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

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

data_shelxa
_database_code_depnum_ccdc_archive 'CCDC 1042624'
_audit_update_record             
;
2015-01-08 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_compound_source        'Isabelle Kirby'
_database_code_CSD               ?
_chemical_name_systematic        
;
 1-(4-nitrophenyl)-3-(phenyl)urea
;
_chemical_name_common            1-(4-nitrophenyl)-3-(phenyl)urea
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 N3 O3'
_chemical_formula_sum            'C13 H11 N3 O3'
_chemical_formula_weight         257.25

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           Monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   4.590(4)
_cell_length_b                   8.336(7)
_cell_length_c                   15.282(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.929(17)
_cell_angle_gamma                90.00
_cell_volume                     580.5(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1424
_cell_measurement_theta_min      3.6
_cell_measurement_theta_max      27.5

_exptl_crystal_description       needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             268
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9872
_exptl_absorpt_correction_T_max  0.9978
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_reflns_number            5340
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.63
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1408
_reflns_number_gt                1298
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'WINGX (Farrugia, 1998)'

_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 > 2σ(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)+(0.0696P)²+0.0690P] 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    4(5)
_refine_ls_number_reflns         1408
_refine_ls_number_parameters     173
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.1159
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.070
_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
C11 C 0.9453(6) 0.7635(4) 0.72921(19) 0.0231(6) Uani 1 1 d . . .
H11 H 1.0373 0.7574 0.7882 0.028 Uiso 1 1 calc R . .
C12 C 1.0365(6) 0.6650(4) 0.66513(18) 0.0233(6) Uani 1 1 d . . .
H12 H 1.1928 0.5917 0.6804 0.028 Uiso 1 1 calc R . .
C13 C 0.9030(6) 0.6717(4) 0.57864(18) 0.0212(6) Uani 1 1 d . . .
H13 H 0.9654 0.6024 0.5352 0.025 Uiso 1 1 calc R . .
C8 C 0.6778(5) 0.7805(4) 0.55639(17) 0.0179(5) Uani 1 1 d . . .
C9 C 0.5857(6) 0.8809(4) 0.62047(19) 0.0230(6) Uani 1 1 d . . .
H9 H 0.4320 0.9557 0.6050 0.028 Uiso 1 1 calc R . .
C10 C 0.7179(6) 0.8718(4) 0.70688(18) 0.0232(6) Uani 1 1 d . . .
H10 H 0.6533 0.9394 0.7507 0.028 Uiso 1 1 calc R . .
C7 C 0.6597(5) 0.7898(4) 0.39564(16) 0.0174(5) Uani 1 1 d . . .
C4 C 0.5593(5) 0.8038(4) 0.23489(17) 0.0190(6) Uani 1 1 d . . .
C5 C 0.7641(6) 0.6915(4) 0.21276(18) 0.0215(6) Uani 1 1 d . . .
H5 H 0.8488 0.6173 0.2557 0.026 Uiso 1 1 calc R . .
C6 C 0.8433(6) 0.6884(4) 0.12829(19) 0.0251(6) Uani 1 1 d . . .
H6 H 0.9831 0.6130 0.1126 0.030 Uiso 1 1 calc R . .
C1 C 0.7151(6) 0.7974(4) 0.06721(18) 0.0255(6) Uani 1 1 d . . .
C2 C 0.5101(7) 0.9078(4) 0.0873(2) 0.0282(7) Uani 1 1 d . . .
H2 H 0.4244 0.9807 0.0438 0.034 Uiso 1 1 calc R . .
C3 C 0.4312(7) 0.9110(4) 0.17162(18) 0.0241(6) Uani 1 1 d . . .
H3 H 0.2897 0.9862 0.1865 0.029 Uiso 1 1 calc R . .
N3 N 0.5259(5) 0.7894(3) 0.46939(13) 0.0200(5) Uani 1 1 d . . .
H3A H 0.3331 0.7950 0.4635 0.024 Uiso 1 1 calc R . .
N2 N 0.4692(5) 0.8068(3) 0.31918(14) 0.0188(5) Uani 1 1 d . . .
H2A H 0.2815 0.8203 0.3236 0.023 Uiso 1 1 calc R . .
N1 N 0.8002(6) 0.7965(4) -0.02183(16) 0.0323(6) Uani 1 1 d . . .
O1 O 0.9265(4) 0.7792(4) 0.39535(12) 0.0220(4) Uani 1 1 d . . .
O2 O 0.9905(6) 0.6992(6) -0.03874(15) 0.0484(7) Uani 1 1 d . . .
O3 O 0.6800(7) 0.8914(5) -0.07619(15) 0.0478(7) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C11 C12 1.381(4) . ?
C11 C10 1.391(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(4) . ?
C12 H12 0.9500 . ?
C13 C8 1.387(4) . ?
C13 H13 0.9500 . ?
C8 C9 1.392(4) . ?
C8 N3 1.427(3) . ?
C9 C10 1.387(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C7 O1 1.228(3) . ?
C7 N3 1.347(3) . ?
C7 N2 1.379(3) . ?
C4 C3 1.394(4) . ?
C4 C5 1.396(4) . ?
C4 N2 1.400(3) . ?
C5 C6 1.383(4) . ?
C5 H5 0.9500 . ?
C6 C1 1.382(4) . ?
C6 H6 0.9500 . ?
C1 C2 1.378(5) . ?
C1 N1 1.460(4) . ?
C2 C3 1.380(4) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
N3 H3A 0.8800 . ?
N2 H2A 0.8800 . ?
N1 O3 1.229(4) . ?
N1 O2 1.242(5) . ?

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
C12 C11 C10 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.9(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C8 C13 C12 119.3(3) . . ?
C8 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C8 C9 120.1(3) . . ?
C13 C8 N3 121.9(2) . . ?
C9 C8 N3 118.0(2) . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 119.9(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
O1 C7 N3 123.9(2) . . ?
O1 C7 N2 122.3(2) . . ?
N3 C7 N2 113.8(2) . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 N2 118.7(3) . . ?
C5 C4 N2 121.1(3) . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C1 C6 C5 118.7(3) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C2 C1 C6 122.3(3) . . ?
C2 C1 N1 118.6(3) . . ?
C6 C1 N1 119.1(3) . . ?
C1 C2 C3 119.0(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C7 N3 C8 124.0(2) . . ?
C7 N3 H3A 118.0 . . ?
C8 N3 H3A 118.0 . . ?
C7 N2 C4 123.4(2) . . ?
C7 N2 H2A 118.3 . . ?
C4 N2 H2A 118.3 . . ?
O3 N1 O2 123.4(3) . . ?
O3 N1 C1 118.6(3) . . ?
O2 N1 C1 118.1(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A O1 0.88 2.03 2.847(4) 154.2 1_455
N2 H2A O1 0.88 2.10 2.883(3) 148.1 1_455

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_shelxa
_database_code_depnum_ccdc_archive 'CCDC 1042625'
_audit_update_record             
;
2015-01-08 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '1-(4-nitrophenyl)-3-phenyl thiourea'
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 N3 O2 S'
_chemical_formula_sum            'C13 H11 N3 O2 S'
_chemical_formula_weight         273.31

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   5.6328(7)
_cell_length_b                   7.7579(9)
_cell_length_c                   28.178(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.324(7)
_cell_angle_gamma                90.00
_cell_volume                     1230.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6421
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9515
_exptl_absorpt_correction_T_max  0.9947
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6629
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2136
_reflns_number_gt                1738
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.0487P)²+0.7248P] 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_number_reflns         2136
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.1002
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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
C1 C 0.0079(4) 0.3901(3) 0.07417(8) 0.0200(5) Uani 1 1 d . . .
C2 C 0.1683(4) 0.4945(3) 0.09936(8) 0.0212(5) Uani 1 1 d . . .
H2 H 0.3130 0.5284 0.0859 0.025 Uiso 1 1 calc R . .
C3 C 0.1146(4) 0.5480(3) 0.14411(8) 0.0217(5) Uani 1 1 d . . .
H3 H 0.2230 0.6183 0.1621 0.026 Uiso 1 1 calc R . .
C4 C -0.0991(4) 0.4987(3) 0.16290(8) 0.0187(5) Uani 1 1 d . . .
C5 C -0.2605(4) 0.3983(3) 0.13671(8) 0.0220(5) Uani 1 1 d . . .
H5 H -0.4081 0.3683 0.1496 0.026 Uiso 1 1 calc R . .
C6 C -0.2073(4) 0.3418(3) 0.09187(8) 0.0231(5) Uani 1 1 d . . .
H6 H -0.3155 0.2717 0.0738 0.028 Uiso 1 1 calc R . .
C7 C -0.0745(4) 0.4849(3) 0.24998(8) 0.0176(5) Uani 1 1 d . . .
C8 C -0.0974(4) 0.4970(3) 0.33691(8) 0.0184(5) Uani 1 1 d . . .
C9 C 0.1224(4) 0.5382(3) 0.35821(8) 0.0210(5) Uani 1 1 d . . .
H9 H 0.2364 0.6006 0.3412 0.025 Uiso 1 1 calc R . .
C10 C 0.1730(4) 0.4869(3) 0.40472(8) 0.0218(5) Uani 1 1 d . . .
H10 H 0.3232 0.5136 0.4195 0.026 Uiso 1 1 calc R . .
C11 C 0.0071(4) 0.3971(3) 0.42982(8) 0.0230(5) Uani 1 1 d . . .
H11 H 0.0431 0.3627 0.4616 0.028 Uiso 1 1 calc R . .
C12 C -0.2120(4) 0.3577(3) 0.40840(8) 0.0224(5) Uani 1 1 d . . .
H12 H -0.3265 0.2962 0.4256 0.027 Uiso 1 1 calc R . .
C13 C -0.2643(4) 0.4078(3) 0.36182(8) 0.0204(5) Uani 1 1 d . . .
H13 H -0.4145 0.3809 0.3471 0.025 Uiso 1 1 calc R . .
N1 N 0.0722(4) 0.3268(3) 0.02712(7) 0.0253(5) Uani 1 1 d . . .
N2 N -0.1614(3) 0.5565(2) 0.20893(7) 0.0207(4) Uani 1 1 d . . .
H2A H -0.2614 0.6432 0.2107 0.025 Uiso 1 1 calc R . .
N3 N -0.1589(3) 0.5549(2) 0.28959(6) 0.0202(4) Uani 1 1 d . . .
H3A H -0.2585 0.6419 0.2863 0.024 Uiso 1 1 calc R . .
O1 O -0.0644(3) 0.2249(2) 0.00645(6) 0.0374(5) Uani 1 1 d . . .
O2 O 0.2582(3) 0.3763(2) 0.01095(6) 0.0363(5) Uani 1 1 d . . .
S1 S 0.11988(10) 0.31879(8) 0.25061(2) 0.02038(19) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.381(3) . ?
C1 C2 1.387(3) . ?
C1 N1 1.473(3) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(3) . ?
C4 N2 1.430(3) . ?
C5 C6 1.382(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N3 1.345(3) . ?
C7 N2 1.356(3) . ?
C7 S1 1.691(2) . ?
C8 C13 1.381(3) . ?
C8 C9 1.391(3) . ?
C8 N3 1.436(3) . ?
C9 C10 1.388(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
N1 O2 1.221(3) . ?
N1 O1 1.233(3) . ?
N2 H2A 0.8800 . ?
N3 H3A 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.4(2) . . ?
C6 C1 N1 119.1(2) . . ?
C2 C1 N1 118.5(2) . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 N2 118.6(2) . . ?
C3 C4 N2 120.5(2) . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C1 C6 C5 118.1(2) . . ?
C1 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
N3 C7 N2 114.5(2) . . ?
N3 C7 S1 123.32(17) . . ?
N2 C7 S1 122.16(17) . . ?
C13 C8 C9 120.5(2) . . ?
C13 C8 N3 119.0(2) . . ?
C9 C8 N3 120.4(2) . . ?
C10 C9 C8 119.1(2) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.8(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 120.0(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C12 119.9(2) . . ?
C8 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
O2 N1 O1 123.6(2) . . ?
O2 N1 C1 118.50(19) . . ?
O1 N1 C1 117.9(2) . . ?
C7 N2 C4 123.50(19) . . ?
C7 N2 H2A 118.3 . . ?
C4 N2 H2A 118.3 . . ?
C7 N3 C8 124.34(19) . . ?
C7 N3 H3A 117.8 . . ?
C8 N3 H3A 117.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A S1 0.88 2.70 3.514(2) 154.1 2_455
N3 H3A S1 0.88 2.63 3.4608(19) 157.0 2_455

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.058

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1042626'
_audit_update_record             
;
2015-01-08 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            1,3-bis(4-nitrophenyl)urea
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 N4 O5'
_chemical_formula_sum            'C13 H10 N4 O5'
_chemical_formula_weight         302.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0032 0.0015 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0108 0.0057 '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 n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'

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

_cell_length_a                   13.8899(18)
_cell_length_b                   24.389(3)
_cell_length_c                   3.6682(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1242.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    35(2)
_cell_measurement_reflns_used    2304
_cell_measurement_theta_min      1.6
_cell_measurement_theta_max      20.0

_exptl_crystal_description       lath
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9873
_exptl_absorpt_correction_T_max  0.9994
_exptl_absorpt_process_details   
;
DTABSCOR: 
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      35(2)
_diffrn_source_type              'DLS beamline I19'
_diffrn_source                   synchrotron

_diffrn_radiation_wavelength     0.68890
_diffrn_radiation_collimation    'Confocal mirrors'

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku Saturn724 (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  CrystalLogic
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_reflns_number            2790
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         26.57
_reflns_number_total             2790
_reflns_number_gt                2755
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'WINGX (Farrugia, 1998)'

_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 > 2σ(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)+(0.0883P)²+0.0248P] 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   0.1(8)
_refine_ls_number_reflns         2790
_refine_ls_number_parameters     199
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.1101
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.132
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.33117(9) 1.06155(5) 0.6045(4) 0.0099(3) Uani 1 1 d . . .
C2 C 1.37660(9) 1.01661(5) 0.4441(4) 0.0104(3) Uani 1 1 d . . .
H2 H 1.4433 1.0178 0.3874 0.013 Uiso 1 1 calc R . .
C3 C 1.32239(9) 0.97025(5) 0.3693(4) 0.0105(3) Uani 1 1 d . . .
H3 H 1.3524 0.9391 0.2631 0.013 Uiso 1 1 calc R . .
C4 C 1.22304(9) 0.96893(5) 0.4495(4) 0.0092(3) Uani 1 1 d . . .
C5 C 1.17803(9) 1.01536(5) 0.6020(4) 0.0106(3) Uani 1 1 d . . .
H5 H 1.1108 1.0152 0.6504 0.013 Uiso 1 1 calc R . .
C6 C 1.23305(9) 1.06142(5) 0.6808(4) 0.0102(3) Uani 1 1 d . . .
H6 H 1.2037 1.0928 0.7867 0.012 Uiso 1 1 calc R . .
C7 C 1.08715(9) 0.90305(5) 0.5057(4) 0.0098(3) Uani 1 1 d . . .
C8 C 0.99999(10) 0.81401(5) 0.5664(4) 0.0091(3) Uani 1 1 d . . .
C9 C 1.01305(9) 0.75693(5) 0.5263(4) 0.0102(3) Uani 1 1 d . . .
H9 H 1.0707 0.7433 0.4200 0.012 Uiso 1 1 calc R . .
C10 C 0.94271(9) 0.72067(5) 0.6403(4) 0.0105(3) Uani 1 1 d . . .
H10 H 0.9512 0.6822 0.6141 0.013 Uiso 1 1 calc R . .
C11 C 0.85890(9) 0.74210(5) 0.7950(4) 0.0095(3) Uani 1 1 d . . .
C12 C 0.84388(8) 0.79835(5) 0.8367(4) 0.0100(2) Uani 1 1 d . . .
H12 H 0.7858 0.8116 0.9416 0.012 Uiso 1 1 calc R . .
C13 C 0.91481(9) 0.83475(5) 0.7229(4) 0.0104(3) Uani 1 1 d . . .
H13 H 0.9060 0.8732 0.7504 0.012 Uiso 1 1 calc R . .
N1 N 1.38906(9) 1.10924(4) 0.7040(4) 0.0118(2) Uani 1 1 d . . .
N2 N 1.17557(8) 0.92010(4) 0.3695(4) 0.0102(2) Uani 1 1 d . . .
H2A H 1.2046 0.8977 0.2169 0.012 Uiso 1 1 calc R . .
N3 N 1.07490(8) 0.84717(5) 0.4442(3) 0.0101(2) Uani 1 1 d . . .
H3A H 1.1196 0.8309 0.3130 0.012 Uiso 1 1 calc R . .
N4 N 0.78707(8) 0.70450(5) 0.9289(3) 0.0103(2) Uani 1 1 d . . .
O1 O 1.03008(7) 0.93222(4) 0.6627(3) 0.0135(2) Uani 1 1 d . . .
O2 O 1.34874(8) 1.14806(4) 0.8583(3) 0.0162(2) Uani 1 1 d . . .
O3 O 1.47594(7) 1.10842(4) 0.6331(4) 0.0178(3) Uani 1 1 d . . .
O4 O 0.79812(7) 0.65456(4) 0.8824(4) 0.0153(2) Uani 1 1 d . . .
O5 O 0.71670(7) 0.72351(4) 1.0937(4) 0.0158(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.3913(16) . ?
C1 C2 1.3949(17) . ?
C1 N1 1.4604(16) . ?
C2 C3 1.3859(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.4114(16) . ?
C3 H3 0.9500 . ?
C4 N2 1.3927(16) . ?
C4 C5 1.4092(17) . ?
C5 C6 1.3890(16) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.2109(17) . ?
C7 N2 1.3894(16) . ?
C7 N3 1.3919(15) . ?
C8 N3 1.3920(16) . ?
C8 C13 1.4090(18) . ?
C8 C9 1.4115(16) . ?
C9 C10 1.3827(17) . ?
C9 H9 0.9500 . ?
C10 C11 1.3967(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.3960(16) . ?
C11 N4 1.4412(15) . ?
C12 C13 1.3902(16) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
N1 O3 1.2346(16) . ?
N1 O2 1.2370(16) . ?
N2 H2A 0.8800 . ?
N3 H3A 0.8800 . ?
N4 O5 1.2392(16) . ?
N4 O4 1.2395(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 121.75(11) . . ?
C6 C1 N1 119.40(11) . . ?
C2 C1 N1 118.82(11) . . ?
C3 C2 C1 118.61(12) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 120.56(12) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
N2 C4 C5 124.11(11) . . ?
N2 C4 C3 116.01(11) . . ?
C5 C4 C3 119.88(11) . . ?
C6 C5 C4 119.23(11) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 119.93(11) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O1 C7 N2 125.02(12) . . ?
O1 C7 N3 124.91(12) . . ?
N2 C7 N3 110.05(11) . . ?
N3 C8 C13 123.39(11) . . ?
N3 C8 C9 116.31(12) . . ?
C13 C8 C9 120.30(11) . . ?
C10 C9 C8 120.56(12) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 118.20(11) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
C10 C11 C12 122.47(12) . . ?
C10 C11 N4 118.51(10) . . ?
C12 C11 N4 118.98(12) . . ?
C13 C12 C11 119.26(11) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C8 119.21(11) . . ?
C12 C13 H13 120.4 . . ?
C8 C13 H13 120.4 . . ?
O3 N1 O2 123.45(12) . . ?
O3 N1 C1 118.20(11) . . ?
O2 N1 C1 118.34(11) . . ?
C7 N2 C4 126.77(11) . . ?
C7 N2 H2A 116.6 . . ?
C4 N2 H2A 116.6 . . ?
C8 N3 C7 127.45(12) . . ?
C8 N3 H3A 116.3 . . ?
C7 N3 H3A 116.3 . . ?
O5 N4 O4 122.16(12) . . ?
O5 N4 C11 118.31(11) . . ?
O4 N4 C11 119.51(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O4 0.88 2.19 3.0670(16) 170.9 3_564
N3 H3A O5 0.88 2.06 2.9161(16) 165.3 3_564

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        26.57
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.085
####################################################################### 
# 
# 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_shelxa
_database_code_depnum_ccdc_archive 'CCDC 1042627'
_audit_update_record             
;
2015-01-08 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            1,3-bis(4-nitrophenyl)thiourea
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 N4 O4 S'
_chemical_formula_sum            'C13 H10 N4 O4 S'
_chemical_formula_weight         318.31

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'
S S 0.1246 0.1234 '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/c
_symmetry_space_group_name_Hall  -P2ybc

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

_cell_length_a                   8.2109(5)
_cell_length_b                   25.4709(18)
_cell_length_c                   12.5244(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.054(2)
_cell_angle_gamma                90.00
_cell_volume                     2604.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    16648
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9521
_exptl_absorpt_correction_T_max  0.9945
_exptl_absorpt_process_details   
;
Jackson, R (1998). REQAB. Private communication to the Rigaku Corporation,
Toyko, Japan.
;
_exptl_special_details           
;
 ?
;
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'

_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_reflns_number            14351
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4557
_reflns_number_gt                3967
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;

_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;

_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;

_computing_structure_solution    
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'WINGX (Farrugia, 1998)'

_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 > 2σ(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)+(0.0829P)²+2.6239P] 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_number_reflns         4557
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1416
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
C1 C 0.0561(3) 0.83635(9) 1.06181(18) 0.0180(5) Uani 1 1 d . . .
C2 C 0.1664(3) 0.85527(9) 0.99413(19) 0.0183(5) Uani 1 1 d . . .
H2 H 0.1965 0.8913 0.9951 0.022 Uiso 1 1 calc R . .
C3 C 0.2308(3) 0.82057(9) 0.92572(18) 0.0175(5) Uani 1 1 d . . .
H3 H 0.3078 0.8327 0.8797 0.021 Uiso 1 1 calc R . .
C4 C 0.1845(3) 0.76755(9) 0.92297(18) 0.0176(5) Uani 1 1 d . . .
C5 C 0.0699(3) 0.75001(10) 0.9901(2) 0.0250(6) Uani 1 1 d . . .
H5 H 0.0355 0.7144 0.9875 0.030 Uiso 1 1 calc R . .
C6 C 0.0067(3) 0.78460(10) 1.0605(2) 0.0242(6) Uani 1 1 d . . .
H6 H -0.0696 0.7728 1.1072 0.029 Uiso 1 1 calc R . .
C7 C 0.2667(3) 0.68231(9) 0.84109(18) 0.0178(5) Uani 1 1 d . . .
C8 C 0.4191(3) 0.61938(9) 0.73077(18) 0.0177(5) Uani 1 1 d . . .
C9 C 0.5193(3) 0.62091(10) 0.64684(19) 0.0212(5) Uani 1 1 d . . .
H9 H 0.5404 0.6536 0.6143 0.025 Uiso 1 1 calc R . .
C10 C 0.5874(3) 0.57579(10) 0.6111(2) 0.0232(5) Uani 1 1 d . . .
H10 H 0.6551 0.5771 0.5541 0.028 Uiso 1 1 calc R . .
C11 C 0.5565(3) 0.52837(10) 0.65878(19) 0.0216(5) Uani 1 1 d . . .
C12 C 0.4593(3) 0.52565(10) 0.7419(2) 0.0235(5) Uani 1 1 d . . .
H12 H 0.4403 0.4928 0.7742 0.028 Uiso 1 1 calc R . .
C13 C 0.3895(3) 0.57086(10) 0.77828(19) 0.0211(5) Uani 1 1 d . . .
H13 H 0.3218 0.5691 0.8352 0.025 Uiso 1 1 calc R . .
C14 C 0.5626(3) 0.67141(9) 1.06611(18) 0.0171(5) Uani 1 1 d . . .
C15 C 0.6496(3) 0.69090(9) 0.98542(19) 0.0186(5) Uani 1 1 d . . .
H15 H 0.6526 0.7275 0.9712 0.022 Uiso 1 1 calc R . .
C16 C 0.7312(3) 0.65588(9) 0.92659(18) 0.0183(5) Uani 1 1 d . . .
H16 H 0.7908 0.6686 0.8709 0.022 Uiso 1 1 calc R . .
C17 C 0.7280(3) 0.60157(9) 0.94742(18) 0.0159(5) Uani 1 1 d . . .
C18 C 0.6382(3) 0.58306(9) 1.02871(19) 0.0203(5) Uani 1 1 d . . .
H18 H 0.6338 0.5465 1.0431 0.024 Uiso 1 1 calc R . .
C19 C 0.5558(3) 0.61813(10) 1.08789(19) 0.0200(5) Uani 1 1 d . . .
H19 H 0.4948 0.6058 1.1432 0.024 Uiso 1 1 calc R . .
C20 C 0.8386(3) 0.51679(9) 0.87898(18) 0.0161(5) Uani 1 1 d . . .
C21 C 0.9936(3) 0.45484(9) 0.76869(18) 0.0170(5) Uani 1 1 d . . .
C22 C 1.1018(3) 0.45747(10) 0.6894(2) 0.0228(5) Uani 1 1 d . . .
H22 H 1.1209 0.4903 0.6568 0.027 Uiso 1 1 calc R . .
C23 C 1.1808(3) 0.41331(11) 0.6580(2) 0.0255(6) Uani 1 1 d . . .
H23 H 1.2549 0.4156 0.6049 0.031 Uiso 1 1 calc R . .
C24 C 1.1510(3) 0.36562(10) 0.7045(2) 0.0212(5) Uani 1 1 d . . .
C25 C 1.0418(3) 0.36157(10) 0.7803(2) 0.0260(6) Uani 1 1 d . . .
H25 H 1.0211 0.3283 0.8104 0.031 Uiso 1 1 calc R . .
C26 C 0.9620(3) 0.40575(10) 0.8129(2) 0.0238(5) Uani 1 1 d . . .
H26 H 0.8862 0.4028 0.8649 0.029 Uiso 1 1 calc R . .
N1 N -0.0089(3) 0.87228(8) 1.13658(16) 0.0213(5) Uani 1 1 d . . .
N2 N 0.2576(3) 0.73586(8) 0.84970(16) 0.0196(4) Uani 1 1 d . . .
H2A H 0.3057 0.7533 0.8011 0.024 Uiso 1 1 calc R . .
N3 N 0.3572(2) 0.66816(8) 0.75951(16) 0.0185(4) Uani 1 1 d . . .
H3A H 0.3806 0.6943 0.7179 0.022 Uiso 1 1 calc R . .
N4 N 0.6271(3) 0.48057(9) 0.61803(19) 0.0274(5) Uani 1 1 d . . .
N5 N 0.4749(3) 0.70742(8) 1.12788(16) 0.0207(5) Uani 1 1 d . . .
N6 N 0.8147(2) 0.57024(7) 0.88095(16) 0.0178(4) Uani 1 1 d . . .
H6A H 0.8619 0.5877 0.8321 0.021 Uiso 1 1 calc R . .
N7 N 0.9257(2) 0.50307(8) 0.79538(16) 0.0180(4) Uani 1 1 d . . .
H7A H 0.9416 0.5289 0.7510 0.022 Uiso 1 1 calc R . .
N8 N 1.2362(3) 0.31891(9) 0.67087(18) 0.0279(5) Uani 1 1 d . . .
O1 O -0.0972(2) 0.85467(8) 1.20170(15) 0.0314(5) Uani 1 1 d . . .
O2 O 0.0257(2) 0.91927(7) 1.13316(16) 0.0313(5) Uani 1 1 d . . .
O3 O 0.5948(3) 0.43834(8) 0.65862(17) 0.0351(5) Uani 1 1 d . . .
O4 O 0.7157(3) 0.48464(8) 0.54485(16) 0.0338(5) Uani 1 1 d . . .
O5 O 0.4003(3) 0.69001(8) 1.20060(15) 0.0321(5) Uani 1 1 d . . .
O6 O 0.4777(2) 0.75471(7) 1.10727(14) 0.0260(4) Uani 1 1 d . . .
O7 O 1.2198(3) 0.27759(8) 0.71868(17) 0.0356(5) Uani 1 1 d . . .
O8 O 1.3209(3) 0.32314(8) 0.59542(17) 0.0379(5) Uani 1 1 d . . .
S1 S 0.17894(9) 0.63997(3) 0.91759(6) 0.0320(2) Uani 1 1 d . . .
S2 S 0.77189(9) 0.47429(3) 0.96427(6) 0.0320(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.378(4) . ?
C1 C2 1.390(3) . ?
C1 N1 1.451(3) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.402(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.399(3) . ?
C4 N2 1.404(3) . ?
C5 C6 1.385(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N2 1.371(3) . ?
C7 N3 1.373(3) . ?
C7 S1 1.657(2) . ?
C8 C9 1.402(3) . ?
C8 N3 1.404(3) . ?
C8 C13 1.404(3) . ?
C9 C10 1.374(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.383(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(4) . ?
C11 N4 1.463(3) . ?
C12 C13 1.385(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.387(3) . ?
C14 C15 1.389(3) . ?
C14 N5 1.441(3) . ?
C15 C16 1.375(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.408(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.400(3) . ?
C17 N6 1.400(3) . ?
C18 C19 1.382(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 N7 1.374(3) . ?
C20 N6 1.376(3) . ?
C20 S2 1.654(2) . ?
C21 C22 1.402(3) . ?
C21 C26 1.403(3) . ?
C21 N7 1.404(3) . ?
C22 C23 1.376(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.377(4) . ?
C24 N8 1.464(3) . ?
C25 C26 1.385(4) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
N1 O1 1.231(3) . ?
N1 O2 1.232(3) . ?
N2 H2A 0.8800 . ?
N3 H3A 0.8800 . ?
N4 O3 1.230(3) . ?
N4 O4 1.233(3) . ?
N5 O5 1.233(3) . ?
N5 O6 1.233(3) . ?
N6 H6A 0.8800 . ?
N7 H7A 0.8800 . ?
N8 O7 1.225(3) . ?
N8 O8 1.236(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.2(2) . . ?
C6 C1 N1 118.9(2) . . ?
C2 C1 N1 118.8(2) . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 120.9(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 N2 124.8(2) . . ?
C3 C4 N2 115.8(2) . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C1 C6 C5 119.1(2) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
N2 C7 N3 111.0(2) . . ?
N2 C7 S1 124.86(18) . . ?
N3 C7 S1 124.18(18) . . ?
C9 C8 N3 115.1(2) . . ?
C9 C8 C13 118.9(2) . . ?
N3 C8 C13 125.9(2) . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.3(2) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 121.2(2) . . ?
C12 C11 N4 120.2(2) . . ?
C10 C11 N4 118.6(2) . . ?
C11 C12 C13 120.0(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C8 119.8(2) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
C19 C14 C15 121.8(2) . . ?
C19 C14 N5 119.0(2) . . ?
C15 C14 N5 119.2(2) . . ?
C16 C15 C14 118.3(2) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
C15 C16 C17 121.2(2) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 N6 125.5(2) . . ?
C18 C17 C16 119.1(2) . . ?
N6 C17 C16 115.4(2) . . ?
C19 C18 C17 119.8(2) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C14 119.7(2) . . ?
C18 C19 H19 120.2 . . ?
C14 C19 H19 120.2 . . ?
N7 C20 N6 110.6(2) . . ?
N7 C20 S2 124.08(18) . . ?
N6 C20 S2 125.32(18) . . ?
C22 C21 C26 118.7(2) . . ?
C22 C21 N7 115.1(2) . . ?
C26 C21 N7 126.2(2) . . ?
C23 C22 C21 121.1(2) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 119.3(2) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C25 C24 C23 121.0(2) . . ?
C25 C24 N8 120.2(2) . . ?
C23 C24 N8 118.8(2) . . ?
C24 C25 C26 120.3(2) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C25 C26 C21 119.7(2) . . ?
C25 C26 H26 120.2 . . ?
C21 C26 H26 120.2 . . ?
O1 N1 O2 122.1(2) . . ?
O1 N1 C1 118.7(2) . . ?
O2 N1 C1 119.2(2) . . ?
C7 N2 C4 130.9(2) . . ?
C7 N2 H2A 114.6 . . ?
C4 N2 H2A 114.6 . . ?
C7 N3 C8 131.5(2) . . ?
C7 N3 H3A 114.3 . . ?
C8 N3 H3A 114.3 . . ?
O3 N4 O4 123.4(2) . . ?
O3 N4 C11 118.2(2) . . ?
O4 N4 C11 118.4(2) . . ?
O5 N5 O6 121.9(2) . . ?
O5 N5 C14 118.9(2) . . ?
O6 N5 C14 119.2(2) . . ?
C20 N6 C17 131.1(2) . . ?
C20 N6 H6A 114.5 . . ?
C17 N6 H6A 114.5 . . ?
C20 N7 C21 131.0(2) . . ?
C20 N7 H7A 114.5 . . ?
C21 N7 H7A 114.5 . . ?
O7 N8 O8 123.2(2) . . ?
O7 N8 C24 118.5(2) . . ?
O8 N8 C24 118.3(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O5 0.88 2.12 2.981(3) 167.3 4_575
N3 H3A O6 0.88 2.11 2.978(3) 166.9 4_575
N6 H6A O1 0.88 2.25 3.093(3) 161.3 4_675
N6 H6A S1 0.88 3.02 3.467(2) 113.8 1_655
N7 H7A O2 0.88 2.15 3.011(3) 166.8 4_675

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.771
_refine_diff_density_min         -0.743
_refine_diff_density_rms         0.074
####################################################################### 
# 
# 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_6615_13
_database_code_depnum_ccdc_archive 'CCDC 1042628'
_audit_update_record             
;
2015-01-08 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;

_audit_creation_date             '19-May-05 T10:19:29-00:00'
_audit_creation_method           'XD routine XDCIF'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_chemical_name_common            '1-(4-nitropheny)-3-phenylurea TEACl'
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 N3 O3, C8 H20 N, Cl'
_chemical_formula_sum            'C21 H31 Cl N4 O3'
_chemical_formula_weight         422.95

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0007 0.0007 '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 0.0777 0.0747 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0018 0.0014 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0040 0.0026 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_cell_length_a                   8.410(6)
_cell_length_b                   24.362(18)
_cell_length_c                   11.143(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.286(7)
_cell_angle_gamma                90
_cell_volume                     2191(3)
_cell_formula_units_Z            4


#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9882
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      34.0
_exptl_crystal_description       tablet
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9859
_exptl_absorpt_correction_T_max  0.9959
_exptl_absorpt_process_details   
;
DTABSCOR: 
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_source_type              'DLS beamline I19'
_diffrn_source                   synchrotron

_diffrn_radiation_wavelength     0.68890
_diffrn_radiation_collimation    'Confocal mirrors'

_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku Saturn724 (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714

_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  CrystalLogic
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_reflns_number            5019
_diffrn_reflns_av_r_equivalents  0.0832
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         26.57
_diffrn_reflns_theta_full        34.169
_diffrn_measured_fraction_theta_full 0.9570

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'Volkov et al, (2006)'
_computing_molecular_graphics    'Volkov et al, (2006)'
_computing_publication_material  'Volkov et al, (2006)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
        ?
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
        calc w1 = 1/[s²(Fo)]
;
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7950
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.057
_refine_ls_R_factor_gt           0.045
_refine_ls_wR_factor_ref         0.046
_refine_ls_goodness_of_fit_ref   1.831
_refine_ls_shift/su_max          0
_refine_ls_hydrogen_treatment    constr
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.085

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_symmetry_multiplicity
CL(1) 0.284672 0.073192 0.441733 0.025 1 4
O(1) 0.111058 0.062976 -0.02781 0.033 1 4
O(2) 0.604397 -0.160218 -0.053713 0.04 1 4
O(3) 0.696736 -0.177884 0.143742 0.042 1 4
N(1) 0.611541 -0.150842 0.055653 0.029 1 4
N(2) 0.250008 0.026795 0.164978 0.024 1 4
N(3) 0.097506 0.104707 0.154181 0.026 1 4
N(5) 0.820025 0.128312 0.502239 0.02 1 4
C(1) 0.515093 -0.105307 0.082784 0.025 1 4
C(2) 0.532057 -0.090855 0.206509 0.024 1 4
C(3) 0.441452 -0.046756 0.230027 0.022 1 4
C(4) 0.332343 -0.017357 0.131364 0.022 1 4
C(5) 0.314749 -0.033545 0.007254 0.029 1 4
C(6) 0.407467 -0.07726 -0.015983 0.03 1 4
C(7) 0.148705 0.064825 0.086262 0.025 1 4
C(8) 0.010042 0.152801 0.106785 0.024 1 4
C(9) 0.021425 0.196255 0.191068 0.028 1 4
C(10) -0.065065 0.245 0.153183 0.034 1 4
C(11) -0.163743 0.251142 0.029938 0.035 1 4
C(12) -0.175409 0.207663 -0.053595 0.034 1 4
C(13) -0.089964 0.158573 -0.016698 0.03 1 4
C(51) 0.840785 0.095544 0.391801 0.021 1 4
C(52) 0.714663 0.049919 0.348031 0.027 1 4
C(53) 0.648381 0.153865 0.472486 0.028 1 4
C(54) 0.602268 0.190431 0.357785 0.036 1 4
C(55) 0.954304 0.171981 0.529667 0.025 1 4
C(56) 0.959542 0.208868 0.639901 0.035 1 4
C(57) 0.836597 0.091039 0.614334 0.026 1 4
C(58) 1.002866 0.063338 0.665246 0.035 1 4
H(2) 0.616326 -0.113061 0.282329 0.036 1 4
H(3) 0.456203 -0.033805 0.325508 0.032 1 4
H(5) 0.2291 -0.010852 -0.066861 0.043 1 4
H(6) 0.401031 -0.090796 -0.109804 0.051 1 4
H(9) 0.100419 0.190094 0.28518 0.043 1 4
H(10) -0.051271 0.277585 0.221455 0.06 1 4
H(11) -0.231596 0.288672 -0.001668 0.059 1 4
H(12) -0.251267 0.212518 -0.149107 0.06 1 4
H(13) -0.10433 0.124556 -0.081436 0.046 1 4
H(51A) 0.966706 0.07924 0.42184 0.034 1 4
H(51B) 0.833632 0.126713 0.32005 0.035 1 4
H(52A) 0.745362 0.030208 0.272795 0.041 1 4
H(52B) 0.591789 0.06501 0.317591 0.047 1 4
H(52C) 0.724166 0.019418 0.417406 0.039 1 4
H(53A) 0.562864 0.11939 0.463583 0.05 1 4
H(53B) 0.650828 0.174409 0.560086 0.052 1 4
H(54A) 0.481457 0.205151 0.350554 0.072 1 4
H(54B) 0.605069 0.16965 0.274929 0.071 1 4
H(54C) 0.679353 0.225501 0.368213 0.068 1 4
H(55A) 1.068127 0.148434 0.541349 0.041 1 4
H(55B) 0.927051 0.19639 0.444111 0.047 1 4
H(56A) 1.057435 0.237549 0.652217 0.064 1 4
H(56B) 0.982447 0.186953 0.72513 0.049 1 4
H(56C) 0.846785 0.229962 0.631286 0.052 1 4
H(57A) 0.804665 0.117257 0.683622 0.046 1 4
H(57B) 0.735715 0.061524 0.583053 0.043 1 4
H(58A) 0.996707 0.036551 0.738658 0.06 1 4
H(58B) 1.098 0.092347 0.701497 0.067 1 4
H(58C) 1.039763 0.040809 0.596299 0.072 1 4
H(2A) 0.274576 0.034353 0.25741 0.031 1 4
H(3A) 0.152839 0.102934 0.246994 0.032 1 4



#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
_atom_rho_multipole_radial_slater_n0
_atom_rho_multipole_radial_slater_zeta0
_atom_rho_multipole_radial_slater_n1
_atom_rho_multipole_radial_slater_zeta1
_atom_rho_multipole_radial_slater_n2
_atom_rho_multipole_radial_slater_zeta2
_atom_rho_multipole_radial_slater_n3
_atom_rho_multipole_radial_slater_zeta3
_atom_rho_multipole_radial_slater_n4
_atom_rho_multipole_radial_slater_zeta4
CL(1) 7.54(6) 0 -0.053(19) -0.01(2) -0.02(2) -0.03(2) 0.03(2) -0.06(2)
-0.015(19) -0.011(19) -0.04(2) 0.02(2) -0.044(19) 0.01(2) -0.003(19) 0.093(19)
0.024(19) 0.04(2) 0.05(2) 0.04(2) -0.04(2) 0.01(2) 0.05(2) -0.02(2) 0.03(2)
0.00(2) 1.010613 1 1 1 1 1 4 4.2587714285714 4 4.2587714285714 4
4.2587714285714 4 4.2587714285714 4 4.2587714285714
O(1) 6.02(4) 0 0 0 -0.071(12) -0.035(15) 0 0 0.077(16) 0 -0.02(2) 0 0 -0.08(2)
0 0 0 -0.03(3) 0 0 0.01(2) 0 0 0 0.01(3) 0 0.996796 1.146904 1.146904 1.146904
1.146904 1.146904 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(2) 5.97(3) 0 -0.084(11) -0.014(11) 0 -0.177(15) 0 0 -0.106(13) -0.006(13) 0
0.086(19) 0.025(18) 0 0 0.036(15) 0.006(15) 0.00(3) 0 0 0.04(2) 0.01(2) 0 0
-0.016(19) 0.018(18) 1.003886 1.086474 1.086474 1.086474 1.086474 1.086474 2
4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(3) 5.9672 0 -0.0837 -0.0135 0 -0.1771 0 0 -0.1057 -0.0055 0 0.0858 0.0253 0 0
0.0364 0.0059 0.0004 0 0 0.0376 0.0064 0 0 -0.0156 0.0183 1.003886 1.086474
1.086474 1.086474 1.086474 1.086474 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
N(1) 4.98(4) 0 0 0 -0.03(2) 0.07(2) 0 0 -0.20(2) 0 0.21(3) 0 0 0.20(3) 0 0 0
0.07(4) 0 0 0.04(4) 0 0 0 -0.09(4) 0 0.998662 0.839998 0.839998 0.839998
0.839998 0.839998 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
N(2) 5.05(4) 0 0.012(14) -0.027(16) 0.042(13) 0.050(15) -0.006(14) -0.023(14)
0.005(14) 0.003(15) 0.02(2) 0.000(19) -0.033(19) -0.027(18) -0.013(19)
0.166(19) 0.042(17) -0.02(3) 0.00(2) 0.00(2) 0.01(2) -0.03(2) 0.01(2) 0.01(2)
-0.01(2) -0.03(2) 1.008594 1.03714 1.03714 1.03714 1.03714 1.03714 2 3.83936 2
3.83936 2 3.83936 3 3.83936 4 3.83936
N(3) 4.99(4) 0 0.004(15) -0.013(16) 0.061(14) 0.059(16) -0.016(15) -0.031(15)
0.006(15) 0.009(14) 0.01(2) 0.04(2) -0.024(19) -0.032(19) 0.020(19) 0.156(19)
-0.018(18) 0.02(3) 0.03(2) -0.01(2) 0.00(2) 0.00(2) 0.03(2) -0.03(2) -0.01(2)
-0.04(2) 1.008594 1.03714 1.03714 1.03714 1.03714 1.03714 2 3.83936 2 3.83936 2
3.83936 3 3.83936 4 3.83936
N(5) 5.20(4) 0 0 0 -0.058(17) 0.031(17) 0 0 0 0 0.24(2) 0 0 0 0 -0.022(19)
-0.18(2) -0.02(3) 0 0 0 0 0.01(3) 0.07(3) 0 0 0.991952 0.872472 0.872472
0.872472 0.872472 0.872472 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
C(1) 4.07(4) 0 0 0 -0.029(13) 0.045(12) 0 0 -0.189(12) 0 0.224(18) 0 0
0.127(16) 0 0 0 0 0 0 0 0 0 0 0 0 1.01374 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762
3 3.1762 4 3.1762
C(2) 3.98(2) 0 0.019(8) 0.056(10) 0 -0.147(9) 0 0 0.025(8) -0.033(8) 0 0.008(9)
0.016(11) 0 0 0.253(10) 0.013(10) 0 0 0 0 0 0 0 0 0 1.019199 1 1 1 1 1 2 3.1762
2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(3) 3.9786 0 0.0189 0.0564 0 -0.1474 0 0 0.0247 -0.0331 0 0.0079 0.0156 0 0
0.253 0.0133 0 0 0 0 0 0 0 0 0 1.019199 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(4) 4.0672 0 0 0 -0.0287 0.0453 0 0 -0.1886 0 0.2235 0 0 0.127 0 0 0 0 0 0 0 0
0 0 0 0 1.01374 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(5) 3.9786 0 0.0189 0.0564 0 -0.1474 0 0 0.0247 -0.0331 0 0.0079 0.0156 0 0
0.253 0.0133 0 0 0 0 0 0 0 0 0 1.019199 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(6) 3.9786 0 0.0189 0.0564 0 -0.1474 0 0 0.0247 -0.0331 0 0.0079 0.0156 0 0
0.253 0.0133 0 0 0 0 0 0 0 0 0 1.019199 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(7) 4.08(6) 0 0 0 0.10(2) 0.24(2) 0 0 -0.18(2) 0 0.28(3) 0 0 0.22(3) 0 0 0 0 0
0 0 0 0 0 0 0 1.008591 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(8) 4.0672 0 0 0 -0.0287 0.0453 0 0 -0.1886 0 0.2235 0 0 0.127 0 0 0 0 0 0 0 0
0 0 0 0 1.01374 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(9) 3.9786 0 0.0189 0.0564 0 -0.1474 0 0 0.0247 -0.0331 0 0.0079 0.0156 0 0
0.253 0.0133 0 0 0 0 0 0 0 0 0 1.019199 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(10) 3.93(3) 0 0 0 0.084(11) 0.059(11) 0 0 0.161(11) 0 -0.207(14) 0 0
0.098(14) 0 0 0 0 0 0 0 0 0 0 0 0 1.017274 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762
3 3.1762 4 3.1762
C(11) 3.9269 0 0 0 0.0838 0.0585 0 0 0.1612 0 -0.207 0 0 0.0983 0 0 0 0 0 0 0 0
0 0 0 0 1.017274 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(12) 3.9269 0 0 0 0.0838 0.0585 0 0 0.1612 0 -0.207 0 0 0.0983 0 0 0 0 0 0 0 0
0 0 0 0 1.017274 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(13) 3.9786 0 0.0189 0.0564 0 -0.1474 0 0 0.0247 -0.0331 0 0.0079 0.0156 0 0
0.253 0.0133 0 0 0 0 0 0 0 0 0 1.019199 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(51) 3.90(3) 0 -0.039(10) 0.000(10) 0 0.014(11) 0 0 -0.060(10) -0.033(10) 0
-0.121(12) -0.160(13) 0 0 0.162(13) -0.019(11) 0 0 0 0 0 0 0 0 0 1.009768 1 1 1
1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(52) 3.75(2) 0 0 0 0.035(11) 0.016(11) 0 0 0 0 0.241(15) 0 0 0 0 0.100(13) 0 0
0 0 0 0 0 0 0 0 1.018393 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(53) 3.8971 0 -0.0392 0.0002 0 0.0136 0 0 -0.0596 -0.0327 0 -0.1213 -0.1596 0
0 0.1615 -0.019 0 0 0 0 0 0 0 0 0 1.009768 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762
3 3.1762 4 3.1762
C(54) 3.7487 0 0 0 0.0351 0.0161 0 0 0 0 0.2405 0 0 0 0 0.1001 0 0 0 0 0 0 0 0
0 0 1.018393 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(55) 3.8971 0 -0.0392 0.0002 0 0.0136 0 0 -0.0596 -0.0327 0 -0.1213 -0.1596 0
0 0.1615 -0.019 0 0 0 0 0 0 0 0 0 1.009768 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762
3 3.1762 4 3.1762
C(56) 3.7487 0 0 0 0.0351 0.0161 0 0 0 0 0.2405 0 0 0 0 0.1001 0 0 0 0 0 0 0 0
0 0 1.018393 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(57) 3.8971 0 -0.0392 0.0002 0 0.0136 0 0 -0.0596 -0.0327 0 -0.1213 -0.1596 0
0 0.1615 -0.019 0 0 0 0 0 0 0 0 0 1.009768 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762
3 3.1762 4 3.1762
C(58) 3.7487 0 0 0 0.0351 0.0161 0 0 0 0 0.2405 0 0 0 0 0.1001 0 0 0 0 0 0 0 0
0 0 1.018393 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
H(2) 1.04(3) 0 0 0 0.17(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13642
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(3) 0.9769 0 0 0 0.1546 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13642 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(5) 0.9769 0 0 0 0.1546 0.0629 0 0 0 0 0.0127 0 0 0 0 0 0 -0.002 0 0 0 0 0 0 0
0 1.13642 1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(6) 0.9769 0 0 0 0.1546 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13642 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(9) 0.9769 0 0 0 0.1546 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13642 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(10) 0.9769 0 0 0 0.1546 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13642 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(11) 0.9769 0 0 0 0.1546 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13642 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(12) 0.9769 0 0 0 0.1546 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13642 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(13) 0.9769 0 0 0 0.1546 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13642 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(51A) 1.03(3) 0 0 0 0.19(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.113134
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(51B) 1.0624 0 0 0 0.1508 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.113134
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(52A) 1.00(3) 0 0 0 0.15(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.114404
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(52B) 1.05 0 0 0 0.1512 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.114404 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(52C) 1.05 0 0 0 0.1512 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.114404 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(53A) 1.0624 0 0 0 0.1508 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.113134
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(53B) 1.0624 0 0 0 0.1508 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.113134
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(54A) 1.05 0 0 0 0.1512 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.114404 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(54B) 1.05 0 0 0 0.1512 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.114404 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(54C) 1.05 0 0 0 0.1512 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.114404 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(55A) 1.01(4) 0 0 0 0.15(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.113134
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(55B) 1.0624 0 0 0 0.1508 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.113134
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(56A) 1.05 0 0 0 0.1512 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.114404 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(56B) 1.05 0 0 0 0.1512 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.114404 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(56C) 1.05 0 0 0 0.1512 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.114404 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(57A) 1.0624 0 0 0 0.1508 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.113134
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(57B) 1.0624 0 0 0 0.1508 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.113134
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(58A) 1.05 0 0 0 0.1512 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.114404 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(58B) 1.05 0 0 0 0.1512 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.114404 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(58C) 1.05 0 0 0 0.1512 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.114404 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(2A) 0.86(4) 0 0 0 0.19(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.138113
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(3A) 0.83(4) 0 0 0 0.23(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.138113
1.2 1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
CL(1) H(2A) Z CL(1) H(3A) Y
O(1) C(7) Z O(1) N(3) X
O(2) N(1) X O(2) O(3) Y
O(3) N(1) X O(3) O(2) Y
N(1) C(1) Z N(1) O(2) Y
N(2) C(4) X N(2) C(7) Y
N(3) C(7) X N(3) C(8) Y
N(5) C(51) Z N(5) C(57) Y
C(1) N(1) Z C(1) C(2) Y
C(2) C(3) X C(2) C(1) Y
C(3) C(2) X C(3) C(4) Y
C(4) N(2) Z C(4) C(5) Y
C(5) C(6) X C(5) C(4) Y
C(6) C(5) X C(6) C(1) Y
C(7) O(1) Z C(7) N(3) Y
C(8) N(3) Z C(8) C(9) Y
C(9) C(10) X C(9) C(8) Y
C(10) DUM1 Z C(10) C(9) X
C(11) DUM2 Z C(11) C(12) X
C(12) DUM3 Z C(12) C(11) X
C(13) C(12) X C(13) C(8) Y
C(51) N(5) X C(51) C(52) Y
C(52) C(51) Z C(52) H(52C) X
C(53) N(5) X C(53) C(54) Y
C(54) C(53) Z C(54) H(54C) X
C(55) N(5) X C(55) C(56) Y
C(56) C(55) Z C(56) H(56B) X
C(57) N(5) X C(57) C(58) Y
C(58) C(57) Z C(58) H(58C) X
H(2) C(2) Z H(2) C(3) Y
H(3) C(3) Z H(3) C(2) Y
H(5) C(5) Z H(5) C(6) Y
H(6) C(6) Z H(6) C(5) Y
H(9) C(9) Z H(9) C(10) Y
H(10) C(10) Z H(10) C(9) Y
H(11) C(11) Z H(11) C(12) Y
H(12) C(12) Z H(12) C(11) Y
H(13) C(13) Z H(13) C(12) Y
H(51A) C(51) Z H(51A) N(5) Y
H(51B) C(51) Z H(51B) N(5) Y
H(52A) C(52) Z H(52A) C(51) Y
H(52B) C(52) Z H(52B) C(51) Y
H(52C) C(52) Z H(52C) C(51) Y
H(53A) C(53) Z H(53A) N(5) Y
H(53B) C(53) Z H(53B) N(5) Y
H(54A) C(54) Z H(54A) C(53) Y
H(54B) C(54) Z H(54B) C(53) Y
H(54C) C(54) Z H(54C) C(53) Y
H(55A) C(55) Z H(55A) N(5) Y
H(55B) C(55) Z H(55B) N(5) Y
H(56A) C(56) Z H(56A) C(55) Y
H(56B) C(56) Z H(56B) C(55) Y
H(56C) C(56) Z H(56C) C(55) Y
H(57A) C(57) Z H(57A) N(5) Y
H(57B) C(57) Z H(57B) N(5) Y
H(58A) C(58) Z H(58A) C(57) Y
H(58B) C(58) Z H(58B) C(57) Y
H(58C) C(58) Z H(58C) C(57) Y
H(2A) N(2) Z H(2A) C(4) Y
H(3A) N(3) Z H(3A) C(7) Y


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(1) C(7) 1.2215807917951 1_555 1_555 yes
O(2) N(1) 1.2246891562303 1_555 1_555 yes
O(3) N(1) 1.2314272719 1_555 1_555 yes
N(1) C(1) 1.4551500301222 1_555 1_555 yes
N(2) C(4) 1.3864392995426 1_555 1_555 yes
N(2) C(7) 1.3908451196381 1_555 1_555 yes
N(2) H(2A) 1.0089963898683 1_555 1_555 yes
N(3) C(7) 1.3729418731261 1_555 1_555 yes
N(3) C(8) 1.4053147236404 1_555 1_555 yes
N(3) H(3A) 1.0090038334068 1_555 1_555 yes
C(1) C(2) 1.3909423976159 1_555 1_555 yes
C(1) C(6) 1.392360460599 1_555 1_555 yes
C(2) C(3) 1.3840182208311 1_555 1_555 yes
C(2) H(2) 1.0830017250427 1_555 1_555 yes
C(3) C(4) 1.4134515604595 1_555 1_555 yes
C(3) H(3) 1.0829995129038 1_555 1_555 yes
C(4) C(5) 1.4054267611067 1_555 1_555 yes
C(5) C(6) 1.3865430378521 1_555 1_555 yes
C(5) H(5) 1.0830001197589 1_555 1_555 yes
C(6) H(6) 1.0830033617171 1_555 1_555 yes
C(8) C(9) 1.4005208278064 1_555 1_555 yes
C(8) C(13) 1.4040540290016 1_555 1_555 yes
C(9) C(10) 1.394737304718 1_555 1_555 yes
C(9) H(9) 1.0829953315962 1_555 1_555 yes
C(10) C(11) 1.3992442760555 1_555 1_555 yes
C(10) H(10) 1.0829966807405 1_555 1_555 yes
C(11) C(12) 1.3952735206432 1_555 1_555 yes
C(11) H(11) 1.0830081666261 1_555 1_555 yes
C(12) C(13) 1.3964100144958 1_555 1_555 yes
C(12) H(12) 1.0829989519786 1_555 1_555 yes
C(13) H(13) 1.0829943598714 1_555 1_555 yes
C(51) C(52) 1.5192923778073 1_555 1_555 yes
C(51) H(51A) 1.0920018795762 1_555 1_555 yes
C(51) H(51B) 1.0920047622798 1_555 1_555 yes
C(52) H(52A) 1.0590007995918 1_555 1_555 yes
C(52) H(52B) 1.0589999435871 1_555 1_555 yes
C(52) H(52C) 1.0590006343582 1_555 1_555 yes
C(53) C(54) 1.5164208750065 1_555 1_555 yes
C(53) H(53A) 1.0920017721194 1_555 1_555 yes
C(53) H(53B) 1.0920040704967 1_555 1_555 yes
C(54) H(54A) 1.058997123621 1_555 1_555 yes
C(54) H(54B) 1.0589974607113 1_555 1_555 yes
C(54) H(54C) 1.0590003476383 1_555 1_555 yes
C(55) C(56) 1.5126001474593 1_555 1_555 yes
C(55) H(55A) 1.0920001656626 1_555 1_555 yes
C(55) H(55B) 1.0920019972888 1_555 1_555 yes
C(56) H(56A) 1.0589961548194 1_555 1_555 yes
C(56) H(56B) 1.0590023258988 1_555 1_555 yes
C(56) H(56C) 1.059004770092 1_555 1_555 yes
C(57) C(58) 1.5124974232765 1_555 1_555 yes
C(57) H(57A) 1.0920054810941 1_555 1_555 yes
C(57) H(57B) 1.0920025069634 1_555 1_555 yes
C(58) H(58A) 1.0590034969129 1_555 1_555 yes
C(58) H(58B) 1.0589986792125 1_555 1_555 yes
C(58) H(58C) 1.0590017092628 1_555 1_555 yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O(2) N(1) O(3) 123.27216344466 1_555 1_555 1_555 yes
O(2) N(1) C(1) 118.31168041515 1_555 1_555 1_555 yes
O(3) N(1) C(1) 118.41552333112 1_555 1_555 1_555 yes
C(4) N(2) C(7) 127.62087982696 1_555 1_555 1_555 yes
C(4) N(2) H(2A) 116.26579869581 1_555 1_555 1_555 yes
C(7) N(2) H(2A) 115.85315530868 1_555 1_555 1_555 yes
C(7) N(3) C(8) 126.50383514386 1_555 1_555 1_555 yes
C(7) N(3) H(3A) 114.13763138439 1_555 1_555 1_555 yes
C(8) N(3) H(3A) 117.59617190831 1_555 1_555 1_555 yes
N(1) C(1) C(2) 119.38537192312 1_555 1_555 1_555 yes
N(1) C(1) C(6) 119.11537159821 1_555 1_555 1_555 yes
C(2) C(1) C(6) 121.49908165761 1_555 1_555 1_555 yes
C(1) C(2) C(3) 118.37751726294 1_555 1_555 1_555 yes
C(1) C(2) H(2) 120.63556971204 1_555 1_555 1_555 yes
C(3) C(2) H(2) 120.97223444752 1_555 1_555 1_555 yes
C(2) C(3) C(4) 121.18904737149 1_555 1_555 1_555 yes
C(2) C(3) H(3) 119.64946015061 1_555 1_555 1_555 yes
C(4) C(3) H(3) 119.14568102622 1_555 1_555 1_555 yes
N(2) C(4) C(3) 116.58114606581 1_555 1_555 1_555 yes
N(2) C(4) C(5) 124.11134613766 1_555 1_555 1_555 yes
C(3) C(4) C(5) 119.30307589494 1_555 1_555 1_555 yes
C(4) C(5) C(6) 119.32448405482 1_555 1_555 1_555 yes
C(4) C(5) H(5) 118.1063061935 1_555 1_555 1_555 yes
C(6) C(5) H(5) 122.56738950454 1_555 1_555 1_555 yes
C(1) C(6) C(5) 120.28431585181 1_555 1_555 1_555 yes
C(1) C(6) H(6) 117.32421324873 1_555 1_555 1_555 yes
C(5) C(6) H(6) 122.38863405128 1_555 1_555 1_555 yes
O(1) C(7) N(2) 124.46010216726 1_555 1_555 1_555 yes
O(1) C(7) N(3) 124.73960508074 1_555 1_555 1_555 yes
N(2) C(7) N(3) 110.79989860823 1_555 1_555 1_555 yes
N(3) C(8) C(9) 116.61874499085 1_555 1_555 1_555 yes
N(3) C(8) C(13) 123.94207719875 1_555 1_555 1_555 yes
C(9) C(8) C(13) 119.40503127124 1_555 1_555 1_555 yes
C(8) C(9) C(10) 120.5866130884 1_555 1_555 1_555 yes
C(8) C(9) H(9) 116.91018672161 1_555 1_555 1_555 yes
C(10) C(9) H(9) 122.50125776529 1_555 1_555 1_555 yes
C(9) C(10) C(11) 120.23475584075 1_555 1_555 1_555 yes
C(9) C(10) H(10) 117.86873877035 1_555 1_555 1_555 yes
C(11) C(10) H(10) 121.88841310627 1_555 1_555 1_555 yes
C(10) C(11) C(12) 119.01023268323 1_555 1_555 1_555 yes
C(10) C(11) H(11) 121.52299579042 1_555 1_555 1_555 yes
C(12) C(11) H(11) 119.4655207381 1_555 1_555 1_555 yes
C(11) C(12) C(13) 121.30835704661 1_555 1_555 1_555 yes
C(11) C(12) H(12) 118.98095294714 1_555 1_555 1_555 yes
C(13) C(12) H(12) 119.70654780202 1_555 1_555 1_555 yes
C(8) C(13) C(12) 119.45127249783 1_555 1_555 1_555 yes
C(8) C(13) H(13) 120.02691890632 1_555 1_555 1_555 yes
C(12) C(13) H(13) 120.47509995152 1_555 1_555 1_555 yes
C(52) C(51) H(51A) 111.2242596887 1_555 1_555 1_555 yes
C(52) C(51) H(51B) 112.55259471155 1_555 1_555 1_555 yes
H(51A) C(51) H(51B) 109.08219379671 1_555 1_555 1_555 yes
C(51) C(52) H(52A) 106.41732644518 1_555 1_555 1_555 yes
C(51) C(52) H(52B) 112.30454485155 1_555 1_555 1_555 yes
C(51) C(52) H(52C) 112.08760226336 1_555 1_555 1_555 yes
H(52A) C(52) H(52B) 109.66297381894 1_555 1_555 1_555 yes
H(52A) C(52) H(52C) 105.93045495066 1_555 1_555 1_555 yes
H(52B) C(52) H(52C) 110.15188624762 1_555 1_555 1_555 yes
C(54) C(53) H(53A) 111.65403084077 1_555 1_555 1_555 yes
C(54) C(53) H(53B) 114.86141237589 1_555 1_555 1_555 yes
H(53A) C(53) H(53B) 106.29300994882 1_555 1_555 1_555 yes
C(53) C(54) H(54A) 106.03312214544 1_555 1_555 1_555 yes
C(53) C(54) H(54B) 113.01830650101 1_555 1_555 1_555 yes
C(53) C(54) H(54C) 112.17674714223 1_555 1_555 1_555 yes
H(54A) C(54) H(54B) 110.5476789788 1_555 1_555 1_555 yes
H(54A) C(54) H(54C) 106.25360758004 1_555 1_555 1_555 yes
H(54B) C(54) H(54C) 108.58728345274 1_555 1_555 1_555 yes
C(56) C(55) H(55A) 112.97732623137 1_555 1_555 1_555 yes
C(56) C(55) H(55B) 109.67142409896 1_555 1_555 1_555 yes
H(55A) C(55) H(55B) 110.63983895042 1_555 1_555 1_555 yes
C(55) C(56) H(56A) 109.98459423489 1_555 1_555 1_555 yes
C(55) C(56) H(56B) 112.66192771816 1_555 1_555 1_555 yes
C(55) C(56) H(56C) 113.15786011552 1_555 1_555 1_555 yes
H(56A) C(56) H(56B) 106.0891245877 1_555 1_555 1_555 yes
H(56A) C(56) H(56C) 109.59716916532 1_555 1_555 1_555 yes
H(56B) C(56) H(56C) 105.01047537929 1_555 1_555 1_555 yes
C(58) C(57) H(57A) 112.36960308263 1_555 1_555 1_555 yes
C(58) C(57) H(57B) 112.31748683846 1_555 1_555 1_555 yes
H(57A) C(57) H(57B) 106.72165419376 1_555 1_555 1_555 yes
C(57) C(58) H(58A) 108.92567683208 1_555 1_555 1_555 yes
C(57) C(58) H(58B) 111.43364656964 1_555 1_555 1_555 yes
C(57) C(58) H(58C) 112.78638214896 1_555 1_555 1_555 yes
H(58A) C(58) H(58B) 108.17791471621 1_555 1_555 1_555 yes
H(58A) C(58) H(58C) 109.19450201217 1_555 1_555 1_555 yes
H(58B) C(58) H(58C) 106.19190117965 1_555 1_555 1_555 yes

####################################################################### 
# 
# 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_cd9
_database_code_depnum_ccdc_archive 'CCDC 1042629'
_audit_update_record             
;
2015-01-08 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;

_audit_creation_date             '15-Jul-07 T09:31:07-00:00'
_audit_creation_method           'XD routine XDCIF'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 1-(4-nitrophenyl)-3-phenylthiourea TMA CL
;
_chemical_name_common            ' 1-(4-nitrophenyl)-3-phenylthiourea TMA CL'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C13 H11 N3 O2 S), C4 H12 N, Cl'
_chemical_formula_sum            'C30 H34 Cl N7 O4 S2'
_chemical_formula_weight         656.21

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z

_cell_length_a                   9.1587(14)
_cell_length_b                   10.2436(16)
_cell_length_c                   17.871(3)
_cell_angle_alpha                87.983(6)
_cell_angle_beta                 79.043(5)
_cell_angle_gamma                72.220(6)
_cell_volume                     1566.9(4)
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6567
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      34.9
_diffrn_reflns_theta_full        62.843
_diffrn_measured_fraction_theta_full 0.964

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7935
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_reflns_number            49621
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         62.84
_reflns_number_total             49621
_reflns_number_gt                44849
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'Volkov et al, (2006)'
_computing_molecular_graphics    'Volkov et al, (2006)'
_computing_publication_material  'Volkov et al, (2006)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
        ?
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
        calc w1 = 1/[s²(Fo)]
;
_refine_ls_extinction_method     none
_refine_ls_number_reflns         33801
_refine_ls_number_parameters     1212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.051
_refine_ls_R_factor_gt           0.035
_refine_ls_wR_factor_ref         0.045
_refine_ls_goodness_of_fit_ref   1.746
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.650
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.055

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_symmetry_multiplicity
CL(1) 0.342529(10) 0.166024(9) 0.278195(5) 0.016 1 2
S(1) 0.288069(16) -0.286337(11) 0.145619(6) 0.021 1 2
S(2) 0.932290(12) 0.130771(13) 0.315415(6) 0.019 1 2
O(1) 0.24039(15) 0.10599(9) -0.18911(4) 0.047 1 2
O(2) 0.32244(9) 0.27223(9) -0.15981(4) 0.034 1 2
O(3) 0.74951(6) 0.53017(4) -0.05424(2) 0.022 1 2
O(4) 0.98947(5) 0.40374(6) -0.06100(2) 0.024 1 2
N(1) 0.28238(6) 0.16855(5) -0.14368(3) 0.027 1 2
N(2) 0.30159(5) -0.02702(4) 0.15343(2) 0.018 1 2
N(3) 0.30899(5) -0.14035(4) 0.26295(2) 0.018 1 2
N(4) 0.85192(4) 0.44363(3) -0.028327(18) 0.017 1 2
N(5) 0.67743(4) 0.20770(4) 0.249628(19) 0.016 1 2
N(6) 0.66174(4) 0.06676(4) 0.346822(19) 0.016 1 2
N(7) 0.04269(4) 0.46487(4) -0.305988(19) 0.016 1 2
C(1) 0.28445(5) 0.11700(4) -0.06664(2) 0.02 1 2
C(2) 0.34815(5) 0.17603(4) -0.01721(2) 0.019 1 2
C(3) 0.35052(5) 0.12535(4) 0.05561(2) 0.017 1 2
C(4) 0.29136(4) 0.01548(4) 0.078981(19) 0.016 1 2
C(5) 0.22331(6) -0.03934(4) 0.02881(2) 0.02 1 2
C(6) 0.22071(6) 0.01152(5) -0.04426(3) 0.022 1 2
C(7) 0.29950(4) -0.14796(4) 0.18797(2) 0.016 1 2
C(8) 0.31851(4) -0.24275(3) 0.31811(2) 0.016 1 2
C(9) 0.23966(5) -0.20101(4) 0.39255(2) 0.019 1 2
C(10) 0.25038(6) -0.29482(5) 0.45125(3) 0.021 1 2
C(11) 0.33876(6) -0.43139(5) 0.43611(3) 0.022 1 2
C(12) 0.41726(6) -0.47297(4) 0.36189(3) 0.022 1 2
C(13) 0.40889(5) -0.37953(4) 0.30288(3) 0.019 1 2
C(14) 0.80903(4) 0.38419(3) 0.044606(18) 0.015 1 2
C(15) 0.65233(4) 0.41485(4) 0.07876(2) 0.018 1 2
C(16) 0.61433(4) 0.35521(4) 0.14757(2) 0.017 1 2
C(17) 0.73140(4) 0.26669(3) 0.182590(17) 0.014 1 2
C(18) 0.88837(4) 0.23783(4) 0.14709(2) 0.016 1 2
C(19) 0.92676(4) 0.29682(4) 0.07782(2) 0.017 1 2
C(20) 0.75385(4) 0.13317(3) 0.303614(17) 0.014 1 2
C(21) 0.68734(4) -0.02683(3) 0.405878(17) 0.014 1 2
C(22) 0.58785(4) -0.10907(4) 0.41831(2) 0.016 1 2
C(23) 0.59811(5) -0.20347(4) 0.47624(2) 0.018 1 2
C(24) 0.70761(5) -0.21761(4) 0.52290(2) 0.018 1 2
C(25) 0.80587(5) -0.13551(4) 0.51088(2) 0.018 1 2
C(26) 0.79698(4) -0.04016(4) 0.452823(19) 0.016 1 2
C(71) -0.05408(7) 0.53089(6) -0.23216(3) 0.024 1 2
C(72) 0.20596(5) 0.46850(6) -0.31141(4) 0.024 1 2
C(73) -0.02391(7) 0.54181(7) -0.37033(3) 0.025 1 2
C(74) 0.04217(6) 0.31975(5) -0.31012(4) 0.025 1 2
H(2) 0.399548 0.256913 -0.035149 0.038 1 2
H(3) 0.400877 0.169939 0.094349 0.036 1 2
H(5) 0.167127 -0.117491 0.045791 0.039 1 2
H(6) 0.170171 -0.028469 -0.084863 0.044 1 2
H(9) 0.166054 -0.095379 0.39949 0.036 1 2
H(10) 0.198496 -0.259538 0.509478 0.041 1 2
H(11) 0.348075 -0.502573 0.482508 0.04 1 2
H(12) 0.482551 -0.578792 0.34622 0.04 1 2
H(13) 0.472504 -0.40988 0.245481 0.035 1 2
H(15) 0.562963 0.481935 0.051098 0.035 1 2
H(16) 0.493641 0.377929 0.176107 0.037 1 2
H(18) 0.98138 0.168927 0.171817 0.036 1 2
H(19) 1.047008 0.271945 0.048337 0.037 1 2
H(22) 0.505059 -0.097003 0.380694 0.032 1 2
H(23) 0.51819 -0.264066 0.484363 0.035 1 2
H(24) 0.709626 -0.289173 0.569055 0.036 1 2
H(25) 0.891543 -0.145839 0.546725 0.035 1 2
H(26) 0.869957 0.026595 0.447009 0.032 1 2
H(71A) -0.058661 0.635492 -0.23348 0.05 1 2
H(71B) 0.004897 0.474881 -0.190076 0.055 1 2
H(71C) -0.168355 0.525066 -0.229727 0.053 1 2
H(72A) 0.205298 0.571885 -0.309455 0.051 1 2
H(72B) 0.266266 0.424813 -0.365662 0.054 1 2
H(72C) 0.247694 0.413045 -0.264676 0.054 1 2
H(73A) -0.024227 0.64444 -0.364561 0.051 1 2
H(73B) -0.13773 0.534454 -0.367298 0.055 1 2
H(73C) 0.049808 0.493117 -0.421115 0.056 1 2
H(74A) -0.074791 0.317485 -0.298669 0.054 1 2
H(74B) 0.081663 0.27095 -0.261278 0.054 1 2
H(74C) 0.105629 0.279362 -0.364547 0.055 1 2
H(2A) 0.316473 0.045098 0.185694 0.039 1 2
H(3A) 0.294655 -0.045524 0.283012 0.039 1 2
H(5A) 0.565494 0.210958 0.251731 0.037 1 2
H(6A) 0.55895 0.077422 0.330768 0.036 1 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
CL(1) 0.01471(3) 0.01641(3) 0.01866(3) -0.00133(2) -0.005525(19) -0.00418(2)
S(1) 0.03022(5) 0.01654(3) 0.02117(4) -0.00061(3) -0.00761(3) -0.01073(3)
S(2) 0.01560(3) 0.02508(4) 0.02102(3) 0.00798(3) -0.00772(3) -0.00938(3)
O(1) 0.0836(6) 0.0349(3) 0.02310(19) 0.00058(18) -0.0250(3) -0.0104(3)
O(2) 0.0330(2) 0.0414(3) 0.02487(19) 0.0132(2) -0.00644(17) -0.0103(2)
O(3) 0.02856(15) 0.01713(11) 0.01713(11) 0.00369(9) -0.00500(10) -0.00367(11)
O(4) 0.02239(13) 0.03158(18) 0.01691(11) 0.00532(11) -0.00117(10) -0.00849(13)
N(1) 0.03125(19) 0.02620(16) 0.01682(13) 0.00074(11) -0.00588(11) 0.00055(15)
N(2) 0.02305(13) 0.01500(10) 0.01646(10) -0.00011(8) -0.00600(9) -0.00727(10)
N(3) 0.02348(13) 0.01387(10) 0.01706(11) 0.00003(8) -0.00603(10) -0.00521(10)
N(4) 0.02125(12) 0.01661(9) 0.01357(8) 0.00159(7) -0.00341(7) -0.00636(9)
N(5) 0.01324(9) 0.01797(11) 0.01612(10) 0.00514(8) -0.00411(8) -0.00446(8)
N(6) 0.01488(10) 0.01812(11) 0.01676(10) 0.00572(8) -0.00617(8) -0.00669(9)
N(7) 0.01421(10) 0.01558(10) 0.01672(10) -0.00020(8) -0.00471(8) -0.00326(8)
C(1) 0.02256(14) 0.01836(12) 0.01632(11) -0.00119(9) -0.00485(10) -0.00117(11)
C(2) 0.01943(12) 0.01715(12) 0.01774(11) 0.00073(9) -0.00310(9) -0.00362(10)
C(3) 0.01880(11) 0.01538(10) 0.01714(11) -0.00030(8) -0.00454(9) -0.00530(9)
C(4) 0.01704(10) 0.01436(10) 0.01611(10) -0.00132(8) -0.00439(8) -0.00434(9)
C(5) 0.02424(15) 0.01774(12) 0.02106(13) -0.00075(10) -0.00929(11) -0.00739(11)
C(6) 0.02815(17) 0.01948(13) 0.02055(13) -0.00206(11) -0.01092(13) -0.00509(13)
C(7) 0.01731(11) 0.01461(10) 0.01686(10) -0.00093(8) -0.00392(8) -0.00561(9)
C(8) 0.01557(10) 0.01364(10) 0.01857(11) 0.00021(8) -0.00494(8) -0.00412(8)
C(9) 0.02279(14) 0.01539(11) 0.01813(12) -0.00029(9) -0.00520(10) -0.00390(10)
C(10) 0.02579(16) 0.01870(13) 0.01998(13) 0.00220(10) -0.00568(12) -0.00688(12)
C(11) 0.02479(16) 0.01686(13) 0.02565(16) 0.00497(11) -0.00809(13) -0.00800(12)
C(12) 0.02123(14) 0.01459(12) 0.02898(17) 0.00222(11) -0.00614(13) -0.00355(11)
C(13) 0.01713(11) 0.01472(11) 0.02363(14) 0.00005(10) -0.00342(10) -0.00242(9)
C(14) 0.01647(10) 0.01486(10) 0.01360(9) 0.00133(7) -0.00334(8) -0.00424(8)
C(15) 0.01623(11) 0.01879(12) 0.01597(10) 0.00382(9) -0.00408(9) -0.00215(9)
C(16) 0.01378(10) 0.01930(12) 0.01617(10) 0.00394(9) -0.00330(8) -0.00217(9)
C(17) 0.01309(9) 0.01369(9) 0.01418(9) 0.00166(7) -0.00318(7) -0.00326(8)
C(18) 0.01348(9) 0.01788(11) 0.01595(10) 0.00343(8) -0.00286(8) -0.00289(9)
C(19) 0.01443(10) 0.01883(12) 0.01569(10) 0.00271(8) -0.00243(8) -0.00399(9)
C(20) 0.01303(9) 0.01342(9) 0.01457(9) 0.00191(7) -0.00387(7) -0.00387(7)
C(21) 0.01385(9) 0.01285(9) 0.01421(9) 0.00160(7) -0.00417(7) -0.00378(7)
C(22) 0.01517(10) 0.01507(10) 0.01803(10) 0.00320(8) -0.00506(8) -0.00536(8)
C(23) 0.01857(11) 0.01536(11) 0.01981(12) 0.00425(9) -0.00460(9) -0.00618(9)
C(24) 0.02162(13) 0.01561(11) 0.01798(11) 0.00455(9) -0.00583(10) -0.00526(10)
C(25) 0.02146(13) 0.01730(11) 0.01686(11) 0.00378(9) -0.00817(10) -0.00577(10)
C(26) 0.01828(11) 0.01572(10) 0.01618(10) 0.00265(8) -0.00703(8) -0.00632(9)
C(71) 0.02913(19) 0.02311(16) 0.01762(13) -0.00193(11) -0.00014(12)
-0.00662(14)
C(72) 0.01685(13) 0.02489(17) 0.0336(2) 0.00174(15) -0.00865(13) -0.00739(12)
C(73) 0.02692(18) 0.0297(2) 0.02032(14) 0.00323(13) -0.01144(13) -0.00537(16)
C(74) 0.02166(16) 0.01760(14) 0.0370(2) -0.00381(14) -0.00523(15) -0.00582(12)
H(2) 0.043706 0.037278 0.037883 0.009389 -0.007105 -0.019397
H(3) 0.047507 0.034167 0.035105 0.002831 -0.017209 -0.021826
H(5) 0.052434 0.039129 0.040783 0.00725 -0.022006 -0.027373
H(6) 0.062754 0.042937 0.036137 0.000793 -0.02817 -0.019243
H(9) 0.046736 0.02343 0.03221 -0.003268 -0.008273 -0.000292
H(10) 0.051804 0.039931 0.025585 0.000073 -0.004099 -0.009189
H(11) 0.050555 0.033243 0.037591 0.013993 -0.009763 -0.013529
H(12) 0.044725 0.021605 0.046509 0.002565 -0.006841 -0.000657
H(13) 0.035021 0.030142 0.031836 -0.001101 0.001441 -0.001868
H(15) 0.028004 0.039244 0.040818 0.018971 -0.01562 -0.010084
H(16) 0.019681 0.051535 0.034031 0.011728 -0.002216 -0.003508
H(18) 0.022813 0.044067 0.035787 0.013811 -0.007833 -0.000888
H(19) 0.022002 0.050206 0.033182 0.008116 0.000707 -0.007188
H(22) 0.030271 0.037465 0.035157 0.008103 -0.016182 -0.014865
H(23) 0.034788 0.033158 0.043569 0.010119 -0.01007 -0.019439
H(24) 0.043332 0.033361 0.03286 0.015492 -0.011747 -0.014216
H(25) 0.04025 0.040402 0.033114 0.01007 -0.021168 -0.016004
H(26) 0.036617 0.032914 0.036552 0.008276 -0.015433 -0.020165
H(71A) 0.068726 0.029921 0.047283 -0.008576 0.0013 -0.014095
H(71B) 0.071442 0.058903 0.029218 0.009022 -0.015625 -0.01122
H(71C) 0.033746 0.064384 0.055823 -0.011032 0.007545 -0.016149
H(72A) 0.045926 0.036652 0.077655 0.002542 -0.015978 -0.021918
H(72B) 0.034022 0.067372 0.054546 -0.015028 0.007361 -0.014704
H(72C) 0.045119 0.061077 0.065904 0.021508 -0.034225 -0.016553
H(73A) 0.070367 0.034956 0.052959 0.013035 -0.026126 -0.014977
H(73B) 0.03799 0.071589 0.062956 0.011267 -0.028461 -0.017137
H(73C) 0.063894 0.070543 0.026122 -0.004953 -0.0054 -0.009284
H(74A) 0.033371 0.04462 0.086391 -0.005219 -0.005609 -0.019908
H(74B) 0.068122 0.035312 0.063958 0.016274 -0.026421 -0.015618
H(74C) 0.058086 0.043616 0.056253 -0.022129 0.005663 -0.013612
H(2A) 0.068934 0.026396 0.032783 0.001456 -0.023116 -0.022719
H(3A) 0.067406 0.019633 0.031717 -0.001571 -0.018175 -0.011983
H(5A) 0.020975 0.052741 0.040522 0.020447 -0.011602 -0.014507
H(6A) 0.025972 0.051385 0.038267 0.01888 -0.016178 -0.018952


#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
_atom_rho_multipole_radial_slater_n0
_atom_rho_multipole_radial_slater_zeta0
_atom_rho_multipole_radial_slater_n1
_atom_rho_multipole_radial_slater_zeta1
_atom_rho_multipole_radial_slater_n2
_atom_rho_multipole_radial_slater_zeta2
_atom_rho_multipole_radial_slater_n3
_atom_rho_multipole_radial_slater_zeta3
_atom_rho_multipole_radial_slater_n4
_atom_rho_multipole_radial_slater_zeta4
CL(1) 7.11(4) 0 0.075(17) -0.044(16) 0.020(17) -0.006(19) -0.042(19) -0.007(18)
-0.045(19) 0.184(19) -0.089(18) -0.015(17) -0.016(17) 0.047(17) 0.050(17)
0.003(17) 0.065(17) 0.063(19) 0.055(17) 0.000(17) -0.001(18) -0.013(18)
-0.117(18) 0.101(18) -0.006(17) -0.053(16) 1.08449 1 1 1 1 1 4 4.2587714285714
4 4.2587714285714 4 4.2587714285714 4 4.2587714285714 4 4.2587714285714
S(1) 5.82(5) 0 0.011(18) -0.158(18) -0.103(19) -0.07(2) -0.03(2) 0.12(2)
-0.26(2) -0.035(19) -0.17(2) 0.12(2) -0.10(2) -0.030(19) -0.005(19) -0.012(18)
0.044(17) 0.14(2) 0.09(2) 0.04(2) -0.01(2) -0.01(2) -0.01(2) 0.03(2) 0.056(17)
0.073(18) 1.106039 1.106039 1.106039 1.106039 1.106039 1.106039 4
3.8512666666667 4 3.8512666666667 4 3.8512666666667 4 3.8512666666667 4
3.8512666666667
S(2) 5.29(5) 0 0.029(18) 0.091(16) 0.073(17) 0.03(2) 0.000(19) -0.053(18)
-0.227(19) 0.132(18) 0.13(2) 0.221(18) -0.049(18) -0.037(18) 0.040(17)
0.006(16) -0.053(16) 0.09(2) 0.14(2) -0.029(19) -0.066(19) 0.062(19) -0.002(18)
0.017(17) 0.159(15) -0.023(15) 1.155289 1.155289 1.155289 1.155289 1.155289
1.155289 4 3.8512666666667 4 3.8512666666667 4 3.8512666666667 4
3.8512666666667 4 3.8512666666667
O(1) 6.28(2) 0 0.045(17) 0.028(15) 0.003(16) -0.07(2) -0.028(18) 0.065(18)
-0.156(18) -0.089(18) 0.043(18) 0.118(18) -0.042(17) -0.022(16) -0.012(16)
0.041(16) 0.087(15) -0.04(2) 0.01(2) 0.05(2) 0.01(2) 0.00(2) 0.05(2) -0.01(2)
0.03(2) -0.003(19) 1.003332 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(2) 6.2825 0 0.0451 0.0281 0.0027 -0.0651 -0.0283 0.065 -0.1563 -0.0888 0.0429
0.1175 -0.0415 -0.0222 -0.012 0.0407 0.0872 -0.0414 0.0141 0.0456 0.0117
-0.0003 0.053 -0.0094 0.0345 -0.0031 1.003332 1 1 1 1 1 2 4.466 2 4.466 2 4.466
3 4.466 4 4.466
O(3) 6.2528 0 -0.0924 0.0013 -0.006 -0.0492 -0.0192 0.0005 -0.1505 -0.0371
0.0225 0.0481 -0.028 -0.0135 -0.0409 0.0518 0.0095 0.002 0.0038 0.0014 0.0026
0.0218 0.0199 -0.0045 0.0242 0.0141 1.003332 1 1 1 1 1 2 4.466 2 4.466 2 4.466
3 4.466 4 4.466
O(4) 6.253(19) 0 -0.092(12) 0.001(11) -0.006(11) -0.049(14) -0.019(12)
0.001(12) -0.151(12) -0.037(12) 0.023(12) 0.048(12) -0.028(11) -0.014(11)
-0.041(11) 0.052(10) 0.010(10) 0.002(16) 0.004(14) 0.001(14) 0.003(14)
0.022(15) 0.020(13) -0.005(13) 0.024(12) 0.014(12) 1.003332 1 1 1 1 1 2 4.466 2
4.466 2 4.466 3 4.466 4 4.466
N(1) 5.04(4) 0 0 0 0.01(2) 0.11(2) 0 0 -0.19(2) 0 0.10(2) 0 0 0.18(2) 0 0 0
0.00(3) 0 0 -0.05(3) 0 0 0 0.04(3) 0 1.014954 1 1 1 1 1 2 3.83936 2 3.83936 2
3.83936 3 3.83936 4 3.83936
N(2) 5.35(4) 0 -0.028(18) -0.063(18) -0.036(16) -0.068(19) 0.035(18) 0.004(17)
0.043(18) -0.018(17) -0.006(19) 0.009(18) 0.085(17) 0.042(17) -0.020(17)
0.173(17) 0.057(17) 0.08(2) 0.01(2) 0.02(2) 0.06(2) -0.04(2) -0.08(2) -0.02(2)
-0.06(2) -0.08(2) 1.009171 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4
3.83936
N(3) 5.38(4) 0 -0.046(18) -0.063(18) -0.015(16) -0.078(19) 0.016(18) 0.015(17)
0.005(17) -0.032(18) 0.023(19) 0.011(18) 0.050(18) 0.018(17) -0.038(18)
0.145(17) 0.039(17) 0.09(2) -0.01(2) -0.03(2) 0.00(2) -0.06(2) 0.01(2) 0.01(2)
0.03(2) -0.07(2) 1.009171 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4
3.83936
N(4) 4.98(3) 0 0 0 0.013(17) 0.088(17) 0 0 -0.174(18) 0 0.164(18) 0 0 0.213(18)
0 0 0 -0.01(2) 0 0 -0.06(2) 0 0 0 0.07(2) 0 1.014954 1 1 1 1 1 2 3.83936 2
3.83936 2 3.83936 3 3.83936 4 3.83936
N(5) 5.35(4) 0 0.007(17) -0.093(18) 0.031(15) -0.017(17) -0.018(16) -0.008(17)
0.020(16) -0.056(17) -0.026(18) -0.012(16) 0.061(17) -0.026(17) 0.009(17)
0.160(15) 0.051(15) 0.05(2) 0.00(2) 0.02(2) 0.01(2) -0.04(2) 0.05(2) -0.02(2)
-0.020(19) -0.079(19) 1.009171 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3
3.83936 4 3.83936
N(6) 5.33(4) 0 -0.046(17) -0.034(18) 0.007(15) -0.039(17) 0.020(17) 0.050(16)
0.046(17) 0.026(17) 0.025(18) 0.015(17) 0.070(17) 0.051(17) -0.057(17)
0.126(16) 0.086(16) 0.04(2) -0.01(2) 0.03(2) 0.01(2) 0.01(2) -0.06(2) 0.00(2)
0.048(19) -0.074(19) 1.009171 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936
4 3.83936
N(7) 5.29(3) 0 0.065(17) 0.002(16) 0.073(16) -0.027(18) 0.033(16) 0.007(17)
0.063(17) -0.001(17) 0.165(17) -0.026(17) 0.015(17) 0.046(17) -0.017(17)
0.033(17) -0.190(17) 0.01(2) -0.01(2) -0.01(2) 0.03(2) -0.05(2) 0.05(2) 0.02(2)
0.03(2) -0.04(2) 1.007759 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4
3.83936
C(1) 4.12(5) 0 0.05(2) 0.05(2) 0.01(2) -0.15(2) -0.04(2) 0.01(2) 0.10(2)
-0.05(2) -0.01(3) 0.03(3) 0.03(2) 0.01(3) 0.03(3) 0.27(3) 0.04(3) 0 0 0 0 0 0 0
0 0 1.039499 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(2) 4.12(5) 0 -0.03(2) 0.02(2) 0.01(2) -0.24(2) 0.04(2) 0.01(2) 0.02(2)
0.03(2) 0.01(3) -0.01(2) 0.02(2) -0.06(3) -0.04(2) 0.24(3) -0.08(3) 0 0 0 0 0 0
0 0 0 1.039499 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(3) 4.10(5) 0 -0.03(2) 0.02(2) 0.014(19) -0.22(2) 0.01(2) 0.00(2) -0.04(2)
-0.02(2) 0.00(2) 0.00(2) 0.04(2) -0.02(2) 0.05(2) 0.23(2) -0.02(2) 0 0 0 0 0 0
0 0 0 1.039499 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(4) 3.99(5) 0 0.05(2) 0.09(2) 0.024(19) -0.22(2) 0.01(2) -0.02(2) 0.00(2)
-0.02(2) -0.01(2) 0.03(2) 0.00(2) 0.03(2) -0.02(2) 0.23(2) -0.06(3) 0 0 0 0 0 0
0 0 0 1.039499 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(5) 4.05(5) 0 -0.04(2) -0.01(2) -0.02(2) -0.24(2) -0.02(2) -0.06(2) 0.04(2)
0.06(2) -0.01(3) 0.03(3) 0.04(2) -0.01(3) 0.02(3) 0.25(3) -0.04(3) 0 0 0 0 0 0
0 0 0 1.039499 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(6) 3.99(6) 0 -0.04(3) 0.01(3) 0.02(2) -0.22(2) 0.00(2) 0.07(2) -0.05(2)
-0.04(3) 0.05(3) 0.03(3) 0.04(3) -0.03(3) 0.02(3) 0.22(3) -0.07(3) 0 0 0 0 0 0
0 0 0 1.039499 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(7) 4.20(4) 0 0.040(19) 0.02(2) 0.14(2) 0.15(2) 0.012(19) 0.03(2) -0.20(2)
0.03(2) 0.23(3) -0.03(2) -0.04(2) 0.21(2) -0.04(2) -0.02(2) 0.03(2) 0 0 0 0 0 0
0 0 0 1.023124 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(8) 3.97(5) 0 0.01(2) 0.03(2) 0.022(19) -0.18(2) 0.02(2) 0.03(2) 0.00(2)
-0.01(2) 0.01(2) 0.06(2) 0.01(2) -0.01(2) -0.01(2) 0.23(2) 0.03(3) 0 0 0 0 0 0
0 0 0 1.034404 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(9) 4.15(5) 0 -0.05(2) 0.04(2) 0.03(2) -0.21(2) -0.01(2) -0.06(2) 0.04(2)
0.00(2) 0.01(3) 0.04(2) 0.04(2) -0.04(3) 0.03(2) 0.21(2) 0.03(2) 0 0 0 0 0 0 0
0 0 1.034404 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(10) 4.09(5) 0 -0.07(3) 0.05(3) 0.03(2) -0.19(2) 0.00(2) 0.01(2) 0.03(2)
-0.08(3) 0.02(3) 0.05(3) -0.01(2) 0.05(3) 0.02(3) 0.24(3) 0.05(3) 0 0 0 0 0 0 0
0 0 1.034404 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(11) 4.19(5) 0 0.04(3) 0.01(3) 0.01(2) -0.25(2) 0.01(2) -0.02(2) -0.05(2)
0.01(3) -0.02(3) 0.00(3) -0.01(2) 0.05(3) -0.03(3) 0.29(3) -0.05(3) 0 0 0 0 0 0
0 0 0 1.034404 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(12) 4.01(5) 0 0.06(3) -0.04(3) -0.01(2) -0.18(2) -0.02(2) -0.01(2) 0.02(2)
0.02(3) -0.05(3) -0.01(3) 0.03(3) -0.04(3) 0.03(3) 0.21(3) -0.08(3) 0 0 0 0 0 0
0 0 0 1.034404 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(13) 4.14(5) 0 0.02(2) -0.04(3) 0.00(2) -0.24(2) 0.04(2) 0.03(2) -0.04(2)
-0.02(2) -0.06(3) 0.00(2) 0.02(2) 0.02(2) -0.03(2) 0.25(3) -0.01(3) 0 0 0 0 0 0
0 0 0 1.034404 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(14) 3.99(4) 0 0.02(2) 0.08(2) -0.004(18) -0.10(2) -0.02(2) -0.025(19) 0.08(2)
-0.04(2) 0.02(2) 0.06(2) 0.01(2) 0.00(2) 0.01(2) 0.25(2) 0.02(2) 0 0 0 0 0 0 0
0 0 1.050827 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(15) 3.90(5) 0 -0.02(2) -0.01(2) 0.014(19) -0.15(2) -0.01(2) -0.01(2) 0.03(2)
0.08(2) -0.01(2) 0.07(2) 0.04(2) 0.02(2) 0.01(2) 0.23(2) -0.01(2) 0 0 0 0 0 0 0
0 0 1.050827 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(16) 4.02(5) 0 -0.02(2) 0.04(2) -0.002(19) -0.17(2) 0.02(2) -0.013(19) 0.00(2)
-0.09(2) -0.02(2) 0.06(2) 0.00(2) 0.03(2) 0.00(2) 0.23(2) 0.00(2) 0 0 0 0 0 0 0
0 0 1.050827 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(17) 4.01(4) 0 0.07(2) 0.13(2) -0.007(18) -0.20(2) 0.02(2) -0.001(19) -0.02(2)
-0.04(2) 0.01(2) 0.02(2) -0.02(2) 0.01(2) 0.01(2) 0.24(2) -0.04(2) 0 0 0 0 0 0
0 0 0 1.050827 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(18) 4.12(5) 0 0.06(2) -0.05(2) 0.026(19) -0.18(2) -0.01(2) -0.02(2) 0.06(2)
0.08(2) 0.00(2) 0.01(2) 0.04(2) 0.03(2) -0.01(2) 0.23(2) -0.01(2) 0 0 0 0 0 0 0
0 0 1.050827 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(19) 4.03(5) 0 0.03(2) -0.04(2) -0.025(19) -0.20(2) -0.03(2) 0.014(19) 0.00(2)
-0.03(2) -0.03(2) 0.01(2) 0.09(2) 0.03(2) -0.02(2) 0.21(2) -0.03(2) 0 0 0 0 0 0
0 0 0 1.050827 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(20) 4.14(4) 0 0.055(18) 0.032(19) 0.16(2) 0.13(2) -0.003(19) -0.05(2)
-0.226(19) -0.014(18) 0.21(3) 0.02(2) -0.03(2) 0.19(2) 0.01(2) 0.02(2) -0.03(2)
0 0 0 0 0 0 0 0 0 1.023124 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4
3.1762
C(21) 4.02(5) 0 0.03(2) 0.04(2) 0.007(19) -0.21(2) -0.02(2) 0.001(18) 0.03(2)
-0.06(2) 0.02(2) 0.00(2) 0.08(2) 0.05(2) -0.01(2) 0.25(2) -0.02(3) 0 0 0 0 0 0
0 0 0 1.039566 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(22) 4.16(5) 0 -0.03(2) 0.02(2) -0.021(18) -0.20(2) -0.05(2) 0.010(19) 0.05(2)
0.03(2) -0.07(2) 0.01(2) 0.01(2) 0.04(2) -0.02(2) 0.23(2) 0.00(2) 0 0 0 0 0 0 0
0 0 1.039566 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(23) 4.16(5) 0 -0.01(2) 0.03(2) -0.02(2) -0.21(2) 0.00(2) 0.032(19) 0.02(2)
-0.08(2) -0.03(2) 0.03(2) 0.05(2) 0.01(2) 0.00(2) 0.25(2) 0.05(3) 0 0 0 0 0 0 0
0 0 1.039566 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(24) 4.15(5) 0 0.06(2) 0.01(2) -0.014(19) -0.22(2) 0.04(2) 0.00(2) -0.03(2)
0.01(2) -0.05(3) -0.03(2) -0.01(2) 0.03(2) 0.04(2) 0.25(3) -0.02(3) 0 0 0 0 0 0
0 0 0 1.039566 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(25) 4.08(5) 0 0.04(2) 0.02(2) -0.049(19) -0.20(2) 0.00(2) -0.04(2) 0.08(2)
0.04(2) 0.02(2) -0.04(2) 0.05(2) -0.02(2) 0.00(2) 0.21(2) 0.02(3) 0 0 0 0 0 0 0
0 0 1.039566 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(26) 4.08(5) 0 0.00(2) -0.04(2) 0.025(19) -0.20(2) 0.00(2) -0.012(19) 0.01(2)
-0.02(2) -0.01(2) 0.02(2) 0.09(2) -0.02(2) -0.04(2) 0.24(2) 0.07(2) 0 0 0 0 0 0
0 0 0 1.039566 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(71) 4.07(6) 0 -0.01(3) 0.01(3) -0.09(2) -0.11(2) 0.01(2) 0.03(2) 0.01(2)
0.01(3) 0.16(3) -0.04(3) 0.04(2) 0.08(3) 0.01(3) 0.04(2) -0.19(3) 0 0 0 0 0 0 0
0 0 1.045632 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(72) 4.08(6) 0 0.09(3) -0.04(3) -0.09(2) -0.15(2) -0.06(2) 0.02(2) 0.00(2)
-0.07(3) 0.17(3) -0.07(3) -0.01(2) 0.06(3) -0.07(3) 0.07(2) -0.17(3) 0 0 0 0 0
0 0 0 0 1.045632 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(73) 4.05(6) 0 0.04(3) -0.15(3) -0.02(2) -0.03(2) 0.04(2) -0.03(2) -0.05(3)
-0.01(3) 0.13(3) 0.00(3) 0.06(3) -0.06(3) 0.02(3) -0.04(2) -0.19(3) 0 0 0 0 0 0
0 0 0 1.045632 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(74) 4.01(6) 0 -0.18(3) -0.02(3) -0.12(2) -0.14(2) 0.05(2) -0.01(2) 0.05(3)
0.13(3) 0.27(3) 0.11(3) -0.03(2) -0.03(3) -0.01(3) -0.10(3) -0.17(3) 0 0 0 0 0
0 0 0 0 1.045632 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
H(2) 0.90(3) 0 0 0 0.14(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(3) 0.85(3) 0 0 0 0.12(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(5) 0.81(3) 0 0 0 0.07(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(6) 0.76(4) 0 0 0 0.13(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(9) 0.86(3) 0 0 0 0.14(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(10) 0.90(4) 0 0 0 0.14(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(11) 0.93(4) 0 0 0 0.06(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(12) 0.90(4) 0 0 0 0.10(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(13) 0.85(3) 0 0 0 0.10(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(15) 0.81(3) 0 0 0 0.14(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(16) 0.89(3) 0 0 0 0.17(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(18) 0.87(3) 0 0 0 0.13(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(19) 0.87(3) 0 0 0 0.10(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(22) 0.89(3) 0 0 0 0.08(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(23) 0.88(3) 0 0 0 0.12(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(24) 0.96(3) 0 0 0 0.07(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(25) 0.89(3) 0 0 0 0.13(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(26) 0.76(3) 0 0 0 0.17(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(71A) 0.91(4) 0 0 0 0.10(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(71B) 0.93(4) 0 0 0 0.08(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(71C) 0.95(4) 0 0 0 0.12(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(72A) 0.96(4) 0 0 0 0.11(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(72B) 1.02(4) 0 0 0 0.08(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(72C) 0.92(4) 0 0 0 0.02(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(73A) 1.00(4) 0 0 0 0.12(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(73B) 0.92(4) 0 0 0 0.04(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(73C) 0.87(4) 0 0 0 0.09(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(74A) 0.88(4) 0 0 0 0.13(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(74B) 0.82(4) 0 0 0 0.05(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(74C) 0.98(4) 0 0 0 0.12(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(2A) 0.77(3) 0 0 0 0.11(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(3A) 0.74(3) 0 0 0 0.09(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(5A) 0.83(3) 0 0 0 0.04(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(6A) 0.73(3) 0 0 0 0.09(3) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
CL(1) H(2A) Z CL(1) H(3A) Y
S(1) C(7) X S(1) N(3) Y
S(2) C(20) X S(2) N(4) Y
O(1) N(1) X O(1) O(2) Y
O(2) N(1) -X O(2) O(1) Y
O(3) N(4) -X O(3) O(4) Y
O(4) N(4) X O(4) O(3) Y
N(1) C(1) Z N(1) O(1) Y
N(2) C(4) X N(2) C(7) Y
N(3) C(8) X N(3) C(7) Y
N(4) C(14) Z N(4) O(3) Y
N(5) C(17) X N(5) C(20) Y
N(6) C(21) X N(6) C(20) Y
N(7) C(71) Z N(7) C(72) Y
C(1) C(6) X C(1) C(2) Y
C(2) C(3) X C(2) C(1) Y
C(3) C(4) X C(3) C(2) Y
C(4) C(5) X C(4) C(3) Y
C(5) C(6) X C(5) C(4) Y
C(6) C(1) X C(6) C(5) Y
C(7) S(1) Z C(7) N(2) Y
C(8) C(9) X C(8) C(13) Y
C(9) C(10) X C(9) C(8) Y
C(10) C(11) X C(10) C(9) Y
C(11) C(12) X C(11) C(10) Y
C(12) C(13) X C(12) C(11) Y
C(13) C(8) X C(13) C(12) Y
C(14) C(19) X C(14) C(15) Y
C(15) C(16) X C(15) C(14) Y
C(16) C(17) X C(16) C(15) Y
C(17) C(18) X C(17) C(16) Y
C(18) C(19) X C(18) C(17) Y
C(19) C(14) X C(19) C(18) Y
C(20) S(2) Z C(20) N(5) Y
C(21) C(26) X C(21) C(22) Y
C(22) C(23) X C(22) C(21) Y
C(23) C(24) X C(23) C(22) Y
C(24) C(25) X C(24) C(23) Y
C(25) C(26) X C(25) C(24) Y
C(26) C(21) X C(26) C(25) Y
C(71) N(7) Z C(71) H(71A) Y
C(72) N(7) Z C(72) H(72A) Y
C(73) N(7) Z C(73) H(73A) Y
C(74) N(7) Z C(74) H(74A) Y
H(2) C(2) Z H(2) C(3) Y
H(3) C(3) Z H(3) C(4) Y
H(5) C(5) Z H(5) C(6) Y
H(6) C(6) Z H(6) C(1) Y
H(9) C(9) Z H(9) C(10) Y
H(10) C(10) Z H(10) C(11) Y
H(11) C(11) Z H(11) C(12) Y
H(12) C(12) Z H(12) C(13) Y
H(13) C(13) Z H(13) C(8) Y
H(15) C(15) Z H(15) C(16) Y
H(16) C(16) Z H(16) C(17) Y
H(18) C(18) Z H(18) C(19) Y
H(19) C(19) Z H(19) C(14) Y
H(22) C(22) Z H(22) C(23) Y
H(23) C(23) Z H(23) C(24) Y
H(24) C(24) Z H(24) C(25) Y
H(25) C(25) Z H(25) C(26) Y
H(26) C(26) Z H(26) C(21) Y
H(71A) C(71) Z H(71A) H(71B) Y
H(71B) C(71) Z H(71B) H(71C) Y
H(71C) C(71) Z H(71C) H(71A) Y
H(72A) C(72) Z H(72A) H(72B) Y
H(72B) C(72) Z H(72B) H(72C) Y
H(72C) C(72) Z H(72C) H(72A) Y
H(73A) C(73) Z H(73A) H(73B) Y
H(73B) C(73) Z H(73B) H(73C) Y
H(73C) C(73) Z H(73C) H(73A) Y
H(74A) C(74) Z H(74A) H(74B) Y
H(74B) C(74) Z H(74B) H(74C) Y
H(74C) C(74) Z H(74C) H(74A) Y
H(2A) N(2) Z H(2A) C(7) Y
H(3A) N(3) Z H(3A) C(7) Y
H(5A) N(5) Z H(5A) C(20) Y
H(6A) N(6) Z H(6A) C(20) Y


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(1) C(7) 1.6700(4) 1_555 1_555 yes
S(2) C(20) 1.6799(3) 1_555 1_555 yes
O(1) N(1) 1.2344(10) 1_555 1_555 yes
O(2) N(1) 1.2336(10) 1_555 1_555 yes
O(3) N(4) 1.2281(5) 1_555 1_555 yes
O(4) N(4) 1.2319(5) 1_555 1_555 yes
N(1) C(1) 1.4585(6) 1_555 1_555 yes
N(2) C(4) 1.3964(5) 1_555 1_555 yes
N(2) C(7) 1.3684(5) 1_555 1_555 yes
N(2) H(2A) 1.0090(4) 1_555 1_555 yes
N(3) C(7) 1.3655(5) 1_555 1_555 yes
N(3) C(8) 1.4085(5) 1_555 1_555 yes
N(3) H(3A) 1.0090(4) 1_555 1_555 yes
N(4) C(14) 1.4558(4) 1_555 1_555 yes
N(5) C(17) 1.3968(4) 1_555 1_555 yes
N(5) C(20) 1.3718(4) 1_555 1_555 yes
N(5) H(5A) 1.0090(3) 1_555 1_555 yes
N(6) C(20) 1.3552(4) 1_555 1_555 yes
N(6) C(21) 1.4048(4) 1_555 1_555 yes
N(6) H(6A) 1.0090(3) 1_555 1_555 yes
C(1) C(2) 1.3911(6) 1_555 1_555 yes
C(1) C(6) 1.3908(8) 1_555 1_555 yes
C(2) C(3) 1.3856(5) 1_555 1_555 yes
C(2) H(2) 1.0830(4) 1_555 1_555 yes
C(3) C(4) 1.4099(5) 1_555 1_555 yes
C(3) H(3) 1.0830(4) 1_555 1_555 yes
C(4) C(5) 1.4032(5) 1_555 1_555 yes
C(5) C(6) 1.3905(6) 1_555 1_555 yes
C(5) H(5) 1.0830(5) 1_555 1_555 yes
C(6) H(6) 1.0830(4) 1_555 1_555 yes
C(8) C(9) 1.4001(5) 1_555 1_555 yes
C(8) C(13) 1.3984(5) 1_555 1_555 yes
C(9) C(10) 1.3942(6) 1_555 1_555 yes
C(9) H(9) 1.0830(4) 1_555 1_555 yes
C(10) C(11) 1.3919(7) 1_555 1_555 yes
C(10) H(10) 1.0830(5) 1_555 1_555 yes
C(11) C(12) 1.3956(7) 1_555 1_555 yes
C(11) H(11) 1.0830(4) 1_555 1_555 yes
C(12) C(13) 1.3960(6) 1_555 1_555 yes
C(12) H(12) 1.0830(4) 1_555 1_555 yes
C(13) H(13) 1.0830(4) 1_555 1_555 yes
C(14) C(15) 1.3914(5) 1_555 1_555 yes
C(14) C(19) 1.3902(5) 1_555 1_555 yes
C(15) C(16) 1.3860(5) 1_555 1_555 yes
C(15) H(15) 1.0830(3) 1_555 1_555 yes
C(16) C(17) 1.4088(5) 1_555 1_555 yes
C(16) H(16) 1.0830(3) 1_555 1_555 yes
C(17) C(18) 1.4013(4) 1_555 1_555 yes
C(18) C(19) 1.3902(5) 1_555 1_555 yes
C(18) H(18) 1.0830(3) 1_555 1_555 yes
C(19) H(19) 1.0830(3) 1_555 1_555 yes
C(21) C(22) 1.4028(5) 1_555 1_555 yes
C(21) C(26) 1.3997(5) 1_555 1_555 yes
C(22) C(23) 1.3881(5) 1_555 1_555 yes
C(22) H(22) 1.0830(4) 1_555 1_555 yes
C(23) C(24) 1.3938(6) 1_555 1_555 yes
C(23) H(23) 1.0830(4) 1_555 1_555 yes
C(24) C(25) 1.3926(6) 1_555 1_555 yes
C(24) H(24) 1.0830(3) 1_555 1_555 yes
C(25) C(26) 1.3961(5) 1_555 1_555 yes
C(25) H(25) 1.0830(4) 1_555 1_555 yes
C(26) H(26) 1.0830(4) 1_555 1_555 yes
C(71) H(71A) 1.0590(6) 1_555 1_555 yes
C(71) H(71B) 1.0590(6) 1_555 1_555 yes
C(71) H(71C) 1.0590(7) 1_555 1_555 yes
C(72) H(72A) 1.0590(6) 1_555 1_555 yes
C(72) H(72B) 1.0590(6) 1_555 1_555 yes
C(72) H(72C) 1.0590(6) 1_555 1_555 yes
C(73) H(73A) 1.0590(7) 1_555 1_555 yes
C(73) H(73B) 1.0590(6) 1_555 1_555 yes
C(73) H(73C) 1.0590(6) 1_555 1_555 yes
C(74) H(74A) 1.0590(6) 1_555 1_555 yes
C(74) H(74B) 1.0590(7) 1_555 1_555 yes
C(74) H(74C) 1.0590(6) 1_555 1_555 yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O(1) N(1) O(2) 123.64(8) 1_555 1_555 1_555 yes
O(1) N(1) C(1) 118.09(6) 1_555 1_555 1_555 yes
O(2) N(1) C(1) 118.27(5) 1_555 1_555 1_555 yes
C(4) N(2) C(7) 131.43(3) 1_555 1_555 1_555 yes
C(4) N(2) H(2A) 112.18(3) 1_555 1_555 1_555 yes
C(7) N(2) H(2A) 116.36(3) 1_555 1_555 1_555 yes
C(7) N(3) C(8) 129.08(3) 1_555 1_555 1_555 yes
C(7) N(3) H(3A) 115.21(3) 1_555 1_555 1_555 yes
C(8) N(3) H(3A) 115.29(3) 1_555 1_555 1_555 yes
O(3) N(4) O(4) 123.44(4) 1_555 1_555 1_555 yes
O(3) N(4) C(14) 118.53(3) 1_555 1_555 1_555 yes
O(4) N(4) C(14) 118.03(3) 1_555 1_555 1_555 yes
C(17) N(5) C(20) 131.64(3) 1_555 1_555 1_555 yes
C(17) N(5) H(5A) 109.88(3) 1_555 1_555 1_555 yes
C(20) N(5) H(5A) 117.70(3) 1_555 1_555 1_555 yes
C(20) N(6) C(21) 132.31(3) 1_555 1_555 1_555 yes
C(20) N(6) H(6A) 115.25(3) 1_555 1_555 1_555 yes
C(21) N(6) H(6A) 112.08(3) 1_555 1_555 1_555 yes
N(1) C(1) C(2) 119.07(5) 1_555 1_555 1_555 yes
N(1) C(1) C(6) 119.11(4) 1_555 1_555 1_555 yes
C(2) C(1) C(6) 121.81(4) 1_555 1_555 1_555 yes
C(1) C(2) C(3) 118.48(4) 1_555 1_555 1_555 yes
C(1) C(2) H(2) 121.61(4) 1_555 1_555 1_555 yes
C(3) C(2) H(2) 119.86(4) 1_555 1_555 1_555 yes
C(2) C(3) C(4) 120.89(4) 1_555 1_555 1_555 yes
C(2) C(3) H(3) 119.06(4) 1_555 1_555 1_555 yes
C(4) C(3) H(3) 120.04(3) 1_555 1_555 1_555 yes
N(2) C(4) C(3) 115.45(3) 1_555 1_555 1_555 yes
N(2) C(4) C(5) 125.08(4) 1_555 1_555 1_555 yes
C(3) C(4) C(5) 119.44(3) 1_555 1_555 1_555 yes
C(4) C(5) C(6) 119.68(4) 1_555 1_555 1_555 yes
C(4) C(5) H(5) 122.20(4) 1_555 1_555 1_555 yes
C(6) C(5) H(5) 118.06(4) 1_555 1_555 1_555 yes
C(1) C(6) C(5) 119.63(4) 1_555 1_555 1_555 yes
C(1) C(6) H(6) 118.36(4) 1_555 1_555 1_555 yes
C(5) C(6) H(6) 122.01(5) 1_555 1_555 1_555 yes
S(1) C(7) N(2) 125.64(3) 1_555 1_555 1_555 yes
S(1) C(7) N(3) 124.20(3) 1_555 1_555 1_555 yes
N(2) C(7) N(3) 110.16(3) 1_555 1_555 1_555 yes
N(3) C(8) C(9) 117.00(3) 1_555 1_555 1_555 yes
N(3) C(8) C(13) 123.36(3) 1_555 1_555 1_555 yes
C(9) C(8) C(13) 119.53(3) 1_555 1_555 1_555 yes
C(8) C(9) C(10) 120.48(4) 1_555 1_555 1_555 yes
C(8) C(9) H(9) 115.50(3) 1_555 1_555 1_555 yes
C(10) C(9) H(9) 123.89(4) 1_555 1_555 1_555 yes
C(9) C(10) C(11) 120.14(4) 1_555 1_555 1_555 yes
C(9) C(10) H(10) 119.81(4) 1_555 1_555 1_555 yes
C(11) C(10) H(10) 119.82(4) 1_555 1_555 1_555 yes
C(10) C(11) C(12) 119.37(4) 1_555 1_555 1_555 yes
C(10) C(11) H(11) 119.29(5) 1_555 1_555 1_555 yes
C(12) C(11) H(11) 121.32(4) 1_555 1_555 1_555 yes
C(11) C(12) C(13) 120.96(4) 1_555 1_555 1_555 yes
C(11) C(12) H(12) 122.54(4) 1_555 1_555 1_555 yes
C(13) C(12) H(12) 116.43(5) 1_555 1_555 1_555 yes
C(8) C(13) C(12) 119.52(4) 1_555 1_555 1_555 yes
C(8) C(13) H(13) 118.87(4) 1_555 1_555 1_555 yes
C(12) C(13) H(13) 121.60(4) 1_555 1_555 1_555 yes
N(4) C(14) C(15) 119.50(3) 1_555 1_555 1_555 yes
N(4) C(14) C(19) 118.67(3) 1_555 1_555 1_555 yes
C(15) C(14) C(19) 121.83(3) 1_555 1_555 1_555 yes
C(14) C(15) C(16) 118.40(3) 1_555 1_555 1_555 yes
C(14) C(15) H(15) 120.21(3) 1_555 1_555 1_555 yes
C(16) C(15) H(15) 121.37(3) 1_555 1_555 1_555 yes
C(15) C(16) C(17) 120.92(3) 1_555 1_555 1_555 yes
C(15) C(16) H(16) 120.33(3) 1_555 1_555 1_555 yes
C(17) C(16) H(16) 118.74(3) 1_555 1_555 1_555 yes
N(5) C(17) C(16) 115.28(3) 1_555 1_555 1_555 yes
N(5) C(17) C(18) 125.07(3) 1_555 1_555 1_555 yes
C(16) C(17) C(18) 119.54(3) 1_555 1_555 1_555 yes
C(17) C(18) C(19) 119.67(3) 1_555 1_555 1_555 yes
C(17) C(18) H(18) 121.61(3) 1_555 1_555 1_555 yes
C(19) C(18) H(18) 118.71(3) 1_555 1_555 1_555 yes
C(14) C(19) C(18) 119.65(3) 1_555 1_555 1_555 yes
C(14) C(19) H(19) 119.67(3) 1_555 1_555 1_555 yes
C(18) C(19) H(19) 120.62(3) 1_555 1_555 1_555 yes
S(2) C(20) N(5) 124.37(2) 1_555 1_555 1_555 yes
S(2) C(20) N(6) 125.81(2) 1_555 1_555 1_555 yes
N(5) C(20) N(6) 109.79(3) 1_555 1_555 1_555 yes
N(6) C(21) C(22) 114.69(3) 1_555 1_555 1_555 yes
N(6) C(21) C(26) 125.92(3) 1_555 1_555 1_555 yes
C(22) C(21) C(26) 119.36(3) 1_555 1_555 1_555 yes
C(21) C(22) C(23) 120.57(3) 1_555 1_555 1_555 yes
C(21) C(22) H(22) 117.58(3) 1_555 1_555 1_555 yes
C(23) C(22) H(22) 121.84(3) 1_555 1_555 1_555 yes
C(22) C(23) C(24) 120.29(4) 1_555 1_555 1_555 yes
C(22) C(23) H(23) 118.23(4) 1_555 1_555 1_555 yes
C(24) C(23) H(23) 121.48(3) 1_555 1_555 1_555 yes
C(23) C(24) C(25) 119.19(3) 1_555 1_555 1_555 yes
C(23) C(24) H(24) 118.55(4) 1_555 1_555 1_555 yes
C(25) C(24) H(24) 122.20(4) 1_555 1_555 1_555 yes
C(24) C(25) C(26) 121.17(4) 1_555 1_555 1_555 yes
C(24) C(25) H(25) 119.78(3) 1_555 1_555 1_555 yes
C(26) C(25) H(25) 119.04(4) 1_555 1_555 1_555 yes
C(21) C(26) C(25) 119.42(3) 1_555 1_555 1_555 yes
C(21) C(26) H(26) 120.96(3) 1_555 1_555 1_555 yes
C(25) C(26) H(26) 119.52(3) 1_555 1_555 1_555 yes
H(71A) C(71) H(71B) 113.69(5) 1_555 1_555 1_555 yes
H(71A) C(71) H(71C) 108.55(5) 1_555 1_555 1_555 yes
H(71B) C(71) H(71C) 114.91(5) 1_555 1_555 1_555 yes
H(72A) C(72) H(72B) 108.91(5) 1_555 1_555 1_555 yes
H(72A) C(72) H(72C) 111.89(5) 1_555 1_555 1_555 yes
H(72B) C(72) H(72C) 114.72(5) 1_555 1_555 1_555 yes
H(73A) C(73) H(73B) 112.21(5) 1_555 1_555 1_555 yes
H(73A) C(73) H(73C) 112.24(6) 1_555 1_555 1_555 yes
H(73B) C(73) H(73C) 110.02(5) 1_555 1_555 1_555 yes
H(74A) C(74) H(74B) 100.49(5) 1_555 1_555 1_555 yes
H(74A) C(74) H(74C) 114.35(6) 1_555 1_555 1_555 yes
H(74B) C(74) H(74C) 118.34(5) 1_555 1_555 1_555 yes

####################################################################### 
# 
# 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_CP**
_database_code_depnum_ccdc_archive 'CCDC 1042630'
_audit_update_record             
;
2015-01-08 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;

_audit_creation_date             '02-Sep-09 T16:23:58-00:00'
_audit_creation_method           'XD routine XDCIF'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#
_chemical_name_systematic        
;
 1,3-bis(4-nitrophenyl)thiourea TEA CL
;
_chemical_name_common            ' 1,3-bis(4-nitrophenyl)thiourea TEA CL'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C13 H10 N4 O4 S), C8 H20 N, Cl'
_chemical_formula_sum            'C34 H40 Cl N9 O8 S2'
_chemical_formula_weight         802.32

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z

_cell_length_a                   8.968(2)
_cell_length_b                   15.649(4)
_cell_length_c                   15.899(4)
_cell_angle_alpha                113.0610(10)
_cell_angle_beta                 103.685(3)
_cell_angle_gamma                101.701(2)
_cell_volume                     1882.6(8)
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6076
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      32.9
_diffrn_reflns_theta_full        60.176
_diffrn_measured_fraction_theta_full 0.9640

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9194
_exptl_absorpt_correction_T_max  0.9677
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_reflns_number            55445
_diffrn_reflns_av_r_equivalents  0.0476
_diffrn_reflns_av_sigmaI/netI    0.0495
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         60.32
_reflns_number_total             55445
_reflns_number_gt                50856
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'Volkov et al, (2006)'
_computing_molecular_graphics    'Volkov et al, (2006)'
_computing_publication_material  'Volkov et al, (2006)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
        ?
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
        calc w1 = 1/[s²(Fo)]
;
_refine_ls_extinction_method     none
_refine_ls_number_reflns         35331
_refine_ls_number_parameters     1446
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.056
_refine_ls_R_factor_gt           0.04
_refine_ls_R_Fsqd_factor         0.054
_refine_ls_wR_factor_ref         0.057
_refine_ls_goodness_of_fit_ref   2.556
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.729
_refine_diff_density_rms         0.070

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_symmetry_multiplicity
CL(1) 0.600441(12) 0.504774(7) 0.776586(8) 0.017 1 2
S(2) 1.203166(13) 0.499949(7) 0.779942(9) 0.017 1 2
S(1) 0.25038(3) 0.531945(11) 0.455483(10) 0.025 1 2
O(5) 1.39635(8) 1.01327(4) 0.92368(6) 0.028 1 2
O(6) 1.21394(13) 1.04199(4) 0.98942(5) 0.031 1 2
O(7) 0.87107(11) 0.00634(5) 0.42044(6) 0.034 1 2
O(8) 0.67305(10) -0.04211(4) 0.46487(5) 0.028 1 2
O(1) 0.51510(12) 1.04451(5) 0.72885(7) 0.033 1 2
O(2) 0.70924(14) 1.06833(5) 0.85460(6) 0.036 1 2
O(3) -0.07505(14) 0.01057(5) 0.22712(6) 0.039 1 2
O(4) 0.12313(12) -0.01743(5) 0.30765(6) 0.033 1 2
N(9) 0.62615(6) 0.71960(3) 1.11349(3) 0.015 1 2
N(5) 1.27662(7) 0.98573(3) 0.94333(3) 0.021 1 2
N(6) 0.96763(5) 0.58123(3) 0.79925(3) 0.016 1 2
N(7) 0.87863(5) 0.41606(3) 0.72217(3) 0.015 1 2
N(8) 0.78458(6) 0.02264(3) 0.47058(3) 0.021 1 2
N(1) 0.59459(8) 1.01422(4) 0.77806(4) 0.024 1 2
N(2) 0.43438(7) 0.60553(3) 0.64443(3) 0.018 1 2
N(3) 0.34283(7) 0.44055(3) 0.56065(3) 0.018 1 2
N(4) 0.05431(7) 0.03864(4) 0.29373(3) 0.023 1 2
C(91) 0.67086(8) 0.78806(3) 1.22115(3) 0.021 1 2
C(92) 0.67355(9) 0.73868(4) 1.28595(4) 0.023 1 2
C(93) 0.74759(8) 0.66601(4) 1.09705(4) 0.023 1 2
C(94) 0.92265(12) 0.73218(12) 1.13258(9) 0.041 1 2
C(95) 0.62407(8) 0.78402(3) 1.06327(3) 0.021 1 2
C(96) 0.58235(8) 0.72994(4) 0.95393(3) 0.021 1 2
C(97) 0.46219(8) 0.64024(4) 1.07275(4) 0.023 1 2
C(98) 0.31845(12) 0.67655(12) 1.07586(9) 0.04 1 2
C(14) 1.20265(6) 0.88083(3) 0.90919(3) 0.017 1 2
C(15) 1.06434(7) 0.84815(3) 0.92852(4) 0.019 1 2
C(16) 0.99301(6) 0.74789(3) 0.89258(4) 0.018 1 2
C(17) 1.05687(5) 0.68025(3) 0.83725(3) 0.014 1 2
C(18) 1.19600(6) 0.71512(3) 0.81872(4) 0.017 1 2
C(19) 1.26980(6) 0.81600(3) 0.85600(4) 0.018 1 2
C(20) 1.01191(5) 0.49933(3) 0.76519(3) 0.013 1 2
C(21) 0.86398(5) 0.31932(3) 0.66150(3) 0.014 1 2
C(22) 0.74057(6) 0.24346(3) 0.65532(4) 0.019 1 2
C(23) 0.71384(7) 0.14551(3) 0.59374(4) 0.02 1 2
C(24) 0.81273(6) 0.12459(3) 0.53820(3) 0.017 1 2
C(25) 0.93435(6) 0.19845(3) 0.54223(4) 0.019 1 2
C(26) 0.95912(6) 0.29613(3) 0.60315(3) 0.018 1 2
C(1) 0.55055(7) 0.90806(3) 0.74253(3) 0.018 1 2
C(2) 0.65802(6) 0.87053(3) 0.78351(3) 0.018 1 2
C(3) 0.61613(6) 0.76926(3) 0.74733(3) 0.017 1 2
C(4) 0.46769(6) 0.70579(3) 0.67207(3) 0.016 1 2
C(5) 0.35899(7) 0.74544(4) 0.63356(4) 0.019 1 2
C(6) 0.40188(7) 0.84685(4) 0.66862(4) 0.02 1 2
C(7) 0.34174(6) 0.52566(3) 0.55588(3) 0.017 1 2
C(8) 0.26876(6) 0.34300(3) 0.48816(3) 0.016 1 2
C(9) 0.34689(6) 0.27650(3) 0.49788(3) 0.017 1 2
C(10) 0.27771(6) 0.17663(3) 0.43440(3) 0.018 1 2
C(11) 0.12954(6) 0.14376(3) 0.35999(3) 0.018 1 2
C(12) 0.05070(7) 0.20797(4) 0.34762(4) 0.02 1 2
C(13) 0.11970(6) 0.30803(4) 0.41190(4) 0.019 1 2
H(91A) 0.790178 0.839426 1.239887 0.042 1 2
H(91B) 0.580863 0.825826 1.223876 0.044 1 2
H(92A) 0.724449 0.794644 1.359314 0.053 1 2
H(92B) 0.757527 0.699868 1.285882 0.05 1 2
H(92C) 0.557175 0.688353 1.265608 0.052 1 2
H(93A) 0.693692 0.616439 1.018725 0.042 1 2
H(93B) 0.737863 0.621823 1.135543 0.045 1 2
H(94A) 0.994948 0.686355 1.117025 0.079 1 2
H(94B) 0.960236 0.777644 1.208771 0.061 1 2
H(94C) 0.94041 0.783595 1.105037 0.065 1 2
H(95A) 0.7483 0.835308 1.095752 0.044 1 2
H(95B) 0.539314 0.822002 1.084501 0.044 1 2
H(96A) 0.598572 0.78441 0.930047 0.054 1 2
H(96B) 0.466317 0.674859 0.91854 0.044 1 2
H(96C) 0.664781 0.694177 0.931659 0.048 1 2
H(97A) 0.449284 0.592163 0.997939 0.041 1 2
H(97B) 0.481844 0.59577 1.110121 0.045 1 2
H(98A) 0.212546 0.61958 1.059407 0.077 1 2
H(98B) 0.310847 0.717428 1.036331 0.059 1 2
H(98C) 0.331065 0.730094 1.145719 0.065 1 2
H(15) 1.019508 0.902501 0.97203 0.042 1 2
H(16) 0.884237 0.717892 0.904172 0.039 1 2
H(18) 1.245269 0.665605 0.773044 0.037 1 2
H(19) 1.378433 0.842093 0.842249 0.039 1 2
H(22) 0.661203 0.25783 0.697223 0.043 1 2
H(23) 0.619113 0.088488 0.591516 0.045 1 2
H(25) 1.004811 0.179371 0.4952 0.043 1 2
H(26) 1.045387 0.355521 0.603028 0.041 1 2
H(6A) 0.848963 0.567283 0.791504 0.036 1 2
H(7A) 0.775328 0.427485 0.730899 0.036 1 2
H(2) 0.769826 0.921468 0.84309 0.036 1 2
H(3) 0.701273 0.738175 0.775022 0.033 1 2
H(5) 0.241923 0.700486 0.576258 0.037 1 2
H(6) 0.311918 0.873776 0.638369 0.039 1 2
H(9) 0.464255 0.303674 0.554732 0.036 1 2
H(10) 0.339989 0.126197 0.442187 0.038 1 2
H(12) -0.063743 0.180844 0.288401 0.043 1 2
H(13) 0.061353 0.358629 0.400181 0.04 1 2
H(2A) 0.49973 0.590301 0.694485 0.041 1 2
H(3A) 0.422742 0.445148 0.620127 0.04 1 2



#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
_atom_rho_multipole_radial_slater_n0
_atom_rho_multipole_radial_slater_zeta0
_atom_rho_multipole_radial_slater_n1
_atom_rho_multipole_radial_slater_zeta1
_atom_rho_multipole_radial_slater_n2
_atom_rho_multipole_radial_slater_zeta2
_atom_rho_multipole_radial_slater_n3
_atom_rho_multipole_radial_slater_zeta3
_atom_rho_multipole_radial_slater_n4
_atom_rho_multipole_radial_slater_zeta4
CL(1) 7.31(9) 0 -0.07(3) 0.00(3) 0.07(3) 0.01(3) 0.19(3) 0.06(3) -0.06(3)
0.00(3) -0.13(2) 0.06(2) 0.04(2) 0.07(2) 0.04(2) 0.02(2) -0.02(2) 0.09(2)
-0.10(2) 0.03(2) -0.05(2) -0.09(2) 0.01(2) -0.06(2) -0.03(2) -0.11(2) 1.019549
1 1 1 1 1 4 4.2587714285714 4 4.2587714285714 4 4.2587714285714 4
4.2587714285714 4 4.2587714285714
S(2) 6.13(10) 0 0.06(4) -0.05(4) 0.01(4) -0.09(4) -0.02(4) 0.02(4) -0.04(4)
0.10(4) -0.08(3) 0.16(3) 0.02(3) 0.04(3) -0.11(3) 0.07(3) -0.01(3) -0.02(3)
0.00(3) -0.02(2) 0.04(2) 0.04(2) 0.15(2) 0.03(2) -0.02(2) -0.04(2) 1.036473
1.036473 1.036473 1.036473 1.036473 1.036473 4 3.8512666666667 4
3.8512666666667 4 3.8512666666667 4 3.8512666666667 4 3.8512666666667
S(1) 4.76(9) 0 0.03(3) 0.20(3) -0.26(4) -0.02(4) 0.13(3) -0.06(4) -0.14(3)
-0.15(3) -0.59(3) 0.07(3) 0.45(3) 0.14(3) 0.11(3) 0.05(2) 0.00(2) 0.16(3)
0.01(3) -0.17(3) -0.07(3) 0.01(3) -0.11(2) 0.02(2) -0.002(19) -0.014(19)
1.166623 1.166623 1.166623 1.166623 1.166623 1.166623 4 3.8512666666667 4
3.8512666666667 4 3.8512666666667 4 3.8512666666667 4 3.8512666666667
O(5) 6.24(4) 0 -0.02(2) -0.023(19) 0.01(2) -0.05(2) -0.01(2) 0.00(2) -0.14(2)
-0.028(19) 0.090(18) 0.068(18) 0.008(16) -0.057(16) -0.105(17) 0.045(15)
0.080(14) 0.04(2) 0.01(2) 0.01(2) 0.03(2) -0.03(2) -0.06(2) -0.008(19)
0.056(18) 0.048(18) 0.996212 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(6) 6.2387 0 -0.0236 -0.0233 0.0054 -0.0489 -0.0072 0.0042 -0.1432 -0.0283
0.0901 0.0677 0.0083 -0.0566 -0.1045 0.0453 0.0797 0.0402 0.0096 0.0083 0.0294
-0.0254 -0.0606 -0.0082 0.0559 0.0481 0.996212 1 1 1 1 1 2 4.466 2 4.466 2
4.466 3 4.466 4 4.466
O(7) 6.32(4) 0 -0.04(2) 0.049(19) 0.07(2) -0.03(2) 0.03(2) -0.03(2) -0.14(2)
0.045(19) -0.03(2) 0.135(19) 0.044(18) -0.010(16) 0.042(17) 0.110(14) 0.065(14)
0.04(3) -0.04(2) 0.04(2) -0.03(2) -0.06(2) -0.016(19) 0.004(19) 0.031(17)
-0.026(17) 0.996212 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(8) 6.3163 0 -0.0371 0.0489 0.074 -0.0303 0.0304 -0.0285 -0.137 0.0452 -0.0311
0.1351 0.0441 -0.0097 0.0417 0.11 0.0653 0.0391 -0.0381 0.0354 -0.0284 -0.0614
-0.0159 0.0043 0.0308 -0.0255 0.996212 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3
4.466 4 4.466
O(1) 6.25(4) 0 -0.03(2) 0.00(2) 0.01(3) -0.03(3) 0.01(3) 0.03(3) -0.15(2)
0.04(2) 0.11(2) 0.11(2) -0.18(2) 0.027(19) -0.006(19) 0.070(16) 0.054(16)
-0.01(3) -0.09(3) 0.04(3) -0.07(3) -0.03(3) 0.06(2) 0.00(2) 0.031(19) 0.044(19)
0.996212 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(2) 6.2538 0 -0.031 0.001 0.0088 -0.0278 0.0109 0.0277 -0.148 0.0358 0.113
0.1056 -0.1848 0.0273 -0.0061 0.0701 0.0536 -0.0063 -0.0877 0.039 -0.0684
-0.0295 0.0637 0.0028 0.0306 0.0443 0.996212 1 1 1 1 1 2 4.466 2 4.466 2 4.466
3 4.466 4 4.466
O(3) 6.19(4) 0 -0.01(2) 0.03(2) 0.06(3) -0.14(3) 0.09(3) -0.06(3) -0.12(2)
-0.01(2) -0.06(2) 0.04(2) -0.07(2) 0.027(19) 0.023(19) 0.008(16) 0.097(16)
-0.05(3) 0.01(3) -0.02(3) 0.00(3) 0.02(3) -0.08(2) 0.01(2) 0.032(19) 0.039(19)
0.996212 1 1 1 1 1 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(4) 6.1921 0 -0.0095 0.0308 0.0606 -0.1427 0.0863 -0.0569 -0.12 -0.0092
-0.0618 0.0438 -0.0685 0.027 0.0225 0.0079 0.0966 -0.049 0.0064 -0.0227 -0.0007
0.0189 -0.0839 0.0075 0.0323 0.0388 0.996212 1 1 1 1 1 2 4.466 2 4.466 2 4.466
3 4.466 4 4.466
N(9) 5.18(6) 0 -0.06(3) -0.05(3) 0.05(3) -0.02(2) 0.00(2) 0.00(2) -0.06(2)
0.00(2) 0.10(2) 0.008(19) 0.018(19) -0.10(2) -0.06(2) 0.02(2) -0.13(2) 0.00(3)
0.01(2) 0.02(2) 0.01(2) 0.01(2) 0.07(2) 0.06(2) -0.04(2) -0.04(2) 0.99681 1 1 1
1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
N(5) 5.21(7) 0 0 0 0.05(3) 0.06(2) 0 0 -0.19(3) 0 0.19(2) 0 0 0.20(3) 0 0 0
0.03(3) 0 0 0.02(3) 0 0 0 0.05(3) 0 0.991497 1 1 1 1 1 2 3.83936 2 3.83936 2
3.83936 3 3.83936 4 3.83936
N(6) 5.42(7) 0 -0.02(3) -0.02(3) 0.01(3) -0.05(2) 0.00(2) -0.07(2) -0.04(2)
0.05(2) 0.03(2) -0.01(2) 0.06(2) -0.01(2) -0.02(2) 0.209(18) 0.045(18) 0.05(3)
-0.05(3) -0.02(3) 0.02(3) -0.02(3) -0.05(2) -0.10(2) -0.01(2) -0.05(2) 1.000747
1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
N(7) 5.33(7) 0 0.00(3) 0.00(3) 0.01(3) 0.00(2) -0.01(2) 0.05(2) -0.02(2)
0.07(2) 0.00(2) 0.04(2) 0.04(2) 0.01(2) -0.05(2) 0.168(18) 0.066(18) 0.01(3)
-0.04(2) 0.03(3) 0.00(3) 0.05(3) -0.01(2) 0.05(2) -0.02(2) -0.02(2) 1.000747 1
1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
N(8) 5.11(7) 0 0 0 -0.01(3) 0.02(2) 0 0 -0.19(3) 0 0.18(2) 0 0 0.11(2) 0 0 0
0.10(3) 0 0 0.05(3) 0 0 0 0.06(3) 0 0.991497 1 1 1 1 1 2 3.83936 2 3.83936 2
3.83936 3 3.83936 4 3.83936
N(1) 5.13(7) 0 0 0 0.02(3) 0.07(3) 0 0 -0.18(3) 0 0.12(3) 0 0 0.26(3) 0 0 0
0.11(3) 0 0 0.02(3) 0 0 0 0.07(3) 0 0.991497 1 1 1 1 1 2 3.83936 2 3.83936 2
3.83936 3 3.83936 4 3.83936
N(2) 5.25(7) 0 -0.03(3) 0.03(3) -0.01(3) -0.01(3) -0.02(2) 0.06(3) 0.01(2)
-0.05(2) 0.07(2) 0.00(2) 0.00(2) -0.04(2) -0.06(2) 0.12(2) -0.014(19) 0.10(3)
0.01(3) -0.02(3) -0.06(3) 0.06(3) -0.02(3) 0.02(3) 0.05(2) -0.05(2) 1.000747 1
1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
N(3) 5.17(7) 0 -0.11(3) 0.02(3) 0.04(3) 0.02(3) 0.04(3) -0.03(3) 0.03(2)
0.01(2) -0.02(2) 0.03(2) 0.08(2) -0.02(2) 0.07(2) 0.12(2) 0.03(2) 0.10(3)
-0.03(3) 0.00(3) 0.08(3) -0.01(3) 0.03(3) 0.02(3) -0.07(2) -0.03(2) 1.000747 1
1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3 3.83936 4 3.83936
N(4) 5.29(7) 0 0 0 0.05(3) 0.07(3) 0 0 -0.22(3) 0 0.19(3) 0 0 0.16(3) 0 0 0
0.01(3) 0 0 0.06(3) 0 0 0 0.06(3) 0 0.991497 1 1 1 1 1 2 3.83936 2 3.83936 2
3.83936 3 3.83936 4 3.83936
C(91) 4.13(10) 0 0.05(4) 0.05(4) -0.14(4) -0.20(3) -0.03(3) -0.03(3) -0.01(3)
0.03(3) 0.25(4) -0.03(3) 0.01(4) -0.11(4) -0.07(4) 0.02(4) -0.24(4) 0 0 0 0 0 0
0 0 0 0.995518 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(92) 4.31(12) 0 0.15(5) 0.01(4) -0.08(4) -0.11(4) 0.00(4) 0.08(3) 0.03(4)
-0.01(4) 0.09(4) 0.10(4) 0.02(3) -0.02(4) 0.04(4) -0.11(4) -0.11(4) 0 0 0 0 0 0
0 0 0 0.994059 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(93) 4.40(11) 0 -0.08(4) 0.11(4) -0.18(4) -0.13(4) 0.04(4) -0.01(3) -0.06(4)
-0.03(4) 0.28(4) 0.03(4) -0.06(4) 0.09(4) 0.08(4) -0.01(4) -0.12(4) 0 0 0 0 0 0
0 0 0 0.995518 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(94) 3.95(15) 0 -0.18(6) -0.03(6) 0.01(5) 0.16(5) 0.10(5) 0.10(5) -0.11(5)
0.11(6) 0.07(6) 0.13(5) 0.14(5) -0.23(5) -0.08(5) -0.06(5) -0.08(6) 0 0 0 0 0 0
0 0 0 0.994059 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(95) 3.83(10) 0 -0.04(4) 0.05(4) -0.06(3) -0.12(3) 0.00(3) 0.02(3) -0.03(4)
0.04(3) 0.17(4) -0.01(3) -0.04(3) 0.03(3) 0.03(3) -0.06(4) -0.05(4) 0 0 0 0 0 0
0 0 0 0.995518 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(96) 4.59(12) 0 0.03(5) -0.04(4) 0.07(4) -0.11(3) 0.15(3) 0.09(3) 0.04(4)
0.08(3) 0.16(4) 0.02(4) 0.02(3) 0.04(4) -0.05(4) 0.00(4) -0.21(4) 0 0 0 0 0 0 0
0 0 0.994059 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(97) 4.21(10) 0 -0.04(4) -0.02(4) -0.04(4) -0.05(4) 0.00(3) -0.08(3) 0.12(4)
0.03(4) 0.17(4) 0.03(4) -0.03(3) 0.05(4) 0.05(4) -0.05(4) -0.18(4) 0 0 0 0 0 0
0 0 0 0.995518 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(98) 4.58(14) 0 0.00(6) -0.14(6) -0.08(5) -0.03(5) 0.12(5) 0.00(5) -0.01(5)
0.00(5) 0.30(5) 0.00(5) 0.18(5) 0.03(5) 0.03(5) 0.10(5) -0.13(5) 0 0 0 0 0 0 0
0 0 0.994059 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(14) 4.07(8) 0 0.08(4) 0.15(4) -0.04(3) -0.09(3) -0.08(3) 0.00(3) 0.10(3)
-0.05(3) -0.01(3) -0.06(3) -0.03(3) -0.02(3) 0.02(3) 0.19(3) 0.14(3) 0 0 0 0 0
0 0 0 0 1.027293 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(15) 3.88(9) 0 0.03(4) -0.03(4) 0.02(3) -0.23(3) -0.07(3) 0.04(3) 0.12(3)
0.05(3) -0.01(4) 0.00(3) 0.07(4) 0.02(3) -0.01(3) 0.22(3) 0.06(3) 0 0 0 0 0 0 0
0 0 1.027293 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(16) 3.82(9) 0 -0.01(4) -0.05(4) 0.04(3) -0.13(3) 0.02(3) 0.02(3) -0.05(3)
-0.06(3) -0.01(4) 0.07(3) -0.03(3) -0.01(3) -0.01(3) 0.21(3) 0.06(3) 0 0 0 0 0
0 0 0 0 1.027293 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(17) 3.96(9) 0 0.01(4) 0.12(3) -0.04(3) -0.12(3) 0.05(3) -0.05(3) 0.01(3)
-0.07(3) -0.03(3) 0.04(3) 0.04(3) -0.01(3) -0.04(3) 0.29(3) -0.04(3) 0 0 0 0 0
0 0 0 0 1.027293 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(18) 4.31(9) 0 0.04(4) 0.00(4) -0.09(3) -0.19(3) 0.02(3) -0.07(3) -0.09(3)
0.00(3) -0.04(4) 0.04(3) -0.01(3) -0.02(3) 0.05(3) 0.33(3) 0.01(3) 0 0 0 0 0 0
0 0 0 1.027293 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(19) 4.05(9) 0 -0.04(4) 0.06(4) -0.05(3) -0.23(3) 0.03(3) -0.03(3) 0.07(3)
0.03(3) -0.02(4) 0.05(3) 0.16(3) 0.00(3) 0.00(3) 0.18(3) 0.01(3) 0 0 0 0 0 0 0
0 0 1.027293 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(20) 3.97(8) 0 -0.03(3) -0.02(3) 0.09(3) 0.15(3) 0.00(3) 0.04(3) -0.15(3)
-0.08(3) 0.15(3) 0.00(3) -0.02(3) 0.19(3) 0.00(3) 0.01(3) 0.07(3) 0 0 0 0 0 0 0
0 0 1.021332 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(21) 3.96(8) 0 -0.03(4) 0.04(4) 0.07(3) -0.16(3) -0.08(3) 0.14(3) 0.02(3)
-0.03(3) 0.01(3) 0.07(3) 0.04(3) -0.02(3) -0.03(3) 0.28(3) -0.07(3) 0 0 0 0 0 0
0 0 0 1.028967 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(22) 4.11(9) 0 0.08(4) -0.08(4) 0.00(3) -0.25(3) 0.01(3) 0.04(3) 0.05(3)
0.02(3) 0.08(4) 0.03(3) 0.10(4) 0.02(3) -0.05(3) 0.26(3) 0.05(3) 0 0 0 0 0 0 0
0 0 1.028967 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(23) 3.99(9) 0 -0.05(4) 0.01(4) 0.05(4) -0.24(3) 0.09(3) -0.03(3) -0.01(3)
0.00(3) 0.03(4) 0.12(4) 0.06(3) -0.08(4) 0.05(3) 0.21(3) -0.07(3) 0 0 0 0 0 0 0
0 0 1.028967 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(24) 3.90(8) 0 -0.04(4) 0.16(4) -0.09(3) -0.14(3) 0.02(3) -0.01(3) -0.02(3)
-0.15(3) 0.02(3) 0.06(3) -0.06(3) -0.07(3) 0.01(3) 0.25(3) 0.03(3) 0 0 0 0 0 0
0 0 0 1.028967 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(25) 4.25(9) 0 0.03(4) -0.01(4) -0.06(3) -0.25(3) 0.04(3) 0.04(3) -0.04(3)
-0.01(3) 0.04(4) -0.01(4) 0.02(3) -0.04(3) 0.01(3) 0.33(3) -0.03(3) 0 0 0 0 0 0
0 0 0 1.028967 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(26) 3.91(9) 0 -0.07(4) 0.01(4) 0.02(3) -0.18(3) -0.07(3) 0.05(3) 0.00(3)
0.00(3) 0.05(4) 0.03(4) 0.11(3) -0.01(3) 0.01(3) 0.18(3) -0.08(3) 0 0 0 0 0 0 0
0 0 1.028967 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(1) 4.14(9) 0 0.11(4) 0.15(4) 0.01(3) -0.14(3) 0.05(3) -0.05(3) 0.05(3)
-0.16(3) 0.04(4) 0.08(3) 0.05(3) 0.06(3) 0.08(3) 0.18(3) 0.07(3) 0 0 0 0 0 0 0
0 0 1.031438 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(2) 4.11(9) 0 0.06(4) 0.01(4) -0.05(4) -0.28(3) 0.04(3) -0.18(3) -0.02(3)
0.06(3) 0.03(4) 0.07(3) 0.02(3) 0.05(3) -0.08(3) 0.32(3) 0.03(3) 0 0 0 0 0 0 0
0 0 1.031438 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(3) 3.80(9) 0 -0.03(4) -0.07(4) -0.02(4) -0.21(3) 0.03(3) -0.04(3) 0.03(3)
0.00(3) 0.06(3) 0.02(3) -0.02(3) -0.04(3) 0.05(3) 0.26(3) 0.10(3) 0 0 0 0 0 0 0
0 0 1.031438 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(4) 3.86(8) 0 -0.04(4) 0.06(4) 0.02(3) -0.24(3) 0.00(3) -0.02(3) 0.07(3)
-0.01(3) 0.00(3) 0.04(3) 0.10(3) -0.04(3) 0.01(3) 0.32(3) 0.06(3) 0 0 0 0 0 0 0
0 0 1.031438 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(5) 3.88(9) 0 0.04(4) 0.05(4) -0.04(4) -0.24(4) 0.00(3) 0.00(3) -0.03(3)
0.10(3) -0.03(4) 0.10(3) 0.04(3) 0.02(3) -0.01(3) 0.21(3) -0.04(3) 0 0 0 0 0 0
0 0 0 1.031438 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(6) 4.25(9) 0 -0.07(4) 0.08(4) 0.02(4) -0.29(4) 0.06(3) 0.03(3) -0.02(3)
-0.01(3) 0.06(4) 0.01(4) 0.08(3) 0.10(4) -0.04(4) 0.28(3) 0.03(3) 0 0 0 0 0 0 0
0 0 1.031438 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(7) 4.06(8) 0 -0.01(3) -0.09(3) 0.13(3) 0.15(3) -0.17(3) -0.01(3) -0.13(3)
0.02(3) 0.19(3) 0.05(3) -0.03(3) 0.16(3) -0.03(3) -0.03(3) -0.09(3) 0 0 0 0 0 0
0 0 0 1.021332 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(8) 4.19(8) 0 0.04(4) -0.04(4) 0.03(3) -0.24(3) 0.05(3) -0.02(3) 0.03(3)
-0.02(3) 0.03(3) 0.02(3) 0.10(3) 0.04(3) 0.00(3) 0.27(3) 0.00(3) 0 0 0 0 0 0 0
0 0 1.033685 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(9) 4.10(9) 0 -0.01(4) -0.04(4) -0.02(3) -0.17(3) 0.03(3) -0.04(3) -0.02(3)
0.07(3) -0.02(3) 0.11(3) -0.03(3) -0.02(3) 0.02(3) 0.09(3) -0.04(3) 0 0 0 0 0 0
0 0 0 1.033685 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(10) 3.85(9) 0 -0.05(4) 0.04(4) 0.01(3) -0.28(3) -0.05(3) 0.01(3) -0.02(3)
-0.03(3) -0.06(4) -0.01(3) 0.10(3) 0.05(3) -0.02(3) 0.26(3) 0.06(3) 0 0 0 0 0 0
0 0 0 1.033685 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(11) 3.97(9) 0 0.08(4) 0.19(4) -0.05(3) -0.11(3) -0.09(3) -0.02(3) 0.04(3)
-0.11(3) 0.08(4) 0.08(3) -0.02(3) -0.06(3) -0.05(3) 0.15(3) -0.04(3) 0 0 0 0 0
0 0 0 0 1.033685 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(12) 4.03(9) 0 0.03(4) 0.00(4) -0.06(4) -0.22(4) -0.04(3) 0.14(3) -0.05(3)
0.12(3) -0.07(4) 0.07(4) 0.01(4) -0.09(4) 0.00(4) 0.22(3) 0.05(3) 0 0 0 0 0 0 0
0 0 1.033685 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(13) 4.04(9) 0 -0.02(4) 0.05(4) 0.09(4) 0.15(3) -0.03(3) -0.06(3) -0.20(3)
-0.01(3) 0.07(4) -0.03(3) 0.02(3) 0.18(3) 0.06(3) 0.01(3) -0.01(3) 0 0 0 0 0 0
0 0 0 1.033685 1 1 1 1 1 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
H(91A) 0.88(6) 0 0 0 -0.02(5) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(91B) 0.88(6) 0 0 0 0.10(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(92A) 0.95(6) 0 0 0 0.12(5) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(92B) 0.90(7) 0 0 0 0.08(5) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(92C) 0.93(7) 0 0 0 0.02(5) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(93A) 0.81(6) 0 0 0 0.05(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(93B) 0.86(6) 0 0 0 0.13(5) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(94A) 1.03(9) 0 0 0 0.28(6) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(94B) 0.84(8) 0 0 0 0.07(6) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(94C) 1.09(9) 0 0 0 0.11(7) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(95A) 0.89(6) 0 0 0 0.19(5) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(95B) 0.85(6) 0 0 0 0.16(5) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(96A) 0.91(6) 0 0 0 0.04(5) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(96B) 0.84(6) 0 0 0 0.06(5) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(96C) 0.97(7) 0 0 0 0.05(5) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(97A) 0.93(6) 0 0 0 0.12(5) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(97B) 0.97(6) 0 0 0 0.19(5) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(98A) 0.62(8) 0 0 0 0.04(6) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(98B) 0.62(8) 0 0 0 0.01(6) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(98C) 0.95(8) 0 0 0 0.05(6) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(15) 0.92(6) 0 0 0 0.12(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(16) 0.92(6) 0 0 0 0.13(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(18) 0.79(6) 0 0 0 0.06(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(19) 0.96(6) 0 0 0 0.08(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(22) 0.82(6) 0 0 0 0.18(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(23) 0.76(6) 0 0 0 0.18(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(25) 0.99(6) 0 0 0 0.10(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(26) 0.70(6) 0 0 0 0.15(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(6A) 0.63(5) 0 0 0 0.16(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(7A) 0.91(5) 0 0 0 0.18(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(2) 0.81(6) 0 0 0 0.22(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(3) 0.75(5) 0 0 0 0.08(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(5) 0.74(6) 0 0 0 0.23(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(6) 0.83(6) 0 0 0 0.13(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(9) 0.92(6) 0 0 0 0.06(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(10) 0.83(6) 0 0 0 0.12(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(12) 0.77(6) 0 0 0 0.18(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(13) 0.87(6) 0 0 0 0.23(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(2A) 0.87(5) 0 0 0 0.21(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(3A) 0.73(5) 0 0 0 0.21(4) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
CL(1) H(6A) Z CL(1) H(7A) Y
S(2) C(20) X S(2) C(26) Y
S(1) C(7) X S(1) C(13) Y
O(5) N(5) X O(5) O(6) Y
O(6) N(5) -X O(6) O(5) Y
O(7) N(8) X O(7) O(8) Y
O(8) N(8) -X O(8) O(7) Y
O(1) N(1) X O(1) O(2) Y
O(2) N(1) -X O(2) O(1) Y
O(3) N(4) X O(3) O(4) Y
O(4) N(4) -X O(4) O(3) Y
N(9) C(91) Z N(9) C(93) Y
N(5) C(14) Z N(5) O(6) Y
N(6) C(17) X N(6) C(20) Y
N(7) C(21) X N(7) C(20) Y
N(8) C(24) Z N(8) O(8) Y
N(1) C(1) Z N(1) O(2) Y
N(2) C(4) X N(2) C(7) Y
N(3) C(8) X N(3) C(7) Y
N(4) C(11) Z N(4) O(4) Y
C(91) N(9) Z C(91) H(91A) Y
C(92) C(91) Z C(92) H(92A) Y
C(93) N(9) Z C(93) H(93A) Y
C(94) C(93) Z C(94) H(94A) Y
C(95) N(9) Z C(95) H(95A) Y
C(96) C(95) Z C(96) H(96A) Y
C(97) N(9) Z C(97) H(97A) Y
C(98) C(97) Z C(98) H(98A) Y
C(14) C(15) X C(14) C(19) Y
C(15) C(16) X C(15) C(14) Y
C(16) C(17) X C(16) C(15) Y
C(17) C(18) X C(17) C(16) Y
C(18) C(19) X C(18) C(17) Y
C(19) C(14) X C(19) C(18) Y
C(20) S(2) Z C(20) N(7) Y
C(21) C(22) X C(21) C(26) Y
C(22) C(23) X C(22) C(21) Y
C(23) C(24) X C(23) C(22) Y
C(24) C(25) X C(24) C(23) Y
C(25) C(24) X C(25) C(26) Y
C(26) C(21) X C(26) C(25) Y
C(1) C(6) X C(1) C(2) Y
C(2) C(3) X C(2) C(1) Y
C(3) C(4) X C(3) C(2) Y
C(4) C(3) X C(4) C(5) Y
C(5) C(6) X C(5) C(4) Y
C(6) C(1) X C(6) C(5) Y
C(7) S(1) Z C(7) N(3) Y
C(8) C(9) X C(8) C(13) Y
C(9) C(10) X C(9) C(8) Y
C(10) C(11) X C(10) C(9) Y
C(11) C(12) X C(11) C(10) Y
C(12) C(13) X C(12) C(11) Y
C(13) C(8) Z C(13) C(12) Y
H(91A) C(91) Z H(91A) H(91B) Y
H(91B) C(91) Z H(91B) H(91A) Y
H(92A) C(92) Z H(92A) H(92B) Y
H(92B) C(92) Z H(92B) H(92C) Y
H(92C) C(92) Z H(92C) H(92A) Y
H(93A) C(93) Z H(93A) H(93B) Y
H(93B) C(93) Z H(93B) H(93A) Y
H(94A) C(94) Z H(94A) H(94B) Y
H(94B) C(94) Z H(94B) H(94C) Y
H(94C) C(94) Z H(94C) H(94A) Y
H(95A) C(95) Z H(95A) H(95B) Y
H(95B) C(95) Z H(95B) H(95A) Y
H(96A) C(96) Z H(96A) H(96B) Y
H(96B) C(96) Z H(96B) H(96C) Y
H(96C) C(96) Z H(96C) H(96A) Y
H(97A) C(97) Z H(97A) H(97B) Y
H(97B) C(97) Z H(97B) H(97A) Y
H(98A) C(98) Z H(98A) H(98B) Y
H(98B) C(98) Z H(98B) H(98C) Y
H(98C) C(98) Z H(98C) H(98A) Y
H(15) C(15) Z H(15) C(16) Y
H(16) C(16) Z H(16) C(17) Y
H(18) C(18) Z H(18) C(19) Y
H(19) C(19) Z H(19) C(14) Y
H(22) C(22) Z H(22) C(23) Y
H(23) C(23) Z H(23) C(24) Y
H(25) C(25) Z H(25) C(26) Y
H(26) C(26) Z H(26) C(21) Y
H(6A) N(6) Z H(6A) C(20) Y
H(7A) N(7) Z H(7A) C(20) Y
H(2) C(2) Z H(2) C(3) Y
H(3) C(3) Z H(3) C(4) Y
H(5) C(5) Z H(5) C(6) Y
H(6) C(6) Z H(6) C(1) Y
H(9) C(9) Z H(9) C(10) Y
H(10) C(10) Z H(10) C(11) Y
H(12) C(12) Z H(12) C(13) Y
H(13) C(13) Z H(13) C(8) Y
H(2A) N(2) Z H(2A) C(7) Y
H(3A) N(3) Z H(3A) C(7) Y


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(2) C(20) 1.6727(4) 1_555 1_555 yes
S(1) C(7) 1.6631(4) 1_555 1_555 yes
O(5) N(5) 1.2300(9) 1_555 1_555 yes
O(6) N(5) 1.2322(8) 1_555 1_555 yes
O(7) N(8) 1.2312(9) 1_555 1_555 yes
O(8) N(8) 1.2285(8) 1_555 1_555 yes
O(1) N(1) 1.2284(9) 1_555 1_555 yes
O(2) N(1) 1.2258(10) 1_555 1_555 yes
O(3) N(4) 1.2280(10) 1_555 1_555 yes
O(4) N(4) 1.2276(9) 1_555 1_555 yes
N(5) C(14) 1.4558(6) 1_555 1_555 yes
N(6) C(17) 1.3934(5) 1_555 1_555 yes
N(6) C(20) 1.3631(5) 1_555 1_555 yes
N(6) H(6A) 1.0090(4) 1_555 1_555 yes
N(7) C(20) 1.3704(5) 1_555 1_555 yes
N(7) C(21) 1.3981(5) 1_555 1_555 yes
N(7) H(7A) 1.0090(4) 1_555 1_555 yes
N(8) C(24) 1.4593(6) 1_555 1_555 yes
N(1) C(1) 1.4588(7) 1_555 1_555 yes
N(2) C(4) 1.3970(6) 1_555 1_555 yes
N(2) C(7) 1.3716(6) 1_555 1_555 yes
N(2) H(2A) 1.0090(5) 1_555 1_555 yes
N(3) C(7) 1.3652(6) 1_555 1_555 yes
N(3) C(8) 1.3958(6) 1_555 1_555 yes
N(3) H(3A) 1.0090(5) 1_555 1_555 yes
N(4) C(11) 1.4584(7) 1_555 1_555 yes
C(91) C(92) 1.5096(7) 1_555 1_555 yes
C(91) H(91A) 1.0920(7) 1_555 1_555 yes
C(91) H(91B) 1.0920(6) 1_555 1_555 yes
C(92) H(92A) 1.0590(5) 1_555 1_555 yes
C(92) H(92B) 1.0590(7) 1_555 1_555 yes
C(92) H(92C) 1.0590(7) 1_555 1_555 yes
C(93) C(94) 1.5228(13) 1_555 1_555 yes
C(93) H(93A) 1.0920(6) 1_555 1_555 yes
C(93) H(93B) 1.0920(6) 1_555 1_555 yes
C(94) H(94A) 1.0590(14) 1_555 1_555 yes
C(94) H(94B) 1.0590(12) 1_555 1_555 yes
C(94) H(94C) 1.0590(18) 1_555 1_555 yes
C(95) C(96) 1.5130(7) 1_555 1_555 yes
C(95) H(95A) 1.0920(6) 1_555 1_555 yes
C(95) H(95B) 1.0920(6) 1_555 1_555 yes
C(96) H(96A) 1.0590(5) 1_555 1_555 yes
C(96) H(96B) 1.0590(6) 1_555 1_555 yes
C(96) H(96C) 1.0590(7) 1_555 1_555 yes
C(97) C(98) 1.5140(13) 1_555 1_555 yes
C(97) H(97A) 1.0920(6) 1_555 1_555 yes
C(97) H(97B) 1.0920(6) 1_555 1_555 yes
C(98) H(98A) 1.0590(13) 1_555 1_555 yes
C(98) H(98B) 1.0590(15) 1_555 1_555 yes
C(98) H(98C) 1.0590(13) 1_555 1_555 yes
C(14) C(15) 1.3931(7) 1_555 1_555 yes
C(14) C(19) 1.3870(6) 1_555 1_555 yes
C(15) C(16) 1.3840(6) 1_555 1_555 yes
C(15) H(15) 1.0830(4) 1_555 1_555 yes
C(16) C(17) 1.4061(5) 1_555 1_555 yes
C(16) H(16) 1.0830(5) 1_555 1_555 yes
C(17) C(18) 1.4018(6) 1_555 1_555 yes
C(18) C(19) 1.3924(6) 1_555 1_555 yes
C(18) H(18) 1.0830(4) 1_555 1_555 yes
C(19) H(19) 1.0830(5) 1_555 1_555 yes
C(21) C(22) 1.4029(5) 1_555 1_555 yes
C(21) C(26) 1.3988(6) 1_555 1_555 yes
C(22) C(23) 1.3892(6) 1_555 1_555 yes
C(22) H(22) 1.0830(5) 1_555 1_555 yes
C(23) C(24) 1.3910(7) 1_555 1_555 yes
C(23) H(23) 1.0830(4) 1_555 1_555 yes
C(24) C(25) 1.3882(6) 1_555 1_555 yes
C(25) C(26) 1.3873(6) 1_555 1_555 yes
C(25) H(25) 1.0830(5) 1_555 1_555 yes
C(26) H(26) 1.0830(4) 1_555 1_555 yes
C(1) C(2) 1.3894(7) 1_555 1_555 yes
C(1) C(6) 1.3910(8) 1_555 1_555 yes
C(2) C(3) 1.3877(6) 1_555 1_555 yes
C(2) H(2) 1.0830(5) 1_555 1_555 yes
C(3) C(4) 1.4033(6) 1_555 1_555 yes
C(3) H(3) 1.0830(4) 1_555 1_555 yes
C(4) C(5) 1.4038(6) 1_555 1_555 yes
C(5) C(6) 1.3911(7) 1_555 1_555 yes
C(5) H(5) 1.0830(5) 1_555 1_555 yes
C(6) H(6) 1.0830(5) 1_555 1_555 yes
C(8) C(9) 1.4029(6) 1_555 1_555 yes
C(8) C(13) 1.4047(7) 1_555 1_555 yes
C(9) C(10) 1.3859(6) 1_555 1_555 yes
C(9) H(9) 1.0830(5) 1_555 1_555 yes
C(10) C(11) 1.3900(7) 1_555 1_555 yes
C(10) H(10) 1.0830(5) 1_555 1_555 yes
C(11) C(12) 1.3877(7) 1_555 1_555 yes
C(12) C(13) 1.3904(7) 1_555 1_555 yes
C(12) H(12) 1.0830(5) 1_555 1_555 yes
C(13) H(13) 1.0830(5) 1_555 1_555 yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O(5) N(5) O(6) 123.63(7) 1_555 1_555 1_555 yes
O(5) N(5) C(14) 118.52(5) 1_555 1_555 1_555 yes
O(6) N(5) C(14) 117.84(6) 1_555 1_555 1_555 yes
C(17) N(6) C(20) 130.53(4) 1_555 1_555 1_555 yes
C(17) N(6) H(6A) 114.93(4) 1_555 1_555 1_555 yes
C(20) N(6) H(6A) 114.40(4) 1_555 1_555 1_555 yes
C(20) N(7) C(21) 128.62(4) 1_555 1_555 1_555 yes
C(20) N(7) H(7A) 115.07(3) 1_555 1_555 1_555 yes
C(21) N(7) H(7A) 116.06(4) 1_555 1_555 1_555 yes
O(7) N(8) O(8) 123.50(6) 1_555 1_555 1_555 yes
O(7) N(8) C(24) 118.24(5) 1_555 1_555 1_555 yes
O(8) N(8) C(24) 118.23(5) 1_555 1_555 1_555 yes
O(1) N(1) O(2) 123.49(8) 1_555 1_555 1_555 yes
O(1) N(1) C(1) 117.92(6) 1_555 1_555 1_555 yes
O(2) N(1) C(1) 118.58(6) 1_555 1_555 1_555 yes
C(4) N(2) C(7) 129.61(4) 1_555 1_555 1_555 yes
C(4) N(2) H(2A) 114.58(4) 1_555 1_555 1_555 yes
C(7) N(2) H(2A) 115.29(4) 1_555 1_555 1_555 yes
C(7) N(3) C(8) 129.87(4) 1_555 1_555 1_555 yes
C(7) N(3) H(3A) 118.28(4) 1_555 1_555 1_555 yes
C(8) N(3) H(3A) 110.89(4) 1_555 1_555 1_555 yes
O(3) N(4) O(4) 123.27(7) 1_555 1_555 1_555 yes
O(3) N(4) C(11) 118.41(6) 1_555 1_555 1_555 yes
O(4) N(4) C(11) 118.32(6) 1_555 1_555 1_555 yes
C(92) C(91) H(91A) 112.14(5) 1_555 1_555 1_555 yes
C(92) C(91) H(91B) 110.96(5) 1_555 1_555 1_555 yes
H(91A) C(91) H(91B) 110.06(4) 1_555 1_555 1_555 yes
C(91) C(92) H(92A) 107.66(5) 1_555 1_555 1_555 yes
C(91) C(92) H(92B) 114.73(5) 1_555 1_555 1_555 yes
C(91) C(92) H(92C) 110.76(5) 1_555 1_555 1_555 yes
H(92A) C(92) H(92B) 100.11(5) 1_555 1_555 1_555 yes
H(92A) C(92) H(92C) 115.98(6) 1_555 1_555 1_555 yes
H(92B) C(92) H(92C) 107.40(5) 1_555 1_555 1_555 yes
C(94) C(93) H(93A) 115.40(7) 1_555 1_555 1_555 yes
C(94) C(93) H(93B) 110.41(8) 1_555 1_555 1_555 yes
H(93A) C(93) H(93B) 108.19(5) 1_555 1_555 1_555 yes
C(93) C(94) H(94A) 107.76(12) 1_555 1_555 1_555 yes
C(93) C(94) H(94B) 108.40(9) 1_555 1_555 1_555 yes
C(93) C(94) H(94C) 115.23(9) 1_555 1_555 1_555 yes
H(94A) C(94) H(94B) 110.49(11) 1_555 1_555 1_555 yes
H(94A) C(94) H(94C) 111.81(11) 1_555 1_555 1_555 yes
H(94B) C(94) H(94C) 103.03(14) 1_555 1_555 1_555 yes
C(96) C(95) H(95A) 108.35(5) 1_555 1_555 1_555 yes
C(96) C(95) H(95B) 113.43(5) 1_555 1_555 1_555 yes
H(95A) C(95) H(95B) 111.06(4) 1_555 1_555 1_555 yes
C(95) C(96) H(96A) 106.48(4) 1_555 1_555 1_555 yes
C(95) C(96) H(96B) 112.06(5) 1_555 1_555 1_555 yes
C(95) C(96) H(96C) 114.77(5) 1_555 1_555 1_555 yes
H(96A) C(96) H(96B) 115.43(5) 1_555 1_555 1_555 yes
H(96A) C(96) H(96C) 101.97(5) 1_555 1_555 1_555 yes
H(96B) C(96) H(96C) 105.95(5) 1_555 1_555 1_555 yes
C(98) C(97) H(97A) 111.37(7) 1_555 1_555 1_555 yes
C(98) C(97) H(97B) 116.39(7) 1_555 1_555 1_555 yes
H(97A) C(97) H(97B) 103.40(5) 1_555 1_555 1_555 yes
C(97) C(98) H(98A) 111.52(13) 1_555 1_555 1_555 yes
C(97) C(98) H(98B) 109.38(7) 1_555 1_555 1_555 yes
C(97) C(98) H(98C) 114.52(9) 1_555 1_555 1_555 yes
H(98A) C(98) H(98B) 118.18(10) 1_555 1_555 1_555 yes
H(98A) C(98) H(98C) 101.99(8) 1_555 1_555 1_555 yes
H(98B) C(98) H(98C) 100.79(14) 1_555 1_555 1_555 yes
N(5) C(14) C(15) 119.27(4) 1_555 1_555 1_555 yes
N(5) C(14) C(19) 118.85(4) 1_555 1_555 1_555 yes
C(15) C(14) C(19) 121.86(4) 1_555 1_555 1_555 yes
C(14) C(15) C(16) 118.25(4) 1_555 1_555 1_555 yes
C(14) C(15) H(15) 118.38(4) 1_555 1_555 1_555 yes
C(16) C(15) H(15) 123.36(5) 1_555 1_555 1_555 yes
C(15) C(16) C(17) 121.22(4) 1_555 1_555 1_555 yes
C(15) C(16) H(16) 121.72(4) 1_555 1_555 1_555 yes
C(17) C(16) H(16) 117.04(4) 1_555 1_555 1_555 yes
N(6) C(17) C(16) 115.78(4) 1_555 1_555 1_555 yes
N(6) C(17) C(18) 124.72(3) 1_555 1_555 1_555 yes
C(16) C(17) C(18) 119.35(3) 1_555 1_555 1_555 yes
C(17) C(18) C(19) 119.68(4) 1_555 1_555 1_555 yes
C(17) C(18) H(18) 121.82(4) 1_555 1_555 1_555 yes
C(19) C(18) H(18) 118.43(4) 1_555 1_555 1_555 yes
C(14) C(19) C(18) 119.61(4) 1_555 1_555 1_555 yes
C(14) C(19) H(19) 121.38(4) 1_555 1_555 1_555 yes
C(18) C(19) H(19) 119.00(4) 1_555 1_555 1_555 yes
S(2) C(20) N(6) 124.89(3) 1_555 1_555 1_555 yes
S(2) C(20) N(7) 124.59(3) 1_555 1_555 1_555 yes
N(6) C(20) N(7) 110.41(4) 1_555 1_555 1_555 yes
N(7) C(21) C(22) 117.43(4) 1_555 1_555 1_555 yes
N(7) C(21) C(26) 122.93(4) 1_555 1_555 1_555 yes
C(22) C(21) C(26) 119.51(3) 1_555 1_555 1_555 yes
C(21) C(22) C(23) 120.98(4) 1_555 1_555 1_555 yes
C(21) C(22) H(22) 122.25(4) 1_555 1_555 1_555 yes
C(23) C(22) H(22) 116.76(4) 1_555 1_555 1_555 yes
C(22) C(23) C(24) 118.20(4) 1_555 1_555 1_555 yes
C(22) C(23) H(23) 119.30(5) 1_555 1_555 1_555 yes
C(24) C(23) H(23) 122.49(4) 1_555 1_555 1_555 yes
N(8) C(24) C(23) 119.55(4) 1_555 1_555 1_555 yes
N(8) C(24) C(25) 118.55(4) 1_555 1_555 1_555 yes
C(23) C(24) C(25) 121.85(4) 1_555 1_555 1_555 yes
C(24) C(25) C(26) 119.58(4) 1_555 1_555 1_555 yes
C(24) C(25) H(25) 119.64(4) 1_555 1_555 1_555 yes
C(26) C(25) H(25) 120.70(4) 1_555 1_555 1_555 yes
C(21) C(26) C(25) 119.84(4) 1_555 1_555 1_555 yes
C(21) C(26) H(26) 118.74(4) 1_555 1_555 1_555 yes
C(25) C(26) H(26) 121.29(4) 1_555 1_555 1_555 yes
N(1) C(1) C(2) 119.18(5) 1_555 1_555 1_555 yes
N(1) C(1) C(6) 119.23(5) 1_555 1_555 1_555 yes
C(2) C(1) C(6) 121.58(4) 1_555 1_555 1_555 yes
C(1) C(2) C(3) 118.50(4) 1_555 1_555 1_555 yes
C(1) C(2) H(2) 118.72(4) 1_555 1_555 1_555 yes
C(3) C(2) H(2) 122.78(4) 1_555 1_555 1_555 yes
C(2) C(3) C(4) 121.07(4) 1_555 1_555 1_555 yes
C(2) C(3) H(3) 119.76(4) 1_555 1_555 1_555 yes
C(4) C(3) H(3) 119.12(4) 1_555 1_555 1_555 yes
N(2) C(4) C(3) 116.31(4) 1_555 1_555 1_555 yes
N(2) C(4) C(5) 124.11(4) 1_555 1_555 1_555 yes
C(3) C(4) C(5) 119.46(4) 1_555 1_555 1_555 yes
C(4) C(5) C(6) 119.55(5) 1_555 1_555 1_555 yes
C(4) C(5) H(5) 123.02(4) 1_555 1_555 1_555 yes
C(6) C(5) H(5) 117.43(4) 1_555 1_555 1_555 yes
C(1) C(6) C(5) 119.80(4) 1_555 1_555 1_555 yes
C(1) C(6) H(6) 123.52(5) 1_555 1_555 1_555 yes
C(5) C(6) H(6) 116.59(5) 1_555 1_555 1_555 yes
S(1) C(7) N(2) 124.74(3) 1_555 1_555 1_555 yes
S(1) C(7) N(3) 124.90(3) 1_555 1_555 1_555 yes
N(2) C(7) N(3) 110.27(4) 1_555 1_555 1_555 yes
N(3) C(8) C(9) 116.05(4) 1_555 1_555 1_555 yes
N(3) C(8) C(13) 124.34(4) 1_555 1_555 1_555 yes
C(9) C(8) C(13) 119.49(4) 1_555 1_555 1_555 yes
C(8) C(9) C(10) 120.95(4) 1_555 1_555 1_555 yes
C(8) C(9) H(9) 119.61(4) 1_555 1_555 1_555 yes
C(10) C(9) H(9) 119.42(4) 1_555 1_555 1_555 yes
C(9) C(10) C(11) 118.46(4) 1_555 1_555 1_555 yes
C(9) C(10) H(10) 120.20(4) 1_555 1_555 1_555 yes
C(11) C(10) H(10) 121.32(4) 1_555 1_555 1_555 yes
N(4) C(11) C(10) 118.94(5) 1_555 1_555 1_555 yes
N(4) C(11) C(12) 119.19(5) 1_555 1_555 1_555 yes
C(10) C(11) C(12) 121.87(4) 1_555 1_555 1_555 yes
C(11) C(12) C(13) 119.55(5) 1_555 1_555 1_555 yes
C(11) C(12) H(12) 120.60(4) 1_555 1_555 1_555 yes
C(13) C(12) H(12) 119.85(5) 1_555 1_555 1_555 yes
C(8) C(13) C(12) 119.66(5) 1_555 1_555 1_555 yes
C(8) C(13) H(13) 120.66(4) 1_555 1_555 1_555 yes
C(12) C(13) H(13) 119.59(5) 1_555 1_555 1_555 yes

####################################################################### 
# 
# 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_shelxa
_database_code_depnum_ccdc_archive 'CCDC 1042631'
_audit_update_record             
;
2015-01-08 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_compound_source        'Isabelle L Kirby'
_database_code_CSD               ?
_chemical_name_systematic        
;
 '1-(4-nitrophenyl)-3-phenylurea with TEACl'
;
_chemical_name_common            '1-(4-nitrophenyl)-3-phenylurea with TEACl'
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 N3 O3, C8 H20 N, Cl'
_chemical_formula_sum            'C21 H31 Cl N4 O3'
_chemical_formula_weight         422.95

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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                   8.393(2)
_cell_length_b                   24.366(6)
_cell_length_c                   11.151(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.570(5)
_cell_angle_gamma                90.00
_cell_volume                     2185.8(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5425
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      31.3

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9603
_exptl_absorpt_correction_T_max  0.9939
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;

_exptl_special_details           
;
 ?
;
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11579
_diffrn_reflns_av_R_equivalents  0.1380
_diffrn_reflns_av_sigmaI/netI    0.1014
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4984
_reflns_number_gt                4116
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;

_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;

_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;

_computing_structure_solution    
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  'WINGX (Farrugia, 1998)'

_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 > 2σ(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)+(0.0509P)²+1.2280P] 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_number_reflns         4984
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0714
_refine_ls_wR_factor_ref         0.1654
_refine_ls_wR_factor_gt          0.1555
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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
C7 C 0.1482(3) 0.06497(10) 1.0858(2) 0.0233(5) Uani 1 1 d . . .
C4 C 0.3323(3) -0.01756(10) 1.1313(2) 0.0223(5) Uani 1 1 d . . .
C3 C 0.4413(3) -0.04678(10) 1.2296(2) 0.0215(5) Uani 1 1 d . . .
H3 H 0.4531 -0.0361 1.3137 0.026 Uiso 1 1 calc R . .
C2 C 0.5314(3) -0.09073(10) 1.2058(2) 0.0222(5) Uani 1 1 d . . .
H2 H 0.6039 -0.1107 1.2726 0.027 Uiso 1 1 calc R . .
C1 C 0.5143(3) -0.10520(10) 1.0829(2) 0.0238(5) Uani 1 1 d . . .
C6 C 0.4073(3) -0.07727(10) 0.9845(2) 0.0274(5) Uani 1 1 d . . .
H6 H 0.3972 -0.0882 0.9009 0.033 Uiso 1 1 calc R . .
C5 C 0.3151(3) -0.03368(10) 1.0072(2) 0.0276(5) Uani 1 1 d . . .
H5 H 0.2408 -0.0147 0.9396 0.033 Uiso 1 1 calc R . .
C8 C 0.0105(3) 0.15288(10) 1.1067(2) 0.0230(5) Uani 1 1 d . . .
C9 C 0.0218(3) 0.19636(11) 1.1900(2) 0.0282(5) Uani 1 1 d . . .
H9 H 0.0896 0.1928 1.2738 0.034 Uiso 1 1 calc R . .
C10 C -0.0646(4) 0.24460(12) 1.1520(3) 0.0336(6) Uani 1 1 d . . .
H10 H -0.0567 0.2737 1.2100 0.040 Uiso 1 1 calc R . .
C11 C -0.1629(3) 0.25059(12) 1.0292(3) 0.0333(6) Uani 1 1 d . . .
H11 H -0.2215 0.2838 1.0025 0.040 Uiso 1 1 calc R . .
C12 C -0.1744(3) 0.20767(12) 0.9465(2) 0.0320(6) Uani 1 1 d . . .
H3A H -0.2413 0.2117 0.8625 0.038 Uiso 1 1 calc R . .
C13 C -0.0902(3) 0.15869(11) 0.9834(2) 0.0289(6) Uani 1 1 d . . .
H13 H -0.1008 0.1294 0.9255 0.035 Uiso 1 1 calc R . .
C51 C 0.0449(3) -0.17180(10) 0.4703(2) 0.0241(5) Uani 1 1 d . . .
H51A H 0.0599 -0.1949 0.5458 0.029 Uiso 1 1 calc R . .
H51B H -0.0641 -0.1532 0.4543 0.029 Uiso 1 1 calc R . .
C57 C 0.3516(3) -0.15425(11) 0.5288(2) 0.0271(5) Uani 1 1 d . . .
H57A H 0.3586 -0.1763 0.4559 0.033 Uiso 1 1 calc R . .
H57B H 0.4349 -0.1245 0.5405 0.033 Uiso 1 1 calc R . .
C55 C 0.1589(3) -0.09564(10) 0.6086(2) 0.0214(5) Uani 1 1 d . . .
H55A H 0.0458 -0.0796 0.5855 0.026 Uiso 1 1 calc R . .
H55B H 0.1678 -0.1210 0.6795 0.026 Uiso 1 1 calc R . .
C53 C 0.1633(3) -0.09140(10) 0.3859(2) 0.0244(5) Uani 1 1 d . . .
H53A H 0.2504 -0.0628 0.4095 0.029 Uiso 1 1 calc R . .
H53B H 0.1859 -0.1136 0.3182 0.029 Uiso 1 1 calc R . .
C54 C -0.0022(4) -0.06351(12) 0.3348(2) 0.0342(6) Uani 1 1 d . . .
H54A H 0.0003 -0.0407 0.2629 0.051 Uiso 1 1 calc R . .
H54B H -0.0250 -0.0404 0.3998 0.051 Uiso 1 1 calc R . .
H54C H -0.0896 -0.0913 0.3083 0.051 Uiso 1 1 calc R . .
C56 C 0.2844(3) -0.04977(10) 0.6518(2) 0.0262(5) Uani 1 1 d . . .
H56A H 0.2628 -0.0308 0.7231 0.039 Uiso 1 1 calc R . .
H56B H 0.2745 -0.0237 0.5832 0.039 Uiso 1 1 calc R . .
H56C H 0.3969 -0.0652 0.6771 0.039 Uiso 1 1 calc R . .
C58 C 0.3977(3) -0.19056(12) 0.6433(3) 0.0353(6) Uani 1 1 d . . .
H58A H 0.5096 -0.2054 0.6549 0.053 Uiso 1 1 calc R . .
H58B H 0.3179 -0.2208 0.6323 0.053 Uiso 1 1 calc R . .
H58C H 0.3956 -0.1690 0.7170 0.053 Uiso 1 1 calc R . .
C52 C 0.0398(4) -0.20890(11) 0.3608(3) 0.0339(6) Uani 1 1 d . . .
H52A H -0.0510 -0.2354 0.3502 0.051 Uiso 1 1 calc R . .
H52B H 0.1456 -0.2286 0.3764 0.051 Uiso 1 1 calc R . .
H52C H 0.0214 -0.1868 0.2846 0.051 Uiso 1 1 calc R . .
N2 N 0.2501(3) 0.02685(8) 1.16454(17) 0.0233(4) Uani 1 1 d . . .
H1 H 0.2641 0.0314 1.2452 0.028 Uiso 1 1 calc R . .
N3 N 0.0973(3) 0.10473(8) 1.15321(18) 0.0253(5) Uani 1 1 d . . .
H2A H 0.1217 0.0995 1.2345 0.030 Uiso 1 1 calc R . .
N1 N 0.6114(3) -0.15074(9) 1.0558(2) 0.0286(5) Uani 1 1 d . . .
N5 N 0.1796(2) -0.12840(8) 0.49827(17) 0.0185(4) Uani 1 1 d . . .
O1 O 0.1112(2) 0.06309(7) 0.97176(15) 0.0309(4) Uani 1 1 d . . .
O2 O 0.6043(3) -0.16023(8) 0.94619(17) 0.0374(5) Uani 1 1 d . . .
O3 O 0.6965(3) -0.17810(8) 1.14426(19) 0.0411(5) Uani 1 1 d . . .
Cl1 Cl 0.28512(7) 0.07306(3) 1.44167(5) 0.02446(17) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C7 O1 1.221(3) . ?
C7 N3 1.367(3) . ?
C7 N2 1.391(3) . ?
C4 N2 1.390(3) . ?
C4 C3 1.405(3) . ?
C4 C5 1.406(3) . ?
C3 C2 1.380(3) . ?
C3 H3 0.9500 . ?
C2 C1 1.382(3) . ?
C2 H2 0.9500 . ?
C1 C6 1.383(3) . ?
C1 N1 1.459(3) . ?
C6 C5 1.379(4) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C8 C9 1.394(4) . ?
C8 C13 1.400(3) . ?
C8 N3 1.400(3) . ?
C9 C10 1.382(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(4) . ?
C12 H3A 0.9500 . ?
C13 H13 0.9500 . ?
C51 C52 1.510(4) . ?
C51 N5 1.514(3) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C57 C58 1.510(4) . ?
C57 N5 1.522(3) . ?
C57 H57A 0.9900 . ?
C57 H57B 0.9900 . ?
C55 C56 1.517(3) . ?
C55 N5 1.518(3) . ?
C55 H55A 0.9900 . ?
C55 H55B 0.9900 . ?
C53 C54 1.505(3) . ?
C53 N5 1.518(3) . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 0.9800 . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
N2 H1 0.8800 . ?
N3 H2A 0.8800 . ?
N1 O2 1.228(3) . ?
N1 O3 1.235(3) . ?

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
O1 C7 N3 124.9(2) . . ?
O1 C7 N2 124.1(2) . . ?
N3 C7 N2 110.97(19) . . ?
N2 C4 C3 116.7(2) . . ?
N2 C4 C5 124.1(2) . . ?
C3 C4 C5 119.2(2) . . ?
C2 C3 C4 120.9(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C2 C1 118.8(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C1 C6 121.4(2) . . ?
C2 C1 N1 119.6(2) . . ?
C6 C1 N1 119.0(2) . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C6 C5 C4 119.4(2) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C9 C8 C13 119.0(2) . . ?
C9 C8 N3 117.4(2) . . ?
C13 C8 N3 123.6(2) . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.2(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 119.2(2) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 121.4(2) . . ?
C11 C12 H3A 119.3 . . ?
C13 C12 H3A 119.3 . . ?
C12 C13 C8 119.4(2) . . ?
C12 C13 H13 120.3 . . ?
C8 C13 H13 120.3 . . ?
C52 C51 N5 115.6(2) . . ?
C52 C51 H51A 108.4 . . ?
N5 C51 H51A 108.4 . . ?
C52 C51 H51B 108.4 . . ?
N5 C51 H51B 108.4 . . ?
H51A C51 H51B 107.4 . . ?
C58 C57 N5 115.4(2) . . ?
C58 C57 H57A 108.4 . . ?
N5 C57 H57A 108.4 . . ?
C58 C57 H57B 108.4 . . ?
N5 C57 H57B 108.4 . . ?
H57A C57 H57B 107.5 . . ?
C56 C55 N5 114.56(19) . . ?
C56 C55 H55A 108.6 . . ?
N5 C55 H55A 108.6 . . ?
C56 C55 H55B 108.6 . . ?
N5 C55 H55B 108.6 . . ?
H55A C55 H55B 107.6 . . ?
C54 C53 N5 115.9(2) . . ?
C54 C53 H53A 108.3 . . ?
N5 C53 H53A 108.3 . . ?
C54 C53 H53B 108.3 . . ?
N5 C53 H53B 108.3 . . ?
H53A C53 H53B 107.4 . . ?
C53 C54 H54A 109.5 . . ?
C53 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C53 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C55 C56 H56A 109.5 . . ?
C55 C56 H56B 109.5 . . ?
H56A C56 H56B 109.5 . . ?
C55 C56 H56C 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C57 C58 H58A 109.5 . . ?
C57 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C57 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C4 N2 C7 127.9(2) . . ?
C4 N2 H1 116.1 . . ?
C7 N2 H1 116.1 . . ?
C7 N3 C8 126.9(2) . . ?
C7 N3 H2A 116.5 . . ?
C8 N3 H2A 116.5 . . ?
O2 N1 O3 123.1(2) . . ?
O2 N1 C1 118.6(2) . . ?
O3 N1 C1 118.3(2) . . ?
C51 N5 C55 106.44(17) . . ?
C51 N5 C53 111.03(17) . . ?
C55 N5 C53 110.64(18) . . ?
C51 N5 C57 111.21(18) . . ?
C55 N5 C57 110.92(17) . . ?
C53 N5 C57 106.67(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1 Cl1 0.88 2.37 3.223(2) 161.8 .
N3 H2A Cl1 0.88 2.41 3.246(2) 157.9 .

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.080
####################################################################### 
# 
# 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_shelxa
_database_code_depnum_ccdc_archive 'CCDC 1042632'
_audit_update_record             
;
2015-01-08 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_compound_source        'Isabelle Kirby'
_database_code_CSD               ?

_chemical_name_systematic        
;
 1-(4-nitrophenyl)-3-phenylthiourea TMA CL
;
_chemical_name_common            ' 1-(4-nitrophenyl)-3-phenylthiourea TMA CL'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C13 H11 N3 O2 S), C4 H12 N, Cl'
_chemical_formula_sum            'C30 H34 Cl N7 O4 S2'
_chemical_formula_weight         656.21

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           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1587(14)
_cell_length_b                   10.2436(16)
_cell_length_c                   17.871(3)
_cell_angle_alpha                87.983(6)
_cell_angle_beta                 79.043(5)
_cell_angle_gamma                72.220(6)
_cell_volume                     1566.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6567
_cell_measurement_theta_min      2.8
_cell_measurement_theta_max      34.9

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7935
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_reflns_number            7168
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         27.48
_reflns_number_total             7168
_reflns_number_gt                7086
_reflns_threshold_expression     >2σ(I)
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_computing_molecular_graphics    ?
_computing_publication_material  'WINGX (Farrugia, 1998)'

_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 > 2σ(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)+(0.0592P)²+0.0978P] 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_number_reflns         7168
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.1088
_refine_ls_wR_factor_gt          0.1082
_refine_ls_goodness_of_fit_ref   1.289
_refine_ls_restrained_S_all      1.289
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.28460(15) 0.11683(12) -0.06648(7) 0.0225(2) Uani 1 1 d . . .
C2 C 0.34831(14) 0.17578(12) -0.01717(7) 0.0212(2) Uani 1 1 d . . .
H2 H 0.3894 0.2491 -0.0330 0.025 Uiso 1 1 calc R . .
C3 C 0.35051(14) 0.12542(12) 0.05528(7) 0.0192(2) Uani 1 1 d . . .
H3 H 0.3925 0.1653 0.0899 0.023 Uiso 1 1 calc R . .
C4 C 0.29140(13) 0.01573(11) 0.07875(7) 0.0180(2) Uani 1 1 d . . .
C5 C 0.22336(15) -0.03914(12) 0.02876(7) 0.0226(2) Uani 1 1 d . . .
H5 H 0.1792 -0.1106 0.0447 0.027 Uiso 1 1 calc R . .
C6 C 0.22097(16) 0.01170(13) -0.04418(7) 0.0248(2) Uani 1 1 d . . .
H6 H 0.1760 -0.0254 -0.0787 0.030 Uiso 1 1 calc R . .
C7 C 0.29944(13) -0.14822(12) 0.18788(7) 0.0186(2) Uani 1 1 d . . .
C8 C 0.31850(13) -0.24269(12) 0.31811(7) 0.0181(2) Uani 1 1 d . . .
C9 C 0.23978(15) -0.20105(12) 0.39235(7) 0.0214(2) Uani 1 1 d . . .
H9 H 0.1785 -0.1081 0.4029 0.026 Uiso 1 1 calc R . .
C10 C 0.25038(15) -0.29450(13) 0.45094(7) 0.0235(2) Uani 1 1 d . . .
H10 H 0.1971 -0.2651 0.5013 0.028 Uiso 1 1 calc R . .
C11 C 0.33890(15) -0.43121(13) 0.43588(7) 0.0242(2) Uani 1 1 d . . .
H11 H 0.3458 -0.4955 0.4757 0.029 Uiso 1 1 calc R . .
C12 C 0.41728(15) -0.47268(13) 0.36169(8) 0.0243(2) Uani 1 1 d . . .
H12 H 0.4771 -0.5659 0.3511 0.029 Uiso 1 1 calc R . .
C13 C 0.40901(14) -0.37934(12) 0.30299(7) 0.0215(2) Uani 1 1 d . . .
H13 H 0.4646 -0.4084 0.2529 0.026 Uiso 1 1 calc R . .
C14 C 0.80891(14) 0.38414(11) 0.04477(6) 0.0170(2) Uani 1 1 d . . .
C15 C 0.65275(14) 0.41474(12) 0.07876(7) 0.0198(2) Uani 1 1 d . . .
H15 H 0.5738 0.4752 0.0554 0.024 Uiso 1 1 calc R . .
C16 C 0.61442(14) 0.35526(12) 0.14748(6) 0.0192(2) Uani 1 1 d . . .
H16 H 0.5079 0.3742 0.1713 0.023 Uiso 1 1 calc R . .
C17 C 0.73130(13) 0.26714(11) 0.18235(6) 0.0159(2) Uani 1 1 d . . .
C18 C 0.88841(13) 0.23792(12) 0.14688(6) 0.0179(2) Uani 1 1 d . . .
H18 H 0.9682 0.1781 0.1700 0.022 Uiso 1 1 calc R . .
C19 C 0.92652(13) 0.29715(12) 0.07774(6) 0.0185(2) Uani 1 1 d . . .
H19 H 1.0326 0.2781 0.0532 0.022 Uiso 1 1 calc R . .
C20 C 0.75418(13) 0.13307(11) 0.30346(6) 0.0161(2) Uani 1 1 d . . .
C21 C 0.68731(13) -0.02667(11) 0.40597(6) 0.0157(2) Uani 1 1 d . . .
C22 C 0.58787(13) -0.10886(12) 0.41820(6) 0.0180(2) Uani 1 1 d . . .
H22 H 0.5129 -0.0999 0.3867 0.022 Uiso 1 1 calc R . .
C23 C 0.59836(14) -0.20324(12) 0.47615(7) 0.0197(2) Uani 1 1 d . . .
H23 H 0.5307 -0.2586 0.4840 0.024 Uiso 1 1 calc R . .
C24 C 0.70751(14) -0.21721(12) 0.52287(7) 0.0205(2) Uani 1 1 d . . .
H24 H 0.7147 -0.2818 0.5626 0.025 Uiso 1 1 calc R . .
C25 C 0.80575(14) -0.13553(12) 0.51071(7) 0.0201(2) Uani 1 1 d . . .
H25 H 0.8805 -0.1449 0.5424 0.024 Uiso 1 1 calc R . .
C26 C 0.79689(14) -0.04000(12) 0.45281(6) 0.0183(2) Uani 1 1 d . . .
H26 H 0.8646 0.0154 0.4453 0.022 Uiso 1 1 calc R . .
C71 C -0.05433(17) 0.53090(14) -0.23216(7) 0.0266(3) Uani 1 1 d . . .
H71A H -0.0538 0.6262 -0.2299 0.040 Uiso 1 1 calc R . .
H71B H -0.0110 0.4810 -0.1896 0.040 Uiso 1 1 calc R . .
H71C H -0.1617 0.5290 -0.2287 0.040 Uiso 1 1 calc R . .
C72 C 0.20592(15) 0.46830(14) -0.31122(8) 0.0266(3) Uani 1 1 d . . .
H72A H 0.2059 0.5637 -0.3088 0.040 Uiso 1 1 calc R . .
H72B H 0.2695 0.4253 -0.3596 0.040 Uiso 1 1 calc R . .
H72C H 0.2496 0.4182 -0.2688 0.040 Uiso 1 1 calc R . .
C73 C -0.02373(17) 0.54098(15) -0.37045(7) 0.0281(3) Uani 1 1 d . . .
H73A H -0.0235 0.6363 -0.3680 0.042 Uiso 1 1 calc R . .
H73B H -0.1311 0.5388 -0.3669 0.042 Uiso 1 1 calc R . .
H73C H 0.0398 0.4979 -0.4189 0.042 Uiso 1 1 calc R . .
C74 C 0.04207(16) 0.31938(13) -0.30952(9) 0.0278(3) Uani 1 1 d . . .
H74A H -0.0653 0.3173 -0.3059 0.042 Uiso 1 1 calc R . .
H74B H 0.0857 0.2692 -0.2671 0.042 Uiso 1 1 calc R . .
H74C H 0.1054 0.2763 -0.3580 0.042 Uiso 1 1 calc R . .
N1 N 0.28197(14) 0.16848(12) -0.14365(6) 0.0292(2) Uani 1 1 d . . .
N2 N 0.30171(12) -0.02695(10) 0.15341(6) 0.0198(2) Uani 1 1 d . . .
H2A H 0.3113 0.0349 0.1835 0.024 Uiso 1 1 calc R . .
N3 N 0.30872(12) -0.14034(10) 0.26282(6) 0.0198(2) Uani 1 1 d . . .
H3A H 0.3086 -0.0601 0.2789 0.024 Uiso 1 1 calc R . .
N4 N 0.85167(12) 0.44366(10) -0.02834(6) 0.0194(2) Uani 1 1 d . . .
N5 N 0.67759(11) 0.20754(10) 0.24940(5) 0.01766(19) Uani 1 1 d . . .
H5A H 0.5763 0.2200 0.2586 0.021 Uiso 1 1 calc R . .
N6 N 0.66169(11) 0.06700(10) 0.34676(6) 0.01781(19) Uani 1 1 d . . .
H6A H 0.5678 0.0864 0.3357 0.021 Uiso 1 1 calc R . .
N7 N 0.04266(11) 0.46470(10) -0.30586(6) 0.01749(19) Uani 1 1 d . . .
O1 O 0.24011(18) 0.10626(12) -0.18885(6) 0.0487(3) Uani 1 1 d . . .
O2 O 0.32225(13) 0.27143(12) -0.15997(6) 0.0359(2) Uani 1 1 d . . .
O3 O 0.74908(11) 0.53051(9) -0.05428(5) 0.02354(19) Uani 1 1 d . . .
O4 O 0.98961(11) 0.40387(10) -0.06109(5) 0.0262(2) Uani 1 1 d . . .
S1 S 0.28790(4) -0.28610(3) 0.145563(17) 0.02401(9) Uani 1 1 d . . .
S2 S 0.93230(3) 0.13071(3) 0.315268(17) 0.02192(9) Uani 1 1 d . . .
Cl1 Cl 0.34265(3) 0.16604(3) 0.278147(15) 0.01868(8) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.3867(18) . ?
C1 C2 1.3891(18) . ?
C1 N1 1.4614(16) . ?
C2 C3 1.3782(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.4084(16) . ?
C3 H3 0.9500 . ?
C4 N2 1.4006(15) . ?
C4 C5 1.4012(16) . ?
C5 C6 1.3881(17) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N3 1.3647(15) . ?
C7 N2 1.3711(15) . ?
C7 S1 1.6657(12) . ?
C8 C13 1.3973(16) . ?
C8 C9 1.3967(16) . ?
C8 N3 1.4095(14) . ?
C9 C10 1.3904(17) . ?
C9 H9 0.9500 . ?
C10 C11 1.3932(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.3947(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.3913(17) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.3854(16) . ?
C14 C15 1.3864(16) . ?
C14 N4 1.4586(14) . ?
C15 C16 1.3844(15) . ?
C15 H15 0.9500 . ?
C16 C17 1.4046(15) . ?
C16 H16 0.9500 . ?
C17 N5 1.3995(14) . ?
C17 C18 1.4019(15) . ?
C18 C19 1.3890(15) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 N6 1.3559(14) . ?
C20 N5 1.3734(14) . ?
C20 S2 1.6771(12) . ?
C21 C26 1.3980(16) . ?
C21 C22 1.4020(15) . ?
C21 N6 1.4074(14) . ?
C22 C23 1.3882(15) . ?
C22 H22 0.9500 . ?
C23 C24 1.3923(17) . ?
C23 H23 0.9500 . ?
C24 C25 1.3891(17) . ?
C24 H24 0.9500 . ?
C25 C26 1.3953(15) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C71 N7 1.4945(14) . ?
C71 H71A 0.9800 . ?
C71 H71B 0.9800 . ?
C71 H71C 0.9800 . ?
C72 N7 1.4918(15) . ?
C72 H72A 0.9800 . ?
C72 H72B 0.9800 . ?
C72 H72C 0.9800 . ?
C73 N7 1.4919(15) . ?
C73 H73A 0.9800 . ?
C73 H73B 0.9800 . ?
C73 H73C 0.9800 . ?
C74 N7 1.4940(15) . ?
C74 H74A 0.9800 . ?
C74 H74B 0.9800 . ?
C74 H74C 0.9800 . ?
N1 O2 1.2281(17) . ?
N1 O1 1.2284(17) . ?
N2 H2A 0.8800 . ?
N3 H3A 0.8800 . ?
N4 O3 1.2310(14) . ?
N4 O4 1.2353(14) . ?
N5 H5A 0.8800 . ?
N6 H6A 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 121.86(11) . . ?
C6 C1 N1 118.95(12) . . ?
C2 C1 N1 119.18(12) . . ?
C3 C2 C1 118.43(11) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 121.00(11) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
N2 C4 C5 124.97(11) . . ?
N2 C4 C3 115.55(10) . . ?
C5 C4 C3 119.45(11) . . ?
C6 C5 C4 119.49(11) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 119.70(12) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N3 C7 N2 109.94(10) . . ?
N3 C7 S1 124.35(9) . . ?
N2 C7 S1 125.71(9) . . ?
C13 C8 C9 119.48(11) . . ?
C13 C8 N3 123.38(11) . . ?
C9 C8 N3 117.03(10) . . ?
C10 C9 C8 120.52(11) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 120.15(12) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 119.26(12) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 120.91(12) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C8 119.66(11) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
C19 C14 C15 122.01(10) . . ?
C19 C14 N4 118.60(10) . . ?
C15 C14 N4 119.39(10) . . ?
C16 C15 C14 118.50(11) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
C15 C16 C17 120.70(11) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
N5 C17 C18 124.81(10) . . ?
N5 C17 C16 115.34(10) . . ?
C18 C17 C16 119.72(10) . . ?
C19 C18 C17 119.47(11) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C14 C19 C18 119.60(11) . . ?
C14 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
N6 C20 N5 109.63(10) . . ?
N6 C20 S2 125.89(9) . . ?
N5 C20 S2 124.44(8) . . ?
C26 C21 C22 119.50(10) . . ?
C26 C21 N6 125.92(10) . . ?
C22 C21 N6 114.55(10) . . ?
C23 C22 C21 120.36(11) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 120.41(11) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C25 C24 C23 119.13(11) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 C26 121.32(11) . . ?
C24 C25 H25 119.3 . . ?
C26 C25 H25 119.3 . . ?
C25 C26 C21 119.29(10) . . ?
C25 C26 H26 120.4 . . ?
C21 C26 H26 120.4 . . ?
N7 C71 H71A 109.5 . . ?
N7 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
N7 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
N7 C72 H72A 109.5 . . ?
N7 C72 H72B 109.5 . . ?
H72A C72 H72B 109.5 . . ?
N7 C72 H72C 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 109.5 . . ?
N7 C73 H73A 109.5 . . ?
N7 C73 H73B 109.5 . . ?
H73A C73 H73B 109.5 . . ?
N7 C73 H73C 109.5 . . ?
H73A C73 H73C 109.5 . . ?
H73B C73 H73C 109.5 . . ?
N7 C74 H74A 109.5 . . ?
N7 C74 H74B 109.5 . . ?
H74A C74 H74B 109.5 . . ?
N7 C74 H74C 109.5 . . ?
H74A C74 H74C 109.5 . . ?
H74B C74 H74C 109.5 . . ?
O2 N1 O1 123.47(13) . . ?
O2 N1 C1 118.31(12) . . ?
O1 N1 C1 118.22(12) . . ?
C7 N2 C4 131.32(10) . . ?
C7 N2 H2A 114.3 . . ?
C4 N2 H2A 114.3 . . ?
C7 N3 C8 129.11(10) . . ?
C7 N3 H3A 115.4 . . ?
C8 N3 H3A 115.4 . . ?
O3 N4 O4 123.39(10) . . ?
O3 N4 C14 118.60(10) . . ?
O4 N4 C14 118.01(10) . . ?
C20 N5 C17 131.70(10) . . ?
C20 N5 H5A 114.1 . . ?
C17 N5 H5A 114.1 . . ?
C20 N6 C21 132.20(10) . . ?
C20 N6 H6A 113.9 . . ?
C21 N6 H6A 113.9 . . ?
C72 N7 C73 109.44(10) . . ?
C72 N7 C74 109.67(10) . . ?
C73 N7 C74 109.44(10) . . ?
C72 N7 C71 109.38(10) . . ?
C73 N7 C71 109.29(10) . . ?
C74 N7 C71 109.61(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A Cl1 0.88 2.31 3.1778(11) 169.6 .
N3 H3A Cl1 0.88 2.43 3.2726(11) 160.7 .
N5 H5A Cl1 0.88 2.33 3.1682(11) 158.9 .
N6 H6A Cl1 0.88 2.39 3.2457(11) 165.1 .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_shelxa
_database_code_depnum_ccdc_archive 'CCDC 1042633'
_audit_update_record             
;
2015-01-08 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ' 1,3-bis(4-nitrophenyl)thiourea TEA CL'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C13 H10 N4 O4 S), C8 H20 N, Cl'
_chemical_formula_sum            'C34 H40 Cl N9 O8 S2'
_chemical_formula_weight         802.32

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           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.968(2)
_cell_length_b                   15.649(4)
_cell_length_c                   15.899(4)
_cell_angle_alpha                113.0610(10)
_cell_angle_beta                 103.685(3)
_cell_angle_gamma                101.701(2)
_cell_volume                     1882.6(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6076
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      32.9

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9194
_exptl_absorpt_correction_T_max  0.9677
_exptl_absorpt_process_details   
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;
_diffrn_reflns_reduction_process 
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_diffrn_source_current           55.0
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_reflns_number            8397
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         27.48
_reflns_number_total             8397
_reflns_number_gt                8195
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

_computing_molecular_graphics    ?
_computing_publication_material  'WINGX (Farrugia, 1998)'

_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 > 2σ(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)+(0.0494P)²+0.2449P] 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_number_reflns         8397
_refine_ls_number_parameters     487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1377
_refine_ls_wR_factor_gt          0.1371
_refine_ls_goodness_of_fit_ref   1.632
_refine_ls_restrained_S_all      1.632
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C91 C 0.6712(2) 0.78835(11) 1.22134(11) 0.0226(3) Uani 1 1 d . . .
H91A H 0.7802 0.8372 1.2448 0.027 Uiso 1 1 calc R . .
H91B H 0.5929 0.8248 1.2287 0.027 Uiso 1 1 calc R . .
C92 C 0.6734(2) 0.73860(12) 1.28592(11) 0.0245(3) Uani 1 1 d . . .
H92A H 0.7034 0.7882 1.3538 0.037 Uiso 1 1 calc R . .
H92B H 0.7529 0.7039 1.2810 0.037 Uiso 1 1 calc R . .
H92C H 0.5652 0.6914 1.2648 0.037 Uiso 1 1 calc R . .
C93 C 0.7476(2) 0.66558(12) 1.09699(12) 0.0253(3) Uani 1 1 d . . .
H93A H 0.7137 0.6213 1.0262 0.030 Uiso 1 1 calc R . .
H93B H 0.7434 0.6239 1.1305 0.030 Uiso 1 1 calc R . .
C94 C 0.9225(2) 0.7317(2) 1.13270(17) 0.0438(5) Uani 1 1 d . . .
H94A H 0.9923 0.6911 1.1192 0.066 Uiso 1 1 calc R . .
H94B H 0.9588 0.7746 1.2031 0.066 Uiso 1 1 calc R . .
H94C H 0.9290 0.7721 1.0987 0.066 Uiso 1 1 calc R . .
C95 C 0.6247(2) 0.78420(11) 1.06340(11) 0.0228(3) Uani 1 1 d . . .
H95A H 0.7333 0.8350 1.0923 0.027 Uiso 1 1 calc R . .
H95B H 0.5452 0.8185 1.0769 0.027 Uiso 1 1 calc R . .
C96 C 0.5825(2) 0.72978(12) 0.95405(11) 0.0229(3) Uani 1 1 d . . .
H96A H 0.5836 0.7765 0.9272 0.034 Uiso 1 1 calc R . .
H96B H 0.4739 0.6803 0.9243 0.034 Uiso 1 1 calc R . .
H96C H 0.6625 0.6973 0.9398 0.034 Uiso 1 1 calc R . .
C97 C 0.4617(2) 0.64012(12) 1.07270(12) 0.0248(3) Uani 1 1 d . . .
H97A H 0.4419 0.5945 1.0040 0.030 Uiso 1 1 calc R . .
H97B H 0.4665 0.6020 1.1098 0.030 Uiso 1 1 calc R . .
C98 C 0.3189(2) 0.6774(2) 1.07602(16) 0.0423(5) Uani 1 1 d . . .
H98A H 0.2185 0.6215 1.0483 0.064 Uiso 1 1 calc R . .
H98B H 0.3108 0.7138 1.0381 0.064 Uiso 1 1 calc R . .
H98C H 0.3350 0.7210 1.1439 0.064 Uiso 1 1 calc R . .
N9 N 0.62619(15) 0.71967(8) 1.11347(9) 0.0161(2) Uani 1 1 d . . .
C14 C 1.20260(18) 0.88041(10) 0.90915(10) 0.0181(3) Uani 1 1 d . . .
C15 C 1.06423(19) 0.84793(11) 0.92849(11) 0.0201(3) Uani 1 1 d . . .
H15 H 1.0199 0.8933 0.9652 0.024 Uiso 1 1 calc R . .
C16 C 0.99311(18) 0.74776(11) 0.89271(11) 0.0189(3) Uani 1 1 d . . .
H16 H 0.8995 0.7241 0.9059 0.023 Uiso 1 1 calc R . .
C17 C 1.05695(17) 0.68049(10) 0.83729(10) 0.0158(3) Uani 1 1 d . . .
C18 C 1.19576(18) 0.71524(10) 0.81856(11) 0.0183(3) Uani 1 1 d . . .
H18 H 1.2392 0.6702 0.7806 0.022 Uiso 1 1 calc R . .
C19 C 1.26967(18) 0.81587(11) 0.85581(11) 0.0191(3) Uani 1 1 d . . .
H19 H 1.3653 0.8402 0.8448 0.023 Uiso 1 1 calc R . .
C20 C 1.01209(17) 0.49931(10) 0.76509(10) 0.0152(2) Uani 1 1 d . . .
C21 C 0.86392(17) 0.31910(10) 0.66143(10) 0.0153(2) Uani 1 1 d . . .
C22 C 0.74043(18) 0.24332(11) 0.65531(11) 0.0197(3) Uani 1 1 d . . .
H22 H 0.6741 0.2592 0.6938 0.024 Uiso 1 1 calc R . .
C23 C 0.71374(19) 0.14549(11) 0.59385(11) 0.0212(3) Uani 1 1 d . . .
H23 H 0.6304 0.0941 0.5899 0.025 Uiso 1 1 calc R . .
C24 C 0.81242(18) 0.12478(10) 0.53833(10) 0.0181(3) Uani 1 1 d . . .
C25 C 0.93440(19) 0.19826(11) 0.54234(11) 0.0204(3) Uani 1 1 d . . .
H25 H 1.0005 0.1818 0.5038 0.025 Uiso 1 1 calc R . .
C26 C 0.95908(18) 0.29596(11) 0.60311(11) 0.0197(3) Uani 1 1 d . . .
H26 H 1.0403 0.3470 0.6051 0.024 Uiso 1 1 calc R . .
N5 N 1.27653(18) 0.98568(9) 0.94338(9) 0.0220(3) Uani 1 1 d . . .
N6 N 0.96778(15) 0.58113(9) 0.79915(9) 0.0172(2) Uani 1 1 d . . .
H6A H 0.8663 0.5695 0.7967 0.021 Uiso 1 1 calc R . .
N7 N 0.87889(15) 0.41611(9) 0.72238(9) 0.0167(2) Uani 1 1 d . . .
H7A H 0.7910 0.4247 0.7349 0.020 Uiso 1 1 calc R . .
N8 N 0.78436(18) 0.02250(9) 0.47065(10) 0.0222(3) Uani 1 1 d . . .
O5 O 1.39614(15) 1.01321(9) 0.92374(10) 0.0290(3) Uani 1 1 d . . .
O6 O 1.21380(19) 1.04190(9) 0.98939(9) 0.0322(3) Uani 1 1 d . . .
O7 O 0.87083(19) 0.00608(9) 0.42081(10) 0.0348(3) Uani 1 1 d . . .
O8 O 0.67289(17) -0.04225(9) 0.46508(9) 0.0295(3) Uani 1 1 d . . .
S2 S 1.20313(4) 0.49997(2) 0.77994(3) 0.01848(10) Uani 1 1 d . . .
Cl1 Cl 0.60047(4) 0.50475(2) 0.77653(2) 0.01831(10) Uani 1 1 d . . .
C1 C 0.5502(2) 0.90761(11) 0.74234(11) 0.0200(3) Uani 1 1 d . . .
C2 C 0.65813(19) 0.87048(11) 0.78350(11) 0.0197(3) Uani 1 1 d . . .
H2 H 0.7581 0.9133 0.8350 0.024 Uiso 1 1 calc R . .
C3 C 0.61609(18) 0.76922(11) 0.74732(10) 0.0185(3) Uani 1 1 d . . .
H3 H 0.6890 0.7423 0.7739 0.022 Uiso 1 1 calc R . .
C4 C 0.46792(18) 0.70604(11) 0.67225(10) 0.0176(3) Uani 1 1 d . . .
C5 C 0.35912(19) 0.74564(12) 0.63367(11) 0.0209(3) Uani 1 1 d . . .
H5 H 0.2569 0.7035 0.5840 0.025 Uiso 1 1 calc R . .
C6 C 0.4021(2) 0.84656(12) 0.66867(11) 0.0218(3) Uani 1 1 d . . .
H6 H 0.3302 0.8740 0.6422 0.026 Uiso 1 1 calc R . .
C7 C 0.34185(18) 0.52580(11) 0.55580(11) 0.0185(3) Uani 1 1 d . . .
C8 C 0.26905(18) 0.34307(11) 0.48830(10) 0.0178(3) Uani 1 1 d . . .
C9 C 0.34679(18) 0.27646(11) 0.49780(11) 0.0189(3) Uani 1 1 d . . .
H9 H 0.4486 0.3002 0.5486 0.023 Uiso 1 1 calc R . .
C10 C 0.27790(19) 0.17683(11) 0.43449(11) 0.0194(3) Uani 1 1 d . . .
H10 H 0.3305 0.1319 0.4416 0.023 Uiso 1 1 calc R . .
C11 C 0.12979(19) 0.14420(11) 0.36031(10) 0.0197(3) Uani 1 1 d . . .
C12 C 0.05104(19) 0.20819(12) 0.34790(11) 0.0221(3) Uani 1 1 d . . .
H12 H -0.0495 0.1839 0.2959 0.027 Uiso 1 1 calc R . .
C13 C 0.12011(19) 0.30823(11) 0.41204(11) 0.0210(3) Uani 1 1 d . . .
H13 H 0.0669 0.3528 0.4044 0.025 Uiso 1 1 calc R . .
N1 N 0.59471(19) 1.01421(10) 0.77803(11) 0.0255(3) Uani 1 1 d . . .
N2 N 0.43437(16) 0.60541(9) 0.64433(9) 0.0196(2) Uani 1 1 d . . .
H2A H 0.4794 0.5913 0.6905 0.023 Uiso 1 1 calc R . .
N3 N 0.34316(16) 0.44086(10) 0.56071(9) 0.0200(2) Uani 1 1 d . . .
H3A H 0.3993 0.4488 0.6183 0.024 Uiso 1 1 calc R . .
N4 N 0.05437(19) 0.03873(10) 0.29375(10) 0.0253(3) Uani 1 1 d . . .
O1 O 0.51404(19) 1.04422(10) 0.72886(11) 0.0352(3) Uani 1 1 d . . .
O2 O 0.7089(2) 1.06813(10) 0.85435(10) 0.0373(3) Uani 1 1 d . . .
O3 O -0.0747(2) 0.01079(10) 0.22710(10) 0.0408(4) Uani 1 1 d . . .
O4 O 0.12328(18) -0.01733(9) 0.30727(10) 0.0341(3) Uani 1 1 d . . .
S1 S 0.24975(6) 0.53184(3) 0.45560(3) 0.02714(11) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C91 C92 1.511(2) . ?
C91 N9 1.5205(18) . ?
C91 H91A 0.9900 . ?
C91 H91B 0.9900 . ?
C92 H92A 0.9800 . ?
C92 H92B 0.9800 . ?
C92 H92C 0.9800 . ?
C93 N9 1.5182(19) . ?
C93 C94 1.521(3) . ?
C93 H93A 0.9900 . ?
C93 H93B 0.9900 . ?
C94 H94A 0.9800 . ?
C94 H94B 0.9800 . ?
C94 H94C 0.9800 . ?
C95 N9 1.5113(18) . ?
C95 C96 1.513(2) . ?
C95 H95A 0.9900 . ?
C95 H95B 0.9900 . ?
C96 H96A 0.9800 . ?
C96 H96B 0.9800 . ?
C96 H96C 0.9800 . ?
C97 C98 1.515(3) . ?
C97 N9 1.5218(19) . ?
C97 H97A 0.9900 . ?
C97 H97B 0.9900 . ?
C98 H98A 0.9800 . ?
C98 H98B 0.9800 . ?
C98 H98C 0.9800 . ?
C14 C19 1.385(2) . ?
C14 C15 1.393(2) . ?
C14 N5 1.4607(18) . ?
C15 C16 1.383(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.4031(19) . ?
C16 H16 0.9500 . ?
C17 N6 1.3973(17) . ?
C17 C18 1.4006(19) . ?
C18 C19 1.3894(19) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 N6 1.3622(17) . ?
C20 N7 1.3696(17) . ?
C20 S2 1.6705(15) . ?
C21 C26 1.3986(19) . ?
C21 N7 1.4018(17) . ?
C21 C22 1.4029(18) . ?
C22 C23 1.387(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.389(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(2) . ?
C24 N8 1.4636(18) . ?
C25 C26 1.387(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
N5 O5 1.229(2) . ?
N5 O6 1.2316(19) . ?
N6 H6A 0.8800 . ?
N7 H7A 0.8800 . ?
N8 O8 1.2292(19) . ?
N8 O7 1.228(2) . ?
C1 C6 1.386(2) . ?
C1 C2 1.389(2) . ?
C1 N1 1.4647(19) . ?
C2 C3 1.387(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.400(2) . ?
C3 H3 0.9500 . ?
C4 N2 1.4015(19) . ?
C4 C5 1.404(2) . ?
C5 C6 1.384(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N3 1.3639(19) . ?
C7 N2 1.3697(19) . ?
C7 S1 1.6602(15) . ?
C8 N3 1.3979(18) . ?
C8 C9 1.401(2) . ?
C8 C13 1.404(2) . ?
C9 C10 1.382(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(2) . ?
C11 N4 1.4634(19) . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
N1 O2 1.222(2) . ?
N1 O1 1.230(2) . ?
N2 H2A 0.8800 . ?
N3 H3A 0.8800 . ?
N4 O4 1.226(2) . ?
N4 O3 1.227(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
C92 C91 N9 115.15(12) . . ?
C92 C91 H91A 108.5 . . ?
N9 C91 H91A 108.5 . . ?
C92 C91 H91B 108.5 . . ?
N9 C91 H91B 108.5 . . ?
H91A C91 H91B 107.5 . . ?
C91 C92 H92A 109.5 . . ?
C91 C92 H92B 109.5 . . ?
H92A C92 H92B 109.5 . . ?
C91 C92 H92C 109.5 . . ?
H92A C92 H92C 109.5 . . ?
H92B C92 H92C 109.5 . . ?
N9 C93 C94 114.80(15) . . ?
N9 C93 H93A 108.6 . . ?
C94 C93 H93A 108.6 . . ?
N9 C93 H93B 108.6 . . ?
C94 C93 H93B 108.6 . . ?
H93A C93 H93B 107.5 . . ?
C93 C94 H94A 109.5 . . ?
C93 C94 H94B 109.5 . . ?
H94A C94 H94B 109.5 . . ?
C93 C94 H94C 109.5 . . ?
H94A C94 H94C 109.5 . . ?
H94B C94 H94C 109.5 . . ?
N9 C95 C96 114.54(12) . . ?
N9 C95 H95A 108.6 . . ?
C96 C95 H95A 108.6 . . ?
N9 C95 H95B 108.6 . . ?
C96 C95 H95B 108.6 . . ?
H95A C95 H95B 107.6 . . ?
C95 C96 H96A 109.5 . . ?
C95 C96 H96B 109.5 . . ?
H96A C96 H96B 109.5 . . ?
C95 C96 H96C 109.5 . . ?
H96A C96 H96C 109.5 . . ?
H96B C96 H96C 109.5 . . ?
C98 C97 N9 115.05(15) . . ?
C98 C97 H97A 108.5 . . ?
N9 C97 H97A 108.5 . . ?
C98 C97 H97B 108.5 . . ?
N9 C97 H97B 108.5 . . ?
H97A C97 H97B 107.5 . . ?
C97 C98 H98A 109.5 . . ?
C97 C98 H98B 109.5 . . ?
H98A C98 H98B 109.5 . . ?
C97 C98 H98C 109.5 . . ?
H98A C98 H98C 109.5 . . ?
H98B C98 H98C 109.5 . . ?
C95 N9 C93 111.54(12) . . ?
C95 N9 C97 111.27(12) . . ?
C93 N9 C97 105.75(12) . . ?
C95 N9 C91 105.84(11) . . ?
C93 N9 C91 110.95(12) . . ?
C97 N9 C91 111.61(12) . . ?
C19 C14 C15 122.13(13) . . ?
C19 C14 N5 118.77(14) . . ?
C15 C14 N5 119.07(13) . . ?
C16 C15 C14 118.13(13) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
C15 C16 C17 121.05(14) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
N6 C17 C18 124.54(13) . . ?
N6 C17 C16 115.75(13) . . ?
C18 C17 C16 119.57(13) . . ?
C19 C18 C17 119.70(13) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C14 C19 C18 119.39(14) . . ?
C14 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
N6 C20 N7 110.35(12) . . ?
N6 C20 S2 124.89(11) . . ?
N7 C20 S2 124.64(11) . . ?
C26 C21 N7 122.87(13) . . ?
C26 C21 C22 119.61(13) . . ?
N7 C21 C22 117.40(13) . . ?
C23 C22 C21 120.93(14) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C24 118.08(13) . . ?
C22 C23 H23 121.0 . . ?
C24 C23 H23 121.0 . . ?
C25 C24 C23 122.18(13) . . ?
C25 C24 N8 118.35(14) . . ?
C23 C24 N8 119.44(13) . . ?
C26 C25 C24 119.41(14) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C25 C26 C21 119.76(13) . . ?
C25 C26 H26 120.1 . . ?
C21 C26 H26 120.1 . . ?
O5 N5 O6 123.62(14) . . ?
O5 N5 C14 118.45(13) . . ?
O6 N5 C14 117.92(14) . . ?
C20 N6 C17 130.65(13) . . ?
C20 N6 H6A 114.7 . . ?
C17 N6 H6A 114.7 . . ?
C20 N7 C21 128.61(12) . . ?
C20 N7 H7A 115.7 . . ?
C21 N7 H7A 115.7 . . ?
O8 N8 O7 123.45(14) . . ?
O8 N8 C24 118.20(14) . . ?
O7 N8 C24 118.32(13) . . ?
C6 C1 C2 121.77(14) . . ?
C6 C1 N1 119.36(14) . . ?
C2 C1 N1 118.86(14) . . ?
C3 C2 C1 118.22(14) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 121.01(14) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
N2 C4 C3 116.29(13) . . ?
N2 C4 C5 124.00(14) . . ?
C3 C4 C5 119.60(14) . . ?
C6 C5 C4 119.39(14) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 119.97(14) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
N3 C7 N2 110.05(13) . . ?
N3 C7 S1 124.89(11) . . ?
N2 C7 S1 124.99(11) . . ?
N3 C8 C9 116.30(13) . . ?
N3 C8 C13 124.18(14) . . ?
C9 C8 C13 119.41(14) . . ?
C10 C9 C8 121.13(14) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C11 118.29(14) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
C12 C11 C10 122.05(14) . . ?
C12 C11 N4 119.13(14) . . ?
C10 C11 N4 118.81(14) . . ?
C11 C12 C13 119.51(14) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C8 119.59(14) . . ?
C12 C13 H13 120.2 . . ?
C8 C13 H13 120.2 . . ?
O2 N1 O1 123.74(15) . . ?
O2 N1 C1 118.64(14) . . ?
O1 N1 C1 117.62(14) . . ?
C7 N2 C4 129.58(13) . . ?
C7 N2 H2A 115.2 . . ?
C4 N2 H2A 115.2 . . ?
C7 N3 C8 129.93(13) . . ?
C7 N3 H3A 115.0 . . ?
C8 N3 H3A 115.0 . . ?
O4 N4 O3 123.24(15) . . ?
O4 N4 C11 118.40(14) . . ?
O3 N4 C11 118.36(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6A Cl1 0.88 2.28 3.1487(14) 167.7 .
N7 H7A Cl1 0.88 2.38 3.2227(14) 159.5 .
N2 H2A Cl1 0.88 2.50 3.3440(14) 162.2 .
N3 H3A Cl1 0.88 2.42 3.2755(15) 165.5 .

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.059
