# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_19
_database_code_depnum_ccdc_archive 'CCDC 1565198'
_audit_update_record             
;
2017-07-27 deposited with the CCDC.
2017-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2-methoxythieno[2,3-d]pyrimidin-4(3H)-one
_chemical_name_common            ?
_chemical_formula_moiety         'C7 H6 N2 O2 S'
_chemical_formula_sum            'C7 H6 N2 O2 S'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         182.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   8.454(4)
_cell_length_b                   12.125(6)
_cell_length_c                   7.206(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.66(2)
_cell_angle_gamma                90
_cell_volume                     738.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    483
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      24.70
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.390
_shelx_estimated_absorpt_T_min   0.926
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2802
_diffrn_reflns_av_unetI/netI     0.0948
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.290
_diffrn_reflns_theta_max         25.772
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             1394
_reflns_number_gt                946
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2014
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1394
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1253
_refine_ls_wR_factor_gt          0.1132
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S7 S 0.41881(10) 0.12622(7) 0.84681(12) 0.0244(3) Uani 1 1 d . . . . .
O1 O -0.1216(3) 0.21645(17) 1.0598(3) 0.0251(6) Uani 1 1 d . . . . .
N1 N 0.1234(3) 0.1661(2) 0.9596(4) 0.0218(7) Uani 1 1 d . . . . .
O2 O 0.1982(3) 0.50023(18) 0.9274(3) 0.0299(6) Uani 1 1 d . . . . .
N3 N 0.0434(3) 0.3517(2) 0.9918(4) 0.0221(7) Uani 1 1 d . . . . .
C7A C 0.2643(4) 0.2093(3) 0.9066(4) 0.0192(7) Uani 1 1 d . . . . .
C2 C 0.0207(4) 0.2412(3) 1.0003(5) 0.0211(8) Uani 1 1 d . . . . .
C6 C 0.5357(4) 0.2397(3) 0.8066(4) 0.0248(8) Uani 1 1 d . . . . .
H6 H 0.6417 0.2353 0.7667 0.030 Uiso 1 1 calc R U . . .
C4A C 0.3028(4) 0.3193(3) 0.8928(5) 0.0220(8) Uani 1 1 d . . . . .
C4 C 0.1844(4) 0.3984(3) 0.9365(4) 0.0219(8) Uani 1 1 d . . . . .
C5 C 0.4595(4) 0.3364(3) 0.8383(5) 0.0259(8) Uani 1 1 d . . . . .
H5 H 0.5063 0.4071 0.8253 0.031 Uiso 1 1 calc R U . . .
C8 C -0.1603(4) 0.1002(3) 1.0620(5) 0.0315(9) Uani 1 1 d . . . . .
H8B H -0.1616 0.0714 0.9349 0.047 Uiso 1 1 calc R U . . .
H8A H -0.2647 0.0901 1.1150 0.047 Uiso 1 1 calc R U . . .
H8C H -0.0807 0.0605 1.1376 0.047 Uiso 1 1 calc R U . . .
H3 H -0.036(5) 0.399(3) 1.027(5) 0.040(11) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S7 C7A 1.715(3) . ?
S7 C6 1.724(3) . ?
O1 C2 1.323(4) . ?
O1 C8 1.447(4) . ?
N1 C2 1.298(4) . ?
N1 C7A 1.365(4) . ?
O2 C4 1.242(4) . ?
N3 C2 1.356(4) . ?
N3 C4 1.389(4) . ?
N3 H3 0.92(4) . ?
C7A C4A 1.377(4) . ?
C6 C5 1.361(5) . ?
C6 H6 0.9500 . ?
C4A C5 1.407(5) . ?
C4A C4 1.428(5) . ?
C5 H5 0.9500 . ?
C8 H8B 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8C 0.9800 . ?

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
C7A S7 C6 91.03(17) . . ?
C2 O1 C8 115.6(3) . . ?
C2 N1 C7A 112.9(3) . . ?
C2 N3 C4 122.7(3) . . ?
C2 N3 H3 119(2) . . ?
C4 N3 H3 118(2) . . ?
N1 C7A C4A 127.0(3) . . ?
N1 C7A S7 121.5(2) . . ?
C4A C7A S7 111.5(3) . . ?
N1 C2 O1 122.3(3) . . ?
N1 C2 N3 125.9(3) . . ?
O1 C2 N3 111.7(3) . . ?
C5 C6 S7 112.5(3) . . ?
C5 C6 H6 123.7 . . ?
S7 C6 H6 123.7 . . ?
C7A C4A C5 112.9(3) . . ?
C7A C4A C4 117.8(3) . . ?
C5 C4A C4 129.3(3) . . ?
O2 C4 N3 120.2(3) . . ?
O2 C4 C4A 126.1(3) . . ?
N3 C4 C4A 113.7(3) . . ?
C6 C5 C4A 112.0(3) . . ?
C6 C5 H5 124.0 . . ?
C4A C5 H5 124.0 . . ?
O1 C8 H8B 109.5 . . ?
O1 C8 H8A 109.5 . . ?
H8B C8 H8A 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C7A C4A -0.4(5) . . . . ?
C2 N1 C7A S7 179.8(2) . . . . ?
C6 S7 C7A N1 -179.4(3) . . . . ?
C6 S7 C7A C4A 0.8(3) . . . . ?
C7A N1 C2 O1 -178.0(3) . . . . ?
C7A N1 C2 N3 0.7(5) . . . . ?
C8 O1 C2 N1 -4.9(5) . . . . ?
C8 O1 C2 N3 176.2(3) . . . . ?
C4 N3 C2 N1 0.1(5) . . . . ?
C4 N3 C2 O1 178.9(3) . . . . ?
C7A S7 C6 C5 0.2(3) . . . . ?
N1 C7A C4A C5 178.6(3) . . . . ?
S7 C7A C4A C5 -1.6(4) . . . . ?
N1 C7A C4A C4 -0.5(5) . . . . ?
S7 C7A C4A C4 179.3(2) . . . . ?
C2 N3 C4 O2 178.5(3) . . . . ?
C2 N3 C4 C4A -1.0(5) . . . . ?
C7A C4A C4 O2 -178.3(3) . . . . ?
C5 C4A C4 O2 2.7(6) . . . . ?
C7A C4A C4 N3 1.2(4) . . . . ?
C5 C4A C4 N3 -177.8(3) . . . . ?
S7 C6 C5 C4A -1.1(4) . . . . ?
C7A C4A C5 C6 1.7(4) . . . . ?
C4 C4A C5 C6 -179.3(3) . . . . ?

_refine_diff_density_max         0.420
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.086

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_15
_database_code_depnum_ccdc_archive 'CCDC 1584774'
_audit_update_record             
;
2017-11-20 deposited with the CCDC.
2017-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'Methyl 2-(1H-tetrazol-1-yl)thiophene-3-carboxylate'
_chemical_name_common            ?
_chemical_formula_moiety         'C7 H6 N4 O2 S'
_chemical_formula_sum            'C7 H6 N4 O2 S'
_exptl_crystal_recrystallization_method CH2Cl2-hexane
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         210.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration ?

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

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

_cell_length_a                   3.9245(5)
_cell_length_b                   18.054(2)
_cell_length_c                   12.6455(15)
_cell_angle_alpha                90
_cell_angle_beta                 98.936(8)
_cell_angle_gamma                90
_cell_volume                     885.09(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2657
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      26.39
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.343
_shelx_estimated_absorpt_T_min   0.904
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5591
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.784
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1710
_reflns_number_gt                1569
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2014
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0754P)²+0.0886P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1710
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0986
_refine_ls_wR_factor_gt          0.0952
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_restrained_S_all      0.920
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S5 S 0.87859(17) 0.18744(3) 0.33190(5) 0.0373(2) Uani 1 1 d . . . . .
O16 O 0.3594(5) -0.05660(9) 0.30257(13) 0.0440(5) Uani 1 1 d . . . . .
N8 N 0.5345(5) 0.14990(10) 0.13806(14) 0.0309(4) Uani 1 1 d . . . . .
O15 O 0.2274(5) 0.00131(10) 0.14500(14) 0.0523(6) Uani 1 1 d . . . . .
C14 C 0.3718(7) 0.00015(12) 0.23609(19) 0.0340(5) Uani 1 1 d . . . . .
N12 N 0.3112(8) 0.22148(14) 0.01379(19) 0.0572(7) Uani 1 1 d . . . . .
N13 N 0.4422(7) 0.16251(14) -0.03304(16) 0.0517(6) Uani 1 1 d . . . . .
C1 C 0.6433(6) 0.12722(12) 0.24549(16) 0.0299(5) Uani 1 1 d . . . . .
C4 C 0.9002(8) 0.12435(15) 0.43274(18) 0.0412(6) Uani 1 1 d . . . . .
H4 H 1.0129 0.1328 0.5020 0.049 Uiso 1 1 calc R U . . .
N11 N 0.3642(7) 0.21525(12) 0.11648(18) 0.0475(6) Uani 1 1 d . . . . .
C3 C 0.7356(7) 0.06074(14) 0.40093(18) 0.0367(5) Uani 1 1 d . . . . .
H3 H 0.7239 0.0206 0.4462 0.044 Uiso 1 1 calc R U . . .
C2 C 0.5818(6) 0.06096(12) 0.29149(17) 0.0311(5) Uani 1 1 d . . . . .
C9 C 0.5780(8) 0.11979(16) 0.04504(18) 0.0435(6) Uani 1 1 d . . . . .
H9 H 0.6886 0.0750 0.0371 0.052 Uiso 1 1 calc R U . . .
C17 C 0.1716(10) -0.12148(13) 0.2580(2) 0.0523(7) Uani 1 1 d . . . . .
H17A H -0.0526 -0.1069 0.2226 0.078 Uiso 1 1 calc R U . . .
H17C H 0.1471 -0.1556 0.3145 0.078 Uiso 1 1 calc R U . . .
H17B H 0.2959 -0.1449 0.2075 0.078 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S5 C4 1.702(2) . ?
S5 C1 1.707(2) . ?
O16 C14 1.331(3) . ?
O16 C17 1.450(3) . ?
N8 C9 1.331(3) . ?
N8 N11 1.363(3) . ?
N8 C1 1.420(3) . ?
O15 C14 1.202(3) . ?
C14 C2 1.482(3) . ?
N12 N11 1.288(3) . ?
N12 N13 1.358(3) . ?
N13 C9 1.300(3) . ?
C1 C2 1.368(3) . ?
C4 C3 1.348(4) . ?
C4 H4 0.9300 . ?
C3 C2 1.421(3) . ?
C3 H3 0.9300 . ?
C9 H9 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17C 0.9600 . ?
C17 H17B 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 S5 C1 90.71(12) . . ?
C14 O16 C17 116.3(2) . . ?
C9 N8 N11 107.6(2) . . ?
C9 N8 C1 131.9(2) . . ?
N11 N8 C1 120.44(18) . . ?
O15 C14 O16 124.1(2) . . ?
O15 C14 C2 125.8(2) . . ?
O16 C14 C2 110.12(19) . . ?
N11 N12 N13 111.0(2) . . ?
C9 N13 N12 105.8(2) . . ?
C2 C1 N8 127.8(2) . . ?
C2 C1 S5 113.48(17) . . ?
N8 C1 S5 118.75(16) . . ?
C3 C4 S5 112.38(18) . . ?
C3 C4 H4 123.8 . . ?
S5 C4 H4 123.8 . . ?
N12 N11 N8 106.0(2) . . ?
C4 C3 C2 113.6(2) . . ?
C4 C3 H3 123.2 . . ?
C2 C3 H3 123.2 . . ?
C1 C2 C3 109.9(2) . . ?
C1 C2 C14 124.7(2) . . ?
C3 C2 C14 125.4(2) . . ?
N13 C9 N8 109.6(2) . . ?
N13 C9 H9 125.2 . . ?
N8 C9 H9 125.2 . . ?
O16 C17 H17A 109.5 . . ?
O16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
O16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17C C17 H17B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 O16 C14 O15 3.1(4) . . . . ?
C17 O16 C14 C2 -177.9(2) . . . . ?
N11 N12 N13 C9 0.0(4) . . . . ?
C9 N8 C1 C2 -55.3(4) . . . . ?
N11 N8 C1 C2 127.9(3) . . . . ?
C9 N8 C1 S5 124.9(3) . . . . ?
N11 N8 C1 S5 -51.8(3) . . . . ?
C4 S5 C1 C2 0.0(2) . . . . ?
C4 S5 C1 N8 179.8(2) . . . . ?
C1 S5 C4 C3 0.1(2) . . . . ?
N13 N12 N11 N8 -0.2(3) . . . . ?
C9 N8 N11 N12 0.4(3) . . . . ?
C1 N8 N11 N12 177.9(2) . . . . ?
S5 C4 C3 C2 -0.2(3) . . . . ?
N8 C1 C2 C3 -179.9(2) . . . . ?
S5 C1 C2 C3 -0.2(3) . . . . ?
N8 C1 C2 C14 -2.5(4) . . . . ?
S5 C1 C2 C14 177.20(19) . . . . ?
C4 C3 C2 C1 0.3(3) . . . . ?
C4 C3 C2 C14 -177.1(2) . . . . ?
O15 C14 C2 C1 -0.7(4) . . . . ?
O16 C14 C2 C1 -179.6(2) . . . . ?
O15 C14 C2 C3 176.3(3) . . . . ?
O16 C14 C2 C3 -2.7(3) . . . . ?
N12 N13 C9 N8 0.3(3) . . . . ?
N11 N8 C9 N13 -0.4(3) . . . . ?
C1 N8 C9 N13 -177.5(2) . . . . ?

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.055

