# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

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

data_1193
_database_code_depnum_ccdc_archive 'CCDC 1832713'
_audit_update_record             
;
2018-03-27 deposited with the CCDC.
2018-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C51 H43 N5 O2 P2 Pd, 2(C H Cl3)'

_chemical_formula_sum            'C53 H45 Cl6 N5 O2 P2 Pd'
_chemical_formula_weight         1164.98

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'
P P 0.1023 0.0942 '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'
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'
Cl Cl 0.1484 0.1585 '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                   12.2631(4)
_cell_length_b                   13.7670(4)
_cell_length_c                   19.0767(6)
_cell_angle_alpha                71.606(2)
_cell_angle_beta                 87.408(3)
_cell_angle_gamma                63.9440(10)
_cell_volume                     2728.97(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9382
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      21.28

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.736
_shelx_estimated_absorpt_T_min   0.867
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6795
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'




_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49975
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.068
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9643
_reflns_number_gt                5235
_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'



_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)+(0.0627P)²+3.2912P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9643
_refine_ls_number_parameters     763
_refine_ls_number_restraints     680
_refine_ls_R_factor_all          0.1193
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1648
_refine_ls_wR_factor_gt          0.1275
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.009
_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
C1 C 0.6160(6) 0.6155(6) 0.5715(3) 0.0761(18) Uani 1 1 d . . . . .
C2 C 0.6050(6) 0.7135(7) 0.5823(4) 0.093(2) Uani 1 1 d . . . . .
H2 H 0.6115 0.7148 0.6303 0.112 Uiso 1 1 calc R U . . .
C3 C 0.5842(8) 0.8095(8) 0.5226(5) 0.131(3) Uani 1 1 d . . . . .
H3 H 0.5763 0.8759 0.5300 0.157 Uiso 1 1 calc R U . . .
C4 C 0.5754(9) 0.8061(10) 0.4518(5) 0.135(3) Uani 1 1 d . . . . .
H4 H 0.5626 0.8705 0.4112 0.163 Uiso 1 1 calc R U . . .
C5 C 0.5849(8) 0.7117(10) 0.4401(4) 0.120(3) Uani 1 1 d . . . . .
H5 H 0.5776 0.7117 0.3918 0.144 Uiso 1 1 calc R U . . .
C6 C 0.6054(6) 0.6141(7) 0.4996(4) 0.096(2) Uani 1 1 d . . . . .
H6 H 0.6120 0.5487 0.4915 0.116 Uiso 1 1 calc R U . . .
C7 C 0.7136(6) 0.3682(6) 0.6224(4) 0.0852(19) Uani 1 1 d . . . . .
C8 C 0.8083(7) 0.3557(7) 0.5793(4) 0.100(2) Uani 1 1 d . . . . .
H8 H 0.8329 0.4134 0.5628 0.120 Uiso 1 1 calc R U . . .
C9 C 0.8678(8) 0.2565(10) 0.5603(5) 0.126(3) Uani 1 1 d . . . . .
H9 H 0.9327 0.2472 0.5315 0.151 Uiso 1 1 calc R U . . .
C10 C 0.8294(11) 0.1730(10) 0.5845(7) 0.153(4) Uani 1 1 d . . . . .
H10 H 0.8688 0.1069 0.5717 0.183 Uiso 1 1 calc R U . . .
C11 C 0.7354(12) 0.1845(10) 0.6266(7) 0.167(5) Uani 1 1 d . . . . .
H11 H 0.7106 0.1269 0.6425 0.200 Uiso 1 1 calc R U . . .
C12 C 0.6771(8) 0.2824(8) 0.6456(5) 0.121(3) Uani 1 1 d . . . . .
H12 H 0.6124 0.2908 0.6743 0.145 Uiso 1 1 calc R U . . .
C13 C 0.4914(6) 0.5047(6) 0.6722(3) 0.0765(18) Uani 1 1 d . . . . .
C14 C 0.3907(6) 0.5726(6) 0.6201(4) 0.090(2) Uani 1 1 d . . . . .
H14 H 0.3994 0.6156 0.5735 0.108 Uiso 1 1 calc R U . . .
C15 C 0.2755(7) 0.5786(8) 0.6355(5) 0.117(3) Uani 1 1 d . . . . .
H15 H 0.2081 0.6259 0.6000 0.141 Uiso 1 1 calc R U . . .
C16 C 0.2641(8) 0.5144(9) 0.7030(5) 0.124(3) Uani 1 1 d . . . . .
H16 H 0.1883 0.5170 0.7137 0.149 Uiso 1 1 calc R U . . .
C17 C 0.3642(9) 0.4445(8) 0.7564(5) 0.118(3) Uani 1 1 d . . . . .
H17 H 0.3554 0.4000 0.8023 0.142 Uiso 1 1 calc R U . . .
C18 C 0.4773(7) 0.4411(7) 0.7416(4) 0.099(2) Uani 1 1 d . . . . .
H18 H 0.5436 0.3962 0.7780 0.119 Uiso 1 1 calc R U . . .
C19 C 0.9155(5) 0.6130(5) 0.8074(3) 0.0674(14) Uani 1 1 d . U . . .
C20 C 0.8547(7) 0.7036(6) 0.7445(4) 0.094(2) Uani 1 1 d . U . . .
H20 H 0.7887 0.7084 0.7190 0.113 Uiso 1 1 calc R U . . .
C21 C 0.8937(9) 0.7888(7) 0.7192(5) 0.134(3) Uani 1 1 d . U . . .
H21 H 0.8539 0.8508 0.6763 0.160 Uiso 1 1 calc R U . . .
C22 C 0.9900(9) 0.7812(8) 0.7572(5) 0.125(3) Uani 1 1 d . U . . .
H22 H 1.0166 0.8373 0.7388 0.150 Uiso 1 1 calc R U . . .
C23 C 1.0481(8) 0.6945(7) 0.8209(5) 0.109(2) Uani 1 1 d . U . . .
H23 H 1.1107 0.6932 0.8475 0.131 Uiso 1 1 calc R U . . .
C24 C 1.0131(6) 0.6075(6) 0.8460(4) 0.0849(18) Uani 1 1 d . U . . .
H24 H 1.0546 0.5455 0.8886 0.102 Uiso 1 1 calc R U . . .
C25 C 0.7824(5) 0.5228(5) 0.9186(3) 0.0606(14) Uani 1 1 d . . . . .
C26 C 0.7774(5) 0.5985(5) 0.9528(3) 0.0712(16) Uani 1 1 d . . . . .
H26 H 0.8173 0.6438 0.9349 0.085 Uiso 1 1 calc R U . . .
C27 C 0.7131(7) 0.6078(6) 1.0139(4) 0.096(2) Uani 1 1 d . . . . .
H27 H 0.7096 0.6596 1.0366 0.115 Uiso 1 1 calc R U . . .
C28 C 0.6545(7) 0.5407(7) 1.0409(4) 0.100(2) Uani 1 1 d . . . . .
H28 H 0.6115 0.5465 1.0820 0.120 Uiso 1 1 calc R U . . .
C29 C 0.6599(6) 0.4657(6) 1.0071(4) 0.090(2) Uani 1 1 d . . . . .
H29 H 0.6216 0.4191 1.0261 0.108 Uiso 1 1 calc R U . . .
C30 C 0.7204(5) 0.4574(5) 0.9460(3) 0.0750(17) Uani 1 1 d . . . . .
H30 H 0.7202 0.4077 0.9225 0.090 Uiso 1 1 calc R U . . .
C31 C 1.0082(5) 0.3714(5) 0.8824(3) 0.0646(15) Uani 1 1 d . . . . .
C32 C 1.1043(6) 0.3423(6) 0.8398(4) 0.0795(18) Uani 1 1 d . . . . .
H32 H 1.0973 0.3913 0.7919 0.095 Uiso 1 1 calc R U . . .
C33 C 1.2097(8) 0.2424(8) 0.8671(6) 0.108(3) Uani 1 1 d . . . . .
H33 H 1.2739 0.2239 0.8381 0.130 Uiso 1 1 calc R U . . .
C34 C 1.2194(9) 0.1702(7) 0.9378(7) 0.123(3) Uani 1 1 d . . . . .
H34 H 1.2901 0.1016 0.9561 0.148 Uiso 1 1 calc R U . . .
C35 C 1.1260(9) 0.1975(7) 0.9819(5) 0.112(3) Uani 1 1 d . . . . .
H35 H 1.1339 0.1484 1.0299 0.135 Uiso 1 1 calc R U . . .
C36 C 1.0204(7) 0.2987(6) 0.9541(4) 0.0855(19) Uani 1 1 d . . . . .
H36 H 0.9572 0.3181 0.9837 0.103 Uiso 1 1 calc R U . . .
C37 C 0.8992(6) 0.4338(6) 0.6993(3) 0.0709(17) Uani 1 1 d . . . . .
C38 C 0.9328(6) 0.5073(7) 0.6445(3) 0.091(2) Uani 1 1 d . . . . .
H38 H 0.8858 0.5861 0.6319 0.109 Uiso 1 1 calc R U . . .
C39 C 1.0352(9) 0.4644(10) 0.6088(5) 0.120(3) Uani 1 1 d . . . . .
H39 H 1.0563 0.5148 0.5725 0.144 Uiso 1 1 calc R U . . .
C40 C 1.1048(8) 0.3504(11) 0.6260(5) 0.128(4) Uani 1 1 d . . . . .
H40 H 1.1729 0.3232 0.6011 0.154 Uiso 1 1 calc R U . . .
C41 C 1.0763(7) 0.2733(8) 0.6804(5) 0.108(3) Uani 1 1 d . . . . .
H41 H 1.1254 0.1949 0.6929 0.129 Uiso 1 1 calc R U . . .
C42 C 0.9721(6) 0.3160(7) 0.7161(4) 0.0791(19) Uani 1 1 d . . . . .
C50 C 0.5363(7) 0.6679(8) 0.7885(4) 0.088(2) Uani 1 1 d . . . . .
C51 C 0.4149(8) 0.7113(7) 0.8202(5) 0.157(4) Uani 1 1 d . . . . .
H51A H 0.3938 0.6494 0.8411 0.235 Uiso 1 1 calc R U . . .
H51B H 0.4215 0.7410 0.8583 0.235 Uiso 1 1 calc R U . . .
H51C H 0.3527 0.7708 0.7814 0.235 Uiso 1 1 calc R U . . .
C53 C 0.1916(10) -0.0031(10) 0.6071(8) 0.194(5) Uani 1 1 d . . . . .
H53 H 0.1405 0.0446 0.6358 0.233 Uiso 1 1 calc R U . . .
P1 P 0.64199(15) 0.49297(15) 0.65318(8) 0.0693(5) Uani 1 1 d . . . . .
P2 P 0.86635(13) 0.50078(12) 0.84013(8) 0.0571(4) Uani 1 1 d . . . . .
Pd1 Pd 0.74873(4) 0.49713(4) 0.74902(2) 0.06030(18) Uani 1 1 d . . . . .
N5 N 0.9371(5) 0.2429(5) 0.7714(4) 0.0851(18) Uani 1 1 d D . . . .
H5A H 0.880(6) 0.273(6) 0.787(4) 0.102 Uiso 1 1 d . U . . .
O1 O 0.5857(4) 0.5641(4) 0.7953(2) 0.0742(11) Uani 1 1 d . . . . .
O2 O 0.5800(5) 0.7349(4) 0.7588(3) 0.1202(19) Uani 1 1 d . . . . .
Cl4 Cl 0.1773(4) 0.0784(4) 0.5090(3) 0.274(2) Uani 1 1 d . . . . .
Cl5 Cl 0.1434(6) -0.1044(4) 0.6015(3) 0.303(3) Uani 1 1 d . . . . .
Cl6 Cl 0.3301(5) -0.0609(6) 0.6351(3) 0.330(3) Uani 1 1 d . . . . .
C43 C 0.984(3) 0.1271(11) 0.8033(16) 0.090(5) Uani 0.515(16) 1 d D U P A 1
C44 C 0.8438(18) 0.112(2) 0.9013(12) 0.097(4) Uani 0.515(16) 1 d D U P A 1
C45 C 0.7269(18) 0.1421(19) 0.8756(13) 0.117(5) Uani 0.515(16) 1 d D U P A 1
H45 H 0.7127 0.1375 0.8296 0.140 Uiso 0.515(16) 1 calc R U P A 1
C46 C 0.627(2) 0.180(2) 0.9172(12) 0.119(5) Uani 0.515(16) 1 d D U P A 1
H46 H 0.5478 0.1996 0.8999 0.143 Uiso 0.515(16) 1 calc R U P A 1
C47 C 0.654(2) 0.186(2) 0.9842(12) 0.113(5) Uani 0.515(16) 1 d D U P A 1
H47 H 0.5905 0.2125 1.0124 0.135 Uiso 0.515(16) 1 calc R U P A 1
C48 C 0.7696(19) 0.1531(19) 1.0109(12) 0.128(5) Uani 0.515(16) 1 d D U P A 1
H48 H 0.7838 0.1574 1.0571 0.153 Uiso 0.515(16) 1 calc R U P A 1
C49 C 0.866(2) 0.1140(17) 0.9710(12) 0.114(5) Uani 0.515(16) 1 d D U P A 1
H49 H 0.9457 0.0892 0.9907 0.137 Uiso 0.515(16) 1 calc R U P A 1
N1 N 0.9454(17) 0.0679(13) 0.8619(10) 0.099(4) Uani 0.515(16) 1 d D U P A 1
N2 N 1.0155(16) -0.0500(13) 0.8806(11) 0.121(4) Uani 0.515(16) 1 d D U P A 1
N3 N 1.0984(16) -0.0587(14) 0.8365(12) 0.127(5) Uani 0.515(16) 1 d D U P A 1
N4 N 1.0843(18) 0.0454(14) 0.7893(11) 0.109(4) Uani 0.515(16) 1 d D U P A 1
C43' C 0.983(3) 0.1309(12) 0.7854(16) 0.087(5) Uani 0.485(16) 1 d D U P A 2
C44' C 0.8307(19) 0.113(2) 0.8772(13) 0.095(4) Uani 0.485(16) 1 d D U P A 2
C45' C 0.7278(19) 0.1130(19) 0.8542(14) 0.118(5) Uani 0.485(16) 1 d D U P A 2
H45' H 0.7246 0.0885 0.8145 0.142 Uiso 0.485(16) 1 calc R U P A 2
C46' C 0.627(2) 0.152(2) 0.8931(13) 0.126(6) Uani 0.485(16) 1 d D U P A 2
H46' H 0.5535 0.1561 0.8774 0.151 Uiso 0.485(16) 1 calc R U P A 2
C47' C 0.633(2) 0.183(2) 0.9537(15) 0.120(6) Uani 0.485(16) 1 d D U P A 2
H47' H 0.5652 0.2067 0.9793 0.144 Uiso 0.485(16) 1 calc R U P A 2
C48' C 0.740(2) 0.179(2) 0.9766(14) 0.128(5) Uani 0.485(16) 1 d D U P A 2
H48' H 0.7465 0.1963 1.0191 0.153 Uiso 0.485(16) 1 calc R U P A 2
C49' C 0.840(2) 0.1482(18) 0.9352(12) 0.107(5) Uani 0.485(16) 1 d D U P A 2
H49' H 0.9106 0.1517 0.9469 0.128 Uiso 0.485(16) 1 calc R U P A 2
N1' N 0.9289(18) 0.0777(14) 0.8341(11) 0.096(4) Uani 0.485(16) 1 d D U P A 2
N2' N 0.9919(16) -0.0342(14) 0.8357(13) 0.114(4) Uani 0.485(16) 1 d D U P A 2
N3' N 1.0715(17) -0.0371(15) 0.7906(12) 0.119(5) Uani 0.485(16) 1 d D U P A 2
N4' N 1.0705(18) 0.0669(14) 0.7536(11) 0.102(4) Uani 0.485(16) 1 d D U P A 2
C52 C 0.5208(12) 0.9414(14) 0.8006(8) 0.134(5) Uani 0.634(6) 1 d D U P B 3
H52 H 0.5456 0.8718 0.7875 0.161 Uiso 0.634(6) 1 calc R U P B 3
Cl1 Cl 0.3664(5) 1.0067(5) 0.7963(4) 0.238(4) Uani 0.634(6) 1 d D U P B 3
Cl2 Cl 0.5718(8) 1.0296(7) 0.7384(4) 0.236(4) Uani 0.634(6) 1 d D U P B 3
Cl3 Cl 0.5880(7) 0.9039(6) 0.8872(3) 0.202(3) Uani 0.634(6) 1 d D U P B 3
C52' C 0.5546(18) 0.946(2) 0.8117(11) 0.163(9) Uani 0.366(6) 1 d D U P B 4
H52' H 0.5472 0.8906 0.7921 0.195 Uiso 0.366(6) 1 calc R U P B 4
Cl1' Cl 0.7068(9) 0.9173(8) 0.8236(7) 0.217(5) Uani 0.366(6) 1 d D U P B 4
Cl2' Cl 0.4708(11) 1.0824(8) 0.7541(5) 0.187(5) Uani 0.366(6) 1 d D U P B 4
Cl3' Cl 0.5030(12) 0.9351(11) 0.8969(6) 0.226(7) Uani 0.366(6) 1 d D U P B 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
C1 C2 1.375(9) . ?
C1 C6 1.390(8) . ?
C1 P1 1.814(6) . ?
C2 C3 1.375(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.341(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(10) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.372(9) . ?
C7 C12 1.381(9) . ?
C7 P1 1.825(7) . ?
C8 C9 1.394(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.370(13) . ?
C9 H9 0.9300 . ?
C10 C11 1.354(13) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(12) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.377(9) . ?
C13 C18 1.389(8) . ?
C13 P1 1.812(6) . ?
C14 C15 1.402(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.354(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.389(11) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(9) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.368(8) . ?
C19 C24 1.395(8) . ?
C19 P2 1.820(5) . ?
C20 C21 1.397(9) . ?
C20 H20 0.9300 . ?
C21 C22 1.361(11) . ?
C21 H21 0.9300 . ?
C22 C23 1.351(11) . ?
C22 H22 0.9300 . ?
C23 C24 1.386(8) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.372(7) . ?
C25 C30 1.391(7) . ?
C25 P2 1.807(5) . ?
C26 C27 1.385(8) . ?
C26 H26 0.9300 . ?
C27 C28 1.373(9) . ?
C27 H27 0.9300 . ?
C28 C29 1.357(9) . ?
C28 H28 0.9300 . ?
C29 C30 1.362(8) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 C32 1.382(8) . ?
C31 C36 1.385(8) . ?
C31 P2 1.830(6) . ?
C32 C33 1.371(10) . ?
C32 H32 0.9300 . ?
C33 C34 1.373(11) . ?
C33 H33 0.9300 . ?
C34 C35 1.377(11) . ?
C34 H34 0.9300 . ?
C35 C36 1.382(9) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 C38 1.395(8) . ?
C37 C42 1.399(9) . ?
C37 Pd1 2.003(6) . ?
C38 C39 1.384(10) . ?
C38 H38 0.9300 . ?
C39 C40 1.351(12) . ?
C39 H39 0.9300 . ?
C40 C41 1.387(12) . ?
C40 H40 0.9300 . ?
C41 C42 1.398(8) . ?
C41 H41 0.9300 . ?
C42 N5 1.407(8) . ?
C50 O2 1.238(8) . ?
C50 O1 1.248(8) . ?
C50 C51 1.518(9) . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C53 Cl6 1.559(11) . ?
C53 Cl5 1.768(13) . ?
C53 Cl4 1.822(13) . ?
C53 H53 0.9800 . ?
P1 Pd1 2.3253(15) . ?
P2 Pd1 2.3346(14) . ?
Pd1 O1 2.088(4) . ?
N5 C43' 1.326(14) . ?
N5 C43 1.364(14) . ?
N5 H5A 0.75(6) . ?
C43 N4 1.342(13) . ?
C43 N1 1.358(13) . ?
C44 C45 1.372(16) . ?
C44 C49 1.380(16) . ?
C44 N1 1.423(15) . ?
C45 C46 1.419(17) . ?
C45 H45 0.9300 . ?
C46 C47 1.369(16) . ?
C46 H46 0.9300 . ?
C47 C48 1.356(17) . ?
C47 H47 0.9300 . ?
C48 C49 1.377(16) . ?
C48 H48 0.9300 . ?
C49 H49 0.9300 . ?
N1 N2 1.392(13) . ?
N2 N3 1.279(15) . ?
N3 N4 1.370(15) . ?
C43' N4' 1.322(13) . ?
C43' N1' 1.333(14) . ?
C44' C45' 1.356(17) . ?
C44' C49' 1.366(17) . ?
C44' N1' 1.418(15) . ?
C45' C46' 1.397(17) . ?
C45' H45' 0.9300 . ?
C46' C47' 1.372(17) . ?
C46' H46' 0.9300 . ?
C47' C48' 1.375(18) . ?
C47' H47' 0.9300 . ?
C48' C49' 1.402(17) . ?
C48' H48' 0.9300 . ?
C49' H49' 0.9300 . ?
N1' N2' 1.377(13) . ?
N2' N3' 1.269(16) . ?
N3' N4' 1.378(16) . ?
C52 Cl1 1.694(13) . ?
C52 Cl3 1.698(14) . ?
C52 Cl2 1.722(14) . ?
C52 H52 0.9800 . ?
C52' Cl3' 1.703(19) . ?
C52' Cl2' 1.706(19) . ?
C52' Cl1' 1.741(19) . ?
C52' H52' 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.6(6) . . ?
C2 C1 P1 117.8(5) . . ?
C6 C1 P1 122.7(6) . . ?
C3 C2 C1 120.5(7) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.0(9) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 121.3(9) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 120.5(8) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.1(8) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C8 C7 C12 119.2(7) . . ?
C8 C7 P1 120.5(6) . . ?
C12 C7 P1 120.2(6) . . ?
C7 C8 C9 120.1(8) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 119.0(9) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C11 C10 C9 121.6(10) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 119.2(10) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C11 C12 C7 120.8(9) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C14 C13 C18 118.7(6) . . ?
C14 C13 P1 122.5(5) . . ?
C18 C13 P1 118.7(6) . . ?
C13 C14 C15 121.5(7) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C16 C15 C14 118.8(8) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C15 C16 C17 120.8(7) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 120.2(7) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C13 119.9(7) . . ?
C17 C18 H18 120.0 . . ?
C13 C18 H18 120.0 . . ?
C20 C19 C24 120.2(6) . . ?
C20 C19 P2 119.1(5) . . ?
C24 C19 P2 120.7(5) . . ?
C19 C20 C21 118.8(7) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 H20 120.6 . . ?
C22 C21 C20 120.1(8) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 121.8(8) . . ?
C23 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
C22 C23 C24 119.0(8) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
C23 C24 C19 119.9(7) . . ?
C23 C24 H24 120.0 . . ?
C19 C24 H24 120.0 . . ?
C26 C25 C30 118.6(5) . . ?
C26 C25 P2 124.3(4) . . ?
C30 C25 P2 117.1(4) . . ?
C25 C26 C27 120.4(6) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C28 C27 C26 120.1(6) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C29 C28 C27 119.4(6) . . ?
C29 C28 H28 120.3 . . ?
C27 C28 H28 120.3 . . ?
C28 C29 C30 121.2(6) . . ?
C28 C29 H29 119.4 . . ?
C30 C29 H29 119.4 . . ?
C29 C30 C25 120.3(6) . . ?
C29 C30 H30 119.9 . . ?
C25 C30 H30 119.9 . . ?
C32 C31 C36 118.9(6) . . ?
C32 C31 P2 118.7(5) . . ?
C36 C31 P2 122.3(5) . . ?
C33 C32 C31 121.1(7) . . ?
C33 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
C32 C33 C34 119.2(8) . . ?
C32 C33 H33 120.4 . . ?
C34 C33 H33 120.4 . . ?
C33 C34 C35 121.1(8) . . ?
C33 C34 H34 119.5 . . ?
C35 C34 H34 119.5 . . ?
C34 C35 C36 119.3(8) . . ?
C34 C35 H35 120.4 . . ?
C36 C35 H35 120.4 . . ?
C35 C36 C31 120.4(7) . . ?
C35 C36 H36 119.8 . . ?
C31 C36 H36 119.8 . . ?
C38 C37 C42 117.5(6) . . ?
C38 C37 Pd1 120.3(6) . . ?
C42 C37 Pd1 122.1(4) . . ?
C39 C38 C37 120.8(8) . . ?
C39 C38 H38 119.6 . . ?
C37 C38 H38 119.6 . . ?
C40 C39 C38 120.7(8) . . ?
C40 C39 H39 119.6 . . ?
C38 C39 H39 119.6 . . ?
C39 C40 C41 120.9(8) . . ?
C39 C40 H40 119.5 . . ?
C41 C40 H40 119.5 . . ?
C40 C41 C42 118.6(8) . . ?
C40 C41 H41 120.7 . . ?
C42 C41 H41 120.7 . . ?
C41 C42 C37 121.4(7) . . ?
C41 C42 N5 121.8(7) . . ?
C37 C42 N5 116.9(5) . . ?
O2 C50 O1 124.6(7) . . ?
O2 C50 C51 119.7(8) . . ?
O1 C50 C51 115.8(7) . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
Cl6 C53 Cl5 111.6(7) . . ?
Cl6 C53 Cl4 106.0(7) . . ?
Cl5 C53 Cl4 100.9(8) . . ?
Cl6 C53 H53 112.5 . . ?
Cl5 C53 H53 112.5 . . ?
Cl4 C53 H53 112.5 . . ?
C13 P1 C1 105.1(3) . . ?
C13 P1 C7 104.4(3) . . ?
C1 P1 C7 105.7(3) . . ?
C13 P1 Pd1 114.25(19) . . ?
C1 P1 Pd1 109.1(2) . . ?
C7 P1 Pd1 117.4(2) . . ?
C25 P2 C19 107.0(3) . . ?
C25 P2 C31 103.5(3) . . ?
C19 P2 C31 103.6(3) . . ?
C25 P2 Pd1 110.97(18) . . ?
C19 P2 Pd1 113.5(2) . . ?
C31 P2 Pd1 117.25(17) . . ?
C37 Pd1 O1 176.52(19) . . ?
C37 Pd1 P1 86.98(16) . . ?
O1 Pd1 P1 89.57(11) . . ?
C37 Pd1 P2 89.40(16) . . ?
O1 Pd1 P2 94.05(11) . . ?
P1 Pd1 P2 176.16(6) . . ?
C43' N5 C42 124.5(10) . . ?
C43 N5 C42 134.4(10) . . ?
C43' N5 H5A 120(6) . . ?
C43 N5 H5A 111(6) . . ?
C42 N5 H5A 114(6) . . ?
C50 O1 Pd1 119.0(4) . . ?
N4 C43 N1 103.7(14) . . ?
N4 C43 N5 128.3(16) . . ?
N1 C43 N5 127.8(15) . . ?
C45 C44 C49 119.3(18) . . ?
C45 C44 N1 122.2(18) . . ?
C49 C44 N1 118.2(17) . . ?
C44 C45 C46 122.0(19) . . ?
C44 C45 H45 119.0 . . ?
C46 C45 H45 119.0 . . ?
C47 C46 C45 116(2) . . ?
C47 C46 H46 121.9 . . ?
C45 C46 H46 121.9 . . ?
C48 C47 C46 122(2) . . ?
C48 C47 H47 118.9 . . ?
C46 C47 H47 118.9 . . ?
C47 C48 C49 121(2) . . ?
C47 C48 H48 119.4 . . ?
C49 C48 H48 119.4 . . ?
C48 C49 C44 119.0(19) . . ?
C48 C49 H49 120.5 . . ?
C44 C49 H49 120.5 . . ?
C43 N1 N2 112.3(13) . . ?
C43 N1 C44 128.0(17) . . ?
N2 N1 C44 119.7(17) . . ?
N3 N2 N1 102.9(14) . . ?
N2 N3 N4 112.8(15) . . ?
C43 N4 N3 108.1(14) . . ?
N4' C43' N5 127.7(16) . . ?
N4' C43' N1' 116.1(15) . . ?
N5 C43' N1' 116.1(15) . . ?
C45' C44' C49' 124(2) . . ?
C45' C44' N1' 114.5(18) . . ?
C49' C44' N1' 121.7(19) . . ?
C44' C45' C46' 116.7(19) . . ?
C44' C45' H45' 121.7 . . ?
C46' C45' H45' 121.7 . . ?
C47' C46' C45' 122(2) . . ?
C47' C46' H46' 119.1 . . ?
C45' C46' H46' 119.1 . . ?
C46' C47' C48' 120(2) . . ?
C46' C47' H47' 120.1 . . ?
C48' C47' H47' 120.1 . . ?
C47' C48' C49' 119(2) . . ?
C47' C48' H48' 120.4 . . ?
C49' C48' H48' 120.4 . . ?
C44' C49' C48' 119(2) . . ?
C44' C49' H49' 120.7 . . ?
C48' C49' H49' 120.7 . . ?
C43' N1' N2' 103.2(14) . . ?
C43' N1' C44' 134.5(18) . . ?
N2' N1' C44' 122.3(19) . . ?
N3' N2' N1' 106.8(16) . . ?
N2' N3' N4' 115.2(15) . . ?
C43' N4' N3' 98.7(13) . . ?
Cl1 C52 Cl3 111.8(9) . . ?
Cl1 C52 Cl2 110.6(9) . . ?
Cl3 C52 Cl2 108.8(9) . . ?
Cl1 C52 H52 108.5 . . ?
Cl3 C52 H52 108.5 . . ?
Cl2 C52 H52 108.5 . . ?
Cl3' C52' Cl2' 107.9(13) . . ?
Cl3' C52' Cl1' 106.5(13) . . ?
Cl2' C52' Cl1' 109.9(14) . . ?
Cl3' C52' H52' 110.8 . . ?
Cl2' C52' H52' 110.8 . . ?
Cl1' C52' H52' 110.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.4(11) . . . . ?
P1 C1 C2 C3 -179.5(6) . . . . ?
C1 C2 C3 C4 -0.4(13) . . . . ?
C2 C3 C4 C5 0.9(15) . . . . ?
C3 C4 C5 C6 -0.8(15) . . . . ?
C4 C5 C6 C1 0.0(12) . . . . ?
C2 C1 C6 C5 0.6(10) . . . . ?
P1 C1 C6 C5 179.6(6) . . . . ?
C12 C7 C8 C9 -0.9(11) . . . . ?
P1 C7 C8 C9 175.7(6) . . . . ?
C7 C8 C9 C10 0.7(13) . . . . ?
C8 C9 C10 C11 -0.2(17) . . . . ?
C9 C10 C11 C12 -0.1(19) . . . . ?
C10 C11 C12 C7 -0.2(17) . . . . ?
C8 C7 C12 C11 0.7(13) . . . . ?
P1 C7 C12 C11 -175.9(8) . . . . ?
C18 C13 C14 C15 -0.1(11) . . . . ?
P1 C13 C14 C15 178.7(6) . . . . ?
C13 C14 C15 C16 -1.1(12) . . . . ?
C14 C15 C16 C17 0.7(14) . . . . ?
C15 C16 C17 C18 0.9(14) . . . . ?
C16 C17 C18 C13 -2.1(12) . . . . ?
C14 C13 C18 C17 1.6(10) . . . . ?
P1 C13 C18 C17 -177.1(6) . . . . ?
C24 C19 C20 C21 1.2(10) . . . . ?
P2 C19 C20 C21 -179.3(6) . . . . ?
C19 C20 C21 C22 -0.5(13) . . . . ?
C20 C21 C22 C23 -2.0(15) . . . . ?
C21 C22 C23 C24 3.7(14) . . . . ?
C22 C23 C24 C19 -2.9(11) . . . . ?
C20 C19 C24 C23 0.5(10) . . . . ?
P2 C19 C24 C23 -179.1(5) . . . . ?
C30 C25 C26 C27 0.9(9) . . . . ?
P2 C25 C26 C27 -178.4(5) . . . . ?
C25 C26 C27 C28 0.4(10) . . . . ?
C26 C27 C28 C29 -0.2(11) . . . . ?
C27 C28 C29 C30 -1.3(12) . . . . ?
C28 C29 C30 C25 2.6(11) . . . . ?
C26 C25 C30 C29 -2.4(9) . . . . ?
P2 C25 C30 C29 177.0(5) . . . . ?
C36 C31 C32 C33 1.0(9) . . . . ?
P2 C31 C32 C33 -175.7(5) . . . . ?
C31 C32 C33 C34 0.3(10) . . . . ?
C32 C33 C34 C35 -1.3(12) . . . . ?
C33 C34 C35 C36 0.9(12) . . . . ?
C34 C35 C36 C31 0.5(11) . . . . ?
C32 C31 C36 C35 -1.5(9) . . . . ?
P2 C31 C36 C35 175.2(5) . . . . ?
C42 C37 C38 C39 -0.5(9) . . . . ?
Pd1 C37 C38 C39 -178.7(5) . . . . ?
C37 C38 C39 C40 0.1(12) . . . . ?
C38 C39 C40 C41 -0.6(14) . . . . ?
C39 C40 C41 C42 1.3(12) . . . . ?
C40 C41 C42 C37 -1.7(10) . . . . ?
C40 C41 C42 N5 179.6(7) . . . . ?
C38 C37 C42 C41 1.3(9) . . . . ?
Pd1 C37 C42 C41 179.5(5) . . . . ?
C38 C37 C42 N5 -180.0(5) . . . . ?
Pd1 C37 C42 N5 -1.8(8) . . . . ?
C14 C13 P1 C1 17.6(6) . . . . ?
C18 C13 P1 C1 -163.7(5) . . . . ?
C14 C13 P1 C7 -93.4(6) . . . . ?
C18 C13 P1 C7 85.4(6) . . . . ?
C14 C13 P1 Pd1 137.2(5) . . . . ?
C18 C13 P1 Pd1 -44.1(6) . . . . ?
C2 C1 P1 C13 93.0(5) . . . . ?
C6 C1 P1 C13 -86.1(6) . . . . ?
C2 C1 P1 C7 -157.0(5) . . . . ?
C6 C1 P1 C7 24.0(6) . . . . ?
C2 C1 P1 Pd1 -29.9(6) . . . . ?
C6 C1 P1 Pd1 151.0(5) . . . . ?
C8 C7 P1 C13 157.0(6) . . . . ?
C12 C7 P1 C13 -26.4(7) . . . . ?
C8 C7 P1 C1 46.4(6) . . . . ?
C12 C7 P1 C1 -137.0(6) . . . . ?
C8 C7 P1 Pd1 -75.4(6) . . . . ?
C12 C7 P1 Pd1 101.2(6) . . . . ?
C26 C25 P2 C19 -10.0(6) . . . . ?
C30 C25 P2 C19 170.7(5) . . . . ?
C26 C25 P2 C31 99.0(5) . . . . ?
C30 C25 P2 C31 -80.3(5) . . . . ?
C26 C25 P2 Pd1 -134.4(5) . . . . ?
C30 C25 P2 Pd1 46.3(5) . . . . ?
C20 C19 P2 C25 -103.5(5) . . . . ?
C24 C19 P2 C25 76.0(5) . . . . ?
C20 C19 P2 C31 147.5(5) . . . . ?
C24 C19 P2 C31 -33.0(5) . . . . ?
C20 C19 P2 Pd1 19.3(6) . . . . ?
C24 C19 P2 Pd1 -161.2(4) . . . . ?
C32 C31 P2 C25 -167.5(4) . . . . ?
C36 C31 P2 C25 15.9(5) . . . . ?
C32 C31 P2 C19 -55.9(5) . . . . ?
C36 C31 P2 C19 127.5(5) . . . . ?
C32 C31 P2 Pd1 70.0(5) . . . . ?
C36 C31 P2 Pd1 -106.6(5) . . . . ?
C41 C42 N5 C43' -13(2) . . . . ?
C37 C42 N5 C43' 168(2) . . . . ?
C41 C42 N5 C43 0(2) . . . . ?
C37 C42 N5 C43 -179(2) . . . . ?
O2 C50 O1 Pd1 -3.5(10) . . . . ?
C51 C50 O1 Pd1 177.1(5) . . . . ?
C42 N5 C43 N4 1(5) . . . . ?
C42 N5 C43 N1 173.4(19) . . . . ?
C49 C44 C45 C46 3(4) . . . . ?
N1 C44 C45 C46 176(2) . . . . ?
C44 C45 C46 C47 0(3) . . . . ?
C45 C46 C47 C48 -2(3) . . . . ?
C46 C47 C48 C49 1(3) . . . . ?
C47 C48 C49 C44 3(3) . . . . ?
C45 C44 C49 C48 -4(3) . . . . ?
N1 C44 C49 C48 -178(2) . . . . ?
N4 C43 N1 N2 -5(3) . . . . ?
N5 C43 N1 N2 -179(3) . . . . ?
N4 C43 N1 C44 178(2) . . . . ?
N5 C43 N1 C44 4(5) . . . . ?
C45 C44 N1 C43 81(3) . . . . ?
C49 C44 N1 C43 -105(3) . . . . ?
C45 C44 N1 N2 -96(3) . . . . ?
C49 C44 N1 N2 78(3) . . . . ?
C43 N1 N2 N3 4(3) . . . . ?
C44 N1 N2 N3 -178.3(17) . . . . ?
N1 N2 N3 N4 -2(2) . . . . ?
N1 C43 N4 N3 4(3) . . . . ?
N5 C43 N4 N3 178(3) . . . . ?
N2 N3 N4 C43 -1(3) . . . . ?
C42 N5 C43' N4' 3(5) . . . . ?
C42 N5 C43' N1' -172.6(16) . . . . ?
C49' C44' C45' C46' 0(4) . . . . ?
N1' C44' C45' C46' -178(2) . . . . ?
C44' C45' C46' C47' -3(3) . . . . ?
C45' C46' C47' C48' 1(4) . . . . ?
C46' C47' C48' C49' 3(4) . . . . ?
C45' C44' C49' C48' 4(4) . . . . ?
N1' C44' C49' C48' -178(2) . . . . ?
C47' C48' C49' C44' -6(3) . . . . ?
N4' C43' N1' N2' 2(3) . . . . ?
N5 C43' N1' N2' 178(3) . . . . ?
N4' C43' N1' C44' -177(2) . . . . ?
N5 C43' N1' C44' -1(4) . . . . ?
C45' C44' N1' C43' 108(3) . . . . ?
C49' C44' N1' C43' -69(4) . . . . ?
C45' C44' N1' N2' -71(3) . . . . ?
C49' C44' N1' N2' 112(3) . . . . ?
C43' N1' N2' N3' 0(2) . . . . ?
C44' N1' N2' N3' 178.8(18) . . . . ?
N1' N2' N3' N4' -1(2) . . . . ?
N5 C43' N4' N3' -178(3) . . . . ?
N1' C43' N4' N3' -3(3) . . . . ?
N2' N3' N4' C43' 3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O2 0.93 2.54 3.459(9) 167.7 .
C20 H20 O2 0.93 2.54 3.214(9) 129.9 .
C41 H41 N4 0.93 2.51 3.13(2) 124.2 .
C41 H41 N4' 0.93 2.14 2.77(2) 124.4 .
C51 H51C Cl6 0.96 2.94 3.723(10) 139.4 1_565
C53 H53 N4' 0.98 2.43 3.32(2) 150.6 1_455
C49 H49 N2 0.93 2.36 2.93(4) 118.7 2_757
C52 H52 O2 0.98 1.99 2.969(19) 174.7 .
C52' H52' O2 0.98 2.29 3.25(3) 165.7 .

_refine_diff_density_max         0.535
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.060



####################################################################### 
# 
# 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_1080
_database_code_depnum_ccdc_archive 'CCDC 1834321'
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 N5 O'
_chemical_formula_sum            'C17 H15 N5 O'
_chemical_formula_weight         305.34

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.7446(4)
_cell_length_b                   11.5290(7)
_cell_length_c                   15.2091(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.140(3)
_cell_angle_gamma                90
_cell_volume                     1480.11(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1309
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      22.37

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            7469
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.246
_diffrn_reflns_theta_max         24.019
_diffrn_reflns_theta_full        24.019
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2323
_reflns_number_gt                1446
_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)+(0.0646P)²+0.0686P] 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         2323
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1397
_refine_ls_wR_factor_gt          0.1156
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.003
_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
C1 C 0.4682(3) 0.2212(2) 0.96796(19) 0.0450(7) Uani 1 1 d . . . . .
H1 H 0.3978 0.1748 0.9262 0.054 Uiso 1 1 calc R U . . .
C2 C 0.5432(3) 0.3140(2) 0.9387(2) 0.0512(8) Uani 1 1 d . . . . .
H2 H 0.5218 0.3294 0.8766 0.061 Uiso 1 1 calc R U . . .
C3 C 0.6487(3) 0.3843(3) 0.9990(2) 0.0502(8) Uani 1 1 d . . . . .
C4 C 0.6761(3) 0.3591(3) 1.0903(2) 0.0574(9) Uani 1 1 d . . . . .
H4 H 0.7464 0.4056 1.1321 0.069 Uiso 1 1 calc R U . . .
C5 C 0.6037(3) 0.2679(3) 1.1227(2) 0.0514(8) Uani 1 1 d . . . . .
H5 H 0.6242 0.2533 1.1848 0.062 Uiso 1 1 calc R U . . .
C6 C 0.4999(3) 0.1990(2) 1.05997(18) 0.0400(7) Uani 1 1 d . . . . .
C7 C 0.7311(3) 0.4834(3) 0.9656(2) 0.0731(11) Uani 1 1 d . . . . .
H7A H 0.7199 0.5526 0.9984 0.110 Uiso 1 1 calc R U . . .
H7B H 0.6844 0.4952 0.9018 0.110 Uiso 1 1 calc R U . . .
H7C H 0.8415 0.4654 0.9755 0.110 Uiso 1 1 calc R U . . .
C8 C 0.3150(3) 0.0244(2) 1.04502(17) 0.0345(6) Uani 1 1 d . . . . .
C9 C 0.1791(3) -0.1356(3) 1.0995(2) 0.0444(7) Uani 1 1 d . . . . .
C10 C 0.0988(3) -0.1457(2) 1.00347(18) 0.0387(7) Uani 1 1 d . . . . .
C11 C -0.0186(3) -0.2300(2) 0.9768(2) 0.0469(8) Uani 1 1 d . . . . .
H11 H -0.0436 -0.2779 1.0202 0.056 Uiso 1 1 calc R U . . .
C12 C -0.0968(3) -0.2423(3) 0.8868(2) 0.0491(8) Uani 1 1 d . . . . .
H12 H -0.1756 -0.2983 0.8699 0.059 Uiso 1 1 calc R U . . .
C13 C -0.0610(3) -0.1728(2) 0.82016(19) 0.0421(7) Uani 1 1 d . . . . .
C14 C 0.0575(3) -0.0891(2) 0.84438(17) 0.0387(7) Uani 1 1 d . . . . .
C15 C 0.1363(3) -0.0736(2) 0.93698(17) 0.0350(6) Uani 1 1 d . . . . .
C16 C -0.1516(3) -0.1890(3) 0.72212(19) 0.0575(9) Uani 1 1 d . . . . .
H16A H -0.1907 -0.1153 0.6964 0.086 Uiso 1 1 calc R U . . .
H16B H -0.2391 -0.2406 0.7189 0.086 Uiso 1 1 calc R U . . .
H16C H -0.0828 -0.2213 0.6886 0.086 Uiso 1 1 calc R U . . .
C17 C 0.1022(3) -0.0155(3) 0.77324(19) 0.0543(8) Uani 1 1 d . . . . .
H17A H 0.1136 -0.0639 0.7240 0.082 Uiso 1 1 calc R U . . .
H17B H 0.2006 0.0232 0.7997 0.082 Uiso 1 1 calc R U . . .
H17C H 0.0209 0.0410 0.7506 0.082 Uiso 1 1 calc R U . . .
N1 N 0.4262(2) 0.10271(19) 1.09195(14) 0.0397(6) Uani 1 1 d . . . . .
N2 N 0.4625(3) 0.0781(2) 1.18337(15) 0.0530(7) Uani 1 1 d . . . . .
N3 N 0.3810(3) -0.0088(2) 1.19717(15) 0.0547(7) Uani 1 1 d . . . . .
N4 N 0.2889(2) -0.04321(19) 1.11376(14) 0.0428(6) Uani 1 1 d . . . . .
N5 N 0.2493(2) 0.01513(18) 0.95932(14) 0.0370(6) Uani 1 1 d . . . . .
O1 O 0.1621(2) -0.1939(2) 1.16277(14) 0.0645(6) 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
C1 C6 1.378(4) . ?
C1 C2 1.388(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.380(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(4) . ?
C3 C7 1.507(4) . ?
C4 C5 1.383(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(4) . ?
C5 H5 0.9300 . ?
C6 N1 1.431(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 N5 1.284(3) . ?
C8 N4 1.370(3) . ?
C8 N1 1.381(3) . ?
C9 O1 1.214(3) . ?
C9 N4 1.413(3) . ?
C9 C10 1.450(4) . ?
C10 C11 1.395(4) . ?
C10 C15 1.412(3) . ?
C11 C12 1.368(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.390(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.393(3) . ?
C13 C16 1.506(4) . ?
C14 C15 1.408(3) . ?
C14 C17 1.505(4) . ?
C15 N5 1.401(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N1 N2 1.372(3) . ?
N2 N3 1.278(3) . ?
N3 N4 1.372(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.9(3) . . ?
C6 C1 H1 120.6 . . ?
C2 C1 H1 120.6 . . ?
C3 C2 C1 121.9(3) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C4 C3 C2 117.2(3) . . ?
C4 C3 C7 121.7(3) . . ?
C2 C3 C7 121.1(3) . . ?
C3 C4 C5 123.0(3) . . ?
C3 C4 H4 118.5 . . ?
C5 C4 H4 118.5 . . ?
C6 C5 C4 118.0(3) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C1 C6 C5 121.1(3) . . ?
C1 C6 N1 120.0(2) . . ?
C5 C6 N1 118.9(3) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N5 C8 N4 127.4(2) . . ?
N5 C8 N1 130.3(2) . . ?
N4 C8 N1 102.3(2) . . ?
O1 C9 N4 120.9(3) . . ?
O1 C9 C10 128.8(3) . . ?
N4 C9 C10 110.2(2) . . ?
C11 C10 C15 119.5(3) . . ?
C11 C10 C9 118.3(2) . . ?
C15 C10 C9 122.2(2) . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 121.3(3) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C14 120.0(3) . . ?
C12 C13 C16 119.4(3) . . ?
C14 C13 C16 120.6(3) . . ?
C13 C14 C15 119.2(2) . . ?
C13 C14 C17 121.0(2) . . ?
C15 C14 C17 119.8(2) . . ?
N5 C15 C14 117.7(2) . . ?
N5 C15 C10 122.5(2) . . ?
C14 C15 C10 119.8(2) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 N1 C8 109.5(2) . . ?
N2 N1 C6 119.9(2) . . ?
C8 N1 C6 130.5(2) . . ?
N3 N2 N1 109.7(2) . . ?
N2 N3 N4 107.0(2) . . ?
C8 N4 N3 111.5(2) . . ?
C8 N4 C9 123.6(2) . . ?
N3 N4 C9 124.9(2) . . ?
C8 N5 C15 114.1(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.2(4) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C1 C2 C3 C7 178.9(3) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C7 C3 C4 C5 -179.2(3) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
C2 C1 C6 N1 -179.0(2) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C4 C5 C6 N1 178.7(2) . . . . ?
O1 C9 C10 C11 2.3(4) . . . . ?
N4 C9 C10 C11 -177.7(2) . . . . ?
O1 C9 C10 C15 -177.4(3) . . . . ?
N4 C9 C10 C15 2.6(3) . . . . ?
C15 C10 C11 C12 -0.2(4) . . . . ?
C9 C10 C11 C12 -179.9(2) . . . . ?
C10 C11 C12 C13 0.6(4) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C11 C12 C13 C16 -179.4(3) . . . . ?
C12 C13 C14 C15 -2.0(4) . . . . ?
C16 C13 C14 C15 177.9(2) . . . . ?
C12 C13 C14 C17 178.0(2) . . . . ?
C16 C13 C14 C17 -2.2(4) . . . . ?
C13 C14 C15 N5 -176.9(2) . . . . ?
C17 C14 C15 N5 3.1(3) . . . . ?
C13 C14 C15 C10 2.5(4) . . . . ?
C17 C14 C15 C10 -177.5(2) . . . . ?
C11 C10 C15 N5 177.9(2) . . . . ?
C9 C10 C15 N5 -2.3(4) . . . . ?
C11 C10 C15 C14 -1.4(4) . . . . ?
C9 C10 C15 C14 178.3(2) . . . . ?
N5 C8 N1 N2 -179.5(2) . . . . ?
N4 C8 N1 N2 1.0(3) . . . . ?
N5 C8 N1 C6 1.6(4) . . . . ?
N4 C8 N1 C6 -177.9(2) . . . . ?
C1 C6 N1 N2 177.5(2) . . . . ?
C5 C6 N1 N2 -1.8(3) . . . . ?
C1 C6 N1 C8 -3.6(4) . . . . ?
C5 C6 N1 C8 177.0(2) . . . . ?
C8 N1 N2 N3 -0.7(3) . . . . ?
C6 N1 N2 N3 178.3(2) . . . . ?
N1 N2 N3 N4 0.1(3) . . . . ?
N5 C8 N4 N3 179.6(2) . . . . ?
N1 C8 N4 N3 -0.9(3) . . . . ?
N5 C8 N4 C9 -1.1(4) . . . . ?
N1 C8 N4 C9 178.4(2) . . . . ?
N2 N3 N4 C8 0.5(3) . . . . ?
N2 N3 N4 C9 -178.8(2) . . . . ?
O1 C9 N4 C8 179.0(2) . . . . ?
C10 C9 N4 C8 -1.0(3) . . . . ?
O1 C9 N4 N3 -1.8(4) . . . . ?
C10 C9 N4 N3 178.2(2) . . . . ?
N4 C8 N5 C15 1.6(4) . . . . ?
N1 C8 N5 C15 -177.8(2) . . . . ?
C14 C15 N5 C8 179.5(2) . . . . ?
C10 C15 N5 C8 0.2(3) . . . . ?

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.044



####################################################################### 
# 
# 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_1159
_database_code_depnum_ccdc_archive 'CCDC 1834323'
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H20 N10 Pd'
_chemical_formula_weight         578.92

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.0025(17)
_cell_length_b                   13.5967(18)
_cell_length_c                   15.1462(14)
_cell_angle_alpha                90
_cell_angle_beta                 116.114(5)
_cell_angle_gamma                90
_cell_volume                     2589.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1607
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      19.92

_exptl_crystal_description       Block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.752
_shelx_estimated_absorpt_T_min   0.877
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            16326
_diffrn_reflns_av_unetI/netI     0.1029
_diffrn_reflns_av_R_equivalents  0.0884
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.652
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4545
_reflns_number_gt                2735
_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)+(0.0402P)²] 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         4545
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1127
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
C1 C 0.5376(6) 0.2801(5) 0.8188(5) 0.063(2) Uani 1 1 d . . . . .
H1 H 0.5944 0.2983 0.8061 0.076 Uiso 1 1 calc R U . . .
C2 C 0.5547(8) 0.2546(6) 0.9126(5) 0.082(3) Uani 1 1 d . . . . .
H2 H 0.6232 0.2553 0.9636 0.098 Uiso 1 1 calc R U . . .
C3 C 0.4722(10) 0.2286(7) 0.9304(6) 0.100(4) Uani 1 1 d . . . . .
H3 H 0.4835 0.2110 0.9937 0.121 Uiso 1 1 calc R U . . .
C4 C 0.3721(9) 0.2279(7) 0.8558(7) 0.103(3) Uani 1 1 d . . . . .
H4 H 0.3158 0.2097 0.8692 0.123 Uiso 1 1 calc R U . . .
C5 C 0.3511(7) 0.2532(6) 0.7609(5) 0.081(3) Uani 1 1 d . . . . .
H5 H 0.2824 0.2533 0.7102 0.097 Uiso 1 1 calc R U . . .
C6 C 0.4378(6) 0.2785(5) 0.7456(5) 0.0499(18) Uani 1 1 d . . . . .
C7 C 0.4522(5) 0.3802(5) 0.6105(4) 0.0385(15) Uani 1 1 d . . . . .
C8 C 0.2518(4) 0.4663(5) 0.2689(4) 0.0364(16) Uani 1 1 d . . . . .
C9 C 0.2322(5) 0.3688(5) 0.2455(4) 0.0481(17) Uani 1 1 d . . . . .
H9 H 0.2607 0.3215 0.2946 0.058 Uiso 1 1 calc R U . . .
C10 C 0.1702(6) 0.3400(6) 0.1489(5) 0.071(2) Uani 1 1 d . . . . .
H10 H 0.1564 0.2738 0.1333 0.085 Uiso 1 1 calc R U . . .
C11 C 0.1296(6) 0.4102(7) 0.0769(5) 0.070(2) Uani 1 1 d . . . . .
H11 H 0.0890 0.3910 0.0120 0.084 Uiso 1 1 calc R U . . .
C12 C 0.1477(5) 0.5072(7) 0.0990(5) 0.067(2) Uani 1 1 d . . . . .
H12 H 0.1182 0.5540 0.0494 0.080 Uiso 1 1 calc R U . . .
C13 C 0.2104(5) 0.5373(5) 0.1957(4) 0.0513(18) Uani 1 1 d . . . . .
H13 H 0.2242 0.6036 0.2109 0.062 Uiso 1 1 calc R U . . .
C14 C 0.5363(5) 0.4987(5) 0.2711(4) 0.0430(16) Uani 1 1 d . . . . .
C15 C 0.4575(6) 0.4623(5) 0.1842(4) 0.059(2) Uani 1 1 d . . . . .
H15 H 0.3868 0.4620 0.1737 0.071 Uiso 1 1 calc R U . . .
C16 C 0.4852(8) 0.4264(6) 0.1131(5) 0.082(3) Uani 1 1 d . . . . .
H16 H 0.4326 0.4011 0.0549 0.098 Uiso 1 1 calc R U . . .
C17 C 0.5866(10) 0.4273(6) 0.1265(7) 0.093(3) Uani 1 1 d . . . . .
H17 H 0.6034 0.4035 0.0775 0.111 Uiso 1 1 calc R U . . .
C18 C 0.6654(8) 0.4629(6) 0.2119(7) 0.088(3) Uani 1 1 d . . . . .
H18 H 0.7355 0.4639 0.2209 0.106 Uiso 1 1 calc R U . . .
C19 C 0.6400(6) 0.4975(5) 0.2850(5) 0.061(2) Uani 1 1 d . . . . .
H19 H 0.6936 0.5201 0.3440 0.073 Uiso 1 1 calc R U . . .
C20 C 0.6998(4) 0.4388(5) 0.5827(4) 0.0359(14) Uani 1 1 d . . . . .
C21 C 0.9006(5) 0.4028(5) 0.6723(4) 0.0432(16) Uani 1 1 d . . . . .
C22 C 0.9483(5) 0.4926(5) 0.6978(5) 0.0586(19) Uani 1 1 d . . . . .
H22 H 0.9121 0.5493 0.6662 0.070 Uiso 1 1 calc R U . . .
C23 C 1.0499(6) 0.4980(7) 0.7704(6) 0.085(3) Uani 1 1 d . . . . .
H23 H 1.0820 0.5591 0.7903 0.102 Uiso 1 1 calc R U . . .
C24 C 1.1055(7) 0.4141(9) 0.8147(6) 0.096(3) Uani 1 1 d . . . . .
H24 H 1.1750 0.4178 0.8637 0.115 Uiso 1 1 calc R U . . .
C25 C 1.0565(7) 0.3263(8) 0.7853(6) 0.093(3) Uani 1 1 d . . . . .
H25 H 1.0943 0.2692 0.8135 0.111 Uiso 1 1 calc R U . . .
C26 C 0.9529(6) 0.3183(5) 0.7150(5) 0.063(2) Uani 1 1 d . . . . .
H26 H 0.9197 0.2574 0.6971 0.076 Uiso 1 1 calc R U . . .
N1 N 0.4189(4) 0.3018(4) 0.6461(3) 0.0485(14) Uani 1 1 d . . . . .
N2 N 0.3831(4) 0.2288(4) 0.5751(4) 0.0577(16) Uani 1 1 d . . . . .
N3 N 0.3934(4) 0.2623(4) 0.5002(3) 0.0504(15) Uani 1 1 d . . . . .
N4 N 0.4368(4) 0.3537(4) 0.5192(3) 0.0375(12) Uani 1 1 d . . . . .
N5 N 0.3204(4) 0.4910(4) 0.3677(3) 0.0367(12) Uani 1 1 d . . . . .
N6 N 0.5076(4) 0.5347(3) 0.3448(3) 0.0357(12) Uani 1 1 d . . . . .
N7 N 0.6255(4) 0.3985(4) 0.4975(3) 0.0372(13) Uani 1 1 d . . . . .
N8 N 0.6751(4) 0.3325(4) 0.4642(3) 0.0525(15) Uani 1 1 d . . . . .
N9 N 0.7747(4) 0.3269(4) 0.5238(3) 0.0532(15) Uani 1 1 d . . . . .
N10 N 0.7927(4) 0.3931(4) 0.5986(3) 0.0438(13) Uani 1 1 d . . . . .
Pd1 Pd 0.46996(4) 0.43650(3) 0.42512(3) 0.03200(16) 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
C1 C6 1.349(9) . ?
C1 C2 1.378(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.344(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.359(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(9) . ?
C5 H5 0.9300 . ?
C6 N1 1.447(7) . ?
C7 N6 1.333(7) 3_666 ?
C7 N4 1.353(6) . ?
C7 N1 1.365(7) . ?
C8 C9 1.368(8) . ?
C8 C13 1.389(8) . ?
C8 N5 1.418(6) . ?
C9 C10 1.389(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(9) . ?
C10 H10 0.9300 . ?
C11 C12 1.358(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.398(8) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.372(8) . ?
C14 C15 1.385(8) . ?
C14 N6 1.428(7) . ?
C15 C16 1.385(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.344(11) . ?
C16 H16 0.9300 . ?
C17 C18 1.367(11) . ?
C17 H17 0.9300 . ?
C18 C19 1.387(9) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 N5 1.320(7) 3_666 ?
C20 N10 1.364(7) . ?
C20 N7 1.366(7) . ?
C21 C26 1.363(8) . ?
C21 C22 1.363(9) . ?
C21 N10 1.436(7) . ?
C22 C23 1.364(9) . ?
C22 H22 0.9300 . ?
C23 C24 1.378(11) . ?
C23 H23 0.9300 . ?
C24 C25 1.350(11) . ?
C24 H24 0.9300 . ?
C25 C26 1.375(9) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
N1 N2 1.385(6) . ?
N2 N3 1.289(6) . ?
N3 N4 1.357(6) . ?
N4 Pd1 2.024(4) . ?
N5 C20 1.320(7) 3_666 ?
N5 Pd1 2.022(4) . ?
N6 C7 1.333(7) 3_666 ?
N6 Pd1 2.026(4) . ?
N7 N8 1.361(6) . ?
N7 Pd1 2.028(5) . ?
N8 N9 1.287(6) . ?
N9 N10 1.381(6) . ?
Pd1 Pd1 2.6748(8) 3_666 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 119.3(7) . . ?
C6 C1 H1 120.3 . . ?
C2 C1 H1 120.3 . . ?
C3 C2 C1 120.0(9) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 119.8(8) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 122.3(9) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C6 C5 C4 116.1(8) . . ?
C6 C5 H5 122.0 . . ?
C4 C5 H5 122.0 . . ?
C1 C6 C5 122.5(6) . . ?
C1 C6 N1 120.0(6) . . ?
C5 C6 N1 117.4(7) . . ?
N6 C7 N4 126.3(5) 3_666 . ?
N6 C7 N1 128.2(5) 3_666 . ?
N4 C7 N1 105.5(5) . . ?
C9 C8 C13 120.1(5) . . ?
C9 C8 N5 117.9(5) . . ?
C13 C8 N5 121.9(6) . . ?
C8 C9 C10 120.4(6) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 119.4(7) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 120.9(7) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 120.3(7) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C8 C13 C12 118.8(7) . . ?
C8 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C19 C14 C15 119.2(6) . . ?
C19 C14 N6 121.8(6) . . ?
C15 C14 N6 119.0(6) . . ?
C16 C15 C14 119.1(7) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C17 C16 C15 121.2(8) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 120.4(8) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C19 119.4(8) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C14 C19 C18 120.5(7) . . ?
C14 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
N5 C20 N10 131.0(5) 3_666 . ?
N5 C20 N7 124.2(5) 3_666 . ?
N10 C20 N7 104.8(5) . . ?
C26 C21 C22 121.8(7) . . ?
C26 C21 N10 116.9(6) . . ?
C22 C21 N10 121.3(6) . . ?
C21 C22 C23 118.9(7) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
C22 C23 C24 120.9(9) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C25 C24 C23 118.4(9) . . ?
C25 C24 H24 120.8 . . ?
C23 C24 H24 120.8 . . ?
C24 C25 C26 122.3(9) . . ?
C24 C25 H25 118.8 . . ?
C26 C25 H25 118.8 . . ?
C21 C26 C25 117.6(7) . . ?
C21 C26 H26 121.2 . . ?
C25 C26 H26 121.2 . . ?
C7 N1 N2 108.9(5) . . ?
C7 N1 C6 130.1(5) . . ?
N2 N1 C6 119.3(5) . . ?
N3 N2 N1 106.7(5) . . ?
N2 N3 N4 110.5(4) . . ?
C7 N4 N3 108.4(4) . . ?
C7 N4 Pd1 126.1(4) . . ?
N3 N4 Pd1 125.5(3) . . ?
C20 N5 C8 123.8(5) 3_666 . ?
C20 N5 Pd1 117.5(4) 3_666 . ?
C8 N5 Pd1 117.3(4) . . ?
C7 N6 C14 119.5(5) 3_666 . ?
C7 N6 Pd1 115.5(3) 3_666 . ?
C14 N6 Pd1 118.7(4) . . ?
N8 N7 C20 108.3(5) . . ?
N8 N7 Pd1 124.7(4) . . ?
C20 N7 Pd1 126.8(4) . . ?
N9 N8 N7 110.6(5) . . ?
N8 N9 N10 106.7(5) . . ?
C20 N10 N9 109.7(5) . . ?
C20 N10 C21 133.7(5) . . ?
N9 N10 C21 116.6(5) . . ?
N5 Pd1 N4 89.50(19) . . ?
N5 Pd1 N6 89.67(19) . . ?
N4 Pd1 N6 172.03(18) . . ?
N5 Pd1 N7 171.41(18) . . ?
N4 Pd1 N7 90.13(19) . . ?
N6 Pd1 N7 89.51(19) . . ?
N5 Pd1 Pd1 90.44(13) . 3_666 ?
N4 Pd1 Pd1 81.16(13) . 3_666 ?
N6 Pd1 Pd1 90.91(13) . 3_666 ?
N7 Pd1 Pd1 81.02(12) . 3_666 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.1(12) . . . . ?
C1 C2 C3 C4 -0.2(14) . . . . ?
C2 C3 C4 C5 0.0(15) . . . . ?
C3 C4 C5 C6 0.6(14) . . . . ?
C2 C1 C6 C5 0.8(11) . . . . ?
C2 C1 C6 N1 -177.9(6) . . . . ?
C4 C5 C6 C1 -1.0(12) . . . . ?
C4 C5 C6 N1 177.7(7) . . . . ?
C13 C8 C9 C10 -0.6(10) . . . . ?
N5 C8 C9 C10 -176.6(6) . . . . ?
C8 C9 C10 C11 0.7(10) . . . . ?
C9 C10 C11 C12 -1.1(12) . . . . ?
C10 C11 C12 C13 1.4(12) . . . . ?
C9 C8 C13 C12 0.9(9) . . . . ?
N5 C8 C13 C12 176.8(5) . . . . ?
C11 C12 C13 C8 -1.3(10) . . . . ?
C19 C14 C15 C16 -0.5(10) . . . . ?
N6 C14 C15 C16 -179.3(6) . . . . ?
C14 C15 C16 C17 -0.8(12) . . . . ?
C15 C16 C17 C18 0.8(14) . . . . ?
C16 C17 C18 C19 0.5(14) . . . . ?
C15 C14 C19 C18 1.8(10) . . . . ?
N6 C14 C19 C18 -179.4(6) . . . . ?
C17 C18 C19 C14 -1.8(12) . . . . ?
C26 C21 C22 C23 -2.3(10) . . . . ?
N10 C21 C22 C23 178.0(6) . . . . ?
C21 C22 C23 C24 2.7(12) . . . . ?
C22 C23 C24 C25 -0.7(14) . . . . ?
C23 C24 C25 C26 -1.8(15) . . . . ?
C22 C21 C26 C25 -0.1(10) . . . . ?
N10 C21 C26 C25 179.6(6) . . . . ?
C24 C25 C26 C21 2.2(13) . . . . ?
N6 C7 N1 N2 -179.9(6) 3_666 . . . ?
N4 C7 N1 N2 -0.3(7) . . . . ?
N6 C7 N1 C6 -15.1(11) 3_666 . . . ?
N4 C7 N1 C6 164.4(6) . . . . ?
C1 C6 N1 C7 -50.4(10) . . . . ?
C5 C6 N1 C7 130.9(7) . . . . ?
C1 C6 N1 N2 113.0(7) . . . . ?
C5 C6 N1 N2 -65.7(8) . . . . ?
C7 N1 N2 N3 -0.6(7) . . . . ?
C6 N1 N2 N3 -167.3(6) . . . . ?
N1 N2 N3 N4 1.3(7) . . . . ?
N6 C7 N4 N3 -179.3(6) 3_666 . . . ?
N1 C7 N4 N3 1.1(7) . . . . ?
N6 C7 N4 Pd1 -0.3(9) 3_666 . . . ?
N1 C7 N4 Pd1 -179.9(4) . . . . ?
N2 N3 N4 C7 -1.6(7) . . . . ?
N2 N3 N4 Pd1 179.4(4) . . . . ?
C9 C8 N5 C20 -135.0(6) . . . 3_666 ?
C13 C8 N5 C20 49.1(8) . . . 3_666 ?
C9 C8 N5 Pd1 58.8(6) . . . . ?
C13 C8 N5 Pd1 -117.2(6) . . . . ?
C19 C14 N6 C7 46.5(8) . . . 3_666 ?
C15 C14 N6 C7 -134.7(6) . . . 3_666 ?
C19 C14 N6 Pd1 -104.4(6) . . . . ?
C15 C14 N6 Pd1 74.4(6) . . . . ?
N5 C20 N7 N8 176.8(5) 3_666 . . . ?
N10 C20 N7 N8 -1.1(6) . . . . ?
N5 C20 N7 Pd1 1.3(8) 3_666 . . . ?
N10 C20 N7 Pd1 -176.6(4) . . . . ?
C20 N7 N8 N9 1.5(7) . . . . ?
Pd1 N7 N8 N9 177.1(4) . . . . ?
N7 N8 N9 N10 -1.3(7) . . . . ?
N5 C20 N10 N9 -177.3(6) 3_666 . . . ?
N7 C20 N10 N9 0.4(6) . . . . ?
N5 C20 N10 C21 0.1(11) 3_666 . . . ?
N7 C20 N10 C21 177.7(6) . . . . ?
N8 N9 N10 C20 0.5(7) . . . . ?
N8 N9 N10 C21 -177.3(5) . . . . ?
C26 C21 N10 C20 131.4(7) . . . . ?
C22 C21 N10 C20 -48.9(10) . . . . ?
C26 C21 N10 N9 -51.4(8) . . . . ?
C22 C21 N10 N9 128.3(6) . . . . ?

_refine_diff_density_max         0.451
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.112



####################################################################### 
# 
# 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_1075
_database_code_depnum_ccdc_archive 'CCDC 1834322'
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 F N5 O'
_chemical_formula_sum            'C15 H10 F N5 O'
_chemical_formula_weight         295.28

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'
F F 0.0171 0.0103 '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                   6.7614(3)
_cell_length_b                   8.5686(4)
_cell_length_c                   11.9894(4)
_cell_angle_alpha                77.8244(14)
_cell_angle_beta                 77.638(2)
_cell_angle_gamma                85.281(2)
_cell_volume                     662.75(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2931
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      25.62

_exptl_crystal_description       REctangular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            9042
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.774
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_full        24.993
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             2276
_reflns_number_gt                1697
_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)+(0.0467P)²+0.1295P] 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         2276
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0873
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
C1 C 0.2112(2) 0.25318(19) 1.06634(13) 0.0352(4) Uani 1 1 d . . . . .
C2 C 0.1482(3) 0.2945(2) 1.17617(14) 0.0434(4) Uani 1 1 d . . . . .
H2 H 0.1093 0.2164 1.2425 0.052 Uiso 1 1 calc R U . . .
C3 C 0.1451(3) 0.4499(2) 1.18349(14) 0.0430(4) Uani 1 1 d . . . . .
C4 C 0.2015(2) 0.5713(2) 1.08738(14) 0.0402(4) Uani 1 1 d . . . . .
H4 H 0.1978 0.6770 1.0958 0.048 Uiso 1 1 calc R U . . .
C5 C 0.2625(2) 0.53215(19) 0.98018(14) 0.0377(4) Uani 1 1 d . . . . .
H5 H 0.3004 0.6125 0.9151 0.045 Uiso 1 1 calc R U . . .
C6 C 0.2692(2) 0.37328(19) 0.96626(13) 0.0325(4) Uani 1 1 d . . . . .
C7 C 0.3345(2) 0.19536(19) 0.85023(13) 0.0344(4) Uani 1 1 d . . . . .
C8 C 0.2167(2) 0.0865(2) 1.05785(14) 0.0409(4) Uani 1 1 d . . . . .
C9 C 0.4668(3) 0.1934(2) 0.63766(14) 0.0398(4) Uani 1 1 d . . . . .
C10 C 0.6421(3) 0.2764(2) 0.61589(15) 0.0496(5) Uani 1 1 d . . . . .
H10 H 0.7060 0.2812 0.6764 0.060 Uiso 1 1 calc R U . . .
C11 C 0.7211(3) 0.3520(2) 0.50397(17) 0.0593(5) Uani 1 1 d . . . . .
H11 H 0.8383 0.4092 0.4883 0.071 Uiso 1 1 calc R U . . .
C12 C 0.6260(3) 0.3426(2) 0.41546(17) 0.0621(6) Uani 1 1 d . . . . .
H12 H 0.6789 0.3936 0.3396 0.075 Uiso 1 1 calc R U . . .
C13 C 0.4527(3) 0.2581(3) 0.43854(16) 0.0606(6) Uani 1 1 d . . . . .
H13 H 0.3917 0.2518 0.3772 0.073 Uiso 1 1 calc R U . . .
C14 C 0.3654(3) 0.1815(2) 0.55093(15) 0.0467(5) Uani 1 1 d . . . . .
C15 C 0.1741(3) 0.0926(3) 0.5753(2) 0.0715(6) Uani 1 1 d . . . . .
H15A H 0.2061 -0.0201 0.5862 0.107 Uiso 1 1 calc R U . . .
H15B H 0.1068 0.1246 0.5107 0.107 Uiso 1 1 calc R U . . .
H15C H 0.0867 0.1164 0.6445 0.107 Uiso 1 1 calc R U . . .
F1 F 0.08444(17) 0.49172(14) 1.28929(9) 0.0649(4) Uani 1 1 d . . . . .
N1 N 0.3330(2) 0.34384(16) 0.85437(11) 0.0372(3) Uani 1 1 d . . . . .
N2 N 0.3868(2) 0.12122(16) 0.75685(11) 0.0410(4) Uani 1 1 d . . . . .
N3 N 0.3682(2) -0.03936(17) 0.79289(13) 0.0515(4) Uani 1 1 d . . . . .
N4 N 0.3048(2) -0.07290(17) 0.90295(13) 0.0512(4) Uani 1 1 d . . . . .
N5 N 0.2818(2) 0.06988(15) 0.94166(11) 0.0391(3) Uani 1 1 d . . . . .
O1 O 0.1750(2) -0.02976(15) 1.13563(10) 0.0606(4) 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
C1 C2 1.404(2) . ?
C1 C6 1.413(2) . ?
C1 C8 1.450(2) . ?
C2 C3 1.351(2) . ?
C2 H2 0.9300 . ?
C3 F1 1.3603(19) . ?
C3 C4 1.388(2) . ?
C4 C5 1.366(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.402(2) . ?
C5 H5 0.9300 . ?
C6 N1 1.3879(19) . ?
C7 N1 1.283(2) . ?
C7 N2 1.369(2) . ?
C7 N5 1.3723(19) . ?
C8 O1 1.2177(19) . ?
C8 N5 1.402(2) . ?
C9 C10 1.381(2) . ?
C9 C14 1.387(2) . ?
C9 N2 1.438(2) . ?
C10 C11 1.374(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.372(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.395(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.498(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
N2 N3 1.3601(19) . ?
N3 N4 1.275(2) . ?
N4 N5 1.3833(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.98(15) . . ?
C2 C1 C8 119.04(14) . . ?
C6 C1 C8 120.98(15) . . ?
C3 C2 C1 118.69(15) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 F1 119.36(15) . . ?
C2 C3 C4 123.09(16) . . ?
F1 C3 C4 117.56(16) . . ?
C5 C4 C3 118.58(16) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 121.33(15) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
N1 C6 C5 117.66(13) . . ?
N1 C6 C1 124.01(15) . . ?
C5 C6 C1 118.33(15) . . ?
N1 C7 N2 130.07(14) . . ?
N1 C7 N5 127.41(14) . . ?
N2 C7 N5 102.52(13) . . ?
O1 C8 N5 120.94(16) . . ?
O1 C8 C1 128.58(16) . . ?
N5 C8 C1 110.47(13) . . ?
C10 C9 C14 122.88(16) . . ?
C10 C9 N2 117.10(15) . . ?
C14 C9 N2 119.99(15) . . ?
C11 C10 C9 119.40(17) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 119.60(19) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.22(18) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 122.20(18) . . ?
C12 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C9 C14 C13 115.69(17) . . ?
C9 C14 C15 122.64(17) . . ?
C13 C14 C15 121.68(17) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7 N1 C6 113.21(13) . . ?
N3 N2 C7 110.18(13) . . ?
N3 N2 C9 122.27(14) . . ?
C7 N2 C9 127.37(14) . . ?
N4 N3 N2 109.77(14) . . ?
N3 N4 N5 106.94(13) . . ?
C7 N5 N4 110.59(13) . . ?
C7 N5 C8 123.91(14) . . ?
N4 N5 C8 125.49(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.2(2) . . . . ?
C8 C1 C2 C3 179.46(15) . . . . ?
C1 C2 C3 F1 180.00(14) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
F1 C3 C4 C5 -179.84(14) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C4 C5 C6 N1 180.00(14) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
C2 C1 C6 N1 -179.84(14) . . . . ?
C8 C1 C6 N1 0.5(2) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
C8 C1 C6 C5 -179.42(14) . . . . ?
C2 C1 C8 O1 -1.0(3) . . . . ?
C6 C1 C8 O1 178.67(17) . . . . ?
C2 C1 C8 N5 179.57(14) . . . . ?
C6 C1 C8 N5 -0.8(2) . . . . ?
C14 C9 C10 C11 0.4(3) . . . . ?
N2 C9 C10 C11 -177.90(16) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 C14 1.0(3) . . . . ?
C10 C9 C14 C13 0.5(3) . . . . ?
N2 C9 C14 C13 178.74(15) . . . . ?
C10 C9 C14 C15 -179.35(18) . . . . ?
N2 C9 C14 C15 -1.1(3) . . . . ?
C12 C13 C14 C9 -1.2(3) . . . . ?
C12 C13 C14 C15 178.68(19) . . . . ?
N2 C7 N1 C6 179.75(15) . . . . ?
N5 C7 N1 C6 -0.1(2) . . . . ?
C5 C6 N1 C7 179.91(14) . . . . ?
C1 C6 N1 C7 0.0(2) . . . . ?
N1 C7 N2 N3 179.18(16) . . . . ?
N5 C7 N2 N3 -0.94(17) . . . . ?
N1 C7 N2 C9 4.1(3) . . . . ?
N5 C7 N2 C9 -175.99(14) . . . . ?
C10 C9 N2 N3 -118.19(18) . . . . ?
C14 C9 N2 N3 63.5(2) . . . . ?
C10 C9 N2 C7 56.3(2) . . . . ?
C14 C9 N2 C7 -122.00(18) . . . . ?
C7 N2 N3 N4 0.92(19) . . . . ?
C9 N2 N3 N4 176.27(14) . . . . ?
N2 N3 N4 N5 -0.46(19) . . . . ?
N1 C7 N5 N4 -179.45(15) . . . . ?
N2 C7 N5 N4 0.66(16) . . . . ?
N1 C7 N5 C8 -0.3(3) . . . . ?
N2 C7 N5 C8 179.83(14) . . . . ?
N3 N4 N5 C7 -0.15(18) . . . . ?
N3 N4 N5 C8 -179.30(15) . . . . ?
O1 C8 N5 C7 -178.81(15) . . . . ?
C1 C8 N5 C7 0.7(2) . . . . ?
O1 C8 N5 N4 0.2(3) . . . . ?
C1 C8 N5 N4 179.74(14) . . . . ?

_refine_diff_density_max         0.127
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.036



