#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/26/1502648.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_1502648
loop_
_publ_author_name
'Soh, Chai Hoon'
'Lam, Yulin'
_publ_section_title
;
 Microwave-assisted synthesis of substituted
 2-(benzylthio)imidazo[1,2a]pyrimidin-5-ones.
;
_journal_issue                   2
_journal_name_full               'Journal of combinatorial chemistry'
_journal_page_first              286
_journal_page_last               291
_journal_paper_doi               10.1021/cc900176x
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C22 H19 N3 O2 S'
_chemical_formula_weight         389.46
_chemical_name_systematic
; 
 2-(benzylthio)-7-methyl-5-oxo-1,5-dihydroimidazo[1,2-a]pyrimidine-6-carbaldehyde  
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.7180(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.4388(9)
_cell_length_b                   15.7401(8)
_cell_length_c                   14.4540(8)
_cell_measurement_reflns_used    6389
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.43
_cell_volume                     3819.1(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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      223(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_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13247
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.9444
_exptl_absorpt_correction_T_min  0.8610
_exptl_absorpt_correction_type   'Sadabs,(Sheldrick 2001)'
_exptl_crystal_colour            PALE
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0419
_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)+(0.0672P)²+1.3864P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1171
_reflns_number_gt                3797
_reflns_number_total             4396
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cc900176x_si_002.cif
_cod_data_source_block
2-(benzylthio)-7-methyl-5-oxo-1,5-dihydroimidazo[1,2-a]pyrimidine-6-carbaldehyde
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1502648
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.28794(2) 0.18056(2) 0.62008(3) 0.04329(13) Uani 1 1 d .
N1 N 0.42035(7) 0.38228(7) 0.63017(8) 0.0348(2) Uani 1 1 d .
N2 N 0.29694(6) 0.35630(7) 0.62735(8) 0.0345(2) Uani 1 1 d .
N3 N 0.33367(7) 0.50173(8) 0.62204(9) 0.0418(3) Uani 1 1 d .
O1 O 0.55177(6) 0.39501(8) 0.63704(9) 0.0556(3) Uani 1 1 d .
O2 O 0.54239(9) 0.65172(9) 0.62123(12) 0.0776(4) Uani 1 1 d .
C1 C 0.48887(8) 0.43150(9) 0.63055(10) 0.0398(3) Uani 1 1 d .
C2 C 0.47206(9) 0.52105(9) 0.62315(9) 0.0414(3) Uani 1 1 d .
C3 C 0.39540(10) 0.55160(9) 0.61972(10) 0.0425(3) Uani 1 1 d .
C4 C 0.34901(8) 0.41922(8) 0.62644(9) 0.0346(3) Uani 1 1 d .
C5 C 0.41300(8) 0.29480(9) 0.63466(9) 0.0369(3) Uani 1 1 d .
H5 H 0.4537 0.2547 0.6388 0.044 Uiso 1 1 calc R
C6 C 0.33646(8) 0.27791(8) 0.63202(9) 0.0346(3) Uani 1 1 d .
C7 C 0.53965(11) 0.57462(11) 0.62083(12) 0.0559(4) Uani 1 1 d .
H7 H 0.5866 0.5462 0.6188 0.067 Uiso 1 1 calc R
C8 C 0.37607(13) 0.64458(10) 0.61257(14) 0.0607(5) Uani 1 1 d .
H8A H 0.3197 0.6524 0.6062 0.091 Uiso 1 1 calc R
H8B H 0.3892 0.6683 0.5568 0.091 Uiso 1 1 calc R
H8C H 0.4068 0.6732 0.6701 0.091 Uiso 1 1 calc R
C9 C 0.21352(8) 0.37008(10) 0.62400(10) 0.0393(3) Uani 1 1 d .
H9A H 0.1819 0.3226 0.5897 0.047 Uiso 1 1 calc R
H9B H 0.1949 0.4220 0.5874 0.047 Uiso 1 1 calc R
C10 C 0.19919(7) 0.37793(8) 0.72243(9) 0.0333(3) Uani 1 1 d .
C11 C 0.12816(8) 0.34858(9) 0.73644(11) 0.0401(3) Uani 1 1 d .
H11 H 0.0911 0.3203 0.6865 0.048 Uiso 1 1 calc R
C12 C 0.11190(9) 0.36102(10) 0.82432(12) 0.0478(4) Uani 1 1 d .
H12 H 0.0636 0.3414 0.8335 0.057 Uiso 1 1 calc R
C13 C 0.16593(10) 0.40179(10) 0.89812(11) 0.0485(4) Uani 1 1 d .
H13 H 0.1542 0.4109 0.9571 0.058 Uiso 1 1 calc R
C14 C 0.23755(10) 0.42932(10) 0.88503(11) 0.0474(3) Uani 1 1 d .
H14 H 0.2751 0.4562 0.9357 0.057 Uiso 1 1 calc R
C15 C 0.25412(8) 0.41739(9) 0.79761(10) 0.0405(3) Uani 1 1 d .
H15 H 0.3029 0.4362 0.7892 0.049 Uiso 1 1 calc R
C16 C 0.27795(8) 0.16177(9) 0.74122(10) 0.0403(3) Uani 1 1 d .
H16A H 0.2526 0.2114 0.7614 0.048 Uiso 1 1 calc R
H16B H 0.2429 0.1128 0.7395 0.048 Uiso 1 1 calc R
C17 C 0.35595(8) 0.14545(8) 0.81421(10) 0.0351(3) Uani 1 1 d .
C18 C 0.38405(9) 0.20055(9) 0.89032(10) 0.0423(3) Uani 1 1 d .
H18 H 0.3548 0.2496 0.8957 0.051 Uiso 1 1 calc R
C19 C 0.45552(10) 0.18378(10) 0.95905(11) 0.0496(4) Uani 1 1 d .
H19 H 0.4743 0.2214 1.0107 0.059 Uiso 1 1 calc R
C20 C 0.49830(10) 0.11266(11) 0.95152(12) 0.0520(4) Uani 1 1 d .
H20 H 0.5460 0.1009 0.9986 0.062 Uiso 1 1 calc R
C21 C 0.47160(10) 0.05803(10) 0.87495(13) 0.0540(4) Uani 1 1 d .
H21 H 0.5016 0.0096 0.8693 0.065 Uiso 1 1 calc R
C22 C 0.40081(9) 0.07442(9) 0.80649(12) 0.0455(3) Uani 1 1 d .
H22 H 0.3829 0.0371 0.7543 0.055 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'
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
C6 S1 C16 102.57(6)
C4 N1 C5 109.33(11)
C4 N1 C1 121.69(11)
C5 N1 C1 128.97(11)
C4 N2 C6 108.85(10)
C4 N2 C9 124.04(11)
C6 N2 C9 127.12(12)
C4 N3 C3 115.00(12)
O1 C1 N1 118.75(13)
O1 C1 C2 128.96(14)
N1 C1 C2 112.30(12)
C3 C2 C1 120.65(13)
C3 C2 C7 124.57(14)
C1 C2 C7 114.79(14)
N3 C3 C2 124.06(13)
N3 C3 C8 113.98(15)
C2 C3 C8 121.96(15)
N3 C4 N2 126.45(12)
N3 C4 N1 126.26(13)
N2 C4 N1 107.29(11)
C6 C5 N1 107.29(11)
C5 C6 N2 107.23(11)
C5 C6 S1 128.86(11)
N2 C6 S1 123.40(10)
O2 C7 C2 127.54(19)
N2 C9 C10 113.44(11)
C15 C10 C11 119.33(13)
C15 C10 C9 121.21(12)
C11 C10 C9 119.40(12)
C10 C11 C12 119.88(14)
C13 C12 C11 120.56(14)
C12 C13 C14 119.62(14)
C13 C14 C15 120.17(14)
C14 C15 C10 120.40(13)
C17 C16 S1 113.40(9)
C18 C17 C22 118.95(14)
C18 C17 C16 120.69(12)
C22 C17 C16 120.36(13)
C17 C18 C19 120.30(14)
C20 C19 C18 120.08(14)
C19 C20 C21 120.13(15)
C20 C21 C22 120.02(15)
C21 C22 C17 120.49(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C6 1.7362(14)
S1 C16 1.8300(14)
N1 C4 1.3610(16)
N1 C5 1.3861(17)
N1 C1 1.4228(17)
N2 C4 1.3460(17)
N2 C6 1.4059(17)
N2 C9 1.4587(16)
N3 C4 1.3241(17)
N3 C3 1.340(2)
O1 C1 1.2191(17)
O2 C7 1.214(2)
C1 C2 1.438(2)
C2 C3 1.409(2)
C2 C7 1.457(2)
C3 C8 1.499(2)
C5 C6 1.3514(19)
C9 C10 1.5148(18)
C10 C15 1.3858(19)
C10 C11 1.3872(18)
C11 C12 1.388(2)
C12 C13 1.376(2)
C13 C14 1.383(2)
C14 C15 1.383(2)
C16 C17 1.501(2)
C17 C18 1.382(2)
C17 C22 1.3863(19)
C18 C19 1.393(2)
C19 C20 1.366(2)
C20 C21 1.379(2)
C21 C22 1.381(2)
