# 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_8
_database_code_depnum_ccdc_archive 'CCDC 2225115'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2022-12-08 deposited with the CCDC.	2023-01-16 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
A small amount of electron density remains around the dichloromethane solvent
molecule.

C-H hydrogen atoms were  visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. N-H hydrogen 
atoms were visible in the Fourier difference map and were refined
with restraints on bond lengths and angles. 

Otherwise, it was not necessary to use any crystallographic restraints
in the final refinement.
;

_cell_length_a                   20.1781(4)
_cell_length_b                   22.0626(4)
_cell_length_c                   19.6871(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.6762(19)
_cell_angle_gamma                90
_cell_volume                     8252.58(14)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c '
_symmetry_space_group_name_Hall  '-C 2yc'

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            8

_chemical_formula_sum            'C40 H43 Cl2 N9 O7 S'
_chemical_formula_moiety         'C37 H35 N9 O6, C2 H6 O S, C H2 Cl2'
_chemical_compound_source        synthesized
_chemical_formula_weight         864.79

_cell_measurement_temperature    150
_cell_measurement_reflns_used    10419
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      73.4

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.07
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_max          0.17

_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             3616
_exptl_absorpt_coefficient_mu    2.400

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            33265
_reflns_number_total             8309
_diffrn_reflns_av_R_equivalents  0.034

_diffrn_reflns_theta_min         3.069
_diffrn_reflns_theta_max         73.745
_diffrn_measured_fraction_theta_max 0.994

_diffrn_reflns_theta_full        72.270
_diffrn_measured_fraction_theta_full 0.998

_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       20
_reflns_limit_h_min              -25
_reflns_limit_h_max              23
_reflns_limit_k_min              0
_reflns_limit_k_max              27
_reflns_limit_l_min              0
_reflns_limit_l_max              24

_oxford_diffrn_Wilson_B_factor   2.24
_oxford_diffrn_Wilson_scale      1.08

_atom_sites_solution_primary     Other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -1.52
_refine_diff_density_max         1.26

# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         7732
_refine_ls_number_restraints     6
_refine_ls_number_parameters     538
_oxford_refine_ls_R_factor_ref   0.0754
_refine_ls_wR_factor_ref         0.1970
_refine_ls_goodness_of_fit_ref   0.9996
_refine_ls_shift/su_max          0.0006900
_refine_ls_shift/su_mean         0.0000357

# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        7732
_refine_ls_R_factor_all          0.0754
_refine_ls_wR_factor_all         0.1970

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6625
_refine_ls_R_factor_gt           0.0671
_refine_ls_wR_factor_gt          0.1880

_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.257E+04 0.433E+04 0.266E+04 0.110E+04 241. 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.61437(13) 0.23700(11) 0.29002(12) 0.0224 1.0000 Uani . . . . . .
C2 C 0.64160(16) 0.28878(13) 0.27461(15) 0.0234 1.0000 Uani . . . . . .
C3 C 0.69490(16) 0.29013(14) 0.24429(15) 0.0259 1.0000 Uani . . . . . .
C4 C 0.72057(16) 0.23593(15) 0.22863(16) 0.0276 1.0000 Uani . . . . . .
C5 C 0.69335(15) 0.18211(14) 0.24426(15) 0.0268 1.0000 Uani . . . . . .
C6 C 0.64007(15) 0.18470(13) 0.27487(14) 0.0232 1.0000 Uani . . . . . .
C7 C 0.60989(15) 0.12921(13) 0.29303(14) 0.0220 1.0000 Uani . . . . . .
C8 C 0.56214(15) 0.12246(13) 0.32845(14) 0.0220 1.0000 Uani . . . . . .
N9 N 0.62831(14) 0.07302(11) 0.27682(14) 0.0278 1.0000 Uani . . . . . .
N10 N 0.59438(14) 0.03223(11) 0.30050(13) 0.0275 1.0000 Uani . . . . . .
N11 N 0.55380(12) 0.06204(11) 0.33194(11) 0.0209 1.0000 Uani . . . . . .
C12 C 0.51392(15) 0.02708(13) 0.36799(15) 0.0241 1.0000 Uani . . . . . .
C13 C 0.55761(15) 0.01599(12) 0.44586(14) 0.0228 1.0000 Uani . . . . . .
O14 O 0.55790(11) 0.07153(9) 0.48352(10) 0.0256 1.0000 Uani . . . . . .
C15 C 0.59535(14) 0.07216(13) 0.55631(14) 0.0203 1.0000 Uani . . . . . .
C16 C 0.63743(15) 0.02468(12) 0.59326(15) 0.0235 1.0000 Uani . . . . . .
C17 C 0.67279(15) 0.02939(13) 0.66713(15) 0.0237 1.0000 Uani . . . . . .
C18 C 0.66594(14) 0.08106(12) 0.70427(14) 0.0191 1.0000 Uani . . . . . .
C19 C 0.62508(15) 0.12888(13) 0.66643(15) 0.0247 1.0000 Uani . . . . . .
C20 C 0.58975(16) 0.12445(13) 0.59308(15) 0.0250 1.0000 Uani . . . . . .
O21 O 0.69629(10) 0.08915(8) 0.77731(10) 0.0210 1.0000 Uani . . . . . .
C22 C 0.74581(14) 0.04456(12) 0.81726(14) 0.0203 1.0000 Uani . . . . . .
C23 C 0.75999(14) 0.05918(12) 0.89619(14) 0.0195 1.0000 Uani D . . . . .
N24 N 0.78830(12) 0.12025(10) 0.91385(12) 0.0180 1.0000 Uani D . . . . .
O25 O 0.90216(11) 0.09020(9) 0.95162(12) 0.0265 1.0000 Uani . . . . . .
C26 C 0.85809(14) 0.13071(12) 0.93825(13) 0.0180 1.0000 Uani D . . . . .
C27 C 0.87889(14) 0.19658(12) 0.94689(13) 0.0181 1.0000 Uani . . . . . .
C28 C 0.83339(14) 0.24204(12) 0.95195(13) 0.0176 1.0000 Uani . . . . . .
C29 C 0.85269(15) 0.30282(12) 0.95372(14) 0.0203 1.0000 Uani . . . . . .
C30 C 0.91949(15) 0.31778(13) 0.95255(14) 0.0239 1.0000 Uani . . . . . .
C31 C 0.96588(15) 0.27225(14) 0.94956(16) 0.0260 1.0000 Uani . . . . . .
C32 C 0.94610(15) 0.21184(13) 0.94674(15) 0.0222 1.0000 Uani . . . . . .
O33 O 0.82458(12) 0.40337(9) 0.97850(12) 0.0301 1.0000 Uani . . . . . .
C34 C 0.80283(15) 0.35304(12) 0.95337(14) 0.0210 1.0000 Uani D . . . . .
N35 N 0.73366(13) 0.34033(10) 0.92150(13) 0.0228 1.0000 Uani D . . . . .
C36 C 0.67994(16) 0.38674(13) 0.90703(15) 0.0245 1.0000 Uani D . . . . .
C37 C 0.66179(17) 0.41192(12) 0.83128(15) 0.0254 1.0000 Uani . . . . . .
O38 O 0.63862(11) 0.36224(9) 0.78181(10) 0.0256 1.0000 Uani . . . . . .
C39 C 0.62462(14) 0.37520(12) 0.70976(14) 0.0203 1.0000 Uani . . . . . .
C40 C 0.61785(15) 0.32541(12) 0.66449(15) 0.0226 1.0000 Uani . . . . . .
C41 C 0.60311(15) 0.33322(13) 0.59132(15) 0.0229 1.0000 Uani . . . . . .
C42 C 0.59432(14) 0.39168(12) 0.56194(14) 0.0188 1.0000 Uani . . . . . .
C43 C 0.60234(15) 0.44140(12) 0.60684(15) 0.0221 1.0000 Uani . . . . . .
C44 C 0.61753(15) 0.43326(12) 0.68084(15) 0.0233 1.0000 Uani . . . . . .
O45 O 0.57797(11) 0.39469(9) 0.48806(10) 0.0235 1.0000 Uani . . . . . .
C46 C 0.56342(17) 0.45282(13) 0.45469(15) 0.0255 1.0000 Uani . . . . . .
C47 C 0.52115(16) 0.44393(13) 0.37604(15) 0.0259 1.0000 Uani . . . . . .
N48 N 0.55973(13) 0.41093(11) 0.33726(12) 0.0230 1.0000 Uani . . . . . .
N49 N 0.59641(15) 0.44108(12) 0.30193(15) 0.0317 1.0000 Uani . . . . . .
N50 N 0.62870(16) 0.40099(12) 0.27580(15) 0.0331 1.0000 Uani . . . . . .
C51 C 0.56848(15) 0.35126(13) 0.33315(15) 0.0232 1.0000 Uani . . . . . .
C52 C 0.61260(15) 0.34457(13) 0.29392(15) 0.0228 1.0000 Uani . . . . . .
S1 S 0.59924(3) 0.20553(3) 0.82371(3) 0.0226 1.0000 Uani . . . . . .
O2 O 0.67363(10) 0.21651(9) 0.87223(12) 0.0270 1.0000 Uani . . . . . .
Cl3 Cl 0.67431(8) 0.20104(7) 0.48362(9) 0.0847 1.0000 Uani . . . . . .
Cl4 Cl 0.73830(8) 0.08448(8) 0.47760(11) 0.0961 1.0000 Uani . . . . . .
C57 C 0.57405(16) 0.13329(14) 0.84820(17) 0.0288 1.0000 Uani . . . . . .
C58 C 0.54440(16) 0.25217(16) 0.85664(17) 0.0322 1.0000 Uani . . . . . .
C59 C 0.7398(3) 0.1491(3) 0.5315(3) 0.0800 1.0000 Uani . . . . . .
H171 H 0.7007 -0.0015 0.6919 0.0311 1.0000 Uiso R . . . . .
H161 H 0.6434 -0.0115 0.5711 0.0298 1.0000 Uiso R . . . . .
H132 H 0.6050 0.0056 0.4481 0.0273 1.0000 Uiso R . . . . .
H131 H 0.5348 -0.0156 0.4648 0.0287 1.0000 Uiso R . . . . .
H122 H 0.5013 -0.0119 0.3426 0.0308 1.0000 Uiso R . . . . .
H121 H 0.4725 0.0515 0.3653 0.0299 1.0000 Uiso R . . . . .
H81 H 0.5408 0.1532 0.3487 0.0287 1.0000 Uiso R . . . . .
H511 H 0.5474 0.3220 0.3522 0.0306 1.0000 Uiso R . . . . .
H472 H 0.5115 0.4836 0.3534 0.0331 1.0000 Uiso R . . . . .
H471 H 0.4767 0.4234 0.3720 0.0330 1.0000 Uiso R . . . . .
H461 H 0.6065 0.4747 0.4608 0.0329 1.0000 Uiso R . . . . .
H462 H 0.5326 0.4746 0.4770 0.0340 1.0000 Uiso R . . . . .
H431 H 0.6030 0.4818 0.5892 0.0268 1.0000 Uiso R . . . . .
H441 H 0.6194 0.4672 0.7096 0.0309 1.0000 Uiso R . . . . .
H371 H 0.7054 0.4286 0.8268 0.0306 1.0000 Uiso R . . . . .
H372 H 0.6253 0.4431 0.8213 0.0308 1.0000 Uiso R . . . . .
H361 H 0.6935 0.4208 0.9432 0.0291 1.0000 Uiso R . . . . .
H362 H 0.6388 0.3645 0.9102 0.0306 1.0000 Uiso R . . . . .
H281 H 0.7891 0.2335 0.9560 0.0230 1.0000 Uiso R . . . . .
H231 H 0.7931 0.0309 0.9248 0.0258 1.0000 Uiso R . . . . .
H232 H 0.7170 0.0563 0.9067 0.0253 1.0000 Uiso R . . . . .
H222 H 0.7891 0.0441 0.8061 0.0250 1.0000 Uiso R . . . . .
H221 H 0.7260 0.0048 0.8051 0.0242 1.0000 Uiso R . . . . .
H321 H 0.9776 0.1818 0.9442 0.0276 1.0000 Uiso R . . . . .
H311 H 1.0110 0.2818 0.9541 0.0327 1.0000 Uiso R . . . . .
H301 H 0.9286 0.3592 0.9546 0.0300 1.0000 Uiso R . . . . .
H401 H 0.6237 0.2846 0.6821 0.0302 1.0000 Uiso R . . . . .
H411 H 0.5966 0.2993 0.5609 0.0277 1.0000 Uiso R . . . . .
H31 H 0.7121 0.3269 0.2345 0.0328 1.0000 Uiso R . . . . .
H41 H 0.7562 0.2359 0.2104 0.0344 1.0000 Uiso R . . . . .
H51 H 0.7106 0.1435 0.2361 0.0326 1.0000 Uiso R . . . . .
H201 H 0.5600 0.1570 0.5677 0.0315 1.0000 Uiso R . . . . .
H191 H 0.6229 0.1656 0.6936 0.0323 1.0000 Uiso R . . . . .
H592 H 0.7834 0.1705 0.5389 0.1000 1.0000 Uiso R . . . . .
H591 H 0.7341 0.1375 0.5785 0.0992 1.0000 Uiso R . . . . .
H571 H 0.5936 0.1021 0.8276 0.0470 1.0000 Uiso R . . . . .
H582 H 0.4967 0.2401 0.8312 0.0497 1.0000 Uiso R . . . . .
H241 H 0.7608(10) 0.1503(8) 0.8975(16) 0.0222 1.0000 Uiso D . . . . .
H573 H 0.5893 0.1297 0.9005 0.0453 1.0000 Uiso R . . . . .
H572 H 0.5220 0.1303 0.8307 0.0462 1.0000 Uiso R . . . . .
H581 H 0.5487 0.2944 0.8447 0.0503 1.0000 Uiso R . . . . .
H351 H 0.7213(10) 0.3038(9) 0.9050(18) 0.0278 1.0000 Uiso D . . . . .
H583 H 0.5552 0.2471 0.9063 0.0511 1.0000 Uiso R . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.986(4)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.346(4) yes
N1 . C6 . 1.339(4) yes
C2 . C3 . 1.395(4) yes
C2 . C52 . 1.467(4) yes
C3 . C4 . 1.379(4) yes
C3 . H31 . 0.927 no
C4 . C5 . 1.386(4) yes
C4 . H41 . 0.905 no
C5 . C6 . 1.400(4) yes
C5 . H51 . 0.954 no
C6 . C7 . 1.464(4) yes
C7 . C8 . 1.375(4) yes
C7 . N9 . 1.363(4) yes
C8 . N11 . 1.348(4) yes
C8 . H81 . 0.958 no
N9 . N10 . 1.308(4) yes
N10 . N11 . 1.352(3) yes
N11 . C12 . 1.459(4) yes
C12 . C13 . 1.509(4) yes
C12 . H122 . 0.984 no
C12 . H121 . 0.980 no
C13 . O14 . 1.431(3) yes
C13 . H132 . 0.969 no
C13 . H131 . 0.976 no
O14 . C15 . 1.377(3) yes
C15 . C16 . 1.390(4) yes
C15 . C20 . 1.387(4) yes
C16 . C17 . 1.392(4) yes
C16 . H161 . 0.938 no
C17 . C18 . 1.386(4) yes
C17 . H171 . 0.914 no
C18 . C19 . 1.391(4) yes
C18 . O21 . 1.372(3) yes
C19 . C20 . 1.382(4) yes
C19 . H191 . 0.979 no
C20 . H201 . 0.961 no
O21 . C22 . 1.434(3) yes
C22 . C23 . 1.517(3) yes
C22 . H222 . 0.970 no
C22 . H221 . 0.960 no
C23 . N24 . 1.459(3) yes
C23 . H231 . 0.948 no
C23 . H232 . 0.960 no
N24 . C26 . 1.346(3) yes
N24 . H241 . 0.855(18) no
O25 . C26 . 1.225(3) yes
C26 . C27 . 1.506(4) yes
C27 . C28 . 1.386(4) yes
C27 . C32 . 1.398(4) yes
C28 . C29 . 1.394(4) yes
C28 . H281 . 0.943 no
C29 . C30 . 1.395(4) yes
C29 . C34 . 1.495(4) yes
C30 . C31 . 1.388(4) yes
C30 . H301 . 0.930 no
C31 . C32 . 1.387(4) yes
C31 . H311 . 0.908 no
C32 . H321 . 0.931 no
O33 . C34 . 1.235(3) yes
C34 . N35 . 1.353(4) yes
N35 . C36 . 1.448(4) yes
N35 . H351 . 0.873(18) no
C36 . C37 . 1.516(4) yes
C36 . H361 . 1.007 no
C36 . H362 . 0.985 no
C37 . O38 . 1.436(3) yes
C37 . H371 . 0.985 no
C37 . H372 . 0.978 no
O38 . C39 . 1.380(3) yes
C39 . C40 . 1.392(4) yes
C39 . C44 . 1.389(4) yes
C40 . C41 . 1.380(4) yes
C40 . H401 . 0.958 no
C41 . C42 . 1.400(4) yes
C41 . H411 . 0.940 no
C42 . C43 . 1.384(4) yes
C42 . O45 . 1.380(3) yes
C43 . C44 . 1.396(4) yes
C43 . H431 . 0.958 no
C44 . H441 . 0.931 no
O45 . C46 . 1.426(3) yes
C46 . C47 . 1.508(4) yes
C46 . H461 . 0.966 no
C46 . H462 . 0.998 no
C47 . N48 . 1.456(4) yes
C47 . H472 . 0.972 no
C47 . H471 . 0.983 no
N48 . N49 . 1.349(3) yes
N48 . C51 . 1.334(4) yes
N49 . N50 . 1.303(4) yes
N50 . C52 . 1.364(4) yes
C51 . C52 . 1.369(4) yes
C51 . H511 . 0.920 no
S1 . O2 . 1.503(2) yes
S1 . C57 . 1.788(3) yes
S1 . C58 . 1.785(3) yes
Cl3 . C59 . 1.764(6) yes
Cl4 . C59 . 1.771(7) yes
C57 . H571 . 0.949 no
C57 . H573 . 0.974 no
C57 . H572 . 0.991 no
C58 . H582 . 0.961 no
C58 . H581 . 0.973 no
C58 . H583 . 0.934 no
C59 . H592 . 0.965 no
C59 . H591 . 1.004 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C6 . 117.6(2) yes
N1 . C2 . C3 . 123.1(3) yes
N1 . C2 . C52 . 115.2(2) yes
C3 . C2 . C52 . 121.7(3) yes
C2 . C3 . C4 . 118.6(3) yes
C2 . C3 . H31 . 120.3 no
C4 . C3 . H31 . 121.1 no
C3 . C4 . C5 . 119.1(3) yes
C3 . C4 . H41 . 119.8 no
C5 . C4 . H41 . 121.0 no
C4 . C5 . C6 . 118.7(3) yes
C4 . C5 . H51 . 122.2 no
C6 . C5 . H51 . 119.1 no
C5 . C6 . N1 . 122.8(3) yes
C5 . C6 . C7 . 120.9(3) yes
N1 . C6 . C7 . 116.2(2) yes
C6 . C7 . C8 . 129.4(3) yes
C6 . C7 . N9 . 122.3(2) yes
C8 . C7 . N9 . 108.3(2) yes
C7 . C8 . N11 . 104.7(2) yes
C7 . C8 . H81 . 128.6 no
N11 . C8 . H81 . 126.6 no
C7 . N9 . N10 . 109.0(2) yes
N9 . N10 . N11 . 107.4(2) yes
N10 . N11 . C8 . 110.6(2) yes
N10 . N11 . C12 . 118.9(2) yes
C8 . N11 . C12 . 130.2(2) yes
N11 . C12 . C13 . 110.5(2) yes
N11 . C12 . H122 . 107.8 no
C13 . C12 . H122 . 109.7 no
N11 . C12 . H121 . 106.4 no
C13 . C12 . H121 . 109.8 no
H122 . C12 . H121 . 112.5 no
C12 . C13 . O14 . 106.7(2) yes
C12 . C13 . H132 . 108.3 no
O14 . C13 . H132 . 110.3 no
C12 . C13 . H131 . 108.4 no
O14 . C13 . H131 . 109.4 no
H132 . C13 . H131 . 113.5 no
C13 . O14 . C15 . 116.9(2) yes
O14 . C15 . C16 . 124.2(2) yes
O14 . C15 . C20 . 116.0(2) yes
C16 . C15 . C20 . 119.8(2) yes
C15 . C16 . C17 . 119.9(2) yes
C15 . C16 . H161 . 123.4 no
C17 . C16 . H161 . 116.7 no
C16 . C17 . C18 . 120.4(3) yes
C16 . C17 . H171 . 120.6 no
C18 . C17 . H171 . 119.0 no
C17 . C18 . C19 . 119.2(2) yes
C17 . C18 . O21 . 124.9(2) yes
C19 . C18 . O21 . 116.0(2) yes
C18 . C19 . C20 . 120.7(3) yes
C18 . C19 . H191 . 117.5 no
C20 . C19 . H191 . 121.8 no
C15 . C20 . C19 . 120.0(3) yes
C15 . C20 . H201 . 119.7 no
C19 . C20 . H201 . 120.2 no
C18 . O21 . C22 . 117.9(2) yes
O21 . C22 . C23 . 105.8(2) yes
O21 . C22 . H222 . 113.4 no
C23 . C22 . H222 . 111.1 no
O21 . C22 . H221 . 109.6 no
C23 . C22 . H221 . 111.7 no
H222 . C22 . H221 . 105.4 no
C22 . C23 . N24 . 111.3(2) yes
C22 . C23 . H231 . 108.7 no
N24 . C23 . H231 . 108.9 no
C22 . C23 . H232 . 109.5 no
N24 . C23 . H232 . 108.6 no
H231 . C23 . H232 . 109.7 no
C23 . N24 . C26 . 121.5(2) yes
C23 . N24 . H241 . 118.3(12) no
C26 . N24 . H241 . 118.0(12) no
N24 . C26 . O25 . 123.2(2) yes
N24 . C26 . C27 . 115.1(2) yes
O25 . C26 . C27 . 121.7(2) yes
C26 . C27 . C28 . 122.7(2) yes
C26 . C27 . C32 . 117.8(2) yes
C28 . C27 . C32 . 119.5(2) yes
C27 . C28 . C29 . 120.8(2) yes
C27 . C28 . H281 . 122.1 no
C29 . C28 . H281 . 117.0 no
C28 . C29 . C30 . 119.4(3) yes
C28 . C29 . C34 . 122.1(2) yes
C30 . C29 . C34 . 118.5(2) yes
C29 . C30 . C31 . 119.9(3) yes
C29 . C30 . H301 . 114.2 no
C31 . C30 . H301 . 125.9 no
C30 . C31 . C32 . 120.5(3) yes
C30 . C31 . H311 . 119.7 no
C32 . C31 . H311 . 119.5 no
C27 . C32 . C31 . 119.8(3) yes
C27 . C32 . H321 . 120.6 no
C31 . C32 . H321 . 119.6 no
C29 . C34 . O33 . 121.1(3) yes
C29 . C34 . N35 . 115.9(2) yes
O33 . C34 . N35 . 123.0(3) yes
C34 . N35 . C36 . 122.1(2) yes
C34 . N35 . H351 . 119.0(12) no
C36 . N35 . H351 . 118.6(12) no
N35 . C36 . C37 . 111.7(2) yes
N35 . C36 . H361 . 112.4 no
C37 . C36 . H361 . 109.9 no
N35 . C36 . H362 . 103.1 no
C37 . C36 . H362 . 108.4 no
H361 . C36 . H362 . 111.2 no
C36 . C37 . O38 . 107.6(2) yes
C36 . C37 . H371 . 107.3 no
O38 . C37 . H371 . 108.7 no
C36 . C37 . H372 . 111.8 no
O38 . C37 . H372 . 110.5 no
H371 . C37 . H372 . 110.7 no
C37 . O38 . C39 . 116.5(2) yes
O38 . C39 . C40 . 115.9(2) yes
O38 . C39 . C44 . 124.7(2) yes
C40 . C39 . C44 . 119.4(2) yes
C39 . C40 . C41 . 120.7(2) yes
C39 . C40 . H401 . 122.4 no
C41 . C40 . H401 . 116.9 no
C40 . C41 . C42 . 119.9(3) yes
C40 . C41 . H411 . 120.1 no
C42 . C41 . H411 . 119.9 no
C41 . C42 . C43 . 119.7(2) yes
C41 . C42 . O45 . 115.6(2) yes
C43 . C42 . O45 . 124.8(2) yes
C42 . C43 . C44 . 120.2(2) yes
C42 . C43 . H431 . 121.2 no
C44 . C43 . H431 . 118.3 no
C43 . C44 . C39 . 120.2(3) yes
C43 . C44 . H441 . 118.7 no
C39 . C44 . H441 . 121.0 no
C42 . O45 . C46 . 117.9(2) yes
O45 . C46 . C47 . 108.3(2) yes
O45 . C46 . H461 . 110.8 no
C47 . C46 . H461 . 111.5 no
O45 . C46 . H462 . 107.0 no
C47 . C46 . H462 . 107.1 no
H461 . C46 . H462 . 111.9 no
C46 . C47 . N48 . 112.7(2) yes
C46 . C47 . H472 . 108.1 no
N48 . C47 . H472 . 105.6 no
C46 . C47 . H471 . 109.2 no
N48 . C47 . H471 . 111.2 no
H472 . C47 . H471 . 109.9 no
C47 . N48 . N49 . 120.5(2) yes
C47 . N48 . C51 . 129.1(2) yes
N49 . N48 . C51 . 110.4(2) yes
N48 . N49 . N50 . 107.6(2) yes
N49 . N50 . C52 . 108.8(2) yes
N48 . C51 . C52 . 105.4(2) yes
N48 . C51 . H511 . 125.4 no
C52 . C51 . H511 . 129.2 no
C2 . C52 . C51 . 128.9(3) yes
C2 . C52 . N50 . 123.2(2) yes
C51 . C52 . N50 . 107.9(3) yes
O2 . S1 . C57 . 106.63(13) yes
O2 . S1 . C58 . 106.55(13) yes
C57 . S1 . C58 . 98.55(16) yes
S1 . C57 . H571 . 109.5 no
S1 . C57 . H573 . 109.9 no
H571 . C57 . H573 . 111.3 no
S1 . C57 . H572 . 109.2 no
H571 . C57 . H572 . 110.4 no
H573 . C57 . H572 . 106.4 no
S1 . C58 . H582 . 106.6 no
S1 . C58 . H581 . 110.3 no
H582 . C58 . H581 . 107.2 no
S1 . C58 . H583 . 110.9 no
H582 . C58 . H583 . 110.6 no
H581 . C58 . H583 . 111.1 no
Cl4 . C59 . Cl3 . 110.1(3) yes
Cl4 . C59 . H592 . 108.4 no
Cl3 . C59 . H592 . 104.1 no
Cl4 . C59 . H591 . 111.3 no
Cl3 . C59 . H591 . 111.1 no
H592 . C59 . H591 . 111.6 no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C16 . H161 . O33 8_646 171.56(9) 0.938 2.306 3.237(4) yes
C47 . H471 . O25 7_454 136.12(8) 0.983 2.530 3.309(4) yes
C43 . H431 . O25 8_656 175.22(8) 0.958 2.514 3.470(4) yes
C28 . H281 . O2 . 134.89(8) 0.943 2.387 3.125(4) yes
C22 . H221 . N9 5_555 154.48(8) 0.960 2.531 3.423(4) yes
C32 . H321 . O45 7_555 158.47(7) 0.931 2.553 3.436(4) yes
C57 . H571 . O21 . 138.05(8) 0.949 2.595 3.361(4) yes
N24 . H241 . O2 . 164(3) 0.855 2.210 3.043(4) yes
C57 . H573 . O33 4_657 152.78(9) 0.974 2.537 3.432(4) yes
N35 . H351 . O2 . 169(3) 0.873 2.152 3.013(4) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 06/06/16 at 17:54:11
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL C    (   59 ) 
CONT H    (  241 ,X'S) 
CONT H    (  351 ,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 132,X'S) H   ( 131,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  22,X'S) H   ( 222,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) H   ( 362,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) H   ( 372,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) 
RIDE C   (  43,X'S) H   ( 431,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) 
RIDE C   (  46,X'S) H   ( 461,X'S) H   ( 462,X'S) 
RIDE C   (  47,X'S) H   ( 472,X'S) H   ( 471,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) 
RIDE C   (  57,X'S) H   ( 571,X'S) H   ( 573,X'S) H   ( 572,X'S) 
RIDE C   (  58,X'S) H   ( 582,X'S) H   ( 581,X'S) H   ( 583,X'S) 
RIDE C   (  59,X'S) H   ( 592,X'S) H   ( 591,X'S) 
END    
;

_iucr_refine_instructions_details_restraints 
;                                                                         
#
# Punched on 06/06/16 at 17:54:11
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            H1-N-R2 
DIST 0.86, 0.02 = 
CONT N ( 24) TO H(241) 
REST 0.022, 0.002 = H(241,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(241) TO N ( 24) TO C(23) 
CONT H(241) TO N ( 24) TO C(26) 
REM            H1-N-R2 
DIST 0.86, 0.02 = 
CONT N ( 35) TO H(351) 
REST 0.027, 0.002 = H(351,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(351) TO N ( 35) TO C(34) 
CONT H(351) TO N ( 35) TO C(36) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DMSO/methanol/dichloromethane'
####################################################################### 
# 
# 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_Zn_8
_database_code_depnum_ccdc_archive 'CCDC 2225118'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2022-12-08 deposited with the CCDC.	2023-01-16 downloaded from the CCDC.
;
#==============================================================================
# start Validation Reply Form
_vrf_PLAT230_Zn_8                
;
PROBLEM: Hirshfeld Test Diff for    C46      --C47      .        9.8 s.u.  
RESPONSE: Crystals were small and weakly diffracting and required the use of
synchrotron radiation. Even using high intensity radiation, data are relatively
weak and data are of relatively poor quality, which is compounded by large 
areas of diffuse electron density believed to result from perchlorate anions
and solvent molecules. As few restraints as possible were used, and the 
data are presented as a guide to the molecular structure only.
;
_vrf_PLAT234_Zn_8                
;
PROBLEM: Large Hirshfeld Difference O71      --C72      .       0.29 Ang.  
RESPONSE: Crystals were small and weakly diffracting and required the use of
synchrotron radiation. Even using high intensity radiation, data are relatively
weak and data are of relatively poor quality, which is compounded by large 
areas of diffuse electron density believed to result from perchlorate anions
and solvent molecules. As few restraints as possible were used, and the 
data are presented as a guide to the molecular structure only..
;
_vrf_PLAT241_Zn_8                
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of        C46 Check 
RESPONSE:  Crystals were small and weakly diffracting and required the use of
synchrotron radiation. Even using high intensity radiation, data are relatively
weak and data are of relatively poor quality, which is compounded by large 
areas of diffuse electron density believed to result from perchlorate anions
and solvent molecules. As few restraints as possible were used, and the 
data are presented as a guide to the molecular structure only.
;
_vrf_PLAT420_Zn_8                
;
PROBLEM: D-H Bond Without Acceptor  O61      --H61B     .     Please Check 
RESPONSE: These are coordinated water and methanol molecules, which presumably
hydrogen bond to solvent molecules or perchlorate anions. As a large
region of diffuse electron density (believed to contain these species) was 
removed using the OLEX mask feature, these hydrogen bond acceptors are not 
present. 
;

_refine_special_details          
;Crystals were small and very weakly diffrating. Even using microfocus
synchrotron radiation, no data could be resolved beyond a resolution of 0.85 A.
The data are of relatively low quality and it was not possible to sensibly
model the positions of the perchlorate anions, or of the (numerous) solvent 
molecules. The diffuse electron density from these species was included in the 
model using the OLEX mask feature.

It appears that the zinc(II) ion is coordinated to two water molecules and one
methanol, although given the quality of the data, it is possible that these 
vary (i.e. that sometimes the water molecules are methanol and vice-versa).

It was necessary to apply DFIX restraints to phenyl rings, four CH2-CH2 bonds 
and the two phenyl-amidecarbon bonds in order to achieve a sensible refinement.

Hydrogen atoms were inserted at calculated positions.,SQUEEZE
;

_audit_creation_date             2022-08-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C38 H43 N9 O9 Zn'
_chemical_formula_sum            'C38 H43 N9 O9 Zn'
_chemical_formula_weight         835.18
_chemical_melting_point          synthesized

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'
Zn Zn 0.2839 1.4301 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'

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                   13.835(3)
_cell_length_b                   26.283(5)
_cell_length_c                   17.570(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.88(3)
_cell_angle_gamma                90
_cell_volume                     5929(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    66965
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.723
_cell_measurement_theta_min      1.470

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02

_exptl_absorpt_correction_type   None

_diffrn_radiation_type           Synchrotron
_diffrn_radiation_source         'MX2 Beamline Australian Synchrotron'
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_measurement_device_type  'Dectris Eiger 16M'
_diffrn_measurement_method       'Omega Scan'

_computing_data_collection       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'

_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            66965
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.723
_diffrn_reflns_theta_max         24.723
_diffrn_reflns_theta_min         1.470
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7390
_reflns_number_total             10091
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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)'
_refine_diff_density_max         0.737
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         10091
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.1516
_refine_ls_R_factor_gt           0.1366
_refine_ls_restrained_S_all      1.005
_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)+(0.1000P)²+28.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3436
_refine_ls_wR_factor_ref         0.3509

_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 C15-C16
 1.4 with sigma of 0.01
 C16-C17
 1.4 with sigma of 0.01
 C17-C18
 1.4 with sigma of 0.01
 C18-C19
 1.4 with sigma of 0.01
 C19-C20
 1.4 with sigma of 0.01
 C20-C15
 1.4 with sigma of 0.01
 C27-C28
 1.4 with sigma of 0.01
 C28-C29
 1.4 with sigma of 0.01
 C29-C30
 1.4 with sigma of 0.01
 C30-C31
 1.4 with sigma of 0.01
 C31-C32
 1.4 with sigma of 0.01
 C32-C27
 1.4 with sigma of 0.01
 C39-C40
 1.4 with sigma of 0.01
 C40-C41
 1.4 with sigma of 0.01
 C41-C42
 1.4 with sigma of 0.01
 C42-C43
 1.4 with sigma of 0.01
 C43-C44
 1.4 with sigma of 0.01
 C44-C39
 1.4 with sigma of 0.01
 C29-C34
 1.5 with sigma of 0.01
 C27-C26
 1.5 with sigma of 0.01
 C23-C22
 1.52 with sigma of 0.01
 C36-C37
 1.52 with sigma of 0.01
 C13-C12
 1.52 with sigma of 0.01
 C46-C47
 1.52 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C22(H22A,H22B), C23(H23A,H23B), C36(H36A,
 H36B), C37(H37A,H37B), C46(H46A,H46B), C47(H47A,H47B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C16(H16), C17(H17), C19(H19), C20(H20),
 C28(H28), C30(H30), C31(H31), C32(H32), C40(H40), C41(H41), C43(H43), C44(H44),
  C51(H51), N24(H24), N35(H35)
3.c X=CH2 refined with riding coordinates:
 O61(H61A,H61B), O81(H81A,H81B)
3.d Idealised Me refined as rotating group:
 C72(H72A,H72B,H72C)
3.e Idealised tetrahedral OH refined as rotating group:
 O71(H71)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
C2 C 0.5865(7) 0.7564(4) 0.6525(5) 0.099(3) Uani 1 1 d . . . . .
C3 C 0.6440(8) 0.7746(4) 0.7322(5) 0.109(3) Uani 1 1 d . . . . .
H3 H 0.648944 0.809177 0.744209 0.131 Uiso 1 1 calc R U . . .
C4 C 0.6926(8) 0.7388(4) 0.7915(6) 0.118(3) Uani 1 1 d . . . . .
H4 H 0.731000 0.748709 0.845119 0.141 Uiso 1 1 calc R U . . .
C5 C 0.6833(8) 0.6883(5) 0.7700(5) 0.121(3) Uani 1 1 d . . . . .
H5 H 0.715673 0.663767 0.809305 0.145 Uiso 1 1 calc R U . . .
C6 C 0.6236(7) 0.6732(4) 0.6867(5) 0.106(3) Uani 1 1 d . . . . .
C7 C 0.5275(7) 0.7920(4) 0.5826(4) 0.094(2) Uani 1 1 d . . . . .
C8 C 0.5112(7) 0.8425(4) 0.5775(5) 0.096(2) Uani 1 1 d . . . . .
H8 H 0.537464 0.866868 0.618496 0.115 Uiso 1 1 calc R U . . .
C12 C 0.4010(7) 0.8995(3) 0.4592(5) 0.099(3) Uani 1 1 d D . . . .
H12A H 0.453046 0.926264 0.476876 0.119 Uiso 1 1 calc R U . . .
H12B H 0.376985 0.896707 0.400001 0.119 Uiso 1 1 calc R U . . .
C13 C 0.3126(7) 0.9119(3) 0.4841(5) 0.101(3) Uani 1 1 d D . . . .
H13A H 0.286242 0.945604 0.464779 0.121 Uiso 1 1 calc R U . . .
H13B H 0.335531 0.911603 0.543470 0.121 Uiso 1 1 calc R U . . .
C15 C 0.1536(7) 0.8730(3) 0.4753(5) 0.098(3) Uani 1 1 d D . . . .
C16 C 0.1403(7) 0.9047(3) 0.5348(5) 0.106(3) Uani 1 1 d D . . . .
H16 H 0.191904 0.928391 0.560903 0.128 Uiso 1 1 calc R U . . .
C17 C 0.0536(7) 0.9024(3) 0.5565(6) 0.106(3) Uani 1 1 d D . . . .
H17 H 0.045809 0.925124 0.594320 0.127 Uiso 1 1 calc R U . . .
C18 C -0.0212(7) 0.8654(3) 0.5206(5) 0.099(3) Uani 1 1 d D . . . .
C19 C -0.0105(7) 0.8338(4) 0.4614(6) 0.113(3) Uani 1 1 d D . . . .
H19 H -0.060153 0.808705 0.438085 0.136 Uiso 1 1 calc R U . . .
C20 C 0.0726(7) 0.8387(4) 0.4362(5) 0.108(3) Uani 1 1 d D . . . .
H20 H 0.074656 0.819073 0.392849 0.130 Uiso 1 1 calc R U . . .
C22 C -0.1044(7) 0.8773(3) 0.6149(6) 0.103(3) Uani 1 1 d D . . . .
H22A H -0.113880 0.913935 0.611228 0.124 Uiso 1 1 calc R U . . .
H22B H -0.039085 0.869558 0.659185 0.124 Uiso 1 1 calc R U . . .
C23 C -0.1948(7) 0.8515(3) 0.6284(6) 0.107(3) Uani 1 1 d D . . . .
H23A H -0.202109 0.865905 0.676741 0.128 Uiso 1 1 calc R U . . .
H23B H -0.258365 0.858629 0.581876 0.128 Uiso 1 1 calc R U . . .
C26 C -0.1204(7) 0.7768(3) 0.7105(6) 0.100(2) Uani 1 1 d D . . . .
C27 C -0.1061(7) 0.7207(3) 0.7061(4) 0.096(2) Uani 1 1 d D . . . .
C28 C -0.0364(6) 0.6989(3) 0.7764(5) 0.100(3) Uani 1 1 d D . . . .
H28 H -0.002203 0.719060 0.821978 0.119 Uiso 1 1 calc R U . . .
C29 C -0.0166(7) 0.6466(3) 0.7797(5) 0.105(3) Uani 1 1 d D . . . .
C30 C -0.0745(8) 0.6166(3) 0.7130(5) 0.125(4) Uani 1 1 d D . . . .
H30 H -0.064405 0.581547 0.716072 0.150 Uiso 1 1 calc R U . . .
C31 C -0.1471(9) 0.6376(3) 0.6418(5) 0.134(4) Uani 1 1 d D . . . .
H31 H -0.184061 0.617401 0.596874 0.160 Uiso 1 1 calc R U . . .
C32 C -0.1620(9) 0.6897(3) 0.6407(6) 0.125(4) Uani 1 1 d D . . . .
H32 H -0.211277 0.704465 0.594334 0.149 Uiso 1 1 calc R U . . .
C34 C 0.0637(7) 0.6243(4) 0.8570(6) 0.107(3) Uani 1 1 d D . . . .
C36 C 0.1579(8) 0.5514(5) 0.9378(7) 0.143(4) Uani 1 1 d D . . . .
H36A H 0.135533 0.517837 0.947445 0.171 Uiso 1 1 calc R U . . .
H36B H 0.169685 0.572199 0.985977 0.171 Uiso 1 1 calc R U . . .
C37 C 0.2569(8) 0.5477(4) 0.9192(7) 0.125(4) Uani 1 1 d D . . . .
H37A H 0.273656 0.580860 0.903260 0.150 Uiso 1 1 calc R U . . .
H37B H 0.314412 0.536970 0.968084 0.150 Uiso 1 1 calc R U . . .
C39 C 0.3198(9) 0.5066(3) 0.8288(6) 0.111(3) Uani 1 1 d D . . . .
C40 C 0.3038(10) 0.4730(4) 0.7635(6) 0.144(5) Uani 1 1 d D . . . .
H40 H 0.242876 0.453858 0.743999 0.172 Uiso 1 1 calc R U . . .
C41 C 0.3779(9) 0.4673(4) 0.7267(7) 0.139(5) Uani 1 1 d D . . . .
H41 H 0.359235 0.449643 0.677405 0.166 Uiso 1 1 calc R U . . .
C42 C 0.4775(9) 0.4872(3) 0.7612(5) 0.121(4) Uani 1 1 d D . . . .
C43 C 0.4932(10) 0.5194(3) 0.8277(6) 0.125(4) Uani 1 1 d D . . . .
H43 H 0.557362 0.535621 0.851143 0.150 Uiso 1 1 calc R U . . .
C44 C 0.4174(8) 0.5288(4) 0.8613(7) 0.146(5) Uani 1 1 d D . . . .
H44 H 0.433044 0.550342 0.906281 0.175 Uiso 1 1 calc R U . . .
C46 C 0.5296(11) 0.4616(5) 0.6563(7) 0.181(7) Uani 1 1 d D . . . .
H46A H 0.458187 0.468896 0.621054 0.218 Uiso 1 1 calc R U . . .
H46B H 0.540238 0.425027 0.658036 0.218 Uiso 1 1 calc R U . . .
C47 C 0.6057(10) 0.4886(4) 0.6257(7) 0.129(4) Uani 1 1 d D . . . .
H47A H 0.676084 0.478644 0.659861 0.154 Uiso 1 1 calc R U . . .
H47B H 0.592983 0.477386 0.570213 0.154 Uiso 1 1 calc R U . . .
C51 C 0.6418(9) 0.5718(4) 0.6857(5) 0.117(3) Uani 1 1 d . . . . .
H51 H 0.689504 0.563273 0.737445 0.140 Uiso 1 1 calc R U . . .
C52 C 0.6036(9) 0.6197(4) 0.6573(5) 0.122(3) Uani 1 1 d . . . . .
C72 C 0.6282(15) 0.6451(7) 0.4250(10) 0.222(8) Uani 1 1 d . . . . .
H72A H 0.626597 0.657496 0.373155 0.333 Uiso 1 1 calc R U . . .
H72B H 0.580717 0.617100 0.416134 0.333 Uiso 1 1 calc R U . . .
H72C H 0.697397 0.634008 0.457565 0.333 Uiso 1 1 calc R U . . .
N1 N 0.5739(6) 0.7083(3) 0.6320(4) 0.100(2) Uani 1 1 d . . . . .
N9 N 0.4701(6) 0.7689(3) 0.5075(4) 0.099(2) Uani 1 1 d . . . . .
N10 N 0.4209(6) 0.8048(3) 0.4567(4) 0.096(2) Uani 1 1 d . . . . .
N11 N 0.4478(6) 0.8493(3) 0.4990(4) 0.101(2) Uani 1 1 d . . . . .
N24 N -0.1832(5) 0.7984(3) 0.6383(4) 0.0942(19) Uani 1 1 d . . . . .
H24 H -0.216659 0.778948 0.597692 0.113 Uiso 1 1 calc R U . . .
N35 N 0.0767(6) 0.5755(3) 0.8631(5) 0.111(3) Uani 1 1 d . . . . .
H35 H 0.038351 0.556306 0.823739 0.133 Uiso 1 1 calc R U . . .
N48 N 0.5980(7) 0.5425(3) 0.6264(4) 0.118(3) Uani 1 1 d . . . . .
N49 N 0.5376(8) 0.5636(4) 0.5593(5) 0.131(3) Uani 1 1 d . . . . .
N50 N 0.5372(8) 0.6142(3) 0.5772(4) 0.133(3) Uani 1 1 d . . . . .
O14 O 0.2320(5) 0.8749(2) 0.4497(4) 0.1085(19) Uani 1 1 d . . . . .
O21 O -0.1061(5) 0.8574(3) 0.5409(4) 0.1096(19) Uani 1 1 d . . . . .
O25 O -0.0836(5) 0.8012(2) 0.7716(4) 0.1078(19) Uani 1 1 d . . . . .
O33 O 0.1205(6) 0.6511(3) 0.9140(4) 0.127(2) Uani 1 1 d . . . . .
O38 O 0.2434(6) 0.5128(2) 0.8559(5) 0.120(2) Uani 1 1 d . . . . .
O45 O 0.5516(7) 0.4808(3) 0.7344(4) 0.129(2) Uani 1 1 d . . . . .
O61 O 0.3830(6) 0.6605(3) 0.3990(3) 0.141(3) Uani 1 1 d . . . . .
H61A H 0.409594 0.655122 0.358265 0.212 Uiso 1 1 calc R U . . .
H61B H 0.312926 0.654331 0.388334 0.212 Uiso 1 1 calc R U . . .
O71 O 0.5978(6) 0.6854(3) 0.4674(4) 0.120(2) Uani 1 1 d . . . . .
H71 H 0.618422 0.712729 0.456813 0.180 Uiso 1 1 calc R U . . .
O81 O 0.3497(7) 0.6821(4) 0.5465(5) 0.161(3) Uani 1 1 d . . . . .
H81A H 0.285357 0.671481 0.509183 0.242 Uiso 1 1 calc R U . . .
H81B H 0.356775 0.691279 0.599450 0.242 Uiso 1 1 calc R U . . .
Zn01 Zn 0.47783(10) 0.68554(4) 0.51141(6) 0.1107(5) 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
C2 C3 1.411(11) . ?
C2 C7 1.518(12) . ?
C2 N1 1.309(11) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(12) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(14) . ?
C5 H5 0.9300 . ?
C5 C6 1.443(12) . ?
C6 C52 1.487(14) . ?
C6 N1 1.327(10) . ?
C7 C8 1.344(12) . ?
C7 N9 1.399(9) . ?
C8 H8 0.9300 . ?
C8 N11 1.343(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.481(8) . ?
C12 N11 1.521(11) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 O14 1.432(9) . ?
C15 C16 1.402(8) . ?
C15 C20 1.402(8) . ?
C15 O14 1.320(10) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.388(8) . ?
C18 C19 1.380(8) . ?
C18 O21 1.366(10) . ?
C19 H19 0.9300 . ?
C19 C20 1.383(8) . ?
C20 H20 0.9300 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.517(8) . ?
C22 O21 1.393(10) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 N24 1.408(10) . ?
C26 C27 1.494(8) . ?
C26 N24 1.365(11) . ?
C26 O25 1.190(10) . ?
C27 C28 1.377(7) . ?
C27 C32 1.386(8) . ?
C28 H28 0.9300 . ?
C28 C29 1.397(8) . ?
C29 C30 1.392(8) . ?
C29 C34 1.517(8) . ?
C30 H30 0.9300 . ?
C30 C31 1.394(8) . ?
C31 H31 0.9300 . ?
C31 C32 1.385(8) . ?
C32 H32 0.9300 . ?
C34 N35 1.294(11) . ?
C34 O33 1.239(11) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 C37 1.524(9) . ?
C36 N35 1.512(12) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C37 O38 1.400(12) . ?
C39 C40 1.399(8) . ?
C39 C44 1.384(9) . ?
C39 O38 1.322(12) . ?
C40 H40 0.9300 . ?
C40 C41 1.410(9) . ?
C41 H41 0.9300 . ?
C41 C42 1.384(9) . ?
C42 C43 1.394(8) . ?
C42 O45 1.288(12) . ?
C43 H43 0.9300 . ?
C43 C44 1.403(9) . ?
C44 H44 0.9300 . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C46 C47 1.524(9) . ?
C46 O45 1.386(12) . ?
C47 H47A 0.9700 . ?
C47 H47B 0.9700 . ?
C47 N48 1.422(12) . ?
C51 H51 0.9300 . ?
C51 C52 1.383(13) . ?
C51 N48 1.257(11) . ?
C52 N50 1.372(11) . ?
C72 H72A 0.9600 . ?
C72 H72B 0.9600 . ?
C72 H72C 0.9600 . ?
C72 O71 1.443(16) . ?
N1 Zn01 2.125(7) . ?
N9 N10 1.302(9) . ?
N9 Zn01 2.194(8) . ?
N10 N11 1.363(9) . ?
N24 H24 0.8600 . ?
N35 H35 0.8600 . ?
N48 N49 1.289(10) . ?
N49 N50 1.367(11) . ?
N50 Zn01 2.196(9) . ?
O61 H61A 0.9300 . ?
O61 H61B 0.9300 . ?
O61 Zn01 2.031(6) . ?
O71 H71 0.8200 . ?
O71 Zn01 2.076(8) . ?
O81 H81A 0.9300 . ?
O81 H81B 0.9300 . ?
O81 Zn01 2.085(8) . ?

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
C3 C2 C7 122.0(9) . . ?
N1 C2 C3 124.6(9) . . ?
N1 C2 C7 113.3(7) . . ?
C2 C3 H3 121.5 . . ?
C4 C3 C2 117.1(9) . . ?
C4 C3 H3 121.5 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.8(9) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(9) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C52 125.1(9) . . ?
N1 C6 C5 119.3(9) . . ?
N1 C6 C52 115.3(8) . . ?
C8 C7 C2 133.5(8) . . ?
C8 C7 N9 110.1(7) . . ?
N9 C7 C2 116.2(8) . . ?
C7 C8 H8 128.4 . . ?
C7 C8 N11 103.2(8) . . ?
N11 C8 H8 128.4 . . ?
H12A C12 H12B 108.4 . . ?
C13 C12 H12A 110.1 . . ?
C13 C12 H12B 110.1 . . ?
C13 C12 N11 108.2(7) . . ?
N11 C12 H12A 110.1 . . ?
N11 C12 H12B 110.1 . . ?
C12 C13 H13A 109.9 . . ?
C12 C13 H13B 109.9 . . ?
C12 C13 O14 109.0(7) . . ?
H13A C13 H13B 108.3 . . ?
O14 C13 H13A 109.9 . . ?
O14 C13 H13B 109.9 . . ?
C20 C15 C16 116.3(9) . . ?
O14 C15 C16 125.7(7) . . ?
O14 C15 C20 117.9(7) . . ?
C15 C16 H16 118.5 . . ?
C17 C16 C15 123.1(8) . . ?
C17 C16 H16 118.5 . . ?
C16 C17 H17 120.7 . . ?
C18 C17 C16 118.6(8) . . ?
C18 C17 H17 120.7 . . ?
C19 C18 C17 119.5(9) . . ?
O21 C18 C17 123.8(8) . . ?
O21 C18 C19 116.6(7) . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.3(9) . . ?
C20 C19 H19 119.4 . . ?
C15 C20 H20 119.6 . . ?
C19 C20 C15 120.8(9) . . ?
C19 C20 H20 119.6 . . ?
H22A C22 H22B 108.9 . . ?
C23 C22 H22A 110.9 . . ?
C23 C22 H22B 110.9 . . ?
O21 C22 H22A 110.9 . . ?
O21 C22 H22B 110.9 . . ?
O21 C22 C23 104.5(7) . . ?
C22 C23 H23A 108.8 . . ?
C22 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
N24 C23 C22 113.6(8) . . ?
N24 C23 H23A 108.8 . . ?
N24 C23 H23B 108.8 . . ?
N24 C26 C27 114.3(8) . . ?
O25 C26 C27 124.0(9) . . ?
O25 C26 N24 121.6(8) . . ?
C28 C27 C26 115.3(7) . . ?
C28 C27 C32 119.1(8) . . ?
C32 C27 C26 125.5(8) . . ?
C27 C28 H28 119.7 . . ?
C27 C28 C29 120.5(8) . . ?
C29 C28 H28 119.7 . . ?
C28 C29 C34 119.0(7) . . ?
C30 C29 C28 118.7(7) . . ?
C30 C29 C34 122.2(8) . . ?
C29 C30 H30 119.1 . . ?
C29 C30 C31 121.8(8) . . ?
C31 C30 H30 119.1 . . ?
C30 C31 H31 121.4 . . ?
C32 C31 C30 117.3(9) . . ?
C32 C31 H31 121.4 . . ?
C27 C32 C31 122.4(9) . . ?
C27 C32 H32 118.8 . . ?
C31 C32 H32 118.8 . . ?
N35 C34 C29 119.5(9) . . ?
O33 C34 C29 122.4(9) . . ?
O33 C34 N35 118.1(8) . . ?
H36A C36 H36B 108.7 . . ?
C37 C36 H36A 110.5 . . ?
C37 C36 H36B 110.5 . . ?
N35 C36 H36A 110.5 . . ?
N35 C36 H36B 110.5 . . ?
N35 C36 C37 106.1(9) . . ?
C36 C37 H37A 109.6 . . ?
C36 C37 H37B 109.6 . . ?
H37A C37 H37B 108.1 . . ?
O38 C37 C36 110.3(9) . . ?
O38 C37 H37A 109.6 . . ?
O38 C37 H37B 109.6 . . ?
C44 C39 C40 115.9(12) . . ?
O38 C39 C40 118.0(10) . . ?
O38 C39 C44 126.0(10) . . ?
C39 C40 H40 119.2 . . ?
C39 C40 C41 121.5(12) . . ?
C41 C40 H40 119.2 . . ?
C40 C41 H41 118.8 . . ?
C42 C41 C40 122.3(11) . . ?
C42 C41 H41 118.8 . . ?
C41 C42 C43 114.6(11) . . ?
O45 C42 C41 126.0(10) . . ?
O45 C42 C43 119.3(11) . . ?
C42 C43 H43 118.3 . . ?
C42 C43 C44 123.4(12) . . ?
C44 C43 H43 118.3 . . ?
C39 C44 C43 121.3(12) . . ?
C39 C44 H44 119.3 . . ?
C43 C44 H44 119.3 . . ?
H46A C46 H46B 108.9 . . ?
C47 C46 H46A 110.8 . . ?
C47 C46 H46B 110.8 . . ?
O45 C46 H46A 110.8 . . ?
O45 C46 H46B 110.8 . . ?
O45 C46 C47 104.7(10) . . ?
C46 C47 H47A 108.9 . . ?
C46 C47 H47B 108.9 . . ?
H47A C47 H47B 107.7 . . ?
N48 C47 C46 113.5(11) . . ?
N48 C47 H47A 108.9 . . ?
N48 C47 H47B 108.9 . . ?
C52 C51 H51 127.5 . . ?
N48 C51 H51 127.5 . . ?
N48 C51 C52 104.9(8) . . ?
C51 C52 C6 137.5(9) . . ?
N50 C52 C6 115.0(9) . . ?
N50 C52 C51 107.1(9) . . ?
H72A C72 H72B 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 109.5 . . ?
O71 C72 H72A 109.5 . . ?
O71 C72 H72B 109.5 . . ?
O71 C72 H72C 109.5 . . ?
C2 N1 C6 119.6(8) . . ?
C2 N1 Zn01 121.1(6) . . ?
C6 N1 Zn01 119.3(6) . . ?
C7 N9 Zn01 113.6(6) . . ?
N10 N9 C7 107.5(7) . . ?
N10 N9 Zn01 138.7(5) . . ?
N9 N10 N11 106.3(6) . . ?
C8 N11 C12 126.2(8) . . ?
C8 N11 N10 112.8(7) . . ?
N10 N11 C12 120.8(6) . . ?
C23 N24 H24 119.0 . . ?
C26 N24 C23 122.1(7) . . ?
C26 N24 H24 119.0 . . ?
C34 N35 C36 121.5(8) . . ?
C34 N35 H35 119.2 . . ?
C36 N35 H35 119.2 . . ?
C51 N48 C47 127.2(8) . . ?
C51 N48 N49 116.3(9) . . ?
N49 N48 C47 116.5(9) . . ?
N48 N49 N50 105.3(8) . . ?
C52 N50 Zn01 115.2(7) . . ?
N49 N50 C52 106.3(8) . . ?
N49 N50 Zn01 137.9(5) . . ?
C15 O14 C13 119.5(6) . . ?
C18 O21 C22 118.0(7) . . ?
C39 O38 C37 118.6(8) . . ?
C42 O45 C46 119.9(10) . . ?
H61A O61 H61B 120.0 . . ?
Zn01 O61 H61A 120.0 . . ?
Zn01 O61 H61B 120.0 . . ?
C72 O71 H71 109.5 . . ?
C72 O71 Zn01 128.4(9) . . ?
Zn01 O71 H71 118.4 . . ?
H81A O81 H81B 120.0 . . ?
Zn01 O81 H81A 120.0 . . ?
Zn01 O81 H81B 120.0 . . ?
N1 Zn01 N9 75.8(3) . . ?
N1 Zn01 N50 75.1(3) . . ?
N9 Zn01 N50 150.9(3) . . ?
O61 Zn01 N1 176.7(3) . . ?
O61 Zn01 N9 106.7(3) . . ?
O61 Zn01 N50 102.4(3) . . ?
O61 Zn01 O71 87.3(3) . . ?
O61 Zn01 O81 87.8(3) . . ?
O71 Zn01 N1 94.7(3) . . ?
O71 Zn01 N9 91.5(3) . . ?
O71 Zn01 N50 90.0(3) . . ?
O71 Zn01 O81 175.0(3) . . ?
O81 Zn01 N1 90.1(3) . . ?
O81 Zn01 N9 90.9(3) . . ?
O81 Zn01 N50 90.0(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 C4 C5 0.6(16) . . . . ?
C2 C7 C8 N11 -176.7(9) . . . . ?
C2 C7 N9 N10 176.7(8) . . . . ?
C2 C7 N9 Zn01 1.3(10) . . . . ?
C3 C2 C7 C8 -3.3(17) . . . . ?
C3 C2 C7 N9 -177.4(9) . . . . ?
C3 C2 N1 C6 -5.3(15) . . . . ?
C3 C2 N1 Zn01 176.3(7) . . . . ?
C3 C4 C5 C6 0.0(17) . . . . ?
C4 C5 C6 C52 -176.6(11) . . . . ?
C4 C5 C6 N1 -3.1(16) . . . . ?
C5 C6 C52 C51 -14(2) . . . . ?
C5 C6 C52 N50 174.5(10) . . . . ?
C5 C6 N1 C2 5.6(15) . . . . ?
C5 C6 N1 Zn01 -175.9(7) . . . . ?
C6 C52 N50 N49 173.6(10) . . . . ?
C6 C52 N50 Zn01 0.6(13) . . . . ?
C7 C2 C3 C4 178.6(9) . . . . ?
C7 C2 N1 C6 178.0(8) . . . . ?
C7 C2 N1 Zn01 -0.5(11) . . . . ?
C7 C8 N11 C12 178.0(8) . . . . ?
C7 C8 N11 N10 2.7(10) . . . . ?
C7 N9 N10 N11 0.5(9) . . . . ?
C8 C7 N9 N10 1.2(10) . . . . ?
C8 C7 N9 Zn01 -174.2(6) . . . . ?
C12 C13 O14 C15 168.1(8) . . . . ?
C13 C12 N11 C8 -77.7(10) . . . . ?
C13 C12 N11 N10 97.2(9) . . . . ?
C15 C16 C17 C18 3.1(15) . . . . ?
C16 C15 C20 C19 -5.9(14) . . . . ?
C16 C15 O14 C13 0.2(14) . . . . ?
C16 C17 C18 C19 -3.4(14) . . . . ?
C16 C17 C18 O21 175.7(8) . . . . ?
C17 C18 C19 C20 -1.0(15) . . . . ?
C17 C18 O21 C22 -17.6(13) . . . . ?
C18 C19 C20 C15 5.8(16) . . . . ?
C19 C18 O21 C22 161.5(9) . . . . ?
C20 C15 C16 C17 1.5(14) . . . . ?
C20 C15 O14 C13 175.7(8) . . . . ?
C22 C23 N24 C26 78.3(11) . . . . ?
C23 C22 O21 C18 -166.7(7) . . . . ?
C26 C27 C28 C29 180.0(9) . . . . ?
C26 C27 C32 C31 -177.8(11) . . . . ?
C27 C26 N24 C23 -171.8(8) . . . . ?
C27 C28 C29 C30 -4.9(15) . . . . ?
C27 C28 C29 C34 177.7(9) . . . . ?
C28 C27 C32 C31 -2.9(17) . . . . ?
C28 C29 C30 C31 3.6(18) . . . . ?
C28 C29 C34 N35 174.6(10) . . . . ?
C28 C29 C34 O33 -8.0(15) . . . . ?
C29 C30 C31 C32 -1.9(19) . . . . ?
C29 C34 N35 C36 178.2(9) . . . . ?
C30 C29 C34 N35 -2.6(16) . . . . ?
C30 C29 C34 O33 174.8(11) . . . . ?
C30 C31 C32 C27 1.5(19) . . . . ?
C32 C27 C28 C29 4.6(15) . . . . ?
C34 C29 C30 C31 -179.2(11) . . . . ?
C36 C37 O38 C39 176.6(8) . . . . ?
C37 C36 N35 C34 -90.6(12) . . . . ?
C39 C40 C41 C42 11.9(19) . . . . ?
C40 C39 C44 C43 2.7(15) . . . . ?
C40 C39 O38 C37 -177.7(8) . . . . ?
C40 C41 C42 C43 -9.3(16) . . . . ?
C40 C41 C42 O45 175.0(11) . . . . ?
C41 C42 C43 C44 4.1(15) . . . . ?
C41 C42 O45 C46 14.1(16) . . . . ?
C42 C43 C44 C39 -1.0(17) . . . . ?
C43 C42 O45 C46 -161.4(10) . . . . ?
C44 C39 C40 C41 -7.9(16) . . . . ?
C44 C39 O38 C37 5.3(14) . . . . ?
C46 C47 N48 C51 84.9(15) . . . . ?
C46 C47 N48 N49 -93.3(12) . . . . ?
C47 C46 O45 C42 145.3(10) . . . . ?
C47 N48 N49 N50 175.4(10) . . . . ?
C51 C52 N50 N49 -0.4(13) . . . . ?
C51 C52 N50 Zn01 -173.4(8) . . . . ?
C51 N48 N49 N50 -3.0(15) . . . . ?
C52 C6 N1 C2 179.8(9) . . . . ?
C52 C6 N1 Zn01 -1.8(12) . . . . ?
C52 C51 N48 C47 -175.5(11) . . . . ?
C52 C51 N48 N49 2.7(15) . . . . ?
N1 C2 C3 C4 2.1(16) . . . . ?
N1 C2 C7 C8 173.5(10) . . . . ?
N1 C2 C7 N9 -0.6(12) . . . . ?
N1 C6 C52 C51 172.2(13) . . . . ?
N1 C6 C52 N50 0.7(15) . . . . ?
N9 C7 C8 N11 -2.4(10) . . . . ?
N9 N10 N11 C8 -2.1(10) . . . . ?
N9 N10 N11 C12 -177.6(7) . . . . ?
N11 C12 C13 O14 -66.0(8) . . . . ?
N24 C26 C27 C28 174.9(8) . . . . ?
N24 C26 C27 C32 -10.0(14) . . . . ?
N35 C36 C37 O38 -67.4(10) . . . . ?
N48 C51 C52 C6 -173.2(14) . . . . ?
N48 C51 C52 N50 -1.2(14) . . . . ?
N48 N49 N50 C52 1.9(13) . . . . ?
N48 N49 N50 Zn01 172.4(9) . . . . ?
O14 C15 C16 C17 177.0(9) . . . . ?
O14 C15 C20 C19 178.3(9) . . . . ?
O21 C18 C19 C20 179.8(9) . . . . ?
O21 C22 C23 N24 63.6(10) . . . . ?
O25 C26 C27 C28 -7.4(14) . . . . ?
O25 C26 C27 C32 167.7(10) . . . . ?
O25 C26 N24 C23 10.4(14) . . . . ?
O33 C34 N35 C36 0.7(16) . . . . ?
O38 C39 C40 C41 174.8(10) . . . . ?
O38 C39 C44 C43 179.7(9) . . . . ?
O45 C42 C43 C44 -179.9(10) . . . . ?
O45 C46 C47 N48 -57.0(12) . . . . ?
Zn01 N9 N10 N11 174.1(7) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.123 -0.550 -0.623 2586.4 909.6 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol/dichloromethane/diethyl ether'
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2225120'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2022-12-08 deposited with the CCDC.	2023-01-16 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 

;
_refine_special_details          
; 
Crystals were fine needles which grew in clusters. Even after many attempts to
obtain a single crystal, the diffraction images suggest the presence of either
a split crystal or a second minor crystal. This resulted in 17 reflections that 
had observed intensities that were significantly higher than calculated by the 
model. We suspect these were due to the split crystal and so these were 
removed manually by inspection of the Fo/Fc plot. Two additional reflections
appeared to be obscured by the beamstop and so these were also removed.

No crystallographic restraints were necessary.
;

_cell_length_a                   24.3689(9)
_cell_length_b                   6.0698(2)
_cell_length_c                   32.7063(13)
_cell_angle_alpha                90
_cell_angle_beta                 107.273(4)
_cell_angle_gamma                90
_cell_volume                     4619.6(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c '
_symmetry_space_group_name_Hall  '-C 2yc'

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

_chemical_formula_sum            'C44 H48 N16 O6'
_chemical_formula_moiety         'C38 H34 N14 O4, 2(C3 H7 N O)'
_chemical_compound_source        synthesized
_chemical_formula_weight         896.97


_cell_measurement_reflns_used    4489
_cell_measurement_theta_min      4.00
_cell_measurement_theta_max      72.4
_cell_measurement_temperature    150

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.03
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_max          0.50

_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1888
_exptl_absorpt_coefficient_mu    0.743

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.721
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            16692
_diffrn_reflns_av_unetI/netI     0.071
_reflns_number_total             4649
_diffrn_reflns_av_R_equivalents  0.042

_diffrn_reflns_theta_min         3.799
_diffrn_reflns_theta_max         73.888
_diffrn_measured_fraction_theta_max 0.989

_diffrn_reflns_theta_full        71.671
_diffrn_measured_fraction_theta_full 0.997

_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       40
_reflns_limit_h_min              -30
_reflns_limit_h_max              28
_reflns_limit_k_min              0
_reflns_limit_k_max              7
_reflns_limit_l_min              0
_reflns_limit_l_max              40

_oxford_diffrn_Wilson_B_factor   2.75
_oxford_diffrn_Wilson_scale      0.21

_atom_sites_solution_primary     other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.41
_refine_diff_density_max         0.42

_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4629
_refine_ls_R_factor_ref          0.0936
_refine_ls_wR_factor_ref         0.1946
_refine_ls_goodness_of_fit_ref   1.0341
_refine_ls_shift/su_max          0.0001374
_refine_ls_shift/su_mean         0.0000124

# Computed with I/sigma = -10 
_reflns_number_all               4630
_refine_ls_R_factor_all          0.0937
_refine_ls_wR_factor_all         0.1946

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3611
_refine_ls_R_factor_gt           0.0759
_refine_ls_wR_factor_gt          0.1848


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.03P)² +31.40P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.07394(12) 0.0442(5) 0.44540(9) 0.0278 1.0000 Uani . . . . . .
C2 C 0.02658(15) -0.0502(6) 0.45012(10) 0.0283 1.0000 Uani . . . . . .
C3 C 0.02654(16) -0.2544(6) 0.46940(12) 0.0330 1.0000 Uani . . . . . .
C4 C 0.07801(17) -0.3659(6) 0.48508(12) 0.0354 1.0000 Uani . . . . . .
C5 C 0.12755(16) -0.2686(6) 0.48127(11) 0.0327 1.0000 Uani . . . . . .
C6 C 0.12338(15) -0.0662(6) 0.46072(11) 0.0289 1.0000 Uani . . . . . .
C7 C -0.02710(15) 0.0749(6) 0.43264(11) 0.0296 1.0000 Uani . . . . . .
C8 C -0.03557(14) 0.2802(6) 0.41454(11) 0.0290 1.0000 Uani . . . . . .
N9 N -0.07900(13) -0.0068(5) 0.43367(11) 0.0355 1.0000 Uani . . . . . .
N10 N -0.11887(13) 0.1407(6) 0.41672(10) 0.0360 1.0000 Uani . . . . . .
N11 N -0.09274(12) 0.3145(5) 0.40537(9) 0.0300 1.0000 Uani . . . . . .
C12 C -0.12652(15) 0.5083(6) 0.38676(12) 0.0350 1.0000 Uani . . . . . .
C13 C -0.12887(16) 0.5401(6) 0.34068(12) 0.0352 1.0000 Uani . . . . . .
O14 O -0.15413(11) 0.3477(4) 0.31777(8) 0.0371 1.0000 Uani . . . . . .
C15 C -0.16943(15) 0.3546(6) 0.27399(11) 0.0305 1.0000 Uani . . . . . .
C16 C -0.16110(16) 0.5312(6) 0.25003(12) 0.0332 1.0000 Uani . . . . . .
C17 C -0.18298(16) 0.5248(6) 0.20521(12) 0.0332 1.0000 Uani . . . . . .
C18 C -0.21212(15) 0.3418(6) 0.18511(11) 0.0301 1.0000 Uani . . . . . .
C19 C -0.21808(15) 0.1594(6) 0.20936(12) 0.0319 1.0000 Uani . . . . . .
C20 C -0.19703(15) 0.1665(6) 0.25325(12) 0.0314 1.0000 Uani . . . . . .
C21 C 0.17430(15) 0.0387(6) 0.45414(11) 0.0290 1.0000 Uani . . . . . .
C22 C 0.18305(14) 0.2520(6) 0.44452(11) 0.0294 1.0000 Uani . . . . . .
N23 N 0.22294(14) -0.0778(6) 0.45640(11) 0.0411 1.0000 Uani . . . . . .
N24 N 0.26106(14) 0.0563(6) 0.44870(11) 0.0401 1.0000 Uani . . . . . .
N25 N 0.23703(12) 0.2574(5) 0.44191(9) 0.0288 1.0000 Uani . . . . . .
C26 C 0.26804(15) 0.4396(7) 0.42990(11) 0.0323 1.0000 Uani . . . . . .
C27 C 0.23873(15) 0.5080(6) 0.38450(11) 0.0315 1.0000 Uani . . . . . .
O28 O 0.23747(11) 0.3206(4) 0.35838(8) 0.0354 1.0000 Uani . . . . . .
O51 O 0.01201(17) -0.3584(7) 0.35402(13) 0.0729 1.0000 Uani . . . . . .
C52 C 0.0466(2) -0.2152(9) 0.35250(17) 0.0585 1.0000 Uani . . . . . .
N53 N 0.03566(17) -0.0209(7) 0.33289(13) 0.0533 1.0000 Uani . . . . . .
C54 C -0.0236(3) 0.0417(11) 0.3117(2) 0.0797 1.0000 Uani . . . . . .
C55 C 0.0806(3) 0.1395(11) 0.3346(2) 0.0825 1.0000 Uani . . . . . .
H31 H -0.0079 -0.3147 0.4719 0.0401 1.0000 Uiso R . . . . .
H41 H 0.0796 -0.5037 0.4981 0.0434 1.0000 Uiso R . . . . .
H51 H 0.1631 -0.3373 0.4924 0.0408 1.0000 Uiso R . . . . .
H81 H -0.0087 0.3800 0.4096 0.0358 1.0000 Uiso R . . . . .
H122 H -0.1100 0.6397 0.4031 0.0432 1.0000 Uiso R . . . . .
H121 H -0.1659 0.4884 0.3883 0.0428 1.0000 Uiso R . . . . .
H132 H -0.1526 0.6689 0.3294 0.0433 1.0000 Uiso R . . . . .
H131 H -0.0907 0.5613 0.3378 0.0430 1.0000 Uiso R . . . . .
H161 H -0.1415 0.6560 0.2633 0.0410 1.0000 Uiso R . . . . .
H171 H -0.1776 0.6460 0.1895 0.0402 1.0000 Uiso R . . . . .
H191 H -0.2358 0.0309 0.1961 0.0393 1.0000 Uiso R . . . . .
H201 H -0.2018 0.0413 0.2690 0.0389 1.0000 Uiso R . . . . .
H221 H 0.1576 0.3701 0.4406 0.0360 1.0000 Uiso R . . . . .
H262 H 0.2680 0.5631 0.4488 0.0400 1.0000 Uiso R . . . . .
H261 H 0.3070 0.3925 0.4328 0.0400 1.0000 Uiso R . . . . .
H272 H 0.2599 0.6290 0.3765 0.0388 1.0000 Uiso R . . . . .
H271 H 0.1995 0.5537 0.3816 0.0390 1.0000 Uiso R . . . . .
H521 H 0.0858 -0.2445 0.3664 0.0691 1.0000 Uiso R . . . . .
H543 H -0.0273 0.2009 0.3119 0.1182 1.0000 Uiso R . . . . .
H542 H -0.0490 -0.0252 0.3259 0.1180 1.0000 Uiso R . . . . .
H541 H -0.0344 -0.0097 0.2824 0.1181 1.0000 Uiso R . . . . .
H553 H 0.0802 0.1779 0.3058 0.1220 1.0000 Uiso R . . . . .
H552 H 0.0743 0.2694 0.3500 0.1218 1.0000 Uiso R . . . . .
H551 H 0.1172 0.0725 0.3495 0.1219 1.0000 Uiso R . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.97(2)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.338(4) yes
N1 . C6 . 1.339(4) yes
C2 . C3 . 1.391(5) yes
C2 . C7 . 1.473(5) yes
C3 . C4 . 1.383(5) yes
C3 . H31 . 0.940 no
C4 . C5 . 1.383(5) yes
C4 . H41 . 0.934 no
C5 . C6 . 1.389(5) yes
C5 . H51 . 0.933 no
C6 . C21 . 1.466(5) yes
C7 . C8 . 1.369(5) yes
C7 . N9 . 1.368(4) yes
C8 . N11 . 1.351(4) yes
C8 . H81 . 0.941 no
N9 . N10 . 1.317(5) yes
N10 . N11 . 1.340(4) yes
N11 . C12 . 1.461(5) yes
C12 . C13 . 1.504(5) yes
C12 . H122 . 0.977 no
C12 . H121 . 0.983 no
C13 . O14 . 1.425(4) yes
C13 . H132 . 0.978 no
C13 . H131 . 0.970 no
O14 . C15 . 1.369(4) yes
C15 . C16 . 1.378(5) yes
C15 . C20 . 1.394(5) yes
C16 . C17 . 1.404(5) yes
C16 . H161 . 0.931 no
C17 . C18 . 1.376(5) yes
C17 . H171 . 0.928 no
C18 . O28 6_555 1.378(4) yes
C18 . C19 . 1.395(5) yes
C19 . C20 . 1.374(5) yes
C19 . H191 . 0.934 no
C20 . H201 . 0.945 no
C21 . C22 . 1.364(5) yes
C21 . N23 . 1.363(5) yes
C22 . N25 . 1.344(4) yes
C22 . H221 . 0.931 no
N23 . N24 . 1.315(5) yes
N24 . N25 . 1.343(4) yes
N25 . C26 . 1.458(5) yes
C26 . C27 . 1.503(5) yes
C26 . H262 . 0.973 no
C26 . H261 . 0.970 no
C27 . O28 . 1.417(4) yes
C27 . H272 . 0.978 no
C27 . H271 . 0.973 no
O51 . C52 . 1.221(6) yes
C52 . N53 . 1.331(7) yes
C52 . H521 . 0.945 no
N53 . C54 . 1.456(7) yes
N53 . C55 . 1.454(6) yes
C54 . H543 . 0.970 no
C54 . H542 . 0.967 no
C54 . H541 . 0.967 no
C55 . H553 . 0.969 no
C55 . H552 . 0.971 no
C55 . H551 . 0.969 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C6 . 117.0(3) yes
N1 . C2 . C3 . 123.4(3) yes
N1 . C2 . C7 . 115.6(3) yes
C3 . C2 . C7 . 121.0(3) yes
C2 . C3 . C4 . 118.8(3) yes
C2 . C3 . H31 . 120.5 no
C4 . C3 . H31 . 120.7 no
C3 . C4 . C5 . 118.5(3) yes
C3 . C4 . H41 . 121.2 no
C5 . C4 . H41 . 120.2 no
C4 . C5 . C6 . 118.8(3) yes
C4 . C5 . H51 . 120.6 no
C6 . C5 . H51 . 120.6 no
C5 . C6 . N1 . 123.5(3) yes
C5 . C6 . C21 . 120.8(3) yes
N1 . C6 . C21 . 115.7(3) yes
C2 . C7 . C8 . 129.8(3) yes
C2 . C7 . N9 . 121.6(3) yes
C8 . C7 . N9 . 108.6(3) yes
C7 . C8 . N11 . 104.4(3) yes
C7 . C8 . H81 . 129.6 no
N11 . C8 . H81 . 125.9 no
C7 . N9 . N10 . 108.4(3) yes
N9 . N10 . N11 . 107.5(3) yes
C8 . N11 . N10 . 111.1(3) yes
C8 . N11 . C12 . 129.2(3) yes
N10 . N11 . C12 . 119.6(3) yes
N11 . C12 . C13 . 111.7(3) yes
N11 . C12 . H122 . 109.9 no
C13 . C12 . H122 . 109.2 no
N11 . C12 . H121 . 108.5 no
C13 . C12 . H121 . 108.7 no
H122 . C12 . H121 . 108.7 no
C12 . C13 . O14 . 107.7(3) yes
C12 . C13 . H132 . 108.9 no
O14 . C13 . H132 . 110.0 no
C12 . C13 . H131 . 111.2 no
O14 . C13 . H131 . 109.5 no
H132 . C13 . H131 . 109.5 no
C13 . O14 . C15 . 117.8(3) yes
O14 . C15 . C16 . 125.3(3) yes
O14 . C15 . C20 . 115.2(3) yes
C16 . C15 . C20 . 119.4(3) yes
C15 . C16 . C17 . 119.9(3) yes
C15 . C16 . H161 . 120.6 no
C17 . C16 . H161 . 119.5 no
C16 . C17 . C18 . 120.2(3) yes
C16 . C17 . H171 . 118.9 no
C18 . C17 . H171 . 120.9 no
O28 6_555 C18 . C17 . 125.3(3) yes
O28 6_555 C18 . C19 . 115.0(3) yes
C17 . C18 . C19 . 119.7(3) yes
C18 . C19 . C20 . 120.0(3) yes
C18 . C19 . H191 . 120.7 no
C20 . C19 . H191 . 119.3 no
C15 . C20 . C19 . 120.7(4) yes
C15 . C20 . H201 . 120.9 no
C19 . C20 . H201 . 118.4 no
C6 . C21 . C22 . 130.0(3) yes
C6 . C21 . N23 . 121.8(3) yes
C22 . C21 . N23 . 108.2(3) yes
C21 . C22 . N25 . 105.1(3) yes
C21 . C22 . H221 . 128.3 no
N25 . C22 . H221 . 126.6 no
C21 . N23 . N24 . 108.7(3) yes
N23 . N24 . N25 . 107.2(3) yes
C22 . N25 . N24 . 110.7(3) yes
C22 . N25 . C26 . 129.1(3) yes
N24 . N25 . C26 . 119.9(3) yes
N25 . C26 . C27 . 110.1(3) yes
N25 . C26 . H262 . 108.3 no
C27 . C26 . H262 . 109.1 no
N25 . C26 . H261 . 108.8 no
C27 . C26 . H261 . 110.0 no
H262 . C26 . H261 . 110.5 no
C26 . C27 . O28 . 107.0(3) yes
C26 . C27 . H272 . 109.8 no
O28 . C27 . H272 . 111.1 no
C26 . C27 . H271 . 109.9 no
O28 . C27 . H271 . 109.0 no
H272 . C27 . H271 . 110.0 no
C27 . O28 . C18 6_555 118.0(3) yes
O51 . C52 . N53 . 127.5(5) yes
O51 . C52 . H521 . 117.2 no
N53 . C52 . H521 . 115.3 no
C52 . N53 . C54 . 119.3(5) yes
C52 . N53 . C55 . 122.3(5) yes
C54 . N53 . C55 . 118.3(5) yes
N53 . C54 . H543 . 109.7 no
N53 . C54 . H542 . 110.4 no
H543 . C54 . H542 . 110.0 no
N53 . C54 . H541 . 109.1 no
H543 . C54 . H541 . 109.3 no
H542 . C54 . H541 . 108.4 no
N53 . C55 . H553 . 109.4 no
N53 . C55 . H552 . 109.4 no
H553 . C55 . H552 . 110.6 no
N53 . C55 . H551 . 107.9 no
H553 . C55 . H551 . 109.4 no
H552 . C55 . H551 . 110.1 no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C8 . H81 . O51 1_565 144 0.94 2.57 3.382(6) yes
C12 . H122 . N9 1_565 171 0.98 2.39 3.362(6) yes
C13 . H131 . O51 1_565 162 0.97 2.45 3.386(6) yes
C26 . H262 . N23 1_565 145 0.97 2.49 3.333(6) yes
C26 . H261 . N10 3_555 123 0.97 2.52 3.159(6) yes



# Manually omitted reflections
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
6 0 4 x .
4 0 6 x .
-6 0 2 x .
-3 1 1 x .
-5 1 15 x .
4 2 6 x .
-3 1 13 x .
5 1 5 x .
5 3 2 x .
-8 0 28 x .
11 1 6 x .
8 0 2 x .
5 1 2 x .
4 0 16 x .
7 3 20 x .
9 1 8 x .
2 0 18 x .
6 0 14 x .
7 1 3 x .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMF'
####################################################################### 
# 
# 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_PdBr_8_chloroform_methanol
_database_code_depnum_ccdc_archive 'CCDC 2225116'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2022-12-08 deposited with the CCDC.	2023-01-16 downloaded from the CCDC.
;
#==============================================================================
# start Validation Reply Form
_vrf_PLAT221_PdBr_8_chloroform_methanol 
;
PROBLEM: Solv./Anion  Resd 4  C   Ueq(max)/Ueq(min) Range        4.4 Ratio 
RESPONSE: This residue is one part of a disordered diethyl ether solvate.
;
_vrf_PLAT223_PdBr_8_chloroform_methanol 
;
PROBLEM: Solv./Anion  Resd 4  H   Ueq(max)/Ueq(min) Range        4.6 Ratio 
RESPONSE: This residue is one part of a disordered diethyl ether solvate.
;
_vrf_PLAT260_PdBr_8_chloroform_methanol 
;
PROBLEM: Large Average Ueq of Residue Including      O103      0.203 Check 
RESPONSE: This residue is one part of a disordered diethyl ether solvate.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 

;
_refine_special_details          
; 
Most of the structure refines very smoothly. The exception is a diethyl ether
solvent molecule located in the centre of the macrocycle. This was modelled 
as disordered over two parts (occupancies 0.5:0.5), and required the use 
of bond distance, bond angle, planarity and thermal and vibrational ellipsoid
restraints for this disordered solvent. Despite these restraints, the thermal
ellipsoids for the diethyl ether atoms are relatively large, resulting in 
Level C CIFcheck alerts.

With the exception of the disordered diethyl ether solvent molecule,
C-H hydrogen atoms were  visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. Amide N-H hydrogen 
atoms were visible in the Fourier difference map and were refined
with restraints on bond lengths and angles. Given the difficulties in modelling
the disordered diethyl ether solvent, the hydrogen atoms on this group were
inserted at calculated positions and used as the basis for a riding model.

;

_cell_length_a                   13.2676(3)
_cell_length_b                   13.9658(4)
_cell_length_c                   14.0241(4)
_cell_angle_alpha                66.859(3)
_cell_angle_beta                 81.243(2)
_cell_angle_gamma                71.620(2)
_cell_volume                     2266.39(12)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
B 0.0090 0.0039 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Pd 0.1215 3.9337 19.3319 0.6987 15.5017 7.9893 5.2954 25.2052 0.6058 76.8986
5.2659 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.6763 1.2805 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            2

_chemical_formula_sum            'C41 H45 B Br F4 N9 O7 Pd'
_chemical_formula_moiety         'C37 H35 Br N9 O6 Pd, B F4, C4 H10 O'
_chemical_compound_source        synthesized
_chemical_formula_weight         1048.97


_cell_measurement_reflns_used    15685
_cell_measurement_theta_min      4.48
_cell_measurement_theta_max      73.04
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.15
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_max          0.22

_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1064
_exptl_absorpt_coefficient_mu    4.980

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.954
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            28193
_diffrn_reflns_av_unetI/netI     0.041
_reflns_number_total             9052
_diffrn_reflns_av_R_equivalents  0.026

_diffrn_reflns_theta_min         3.512
_diffrn_reflns_theta_max         73.294
_diffrn_measured_fraction_theta_max 0.994

_diffrn_reflns_theta_full        71.828
_diffrn_measured_fraction_theta_full 0.999

_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_reflns_limit_h_min              -16
_reflns_limit_h_max              16
_reflns_limit_k_min              -15
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   1.48
_oxford_diffrn_Wilson_scale      0.08

_atom_sites_solution_primary     other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.98
_refine_diff_density_max         1.04


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     94
_refine_ls_number_parameters     630
_refine_ls_number_reflns         9052
_refine_ls_R_factor_ref          0.0367
_refine_ls_wR_factor_ref         0.0922
_refine_ls_goodness_of_fit_ref   1.0137
_refine_ls_shift/su_max          0.0010595
_refine_ls_shift/su_mean         0.0000345

# Computed with I/sigma = -10 
_reflns_number_all               9052
_refine_ls_R_factor_all          0.0367
_refine_ls_wR_factor_all         0.0922

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                8661
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_gt          0.0910


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 5.02P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.62752(19) 0.37336(19) 0.41775(18) 0.0179 1.0000 Uani . . . . . .
C2 C 0.6240(2) 0.4228(2) 0.3143(2) 0.0198 1.0000 Uani . . . . . .
C3 C 0.6249(3) 0.3652(2) 0.2533(2) 0.0234 1.0000 Uani . . . . . .
C4 C 0.6303(3) 0.2555(2) 0.3025(2) 0.0257 1.0000 Uani . . . . . .
C5 C 0.6343(2) 0.2052(2) 0.4098(2) 0.0228 1.0000 Uani . . . . . .
C6 C 0.6326(2) 0.2676(2) 0.4666(2) 0.0196 1.0000 Uani . . . . . .
C7 C 0.6195(2) 0.5368(2) 0.2819(2) 0.0190 1.0000 Uani . . . . . .
C8 C 0.6144(2) 0.6237(2) 0.1897(2) 0.0185 1.0000 Uani . . . . . .
N9 N 0.62068(19) 0.57414(19) 0.35902(18) 0.0186 1.0000 Uani . . . . . .
N10 N 0.6160(2) 0.6770(2) 0.32064(19) 0.0207 1.0000 Uani . . . . . .
N11 N 0.61227(19) 0.70648(19) 0.21849(18) 0.0197 1.0000 Uani . . . . . .
C12 C 0.6162(2) 0.8165(2) 0.1495(2) 0.0214 1.0000 Uani . . . . . .
C13 C 0.7251(2) 0.8113(2) 0.0973(2) 0.0224 1.0000 Uani . . . . . .
O14 O 0.79896(18) 0.7590(2) 0.17800(17) 0.0298 1.0000 Uani . . . . . .
C15 C 0.9057(2) 0.7452(3) 0.1506(2) 0.0255 1.0000 Uani . . . . . .
C16 C 0.9454(2) 0.7882(2) 0.0510(2) 0.0250 1.0000 Uani . . . . . .
C17 C 1.0553(3) 0.7732(3) 0.0336(3) 0.0270 1.0000 Uani . . . . . .
C18 C 1.1228(2) 0.7152(3) 0.1160(3) 0.0275 1.0000 Uani . . . . . .
C19 C 1.0821(3) 0.6707(3) 0.2159(3) 0.0348 1.0000 Uani . . . . . .
C20 C 0.9739(3) 0.6857(3) 0.2331(3) 0.0342 1.0000 Uani . . . . . .
O21 O 1.23014(18) 0.7024(2) 0.1082(2) 0.0348 1.0000 Uani . . . . . .
C22 C 1.2877(3) 0.6960(3) 0.0150(3) 0.0278 1.0000 Uani . . . . . .
C23 C 1.3909(2) 0.6079(2) 0.0504(2) 0.0250 1.0000 Uani D . . . . .
N24 N 1.3692(2) 0.5048(2) 0.11378(19) 0.0234 1.0000 Uani D . . . . .
O25 O 1.33372(19) 0.47953(18) -0.02544(16) 0.0289 1.0000 Uani . . . . . .
C26 C 1.3337(2) 0.4524(2) 0.0698(2) 0.0218 1.0000 Uani D . . . . .
C27 C 1.2929(2) 0.3591(2) 0.1403(2) 0.0216 1.0000 Uani . . . . . .
C28 C 1.3309(2) 0.2943(2) 0.2393(2) 0.0199 1.0000 Uani . . . . . .
C29 C 1.2940(2) 0.2044(2) 0.2982(2) 0.0207 1.0000 Uani . . . . . .
C30 C 1.2193(3) 0.1806(3) 0.2585(3) 0.0281 1.0000 Uani . . . . . .
C31 C 1.1786(3) 0.2476(3) 0.1613(3) 0.0319 1.0000 Uani . . . . . .
C32 C 1.2163(3) 0.3356(3) 0.1020(2) 0.0285 1.0000 Uani . . . . . .
O33 O 1.35305(19) 0.02822(17) 0.42463(17) 0.0268 1.0000 Uani . . . . . .
C34 C 1.3373(2) 0.1259(2) 0.4018(2) 0.0212 1.0000 Uani D . . . . .
N35 N 1.3558(2) 0.1690(2) 0.46567(19) 0.0240 1.0000 Uani D . . . . .
C36 C 1.3933(2) 0.1034(3) 0.5709(2) 0.0242 1.0000 Uani D . . . . .
C37 C 1.3038(2) 0.0883(3) 0.6509(2) 0.0239 1.0000 Uani . . . . . .
O38 O 1.25102(18) 0.0242(2) 0.63063(18) 0.0301 1.0000 Uani . . . . . .
C39 C 1.1562(3) 0.0163(3) 0.6827(3) 0.0263 1.0000 Uani . . . . . .
C40 C 1.1211(2) 0.0429(3) 0.7698(2) 0.0259 1.0000 Uani . . . . . .
C41 C 1.0204(2) 0.0374(3) 0.8142(2) 0.0252 1.0000 Uani . . . . . .
C42 C 0.9559(2) 0.0047(2) 0.7719(2) 0.0243 1.0000 Uani . . . . . .
C43 C 0.9932(3) -0.0263(4) 0.6870(3) 0.0411 1.0000 Uani . . . . . .
C44 C 1.0927(3) -0.0209(4) 0.6430(3) 0.0417 1.0000 Uani . . . . . .
O45 O 0.85344(17) 0.00091(18) 0.80827(18) 0.0260 1.0000 Uani . . . . . .
C46 C 0.7998(2) 0.0689(2) 0.8650(2) 0.0212 1.0000 Uani . . . . . .
C47 C 0.6818(2) 0.0959(2) 0.8521(2) 0.0213 1.0000 Uani . . . . . .
N48 N 0.65484(19) 0.1680(2) 0.74411(17) 0.0189 1.0000 Uani . . . . . .
N49 N 0.6490(2) 0.2719(2) 0.71519(18) 0.0204 1.0000 Uani . . . . . .
N50 N 0.63968(19) 0.31215(19) 0.61416(18) 0.0187 1.0000 Uani . . . . . .
C51 C 0.6500(2) 0.1388(2) 0.6635(2) 0.0190 1.0000 Uani . . . . . .
C52 C 0.6395(2) 0.2338(2) 0.5786(2) 0.0190 1.0000 Uani . . . . . .
C101 C 0.9419(7) 0.2759(19) 0.5184(14) 0.1562 0.5000 Uani D U . . 1 .
C102 C 0.9230(8) 0.3800(15) 0.4292(16) 0.1868 0.5000 Uani D U . . 1 .
O113 O 0.8777(6) 0.3755(7) 0.3576(6) 0.1289 0.5000 Uani D U . . 2 .
C104 C 0.9064(8) 0.4414(15) 0.2468(16) 0.2326 0.5000 Uani D U . . 1 .
C105 C 0.9045(8) 0.400(2) 0.1649(16) 0.2227 0.5000 Uani D U . . 1 .
Pd1 Pd 0.630728(15) 0.457908(15) 0.501637(14) 0.0165 1.0000 Uani . . . . . .
Br1 Br 0.64991(3) 0.55518(3) 0.60372(2) 0.0289 1.0000 Uani . . . . . .
F15 F 0.62799(18) 0.05460(17) 0.08439(16) 0.0398 1.0000 Uani . . . . . .
B11 B 0.5286(3) 0.1162(3) 0.1092(3) 0.0251 1.0000 Uani . . . . . .
F12 F 0.4592(2) 0.0549(2) 0.1441(3) 0.0715 1.0000 Uani . . . . . .
F14 F 0.5427(2) 0.1500(2) 0.1840(2) 0.0541 1.0000 Uani . . . . . .
F13 F 0.4929(2) 0.2065(2) 0.02070(19) 0.0547 1.0000 Uani . . . . . .
C111 C 0.8893(19) 0.2756(11) 0.5432(10) 0.2625 0.5000 Uani D U . . 2 .
C112 C 0.9461(11) 0.3010(8) 0.4439(9) 0.2230 0.5000 Uani D U . . 2 .
O103 O 0.9184(7) 0.3530(14) 0.3420(14) 0.2153 0.5000 Uani D U . . 1 .
C114 C 0.9513(7) 0.3871(7) 0.2738(7) 0.1086 0.5000 Uani D U . . 2 .
C115 C 0.9010(8) 0.4588(7) 0.1743(7) 0.0598 0.5000 Uani D U . . 2 .
H31 H 0.6220 0.3997 0.1808 0.0285 1.0000 Uiso R . . . . .
H41 H 0.6316 0.2168 0.2613 0.0313 1.0000 Uiso R . . . . .
H51 H 0.6360 0.1327 0.4430 0.0273 1.0000 Uiso R . . . . .
H81 H 0.6143 0.6264 0.1230 0.0226 1.0000 Uiso R . . . . .
H121 H 0.6025 0.8601 0.1916 0.0259 1.0000 Uiso R . . . . .
H122 H 0.5619 0.8459 0.0985 0.0257 1.0000 Uiso R . . . . .
H131 H 0.7291 0.8857 0.0584 0.0267 1.0000 Uiso R . . . . .
H132 H 0.7402 0.7715 0.0510 0.0269 1.0000 Uiso R . . . . .
H161 H 0.8994 0.8270 -0.0056 0.0301 1.0000 Uiso R . . . . .
H171 H 1.0833 0.8036 -0.0341 0.0330 1.0000 Uiso R . . . . .
H191 H 1.1290 0.6280 0.2734 0.0412 1.0000 Uiso R . . . . .
H201 H 0.9459 0.6557 0.3004 0.0410 1.0000 Uiso R . . . . .
H221 H 1.3017 0.7649 -0.0271 0.0328 1.0000 Uiso R . . . . .
H222 H 1.2477 0.6763 -0.0249 0.0322 1.0000 Uiso R . . . . .
H231 H 1.4262 0.6271 0.0929 0.0299 1.0000 Uiso R . . . . .
H232 H 1.4352 0.6008 -0.0101 0.0299 1.0000 Uiso R . . . . .
H281 H 1.3806 0.3115 0.2649 0.0235 1.0000 Uiso R . . . . .
H301 H 1.1968 0.1172 0.2997 0.0340 1.0000 Uiso R . . . . .
H311 H 1.1282 0.2318 0.1344 0.0379 1.0000 Uiso R . . . . .
H321 H 1.1896 0.3790 0.0353 0.0348 1.0000 Uiso R . . . . .
H362 H 1.4337 0.1403 0.5884 0.0286 1.0000 Uiso R . . . . .
H361 H 1.4396 0.0338 0.5721 0.0293 1.0000 Uiso R . . . . .
H371 H 1.3302 0.0528 0.7208 0.0290 1.0000 Uiso R . . . . .
H372 H 1.2545 0.1586 0.6428 0.0289 1.0000 Uiso R . . . . .
H401 H 1.1637 0.0645 0.7998 0.0309 1.0000 Uiso R . . . . .
H411 H 0.9957 0.0570 0.8718 0.0302 1.0000 Uiso R . . . . .
H431 H 0.9512 -0.0523 0.6601 0.0488 1.0000 Uiso R . . . . .
H441 H 1.1179 -0.0411 0.5847 0.0503 1.0000 Uiso R . . . . .
H462 H 0.8155 0.0319 0.9375 0.0263 1.0000 Uiso R . . . . .
H461 H 0.8216 0.1348 0.8384 0.0252 1.0000 Uiso R . . . . .
H471 H 0.6426 0.1339 0.8973 0.0258 1.0000 Uiso R . . . . .
H472 H 0.6593 0.0315 0.8665 0.0255 1.0000 Uiso R . . . . .
H511 H 0.6550 0.0702 0.6679 0.0231 1.0000 Uiso R . . . . .
H241 H 1.357(3) 0.492(2) 0.1780(15) 0.028(2) 1.0000 Uiso D . . . . .
H351 H 1.343(3) 0.2379(15) 0.4446(17) 0.028(2) 1.0000 Uiso D . . . . .
H1011 H 0.9457 0.2872 0.5801 0.1810 0.5000 Uiso R . . . 1 .
H1012 H 1.0073 0.2286 0.5060 0.1810 0.5000 Uiso R . . . 1 .
H1013 H 0.8859 0.2444 0.5258 0.1810 0.5000 Uiso R . . . 1 .
H1021 H 0.9871 0.3666 0.4607 0.2155 0.5000 Uiso R . . . 1 .
H1022 H 0.8648 0.3891 0.4766 0.2155 0.5000 Uiso R . . . 1 .
H1041 H 0.9636 0.4726 0.2339 0.2768 0.5000 Uiso R . . . 1 .
H1042 H 0.8413 0.4944 0.2492 0.2768 0.5000 Uiso R . . . 1 .
H1051 H 0.8954 0.4589 0.0999 0.2607 0.5000 Uiso R . . . 1 .
H1052 H 0.9697 0.3470 0.1632 0.2607 0.5000 Uiso R . . . 1 .
H1053 H 0.8474 0.3688 0.1785 0.2607 0.5000 Uiso R . . . 1 .
H1111 H 0.9376 0.2270 0.5965 0.3226 0.5000 Uiso R . . . 2 .
H1112 H 0.8562 0.3406 0.5560 0.3226 0.5000 Uiso R . . . 2 .
H1113 H 0.8368 0.2429 0.5423 0.3226 0.5000 Uiso R . . . 2 .
H1121 H 0.9988 0.3329 0.4462 0.2704 0.5000 Uiso R . . . 2 .
H1122 H 0.9794 0.2353 0.4325 0.2704 0.5000 Uiso R . . . 2 .
H1141 H 1.0023 0.4165 0.2845 0.1316 0.5000 Uiso R . . . 2 .
H1142 H 0.9859 0.3175 0.2709 0.1316 0.5000 Uiso R . . . 2 .
H1151 H 0.9537 0.4639 0.1199 0.0709 0.5000 Uiso R . . . 2 .
H1152 H 0.8666 0.5289 0.1761 0.0709 0.5000 Uiso R . . . 2 .
H1153 H 0.8502 0.4299 0.1625 0.0709 0.5000 Uiso R . . . 2 .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.17(2)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.341(4) yes
N1 . C6 . 1.346(4) yes
N1 . Pd1 . 1.980(2) yes
C2 . C3 . 1.382(4) yes
C2 . C7 . 1.457(4) yes
C3 . C4 . 1.394(4) yes
C3 . H31 . 0.939 no
C4 . C5 . 1.389(4) yes
C4 . H41 . 0.930 no
C5 . C6 . 1.387(4) yes
C5 . H51 . 0.927 no
C6 . C52 . 1.461(4) yes
C7 . C8 . 1.375(4) yes
C7 . N9 . 1.377(4) yes
C7 . Pd1 . 2.846(3) yes
C8 . N11 . 1.358(4) yes
C8 . H81 . 0.921 no
N9 . N10 . 1.305(3) yes
N9 . Pd1 . 2.011(2) yes
N10 . N11 . 1.330(3) yes
N11 . C12 . 1.471(3) yes
C12 . C13 . 1.512(4) yes
C12 . H121 . 0.966 no
C12 . H122 . 0.969 no
C13 . O14 . 1.418(4) yes
C13 . H131 . 0.980 no
C13 . H132 . 0.972 no
O14 . C15 . 1.383(4) yes
C15 . C16 . 1.380(4) yes
C15 . C20 . 1.391(5) yes
C16 . C17 . 1.402(4) yes
C16 . H161 . 0.948 no
C17 . C18 . 1.384(5) yes
C17 . H171 . 0.946 no
C18 . C19 . 1.392(5) yes
C18 . O21 . 1.371(4) yes
C19 . C20 . 1.380(5) yes
C19 . H191 . 0.966 no
C20 . H201 . 0.942 no
O21 . C22 . 1.430(4) yes
C22 . C23 . 1.516(4) yes
C22 . H221 . 0.970 no
C22 . H222 . 0.987 no
C23 . N24 . 1.458(4) yes
C23 . H231 . 0.969 no
C23 . H232 . 0.976 no
N24 . C26 . 1.340(4) yes
N24 . H241 . 0.848(18) no
O25 . C26 . 1.237(4) yes
C26 . C27 . 1.496(4) yes
C27 . C28 . 1.392(4) yes
C27 . C32 . 1.395(4) yes
C28 . C29 . 1.396(4) yes
C28 . H281 . 0.928 no
C29 . C30 . 1.386(4) yes
C29 . C34 . 1.500(4) yes
C30 . C31 . 1.389(5) yes
C30 . H301 . 0.959 no
C31 . C32 . 1.381(5) yes
C31 . H311 . 0.935 no
C32 . H321 . 0.942 no
O33 . C34 . 1.227(4) yes
C34 . N35 . 1.345(4) yes
N35 . C36 . 1.462(4) yes
N35 . H351 . 0.854(18) no
C36 . C37 . 1.511(4) yes
C36 . H362 . 0.962 no
C36 . H361 . 0.968 no
C37 . O38 . 1.424(4) yes
C37 . H371 . 0.970 no
C37 . H372 . 0.967 no
O38 . C39 . 1.369(4) yes
C39 . C40 . 1.385(4) yes
C39 . C44 . 1.391(5) yes
C40 . C41 . 1.397(4) yes
C40 . H401 . 0.931 no
C41 . C42 . 1.381(4) yes
C41 . H411 . 0.934 no
C42 . C43 . 1.393(5) yes
C42 . O45 . 1.387(4) yes
C43 . C44 . 1.380(5) yes
C43 . H431 . 0.941 no
C44 . H441 . 0.949 no
O45 . C46 . 1.427(3) yes
C46 . C47 . 1.513(4) yes
C46 . H462 . 0.963 no
C46 . H461 . 0.967 no
C47 . N48 . 1.475(3) yes
C47 . H471 . 0.972 no
C47 . H472 . 0.972 no
N48 . N49 . 1.323(3) yes
N48 . C51 . 1.359(4) yes
N49 . N50 . 1.312(3) yes
N50 . C52 . 1.370(4) yes
N50 . Pd1 . 2.007(2) yes
C51 . C52 . 1.375(4) yes
C51 . H511 . 0.918 no
C52 . Pd1 . 2.851(3) yes
C101 . C102 . 1.475(10) yes
C101 . H1011 . 0.950 no
C101 . H1012 . 0.950 no
C101 . H1013 . 0.950 no
C102 . O103 . 1.430(10) yes
C102 . H1021 . 0.950 no
C102 . H1022 . 0.950 no
O113 . C112 . 1.456(9) yes
O113 . C114 . 1.401(8) yes
C104 . C105 . 1.480(10) yes
C104 . O103 . 1.407(10) yes
C104 . H1041 . 0.950 no
C104 . H1042 . 0.950 no
C105 . H1051 . 0.950 no
C105 . H1052 . 0.950 no
C105 . H1053 . 0.950 no
Pd1 . Br1 . 2.4120(3) yes
F15 . B11 . 1.407(4) yes
B11 . F12 . 1.361(4) yes
B11 . F14 . 1.365(4) yes
B11 . F13 . 1.388(4) yes
C111 . C112 . 1.448(9) yes
C111 . H1111 . 0.950 no
C111 . H1112 . 0.950 no
C111 . H1113 . 0.950 no
C112 . H1121 . 0.950 no
C112 . H1122 . 0.950 no
C114 . C115 . 1.470(8) yes
C114 . H1141 . 0.950 no
C114 . H1142 . 0.950 no
C115 . H1151 . 0.950 no
C115 . H1152 . 0.950 no
C115 . H1153 . 0.950 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C6 . 122.6(2) yes
C2 . N1 . Pd1 . 118.66(19) yes
C6 . N1 . Pd1 . 118.69(19) yes
N1 . C2 . C3 . 120.1(3) yes
N1 . C2 . C7 . 111.3(2) yes
C3 . C2 . C7 . 128.6(3) yes
C2 . C3 . C4 . 118.1(3) yes
C2 . C3 . H31 . 120.4 no
C4 . C3 . H31 . 121.5 no
C3 . C4 . C5 . 121.2(3) yes
C3 . C4 . H41 . 118.0 no
C5 . C4 . H41 . 120.8 no
C4 . C5 . C6 . 117.8(3) yes
C4 . C5 . H51 . 121.6 no
C6 . C5 . H51 . 120.6 no
C5 . C6 . N1 . 120.1(3) yes
C5 . C6 . C52 . 128.6(3) yes
N1 . C6 . C52 . 111.3(2) yes
C2 . C7 . C8 . 136.6(3) yes
C2 . C7 . N9 . 116.9(2) yes
C8 . C7 . N9 . 106.5(2) yes
C2 . C7 . Pd1 . 76.31(16) yes
C8 . C7 . Pd1 . 147.1(2) yes
N9 . C7 . Pd1 . 40.60(13) yes
C7 . C8 . N11 . 104.0(2) yes
C7 . C8 . H81 . 129.1 no
N11 . C8 . H81 . 126.8 no
C7 . N9 . N10 . 111.3(2) yes
C7 . N9 . Pd1 . 112.95(18) yes
N10 . N9 . Pd1 . 135.79(19) yes
N9 . N10 . N11 . 105.3(2) yes
C8 . N11 . N10 . 113.0(2) yes
C8 . N11 . C12 . 126.9(2) yes
N10 . N11 . C12 . 119.8(2) yes
N11 . C12 . C13 . 109.4(2) yes
N11 . C12 . H121 . 107.8 no
C13 . C12 . H121 . 110.0 no
N11 . C12 . H122 . 108.6 no
C13 . C12 . H122 . 110.7 no
H121 . C12 . H122 . 110.2 no
C12 . C13 . O14 . 106.3(2) yes
C12 . C13 . H131 . 108.3 no
O14 . C13 . H131 . 109.8 no
C12 . C13 . H132 . 112.4 no
O14 . C13 . H132 . 110.1 no
H131 . C13 . H132 . 110.0 no
C13 . O14 . C15 . 117.9(2) yes
O14 . C15 . C16 . 124.7(3) yes
O14 . C15 . C20 . 114.7(3) yes
C16 . C15 . C20 . 120.5(3) yes
C15 . C16 . C17 . 119.5(3) yes
C15 . C16 . H161 . 120.7 no
C17 . C16 . H161 . 119.8 no
C16 . C17 . C18 . 119.9(3) yes
C16 . C17 . H171 . 120.2 no
C18 . C17 . H171 . 119.9 no
C17 . C18 . C19 . 120.1(3) yes
C17 . C18 . O21 . 124.3(3) yes
C19 . C18 . O21 . 115.5(3) yes
C18 . C19 . C20 . 119.9(3) yes
C18 . C19 . H191 . 120.6 no
C20 . C19 . H191 . 119.5 no
C15 . C20 . C19 . 120.0(3) yes
C15 . C20 . H201 . 119.6 no
C19 . C20 . H201 . 120.3 no
C18 . O21 . C22 . 119.5(3) yes
O21 . C22 . C23 . 105.3(3) yes
O21 . C22 . H221 . 110.1 no
C23 . C22 . H221 . 110.5 no
O21 . C22 . H222 . 110.8 no
C23 . C22 . H222 . 110.3 no
H221 . C22 . H222 . 109.7 no
C22 . C23 . N24 . 110.2(2) yes
C22 . C23 . H231 . 108.5 no
N24 . C23 . H231 . 108.0 no
C22 . C23 . H232 . 109.5 no
N24 . C23 . H232 . 109.5 no
H231 . C23 . H232 . 111.2 no
C23 . N24 . C26 . 120.0(3) yes
C23 . N24 . H241 . 116.9(14) no
C26 . N24 . H241 . 118.9(14) no
N24 . C26 . O25 . 122.0(3) yes
N24 . C26 . C27 . 117.6(3) yes
O25 . C26 . C27 . 120.4(3) yes
C26 . C27 . C28 . 122.6(3) yes
C26 . C27 . C32 . 117.4(3) yes
C28 . C27 . C32 . 120.0(3) yes
C27 . C28 . C29 . 119.4(3) yes
C27 . C28 . H281 . 119.4 no
C29 . C28 . H281 . 121.1 no
C28 . C29 . C30 . 120.1(3) yes
C28 . C29 . C34 . 122.6(3) yes
C30 . C29 . C34 . 117.2(3) yes
C29 . C30 . C31 . 120.3(3) yes
C29 . C30 . H301 . 118.5 no
C31 . C30 . H301 . 121.2 no
C30 . C31 . C32 . 119.8(3) yes
C30 . C31 . H311 . 120.4 no
C32 . C31 . H311 . 119.8 no
C27 . C32 . C31 . 120.3(3) yes
C27 . C32 . H321 . 120.8 no
C31 . C32 . H321 . 118.9 no
C29 . C34 . O33 . 120.0(3) yes
C29 . C34 . N35 . 116.4(3) yes
O33 . C34 . N35 . 123.6(3) yes
C34 . N35 . C36 . 122.8(3) yes
C34 . N35 . H351 . 118.5(13) no
C36 . N35 . H351 . 118.7(13) no
N35 . C36 . C37 . 112.9(3) yes
N35 . C36 . H362 . 107.9 no
C37 . C36 . H362 . 107.8 no
N35 . C36 . H361 . 109.0 no
C37 . C36 . H361 . 110.4 no
H362 . C36 . H361 . 108.7 no
C36 . C37 . O38 . 107.4(2) yes
C36 . C37 . H371 . 111.3 no
O38 . C37 . H371 . 110.3 no
C36 . C37 . H372 . 108.7 no
O38 . C37 . H372 . 109.0 no
H371 . C37 . H372 . 110.0 no
C37 . O38 . C39 . 116.9(2) yes
O38 . C39 . C40 . 124.5(3) yes
O38 . C39 . C44 . 116.0(3) yes
C40 . C39 . C44 . 119.6(3) yes
C39 . C40 . C41 . 120.1(3) yes
C39 . C40 . H401 . 121.1 no
C41 . C40 . H401 . 118.8 no
C40 . C41 . C42 . 120.1(3) yes
C40 . C41 . H411 . 120.4 no
C42 . C41 . H411 . 119.5 no
C41 . C42 . C43 . 119.6(3) yes
C41 . C42 . O45 . 124.1(3) yes
C43 . C42 . O45 . 116.4(3) yes
C42 . C43 . C44 . 120.3(3) yes
C42 . C43 . H431 . 120.0 no
C44 . C43 . H431 . 119.7 no
C39 . C44 . C43 . 120.2(3) yes
C39 . C44 . H441 . 119.3 no
C43 . C44 . H441 . 120.4 no
C42 . O45 . C46 . 116.5(2) yes
O45 . C46 . C47 . 107.7(2) yes
O45 . C46 . H462 . 110.5 no
C47 . C46 . H462 . 109.5 no
O45 . C46 . H461 . 110.2 no
C47 . C46 . H461 . 109.9 no
H462 . C46 . H461 . 109.2 no
C46 . C47 . N48 . 109.6(2) yes
C46 . C47 . H471 . 109.6 no
N48 . C47 . H471 . 108.0 no
C46 . C47 . H472 . 112.2 no
N48 . C47 . H472 . 107.3 no
H471 . C47 . H472 . 110.1 no
C47 . N48 . N49 . 118.5(2) yes
C47 . N48 . C51 . 127.5(2) yes
N49 . N48 . C51 . 113.2(2) yes
N48 . N49 . N50 . 105.3(2) yes
N49 . N50 . C52 . 110.9(2) yes
N49 . N50 . Pd1 . 135.19(19) yes
C52 . N50 . Pd1 . 113.84(18) yes
N48 . C51 . C52 . 103.7(2) yes
N48 . C51 . H511 . 125.9 no
C52 . C51 . H511 . 130.4 no
C6 . C52 . C51 . 136.7(3) yes
C6 . C52 . N50 . 116.4(2) yes
C51 . C52 . N50 . 106.9(2) yes
C6 . C52 . Pd1 . 76.30(16) yes
C51 . C52 . Pd1 . 146.9(2) yes
N50 . C52 . Pd1 . 40.08(13) yes
C102 . C101 . H1011 . 110.0 no
C102 . C101 . H1012 . 108.5 no
H1011 . C101 . H1012 . 109.5 no
C102 . C101 . H1013 . 109.9 no
H1011 . C101 . H1013 . 109.5 no
H1012 . C101 . H1013 . 109.5 no
C101 . C102 . O103 . 104.9(9) yes
C101 . C102 . H1021 . 70.5 no
O103 . C102 . H1021 . 123.9 no
C101 . C102 . H1022 . 74.3 no
O103 . C102 . H1022 . 123.3 no
H1021 . C102 . H1022 . 109.5 no
C112 . O113 . C114 . 101.4(7) yes
C105 . C104 . O103 . 107.4(9) yes
C105 . C104 . H1041 . 110.5 no
O103 . C104 . H1041 . 110.4 no
C105 . C104 . H1042 . 110.1 no
O103 . C104 . H1042 . 109.0 no
H1041 . C104 . H1042 . 109.5 no
C104 . C105 . H1051 . 108.8 no
C104 . C105 . H1052 . 109.6 no
H1051 . C105 . H1052 . 109.5 no
C104 . C105 . H1053 . 110.0 no
H1051 . C105 . H1053 . 109.5 no
H1052 . C105 . H1053 . 109.5 no
N9 . Pd1 . N50 . 159.92(9) yes
N9 . Pd1 . N1 . 80.10(9) yes
N50 . Pd1 . N1 . 79.81(9) yes
N9 . Pd1 . C7 . 26.45(9) yes
N50 . Pd1 . C7 . 133.47(9) yes
N1 . Pd1 . C7 . 53.66(9) yes
N9 . Pd1 . C52 . 133.84(9) yes
N50 . Pd1 . C52 . 26.07(9) yes
N1 . Pd1 . C52 . 53.74(9) yes
C7 . Pd1 . C52 . 107.40(8) yes
N9 . Pd1 . Br1 . 100.45(7) yes
N50 . Pd1 . Br1 . 99.57(7) yes
N1 . Pd1 . Br1 . 175.42(7) yes
C7 . Pd1 . Br1 . 126.73(6) yes
C52 . Pd1 . Br1 . 125.53(6) yes
F15 . B11 . F12 . 110.0(3) yes
F15 . B11 . F14 . 108.1(3) yes
F12 . B11 . F14 . 110.4(3) yes
F15 . B11 . F13 . 107.9(3) yes
F12 . B11 . F13 . 111.5(3) yes
F14 . B11 . F13 . 108.8(3) yes
C112 . C111 . H1111 . 109.7 no
C112 . C111 . H1112 . 109.1 no
H1111 . C111 . H1112 . 109.5 no
C112 . C111 . H1113 . 109.6 no
H1111 . C111 . H1113 . 109.5 no
H1112 . C111 . H1113 . 109.5 no
O113 . C112 . C111 . 113.3(8) yes
O113 . C112 . H1121 . 108.6 no
C111 . C112 . H1121 . 108.6 no
O113 . C112 . H1122 . 108.7 no
C111 . C112 . H1122 . 108.2 no
H1121 . C112 . H1122 . 109.5 no
C102 . O103 . C104 . 114.0(9) yes
O113 . C114 . C115 . 112.4(6) yes
O113 . C114 . H1141 . 109.0 no
C115 . C114 . H1141 . 108.7 no
O113 . C114 . H1142 . 108.4 no
C115 . C114 . H1142 . 108.8 no
H1141 . C114 . H1142 . 109.5 no
C114 . C115 . H1151 . 109.4 no
C114 . C115 . H1152 . 109.5 no
H1151 . C115 . H1152 . 109.5 no
C114 . C115 . H1153 . 109.5 no
H1151 . C115 . H1153 . 109.5 no
H1152 . C115 . H1153 . 109.5 no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C3 . H31 . O25 2_765 152 0.94 2.30 3.160(8) yes
C5 . H51 . O33 2_756 158 0.93 2.26 3.142(8) yes
C8 . H81 . O25 2_765 142 0.92 2.28 3.059(8) yes
C46 . H461 . O21 2_766 132 0.97 2.53 3.256(8) yes
C51 . H511 . O33 2_756 144 0.92 2.26 3.052(8) yes


# end of ARCHIVE-HKL.CIF 
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol/chloroform/diethyl ether'
####################################################################### 
# 
# 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_PdBr_8_acetonitrile
_database_code_depnum_ccdc_archive 'CCDC 2225119'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2022-12-08 deposited with the CCDC.	2023-01-16 downloaded from the CCDC.
;
#==============================================================================
# start Validation Reply Form
_vrf_PLAT029_PdBr_8_acetonitrile 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.867 Why?  
RESPONSE: Low data completion ratio is due to the limitations of the instrument
available at the Australian Synchrotron operating under rotation data 
collection with a fixed detector and affects some high angle data.
;
_vrf_PLAT260_PdBr_8_acetonitrile 
;
PROBLEM: Large Average Ueq of Residue Including      O103      0.133 Check 
RESPONSE: This is the disordered diethyl ether solvate.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 

;
_refine_special_details          
; 
Most of the structure refines very smoothly. The exception is a diethyl ether
solvent molecule located in the centre of the macrocycle. This was modelled 
as disordered over two parts (occupancies 0.65:0.35), and required the use 
of bond distance, bond angle, and thermal and vibrational ellipsoid
restraints for this disordered solvent. 

With the exception of the disordered diethyl ether solvent molecule,
C-H hydrogen atoms were  visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. Amide N-H hydrogen 
atoms were initially inserted at calculated positions and were then refined
with restraints on bond lengths and angles. 
;

_cell_length_a                   13.238(3)
_cell_length_b                   13.973(3)
_cell_length_c                   14.000(3)
_cell_angle_alpha                66.81(3)
_cell_angle_beta                 81.10(3)
_cell_angle_gamma                71.56(3)
_cell_volume                     2256.8(10)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Pd -0.9988 1.0072 19.3319 0.6987 15.5017 7.9893 5.2954 25.2052 0.6058 76.8986
5.2659 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

_chemical_formula_sum            'C41 H45 B Br F4 N9 O7 Pd'
_chemical_formula_moiety         'C37 H35 Br N9 O6 Pd, B F4, C4 H10 O'
_chemical_compound_source        synthesized
_chemical_formula_weight         1048.97


_cell_measurement_reflns_used    28059
_cell_measurement_theta_min      1.58
_cell_measurement_theta_max      26.4
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_max          0.10

_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1064
_exptl_absorpt_coefficient_mu    1.372

_diffrn_measurement_device_type  Synchrotron
_diffrn_radiation_source         'MX1 Beamline Australian Synchrotron'
_diffrn_measurement_device       'ADSC Quantum 210r'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_method       'φ scans'

_computing_data_collection       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      100
_diffrn_reflns_number            28059
_diffrn_reflns_av_unetI/netI     0.043
_reflns_number_total             7831
_diffrn_reflns_av_R_equivalents  0.030


_diffrn_reflns_theta_min         1.583
_diffrn_reflns_theta_max         26.365
_diffrn_measured_fraction_theta_max 0.848

_diffrn_reflns_theta_full        25.047
_diffrn_measured_fraction_theta_full 0.867

_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -16
_reflns_limit_h_max              16
_reflns_limit_k_min              -14
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   2.47
_oxford_diffrn_Wilson_scale      26.24

_atom_sites_solution_primary     other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -2.19
_refine_diff_density_max         1.36


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     78
_refine_ls_number_parameters     630
_refine_ls_number_reflns         7831
_refine_ls_R_factor_ref          0.0557
_refine_ls_wR_factor_ref         0.1527
_refine_ls_goodness_of_fit_ref   0.9940
_refine_ls_shift/su_max          0.0007054
_refine_ls_shift/su_mean         0.0000236

# Computed with I/sigma = -10 
_reflns_number_all               7831
_refine_ls_R_factor_all          0.0557
_refine_ls_wR_factor_all         0.1527

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6909
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_gt          0.1467

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.13P)² + 1.05P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.3723(2) 0.1274(2) 0.5820(2) 0.0284 1.0000 Uani . . . . . .
C2 C 0.3663(3) 0.2328(3) 0.5323(3) 0.0321 1.0000 Uani . . . . . .
C3 C 0.3645(3) 0.2956(3) 0.5887(3) 0.0340 1.0000 Uani . . . . . .
C4 C 0.3682(3) 0.2451(3) 0.6967(3) 0.0364 1.0000 Uani . . . . . .
C5 C 0.3742(3) 0.1355(3) 0.7459(3) 0.0353 1.0000 Uani . . . . . .
C6 C 0.3748(3) 0.0776(3) 0.6846(3) 0.0313 1.0000 Uani . . . . . .
C7 C 0.3593(3) 0.2673(3) 0.4196(3) 0.0307 1.0000 Uani . . . . . .
C8 C 0.3489(3) 0.3616(3) 0.3347(3) 0.0316 1.0000 Uani . . . . . .
N9 N 0.3604(2) 0.1878(2) 0.3848(2) 0.0301 1.0000 Uani . . . . . .
N10 N 0.3507(2) 0.2279(2) 0.2830(2) 0.0322 1.0000 Uani . . . . . .
N11 N 0.3445(2) 0.3333(2) 0.2539(2) 0.0303 1.0000 Uani . . . . . .
C12 C 0.3189(3) 0.4040(3) 0.1461(3) 0.0328 1.0000 Uani . . . . . .
C13 C 0.2003(3) 0.4315(3) 0.1330(3) 0.0323 1.0000 Uani . . . . . .
O14 O 0.1461(2) 0.4998(2) 0.1899(2) 0.0356 1.0000 Uani . . . . . .
C15 C 0.0435(3) 0.4959(3) 0.2267(3) 0.0355 1.0000 Uani . . . . . .
C16 C -0.0210(3) 0.4627(3) 0.1851(3) 0.0351 1.0000 Uani . . . . . .
C17 C -0.1217(3) 0.4571(3) 0.2296(3) 0.0356 1.0000 Uani . . . . . .
C18 C -0.1576(3) 0.4848(3) 0.3166(3) 0.0360 1.0000 Uani . . . . . .
C19 C -0.0938(4) 0.5224(4) 0.3552(4) 0.0486 1.0000 Uani . . . . . .
C20 C 0.0059(4) 0.5283(4) 0.3107(4) 0.0469 1.0000 Uani . . . . . .
O21 O -0.2523(2) 0.4768(2) 0.3691(2) 0.0387 1.0000 Uani . . . . . .
C22 C -0.3055(3) 0.4123(3) 0.3493(3) 0.0331 1.0000 Uani . . . . . .
C23 C -0.3952(3) 0.3963(3) 0.4305(3) 0.0342 1.0000 Uani D . . . . .
N24 N -0.3567(3) 0.3311(3) 0.5355(2) 0.0345 1.0000 Uani D . . . . .
O25 O -0.3528(2) 0.4716(2) 0.5763(2) 0.0371 1.0000 Uani . . . . . .
C26 C -0.3369(3) 0.3734(3) 0.5991(3) 0.0324 1.0000 Uani D . . . . .
C27 C -0.2933(3) 0.2953(3) 0.7025(3) 0.0327 1.0000 Uani . . . . . .
C28 C -0.3303(3) 0.2047(3) 0.7617(3) 0.0319 1.0000 Uani . . . . . .
C29 C -0.2911(3) 0.1397(3) 0.8607(3) 0.0339 1.0000 Uani . . . . . .
C30 C -0.2142(3) 0.1628(3) 0.8982(3) 0.0374 1.0000 Uani . . . . . .
C31 C -0.1760(3) 0.2509(3) 0.8380(3) 0.0398 1.0000 Uani . . . . . .
C32 C -0.2174(3) 0.3177(3) 0.7417(3) 0.0370 1.0000 Uani . . . . . .
O33 O -0.3322(2) 0.0196(2) 1.0270(2) 0.0378 1.0000 Uani . . . . . .
C34 C -0.3333(3) 0.0468(3) 0.9316(3) 0.0331 1.0000 Uani D . . . . .
N35 N -0.3699(3) -0.0050(2) 0.8884(2) 0.0344 1.0000 Uani D . . . . .
C36 C -0.3926(3) -0.1080(3) 0.9520(3) 0.0341 1.0000 Uani D . . . . .
C37 C -0.2888(3) -0.1967(3) 0.9873(3) 0.0369 1.0000 Uani . . . . . .
O38 O -0.2313(2) -0.2027(2) 0.8929(2) 0.0429 1.0000 Uani . . . . . .
C39 C -0.1235(3) -0.2160(3) 0.8849(3) 0.0358 1.0000 Uani . . . . . .
C40 C -0.0834(3) -0.1706(3) 0.7843(3) 0.0425 1.0000 Uani . . . . . .
C41 C 0.0253(3) -0.1858(3) 0.7670(3) 0.0411 1.0000 Uani . . . . . .
C42 C 0.0942(3) -0.2457(3) 0.8494(3) 0.0355 1.0000 Uani . . . . . .
C43 C 0.0543(3) -0.2887(3) 0.9497(3) 0.0344 1.0000 Uani . . . . . .
C44 C -0.0561(3) -0.2736(3) 0.9677(3) 0.0365 1.0000 Uani . . . . . .
O45 O 0.2006(2) -0.2593(2) 0.8221(2) 0.0380 1.0000 Uani . . . . . .
C46 C 0.2750(3) -0.3116(3) 0.9030(3) 0.0335 1.0000 Uani . . . . . .
C47 C 0.3842(3) -0.3165(3) 0.8495(3) 0.0325 1.0000 Uani . . . . . .
N48 N 0.3886(2) -0.2066(2) 0.7818(2) 0.0300 1.0000 Uani . . . . . .
N49 N 0.3849(2) -0.1775(2) 0.6787(2) 0.0327 1.0000 Uani . . . . . .
N50 N 0.3798(2) -0.0736(2) 0.6398(2) 0.0297 1.0000 Uani . . . . . .
C51 C 0.3853(3) -0.1232(3) 0.8095(3) 0.0318 1.0000 Uani . . . . . .
C52 C 0.3802(3) -0.0370(3) 0.7175(3) 0.0306 1.0000 Uani . . . . . .
C111 C 0.0671(15) 0.2376(11) 0.4831(12) 0.1124 0.6500 Uani D U . . 2 .
C112 C 0.0784(9) 0.1206(9) 0.5442(7) 0.1073 0.6500 Uani D U . . 2 .
O113 O 0.1241(5) 0.0870(8) 0.6417(5) 0.0983 0.6500 Uani D U . . 2 .
C104 C 0.048(2) 0.152(3) 0.7330(15) 0.1796 0.3500 Uani D U . . 1 .
C105 C 0.098(3) 0.053(3) 0.8223(17) 0.1665 0.3500 Uani D U . . 1 .
Pd1 Pd 0.36927(2) 0.04234(2) 0.497155(19) 0.0291 1.0000 Uani . . . . . .
Br1 Br 0.35064(3) -0.05517(3) 0.39460(3) 0.0383 1.0000 Uani . . . . . .
F13 F 0.4918(2) 0.7061(2) 0.02132(19) 0.0540 1.0000 Uani . . . . . .
B11 B 0.5284(4) 0.6163(3) 0.1101(3) 0.0352 1.0000 Uani . . . . . .
F12 F 0.5421(2) 0.6500(2) 0.1858(2) 0.0543 1.0000 Uani . . . . . .
F14 F 0.6271(2) 0.55363(18) 0.08575(17) 0.0451 1.0000 Uani . . . . . .
F15 F 0.4573(2) 0.5548(2) 0.1447(3) 0.0639 1.0000 Uani . . . . . .
C102 C 0.068(2) 0.2432(11) 0.5509(13) 0.1116 0.3500 Uani D U . . 1 .
C115 C 0.0959(9) 0.0426(9) 0.8213(7) 0.0672 0.6500 Uani D U . . 2 .
C114 C 0.0480(7) 0.1003(8) 0.7179(7) 0.0757 0.6500 Uani D U . . 2 .
O103 O 0.1139(11) 0.1574(10) 0.6429(9) 0.0858 0.3500 Uani D U . . 1 .
C101 C 0.043(3) 0.2005(19) 0.478(2) 0.1205 0.3500 Uani D U . . 1 .
H31 H 0.3599 0.3691 0.5560 0.0413 1.0000 Uiso R . . . . .
H41 H 0.3670 0.2850 0.7369 0.0437 1.0000 Uiso R . . . . .
H51 H 0.3782 0.1017 0.8183 0.0432 1.0000 Uiso R . . . . .
H81 H 0.3457 0.4306 0.3323 0.0386 1.0000 Uiso R . . . . .
H121 H 0.3379 0.4709 0.1319 0.0394 1.0000 Uiso R . . . . .
H122 H 0.3603 0.3683 0.0996 0.0393 1.0000 Uiso R . . . . .
H131 H 0.1852 0.4713 0.0583 0.0391 1.0000 Uiso R . . . . .
H132 H 0.1781 0.3655 0.1588 0.0385 1.0000 Uiso R . . . . .
H161 H 0.0033 0.4442 0.1272 0.0412 1.0000 Uiso R . . . . .
H171 H -0.1658 0.4352 0.1994 0.0447 1.0000 Uiso R . . . . .
H191 H -0.1187 0.5432 0.4137 0.0560 1.0000 Uiso R . . . . .
H201 H 0.0481 0.5530 0.3374 0.0563 1.0000 Uiso R . . . . .
H221 H -0.3335 0.4488 0.2797 0.0399 1.0000 Uiso R . . . . .
H222 H -0.2563 0.3425 0.3549 0.0403 1.0000 Uiso R . . . . .
H231 H -0.4401 0.4664 0.4304 0.0419 1.0000 Uiso R . . . . .
H232 H -0.4363 0.3572 0.4150 0.0425 1.0000 Uiso R . . . . .
H281 H -0.3787 0.1867 0.7335 0.0390 1.0000 Uiso R . . . . .
H301 H -0.1886 0.1188 0.9649 0.0453 1.0000 Uiso R . . . . .
H311 H -0.1226 0.2652 0.8628 0.0482 1.0000 Uiso R . . . . .
H321 H -0.1940 0.3786 0.7027 0.0444 1.0000 Uiso R . . . . .
H362 H -0.4381 -0.0993 1.0111 0.0418 1.0000 Uiso R . . . . .
H361 H -0.4299 -0.1271 0.9098 0.0424 1.0000 Uiso R . . . . .
H371 H -0.3006 -0.2667 1.0296 0.0448 1.0000 Uiso R . . . . .
H372 H -0.2486 -0.1776 1.0266 0.0449 1.0000 Uiso R . . . . .
H401 H -0.1315 -0.1277 0.7284 0.0515 1.0000 Uiso R . . . . .
H411 H 0.0532 -0.1561 0.7012 0.0491 1.0000 Uiso R . . . . .
H431 H 0.1002 -0.3258 1.0049 0.0417 1.0000 Uiso R . . . . .
H441 H -0.0852 -0.3021 1.0346 0.0446 1.0000 Uiso R . . . . .
H462 H 0.2612 -0.2718 0.9494 0.0402 1.0000 Uiso R . . . . .
H461 H 0.2703 -0.3843 0.9425 0.0403 1.0000 Uiso R . . . . .
H471 H 0.4387 -0.3483 0.9019 0.0391 1.0000 Uiso R . . . . .
H472 H 0.3968 -0.3591 0.8060 0.0391 1.0000 Uiso R . . . . .
H511 H 0.3860 -0.1258 0.8778 0.0371 1.0000 Uiso R . . . . .
H1111 H 0.0687 0.2539 0.4098 0.1681 0.6500 Uiso R . . . 2 .
H1113 H -0.0021 0.2716 0.5056 0.1680 0.6500 Uiso R . . . 2 .
H1112 H 0.1220 0.2581 0.5017 0.1680 0.6500 Uiso R . . . 2 .
H1121 H 0.0091 0.1060 0.5548 0.1229 0.6500 Uiso R . . . 2 .
H1122 H 0.1266 0.0819 0.5026 0.1232 0.6500 Uiso R . . . 2 .
H1021 H 0.1071 0.2975 0.5257 0.1331 0.3500 Uiso R . . . 1 .
H1022 H -0.0044 0.2743 0.5702 0.1331 0.3500 Uiso R . . . 1 .
H1151 H 0.0439 0.0147 0.8726 0.1120 0.6500 Uiso R . . . 2 .
H1152 H 0.1164 0.0939 0.8390 0.1117 0.6500 Uiso R . . . 2 .
H1153 H 0.1574 -0.0158 0.8183 0.1123 0.6500 Uiso R . . . 2 .
H1141 H 0.0231 0.1780 0.7027 0.0935 0.6500 Uiso R . . . 2 .
H1142 H -0.0115 0.0736 0.7141 0.0931 0.6500 Uiso R . . . 2 .
H351 H -0.360(3) 0.009(2) 0.8232(15) 0.041(2) 1.0000 Uiso D . . . . .
H241 H -0.341(3) 0.2611(16) 0.5546(19) 0.041(2) 1.0000 Uiso D . . . . .
H1011 H 0.0089 0.2595 0.4192 0.1245 0.3500 Uiso R . . . 1 .
H1012 H 0.1142 0.1696 0.4580 0.1245 0.3500 Uiso R . . . 1 .
H1013 H 0.0055 0.1472 0.5023 0.1245 0.3500 Uiso R . . . 1 .
H1041 H 0.0298 0.2162 0.7471 0.2208 0.3500 Uiso R . . . 1 .
H1042 H -0.0145 0.1399 0.7201 0.2208 0.3500 Uiso R . . . 1 .
H1051 H 0.0534 0.0491 0.8827 0.2008 0.3500 Uiso R . . . 1 .
H1052 H 0.1654 0.0570 0.8339 0.2008 0.3500 Uiso R . . . 1 .
H1053 H 0.1086 -0.0107 0.8075 0.2008 0.3500 Uiso R . . . 1 .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.17456(13)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.340(5) yes
N1 . C6 . 1.327(5) yes
N1 . Pd1 . 1.995(3) yes
C2 . C3 . 1.386(5) yes
C2 . C7 . 1.465(5) yes
C3 . C4 . 1.396(5) yes
C3 . H31 . 0.931 no
C4 . C5 . 1.390(5) yes
C4 . H41 . 0.931 no
C5 . C6 . 1.391(5) yes
C5 . H51 . 0.937 no
C6 . C52 . 1.463(5) yes
C7 . C8 . 1.368(5) yes
C7 . N9 . 1.373(4) yes
C8 . N11 . 1.352(5) yes
C8 . H81 . 0.939 no
N9 . N10 . 1.319(4) yes
N9 . Pd1 . 2.002(3) yes
N10 . N11 . 1.343(4) yes
N11 . C12 . 1.463(4) yes
C12 . C13 . 1.516(5) yes
C12 . H121 . 0.982 no
C12 . H122 . 0.971 no
C13 . O14 . 1.433(4) yes
C13 . H131 . 0.989 no
C13 . H132 . 0.971 no
O14 . C15 . 1.387(4) yes
C15 . C16 . 1.379(6) yes
C15 . C20 . 1.390(6) yes
C16 . C17 . 1.393(5) yes
C16 . H161 . 0.928 no
C17 . C18 . 1.392(5) yes
C17 . H171 . 0.951 no
C18 . C19 . 1.388(6) yes
C18 . O21 . 1.365(4) yes
C19 . C20 . 1.382(6) yes
C19 . H191 . 0.952 no
C20 . H201 . 0.927 no
O21 . C22 . 1.429(4) yes
C22 . C23 . 1.518(5) yes
C22 . H221 . 0.975 no
C22 . H222 . 0.966 no
C23 . N24 . 1.460(5) yes
C23 . H231 . 0.971 no
C23 . H232 . 0.979 no
N24 . C26 . 1.340(5) yes
N24 . H241 . 0.868(18) no
O25 . C26 . 1.233(4) yes
C26 . C27 . 1.496(5) yes
C27 . C28 . 1.403(5) yes
C27 . C32 . 1.384(6) yes
C28 . C29 . 1.395(5) yes
C28 . H281 . 0.942 no
C29 . C30 . 1.386(6) yes
C29 . C34 . 1.502(5) yes
C30 . C31 . 1.389(5) yes
C30 . H301 . 0.937 no
C31 . C32 . 1.379(6) yes
C31 . H311 . 0.938 no
C32 . H321 . 0.931 no
O33 . C34 . 1.237(4) yes
C34 . N35 . 1.335(5) yes
N35 . C36 . 1.462(5) yes
N35 . H351 . 0.852(19) no
C36 . C37 . 1.522(5) yes
C36 . H362 . 0.970 no
C36 . H361 . 0.980 no
C37 . O38 . 1.438(5) yes
C37 . H371 . 0.971 no
C37 . H372 . 0.976 no
O38 . C39 . 1.373(5) yes
C39 . C40 . 1.395(6) yes
C39 . C44 . 1.385(5) yes
C40 . C41 . 1.383(6) yes
C40 . H401 . 0.959 no
C41 . C42 . 1.393(6) yes
C41 . H411 . 0.921 no
C42 . C43 . 1.386(5) yes
C42 . O45 . 1.374(5) yes
C43 . C44 . 1.406(5) yes
C43 . H431 . 0.931 no
C44 . H441 . 0.935 no
O45 . C46 . 1.423(5) yes
C46 . C47 . 1.516(5) yes
C46 . H462 . 0.974 no
C46 . H461 . 0.962 no
C47 . N48 . 1.468(4) yes
C47 . H471 . 0.980 no
C47 . H472 . 0.971 no
N48 . N49 . 1.341(4) yes
N48 . C51 . 1.352(5) yes
N49 . N50 . 1.318(4) yes
N50 . C52 . 1.372(4) yes
N50 . Pd1 . 2.007(3) yes
C51 . C52 . 1.367(5) yes
C51 . H511 . 0.943 no
C52 . Pd1 . 2.847(4) yes
C111 . C112 . 1.487(9) yes
C111 . H1111 . 0.958 no
C111 . H1113 . 0.958 no
C111 . H1112 . 0.963 no
C112 . O113 . 1.422(8) yes
C112 . H1121 . 0.978 no
C112 . H1122 . 0.977 no
O113 . C114 . 1.376(7) yes
C104 . C105 . 1.493(10) yes
C104 . O103 . 1.406(9) yes
C104 . H1041 . 0.950 no
C104 . H1042 . 0.950 no
C105 . H1051 . 0.950 no
C105 . H1052 . 0.950 no
C105 . H1053 . 0.950 no
Pd1 . Br1 . 2.4168(7) yes
F13 . B11 . 1.389(5) yes
B11 . F12 . 1.374(5) yes
B11 . F14 . 1.401(5) yes
B11 . F15 . 1.379(5) yes
C102 . O103 . 1.423(9) yes
C102 . C101 . 1.494(10) yes
C102 . H1021 . 0.970 no
C102 . H1022 . 0.969 no
C115 . C114 . 1.480(8) yes
C115 . H1151 . 0.968 no
C115 . H1152 . 0.965 no
C115 . H1153 . 0.963 no
C114 . H1141 . 0.972 no
C114 . H1142 . 0.989 no
C101 . H1011 . 0.950 no
C101 . H1012 . 0.950 no
C101 . H1013 . 0.950 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C6 . 123.9(3) yes
C2 . N1 . Pd1 . 117.9(2) yes
C6 . N1 . Pd1 . 118.1(2) yes
N1 . C2 . C3 . 119.7(3) yes
N1 . C2 . C7 . 112.2(3) yes
C3 . C2 . C7 . 128.0(3) yes
C2 . C3 . C4 . 117.6(3) yes
C2 . C3 . H31 . 121.4 no
C4 . C3 . H31 . 121.0 no
C3 . C4 . C5 . 121.2(3) yes
C3 . C4 . H41 . 119.8 no
C5 . C4 . H41 . 119.0 no
C4 . C5 . C6 . 118.2(3) yes
C4 . C5 . H51 . 120.8 no
C6 . C5 . H51 . 121.0 no
C5 . C6 . N1 . 119.4(3) yes
C5 . C6 . C52 . 128.5(3) yes
N1 . C6 . C52 . 112.1(3) yes
C2 . C7 . C8 . 137.1(3) yes
C2 . C7 . N9 . 115.6(3) yes
C8 . C7 . N9 . 107.2(3) yes
C7 . C8 . N11 . 104.3(3) yes
C7 . C8 . H81 . 128.3 no
N11 . C8 . H81 . 127.3 no
C7 . N9 . N10 . 110.7(3) yes
C7 . N9 . Pd1 . 114.4(2) yes
N10 . N9 . Pd1 . 134.8(2) yes
N9 . N10 . N11 . 104.8(3) yes
C8 . N11 . N10 . 112.9(3) yes
C8 . N11 . C12 . 128.4(3) yes
N10 . N11 . C12 . 118.0(3) yes
N11 . C12 . C13 . 109.3(3) yes
N11 . C12 . H121 . 107.6 no
C13 . C12 . H121 . 109.2 no
N11 . C12 . H122 . 109.6 no
C13 . C12 . H122 . 111.4 no
H121 . C12 . H122 . 109.5 no
C12 . C13 . O14 . 107.8(3) yes
C12 . C13 . H131 . 108.6 no
O14 . C13 . H131 . 109.4 no
C12 . C13 . H132 . 110.1 no
O14 . C13 . H132 . 110.7 no
H131 . C13 . H132 . 110.2 no
C13 . O14 . C15 . 116.5(3) yes
O14 . C15 . C16 . 124.2(3) yes
O14 . C15 . C20 . 116.2(4) yes
C16 . C15 . C20 . 119.7(4) yes
C15 . C16 . C17 . 120.4(3) yes
C15 . C16 . H161 . 119.3 no
C17 . C16 . H161 . 120.4 no
C16 . C17 . C18 . 120.0(4) yes
C16 . C17 . H171 . 119.5 no
C18 . C17 . H171 . 120.5 no
C17 . C18 . C19 . 119.1(4) yes
C17 . C18 . O21 . 124.6(4) yes
C19 . C18 . O21 . 116.3(3) yes
C18 . C19 . C20 . 120.7(4) yes
C18 . C19 . H191 . 119.4 no
C20 . C19 . H191 . 119.9 no
C15 . C20 . C19 . 120.0(4) yes
C15 . C20 . H201 . 120.0 no
C19 . C20 . H201 . 120.0 no
C18 . O21 . C22 . 117.1(3) yes
O21 . C22 . C23 . 107.7(3) yes
O21 . C22 . H221 . 110.0 no
C23 . C22 . H221 . 110.5 no
O21 . C22 . H222 . 110.0 no
C23 . C22 . H222 . 109.5 no
H221 . C22 . H222 . 109.1 no
C22 . C23 . N24 . 112.8(3) yes
C22 . C23 . H231 . 109.6 no
N24 . C23 . H231 . 107.9 no
C22 . C23 . H232 . 109.0 no
N24 . C23 . H232 . 106.6 no
H231 . C23 . H232 . 110.9 no
C23 . N24 . C26 . 123.3(3) yes
C23 . N24 . H241 . 117.3(13) no
C26 . N24 . H241 . 119.1(13) no
N24 . C26 . O25 . 123.5(3) yes
N24 . C26 . C27 . 116.8(3) yes
O25 . C26 . C27 . 119.7(3) yes
C26 . C27 . C28 . 122.4(3) yes
C26 . C27 . C32 . 117.6(3) yes
C28 . C27 . C32 . 119.9(3) yes
C27 . C28 . C29 . 119.0(3) yes
C27 . C28 . H281 . 120.0 no
C29 . C28 . H281 . 120.9 no
C28 . C29 . C30 . 120.2(3) yes
C28 . C29 . C34 . 121.8(3) yes
C30 . C29 . C34 . 117.9(3) yes
C29 . C30 . C31 . 120.3(4) yes
C29 . C30 . H301 . 119.5 no
C31 . C30 . H301 . 120.1 no
C30 . C31 . C32 . 119.6(4) yes
C30 . C31 . H311 . 120.2 no
C32 . C31 . H311 . 120.2 no
C27 . C32 . C31 . 120.8(3) yes
C27 . C32 . H321 . 119.6 no
C31 . C32 . H321 . 119.6 no
C29 . C34 . O33 . 119.9(3) yes
C29 . C34 . N35 . 118.1(3) yes
O33 . C34 . N35 . 122.0(3) yes
C34 . N35 . C36 . 120.5(3) yes
C34 . N35 . H351 . 119.0(14) no
C36 . N35 . H351 . 117.2(14) no
N35 . C36 . C37 . 109.8(3) yes
N35 . C36 . H362 . 108.8 no
C37 . C36 . H362 . 111.1 no
N35 . C36 . H361 . 108.6 no
C37 . C36 . H361 . 109.2 no
H362 . C36 . H361 . 109.4 no
C36 . C37 . O38 . 105.0(3) yes
C36 . C37 . H371 . 112.3 no
O38 . C37 . H371 . 109.1 no
C36 . C37 . H372 . 110.6 no
O38 . C37 . H372 . 110.6 no
H371 . C37 . H372 . 109.1 no
C37 . O38 . C39 . 119.2(3) yes
O38 . C39 . C40 . 115.0(4) yes
O38 . C39 . C44 . 124.2(3) yes
C40 . C39 . C44 . 120.8(4) yes
C39 . C40 . C41 . 119.4(4) yes
C39 . C40 . H401 . 119.7 no
C41 . C40 . H401 . 120.9 no
C40 . C41 . C42 . 120.4(4) yes
C40 . C41 . H411 . 120.6 no
C42 . C41 . H411 . 119.1 no
C41 . C42 . C43 . 120.4(4) yes
C41 . C42 . O45 . 115.1(3) yes
C43 . C42 . O45 . 124.5(4) yes
C42 . C43 . C44 . 119.5(4) yes
C42 . C43 . H431 . 120.1 no
C44 . C43 . H431 . 120.4 no
C43 . C44 . C39 . 119.6(4) yes
C43 . C44 . H441 . 121.3 no
C39 . C44 . H441 . 119.1 no
C42 . O45 . C46 . 118.2(3) yes
O45 . C46 . C47 . 106.0(3) yes
O45 . C46 . H462 . 110.8 no
C47 . C46 . H462 . 111.7 no
O45 . C46 . H461 . 110.0 no
C47 . C46 . H461 . 109.2 no
H462 . C46 . H461 . 109.1 no
C46 . C47 . N48 . 109.5(3) yes
C46 . C47 . H471 . 109.5 no
N48 . C47 . H471 . 109.6 no
C46 . C47 . H472 . 109.7 no
N48 . C47 . H472 . 107.7 no
H471 . C47 . H472 . 110.7 no
C47 . N48 . N49 . 118.6(3) yes
C47 . N48 . C51 . 128.2(3) yes
N49 . N48 . C51 . 112.8(3) yes
N48 . N49 . N50 . 104.9(3) yes
N49 . N50 . C52 . 110.8(3) yes
N49 . N50 . Pd1 . 135.7(2) yes
C52 . N50 . Pd1 . 113.5(2) yes
N48 . C51 . C52 . 104.4(3) yes
N48 . C51 . H511 . 126.6 no
C52 . C51 . H511 . 129.0 no
C6 . C52 . N50 . 116.3(3) yes
C6 . C52 . C51 . 136.6(3) yes
N50 . C52 . C51 . 107.1(3) yes
C6 . C52 . Pd1 . 76.0(2) yes
N50 . C52 . Pd1 . 40.28(15) yes
C51 . C52 . Pd1 . 147.4(3) yes
C112 . C111 . H1111 . 111.9 no
C112 . C111 . H1113 . 102.3 no
H1111 . C111 . H1113 . 110.0 no
C112 . C111 . H1112 . 109.1 no
H1111 . C111 . H1112 . 111.6 no
H1113 . C111 . H1112 . 111.6 no
C111 . C112 . O113 . 111.2(8) yes
C111 . C112 . H1121 . 110.4 no
O113 . C112 . H1121 . 110.1 no
C111 . C112 . H1122 . 105.5 no
O113 . C112 . H1122 . 109.1 no
H1121 . C112 . H1122 . 110.4 no
C112 . O113 . C114 . 112.0(6) yes
C105 . C104 . O103 . 109.7(9) yes
C105 . C104 . H1041 . 113.1 no
O103 . C104 . H1041 . 112.5 no
C105 . C104 . H1042 . 105.8 no
O103 . C104 . H1042 . 105.7 no
H1041 . C104 . H1042 . 109.5 no
C104 . C105 . H1051 . 109.2 no
C104 . C105 . H1052 . 109.0 no
H1051 . C105 . H1052 . 109.5 no
C104 . C105 . H1053 . 110.2 no
H1051 . C105 . H1053 . 109.5 no
H1052 . C105 . H1053 . 109.5 no
N50 . Pd1 . N9 . 159.76(12) yes
N50 . Pd1 . N1 . 79.93(12) yes
N9 . Pd1 . N1 . 79.83(12) yes
N50 . Pd1 . C52 . 26.23(11) yes
N9 . Pd1 . C52 . 133.53(11) yes
N1 . Pd1 . C52 . 53.71(11) yes
N50 . Pd1 . Br1 . 100.59(9) yes
N9 . Pd1 . Br1 . 99.60(9) yes
N1 . Pd1 . Br1 . 175.52(8) yes
C52 . Pd1 . Br1 . 126.63(8) yes
F13 . B11 . F12 . 109.4(3) yes
F13 . B11 . F14 . 108.6(3) yes
F12 . B11 . F14 . 108.7(3) yes
F13 . B11 . F15 . 110.2(4) yes
F12 . B11 . F15 . 110.4(3) yes
F14 . B11 . F15 . 109.4(3) yes
O103 . C102 . C101 . 111.4(9) yes
O103 . C102 . H1021 . 110.6 no
C101 . C102 . H1021 . 120.0 no
O103 . C102 . H1022 . 105.9 no
C101 . C102 . H1022 . 97.0 no
H1021 . C102 . H1022 . 110.3 no
C114 . C115 . H1151 . 109.6 no
C114 . C115 . H1152 . 108.0 no
H1151 . C115 . H1152 . 109.4 no
C114 . C115 . H1153 . 109.1 no
H1151 . C115 . H1153 . 110.4 no
H1152 . C115 . H1153 . 110.3 no
C115 . C114 . O113 . 110.0(6) yes
C115 . C114 . H1141 . 110.3 no
O113 . C114 . H1141 . 105.6 no
C115 . C114 . H1142 . 111.1 no
O113 . C114 . H1142 . 109.6 no
H1141 . C114 . H1142 . 110.0 no
C102 . O103 . C104 . 114.2(9) yes
C102 . C101 . H1011 . 109.5 no
C102 . C101 . H1012 . 98.0 no
H1011 . C101 . H1012 . 109.5 no
C102 . C101 . H1013 . 120.1 no
H1011 . C101 . H1013 . 109.5 no
H1012 . C101 . H1013 . 109.5 no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C3 . H31 . O25 2_566 158 0.93 2.25 3.133(10) yes
C5 . H51 . O33 2_557 150 0.94 2.30 3.148(10) yes
C8 . H81 . O25 2_566 146 0.94 2.24 3.061(10) yes
C13 . H132 . O38 2_556 132 0.97 2.51 3.248(10) yes
C51 . H511 . O33 2_557 141 0.94 2.25 3.050(10) yes



# end of ARCHIVE-HKL.CIF 
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile/diethyl ether'
####################################################################### 
# 
# 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_PdCl_8
_database_code_depnum_ccdc_archive 'CCDC 2225121'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2022-12-08 deposited with the CCDC.	2023-01-16 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
; 
Hydrogen atoms were visible in the Fourier difference map. The N-H  
protons were refined with restraints on bond lengths and angles. The C-H
protons were initially refined with restraints on bond lengths and angles, 
after which the positions were used as the basis for a riding model. 

Apart from restraints on N-H bond lengths and angles, it was not 
necessary to use any crystallographic restraints.
;

_cell_length_a                   9.3736(4)
_cell_length_b                   14.5616(7)
_cell_length_c                   17.2045(5)
_cell_angle_alpha                75.166(3)
_cell_angle_beta                 77.178(3)
_cell_angle_gamma                75.894(4)
_cell_volume                     2169.50(16)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Pd -0.9988 1.0072 19.3319 0.6987 15.5017 7.9893 5.2954 25.2052 0.6058 76.8986
5.2659 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2


_chemical_formula_sum            'C41 H41 B Cl F4 N11 O6 Pd'
_chemical_formula_moiety         'C37 H35 Cl N9 O6 Pd, B F4, 2(C2 H3 N)'
_chemical_compound_source        synthesized
_chemical_formula_weight         1012.50


_cell_measurement_reflns_used    8172
_cell_measurement_theta_min      3.69
_cell_measurement_theta_max      26.58
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_max          0.22

_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1031.995
_exptl_absorpt_coefficient_mu    0.568

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro, (Agilent, 2011)'
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

_computing_data_collection       'CrysAlisPro, (Agilent, 2011)'
_computing_cell_refinement       'CrysAlisPro, (Agilent, 2011)'
_computing_data_reduction        'CrysAlisPro, (Agilent, 2011)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            27393
_diffrn_reflns_av_unetI/netI     0.098
_reflns_number_total             7728
_diffrn_reflns_av_R_equivalents  0.063

_diffrn_reflns_theta_min         3.351
_diffrn_reflns_theta_max         25.129
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        26.372
_diffrn_measured_fraction_theta_full 0.997

_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              -17
_reflns_limit_k_max              18
_reflns_limit_l_min              0
_reflns_limit_l_max              21

_oxford_diffrn_Wilson_B_factor   1.65
_oxford_diffrn_Wilson_scale      1.37

_atom_sites_solution_primary     other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.82
_refine_diff_density_max         0.93


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     8
_refine_ls_number_parameters     594
_refine_ls_number_reflns         7727
_refine_ls_R_factor_ref          0.0681
_refine_ls_wR_factor_ref         0.0993
_refine_ls_goodness_of_fit_ref   1.0045
_refine_ls_shift/su_max          0.0016807
_refine_ls_shift/su_mean         0.0000264


# Computed with I/sigma = -10 
_reflns_number_all               7728
_refine_ls_R_factor_all          0.0682
_refine_ls_wR_factor_all         0.0993

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6034
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_gt          0.0877


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.03P)² + 1.92P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.6710(3) 0.5204(2) 0.58669(17) 0.0178 1.0000 Uani . . . . . .
C2 C 0.8059(4) 0.4627(3) 0.5948(2) 0.0216 1.0000 Uani . . . . . .
C3 C 0.9250(4) 0.5026(3) 0.5944(2) 0.0277 1.0000 Uani . . . . . .
C4 C 0.9026(5) 0.6022(3) 0.5852(2) 0.0311 1.0000 Uani . . . . . .
C5 C 0.7634(4) 0.6610(3) 0.5767(2) 0.0279 1.0000 Uani . . . . . .
C6 C 0.6481(4) 0.6172(3) 0.5777(2) 0.0212 1.0000 Uani . . . . . .
C7 C 0.7995(4) 0.3609(3) 0.6076(2) 0.0220 1.0000 Uani . . . . . .
C8 C 0.8954(4) 0.2732(3) 0.6214(2) 0.0238 1.0000 Uani . . . . . .
N9 N 0.6614(3) 0.3406(2) 0.61310(18) 0.0217 1.0000 Uani . . . . . .
N10 N 0.6673(4) 0.2468(2) 0.62946(18) 0.0238 1.0000 Uani . . . . . .
N11 N 0.8111(4) 0.2066(2) 0.63448(18) 0.0238 1.0000 Uani . . . . . .
C12 C 0.8532(5) 0.1006(3) 0.6624(2) 0.0286 1.0000 Uani . . . . . .
C13 C 0.8239(4) 0.0727(3) 0.7545(2) 0.0280 1.0000 Uani . . . . . .
O14 O 0.6662(3) 0.0934(2) 0.77997(15) 0.0310 1.0000 Uani . . . . . .
C15 C 0.6149(5) 0.1038(3) 0.8595(2) 0.0276 1.0000 Uani . . . . . .
C16 C 0.6910(5) 0.0624(3) 0.9230(2) 0.0323 1.0000 Uani . . . . . .
C17 C 0.6293(5) 0.0773(3) 1.0015(3) 0.0363 1.0000 Uani . . . . . .
C18 C 0.4889(5) 0.1356(3) 1.0140(3) 0.0346 1.0000 Uani . . . . . .
C19 C 0.4115(5) 0.1774(3) 0.9504(3) 0.0380 1.0000 Uani . . . . . .
C20 C 0.4731(5) 0.1614(3) 0.8733(3) 0.0354 1.0000 Uani . . . . . .
O21 O 0.4161(3) 0.1574(2) 1.08864(17) 0.0437 1.0000 Uani . . . . . .
C22 C 0.4837(5) 0.1121(3) 1.1587(2) 0.0394 1.0000 Uani . . . . . .
C23 C 0.3796(5) 0.1512(3) 1.2294(3) 0.0421 1.0000 Uani D . . . . .
N24 N 0.3756(4) 0.2532(3) 1.2205(2) 0.0338 1.0000 Uani D . . . . .
O25 O 0.5910(3) 0.2246(2) 1.26713(17) 0.0403 1.0000 Uani . . . . . .
C26 C 0.4882(5) 0.2822(3) 1.2382(2) 0.0302 1.0000 Uani D . . . . .
C27 C 0.4825(5) 0.3893(3) 1.2216(2) 0.0293 1.0000 Uani . . . . . .
C28 C 0.3527(5) 0.4600(3) 1.2174(2) 0.0322 1.0000 Uani . . . . . .
C29 C 0.3606(5) 0.5589(3) 1.2025(2) 0.0336 1.0000 Uani . . . . . .
C30 C 0.4980(6) 0.5828(4) 1.1932(3) 0.0462 1.0000 Uani . . . . . .
C31 C 0.6253(6) 0.5135(4) 1.1961(3) 0.0539 1.0000 Uani . . . . . .
C32 C 0.6172(5) 0.4175(3) 1.2112(3) 0.0420 1.0000 Uani . . . . . .
O33 O 0.2380(4) 0.7205(2) 1.20551(19) 0.0519 1.0000 Uani . . . . . .
C34 C 0.2278(6) 0.6392(3) 1.1994(2) 0.0414 1.0000 Uani D . . . . .
N35 N 0.0991(4) 0.6214(3) 1.1908(2) 0.0445 1.0000 Uani D . . . . .
C36 C -0.0320(6) 0.7021(3) 1.1818(3) 0.0477 1.0000 Uani D . . . . .
C37 C -0.0259(6) 0.7572(3) 1.0941(3) 0.0482 1.0000 Uani . . . . . .
O38 O -0.0473(4) 0.6920(2) 1.05154(19) 0.0483 1.0000 Uani . . . . . .
C39 C -0.0228(5) 0.7163(3) 0.9665(3) 0.0404 1.0000 Uani . . . . . .
C40 C 0.0202(5) 0.7998(3) 0.9197(3) 0.0388 1.0000 Uani . . . . . .
C41 C 0.0441(5) 0.8165(3) 0.8332(3) 0.0351 1.0000 Uani . . . . . .
C42 C 0.0219(5) 0.7480(3) 0.7973(3) 0.0321 1.0000 Uani . . . . . .
C43 C -0.0242(5) 0.6643(3) 0.8465(3) 0.0394 1.0000 Uani . . . . . .
C44 C -0.0464(5) 0.6490(3) 0.9295(3) 0.0448 1.0000 Uani . . . . . .
O45 O 0.0436(3) 0.75350(19) 0.71425(17) 0.0341 1.0000 Uani . . . . . .
C46 C 0.0880(5) 0.8380(3) 0.6611(2) 0.0298 1.0000 Uani . . . . . .
C47 C 0.1298(4) 0.8168(3) 0.5768(2) 0.0279 1.0000 Uani . . . . . .
N48 N 0.2677(3) 0.7425(2) 0.57177(18) 0.0221 1.0000 Uani . . . . . .
N49 N 0.2582(3) 0.6493(2) 0.58265(18) 0.0227 1.0000 Uani . . . . . .
N50 N 0.3967(3) 0.6006(2) 0.58362(18) 0.0206 1.0000 Uani . . . . . .
C51 C 0.4078(4) 0.7537(3) 0.5665(2) 0.0221 1.0000 Uani . . . . . .
C52 C 0.4915(4) 0.6621(3) 0.5740(2) 0.0207 1.0000 Uani . . . . . .
N101 N 0.2820(6) 0.5035(4) 1.0336(3) 0.0802 1.0000 Uani . . . . . .
C102 C 0.3283(6) 0.5754(5) 1.0079(3) 0.0585 1.0000 Uani . . . . . .
C103 C 0.3849(6) 0.6638(4) 0.9798(3) 0.0540 1.0000 Uani . . . . . .
N111 N 0.1777(6) 0.0585(4) 0.7606(4) 0.0920 1.0000 Uani . . . . . .
C112 C 0.2788(7) 0.0767(4) 0.7130(4) 0.0598 1.0000 Uani . . . . . .
C113 C 0.4073(6) 0.0997(4) 0.6550(3) 0.0580 1.0000 Uani . . . . . .
Pd1 Pd 0.49802(3) 0.45956(2) 0.600128(18) 0.0200 1.0000 Uani . . . . . .
Cl1 Cl 0.29910(11) 0.38508(7) 0.62353(6) 0.0294 1.0000 Uani . . . . . .
F13 F 0.1453(3) 0.13775(18) 0.52871(14) 0.0433 1.0000 Uani . . . . . .
B11 B 0.2455(5) 0.0682(3) 0.4916(3) 0.0285 1.0000 Uani . . . . . .
F15 F 0.3695(3) 0.10649(18) 0.45029(17) 0.0513 1.0000 Uani . . . . . .
F12 F 0.2863(3) -0.01207(18) 0.55106(17) 0.0587 1.0000 Uani . . . . . .
F14 F 0.1789(3) 0.0431(2) 0.43893(18) 0.0617 1.0000 Uani . . . . . .
H511 H 0.4400 0.8112 0.5589 0.0280 1.0000 Uiso R . . . . .
H81 H 0.9994 0.2607 0.6213 0.0314 1.0000 Uiso R . . . . .
H122 H 0.7951 0.0684 0.6410 0.0359 1.0000 Uiso R . . . . .
H121 H 0.9592 0.0821 0.6423 0.0357 1.0000 Uiso R . . . . .
H131 H 0.8622 0.0039 0.7715 0.0352 1.0000 Uiso R . . . . .
H132 H 0.8698 0.1105 0.7770 0.0347 1.0000 Uiso R . . . . .
H161 H 0.7868 0.0237 0.9138 0.0394 1.0000 Uiso R . . . . .
H171 H 0.6810 0.0482 1.0448 0.0441 1.0000 Uiso R . . . . .
H221 H 0.4929 0.0415 1.1696 0.0469 1.0000 Uiso R . . . . .
H222 H 0.5851 0.1266 1.1503 0.0473 1.0000 Uiso R . . . . .
H231 H 0.2806 0.1404 1.2303 0.0540 1.0000 Uiso R . . . . .
H232 H 0.4132 0.1162 1.2810 0.0538 1.0000 Uiso R . . . . .
H281 H 0.2614 0.4411 1.2255 0.0380 1.0000 Uiso R . . . . .
H361 H -0.1240 0.6762 1.1987 0.0583 1.0000 Uiso R . . . . .
H362 H -0.0295 0.7468 1.2146 0.0582 1.0000 Uiso R . . . . .
H371 H -0.1061 0.8148 1.0888 0.0571 1.0000 Uiso R . . . . .
H372 H 0.0697 0.7777 1.0714 0.0573 1.0000 Uiso R . . . . .
H401 H 0.0354 0.8461 0.9442 0.0475 1.0000 Uiso R . . . . .
H411 H 0.0757 0.8733 0.8008 0.0457 1.0000 Uiso R . . . . .
H462 H 0.0046 0.8934 0.6609 0.0357 1.0000 Uiso R . . . . .
H461 H 0.1734 0.8514 0.6776 0.0360 1.0000 Uiso R . . . . .
H471 H 0.0516 0.7924 0.5647 0.0339 1.0000 Uiso R . . . . .
H472 H 0.1483 0.8739 0.5369 0.0337 1.0000 Uiso R . . . . .
H431 H -0.0377 0.6179 0.8217 0.0489 1.0000 Uiso R . . . . .
H441 H -0.0790 0.5928 0.9615 0.0544 1.0000 Uiso R . . . . .
H301 H 0.5023 0.6488 1.1851 0.0573 1.0000 Uiso R . . . . .
H311 H 0.7192 0.5314 1.1877 0.0655 1.0000 Uiso R . . . . .
H321 H 0.7039 0.3694 1.2146 0.0530 1.0000 Uiso R . . . . .
H191 H 0.3180 0.2181 0.9599 0.0455 1.0000 Uiso R . . . . .
H201 H 0.4198 0.1884 0.8298 0.0430 1.0000 Uiso R . . . . .
H31 H 1.0186 0.4642 0.5993 0.0360 1.0000 Uiso R . . . . .
H41 H 0.9831 0.6310 0.5850 0.0389 1.0000 Uiso R . . . . .
H51 H 0.7509 0.7287 0.5704 0.0376 1.0000 Uiso R . . . . .
H1132 H 0.3791 0.1599 0.6169 0.0902 1.0000 Uiso R . . . . .
H1131 H 0.4809 0.1054 0.6831 0.0901 1.0000 Uiso R . . . . .
H1133 H 0.4465 0.0473 0.6270 0.0902 1.0000 Uiso R . . . . .
H1033 H 0.3475 0.6994 0.9297 0.0823 1.0000 Uiso R . . . . .
H1032 H 0.3545 0.7023 1.0208 0.0820 1.0000 Uiso R . . . . .
H1031 H 0.4962 0.6437 0.9701 0.0816 1.0000 Uiso R . . . . .
H351 H 0.086(3) 0.5611(14) 1.196(3) 0.053(2) 1.0000 Uiso D . . . . .
H241 H 0.321(4) 0.2927(14) 1.189(2) 0.041(2) 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.6389(9)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.351(4) yes
N1 . C6 . 1.346(4) yes
N1 . Pd1 . 1.974(3) yes
C2 . C3 . 1.376(5) yes
C2 . C7 . 1.456(5) yes
C3 . C4 . 1.385(5) yes
C3 . H31 . 0.927 no
C4 . C5 . 1.390(5) yes
C4 . H41 . 0.949 no
C5 . C6 . 1.377(5) yes
C5 . H51 . 0.945 no
C6 . C52 . 1.462(5) yes
C7 . C8 . 1.369(5) yes
C7 . N9 . 1.374(5) yes
C7 . Pd1 . 2.856(4) yes
C8 . N11 . 1.341(5) yes
C8 . H81 . 0.946 no
N9 . N10 . 1.311(4) yes
N9 . Pd1 . 2.014(3) yes
N10 . N11 . 1.345(4) yes
N11 . C12 . 1.476(5) yes
C12 . C13 . 1.511(5) yes
C12 . H122 . 0.976 no
C12 . H121 . 0.971 no
C13 . O14 . 1.425(5) yes
C13 . H131 . 0.969 no
C13 . H132 . 0.967 no
O14 . C15 . 1.381(4) yes
C15 . C16 . 1.366(5) yes
C15 . C20 . 1.395(6) yes
C16 . C17 . 1.396(6) yes
C16 . H161 . 0.940 no
C17 . C18 . 1.386(6) yes
C17 . H171 . 0.932 no
C18 . C19 . 1.375(6) yes
C18 . O21 . 1.389(5) yes
C19 . C20 . 1.377(6) yes
C19 . H191 . 0.938 no
C20 . H201 . 0.940 no
O21 . C22 . 1.420(5) yes
C22 . C23 . 1.521(6) yes
C22 . H221 . 0.982 no
C22 . H222 . 0.995 no
C23 . N24 . 1.446(5) yes
C23 . H231 . 0.975 no
C23 . H232 . 0.980 no
N24 . C26 . 1.345(5) yes
N24 . H241 . 0.841(18) no
O25 . C26 . 1.219(5) yes
C26 . C27 . 1.501(6) yes
C27 . C28 . 1.392(6) yes
C27 . C32 . 1.383(6) yes
C28 . C29 . 1.414(6) yes
C28 . H281 . 0.933 no
C29 . C30 . 1.380(6) yes
C29 . C34 . 1.486(6) yes
C30 . C31 . 1.364(7) yes
C30 . H301 . 0.945 no
C31 . C32 . 1.373(6) yes
C31 . H311 . 0.949 no
C32 . H321 . 0.936 no
O33 . C34 . 1.242(5) yes
C34 . N35 . 1.340(6) yes
N35 . C36 . 1.484(6) yes
N35 . H351 . 0.894(18) no
C36 . C37 . 1.513(6) yes
C36 . H361 . 0.981 no
C36 . H362 . 0.972 no
C37 . O38 . 1.411(5) yes
C37 . H371 . 0.980 no
C37 . H372 . 0.980 no
O38 . C39 . 1.395(5) yes
C39 . C40 . 1.372(6) yes
C39 . C44 . 1.379(6) yes
C40 . C41 . 1.421(6) yes
C40 . H401 . 0.934 no
C41 . C42 . 1.375(6) yes
C41 . H411 . 0.945 no
C42 . C43 . 1.398(6) yes
C42 . O45 . 1.383(5) yes
C43 . C44 . 1.363(6) yes
C43 . H431 . 0.931 no
C44 . H441 . 0.940 no
O45 . C46 . 1.425(5) yes
C46 . C47 . 1.506(5) yes
C46 . H462 . 0.977 no
C46 . H461 . 0.983 no
C47 . N48 . 1.472(5) yes
C47 . H471 . 0.969 no
C47 . H472 . 0.958 no
N48 . N49 . 1.345(4) yes
N48 . C51 . 1.342(5) yes
N49 . N50 . 1.320(4) yes
N50 . C52 . 1.367(5) yes
N50 . Pd1 . 2.018(3) yes
C51 . C52 . 1.363(5) yes
C51 . H511 . 0.927 no
C52 . Pd1 . 2.855(4) yes
N101 . C102 . 1.176(7) yes
C102 . C103 . 1.438(8) yes
C103 . H1033 . 0.976 no
C103 . H1032 . 0.965 no
C103 . H1031 . 1.000 no
N111 . C112 . 1.142(7) yes
C112 . C113 . 1.433(8) yes
C113 . H1132 . 0.968 no
C113 . H1131 . 0.956 no
C113 . H1133 . 0.960 no
Pd1 . Cl1 . 2.2900(10) yes
F13 . B11 . 1.385(5) yes
B11 . F15 . 1.383(5) yes
B11 . F12 . 1.379(5) yes
B11 . F14 . 1.370(5) yes

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C6 . 122.1(3) yes
C2 . N1 . Pd1 . 118.7(3) yes
C6 . N1 . Pd1 . 118.9(2) yes
N1 . C2 . C3 . 119.9(3) yes
N1 . C2 . C7 . 111.3(3) yes
C3 . C2 . C7 . 128.7(3) yes
C2 . C3 . C4 . 118.5(4) yes
C2 . C3 . H31 . 121.1 no
C4 . C3 . H31 . 120.4 no
C3 . C4 . C5 . 121.2(4) yes
C3 . C4 . H41 . 119.7 no
C5 . C4 . H41 . 119.1 no
C4 . C5 . C6 . 117.9(4) yes
C4 . C5 . H51 . 119.7 no
C6 . C5 . H51 . 122.5 no
C5 . C6 . N1 . 120.4(3) yes
C5 . C6 . C52 . 128.2(3) yes
N1 . C6 . C52 . 111.2(3) yes
C2 . C7 . C8 . 137.2(4) yes
C2 . C7 . N9 . 116.5(3) yes
C8 . C7 . N9 . 106.2(3) yes
C2 . C7 . Pd1 . 76.2(2) yes
C8 . C7 . Pd1 . 146.4(3) yes
N9 . C7 . Pd1 . 40.30(17) yes
C7 . C8 . N11 . 105.3(3) yes
C7 . C8 . H81 . 128.4 no
N11 . C8 . H81 . 126.3 no
C7 . N9 . N10 . 111.2(3) yes
C7 . N9 . Pd1 . 113.5(2) yes
N10 . N9 . Pd1 . 135.2(3) yes
N9 . N10 . N11 . 104.9(3) yes
N10 . N11 . C8 . 112.4(3) yes
N10 . N11 . C12 . 118.9(3) yes
C8 . N11 . C12 . 128.2(3) yes
N11 . C12 . C13 . 110.4(3) yes
N11 . C12 . H122 . 109.9 no
C13 . C12 . H122 . 108.9 no
N11 . C12 . H121 . 107.1 no
C13 . C12 . H121 . 109.7 no
H122 . C12 . H121 . 110.9 no
C12 . C13 . O14 . 107.1(3) yes
C12 . C13 . H131 . 108.9 no
O14 . C13 . H131 . 109.8 no
C12 . C13 . H132 . 110.1 no
O14 . C13 . H132 . 109.5 no
H131 . C13 . H132 . 111.3 no
C13 . O14 . C15 . 117.0(3) yes
O14 . C15 . C16 . 125.2(4) yes
O14 . C15 . C20 . 115.2(3) yes
C16 . C15 . C20 . 119.6(4) yes
C15 . C16 . C17 . 120.9(4) yes
C15 . C16 . H161 . 119.8 no
C17 . C16 . H161 . 119.3 no
C16 . C17 . C18 . 118.8(4) yes
C16 . C17 . H171 . 120.7 no
C18 . C17 . H171 . 120.6 no
C17 . C18 . C19 . 120.6(4) yes
C17 . C18 . O21 . 124.5(4) yes
C19 . C18 . O21 . 114.9(4) yes
C18 . C19 . C20 . 120.1(4) yes
C18 . C19 . H191 . 119.2 no
C20 . C19 . H191 . 120.7 no
C15 . C20 . C19 . 120.0(4) yes
C15 . C20 . H201 . 119.4 no
C19 . C20 . H201 . 120.6 no
C18 . O21 . C22 . 118.6(3) yes
O21 . C22 . C23 . 106.1(4) yes
O21 . C22 . H221 . 110.4 no
C23 . C22 . H221 . 109.4 no
O21 . C22 . H222 . 110.4 no
C23 . C22 . H222 . 112.1 no
H221 . C22 . H222 . 108.6 no
C22 . C23 . N24 . 111.4(4) yes
C22 . C23 . H231 . 107.4 no
N24 . C23 . H231 . 110.4 no
C22 . C23 . H232 . 110.0 no
N24 . C23 . H232 . 108.4 no
H231 . C23 . H232 . 109.2 no
C23 . N24 . C26 . 120.2(4) yes
C23 . N24 . H241 . 117.4(14) no
C26 . N24 . H241 . 118.7(14) no
N24 . C26 . O25 . 122.0(4) yes
N24 . C26 . C27 . 117.4(4) yes
O25 . C26 . C27 . 120.6(4) yes
C26 . C27 . C28 . 124.7(4) yes
C26 . C27 . C32 . 116.3(4) yes
C28 . C27 . C32 . 119.0(4) yes
C27 . C28 . C29 . 119.8(4) yes
C27 . C28 . H281 . 119.1 no
C29 . C28 . H281 . 121.1 no
C28 . C29 . C30 . 118.7(4) yes
C28 . C29 . C34 . 123.6(4) yes
C30 . C29 . C34 . 117.6(4) yes
C29 . C30 . C31 . 121.4(5) yes
C29 . C30 . H301 . 118.4 no
C31 . C30 . H301 . 120.2 no
C30 . C31 . C32 . 119.7(5) yes
C30 . C31 . H311 . 120.2 no
C32 . C31 . H311 . 120.1 no
C27 . C32 . C31 . 121.4(4) yes
C27 . C32 . H321 . 118.4 no
C31 . C32 . H321 . 120.2 no
C29 . C34 . O33 . 119.6(5) yes
C29 . C34 . N35 . 118.7(4) yes
O33 . C34 . N35 . 121.8(5) yes
C34 . N35 . C36 . 119.5(4) yes
C34 . N35 . H351 . 122.0(13) no
C36 . N35 . H351 . 118.2(13) no
N35 . C36 . C37 . 111.1(4) yes
N35 . C36 . H361 . 109.7 no
C37 . C36 . H361 . 108.2 no
N35 . C36 . H362 . 108.2 no
C37 . C36 . H362 . 107.9 no
H361 . C36 . H362 . 111.8 no
C36 . C37 . O38 . 105.0(4) yes
C36 . C37 . H371 . 111.4 no
O38 . C37 . H371 . 109.2 no
C36 . C37 . H372 . 112.1 no
O38 . C37 . H372 . 110.7 no
H371 . C37 . H372 . 108.3 no
C37 . O38 . C39 . 118.4(4) yes
O38 . C39 . C40 . 125.2(4) yes
O38 . C39 . C44 . 114.9(4) yes
C40 . C39 . C44 . 119.9(4) yes
C39 . C40 . C41 . 120.4(4) yes
C39 . C40 . H401 . 120.6 no
C41 . C40 . H401 . 119.0 no
C40 . C41 . C42 . 118.8(4) yes
C40 . C41 . H411 . 120.6 no
C42 . C41 . H411 . 120.6 no
C41 . C42 . C43 . 119.5(4) yes
C41 . C42 . O45 . 125.2(4) yes
C43 . C42 . O45 . 115.3(4) yes
C42 . C43 . C44 . 121.1(4) yes
C42 . C43 . H431 . 118.9 no
C44 . C43 . H431 . 120.0 no
C39 . C44 . C43 . 120.2(5) yes
C39 . C44 . H441 . 120.0 no
C43 . C44 . H441 . 119.8 no
C42 . O45 . C46 . 117.8(3) yes
O45 . C46 . C47 . 106.2(3) yes
O45 . C46 . H462 . 110.4 no
C47 . C46 . H462 . 108.4 no
O45 . C46 . H461 . 110.1 no
C47 . C46 . H461 . 111.0 no
H462 . C46 . H461 . 110.7 no
C46 . C47 . N48 . 109.8(3) yes
C46 . C47 . H471 . 110.5 no
N48 . C47 . H471 . 108.2 no
C46 . C47 . H472 . 110.4 no
N48 . C47 . H472 . 107.7 no
H471 . C47 . H472 . 110.3 no
C47 . N48 . N49 . 119.2(3) yes
C47 . N48 . C51 . 127.6(3) yes
N49 . N48 . C51 . 112.8(3) yes
N48 . N49 . N50 . 104.6(3) yes
N49 . N50 . C52 . 110.7(3) yes
N49 . N50 . Pd1 . 135.6(3) yes
C52 . N50 . Pd1 . 113.7(2) yes
N48 . C51 . C52 . 104.7(3) yes
N48 . C51 . H511 . 127.4 no
C52 . C51 . H511 . 127.9 no
C6 . C52 . N50 . 116.4(3) yes
C6 . C52 . C51 . 136.3(4) yes
N50 . C52 . C51 . 107.3(3) yes
C6 . C52 . Pd1 . 76.1(2) yes
N50 . C52 . Pd1 . 40.34(16) yes
C51 . C52 . Pd1 . 147.6(3) yes
N101 . C102 . C103 . 177.7(6) yes
C102 . C103 . H1033 . 108.4 no
C102 . C103 . H1032 . 110.6 no
H1033 . C103 . H1032 . 110.7 no
C102 . C103 . H1031 . 106.0 no
H1033 . C103 . H1031 . 111.7 no
H1032 . C103 . H1031 . 109.3 no
N111 . C112 . C113 . 178.6(6) yes
C112 . C113 . H1132 . 109.6 no
C112 . C113 . H1131 . 109.3 no
H1132 . C113 . H1131 . 110.1 no
C112 . C113 . H1133 . 107.7 no
H1132 . C113 . H1133 . 110.7 no
H1131 . C113 . H1133 . 109.3 no
N50 . Pd1 . N9 . 159.58(12) yes
N50 . Pd1 . N1 . 79.70(12) yes
N9 . Pd1 . N1 . 79.89(12) yes
N50 . Pd1 . C52 . 26.00(11) yes
N9 . Pd1 . C52 . 133.57(12) yes
N1 . Pd1 . C52 . 53.70(11) yes
N50 . Pd1 . C7 . 133.39(12) yes
N9 . Pd1 . C7 . 26.19(12) yes
N1 . Pd1 . C7 . 53.70(11) yes
C52 . Pd1 . C7 . 107.39(11) yes
N50 . Pd1 . Cl1 . 101.60(9) yes
N9 . Pd1 . Cl1 . 98.75(9) yes
N1 . Pd1 . Cl1 . 176.63(9) yes
C52 . Pd1 . Cl1 . 127.51(8) yes
C7 . Pd1 . Cl1 . 124.86(8) yes
F13 . B11 . F15 . 108.3(3) yes
F13 . B11 . F12 . 108.8(4) yes
F15 . B11 . F12 . 110.0(4) yes
F13 . B11 . F14 . 109.3(4) yes
F15 . B11 . F14 . 110.7(4) yes
F12 . B11 . F14 . 109.8(4) yes

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C13 . H132 . O33 2_667 125 0.97 2.49 3.149(6) yes
C46 . H461 . O25 2_667 144 0.98 2.49 3.339(6) yes
C19 . H191 . O38 2_567 161 0.94 2.58 3.482(6) yes
C103 . H1031 . N101 2_667 145 1.00 2.60 3.463(6) yes


# end of ARCHIVE-HKL.CIF 
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile/diethyl ether'
####################################################################### 
# 
# 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_PdI_8
_database_code_depnum_ccdc_archive 'CCDC 2225117'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2022-12-08 deposited with the CCDC.	2023-01-16 downloaded from the CCDC.
;
#==============================================================================
# start Validation Reply Form
_vrf_THETM01_PdI_8               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: Crystals were small and weakly diffracting. Even with the use of 
synchrotron radiation, it was not possible to obtain diffraction beyond 0.90 A.
;
_vrf_PLAT027_PdI_8               
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      17.44 Degree
RESPONSE: Crystals were small and weakly diffracting. Even with the use of 
synchrotron radiation, it was not possible to obtain diffraction beyond 0.90 A.
;
_vrf_PLAT029_PdI_8               
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.871 Why?  
RESPONSE: Low data completion ratio is due to the limitations of the instrument
available at the Australian Synchrotron operating under rotation data 
collection with a fixed detector and affects some high angle data.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 

;
_refine_special_details          
; 
Crystals were very small and weakly diffracting, and required the use of 
synchrotron radiation. Even using synchrotron radiation, diffraction was quite
weak and no data was observed beyond 0.90 A. Despite this, refinement proceeded
very smoothly. It was necessary to add restraints to B-F bond lengths and 
thermal and vibrational ellipsoid parameters of the BF4- anion but the core of
the complex refined easily without restraints. N-H hydrogen atoms were 
initially inserted at calculated positions but their positions were then 
refined with restraints on N-H bond lengths and C-N-H angles.
;

_cell_length_a                   9.660(19)
_cell_length_b                   13.938(3)
_cell_length_c                   17.090(3)
_cell_angle_alpha                109.45(3)
_cell_angle_beta                 100.95(3)
_cell_angle_gamma                100.13(3)
_cell_volume                     2057.9(10)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Pd -0.9988 1.0072 19.3319 0.6987 15.5017 7.9893 5.2954 25.2052 0.6058 76.8986
5.2659 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

_chemical_formula_sum            'C39 H38 B F4 I N10 O6 Pd'
_chemical_formula_moiety         'C37 H35 I N9 O6 Pd, B F4 , C2 H3 N'
_chemical_compound_source        synthesized
_chemical_formula_weight         1062.90


_cell_measurement_reflns_used    17348
_cell_measurement_theta_min      1.31
_cell_measurement_theta_max      23.3
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_max          0.10

_exptl_crystal_density_diffrn    1.715
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1059.996
_exptl_absorpt_coefficient_mu    1.280

_diffrn_measurement_device_type  Synchrotron
_diffrn_radiation_source         'MX1 Beamline Australian Synchrotron'
_diffrn_measurement_device       'ADSC Quantum 210r'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_method       'φ scans'

_computing_data_collection       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      100
_diffrn_reflns_number            17348
_diffrn_reflns_av_unetI/netI     0.049
_reflns_number_total             4968
_diffrn_reflns_av_R_equivalents  0.033

_diffrn_reflns_theta_min         1.312
_diffrn_reflns_theta_max         23.256
_diffrn_measured_fraction_theta_max 0.839

_diffrn_reflns_theta_full        17.442
_diffrn_measured_fraction_theta_full 0.871


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -10
_reflns_limit_h_max              9
_reflns_limit_k_min              -15
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   5.88
_oxford_diffrn_Wilson_scale      16.36

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -2.25
_refine_diff_density_max         1.72


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     76
_refine_ls_number_parameters     567
_refine_ls_number_reflns         4965
_refine_ls_R_factor_ref          0.0976
_refine_ls_wR_factor_ref         0.2522
_refine_ls_goodness_of_fit_ref   0.9846
_refine_ls_shift/su_max          0.0007617
_refine_ls_shift/su_mean         0.0000218


# Computed with I/sigma = -10 
_reflns_number_all               4968
_refine_ls_R_factor_all          0.0978
_refine_ls_wR_factor_all         0.2555

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3684
_refine_ls_R_factor_gt           0.0800
_refine_ls_wR_factor_gt          0.2097


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.18P)² + 8.87P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.2933(10) 0.6067(7) 0.5843(6) 0.0601 1.0000 Uani . . . . . .
C2 C 0.1861(12) 0.6507(8) 0.5703(7) 0.0600 1.0000 Uani . . . . . .
C3 C 0.0534(13) 0.6219(8) 0.5884(7) 0.0621 1.0000 Uani . . . . . .
C4 C 0.0423(13) 0.5465(9) 0.6253(8) 0.0672 1.0000 Uani . . . . . .
C5 C 0.1535(13) 0.4996(8) 0.6408(7) 0.0638 1.0000 Uani . . . . . .
C6 C 0.2829(13) 0.5332(8) 0.6204(7) 0.0602 1.0000 Uani . . . . . .
C7 C 0.2269(12) 0.7325(9) 0.5366(7) 0.0597 1.0000 Uani . . . . . .
C8 C 0.1695(13) 0.8055(8) 0.5144(7) 0.0607 1.0000 Uani . . . . . .
N9 N 0.3712(10) 0.7533(7) 0.5316(5) 0.0582 1.0000 Uani . . . . . .
N10 N 0.4008(10) 0.8331(7) 0.5078(6) 0.0616 1.0000 Uani . . . . . .
N11 N 0.2752(10) 0.8636(7) 0.4982(6) 0.0611 1.0000 Uani . . . . . .
C12 C 0.2782(13) 0.9636(8) 0.4837(7) 0.0600 1.0000 Uani . . . . . .
C13 C 0.3120(11) 1.0539(8) 0.5704(7) 0.0544 1.0000 Uani . . . . . .
O14 O 0.4505(8) 1.0556(5) 0.6173(4) 0.0584 1.0000 Uani . . . . . .
C15 C 0.5078(12) 1.1335(8) 0.6990(7) 0.0531 1.0000 Uani . . . . . .
C16 C 0.4359(12) 1.2056(8) 0.7370(7) 0.0602 1.0000 Uani . . . . . .
C17 C 0.5037(13) 1.2849(8) 0.8194(7) 0.0618 1.0000 Uani . . . . . .
C18 C 0.6420(13) 1.2885(8) 0.8608(7) 0.0602 1.0000 Uani . . . . . .
C19 C 0.7120(12) 1.2135(8) 0.8236(8) 0.0627 1.0000 Uani . . . . . .
C20 C 0.6482(13) 1.1373(8) 0.7432(7) 0.0607 1.0000 Uani . . . . . .
O21 O 0.7215(9) 1.3612(6) 0.9420(5) 0.0666 1.0000 Uani . . . . . .
C22 C 0.6523(13) 1.4352(9) 0.9903(7) 0.0681 1.0000 Uani . . . . . .
C23 C 0.7450(14) 1.4782(9) 1.0823(7) 0.0685 1.0000 Uani D . . . . .
N24 N 0.7276(11) 1.3986(7) 1.1214(6) 0.0641 1.0000 Uani D . . . . .
O25 O 0.5192(9) 1.4329(6) 1.1486(5) 0.0734 1.0000 Uani . . . . . .
C26 C 0.6072(14) 1.3792(9) 1.1474(7) 0.0640 1.0000 Uani D . . . . .
C27 C 0.5851(12) 1.2895(8) 1.1784(7) 0.0557 1.0000 Uani . . . . . .
C28 C 0.6912(13) 1.2376(8) 1.1963(7) 0.0600 1.0000 Uani . . . . . .
C29 C 0.6622(14) 1.1562(8) 1.2249(7) 0.0672 1.0000 Uani . . . . . .
C30 C 0.5220(14) 1.1269(9) 1.2368(8) 0.0746 1.0000 Uani . . . . . .
C31 C 0.4172(15) 1.1768(9) 1.2186(8) 0.0710 1.0000 Uani . . . . . .
C32 C 0.4477(15) 1.2570(9) 1.1891(8) 0.0735 1.0000 Uani . . . . . .
O33 O 0.7705(11) 1.0674(7) 1.3059(6) 0.0829 1.0000 Uani . . . . . .
C34 C 0.7686(15) 1.0994(8) 1.2467(8) 0.0701 1.0000 Uani D . . . . .
N35 N 0.8667(10) 1.0846(7) 1.1994(6) 0.0627 1.0000 Uani D . . . . .
C36 C 0.9778(14) 1.0307(9) 1.2160(8) 0.0697 1.0000 Uani D . . . . .
C37 C 0.9430(15) 0.9170(9) 1.1568(7) 0.0694 1.0000 Uani . . . . . .
O38 O 0.9413(9) 0.9177(6) 1.0728(5) 0.0704 1.0000 Uani . . . . . .
C39 C 0.9258(13) 0.8216(8) 1.0070(8) 0.0631 1.0000 Uani . . . . . .
C40 C 0.9335(13) 0.8288(8) 0.9282(7) 0.0636 1.0000 Uani . . . . . .
C41 C 0.9186(13) 0.7379(9) 0.8587(7) 0.0646 1.0000 Uani . . . . . .
C42 C 0.8989(12) 0.6423(8) 0.8669(7) 0.0569 1.0000 Uani . . . . . .
C43 C 0.8982(12) 0.6362(8) 0.9462(7) 0.0605 1.0000 Uani . . . . . .
C44 C 0.9105(13) 0.7279(8) 1.0172(8) 0.0643 1.0000 Uani . . . . . .
O45 O 0.8809(8) 0.5555(5) 0.7921(5) 0.0632 1.0000 Uani . . . . . .
C46 C 0.7943(12) 0.4577(8) 0.7874(7) 0.0621 1.0000 Uani . . . . . .
C47 C 0.7158(12) 0.3944(8) 0.6940(7) 0.0614 1.0000 Uani . . . . . .
N48 N 0.6076(10) 0.4448(6) 0.6632(6) 0.0590 1.0000 Uani . . . . . .
N49 N 0.6493(10) 0.5176(7) 0.6297(6) 0.0596 1.0000 Uani . . . . . .
N50 N 0.5339(10) 0.5542(6) 0.6141(6) 0.0595 1.0000 Uani . . . . . .
C51 C 0.4671(13) 0.4324(8) 0.6659(7) 0.0630 1.0000 Uani . . . . . .
C52 C 0.4204(13) 0.5026(8) 0.6338(7) 0.0607 1.0000 Uani . . . . . .
I1 I 0.73791(8) 0.75335(6) 0.56315(5) 0.0672 1.0000 Uani . . . . . .
Pd1 Pd 0.48638(9) 0.66342(6) 0.56992(5) 0.0581 1.0000 Uani . . . . . .
F14 F 1.0456(10) 0.7019(7) 0.3274(6) 0.1146 1.0000 Uani D U . . . .
B11 B 0.9394(11) 0.7404(7) 0.2942(7) 0.0834 1.0000 Uani D U . . . .
F15 F 0.8069(11) 0.6824(9) 0.2902(10) 0.1549 1.0000 Uani D U . . . .
F12 F 0.9643(11) 0.8462(6) 0.3326(6) 0.1192 1.0000 Uani D U . . . .
F13 F 0.9329(17) 0.7183(7) 0.2104(5) 0.1666 1.0000 Uani D U . . . .
N101 N 0.3017(16) 0.9154(11) 0.9906(9) 0.0993 1.0000 Uani . . . . . .
C102 C 0.4073(19) 0.8984(10) 1.0222(9) 0.0798 1.0000 Uani . . . . . .
C103 C 0.5392(16) 0.8768(10) 1.0564(9) 0.0859 1.0000 Uani . . . . . .
H31 H -0.0226 0.6525 0.5765 0.0752 1.0000 Uiso R . . . . .
H41 H -0.0423 0.5275 0.6405 0.0802 1.0000 Uiso R . . . . .
H51 H 0.1425 0.4484 0.6642 0.0762 1.0000 Uiso R . . . . .
H81 H 0.0761 0.8143 0.5118 0.0752 1.0000 Uiso R . . . . .
H121 H 0.3544 0.9765 0.4553 0.0742 1.0000 Uiso R . . . . .
H122 H 0.1843 0.9578 0.4473 0.0742 1.0000 Uiso R . . . . .
H131 H 0.3136 1.1194 0.5619 0.0660 1.0000 Uiso R . . . . .
H132 H 0.2375 1.0399 0.5993 0.0660 1.0000 Uiso R . . . . .
H161 H 0.3414 1.2019 0.7088 0.0740 1.0000 Uiso R . . . . .
H171 H 0.4548 1.3340 0.8453 0.0719 1.0000 Uiso R . . . . .
H191 H 0.8049 1.2165 0.8536 0.0760 1.0000 Uiso R . . . . .
H201 H 0.6961 1.0867 0.7172 0.0700 1.0000 Uiso R . . . . .
H221 H 0.6498 1.4921 0.9691 0.0811 1.0000 Uiso R . . . . .
H222 H 0.5536 1.3987 0.9852 0.0809 1.0000 Uiso R . . . . .
H231 H 0.8468 1.4980 1.0827 0.0811 1.0000 Uiso R . . . . .
H232 H 0.7165 1.5383 1.1160 0.0810 1.0000 Uiso R . . . . .
H281 H 0.7810 1.2582 1.1878 0.0679 1.0000 Uiso R . . . . .
H301 H 0.5014 1.0726 1.2568 0.0911 1.0000 Uiso R . . . . .
H311 H 0.3248 1.1567 1.2264 0.0851 1.0000 Uiso R . . . . .
H321 H 0.3760 1.2903 1.1763 0.0853 1.0000 Uiso R . . . . .
H361 H 1.0701 1.0681 1.2110 0.0849 1.0000 Uiso R . . . . .
H362 H 0.9922 1.0360 1.2759 0.0851 1.0000 Uiso R . . . . .
H371 H 1.0162 0.8838 1.1752 0.0851 1.0000 Uiso R . . . . .
H372 H 0.8472 0.8793 1.1566 0.0851 1.0000 Uiso R . . . . .
H401 H 0.9474 0.8938 0.9226 0.0741 1.0000 Uiso R . . . . .
H411 H 0.9234 0.7409 0.8055 0.0782 1.0000 Uiso R . . . . .
H431 H 0.8896 0.5716 0.9520 0.0720 1.0000 Uiso R . . . . .
H441 H 0.9075 0.7243 1.0698 0.0782 1.0000 Uiso R . . . . .
H461 H 0.8562 0.4193 0.8096 0.0750 1.0000 Uiso R . . . . .
H462 H 0.7246 0.4704 0.8209 0.0752 1.0000 Uiso R . . . . .
H471 H 0.7853 0.3898 0.6603 0.0731 1.0000 Uiso R . . . . .
H472 H 0.6642 0.3244 0.6870 0.0731 1.0000 Uiso R . . . . .
H511 H 0.4148 0.3863 0.6863 0.0790 1.0000 Uiso R . . . . .
H1031 H 0.5497 0.8890 1.1169 0.1311 1.0000 Uiso R . . . . .
H1032 H 0.5385 0.8034 1.0263 0.1310 1.0000 Uiso R . . . . .
H1033 H 0.6210 0.9218 1.0510 0.1310 1.0000 Uiso R . . . . .
H241 H 0.768(6) 1.348(3) 1.105(4) 0.076(2) 1.0000 Uiso D . . . . .
H351 H 0.849(7) 1.093(7) 1.151(3) 0.074(2) 1.0000 Uiso D . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.2270(4)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C2 . 1.317(14) yes
N1 . C6 . 1.361(15) yes
N1 . Pd1 . 1.987(9) yes
C2 . C3 . 1.397(16) yes
C2 . C7 . 1.466(16) yes
C3 . C4 . 1.393(17) yes
C3 . H31 . 0.934 no
C4 . C5 . 1.381(16) yes
C4 . H41 . 0.925 no
C5 . C6 . 1.404(16) yes
C5 . H51 . 0.927 no
C6 . C52 . 1.466(16) yes
C7 . C8 . 1.364(16) yes
C7 . N9 . 1.398(15) yes
C8 . N11 . 1.320(14) yes
C8 . H81 . 0.927 no
N9 . N10 . 1.312(12) yes
N9 . Pd1 . 1.998(9) yes
N10 . N11 . 1.353(12) yes
N11 . C12 . 1.492(14) yes
C12 . C13 . 1.522(14) yes
C12 . H121 . 0.977 no
C12 . H122 . 0.971 no
C13 . O14 . 1.415(12) yes
C13 . H131 . 0.971 no
C13 . H132 . 0.974 no
O14 . C15 . 1.385(12) yes
C15 . C16 . 1.377(15) yes
C15 . C20 . 1.404(15) yes
C16 . C17 . 1.412(15) yes
C16 . H161 . 0.932 no
C17 . C18 . 1.371(16) yes
C17 . H171 . 0.937 no
C18 . C19 . 1.388(15) yes
C18 . O21 . 1.388(13) yes
C19 . C20 . 1.368(15) yes
C19 . H191 . 0.931 no
C20 . H201 . 0.945 no
O21 . C22 . 1.441(13) yes
C22 . C23 . 1.511(16) yes
C22 . H221 . 0.977 no
C22 . H222 . 0.972 no
C23 . N24 . 1.476(15) yes
C23 . H231 . 0.972 no
C23 . H232 . 0.964 no
N24 . C26 . 1.337(15) yes
N24 . H241 . 0.86(2) no
O25 . C26 . 1.227(14) yes
C26 . C27 . 1.509(17) yes
C27 . C28 . 1.399(16) yes
C27 . C32 . 1.391(17) yes
C28 . C29 . 1.384(16) yes
C28 . H281 . 0.918 no
C29 . C30 . 1.417(18) yes
C29 . C34 . 1.470(18) yes
C30 . C31 . 1.370(18) yes
C30 . H301 . 0.936 no
C31 . C32 . 1.381(18) yes
C31 . H311 . 0.935 no
C32 . H321 . 0.931 no
O33 . C34 . 1.233(15) yes
C34 . N35 . 1.357(15) yes
N35 . C36 . 1.451(14) yes
N35 . H351 . 0.86(2) no
C36 . C37 . 1.504(15) yes
C36 . H361 . 0.984 no
C36 . H362 . 0.983 no
C37 . O38 . 1.437(14) yes
C37 . H371 . 0.970 no
C37 . H372 . 0.980 no
O38 . C39 . 1.394(12) yes
C39 . C40 . 1.398(16) yes
C39 . C44 . 1.361(16) yes
C40 . C41 . 1.380(15) yes
C40 . H401 . 0.932 no
C41 . C42 . 1.371(16) yes
C41 . H411 . 0.933 no
C42 . C43 . 1.385(15) yes
C42 . O45 . 1.393(12) yes
C43 . C44 . 1.407(15) yes
C43 . H431 . 0.930 no
C44 . H441 . 0.922 no
O45 . C46 . 1.436(12) yes
C46 . C47 . 1.505(15) yes
C46 . H461 . 0.974 no
C46 . H462 . 0.966 no
C47 . N48 . 1.469(14) yes
C47 . H471 . 0.962 no
C47 . H472 . 0.971 no
N48 . N49 . 1.361(12) yes
N48 . C51 . 1.349(15) yes
N49 . N50 . 1.323(12) yes
N50 . C52 . 1.362(15) yes
N50 . Pd1 . 1.995(9) yes
C51 . C52 . 1.371(16) yes
C51 . H511 . 0.945 no
C52 . Pd1 . 2.831(11) yes
I1 . Pd1 . 2.5730(13) yes
F14 . B11 . 1.356(9) yes
B11 . F15 . 1.365(9) yes
B11 . F12 . 1.354(8) yes
B11 . F13 . 1.348(9) yes
N101 . C102 . 1.162(19) yes
C102 . C103 . 1.42(2) yes
C103 . H1031 . 0.972 no
C103 . H1032 . 0.979 no
C103 . H1033 . 0.958 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . N1 . C6 . 121.6(10) yes
C2 . N1 . Pd1 . 119.7(8) yes
C6 . N1 . Pd1 . 118.0(7) yes
N1 . C2 . C3 . 122.2(10) yes
N1 . C2 . C7 . 111.5(10) yes
C3 . C2 . C7 . 126.3(11) yes
C2 . C3 . C4 . 116.3(11) yes
C2 . C3 . H31 . 121.1 no
C4 . C3 . H31 . 122.6 no
C3 . C4 . C5 . 122.5(11) yes
C3 . C4 . H41 . 119.0 no
C5 . C4 . H41 . 118.5 no
C4 . C5 . C6 . 117.3(11) yes
C4 . C5 . H51 . 120.8 no
C6 . C5 . H51 . 121.9 no
C5 . C6 . N1 . 120.0(10) yes
C5 . C6 . C52 . 129.7(11) yes
N1 . C6 . C52 . 110.3(10) yes
C2 . C7 . C8 . 138.8(11) yes
C2 . C7 . N9 . 115.3(10) yes
C8 . C7 . N9 . 105.5(10) yes
C7 . C8 . N11 . 106.1(11) yes
C7 . C8 . H81 . 127.9 no
N11 . C8 . H81 . 125.9 no
C7 . N9 . N10 . 110.8(9) yes
C7 . N9 . Pd1 . 113.8(7) yes
N10 . N9 . Pd1 . 135.2(8) yes
N9 . N10 . N11 . 104.5(9) yes
N10 . N11 . C8 . 113.1(9) yes
N10 . N11 . C12 . 118.0(9) yes
C8 . N11 . C12 . 128.2(9) yes
N11 . C12 . C13 . 108.8(8) yes
N11 . C12 . H121 . 109.5 no
C13 . C12 . H121 . 109.1 no
N11 . C12 . H122 . 109.4 no
C13 . C12 . H122 . 110.6 no
H121 . C12 . H122 . 109.4 no
C12 . C13 . O14 . 105.7(8) yes
C12 . C13 . H131 . 109.6 no
O14 . C13 . H131 . 111.3 no
C12 . C13 . H132 . 109.0 no
O14 . C13 . H132 . 110.8 no
H131 . C13 . H132 . 110.2 no
C13 . O14 . C15 . 116.9(8) yes
O14 . C15 . C16 . 123.8(10) yes
O14 . C15 . C20 . 116.3(9) yes
C16 . C15 . C20 . 119.9(10) yes
C15 . C16 . C17 . 120.5(11) yes
C15 . C16 . H161 . 120.2 no
C17 . C16 . H161 . 119.3 no
C16 . C17 . C18 . 118.7(10) yes
C16 . C17 . H171 . 120.5 no
C18 . C17 . H171 . 120.8 no
C17 . C18 . C19 . 120.6(11) yes
C17 . C18 . O21 . 125.2(10) yes
C19 . C18 . O21 . 114.2(10) yes
C18 . C19 . C20 . 121.0(11) yes
C18 . C19 . H191 . 119.0 no
C20 . C19 . H191 . 120.0 no
C15 . C20 . C19 . 119.2(10) yes
C15 . C20 . H201 . 119.4 no
C19 . C20 . H201 . 121.4 no
C18 . O21 . C22 . 118.6(9) yes
O21 . C22 . C23 . 105.4(10) yes
O21 . C22 . H221 . 110.7 no
C23 . C22 . H221 . 110.4 no
O21 . C22 . H222 . 109.3 no
C23 . C22 . H222 . 111.2 no
H221 . C22 . H222 . 109.9 no
C22 . C23 . N24 . 111.4(9) yes
C22 . C23 . H231 . 108.6 no
N24 . C23 . H231 . 108.4 no
C22 . C23 . H232 . 109.6 no
N24 . C23 . H232 . 108.4 no
H231 . C23 . H232 . 110.5 no
C23 . N24 . C26 . 118.6(10) yes
C23 . N24 . H241 . 117.2(18) no
C26 . N24 . H241 . 117.4(18) no
N24 . C26 . O25 . 122.2(11) yes
N24 . C26 . C27 . 117.2(11) yes
O25 . C26 . C27 . 120.5(11) yes
C26 . C27 . C28 . 124.9(10) yes
C26 . C27 . C32 . 116.4(11) yes
C28 . C27 . C32 . 118.6(11) yes
C27 . C28 . C29 . 121.3(11) yes
C27 . C28 . H281 . 118.3 no
C29 . C28 . H281 . 120.4 no
C28 . C29 . C30 . 118.4(12) yes
C28 . C29 . C34 . 124.5(12) yes
C30 . C29 . C34 . 117.1(11) yes
C29 . C30 . C31 . 120.5(13) yes
C29 . C30 . H301 . 119.2 no
C31 . C30 . H301 . 120.3 no
C30 . C31 . C32 . 120.2(12) yes
C30 . C31 . H311 . 119.9 no
C32 . C31 . H311 . 119.9 no
C27 . C32 . C31 . 120.9(12) yes
C27 . C32 . H321 . 119.2 no
C31 . C32 . H321 . 119.9 no
C29 . C34 . O33 . 121.8(11) yes
C29 . C34 . N35 . 117.1(11) yes
O33 . C34 . N35 . 121.1(12) yes
C34 . N35 . C36 . 121.8(10) yes
C34 . N35 . H351 . 118.4(17) no
C36 . N35 . H351 . 117.9(17) no
N35 . C36 . C37 . 114.9(10) yes
N35 . C36 . H361 . 108.8 no
C37 . C36 . H361 . 108.2 no
N35 . C36 . H362 . 107.2 no
C37 . C36 . H362 . 109.7 no
H361 . C36 . H362 . 107.8 no
C36 . C37 . O38 . 105.8(10) yes
C36 . C37 . H371 . 110.7 no
O38 . C37 . H371 . 110.9 no
C36 . C37 . H372 . 109.9 no
O38 . C37 . H372 . 110.3 no
H371 . C37 . H372 . 109.1 no
C37 . O38 . C39 . 117.3(9) yes
O38 . C39 . C40 . 114.3(10) yes
O38 . C39 . C44 . 124.3(11) yes
C40 . C39 . C44 . 121.3(10) yes
C39 . C40 . C41 . 118.9(10) yes
C39 . C40 . H401 . 120.4 no
C41 . C40 . H401 . 120.6 no
C40 . C41 . C42 . 120.7(11) yes
C40 . C41 . H411 . 120.4 no
C42 . C41 . H411 . 118.9 no
C41 . C42 . C43 . 120.2(10) yes
C41 . C42 . O45 . 115.8(10) yes
C43 . C42 . O45 . 124.0(9) yes
C42 . C43 . C44 . 119.8(10) yes
C42 . C43 . H431 . 119.8 no
C44 . C43 . H431 . 120.5 no
C43 . C44 . C39 . 119.1(11) yes
C43 . C44 . H441 . 120.4 no
C39 . C44 . H441 . 120.6 no
C42 . O45 . C46 . 115.4(8) yes
O45 . C46 . C47 . 107.3(9) yes
O45 . C46 . H461 . 110.5 no
C47 . C46 . H461 . 110.0 no
O45 . C46 . H462 . 110.5 no
C47 . C46 . H462 . 110.1 no
H461 . C46 . H462 . 108.5 no
C46 . C47 . N48 . 110.4(9) yes
C46 . C47 . H471 . 109.4 no
N48 . C47 . H471 . 109.0 no
C46 . C47 . H472 . 110.1 no
N48 . C47 . H472 . 107.8 no
H471 . C47 . H472 . 110.2 no
C47 . N48 . N49 . 119.0(9) yes
C47 . N48 . C51 . 128.8(10) yes
N49 . N48 . C51 . 112.2(9) yes
N48 . N49 . N50 . 105.1(8) yes
N49 . N50 . C52 . 110.1(9) yes
N49 . N50 . Pd1 . 136.3(7) yes
C52 . N50 . Pd1 . 113.6(8) yes
N48 . C51 . C52 . 104.2(10) yes
N48 . C51 . H511 . 127.1 no
C52 . C51 . H511 . 128.7 no
C6 . C52 . C51 . 134.1(11) yes
C6 . C52 . N50 . 117.5(10) yes
C51 . C52 . N50 . 108.3(11) yes
C6 . C52 . Pd1 . 77.3(6) yes
C51 . C52 . Pd1 . 148.5(9) yes
N50 . C52 . Pd1 . 40.2(5) yes
N9 . Pd1 . N50 . 159.8(4) yes
N9 . Pd1 . N1 . 79.5(4) yes
N50 . Pd1 . N1 . 80.3(4) yes
N9 . Pd1 . C52 . 133.6(4) yes
N50 . Pd1 . C52 . 26.2(4) yes
N1 . Pd1 . C52 . 54.2(4) yes
N9 . Pd1 . I1 . 98.4(3) yes
N50 . Pd1 . I1 . 101.7(3) yes
N1 . Pd1 . I1 . 174.5(2) yes
C52 . Pd1 . I1 . 127.6(2) yes
F14 . B11 . F15 . 109.0(9) yes
F14 . B11 . F12 . 113.5(9) yes
F15 . B11 . F12 . 115.9(10) yes
F14 . B11 . F13 . 108.3(10) yes
F15 . B11 . F13 . 102.3(11) yes
F12 . B11 . F13 . 107.1(9) yes
N101 . C102 . C103 . 176.7(16) yes
C102 . C103 . H1031 . 109.4 no
C102 . C103 . H1032 . 111.1 no
H1031 . C103 . H1032 . 108.0 no
C102 . C103 . H1033 . 110.1 no
H1031 . C103 . H1033 . 109.2 no
H1032 . C103 . H1033 . 109.0 no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C12 . H121 . O14 2_676 159 0.98 2.47 3.403(18) yes
C13 . H132 . O33 2_677 128 0.97 2.55 3.240(18) yes
N35 . H351 . N101 2_677 157(6) 0.86(2) 2.53(4) 3.344(18) yes


# end of ARCHIVE-HKL.CIF 
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile/diethyl ether'
####################################################################### 
# 
# 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_8Br
_database_code_depnum_ccdc_archive 'CCDC 2225744'
loop_
_audit_author_name
_audit_author_address
'Nicholas White'
;Australian National University
Australia
;
_audit_update_record             
;
2022-12-12 deposited with the CCDC.	2023-01-16 downloaded from the CCDC.
;
#==============================================================================
# start Validation Reply Form
_vrf_PLAT029_8Br                 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.923 Why?  
RESPONSE: Low data completion ratio is due to the limitations of the instrument
available at the Australian Synchrotron operating under rotation data 
collection with a fixed detector and affects some high angle data.
;

_vrf_PLAT094_8Br                 
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       4.22 Report
RESPONSE: Residual electron density is located close to the bromide anions.
;
_vrf_PLAT097_8Br                 
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       3.59 eA-3  
RESPONSE: Residual electron density is located close to the bromide anions.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 

;
_refine_special_details          
; 
The asymmetric unit contains two macrocycles, two bromide anions and two TBA 
cations, as well as one acetonitrile solvate and a half occupancy water 
molecule located very close to the inversion centre, such that one of its
hydrogen atoms is located on the inversion centre.

C-H hydrogen atoms were  visible in the Fourier difference map and 
were initially refined with restraints on bond lengths and angles, after which 
the positions were used as the basis for a riding model. Amide N-H hydrogen 
atoms were visible in the Fourier difference map and were refined
with restraints on bond lengths and angles. One of the hydrogen atoms of 
the half occupancy water molecule was located on the centre of inversion, the 
other was inserted at an idealised hydrogen bonding position.
;

_cell_length_a                   16.286(3)
_cell_length_b                   16.323(3)
_cell_length_c                   21.177(4)
_cell_angle_alpha                106.89(3)
_cell_angle_beta                 90.64(3)
_cell_angle_gamma                92.77(3)
_cell_volume                     5378(2)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

_chemical_formula_sum            'C108 H146 Br2 N21 O12.50'
_chemical_formula_moiety         
'2(C37 H35 N9 O6), 2(C16 H36 N), C2 H3 N, 0.5(H 2 O), 2(Br)'
_chemical_compound_source        synthesized
_chemical_formula_weight         2098.29


_cell_measurement_reflns_used    37252
_cell_measurement_theta_min      1.01
_cell_measurement_theta_max      26.4
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.05
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_max          0.20

_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             2222
_exptl_absorpt_coefficient_mu    0.824

_diffrn_radiation_type           Synchrotron
_diffrn_radiation_source         'MX2 Beamline Australian Synchrotron'
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_measurement_device_type  'Dectris Eiger 16M'
_diffrn_measurement_method       'Omega Scan'

_computing_data_collection       'AS QEGUI'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      100
_diffrn_reflns_number            37252
_diffrn_reflns_av_unetI/netI     0.067
_reflns_number_total             20284
_diffrn_reflns_av_R_equivalents  0.048

_diffrn_reflns_theta_min         1.005
_diffrn_reflns_theta_max         26.372
_diffrn_measured_fraction_theta_max 0.921

_diffrn_reflns_theta_full        25.053
_diffrn_measured_fraction_theta_full 0.923

_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_reflns_limit_h_min              -20
_reflns_limit_h_max              20
_reflns_limit_k_min              -20
_reflns_limit_k_max              19
_reflns_limit_l_min              0
_reflns_limit_l_max              26

_oxford_diffrn_Wilson_B_factor   2.41
_oxford_diffrn_Wilson_scale      52.16

_atom_sites_solution_primary     other
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.85
_refine_diff_density_max         3.59

_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     3
_refine_ls_number_parameters     1297
_refine_ls_number_reflns         20281
_refine_ls_R_factor_ref          0.0686
_refine_ls_wR_factor_ref         0.1774
_refine_ls_goodness_of_fit_ref   0.9952
_refine_ls_shift/su_max          0.0253981
_refine_ls_shift/su_mean         0.0000756

# Computed with I/sigma = -10 
_reflns_number_all               20281
_refine_ls_R_factor_all          0.0686
_refine_ls_wR_factor_all         0.1774

# Computed with I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                17253
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_gt          0.1676


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.13P)² + 2.29P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atoms attached to an atom.
# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N201 N 0.02391(13) 0.79146(13) 0.71701(10) 0.0227 1.0000 Uani . . . . . .
C202 C -0.00777(16) 0.72558(16) 0.65362(12) 0.0261 1.0000 Uani . . . . . .
C203 C -0.07646(17) 0.75336(17) 0.61747(13) 0.0299 1.0000 Uani . . . . . .
C204 C -0.09129(18) 0.69080(18) 0.54880(13) 0.0323 1.0000 Uani . . . . . .
C205 C -0.1629(2) 0.7156(2) 0.51273(14) 0.0386 1.0000 Uani . . . . . .
C211 C -0.04404(15) 0.81549(16) 0.76652(12) 0.0236 1.0000 Uani . . . . . .
C212 C -0.07801(16) 0.74503(17) 0.79441(13) 0.0282 1.0000 Uani . . . . . .
C213 C -0.14618(16) 0.77937(18) 0.84215(13) 0.0287 1.0000 Uani . . . . . .
C214 C -0.17262(19) 0.7188(2) 0.88151(15) 0.0383 1.0000 Uani . . . . . .
C221 C 0.09304(15) 0.75022(16) 0.74334(12) 0.0244 1.0000 Uani . . . . . .
C222 C 0.13162(16) 0.80298(18) 0.80934(14) 0.0307 1.0000 Uani . . . . . .
C223 C 0.20222(16) 0.75684(18) 0.82964(14) 0.0304 1.0000 Uani . . . . . .
C224 C 0.1773(2) 0.6714(2) 0.83993(18) 0.0447 1.0000 Uani . . . . . .
C231 C 0.05401(15) 0.87466(15) 0.70395(12) 0.0230 1.0000 Uani . . . . . .
C232 C 0.11667(17) 0.86603(16) 0.65011(13) 0.0280 1.0000 Uani . . . . . .
C233 C 0.14395(16) 0.95486(17) 0.64422(12) 0.0266 1.0000 Uani . . . . . .
C234 C 0.20113(18) 1.00718(19) 0.70004(14) 0.0342 1.0000 Uani . . . . . .
N301 N 0.50899(13) 0.79222(13) 0.21087(10) 0.0226 1.0000 Uani . . . . . .
C302 C 0.48046(16) 0.74793(17) 0.13975(12) 0.0271 1.0000 Uani . . . . . .
C303 C 0.42119(17) 0.79583(18) 0.10962(13) 0.0292 1.0000 Uani . . . . . .
C304 C 0.40216(17) 0.7460(2) 0.03732(13) 0.0345 1.0000 Uani . . . . . .
C305 C 0.3342(2) 0.7835(2) 0.00654(15) 0.0445 1.0000 Uani . . . . . .
C311 C 0.54182(15) 0.88359(16) 0.22000(12) 0.0237 1.0000 Uani . . . . . .
C312 C 0.61185(16) 0.89734(16) 0.17674(13) 0.0267 1.0000 Uani . . . . . .
C313 C 0.61851(17) 0.99281(17) 0.18233(14) 0.0305 1.0000 Uani . . . . . .
C314 C 0.68964(17) 1.02092(18) 0.14653(14) 0.0310 1.0000 Uani . . . . . .
C321 C 0.57399(16) 0.73776(16) 0.22685(13) 0.0270 1.0000 Uani . . . . . .
C322 C 0.60703(16) 0.76475(17) 0.29781(13) 0.0285 1.0000 Uani . . . . . .
C323 C 0.64576(16) 0.68822(18) 0.31152(14) 0.0303 1.0000 Uani . . . . . .
C324 C 0.67830(19) 0.7089(2) 0.38201(15) 0.0387 1.0000 Uani . . . . . .
C331 C 0.43676(15) 0.80133(17) 0.25771(12) 0.0252 1.0000 Uani . . . . . .
C332 C 0.40273(17) 0.72091(18) 0.27195(13) 0.0302 1.0000 Uani . . . . . .
C333 C 0.33256(17) 0.7442(2) 0.32081(13) 0.0329 1.0000 Uani . . . . . .
C334 C 0.35923(18) 0.80605(19) 0.38789(13) 0.0331 1.0000 Uani . . . . . .
N401 N 0.22070(18) 0.65584(18) 0.62647(14) 0.0462 1.0000 Uani . . . . . .
C402 C 0.21334(17) 0.58401(19) 0.61419(15) 0.0341 1.0000 Uani . . . . . .
C403 C 0.2033(2) 0.4915(2) 0.5974(2) 0.0504 1.0000 Uani . . . . . .
N1 N 0.17259(13) 0.00154(13) 0.02801(10) 0.0233 1.0000 Uani . . . . . .
C2 C 0.17498(15) -0.04638(16) 0.06956(12) 0.0241 1.0000 Uani . . . . . .
C3 C 0.12064(16) -0.11705(17) 0.06471(13) 0.0277 1.0000 Uani . . . . . .
C4 C 0.06137(16) -0.13865(17) 0.01477(13) 0.0280 1.0000 Uani . . . . . .
C5 C 0.05741(15) -0.08981(16) -0.02856(12) 0.0252 1.0000 Uani . . . . . .
C6 C 0.11450(15) -0.02078(16) -0.02059(12) 0.0224 1.0000 Uani . . . . . .
C7 C 0.23889(16) -0.02172(16) 0.12233(12) 0.0246 1.0000 Uani . . . . . .
C8 C 0.29301(16) 0.04844(16) 0.14099(12) 0.0250 1.0000 Uani . . . . . .
N9 N 0.25266(15) -0.07207(15) 0.16243(11) 0.0300 1.0000 Uani . . . . . .
N10 N 0.31338(15) -0.03550(14) 0.20480(11) 0.0300 1.0000 Uani . . . . . .
N11 N 0.33777(13) 0.03775(13) 0.19132(10) 0.0239 1.0000 Uani . . . . . .
C12 C 0.40074(16) 0.09491(17) 0.23393(13) 0.0268 1.0000 Uani . . . . . .
C13 C 0.36490(16) 0.17406(16) 0.27871(12) 0.0260 1.0000 Uani . . . . . .
O14 O 0.35199(11) 0.23297(12) 0.24162(9) 0.0266 1.0000 Uani . . . . . .
C15 C 0.32328(15) 0.31067(16) 0.27695(13) 0.0248 1.0000 Uani . . . . . .
C16 C 0.29188(16) 0.32670(17) 0.33967(13) 0.0287 1.0000 Uani . . . . . .
C17 C 0.26360(16) 0.40722(17) 0.37195(13) 0.0290 1.0000 Uani . . . . . .
C18 C 0.26706(15) 0.47163(16) 0.34161(13) 0.0251 1.0000 Uani . . . . . .
C19 C 0.29877(16) 0.45583(17) 0.27856(13) 0.0268 1.0000 Uani . . . . . .
C20 C 0.32674(16) 0.37587(17) 0.24659(13) 0.0274 1.0000 Uani . . . . . .
O21 O 0.24253(11) 0.55360(11) 0.37017(9) 0.0271 1.0000 Uani . . . . . .
C22 C 0.21919(17) 0.57284(17) 0.43730(13) 0.0292 1.0000 Uani . . . . . .
C23 C 0.20756(17) 0.66754(18) 0.46301(13) 0.0304 1.0000 Uani . . . . . .
N24 N 0.13097(13) 0.69186(14) 0.43886(11) 0.0270 1.0000 Uani . . . . . .
C25 C 0.11403(16) 0.77475(16) 0.45765(12) 0.0251 1.0000 Uani . . . . . .
O26 O 0.16285(11) 0.83088(12) 0.49146(9) 0.0313 1.0000 Uani . . . . . .
C27 C 0.03189(16) 0.79764(16) 0.43738(12) 0.0242 1.0000 Uani . . . . . .
C28 C -0.01202(15) 0.74728(15) 0.38164(12) 0.0237 1.0000 Uani . . . . . .
C29 C -0.08638(16) 0.77262(16) 0.36326(12) 0.0237 1.0000 Uani . . . . . .
C30 C -0.11815(16) 0.84894(16) 0.40106(13) 0.0257 1.0000 Uani . . . . . .
C31 C -0.07570(17) 0.89844(16) 0.45743(13) 0.0276 1.0000 Uani . . . . . .
C32 C -0.00073(16) 0.87370(16) 0.47523(13) 0.0265 1.0000 Uani . . . . . .
O33 O -0.17650(12) 0.75754(13) 0.27078(9) 0.0323 1.0000 Uani . . . . . .
C34 C -0.13239(16) 0.72205(17) 0.30119(12) 0.0252 1.0000 Uani . . . . . .
N35 N -0.12240(14) 0.63695(14) 0.28286(11) 0.0281 1.0000 Uani . . . . . .
C36 C -0.15600(17) 0.58105(18) 0.22030(13) 0.0305 1.0000 Uani . . . . . .
C37 C -0.08680(16) 0.55068(17) 0.17312(12) 0.0271 1.0000 Uani . . . . . .
O38 O -0.12604(11) 0.50068(12) 0.11241(9) 0.0278 1.0000 Uani . . . . . .
C39 C -0.07693(16) 0.45129(16) 0.06557(12) 0.0246 1.0000 Uani . . . . . .
C40 C 0.00801(15) 0.45670(16) 0.06825(12) 0.0251 1.0000 Uani . . . . . .
C41 C 0.05221(15) 0.40377(16) 0.01754(12) 0.0234 1.0000 Uani . . . . . .
C42 C 0.01072(15) 0.34598(15) -0.03532(12) 0.0232 1.0000 Uani . . . . . .
C43 C -0.07485(15) 0.34203(16) -0.03866(13) 0.0255 1.0000 Uani . . . . . .
C44 C -0.11830(15) 0.39393(16) 0.01176(13) 0.0257 1.0000 Uani . . . . . .
O45 O 0.04645(10) 0.28875(11) -0.08794(9) 0.0264 1.0000 Uani . . . . . .
C46 C 0.13403(15) 0.28672(16) -0.08589(13) 0.0245 1.0000 Uani . . . . . .
C47 C 0.15669(15) 0.20501(16) -0.13562(12) 0.0240 1.0000 Uani . . . . . .
N48 N 0.13043(12) 0.12995(13) -0.11506(10) 0.0223 1.0000 Uani . . . . . .
N49 N 0.07606(13) 0.06980(14) -0.15210(10) 0.0253 1.0000 Uani . . . . . .
N50 N 0.06524(13) 0.01014(14) -0.12220(10) 0.0249 1.0000 Uani . . . . . .
C51 C 0.15450(15) 0.10935(16) -0.06071(12) 0.0219 1.0000 Uani . . . . . .
C52 C 0.11243(14) 0.03248(16) -0.06574(12) 0.0222 1.0000 Uani . . . . . .
N101 N 0.31081(13) 1.01017(14) 0.48395(10) 0.0249 1.0000 Uani . . . . . .
C102 C 0.30131(15) 1.05716(16) 0.44164(12) 0.0241 1.0000 Uani . . . . . .
C103 C 0.35552(17) 1.12565(17) 0.44064(13) 0.0282 1.0000 Uani . . . . . .
C104 C 0.42358(18) 1.14374(18) 0.48265(13) 0.0321 1.0000 Uani . . . . . .
C105 C 0.43558(16) 1.09556(17) 0.52516(13) 0.0289 1.0000 Uani . . . . . .
C106 C 0.37701(15) 1.02949(16) 0.52445(12) 0.0242 1.0000 Uani . . . . . .
C107 C 0.23060(15) 1.03124(16) 0.39538(12) 0.0243 1.0000 Uani . . . . . .
C108 C 0.17705(15) 0.96030(16) 0.38365(12) 0.0236 1.0000 Uani . . . . . .
N109 N 0.20932(13) 1.07754(14) 0.35412(11) 0.0277 1.0000 Uani . . . . . .
N110 N 0.14522(14) 1.03871(14) 0.31743(11) 0.0275 1.0000 Uani . . . . . .
N111 N 0.12557(12) 0.96727(13) 0.33555(10) 0.0230 1.0000 Uani . . . . . .
C112 C 0.05750(15) 0.90936(16) 0.30061(13) 0.0241 1.0000 Uani . . . . . .
C113 C 0.08546(16) 0.83683(16) 0.24420(12) 0.0253 1.0000 Uani . . . . . .
O114 O 0.12291(11) 0.77617(11) 0.27089(8) 0.0249 1.0000 Uani . . . . . .
C115 C 0.15757(14) 0.70939(16) 0.22383(12) 0.0219 1.0000 Uani . . . . . .
C116 C 0.13987(15) 0.62621(16) 0.22586(12) 0.0242 1.0000 Uani . . . . . .
C117 C 0.17487(15) 0.55817(16) 0.18116(13) 0.0249 1.0000 Uani . . . . . .
C118 C 0.22777(15) 0.57252(16) 0.13397(12) 0.0237 1.0000 Uani . . . . . .
C119 C 0.24761(15) 0.65614(16) 0.13314(12) 0.0234 1.0000 Uani . . . . . .
C120 C 0.21229(14) 0.72461(15) 0.17839(12) 0.0225 1.0000 Uani . . . . . .
O121 O 0.25622(11) 0.50104(11) 0.08897(9) 0.0273 1.0000 Uani . . . . . .
C122 C 0.31634(16) 0.51608(16) 0.04425(13) 0.0262 1.0000 Uani . . . . . .
C123 C 0.33430(16) 0.43165(17) -0.00470(13) 0.0280 1.0000 Uani . . . . . .
N124 N 0.37339(13) 0.37531(14) 0.02696(11) 0.0262 1.0000 Uani . . . . . .
O125 O 0.30508(11) 0.25538(12) -0.03640(9) 0.0310 1.0000 Uani . . . . . .
C126 C 0.35618(14) 0.29101(16) 0.00824(12) 0.0228 1.0000 Uani . . . . . .
C127 C 0.40317(14) 0.23782(16) 0.04163(12) 0.0220 1.0000 Uani . . . . . .
C128 C 0.45670(14) 0.27273(16) 0.09549(11) 0.0222 1.0000 Uani . . . . . .
C129 C 0.50413(15) 0.22006(16) 0.12014(12) 0.0234 1.0000 Uani . . . . . .
C130 C 0.49787(17) 0.13116(16) 0.09106(13) 0.0274 1.0000 Uani . . . . . .
C131 C 0.44243(17) 0.09616(17) 0.03866(13) 0.0289 1.0000 Uani . . . . . .
C132 C 0.39525(16) 0.14874(16) 0.01447(12) 0.0255 1.0000 Uani . . . . . .
O133 O 0.57484(12) 0.20999(13) 0.21612(9) 0.0328 1.0000 Uani . . . . . .
C134 C 0.55962(15) 0.25492(17) 0.18031(12) 0.0247 1.0000 Uani . . . . . .
N135 N 0.59013(13) 0.33596(14) 0.19142(10) 0.0259 1.0000 Uani . . . . . .
C136 C 0.62855(16) 0.38325(18) 0.25516(13) 0.0282 1.0000 Uani . . . . . .
C137 C 0.56429(16) 0.43654(17) 0.29675(12) 0.0263 1.0000 Uani . . . . . .
O138 O 0.59954(11) 0.47623(12) 0.36124(9) 0.0269 1.0000 Uani . . . . . .
C139 C 0.55011(15) 0.53228(16) 0.40408(12) 0.0236 1.0000 Uani . . . . . .
C140 C 0.47691(16) 0.55914(17) 0.38495(13) 0.0276 1.0000 Uani . . . . . .
C141 C 0.43205(16) 0.61711(17) 0.43090(13) 0.0269 1.0000 Uani . . . . . .
C142 C 0.45892(15) 0.64697(16) 0.49621(12) 0.0244 1.0000 Uani . . . . . .
C143 C 0.53129(16) 0.61909(16) 0.51623(12) 0.0251 1.0000 Uani . . . . . .
C144 C 0.57669(16) 0.56163(17) 0.47012(12) 0.0256 1.0000 Uani . . . . . .
O145 O 0.40904(11) 0.70542(12) 0.53656(9) 0.0277 1.0000 Uani . . . . . .
C146 C 0.42730(17) 0.73157(17) 0.60560(12) 0.0278 1.0000 Uani . . . . . .
C147 C 0.36868(17) 0.79955(17) 0.63738(12) 0.0273 1.0000 Uani . . . . . .
N148 N 0.38362(13) 0.87703(14) 0.61701(10) 0.0248 1.0000 Uani . . . . . .
N149 N 0.44447(14) 0.93475(15) 0.64705(11) 0.0295 1.0000 Uani . . . . . .
N150 N 0.44683(14) 0.99533(15) 0.61743(11) 0.0293 1.0000 Uani . . . . . .
C151 C 0.34680(15) 0.89981(16) 0.56792(12) 0.0245 1.0000 Uani . . . . . .
C152 C 0.38774(16) 0.97599(16) 0.56854(12) 0.0254 1.0000 Uani . . . . . .
Br2 Br 0.51946(2) 0.501278(18) 0.137426(15) 0.0405 1.0000 Uani . . . . . .
Br1 Br 0.007479(18) 0.513424(18) 0.343360(17) 0.0397 1.0000 Uani . . . . . .
H2021 H -0.0246 0.6746 0.6649 0.0309 1.0000 Uiso R . . . . .
H2022 H 0.0382 0.7138 0.6252 0.0306 1.0000 Uiso R . . . . .
H2031 H -0.1263 0.7554 0.6425 0.0355 1.0000 Uiso R . . . . .
H2032 H -0.0624 0.8103 0.6136 0.0354 1.0000 Uiso R . . . . .
H2041 H -0.1006 0.6342 0.5537 0.0390 1.0000 Uiso R . . . . .
H2042 H -0.0423 0.6901 0.5230 0.0391 1.0000 Uiso R . . . . .
H2052 H -0.1659 0.6807 0.4678 0.0584 1.0000 Uiso R . . . . .
H2053 H -0.2136 0.7085 0.5337 0.0576 1.0000 Uiso R . . . . .
H2051 H -0.1547 0.7751 0.5137 0.0577 1.0000 Uiso R . . . . .
H2111 H -0.0222 0.8630 0.8023 0.0283 1.0000 Uiso R . . . . .
H2112 H -0.0885 0.8337 0.7444 0.0274 1.0000 Uiso R . . . . .
H2121 H -0.0345 0.7259 0.8175 0.0342 1.0000 Uiso R . . . . .
H2122 H -0.0997 0.6964 0.7589 0.0340 1.0000 Uiso R . . . . .
H2131 H -0.1275 0.8345 0.8721 0.0356 1.0000 Uiso R . . . . .
H2132 H -0.1936 0.7876 0.8162 0.0347 1.0000 Uiso R . . . . .
H2142 H -0.2183 0.7417 0.9089 0.0574 1.0000 Uiso R . . . . .
H2143 H -0.1280 0.7110 0.9089 0.0580 1.0000 Uiso R . . . . .
H2141 H -0.1912 0.6645 0.8520 0.0576 1.0000 Uiso R . . . . .
H2211 H 0.0719 0.6966 0.7477 0.0289 1.0000 Uiso R . . . . .
H2212 H 0.1351 0.7404 0.7114 0.0283 1.0000 Uiso R . . . . .
H2221 H 0.0910 0.8103 0.8425 0.0372 1.0000 Uiso R . . . . .
H2222 H 0.1510 0.8588 0.8064 0.0371 1.0000 Uiso R . . . . .
H2231 H 0.2263 0.7938 0.8708 0.0375 1.0000 Uiso R . . . . .
H2232 H 0.2436 0.7486 0.7957 0.0368 1.0000 Uiso R . . . . .
H2242 H 0.2216 0.6504 0.8596 0.0677 1.0000 Uiso R . . . . .
H2243 H 0.1321 0.6777 0.8683 0.0680 1.0000 Uiso R . . . . .
H2241 H 0.1616 0.6302 0.7985 0.0682 1.0000 Uiso R . . . . .
H2311 H 0.0778 0.9111 0.7453 0.0269 1.0000 Uiso R . . . . .
H2312 H 0.0060 0.9003 0.6925 0.0270 1.0000 Uiso R . . . . .
H2321 H 0.1646 0.8391 0.6608 0.0344 1.0000 Uiso R . . . . .
H2322 H 0.0921 0.8321 0.6084 0.0340 1.0000 Uiso R . . . . .
H2331 H 0.0965 0.9871 0.6423 0.0313 1.0000 Uiso R . . . . .
H2332 H 0.1729 0.9464 0.6031 0.0312 1.0000 Uiso R . . . . .
H2342 H 0.2128 1.0628 0.6940 0.0513 1.0000 Uiso R . . . . .
H2343 H 0.1762 1.0137 0.7416 0.0510 1.0000 Uiso R . . . . .
H2341 H 0.2514 0.9778 0.6982 0.0503 1.0000 Uiso R . . . . .
H3021 H 0.5300 0.7381 0.1138 0.0322 1.0000 Uiso R . . . . .
H3022 H 0.4544 0.6941 0.1396 0.0329 1.0000 Uiso R . . . . .
H3031 H 0.4458 0.8509 0.1105 0.0350 1.0000 Uiso R . . . . .
H3032 H 0.3709 0.8043 0.1341 0.0340 1.0000 Uiso R . . . . .
H3041 H 0.4513 0.7456 0.0122 0.0406 1.0000 Uiso R . . . . .
H3042 H 0.3855 0.6862 0.0349 0.0410 1.0000 Uiso R . . . . .
H3052 H 0.3258 0.7508 -0.0391 0.0668 1.0000 Uiso R . . . . .
H3053 H 0.3485 0.8420 0.0092 0.0672 1.0000 Uiso R . . . . .
H3051 H 0.2841 0.7813 0.0294 0.0662 1.0000 Uiso R . . . . .
H3111 H 0.5590 0.9067 0.2660 0.0283 1.0000 Uiso R . . . . .
H3112 H 0.4960 0.9148 0.2119 0.0285 1.0000 Uiso R . . . . .
H3121 H 0.6626 0.8807 0.1923 0.0317 1.0000 Uiso R . . . . .
H3122 H 0.6002 0.8635 0.1311 0.0325 1.0000 Uiso R . . . . .
H3131 H 0.6245 1.0259 0.2285 0.0372 1.0000 Uiso R . . . . .
H3132 H 0.5678 1.0055 0.1628 0.0377 1.0000 Uiso R . . . . .
H3142 H 0.6907 1.0815 0.1530 0.0465 1.0000 Uiso R . . . . .
H3143 H 0.7400 1.0068 0.1631 0.0466 1.0000 Uiso R . . . . .
H3141 H 0.6837 0.9928 0.0994 0.0466 1.0000 Uiso R . . . . .
H3211 H 0.6191 0.7396 0.1982 0.0312 1.0000 Uiso R . . . . .
H3212 H 0.5510 0.6797 0.2167 0.0321 1.0000 Uiso R . . . . .
H3221 H 0.6493 0.8120 0.3041 0.0350 1.0000 Uiso R . . . . .
H3222 H 0.5625 0.7827 0.3280 0.0338 1.0000 Uiso R . . . . .
H3231 H 0.6915 0.6731 0.2825 0.0367 1.0000 Uiso R . . . . .
H3232 H 0.6058 0.6403 0.3034 0.0367 1.0000 Uiso R . . . . .
H3242 H 0.7079 0.6624 0.3887 0.0572 1.0000 Uiso R . . . . .
H3243 H 0.7139 0.7600 0.3933 0.0577 1.0000 Uiso R . . . . .
H3241 H 0.6326 0.7185 0.4116 0.0577 1.0000 Uiso R . . . . .
H3311 H 0.4569 0.8412 0.2988 0.0305 1.0000 Uiso R . . . . .
H3312 H 0.3933 0.8268 0.2386 0.0300 1.0000 Uiso R . . . . .
H3321 H 0.4457 0.6964 0.2912 0.0352 1.0000 Uiso R . . . . .
H3322 H 0.3820 0.6787 0.2320 0.0356 1.0000 Uiso R . . . . .
H3331 H 0.2896 0.7694 0.3015 0.0388 1.0000 Uiso R . . . . .
H3332 H 0.3106 0.6913 0.3280 0.0392 1.0000 Uiso R . . . . .
H3342 H 0.3132 0.8153 0.4163 0.0500 1.0000 Uiso R . . . . .
H3343 H 0.3793 0.8600 0.3832 0.0497 1.0000 Uiso R . . . . .
H3341 H 0.4018 0.7816 0.4075 0.0493 1.0000 Uiso R . . . . .
H4031 H 0.2433 0.4722 0.6228 0.0752 1.0000 Uiso R . . . . .
H4032 H 0.1486 0.4760 0.6080 0.0749 1.0000 Uiso R . . . . .
H4033 H 0.2118 0.4675 0.5511 0.0754 1.0000 Uiso R . . . . .
H31 H 0.1245 -0.1482 0.0951 0.0334 1.0000 Uiso R . . . . .
H41 H 0.0249 -0.1861 0.0105 0.0346 1.0000 Uiso R . . . . .
H51 H 0.0179 -0.1017 -0.0623 0.0300 1.0000 Uiso R . . . . .
H81 H 0.2990 0.0949 0.1241 0.0291 1.0000 Uiso R . . . . .
H121 H 0.4249 0.0631 0.2603 0.0322 1.0000 Uiso R . . . . .
H122 H 0.4437 0.1106 0.2079 0.0319 1.0000 Uiso R . . . . .
H131 H 0.4028 0.1997 0.3147 0.0302 1.0000 Uiso R . . . . .
H132 H 0.3137 0.1598 0.2968 0.0307 1.0000 Uiso R . . . . .
H161 H 0.2899 0.2844 0.3612 0.0350 1.0000 Uiso R . . . . .
H171 H 0.2421 0.4170 0.4139 0.0344 1.0000 Uiso R . . . . .
H191 H 0.3025 0.4990 0.2582 0.0320 1.0000 Uiso R . . . . .
H201 H 0.3488 0.3659 0.2047 0.0333 1.0000 Uiso R . . . . .
H222 H 0.2609 0.5582 0.4637 0.0339 1.0000 Uiso R . . . . .
H221 H 0.1687 0.5413 0.4408 0.0357 1.0000 Uiso R . . . . .
H232 H 0.2064 0.6825 0.5107 0.0371 1.0000 Uiso R . . . . .
H231 H 0.2533 0.6989 0.4505 0.0374 1.0000 Uiso R . . . . .
H281 H 0.0101 0.6966 0.3559 0.0294 1.0000 Uiso R . . . . .
H301 H -0.1676 0.8666 0.3884 0.0306 1.0000 Uiso R . . . . .
H311 H -0.0979 0.9483 0.4830 0.0325 1.0000 Uiso R . . . . .
H321 H 0.0291 0.9071 0.5120 0.0316 1.0000 Uiso R . . . . .
H361 H -0.1938 0.6119 0.2017 0.0366 1.0000 Uiso R . . . . .
H362 H -0.1844 0.5328 0.2290 0.0366 1.0000 Uiso R . . . . .
H372 H -0.0568 0.5991 0.1663 0.0332 1.0000 Uiso R . . . . .
H371 H -0.0499 0.5168 0.1903 0.0329 1.0000 Uiso R . . . . .
H401 H 0.0365 0.4959 0.1035 0.0303 1.0000 Uiso R . . . . .
H411 H 0.1097 0.4074 0.0189 0.0277 1.0000 Uiso R . . . . .
H431 H -0.1028 0.3044 -0.0753 0.0311 1.0000 Uiso R . . . . .
H441 H -0.1758 0.3909 0.0095 0.0304 1.0000 Uiso R . . . . .
H462 H 0.1585 0.3359 -0.0969 0.0290 1.0000 Uiso R . . . . .
H461 H 0.1530 0.2881 -0.0422 0.0290 1.0000 Uiso R . . . . .
H471 H 0.2152 0.2058 -0.1397 0.0290 1.0000 Uiso R . . . . .
H472 H 0.1306 0.2001 -0.1776 0.0288 1.0000 Uiso R . . . . .
H511 H 0.1919 0.1405 -0.0284 0.0262 1.0000 Uiso R . . . . .
H1031 H 0.3459 1.1584 0.4125 0.0343 1.0000 Uiso R . . . . .
H1041 H 0.4609 1.1879 0.4815 0.0385 1.0000 Uiso R . . . . .
H1051 H 0.4809 1.1062 0.5544 0.0349 1.0000 Uiso R . . . . .
H1081 H 0.1754 0.9164 0.4037 0.0282 1.0000 Uiso R . . . . .
H1122 H 0.0217 0.9438 0.2828 0.0286 1.0000 Uiso R . . . . .
H1121 H 0.0285 0.8878 0.3325 0.0283 1.0000 Uiso R . . . . .
H1131 H 0.1239 0.8575 0.2175 0.0296 1.0000 Uiso R . . . . .
H1132 H 0.0383 0.8096 0.2174 0.0301 1.0000 Uiso R . . . . .
H1161 H 0.1051 0.6162 0.2573 0.0289 1.0000 Uiso R . . . . .
H1171 H 0.1635 0.5020 0.1827 0.0294 1.0000 Uiso R . . . . .
H1191 H 0.2840 0.6666 0.1022 0.0270 1.0000 Uiso R . . . . .
H1201 H 0.2246 0.7801 0.1776 0.0270 1.0000 Uiso R . . . . .
H1221 H 0.3659 0.5429 0.0695 0.0320 1.0000 Uiso R . . . . .
H1222 H 0.2954 0.5534 0.0205 0.0315 1.0000 Uiso R . . . . .
H1231 H 0.3710 0.4429 -0.0373 0.0331 1.0000 Uiso R . . . . .
H1232 H 0.2834 0.4037 -0.0257 0.0344 1.0000 Uiso R . . . . .
H1281 H 0.4593 0.3310 0.1142 0.0269 1.0000 Uiso R . . . . .
H1301 H 0.5316 0.0969 0.1064 0.0324 1.0000 Uiso R . . . . .
H1311 H 0.4371 0.0366 0.0198 0.0352 1.0000 Uiso R . . . . .
H1321 H 0.3578 0.1251 -0.0206 0.0303 1.0000 Uiso R . . . . .
H1362 H 0.6743 0.4201 0.2486 0.0333 1.0000 Uiso R . . . . .
H1361 H 0.6481 0.3425 0.2764 0.0338 1.0000 Uiso R . . . . .
H1372 H 0.5496 0.4803 0.2778 0.0323 1.0000 Uiso R . . . . .
H1371 H 0.5153 0.4009 0.2991 0.0322 1.0000 Uiso R . . . . .
H1401 H 0.4575 0.5377 0.3410 0.0326 1.0000 Uiso R . . . . .
H1411 H 0.3835 0.6358 0.4177 0.0313 1.0000 Uiso R . . . . .
H1431 H 0.5492 0.6382 0.5602 0.0299 1.0000 Uiso R . . . . .
H1441 H 0.6256 0.5420 0.4829 0.0306 1.0000 Uiso R . . . . .
H1461 H 0.4823 0.7562 0.6142 0.0322 1.0000 Uiso R . . . . .
H1462 H 0.4204 0.6832 0.6233 0.0326 1.0000 Uiso R . . . . .
H1471 H 0.3768 0.8147 0.6845 0.0329 1.0000 Uiso R . . . . .
H1472 H 0.3125 0.7776 0.6245 0.0327 1.0000 Uiso R . . . . .
H1511 H 0.3036 0.8705 0.5409 0.0300 1.0000 Uiso R . . . . .
H1351 H 0.5752 0.3646 0.1662 0.0309 1.0000 Uiso R . . . . .
H351 H -0.0908 0.6151 0.3059 0.0341 1.0000 Uiso R . . . . .
H241 H 0.0945 0.6556 0.4172 0.0323 1.0000 Uiso R . . . . .
H1241 H 0.4150 0.3948 0.0514 0.0304 1.0000 Uiso R . . . . .
O501 O 0.946993(10) 0.457776(10) 0.482064(10) 0.0874 0.5000 Uani . . . . 1 .
H5012 H 1.0000 0.5000 0.5000 0.1317 1.0000 Uiso RS . . . 1 .
H5011 H 0.9619 0.4715 0.4480 0.1032 0.5000 Uiso R . . . 1 .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.14276(6)

loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N201 . C202 . 1.522(3) yes
N201 . C211 . 1.519(3) yes
N201 . C221 . 1.519(3) yes
N201 . C231 . 1.523(3) yes
C202 . C203 . 1.508(4) yes
C202 . H2021 . 0.959 no
C202 . H2022 . 0.957 no
C203 . C204 . 1.523(4) yes
C203 . H2031 . 0.971 no
C203 . H2032 . 0.974 no
C204 . C205 . 1.521(4) yes
C204 . H2041 . 0.964 no
C204 . H2042 . 0.971 no
C205 . H2052 . 0.956 no
C205 . H2053 . 0.958 no
C205 . H2051 . 0.969 no
C211 . C212 . 1.523(3) yes
C211 . H2111 . 0.963 no
C211 . H2112 . 0.963 no
C212 . C213 . 1.525(3) yes
C212 . H2121 . 0.971 no
C212 . H2122 . 0.970 no
C213 . C214 . 1.517(4) yes
C213 . H2131 . 0.971 no
C213 . H2132 . 0.980 no
C214 . H2142 . 0.969 no
C214 . H2143 . 0.962 no
C214 . H2141 . 0.957 no
C221 . C222 . 1.523(4) yes
C221 . H2211 . 0.956 no
C221 . H2212 . 0.954 no
C222 . C223 . 1.528(4) yes
C222 . H2221 . 0.956 no
C222 . H2222 . 0.969 no
C223 . C224 . 1.510(4) yes
C223 . H2231 . 0.970 no
C223 . H2232 . 0.975 no
C224 . H2242 . 0.955 no
C224 . H2243 . 0.947 no
C224 . H2241 . 0.960 no
C231 . C232 . 1.519(3) yes
C231 . H2311 . 0.968 no
C231 . H2312 . 0.965 no
C232 . C233 . 1.536(4) yes
C232 . H2321 . 0.970 no
C232 . H2322 . 0.965 no
C233 . C234 . 1.519(4) yes
C233 . H2331 . 0.962 no
C233 . H2332 . 0.972 no
C234 . H2342 . 0.963 no
C234 . H2343 . 0.953 no
C234 . H2341 . 0.963 no
N301 . C302 . 1.525(3) yes
N301 . C311 . 1.517(3) yes
N301 . C321 . 1.511(3) yes
N301 . C331 . 1.532(3) yes
C302 . C303 . 1.516(4) yes
C302 . H3021 . 0.974 no
C302 . H3022 . 0.957 no
C303 . C304 . 1.531(4) yes
C303 . H3031 . 0.960 no
C303 . H3032 . 0.968 no
C304 . C305 . 1.518(5) yes
C304 . H3041 . 0.965 no
C304 . H3042 . 0.987 no
C305 . H3052 . 0.964 no
C305 . H3053 . 0.957 no
C305 . H3051 . 0.958 no
C311 . C312 . 1.519(3) yes
C311 . H3111 . 0.970 no
C311 . H3112 . 0.965 no
C312 . C313 . 1.527(4) yes
C312 . H3121 . 0.966 no
C312 . H3122 . 0.975 no
C313 . C314 . 1.516(3) yes
C313 . H3131 . 0.971 no
C313 . H3132 . 0.977 no
C314 . H3142 . 0.957 no
C314 . H3143 . 0.953 no
C314 . H3141 . 0.971 no
C321 . C322 . 1.522(4) yes
C321 . H3211 . 0.963 no
C321 . H3212 . 0.964 no
C322 . C323 . 1.525(4) yes
C322 . H3221 . 0.986 no
C322 . H3222 . 0.970 no
C323 . C324 . 1.515(4) yes
C323 . H3231 . 0.967 no
C323 . H3232 . 0.967 no
C324 . H3242 . 0.962 no
C324 . H3243 . 0.962 no
C324 . H3241 . 0.967 no
C331 . C332 . 1.511(3) yes
C331 . H3311 . 0.966 no
C331 . H3312 . 0.978 no
C332 . C333 . 1.537(4) yes
C332 . H3321 . 0.966 no
C332 . H3322 . 0.967 no
C333 . C334 . 1.529(4) yes
C333 . H3331 . 0.972 no
C333 . H3332 . 0.970 no
C334 . H3342 . 0.957 no
C334 . H3343 . 0.958 no
C334 . H3341 . 0.964 no
N401 . C402 . 1.125(4) yes
C402 . C403 . 1.447(4) yes
C403 . H4031 . 0.961 no
C403 . H4032 . 0.961 no
C403 . H4033 . 0.959 no
N1 . C2 . 1.338(3) yes
N1 . C6 . 1.347(3) yes
C2 . C3 . 1.398(4) yes
C2 . C7 . 1.472(4) yes
C3 . C4 . 1.379(4) yes
C3 . H31 . 0.933 no
C4 . C5 . 1.382(4) yes
C4 . H41 . 0.935 no
C5 . C6 . 1.395(3) yes
C5 . H51 . 0.926 no
C6 . C52 . 1.469(3) yes
C7 . C8 . 1.370(4) yes
C7 . N9 . 1.366(3) yes
C8 . N11 . 1.342(3) yes
C8 . H81 . 0.930 no
N9 . N10 . 1.323(3) yes
N10 . N11 . 1.351(3) yes
N11 . C12 . 1.461(3) yes
C12 . C13 . 1.511(4) yes
C12 . H121 . 0.959 no
C12 . H122 . 0.965 no
C13 . O14 . 1.428(3) yes
C13 . H131 . 0.957 no
C13 . H132 . 0.968 no
O14 . C15 . 1.379(3) yes
C15 . C16 . 1.386(4) yes
C15 . C20 . 1.394(4) yes
C16 . C17 . 1.397(4) yes
C16 . H161 . 0.932 no
C17 . C18 . 1.382(4) yes
C17 . H171 . 0.931 no
C18 . C19 . 1.394(4) yes
C18 . O21 . 1.379(3) yes
C19 . C20 . 1.386(4) yes
C19 . H191 . 0.926 no
C20 . H201 . 0.934 no
O21 . C22 . 1.424(3) yes
C22 . C23 . 1.504(4) yes
C22 . H222 . 0.958 no
C22 . H221 . 0.963 no
C23 . N24 . 1.458(4) yes
C23 . H232 . 0.967 no
C23 . H231 . 0.967 no
N24 . C25 . 1.338(3) yes
N24 . H241 . 0.846 no
C25 . O26 . 1.233(3) yes
C25 . C27 . 1.497(4) yes
C27 . C28 . 1.393(4) yes
C27 . C32 . 1.400(3) yes
C28 . C29 . 1.386(4) yes
C28 . H281 . 0.939 no
C29 . C30 . 1.397(3) yes
C29 . C34 . 1.503(4) yes
C30 . C31 . 1.387(4) yes
C30 . H301 . 0.930 no
C31 . C32 . 1.386(4) yes
C31 . H311 . 0.929 no
C32 . H321 . 0.927 no
O33 . C34 . 1.230(3) yes
C34 . N35 . 1.348(3) yes
N35 . C36 . 1.456(3) yes
N35 . H351 . 0.862 no
C36 . C37 . 1.518(4) yes
C36 . H361 . 0.963 no
C36 . H362 . 0.958 no
C37 . O38 . 1.431(3) yes
C37 . H372 . 0.957 no
C37 . H371 . 0.972 no
O38 . C39 . 1.374(3) yes
C39 . C40 . 1.381(4) yes
C39 . C44 . 1.389(4) yes
C40 . C41 . 1.399(3) yes
C40 . H401 . 0.931 no
C41 . C42 . 1.381(4) yes
C41 . H411 . 0.934 no
C42 . C43 . 1.392(4) yes
C42 . O45 . 1.384(3) yes
C43 . C44 . 1.381(4) yes
C43 . H431 . 0.935 no
C44 . H441 . 0.936 no
O45 . C46 . 1.429(3) yes
C46 . C47 . 1.505(3) yes
C46 . H462 . 0.967 no
C46 . H461 . 0.967 no
C47 . N48 . 1.462(3) yes
C47 . H471 . 0.957 no
C47 . H472 . 0.961 no
N48 . N49 . 1.348(3) yes
N48 . C51 . 1.349(3) yes
N49 . N50 . 1.313(3) yes
N50 . C52 . 1.361(3) yes
C51 . C52 . 1.376(3) yes
C51 . H511 . 0.925 no
N101 . C102 . 1.350(3) yes
N101 . C106 . 1.337(3) yes
C102 . C103 . 1.396(4) yes
C102 . C107 . 1.467(4) yes
C103 . C104 . 1.379(4) yes
C103 . H1031 . 0.925 no
C104 . C105 . 1.375(4) yes
C104 . H1041 . 0.926 no
C105 . C106 . 1.402(4) yes
C105 . H1051 . 0.934 no
C106 . C152 . 1.466(4) yes
C107 . C108 . 1.376(3) yes
C107 . N109 . 1.363(3) yes
C108 . N111 . 1.346(3) yes
C108 . H1081 . 0.932 no
N109 . N110 . 1.314(3) yes
N110 . N111 . 1.355(3) yes
N111 . C112 . 1.464(3) yes
C112 . C113 . 1.509(3) yes
C112 . H1122 . 0.973 no
C112 . H1121 . 0.965 no
C113 . O114 . 1.431(3) yes
C113 . H1131 . 0.961 no
C113 . H1132 . 0.959 no
O114 . C115 . 1.393(3) yes
C115 . C116 . 1.387(3) yes
C115 . C120 . 1.385(3) yes
C116 . C117 . 1.384(4) yes
C116 . H1161 . 0.924 no
C117 . C118 . 1.390(4) yes
C117 . H1171 . 0.937 no
C118 . C119 . 1.393(3) yes
C118 . O121 . 1.378(3) yes
C119 . C120 . 1.396(3) yes
C119 . H1191 . 0.934 no
C120 . H1201 . 0.922 no
O121 . C122 . 1.431(3) yes
C122 . C123 . 1.508(3) yes
C122 . H1221 . 0.974 no
C122 . H1222 . 0.966 no
C123 . N124 . 1.451(3) yes
C123 . H1231 . 0.969 no
C123 . H1232 . 0.965 no
N124 . C126 . 1.331(3) yes
N124 . H1241 . 0.838 no
O125 . C126 . 1.241(3) yes
C126 . C127 . 1.499(4) yes
C127 . C128 . 1.392(3) yes
C127 . C132 . 1.398(4) yes
C128 . C129 . 1.387(4) yes
C128 . H1281 . 0.916 no
C129 . C130 . 1.400(4) yes
C129 . C134 . 1.506(4) yes
C130 . C131 . 1.390(4) yes
C130 . H1301 . 0.922 no
C131 . C132 . 1.378(4) yes
C131 . H1311 . 0.937 no
C132 . H1321 . 0.934 no
O133 . C134 . 1.229(3) yes
C134 . N135 . 1.343(3) yes
N135 . C136 . 1.462(3) yes
N135 . H1351 . 0.847 no
C136 . C137 . 1.514(3) yes
C136 . H1362 . 0.972 no
C136 . H1361 . 0.968 no
C137 . O138 . 1.430(3) yes
C137 . H1372 . 0.953 no
C137 . H1371 . 0.975 no
O138 . C139 . 1.383(3) yes
C139 . C140 . 1.386(4) yes
C139 . C144 . 1.396(3) yes
C140 . C141 . 1.387(4) yes
C140 . H1401 . 0.940 no
C141 . C142 . 1.384(4) yes
C141 . H1411 . 0.930 no
C142 . C143 . 1.389(4) yes
C142 . O145 . 1.384(3) yes
C143 . C144 . 1.390(4) yes
C143 . H1431 . 0.930 no
C144 . H1441 . 0.938 no
O145 . C146 . 1.422(3) yes
C146 . C147 . 1.509(4) yes
C146 . H1461 . 0.957 no
C146 . H1462 . 0.970 no
C147 . N148 . 1.461(3) yes
C147 . H1471 . 0.962 no
C147 . H1472 . 0.973 no
N148 . N149 . 1.350(3) yes
N148 . C151 . 1.346(3) yes
N149 . N150 . 1.315(3) yes
N150 . C152 . 1.362(3) yes
C151 . C152 . 1.379(4) yes
C151 . H1511 . 0.923 no
O501 . H5012 . 1.071 no
O501 . H5011 . 0.850 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C202 . N201 . C211 . 111.20(19) yes
C202 . N201 . C221 . 105.86(19) yes
C211 . N201 . C221 . 111.54(19) yes
C202 . N201 . C231 . 111.09(19) yes
C211 . N201 . C231 . 105.76(18) yes
C221 . N201 . C231 . 111.50(19) yes
N201 . C202 . C203 . 115.5(2) yes
N201 . C202 . H2021 . 107.1 no
C203 . C202 . H2021 . 110.6 no
N201 . C202 . H2022 . 106.2 no
C203 . C202 . H2022 . 108.4 no
H2021 . C202 . H2022 . 108.9 no
C202 . C203 . C204 . 110.8(2) yes
C202 . C203 . H2031 . 108.9 no
C204 . C203 . H2031 . 109.3 no
C202 . C203 . H2032 . 109.6 no
C204 . C203 . H2032 . 109.4 no
H2031 . C203 . H2032 . 108.9 no
C203 . C204 . C205 . 111.5(3) yes
C203 . C204 . H2041 . 107.8 no
C205 . C204 . H2041 . 111.7 no
C203 . C204 . H2042 . 109.7 no
C205 . C204 . H2042 . 108.7 no
H2041 . C204 . H2042 . 107.4 no
C204 . C205 . H2052 . 109.9 no
C204 . C205 . H2053 . 110.4 no
H2052 . C205 . H2053 . 109.5 no
C204 . C205 . H2051 . 109.3 no
H2052 . C205 . H2051 . 108.9 no
H2053 . C205 . H2051 . 108.8 no
N201 . C211 . C212 . 116.3(2) yes
N201 . C211 . H2111 . 106.8 no
C212 . C211 . H2111 . 109.0 no
N201 . C211 . H2112 . 106.8 no
C212 . C211 . H2112 . 108.1 no
H2111 . C211 . H2112 . 109.7 no
C211 . C212 . C213 . 109.5(2) yes
C211 . C212 . H2121 . 109.9 no
C213 . C212 . H2121 . 109.4 no
C211 . C212 . H2122 . 110.0 no
C213 . C212 . H2122 . 109.6 no
H2121 . C212 . H2122 . 108.4 no
C212 . C213 . C214 . 112.8(2) yes
C212 . C213 . H2131 . 109.1 no
C214 . C213 . H2131 . 109.6 no
C212 . C213 . H2132 . 107.8 no
C214 . C213 . H2132 . 108.8 no
H2131 . C213 . H2132 . 108.7 no
C213 . C214 . H2142 . 109.6 no
C213 . C214 . H2143 . 111.0 no
H2142 . C214 . H2143 . 109.5 no
C213 . C214 . H2141 . 109.6 no
H2142 . C214 . H2141 . 107.7 no
H2143 . C214 . H2141 . 109.4 no
N201 . C221 . C222 . 115.4(2) yes
N201 . C221 . H2211 . 108.1 no
C222 . C221 . H2211 . 108.5 no
N201 . C221 . H2212 . 107.3 no
C222 . C221 . H2212 . 108.0 no
H2211 . C221 . H2212 . 109.4 no
C221 . C222 . C223 . 110.8(2) yes
C221 . C222 . H2221 . 109.1 no
C223 . C222 . H2221 . 107.8 no
C221 . C222 . H2222 . 109.7 no
C223 . C222 . H2222 . 110.5 no
H2221 . C222 . H2222 . 109.0 no
C222 . C223 . C224 . 114.6(2) yes
C222 . C223 . H2231 . 107.8 no
C224 . C223 . H2231 . 108.0 no
C222 . C223 . H2232 . 108.2 no
C224 . C223 . H2232 . 109.3 no
H2231 . C223 . H2232 . 108.7 no
C223 . C224 . H2242 . 110.7 no
C223 . C224 . H2243 . 109.7 no
H2242 . C224 . H2243 . 108.5 no
C223 . C224 . H2241 . 110.3 no
H2242 . C224 . H2241 . 108.9 no
H2243 . C224 . H2241 . 108.8 no
N201 . C231 . C232 . 115.86(19) yes
N201 . C231 . H2311 . 106.3 no
C232 . C231 . H2311 . 109.3 no
N201 . C231 . H2312 . 106.6 no
C232 . C231 . H2312 . 109.4 no
H2311 . C231 . H2312 . 109.2 no
C231 . C232 . C233 . 110.2(2) yes
C231 . C232 . H2321 . 109.8 no
C233 . C232 . H2321 . 108.5 no
C231 . C232 . H2322 . 109.4 no
C233 . C232 . H2322 . 108.7 no
H2321 . C232 . H2322 . 110.2 no
C232 . C233 . C234 . 114.0(2) yes
C232 . C233 . H2331 . 109.8 no
C234 . C233 . H2331 . 108.7 no
C232 . C233 . H2332 . 107.7 no
C234 . C233 . H2332 . 107.9 no
H2331 . C233 . H2332 . 108.5 no
C233 . C234 . H2342 . 108.8 no
C233 . C234 . H2343 . 110.4 no
H2342 . C234 . H2343 . 109.6 no
C233 . C234 . H2341 . 108.2 no
H2342 . C234 . H2341 . 109.7 no
H2343 . C234 . H2341 . 110.1 no
C302 . N301 . C311 . 111.89(19) yes
C302 . N301 . C321 . 106.13(19) yes
C311 . N301 . C321 . 111.73(19) yes
C302 . N301 . C331 . 110.91(19) yes
C311 . N301 . C331 . 104.36(18) yes
C321 . N301 . C331 . 111.95(19) yes
N301 . C302 . C303 . 116.1(2) yes
N301 . C302 . H3021 . 106.4 no
C303 . C302 . H3021 . 109.6 no
N301 . C302 . H3022 . 106.3 no
C303 . C302 . H3022 . 108.7 no
H3021 . C302 . H3022 . 109.6 no
C302 . C303 . C304 . 109.9(2) yes
C302 . C303 . H3031 . 109.9 no
C304 . C303 . H3031 . 107.6 no
C302 . C303 . H3032 . 110.5 no
C304 . C303 . H3032 . 110.1 no
H3031 . C303 . H3032 . 108.7 no
C303 . C304 . C305 . 112.9(3) yes
C303 . C304 . H3041 . 109.2 no
C305 . C304 . H3041 . 108.9 no
C303 . C304 . H3042 . 108.5 no
C305 . C304 . H3042 . 108.9 no
H3041 . C304 . H3042 . 108.3 no
C304 . C305 . H3052 . 109.5 no
C304 . C305 . H3053 . 110.5 no
H3052 . C305 . H3053 . 109.3 no
C304 . C305 . H3051 . 109.9 no
H3052 . C305 . H3051 . 109.1 no
H3053 . C305 . H3051 . 108.6 no
N301 . C311 . C312 . 117.6(2) yes
N301 . C311 . H3111 . 106.6 no
C312 . C311 . H3111 . 109.3 no
N301 . C311 . H3112 . 106.6 no
C312 . C311 . H3112 . 108.2 no
H3111 . C311 . H3112 . 108.3 no
C311 . C312 . C313 . 107.2(2) yes
C311 . C312 . H3121 . 109.7 no
C313 . C312 . H3121 . 109.7 no
C311 . C312 . H3122 . 109.9 no
C313 . C312 . H3122 . 110.5 no
H3121 . C312 . H3122 . 109.8 no
C312 . C313 . C314 . 115.3(2) yes
C312 . C313 . H3131 . 109.5 no
C314 . C313 . H3131 . 107.3 no
C312 . C313 . H3132 . 106.6 no
C314 . C313 . H3132 . 107.4 no
H3131 . C313 . H3132 . 110.8 no
C313 . C314 . H3142 . 110.7 no
C313 . C314 . H3143 . 109.4 no
H3142 . C314 . H3143 . 109.0 no
C313 . C314 . H3141 . 110.1 no
H3142 . C314 . H3141 . 107.7 no
H3143 . C314 . H3141 . 109.9 no
N301 . C321 . C322 . 116.1(2) yes
N301 . C321 . H3211 . 106.8 no
C322 . C321 . H3211 . 108.4 no
N301 . C321 . H3212 . 107.9 no
C322 . C321 . H3212 . 108.3 no
H3211 . C321 . H3212 . 109.2 no
C321 . C322 . C323 . 108.6(2) yes
C321 . C322 . H3221 . 109.8 no
C323 . C322 . H3221 . 109.1 no
C321 . C322 . H3222 . 110.0 no
C323 . C322 . H3222 . 109.1 no
H3221 . C322 . H3222 . 110.2 no
C322 . C323 . C324 . 112.1(2) yes
C322 . C323 . H3231 . 107.9 no
C324 . C323 . H3231 . 108.0 no
C322 . C323 . H3232 . 110.1 no
C324 . C323 . H3232 . 108.6 no
H3231 . C323 . H3232 . 110.1 no
C323 . C324 . H3242 . 111.3 no
C323 . C324 . H3243 . 110.8 no
H3242 . C324 . H3243 . 109.1 no
C323 . C324 . H3241 . 109.2 no
H3242 . C324 . H3241 . 108.2 no
H3243 . C324 . H3241 . 108.2 no
N301 . C331 . C332 . 117.3(2) yes
N301 . C331 . H3311 . 105.3 no
C332 . C331 . H3311 . 108.2 no
N301 . C331 . H3312 . 106.3 no
C332 . C331 . H3312 . 109.8 no
H3311 . C331 . H3312 . 109.8 no
C331 . C332 . C333 . 109.0(2) yes
C331 . C332 . H3321 . 109.4 no
C333 . C332 . H3321 . 109.4 no
C331 . C332 . H3322 . 111.3 no
C333 . C332 . H3322 . 109.2 no
H3321 . C332 . H3322 . 108.5 no
C332 . C333 . C334 . 114.1(2) yes
C332 . C333 . H3331 . 109.3 no
C334 . C333 . H3331 . 108.8 no
C332 . C333 . H3332 . 107.4 no
C334 . C333 . H3332 . 108.0 no
H3331 . C333 . H3332 . 109.2 no
C333 . C334 . H3342 . 109.4 no
C333 . C334 . H3343 . 110.7 no
H3342 . C334 . H3343 . 108.8 no
C333 . C334 . H3341 . 109.6 no
H3342 . C334 . H3341 . 108.9 no
H3343 . C334 . H3341 . 109.4 no
N401 . C402 . C403 . 179.1(4) yes
C402 . C403 . H4031 . 108.1 no
C402 . C403 . H4032 . 108.9 no
H4031 . C403 . H4032 . 110.3 no
C402 . C403 . H4033 . 109.0 no
H4031 . C403 . H4033 . 110.5 no
H4032 . C403 . H4033 . 110.0 no
C2 . N1 . C6 . 117.2(2) yes
N1 . C2 . C3 . 123.3(2) yes
N1 . C2 . C7 . 116.8(2) yes
C3 . C2 . C7 . 119.9(2) yes
C2 . C3 . C4 . 118.6(2) yes
C2 . C3 . H31 . 120.1 no
C4 . C3 . H31 . 121.3 no
C3 . C4 . C5 . 119.1(2) yes
C3 . C4 . H41 . 119.8 no
C5 . C4 . H41 . 121.1 no
C4 . C5 . C6 . 118.6(2) yes
C4 . C5 . H51 . 121.7 no
C6 . C5 . H51 . 119.7 no
C5 . C6 . N1 . 123.2(2) yes
C5 . C6 . C52 . 120.2(2) yes
N1 . C6 . C52 . 116.6(2) yes
C2 . C7 . C8 . 130.6(2) yes
C2 . C7 . N9 . 121.3(2) yes
C8 . C7 . N9 . 108.2(2) yes
C7 . C8 . N11 . 105.2(2) yes
C7 . C8 . H81 . 129.5 no
N11 . C8 . H81 . 125.2 no
C7 . N9 . N10 . 108.8(2) yes
N9 . N10 . N11 . 106.9(2) yes
N10 . N11 . C8 . 111.0(2) yes
N10 . N11 . C12 . 118.8(2) yes
C8 . N11 . C12 . 130.0(2) yes
N11 . C12 . C13 . 111.9(2) yes
N11 . C12 . H121 . 106.8 no
C13 . C12 . H121 . 109.2 no
N11 . C12 . H122 . 110.6 no
C13 . C12 . H122 . 110.5 no
H121 . C12 . H122 . 107.6 no
C12 . C13 . O14 . 108.6(2) yes
C12 . C13 . H131 . 109.2 no
O14 . C13 . H131 . 109.7 no
C12 . C13 . H132 . 111.1 no
O14 . C13 . H132 . 110.3 no
H131 . C13 . H132 . 108.0 no
C13 . O14 . C15 . 115.35(19) yes
O14 . C15 . C16 . 123.9(2) yes
O14 . C15 . C20 . 116.8(2) yes
C16 . C15 . C20 . 119.3(2) yes
C15 . C16 . C17 . 120.3(3) yes
C15 . C16 . H161 . 120.7 no
C17 . C16 . H161 . 118.9 no
C16 . C17 . C18 . 120.2(2) yes
C16 . C17 . H171 . 119.5 no
C18 . C17 . H171 . 120.4 no
C17 . C18 . C19 . 119.7(2) yes
C17 . C18 . O21 . 124.3(2) yes
C19 . C18 . O21 . 116.0(2) yes
C18 . C19 . C20 . 120.1(2) yes
C18 . C19 . H191 . 120.3 no
C20 . C19 . H191 . 119.6 no
C15 . C20 . C19 . 120.5(2) yes
C15 . C20 . H201 . 119.8 no
C19 . C20 . H201 . 119.7 no
C18 . O21 . C22 . 116.1(2) yes
O21 . C22 . C23 . 108.5(2) yes
O21 . C22 . H222 . 110.9 no
C23 . C22 . H222 . 108.8 no
O21 . C22 . H221 . 110.4 no
C23 . C22 . H221 . 109.7 no
H222 . C22 . H221 . 108.6 no
C22 . C23 . N24 . 112.6(2) yes
C22 . C23 . H232 . 107.8 no
N24 . C23 . H232 . 108.4 no
C22 . C23 . H231 . 109.6 no
N24 . C23 . H231 . 109.3 no
H232 . C23 . H231 . 109.1 no
C23 . N24 . C25 . 118.2(2) yes
C23 . N24 . H241 . 123.0 no
C25 . N24 . H241 . 118.4 no
N24 . C25 . O26 . 122.1(3) yes
N24 . C25 . C27 . 117.5(2) yes
O26 . C25 . C27 . 120.3(2) yes
C25 . C27 . C28 . 122.5(2) yes
C25 . C27 . C32 . 118.4(2) yes
C28 . C27 . C32 . 119.1(3) yes
C27 . C28 . C29 . 120.6(2) yes
C27 . C28 . H281 . 119.2 no
C29 . C28 . H281 . 120.2 no
C28 . C29 . C30 . 120.0(2) yes
C28 . C29 . C34 . 121.5(2) yes
C30 . C29 . C34 . 118.5(2) yes
C29 . C30 . C31 . 119.8(3) yes
C29 . C30 . H301 . 120.2 no
C31 . C30 . H301 . 120.0 no
C30 . C31 . C32 . 120.2(2) yes
C30 . C31 . H311 . 119.4 no
C32 . C31 . H311 . 120.5 no
C27 . C32 . C31 . 120.4(2) yes
C27 . C32 . H321 . 118.5 no
C31 . C32 . H321 . 121.1 no
C29 . C34 . O33 . 120.9(2) yes
C29 . C34 . N35 . 115.3(2) yes
O33 . C34 . N35 . 123.7(3) yes
C34 . N35 . C36 . 121.5(2) yes
C34 . N35 . H351 . 120.3 no
C36 . N35 . H351 . 117.8 no
N35 . C36 . C37 . 109.8(2) yes
N35 . C36 . H361 . 109.3 no
C37 . C36 . H361 . 110.2 no
N35 . C36 . H362 . 107.8 no
C37 . C36 . H362 . 109.8 no
H361 . C36 . H362 . 109.9 no
C36 . C37 . O38 . 105.6(2) yes
C36 . C37 . H372 . 109.6 no
O38 . C37 . H372 . 109.7 no
C36 . C37 . H371 . 110.9 no
O38 . C37 . H371 . 111.2 no
H372 . C37 . H371 . 109.7 no
C37 . O38 . C39 . 117.1(2) yes
O38 . C39 . C40 . 124.8(2) yes
O38 . C39 . C44 . 115.5(2) yes
C40 . C39 . C44 . 119.7(2) yes
C39 . C40 . C41 . 120.2(2) yes
C39 . C40 . H401 . 120.5 no
C41 . C40 . H401 . 119.3 no
C40 . C41 . C42 . 119.8(2) yes
C40 . C41 . H411 . 120.6 no
C42 . C41 . H411 . 119.6 no
C41 . C42 . C43 . 119.9(2) yes
C41 . C42 . O45 . 125.9(2) yes
C43 . C42 . O45 . 114.2(2) yes
C42 . C43 . C44 . 120.1(2) yes
C42 . C43 . H431 . 119.7 no
C44 . C43 . H431 . 120.2 no
C39 . C44 . C43 . 120.3(2) yes
C39 . C44 . H441 . 119.8 no
C43 . C44 . H441 . 120.0 no
C42 . O45 . C46 . 116.96(19) yes
O45 . C46 . C47 . 107.3(2) yes
O45 . C46 . H462 . 109.8 no
C47 . C46 . H462 . 110.3 no
O45 . C46 . H461 . 110.0 no
C47 . C46 . H461 . 110.4 no
H462 . C46 . H461 . 109.0 no
C46 . C47 . N48 . 111.30(19) yes
C46 . C47 . H471 . 108.9 no
N48 . C47 . H471 . 108.4 no
C46 . C47 . H472 . 109.9 no
N48 . C47 . H472 . 108.3 no
H471 . C47 . H472 . 110.0 no
C47 . N48 . N49 . 120.9(2) yes
C47 . N48 . C51 . 128.1(2) yes
N49 . N48 . C51 . 110.9(2) yes
N48 . N49 . N50 . 107.4(2) yes
N49 . N50 . C52 . 108.7(2) yes
N48 . C51 . C52 . 104.4(2) yes
N48 . C51 . H511 . 126.5 no
C52 . C51 . H511 . 129.1 no
C6 . C52 . C51 . 128.9(2) yes
C6 . C52 . N50 . 122.6(2) yes
C51 . C52 . N50 . 108.5(2) yes
C102 . N101 . C106 . 117.3(2) yes
N101 . C102 . C103 . 122.8(2) yes
N101 . C102 . C107 . 115.9(2) yes
C103 . C102 . C107 . 121.3(2) yes
C102 . C103 . C104 . 118.6(3) yes
C102 . C103 . H1031 . 120.7 no
C104 . C103 . H1031 . 120.6 no
C103 . C104 . C105 . 119.6(3) yes
C103 . C104 . H1041 . 119.5 no
C105 . C104 . H1041 . 120.9 no
C104 . C105 . C106 . 118.2(3) yes
C104 . C105 . H1051 . 121.8 no
C106 . C105 . H1051 . 120.0 no
C105 . C106 . N101 . 123.4(2) yes
C105 . C106 . C152 . 120.1(2) yes
N101 . C106 . C152 . 116.5(2) yes
C102 . C107 . C108 . 129.4(2) yes
C102 . C107 . N109 . 122.1(2) yes
C108 . C107 . N109 . 108.4(2) yes
C107 . C108 . N111 . 104.5(2) yes
C107 . C108 . H1081 . 129.2 no
N111 . C108 . H1081 . 126.3 no
C107 . N109 . N110 . 109.1(2) yes
N109 . N110 . N111 . 106.8(2) yes
N110 . N111 . C108 . 111.2(2) yes
N110 . N111 . C112 . 118.7(2) yes
C108 . N111 . C112 . 130.1(2) yes
N111 . C112 . C113 . 113.0(2) yes
N111 . C112 . H1122 . 106.5 no
C113 . C112 . H1122 . 108.6 no
N111 . C112 . H1121 . 107.7 no
C113 . C112 . H1121 . 111.1 no
H1122 . C112 . H1121 . 110.0 no
C112 . C113 . O114 . 108.6(2) yes
C112 . C113 . H1131 . 111.1 no
O114 . C113 . H1131 . 110.0 no
C112 . C113 . H1132 . 108.6 no
O114 . C113 . H1132 . 109.3 no
H1131 . C113 . H1132 . 109.2 no
C113 . O114 . C115 . 114.13(18) yes
O114 . C115 . C116 . 118.2(2) yes
O114 . C115 . C120 . 121.7(2) yes
C116 . C115 . C120 . 120.0(2) yes
C115 . C116 . C117 . 120.0(2) yes
C115 . C116 . H1161 . 120.1 no
C117 . C116 . H1161 . 119.9 no
C116 . C117 . C118 . 120.4(2) yes
C116 . C117 . H1171 . 120.3 no
C118 . C117 . H1171 . 119.3 no
C117 . C118 . C119 . 119.6(2) yes
C117 . C118 . O121 . 116.7(2) yes
C119 . C118 . O121 . 123.6(2) yes
C118 . C119 . C120 . 119.8(2) yes
C118 . C119 . H1191 . 120.4 no
C120 . C119 . H1191 . 119.9 no
C119 . C120 . C115 . 120.1(2) yes
C119 . C120 . H1201 . 120.1 no
C115 . C120 . H1201 . 119.8 no
C118 . O121 . C122 . 116.54(19) yes
O121 . C122 . C123 . 108.9(2) yes
O121 . C122 . H1221 . 108.7 no
C123 . C122 . H1221 . 110.7 no
O121 . C122 . H1222 . 109.9 no
C123 . C122 . H1222 . 108.8 no
H1221 . C122 . H1222 . 109.7 no
C122 . C123 . N124 . 111.7(2) yes
C122 . C123 . H1231 . 108.5 no
N124 . C123 . H1231 . 108.7 no
C122 . C123 . H1232 . 109.0 no
N124 . C123 . H1232 . 108.8 no
H1231 . C123 . H1232 . 110.2 no
C123 . N124 . C126 . 121.8(2) yes
C123 . N124 . H1241 . 118.1 no
C126 . N124 . H1241 . 118.6 no
N124 . C126 . O125 . 122.7(3) yes
N124 . C126 . C127 . 117.7(2) yes
O125 . C126 . C127 . 119.5(2) yes
C126 . C127 . C128 . 123.4(2) yes
C126 . C127 . C132 . 117.4(2) yes
C128 . C127 . C132 . 119.1(2) yes
C127 . C128 . C129 . 120.4(2) yes
C127 . C128 . H1281 . 118.3 no
C129 . C128 . H1281 . 121.3 no
C128 . C129 . C130 . 120.0(2) yes
C128 . C129 . C134 . 122.0(2) yes
C130 . C129 . C134 . 118.0(2) yes
C129 . C130 . C131 . 119.6(2) yes
C129 . C130 . H1301 . 119.3 no
C131 . C130 . H1301 . 121.1 no
C130 . C131 . C132 . 120.3(2) yes
C130 . C131 . H1311 . 119.8 no
C132 . C131 . H1311 . 119.9 no
C127 . C132 . C131 . 120.6(2) yes
C127 . C132 . H1321 . 119.3 no
C131 . C132 . H1321 . 120.1 no
C129 . C134 . O133 . 120.3(2) yes
C129 . C134 . N135 . 116.2(2) yes
O133 . C134 . N135 . 123.6(2) yes
C134 . N135 . C136 . 120.9(2) yes
C134 . N135 . H1351 . 119.1 no
C136 . N135 . H1351 . 117.6 no
N135 . C136 . C137 . 108.1(2) yes
N135 . C136 . H1362 . 109.8 no
C137 . C136 . H1362 . 110.2 no
N135 . C136 . H1361 . 108.6 no
C137 . C136 . H1361 . 110.1 no
H1362 . C136 . H1361 . 110.0 no
C136 . C137 . O138 . 108.1(2) yes
C136 . C137 . H1372 . 109.4 no
O138 . C137 . H1372 . 108.7 no
C136 . C137 . H1371 . 110.7 no
O138 . C137 . H1371 . 110.7 no
H1372 . C137 . H1371 . 109.2 no
C137 . O138 . C139 . 115.18(19) yes
O138 . C139 . C140 . 123.7(2) yes
O138 . C139 . C144 . 116.7(2) yes
C140 . C139 . C144 . 119.6(2) yes
C139 . C140 . C141 . 119.9(2) yes
C139 . C140 . H1401 . 120.0 no
C141 . C140 . H1401 . 120.1 no
C140 . C141 . C142 . 120.4(2) yes
C140 . C141 . H1411 . 119.7 no
C142 . C141 . H1411 . 119.9 no
C141 . C142 . C143 . 120.1(2) yes
C141 . C142 . O145 . 114.5(2) yes
C143 . C142 . O145 . 125.4(2) yes
C142 . C143 . C144 . 119.5(2) yes
C142 . C143 . H1431 . 120.6 no
C144 . C143 . H1431 . 119.9 no
C139 . C144 . C143 . 120.4(2) yes
C139 . C144 . H1441 . 119.0 no
C143 . C144 . H1441 . 120.5 no
C142 . O145 . C146 . 117.8(2) yes
O145 . C146 . C147 . 107.2(2) yes
O145 . C146 . H1461 . 110.3 no
C147 . C146 . H1461 . 108.5 no
O145 . C146 . H1462 . 110.4 no
C147 . C146 . H1462 . 110.3 no
H1461 . C146 . H1462 . 110.0 no
C146 . C147 . N148 . 111.6(2) yes
C146 . C147 . H1471 . 108.7 no
N148 . C147 . H1471 . 108.0 no
C146 . C147 . H1472 . 109.4 no
N148 . C147 . H1472 . 108.4 no
H1471 . C147 . H1472 . 110.9 no
C147 . N148 . N149 . 119.6(2) yes
C147 . N148 . C151 . 128.9(2) yes
N149 . N148 . C151 . 111.4(2) yes
N148 . N149 . N150 . 106.9(2) yes
N149 . N150 . C152 . 108.9(2) yes
N148 . C151 . C152 . 104.2(2) yes
N148 . C151 . H1511 . 126.8 no
C152 . C151 . H1511 . 129.0 no
C106 . C152 . C151 . 129.3(2) yes
C106 . C152 . N150 . 122.1(2) yes
C151 . C152 . N150 . 108.5(2) yes
H5012 . O501 . H5011 . 77.5 no
O501 2_766 H5012 . O501 . 180.0 no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C221 . H2212 . N401 . 156 0.95 2.43 3.321(4) yes
C233 . H2332 . O26 . 134 0.97 2.56 3.306(4) yes
C311 . H3111 . N150 2_676 156 0.97 2.53 3.433(4) yes
C323 . H3231 . O33 1_655 132 0.97 2.55 3.273(4) yes
C12 . H122 . O133 . 143 0.97 2.59 3.411(4) yes
C22 . H221 . O501 2_666 141 0.96 2.51 3.311(4) yes
C47 . H472 . O33 2_565 132 0.96 2.39 3.113(4) yes
C120 . H1201 . N9 1_565 174 0.92 2.55 3.465(4) yes
C147 . H1471 . O133 2_666 153 0.96 2.39 3.275(4) yes
C147 . H1472 . N401 . 139 0.97 2.44 3.239(4) yes
C151 . H1511 . O26 . 161 0.92 2.48 3.372(4) yes
O501 . H5012 . O501 2_766 180 1.07 1.07 2.142(4) yes


# Manually omitted reflections
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
0 -2 4 x .
-2 -1 4 x .
8 -4 22 x .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile/diethyl ether'
