# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_s4023ma
_database_code_depnum_ccdc_archive 'CCDC 1062574'
_audit_update_record             
;
2015-04-30 deposited with the CCDC.
2015-08-21 downloaded from the CCDC.
;
#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------# 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'racemic CbzMeValAib4OtBu'
_chemical_name_common            Cbz-(rac)-(\aMe)ValAib4OtBu
_chemical_melting_point          '488-489 '
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H55 N5 O8'
_chemical_formula_weight         661.83

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   11.4534(8)
_cell_length_b                   11.6801(9)
_cell_length_c                   14.4308(11)
_cell_angle_alpha                96.466(5)
_cell_angle_beta                 102.806(4)
_cell_angle_gamma                90.975(4)
_cell_volume                     1868.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5705
_cell_measurement_theta_min      3.81
_cell_measurement_theta_max      70.08

_exptl_crystal_description       prism
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716
_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75506
_exptl_absorpt_correction_T_max  0.9537
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14758
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         70.15
_reflns_number_total             6723
_reflns_number_gt                5516
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0722P)²+0.6805P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6723
_refine_ls_number_parameters     472
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1505
_refine_ls_wR_factor_gt          0.1417
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.089
_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
C1 C 1.2651(3) -0.0929(3) 0.75605(18) 0.0301(11) Uani 0.500(4) 1 d PGD A 1
C2 C 1.1902(3) -0.1883(2) 0.75444(18) 0.0370(10) Uani 0.500(4) 1 d PG A 1
H2 H 1.1587 -0.2357 0.6959 0.044 Uiso 0.500(4) 1 calc PR A 1
C3 C 1.1612(3) -0.2144(2) 0.8385(2) 0.0460(12) Uani 0.500(4) 1 d PG A 1
H3 H 1.1100 -0.2797 0.8374 0.055 Uiso 0.500(4) 1 calc PR A 1
C4 C 1.2072(3) -0.1451(3) 0.92414(19) 0.0514(17) Uani 0.500(4) 1 d PG A 1
H4 H 1.1874 -0.1630 0.9816 0.062 Uiso 0.500(4) 1 calc PR A 1
C5 C 1.2821(3) -0.0497(3) 0.92575(18) 0.0445(12) Uani 0.500(4) 1 d PG A 1
H5 H 1.3136 -0.0024 0.9843 0.053 Uiso 0.500(4) 1 calc PR A 1
C6 C 1.3111(3) -0.0236(2) 0.8417(2) 0.0387(11) Uani 0.500(4) 1 d PG A 1
H6 H 1.3623 0.0416 0.8428 0.046 Uiso 0.500(4) 1 calc PR A 1
C7 C 1.306(3) -0.0804(3) 0.6649(10) 0.0408(6) Uani 0.500(4) 1 d PD A 1
H7A H 1.3857 -0.1133 0.6687 0.049 Uiso 0.500(4) 1 calc PR A 1
H7B H 1.2490 -0.1236 0.6098 0.049 Uiso 0.500(4) 1 calc PR A 1
C8 C 1.20965(16) 0.09552(19) 0.63977(13) 0.0327(4) Uani 1 1 d . A .
C9 C 1.13269(16) 0.2867(2) 0.61099(13) 0.0338(4) Uani 1 1 d . . .
C10 C 1.19322(18) 0.4073(2) 0.61451(14) 0.0381(5) Uani 1 1 d . . .
H10 H 1.2638 0.4154 0.6701 0.046 Uiso 1 1 calc R . .
C11 C 1.1119(2) 0.5063(2) 0.63125(16) 0.0451(5) Uani 1 1 d . . .
H11A H 1.1515 0.5795 0.6260 0.068 Uiso 1 1 calc R . .
H11B H 1.0958 0.5078 0.6953 0.068 Uiso 1 1 calc R . .
H11C H 1.0361 0.4949 0.5831 0.068 Uiso 1 1 calc R . .
C12 C 1.2414(2) 0.4182(3) 0.52444(16) 0.0522(6) Uani 1 1 d . . .
H12A H 1.1741 0.4174 0.4689 0.078 Uiso 1 1 calc R . .
H12B H 1.2920 0.3533 0.5140 0.078 Uiso 1 1 calc R . .
H12C H 1.2888 0.4908 0.5330 0.078 Uiso 1 1 calc R . .
C13 C 1.0441(2) 0.2477(3) 0.51476(14) 0.0492(6) Uani 1 1 d . . .
H13A H 1.0874 0.2415 0.4631 0.074 Uiso 1 1 calc R . .
H13B H 0.9821 0.3044 0.5026 0.074 Uiso 1 1 calc R . .
H13C H 1.0066 0.1725 0.5175 0.074 Uiso 1 1 calc R . .
C14 C 1.06172(15) 0.29070(17) 0.69055(13) 0.0291(4) Uani 1 1 d . . .
C15 C 1.07024(16) 0.28842(18) 0.86283(13) 0.0322(4) Uani 1 1 d . . .
C16 C 1.03109(19) 0.41089(19) 0.88446(15) 0.0393(5) Uani 1 1 d . . .
H16A H 1.1007 0.4649 0.8969 0.059 Uiso 1 1 calc R . .
H16B H 0.9963 0.4157 0.9409 0.059 Uiso 1 1 calc R . .
H16C H 0.9711 0.4307 0.8295 0.059 Uiso 1 1 calc R . .
C17 C 1.16357(18) 0.2540(2) 0.94704(14) 0.0405(5) Uani 1 1 d . . .
H17A H 1.1882 0.1757 0.9309 0.061 Uiso 1 1 calc R . .
H17B H 1.1289 0.2563 1.0035 0.061 Uiso 1 1 calc R . .
H17C H 1.2335 0.3079 0.9608 0.061 Uiso 1 1 calc R . .
C18 C 0.96129(15) 0.20256(17) 0.84540(13) 0.0283(4) Uani 1 1 d . . .
C19 C 0.86254(17) 0.01780(17) 0.76544(15) 0.0331(4) Uani 1 1 d . . .
C20 C 0.86493(19) -0.04568(19) 0.85219(16) 0.0397(5) Uani 1 1 d . . .
H20A H 0.9389 -0.0877 0.8660 0.060 Uiso 1 1 calc R . .
H20B H 0.7957 -0.1003 0.8389 0.060 Uiso 1 1 calc R . .
H20C H 0.8617 0.0100 0.9076 0.060 Uiso 1 1 calc R . .
C21 C 0.87852(18) -0.06557(18) 0.67959(16) 0.0389(5) Uani 1 1 d . . .
H21A H 0.8790 -0.0226 0.6252 0.058 Uiso 1 1 calc R . .
H21B H 0.8122 -0.1237 0.6622 0.058 Uiso 1 1 calc R . .
H21C H 0.9546 -0.1038 0.6965 0.058 Uiso 1 1 calc R . .
C22 C 0.74067(16) 0.07269(17) 0.73371(13) 0.0311(4) Uani 1 1 d . . .
C23 C 0.63454(15) 0.22001(18) 0.63796(12) 0.0294(4) Uani 1 1 d . . .
C24 C 0.67449(17) 0.3175(2) 0.58778(13) 0.0371(5) Uani 1 1 d . . .
H24A H 0.7302 0.3714 0.6347 0.056 Uiso 1 1 calc R . .
H24B H 0.6043 0.3584 0.5586 0.056 Uiso 1 1 calc R . .
H24C H 0.7145 0.2850 0.5380 0.056 Uiso 1 1 calc R . .
C25 C 0.54750(17) 0.1346(2) 0.56478(14) 0.0411(5) Uani 1 1 d . . .
H25A H 0.5888 0.0993 0.5168 0.062 Uiso 1 1 calc R . .
H25B H 0.4788 0.1756 0.5332 0.062 Uiso 1 1 calc R . .
H25C H 0.5195 0.0743 0.5977 0.062 Uiso 1 1 calc R . .
C26 C 0.57055(14) 0.27863(15) 0.71223(12) 0.0233(4) Uani 1 1 d . . .
C27 C 0.58516(15) 0.37130(16) 0.87501(12) 0.0243(4) Uani 1 1 d . . .
C28 C 0.68916(17) 0.4123(2) 0.96003(13) 0.0368(5) Uani 1 1 d . . .
H28A H 0.7289 0.3453 0.9858 0.055 Uiso 1 1 calc R . .
H28B H 0.6581 0.4577 1.0100 0.055 Uiso 1 1 calc R . .
H28C H 0.7469 0.4601 0.9387 0.055 Uiso 1 1 calc R . .
C29 C 0.49308(18) 0.29794(17) 0.90670(14) 0.0319(4) Uani 1 1 d . . .
H29A H 0.4272 0.2727 0.8517 0.048 Uiso 1 1 calc R . .
H29B H 0.4616 0.3437 0.9562 0.048 Uiso 1 1 calc R . .
H29C H 0.5313 0.2303 0.9326 0.048 Uiso 1 1 calc R . .
C30 C 0.52740(16) 0.47939(15) 0.83702(12) 0.0255(4) Uani 1 1 d . . .
C31 C 0.5723(3) 0.6443(2) 0.75736(15) 0.0597(8) Uani 1 1 d . . .
C32 C 0.5575(3) 0.7378(2) 0.83526(15) 0.0526(7) Uani 1 1 d . . .
H32A H 0.4837 0.7214 0.8560 0.079 Uiso 1 1 calc R . .
H32B H 0.5529 0.8126 0.8103 0.079 Uiso 1 1 calc R . .
H32C H 0.6263 0.7398 0.8898 0.079 Uiso 1 1 calc R . .
C33 C 0.4602(4) 0.6235(2) 0.67708(17) 0.0884(14) Uani 1 1 d . . .
H33A H 0.4726 0.5602 0.6300 0.133 Uiso 1 1 calc R . .
H33B H 0.4439 0.6937 0.6459 0.133 Uiso 1 1 calc R . .
H33C H 0.3919 0.6031 0.7036 0.133 Uiso 1 1 calc R . .
C34 C 0.6827(5) 0.6704(3) 0.7205(2) 0.1080(18) Uani 1 1 d . . .
H34A H 0.7529 0.6809 0.7741 0.162 Uiso 1 1 calc R . .
H34B H 0.6720 0.7411 0.6894 0.162 Uiso 1 1 calc R . .
H34C H 0.6945 0.6061 0.6741 0.162 Uiso 1 1 calc R . .
N1 N 1.22965(13) 0.20625(16) 0.62893(11) 0.0331(4) Uani 1 1 d . . .
H1 H 1.3036 0.2314 0.6327 0.040 Uiso 1 1 calc R . .
N2 N 1.12475(13) 0.27973(15) 0.77932(11) 0.0293(3) Uani 1 1 d . . .
H2A H 1.2017 0.2668 0.7877 0.035 Uiso 1 1 calc R . .
N3 N 0.96131(13) 0.10596(14) 0.78610(11) 0.0299(3) Uani 1 1 d . . .
H3A H 1.0221 0.0947 0.7586 0.036 Uiso 1 1 calc R . .
N4 N 0.74169(13) 0.16283(14) 0.68238(11) 0.0291(4) Uani 1 1 d . . .
H4A H 0.8114 0.1887 0.6753 0.035 Uiso 1 1 calc R . .
N5 N 0.63461(13) 0.30539(14) 0.80164(10) 0.0266(3) Uani 1 1 d . . .
H5A H 0.7086 0.2827 0.8168 0.032 Uiso 1 1 calc R . .
O1 O 1.31244(12) 0.03906(15) 0.65088(11) 0.0420(4) Uani 1 1 d D . .
O2 O 1.11303(12) 0.05118(14) 0.64073(11) 0.0417(4) Uani 1 1 d . . .
O3 O 0.95375(11) 0.30565(12) 0.67318(9) 0.0323(3) Uani 1 1 d . . .
O4 O 0.88057(11) 0.22376(12) 0.88792(9) 0.0316(3) Uani 1 1 d . . .
O5 O 0.64892(12) 0.03084(13) 0.74937(11) 0.0386(3) Uani 1 1 d . . .
O6 O 0.46704(11) 0.30941(12) 0.68693(9) 0.0283(3) Uani 1 1 d . . .
O7 O 0.43184(12) 0.51181(12) 0.84729(10) 0.0334(3) Uani 1 1 d . . .
O8 O 0.60313(14) 0.53509(12) 0.79757(10) 0.0385(4) Uani 1 1 d . . .
C1S C 1.3134(3) -0.0740(3) 0.78660(15) 0.0314(11) Uani 0.500(4) 1 d PGD A 2
C2S C 1.2283(2) -0.1339(3) 0.81995(19) 0.0383(11) Uani 0.500(4) 1 d PG A 2
H2S H 1.1673 -0.1809 0.7761 0.046 Uiso 0.500(4) 1 calc PR A 2
C3S C 1.2324(3) -0.1251(3) 0.9175(2) 0.0479(17) Uani 0.500(4) 1 d PG A 2
H3S H 1.1742 -0.1660 0.9403 0.057 Uiso 0.500(4) 1 calc PR A 2
C4S C 1.3217(3) -0.0564(3) 0.98169(15) 0.0413(11) Uani 0.500(4) 1 d PG A 2
H4S H 1.3245 -0.0503 1.0484 0.050 Uiso 0.500(4) 1 calc PR A 2
C5S C 1.4068(2) 0.0035(2) 0.94834(17) 0.0406(11) Uani 0.500(4) 1 d PG A 2
H5S H 1.4678 0.0505 0.9922 0.049 Uiso 0.500(4) 1 calc PR A 2
C6S C 1.4026(2) -0.0053(2) 0.85079(18) 0.0347(10) Uani 0.500(4) 1 d PG A 2
H6S H 1.4608 0.0357 0.8280 0.042 Uiso 0.500(4) 1 calc PR A 2
C7S C 1.305(3) -0.0736(3) 0.6806(10) 0.0408(6) Uani 0.500(4) 1 d PD A 2
H7C H 1.3703 -0.1193 0.6626 0.049 Uiso 0.500(4) 1 calc PR A 2
H7D H 1.2280 -0.1125 0.6451 0.049 Uiso 0.500(4) 1 calc PR A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 C7 1.512(8) . ?
C2 C3 1.3900 . ?
C2 H2 0.9500 . ?
C3 C4 1.3900 . ?
C3 H3 0.9500 . ?
C4 C5 1.3900 . ?
C4 H4 0.9500 . ?
C5 C6 1.3900 . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.436(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O2 1.217(2) . ?
C8 N1 1.342(3) . ?
C8 O1 1.347(2) . ?
C9 N1 1.465(3) . ?
C9 C13 1.544(3) . ?
C9 C14 1.544(3) . ?
C9 C10 1.549(3) . ?
C10 C11 1.529(3) . ?
C10 C12 1.537(3) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 O3 1.226(2) . ?
C14 N2 1.345(2) . ?
C15 N2 1.470(2) . ?
C15 C16 1.526(3) . ?
C15 C17 1.526(3) . ?
C15 C18 1.545(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 O4 1.232(2) . ?
C18 N3 1.337(2) . ?
C19 N3 1.473(2) . ?
C19 C20 1.521(3) . ?
C19 C21 1.534(3) . ?
C19 C22 1.543(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 O5 1.228(2) . ?
C22 N4 1.355(3) . ?
C23 N4 1.462(3) . ?
C23 C24 1.531(3) . ?
C23 C26 1.535(2) . ?
C23 C25 1.539(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 O6 1.233(2) . ?
C26 N5 1.335(2) . ?
C27 N5 1.460(2) . ?
C27 C29 1.525(2) . ?
C27 C28 1.534(2) . ?
C27 C30 1.535(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 O7 1.199(2) . ?
C30 O8 1.335(2) . ?
C31 O8 1.476(3) . ?
C31 C34 1.515(5) . ?
C31 C32 1.517(3) . ?
C31 C33 1.522(4) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
N1 H1 0.8800 . ?
N2 H2A 0.8800 . ?
N3 H3A 0.8800 . ?
N4 H4A 0.8800 . ?
N5 H5A 0.8800 . ?
O1 C7S 1.436(3) . ?
C1S C2S 1.3900 . ?
C1S C6S 1.3900 . ?
C1S C7S 1.512(7) . ?
C2S C3S 1.3900 . ?
C2S H2S 0.9500 . ?
C3S C4S 1.3900 . ?
C3S H3S 0.9500 . ?
C4S C5S 1.3900 . ?
C4S H4S 0.9500 . ?
C5S C6S 1.3900 . ?
C5S H5S 0.9500 . ?
C6S H6S 0.9500 . ?
C7S H7C 0.9900 . ?
C7S H7D 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.0 . . ?
C2 C1 C7 116.4(8) . . ?
C6 C1 C7 123.0(10) . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O1 C7 C1 110.1(4) . . ?
O1 C7 H7A 109.6 . . ?
C1 C7 H7A 109.6 . . ?
O1 C7 H7B 109.6 . . ?
C1 C7 H7B 109.6 . . ?
H7A C7 H7B 108.2 . . ?
O2 C8 N1 125.53(19) . . ?
O2 C8 O1 123.9(2) . . ?
N1 C8 O1 110.54(16) . . ?
N1 C9 C13 110.69(18) . . ?
N1 C9 C14 110.14(16) . . ?
C13 C9 C14 107.64(15) . . ?
N1 C9 C10 106.48(15) . . ?
C13 C9 C10 113.09(19) . . ?
C14 C9 C10 108.79(17) . . ?
C11 C10 C12 110.47(19) . . ?
C11 C10 C9 113.16(17) . . ?
C12 C10 C9 111.7(2) . . ?
C11 C10 H10 107.1 . . ?
C12 C10 H10 107.1 . . ?
C9 C10 H10 107.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 N2 122.20(17) . . ?
O3 C14 C9 121.09(16) . . ?
N2 C14 C9 116.69(15) . . ?
N2 C15 C16 110.42(17) . . ?
N2 C15 C17 107.47(16) . . ?
C16 C15 C17 111.12(16) . . ?
N2 C15 C18 110.71(14) . . ?
C16 C15 C18 109.67(15) . . ?
C17 C15 C18 107.40(17) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 N3 122.95(16) . . ?
O4 C18 C15 119.42(16) . . ?
N3 C18 C15 117.60(15) . . ?
N3 C19 C20 110.42(16) . . ?
N3 C19 C21 107.37(15) . . ?
C20 C19 C21 110.86(18) . . ?
N3 C19 C22 110.73(16) . . ?
C20 C19 C22 111.06(16) . . ?
C21 C19 C22 106.27(16) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O5 C22 N4 123.41(19) . . ?
O5 C22 C19 120.85(19) . . ?
N4 C22 C19 115.56(15) . . ?
N4 C23 C24 107.85(15) . . ?
N4 C23 C26 112.22(14) . . ?
C24 C23 C26 105.58(16) . . ?
N4 C23 C25 110.90(17) . . ?
C24 C23 C25 109.84(16) . . ?
C26 C23 C25 110.27(14) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O6 C26 N5 121.81(16) . . ?
O6 C26 C23 120.11(15) . . ?
N5 C26 C23 117.71(15) . . ?
N5 C27 C29 110.91(15) . . ?
N5 C27 C28 108.02(14) . . ?
C29 C27 C28 110.51(16) . . ?
N5 C27 C30 110.11(14) . . ?
C29 C27 C30 110.01(15) . . ?
C28 C27 C30 107.19(15) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O7 C30 O8 125.71(18) . . ?
O7 C30 C27 124.41(16) . . ?
O8 C30 C27 109.72(16) . . ?
O8 C31 C34 101.4(3) . . ?
O8 C31 C32 110.59(17) . . ?
C34 C31 C32 110.6(2) . . ?
O8 C31 C33 109.15(18) . . ?
C34 C31 C33 112.2(3) . . ?
C32 C31 C33 112.4(3) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C8 N1 C9 122.33(16) . . ?
C8 N1 H1 118.8 . . ?
C9 N1 H1 118.8 . . ?
C14 N2 C15 122.59(15) . . ?
C14 N2 H2A 118.7 . . ?
C15 N2 H2A 118.7 . . ?
C18 N3 C19 121.97(15) . . ?
C18 N3 H3A 119.0 . . ?
C19 N3 H3A 119.0 . . ?
C22 N4 C23 124.32(15) . . ?
C22 N4 H4A 117.8 . . ?
C23 N4 H4A 117.8 . . ?
C26 N5 C27 121.73(14) . . ?
C26 N5 H5A 119.1 . . ?
C27 N5 H5A 119.1 . . ?
C8 O1 C7 117.2(15) . . ?
C8 O1 C7S 114.7(15) . . ?
C7 O1 C7S 9.4(2) . . ?
C30 O8 C31 121.5(2) . . ?
C2S C1S C6S 120.0 . . ?
C2S C1S C7S 121.2(12) . . ?
C6S C1S C7S 118.6(12) . . ?
C1S C2S C3S 120.0 . . ?
C1S C2S H2S 120.0 . . ?
C3S C2S H2S 120.0 . . ?
C4S C3S C2S 120.0 . . ?
C4S C3S H3S 120.0 . . ?
C2S C3S H3S 120.0 . . ?
C3S C4S C5S 120.0 . . ?
C3S C4S H4S 120.0 . . ?
C5S C4S H4S 120.0 . . ?
C4S C5S C6S 120.0 . . ?
C4S C5S H5S 120.0 . . ?
C6S C5S H5S 120.0 . . ?
C5S C6S C1S 120.0 . . ?
C5S C6S H6S 120.0 . . ?
C1S C6S H6S 120.0 . . ?
O1 C7S C1S 114.6(5) . . ?
O1 C7S H7C 108.6 . . ?
C1S C7S H7C 108.6 . . ?
O1 C7S H7D 108.6 . . ?
C1S C7S H7D 108.6 . . ?
H7C C7S H7D 107.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.0 . . . . ?
C7 C1 C2 C3 171.6(14) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C7 C1 C6 C5 -171.1(13) . . . . ?
C2 C1 C7 O1 143.4(15) . . . . ?
C6 C1 C7 O1 -45(3) . . . . ?
N1 C9 C10 C11 -160.38(16) . . . . ?
C13 C9 C10 C11 77.8(2) . . . . ?
C14 C9 C10 C11 -41.7(2) . . . . ?
N1 C9 C10 C12 74.22(19) . . . . ?
C13 C9 C10 C12 -47.6(2) . . . . ?
C14 C9 C10 C12 -167.11(16) . . . . ?
N1 C9 C14 O3 -146.58(18) . . . . ?
C13 C9 C14 O3 -25.8(3) . . . . ?
C10 C9 C14 O3 97.1(2) . . . . ?
N1 C9 C14 N2 34.9(2) . . . . ?
C13 C9 C14 N2 155.71(19) . . . . ?
C10 C9 C14 N2 -81.4(2) . . . . ?
N2 C15 C18 O4 -153.71(18) . . . . ?
C16 C15 C18 O4 -31.6(2) . . . . ?
C17 C15 C18 O4 89.2(2) . . . . ?
N2 C15 C18 N3 28.2(2) . . . . ?
C16 C15 C18 N3 150.32(18) . . . . ?
C17 C15 C18 N3 -88.8(2) . . . . ?
N3 C19 C22 O5 -150.65(17) . . . . ?
C20 C19 C22 O5 -27.6(2) . . . . ?
C21 C19 C22 O5 93.1(2) . . . . ?
N3 C19 C22 N4 34.0(2) . . . . ?
C20 C19 C22 N4 157.06(16) . . . . ?
C21 C19 C22 N4 -82.28(19) . . . . ?
N4 C23 C26 O6 -164.83(16) . . . . ?
C24 C23 C26 O6 77.94(19) . . . . ?
C25 C23 C26 O6 -40.7(2) . . . . ?
N4 C23 C26 N5 22.1(2) . . . . ?
C24 C23 C26 N5 -95.17(19) . . . . ?
C25 C23 C26 N5 146.23(18) . . . . ?
N5 C27 C30 O7 135.31(17) . . . . ?
C29 C27 C30 O7 12.8(2) . . . . ?
C28 C27 C30 O7 -107.42(19) . . . . ?
N5 C27 C30 O8 -49.13(18) . . . . ?
C29 C27 C30 O8 -171.66(14) . . . . ?
C28 C27 C30 O8 68.14(18) . . . . ?
O2 C8 N1 C9 -3.7(3) . . . . ?
O1 C8 N1 C9 177.10(16) . . . . ?
C13 C9 N1 C8 -63.1(2) . . . . ?
C14 C9 N1 C8 55.9(2) . . . . ?
C10 C9 N1 C8 173.65(17) . . . . ?
O3 C14 N2 C15 -2.0(3) . . . . ?
C9 C14 N2 C15 176.48(18) . . . . ?
C16 C15 N2 C14 -66.9(2) . . . . ?
C17 C15 N2 C14 171.76(18) . . . . ?
C18 C15 N2 C14 54.8(2) . . . . ?
O4 C18 N3 C19 1.3(3) . . . . ?
C15 C18 N3 C19 179.27(17) . . . . ?
C20 C19 N3 C18 -71.4(2) . . . . ?
C21 C19 N3 C18 167.68(19) . . . . ?
C22 C19 N3 C18 52.1(2) . . . . ?
O5 C22 N4 C23 -1.2(3) . . . . ?
C19 C22 N4 C23 174.06(15) . . . . ?
C24 C23 N4 C22 179.54(16) . . . . ?
C26 C23 N4 C22 63.7(2) . . . . ?
C25 C23 N4 C22 -60.2(2) . . . . ?
O6 C26 N5 C27 0.9(3) . . . . ?
C23 C26 N5 C27 173.87(16) . . . . ?
C29 C27 N5 C26 72.7(2) . . . . ?
C28 C27 N5 C26 -166.07(17) . . . . ?
C30 C27 N5 C26 -49.3(2) . . . . ?
O2 C8 O1 C7 -0.2(6) . . . . ?
N1 C8 O1 C7 179.0(5) . . . . ?
O2 C8 O1 C7S -10.2(7) . . . . ?
N1 C8 O1 C7S 169.0(6) . . . . ?
C1 C7 O1 C8 -62(2) . . . . ?
C1 C7 O1 C7S 15(17) . . . . ?
O7 C30 O8 C31 -2.8(3) . . . . ?
C27 C30 O8 C31 -178.32(14) . . . . ?
C34 C31 O8 C30 -178.77(18) . . . . ?
C32 C31 O8 C30 63.9(3) . . . . ?
C33 C31 O8 C30 -60.2(3) . . . . ?
C6S C1S C2S C3S 0.0 . . . . ?
C7S C1S C2S C3S -174.6(10) . . . . ?
C1S C2S C3S C4S 0.0 . . . . ?
C2S C3S C4S C5S 0.0 . . . . ?
C3S C4S C5S C6S 0.0 . . . . ?
C4S C5S C6S C1S 0.0 . . . . ?
C2S C1S C6S C5S 0.0 . . . . ?
C7S C1S C6S C5S 174.8(11) . . . . ?
C8 O1 C7S C1S -80(3) . . . . ?
C7 O1 C7S C1S 172(21) . . . . ?
C2S C1S C7S O1 128.4(19) . . . . ?
C6S C1S C7S O1 -46(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O6 0.88 2.02 2.863(2) 160.3 1_655
N3 H3A O2 0.88 2.20 3.030(2) 157.0 .
N4 H4A O3 0.88 2.12 2.9588(19) 159.9 .
N5 H5A O4 0.88 2.17 3.033(2) 165.9 .

_diffrn_measured_fraction_theta_max 0.946
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 0.954
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.050
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
