# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_4no2-pyrole
_database_code_depnum_ccdc_archive 'CCDC 1400572'
_audit_update_record             
;
2015-05-13 deposited with the CCDC.
2018-04-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 N2 O4'
_chemical_formula_sum            'C18 H14 N2 O4'
_chemical_formula_weight         322.31

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'


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

_cell_length_a                   8.0230(6)
_cell_length_b                   10.5211(8)
_cell_length_c                   18.4479(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1557.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1096
_cell_measurement_theta_min      3.8540
_cell_measurement_theta_max      25.0100

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'Omega Scan'
_diffrn_detector_area_resol_mean 16.1049
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4243
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0639
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.84
_diffrn_reflns_theta_max         26.00
_reflns_number_total             1762
_reflns_number_gt                1184
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0412P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(3)
_refine_ls_number_reflns         1762
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1085
_refine_ls_wR_factor_gt          0.0913
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8515(4) 0.6305(3) 0.28095(17) 0.0409(8) Uani 1 1 d . . .
C2 C 0.7556(5) 0.5252(3) 0.29505(19) 0.0375(9) Uani 1 1 d . . .
C3 C 0.6261(4) 0.5262(4) 0.2453(2) 0.0380(9) Uani 1 1 d . . .
C4 C 0.6474(5) 0.6319(3) 0.1993(2) 0.0452(10) Uani 1 1 d . . .
H4 H 0.5791 0.6550 0.1608 0.054 Uiso 1 1 calc R . .
C5 C 0.7868(5) 0.6936(4) 0.2220(2) 0.0490(10) Uani 1 1 d . . .
H5 H 0.8312 0.7666 0.2011 0.059 Uiso 1 1 calc R . .
C6 C 0.4828(5) 0.4425(4) 0.2446(2) 0.0516(11) Uani 1 1 d . . .
H6 H 0.4794 0.3768 0.2783 0.062 Uiso 1 1 calc R . .
O6 O 0.3668(3) 0.4528(3) 0.20255(17) 0.0644(8) Uani 1 1 d . . .
C7 C 0.9933(4) 0.6777(4) 0.3204(2) 0.0388(9) Uani 1 1 d . . .
C8 C 1.1327(5) 0.6051(3) 0.3305(2) 0.0450(10) Uani 1 1 d . . .
H8 H 1.1358 0.5226 0.3125 0.054 Uiso 1 1 calc R . .
C9 C 1.2700(5) 0.6536(4) 0.3674(2) 0.0455(10) Uani 1 1 d . . .
H9 H 1.3631 0.6029 0.3758 0.055 Uiso 1 1 calc R . .
C10 C 1.2662(5) 0.7788(4) 0.3915(2) 0.0427(10) Uani 1 1 d . . .
O10 O 1.3923(3) 0.8364(3) 0.42831(17) 0.0611(8) Uani 1 1 d . . .
C11 C 1.1266(5) 0.8516(4) 0.3793(2) 0.0473(10) Uani 1 1 d . . .
H11 H 1.1248 0.9357 0.3948 0.057 Uiso 1 1 calc R . .
C12 C 0.9905(5) 0.8023(4) 0.3446(2) 0.0456(10) Uani 1 1 d . . .
H12 H 0.8963 0.8523 0.3373 0.055 Uiso 1 1 calc R . .
C13 C 1.5459(5) 0.7691(5) 0.4365(3) 0.0706(14) Uani 1 1 d . . .
H13A H 1.5286 0.6960 0.4668 0.106 Uiso 1 1 calc R . .
H13B H 1.6272 0.8238 0.4585 0.106 Uiso 1 1 calc R . .
H13C H 1.5851 0.7421 0.3898 0.106 Uiso 1 1 calc R . .
C14 C 0.7904(4) 0.4317(3) 0.3517(2) 0.0366(9) Uani 1 1 d . . .
C15 C 0.7807(5) 0.3024(3) 0.3330(2) 0.0443(10) Uani 1 1 d . . .
H15 H 0.7579 0.2799 0.2853 0.053 Uiso 1 1 calc R . .
C16 C 0.8044(5) 0.2085(4) 0.3838(2) 0.0487(11) Uani 1 1 d . . .
H16 H 0.7954 0.1232 0.3711 0.058 Uiso 1 1 calc R . .
C17 C 0.8414(5) 0.2429(4) 0.4535(2) 0.0465(10) Uani 1 1 d . . .
N17 N 0.8660(5) 0.1424(4) 0.5078(2) 0.0660(11) Uani 1 1 d . . .
O17A O 0.8693(6) 0.0338(3) 0.48736(19) 0.1093(15) Uani 1 1 d . . .
O17B O 0.8841(6) 0.1707(3) 0.56998(19) 0.1142(16) Uani 1 1 d . . .
C18 C 0.8522(5) 0.3690(4) 0.4744(2) 0.0514(11) Uani 1 1 d . . .
H18 H 0.8760 0.3903 0.5223 0.062 Uiso 1 1 calc R . .
C19 C 0.8273(5) 0.4623(4) 0.4234(2) 0.0465(10) Uani 1 1 d . . .
H19 H 0.8352 0.5472 0.4369 0.056 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.374(4) . ?
N1 C5 1.375(4) . ?
N1 C7 1.440(5) . ?
C2 C3 1.387(5) . ?
C2 C14 1.462(5) . ?
C3 C4 1.408(5) . ?
C3 C6 1.448(5) . ?
C4 C5 1.360(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 O6 1.217(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.367(5) . ?
C7 C12 1.385(5) . ?
C8 C9 1.392(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.392(5) . ?
C9 H9 0.9300 . ?
C10 O10 1.361(4) . ?
C10 C11 1.375(5) . ?
O10 C13 1.430(5) . ?
C11 C12 1.368(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C19 1.393(5) . ?
C14 C15 1.405(5) . ?
C15 C16 1.375(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.369(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(5) . ?
C17 N17 1.469(5) . ?
N17 O17B 1.195(5) . ?
N17 O17A 1.203(5) . ?
C18 C19 1.375(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C5 109.1(3) . . ?
C2 N1 C7 128.7(3) . . ?
C5 N1 C7 122.1(3) . . ?
N1 C2 C3 106.7(3) . . ?
N1 C2 C14 124.8(3) . . ?
C3 C2 C14 128.4(3) . . ?
C2 C3 C4 108.3(3) . . ?
C2 C3 C6 126.6(4) . . ?
C4 C3 C6 124.8(4) . . ?
C5 C4 C3 106.9(3) . . ?
C5 C4 H4 126.5 . . ?
C3 C4 H4 126.5 . . ?
C4 C5 N1 108.9(3) . . ?
C4 C5 H5 125.6 . . ?
N1 C5 H5 125.6 . . ?
O6 C6 C3 123.9(4) . . ?
O6 C6 H6 118.0 . . ?
C3 C6 H6 118.0 . . ?
C8 C7 C12 119.9(4) . . ?
C8 C7 N1 121.5(3) . . ?
C12 C7 N1 118.4(3) . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C10 119.1(4) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
O10 C10 C11 116.1(3) . . ?
O10 C10 C9 124.4(4) . . ?
C11 C10 C9 119.5(4) . . ?
C10 O10 C13 118.3(3) . . ?
C12 C11 C10 121.1(4) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C7 119.7(4) . . ?
C11 C12 H12 120.1 . . ?
C7 C12 H12 120.1 . . ?
O10 C13 H13A 109.5 . . ?
O10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 117.9(4) . . ?
C19 C14 C2 124.3(3) . . ?
C15 C14 C2 117.8(3) . . ?
C16 C15 C14 121.4(4) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C17 C16 C15 118.7(4) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C16 C17 C18 122.0(4) . . ?
C16 C17 N17 118.5(4) . . ?
C18 C17 N17 119.5(4) . . ?
O17B N17 O17A 122.3(4) . . ?
O17B N17 C17 119.4(4) . . ?
O17A N17 C17 118.3(4) . . ?
C19 C18 C17 118.9(4) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C18 C19 C14 121.1(3) . . ?
C18 C19 H19 119.4 . . ?
C14 C19 H19 119.4 . . ?

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
C5 N1 C2 C3 -2.1(4) . . . . ?
C7 N1 C2 C3 175.1(3) . . . . ?
C5 N1 C2 C14 177.1(3) . . . . ?
C7 N1 C2 C14 -5.8(6) . . . . ?
N1 C2 C3 C4 1.7(4) . . . . ?
C14 C2 C3 C4 -177.4(3) . . . . ?
N1 C2 C3 C6 -172.1(4) . . . . ?
C14 C2 C3 C6 8.8(6) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C6 C3 C4 C5 173.3(4) . . . . ?
C3 C4 C5 N1 -0.6(4) . . . . ?
C2 N1 C5 C4 1.7(4) . . . . ?
C7 N1 C5 C4 -175.7(3) . . . . ?
C2 C3 C6 O6 174.8(4) . . . . ?
C4 C3 C6 O6 2.0(7) . . . . ?
C2 N1 C7 C8 58.8(5) . . . . ?
C5 N1 C7 C8 -124.4(4) . . . . ?
C2 N1 C7 C12 -125.2(4) . . . . ?
C5 N1 C7 C12 51.7(5) . . . . ?
C12 C7 C8 C9 2.5(6) . . . . ?
N1 C7 C8 C9 178.5(3) . . . . ?
C7 C8 C9 C10 -2.5(6) . . . . ?
C8 C9 C10 O10 179.8(3) . . . . ?
C8 C9 C10 C11 0.7(6) . . . . ?
C11 C10 O10 C13 -174.2(4) . . . . ?
C9 C10 O10 C13 6.7(6) . . . . ?
O10 C10 C11 C12 -178.2(3) . . . . ?
C9 C10 C11 C12 1.0(6) . . . . ?
C10 C11 C12 C7 -0.9(6) . . . . ?
C8 C7 C12 C11 -0.8(6) . . . . ?
N1 C7 C12 C11 -176.9(3) . . . . ?
N1 C2 C14 C19 48.7(5) . . . . ?
C3 C2 C14 C19 -132.4(4) . . . . ?
N1 C2 C14 C15 -133.4(4) . . . . ?
C3 C2 C14 C15 45.5(5) . . . . ?
C19 C14 C15 C16 0.9(6) . . . . ?
C2 C14 C15 C16 -177.1(4) . . . . ?
C14 C15 C16 C17 -1.3(6) . . . . ?
C15 C16 C17 C18 1.3(6) . . . . ?
C15 C16 C17 N17 179.7(4) . . . . ?
C16 C17 N17 O17B -173.6(5) . . . . ?
C18 C17 N17 O17B 4.8(7) . . . . ?
C16 C17 N17 O17A 7.4(7) . . . . ?
C18 C17 N17 O17A -174.1(5) . . . . ?
C16 C17 C18 C19 -0.9(7) . . . . ?
N17 C17 C18 C19 -179.3(4) . . . . ?
C17 C18 C19 C14 0.5(6) . . . . ?
C15 C14 C19 C18 -0.5(6) . . . . ?
C2 C14 C19 C18 177.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_an0toh
_database_code_depnum_ccdc_archive 'CCDC 1471798'
_audit_update_record             
;
2016-04-01 deposited with the CCDC.
2018-04-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H19 Cl N2 O3 S'
_chemical_formula_sum            'C26 H19 Cl N2 O3 S'
_chemical_formula_weight         474.94

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   p21/n

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

_cell_length_a                   9.9462(7)
_cell_length_b                   15.4122(9)
_cell_length_c                   15.2477(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.432(7)
_cell_angle_gamma                90.00
_cell_volume                     2322.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2754
_cell_measurement_theta_min      4.1020
_cell_measurement_theta_max      27.6100

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_T_min  0.62530
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Crys Alis RED'


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10516
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0576
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.70
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4546
_reflns_number_gt                2862
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction,2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek,2009)'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0585P)²+0.1834P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0011(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4546
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1347
_refine_ls_wR_factor_gt          0.1143
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl -0.16363(12) -0.20983(7) 0.10171(7) 0.1059(4) Uani 1 1 d . . .
O1 O 0.59662(17) 0.12279(13) 0.20991(13) 0.0607(6) Uani 1 1 d . . .
O2 O 0.4258(2) 0.19136(12) 0.10010(13) 0.0599(6) Uani 1 1 d . . .
O3 O 0.4347(2) 0.08600(14) 0.62278(14) 0.0700(6) Uani 1 1 d . . .
N1 N 0.1585(2) -0.06370(14) 0.41642(14) 0.0440(5) Uani 1 1 d . . .
N2 N 0.35946(19) 0.13450(13) 0.24161(13) 0.0398(5) Uani 1 1 d . . .
S1 S 0.46419(7) 0.12539(4) 0.16344(5) 0.0465(2) Uani 1 1 d . . .
C1 C 0.1439(3) -0.11643(17) 0.26560(19) 0.0530(7) Uani 1 1 d . . .
H1 H 0.2363 -0.1072 0.2654 0.064 Uiso 1 1 calc R . .
C2 C 0.0664(3) -0.1504(2) 0.1915(2) 0.0659(9) Uani 1 1 d . . .
H2 H 0.1066 -0.1633 0.1408 0.079 Uiso 1 1 calc R . .
C3 C -0.0698(4) -0.16470(19) 0.1935(2) 0.0618(8) Uani 1 1 d . . .
C4 C -0.1322(3) -0.14502(18) 0.2666(2) 0.0591(8) Uani 1 1 d . . .
H4 H -0.2244 -0.1546 0.2670 0.071 Uiso 1 1 calc R . .
C5 C -0.0560(3) -0.11071(17) 0.33993(19) 0.0495(7) Uani 1 1 d . . .
H5 H -0.0972 -0.0970 0.3900 0.059 Uiso 1 1 calc R . .
C6 C 0.0806(3) -0.09688(16) 0.33889(17) 0.0419(6) Uani 1 1 d . . .
C7 C 0.1639(3) -0.10271(19) 0.49841(18) 0.0530(7) Uani 1 1 d . . .
H7 H 0.1153 -0.1516 0.5117 0.064 Uiso 1 1 calc R . .
C8 C 0.2513(3) -0.05832(19) 0.55602(18) 0.0511(7) Uani 1 1 d . . .
H8 H 0.2739 -0.0715 0.6154 0.061 Uiso 1 1 calc R . .
C9 C 0.3024(2) 0.01219(17) 0.50950(17) 0.0411(6) Uani 1 1 d . . .
C10 C 0.2432(2) 0.00684(16) 0.42231(16) 0.0381(6) Uani 1 1 d . . .
C11 C 0.3920(3) 0.07974(18) 0.54501(19) 0.0493(7) Uani 1 1 d . . .
H11 H 0.4191 0.1212 0.5063 0.059 Uiso 1 1 calc R . .
C12 C 0.3790(2) 0.07998(15) 0.31548(16) 0.0384(6) Uani 1 1 d . . .
H12 H 0.4626 0.0591 0.3401 0.046 Uiso 1 1 calc R . .
C13 C 0.2604(2) 0.06198(15) 0.34596(16) 0.0370(6) Uani 1 1 d . . .
C14 C 0.1549(2) 0.10546(15) 0.28876(16) 0.0370(6) Uani 1 1 d . . .
C15 C 0.0149(2) 0.11258(17) 0.28887(19) 0.0501(7) Uani 1 1 d . . .
H15 H -0.0288 0.0846 0.3317 0.060 Uiso 1 1 calc R . .
C16 C -0.0566(3) 0.1613(2) 0.2252(2) 0.0646(9) Uani 1 1 d . . .
H16 H -0.1499 0.1661 0.2245 0.078 Uiso 1 1 calc R . .
C17 C 0.0077(3) 0.2037(2) 0.1615(2) 0.0680(9) Uani 1 1 d . . .
H17 H -0.0438 0.2365 0.1190 0.082 Uiso 1 1 calc R . .
C18 C 0.1464(3) 0.19881(18) 0.15918(19) 0.0541(8) Uani 1 1 d . . .
H18 H 0.1890 0.2276 0.1164 0.065 Uiso 1 1 calc R . .
C19 C 0.2181(2) 0.14896(15) 0.22382(16) 0.0383(6) Uani 1 1 d . . .
C20 C 0.4248(2) 0.02286(16) 0.11735(17) 0.0419(6) Uani 1 1 d . . .
C21 C 0.3302(3) 0.01550(18) 0.04393(18) 0.0518(7) Uani 1 1 d . . .
H21 H 0.2902 0.0647 0.0170 0.062 Uiso 1 1 calc R . .
C22 C 0.2964(3) -0.0662(2) 0.01146(19) 0.0571(8) Uani 1 1 d . . .
H22 H 0.2338 -0.0714 -0.0383 0.068 Uiso 1 1 calc R . .
C23 C 0.3527(3) -0.14034(18) 0.05072(19) 0.0489(7) Uani 1 1 d . . .
C24 C 0.4468(3) -0.13085(19) 0.1240(2) 0.0568(8) Uani 1 1 d . . .
H24 H 0.4867 -0.1800 0.1510 0.068 Uiso 1 1 calc R . .
C25 C 0.4828(3) -0.05033(18) 0.15797(19) 0.0532(7) Uani 1 1 d . . .
H25 H 0.5455 -0.0453 0.2077 0.064 Uiso 1 1 calc R . .
C26 C 0.3136(3) -0.2292(2) 0.0155(2) 0.0699(9) Uani 1 1 d . . .
H26A H 0.2291 -0.2460 0.0354 0.105 Uiso 1 1 calc R . .
H26B H 0.3824 -0.2702 0.0366 0.105 Uiso 1 1 calc R . .
H26C H 0.3043 -0.2280 -0.0478 0.105 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl C3 1.739(3) . ?
O1 S1 1.4245(19) . ?
O2 S1 1.4247(19) . ?
O3 C11 1.218(3) . ?
N1 C10 1.372(3) . ?
N1 C7 1.383(3) . ?
N1 C6 1.433(3) . ?
N2 C12 1.401(3) . ?
N2 C19 1.420(3) . ?
N2 S1 1.674(2) . ?
S1 C20 1.756(3) . ?
C1 C6 1.376(4) . ?
C1 C2 1.397(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(4) . ?
C4 C5 1.383(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9300 . ?
C7 C8 1.350(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.423(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.395(3) . ?
C9 C11 1.436(4) . ?
C10 C13 1.467(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.344(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.451(3) . ?
C14 C15 1.397(3) . ?
C14 C19 1.401(3) . ?
C15 C16 1.362(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.385(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.386(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(3) . ?
C18 H18 0.9300 . ?
C20 C25 1.382(4) . ?
C20 C21 1.384(3) . ?
C21 C22 1.381(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.379(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.383(4) . ?
C23 C26 1.506(4) . ?
C24 C25 1.377(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C7 108.9(2) . . ?
C10 N1 C6 127.4(2) . . ?
C7 N1 C6 123.6(2) . . ?
C12 N2 C19 107.04(19) . . ?
C12 N2 S1 118.72(17) . . ?
C19 N2 S1 123.99(17) . . ?
O1 S1 O2 121.34(12) . . ?
O1 S1 N2 105.22(11) . . ?
O2 S1 N2 106.36(11) . . ?
O1 S1 C20 109.03(12) . . ?
O2 S1 C20 109.88(12) . . ?
N2 S1 C20 103.39(11) . . ?
C6 C1 C2 118.5(3) . . ?
C6 C1 H1 120.7 . . ?
C2 C1 H1 120.7 . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 121.4(3) . . ?
C4 C3 Cl 119.5(3) . . ?
C2 C3 Cl 119.1(3) . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C1 C6 C5 121.2(3) . . ?
C1 C6 N1 119.6(2) . . ?
C5 C6 N1 119.2(2) . . ?
C8 C7 N1 109.0(2) . . ?
C8 C7 H7 125.5 . . ?
N1 C7 H7 125.5 . . ?
C7 C8 C9 107.6(2) . . ?
C7 C8 H8 126.2 . . ?
C9 C8 H8 126.2 . . ?
C10 C9 C8 107.1(2) . . ?
C10 C9 C11 125.5(2) . . ?
C8 C9 C11 127.4(2) . . ?
N1 C10 C9 107.5(2) . . ?
N1 C10 C13 122.2(2) . . ?
C9 C10 C13 130.4(2) . . ?
O3 C11 C9 123.9(3) . . ?
O3 C11 H11 118.0 . . ?
C9 C11 H11 118.0 . . ?
C13 C12 N2 110.7(2) . . ?
C13 C12 H12 124.7 . . ?
N2 C12 H12 124.7 . . ?
C12 C13 C14 107.5(2) . . ?
C12 C13 C10 125.4(2) . . ?
C14 C13 C10 127.1(2) . . ?
C15 C14 C19 119.3(2) . . ?
C15 C14 C13 133.6(2) . . ?
C19 C14 C13 107.1(2) . . ?
C16 C15 C14 118.9(3) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C17 121.0(3) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C16 C17 C18 122.1(3) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C19 C18 C17 116.5(3) . . ?
C19 C18 H18 121.7 . . ?
C17 C18 H18 121.7 . . ?
C18 C19 C14 122.2(2) . . ?
C18 C19 N2 130.1(2) . . ?
C14 C19 N2 107.6(2) . . ?
C25 C20 C21 120.5(2) . . ?
C25 C20 S1 119.5(2) . . ?
C21 C20 S1 119.9(2) . . ?
C22 C21 C20 118.7(3) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C23 C22 C21 121.9(3) . . ?
C23 C22 H22 119.0 . . ?
C21 C22 H22 119.0 . . ?
C22 C23 C24 117.9(3) . . ?
C22 C23 C26 121.5(3) . . ?
C24 C23 C26 120.6(3) . . ?
C25 C24 C23 121.6(3) . . ?
C25 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C24 C25 C20 119.3(3) . . ?
C24 C25 H25 120.4 . . ?
C20 C25 H25 120.4 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N2 S1 O1 -46.7(2) . . . . ?
C19 N2 S1 O1 172.71(18) . . . . ?
C12 N2 S1 O2 -176.63(17) . . . . ?
C19 N2 S1 O2 42.8(2) . . . . ?
C12 N2 S1 C20 67.6(2) . . . . ?
C19 N2 S1 C20 -73.0(2) . . . . ?
C6 C1 C2 C3 -1.0(4) . . . . ?
C1 C2 C3 C4 1.1(5) . . . . ?
C1 C2 C3 Cl -178.2(2) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
Cl C3 C4 C5 178.8(2) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
C2 C1 C6 N1 178.7(2) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C4 C5 C6 N1 -178.2(2) . . . . ?
C10 N1 C6 C1 53.9(4) . . . . ?
C7 N1 C6 C1 -122.6(3) . . . . ?
C10 N1 C6 C5 -127.8(3) . . . . ?
C7 N1 C6 C5 55.7(3) . . . . ?
C10 N1 C7 C8 -0.3(3) . . . . ?
C6 N1 C7 C8 176.7(2) . . . . ?
N1 C7 C8 C9 0.7(3) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C7 C8 C9 C11 176.0(3) . . . . ?
C7 N1 C10 C9 -0.1(3) . . . . ?
C6 N1 C10 C9 -177.1(2) . . . . ?
C7 N1 C10 C13 179.8(2) . . . . ?
C6 N1 C10 C13 2.8(4) . . . . ?
C8 C9 C10 N1 0.5(3) . . . . ?
C11 C9 C10 N1 -176.3(2) . . . . ?
C8 C9 C10 C13 -179.3(2) . . . . ?
C11 C9 C10 C13 3.8(4) . . . . ?
C10 C9 C11 O3 174.6(3) . . . . ?
C8 C9 C11 O3 -1.6(4) . . . . ?
C19 N2 C12 C13 -1.8(3) . . . . ?
S1 N2 C12 C13 -148.42(18) . . . . ?
N2 C12 C13 C14 1.0(3) . . . . ?
N2 C12 C13 C10 179.9(2) . . . . ?
N1 C10 C13 C12 -124.3(3) . . . . ?
C9 C10 C13 C12 55.6(4) . . . . ?
N1 C10 C13 C14 54.5(4) . . . . ?
C9 C10 C13 C14 -125.7(3) . . . . ?
C12 C13 C14 C15 -177.8(3) . . . . ?
C10 C13 C14 C15 3.2(4) . . . . ?
C12 C13 C14 C19 0.2(3) . . . . ?
C10 C13 C14 C19 -178.7(2) . . . . ?
C19 C14 C15 C16 0.5(4) . . . . ?
C13 C14 C15 C16 178.4(3) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
C15 C16 C17 C18 0.1(5) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
C17 C18 C19 C14 -0.1(4) . . . . ?
C17 C18 C19 N2 -176.7(3) . . . . ?
C15 C14 C19 C18 -0.2(4) . . . . ?
C13 C14 C19 C18 -178.6(2) . . . . ?
C15 C14 C19 N2 177.1(2) . . . . ?
C13 C14 C19 N2 -1.3(3) . . . . ?
C12 N2 C19 C18 178.9(3) . . . . ?
S1 N2 C19 C18 -36.7(4) . . . . ?
C12 N2 C19 C14 1.9(3) . . . . ?
S1 N2 C19 C14 146.31(18) . . . . ?
O1 S1 C20 C25 28.6(3) . . . . ?
O2 S1 C20 C25 163.8(2) . . . . ?
N2 S1 C20 C25 -83.0(2) . . . . ?
O1 S1 C20 C21 -155.3(2) . . . . ?
O2 S1 C20 C21 -20.0(3) . . . . ?
N2 S1 C20 C21 93.2(2) . . . . ?
C25 C20 C21 C22 -0.8(4) . . . . ?
S1 C20 C21 C22 -177.0(2) . . . . ?
C20 C21 C22 C23 0.9(4) . . . . ?
C21 C22 C23 C24 -0.8(4) . . . . ?
C21 C22 C23 C26 179.1(3) . . . . ?
C22 C23 C24 C25 0.8(4) . . . . ?
C26 C23 C24 C25 -179.2(3) . . . . ?
C23 C24 C25 C20 -0.8(4) . . . . ?
C21 C20 C25 C24 0.8(4) . . . . ?
S1 C20 C25 C24 176.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.044
