# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1409744'
_audit_update_record             
;
2015-06-30 deposited with the CCDC.
2015-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H8 O2, C H4 N2 S'
_chemical_formula_sum            'C15 H12 N2 O2 S'
_chemical_formula_weight         284.33

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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.9816(9)
_cell_length_b                   13.5266(6)
_cell_length_c                   8.5608(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1387.45(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    295
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prisms
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.77
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.32
_exptl_absorpt_coefficient_mu    0.235
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      295
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6783
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.200
_diffrn_reflns_theta_max         26.990
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1502
_reflns_number_gt                958
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0606P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1502
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0984
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_restrained_S_all      0.946
_refine_ls_shift/su_max          0.001
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.09584(13) 0.98618(10) -0.14389(18) 0.0509(4) Uani 1 1 d . . . . .
C2 C -0.05080(12) 0.89763(9) -0.20202(18) 0.0483(4) Uani 1 1 d . . . . .
C3 C -0.10720(16) 0.81060(11) -0.1634(2) 0.0683(5) Uani 1 1 d . . . . .
H3 H -0.0818 0.7507 -0.2030 0.082 Uiso 1 1 calc R U . . .
C4 C -0.19954(18) 0.81186(14) -0.0680(3) 0.0858(6) Uani 1 1 d . . . . .
H4 H -0.2354 0.7527 -0.0444 0.103 Uiso 1 1 calc R U . . .
C5 C -0.23968(16) 0.89823(16) -0.0073(2) 0.0855(6) Uani 1 1 d . . . . .
H5 H -0.3010 0.8978 0.0593 0.103 Uiso 1 1 calc R U . . .
C6 C -0.18837(16) 0.98574(13) -0.0460(2) 0.0697(5) Uani 1 1 d . . . . .
H6 H -0.2157 1.0450 -0.0064 0.084 Uiso 1 1 calc R U . . .
C7 C -0.04588(13) 1.08112(10) -0.1884(2) 0.0551(4) Uani 1 1 d . . . . .
C8 C 0.0000 0.58159(14) 0.2500 0.0475(5) Uani 1 2 d S T P . .
N1 N -0.02004(14) 0.63191(11) 0.12128(16) 0.0664(5) Uani 1 1 d . . . . .
O1 O -0.07533(11) 1.15966(7) -0.13307(14) 0.0806(4) Uani 1 1 d . . . . .
S1 S 0.0000 0.45628(4) 0.2500 0.0635(3) Uani 1 2 d S T P . .
H1A H -0.0224(11) 0.6007(10) 0.030(2) 0.055(4) Uiso 1 1 d . . . . .
H1B H -0.0163(14) 0.6935(15) 0.125(2) 0.071(5) Uiso 1 1 d . . . . .

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
C1 0.0463(10) 0.0441(8) 0.0622(9) 0.0010(7) -0.0080(8) 0.0028(7)
C2 0.0478(10) 0.0345(7) 0.0627(9) 0.0035(6) -0.0150(7) -0.0026(6)
C3 0.0667(13) 0.0442(9) 0.0940(13) 0.0065(8) -0.0098(11) -0.0082(8)
C4 0.0696(15) 0.0740(12) 0.1138(16) 0.0209(11) -0.0036(12) -0.0264(11)
C5 0.0573(13) 0.1001(14) 0.0991(15) 0.0146(12) 0.0096(12) -0.0082(10)
C6 0.0582(12) 0.0703(10) 0.0804(12) -0.0007(9) -0.0019(10) 0.0077(8)
C7 0.0627(12) 0.0350(8) 0.0676(9) -0.0014(7) -0.0126(7) 0.0056(6)
C8 0.0651(15) 0.0364(10) 0.0411(10) 0.000 0.0007(10) 0.000
N1 0.1234(15) 0.0327(7) 0.0430(8) 0.0042(6) -0.0020(7) 0.0057(7)
O1 0.0992(11) 0.0415(6) 0.1011(10) -0.0109(6) 0.0041(8) 0.0132(6)
S1 0.1161(6) 0.0314(3) 0.0428(3) 0.000 -0.0129(3) 0.000

_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
C1 C6 1.390(2) . ?
C1 C2 1.4048(19) . ?
C1 C7 1.467(2) . ?
C2 C3 1.397(2) . ?
C2 C2 1.469(3) 3_554 ?
C3 C4 1.375(3) . ?
C4 C5 1.366(3) . ?
C5 C6 1.374(3) . ?
C7 O1 1.2154(17) . ?
C7 C7 1.524(3) 3_554 ?
C8 N1 1.3173(15) . ?
C8 N1 1.3173(15) 3 ?
C8 S1 1.6949(19) . ?

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
C6 C1 C2 121.09(14) . . ?
C6 C1 C7 119.05(14) . . ?
C2 C1 C7 119.85(15) . . ?
C3 C2 C1 116.68(15) . . ?
C3 C2 C2 122.22(10) . 3_554 ?
C1 C2 C2 121.10(9) . 3_554 ?
C4 C3 C2 121.27(16) . . ?
C5 C4 C3 121.31(16) . . ?
C4 C5 C6 119.19(19) . . ?
C5 C6 C1 120.38(18) . . ?
O1 C7 C1 123.08(16) . . ?
O1 C7 C7 118.62(10) . 3_554 ?
C1 C7 C7 118.29(9) . 3_554 ?
N1 C8 N1 117.8(2) . 3 ?
N1 C8 S1 121.11(10) . . ?
N1 C8 S1 121.11(10) 3 . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.035

_shelxl_version_number           2013-4

_shelx_res_file                  
;
TITL PROFF_MMM_SMART_FY in Pbcn
CELL  0.71073  11.9816  13.5266   8.5608   90.000   90.000   90.000
ZERR     4.00   0.0009   0.0006   0.0004    0.000    0.000    0.000
LATT   1
SYMM  1/2 - X, 1/2 - Y, 1/2 + Z
SYMM  - X,   Y, 1/2 - Z
SYMM  1/2 + X, 1/2 - Y, - Z
SFAC  C    H    N    O    S
UNIT  60   48   8    8    4
MERG   2
OMIT    -1.00  54.00
FMAP   2
PLAN   20
ACTA
BOND
L.S.   9
WGHT    0.060600
FVAR       9.54860
MOLE    1
C1    1   -0.095836    0.986177   -0.143894    11.00000    0.04634    0.04415 =
         0.06216    0.00105   -0.00804    0.00280
C2    1   -0.050798    0.897627   -0.202016    11.00000    0.04779    0.03451 =
         0.06268    0.00349   -0.01500   -0.00260
C3    1   -0.107204    0.810596   -0.163445    11.00000    0.06671    0.04425 =
         0.09399    0.00649   -0.00983   -0.00822
AFIX  43
H3    2   -0.081826    0.750650   -0.203046    11.00000   -1.20000
AFIX   0
C4    1   -0.199544    0.811865   -0.068034    11.00000    0.06960    0.07403 =
         0.11383    0.02093   -0.00358   -0.02636
AFIX  43
H4    2   -0.235375    0.752744   -0.044362    11.00000   -1.20000
AFIX   0
C5    1   -0.239676    0.898231   -0.007348    11.00000    0.05732    0.10014 =
         0.09906    0.01459    0.00957   -0.00817
AFIX  43
H5    2   -0.300969    0.897814    0.059301    11.00000   -1.20000
AFIX   0
C6    1   -0.188373    0.985737   -0.045984    11.00000    0.05823    0.07032 =
         0.08043   -0.00066   -0.00195    0.00769
AFIX  43
H6    2   -0.215724    1.045002   -0.006395    11.00000   -1.20000
AFIX   0
C7    1   -0.045884    1.081116   -0.188357    11.00000    0.06274    0.03502 =
         0.06762   -0.00139   -0.01260    0.00563
C8    1    0.000000    0.581586    0.250000    10.50000    0.06508    0.03635 =
         0.04112    0.00000    0.00066    0.00000
N1    3   -0.020037    0.631909    0.121280    11.00000    0.12336    0.03269 =
         0.04302    0.00424   -0.00202    0.00569
O1    4   -0.075328    1.159662   -0.133074    11.00000    0.09923    0.04146 =
         0.10108   -0.01094    0.00412    0.01318
S1    5    0.000000    0.456282    0.250000    10.50000    0.11614    0.03138 =
         0.04284    0.00000   -0.01288    0.00000
MOLE    0
H1A   2   -0.022447    0.600723    0.030497    11.00000    0.05530
H1B   2   -0.016255    0.693498    0.125113    11.00000    0.07114
HKLF    4

REM  PROFF_MMM_SMART_FY in Pbcn
REM R1 =  0.0370 for     958 Fo > 4sig(Fo)  and  0.0622 for all    1502 data
REM    100 parameters refined using      0 restraints

END

WGHT      0.0605      0.0000

REM Highest difference peak  0.212,  deepest hole -0.185,  1-sigma level  0.035
Q1    1   0.0000  0.5336  0.2500  10.50000  0.05    0.18
Q2    1  -0.1010  1.1721 -0.2386  11.00000  0.05    0.14
Q3    1  -0.0811  0.9390 -0.2000  11.00000  0.05    0.12
Q4    1  -0.0555  0.9403 -0.1607  11.00000  0.05    0.12
Q5    1  -0.0574  0.8557 -0.1501  11.00000  0.05    0.12
Q6    1  -0.1464  0.9127 -0.3362  11.00000  0.05    0.12
Q7    1  -0.0693  1.0166 -0.1667  11.00000  0.05    0.12
Q8    1   0.0081  0.8914 -0.2114  11.00000  0.05    0.11
Q9    1  -0.0205  0.4530  0.1277  11.00000  0.05    0.10
Q10   1  -0.0648  0.7390 -0.2673  11.00000  0.05    0.10
Q11   1   0.0064  0.4307  0.1513  11.00000  0.05    0.10
Q12   1  -0.1171  1.0159  0.1209  11.00000  0.05    0.10
Q13   1   0.0054  0.5978  0.3080  11.00000  0.05    0.10
Q14   1  -0.0597  0.4906  0.2426  11.00000  0.05    0.10
Q15   1  -0.1989  1.0689  0.0525  11.00000  0.05    0.09
Q16   1  -0.0862  0.8720 -0.2282  11.00000  0.05    0.09
Q17   1   0.0000  1.0728 -0.2500  10.50000  0.05    0.09
Q18   1  -0.1596  1.0388 -0.3280  11.00000  0.05    0.09
Q19   1  -0.1414  0.9512  0.1494  11.00000  0.05    0.09
Q20   1  -0.3250  0.7112  0.1008  11.00000  0.05    0.08
;
_shelx_res_checksum              87295

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
