# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_xg0114
_database_code_depnum_ccdc_archive 'CCDC 1893693'
loop_
_audit_author_name
_audit_author_address
'Zhang Hongyang'
;Hong Kong Baptist University
Hong Kong
;
_audit_update_record             
;
2019-01-26 deposited with the CCDC.	2020-02-03 downloaded from the CCDC.
;
_audit_creation_date             2019-01-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C10 H2 N4, C12 H6 N'
_chemical_formula_sum            'C22 H8 N5'
_chemical_formula_weight         342.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.009(4)
_cell_length_b                   7.859(4)
_cell_length_c                   7.860(4)
_cell_angle_alpha                73.65(4)
_cell_angle_beta                 84.33(4)
_cell_angle_gamma                88.87(5)
_cell_volume                     413.4(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    462
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4940
_cell_measurement_theta_min      5.8090
_shelx_estimated_absorpt_T_max   0.928
_shelx_estimated_absorpt_T_min   0.916
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             175
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0784
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2679
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.421
_diffrn_reflns_theta_min         5.868
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  36.00   1.00    1.00    --   40.73 -37.00  60.00   64
  2  ω     37.00  65.00   1.00    1.00    --   40.73 -37.00  60.00   28
  3  ω     59.00  90.00   1.00    1.00    --   40.73-125.00 150.00   31
  4  ω     50.00 118.00   1.00    1.50    --  106.95 -45.00  60.00   68
  5  ω    106.00 137.00   1.00    1.50    --  106.95 -77.00  90.00   31
  6  ω     59.00 178.00   1.00    1.50    --  106.95  15.00   0.00  119
  7  ω     95.00 145.00   1.00    1.50    --  106.95 125.00  30.00   50
  8  ω     88.00 122.00   1.00    1.50    --  106.95  45.00-120.00   34
  9  ω     37.00 114.00   1.00    1.50    --  106.95 -61.00 -90.00   77
 10  ω     60.00 121.00   1.00    1.50    --  106.95-125.00 -60.00   61
 11  ω     59.00 109.00   1.00    1.50    --  106.95 -94.00  30.00   50
 12  ω     57.00  91.00   1.00    1.50    --  106.95 -94.00 150.00   34
 13  ω     39.00  66.00   1.00    1.50    --  106.95 -77.00  90.00   27
 14  ω     37.00 133.00   1.00    1.50    --  106.95 -30.00 -30.00   96
 15  ω    -93.00 -61.00   1.00    1.00    --  -40.73-170.00 -77.00   32
 16  ω    -95.00  -8.00   1.00    1.00    --  -40.73 -77.00 -60.00   87
 17  ω   -114.00 -22.00   1.00    1.00    --  -40.73 -37.00-180.00   92
 18  ω    102.00 128.00   1.00    2.25    --  106.95 125.00-180.00   26
 19  ω    153.00 178.00   1.00    2.25    --  106.95 125.00  90.00   25
 20  ω     49.00  85.00   1.00    2.25    --  106.95 -77.00-180.00   36
 21  ω    113.00 139.00   1.00    2.25    --  106.95 125.00  90.00   26
 22  ω     84.00 109.00   1.00    2.25    --  106.95 -94.00  60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0280162000
_diffrn_orient_matrix_UB_12      -0.0713101000
_diffrn_orient_matrix_UB_13      -0.1595735000
_diffrn_orient_matrix_UB_21      0.0289053000
_diffrn_orient_matrix_UB_22      0.1887736000
_diffrn_orient_matrix_UB_23      -0.1268539000
_diffrn_orient_matrix_UB_31      0.2170879000
_diffrn_orient_matrix_UB_32      -0.0325912000
_diffrn_orient_matrix_UB_33      -0.0238914000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1003
_reflns_number_total             1587
_reflns_odcompleteness_completeness 99.19
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.301
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.595
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1587
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0519
_refine_ls_restrained_S_all      2.557
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1659
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C1, C2, C3, C4, C5, C6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6: within 2A with sigma of 0.002
and sigma for terminal atoms of 0.004
4. Others
 Fixed Sof: N1(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C4(H4), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
N3 N 0.3456(5) 0.4901(5) 0.7029(4) 0.0593(9) Uani 1 1 d . . . . .
C8 C 0.4451(4) 0.8263(4) 0.5692(4) 0.0388(8) Uani 1 1 d . . . . .
C10 C 0.3925(5) 0.8679(4) 0.8665(5) 0.0425(9) Uani 1 1 d . . . . .
N2 N 0.3428(5) 0.8153(4) 1.0186(4) 0.0568(9) Uani 1 1 d . . . . .
C7 C 0.4463(4) 0.9303(4) 0.6850(4) 0.0377(8) Uani 1 1 d . . . . .
C11 C 0.4962(4) 0.8856(4) 0.3891(4) 0.0367(7) Uani 1 1 d . . . . .
H11 H 0.493937 0.810064 0.317095 0.044 Uiso 1 1 calc R . . . .
C9 C 0.3915(4) 0.6418(4) 0.6397(4) 0.0402(8) Uani 1 1 d . . . . .
C1 C 0.9577(6) 0.8537(7) 0.5214(8) 0.0868(4) Uani 1 1 d . U . . .
C4 C 0.8695(6) 0.7767(8) 0.8704(8) 0.0872(4) Uani 1 1 d . U . . .
H4 H 0.844691 0.767035 0.991147 0.105 Uiso 1 1 calc R . . . .
C5 C 0.8364(6) 0.6315(7) 0.8238(8) 0.0871(4) Uani 1 1 d . U . . .
H5 H 0.792596 0.526451 0.906272 0.104 Uiso 1 1 calc R . . . .
C2 C 0.9582(6) 0.9496(7) 0.6257(8) 0.0876(4) Uani 1 1 d . U . . .
C6 C 0.8758(6) 0.6489(7) 0.6229(7) 0.0864(3) Uani 1 1 d . U . . .
H6 H 0.857161 0.560793 0.568168 0.104 Uiso 1 1 calc R . . . .
C3 C 0.9273(6) 0.9196(8) 0.7782(8) 0.0880(4) Uani 1 1 d . U . . .
N1 N 1.0021(8) 0.8929(7) 0.3415(7) 0.0499(14) Uani 0.5 1 d . . P . .


_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
N3 C9 1.192(5) . ?
C8 C7 1.385(5) . ?
C8 C11 1.372(4) . ?
C8 C9 1.442(4) . ?
C10 N2 1.169(5) . ?
C10 C7 1.388(5) . ?
C7 C11 1.448(4) 2_676 ?
C11 H11 0.9300 . ?
C1 C2 1.260(9) . ?
C1 C2 1.723(7) 2_776 ?
C1 C6 1.667(7) . ?
C1 N1 1.365(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.324(9) . ?
C4 C3 1.205(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.543(8) . ?
C2 C2 1.945(11) 2_776 ?
C2 C3 1.154(8) . ?
C2 N1 1.372(9) 2_776 ?
C6 H6 0.9300 . ?
C3 N1 1.568(7) 2_776 ?

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
C7 C8 C9 119.0(3) . . ?
C11 C8 C7 124.4(3) . . ?
C11 C8 C9 116.6(3) . . ?
N2 C10 C7 178.4(4) . . ?
C8 C7 C10 123.4(3) . . ?
C8 C7 C11 117.8(3) . 2_676 ?
C10 C7 C11 118.8(3) . 2_676 ?
C8 C11 C7 117.8(3) . 2_676 ?
C8 C11 H11 121.1 . . ?
C7 C11 H11 121.1 2_676 . ?
N3 C9 C8 178.0(3) . . ?
C2 C1 C2 79.7(5) . 2_776 ?
C2 C1 C6 112.9(5) . . ?
C2 C1 N1 130.9(5) . . ?
C6 C1 C2 167.3(6) . 2_776 ?
N1 C1 C2 51.2(4) . 2_776 ?
N1 C1 C6 116.1(5) . . ?
C5 C4 H4 115.4 . . ?
C3 C4 H4 115.4 . . ?
C3 C4 C5 129.1(7) . . ?
C4 C5 H5 122.4 . . ?
C4 C5 C6 115.2(5) . . ?
C6 C5 H5 122.4 . . ?
C1 C2 C1 100.3(5) . 2_776 ?
C1 C2 C2 39.6(3) 2_776 2_776 ?
C1 C2 C2 60.7(4) . 2_776 ?
C1 C2 N1 151.0(5) . 2_776 ?
C3 C2 C1 132.6(6) . . ?
C3 C2 C1 126.9(6) . 2_776 ?
C3 C2 C2 166.1(7) . 2_776 ?
C3 C2 N1 76.2(5) . 2_776 ?
N1 C2 C1 50.8(4) 2_776 2_776 ?
N1 C2 C2 90.4(4) 2_776 2_776 ?
C1 C6 H6 126.0 . . ?
C5 C6 C1 107.9(5) . . ?
C5 C6 H6 126.0 . . ?
C4 C3 N1 178.8(5) . 2_776 ?
C2 C3 C4 122.0(7) . . ?
C2 C3 N1 58.2(4) . 2_776 ?
C1 N1 C2 78.0(5) . 2_776 ?
C1 N1 C3 123.6(6) . 2_776 ?
C2 N1 C3 45.6(4) 2_776 2_776 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.800
_oxdiff_exptl_absorpt_empirical_full_min 0.394
####################################################################### 
# 
# 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 1893697'
loop_
_audit_author_name
_audit_author_address
'Zhang hongyang'
;Hong Kong Baptist University
Hong Kong
;
_audit_update_record             
;
2019-01-26 deposited with the CCDC.	2020-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H12 N4'
_chemical_formula_weight         344.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.1773(6)
_cell_length_b                   7.7832(6)
_cell_length_c                   7.9353(6)
_cell_angle_alpha                73.799(3)
_cell_angle_beta                 83.803(3)
_cell_angle_gamma                88.445(3)
_cell_volume                     423.19(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4189
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      34.83

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             178
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.40
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6018
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_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            5824
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.688
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1723
_reflns_number_gt                1522
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0928P)²+0.4794P] 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         1723
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   0.611
_refine_ls_restrained_S_all      0.611
_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
N1 N 0.63308(16) 0.69355(15) -0.01721(14) 0.0338(3) Uani 1 1 d . . . . .
N2 N 0.34211(17) -0.00899(14) 0.69567(15) 0.0347(3) Uani 1 1 d . . . . .
C1 C 1.0576(3) 0.6864(5) 0.4700(2) 0.0239(8) Uani 0.5 1 d G . P . .
C2 C 1.1238(5) 0.8506(4) 0.3614(5) 0.0324(10) Uani 0.5 1 d G . P . .
H2 H 1.1451 0.9454 0.4109 0.039 Uiso 0.5 1 calc R U P . .
C3 C 1.1588(7) 0.8762(4) 0.1804(4) 0.0398(11) Uani 0.5 1 d G . P . .
H3 H 1.2040 0.9884 0.1061 0.048 Uiso 0.5 1 calc R U P . .
C4 C 1.1277(7) 0.7375(5) 0.1079(2) 0.0394(11) Uani 0.5 1 d G . P . .
H4 H 1.1516 0.7550 -0.0158 0.047 Uiso 0.5 1 calc R U P . .
C5 C 1.0615(4) 0.5733(4) 0.2166(5) 0.0312(7) Uani 0.5 1 d G . P . .
H5 H 1.0402 0.4785 0.1671 0.037 Uiso 0.5 1 calc R U P . .
C6 C 1.0265(2) 0.5477(3) 0.3976(4) 0.0233(6) Uani 0.5 1 d G . P . .
C7 C 0.9530(3) 0.4382(3) 0.6985(5) 0.0271(8) Uani 0.5 1 d G . P . .
C8 C 0.8930(6) 0.3123(5) 0.8560(3) 0.0330(9) Uani 0.5 1 d G . P . .
H8 H 0.8876 0.3427 0.9644 0.040 Uiso 0.5 1 calc R U P . .
C9 C 0.8411(7) 0.1419(4) 0.8551(3) 0.0380(11) Uani 0.5 1 d G . P . .
H9 H 0.8001 0.0558 0.9627 0.046 Uiso 0.5 1 calc R U P . .
C10 C 0.8490(5) 0.0974(3) 0.6965(5) 0.0344(9) Uani 0.5 1 d G . P . .
H10 H 0.8135 -0.0191 0.6959 0.041 Uiso 0.5 1 calc R U P . .
C11 C 0.9090(3) 0.2233(5) 0.5390(3) 0.0270(6) Uani 0.5 1 d G . P . .
H11 H 0.9144 0.1929 0.4306 0.032 Uiso 0.5 1 calc R U P . .
C12 C 0.9610(3) 0.3938(4) 0.5399(3) 0.0213(7) Uani 0.5 1 d G . P . .
C13 C 0.54333(15) 0.56835(14) 0.31869(14) 0.0202(3) Uani 1 1 d . . . . .
C14 C 0.48599(16) 0.39150(15) 0.38759(14) 0.0223(3) Uani 1 1 d . . . . .
H14 H 0.4764 0.3180 0.3113 0.027 Uiso 1 1 calc R U . . .
C15 C 0.44269(15) 0.32225(14) 0.56853(14) 0.0205(3) Uani 1 1 d . . . . .
C16 C 0.59160(16) 0.63949(15) 0.13135(15) 0.0240(3) Uani 1 1 d . . . . .
C17 C 0.38575(16) 0.13808(15) 0.64035(14) 0.0247(3) Uani 1 1 d . . . . .
C18 C 1.0097(4) 0.6286(4) 0.6663(4) 0.0321(6) Uani 0.5 1 d . . P . .
H18A H 1.1196 0.6383 0.7287 0.038 Uiso 0.5 1 calc R U P . .
H18B H 0.9055 0.7002 0.7037 0.038 Uiso 0.5 1 calc R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C16 1.1444(16) . ?
N2 C17 1.1447(16) . ?
C1 C12 0.669(3) 2_766 ?
C1 C11 0.731(2) 2_766 ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 C18 1.499(3) . ?
C1 C7 1.8667(18) 2_766 ?
C1 C10 1.912(5) 2_766 ?
C1 C6 1.909(7) 2_766 ?
C2 C3 1.3900 . ?
C2 C12 1.9312(19) 2_766 ?
C2 H2 0.9500 . ?
C3 C4 1.3900 . ?
C3 H3 0.9500 . ?
C4 C5 1.3900 . ?
C4 H4 0.9500 . ?
C5 C6 1.3900 . ?
C5 C12 2.008(5) 2_766 ?
C5 H5 0.9500 . ?
C6 C7 0.738(2) 2_766 ?
C6 C12 0.774(4) 2_766 ?
C6 C12 1.447(2) . ?
C6 C6 1.595(6) 2_766 ?
C6 C18 1.627(4) 2_766 ?
C6 C1 1.909(5) 2_766 ?
C6 C8 2.032(2) 2_766 ?
C7 C5 0.652(3) 2_766 ?
C7 C6 0.738(3) 2_766 ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C7 C18 1.492(3) . ?
C7 C4 1.801(5) 2_766 ?
C7 C1 1.8667(18) 2_766 ?
C7 C12 2.020(7) 2_766 ?
C8 C9 1.3900 . ?
C8 C6 2.032(3) 2_766 ?
C8 H8 0.9500 . ?
C9 C10 1.3900 . ?
C9 H9 0.9500 . ?
C10 C11 1.3900 . ?
C10 H10 0.9500 . ?
C11 C12 1.3900 . ?
C11 H11 0.9500 . ?
C12 C1 0.6690(18) 2_766 ?
C12 C6 0.774(4) 2_766 ?
C12 C18 1.684(4) 2_766 ?
C12 C12 1.685(6) 2_766 ?
C12 C2 1.9312(19) 2_766 ?
C12 C5 2.008(4) 2_766 ?
C12 C7 2.020(4) 2_766 ?
C13 C14 1.3875(16) . ?
C13 C15 1.4090(15) 2_666 ?
C13 C16 1.4410(15) . ?
C14 C15 1.3891(15) . ?
C14 H14 0.9500 . ?
C15 C13 1.4089(15) 2_666 ?
C15 C17 1.4396(15) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?

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 C1 C11 166.5(12) 2_766 2_766 ?
C12 C1 C2 136.5(4) 2_766 . ?
C11 C1 C2 31.0(9) 2_766 . ?
C12 C1 C6 16.8(4) 2_766 . ?
C11 C1 C6 150.8(9) 2_766 . ?
C2 C1 C6 120.0 . . ?
C12 C1 C18 94.0(6) 2_766 . ?
C11 C1 C18 98.5(6) 2_766 . ?
C2 C1 C18 129.4(3) . . ?
C6 C1 C18 110.6(3) . . ?
C12 C1 C7 36.8(3) 2_766 2_766 ?
C11 C1 C7 130.7(9) 2_766 2_766 ?
C2 C1 C7 99.85(10) . 2_766 ?
C6 C1 C7 20.15(10) . 2_766 ?
C18 C1 C7 130.8(3) . 2_766 ?
C12 C1 C10 131.4(8) 2_766 2_766 ?
C11 C1 C10 36.1(4) 2_766 2_766 ?
C2 C1 C10 5.2(5) . 2_766 ?
C6 C1 C10 114.9(5) . 2_766 ?
C18 C1 C10 134.5(3) . 2_766 ?
C7 C1 C10 94.7(5) 2_766 2_766 ?
C12 C1 C6 38.6(7) 2_766 2_766 ?
C11 C1 C6 153.7(6) 2_766 2_766 ?
C2 C1 C6 175.0(4) . 2_766 ?
C6 C1 C6 55.2(4) . 2_766 ?
C18 C1 C6 55.46(17) . 2_766 ?
C7 C1 C6 75.3(4) 2_766 2_766 ?
C10 C1 C6 169.8(2) 2_766 2_766 ?
C1 C2 C3 120.0 . . ?
C1 C2 C12 13.78(15) . 2_766 ?
C3 C2 C12 106.24(15) . 2_766 ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C12 C2 H2 133.8 2_766 . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 C12 103.99(6) . 2_766 ?
C6 C5 C12 16.03(6) . 2_766 ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C12 C5 H5 136.0 2_766 . ?
C7 C6 C12 133.6(4) 2_766 2_766 ?
C7 C6 C5 1.1(3) 2_766 . ?
C12 C6 C5 134.3(2) 2_766 . ?
C7 C6 C1 119.4(2) 2_766 . ?
C12 C6 C1 14.4(2) 2_766 . ?
C5 C6 C1 120.0 . . ?
C7 C6 C12 132.5(5) 2_766 . ?
C12 C6 C12 93.8(3) 2_766 . ?
C5 C6 C12 131.9(4) . . ?
C1 C6 C12 108.1(4) . . ?
C7 C6 C6 161.3(5) 2_766 2_766 ?
C12 C6 C6 64.8(4) 2_766 2_766 ?
C5 C6 C6 160.8(5) . 2_766 ?
C1 C6 C6 79.2(5) . 2_766 ?
C12 C6 C6 28.95(10) . 2_766 ?
C7 C6 C18 66.3(3) 2_766 2_766 ?
C12 C6 C18 159.6(3) 2_766 2_766 ?
C5 C6 C18 65.8(2) . 2_766 ?
C1 C6 C18 174.0(2) . 2_766 ?
C12 C6 C18 66.2(3) . 2_766 ?
C6 C6 C18 95.1(3) 2_766 2_766 ?
C7 C6 C1 115.7(4) 2_766 2_766 ?
C12 C6 C1 110.5(3) 2_766 2_766 ?
C5 C6 C1 115.2(3) . 2_766 ?
C1 C6 C1 124.8(3) . 2_766 ?
C12 C6 C1 16.75(14) . 2_766 ?
C6 C6 C1 45.7(2) 2_766 2_766 ?
C18 C6 C1 49.41(16) 2_766 2_766 ?
C7 C6 C8 23.9(5) 2_766 2_766 ?
C12 C6 C8 109.8(3) 2_766 2_766 ?
C5 C6 C8 24.5(4) . 2_766 ?
C1 C6 C8 95.5(4) . 2_766 ?
C12 C6 C8 156.36(14) . 2_766 ?
C6 C6 C8 174.4(3) 2_766 2_766 ?
C18 C6 C8 90.2(2) 2_766 2_766 ?
C1 C6 C8 139.62(17) 2_766 2_766 ?
C5 C7 C6 177.6(11) 2_766 2_766 ?
C5 C7 C8 37.5(9) 2_766 . ?
C6 C7 C8 143.7(3) 2_766 . ?
C5 C7 C12 157.5(9) 2_766 . ?
C6 C7 C12 23.8(3) 2_766 . ?
C8 C7 C12 120.0 . . ?
C5 C7 C18 92.1(7) 2_766 . ?
C6 C7 C18 86.7(6) 2_766 . ?
C8 C7 C18 129.6(3) . . ?
C12 C7 C18 110.4(3) . . ?
C5 C7 C4 42.3(4) 2_766 2_766 ?
C6 C7 C4 139.0(8) 2_766 2_766 ?
C8 C7 C4 4.7(5) . 2_766 ?
C12 C7 C4 115.3(5) . 2_766 ?
C18 C7 C4 134.3(3) . 2_766 ?
C5 C7 C1 140.8(9) 2_766 2_766 ?
C6 C7 C1 40.4(3) 2_766 2_766 ?
C8 C7 C1 103.27(7) . 2_766 ?
C12 C7 C1 16.75(7) . 2_766 ?
C18 C7 C1 127.1(3) . 2_766 ?
C4 C7 C1 98.5(5) 2_766 2_766 ?
C5 C7 C12 146.9(6) 2_766 2_766 ?
C6 C7 C12 31.9(7) 2_766 2_766 ?
C8 C7 C12 175.6(4) . 2_766 ?
C12 C7 C12 55.6(4) . 2_766 ?
C18 C7 C12 54.85(17) . 2_766 ?
C4 C7 C12 170.86(19) 2_766 2_766 ?
C1 C7 C12 72.3(4) 2_766 2_766 ?
C9 C8 C7 120.0 . . ?
C9 C8 C6 107.59(12) . 2_766 ?
C7 C8 C6 12.42(12) . 2_766 ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C6 C8 H8 132.4 2_766 . ?
C8 C9 C10 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 120.0 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C1 C12 C6 148.8(4) 2_766 2_766 ?
C1 C12 C11 7.0(2) 2_766 . ?
C6 C12 C11 142.5(2) 2_766 . ?
C1 C12 C7 126.5(2) 2_766 . ?
C6 C12 C7 22.6(2) 2_766 . ?
C11 C12 C7 120.0 . . ?
C1 C12 C6 124.7(5) 2_766 . ?
C6 C12 C6 86.2(3) 2_766 . ?
C11 C12 C6 131.2(4) . . ?
C7 C12 C6 108.8(4) . . ?
C1 C12 C18 62.6(3) 2_766 2_766 ?
C6 C12 C18 148.1(2) 2_766 2_766 ?
C11 C12 C18 69.2(3) . 2_766 ?
C7 C12 C18 170.6(3) . 2_766 ?
C6 C12 C18 62.1(2) . 2_766 ?
C1 C12 C12 151.8(5) 2_766 2_766 ?
C6 C12 C12 59.0(4) 2_766 2_766 ?
C11 C12 C12 158.5(5) . 2_766 ?
C7 C12 C12 81.5(5) . 2_766 ?
C6 C12 C12 27.28(11) . 2_766 ?
C18 C12 C12 89.3(3) 2_766 2_766 ?
C1 C12 C2 29.7(4) 2_766 2_766 ?
C6 C12 C2 119.4(3) 2_766 2_766 ?
C11 C12 C2 23.1(4) . 2_766 ?
C7 C12 C2 96.9(4) . 2_766 ?
C6 C12 C2 154.34(17) . 2_766 ?
C18 C12 C2 92.3(2) 2_766 2_766 ?
C12 C12 C2 178.0(4) 2_766 2_766 ?
C1 C12 C5 119.3(4) 2_766 2_766 ?
C6 C12 C5 29.72(18) 2_766 2_766 ?
C11 C12 C5 112.9(3) . 2_766 ?
C7 C12 C5 7.1(3) . 2_766 ?
C6 C12 C5 115.9(2) . 2_766 ?
C18 C12 C5 177.1(2) 2_766 2_766 ?
C12 C12 C5 88.6(3) 2_766 2_766 ?
C2 C12 C5 89.75(14) 2_766 2_766 ?
C1 C12 C7 109.1(4) 2_766 2_766 ?
C6 C12 C7 101.8(2) 2_766 2_766 ?
C11 C12 C7 115.6(3) . 2_766 ?
C7 C12 C7 124.4(3) . 2_766 ?
C6 C12 C7 15.64(14) . 2_766 ?
C18 C12 C7 46.42(13) 2_766 2_766 ?
C12 C12 C7 42.9(2) 2_766 2_766 ?
C2 C12 C7 138.70(17) 2_766 2_766 ?
C5 C12 C7 131.53(13) 2_766 2_766 ?
C14 C13 C15 120.25(10) . 2_666 ?
C14 C13 C16 119.84(9) . . ?
C15 C13 C16 119.90(10) 2_666 . ?
C15 C14 C13 119.76(10) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C13 119.99(10) . 2_666 ?
C14 C15 C17 119.79(10) . . ?
C13 C15 C17 120.22(10) 2_666 . ?
N1 C16 C13 178.55(13) . . ?
N2 C17 C15 179.05(13) . . ?
C7 C18 C1 102.08(17) . . ?
C7 C18 H18A 111.4 . . ?
C1 C18 H18A 111.4 . . ?
C7 C18 H18B 111.4 . . ?
C1 C18 H18B 111.4 . . ?
H18A C18 H18B 109.2 . . ?

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1893695'
loop_
_audit_author_name
_audit_author_address
'Zhang hongyang'
;Hong Kong Baptist University
Hong Kong
;
_audit_update_record             
;
2019-01-26 deposited with the CCDC.	2020-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H10 N4 S'
_chemical_formula_weight         362.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.1602(16)
_cell_length_b                   7.8240(17)
_cell_length_c                   7.9224(17)
_cell_angle_alpha                72.92(2)
_cell_angle_beta                 86.08(2)
_cell_angle_gamma                89.28(2)
_cell_volume                     423.25(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4351
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      34.04

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_F_000             186
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.205
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6360
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_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            6719
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.723
_diffrn_reflns_theta_max         26.358
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             1702
_reflns_number_gt                1542
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1552P)²+0.8925P] 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         1702
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0867
_refine_ls_wR_factor_ref         0.2837
_refine_ls_wR_factor_gt          0.2777
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.159
_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
S1 S 1.0073(3) 0.6523(3) 0.6801(3) 0.0313(6) Uani 0.5 1 d . . P . .
N1 N 0.6409(5) 0.6931(5) -0.0145(4) 0.0357(8) Uani 1 1 d . . . . .
N2 N 0.3405(5) -0.0106(4) 0.6964(4) 0.0350(8) Uani 1 1 d . . . . .
C1 C 1.0616(9) 0.6928(11) 0.4547(8) 0.024(2) Uani 0.5 1 d G . P . .
C2 C 1.1263(14) 0.8529(9) 0.3359(13) 0.034(3) Uani 0.5 1 d G . P . .
H2 H 1.1460 0.9537 0.3763 0.041 Uiso 0.5 1 calc R U P . .
C3 C 1.1621(18) 0.8654(10) 0.1580(11) 0.051(8) Uani 0.5 1 d G . P . .
H3 H 1.2064 0.9748 0.0768 0.061 Uiso 0.5 1 calc R U P . .
C4 C 1.1333(16) 0.7178(13) 0.0989(7) 0.033(3) Uani 0.5 1 d G . P . .
H4 H 1.1578 0.7264 -0.0227 0.039 Uiso 0.5 1 calc R U P . .
C5 C 1.0685(10) 0.5577(9) 0.2177(11) 0.033(2) Uani 0.5 1 d G . P . .
H5 H 1.0488 0.4569 0.1773 0.040 Uiso 0.5 1 calc R U P . .
C6 C 1.0327(7) 0.5452(8) 0.3956(10) 0.0224(18) Uani 0.5 1 d G . P . .
C7 C 0.9437(9) 0.4344(7) 0.6996(11) 0.027(2) Uani 0.5 1 d G . P . .
C8 C 0.8775(13) 0.3057(12) 0.8531(8) 0.035(3) Uani 0.5 1 d G . P . .
H8 H 0.8654 0.3336 0.9623 0.042 Uiso 0.5 1 calc R U P . .
C9 C 0.8288(15) 0.1364(11) 0.8470(7) 0.031(6) Uani 0.5 1 d G . P . .
H9 H 0.7836 0.0484 0.9519 0.037 Uiso 0.5 1 calc R U P . .
C10 C 0.8464(12) 0.0956(8) 0.6873(10) 0.029(2) Uani 0.5 1 d G . P . .
H10 H 0.8132 -0.0202 0.6831 0.035 Uiso 0.5 1 calc R U P . .
C11 C 0.9126(8) 0.2243(11) 0.5338(7) 0.0263(17) Uani 0.5 1 d G . P . .
H11 H 0.9247 0.1964 0.4246 0.032 Uiso 0.5 1 calc R U P . .
C12 C 0.9613(7) 0.3937(9) 0.5399(8) 0.0197(18) Uani 0.5 1 d G . P . .
C13 C 0.5477(4) 0.5674(4) 0.3194(4) 0.0212(8) Uani 1 1 d . . . . .
C14 C 0.4909(5) 0.3904(4) 0.3885(4) 0.0228(8) Uani 1 1 d . . . . .
H14 H 0.4848 0.3161 0.3133 0.027 Uiso 1 1 calc R U . . .
C15 C 0.4432(4) 0.3225(4) 0.5683(4) 0.0205(7) Uani 1 1 d . . . . .
C16 C 0.5991(5) 0.6395(4) 0.1326(4) 0.0246(8) Uani 1 1 d . . . . .
C17 C 0.3851(5) 0.1369(4) 0.6406(4) 0.0251(8) Uani 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
S1 C5 1.682(16) 2_766 ?
S1 C7 1.730(6) . ?
S1 C1 1.737(6) . ?
S1 C11 1.747(15) 2_766 ?
S1 C6 1.846(16) 2_766 ?
S1 C12 1.879(15) 2_766 ?
N1 C16 1.137(5) . ?
N2 C17 1.148(5) . ?
C1 C12 0.686(7) 2_766 ?
C1 C11 0.710(8) 2_766 ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 C7 1.791(6) 2_766 ?
C1 C10 1.809(9) 2_766 ?
C1 C6 1.989(16) 2_766 ?
C2 C3 1.3900 . ?
C2 C12 1.978(7) 2_766 ?
C2 H2 0.9500 . ?
C3 C4 1.3900 . ?
C3 H3 0.9500 . ?
C4 C5 1.3900 . ?
C4 H4 0.9500 . ?
C5 C6 1.3900 . ?
C5 H5 0.9500 . ?
C6 C7 0.731(7) 2_766 ?
C6 C12 0.799(9) 2_766 ?
C6 C12 1.454(5) . ?
C6 C6 1.635(13) 2_766 ?
C6 S1 1.846(9) 2_766 ?
C6 C1 1.989(12) 2_766 ?
C6 C8 2.038(7) 2_766 ?
C7 C5 0.676(10) 2_766 ?
C7 C6 0.731(8) 2_766 ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C7 C4 1.747(9) 2_766 ?
C7 C1 1.791(6) 2_766 ?
C8 C9 1.3900 . ?
C8 C6 2.038(8) 2_766 ?
C8 H8 0.9500 . ?
C9 C10 1.3900 . ?
C9 H9 0.9500 . ?
C10 C11 1.3900 . ?
C10 H10 0.9500 . ?
C11 C12 1.3900 . ?
C11 H11 0.9500 . ?
C12 C1 0.686(6) 2_766 ?
C12 C6 0.799(10) 2_766 ?
C12 C12 1.683(12) 2_766 ?
C12 S1 1.879(8) 2_766 ?
C12 C2 1.978(6) 2_766 ?
C13 C14 1.386(5) . ?
C13 C15 1.414(4) 2_666 ?
C13 C16 1.443(4) . ?
C14 C15 1.386(4) . ?
C14 H14 0.9500 . ?
C15 C13 1.414(4) 2_666 ?
C15 C17 1.451(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S1 C7 22.8(4) 2_766 . ?
C5 S1 C1 113.5(3) 2_766 . ?
C7 S1 C1 90.7(2) . . ?
C5 S1 C11 136.9(4) 2_766 2_766 ?
C7 S1 C11 114.2(3) . 2_766 ?
C1 S1 C11 23.5(3) . 2_766 ?
C5 S1 C6 46.1(4) 2_766 2_766 ?
C7 S1 C6 23.3(3) . 2_766 ?
C1 S1 C6 67.4(3) . 2_766 ?
C11 S1 C6 90.8(5) 2_766 2_766 ?
C5 S1 C12 92.1(5) 2_766 2_766 ?
C7 S1 C12 69.3(3) . 2_766 ?
C1 S1 C12 21.4(2) . 2_766 ?
C11 S1 C12 44.9(4) 2_766 2_766 ?
C6 S1 C12 45.94(17) 2_766 2_766 ?
C12 C1 C11 169(2) 2_766 2_766 ?
C12 C1 C2 142.4(9) 2_766 . ?
C11 C1 C2 47.7(15) 2_766 . ?
C12 C1 C6 22.4(9) 2_766 . ?
C11 C1 C6 167.2(16) 2_766 . ?
C2 C1 C6 120.0 . . ?
C12 C1 S1 91.0(12) 2_766 . ?
C11 C1 S1 79.1(12) 2_766 . ?
C2 C1 S1 126.6(6) . . ?
C6 C1 S1 113.4(6) . . ?
C12 C1 C7 44.7(7) 2_766 2_766 ?
C11 C1 C7 145.1(17) 2_766 2_766 ?
C2 C1 C7 97.6(3) . 2_766 ?
C6 C1 C7 22.4(3) . 2_766 ?
S1 C1 C7 135.7(6) . 2_766 ?
C12 C1 C10 145.7(16) 2_766 2_766 ?
C11 C1 C10 44.1(8) 2_766 2_766 ?
C2 C1 C10 4.0(7) . 2_766 ?
C6 C1 C10 123.5(8) . 2_766 ?
S1 C1 C10 123.1(6) . 2_766 ?
C7 C1 C10 101.1(10) 2_766 2_766 ?
C12 C1 C6 32.1(14) 2_766 2_766 ?
C11 C1 C6 137.9(11) 2_766 2_766 ?
C2 C1 C6 174.4(8) . 2_766 ?
C6 C1 C6 54.5(8) . 2_766 ?
S1 C1 C6 58.9(3) . 2_766 ?
C7 C1 C6 76.8(8) 2_766 2_766 ?
C10 C1 C6 177.5(8) 2_766 2_766 ?
C1 C2 C3 120.0 . . ?
C1 C2 C12 12.2(3) . 2_766 ?
C3 C2 C12 107.8(3) . 2_766 ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C12 C2 H2 132.2 2_766 . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C7 C6 C12 130.4(11) 2_766 2_766 ?
C7 C6 C5 8.7(7) 2_766 . ?
C12 C6 C5 139.1(6) 2_766 . ?
C7 C6 C1 111.3(7) 2_766 . ?
C12 C6 C1 19.1(6) 2_766 . ?
C5 C6 C1 120.0 . . ?
C7 C6 C12 137.6(11) 2_766 . ?
C12 C6 C12 92.0(8) 2_766 . ?
C5 C6 C12 129.0(9) . . ?
C1 C6 C12 111.0(9) . . ?
C7 C6 C6 166.9(12) 2_766 2_766 ?
C12 C6 C6 62.7(9) 2_766 2_766 ?
C5 C6 C6 158.2(11) . 2_766 ?
C1 C6 C6 81.8(11) . 2_766 ?
C12 C6 C6 29.3(3) . 2_766 ?
C7 C6 S1 69.4(6) 2_766 2_766 ?
C12 C6 S1 160.2(7) 2_766 2_766 ?
C5 C6 S1 60.7(4) . 2_766 ?
C1 C6 S1 179.2(5) . 2_766 ?
C12 C6 S1 68.2(6) . 2_766 ?
C6 C6 S1 97.5(7) 2_766 2_766 ?
C7 C6 C1 123.1(9) 2_766 2_766 ?
C12 C6 C1 106.5(7) 2_766 2_766 ?
C5 C6 C1 114.4(7) . 2_766 ?
C1 C6 C1 125.5(7) . 2_766 ?
C12 C6 C1 14.5(3) . 2_766 ?
C6 C6 C1 43.8(5) 2_766 2_766 ?
S1 C6 C1 53.7(3) 2_766 2_766 ?
C7 C6 C8 22.4(9) 2_766 2_766 ?
C12 C6 C8 108.0(6) 2_766 2_766 ?
C5 C6 C8 31.1(6) . 2_766 ?
C1 C6 C8 88.9(6) . 2_766 ?
C12 C6 C8 160.1(5) . 2_766 ?
C6 C6 C8 170.7(7) 2_766 2_766 ?
S1 C6 C8 91.8(5) 2_766 2_766 ?
C1 C6 C8 145.5(5) 2_766 2_766 ?
C5 C7 C6 162(2) 2_766 2_766 ?
C5 C7 C8 52.1(16) 2_766 . ?
C6 C7 C8 146.0(8) 2_766 . ?
C5 C7 C12 172.1(16) 2_766 . ?
C6 C7 C12 26.0(8) 2_766 . ?
C8 C7 C12 120.0 . . ?
C5 C7 S1 74.7(13) 2_766 . ?
C6 C7 S1 87.3(11) 2_766 . ?
C8 C7 S1 126.7(5) . . ?
C12 C7 S1 113.2(5) . . ?
C5 C7 C4 48.1(8) 2_766 2_766 ?
C6 C7 C4 149.9(16) 2_766 2_766 ?
C8 C7 C4 4.1(9) . 2_766 ?
C12 C7 C4 123.9(9) . 2_766 ?
S1 C7 C4 122.8(7) . 2_766 ?
C5 C7 C1 151.7(18) 2_766 2_766 ?
C6 C7 C1 46.3(6) 2_766 2_766 ?
C8 C7 C1 99.7(3) . 2_766 ?
C12 C7 C1 20.3(3) . 2_766 ?
S1 C7 C1 133.6(6) . 2_766 ?
C4 C7 C1 103.6(10) 2_766 2_766 ?
C9 C8 C7 120.0 . . ?
C9 C8 C6 108.4(3) . 2_766 ?
C7 C8 C6 11.6(3) . 2_766 ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C6 C8 H8 131.6 2_766 . ?
C8 C9 C10 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 120.0 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C1 C12 C6 138.5(11) 2_766 2_766 ?
C1 C12 C11 5.4(7) 2_766 . ?
C6 C12 C11 143.6(6) 2_766 . ?
C1 C12 C7 114.9(7) 2_766 . ?
C6 C12 C7 23.6(6) 2_766 . ?
C11 C12 C7 120.0 . . ?
C1 C12 C6 133.4(12) 2_766 . ?
C6 C12 C6 88.0(8) 2_766 . ?
C11 C12 C6 128.3(9) . . ?
C7 C12 C6 111.7(9) . . ?
C1 C12 C12 161.6(13) 2_766 2_766 ?
C6 C12 C12 59.7(8) 2_766 2_766 ?
C11 C12 C12 156.7(10) . 2_766 ?
C7 C12 C12 83.3(10) . 2_766 ?
C6 C12 C12 28.3(3) . 2_766 ?
C1 C12 S1 67.6(7) 2_766 2_766 ?
C6 C12 S1 153.8(6) 2_766 2_766 ?
C11 C12 S1 62.5(4) . 2_766 ?
C7 C12 S1 177.3(4) . 2_766 ?
C6 C12 S1 65.8(6) . 2_766 ?
C12 C12 S1 94.2(7) 2_766 2_766 ?
C1 C12 C2 25.4(11) 2_766 2_766 ?
C6 C12 C2 113.1(7) 2_766 2_766 ?
C11 C12 C2 30.5(7) . 2_766 ?
C7 C12 C2 89.5(7) . 2_766 ?
C6 C12 C2 158.8(6) . 2_766 ?
C12 C12 C2 172.7(8) 2_766 2_766 ?
S1 C12 C2 93.0(5) 2_766 2_766 ?
C14 C13 C15 120.1(3) . 2_666 ?
C14 C13 C16 120.1(3) . . ?
C15 C13 C16 119.8(3) 2_666 . ?
C15 C14 C13 119.5(3) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C13 120.4(3) . 2_666 ?
C14 C15 C17 119.4(3) . . ?
C13 C15 C17 120.2(3) 2_666 . ?
N1 C16 C13 178.6(4) . . ?
N2 C17 C15 179.2(4) . . ?

_refine_diff_density_max         0.918
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.105

