# 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_L1
_audit_block_doi                 10.5517/ccdc.csd.cc1n5cy4
_database_code_depnum_ccdc_archive 'CCDC 1524516'
_audit_update_record             
;
2016-12-26 deposited with the CCDC.
2017-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H19 N3'
_chemical_formula_sum            'C22 H19 N3'
_chemical_formula_weight         325.40

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'

_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                   9.727(4)
_cell_length_b                   10.001(4)
_cell_length_c                   11.403(4)
_cell_angle_alpha                113.392(10)
_cell_angle_beta                 96.236(10)
_cell_angle_gamma                113.408(8)
_cell_volume                     886.3(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    294
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      17.71

_exptl_crystal_description       cube
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      1.219
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4545
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_sigmaI/netI    0.1545
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3072
_reflns_number_gt                1195
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0397P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3072
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2039
_refine_ls_R_factor_gt           0.0688
_refine_ls_wR_factor_ref         0.1437
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   0.885
_refine_ls_restrained_S_all      0.885
_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
C12 C 0.5432(4) 0.0493(4) 0.2940(4) 0.0429(10) Uani 1 1 d . . .
N2 N 0.6925(4) 0.1423(4) 0.5024(3) 0.0535(9) Uani 1 1 d . . .
C13 C 0.4942(5) 0.1485(4) 0.3905(4) 0.0485(10) Uani 1 1 d . . .
C7 C 0.6700(4) 0.0490(4) 0.3677(4) 0.0469(10) Uani 1 1 d . . .
C14 C 0.5889(5) 0.1999(4) 0.5147(4) 0.0550(11) Uani 1 1 d . . .
H14 H 0.5822 0.2657 0.5963 0.066 Uiso 1 1 calc R . .
C11 C 0.4951(5) -0.0377(5) 0.1539(4) 0.0594(11) Uani 1 1 d . . .
H11 H 0.4120 -0.0406 0.1024 0.071 Uiso 1 1 calc R . .
C8 C 0.7472(5) -0.0327(5) 0.3073(5) 0.0658(13) Uani 1 1 d . . .
H8 H 0.8302 -0.0309 0.3580 0.079 Uiso 1 1 calc R . .
C10 C 0.5735(6) -0.1192(5) 0.0939(4) 0.0743(13) Uani 1 1 d . . .
H10 H 0.5430 -0.1772 0.0004 0.089 Uiso 1 1 calc R . .
C9 C 0.6982(6) -0.1175(5) 0.1695(6) 0.0772(14) Uani 1 1 d . . .
H9 H 0.7485 -0.1747 0.1256 0.093 Uiso 1 1 calc R . .
N3 N 0.2806(4) 0.1375(4) 0.2536(4) 0.0628(10) Uani 1 1 d . . .
C6 C 0.8138(4) 0.1727(5) 0.6123(4) 0.0661(12) Uani 1 1 d . . .
H6A H 0.8194 0.0711 0.5894 0.079 Uiso 1 1 calc R . .
H6B H 0.7831 0.2013 0.6932 0.079 Uiso 1 1 calc R . .
C16 C 0.1521(5) 0.1779(5) 0.2473(4) 0.0750(13) Uani 1 1 d . . .
H16A H 0.1587 0.2483 0.3380 0.090 Uiso 1 1 calc R . .
H16B H 0.0519 0.0762 0.2079 0.090 Uiso 1 1 calc R . .
C22 C 0.2953(5) 0.3988(5) 0.1865(4) 0.0678(12) Uani 1 1 d . . .
H22 H 0.3876 0.4318 0.2493 0.081 Uiso 1 1 calc R . .
C17 C 0.1568(5) 0.2649(5) 0.1662(4) 0.0610(12) Uani 1 1 d . . .
C18 C 0.0238(5) 0.2194(6) 0.0710(5) 0.0775(14) Uani 1 1 d . . .
H18 H -0.0713 0.1290 0.0537 0.093 Uiso 1 1 calc R . .
C19 C 0.0289(7) 0.3056(8) 0.0008(5) 0.0960(17) Uani 1 1 d . . .
H19 H -0.0626 0.2725 -0.0630 0.115 Uiso 1 1 calc R . .
C15 C 0.3690(5) 0.1864(4) 0.3678(4) 0.0555(11) Uani 1 1 d . . .
H15 H 0.3520 0.2520 0.4431 0.067 Uiso 1 1 calc R . .
C21 C 0.3007(6) 0.4850(6) 0.1162(5) 0.0788(14) Uani 1 1 d . . .
H21 H 0.3954 0.5744 0.1316 0.095 Uiso 1 1 calc R . .
C20 C 0.1652(8) 0.4376(7) 0.0236(5) 0.0897(16) Uani 1 1 d . . .
H20 H 0.1670 0.4958 -0.0232 0.108 Uiso 1 1 calc R . .
N1 N 1.0927(4) 0.2780(4) 0.6639(3) 0.0695(10) Uani 1 1 d . . .
C5 C 0.9767(5) 0.3113(5) 0.6417(3) 0.0512(11) Uani 1 1 d . . .
C1 C 1.2376(5) 0.3994(6) 0.6967(4) 0.0792(14) Uani 1 1 d . . .
H1 H 1.3209 0.3788 0.7130 0.095 Uiso 1 1 calc R . .
C4 C 1.0014(5) 0.4595(5) 0.6506(4) 0.0802(14) Uani 1 1 d . . .
H4 H 0.9164 0.4773 0.6332 0.096 Uiso 1 1 calc R . .
C2 C 1.2743(5) 0.5515(6) 0.7084(4) 0.0718(13) Uani 1 1 d . . .
H2 H 1.3783 0.6313 0.7312 0.086 Uiso 1 1 calc R . .
C3 C 1.1517(6) 0.5813(6) 0.6852(5) 0.0935(16) Uani 1 1 d . . .
H3 H 1.1704 0.6836 0.6928 0.112 Uiso 1 1 calc R . .

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
C12 0.042(2) 0.035(2) 0.050(3) 0.022(2) 0.013(2) 0.015(2)
N2 0.048(2) 0.054(2) 0.061(3) 0.035(2) 0.010(2) 0.0206(19)
C13 0.048(3) 0.043(3) 0.052(3) 0.027(2) 0.007(2) 0.018(2)
C7 0.044(3) 0.038(3) 0.061(3) 0.026(2) 0.021(2) 0.018(2)
C14 0.061(3) 0.049(3) 0.054(3) 0.025(2) 0.018(2) 0.025(2)
C11 0.063(3) 0.051(3) 0.062(3) 0.028(2) 0.012(2) 0.027(2)
C8 0.058(3) 0.051(3) 0.089(4) 0.038(3) 0.018(3) 0.024(3)
C10 0.087(4) 0.062(3) 0.064(3) 0.022(3) 0.024(3) 0.036(3)
C9 0.073(4) 0.061(3) 0.105(4) 0.035(3) 0.033(3) 0.042(3)
N3 0.056(2) 0.061(2) 0.076(3) 0.035(2) 0.013(2) 0.031(2)
C6 0.052(3) 0.067(3) 0.076(3) 0.047(3) 0.002(2) 0.017(2)
C16 0.061(3) 0.089(4) 0.100(4) 0.056(3) 0.029(3) 0.047(3)
C22 0.063(3) 0.064(3) 0.073(3) 0.029(3) 0.010(3) 0.035(3)
C17 0.057(3) 0.061(3) 0.070(3) 0.028(3) 0.018(3) 0.037(3)
C18 0.064(3) 0.084(4) 0.084(4) 0.034(3) 0.010(3) 0.046(3)
C19 0.103(5) 0.117(5) 0.076(4) 0.039(4) 0.007(4) 0.072(4)
C15 0.060(3) 0.050(3) 0.066(3) 0.033(3) 0.026(3) 0.029(2)
C21 0.092(4) 0.075(3) 0.089(4) 0.047(3) 0.033(3) 0.050(3)
C20 0.133(5) 0.097(5) 0.079(4) 0.048(4) 0.039(4) 0.084(4)
N1 0.052(2) 0.064(3) 0.099(3) 0.052(2) 0.013(2) 0.024(2)
C5 0.045(3) 0.050(3) 0.056(3) 0.032(2) 0.004(2) 0.018(2)
C1 0.054(3) 0.083(4) 0.111(4) 0.059(3) 0.020(3) 0.031(3)
C4 0.055(3) 0.058(3) 0.134(4) 0.055(3) 0.020(3) 0.027(3)
C2 0.053(3) 0.070(4) 0.079(3) 0.040(3) 0.014(3) 0.015(3)
C3 0.059(3) 0.062(3) 0.156(5) 0.067(3) 0.021(3) 0.015(3)

_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
C12 C11 1.392(4) . ?
C12 C7 1.417(5) . ?
C12 C13 1.430(5) . ?
N2 C14 1.339(4) . ?
N2 C7 1.380(4) . ?
N2 C6 1.466(4) . ?
C13 C14 1.371(4) . ?
C13 C15 1.439(5) . ?
C7 C8 1.363(5) . ?
C11 C10 1.370(5) . ?
C8 C9 1.368(5) . ?
C10 C9 1.400(5) . ?
N3 C15 1.262(4) . ?
N3 C16 1.461(4) . ?
C6 C5 1.522(5) . ?
C16 C17 1.493(5) . ?
C22 C21 1.382(5) . ?
C22 C17 1.384(5) . ?
C17 C18 1.376(5) . ?
C18 C19 1.382(6) . ?
C19 C20 1.352(6) . ?
C21 C20 1.372(6) . ?
N1 C5 1.323(4) . ?
N1 C1 1.329(5) . ?
C5 C4 1.363(5) . ?
C1 C2 1.362(5) . ?
C4 C3 1.362(5) . ?
C2 C3 1.363(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
C11 C12 C7 118.6(4) . . ?
C11 C12 C13 134.6(4) . . ?
C7 C12 C13 106.8(4) . . ?
C14 N2 C7 109.5(3) . . ?
C14 N2 C6 126.6(4) . . ?
C7 N2 C6 123.9(4) . . ?
C14 C13 C12 106.1(4) . . ?
C14 C13 C15 125.0(4) . . ?
C12 C13 C15 128.9(4) . . ?
C8 C7 N2 130.4(4) . . ?
C8 C7 C12 122.8(4) . . ?
N2 C7 C12 106.8(3) . . ?
N2 C14 C13 110.7(3) . . ?
C10 C11 C12 118.3(4) . . ?
C7 C8 C9 117.7(4) . . ?
C11 C10 C9 121.8(4) . . ?
C8 C9 C10 120.8(4) . . ?
C15 N3 C16 118.4(4) . . ?
N2 C6 C5 113.3(3) . . ?
N3 C16 C17 112.4(3) . . ?
C21 C22 C17 122.0(4) . . ?
C18 C17 C22 116.9(4) . . ?
C18 C17 C16 121.9(4) . . ?
C22 C17 C16 121.1(4) . . ?
C17 C18 C19 121.1(5) . . ?
C20 C19 C18 120.9(5) . . ?
N3 C15 C13 125.0(4) . . ?
C20 C21 C22 119.4(5) . . ?
C19 C20 C21 119.6(5) . . ?
C5 N1 C1 115.8(4) . . ?
N1 C5 C4 123.1(4) . . ?
N1 C5 C6 114.0(4) . . ?
C4 C5 C6 122.9(4) . . ?
N1 C1 C2 125.5(4) . . ?
C3 C4 C5 119.4(4) . . ?
C1 C2 C3 117.0(4) . . ?
C4 C3 C2 119.2(4) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_L3
_audit_block_doi                 10.5517/ccdc.csd.cc1n5cz5
_database_code_depnum_ccdc_archive 'CCDC 1524517'
_audit_update_record             
;
2016-12-26 deposited with the CCDC.
2017-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 N2 S'
_chemical_formula_sum            'C13 H10 N2 S'
_chemical_formula_weight         226.29

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   8.1295(19)
_cell_length_b                   15.338(4)
_cell_length_c                   18.901(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2356.8(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2076
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      1.276
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944.0
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21062
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2076
_reflns_number_gt                1569
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0788P)²+0.5214P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2076
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1299
_refine_ls_wR_factor_gt          0.1175
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_restrained_S_all      0.950
_refine_ls_shift/su_max          0.132
_refine_ls_shift/su_mean         0.007

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
S1 S 0.04025(8) 0.05171(4) 0.28232(4) 0.0684(3) Uani 1 1 d . . .
C6 C 0.0792(3) 0.16274(14) 0.29414(12) 0.0554(6) Uani 1 1 d . . .
C7 C 0.1652(2) 0.20421(13) 0.35119(11) 0.0534(5) Uani 1 1 d . . .
C1 C -0.1322(3) 0.02949(13) 0.33612(11) 0.0494(5) Uani 1 1 d . . .
C12 C 0.1856(3) 0.29178(13) 0.33099(13) 0.0562(6) Uani 1 1 d . . .
C13 C 0.0525(3) 0.22489(15) 0.24390(14) 0.0615(6) Uani 1 1 d . . .
H10 H -0.0007 0.2156 0.2010 0.074 Uiso 1 1 calc R . .
C5 C -0.3099(3) -0.07735(17) 0.36985(13) 0.0711(7) Uani 1 1 d . . .
H4 H -0.3444 -0.1351 0.3672 0.085 Uiso 1 1 calc R . .
C2 C -0.2122(3) 0.09052(15) 0.37755(12) 0.0599(6) Uani 1 1 d . . .
H1 H -0.1759 0.1480 0.3796 0.072 Uiso 1 1 calc R . .
C4 C -0.3966(3) -0.02161(19) 0.41189(14) 0.0806(8) Uani 1 1 d . . .
H3 H -0.4873 -0.0410 0.4375 0.097 Uiso 1 1 calc R . .
C3 C -0.3469(3) 0.06382(18) 0.41556(14) 0.0764(7) Uani 1 1 d . . .
H2 H -0.4040 0.1033 0.4436 0.092 Uiso 1 1 calc R . .
C8 C 0.2294(3) 0.17666(17) 0.41599(13) 0.0716(7) Uani 1 1 d . . .
H5 H 0.2155 0.1194 0.4311 0.086 Uiso 1 1 calc R . .
C10 C 0.3352(4) 0.3214(2) 0.43514(17) 0.0912(9) Uani 1 1 d . . .
H7 H 0.3949 0.3594 0.4636 0.109 Uiso 1 1 calc R . .
C9 C 0.3134(4) 0.2356(2) 0.45689(15) 0.0917(9) Uani 1 1 d . . .
H6 H 0.3566 0.2178 0.5001 0.110 Uiso 1 1 calc R . .
N1 N -0.1785(2) -0.05360(10) 0.33230(9) 0.0559(5) Uani 1 1 d . . .
N2 N 0.1152(3) 0.30218(13) 0.26578(12) 0.0654(6) Uani 1 1 d . . .
C11 C 0.2714(3) 0.35083(16) 0.37325(15) 0.0750(7) Uani 1 1 d . . .
H8 H 0.2845 0.4086 0.3595 0.090 Uiso 1 1 calc R . .
H9 H 0.115(4) 0.3451(18) 0.2404(14) 0.078(9) Uiso 1 1 d . . .

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
S1 0.0706(5) 0.0455(4) 0.0890(5) -0.0091(3) 0.0280(3) -0.0021(3)
C6 0.0504(12) 0.0428(12) 0.0730(15) 0.0038(10) 0.0103(11) 0.0015(9)
C7 0.0497(12) 0.0448(11) 0.0659(14) 0.0059(10) 0.0132(10) 0.0066(10)
C1 0.0538(12) 0.0433(11) 0.0510(12) 0.0002(9) -0.0025(9) -0.0011(9)
C12 0.0504(12) 0.0446(12) 0.0735(15) 0.0030(10) 0.0141(11) 0.0044(10)
C13 0.0560(14) 0.0564(14) 0.0721(15) 0.0062(12) 0.0012(11) 0.0066(11)
C5 0.0839(18) 0.0618(14) 0.0675(15) 0.0056(12) -0.0013(14) -0.0232(14)
C2 0.0640(14) 0.0509(13) 0.0649(14) -0.0105(10) 0.0067(12) -0.0024(11)
C4 0.0777(17) 0.097(2) 0.0669(16) -0.0022(15) 0.0190(14) -0.0264(16)
C3 0.0727(17) 0.0854(19) 0.0710(16) -0.0176(13) 0.0193(13) -0.0053(14)
C8 0.0791(17) 0.0690(15) 0.0668(15) 0.0090(13) 0.0092(14) 0.0080(13)
C10 0.086(2) 0.099(2) 0.089(2) -0.0285(18) 0.0020(17) -0.0073(18)
C9 0.100(2) 0.107(2) 0.0673(17) -0.0016(16) -0.0057(16) 0.0106(19)
N1 0.0654(12) 0.0436(10) 0.0587(11) 0.0007(8) -0.0007(9) -0.0062(8)
N2 0.0691(13) 0.0463(12) 0.0808(15) 0.0185(11) 0.0070(11) 0.0080(10)
C11 0.0699(16) 0.0540(14) 0.101(2) -0.0103(14) 0.0204(16) -0.0063(12)

_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 C6 1.746(2) . ?
S1 C1 1.765(2) . ?
C6 C13 1.363(3) . ?
C6 C7 1.434(3) . ?
C7 C8 1.397(3) . ?
C7 C12 1.406(3) . ?
C1 N1 1.331(2) . ?
C1 C2 1.383(3) . ?
C12 N2 1.368(3) . ?
C12 C11 1.395(3) . ?
C13 N2 1.355(3) . ?
C5 N1 1.333(3) . ?
C5 C4 1.363(4) . ?
C2 C3 1.372(3) . ?
C4 C3 1.373(4) . ?
C8 C9 1.372(4) . ?
C10 C11 1.357(4) . ?
C10 C9 1.390(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
C6 S1 C1 104.98(10) . . ?
C13 C6 C7 106.9(2) . . ?
C13 C6 S1 124.35(19) . . ?
C7 C6 S1 128.09(17) . . ?
C8 C7 C12 118.9(2) . . ?
C8 C7 C6 135.0(2) . . ?
C12 C7 C6 106.08(19) . . ?
N1 C1 C2 123.1(2) . . ?
N1 C1 S1 112.22(15) . . ?
C2 C1 S1 124.69(17) . . ?
N2 C12 C11 130.5(2) . . ?
N2 C12 C7 107.9(2) . . ?
C11 C12 C7 121.6(2) . . ?
C6 C13 N2 109.8(2) . . ?
N1 C5 C4 123.6(2) . . ?
C3 C2 C1 118.0(2) . . ?
C5 C4 C3 118.4(2) . . ?
C2 C3 C4 119.6(2) . . ?
C9 C8 C7 118.7(2) . . ?
C11 C10 C9 121.4(3) . . ?
C8 C9 C10 121.4(3) . . ?
C1 N1 C5 117.3(2) . . ?
C13 N2 C12 109.3(2) . . ?
C10 C11 C12 117.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_Complex3
_audit_block_doi                 10.5517/ccdc.csd.cc1n5d18
_database_code_depnum_ccdc_archive 'CCDC 1524519'
_audit_update_record             
;
2016-12-26 deposited with the CCDC.
2017-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H20 Cl4 N4 Pd2 S2,C H2 Cl2'
_chemical_formula_sum            'C27 H20 Cl4 N4 Pd2 S2'
_chemical_formula_weight         819.19

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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'
'-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                   14.7535(16)
_cell_length_b                   13.5197(15)
_cell_length_c                   15.5348(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.195(2)
_cell_angle_gamma                90.00
_cell_volume                     2889.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4787
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      25.72

_exptl_crystal_description       cube
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      1.883
_exptl_crystal_density_diffrn    1.883
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1608.0
_exptl_absorpt_coefficient_mu    1.786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.558
_exptl_absorpt_correction_T_max  0.632
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13706
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.11
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2542
_reflns_number_gt                2306
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0346P)²+8.0406P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2542
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0753
_refine_ls_wR_factor_gt          0.0734
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.511150(18) 0.320572(18) 0.970157(17) 0.03123(11) Uani 1 1 d . . .
S1 S 0.37166(8) 0.36482(7) 0.76277(6) 0.0487(3) Uani 1 1 d . . .
Cl1 Cl 0.61661(8) 0.21280(7) 1.07775(8) 0.0595(3) Uani 1 1 d . . .
N2 N 0.5787(2) 0.43408(19) 1.05296(19) 0.0320(6) Uani 1 1 d . . .
N1 N 0.4482(2) 0.2124(2) 0.8744(2) 0.0357(7) Uani 1 1 d . . .
C6 C 0.4051(2) 0.4137(2) 0.8776(2) 0.0340(7) Uani 1 1 d . . .
C13 C 0.4514(3) 0.5107(2) 0.8935(2) 0.0346(7) Uani 1 1 d . . .
H13 H 0.4969 0.5309 0.8685 0.041 Uiso 1 1 calc R . .
C12 C 0.6556(2) 0.4849(2) 1.0371(2) 0.0343(7) Uani 1 1 d . . .
C7 C 0.6693(2) 0.5767(2) 1.0804(2) 0.0349(8) Uani 1 1 d . . .
C11 C 0.7126(3) 0.4521(3) 0.9890(3) 0.0434(9) Uani 1 1 d . . .
H11 H 0.7024 0.3907 0.9601 0.052 Uiso 1 1 calc R . .
C5 C 0.3916(3) 0.2392(3) 0.7878(3) 0.0399(8) Uani 1 1 d . . .
C4 C 0.3505(3) 0.1695(3) 0.7195(3) 0.0545(11) Uani 1 1 d . . .
H4 H 0.3113 0.1892 0.6604 0.065 Uiso 1 1 calc R . .
C2 C 0.4250(3) 0.0433(3) 0.8278(3) 0.0533(11) Uani 1 1 d . . .
H2 H 0.4373 -0.0232 0.8428 0.064 Uiso 1 1 calc R . .
C1 C 0.4632(3) 0.1149(3) 0.8927(3) 0.0430(9) Uani 1 1 d . . .
H1 H 0.5014 0.0957 0.9523 0.052 Uiso 1 1 calc R . .
C8 C 0.7430(3) 0.6390(3) 1.0772(3) 0.0447(9) Uani 1 1 d . . .
H8 H 0.7534 0.7005 1.1060 0.054 Uiso 1 1 calc R . .
C9 C 0.8006(3) 0.6056(3) 1.0292(3) 0.0506(10) Uani 1 1 d . . .
H9 H 0.8507 0.6456 1.0261 0.061 Uiso 1 1 calc R . .
C10 C 0.7853(3) 0.5145(3) 0.9859(3) 0.0506(10) Uani 1 1 d . . .
H10 H 0.8248 0.4949 0.9540 0.061 Uiso 1 1 calc R . .
C3 C 0.3680(3) 0.0714(3) 0.7399(3) 0.0583(12) Uani 1 1 d . . .
H3 H 0.3415 0.0239 0.6945 0.070 Uiso 1 1 calc R . .
C14 C 0.5000 0.2696(6) 0.2500 0.124(4) Uani 1 2 d S . .
H14A H 0.4866 0.2275 0.2945 0.149 Uiso 0.50 1 calc PR . .
H14B H 0.5134 0.2275 0.2055 0.149 Uiso 0.50 1 calc PR . .
Cl2 Cl 0.60349(13) 0.34464(14) 0.30771(11) 0.1086(6) Uani 1 1 d . . .

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
Pd1 0.03454(17) 0.02194(16) 0.03318(17) -0.00219(10) 0.00737(12) 0.00002(10)
S1 0.0663(7) 0.0373(5) 0.0318(5) -0.0042(4) 0.0050(5) 0.0033(5)
Cl1 0.0665(7) 0.0307(5) 0.0574(6) 0.0002(4) -0.0064(5) 0.0104(5)
N2 0.0338(15) 0.0223(13) 0.0328(14) -0.0003(12) 0.0034(12) -0.0002(11)
N1 0.0384(16) 0.0290(15) 0.0394(17) -0.0071(13) 0.0138(14) -0.0029(13)
C6 0.0369(18) 0.0264(17) 0.0336(18) -0.0025(14) 0.0066(15) 0.0020(14)
C13 0.0375(18) 0.0294(18) 0.0328(17) 0.0064(15) 0.0078(15) 0.0029(14)
C12 0.0349(18) 0.0276(17) 0.0340(17) 0.0013(14) 0.0048(14) 0.0026(14)
C7 0.0346(18) 0.0267(17) 0.0373(19) 0.0035(14) 0.0056(15) 0.0034(14)
C11 0.050(2) 0.035(2) 0.043(2) -0.0003(16) 0.0136(18) 0.0041(17)
C5 0.042(2) 0.036(2) 0.041(2) -0.0095(16) 0.0131(17) -0.0007(16)
C4 0.060(3) 0.046(2) 0.046(2) -0.0159(18) 0.004(2) 0.000(2)
C2 0.067(3) 0.028(2) 0.066(3) -0.0115(19) 0.026(2) -0.0067(19)
C1 0.054(2) 0.0291(19) 0.047(2) -0.0026(16) 0.0190(18) 0.0000(17)
C8 0.042(2) 0.0308(19) 0.053(2) 0.0024(17) 0.0082(18) -0.0027(16)
C9 0.042(2) 0.044(2) 0.066(3) 0.014(2) 0.019(2) -0.0020(18)
C10 0.047(2) 0.051(3) 0.060(3) 0.009(2) 0.027(2) 0.0075(19)
C3 0.059(3) 0.045(2) 0.062(3) -0.027(2) 0.010(2) -0.008(2)
C14 0.230(13) 0.050(5) 0.102(7) 0.000 0.072(8) 0.000
Cl2 0.1085(12) 0.1135(13) 0.0792(10) -0.0128(9) 0.0045(9) 0.0597(11)

_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
Pd1 N2 2.019(3) . ?
Pd1 N1 2.053(3) . ?
Pd1 C6 2.115(3) . ?
Pd1 Cl1 2.3360(10) . ?
S1 C5 1.743(4) . ?
S1 C6 1.795(3) . ?
N2 C13 1.310(4) 5_667 ?
N2 C12 1.421(4) . ?
N1 C1 1.349(5) . ?
N1 C5 1.351(5) . ?
C6 C13 1.457(5) . ?
C6 C7 1.472(5) 5_667 ?
C13 N2 1.310(4) 5_667 ?
C12 C11 1.385(5) . ?
C12 C7 1.391(5) . ?
C7 C8 1.390(5) . ?
C7 C6 1.472(5) 5_667 ?
C11 C10 1.379(6) . ?
C5 C4 1.384(5) . ?
C4 C3 1.366(6) . ?
C2 C1 1.364(5) . ?
C2 C3 1.374(6) . ?
C8 C9 1.395(6) . ?
C9 C10 1.381(6) . ?
C14 Cl2 1.781(5) . ?
C14 Cl2 1.781(5) 2_655 ?

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
N2 Pd1 N1 173.15(11) . . ?
N2 Pd1 C6 93.11(12) . . ?
N1 Pd1 C6 84.34(12) . . ?
N2 Pd1 Cl1 88.31(8) . . ?
N1 Pd1 Cl1 94.82(9) . . ?
C6 Pd1 Cl1 174.46(10) . . ?
C5 S1 C6 99.99(16) . . ?
C13 N2 C12 108.0(3) 5_667 . ?
C13 N2 Pd1 129.5(2) 5_667 . ?
C12 N2 Pd1 119.9(2) . . ?
C1 N1 C5 117.8(3) . . ?
C1 N1 Pd1 123.1(2) . . ?
C5 N1 Pd1 119.0(2) . . ?
C13 C6 C7 102.9(3) . 5_667 ?
C13 C6 S1 116.3(3) . . ?
C7 C6 S1 119.4(2) 5_667 . ?
C13 C6 Pd1 103.6(2) . . ?
C7 C6 Pd1 103.7(2) 5_667 . ?
S1 C6 Pd1 109.08(16) . . ?
N2 C13 C6 112.1(3) 5_667 . ?
C11 C12 C7 122.4(3) . . ?
C11 C12 N2 128.1(3) . . ?
C7 C12 N2 109.5(3) . . ?
C8 C7 C12 120.1(3) . . ?
C8 C7 C6 132.9(3) . 5_667 ?
C12 C7 C6 107.0(3) . 5_667 ?
C10 C11 C12 117.1(4) . . ?
N1 C5 C4 121.5(4) . . ?
N1 C5 S1 118.5(3) . . ?
C4 C5 S1 120.0(3) . . ?
C3 C4 C5 119.3(4) . . ?
C1 C2 C3 118.6(4) . . ?
N1 C1 C2 123.0(4) . . ?
C7 C8 C9 117.3(4) . . ?
C10 C9 C8 121.6(4) . . ?
C11 C10 C9 121.4(4) . . ?
C4 C3 C2 119.7(4) . . ?
Cl2 C14 Cl2 110.6(5) . 2_655 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.661
_refine_diff_density_rms         0.077
####################################################################### 
# 
# 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_B
_audit_block_doi                 10.5517/ccdc.csd.cc1n5cw2
_database_code_depnum_ccdc_archive 'CCDC 1524514'
_audit_update_record             
;
2016-12-26 deposited with the CCDC.
2017-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 N O'
_chemical_formula_sum            'C12 H9 N O'
_chemical_formula_weight         183.20

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   8.5285(18)
_cell_length_b                   15.890(3)
_cell_length_c                   7.5691(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.881(3)
_cell_angle_gamma                90.00
_cell_volume                     930.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1627
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      24.99

_exptl_crystal_description       cube
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      1.308
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384.0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8759
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1627
_reflns_number_gt                1358
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0537P)²+0.1519P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1627
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.34855(15) 0.07537(7) 0.64231(16) 0.0431(3) Uani 1 1 d . . .
O1 O 0.33001(16) -0.20584(7) 0.49057(18) 0.0668(4) Uani 1 1 d . . .
C11 C 0.24694(19) 0.01487(9) 0.5260(2) 0.0450(4) Uani 1 1 d . . .
H11 H 0.1361 0.0237 0.4296 0.054 Uiso 1 1 calc R . .
C5 C 0.6478(2) 0.07710(10) 0.9123(2) 0.0494(4) Uani 1 1 d . . .
H5 H 0.6500 0.1343 0.9395 0.059 Uiso 1 1 calc R . .
C10 C 0.32914(18) -0.06171(9) 0.5688(2) 0.0425(4) Uani 1 1 d . . .
C4 C 0.50395(17) 0.03937(9) 0.76816(19) 0.0407(4) Uani 1 1 d . . .
C9 C 0.49653(18) -0.04686(9) 0.72539(19) 0.0408(4) Uani 1 1 d . . .
C2 C 0.1507(2) 0.18943(9) 0.4799(2) 0.0532(4) Uani 1 1 d . . .
C8 C 0.6398(2) -0.09696(10) 0.8307(2) 0.0509(4) Uani 1 1 d . . .
H8 H 0.6386 -0.1543 0.8057 0.061 Uiso 1 1 calc R . .
C7 C 0.7825(2) -0.05980(11) 0.9722(2) 0.0587(5) Uani 1 1 d . . .
H7 H 0.8792 -0.0925 1.0428 0.070 Uiso 1 1 calc R . .
C3 C 0.3142(2) 0.16571(9) 0.6380(2) 0.0551(4) Uani 1 1 d . . .
H3A H 0.3131 0.1822 0.7609 0.066 Uiso 1 1 calc R . .
H3B H 0.4070 0.1961 0.6243 0.066 Uiso 1 1 calc R . .
C1 C 0.0189(2) 0.20938(11) 0.3541(3) 0.0667(5) Uani 1 1 d . . .
H1 H -0.0859 0.2252 0.2542 0.080 Uiso 1 1 calc R . .
C12 C 0.2583(2) -0.13750(10) 0.4650(2) 0.0522(4) Uani 1 1 d . . .
H12 H 0.1462 -0.1346 0.3680 0.063 Uiso 1 1 calc R . .
C6 C 0.7861(2) 0.02597(11) 1.0124(2) 0.0574(5) Uani 1 1 d . . .
H6 H 0.8850 0.0490 1.1096 0.069 Uiso 1 1 calc R . .

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
N1 0.0414(7) 0.0374(7) 0.0433(7) 0.0012(5) 0.0107(5) 0.0011(5)
O1 0.0718(8) 0.0405(7) 0.0778(9) -0.0055(6) 0.0216(7) -0.0026(6)
C11 0.0394(8) 0.0459(9) 0.0415(8) 0.0011(6) 0.0091(6) -0.0012(6)
C5 0.0481(9) 0.0484(9) 0.0461(8) -0.0035(7) 0.0144(7) -0.0038(7)
C10 0.0424(8) 0.0400(8) 0.0410(8) 0.0022(6) 0.0135(7) -0.0023(6)
C4 0.0405(8) 0.0410(8) 0.0384(7) 0.0033(6) 0.0144(6) 0.0010(6)
C9 0.0426(8) 0.0393(8) 0.0404(8) 0.0039(6) 0.0171(7) 0.0004(6)
C2 0.0566(10) 0.0388(8) 0.0620(10) 0.0052(7) 0.0230(9) 0.0071(7)
C8 0.0518(9) 0.0427(8) 0.0556(9) 0.0085(7) 0.0200(8) 0.0079(7)
C7 0.0431(9) 0.0652(11) 0.0563(10) 0.0138(8) 0.0097(8) 0.0104(8)
C3 0.0545(10) 0.0381(8) 0.0621(10) 0.0003(7) 0.0143(8) 0.0046(7)
C1 0.0611(11) 0.0504(10) 0.0729(12) 0.0123(9) 0.0129(10) 0.0109(9)
C12 0.0528(9) 0.0440(9) 0.0526(9) -0.0004(7) 0.0152(8) -0.0073(7)
C6 0.0421(9) 0.0686(11) 0.0484(9) 0.0004(8) 0.0063(7) -0.0043(8)

_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 C11 1.3449(18) . ?
N1 C4 1.3888(17) . ?
N1 C3 1.4628(19) . ?
O1 C12 1.2211(19) . ?
C11 C10 1.373(2) . ?
C5 C6 1.369(2) . ?
C5 C4 1.389(2) . ?
C10 C12 1.426(2) . ?
C10 C9 1.4403(19) . ?
C4 C9 1.403(2) . ?
C9 C8 1.394(2) . ?
C2 C1 1.171(2) . ?
C2 C3 1.454(2) . ?
C8 C7 1.371(2) . ?
C7 C6 1.394(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
C11 N1 C4 108.70(12) . . ?
C11 N1 C3 128.25(12) . . ?
C4 N1 C3 122.96(12) . . ?
N1 C11 C10 110.76(13) . . ?
C6 C5 C4 116.70(15) . . ?
C11 C10 C12 124.22(14) . . ?
C11 C10 C9 106.26(12) . . ?
C12 C10 C9 129.43(14) . . ?
C5 C4 N1 129.32(14) . . ?
C5 C4 C9 122.82(13) . . ?
N1 C4 C9 107.85(12) . . ?
C8 C9 C4 118.83(13) . . ?
C8 C9 C10 134.74(14) . . ?
C4 C9 C10 106.42(12) . . ?
C1 C2 C3 179.11(19) . . ?
C7 C8 C9 118.51(15) . . ?
C8 C7 C6 121.47(15) . . ?
C2 C3 N1 112.74(13) . . ?
O1 C12 C10 126.59(16) . . ?
C5 C6 C7 121.66(15) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_Complex2
_audit_block_doi                 10.5517/ccdc.csd.cc1n5d07
_database_code_depnum_ccdc_archive 'CCDC 1524518'
_audit_update_record             
;
2016-12-26 deposited with the CCDC.
2017-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H22 Cl N5 Pd'
_chemical_formula_sum            'C26 H22 Cl N5 Pd'
_chemical_formula_weight         546.34

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 '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/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   10.450(6)
_cell_length_b                   12.734(8)
_cell_length_c                   18.174(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.019(11)
_cell_angle_gamma                90.00
_cell_volume                     2347(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2424
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      18.21

_exptl_crystal_description       cube
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      1.547
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.727
_exptl_absorpt_correction_T_max  0.773
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21242
_diffrn_reflns_av_R_equivalents  0.1182
_diffrn_reflns_av_sigmaI/netI    0.0872
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         24.99
_reflns_number_total             4126
_reflns_number_gt                3060
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0519P)²+4.5405P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4126
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1273
_refine_ls_R_factor_gt           0.0873
_refine_ls_wR_factor_ref         0.1687
_refine_ls_wR_factor_gt          0.1527
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_restrained_S_all      1.168
_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
Pd1 Pd 0.98755(6) 0.97523(5) 0.13267(3) 0.0510(3) Uani 1 1 d . . .
Cl1 Cl 1.1773(3) 0.8721(2) 0.18850(14) 0.0812(8) Uani 1 1 d . . .
N3 N 0.9314(7) 0.8918(5) 0.0351(4) 0.0538(18) Uani 1 1 d . . .
N2 N 0.7348(6) 1.0607(5) 0.0328(4) 0.0471(17) Uani 1 1 d . . .
N1 N 1.0055(7) 1.0784(6) 0.2221(4) 0.0579(19) Uani 1 1 d . . .
C14 C 0.5323(9) 1.1687(8) -0.0150(5) 0.063(2) Uani 1 1 d . . .
H14 H 0.5046 1.1329 -0.0607 0.076 Uiso 1 1 calc R . .
C16 C 0.8335(8) 1.0623(7) 0.0972(5) 0.049(2) Uani 1 1 d . . .
C18 C 0.8246(8) 0.9085(6) -0.0244(4) 0.049(2) Uani 1 1 d . . .
C10 C 0.6895(8) 1.1924(7) 0.1066(5) 0.053(2) Uani 1 1 d . . .
C15 C 0.6464(8) 1.1406(7) 0.0379(5) 0.049(2) Uani 1 1 d . . .
C13 C 0.4615(9) 1.2521(8) 0.0030(6) 0.074(3) Uani 1 1 d . . .
H13 H 0.3847 1.2737 -0.0312 0.089 Uiso 1 1 calc R . .
C9 C 0.8114(8) 1.1412(7) 0.1449(5) 0.052(2) Uani 1 1 d . . .
C22 C 0.8464(10) 0.5098(9) -0.1271(7) 0.080(3) Uani 1 1 d . . .
H22 H 0.8795 0.5169 -0.1700 0.096 Uiso 1 1 calc R . .
N5 N 0.9294(7) 0.7706(6) -0.0454(4) 0.0564(19) Uani 1 1 d . . .
C8 C 0.9104(9) 1.1449(8) 0.2140(5) 0.060(2) Uani 1 1 d . . .
H8 H 0.9067 1.1933 0.2517 0.072 Uiso 1 1 calc R . .
C12 C 0.5034(10) 1.3041(8) 0.0715(6) 0.076(3) Uani 1 1 d . . .
H12 H 0.4531 1.3597 0.0823 0.091 Uiso 1 1 calc R . .
C19 C 0.8239(8) 0.8314(7) -0.0752(5) 0.056(2) Uani 1 1 d . . .
H19 H 0.7630 0.8220 -0.1214 0.067 Uiso 1 1 calc R . .
C6 C 1.4381(12) 1.1878(14) 0.2657(7) 0.106(5) Uani 1 1 d . . .
H6 H 1.5147 1.1625 0.2545 0.128 Uiso 1 1 calc R . .
C2 C 1.2220(8) 1.1550(10) 0.2881(5) 0.063(3) Uani 1 1 d . . .
C7 C 1.3370(11) 1.1184(10) 0.2719(5) 0.088(3) Uani 1 1 d . . .
H7 H 1.3474 1.0468 0.2651 0.105 Uiso 1 1 calc R . .
C1 C 1.1123(9) 1.0830(9) 0.2930(5) 0.075(3) Uani 1 1 d . . .
H1A H 1.0750 1.1057 0.3342 0.090 Uiso 1 1 calc R . .
H1B H 1.1477 1.0129 0.3049 0.090 Uiso 1 1 calc R . .
C11 C 0.6181(9) 1.2764(8) 0.1249(5) 0.066(3) Uani 1 1 d . . .
H11 H 0.6455 1.3123 0.1705 0.080 Uiso 1 1 calc R . .
C5 C 1.4236(13) 1.2906(14) 0.2761(7) 0.102(4) Uani 1 1 d . . .
H5 H 1.4919 1.3362 0.2735 0.123 Uiso 1 1 calc R . .
C3 C 1.2115(10) 1.2621(10) 0.2958(5) 0.080(3) Uani 1 1 d . . .
H3 H 1.1344 1.2893 0.3051 0.096 Uiso 1 1 calc R . .
C4 C 1.3104(13) 1.3300(11) 0.2902(7) 0.103(4) Uani 1 1 d . . .
H4 H 1.3006 1.4019 0.2960 0.124 Uiso 1 1 calc R . .
N4 N 0.9944(7) 0.8072(6) 0.0222(4) 0.0572(19) Uani 1 1 d . . .
C26 C 0.8249(10) 0.5730(8) -0.0075(5) 0.067(3) Uani 1 1 d . . .
H26 H 0.8453 0.6223 0.0313 0.080 Uiso 1 1 calc R . .
C20 C 0.9691(10) 0.6720(8) -0.0748(6) 0.076(3) Uani 1 1 d . . .
H20A H 1.0574 0.6538 -0.0463 0.091 Uiso 1 1 calc R . .
H20B H 0.9717 0.6817 -0.1273 0.091 Uiso 1 1 calc R . .
C21 C 0.8775(8) 0.5836(7) -0.0697(5) 0.053(2) Uani 1 1 d . . .
C25 C 0.7426(12) 0.4907(9) -0.0021(7) 0.088(3) Uani 1 1 d . . .
H25 H 0.7065 0.4847 0.0397 0.106 Uiso 1 1 calc R . .
C24 C 0.7145(12) 0.4176(10) -0.0590(9) 0.103(4) Uani 1 1 d . . .
H24 H 0.6593 0.3614 -0.0557 0.123 Uiso 1 1 calc R . .
C23 C 0.7678(13) 0.4271(10) -0.1211(9) 0.108(4) Uani 1 1 d . . .
H23 H 0.7497 0.3764 -0.1590 0.130 Uiso 1 1 calc R . .
C17 C 0.7278(9) 0.9973(6) -0.0331(5) 0.056(2) Uani 1 1 d . . .
H17A H 0.7406 1.0424 -0.0737 0.068 Uiso 1 1 calc R . .
H17B H 0.6395 0.9683 -0.0488 0.068 Uiso 1 1 calc R . .

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
Pd1 0.0490(4) 0.0587(4) 0.0379(4) 0.0119(3) -0.0036(3) -0.0035(4)
Cl1 0.0790(17) 0.0811(18) 0.0651(16) 0.0172(13) -0.0182(13) 0.0125(14)
N3 0.052(4) 0.047(4) 0.053(5) 0.002(3) -0.004(3) 0.003(4)
N2 0.049(4) 0.047(4) 0.042(4) 0.005(3) 0.004(3) -0.002(3)
N1 0.046(4) 0.084(5) 0.041(4) 0.005(4) 0.006(3) -0.004(4)
C14 0.055(6) 0.070(7) 0.059(6) -0.004(5) 0.001(5) 0.002(5)
C16 0.042(5) 0.055(5) 0.042(5) 0.009(4) -0.004(4) 0.002(4)
C18 0.053(5) 0.044(5) 0.041(5) -0.004(4) -0.003(4) -0.003(4)
C10 0.047(5) 0.060(6) 0.052(6) 0.002(4) 0.015(4) -0.006(4)
C15 0.046(5) 0.057(5) 0.043(5) 0.003(4) 0.006(4) -0.008(4)
C13 0.054(6) 0.085(8) 0.071(7) 0.010(6) -0.010(5) 0.014(6)
C9 0.045(5) 0.066(6) 0.043(5) 0.002(4) 0.007(4) -0.008(4)
C22 0.056(6) 0.084(8) 0.098(8) -0.025(6) 0.014(6) 0.005(6)
N5 0.055(4) 0.052(5) 0.054(5) -0.003(4) -0.002(4) -0.002(4)
C8 0.064(6) 0.073(7) 0.046(5) -0.004(5) 0.018(5) -0.009(5)
C12 0.067(7) 0.083(8) 0.075(8) -0.003(6) 0.012(6) 0.016(6)
C19 0.050(5) 0.064(6) 0.048(5) 0.007(5) 0.002(4) -0.003(5)
C6 0.060(8) 0.180(15) 0.071(8) -0.018(9) 0.000(6) 0.006(10)
C2 0.038(5) 0.110(9) 0.036(5) -0.002(5) -0.003(4) -0.003(6)
C7 0.070(8) 0.121(10) 0.058(7) -0.003(6) -0.012(6) 0.004(7)
C1 0.070(7) 0.107(8) 0.036(5) -0.002(5) -0.011(5) 0.000(6)
C11 0.063(6) 0.081(7) 0.053(6) -0.008(5) 0.011(5) 0.004(5)
C5 0.064(8) 0.160(14) 0.075(8) -0.012(9) 0.001(6) -0.031(9)
C3 0.058(6) 0.113(10) 0.062(7) -0.018(6) -0.003(5) -0.006(7)
C4 0.085(9) 0.118(11) 0.096(10) -0.012(8) -0.002(7) -0.022(9)
N4 0.055(4) 0.055(5) 0.053(5) 0.003(4) -0.003(4) 0.005(4)
C26 0.074(7) 0.064(6) 0.054(6) 0.008(5) -0.002(5) 0.006(6)
C20 0.070(7) 0.084(8) 0.069(7) -0.014(6) 0.008(5) 0.020(6)
C21 0.048(5) 0.049(6) 0.051(6) -0.004(4) -0.009(4) 0.010(4)
C25 0.100(9) 0.071(8) 0.089(9) 0.020(7) 0.011(7) 0.011(7)
C24 0.078(8) 0.064(8) 0.160(14) 0.013(9) 0.017(9) -0.003(7)
C23 0.098(10) 0.085(9) 0.135(13) -0.045(9) 0.019(9) -0.022(8)
C17 0.064(6) 0.046(6) 0.054(6) 0.004(4) 0.005(4) -0.003(4)

_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
Pd1 C16 1.932(8) . ?
Pd1 N3 2.028(7) . ?
Pd1 N1 2.063(7) . ?
Pd1 Cl1 2.390(3) . ?
N3 N4 1.313(9) . ?
N3 C18 1.369(9) . ?
N2 C16 1.359(9) . ?
N2 C15 1.391(10) . ?
N2 C17 1.432(10) . ?
N1 C8 1.287(11) . ?
N1 C1 1.487(10) . ?
C14 C13 1.379(12) . ?
C14 C15 1.386(11) . ?
C16 C9 1.382(11) . ?
C18 C19 1.346(11) . ?
C18 C17 1.500(11) . ?
C10 C15 1.388(11) . ?
C10 C11 1.389(12) . ?
C10 C9 1.450(11) . ?
C13 C12 1.384(13) . ?
C9 C8 1.422(11) . ?
C22 C23 1.356(15) . ?
C22 C21 1.384(12) . ?
N5 N4 1.335(9) . ?
N5 C19 1.348(10) . ?
N5 C20 1.464(11) . ?
C12 C11 1.392(12) . ?
C6 C5 1.336(17) . ?
C6 C7 1.403(16) . ?
C2 C3 1.378(14) . ?
C2 C7 1.385(13) . ?
C2 C1 1.487(13) . ?
C5 C4 1.365(16) . ?
C3 C4 1.370(15) . ?
C26 C25 1.374(14) . ?
C26 C21 1.378(12) . ?
C20 C21 1.495(13) . ?
C25 C24 1.368(16) . ?
C24 C23 1.380(16) . ?

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
C16 Pd1 N3 88.2(3) . . ?
C16 Pd1 N1 78.9(3) . . ?
N3 Pd1 N1 167.0(3) . . ?
C16 Pd1 Cl1 174.5(3) . . ?
N3 Pd1 Cl1 96.8(2) . . ?
N1 Pd1 Cl1 96.2(2) . . ?
N4 N3 C18 109.6(7) . . ?
N4 N3 Pd1 122.3(5) . . ?
C18 N3 Pd1 128.1(6) . . ?
C16 N2 C15 108.1(7) . . ?
C16 N2 C17 127.1(7) . . ?
C15 N2 C17 124.5(7) . . ?
C8 N1 C1 118.0(8) . . ?
C8 N1 Pd1 114.1(6) . . ?
C1 N1 Pd1 127.8(6) . . ?
C13 C14 C15 117.1(9) . . ?
N2 C16 C9 110.0(7) . . ?
N2 C16 Pd1 132.5(7) . . ?
C9 C16 Pd1 117.4(6) . . ?
C19 C18 N3 107.2(7) . . ?
C19 C18 C17 125.9(7) . . ?
N3 C18 C17 126.9(7) . . ?
C15 C10 C11 120.4(8) . . ?
C15 C10 C9 105.8(8) . . ?
C11 C10 C9 133.8(8) . . ?
C14 C15 C10 122.6(9) . . ?
C14 C15 N2 128.1(8) . . ?
C10 C15 N2 109.4(7) . . ?
C14 C13 C12 120.7(9) . . ?
C16 C9 C8 112.4(8) . . ?
C16 C9 C10 106.7(7) . . ?
C8 C9 C10 140.9(9) . . ?
C23 C22 C21 120.2(11) . . ?
N4 N5 C19 110.7(7) . . ?
N4 N5 C20 120.5(7) . . ?
C19 N5 C20 128.5(8) . . ?
N1 C8 C9 117.1(9) . . ?
C13 C12 C11 122.5(9) . . ?
C18 C19 N5 106.0(8) . . ?
C5 C6 C7 119.5(13) . . ?
C3 C2 C7 116.7(11) . . ?
C3 C2 C1 121.5(10) . . ?
C7 C2 C1 121.7(11) . . ?
C2 C7 C6 120.9(12) . . ?
C2 C1 N1 113.6(8) . . ?
C10 C11 C12 116.8(9) . . ?
C6 C5 C4 121.3(14) . . ?
C4 C3 C2 122.5(11) . . ?
C5 C4 C3 119.1(13) . . ?
N3 N4 N5 106.5(6) . . ?
C25 C26 C21 121.0(10) . . ?
N5 C20 C21 112.4(8) . . ?
C26 C21 C22 119.0(10) . . ?
C26 C21 C20 120.9(8) . . ?
C22 C21 C20 120.1(9) . . ?
C24 C25 C26 119.2(12) . . ?
C25 C24 C23 120.2(12) . . ?
C22 C23 C24 120.4(12) . . ?
N2 C17 C18 116.1(7) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.741
_refine_diff_density_min         -1.220
_refine_diff_density_rms         0.093
####################################################################### 
# 
# 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_A
_audit_block_doi                 10.5517/ccdc.csd.cc1n5cv1
_database_code_depnum_ccdc_archive 'CCDC 1524513'
_audit_update_record             
;
2016-12-26 deposited with the CCDC.
2017-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 N2 O'
_chemical_formula_sum            'C15 H12 N2 O'
_chemical_formula_weight         236.27

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/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   11.737(3)
_cell_length_b                   12.583(3)
_cell_length_c                   8.430(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.108(6)
_cell_angle_gamma                90.00
_cell_volume                     1207.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5054
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      25.00

_exptl_crystal_description       cube
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      1.300
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5054
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0524
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2066
_reflns_number_gt                1419
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0501P)²+0.0086P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2066
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1142
_refine_ls_wR_factor_gt          0.1036
_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
N2 N 0.14008(13) 0.87788(12) 0.13071(18) 0.0468(4) Uani 1 1 d . . .
C12 C 0.07456(15) 0.91564(14) -0.1385(2) 0.0438(5) Uani 1 1 d . . .
O1 O -0.16952(12) 0.83636(12) -0.3194(2) 0.0728(5) Uani 1 1 d . . .
C14 C 0.03477(15) 0.83084(15) 0.0764(2) 0.0491(5) Uani 1 1 d . . .
H14 H -0.0024 0.7905 0.1414 0.059 Uiso 1 1 calc R . .
C11 C 0.08073(18) 0.96269(15) -0.2858(3) 0.0541(5) Uani 1 1 d . . .
H11 H 0.0212 0.9521 -0.3798 0.065 Uiso 1 1 calc R . .
C13 C -0.01062(15) 0.84988(14) -0.0868(2) 0.0448(5) Uani 1 1 d . . .
C7 C 0.16706(15) 0.93231(14) 0.0004(2) 0.0434(5) Uani 1 1 d . . .
C6 C 0.20947(16) 0.88127(16) 0.2990(2) 0.0573(6) Uani 1 1 d . . .
H6A H 0.1678 0.8433 0.3677 0.069 Uiso 1 1 calc R . .
H6B H 0.2174 0.9546 0.3353 0.069 Uiso 1 1 calc R . .
C5 C 0.33040(16) 0.83355(16) 0.3216(2) 0.0506(5) Uani 1 1 d . . .
C15 C -0.12436(17) 0.81638(16) -0.1764(3) 0.0556(6) Uani 1 1 d . . .
H15 H -0.1680 0.7756 -0.1206 0.067 Uiso 1 1 calc R . .
C10 C 0.17560(19) 1.02462(16) -0.2899(3) 0.0620(6) Uani 1 1 d . . .
H10 H 0.1802 1.0564 -0.3877 0.074 Uiso 1 1 calc R . .
N1 N 0.41896(16) 0.89591(14) 0.3920(2) 0.0742(6) Uani 1 1 d . . .
C8 C 0.26330(17) 0.99498(14) -0.0030(3) 0.0532(5) Uani 1 1 d . . .
H8 H 0.3238 1.0055 0.0900 0.064 Uiso 1 1 calc R . .
C9 C 0.26551(19) 1.04098(16) -0.1500(3) 0.0632(6) Uani 1 1 d . . .
H9 H 0.3286 1.0841 -0.1563 0.076 Uiso 1 1 calc R . .
C4 C 0.34569(18) 0.73159(18) 0.2733(3) 0.0658(6) Uani 1 1 d . . .
H4 H 0.2814 0.6899 0.2238 0.079 Uiso 1 1 calc R . .
C1 C 0.5268(2) 0.8560(2) 0.4176(3) 0.0893(8) Uani 1 1 d . . .
H1 H 0.5898 0.8989 0.4680 0.107 Uiso 1 1 calc R . .
C3 C 0.4579(2) 0.6923(2) 0.2994(3) 0.0848(8) Uani 1 1 d . . .
H3 H 0.4711 0.6237 0.2670 0.102 Uiso 1 1 calc R . .
C2 C 0.5499(2) 0.7560(3) 0.3740(3) 0.0877(9) Uani 1 1 d . . .
H2 H 0.6268 0.7312 0.3945 0.105 Uiso 1 1 calc R . .

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
N2 0.0458(9) 0.0529(10) 0.0416(10) 0.0051(8) 0.0107(7) 0.0030(8)
C12 0.0492(11) 0.0358(10) 0.0459(12) -0.0006(9) 0.0108(9) 0.0067(9)
O1 0.0598(9) 0.0789(11) 0.0708(11) -0.0062(9) -0.0012(8) 0.0042(8)
C14 0.0449(11) 0.0481(12) 0.0586(14) 0.0072(10) 0.0211(10) 0.0035(9)
C11 0.0646(13) 0.0488(12) 0.0474(13) 0.0048(10) 0.0105(10) 0.0050(11)
C13 0.0425(10) 0.0405(11) 0.0507(13) 0.0024(9) 0.0102(9) 0.0049(9)
C7 0.0492(11) 0.0366(11) 0.0467(12) 0.0014(9) 0.0163(9) 0.0034(9)
C6 0.0599(13) 0.0658(14) 0.0463(13) 0.0042(10) 0.0131(10) 0.0058(11)
C5 0.0534(12) 0.0559(14) 0.0408(12) 0.0079(10) 0.0082(9) 0.0006(11)
C15 0.0485(12) 0.0494(13) 0.0690(16) -0.0028(11) 0.0147(11) 0.0074(10)
C10 0.0835(16) 0.0500(13) 0.0557(15) 0.0114(10) 0.0233(12) -0.0012(12)
N1 0.0628(13) 0.0701(13) 0.0815(15) -0.0056(11) 0.0019(10) -0.0074(11)
C8 0.0551(12) 0.0493(12) 0.0553(14) -0.0046(10) 0.0135(10) -0.0085(10)
C9 0.0738(15) 0.0531(13) 0.0685(17) 0.0010(11) 0.0285(13) -0.0139(11)
C4 0.0577(14) 0.0558(15) 0.0799(17) 0.0017(12) 0.0087(11) -0.0013(11)
C1 0.0571(16) 0.091(2) 0.109(2) 0.0058(17) 0.0009(14) -0.0127(16)
C3 0.0753(18) 0.0615(16) 0.119(2) 0.0127(15) 0.0261(16) 0.0150(14)
C2 0.0520(15) 0.097(2) 0.114(2) 0.0300(18) 0.0204(15) 0.0117(15)

_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
N2 C14 1.346(2) . ?
N2 C7 1.395(2) . ?
N2 C6 1.454(2) . ?
C12 C11 1.393(3) . ?
C12 C7 1.405(2) . ?
C12 C13 1.445(2) . ?
O1 C15 1.219(2) . ?
C14 C13 1.370(2) . ?
C11 C10 1.366(3) . ?
C13 C15 1.428(3) . ?
C7 C8 1.384(2) . ?
C6 C5 1.510(3) . ?
C5 N1 1.322(2) . ?
C5 C4 1.371(3) . ?
C10 C9 1.393(3) . ?
N1 C1 1.330(3) . ?
C8 C9 1.374(3) . ?
C4 C3 1.373(3) . ?
C1 C2 1.356(3) . ?
C3 C2 1.369(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
C14 N2 C7 108.29(15) . . ?
C14 N2 C6 126.47(16) . . ?
C7 N2 C6 124.97(16) . . ?
C11 C12 C7 118.81(18) . . ?
C11 C12 C13 134.64(18) . . ?
C7 C12 C13 106.54(16) . . ?
N2 C14 C13 111.41(17) . . ?
C10 C11 C12 119.0(2) . . ?
C14 C13 C15 124.37(18) . . ?
C14 C13 C12 105.96(16) . . ?
C15 C13 C12 129.48(18) . . ?
C8 C7 N2 129.76(18) . . ?
C8 C7 C12 122.44(18) . . ?
N2 C7 C12 107.79(16) . . ?
N2 C6 C5 113.41(16) . . ?
N1 C5 C4 122.90(19) . . ?
N1 C5 C6 115.65(19) . . ?
C4 C5 C6 121.45(19) . . ?
O1 C15 C13 126.0(2) . . ?
C11 C10 C9 121.1(2) . . ?
C5 N1 C1 117.5(2) . . ?
C9 C8 C7 117.00(19) . . ?
C8 C9 C10 121.6(2) . . ?
C5 C4 C3 118.6(2) . . ?
N1 C1 C2 123.5(2) . . ?
C2 C3 C4 118.8(2) . . ?
C1 C2 C3 118.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.030
