# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_F4_23_iper2
_database_code_depnum_ccdc_archive 'CCDC 1553610'
_audit_update_record             
;
2017-06-01 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date             2015-01-16
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;

_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H6 F4 O4 S'
_chemical_formula_sum            'C13 H6 F4 O4 S'
_chemical_formula_weight         334.24
_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'
F F 0.0171 0.0103 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   6.2517(5)
_cell_length_b                   7.3716(5)
_cell_length_c                   26.471(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1219.94(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9868
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.51
_cell_measurement_theta_min      2.87
_exptl_absorpt_coefficient_mu    0.335
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1018 before and 0.0401 after correction.
The Ratio of minimum to maximum transmission is 0.9350.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            25897
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.87
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  D8Venture
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'ImuS microsource'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                3439
_reflns_number_total             3576
_reflns_threshold_expression     >2sigma(I)
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_coef       0.0053(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3576
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0259
_refine_ls_restrained_S_all      1.071
_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)+(0.0400P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0677
_refine_ls_wR_factor_ref         0.0690
_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    
;
;
_atom_sites_solution_hydrogens   difmap
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.78709(5) 0.73953(4) 0.643995(11) 0.01434(7) Uani 1 d . . .
F1 F 0.79935(16) 0.09575(10) 0.47316(3) 0.01750(16) Uani 1 d . . .
F2 F 0.79837(15) 0.14943(10) 0.37131(3) 0.01872(16) Uani 1 d . . .
F3 F 0.78595(15) 0.49207(10) 0.33373(3) 0.01918(16) Uani 1 d . . .
F4 F 0.77718(14) 0.78054(9) 0.39773(3) 0.01568(15) Uani 1 d . . .
O1 O 0.78930(18) 0.37217(11) 0.53854(3) 0.01383(17) Uani 1 d . . .
O2 O 0.77316(16) 0.73883(12) 0.49786(3) 0.01416(17) Uani 1 d . . .
O3 O 0.83210(17) 0.40805(13) 0.70153(3) 0.0177(2) Uani 1 d . . .
O4 O 0.81289(17) 0.20642(13) 0.63758(3) 0.0190(2) Uani 1 d . . .
C1 C 0.7919(2) 0.52099(16) 0.62036(4) 0.0128(2) Uani 1 d . . .
C2 C 0.7861(2) 0.52396(15) 0.56869(4) 0.0116(2) Uani 1 d . . .
C3 C 0.7787(2) 0.70206(15) 0.54889(4) 0.0114(2) Uani 1 d . . .
C4 C 0.7786(2) 0.83338(16) 0.58486(4) 0.0137(2) Uani 1 d . . .
C5 C 0.7886(2) 0.41067(16) 0.48740(4) 0.0113(2) Uani 1 d . . .
C6 C 0.7943(2) 0.26465(15) 0.45456(4) 0.0122(2) Uani 1 d . . .
C7 C 0.7937(2) 0.29124(15) 0.40279(4) 0.0129(2) Uani 1 d . . .
C8 C 0.7872(2) 0.46535(17) 0.38379(4) 0.0130(2) Uani 1 d . . .
C9 C 0.7814(2) 0.61207(15) 0.41632(4) 0.0121(2) Uani 1 d . . .
C10 C 0.7810(2) 0.58598(15) 0.46819(4) 0.0109(2) Uani 1 d . . .
C11 C 0.8114(2) 0.36050(17) 0.65290(4) 0.0137(2) Uani 1 d . . .
C12 C 0.8737(2) 0.2605(2) 0.73715(5) 0.0209(3) Uani 1 d . . .
C13 C 0.6730(3) 0.1642(2) 0.75216(6) 0.0292(3) Uani 1 d . . .
H4 H 0.776(3) 0.957(3) 0.5802(7) 0.027(5) Uiso 1 d . . .
H12A H 0.942(3) 0.317(3) 0.7656(6) 0.019(4) Uiso 1 d . . .
H12B H 0.977(4) 0.179(3) 0.7213(8) 0.042(6) Uiso 1 d . . .
H13A H 0.710(4) 0.076(3) 0.7786(8) 0.034(5) Uiso 1 d . . .
H13B H 0.567(4) 0.236(3) 0.7643(8) 0.040(6) Uiso 1 d . . .
H13C H 0.608(4) 0.096(3) 0.7245(8) 0.038(6) Uiso 1 d . . .


_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 C1 1.7285(12) . ?
S1 C4 1.7124(13) . ?
F1 C6 1.3393(13) . ?
F2 C7 1.3371(13) . ?
F3 C8 1.3397(13) . ?
F4 C9 1.3361(12) . ?
O1 C2 1.3745(13) . ?
O1 C5 1.3832(13) . ?
O2 C3 1.3781(14) . ?
O2 C10 1.3744(13) . ?
O3 C11 1.3405(14) . ?
O3 C12 1.4626(17) . ?
O4 C11 1.2060(16) . ?
C1 C2 1.3684(15) . ?
C1 C11 1.4685(17) . ?
C2 C3 1.4144(16) . ?
C3 C4 1.3579(16) . ?
C4 H4 0.92(2) . ?
C5 C6 1.3841(15) . ?
C5 C10 1.3896(16) . ?
C6 C7 1.3844(15) . ?
C7 C8 1.3791(16) . ?
C8 C9 1.3829(16) . ?
C9 C10 1.3864(16) . ?
C12 C13 1.495(2) . ?
C12 H12A 0.962(18) . ?
C12 H12B 0.98(2) . ?
C13 H13A 0.98(2) . ?
C13 H13B 0.91(2) . ?
C13 H13C 0.98(2) . ?

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
C4 S1 C1 92.65(6) . . ?
C2 O1 C5 113.65(9) . . ?
C10 O2 C3 113.45(9) . . ?
C11 O3 C12 116.22(10) . . ?
C2 C1 S1 110.27(9) . . ?
C2 C1 C11 126.97(11) . . ?
C11 C1 S1 122.69(9) . . ?
O1 C2 C3 122.74(10) . . ?
C1 C2 O1 124.54(10) . . ?
C1 C2 C3 112.72(10) . . ?
O2 C3 C2 123.14(10) . . ?
C4 C3 O2 123.17(11) . . ?
C4 C3 C2 113.69(10) . . ?
S1 C4 H4 121.6(12) . . ?
C3 C4 S1 110.67(9) . . ?
C3 C4 H4 127.7(12) . . ?
O1 C5 C6 117.07(10) . . ?
O1 C5 C10 123.31(10) . . ?
C6 C5 C10 119.62(10) . . ?
F1 C6 C5 119.52(10) . . ?
F1 C6 C7 119.71(10) . . ?
C5 C6 C7 120.77(10) . . ?
F2 C7 C6 120.41(10) . . ?
F2 C7 C8 120.07(10) . . ?
C8 C7 C6 119.52(10) . . ?
F3 C8 C7 119.85(11) . . ?
F3 C8 C9 120.04(11) . . ?
C7 C8 C9 120.11(10) . . ?
F4 C9 C8 119.88(10) . . ?
F4 C9 C10 119.59(10) . . ?
C8 C9 C10 120.54(10) . . ?
O2 C10 C5 123.67(10) . . ?
O2 C10 C9 116.89(10) . . ?
C9 C10 C5 119.44(10) . . ?
O3 C11 C1 111.14(10) . . ?
O4 C11 O3 124.64(12) . . ?
O4 C11 C1 124.21(11) . . ?
O3 C12 C13 112.03(13) . . ?
O3 C12 H12A 105.0(11) . . ?
O3 C12 H12B 107.2(13) . . ?
C13 C12 H12A 111.9(11) . . ?
C13 C12 H12B 112.4(14) . . ?
H12A C12 H12B 107.9(17) . . ?
C12 C13 H13A 107.6(13) . . ?
C12 C13 H13B 115.6(16) . . ?
C12 C13 H13C 113.3(13) . . ?
H13A C13 H13B 107.7(17) . . ?
H13A C13 H13C 107.1(17) . . ?
H13B C13 H13C 105.2(19) . . ?

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
C1 C11 O3 C12 -174.29(11) . . . . ?
C12 O3 C11 O4 4.3(2) . . . . ?
C13 C12 O3 C11 -82.03(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_5CF3_PyDOT_iper7
_database_code_depnum_ccdc_archive 'CCDC 1553617'
_audit_update_record             
;
2017-06-01 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date             2015-01-22
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;

_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H4 F3 N O2 S'
_chemical_formula_sum            'C10 H4 F3 N O2 S'
_chemical_formula_weight         259.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H4 F3 N1 S1 O2'
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'
F F 0.0171 0.0103 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.0124(2)
_cell_length_b                   22.0636(7)
_cell_length_c                   7.2454(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.282(3)
_cell_angle_gamma                90.00
_cell_volume                     953.39(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4389
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      31.5370
_cell_measurement_theta_min      3.3710
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.806
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            14144
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.85
_diffrn_ambient_temperature      120.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   68.00   94.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  178.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega   56.00   98.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000   60.0000 42

#__ type_ start__ end____ width___ exp.time_
  3 omega   52.00   78.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  178.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -22.00   69.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000  -90.0000 91

#__ type_ start__ end____ width___ exp.time_
  5 omega    1.00   70.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000   30.0000 69

#__ type_ start__ end____ width___ exp.time_
  6 omega  -36.00   89.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587    0.0000 -120.0000 125

#__ type_ start__ end____ width___ exp.time_
  7 omega    9.00   71.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000  150.0000 62

#__ type_ start__ end____ width___ exp.time_
  8 omega   -1.00   99.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000 -150.0000 100

#__ type_ start__ end____ width___ exp.time_
  9 omega    9.00   61.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000   30.0000 52

#__ type_ start__ end____ width___ exp.time_
 10 omega    9.00   98.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000  -30.0000 89
;
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ω-scan
_diffrn_orient_matrix_UB_11      0.0063332000
_diffrn_orient_matrix_UB_12      0.0320306000
_diffrn_orient_matrix_UB_13      -0.0060327000
_diffrn_orient_matrix_UB_21      0.0033849000
_diffrn_orient_matrix_UB_22      0.0021539000
_diffrn_orient_matrix_UB_23      0.0979821000
_diffrn_orient_matrix_UB_31      0.1187161000
_diffrn_orient_matrix_UB_32      -0.0017602000
_diffrn_orient_matrix_UB_33      0.0100506000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2066
_reflns_number_total             2527
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2527
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.044
_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)+(0.0350P)²+0.3500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0864
_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    
;
;
_atom_sites_solution_hydrogens   difmap
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S -0.15100(7) 0.647205(18) 0.11800(6) 0.02100(12) Uani 1 d . . .
F1 F 0.19808(17) 0.24041(4) 0.47498(15) 0.0292(3) Uani 1 d . . .
F2 F 0.47939(16) 0.30048(5) 0.55201(15) 0.0278(2) Uani 1 d . . .
F3 F 0.39991(17) 0.27102(5) 0.26764(14) 0.0274(2) Uani 1 d . . .
O1 O 0.18497(18) 0.50642(5) 0.32113(18) 0.0220(3) Uani 1 d . . .
O2 O -0.28312(18) 0.47754(5) 0.19870(17) 0.0209(3) Uani 1 d . . .
N1 N -0.2138(2) 0.37926(6) 0.27169(19) 0.0184(3) Uani 1 d . . .
C1 C 0.0828(3) 0.60874(7) 0.2181(2) 0.0198(3) Uani 1 d . . .
C2 C 0.0330(3) 0.54933(7) 0.2430(2) 0.0170(3) Uani 1 d . . .
C3 C -0.1957(3) 0.53522(7) 0.1826(2) 0.0171(3) Uani 1 d . . .
C4 C -0.3166(3) 0.58339(7) 0.1099(2) 0.0201(3) Uani 1 d . . .
C5 C 0.0995(3) 0.44797(7) 0.3185(2) 0.0164(3) Uani 1 d . . .
C6 C 0.2441(3) 0.40082(7) 0.3738(2) 0.0175(3) Uani 1 d . . .
C7 C 0.1554(3) 0.34244(7) 0.3772(2) 0.0169(3) Uani 1 d . . .
C8 C -0.0734(3) 0.33375(7) 0.3288(2) 0.0180(3) Uani 1 d . . .
C9 C -0.1280(2) 0.43431(7) 0.2646(2) 0.0165(3) Uani 1 d . . .
C10 C 0.3070(3) 0.28908(7) 0.4188(2) 0.0196(3) Uani 1 d . . .
H1 H 0.223(3) 0.6292(9) 0.249(3) 0.029(5) Uiso 1 d . . .
H4 H -0.468(3) 0.5844(9) 0.053(3) 0.031(5) Uiso 1 d . . .
H6 H 0.401(3) 0.4095(9) 0.407(3) 0.031(5) Uiso 1 d . . .
H8 H -0.135(3) 0.2942(9) 0.334(3) 0.027(5) Uiso 1 d . . .


_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 C1 1.7214(17) . ?
S1 C4 1.7210(17) . ?
F1 C10 1.3474(18) . ?
F2 C10 1.3472(19) . ?
F3 C10 1.3509(18) . ?
O1 C2 1.3857(19) . ?
O1 C5 1.3876(18) . ?
O2 C3 1.3873(18) . ?
O2 C9 1.3764(18) . ?
N1 C8 1.343(2) . ?
N1 C9 1.3230(19) . ?
C1 C2 1.362(2) . ?
C1 H1 0.96(2) . ?
C2 C3 1.424(2) . ?
C3 C4 1.356(2) . ?
C4 H4 0.95(2) . ?
C5 C6 1.382(2) . ?
C5 C9 1.407(2) . ?
C6 C7 1.396(2) . ?
C6 H6 0.97(2) . ?
C7 C8 1.389(2) . ?
C7 C10 1.496(2) . ?
C8 H8 0.950(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
C4 S1 C1 92.80(8) . . ?
C2 O1 C5 113.93(12) . . ?
C9 O2 C3 114.69(12) . . ?
C9 N1 C8 117.76(13) . . ?
S1 C1 H1 120.9(12) . . ?
C2 C1 S1 110.43(12) . . ?
C2 C1 H1 128.7(12) . . ?
O1 C2 C3 122.51(14) . . ?
C1 C2 O1 124.56(14) . . ?
C1 C2 C3 112.93(15) . . ?
O2 C3 C2 122.41(14) . . ?
C4 C3 O2 124.19(14) . . ?
C4 C3 C2 113.40(14) . . ?
S1 C4 H4 120.9(12) . . ?
C3 C4 S1 110.43(12) . . ?
C3 C4 H4 128.5(12) . . ?
O1 C5 C9 123.24(14) . . ?
C6 C5 O1 118.53(14) . . ?
C6 C5 C9 118.23(14) . . ?
C5 C6 C7 118.18(14) . . ?
C5 C6 H6 118.9(12) . . ?
C7 C6 H6 122.9(12) . . ?
C6 C7 C10 120.35(14) . . ?
C8 C7 C6 119.43(14) . . ?
C8 C7 C10 120.07(14) . . ?
N1 C8 C7 122.55(15) . . ?
N1 C8 H8 117.7(12) . . ?
C7 C8 H8 119.7(12) . . ?
O2 C9 C5 122.69(14) . . ?
N1 C9 O2 113.55(13) . . ?
N1 C9 C5 123.77(14) . . ?
F1 C10 F3 106.06(13) . . ?
F1 C10 C7 112.37(13) . . ?
F2 C10 F1 106.96(13) . . ?
F2 C10 F3 106.05(12) . . ?
F2 C10 C7 113.03(14) . . ?
F3 C10 C7 111.88(13) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 -1 0 0.0377 -0.0001 -1.0007 -0.0001 -0.0321 -0.0022 0.0017
0 1 0 0.0377 0.0001 1.0007 0.0001 0.0321 0.0022 -0.0017
1 0 0 0.0935 0.9991 -0.0000 -0.0005 0.0063 0.0033 0.1186
-1 0 -2 0.1051 -1.0006 -0.0013 -2.0001 0.0057 -0.1994 -0.1389
-1 0 1 0.0626 -0.9984 0.0007 1.0008 -0.0123 0.0947 -0.1085
0 0 -1 0.1131 -0.0007 -0.0007 -1.0003 0.0060 -0.0980 -0.0101

_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_56Cl2_PyDOT_iper6
_database_code_depnum_ccdc_archive 'CCDC 1553615'
_audit_update_record             
;
2017-06-01 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date             2015-01-20
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;

_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C9 H3 Cl2 N O2 S'
_chemical_formula_sum            'C9 H3 Cl2 N O2 S'
_chemical_formula_weight         260.08
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 H3 N1 O2 Cl2 S1'
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'
Cl Cl 0.1484 0.1585 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.0302(5)
_cell_length_b                   5.89058(13)
_cell_length_c                   18.9311(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.094(3)
_cell_angle_gamma                90.00
_cell_volume                     1888.26(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5586
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      32.5030
_cell_measurement_theta_min      2.2630
_exptl_absorpt_coefficient_mu    0.880
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.830
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.2578
_exptl_crystal_size_mid          0.2007
_exptl_crystal_size_min          0.0329
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            14968
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.29
_diffrn_ambient_temperature      120.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -68.00  -34.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  106.0000 -132.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega   45.00   84.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -178.0000  -60.0000 39

#__ type_ start__ end____ width___ exp.time_
  3 omega   16.00   71.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000   30.0000 55

#__ type_ start__ end____ width___ exp.time_
  4 omega   46.00   71.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega  -29.00   45.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  -57.0000  -90.0000 74

#__ type_ start__ end____ width___ exp.time_
  6 omega   13.00   95.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   57.0000  150.0000 82

#__ type_ start__ end____ width___ exp.time_
  7 omega  -44.00   73.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  -19.0000  -30.0000 117

#__ type_ start__ end____ width___ exp.time_
  8 omega  -97.00   -7.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  -57.0000  -90.0000 90

#__ type_ start__ end____ width___ exp.time_
  9 omega -104.00  -35.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337 -178.0000   30.0000 69

#__ type_ start__ end____ width___ exp.time_
 10 omega  -98.00  -73.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  -77.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 11 omega  -98.00    2.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  -77.0000   30.0000 100
;
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0237448000
_diffrn_orient_matrix_UB_12      -0.0058001000
_diffrn_orient_matrix_UB_13      -0.0385762000
_diffrn_orient_matrix_UB_21      -0.0122032000
_diffrn_orient_matrix_UB_22      0.1138820000
_diffrn_orient_matrix_UB_23      0.0014484000
_diffrn_orient_matrix_UB_31      0.0322738000
_diffrn_orient_matrix_UB_32      0.0387806000
_diffrn_orient_matrix_UB_33      -0.0100487000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2383
_reflns_number_total             2764
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2764
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0309
_refine_ls_restrained_S_all      1.048
_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)+(0.0330P)²+0.9500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0743
_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    
;
;
_atom_sites_solution_hydrogens   difmap
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.25620(2) 0.37629(7) 0.68811(2) 0.02064(10) Uani 1 d . . .
Cl2 Cl 0.36123(2) -0.06984(6) 0.70183(2) 0.02406(10) Uani 1 d . . .
S1 S 0.45845(2) 0.54509(7) 0.33112(2) 0.02069(10) Uani 1 d . . .
O1 O 0.33801(6) 0.58976(18) 0.46560(6) 0.0194(2) Uani 1 d . . .
O2 O 0.42323(7) 0.16319(18) 0.48350(6) 0.0221(2) Uani 1 d . . .
N1 N 0.38631(8) 0.0805(2) 0.58282(7) 0.0179(3) Uani 1 d . . .
C1 C 0.39726(9) 0.6744(3) 0.37157(9) 0.0199(3) Uani 1 d . . .
C2 C 0.38595(8) 0.5373(2) 0.42424(8) 0.0161(3) Uani 1 d . . .
C3 C 0.42726(9) 0.3283(3) 0.43289(8) 0.0170(3) Uani 1 d . . .
C4 C 0.46990(9) 0.3076(3) 0.38672(9) 0.0193(3) Uani 1 d . . .
C5 C 0.34166(8) 0.4332(2) 0.52092(8) 0.0155(3) Uani 1 d . . .
C6 C 0.30186(8) 0.4801(3) 0.56993(8) 0.0169(3) Uani 1 d . . .
C7 C 0.30554(8) 0.3242(2) 0.62641(8) 0.0158(3) Uani 1 d . . .
C8 C 0.34954(9) 0.1278(2) 0.63084(8) 0.0166(3) Uani 1 d . . .
C9 C 0.38279(8) 0.2278(2) 0.52940(8) 0.0164(3) Uani 1 d . . .
H1 H 0.3758(11) 0.818(3) 0.3559(11) 0.030(5) Uiso 1 d . . .
H4 H 0.5043(11) 0.185(3) 0.3856(11) 0.027(5) Uiso 1 d . . .
H6 H 0.2716(11) 0.620(3) 0.5645(11) 0.026(5) Uiso 1 d . . .


_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
Cl1 C7 1.7215(15) . ?
Cl2 C8 1.7354(15) . ?
S1 C1 1.7218(16) . ?
S1 C4 1.7201(16) . ?
O1 C2 1.3861(17) . ?
O1 C5 1.3799(17) . ?
O2 C3 1.3845(18) . ?
O2 C9 1.3663(17) . ?
N1 C8 1.3259(19) . ?
N1 C9 1.3172(19) . ?
C1 C2 1.352(2) . ?
C1 H1 0.93(2) . ?
C2 C3 1.419(2) . ?
C3 C4 1.353(2) . ?
C4 H4 0.96(2) . ?
C5 C6 1.382(2) . ?
C5 C9 1.399(2) . ?
C6 C7 1.394(2) . ?
C6 H6 0.977(19) . ?
C7 C8 1.389(2) . ?

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
C4 S1 C1 92.77(8) . . ?
C5 O1 C2 113.77(11) . . ?
C9 O2 C3 114.26(11) . . ?
C9 N1 C8 118.96(13) . . ?
S1 C1 H1 121.2(12) . . ?
C2 C1 S1 110.22(12) . . ?
C2 C1 H1 128.6(12) . . ?
O1 C2 C3 122.20(13) . . ?
C1 C2 O1 124.37(13) . . ?
C1 C2 C3 113.42(13) . . ?
O2 C3 C2 122.62(13) . . ?
C4 C3 O2 124.06(13) . . ?
C4 C3 C2 113.32(14) . . ?
S1 C4 H4 122.9(12) . . ?
C3 C4 S1 110.27(12) . . ?
C3 C4 H4 126.8(12) . . ?
O1 C5 C6 118.38(13) . . ?
O1 C5 C9 123.39(13) . . ?
C6 C5 C9 118.22(13) . . ?
C5 C6 C7 118.98(13) . . ?
C5 C6 H6 120.0(11) . . ?
C7 C6 H6 121.1(11) . . ?
C6 C7 Cl1 120.23(11) . . ?
C8 C7 Cl1 121.68(12) . . ?
C8 C7 C6 118.09(13) . . ?
N1 C8 Cl2 115.69(11) . . ?
N1 C8 C7 122.93(14) . . ?
C7 C8 Cl2 121.37(11) . . ?
O2 C9 C5 123.04(13) . . ?
N1 C9 O2 114.17(12) . . ?
N1 C9 C5 122.79(13) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 -1 0.0165 0.0006 0.0002 -1.0004 0.0386 -0.0014 0.0101
0 0 1 0.0165 -0.0006 -0.0002 1.0004 -0.0386 0.0014 -0.0101
1 0 -1 0.0752 0.9999 0.0001 -1.0002 0.0148 -0.0136 0.0423
-1 0 1 0.0752 -0.9999 -0.0001 1.0002 -0.0148 0.0136 -0.0423
1 1 -1 0.1171 0.9998 1.0001 -1.0000 0.0090 0.1002 0.0811
-1 -1 1 0.1171 -0.9998 -1.0001 1.0000 -0.0090 -0.1002 -0.0811
-1 1 0 0.1197 -0.9994 1.0000 0.0001 0.0179 0.1261 0.0065
1 -1 0 0.1197 0.9994 -1.0000 -0.0001 -0.0179 -0.1261 -0.0065

_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_QxDOT_iper3b
_database_code_depnum_ccdc_archive 'CCDC 1553616'
_audit_update_record             
;
2017-06-01 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date             2015-01-19
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;

_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H6 N2 O2 S'
_chemical_formula_sum            'C12 H6 N2 O2 S'
_chemical_formula_weight         242.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H6 N2 O2 S1'
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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.43002(16)
_cell_length_b                   21.1250(7)
_cell_length_c                   10.8195(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.714(3)
_cell_angle_gamma                90.00
_cell_volume                     1011.40(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3195
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      30.8600
_cell_measurement_theta_min      2.0970
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.4031
_exptl_crystal_size_mid          0.0659
_exptl_crystal_size_min          0.0524
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14911
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.93
_diffrn_ambient_temperature      120.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -44.00   38.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337   57.0000   30.0000 82

#__ type_ start__ end____ width___ exp.time_
  2 omega  -99.00   14.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  -19.0000 -150.0000 113

#__ type_ start__ end____ width___ exp.time_
  3 omega  -81.00  -11.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  131.0000   34.0000 70

#__ type_ start__ end____ width___ exp.time_
  4 omega  -98.00  -16.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  -77.0000 -180.0000 82

#__ type_ start__ end____ width___ exp.time_
  5 omega  -80.00  -48.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  178.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
  6 omega   40.00   88.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -131.0000  -35.0000 48

#__ type_ start__ end____ width___ exp.time_
  7 omega -104.00  -35.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337 -178.0000  150.0000 69

#__ type_ start__ end____ width___ exp.time_
  8 omega  -98.00   -3.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  -77.0000  150.0000 95

#__ type_ start__ end____ width___ exp.time_
  9 omega  -97.00   -7.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  -57.0000   30.0000 90
;
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ω-scan
_diffrn_orient_matrix_UB_11      -0.0021687000
_diffrn_orient_matrix_UB_12      -0.0335550000
_diffrn_orient_matrix_UB_13      -0.0023406000
_diffrn_orient_matrix_UB_21      -0.1600654000
_diffrn_orient_matrix_UB_22      0.0003986000
_diffrn_orient_matrix_UB_23      0.0010670000
_diffrn_orient_matrix_UB_31      -0.0101249000
_diffrn_orient_matrix_UB_32      0.0012124000
_diffrn_orient_matrix_UB_33      -0.0655304000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2083
_reflns_number_total             2675
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2675
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.018
_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)+(0.0400P)²+0.4400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.1033
_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    
;
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S -0.64539(11) 0.61004(2) 0.17953(4) 0.01966(13) Uani 1 d . . .
O1 O -0.2889(3) 0.47826(6) 0.38838(11) 0.0198(3) Uani 1 d . . .
O2 O -0.0865(3) 0.47152(6) 0.13815(11) 0.0192(3) Uani 1 d . . .
N1 N 0.0116(3) 0.39538(7) 0.43895(13) 0.0168(3) Uani 1 d . . .
N2 N 0.2072(3) 0.38850(7) 0.19470(13) 0.0171(3) Uani 1 d . . .
C1 C -0.5832(4) 0.56842(8) 0.31482(17) 0.0187(4) Uani 1 d . . .
C2 C -0.3867(4) 0.52076(8) 0.29741(16) 0.0161(4) Uani 1 d . . .
C3 C -0.2877(4) 0.51710(8) 0.17517(16) 0.0164(4) Uani 1 d . . .
C4 C -0.4076(4) 0.56276(9) 0.09935(17) 0.0181(4) Uani 1 d . . .
C5 C -0.0834(4) 0.43423(8) 0.35340(16) 0.0152(3) Uani 1 d . . .
C6 C 0.0161(4) 0.43074(8) 0.22835(16) 0.0160(4) Uani 1 d . . .
C7 C 0.2127(4) 0.34950(8) 0.40583(16) 0.0166(4) Uani 1 d . . .
C8 C 0.3196(4) 0.30488(9) 0.49424(18) 0.0206(4) Uani 1 d . . .
C9 C 0.5166(5) 0.25821(9) 0.46083(19) 0.0240(4) Uani 1 d . . .
C10 C 0.6147(5) 0.25510(9) 0.33936(19) 0.0240(4) Uani 1 d . . .
C11 C 0.5151(4) 0.29835(9) 0.25212(18) 0.0217(4) Uani 1 d . . .
C12 C 0.3110(4) 0.34610(8) 0.28339(16) 0.0166(4) Uani 1 d . . .
H4 H -0.370(5) 0.5708(9) 0.0184(19) 0.017(5) Uiso 1 d . . .
H9 H 0.586(5) 0.2273(10) 0.5182(19) 0.028(6) Uiso 1 d . . .
H8 H 0.251(5) 0.3088(9) 0.576(2) 0.023(5) Uiso 1 d . . .
H11 H 0.580(5) 0.2985(10) 0.167(2) 0.027(6) Uiso 1 d . . .
H1 H -0.680(5) 0.5806(10) 0.387(2) 0.028(6) Uiso 1 d . . .
H10 H 0.756(6) 0.2247(11) 0.322(2) 0.035(7) Uiso 1 d . . .


_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 C1 1.7184(19) . ?
S1 C4 1.7166(19) . ?
O1 C2 1.386(2) . ?
O1 C5 1.367(2) . ?
O2 C3 1.384(2) . ?
O2 C6 1.363(2) . ?
N1 C5 1.292(2) . ?
N1 C7 1.375(2) . ?
N2 C6 1.294(2) . ?
N2 C12 1.376(2) . ?
C1 C2 1.350(3) . ?
C1 H1 0.95(2) . ?
C2 C3 1.415(2) . ?
C3 C4 1.358(2) . ?
C4 H4 0.92(2) . ?
C5 C6 1.444(2) . ?
C7 C8 1.409(2) . ?
C7 C12 1.416(3) . ?
C8 C9 1.376(3) . ?
C8 H8 0.96(2) . ?
C9 C10 1.405(3) . ?
C9 H9 0.94(2) . ?
C10 C11 1.372(3) . ?
C10 H10 0.92(2) . ?
C11 C12 1.407(3) . ?
C11 H11 0.97(2) . ?

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
C4 S1 C1 93.18(9) . . ?
C5 O1 C2 115.71(13) . . ?
C6 O2 C3 115.45(13) . . ?
C5 N1 C7 116.99(15) . . ?
C6 N2 C12 117.01(15) . . ?
S1 C1 H1 120.3(13) . . ?
C2 C1 S1 109.94(14) . . ?
C2 C1 H1 129.8(13) . . ?
O1 C2 C3 121.85(16) . . ?
C1 C2 O1 124.46(16) . . ?
C1 C2 C3 113.68(16) . . ?
O2 C3 C2 122.74(15) . . ?
C4 C3 O2 123.92(16) . . ?
C4 C3 C2 113.33(16) . . ?
S1 C4 H4 121.2(13) . . ?
C3 C4 S1 109.86(14) . . ?
C3 C4 H4 128.8(13) . . ?
O1 C5 C6 122.04(15) . . ?
N1 C5 O1 115.60(15) . . ?
N1 C5 C6 122.34(16) . . ?
O2 C6 C5 122.15(15) . . ?
N2 C6 O2 115.75(15) . . ?
N2 C6 C5 122.10(16) . . ?
N1 C7 C8 119.71(17) . . ?
N1 C7 C12 120.75(16) . . ?
C8 C7 C12 119.54(17) . . ?
C7 C8 H8 117.6(12) . . ?
C9 C8 C7 119.86(18) . . ?
C9 C8 H8 122.6(12) . . ?
C8 C9 C10 120.48(18) . . ?
C8 C9 H9 121.0(14) . . ?
C10 C9 H9 118.5(14) . . ?
C9 C10 H10 118.0(15) . . ?
C11 C10 C9 120.58(19) . . ?
C11 C10 H10 121.3(15) . . ?
C10 C11 C12 120.12(18) . . ?
C10 C11 H11 123.4(13) . . ?
C12 C11 H11 116.5(13) . . ?
N2 C12 C7 120.80(16) . . ?
N2 C12 C11 119.78(17) . . ?
C11 C12 C7 119.42(16) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2 1 -2 0.1664 -2.0000 1.0001 -2.0000 -0.0245 0.3184 0.1525
2 -1 2 0.1664 2.0000 -1.0001 2.0000 0.0245 -0.3184 -0.1525
0 -1 0 0.0262 -0.0000 -1.0000 -0.0000 0.0336 -0.0004 -0.0012
0 1 0 0.0262 0.0000 1.0000 0.0000 -0.0336 0.0004 0.0012
0 0 -1 0.0329 -0.0000 0.0000 -1.0000 0.0023 -0.0011 0.0655
0 0 1 0.0329 0.0000 -0.0000 1.0000 -0.0023 0.0011 -0.0655

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_36F2_PheDOT_iper4
_database_code_depnum_ccdc_archive 'CCDC 1553611'
_audit_update_record             
;
2017-06-01 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date             2015-01-20
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;

_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H4 F2 O2 S'
_chemical_formula_sum            'C10 H4 F2 O2 S'
_chemical_formula_weight         226.19
_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'
F F 0.0171 0.0103 '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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z+1/2'
4 '-x, y+1/2, -z'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z-1/2'
8 'x, -y-1/2, z'

_cell_length_a                   19.8371(6)
_cell_length_b                   11.5899(4)
_cell_length_c                   3.70810(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     852.53(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4613
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      30.28
_cell_measurement_theta_min      2.70
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1522 before and 0.0711 after correction.
The Ratio of minimum to maximum transmission is 0.8269.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'dull colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            15895
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.70
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  D8Venture
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'ImuS microsource'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                956
_reflns_number_total             1181
_reflns_threshold_expression     >2sigma(I)
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     78
_refine_ls_number_reflns         1181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0370
_refine_ls_restrained_S_all      1.060
_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)+(0.0420P)²+0.5500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0910
_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    
;
;
_atom_sites_solution_hydrogens   difmap
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
S1 S 0.84592(3) 0.2500 0.89596(17) 0.01909(17) Uani 1 d . . 2 S T P
F1 F 0.56856(5) 0.48367(8) 0.3160(3) 0.0247(3) Uani 1 d . . 1 . . .
O1 O 0.67582(5) 0.37524(9) 0.5704(3) 0.0169(3) Uani 1 d . . 1 . . .
C1 C 0.78996(8) 0.35718(15) 0.7876(5) 0.0177(4) Uani 1 d . . 1 . . .
C2 C 0.73104(8) 0.31086(13) 0.6761(4) 0.0136(3) Uani 1 d . . 1 . . .
C3 C 0.62306(8) 0.30998(13) 0.4431(4) 0.0123(3) Uani 1 d . . 1 . . .
C4 C 0.56686(8) 0.36673(13) 0.3128(4) 0.0148(3) Uani 1 d . . 1 . . .
C5 C 0.51116(8) 0.30989(15) 0.1855(5) 0.0175(4) Uani 1 d . . 1 . . .
H1 H 0.8020(10) 0.4335(18) 0.815(6) 0.024(5) Uiso 1 d . . 1 . . .
H5 H 0.4746(10) 0.3539(18) 0.100(6) 0.029(6) Uiso 1 d . . 1 . . .


_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 C1 1.7138(18) 8_565 ?
S1 C1 1.7138(18) . ?
F1 C4 1.3557(18) . ?
O1 C2 1.3822(19) . ?
O1 C3 1.3748(18) . ?
C1 C2 1.351(2) . ?
C1 H1 0.92(2) . ?
C2 C2 1.411(3) 8_565 ?
C3 C3 1.390(3) 8_565 ?
C3 C4 1.382(2) . ?
C4 C5 1.370(2) . ?
C5 C5 1.388(3) 8_565 ?
C5 H5 0.94(2) . ?

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
C1 S1 C1 92.91(11) 8_565 . ?
C3 O1 C2 113.81(12) . . ?
S1 C1 H1 120.1(13) . . ?
C2 C1 S1 110.13(13) . . ?
C2 C1 H1 129.8(13) . . ?
O1 C2 C2 122.67(8) . 8_565 ?
C1 C2 O1 123.91(14) . . ?
C1 C2 C2 113.42(10) . 8_565 ?
O1 C3 C3 123.37(8) . 8_565 ?
O1 C3 C4 118.19(14) . . ?
C4 C3 C3 118.43(9) . 8_565 ?
F1 C4 C3 116.92(14) . . ?
F1 C4 C5 120.24(14) . . ?
C5 C4 C3 122.84(15) . . ?
C4 C5 C5 118.73(10) . 8_565 ?
C4 C5 H5 118.5(13) . . ?
C5 C5 H5 122.8(13) 8_565 . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_PzDOT_iper3
_database_code_depnum_ccdc_archive 'CCDC 1553614'
_audit_update_record             
;
2017-06-01 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date             2015-02-11
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;

_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C8 H4 N2 O2 S'
_chemical_formula_sum            'C8 H4 N2 O2 S'
_chemical_formula_weight         192.19
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   17.3384(3)
_cell_length_b                   6.74570(10)
_cell_length_c                   14.5495(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.8015(15)
_cell_angle_gamma                90.00
_cell_volume                     1544.75(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8927
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      29.63
_cell_measurement_theta_min      2.59
_exptl_absorpt_coefficient_mu    0.378
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0666 before and 0.0541 after correction.
The Ratio of minimum to maximum transmission is 0.9054.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0729
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            34104
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.39
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  '3-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'ImuS microsource'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                3414
_reflns_number_total             4513
_reflns_threshold_expression     >2sigma(I)
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4513
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0433
_refine_ls_restrained_S_all      1.032
_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)+(0.0400P)²+0.6000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0952
_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. Twinned data refinement
 Scales: 0.7132(12) 0.2868(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C7(H7), C8(H8), C1A(H1A), C4A(H4A), C7A(H7A), C8A(H8A)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.33781(4) 0.29411(11) 0.38596(5) 0.02100(16) Uani 1 d . . .
O1 O 0.56484(10) 0.2391(2) 0.59820(14) 0.0161(4) Uani 1 d . . .
O2 O 0.45461(9) 0.4589(2) 0.66529(12) 0.0170(4) Uani 1 d . . .
N1 N 0.66650(12) 0.2497(3) 0.75814(17) 0.0167(5) Uani 1 d . . .
N2 N 0.56159(13) 0.4667(3) 0.82199(15) 0.0191(4) Uani 1 d . . .
C1 C 0.44215(15) 0.2190(4) 0.4384(2) 0.0175(5) Uani 1 d . . .
H1 H 0.4686 0.1459 0.4037 0.021 Uiso 1 calc . . R
C2 C 0.48109(14) 0.2782(3) 0.53534(19) 0.0140(5) Uani 1 d . . .
C3 C 0.42717(14) 0.3848(3) 0.56835(17) 0.0147(5) Uani 1 d . . .
C4 C 0.34752(15) 0.4081(3) 0.49577(18) 0.0178(5) Uani 1 d . . .
H4 H 0.3033 0.4775 0.5043 0.021 Uiso 1 calc . . R
C5 C 0.58937(14) 0.2981(4) 0.69618(17) 0.0143(5) Uani 1 d . . .
C6 C 0.53580(14) 0.4067(3) 0.72846(18) 0.0141(5) Uani 1 d . . .
C7 C 0.69316(15) 0.3120(4) 0.85441(18) 0.0203(5) Uani 1 d . . .
H7 H 0.7494 0.2814 0.9016 0.024 Uiso 1 calc . . R
C8 C 0.64165(15) 0.4181(4) 0.88629(19) 0.0215(5) Uani 1 d . . .
H8 H 0.6627 0.4584 0.9551 0.026 Uiso 1 calc . . R
S1A S 1.17038(4) 0.28791(11) 0.55460(5) 0.02196(17) Uani 1 d . . .
O1A O 1.05132(10) 0.4659(3) 0.71248(12) 0.0178(4) Uani 1 d . . .
O2A O 0.94136(10) 0.2497(2) 0.53390(13) 0.0154(4) Uani 1 d . . .
N1A N 0.94520(12) 0.4664(3) 0.76365(15) 0.0182(4) Uani 1 d . . .
N2A N 0.84042(13) 0.2512(3) 0.59430(18) 0.0177(5) Uani 1 d . . .
C1A C 1.16015(14) 0.4058(4) 0.65346(19) 0.0188(5) Uani 1 d . . .
H1A H 1.2046 0.4733 0.7068 0.023 Uiso 1 calc . . R
C2A C 1.07999(14) 0.3888(3) 0.64443(17) 0.0145(5) Uani 1 d . . .
C3A C 1.02600(14) 0.2830(3) 0.55705(19) 0.0141(5) Uani 1 d . . .
C4A C 1.06570(16) 0.2187(4) 0.5002(2) 0.0197(5) Uani 1 d . . .
H4A H 1.0394 0.1458 0.4390 0.024 Uiso 1 calc . . R
C5A C 0.97030(13) 0.4110(3) 0.69509(17) 0.0137(4) Uani 1 d . . .
C6A C 0.91705(14) 0.3030(3) 0.60903(16) 0.0132(4) Uani 1 d . . .
C7A C 0.86620(16) 0.4127(4) 0.74947(19) 0.0218(5) Uani 1 d . . .
H7A H 0.8457 0.4500 0.7981 0.026 Uiso 1 calc . . R
C8A C 0.81491(15) 0.3055(4) 0.66643(19) 0.0201(5) Uani 1 d . . .
H8A H 0.7599 0.2682 0.6594 0.024 Uiso 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 C1 1.719(2) . ?
S1 C4 1.717(3) . ?
O1 C2 1.379(3) . ?
O1 C5 1.365(3) . ?
O2 C3 1.379(3) . ?
O2 C6 1.366(3) . ?
N1 C5 1.303(3) . ?
N1 C7 1.345(3) . ?
N2 C6 1.306(3) . ?
N2 C8 1.349(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.343(3) . ?
C2 C3 1.414(3) . ?
C3 C4 1.350(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.409(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.369(4) . ?
C8 H8 0.9500 . ?
S1A C1A 1.717(3) . ?
S1A C4A 1.713(3) . ?
O1A C2A 1.382(3) . ?
O1A C5A 1.370(3) . ?
O2A C3A 1.379(3) . ?
O2A C6A 1.374(3) . ?
N1A C5A 1.299(3) . ?
N1A C7A 1.346(3) . ?
N2A C6A 1.302(3) . ?
N2A C8A 1.349(3) . ?
C1A H1A 0.9500 . ?
C1A C2A 1.345(3) . ?
C2A C3A 1.416(3) . ?
C3A C4A 1.351(4) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.407(3) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.368(4) . ?
C8A H8A 0.9500 . ?

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
C4 S1 C1 92.56(12) . . ?
C5 O1 C2 114.66(19) . . ?
C6 O2 C3 114.25(18) . . ?
C5 N1 C7 116.5(2) . . ?
C6 N2 C8 116.8(2) . . ?
S1 C1 H1 124.7 . . ?
C2 C1 S1 110.52(19) . . ?
C2 C1 H1 124.7 . . ?
O1 C2 C3 122.3(2) . . ?
C1 C2 O1 124.4(2) . . ?
C1 C2 C3 113.3(2) . . ?
O2 C3 C2 122.6(2) . . ?
C4 C3 O2 123.9(2) . . ?
C4 C3 C2 113.5(2) . . ?
S1 C4 H4 124.9 . . ?
C3 C4 S1 110.16(19) . . ?
C3 C4 H4 124.9 . . ?
O1 C5 C6 122.7(2) . . ?
N1 C5 O1 115.4(2) . . ?
N1 C5 C6 121.9(2) . . ?
O2 C6 C5 123.2(2) . . ?
N2 C6 O2 115.3(2) . . ?
N2 C6 C5 121.5(2) . . ?
N1 C7 H7 119.1 . . ?
N1 C7 C8 121.9(2) . . ?
C8 C7 H7 119.1 . . ?
N2 C8 C7 121.3(2) . . ?
N2 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C4A S1A C1A 92.96(12) . . ?
C5A O1A C2A 114.52(18) . . ?
C6A O2A C3A 114.40(18) . . ?
C5A N1A C7A 116.9(2) . . ?
C6A N2A C8A 116.4(2) . . ?
S1A C1A H1A 124.9 . . ?
C2A C1A S1A 110.13(19) . . ?
C2A C1A H1A 124.9 . . ?
O1A C2A C3A 122.1(2) . . ?
C1A C2A O1A 124.4(2) . . ?
C1A C2A C3A 113.4(2) . . ?
O2A C3A C2A 122.4(2) . . ?
C4A C3A O2A 124.2(2) . . ?
C4A C3A C2A 113.4(2) . . ?
S1A C4A H4A 125.0 . . ?
C3A C4A S1A 110.1(2) . . ?
C3A C4A H4A 125.0 . . ?
O1A C5A C6A 122.9(2) . . ?
N1A C5A O1A 115.3(2) . . ?
N1A C5A C6A 121.7(2) . . ?
O2A C6A C5A 122.5(2) . . ?
N2A C6A O2A 115.5(2) . . ?
N2A C6A C5A 121.9(2) . . ?
N1A C7A H7A 119.3 . . ?
N1A C7A C8A 121.3(2) . . ?
C8A C7A H7A 119.3 . . ?
N2A C8A C7A 121.8(2) . . ?
N2A C8A H8A 119.1 . . ?
C7A C8A H8A 119.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.7132(12)
2 0.2868(12)

####################################################################### 
# 
# 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_F4_PheDOT_iper1
_database_code_depnum_ccdc_archive 'CCDC 1553612'
_audit_update_record             
;
2017-06-01 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date             2015-01-16
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4987)
;

_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H2 F4 O2 S'
_chemical_formula_sum            'C10 H2 F4 O2 S'
_chemical_formula_weight         262.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H2 F4 O2 S1'
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'
F F 0.0171 0.0103 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   5.8022(9)
_cell_length_b                   7.6384(9)
_cell_length_c                   11.243(2)
_cell_angle_alpha                108.558(15)
_cell_angle_beta                 94.513(15)
_cell_angle_gamma                104.161(12)
_cell_volume                     451.33(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1029
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      32.5470
_cell_measurement_theta_min      1.9970
_exptl_absorpt_coefficient_mu    0.407
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull light colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.929
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.4694
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.0199
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0713
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5934
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.90
_diffrn_ambient_temperature      120.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -31.00   49.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712  -57.0000  150.0000 80

#__ type_ start__ end____ width___ exp.time_
  2 omega   33.00  105.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712 -164.0000  168.0000 72

#__ type_ start__ end____ width___ exp.time_
  3 omega   72.00   99.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712 -178.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega   44.00   82.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712 -118.0000  -41.0000 38

#__ type_ start__ end____ width___ exp.time_
  5 omega   18.00   94.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712   57.0000   30.0000 76

#__ type_ start__ end____ width___ exp.time_
  6 omega   80.00  106.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712 -178.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega  -44.00   73.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       29.2712  -19.0000 -150.0000 117

#__ type_ start__ end____ width___ exp.time_
  8 omega  -97.00   -7.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.4900  -57.0000  150.0000 90

#__ type_ start__ end____ width___ exp.time_
  9 omega -104.00  -52.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.4900 -178.0000  -90.0000 52

#__ type_ start__ end____ width___ exp.time_
 10 omega  -99.00    2.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.4900  -77.0000  -90.0000 101
;
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ω-scan
_diffrn_orient_matrix_UB_11      -0.0271520000
_diffrn_orient_matrix_UB_12      -0.0232805000
_diffrn_orient_matrix_UB_13      -0.0667970000
_diffrn_orient_matrix_UB_21      -0.1140699000
_diffrn_orient_matrix_UB_22      -0.0620834000
_diffrn_orient_matrix_UB_23      -0.0014256000
_diffrn_orient_matrix_UB_31      -0.0512011000
_diffrn_orient_matrix_UB_32      0.0777757000
_diffrn_orient_matrix_UB_33      0.0098557000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1516
_reflns_number_total             2173
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0581
_refine_ls_restrained_S_all      1.019
_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)+(0.0700P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1554
_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
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4)
;
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.49907(15) 0.46083(11) 1.20505(7) 0.0266(2) Uani 1 d . . .
F1 F 0.9581(3) 0.1334(3) 0.69482(16) 0.0286(4) Uani 1 d . . .
F2 F 0.7222(3) -0.1661(3) 0.48046(16) 0.0343(5) Uani 1 d . . .
F3 F 0.2544(4) -0.3629(3) 0.46873(17) 0.0383(5) Uani 1 d . . .
F4 F 0.0294(3) -0.2580(3) 0.67226(17) 0.0301(5) Uani 1 d . . .
O1 O 0.7532(4) 0.2374(3) 0.90127(19) 0.0237(5) Uani 1 d . . .
O2 O 0.2506(4) 0.0324(3) 0.88677(19) 0.0234(5) Uani 1 d . . .
C1 C 0.7151(6) 0.4419(4) 1.1090(3) 0.0250(7) Uani 1 d . . .
H1 H 0.8717 0.5234 1.1297 0.030 Uiso 1 calc . . R
C2 C 0.6230(6) 0.2902(4) 0.9983(3) 0.0211(6) Uani 1 d . . .
C3 C 0.3788(6) 0.1911(4) 0.9913(3) 0.0215(6) Uani 1 d . . .
C4 C 0.2861(6) 0.2664(4) 1.0962(3) 0.0233(7) Uani 1 d . . .
H4 H 0.1290 0.2192 1.1076 0.028 Uiso 1 calc . . R
C5 C 0.6175(6) 0.0894(4) 0.7943(3) 0.0208(6) Uani 1 d . . .
C6 C 0.7299(5) 0.0361(4) 0.6901(3) 0.0224(6) Uani 1 d . . .
C7 C 0.6096(6) -0.1154(5) 0.5807(3) 0.0260(7) Uani 1 d . . .
C8 C 0.3738(6) -0.2145(4) 0.5749(3) 0.0254(7) Uani 1 d . . .
C9 C 0.2586(5) -0.1616(4) 0.6775(3) 0.0242(7) Uani 1 d . . .
C10 C 0.3793(5) -0.0098(4) 0.7876(3) 0.0209(6) Uani 1 d . . .


_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 C1 1.720(3) . ?
S1 C4 1.714(3) . ?
F1 C6 1.338(4) . ?
F2 C7 1.345(3) . ?
F3 C8 1.347(3) . ?
F4 C9 1.340(4) . ?
O1 C2 1.386(3) . ?
O1 C5 1.376(4) . ?
O2 C3 1.385(4) . ?
O2 C10 1.387(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.361(4) . ?
C2 C3 1.416(4) . ?
C3 C4 1.353(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(4) . ?
C5 C10 1.388(4) . ?
C6 C7 1.379(4) . ?
C7 C8 1.377(5) . ?
C8 C9 1.378(4) . ?
C9 C10 1.386(4) . ?

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
C4 S1 C1 92.94(15) . . ?
C5 O1 C2 113.5(2) . . ?
C3 O2 C10 113.3(2) . . ?
S1 C1 H1 125.0 . . ?
C2 C1 S1 110.0(2) . . ?
C2 C1 H1 125.0 . . ?
O1 C2 C3 123.0(3) . . ?
C1 C2 O1 123.8(3) . . ?
C1 C2 C3 113.2(3) . . ?
O2 C3 C2 122.6(3) . . ?
C4 C3 O2 124.0(3) . . ?
C4 C3 C2 113.4(3) . . ?
S1 C4 H4 124.8 . . ?
C3 C4 S1 110.5(2) . . ?
C3 C4 H4 124.8 . . ?
O1 C5 C6 117.2(3) . . ?
O1 C5 C10 123.5(3) . . ?
C6 C5 C10 119.2(3) . . ?
F1 C6 C5 119.6(3) . . ?
F1 C6 C7 119.4(3) . . ?
C7 C6 C5 120.9(3) . . ?
F2 C7 C6 120.2(3) . . ?
F2 C7 C8 120.2(3) . . ?
C8 C7 C6 119.6(3) . . ?
F3 C8 C7 120.2(3) . . ?
F3 C8 C9 119.7(3) . . ?
C7 C8 C9 120.1(3) . . ?
F4 C9 C8 120.2(3) . . ?
F4 C9 C10 119.4(3) . . ?
C8 C9 C10 120.4(3) . . ?
O2 C10 C5 123.7(3) . . ?
C9 C10 O2 116.6(3) . . ?
C9 C10 C5 119.7(3) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 -1 0.0100 0.0009 -0.0007 -0.9998 0.0668 0.0014 -0.0100
0 0 1 0.0100 -0.0009 0.0007 0.9998 -0.0668 -0.0014 0.0100
1 0 0 0.1628 0.9995 0.0009 0.0017 -0.0273 -0.1141 -0.0511
-1 0 0 0.1738 -0.9995 -0.0009 -0.0017 0.0273 0.1141 0.0511
-1 2 0 0.1049 -1.0014 2.0000 -0.0010 -0.0193 -0.0099 0.2068
1 -2 0 0.1049 1.0014 -2.0000 0.0010 0.0193 0.0099 -0.2068

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_3NO2_iper5
_database_code_depnum_ccdc_archive 'CCDC 1553613'
_audit_update_record             
;
2017-06-01 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date             2015-01-20
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;

_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H4 F3 N O4 S'
_chemical_formula_sum            'C11 H4 F3 N O4 S'
_chemical_formula_weight         303.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H4 N1 O4 F3 S1'
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'
F F 0.0171 0.0103 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.2118(10)
_cell_length_b                   7.0519(13)
_cell_length_c                   14.316(2)
_cell_angle_alpha                79.354(14)
_cell_angle_beta                 79.598(13)
_cell_angle_gamma                65.073(16)
_cell_volume                     555.18(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1258
_cell_measurement_temperature    200.0
_cell_measurement_theta_max      28.5900
_cell_measurement_theta_min      2.9120
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull yellowish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.814
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.4103
_exptl_crystal_size_mid          0.1343
_exptl_crystal_size_min          0.0691
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5400
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.91
_diffrn_ambient_temperature      200.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -95.00  -54.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337 -178.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
  2 omega -101.00  -61.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337 -178.0000   60.0000 40

#__ type_ start__ end____ width___ exp.time_
  3 omega  -66.00   45.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337    0.0000   60.0000 111

#__ type_ start__ end____ width___ exp.time_
  4 omega  -99.00   -5.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  -38.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
  5 omega  -18.00   66.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
  6 omega   -1.00   49.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000   30.0000 50

#__ type_ start__ end____ width___ exp.time_
  7 omega  -28.00   -2.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  133.0000   90.3473 26

#__ type_ start__ end____ width___ exp.time_
  8 omega -101.00  -25.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -28.3337  -38.0000 -120.0000 76
;
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0143563000
_diffrn_orient_matrix_UB_12      -0.0114427000
_diffrn_orient_matrix_UB_13      0.0507384000
_diffrn_orient_matrix_UB_21      -0.1128112000
_diffrn_orient_matrix_UB_22      0.0865167000
_diffrn_orient_matrix_UB_23      -0.0004152000
_diffrn_orient_matrix_UB_31      -0.0559973000
_diffrn_orient_matrix_UB_32      -0.0697956000
_diffrn_orient_matrix_UB_33      0.0010651000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1726
_reflns_number_total             2411
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.821
_refine_diff_density_min         -0.773
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2411
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0830
_refine_ls_restrained_S_all      1.067
_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)+(0.1200P)²+1.0900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2125
_refine_ls_wR_factor_ref         0.2398
_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. Restrained distances
 F3-C11 \\sim F3A-C11 \\sim F1-C11 \\sim F1A-C11 \\sim F2-C11 \\sim F2A-C11
 with sigma of 0.005
 O3A-N1 \\sim O3-N1 \\sim O4-N1 \\sim O4A-N1
 with sigma of 0.005
2. Others
 Fixed Sof: F1(0.5) F1A(0.5) F2(0.5) F2A(0.5) F3(0.5) F3A(0.5) O3(0.5)
 O3A(0.5) O4(0.5) O4A(0.5)
;
_atom_sites_solution_hydrogens   difmap
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 1.2072(2) 0.81870(19) 0.30519(8) 0.0389(4) Uani 1 d . . .
F1 F 0.7778(10) 0.0241(12) 0.0348(5) 0.048(2) Uiso 0.50 d A 1 D
F1A F 0.7705(12) -0.0267(12) 0.0531(6) 0.064(3) Uiso 0.50 d A 2 D
F2 F 0.5105(12) -0.0224(9) 0.1354(4) 0.0538(16) Uiso 0.50 d A 1 D
F2A F 0.4060(9) 0.0709(10) 0.1307(4) 0.0427(13) Uiso 0.50 d A 2 D
F3 F 0.4303(16) 0.2784(13) 0.0384(7) 0.079(3) Uiso 0.50 d A 1 D
F3A F 0.4945(14) 0.2767(9) 0.0213(5) 0.0463(19) Uiso 0.50 d A 2 D
O1 O 0.8422(6) 0.4741(5) 0.3620(2) 0.0420(8) Uani 1 d B . .
O2 O 0.9920(7) 0.5342(6) 0.1596(2) 0.0450(9) Uani 1 d . . .
O3 O 0.6717(16) 0.2428(15) 0.4923(5) 0.058(2) Uiso 0.50 d B 1 D
O3A O 0.7427(11) 0.1682(11) 0.4796(5) 0.0344(15) Uiso 0.50 d B 2 D
O4 O 0.3759(11) 0.2341(18) 0.4574(8) 0.054(3) Uiso 0.50 d B 1 D
O4A O 0.3889(11) 0.1994(16) 0.4416(7) 0.044(3) Uiso 0.50 d B 2 D
N1 N 0.5786(6) 0.2254(7) 0.4277(3) 0.0455(10) Uani 1 d . . D
C1 C 1.0432(9) 0.6919(7) 0.3768(4) 0.0367(10) Uani 1 d . . .
C2 C 0.9704(8) 0.5955(7) 0.3241(3) 0.0351(10) Uani 1 d . . .
C3 C 1.0464(8) 0.6232(7) 0.2253(3) 0.0359(10) Uani 1 d . . .
C4 C 1.1732(9) 0.7416(8) 0.2038(3) 0.0377(10) Uani 1 d . . .
C5 C 0.7873(8) 0.3883(7) 0.2961(3) 0.0337(10) Uani 1 d . . .
C6 C 0.6501(8) 0.2706(7) 0.3256(3) 0.0345(10) Uani 1 d B . .
C7 C 0.5824(8) 0.1862(8) 0.2623(3) 0.0374(10) Uani 1 d . . .
C8 C 0.6567(8) 0.2170(7) 0.1658(3) 0.0366(10) Uani 1 d A . .
C9 C 0.7943(9) 0.3330(8) 0.1334(3) 0.0376(10) Uani 1 d . . .
C10 C 0.8583(8) 0.4190(7) 0.1973(3) 0.0341(10) Uani 1 d B . .
C11 C 0.5874(6) 0.1296(6) 0.0945(3) 0.0441(12) Uani 1 d . . D
H1 H 1.027(10) 0.687(9) 0.436(5) 0.055(17) Uiso 1 d . . .
H4 H 1.234(11) 0.786(10) 0.148(5) 0.062(18) Uiso 1 d . . .
H7 H 0.500(9) 0.112(8) 0.283(4) 0.038(13) Uiso 1 d . . .
H9 H 0.843(10) 0.355(9) 0.080(4) 0.046(16) Uiso 1 d . . .


_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 C1 1.715(5) . ?
S1 C4 1.717(5) . ?
F1 C11 1.347(4) . ?
F1A C11 1.343(4) . ?
F2 C11 1.349(4) . ?
F2A C11 1.346(4) . ?
F3 C11 1.345(4) . ?
F3A C11 1.349(4) . ?
O1 C2 1.381(5) . ?
O1 C5 1.369(5) . ?
O2 C3 1.381(5) . ?
O2 C10 1.373(5) . ?
O3 N1 1.224(5) . ?
O3A N1 1.253(4) . ?
O4 N1 1.233(5) . ?
O4A N1 1.243(4) . ?
N1 C6 1.467(6) . ?
C1 C2 1.345(6) . ?
C1 H1 0.83(6) . ?
C2 C3 1.413(6) . ?
C3 C4 1.336(6) . ?
C4 H4 0.88(7) . ?
C5 C6 1.390(6) . ?
C5 C10 1.408(6) . ?
C6 C7 1.378(6) . ?
C7 C8 1.382(7) . ?
C7 H7 0.86(5) . ?
C8 C9 1.386(6) . ?
C8 C11 1.490(6) . ?
C9 C10 1.379(7) . ?
C9 H9 0.78(6) . ?

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
C1 S1 C4 92.1(2) . . ?
C5 O1 C2 114.8(3) . . ?
C10 O2 C3 115.1(3) . . ?
O3 N1 O3A 26.2(5) . . ?
O3 N1 O4 110.3(8) . . ?
O3 N1 O4A 123.0(7) . . ?
O3 N1 C6 124.3(5) . . ?
O3A N1 C6 114.3(5) . . ?
O4 N1 O3A 124.1(7) . . ?
O4 N1 O4A 15.7(7) . . ?
O4 N1 C6 121.5(6) . . ?
O4A N1 O3A 130.9(7) . . ?
O4A N1 C6 111.8(6) . . ?
S1 C1 H1 121(4) . . ?
C2 C1 S1 110.5(4) . . ?
C2 C1 H1 128(4) . . ?
O1 C2 C3 122.7(4) . . ?
C1 C2 O1 124.0(4) . . ?
C1 C2 C3 113.2(4) . . ?
O2 C3 C2 121.9(4) . . ?
C4 C3 O2 124.8(4) . . ?
C4 C3 C2 113.2(4) . . ?
S1 C4 H4 119(4) . . ?
C3 C4 S1 110.9(4) . . ?
C3 C4 H4 130(4) . . ?
O1 C5 C6 119.9(4) . . ?
O1 C5 C10 122.7(4) . . ?
C6 C5 C10 117.4(4) . . ?
C5 C6 N1 120.1(4) . . ?
C7 C6 N1 117.3(4) . . ?
C7 C6 C5 122.6(4) . . ?
C6 C7 C8 118.8(4) . . ?
C6 C7 H7 120(3) . . ?
C8 C7 H7 121(3) . . ?
C7 C8 C9 120.5(4) . . ?
C7 C8 C11 120.8(4) . . ?
C9 C8 C11 118.7(4) . . ?
C8 C9 H9 126(4) . . ?
C10 C9 C8 120.1(4) . . ?
C10 C9 H9 114(4) . . ?
O2 C10 C5 122.7(4) . . ?
O2 C10 C9 116.7(4) . . ?
C9 C10 C5 120.6(4) . . ?
F1 C11 F2 101.6(5) . . ?
F1 C11 F3A 90.4(5) . . ?
F1 C11 C8 111.6(5) . . ?
F1A C11 F1 17.8(5) . . ?
F1A C11 F2 84.6(6) . . ?
F1A C11 F2A 110.7(6) . . ?
F1A C11 F3 117.9(7) . . ?
F1A C11 F3A 104.9(6) . . ?
F1A C11 C8 114.0(5) . . ?
F2 C11 F3A 125.2(5) . . ?
F2 C11 C8 112.4(4) . . ?
F2A C11 F1 125.1(5) . . ?
F2A C11 F2 30.4(3) . . ?
F2A C11 F3A 101.9(5) . . ?
F2A C11 C8 112.4(4) . . ?
F3 C11 F1 105.8(7) . . ?
F3 C11 F2 111.4(6) . . ?
F3 C11 F2A 85.1(6) . . ?
F3 C11 F3A 18.1(6) . . ?
F3 C11 C8 113.3(6) . . ?
F3A C11 C8 112.0(4) . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 0 1 0.0346 0.0000 -0.0000 1.0000 0.0507 -0.0004 0.0011
0 0 -1 0.0346 -0.0000 0.0000 -1.0000 -0.0507 0.0004 -0.0011
1 2 1 0.0418 1.0000 2.0000 1.0000 0.0135 0.0598 -0.1945
0 2 1 0.1236 0.0000 2.0000 1.0000 0.0279 0.1726 -0.1385
1 0 0 0.2038 1.0000 -0.0000 -0.0000 -0.0144 -0.1128 -0.0560
-1 -1 -1 0.0705 -1.0000 -1.0000 -1.0000 -0.0249 0.0267 0.1247
-1 -3 -1 0.0946 -1.0000 -3.0000 -1.0000 -0.0021 -0.1463 0.2643

_olex2_submission_special_instructions 'No special instructions were received'

