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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mk135
# structure Linda JW Shimon, Weizmann Institute 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H25 N5 O5'
_chemical_formula_sum            'C23 H25 N5 O5'
_chemical_formula_weight         451.48
_chemical_absolute_configuration rm

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   5.5457(3)
_cell_length_b                   8.9659(3)
_cell_length_c                   42.4254(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2109.48(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9465
_cell_measurement_theta_min      3.8
_cell_measurement_theta_max      26.21

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9699
_exptl_absorpt_correction_T_max  0.9980
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker KappaApexII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9463
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         26.33
_reflns_number_total             4002
_reflns_number_gt                3551
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Apex2'
_computing_cell_refinement       'Bruker Apex2'
_computing_data_reduction        'Bruker Apex2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0590P)²+0.4166P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.1(11)
_refine_ls_number_reflns         4002
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1028
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1' C -0.5983(4) 0.4023(2) 0.95682(4) 0.0161(4) Uani 1 1 d . . .
H1 H -0.7364 0.3783 0.9711 0.019 Uiso 1 1 calc R . .
C2' C -0.4684(4) 0.5412(2) 0.96883(4) 0.0178(4) Uani 1 1 d . . .
H2A H -0.4599 0.5429 0.9921 0.021 Uiso 1 1 calc R . .
H2B H -0.3036 0.5492 0.9600 0.021 Uiso 1 1 calc R . .
C3' C -0.6316(4) 0.6629(2) 0.95634(4) 0.0180(4) Uani 1 1 d . . .
H3A H -0.5431 0.7594 0.9540 0.022 Uiso 1 1 calc R . .
C4' C -0.7117(4) 0.6017(2) 0.92443(4) 0.0185(4) Uani 1 1 d . . .
H4 H -0.8850 0.6276 0.9209 0.022 Uiso 1 1 calc R . .
C5' C -0.5631(5) 0.6565(2) 0.89663(5) 0.0267(5) Uani 1 1 d . . .
H5A H -0.6075 0.5981 0.8777 0.032 Uiso 1 1 calc R . .
H5B H -0.6040 0.7622 0.8925 0.032 Uiso 1 1 calc R . .
O1 O -0.6872(3) 0.44114(14) 0.92653(3) 0.0199(3) Uani 1 1 d . . .
O2 O -0.8295(3) 0.67637(15) 0.97801(3) 0.0214(3) Uani 1 1 d . . .
H2 H -0.9313 0.7367 0.9708 0.032 Uiso 1 1 calc R . .
O3 O -0.3081(3) 0.64452(18) 0.90158(4) 0.0322(4) Uani 1 1 d . . .
H3B H -0.2632 0.7107 0.9143 0.048 Uiso 1 1 calc R . .
O4 O -0.6189(3) 0.15793(14) 0.99587(3) 0.0212(3) Uani 1 1 d . . .
O5 O -0.0723(3) -0.10843(15) 0.94045(3) 0.0240(4) Uani 1 1 d . . .
N1 N -0.4468(3) 0.27064(16) 0.95300(3) 0.0156(4) Uani 1 1 d . . .
N3 N -0.3358(3) 0.03225(17) 0.96774(3) 0.0161(4) Uani 1 1 d . . .
H3N H -0.3521 -0.0438 0.9807 0.019 Uiso 1 1 calc R . .
N4 N 0.5242(4) 0.1440(2) 0.82006(4) 0.0273(4) Uani 1 1 d . . .
N5 N 0.4820(4) 0.2367(2) 0.79835(4) 0.0275(4) Uani 1 1 d . . .
N6 N 1.0478(5) 0.2062(2) 0.68934(4) 0.0418(6) Uani 1 1 d . . .
C2 C -0.4780(4) 0.1545(2) 0.97393(4) 0.0171(4) Uani 1 1 d . . .
C4 C -0.1701(4) 0.0145(2) 0.94359(4) 0.0168(4) Uani 1 1 d . . .
C5 C -0.1338(4) 0.1459(2) 0.92385(4) 0.0171(4) Uani 1 1 d . . .
C6 C -0.2728(4) 0.2659(2) 0.93019(4) 0.0161(4) Uani 1 1 d . . .
H6 H -0.2479 0.3533 0.9179 0.019 Uiso 1 1 calc R . .
C7 C 0.0374(4) 0.1459(2) 0.89724(4) 0.0176(4) Uani 1 1 d . . .
C8 C -0.0126(4) 0.2337(2) 0.87044(4) 0.0224(5) Uani 1 1 d . . .
H8 H -0.1568 0.2908 0.8697 0.027 Uiso 1 1 calc R . .
C9 C 0.1449(4) 0.2382(2) 0.84515(5) 0.0252(5) Uani 1 1 d . . .
H9 H 0.1088 0.2987 0.8274 0.030 Uiso 1 1 calc R . .
C10 C 0.3563(4) 0.1541(2) 0.84566(5) 0.0222(5) Uani 1 1 d . . .
C11 C 0.4071(4) 0.0673(2) 0.87190(5) 0.0224(5) Uani 1 1 d . . .
H11 H 0.5509 0.0098 0.8725 0.027 Uiso 1 1 calc R . .
C12 C 0.2497(4) 0.0638(2) 0.89732(4) 0.0199(5) Uani 1 1 d . . .
H12 H 0.2880 0.0041 0.9151 0.024 Uiso 1 1 calc R . .
C13 C 0.6381(5) 0.2259(3) 0.77213(5) 0.0271(5) Uani 1 1 d . . .
C14 C 0.8309(5) 0.1291(3) 0.76968(5) 0.0323(6) Uani 1 1 d . . .
H14 H 0.8695 0.0659 0.7869 0.039 Uiso 1 1 calc R . .
C15 C 0.9683(5) 0.1227(3) 0.74264(5) 0.0368(6) Uani 1 1 d . . .
H15 H 1.0995 0.0548 0.7414 0.044 Uiso 1 1 calc R . .
C16 C 0.9154(5) 0.2164(3) 0.71677(5) 0.0297(6) Uani 1 1 d . . .
C17 C 0.7228(5) 0.3165(3) 0.71977(5) 0.0328(6) Uani 1 1 d . . .
H17 H 0.6854 0.3823 0.7029 0.039 Uiso 1 1 calc R . .
C18 C 0.5868(5) 0.3200(3) 0.74706(5) 0.0329(6) Uani 1 1 d . . .
H18 H 0.4561 0.3881 0.7487 0.039 Uiso 1 1 calc R . .
C19 C 1.0060(6) 0.3082(3) 0.66372(5) 0.0405(7) Uani 1 1 d . . .
H19A H 1.0505 0.4094 0.6703 0.061 Uiso 1 1 calc R . .
H19B H 0.8350 0.3061 0.6579 0.061 Uiso 1 1 calc R . .
H19C H 1.1040 0.2787 0.6455 0.061 Uiso 1 1 calc R . .
C20 C 1.2310(6) 0.0917(3) 0.68554(6) 0.0423(7) Uani 1 1 d . . .
H20A H 1.1627 -0.0057 0.6910 0.063 Uiso 1 1 calc R . .
H20B H 1.3675 0.1134 0.6995 0.063 Uiso 1 1 calc R . .
H20C H 1.2863 0.0903 0.6636 0.063 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
C1' O1 1.420(2) . ?
C1' N1 1.458(3) . ?
C1' C2' 1.527(3) . ?
C1' H1 1.0000 . ?
C2' C3' 1.513(3) . ?
C2' H2A 0.9900 . ?
C2' H2B 0.9900 . ?
C3' O2 1.437(3) . ?
C3' C4' 1.526(3) . ?
C3' H3A 1.0000 . ?
C4' O1 1.449(2) . ?
C4' C5' 1.520(3) . ?
C4' H4 1.0000 . ?
C5' O3 1.434(3) . ?
C5' H5A 0.9900 . ?
C5' H5B 0.9900 . ?
O2 H2 0.8400 . ?
O3 H3B 0.8400 . ?
O4 C2 1.216(2) . ?
O5 C4 1.236(2) . ?
N1 C6 1.367(3) . ?
N1 C2 1.380(2) . ?
N3 C2 1.376(3) . ?
N3 C4 1.385(3) . ?
N3 H3N 0.8800 . ?
N4 N5 1.263(2) . ?
N4 C10 1.433(3) . ?
N5 C13 1.413(3) . ?
N6 C16 1.379(3) . ?
N6 C19 1.439(3) . ?
N6 C20 1.453(4) . ?
C4 C5 1.459(3) . ?
C5 C6 1.351(3) . ?
C5 C7 1.476(3) . ?
C6 H6 0.9500 . ?
C7 C12 1.388(3) . ?
C7 C8 1.411(3) . ?
C8 C9 1.384(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(3) . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.381(3) . ?
C13 C18 1.387(3) . ?
C14 C15 1.379(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.413(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.400(4) . ?
C17 C18 1.382(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1' N1 107.35(14) . . ?
O1 C1' C2' 105.41(15) . . ?
N1 C1' C2' 115.21(18) . . ?
O1 C1' H1 109.6 . . ?
N1 C1' H1 109.6 . . ?
C2' C1' H1 109.6 . . ?
C3' C2' C1' 100.91(16) . . ?
C3' C2' H2A 111.6 . . ?
C1' C2' H2A 111.6 . . ?
C3' C2' H2B 111.6 . . ?
C1' C2' H2B 111.6 . . ?
H2A C2' H2B 109.4 . . ?
O2 C3' C2' 107.06(15) . . ?
O2 C3' C4' 112.06(18) . . ?
C2' C3' C4' 103.05(15) . . ?
O2 C3' H3A 111.4 . . ?
C2' C3' H3A 111.4 . . ?
C4' C3' H3A 111.4 . . ?
O1 C4' C5' 108.55(17) . . ?
O1 C4' C3' 105.97(15) . . ?
C5' C4' C3' 114.47(18) . . ?
O1 C4' H4 109.2 . . ?
C5' C4' H4 109.2 . . ?
C3' C4' H4 109.2 . . ?
O3 C5' C4' 113.37(18) . . ?
O3 C5' H5A 108.9 . . ?
C4' C5' H5A 108.9 . . ?
O3 C5' H5B 108.9 . . ?
C4' C5' H5B 108.9 . . ?
H5A C5' H5B 107.7 . . ?
C1' O1 C4' 109.38(13) . . ?
C3' O2 H2 109.5 . . ?
C5' O3 H3B 109.5 . . ?
C6 N1 C2 121.41(17) . . ?
C6 N1 C1' 120.69(15) . . ?
C2 N1 C1' 117.84(16) . . ?
C2 N3 C4 127.80(16) . . ?
C2 N3 H3N 116.1 . . ?
C4 N3 H3N 116.1 . . ?
N5 N4 C10 112.99(19) . . ?
N4 N5 C13 114.56(19) . . ?
C16 N6 C19 120.6(2) . . ?
C16 N6 C20 120.85(19) . . ?
C19 N6 C20 118.5(2) . . ?
O4 C2 N3 122.33(17) . . ?
O4 C2 N1 123.68(18) . . ?
N3 C2 N1 113.98(17) . . ?
O5 C4 N3 118.25(17) . . ?
O5 C4 C5 126.71(18) . . ?
N3 C4 C5 115.03(16) . . ?
C6 C5 C4 116.77(17) . . ?
C6 C5 C7 121.31(17) . . ?
C4 C5 C7 121.85(17) . . ?
C5 C6 N1 124.61(17) . . ?
C5 C6 H6 117.7 . . ?
N1 C6 H6 117.7 . . ?
C12 C7 C8 117.69(19) . . ?
C12 C7 C5 122.96(17) . . ?
C8 C7 C5 119.34(19) . . ?
C9 C8 C7 121.1(2) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 120.20(18) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 119.12(19) . . ?
C11 C10 N4 116.1(2) . . ?
C9 C10 N4 124.68(19) . . ?
C10 C11 C12 120.6(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 121.28(19) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
C14 C13 C18 118.9(2) . . ?
C14 C13 N5 125.23(19) . . ?
C18 C13 N5 115.9(2) . . ?
C15 C14 C13 121.1(2) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 120.5(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
N6 C16 C17 121.7(2) . . ?
N6 C16 C15 120.4(2) . . ?
C17 C16 C15 117.9(2) . . ?
C18 C17 C16 120.5(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C13 121.1(2) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
N6 C19 H19A 109.5 . . ?
N6 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N6 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N6 C20 H20A 109.5 . . ?
N6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        26.33
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 972500'
