C4 0.8270(5) 0.20481(13) 0.05354(9) 0.0464 Uani 1.0000 . .
C C7 0.9265(5) 0.17257(14) 0.12603(9) 0.0474 Uani 1.0000 . .
C C9 0.2551(5) 0.35366(14) 0.12396(9) 0.0472 Uani 1.0000 . .
C C5 0.6013(5) 0.25573(13) 0.11962(8) 0.0410 Uani 1.0000 . .
C C3 1.0207(6) 0.15826(14) 0.04040(10) 0.0525 Uani 1.0000 . .
C C2 1.1724(6) 0.11813(15) 0.06988(11) 0.0573 Uani 1.0000 . .
C C1 1.1255(6) 0.12480(15) 0.11196(11) 0.0561 Uani 1.0000 . .
C C6 0.6478(5) 0.23742(16) 0.16209(9) 0.0494 Uani 1.0000 . .
C C10 0.0715(5) 0.40096(14) 0.10800(9) 0.0473 Uani 1.0000 . .
C C8 0.4160(5) 0.30513(13) 0.09821(9) 0.0417 Uani 1.0000 . .
C C11 -0.2533(6) 0.47334(16) 0.04946(12) 0.0704 Uani 1.0000 . .
C C13 0.5083(7) 0.2619(2) 0.20158(10) 0.0723 Uani 1.0000 . .
C C12 0.0018(9) 0.4409(2) 0.19285(13) 0.0992 Uani 1.0000 . .
H H2 1.3072 0.0877 0.0601 0.0687 Uiso 1.0000 . .
H H4 0.7197 0.2326 0.0346 0.0557 Uiso 1.0000 . .
H H9 0.2801 0.3530 0.1530 0.0562 Uiso 1.0000 . .
H H1 1.2232 0.0990 0.1323 0.0665 Uiso 1.0000 . .
H H113 -0.2078 0.5201 0.0623 0.1052 Uiso 1.0000 . .
H H112 -0.2875 0.4811 0.0199 0.1058 Uiso 1.0000 . .
H H111 -0.4050 0.4535 0.0630 0.1059 Uiso 1.0000 . .
H H3 1.0530 0.1538 0.0113 0.0637 Uiso 1.0000 . .
H H132 0.5316 0.3152 0.2061 0.1075 Uiso 1.0000 . .
H H133 0.3256 0.2531 0.1989 0.1079 Uiso 1.0000 . .
H H131 0.5739 0.2357 0.2257 0.1077 Uiso 1.0000 . .
H H22w 1.0875 0.0824 0.2392 0.1108 Uiso 1.0000 . .
H H123 -0.0206 0.3876 0.1991 0.1488 Uiso 1.0000 . .
H H21w 0.9353 0.1136 0.2140 0.1109 Uiso 1.0000 . .
H H122 0.1833 0.4544 0.1939 0.1486 Uiso 1.0000 . .
H H121 -0.0960 0.4706 0.2124 0.1492 Uiso 1.0000 . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 'International Tables Vol C 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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 S1 C11 . . . 103.68(15) ?
C10 S2 C12 . . . 103.50(16) ?
C4 N1 C7 . . . 121.1(2) ?
C4 N1 C5 . . . 131.9(2) ?
C7 N1 C5 . . . 107.0(2) ?
H22w O2w H21w . . . 98.6 no
C7 N2 C6 . . . 106.4(2) ?
N1 C4 C3 . . . 118.7(3) ?
N1 C4 H4 . . . 117.7 no
C3 C4 H4 . . . 123.6 no
N1 C7 N2 . . . 110.8(2) ?
N1 C7 C1 . . . 119.5(3) ?
N2 C7 C1 . . . 129.7(3) ?
C10 C9 C8 . . . 124.1(3) ?
C10 C9 H9 . . . 118.0 no
C8 C9 H9 . . . 117.8 no
N1 C5 C6 . . . 104.5(2) ?
N1 C5 C8 . . . 121.6(2) ?
C6 C5 C8 . . . 133.9(2) ?
C4 C3 C2 . . . 121.1(3) ?
C4 C3 H3 . . . 118.7 no
C2 C3 H3 . . . 120.3 no
C3 C2 C1 . . . 120.1(3) ?
C3 C2 H2 . . . 119.3 no
C1 C2 H2 . . . 120.5 no
C7 C1 C2 . . . 119.5(3) ?
C7 C1 H1 . . . 118.4 no
C2 C1 H1 . . . 122.0 no
C5 C6 N2 . . . 111.3(2) ?
C5 C6 C13 . . . 130.0(3) ?
N2 C6 C13 . . . 118.7(3) ?
S1 C10 S2 . . . 115.83(15) ?
S1 C10 C9 . . . 121.4(2) ?
S2 C10 C9 . . . 122.7(2) ?
C5 C8 C9 . . . 118.4(2) ?
C5 C8 O1 . . . 120.6(2) ?
C9 C8 O1 . . . 121.0(2) ?
S1 C11 H113 . . . 110.7 no
S1 C11 H112 . . . 107.3 no
H113 C11 H112 . . . 109.3 no
S1 C11 H111 . . . 110.4 no
H113 C11 H111 . . . 109.6 no
H112 C11 H111 . . . 109.5 no
C6 C13 H132 . . . 110.3 no
C6 C13 H133 . . . 110.5 no
H132 C13 H133 . . . 107.1 no
C6 C13 H131 . . . 110.4 no
H132 C13 H131 . . . 108.6 no
H133 C13 H131 . . . 109.9 no
S2 C12 H123 . . . 109.3 no
S2 C12 H122 . . . 108.2 no
H123 C12 H122 . . . 110.5 no
S2 C12 H121 . . . 108.0 no
H123 C12 H121 . . . 110.3 no
H122 C12 H121 . . . 110.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C10 . . 1.750(3) ?
S1 C11 . . 1.806(3) ?
S2 C10 . . 1.748(3) ?
S2 C12 . . 1.791(4) ?
O1 C8 . . 1.237(3) ?
N1 C4 . . 1.379(3) ?
N1 C7 . . 1.380(3) ?
N1 C5 . . 1.406(3) ?
O2w H22w . . 0.822 no
O2w H21w . . 0.817 no
N2 C7 . . 1.340(4) ?
N2 C6 . . 1.356(3) ?
C4 C3 . . 1.358(4) ?
C4 H4 . . 0.948 no
C7 C1 . . 1.401(4) ?
C9 C10 . . 1.359(3) ?
C9 C8 . . 1.443(4) ?
C9 H9 . . 0.922 no
C5 C6 . . 1.393(4) ?
C5 C8 . . 1.459(3) ?
C3 C2 . . 1.405(4) ?
C3 H3 . . 0.930 no
C2 C1 . . 1.348(4) ?
C2 H2 . . 0.931 no
C1 H1 . . 0.932 no
C6 C13 . . 1.496(4) ?
C11 H113 . . 0.952 no
C11 H112 . . 0.954 no
C11 H111 . . 0.955 no
C13 H132 . . 0.966 no
C13 H133 . . 0.956 no
C13 H131 . . 0.951 no
C12 H123 . . 0.974 no
C12 H122 . . 0.964 no
C12 H121 . . 0.953 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C4 H4 O1 . . . 0.95 2.23 2.840(4) 121 yes
C3 H3 O1 . . 4_555 0.93 2.45 3.242(4) 143 yes
O2w H22w O2w . . 8_555 0.82 2.05 2.862(4) 168 yes
O2w H21w N2 . . . 0.82 2.06 2.849(4) 164 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26000858
