# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_yangyh_0114_1
_database_code_depnum_ccdc_archive 'CCDC 1040952'
_audit_update_record             
;
2014-12-25 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;
_audit_creation_date             2014-01-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_chemical_name_common            3a
_chemical_name_systematic        'Thiazolo Pyrone'
_chemical_formula_moiety         'C20 H17 N O2 S'
_chemical_formula_sum            'C20 H17 N O2 S'
_chemical_formula_weight         335.41
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   5.7758(5)
_cell_length_b                   20.0870(19)
_cell_length_c                   7.3139(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.951(8)
_cell_angle_gamma                90.00
_cell_volume                     847.42(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1108
_cell_measurement_temperature    295.3(3)
_cell_measurement_theta_max      25.9210
_cell_measurement_theta_min      4.0570
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3502
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.45
_diffrn_ambient_temperature      295.3(3)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1101796000
_diffrn_orient_matrix_UB_12      -0.0150846000
_diffrn_orient_matrix_UB_13      0.0151904000
_diffrn_orient_matrix_UB_21      -0.0325848000
_diffrn_orient_matrix_UB_22      -0.0254622000
_diffrn_orient_matrix_UB_23      -0.0636236000
_diffrn_orient_matrix_UB_31      0.0435847000
_diffrn_orient_matrix_UB_32      0.0192901000
_diffrn_orient_matrix_UB_33      -0.0718043000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1878
_reflns_number_total             2273
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.28(15)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2273
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0639
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0780P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1582
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C15(H15), C16(H16), C18(H18), C12(H12), C9(H9), C11(H11),
 C17(H17), C14(H14)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S -0.0088(2) 0.23899(7) 0.57729(16) 0.0573(4) Uani 1 1 d . . .
N1 N 0.3427(7) 0.1653(2) 0.5227(6) 0.0577(10) Uani 1 1 d . . .
O2 O 0.5006(6) 0.2149(2) 0.2680(5) 0.0698(11) Uani 1 1 d . . .
C13 C 0.2320(7) 0.3802(2) 0.3590(5) 0.0461(10) Uani 1 1 d . . .
C5 C 0.1561(8) 0.2586(2) 0.3945(7) 0.0525(12) Uani 1 1 d . . .
C1 C 0.1358(8) 0.3174(3) 0.2714(6) 0.0511(11) Uani 1 1 d . . .
H1 H -0.0292 0.3247 0.2399 0.061 Uiso 1 1 calc . . R
C6 C 0.1741(8) 0.1733(3) 0.6342(6) 0.0523(11) Uani 1 1 d . . .
C2 C 0.2547(8) 0.2966(3) 0.0929(6) 0.0539(12) Uani 1 1 d . . .
H2 H 0.1498 0.2642 0.0322 0.065 Uiso 1 1 calc . . R
C7 C 0.1489(9) 0.1327(3) 0.7997(7) 0.0539(12) Uani 1 1 d . . .
C4 C 0.3276(8) 0.2131(3) 0.3925(7) 0.0538(12) Uani 1 1 d . . .
O1 O 0.6493(7) 0.2666(2) 0.0401(6) 0.0828(13) Uani 1 1 d . . .
C3 C 0.4841(9) 0.2601(3) 0.1282(7) 0.0584(14) Uani 1 1 d . . .
C8 C 0.3172(10) 0.0868(3) 0.8557(8) 0.0663(14) Uani 1 1 d . . .
H8 H 0.4448 0.0801 0.7853 0.080 Uiso 1 1 calc . . R
C19 C 0.2814(10) 0.3519(3) -0.0450(8) 0.0691(15) Uani 1 1 d . . .
H19A H 0.3588 0.3339 -0.1488 0.083 Uiso 1 1 calc . . R
H19B H 0.3816 0.3858 0.0106 0.083 Uiso 1 1 calc . . R
C10 C 0.1112(11) 0.0616(4) 1.1208(8) 0.0766(17) Uani 1 1 d . . .
H10 H 0.0987 0.0378 1.2289 0.092 Uiso 1 1 calc . . R
C15 C 0.5350(10) 0.4379(3) 0.5352(8) 0.0713(15) Uani 1 1 d . . .
H15 H 0.6805 0.4373 0.5958 0.086 Uiso 1 1 calc . . R
C16 C 0.4130(12) 0.4961(3) 0.5258(8) 0.0758(17) Uani 1 1 d . . .
H16 H 0.4716 0.5344 0.5826 0.091 Uiso 1 1 calc . . R
C18 C 0.1110(9) 0.4389(3) 0.3529(7) 0.0617(13) Uani 1 1 d . . .
H18 H -0.0362 0.4399 0.2950 0.074 Uiso 1 1 calc . . R
C12 C -0.0417(10) 0.1403(3) 0.9071(7) 0.0652(14) Uani 1 1 d . . .
H12 H -0.1614 0.1687 0.8679 0.078 Uiso 1 1 calc . . R
C9 C 0.2966(11) 0.0511(3) 1.0151(8) 0.0785(17) Uani 1 1 d . . .
H9 H 0.4088 0.0199 1.0508 0.094 Uiso 1 1 calc . . R
C11 C -0.0563(11) 0.1071(3) 1.0678(8) 0.0740(17) Uani 1 1 d . . .
H11 H -0.1795 0.1151 1.1417 0.089 Uiso 1 1 calc . . R
C17 C 0.2021(12) 0.4968(3) 0.4305(7) 0.0735(17) Uani 1 1 d . . .
H17 H 0.1195 0.5364 0.4180 0.088 Uiso 1 1 calc . . R
C20 C 0.0580(12) 0.3848(4) -0.1153(7) 0.0788(17) Uani 1 1 d . . .
H20A H 0.0897 0.4145 -0.2137 0.118 Uiso 1 1 calc . . GR
H20B H -0.0074 0.4094 -0.0179 0.118 Uiso 1 1 calc . . GR
H20C H -0.0498 0.3513 -0.1588 0.118 Uiso 1 1 calc . . GR
C14 C 0.4484(8) 0.3802(3) 0.4575(7) 0.0597(12) Uani 1 1 d . . .
H14 H 0.5330 0.3410 0.4699 0.072 Uiso 1 1 calc . . R


_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 C5 1.726(5) . ?
S1 C6 1.728(5) . ?
N1 C6 1.312(6) . ?
N1 C4 1.351(6) . ?
O2 C4 1.387(6) . ?
O2 C3 1.367(6) . ?
C13 C1 1.508(7) . ?
C13 C18 1.370(7) . ?
C13 C14 1.410(6) . ?
C5 C1 1.487(7) . ?
C5 C4 1.349(7) . ?
C1 H1 0.9800 . ?
C1 C2 1.563(6) . ?
C6 C7 1.473(7) . ?
C2 H2 0.9800 . ?
C2 C3 1.525(7) . ?
C2 C19 1.513(7) . ?
C7 C8 1.386(7) . ?
C7 C12 1.393(7) . ?
O1 C3 1.186(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(8) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.515(8) . ?
C10 H10 0.9300 . ?
C10 C9 1.369(9) . ?
C10 C11 1.372(9) . ?
C15 H15 0.9300 . ?
C15 C16 1.365(9) . ?
C15 C14 1.373(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.372(9) . ?
C18 H18 0.9300 . ?
C18 C17 1.386(8) . ?
C12 H12 0.9300 . ?
C12 C11 1.358(7) . ?
C9 H9 0.9300 . ?
C11 H11 0.9300 . ?
C17 H17 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C14 H14 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
C5 S1 C6 90.3(2) . . ?
C6 N1 C4 109.1(4) . . ?
C3 O2 C4 119.0(4) . . ?
C18 C13 C1 122.0(4) . . ?
C18 C13 C14 117.0(5) . . ?
C14 C13 C1 121.0(4) . . ?
C1 C5 S1 128.4(3) . . ?
C4 C5 S1 106.8(4) . . ?
C4 C5 C1 124.6(4) . . ?
C13 C1 H1 107.9 . . ?
C13 C1 C2 114.2(4) . . ?
C5 C1 C13 113.1(4) . . ?
C5 C1 H1 107.9 . . ?
C5 C1 C2 105.6(4) . . ?
C2 C1 H1 107.9 . . ?
N1 C6 S1 114.1(4) . . ?
N1 C6 C7 123.4(5) . . ?
C7 C6 S1 122.4(4) . . ?
C1 C2 H2 105.5 . . ?
C3 C2 C1 113.7(4) . . ?
C3 C2 H2 105.5 . . ?
C19 C2 C1 115.1(4) . . ?
C19 C2 H2 105.5 . . ?
C19 C2 C3 110.4(4) . . ?
C8 C7 C6 120.9(5) . . ?
C8 C7 C12 117.9(5) . . ?
C12 C7 C6 121.2(5) . . ?
N1 C4 O2 117.3(4) . . ?
C5 C4 N1 119.7(4) . . ?
C5 C4 O2 122.9(5) . . ?
O2 C3 C2 118.2(4) . . ?
O1 C3 O2 116.9(5) . . ?
O1 C3 C2 124.8(5) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.4(5) . . ?
C9 C8 H8 119.8 . . ?
C2 C19 H19A 108.4 . . ?
C2 C19 H19B 108.4 . . ?
C2 C19 C20 115.6(4) . . ?
H19A C19 H19B 107.4 . . ?
C20 C19 H19A 108.4 . . ?
C20 C19 H19B 108.4 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.2(5) . . ?
C11 C10 H10 119.9 . . ?
C16 C15 H15 119.1 . . ?
C16 C15 C14 121.7(5) . . ?
C14 C15 H15 119.1 . . ?
C15 C16 H16 120.8 . . ?
C15 C16 C17 118.5(5) . . ?
C17 C16 H16 120.8 . . ?
C13 C18 H18 119.1 . . ?
C13 C18 C17 121.7(5) . . ?
C17 C18 H18 119.1 . . ?
C7 C12 H12 119.3 . . ?
C11 C12 C7 121.4(5) . . ?
C11 C12 H12 119.3 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.1(6) . . ?
C10 C9 H9 119.9 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(5) . . ?
C12 C11 H11 120.1 . . ?
C16 C17 C18 120.6(5) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(5) . . ?
C15 C14 H14 119.8 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C5 C1 C13 75.9(5) . . . . ?
S1 C5 C1 C2 -158.5(4) . . . . ?
S1 C5 C4 N1 -1.1(6) . . . . ?
S1 C5 C4 O2 -177.2(4) . . . . ?
S1 C6 C7 C8 -170.6(4) . . . . ?
S1 C6 C7 C12 8.0(7) . . . . ?
N1 C6 C7 C8 5.7(7) . . . . ?
N1 C6 C7 C12 -175.7(5) . . . . ?
C13 C1 C2 C3 80.9(5) . . . . ?
C13 C1 C2 C19 -48.0(5) . . . . ?
C13 C18 C17 C16 -3.7(8) . . . . ?
C5 S1 C6 N1 -1.5(4) . . . . ?
C5 S1 C6 C7 175.1(4) . . . . ?
C5 C1 C2 C3 -44.0(5) . . . . ?
C5 C1 C2 C19 -172.8(4) . . . . ?
C1 C13 C18 C17 -178.7(5) . . . . ?
C1 C13 C14 C15 179.4(5) . . . . ?
C1 C5 C4 N1 173.2(4) . . . . ?
C1 C5 C4 O2 -2.9(7) . . . . ?
C1 C2 C3 O2 39.7(6) . . . . ?
C1 C2 C3 O1 -142.4(5) . . . . ?
C1 C2 C19 C20 -59.1(7) . . . . ?
C6 S1 C5 C1 -172.7(4) . . . . ?
C6 S1 C5 C4 1.4(4) . . . . ?
C6 N1 C4 O2 176.3(4) . . . . ?
C6 N1 C4 C5 0.0(6) . . . . ?
C6 C7 C8 C9 177.3(5) . . . . ?
C6 C7 C12 C11 -174.4(5) . . . . ?
C7 C8 C9 C10 -1.1(9) . . . . ?
C7 C12 C11 C10 -4.5(9) . . . . ?
C4 N1 C6 S1 1.1(5) . . . . ?
C4 N1 C6 C7 -175.4(4) . . . . ?
C4 O2 C3 C2 -12.1(6) . . . . ?
C4 O2 C3 O1 169.8(5) . . . . ?
C4 C5 C1 C13 -97.1(5) . . . . ?
C4 C5 C1 C2 28.5(6) . . . . ?
C3 O2 C4 N1 176.3(4) . . . . ?
C3 O2 C4 C5 -7.5(7) . . . . ?
C3 C2 C19 C20 170.5(5) . . . . ?
C8 C7 C12 C11 4.1(8) . . . . ?
C19 C2 C3 O2 170.9(4) . . . . ?
C19 C2 C3 O1 -11.2(8) . . . . ?
C15 C16 C17 C18 2.8(8) . . . . ?
C16 C15 C14 C13 2.3(9) . . . . ?
C18 C13 C1 C5 -131.8(4) . . . . ?
C18 C13 C1 C2 107.3(5) . . . . ?
C18 C13 C14 C15 -3.0(7) . . . . ?
C12 C7 C8 C9 -1.3(8) . . . . ?
C9 C10 C11 C12 2.0(10) . . . . ?
C11 C10 C9 C8 0.7(10) . . . . ?
C14 C13 C1 C5 45.7(6) . . . . ?
C14 C13 C1 C2 -75.1(5) . . . . ?
C14 C13 C18 C17 3.6(7) . . . . ?
C14 C15 C16 C17 -2.2(9) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: PE and EA'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_yangyh_0114_2
_database_code_depnum_ccdc_archive 'CCDC 1040953'
_audit_update_record             
;
2014-12-25 deposited with the CCDC.
2015-03-23 downloaded from the CCDC.
;
_audit_creation_date             2014-01-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_chemical_name_common            3a'
_chemical_name_systematic        "Thiazolo Pyrone 3a'"
_chemical_formula_moiety         'C20 H17 N O2 S'
_chemical_formula_sum            'C20 H17 N O2 S'
_chemical_formula_weight         335.41
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   5.7825(17)
_cell_length_b                   20.098(2)
_cell_length_c                   7.3110(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.824(15)
_cell_angle_gamma                90.00
_cell_volume                     848.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    939
_cell_measurement_temperature    294.59(10)
_cell_measurement_theta_max      22.0720
_cell_measurement_theta_min      4.0570
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.27
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0986
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3528
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.45
_diffrn_ambient_temperature      294.59(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0969360000
_diffrn_orient_matrix_UB_12      -0.0182130000
_diffrn_orient_matrix_UB_13      0.0363501000
_diffrn_orient_matrix_UB_21      0.0278173000
_diffrn_orient_matrix_UB_22      -0.0093033000
_diffrn_orient_matrix_UB_23      -0.0898293000
_diffrn_orient_matrix_UB_31      0.0703053000
_diffrn_orient_matrix_UB_32      0.0288016000
_diffrn_orient_matrix_UB_33      -0.0060585000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2081
_reflns_number_total             2860
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(16)
_refine_ls_extinction_coef       0.073(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.908
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2860
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0569
_refine_ls_restrained_S_all      0.908
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1407
_refine_ls_wR_factor_ref         0.1877
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S -1.0084(2) -0.08632(7) -0.42270(18) 0.0564(4) Uani 1 1 d . . .
O1 O -0.3501(7) -0.1139(2) -0.9601(6) 0.0792(12) Uani 1 1 d . . .
O2 O -0.4988(6) -0.06173(19) -0.7318(5) 0.0664(11) Uani 1 1 d . . .
N1 N -0.6534(8) -0.0125(2) -0.4790(7) 0.0608(11) Uani 1 1 d . . .
C1 C -0.8633(8) -0.1642(2) -0.7296(7) 0.0484(11) Uani 1 1 d . . .
H1 H -1.0279 -0.1717 -0.7611 0.058 Uiso 1 1 calc . . R
C2 C -0.7439(9) -0.1434(3) -0.9079(7) 0.0538(12) Uani 1 1 d . . .
H2 H -0.8479 -0.1108 -0.9685 0.065 Uiso 1 1 calc . . R
C3 C -0.5193(9) -0.1077(3) -0.8707(8) 0.0585(13) Uani 1 1 d . . .
C4 C -0.6728(9) -0.0603(2) -0.6081(7) 0.0514(11) Uani 1 1 d . . .
C5 C -0.8437(8) -0.1060(2) -0.6030(7) 0.0498(12) Uani 1 1 d . . .
C6 C -0.8240(9) -0.0205(2) -0.3662(7) 0.0526(12) Uani 1 1 d . . .
C7 C -0.8516(10) 0.0197(2) -0.2008(7) 0.0544(12) Uani 1 1 d . . .
C8 C -0.6813(11) 0.0657(3) -0.1462(9) 0.0697(15) Uani 1 1 d . . .
H8 H -0.5539 0.0720 -0.2171 0.084 Uiso 1 1 calc . . R
C9 C -0.7008(12) 0.1018(3) 0.0123(10) 0.0803(19) Uani 1 1 d . . .
H9 H -0.5884 0.1331 0.0463 0.096 Uiso 1 1 calc . . R
C10 C -0.8846(12) 0.0919(3) 0.1202(10) 0.0752(17) Uani 1 1 d . . .
H10 H -0.8940 0.1156 0.2289 0.090 Uiso 1 1 calc . . R
C11 C -1.0572(13) 0.0466(3) 0.0682(10) 0.0787(18) Uani 1 1 d . . .
H11 H -1.1828 0.0402 0.1410 0.094 Uiso 1 1 calc . . R
C12 C -1.0403(11) 0.0112(3) -0.0928(8) 0.0654(15) Uani 1 1 d . . .
H12 H -1.1565 -0.0187 -0.1291 0.078 Uiso 1 1 calc . . R
C13 C -0.7663(8) -0.2268(2) -0.6392(6) 0.0465(10) Uani 1 1 d . . .
C14 C -0.8888(10) -0.2866(3) -0.6458(7) 0.0593(13) Uani 1 1 d . . .
H14 H -1.0349 -0.2879 -0.7048 0.071 Uiso 1 1 calc . . R
C15 C -0.7981(12) -0.3436(3) -0.5670(8) 0.0687(16) Uani 1 1 d . . .
H15 H -0.8822 -0.3830 -0.5764 0.082 Uiso 1 1 calc . . R
C16 C -0.5877(12) -0.3434(3) -0.4755(8) 0.0712(17) Uani 1 1 d . . .
H16 H -0.5266 -0.3821 -0.4230 0.085 Uiso 1 1 calc . . R
C17 C -0.4673(11) -0.2841(3) -0.4627(8) 0.0721(17) Uani 1 1 d . . .
H17 H -0.3253 -0.2828 -0.3974 0.086 Uiso 1 1 calc . . R
C18 C -0.5523(9) -0.2272(3) -0.5440(7) 0.0572(13) Uani 1 1 d . . .
H18 H -0.4656 -0.1883 -0.5354 0.069 Uiso 1 1 calc . . R
C19 C -0.7165(11) -0.1990(3) -1.0469(8) 0.0683(16) Uani 1 1 d . . .
H19A H -0.6394 -0.1812 -1.1511 0.082 Uiso 1 1 calc . . R
H19B H -0.6174 -0.2332 -0.9917 0.082 Uiso 1 1 calc . . R
C20 C -0.9433(11) -0.2308(3) -1.1147(8) 0.0762(17) Uani 1 1 d . . .
H20A H -0.9139 -0.2627 -1.2085 0.114 Uiso 1 1 calc . . GR
H20B H -1.0460 -0.1970 -1.1638 0.114 Uiso 1 1 calc . . GR
H20C H -1.0132 -0.2527 -1.0147 0.114 Uiso 1 1 calc . . GR


_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 C5 1.710(5) . ?
S1 C6 1.737(5) . ?
O1 C3 1.210(6) . ?
O2 C3 1.373(6) . ?
O2 C4 1.386(6) . ?
N1 C4 1.347(7) . ?
N1 C6 1.326(7) . ?
C1 H1 0.9800 . ?
C1 C2 1.561(7) . ?
C1 C5 1.492(7) . ?
C1 C13 1.517(7) . ?
C2 H2 0.9800 . ?
C2 C3 1.497(7) . ?
C2 C19 1.524(7) . ?
C4 C5 1.351(7) . ?
C6 C7 1.469(7) . ?
C7 C8 1.394(8) . ?
C7 C12 1.389(8) . ?
C8 H8 0.9300 . ?
C8 C9 1.377(9) . ?
C9 H9 0.9300 . ?
C9 C10 1.369(10) . ?
C10 H10 0.9300 . ?
C10 C11 1.390(9) . ?
C11 H11 0.9300 . ?
C11 C12 1.384(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.394(7) . ?
C13 C18 1.390(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.374(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.359(9) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(9) . ?
C17 H17 0.9300 . ?
C17 C18 1.369(7) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.520(8) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C5 S1 C6 90.0(2) . . ?
C3 O2 C4 117.2(4) . . ?
C6 N1 C4 108.1(4) . . ?
C2 C1 H1 108.0 . . ?
C5 C1 H1 108.0 . . ?
C5 C1 C2 106.6(4) . . ?
C5 C1 C13 111.4(4) . . ?
C13 C1 H1 108.0 . . ?
C13 C1 C2 114.6(4) . . ?
C1 C2 H2 105.6 . . ?
C3 C2 C1 113.1(4) . . ?
C3 C2 H2 105.6 . . ?
C3 C2 C19 110.8(4) . . ?
C19 C2 C1 115.2(4) . . ?
C19 C2 H2 105.6 . . ?
O1 C3 O2 115.2(5) . . ?
O1 C3 C2 124.8(5) . . ?
O2 C3 C2 119.9(5) . . ?
N1 C4 O2 115.7(4) . . ?
N1 C4 C5 120.1(5) . . ?
C5 C4 O2 124.1(5) . . ?
C1 C5 S1 129.1(3) . . ?
C4 C5 S1 107.5(4) . . ?
C4 C5 C1 123.3(4) . . ?
N1 C6 S1 114.2(4) . . ?
N1 C6 C7 124.1(5) . . ?
C7 C6 S1 121.6(4) . . ?
C8 C7 C6 119.7(5) . . ?
C12 C7 C6 121.4(5) . . ?
C12 C7 C8 118.9(5) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.3(6) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.5(6) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.3(6) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.3(6) . . ?
C12 C11 H11 120.3 . . ?
C7 C12 H12 119.6 . . ?
C11 C12 C7 120.7(6) . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C1 121.6(4) . . ?
C18 C13 C1 121.6(4) . . ?
C18 C13 C14 116.8(4) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.4(5) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.2(5) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 H16 120.9 . . ?
C15 C16 C17 118.1(5) . . ?
C17 C16 H16 120.9 . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.5(5) . . ?
C18 C17 H17 119.2 . . ?
C13 C18 H18 119.5 . . ?
C17 C18 C13 120.9(5) . . ?
C17 C18 H18 119.5 . . ?
C2 C19 H19A 108.7 . . ?
C2 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C20 C19 C2 114.2(5) . . ?
C20 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C6 C7 C8 170.8(4) . . . . ?
S1 C6 C7 C12 -6.7(7) . . . . ?
O2 C4 C5 S1 177.2(4) . . . . ?
O2 C4 C5 C1 0.8(8) . . . . ?
N1 C4 C5 S1 2.5(6) . . . . ?
N1 C4 C5 C1 -173.9(4) . . . . ?
N1 C6 C7 C8 -5.7(7) . . . . ?
N1 C6 C7 C12 176.8(5) . . . . ?
C1 C2 C3 O1 142.9(5) . . . . ?
C1 C2 C3 O2 -40.4(6) . . . . ?
C1 C2 C19 C20 59.1(6) . . . . ?
C1 C13 C14 C15 178.6(5) . . . . ?
C1 C13 C18 C17 179.8(5) . . . . ?
C2 C1 C5 S1 157.6(4) . . . . ?
C2 C1 C5 C4 -26.8(6) . . . . ?
C2 C1 C13 C14 -107.1(5) . . . . ?
C2 C1 C13 C18 73.6(6) . . . . ?
C3 O2 C4 N1 -176.9(4) . . . . ?
C3 O2 C4 C5 8.2(7) . . . . ?
C3 C2 C19 C20 -171.0(5) . . . . ?
C4 O2 C3 O1 -170.1(5) . . . . ?
C4 O2 C3 C2 13.0(7) . . . . ?
C4 N1 C6 S1 -0.8(5) . . . . ?
C4 N1 C6 C7 175.9(4) . . . . ?
C5 S1 C6 N1 1.8(4) . . . . ?
C5 S1 C6 C7 -175.0(4) . . . . ?
C5 C1 C2 C3 43.6(5) . . . . ?
C5 C1 C2 C19 172.4(4) . . . . ?
C5 C1 C13 C14 131.8(5) . . . . ?
C5 C1 C13 C18 -47.5(6) . . . . ?
C6 S1 C5 C1 173.8(4) . . . . ?
C6 S1 C5 C4 -2.3(4) . . . . ?
C6 N1 C4 O2 -176.3(4) . . . . ?
C6 N1 C4 C5 -1.2(6) . . . . ?
C6 C7 C8 C9 -177.5(5) . . . . ?
C6 C7 C12 C11 176.2(5) . . . . ?
C7 C8 C9 C10 1.5(10) . . . . ?
C8 C7 C12 C11 -1.3(8) . . . . ?
C8 C9 C10 C11 -1.9(10) . . . . ?
C9 C10 C11 C12 0.6(10) . . . . ?
C10 C11 C12 C7 1.0(9) . . . . ?
C12 C7 C8 C9 0.0(8) . . . . ?
C13 C1 C2 C3 -80.1(5) . . . . ?
C13 C1 C2 C19 48.6(5) . . . . ?
C13 C1 C5 S1 -76.7(5) . . . . ?
C13 C1 C5 C4 98.9(5) . . . . ?
C13 C14 C15 C16 1.7(9) . . . . ?
C14 C13 C18 C17 0.6(8) . . . . ?
C14 C15 C16 C17 0.4(9) . . . . ?
C15 C16 C17 C18 -2.0(10) . . . . ?
C16 C17 C18 C13 1.5(9) . . . . ?
C18 C13 C14 C15 -2.1(8) . . . . ?
C19 C2 C3 O1 11.9(8) . . . . ?
C19 C2 C3 O2 -171.4(4) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: PE and EA'
