# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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#######################################################################

data_cl-pd-841
_database_code_depnum_ccdc_archive 'CCDC 902206'
_audit_update_record             
;
2012-09-19 deposited with the CCDC.
2014-11-20 downloaded from the CCDC.
;
#TrackingRef '14073_web_deposit_cif_file_0_PascalRetailleau_1348074333.cl-pd-841_final.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(R)-dibenzyl 1-(1-oxo-1-(((prop-2-yn-1-yloxy)carbonyl)amino)propan-2-yl)
hydrazine-1,2-dicarboxylate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H23 N3 O7'
_chemical_formula_sum            'C23 H23 N3 O7'
_chemical_formula_weight         453.44
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   8.2230(10)
_cell_length_b                   20.352(2)
_cell_length_c                   14.300(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.020(7)
_cell_angle_gamma                90.00
_cell_volume                     2311.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    183(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    0.819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.689
_exptl_absorpt_correction_T_max  0.884
_exptl_absorpt_process_details   'FS_ABSCOR (Rigaku, 2009)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      183(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku rapid II RAXIS conversion'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_type            
'RAPID II large area curved imaging plate detector '
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19875
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_sigmaI/netI    0.0881
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         68.12
_reflns_number_total             7499
_reflns_number_gt                4021
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
10 reflections were omitted due to large e.s.d (setup configuration with
partial chi-arm).
Absolute configuration C17: R (C40: R).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0764P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
'Flack H D (1983), Acta Cryst. A39, 876-881;3283 Friedel pairs'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_number_reflns         7489
_refine_ls_number_parameters     610
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1126
_refine_ls_R_factor_gt           0.0655
_refine_ls_wR_factor_ref         0.1916
_refine_ls_wR_factor_gt          0.1356
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0997(6) 0.1140(2) 0.8033(3) 0.0868(14) Uani 1 1 d . . .
O2 O 0.5166(5) 0.50153(18) 0.9225(3) 0.0688(11) Uani 1 1 d . . .
O3 O 0.7408(5) 0.49504(18) 1.0555(3) 0.0738(12) Uani 1 1 d . . .
O4 O 0.2763(6) 0.6857(2) 0.9171(3) 0.0804(13) Uani 1 1 d . . .
O5 O 0.3716(5) 0.6208(2) 1.0483(3) 0.0808(13) Uani 1 1 d . . .
O6 O 0.2259(5) 0.31011(19) 0.7999(3) 0.0730(12) Uani 1 1 d . . .
O7 O 0.3754(5) 0.68326(19) 0.6962(3) 0.0747(12) Uani 1 1 d . . .
O8 O 0.1837(5) 0.5754(2) 0.6049(3) 0.0743(12) Uani 1 1 d . . .
O9 O 0.1337(5) 0.19211(19) 0.4383(3) 0.0729(11) Uani 1 1 d . . .
O10 O 0.2355(5) 0.48778(19) 0.7072(3) 0.0727(12) Uani 1 1 d . . .
O11 O 0.2736(6) 0.2222(2) 0.9000(3) 0.0802(13) Uani 1 1 d . . .
O12 O -0.2393(5) 0.30207(17) 0.4542(3) 0.0688(11) Uani 1 1 d . . .
O13 O 0.2619(5) 0.1230(2) 0.5614(3) 0.0817(13) Uani 1 1 d . . .
O14 O -0.0094(5) 0.29721(19) 0.5813(3) 0.0709(11) Uani 1 1 d . . .
N1 N 0.5249(6) 0.6329(2) 0.9408(3) 0.0578(12) Uani 1 1 d . . .
N2 N 0.6458(7) 0.5929(2) 0.9997(3) 0.0622(14) Uani 1 1 d . . .
H2N H 0.695(7) 0.617(3) 1.044(4) 0.075 Uiso 1 1 d . . .
N3 N 0.3523(6) 0.5831(2) 0.7615(3) 0.0573(13) Uani 1 1 d . . .
H3N H 0.397(7) 0.558(3) 0.803(4) 0.069 Uiso 1 1 d . . .
N4 N -0.1333(6) 0.2042(2) 0.5021(3) 0.0587(12) Uani 1 1 d D . .
H4N H -0.183(6) 0.189(3) 0.445(2) 0.070 Uiso 1 1 d D . .
N5 N 0.0030(6) 0.1657(2) 0.5546(3) 0.0556(12) Uani 1 1 d . . .
N6 N 0.1229(7) 0.2151(2) 0.7382(3) 0.0631(13) Uani 1 1 d D . .
H6N H 0.080(6) 0.238(2) 0.684(2) 0.076 Uiso 1 1 d D . .
C1 C 0.3816(9) 0.6498(3) 0.9668(4) 0.0679(16) Uani 1 1 d . . .
C2 C 0.2330(9) 0.6415(4) 1.0872(5) 0.095(2) Uani 1 1 d . . .
H2A H 0.2033 0.6053 1.1260 0.115 Uiso 1 1 calc R . .
H2B H 0.1333 0.6510 1.0331 0.115 Uiso 1 1 calc R . .
C3 C 0.2775(9) 0.7015(3) 1.1497(5) 0.0761(18) Uani 1 1 d . . .
C4 C 0.4169(9) 0.7017(3) 1.2270(5) 0.0799(19) Uani 1 1 d . . .
H4 H 0.4885 0.6644 1.2403 0.096 Uiso 1 1 calc R . .
C5 C 0.4525(10) 0.7572(4) 1.2859(5) 0.095(2) Uani 1 1 d . . .
H5 H 0.5483 0.7569 1.3400 0.114 Uiso 1 1 calc R . .
C6 C 0.3543(13) 0.8114(5) 1.2681(7) 0.120(3) Uani 1 1 d . . .
H6 H 0.3804 0.8490 1.3086 0.144 Uiso 1 1 calc R . .
C7 C 0.2173(12) 0.8107(5) 1.1909(7) 0.116(3) Uani 1 1 d . . .
H7 H 0.1472 0.8484 1.1771 0.139 Uiso 1 1 calc R . .
C8 C 0.1783(10) 0.7563(4) 1.1323(6) 0.100(2) Uani 1 1 d . . .
H8 H 0.0811 0.7569 1.0790 0.120 Uiso 1 1 calc R . .
C9 C 0.6239(8) 0.5269(3) 0.9872(4) 0.0609(16) Uani 1 1 d . . .
C10 C 0.7238(8) 0.4249(2) 1.0547(5) 0.0673(17) Uani 1 1 d . . .
H10A H 0.7504 0.4064 0.9964 0.081 Uiso 1 1 calc R . .
H10B H 0.6067 0.4126 1.0535 0.081 Uiso 1 1 calc R . .
C11 C 0.8403(8) 0.3989(3) 1.1421(4) 0.0669(17) Uani 1 1 d . . .
C12 C 0.9427(9) 0.4381(3) 1.2114(5) 0.083(2) Uani 1 1 d . . .
H12 H 0.9429 0.4842 1.2009 0.100 Uiso 1 1 calc R . .
C13 C 1.0440(9) 0.4129(3) 1.2949(5) 0.096(2) Uani 1 1 d . . .
H13 H 1.1127 0.4413 1.3414 0.115 Uiso 1 1 calc R . .
C14 C 1.0462(11) 0.3455(4) 1.3115(6) 0.102(2) Uani 1 1 d . . .
H14 H 1.1148 0.3274 1.3697 0.122 Uiso 1 1 calc R . .
C15 C 0.9476(11) 0.3058(4) 1.2424(6) 0.105(3) Uani 1 1 d . . .
H15 H 0.9489 0.2596 1.2523 0.126 Uiso 1 1 calc R . .
C16 C 0.8454(8) 0.3325(3) 1.1577(5) 0.088(2) Uani 1 1 d . . .
H16 H 0.7784 0.3042 1.1101 0.105 Uiso 1 1 calc R . .
C17 C 0.5589(7) 0.6594(2) 0.8513(3) 0.0535(13) Uani 1 1 d . . .
H17 H 0.6585 0.6345 0.8422 0.064 Uiso 1 1 calc R . .
C18 C 0.6130(8) 0.7310(3) 0.8619(4) 0.0730(17) Uani 1 1 d . . .
H18A H 0.5191 0.7581 0.8699 0.109 Uiso 1 1 calc R . .
H18B H 0.6461 0.7450 0.8039 0.109 Uiso 1 1 calc R . .
H18C H 0.7087 0.7359 0.9188 0.109 Uiso 1 1 calc R . .
C19 C 0.4167(7) 0.6449(3) 0.7622(4) 0.0555(14) Uani 1 1 d . . .
C20 C 0.2510(8) 0.5520(3) 0.6827(4) 0.0625(15) Uani 1 1 d . . .
C21 C 0.1440(8) 0.4459(3) 0.6298(4) 0.0746(18) Uani 1 1 d . . .
H21A H 0.1060 0.4059 0.6573 0.089 Uiso 1 1 calc R . .
H21B H 0.0432 0.4694 0.5914 0.089 Uiso 1 1 calc R . .
C22 C 0.2497(10) 0.4279(4) 0.5681(5) 0.088(2) Uani 1 1 d . . .
C23 C 0.3354(10) 0.4164(5) 0.5157(6) 0.128(3) Uani 1 1 d . . .
H23 H 0.4045 0.4072 0.4734 0.153 Uiso 1 1 calc R . .
C24 C 0.1444(9) 0.1575(3) 0.5203(4) 0.0655(16) Uani 1 1 d . . .
C25 C 0.2708(8) 0.1772(3) 0.3929(4) 0.0795(19) Uani 1 1 d . . .
H25A H 0.3774 0.1712 0.4437 0.095 Uiso 1 1 calc R . .
H25B H 0.2858 0.2144 0.3513 0.095 Uiso 1 1 calc R . .
C26 C 0.2314(8) 0.1160(3) 0.3332(4) 0.0651(16) Uani 1 1 d . . .
C27 C 0.0930(8) 0.1152(4) 0.2513(5) 0.086(2) Uani 1 1 d . . .
H27 H 0.0234 0.1530 0.2359 0.103 Uiso 1 1 calc R . .
C28 C 0.0569(9) 0.0602(4) 0.1928(5) 0.096(2) Uani 1 1 d . . .
H28 H -0.0359 0.0598 0.1371 0.115 Uiso 1 1 calc R . .
C29 C 0.1599(10) 0.0059(4) 0.2180(6) 0.100(2) Uani 1 1 d . . .
H29 H 0.1344 -0.0327 0.1797 0.120 Uiso 1 1 calc R . .
C30 C 0.2964(11) 0.0058(4) 0.2958(6) 0.107(3) Uani 1 1 d . . .
H30 H 0.3682 -0.0315 0.3090 0.128 Uiso 1 1 calc R . .
C31 C 0.3305(9) 0.0610(3) 0.3562(5) 0.085(2) Uani 1 1 d . . .
H31 H 0.4217 0.0604 0.4128 0.103 Uiso 1 1 calc R . .
C32 C -0.1176(8) 0.2702(3) 0.5185(4) 0.0601(16) Uani 1 1 d . . .
C33 C -0.2304(9) 0.3725(3) 0.4654(4) 0.080(2) Uani 1 1 d . . .
H33A H -0.1140 0.3878 0.4711 0.096 Uiso 1 1 calc R . .
H33B H -0.2625 0.3854 0.5250 0.096 Uiso 1 1 calc R . .
C34 C -0.3501(8) 0.4036(3) 0.3775(5) 0.0669(16) Uani 1 1 d . . .
C35 C -0.4536(9) 0.3697(3) 0.3040(5) 0.082(2) Uani 1 1 d . . .
H35 H -0.4542 0.3231 0.3062 0.099 Uiso 1 1 calc R . .
C36 C -0.5586(10) 0.4018(4) 0.2256(5) 0.103(3) Uani 1 1 d . . .
H36 H -0.6298 0.3770 0.1750 0.124 Uiso 1 1 calc R . .
C37 C -0.5604(11) 0.4677(4) 0.2207(5) 0.102(2) Uani 1 1 d . . .
H37 H -0.6335 0.4895 0.1673 0.122 Uiso 1 1 calc R . .
C38 C -0.4552(10) 0.5035(4) 0.2937(6) 0.097(2) Uani 1 1 d . . .
H38 H -0.4538 0.5501 0.2900 0.116 Uiso 1 1 calc R . .
C39 C -0.3538(9) 0.4722(3) 0.3708(6) 0.090(2) Uani 1 1 d . . .
H39 H -0.2838 0.4974 0.4214 0.108 Uiso 1 1 calc R . .
C40 C -0.0175(7) 0.1239(3) 0.6332(3) 0.0602(14) Uani 1 1 d . . .
H40 H 0.0341 0.0805 0.6251 0.072 Uiso 1 1 calc R . .
C41 C -0.2014(8) 0.1109(3) 0.6302(4) 0.090(2) Uani 1 1 d . . .
H41A H -0.2598 0.1527 0.6309 0.135 Uiso 1 1 calc R . .
H41B H -0.2074 0.0847 0.6868 0.135 Uiso 1 1 calc R . .
H41C H -0.2550 0.0867 0.5710 0.135 Uiso 1 1 calc R . .
C42 C 0.0747(7) 0.1498(3) 0.7328(4) 0.0597(15) Uani 1 1 d . . .
C43 C 0.2148(8) 0.2458(3) 0.8220(5) 0.0664(17) Uani 1 1 d . . .
C44 C 0.3277(9) 0.3502(3) 0.8777(4) 0.0766(19) Uani 1 1 d . . .
H44A H 0.4243 0.3241 0.9150 0.092 Uiso 1 1 calc R . .
H44B H 0.3726 0.3885 0.8496 0.092 Uiso 1 1 calc R . .
C45 C 0.2292(11) 0.3732(4) 0.9422(5) 0.087(2) Uani 1 1 d . . .
C46 C 0.1520(10) 0.3932(6) 0.9928(6) 0.141(4) Uani 1 1 d . . .
H46 H 0.0884 0.4097 1.0345 0.169 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C42 1.217(6) . ?
O2 C9 1.215(6) . ?
O3 C9 1.346(6) . ?
O3 C10 1.434(6) . ?
O4 C1 1.212(7) . ?
O5 C1 1.328(7) . ?
O5 C2 1.454(7) . ?
O6 C43 1.355(6) . ?
O6 C44 1.456(6) . ?
O7 C19 1.204(6) . ?
O8 C20 1.205(6) . ?
O9 C24 1.351(7) . ?
O9 C25 1.472(6) . ?
O10 C20 1.367(7) . ?
O10 C21 1.445(6) . ?
O11 C43 1.196(6) . ?
O12 C32 1.339(6) . ?
O12 C33 1.443(6) . ?
O13 C24 1.216(7) . ?
O14 C32 1.220(6) . ?
N1 C1 1.368(7) . ?
N1 N2 1.388(6) . ?
N1 C17 1.481(6) . ?
N2 C9 1.362(7) . ?
N2 H2N 0.82(5) . ?
N3 C19 1.363(7) . ?
N3 C20 1.370(7) . ?
N3 H3N 0.80(5) . ?
N4 C32 1.362(7) . ?
N4 N5 1.414(6) . ?
N4 H4N 0.864(19) . ?
N5 C24 1.384(7) . ?
N5 C40 1.454(6) . ?
N6 C42 1.383(7) . ?
N6 C43 1.389(7) . ?
N6 H6N 0.892(19) . ?
C2 C3 1.502(9) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C8 1.365(9) . ?
C3 C4 1.371(9) . ?
C4 C5 1.394(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.352(10) . ?
C5 H5 0.9500 . ?
C6 C7 1.358(10) . ?
C6 H6 0.9500 . ?
C7 C8 1.375(11) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C10 C11 1.462(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.369(7) . ?
C11 C12 1.377(8) . ?
C12 C13 1.366(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.368(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(8) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.518(7) . ?
C17 C19 1.519(7) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C21 C22 1.437(10) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.177(10) . ?
C23 H23 0.9500 . ?
C25 C26 1.498(8) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C31 1.373(8) . ?
C26 C27 1.406(8) . ?
C27 C28 1.382(9) . ?
C27 H27 0.9500 . ?
C28 C29 1.382(10) . ?
C28 H28 0.9500 . ?
C29 C30 1.360(9) . ?
C29 H29 0.9500 . ?
C30 C31 1.401(9) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C33 C34 1.519(8) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.356(8) . ?
C34 C39 1.400(8) . ?
C35 C36 1.388(8) . ?
C35 H35 0.9500 . ?
C36 C37 1.343(9) . ?
C36 H36 0.9500 . ?
C37 C38 1.378(9) . ?
C37 H37 0.9500 . ?
C38 C39 1.357(8) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 C42 1.523(7) . ?
C40 C41 1.525(7) . ?
C40 H40 1.0000 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C44 C45 1.453(10) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C46 1.154(10) . ?
C46 H46 0.9500 . ?

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
C9 O3 C10 115.1(5) . . ?
C1 O5 C2 116.1(5) . . ?
C43 O6 C44 115.1(4) . . ?
C24 O9 C25 112.9(5) . . ?
C20 O10 C21 115.5(5) . . ?
C32 O12 C33 113.5(5) . . ?
C1 N1 N2 121.0(5) . . ?
C1 N1 C17 120.8(5) . . ?
N2 N1 C17 118.2(4) . . ?
C9 N2 N1 116.7(5) . . ?
C9 N2 H2N 135(4) . . ?
N1 N2 H2N 105(4) . . ?
C19 N3 C20 125.8(5) . . ?
C19 N3 H3N 119(4) . . ?
C20 N3 H3N 113(4) . . ?
C32 N4 N5 115.3(5) . . ?
C32 N4 H4N 121(4) . . ?
N5 N4 H4N 114(4) . . ?
C24 N5 N4 120.2(5) . . ?
C24 N5 C40 118.6(5) . . ?
N4 N5 C40 120.0(5) . . ?
C42 N6 C43 124.4(5) . . ?
C42 N6 H6N 114(4) . . ?
C43 N6 H6N 121(4) . . ?
O4 C1 O5 125.8(6) . . ?
O4 C1 N1 121.8(5) . . ?
O5 C1 N1 112.4(6) . . ?
O5 C2 C3 111.7(6) . . ?
O5 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
O5 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C8 C3 C4 118.7(8) . . ?
C8 C3 C2 120.9(7) . . ?
C4 C3 C2 120.4(6) . . ?
C3 C4 C5 119.4(7) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 121.7(8) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 118.2(9) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
C6 C7 C8 121.2(9) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C3 C8 C7 120.8(8) . . ?
C3 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
O2 C9 O3 126.1(5) . . ?
O2 C9 N2 124.3(6) . . ?
O3 C9 N2 109.5(5) . . ?
O3 C10 C11 108.2(5) . . ?
O3 C10 H10A 110.1 . . ?
C11 C10 H10A 110.1 . . ?
O3 C10 H10B 110.1 . . ?
C11 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
C16 C11 C12 117.9(6) . . ?
C16 C11 C10 118.8(6) . . ?
C12 C11 C10 123.3(5) . . ?
C13 C12 C11 122.2(6) . . ?
C13 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C12 C13 C14 119.8(7) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 118.7(7) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C16 120.6(7) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 120.8(6) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
N1 C17 C18 112.3(4) . . ?
N1 C17 C19 112.1(4) . . ?
C18 C17 C19 114.4(5) . . ?
N1 C17 H17 105.7 . . ?
C18 C17 H17 105.7 . . ?
C19 C17 H17 105.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O7 C19 N3 124.3(5) . . ?
O7 C19 C17 122.0(5) . . ?
N3 C19 C17 113.5(5) . . ?
O8 C20 O10 124.3(6) . . ?
O8 C20 N3 127.8(6) . . ?
O10 C20 N3 107.9(5) . . ?
C22 C21 O10 110.1(5) . . ?
C22 C21 H21A 109.6 . . ?
O10 C21 H21A 109.6 . . ?
C22 C21 H21B 109.6 . . ?
O10 C21 H21B 109.6 . . ?
H21A C21 H21B 108.2 . . ?
C23 C22 C21 176.4(10) . . ?
C22 C23 H23 180.0 . . ?
O13 C24 O9 125.9(6) . . ?
O13 C24 N5 122.3(6) . . ?
O9 C24 N5 111.8(6) . . ?
O9 C25 C26 110.2(5) . . ?
O9 C25 H25A 109.6 . . ?
C26 C25 H25A 109.6 . . ?
O9 C25 H25B 109.6 . . ?
C26 C25 H25B 109.6 . . ?
H25A C25 H25B 108.1 . . ?
C31 C26 C27 119.5(7) . . ?
C31 C26 C25 120.9(6) . . ?
C27 C26 C25 119.6(6) . . ?
C28 C27 C26 120.9(7) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C27 C28 C29 117.9(7) . . ?
C27 C28 H28 121.0 . . ?
C29 C28 H28 121.0 . . ?
C30 C29 C28 122.3(8) . . ?
C30 C29 H29 118.8 . . ?
C28 C29 H29 118.8 . . ?
C29 C30 C31 119.6(8) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
C26 C31 C30 119.6(7) . . ?
C26 C31 H31 120.2 . . ?
C30 C31 H31 120.2 . . ?
O14 C32 O12 124.0(5) . . ?
O14 C32 N4 126.2(6) . . ?
O12 C32 N4 109.8(5) . . ?
O12 C33 C34 108.5(5) . . ?
O12 C33 H33A 110.0 . . ?
C34 C33 H33A 110.0 . . ?
O12 C33 H33B 110.0 . . ?
C34 C33 H33B 110.0 . . ?
H33A C33 H33B 108.4 . . ?
C35 C34 C39 117.1(6) . . ?
C35 C34 C33 124.9(6) . . ?
C39 C34 C33 118.0(6) . . ?
C34 C35 C36 121.4(6) . . ?
C34 C35 H35 119.3 . . ?
C36 C35 H35 119.3 . . ?
C37 C36 C35 120.5(7) . . ?
C37 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C36 C37 C38 119.5(7) . . ?
C36 C37 H37 120.3 . . ?
C38 C37 H37 120.3 . . ?
C39 C38 C37 120.0(7) . . ?
C39 C38 H38 120.0 . . ?
C37 C38 H38 120.0 . . ?
C38 C39 C34 121.4(7) . . ?
C38 C39 H39 119.3 . . ?
C34 C39 H39 119.3 . . ?
N5 C40 C42 113.1(4) . . ?
N5 C40 C41 113.1(5) . . ?
C42 C40 C41 109.7(4) . . ?
N5 C40 H40 106.8 . . ?
C42 C40 H40 106.8 . . ?
C41 C40 H40 106.8 . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
O1 C42 N6 123.0(5) . . ?
O1 C42 C40 120.2(5) . . ?
N6 C42 C40 116.7(5) . . ?
O11 C43 O6 124.8(6) . . ?
O11 C43 N6 128.4(6) . . ?
O6 C43 N6 106.7(5) . . ?
C45 C44 O6 111.2(6) . . ?
C45 C44 H44A 109.4 . . ?
O6 C44 H44A 109.4 . . ?
C45 C44 H44B 109.4 . . ?
O6 C44 H44B 109.4 . . ?
H44A C44 H44B 108.0 . . ?
C46 C45 C44 178.1(10) . . ?
C45 C46 H46 180.0 . . ?

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
C1 N1 N2 C9 86.9(6) . . . . ?
C17 N1 N2 C9 -96.0(6) . . . . ?
C32 N4 N5 C24 -83.7(6) . . . . ?
C32 N4 N5 C40 108.9(5) . . . . ?
C2 O5 C1 O4 -9.0(9) . . . . ?
C2 O5 C1 N1 173.4(5) . . . . ?
N2 N1 C1 O4 178.6(5) . . . . ?
C17 N1 C1 O4 1.6(9) . . . . ?
N2 N1 C1 O5 -3.7(7) . . . . ?
C17 N1 C1 O5 179.3(4) . . . . ?
C1 O5 C2 C3 -85.7(7) . . . . ?
O5 C2 C3 C8 125.8(6) . . . . ?
O5 C2 C3 C4 -55.7(8) . . . . ?
C8 C3 C4 C5 0.6(9) . . . . ?
C2 C3 C4 C5 -177.9(6) . . . . ?
C3 C4 C5 C6 -0.9(11) . . . . ?
C4 C5 C6 C7 0.4(13) . . . . ?
C5 C6 C7 C8 0.3(13) . . . . ?
C4 C3 C8 C7 0.1(11) . . . . ?
C2 C3 C8 C7 178.6(7) . . . . ?
C6 C7 C8 C3 -0.6(12) . . . . ?
C10 O3 C9 O2 -5.9(9) . . . . ?
C10 O3 C9 N2 175.6(5) . . . . ?
N1 N2 C9 O2 7.6(9) . . . . ?
N1 N2 C9 O3 -173.9(4) . . . . ?
C9 O3 C10 C11 -170.4(5) . . . . ?
O3 C10 C11 C16 179.5(6) . . . . ?
O3 C10 C11 C12 1.3(9) . . . . ?
C16 C11 C12 C13 -1.7(10) . . . . ?
C10 C11 C12 C13 176.5(7) . . . . ?
C11 C12 C13 C14 0.3(11) . . . . ?
C12 C13 C14 C15 1.0(12) . . . . ?
C13 C14 C15 C16 -0.9(12) . . . . ?
C12 C11 C16 C15 1.8(10) . . . . ?
C10 C11 C16 C15 -176.5(7) . . . . ?
C14 C15 C16 C11 -0.6(11) . . . . ?
C1 N1 C17 C18 74.5(6) . . . . ?
N2 N1 C17 C18 -102.5(6) . . . . ?
C1 N1 C17 C19 -56.0(6) . . . . ?
N2 N1 C17 C19 127.0(5) . . . . ?
C20 N3 C19 O7 9.8(9) . . . . ?
C20 N3 C19 C17 -165.0(5) . . . . ?
N1 C17 C19 O7 144.1(5) . . . . ?
C18 C17 C19 O7 14.7(7) . . . . ?
N1 C17 C19 N3 -41.0(6) . . . . ?
C18 C17 C19 N3 -170.4(5) . . . . ?
C21 O10 C20 O8 5.8(9) . . . . ?
C21 O10 C20 N3 -174.9(5) . . . . ?
C19 N3 C20 O8 -10.2(10) . . . . ?
C19 N3 C20 O10 170.4(5) . . . . ?
C20 O10 C21 C22 78.3(7) . . . . ?
O10 C21 C22 C23 -73(13) . . . . ?
C25 O9 C24 O13 8.3(8) . . . . ?
C25 O9 C24 N5 -172.0(4) . . . . ?
N4 N5 C24 O13 -177.4(5) . . . . ?
C40 N5 C24 O13 -9.8(8) . . . . ?
N4 N5 C24 O9 2.9(7) . . . . ?
C40 N5 C24 O9 170.4(4) . . . . ?
C24 O9 C25 C26 82.1(6) . . . . ?
O9 C25 C26 C31 -116.6(6) . . . . ?
O9 C25 C26 C27 64.7(6) . . . . ?
C31 C26 C27 C28 -1.0(9) . . . . ?
C25 C26 C27 C28 177.7(6) . . . . ?
C26 C27 C28 C29 0.7(10) . . . . ?
C27 C28 C29 C30 -2.0(11) . . . . ?
C28 C29 C30 C31 3.5(12) . . . . ?
C27 C26 C31 C30 2.4(9) . . . . ?
C25 C26 C31 C30 -176.3(6) . . . . ?
C29 C30 C31 C26 -3.7(11) . . . . ?
C33 O12 C32 O14 0.4(8) . . . . ?
C33 O12 C32 N4 -179.0(5) . . . . ?
N5 N4 C32 O14 -9.4(8) . . . . ?
N5 N4 C32 O12 170.0(4) . . . . ?
C32 O12 C33 C34 168.6(5) . . . . ?
O12 C33 C34 C35 3.2(9) . . . . ?
O12 C33 C34 C39 -176.3(5) . . . . ?
C39 C34 C35 C36 0.0(10) . . . . ?
C33 C34 C35 C36 -179.5(6) . . . . ?
C34 C35 C36 C37 -0.1(12) . . . . ?
C35 C36 C37 C38 0.8(12) . . . . ?
C36 C37 C38 C39 -1.5(12) . . . . ?
C37 C38 C39 C34 1.4(11) . . . . ?
C35 C34 C39 C38 -0.7(10) . . . . ?
C33 C34 C39 C38 178.9(6) . . . . ?
C24 N5 C40 C42 84.6(6) . . . . ?
N4 N5 C40 C42 -107.8(5) . . . . ?
C24 N5 C40 C41 -149.9(5) . . . . ?
N4 N5 C40 C41 17.7(6) . . . . ?
C43 N6 C42 O1 4.9(10) . . . . ?
C43 N6 C42 C40 -176.8(5) . . . . ?
N5 C40 C42 O1 -164.1(5) . . . . ?
C41 C40 C42 O1 68.6(7) . . . . ?
N5 C40 C42 N6 17.5(7) . . . . ?
C41 C40 C42 N6 -109.8(6) . . . . ?
C44 O6 C43 O11 4.2(9) . . . . ?
C44 O6 C43 N6 -176.4(5) . . . . ?
C42 N6 C43 O11 3.8(11) . . . . ?
C42 N6 C43 O6 -175.6(5) . . . . ?
C43 O6 C44 C45 -85.1(7) . . . . ?
O6 C44 C45 C46 -120(27) . . . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        68.12
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.055




