# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2010


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Zhuang-Ping Zhan'
_publ_contact_author_email       ZPZHAN@XMU.EDU.CN

_publ_section_title              
;
Facile One-Pot Synthesis of Three
Different Substituted Thiazoles from Propargylic Alcohols
;
loop_
_publ_author_name
'Zhuang-Ping Zhan.'
'Li Chen.'
'Xun Gao.'
'Min Lin.'
'Yingming Pan.'

# Attachment 'P.cif'

data_p
_database_code_depnum_ccdc_archive 'CCDC 751760'
#TrackingRef 'P.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H19 N S'
_chemical_formula_weight         353.46

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Fdd2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   17.699(4)
_cell_length_b                   74.502(18)
_cell_length_c                   5.7208(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     7544(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1649
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      19.78

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2976
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14565
_diffrn_reflns_av_R_equivalents  0.1042
_diffrn_reflns_av_sigmaI/netI    0.0967
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -90
_diffrn_reflns_limit_k_max       89
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.09
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3678
_reflns_number_gt                2142
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.1070P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(18)
_refine_ls_number_reflns         3678
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1190
_refine_ls_R_factor_gt           0.0722
_refine_ls_wR_factor_ref         0.2081
_refine_ls_wR_factor_gt          0.1786
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_restrained_S_all      0.943
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.49760(7) 0.029935(19) 0.3692(3) 0.0663(4) Uani 1 1 d . . .
N1 N 0.5866(2) 0.05446(6) 0.5104(8) 0.0629(12) Uani 1 1 d . . .
C13 C 0.6088(3) 0.02553(8) 0.7019(10) 0.0606(14) Uani 1 1 d . . .
C19 C 0.4246(3) 0.05446(7) 0.0844(9) 0.0578(14) Uani 1 1 d . . .
C20 C 0.4375(3) 0.06362(8) -0.1201(10) 0.0680(15) Uani 1 1 d . . .
H20 H 0.4859 0.0676 -0.1556 0.082 Uiso 1 1 calc R . .
C11 C 0.4869(3) 0.05100(7) 0.2521(10) 0.0582(13) Uani 1 1 d . . .
C10 C 0.5392(3) 0.06207(7) 0.3436(9) 0.0585(13) Uani 1 1 d . . .
C7 C 0.6672(3) 0.09647(8) 0.1808(11) 0.0733(17) Uani 1 1 d . . .
H7 H 0.6662 0.1018 0.3278 0.088 Uiso 1 1 calc R . .
C12 C 0.5724(2) 0.03787(7) 0.5421(9) 0.0533(13) Uani 1 1 d . . .
C6 C 0.7318(3) 0.10115(8) 0.0345(11) 0.0631(15) Uani 1 1 d . . .
C23 C 0.2944(3) 0.05147(8) -0.0223(11) 0.0693(16) Uani 1 1 d . . .
H23 H 0.2460 0.0475 0.0134 0.083 Uiso 1 1 calc R . .
C8 C 0.6119(3) 0.08607(7) 0.1342(12) 0.0664(14) Uani 1 1 d . . .
H8 H 0.6113 0.0808 -0.0131 0.080 Uiso 1 1 calc R . .
C24 C 0.3070(3) 0.06060(8) -0.2265(11) 0.0680(16) Uani 1 1 d . . .
H24 H 0.2677 0.0625 -0.3315 0.082 Uiso 1 1 calc R . .
C21 C 0.3524(3) 0.04817(7) 0.1297(10) 0.0585(13) Uani 1 1 d . . .
H21 H 0.3433 0.0416 0.2652 0.070 Uiso 1 1 calc R . .
C5 C 0.7469(3) 0.09287(8) -0.1747(11) 0.0694(16) Uani 1 1 d . . .
H5 H 0.7146 0.0840 -0.2306 0.083 Uiso 1 1 calc R . .
C18 C 0.6775(4) 0.00329(10) 1.0232(12) 0.083(2) Uani 1 1 d . . .
H18 H 0.7002 -0.0042 1.1322 0.100 Uiso 1 1 calc R . .
C14 C 0.6507(3) 0.03255(8) 0.8882(11) 0.0711(15) Uani 1 1 d . . .
H14 H 0.6556 0.0449 0.9072 0.085 Uiso 1 1 calc R . .
C22 C 0.3782(3) 0.06688(8) -0.2745(10) 0.0718(16) Uani 1 1 d . . .
H22 H 0.3870 0.0733 -0.4109 0.086 Uiso 1 1 calc R . .
C16 C 0.6848(3) 0.02086(10) 1.0437(11) 0.0776(17) Uani 1 1 d . . .
H16 H 0.7134 0.0255 1.1659 0.093 Uiso 1 1 calc R . .
C9 C 0.5464(3) 0.08152(7) 0.2983(10) 0.0641(15) Uani 1 1 d . . .
H9A H 0.5539 0.0877 0.4457 0.077 Uiso 1 1 calc R . .
H9B H 0.4997 0.0859 0.2303 0.077 Uiso 1 1 calc R . .
C3 C 0.8090(4) 0.09764(9) -0.3004(12) 0.0788(18) Uani 1 1 d . . .
H3 H 0.8197 0.0917 -0.4392 0.095 Uiso 1 1 calc R . .
C15 C 0.6032(3) 0.00728(8) 0.6852(11) 0.0750(18) Uani 1 1 d . . .
H15 H 0.5755 0.0023 0.5629 0.090 Uiso 1 1 calc R . .
C4 C 0.7796(3) 0.11439(8) 0.1054(12) 0.0782(17) Uani 1 1 d . . .
H4 H 0.7701 0.1203 0.2456 0.094 Uiso 1 1 calc R . .
C2 C 0.8420(4) 0.11933(10) -0.0253(15) 0.102(2) Uani 1 1 d . . .
H2 H 0.8742 0.1284 0.0260 0.122 Uiso 1 1 calc R . .
C17 C 0.6370(4) -0.00394(8) 0.8431(13) 0.085(2) Uani 1 1 d . . .
H17 H 0.6325 -0.0163 0.8279 0.102 Uiso 1 1 calc R . .
C1 C 0.8550(4) 0.11077(9) -0.2281(14) 0.0847(19) Uani 1 1 d . . .
H1 H 0.8964 0.1140 -0.3191 0.102 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0528(8) 0.0740(9) 0.0721(8) 0.0055(9) -0.0116(7) -0.0096(7)
N1 0.044(2) 0.080(3) 0.065(3) 0.009(3) 0.008(2) 0.001(2)
C13 0.047(3) 0.071(4) 0.064(4) 0.004(3) 0.011(3) -0.004(3)
C19 0.048(3) 0.065(3) 0.060(4) -0.011(3) 0.000(3) 0.006(2)
C20 0.047(3) 0.095(4) 0.062(3) 0.008(3) 0.012(3) 0.008(3)
C11 0.045(3) 0.065(3) 0.064(3) 0.001(3) 0.011(3) 0.000(3)
C10 0.049(3) 0.071(3) 0.055(3) 0.005(3) 0.007(3) 0.005(3)
C7 0.068(4) 0.075(4) 0.077(4) 0.001(3) -0.001(3) 0.010(3)
C12 0.032(3) 0.075(4) 0.053(3) 0.001(3) -0.005(2) -0.012(2)
C6 0.052(3) 0.071(4) 0.066(4) 0.006(3) -0.002(3) 0.006(3)
C23 0.047(3) 0.084(4) 0.077(4) -0.014(3) -0.012(3) -0.001(3)
C8 0.061(3) 0.064(3) 0.074(4) 0.007(3) -0.002(3) -0.006(3)
C24 0.059(4) 0.084(4) 0.061(4) -0.010(3) -0.015(3) 0.010(3)
C21 0.050(3) 0.065(3) 0.061(3) -0.007(3) 0.001(3) -0.002(2)
C5 0.067(4) 0.067(4) 0.075(4) 0.004(3) -0.005(3) -0.002(3)
C18 0.075(4) 0.106(5) 0.068(4) 0.021(4) -0.003(3) 0.015(4)
C14 0.069(4) 0.074(4) 0.071(4) -0.005(3) -0.002(3) -0.005(3)
C22 0.075(4) 0.091(4) 0.050(3) 0.007(3) -0.003(3) 0.014(3)
C16 0.073(4) 0.096(5) 0.064(4) 0.002(4) -0.011(3) -0.006(4)
C9 0.043(3) 0.083(4) 0.066(4) -0.005(3) -0.002(3) 0.003(3)
C3 0.074(4) 0.083(4) 0.079(4) 0.000(3) 0.014(3) 0.008(4)
C15 0.064(4) 0.079(4) 0.082(4) 0.012(3) -0.023(3) -0.001(3)
C4 0.064(4) 0.098(4) 0.073(4) -0.006(4) 0.001(4) -0.011(3)
C2 0.092(5) 0.108(6) 0.105(6) -0.008(5) -0.002(5) -0.040(4)
C17 0.083(4) 0.073(4) 0.098(5) 0.019(4) -0.020(4) -0.002(3)
C1 0.063(4) 0.089(4) 0.102(5) 0.016(4) 0.015(4) -0.003(4)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C11 1.717(6) . ?
S1 C12 1.756(5) . ?
N1 C12 1.274(6) . ?
N1 C10 1.391(6) . ?
C13 C15 1.366(7) . ?
C13 C14 1.400(8) . ?
C13 C12 1.448(7) . ?
C19 C20 1.373(7) . ?
C19 C21 1.386(7) . ?
C19 C11 1.483(7) . ?
C20 C22 1.393(7) . ?
C20 H20 0.9300 . ?
C11 C10 1.346(7) . ?
C10 C9 1.478(7) . ?
C7 C8 1.277(7) . ?
C7 C6 1.459(8) . ?
C7 H7 0.9300 . ?
C6 C4 1.362(8) . ?
C6 C5 1.372(8) . ?
C23 C21 1.367(7) . ?
C23 C24 1.370(8) . ?
C23 H23 0.9300 . ?
C8 C9 1.530(7) . ?
C8 H8 0.9300 . ?
C24 C22 1.373(8) . ?
C24 H24 0.9300 . ?
C21 H21 0.9300 . ?
C5 C3 1.361(8) . ?
C5 H5 0.9300 . ?
C18 C16 1.321(8) . ?
C18 C17 1.366(9) . ?
C18 H18 0.9300 . ?
C14 C16 1.383(8) . ?
C14 H14 0.9300 . ?
C22 H22 0.9300 . ?
C16 H16 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C3 C1 1.338(9) . ?
C3 H3 0.9300 . ?
C15 C17 1.369(8) . ?
C15 H15 0.9300 . ?
C4 C2 1.383(9) . ?
C4 H4 0.9300 . ?
C2 C1 1.344(10) . ?
C2 H2 0.9300 . ?
C17 H17 0.9300 . ?
C1 H1 0.9300 . ?

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
_geom_angle_publ_flag
C11 S1 C12 89.7(3) . . ?
C12 N1 C10 112.0(4) . . ?
C15 C13 C14 117.7(6) . . ?
C15 C13 C12 123.7(5) . . ?
C14 C13 C12 118.6(5) . . ?
C20 C19 C21 118.7(5) . . ?
C20 C19 C11 120.9(5) . . ?
C21 C19 C11 120.4(5) . . ?
C19 C20 C22 120.1(5) . . ?
C19 C20 H20 119.9 . . ?
C22 C20 H20 119.9 . . ?
C10 C11 C19 131.0(5) . . ?
C10 C11 S1 109.4(4) . . ?
C19 C11 S1 119.6(4) . . ?
C11 C10 N1 115.6(5) . . ?
C11 C10 C9 126.3(5) . . ?
N1 C10 C9 117.9(5) . . ?
C8 C7 C6 128.8(6) . . ?
C8 C7 H7 115.6 . . ?
C6 C7 H7 115.6 . . ?
N1 C12 C13 128.2(5) . . ?
N1 C12 S1 113.3(4) . . ?
C13 C12 S1 118.5(4) . . ?
C4 C6 C5 117.7(6) . . ?
C4 C6 C7 119.3(6) . . ?
C5 C6 C7 123.0(6) . . ?
C21 C23 C24 120.7(6) . . ?
C21 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C7 C8 C9 126.0(6) . . ?
C7 C8 H8 117.0 . . ?
C9 C8 H8 117.0 . . ?
C23 C24 C22 119.2(6) . . ?
C23 C24 H24 120.4 . . ?
C22 C24 H24 120.4 . . ?
C23 C21 C19 120.8(6) . . ?
C23 C21 H21 119.6 . . ?
C19 C21 H21 119.6 . . ?
C3 C5 C6 120.0(6) . . ?
C3 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C16 C18 C17 120.6(6) . . ?
C16 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C16 C14 C13 119.0(5) . . ?
C16 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C24 C22 C20 120.4(6) . . ?
C24 C22 H22 119.8 . . ?
C20 C22 H22 119.8 . . ?
C18 C16 C14 121.7(6) . . ?
C18 C16 H16 119.2 . . ?
C14 C16 H16 119.2 . . ?
C10 C9 C8 112.9(4) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C1 C3 C5 121.3(6) . . ?
C1 C3 H3 119.4 . . ?
C5 C3 H3 119.4 . . ?
C13 C15 C17 121.9(6) . . ?
C13 C15 H15 119.0 . . ?
C17 C15 H15 119.0 . . ?
C6 C4 C2 121.9(6) . . ?
C6 C4 H4 119.1 . . ?
C2 C4 H4 119.1 . . ?
C1 C2 C4 118.5(7) . . ?
C1 C2 H2 120.8 . . ?
C4 C2 H2 120.8 . . ?
C18 C17 C15 119.2(6) . . ?
C18 C17 H17 120.4 . . ?
C15 C17 H17 120.4 . . ?
C3 C1 C2 120.7(7) . . ?
C3 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.080