# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_2_a
_database_code_depnum_ccdc_archive 'CCDC 2068483'
loop_
_audit_author_name
_audit_author_address
'Kerem Kaya'
;Istanbul Technical University, Chemistry Department
Turkey
;
_audit_update_record             
;
2021-03-07 deposited with the CCDC.	2023-03-17 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            'C30 H22 Cl N5 O Pd'
_chemical_formula_weight         610.37

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'
Cl Cl 0.1484 0.1585 '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'
Pd Pd -0.9988 1.0072 '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                   8.6324(9)
_cell_length_b                   10.5581(12)
_cell_length_c                   16.7354(17)
_cell_angle_alpha                79.298(7)
_cell_angle_beta                 87.886(7)
_cell_angle_gamma                70.496(7)
_cell_volume                     1412.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    303(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      5
_cell_measurement_theta_max      26

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   0.878
_exptl_transmission_factor_max   0.955
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.783
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi_scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      303(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Sealed_Tube
_diffrn_measurement_device_type  Bruker_D8_VENTURE
_diffrn_measurement_method       omega_scans
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20957
_diffrn_reflns_av_unetI/netI     0.1878
_diffrn_reflns_av_R_equivalents  0.1756
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.218
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4965
_reflns_number_gt                2456
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1111P)²+0.9952P] 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         4965
_refine_ls_number_parameters     345
_refine_ls_number_restraints     417
_refine_ls_R_factor_all          0.1901
_refine_ls_R_factor_gt           0.0824
_refine_ls_wR_factor_ref         0.2409
_refine_ls_wR_factor_gt          0.2033
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.063
_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
Pd Pd 0.46565(11) 0.25801(9) 0.63809(5) 0.0444(4) Uani 1 1 d . . . . .
Cl Cl 0.4956(5) 0.1864(4) 0.7787(2) 0.0838(11) Uani 1 1 d . . . . .
N1 N 0.2721(10) 0.1879(8) 0.6348(6) 0.046(2) Uani 1 1 d . . . . .
N3 N 0.4876(10) 0.2617(8) 0.5231(5) 0.041(2) Uani 1 1 d . . . . .
N5 N 0.6313(11) 0.3593(9) 0.6349(5) 0.047(2) Uani 1 1 d . . . . .
N4 N 0.7056(10) 0.3575(9) 0.4938(5) 0.046(2) Uani 1 1 d . . . . .
N2 N 0.3097(11) 0.1387(9) 0.5006(5) 0.048(2) Uani 1 1 d . . . . .
O1 O 0.7575(12) 0.2267(10) 0.1935(5) 0.085(3) Uani 1 1 d . . . . .
C15 C 0.4933(13) 0.1943(11) 0.3987(6) 0.0454(16) Uani 1 1 d . U . . .
C8 C 0.7143(13) 0.3915(11) 0.5693(7) 0.047(2) Uani 1 1 d . U . . .
C14 C 0.6023(13) 0.3036(11) 0.4749(6) 0.0434(19) Uani 1 1 d . U . . .
C13 C 0.4182(13) 0.1963(11) 0.4804(6) 0.043(2) Uani 1 1 d . U . . .
C18 C 0.4681(13) 0.1385(11) 0.3330(6) 0.0480(18) Uani 1 1 d . U . . .
H18 H 0.3927 0.0924 0.3349 0.058 Uiso 1 1 calc R U . . .
C16 C 0.6029(13) 0.2643(11) 0.3951(6) 0.0450(16) Uani 1 1 d . U . . .
C10 C 0.8182(13) 0.4683(11) 0.5737(7) 0.0482(19) Uani 1 1 d . U . . .
H10 H 0.8732 0.4905 0.5272 0.058 Uiso 1 1 calc R U . . .
C6 C 0.2331(13) 0.1389(11) 0.5719(7) 0.048(2) Uani 1 1 d . U . . .
C1 C 0.1746(14) 0.1907(12) 0.7008(8) 0.061(2) Uani 1 1 d . U . . .
H1 H 0.1937 0.2316 0.7424 0.073 Uiso 1 1 calc R U . . .
C5 C 0.1085(13) 0.0828(11) 0.5797(7) 0.053(2) Uani 1 1 d . U . . .
H5 H 0.0857 0.0478 0.5362 0.063 Uiso 1 1 calc R U . . .
C17 C 0.6947(13) 0.2826(11) 0.3272(6) 0.0479(17) Uani 1 1 d . U . . .
H17 H 0.7683 0.3305 0.3245 0.058 Uiso 1 1 calc R U . . .
C19 C 0.5594(14) 0.1548(11) 0.2657(7) 0.0511(18) Uani 1 1 d . U . . .
H19 H 0.5467 0.1182 0.2209 0.061 Uiso 1 1 calc R U . . .
C20 C 0.6686(14) 0.2237(12) 0.2629(7) 0.0505(18) Uani 1 1 d . U . . .
C2 C 0.0514(14) 0.1371(12) 0.7093(7) 0.060(2) Uani 1 1 d . U . . .
H2 H -0.0108 0.1407 0.7559 0.072 Uiso 1 1 calc R U . . .
C7 C 0.6561(14) 0.4025(12) 0.7025(7) 0.054(2) Uani 1 1 d . U . . .
H7 H 0.6025 0.3799 0.7495 0.064 Uiso 1 1 calc R U . . .
C3 C 0.0179(14) 0.0761(12) 0.6470(8) 0.0577(19) Uani 1 1 d . U . . .
C11 C 0.8421(14) 0.5108(11) 0.6405(7) 0.0503(18) Uani 1 1 d . U . . .
C4 C -0.1125(14) 0.0100(13) 0.6551(8) 0.065(3) Uani 1 1 d . U . . .
H4A H -0.1767 0.0371 0.6054 0.097 Uiso 1 1 calc R U . . .
H4B H -0.1825 0.0382 0.6990 0.097 Uiso 1 1 calc R U . . .
H4C H -0.0617 -0.0876 0.6661 0.097 Uiso 1 1 calc R U . . .
C9 C 0.7560(14) 0.4778(12) 0.7055(7) 0.054(2) Uani 1 1 d . U . . .
H9 H 0.7654 0.5074 0.7535 0.064 Uiso 1 1 calc R U . . .
C21 C 0.8380(18) 0.3201(16) 0.1713(7) 0.074(2) Uani 1 1 d . U . . .
C12 C 0.9608(14) 0.5852(12) 0.6449(7) 0.062(3) Uani 1 1 d . U . . .
H12A H 1.0671 0.5204 0.6624 0.093 Uiso 1 1 calc R U . . .
H12B H 0.9233 0.6459 0.6831 0.093 Uiso 1 1 calc R U . . .
H12C H 0.9683 0.6369 0.5922 0.093 Uiso 1 1 calc R U . . .
C22 C 0.9997(17) 0.2736(16) 0.1556(7) 0.077(2) Uani 1 1 d . U . . .
H22 H 1.0578 0.1803 0.1657 0.092 Uiso 1 1 calc R U . . .
C24 C 1.0795(18) 0.3683(17) 0.1238(8) 0.081(2) Uani 1 1 d . U . . .
C23 C 0.7519(18) 0.4591(15) 0.1595(7) 0.079(2) Uani 1 1 d . U . . .
H23 H 0.6415 0.4897 0.1724 0.095 Uiso 1 1 calc R U . . .
C25 C 0.8273(19) 0.5504(16) 0.1293(8) 0.083(2) Uani 1 1 d . U . . .
H25 H 0.7677 0.6434 0.1207 0.100 Uiso 1 1 calc R U . . .
C26 C 0.9920(19) 0.5074(17) 0.1109(8) 0.085(2) Uani 1 1 d . U . . .
C28 C 1.325(2) 0.4241(18) 0.0756(9) 0.095(3) Uani 1 1 d . U . . .
H28 H 1.4353 0.3964 0.0627 0.114 Uiso 1 1 calc R U . . .
C30 C 1.232(2) 0.5548(18) 0.0644(9) 0.097(3) Uani 1 1 d . U . . .
H30 H 1.2835 0.6179 0.0434 0.116 Uiso 1 1 calc R U . . .
C29 C 1.075(2) 0.6044(18) 0.0800(8) 0.094(2) Uani 1 1 d . U . . .
H29 H 1.0197 0.6981 0.0714 0.112 Uiso 1 1 calc R U . . .
C27 C 1.2472(19) 0.3318(18) 0.1075(8) 0.090(2) Uani 1 1 d . U . . .
H27 H 1.3102 0.2396 0.1189 0.108 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd N3 1.921(8) . ?
Pd N5 2.046(8) . ?
Pd N1 2.047(8) . ?
Pd Cl 2.330(3) . ?
N1 C6 1.354(13) . ?
N1 C1 1.363(13) . ?
N3 C13 1.355(12) . ?
N3 C14 1.388(12) . ?
N5 C8 1.342(12) . ?
N5 C7 1.346(13) . ?
N4 C14 1.283(12) . ?
N4 C8 1.387(13) . ?
N2 C13 1.282(12) . ?
N2 C6 1.344(13) . ?
O1 C20 1.370(12) . ?
O1 C21 1.377(15) . ?
C15 C16 1.375(13) . ?
C15 C18 1.395(14) . ?
C15 C13 1.492(14) . ?
C8 C10 1.408(13) . ?
C14 C16 1.470(14) . ?
C18 C19 1.369(13) . ?
C18 H18 0.9300 . ?
C16 C17 1.382(13) . ?
C10 C11 1.326(14) . ?
C10 H10 0.9300 . ?
C6 C5 1.382(14) . ?
C1 C2 1.353(14) . ?
C1 H1 0.9300 . ?
C5 C3 1.353(14) . ?
C5 H5 0.9300 . ?
C17 C20 1.398(14) . ?
C17 H17 0.9300 . ?
C19 C20 1.365(14) . ?
C19 H19 0.9300 . ?
C2 C3 1.407(16) . ?
C2 H2 0.9300 . ?
C7 C9 1.362(14) . ?
C7 H7 0.9300 . ?
C3 C4 1.500(14) . ?
C11 C9 1.353(14) . ?
C11 C12 1.495(14) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C9 H9 0.9300 . ?
C21 C22 1.350(17) . ?
C21 C23 1.386(19) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C22 C24 1.412(18) . ?
C22 H22 0.9300 . ?
C24 C26 1.39(2) . ?
C24 C27 1.398(18) . ?
C23 C25 1.350(17) . ?
C23 H23 0.9300 . ?
C25 C26 1.382(18) . ?
C25 H25 0.9300 . ?
C26 C29 1.449(19) . ?
C28 C30 1.32(2) . ?
C28 C27 1.378(18) . ?
C28 H28 0.9300 . ?
C30 C29 1.315(19) . ?
C30 H30 0.9300 . ?
C29 H29 0.9300 . ?
C27 H27 0.9300 . ?

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
N3 Pd N5 89.8(3) . . ?
N3 Pd N1 88.9(3) . . ?
N5 Pd N1 170.6(3) . . ?
N3 Pd Cl 162.4(3) . . ?
N5 Pd Cl 92.8(3) . . ?
N1 Pd Cl 91.3(3) . . ?
C6 N1 C1 117.2(9) . . ?
C6 N1 Pd 125.0(7) . . ?
C1 N1 Pd 117.8(8) . . ?
C13 N3 C14 108.7(8) . . ?
C13 N3 Pd 124.2(7) . . ?
C14 N3 Pd 125.7(7) . . ?
C8 N5 C7 116.3(9) . . ?
C8 N5 Pd 125.3(7) . . ?
C7 N5 Pd 118.4(7) . . ?
C14 N4 C8 123.7(9) . . ?
C13 N2 C6 124.4(9) . . ?
C20 O1 C21 122.1(9) . . ?
C16 C15 C18 121.3(10) . . ?
C16 C15 C13 106.9(9) . . ?
C18 C15 C13 131.8(9) . . ?
N5 C8 N4 125.4(9) . . ?
N5 C8 C10 119.8(10) . . ?
N4 C8 C10 114.7(9) . . ?
N4 C14 N3 129.2(10) . . ?
N4 C14 C16 121.4(9) . . ?
N3 C14 C16 109.1(8) . . ?
N2 C13 N3 130.6(10) . . ?
N2 C13 C15 120.6(9) . . ?
N3 C13 C15 108.7(9) . . ?
C19 C18 C15 116.9(9) . . ?
C19 C18 H18 121.6 . . ?
C15 C18 H18 121.6 . . ?
C15 C16 C17 122.4(10) . . ?
C15 C16 C14 106.5(9) . . ?
C17 C16 C14 131.0(9) . . ?
C11 C10 C8 123.6(10) . . ?
C11 C10 H10 118.2 . . ?
C8 C10 H10 118.2 . . ?
N2 C6 N1 124.3(9) . . ?
N2 C6 C5 116.0(10) . . ?
N1 C6 C5 119.7(10) . . ?
C2 C1 N1 123.6(12) . . ?
C2 C1 H1 118.2 . . ?
N1 C1 H1 118.2 . . ?
C3 C5 C6 123.6(11) . . ?
C3 C5 H5 118.2 . . ?
C6 C5 H5 118.2 . . ?
C16 C17 C20 115.0(9) . . ?
C16 C17 H17 122.5 . . ?
C20 C17 H17 122.5 . . ?
C20 C19 C18 121.4(10) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C19 C20 O1 115.3(10) . . ?
C19 C20 C17 123.1(10) . . ?
O1 C20 C17 121.6(9) . . ?
C1 C2 C3 119.6(11) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
N5 C7 C9 123.1(10) . . ?
N5 C7 H7 118.5 . . ?
C9 C7 H7 118.5 . . ?
C5 C3 C2 115.8(10) . . ?
C5 C3 C4 122.6(11) . . ?
C2 C3 C4 121.6(10) . . ?
C10 C11 C9 115.3(10) . . ?
C10 C11 C12 122.5(10) . . ?
C9 C11 C12 122.1(10) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C11 C9 C7 121.8(11) . . ?
C11 C9 H9 119.1 . . ?
C7 C9 H9 119.1 . . ?
C22 C21 O1 118.6(14) . . ?
C22 C21 C23 120.7(14) . . ?
O1 C21 C23 120.5(13) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C21 C22 C24 119.2(15) . . ?
C21 C22 H22 120.4 . . ?
C24 C22 H22 120.4 . . ?
C26 C24 C27 116.2(14) . . ?
C26 C24 C22 119.7(14) . . ?
C27 C24 C22 124.0(16) . . ?
C25 C23 C21 120.4(15) . . ?
C25 C23 H23 119.8 . . ?
C21 C23 H23 119.8 . . ?
C23 C25 C26 120.8(16) . . ?
C23 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C25 C26 C24 119.1(14) . . ?
C25 C26 C29 121.3(16) . . ?
C24 C26 C29 119.6(15) . . ?
C30 C28 C27 115.9(16) . . ?
C30 C28 H28 122.0 . . ?
C27 C28 H28 122.0 . . ?
C29 C30 C28 126.8(17) . . ?
C29 C30 H30 116.6 . . ?
C28 C30 H30 116.6 . . ?
C30 C29 C26 117.4(17) . . ?
C30 C29 H29 121.3 . . ?
C26 C29 H29 121.3 . . ?
C28 C27 C24 124.0(17) . . ?
C28 C27 H27 118.0 . . ?
C24 C27 H27 118.0 . . ?

_refine_diff_density_max         1.101
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.155

####################################################################### 
# 
# 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_bpi_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2068484'
loop_
_audit_author_name
_audit_author_address
'Kerem Kaya'
;Istanbul Technical University, Chemistry Department
Turkey
;
_audit_update_record             
;
2021-03-07 deposited with the CCDC.	2023-03-17 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H23 N5 O'
_chemical_formula_weight         469.53
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.3202(3)
_cell_length_b                   10.3082(5)
_cell_length_c                   19.4392(9)
_cell_angle_alpha                82.097(2)
_cell_angle_beta                 83.015(2)
_cell_angle_gamma                79.848(2)
_cell_volume                     1228.62(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    24
_cell_measurement_temperature    306(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      5
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   Multi_scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.030
_exptl_transmission_factor_max   0.987
_exptl_transmission_factor_min   0.921
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            51037
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.393
_diffrn_ambient_temperature      306(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  Bruker_D8_VENTURE
_diffrn_measurement_method       omega_and_phi_scans
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   Sealed_Tube
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3101
_reflns_number_total             4334
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    ?
_computing_publication_material  ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    ?
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0638P)²+0.2147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1275
_refine_special_details          ?
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8848(2) 0.28063(15) 0.84520(7) 0.0771(4) Uani 1 1 d . . . . .
N1 N -0.3328(2) 0.72698(15) 0.80825(9) 0.0622(4) Uani 1 1 d . . . . .
N2 N -0.0700(2) 0.64169(15) 0.88903(8) 0.0586(4) Uani 1 1 d . . . . .
N3 N 0.0570(2) 0.60144(14) 0.77105(7) 0.0516(4) Uani 1 1 d . . . . .
H13 H -0.0537 0.6424 0.7508 0.062 Uiso 1 1 calc R U . . .
N4 N 0.2883(2) 0.53041(14) 0.67041(7) 0.0499(4) Uani 1 1 d . . . . .
N5 N -0.0695(2) 0.62169(17) 0.64330(8) 0.0646(4) Uani 1 1 d . . . . .
C1 C -0.5260(3) 0.7992(2) 0.79724(13) 0.0727(6) Uani 1 1 d . . . . .
H1 H -0.5724 0.8053 0.7531 0.087 Uiso 1 1 calc R U . . .
C2 C -0.6582(3) 0.8640(2) 0.84623(15) 0.0864(7) Uani 1 1 d . . . . .
H2 H -0.7908 0.9130 0.8355 0.104 Uiso 1 1 calc R U . . .
C3 C -0.5945(4) 0.8566(2) 0.91172(15) 0.0945(8) Uani 1 1 d . . . . .
C4 C -0.7371(6) 0.9262(4) 0.96908(18) 0.1682(18) Uani 1 1 d . . . . .
H3 H -0.8715 0.8927 0.9780 0.252 Uiso 1 1 calc R U . . .
H4 H -0.7647 1.0200 0.9545 0.252 Uiso 1 1 calc R U . . .
H5 H -0.6652 0.9099 1.0109 0.252 Uiso 1 1 calc R U . . .
C5 C -0.3942(3) 0.7829(2) 0.92431(12) 0.0810(7) Uani 1 1 d . . . . .
H6 H -0.3444 0.7767 0.9679 0.097 Uiso 1 1 calc R U . . .
C6 C -0.2687(3) 0.71850(18) 0.87179(11) 0.0589(5) Uani 1 1 d . . . . .
C7 C -0.2002(3) 0.6728(2) 0.59354(12) 0.0763(6) Uani 1 1 d . . . . .
H7 H -0.3467 0.6960 0.6072 0.092 Uiso 1 1 calc R U . . .
C8 C 0.1409(3) 0.58698(16) 0.62214(9) 0.0496(4) Uani 1 1 d . . . . .
C9 C -0.1319(3) 0.6931(2) 0.52438(12) 0.0728(6) Uani 1 1 d . . . . .
H8 H -0.2303 0.7300 0.4924 0.087 Uiso 1 1 calc R U . . .
C10 C 0.2205(3) 0.60335(17) 0.55246(9) 0.0538(4) Uani 1 1 d . . . . .
H12 H 0.3669 0.5770 0.5397 0.065 Uiso 1 1 calc R U . . .
C11 C 0.0849(3) 0.65842(18) 0.50183(10) 0.0604(5) Uani 1 1 d . . . . .
C12 C 0.1656(4) 0.6785(2) 0.42607(11) 0.0862(7) Uani 1 1 d . . . . .
H9 H 0.1536 0.7719 0.4106 0.129 Uiso 1 1 calc R U . . .
H10 H 0.0808 0.6392 0.3995 0.129 Uiso 1 1 calc R U . . .
H11 H 0.3141 0.6375 0.4196 0.129 Uiso 1 1 calc R U . . .
C13 C 0.0685(3) 0.59147(16) 0.84204(9) 0.0498(4) Uani 1 1 d . . . . .
C14 C 0.2410(3) 0.53902(16) 0.73599(9) 0.0461(4) Uani 1 1 d . . . . .
C15 C 0.2809(3) 0.51137(17) 0.85412(9) 0.0503(4) Uani 1 1 d . . . . .
C16 C 0.3848(3) 0.48037(16) 0.79027(9) 0.0465(4) Uani 1 1 d . . . . .
C17 C 0.5883(3) 0.40433(17) 0.78400(9) 0.0530(4) Uani 1 1 d . . . . .
H14 H 0.6580 0.3853 0.7407 0.064 Uiso 1 1 calc R U . . .
C18 C 0.3793(3) 0.4676(2) 0.91435(10) 0.0652(5) Uani 1 1 d . . . . .
H15 H 0.3113 0.4891 0.9574 0.078 Uiso 1 1 calc R U . . .
C19 C 0.5816(3) 0.3911(2) 0.90905(10) 0.0684(6) Uani 1 1 d . . . . .
H16 H 0.6514 0.3611 0.9491 0.082 Uiso 1 1 calc R U . . .
C20 C 0.6824(3) 0.35827(19) 0.84475(10) 0.0596(5) Uani 1 1 d . . . . .
C21 C 0.9434(3) 0.19655(18) 0.79347(10) 0.0564(5) Uani 1 1 d . . . . .
C22 C 0.8128(3) 0.1031(2) 0.78650(12) 0.0722(6) Uani 1 1 d . . . . .
H17 H 0.6853 0.0988 0.8155 0.087 Uiso 1 1 calc R U . . .
C23 C 0.8741(3) 0.0192(2) 0.73709(13) 0.0755(6) Uani 1 1 d . . . . .
H19 H 0.7871 -0.0426 0.7327 0.091 Uiso 1 1 calc R U . . .
C24 C 1.0646(3) 0.02334(17) 0.69270(11) 0.0619(5) Uani 1 1 d . . . . .
C25 C 1.1972(3) 0.11583(17) 0.70111(9) 0.0533(4) Uani 1 1 d . . . . .
C26 C 1.1301(3) 0.20223(17) 0.75311(10) 0.0540(5) Uani 1 1 d . . . . .
H18 H 1.2162 0.2633 0.7593 0.065 Uiso 1 1 calc R U . . .
C27 C 1.3892(3) 0.1190(2) 0.65692(11) 0.0743(6) Uani 1 1 d . . . . .
H23 H 1.4786 0.1789 0.6621 0.089 Uiso 1 1 calc R U . . .
C28 C 1.4477(4) 0.0364(3) 0.60668(13) 0.0961(8) Uani 1 1 d . . . . .
H22 H 1.5766 0.0400 0.5783 0.115 Uiso 1 1 calc R U . . .
C29 C 1.3174(5) -0.0528(3) 0.59748(15) 0.1025(9) Uani 1 1 d . . . . .
H21 H 1.3585 -0.1084 0.5627 0.123 Uiso 1 1 calc R U . . .
C30 C 1.1306(5) -0.0599(2) 0.63857(14) 0.0877(7) Uani 1 1 d . . . . .
H20 H 1.0438 -0.1200 0.6315 0.105 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C20 1.384(2) . ?
O1 C21 1.391(2) . ?
N1 C1 1.338(2) . ?
N1 C6 1.333(2) . ?
N2 C6 1.413(2) . ?
N2 C13 1.282(2) . ?
N3 H13 0.8600 . ?
N3 C13 1.379(2) . ?
N3 C14 1.377(2) . ?
N4 C8 1.400(2) . ?
N4 C14 1.285(2) . ?
N5 C7 1.340(2) . ?
N5 C8 1.343(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.355(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(4) . ?
C3 C4 1.523(3) . ?
C4 H3 0.9600 . ?
C4 H4 0.9600 . ?
C4 H5 0.9600 . ?
C5 C3 1.387(3) . ?
C5 H6 0.9300 . ?
C6 C5 1.384(3) . ?
C7 H7 0.9300 . ?
C8 C10 1.385(2) . ?
C9 C7 1.360(3) . ?
C9 H8 0.9300 . ?
C10 H12 0.9300 . ?
C10 C11 1.381(2) . ?
C11 C9 1.386(3) . ?
C11 C12 1.498(3) . ?
C12 H9 0.9600 . ?
C12 H10 0.9600 . ?
C12 H11 0.9600 . ?
C13 C15 1.474(2) . ?
C15 C18 1.376(2) . ?
C16 C14 1.473(2) . ?
C16 C15 1.382(2) . ?
C16 C17 1.384(2) . ?
C17 H14 0.9300 . ?
C17 C20 1.375(2) . ?
C18 H15 0.9300 . ?
C18 C19 1.379(3) . ?
C19 H16 0.9300 . ?
C20 C19 1.389(3) . ?
C21 C22 1.404(3) . ?
C22 H17 0.9300 . ?
C23 C22 1.357(3) . ?
C23 H19 0.9300 . ?
C24 C23 1.397(3) . ?
C24 C30 1.426(3) . ?
C25 C24 1.413(3) . ?
C25 C26 1.416(2) . ?
C25 C27 1.402(3) . ?
C26 C21 1.341(3) . ?
C26 H18 0.9300 . ?
C27 H23 0.9300 . ?
C27 C28 1.358(3) . ?
C28 H22 0.9300 . ?
C29 C28 1.380(4) . ?
C29 H21 0.9300 . ?
C30 C29 1.350(4) . ?
C30 H20 0.9300 . ?

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
C20 O1 C21 116.68(14) . . ?
C6 N1 C1 117.25(18) . . ?
C13 N2 C6 121.19(16) . . ?
C13 N3 H13 123.5 . . ?
C14 N3 H13 123.5 . . ?
C14 N3 C13 113.01(14) . . ?
C14 N4 C8 121.14(14) . . ?
C7 N5 C8 116.76(17) . . ?
N1 C1 H1 117.9 . . ?
N1 C1 C2 124.2(2) . . ?
C2 C1 H1 117.9 . . ?
C1 C2 H2 120.4 . . ?
C1 C2 C3 119.3(2) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 121.6(2) . . ?
C2 C3 C5 117.6(2) . . ?
C5 C3 C4 120.8(3) . . ?
C3 C4 H3 109.5 . . ?
C3 C4 H4 109.5 . . ?
C3 C4 H5 109.5 . . ?
H4 C4 H3 109.5 . . ?
H4 C4 H5 109.5 . . ?
H5 C4 H3 109.5 . . ?
C3 C5 H6 120.1 . . ?
C6 C5 C3 119.8(2) . . ?
C6 C5 H6 120.1 . . ?
N1 C6 N2 121.45(16) . . ?
N1 C6 C5 121.83(18) . . ?
C5 C6 N2 116.71(19) . . ?
N5 C7 H7 117.9 . . ?
N5 C7 C9 124.13(19) . . ?
C9 C7 H7 117.9 . . ?
N5 C8 N4 120.63(16) . . ?
N5 C8 C10 122.04(16) . . ?
C10 C8 N4 117.32(15) . . ?
C7 C9 H8 120.1 . . ?
C7 C9 C11 119.74(18) . . ?
C11 C9 H8 120.1 . . ?
C8 C10 H12 119.7 . . ?
C11 C10 C8 120.64(17) . . ?
C11 C10 H12 119.7 . . ?
C9 C11 C12 121.21(19) . . ?
C10 C11 C9 116.67(18) . . ?
C10 C11 C12 122.12(19) . . ?
C11 C12 H9 109.5 . . ?
C11 C12 H10 109.5 . . ?
C11 C12 H11 109.5 . . ?
H9 C12 H10 109.5 . . ?
H11 C12 H9 109.5 . . ?
H11 C12 H10 109.5 . . ?
N2 C13 N3 128.97(16) . . ?
N2 C13 C15 125.64(16) . . ?
N3 C13 C15 105.38(14) . . ?
N3 C14 C16 105.37(14) . . ?
N4 C14 N3 130.03(15) . . ?
N4 C14 C16 124.60(14) . . ?
C16 C15 C13 108.00(15) . . ?
C18 C15 C13 131.59(16) . . ?
C18 C15 C16 120.42(16) . . ?
C15 C16 C14 108.22(14) . . ?
C15 C16 C17 122.15(16) . . ?
C17 C16 C14 129.62(15) . . ?
C16 C17 H14 121.6 . . ?
C20 C17 C16 116.88(16) . . ?
C20 C17 H14 121.6 . . ?
C15 C18 H15 120.9 . . ?
C15 C18 C19 118.15(17) . . ?
C19 C18 H15 120.9 . . ?
C18 C19 H16 119.5 . . ?
C18 C19 C20 120.91(17) . . ?
C20 C19 H16 119.5 . . ?
O1 C20 C19 116.32(16) . . ?
C17 C20 O1 122.19(16) . . ?
C17 C20 C19 121.45(16) . . ?
O1 C21 C22 119.87(18) . . ?
C26 C21 O1 119.00(17) . . ?
C26 C21 C22 121.06(18) . . ?
C21 C22 H17 120.3 . . ?
C23 C22 C21 119.48(19) . . ?
C23 C22 H17 120.3 . . ?
C22 C23 H19 119.2 . . ?
C22 C23 C24 121.58(19) . . ?
C24 C23 H19 119.2 . . ?
C23 C24 C25 118.50(19) . . ?
C23 C24 C30 123.2(2) . . ?
C25 C24 C30 118.3(2) . . ?
C24 C25 C26 118.89(17) . . ?
C27 C25 C24 118.39(18) . . ?
C27 C25 C26 122.72(18) . . ?
C21 C26 C25 120.46(17) . . ?
C21 C26 H18 119.8 . . ?
C25 C26 H18 119.8 . . ?
C25 C27 H23 119.3 . . ?
C28 C27 C25 121.4(2) . . ?
C28 C27 H23 119.3 . . ?
C27 C28 H22 119.8 . . ?
C27 C28 C29 120.5(3) . . ?
C29 C28 H22 119.8 . . ?
C28 C29 H21 119.7 . . ?
C30 C29 C28 120.5(2) . . ?
C30 C29 H21 119.7 . . ?
C24 C30 H20 119.6 . . ?
C29 C30 C24 120.9(2) . . ?
C29 C30 H20 119.6 . . ?

