# 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_s3910ma
#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------# 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H22 N4 O3'
_chemical_formula_weight         270.34

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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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                   9.23450(10)
_cell_length_b                   10.44030(10)
_cell_length_c                   15.8938(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1532.34(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6954
_cell_measurement_theta_min      5.07
_cell_measurement_theta_max      72.43

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.794158
_exptl_absorpt_correction_T_max  0.8605
_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_reflns_number            8405
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.07
_diffrn_reflns_theta_max         72.42
_reflns_number_total             2966
_reflns_number_gt                2923
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0343P)²+0.3011P] 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   -0.01(14)
_refine_ls_number_reflns         2966
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_ref         0.0677
_refine_ls_wR_factor_gt          0.0674
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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 0.38443(11) 0.74774(10) 0.28758(7) 0.0164(2) Uani 1 1 d . . .
C2 C 0.53235(13) 0.71520(12) 0.32379(8) 0.0234(3) Uani 1 1 d . . .
H2A H 0.5950 0.7908 0.3210 0.035 Uiso 1 1 calc R . .
H2B H 0.5758 0.6455 0.2911 0.035 Uiso 1 1 calc R . .
H2C H 0.5216 0.6883 0.3825 0.035 Uiso 1 1 calc R . .
C3 C 0.39767(14) 0.80336(11) 0.19875(8) 0.0227(3) Uani 1 1 d . . .
H3A H 0.3010 0.8232 0.1770 0.034 Uiso 1 1 calc R . .
H3B H 0.4446 0.7406 0.1619 0.034 Uiso 1 1 calc R . .
H3C H 0.4559 0.8818 0.2006 0.034 Uiso 1 1 calc R . .
C4 C 0.28886(12) 0.62729(10) 0.28062(7) 0.0149(2) Uani 1 1 d . . .
C5 C 0.04371(12) 0.53847(10) 0.28071(6) 0.0136(2) Uani 1 1 d . . .
C6 C -0.11041(12) 0.59347(11) 0.28717(8) 0.0182(2) Uani 1 1 d . . .
H6A H -0.1268 0.6259 0.3442 0.027 Uiso 1 1 calc R . .
H6B H -0.1810 0.5260 0.2747 0.027 Uiso 1 1 calc R . .
H6C H -0.1217 0.6635 0.2467 0.027 Uiso 1 1 calc R . .
C7 C 0.06237(13) 0.42876(11) 0.34345(7) 0.0185(2) Uani 1 1 d . . .
H7A H 0.1606 0.3939 0.3388 0.028 Uiso 1 1 calc R . .
H7B H -0.0083 0.3613 0.3311 0.028 Uiso 1 1 calc R . .
H7C H 0.0468 0.4608 0.4007 0.028 Uiso 1 1 calc R . .
C8 C 0.05832(11) 0.48730(10) 0.19048(6) 0.0131(2) Uani 1 1 d . . .
C9 C 0.09265(13) 0.55356(11) 0.04445(7) 0.0177(2) Uani 1 1 d . . .
C10 C 0.14409(16) 0.68059(11) 0.00830(7) 0.0265(3) Uani 1 1 d . . .
H10A H 0.0770 0.7487 0.0250 0.040 Uiso 1 1 calc R . .
H10B H 0.1473 0.6749 -0.0532 0.040 Uiso 1 1 calc R . .
H10C H 0.2411 0.7000 0.0298 0.040 Uiso 1 1 calc R . .
C11 C 0.19940(14) 0.44735(12) 0.02356(7) 0.0237(3) Uani 1 1 d . . .
H11A H 0.2923 0.4649 0.0511 0.036 Uiso 1 1 calc R . .
H11B H 0.2135 0.4434 -0.0375 0.036 Uiso 1 1 calc R . .
H11C H 0.1612 0.3653 0.0436 0.036 Uiso 1 1 calc R . .
C12 C -0.06129(14) 0.52430(12) 0.01650(7) 0.0234(3) Uani 1 1 d . . .
H12A H -0.0904 0.4403 0.0382 0.035 Uiso 1 1 calc R . .
H12B H -0.0658 0.5236 -0.0451 0.035 Uiso 1 1 calc R . .
H12C H -0.1269 0.5901 0.0384 0.035 Uiso 1 1 calc R . .
N1 N 0.41814(16) 1.02356(14) 0.39467(11) 0.0538(4) Uani 1 1 d . . .
N2 N 0.37091(11) 0.93243(10) 0.36785(7) 0.0244(2) Uani 1 1 d . . .
N3 N 0.30461(11) 0.83967(10) 0.34276(7) 0.0257(2) Uani 1 1 d . . .
N4 N 0.14681(10) 0.64199(9) 0.29665(6) 0.01371(18) Uani 1 1 d . . .
O1 O 0.34168(9) 0.52582(8) 0.25656(6) 0.02111(18) Uani 1 1 d . . .
O2 O 0.03068(9) 0.37781(7) 0.17195(5) 0.01741(17) Uani 1 1 d . . .
O3 O 0.09203(9) 0.57996(7) 0.13620(5) 0.01638(17) Uani 1 1 d . . .
H4 H 0.1128(17) 0.7161(15) 0.3108(9) 0.022(4) Uiso 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
C1 N3 1.4946(15) . ?
C1 C2 1.5207(15) . ?
C1 C3 1.5315(16) . ?
C1 C4 1.5402(15) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 O1 1.2274(14) . ?
C4 N4 1.3450(14) . ?
C5 N4 1.4624(13) . ?
C5 C7 1.5284(14) . ?
C5 C8 1.5364(14) . ?
C5 C6 1.5381(15) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 O2 1.2077(13) . ?
C8 O3 1.3330(13) . ?
C9 O3 1.4841(13) . ?
C9 C12 1.5204(17) . ?
C9 C11 1.5204(16) . ?
C9 C10 1.5214(15) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N1 N2 1.1301(16) . ?
N2 N3 1.2131(15) . ?
N4 H4 0.864(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C1 C2 111.37(10) . . ?
N3 C1 C3 109.69(9) . . ?
C2 C1 C3 111.22(9) . . ?
N3 C1 C4 106.49(9) . . ?
C2 C1 C4 111.07(9) . . ?
C3 C1 C4 106.81(9) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C4 N4 123.03(10) . . ?
O1 C4 C1 119.96(10) . . ?
N4 C4 C1 116.88(9) . . ?
N4 C5 C7 111.56(9) . . ?
N4 C5 C8 111.19(8) . . ?
C7 C5 C8 109.78(9) . . ?
N4 C5 C6 108.36(9) . . ?
C7 C5 C6 109.91(9) . . ?
C8 C5 C6 105.87(8) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 O3 125.35(10) . . ?
O2 C8 C5 122.56(9) . . ?
O3 C8 C5 111.85(9) . . ?
O3 C9 C12 108.72(9) . . ?
O3 C9 C11 110.64(9) . . ?
C12 C9 C11 113.32(10) . . ?
O3 C9 C10 102.14(9) . . ?
C12 C9 C10 110.90(10) . . ?
C11 C9 C10 110.54(10) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 N2 N3 172.23(14) . . ?
N2 N3 C1 117.17(10) . . ?
C4 N4 C5 121.19(9) . . ?
C4 N4 H4 120.4(11) . . ?
C5 N4 H4 118.0(11) . . ?
C8 O3 C9 120.13(8) . . ?

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
N3 C1 C4 O1 -162.28(10) . . . . ?
C2 C1 C4 O1 -40.87(14) . . . . ?
C3 C1 C4 O1 80.56(13) . . . . ?
N3 C1 C4 N4 21.88(13) . . . . ?
C2 C1 C4 N4 143.29(10) . . . . ?
C3 C1 C4 N4 -95.27(11) . . . . ?
N4 C5 C8 O2 150.62(10) . . . . ?
C7 C5 C8 O2 26.69(15) . . . . ?
C6 C5 C8 O2 -91.90(12) . . . . ?
N4 C5 C8 O3 -34.77(12) . . . . ?
C7 C5 C8 O3 -158.71(9) . . . . ?
C6 C5 C8 O3 82.70(11) . . . . ?
N1 N2 N3 C1 172.5(11) . . . . ?
C2 C1 N3 N2 46.93(15) . . . . ?
C3 C1 N3 N2 -76.62(14) . . . . ?
C4 C1 N3 N2 168.15(11) . . . . ?
O1 C4 N4 C5 -4.19(16) . . . . ?
C1 C4 N4 C5 171.51(9) . . . . ?
C7 C5 N4 C4 70.76(12) . . . . ?
C8 C5 N4 C4 -52.16(13) . . . . ?
C6 C5 N4 C4 -168.11(10) . . . . ?
O2 C8 O3 C9 2.23(16) . . . . ?
C5 C8 O3 C9 -172.19(9) . . . . ?
C12 C9 O3 C8 65.78(12) . . . . ?
C11 C9 O3 C8 -59.28(13) . . . . ?
C10 C9 O3 C8 -176.96(10) . . . . ?

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
N4 H4 O2 0.864(16) 2.164(16) 2.9995(12) 162.5(14) 3

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        66.60
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.031
_database_code_depnum_ccdc_archive 'CCDC 984593'
#######################################################################
#
#                 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_s3887ma
#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------#

_audit_creation_date             
;
'Wed Sep 25 21:23:33 2013'
;
_audit_creation_method           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_cell_measurement_temperature    150.06(15)
_chemical_formula_sum            'C16 H29 N5 O4'
_chemical_formula_weight         355.44

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'


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

_cell_length_a                   10.2430(2)
_cell_length_b                   10.7344(2)
_cell_length_c                   17.9400(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.2641(19)
_cell_angle_gamma                90.00
_cell_volume                     1956.72(7)
_cell_formula_units_Z            4
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.088
_exptl_crystal_density_diffrn    1.207
_diffrn_reflns_number            20582
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         29.45
_reflns_number_total             4895
_reflns_number_gt                3842
_reflns_threshold_expression     >2sigma(I)
_cell_measurement_reflns_used    7722
_cell_measurement_theta_min      3.7280
_cell_measurement_theta_max      29.2670
_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.2500
_exptl_crystal_size_mid          0.2200
_exptl_crystal_size_min          0.1700
_exptl_absorpt_correction_T_min  0.90394
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150.06(15)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_detector_area_resol_mean 10.3705
_diffrn_orient_matrix_UB_11      -0.0443717000
_diffrn_orient_matrix_UB_12      0.0127627000
_diffrn_orient_matrix_UB_13      0.0263356000
_diffrn_orient_matrix_UB_21      0.0165869000
_diffrn_orient_matrix_UB_22      0.0641330000
_diffrn_orient_matrix_UB_23      -0.0007129000
_diffrn_orient_matrix_UB_31      -0.0512915000
_diffrn_orient_matrix_UB_32      0.0096852000
_diffrn_orient_matrix_UB_33      -0.0298792000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -85.00   11.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6555  -37.0000   30.0000 96

#__ type_ start__ end____ width___ exp.time_
  2 omega  -41.00   -9.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6555   55.0000   69.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega  -16.00   29.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6555  -99.0000 -150.0000 45

#__ type_ start__ end____ width___ exp.time_
  4 omega  -25.00   49.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6555   57.0000 -180.0000 74

#__ type_ start__ end____ width___ exp.time_
  5 omega   54.00  100.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       11.6555 -178.0000   90.0000 46

#__ type_ start__ end____ width___ exp.time_
  6 omega   36.00   85.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       11.6555 -178.0000   30.0000 49

#__ type_ start__ end____ width___ exp.time_
  7 omega   37.00   77.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       11.6555   57.0000 -120.0000 40

;
_diffrn_measurement_method       'ω scans'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_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)+(0.0389P)²+0.5853P] 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_number_reflns         4895
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.0987
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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 0.30680(10) 0.87302(10) 0.06674(6) 0.0180(2) Uani 1 1 d . . .
C2 C 0.38823(12) 0.86442(12) 0.00180(7) 0.0251(3) Uani 1 1 d . . .
H2A H 0.3851 0.7790 -0.0176 0.038 Uiso 1 1 calc R . .
H2B H 0.4796 0.8871 0.0194 0.038 Uiso 1 1 calc R . .
H2C H 0.3525 0.9216 -0.0382 0.038 Uiso 1 1 calc R . .
C3 C 0.29384(13) 1.00684(11) 0.09316(7) 0.0268(3) Uani 1 1 d . . .
H3A H 0.2527 1.0578 0.0513 0.040 Uiso 1 1 calc R . .
H3B H 0.3813 1.0402 0.1110 0.040 Uiso 1 1 calc R . .
H3C H 0.2392 1.0087 0.1342 0.040 Uiso 1 1 calc R . .
C4 C 0.37402(11) 0.79530(10) 0.13269(6) 0.0178(2) Uani 1 1 d . . .
C5 C 0.35176(11) 0.61507(10) 0.21727(6) 0.0183(2) Uani 1 1 d . . .
C6 C 0.47562(11) 0.54483(11) 0.20163(7) 0.0245(3) Uani 1 1 d . . .
H6A H 0.4554 0.4939 0.1563 0.037 Uiso 1 1 calc R . .
H6B H 0.5057 0.4909 0.2444 0.037 Uiso 1 1 calc R . .
H6C H 0.5450 0.6048 0.1942 0.037 Uiso 1 1 calc R . .
C7 C 0.37432(13) 0.68838(12) 0.29068(7) 0.0272(3) Uani 1 1 d . . .
H7A H 0.4427 0.7512 0.2873 0.041 Uiso 1 1 calc R . .
H7B H 0.4024 0.6314 0.3323 0.041 Uiso 1 1 calc R . .
H7C H 0.2923 0.7296 0.2995 0.041 Uiso 1 1 calc R . .
C8 C 0.23782(11) 0.52025(10) 0.21890(6) 0.0190(2) Uani 1 1 d . . .
C9 C 0.16797(11) 0.33289(10) 0.28612(7) 0.0196(2) Uani 1 1 d . . .
C10 C 0.02468(12) 0.37315(13) 0.28802(8) 0.0293(3) Uani 1 1 d . . .
H10A H 0.0214 0.4380 0.3262 0.044 Uiso 1 1 calc R . .
H10B H -0.0275 0.3012 0.3004 0.044 Uiso 1 1 calc R . .
H10C H -0.0114 0.4060 0.2387 0.044 Uiso 1 1 calc R . .
C11 C 0.17860(14) 0.23641(12) 0.22471(7) 0.0306(3) Uani 1 1 d . . .
H11A H 0.1495 0.2735 0.1755 0.046 Uiso 1 1 calc R . .
H11B H 0.1228 0.1646 0.2326 0.046 Uiso 1 1 calc R . .
H11C H 0.2703 0.2091 0.2266 0.046 Uiso 1 1 calc R . .
C12 C 0.21454(11) 0.28443(10) 0.36560(6) 0.0188(2) Uani 1 1 d . . .
C13 C 0.21635(11) 0.09543(11) 0.44274(7) 0.0210(2) Uani 1 1 d . . .
C14 C 0.19273(15) -0.03888(12) 0.41866(8) 0.0345(3) Uani 1 1 d . . .
H14A H 0.1049 -0.0468 0.3903 0.052 Uiso 1 1 calc R . .
H14B H 0.1989 -0.0924 0.4632 0.052 Uiso 1 1 calc R . .
H14C H 0.2592 -0.0643 0.3869 0.052 Uiso 1 1 calc R . .
C15 C 0.35471(12) 0.11400(14) 0.48281(8) 0.0321(3) Uani 1 1 d . . .
H15A H 0.4186 0.1007 0.4473 0.048 Uiso 1 1 calc R . .
H15B H 0.3711 0.0543 0.5243 0.048 Uiso 1 1 calc R . .
H15C H 0.3637 0.1990 0.5027 0.048 Uiso 1 1 calc R . .
C16 C 0.11256(12) 0.13998(12) 0.48944(8) 0.0278(3) Uani 1 1 d . . .
H16A H 0.1282 0.2277 0.5027 0.042 Uiso 1 1 calc R . .
H16B H 0.1169 0.0900 0.5354 0.042 Uiso 1 1 calc R . .
H16C H 0.0253 0.1310 0.4605 0.042 Uiso 1 1 calc R . .
N1 N 0.04988(15) 0.89045(17) -0.06569(9) 0.0740(6) Uani 1 1 d . . .
N2 N 0.11380(11) 0.86028(11) -0.01297(7) 0.0362(3) Uani 1 1 d . . .
N3 N 0.17300(10) 0.81862(10) 0.04531(6) 0.0249(2) Uani 1 1 d . . .
N4 N 0.30694(10) 0.69834(9) 0.15465(6) 0.0196(2) Uani 1 1 d . . .
N5 N 0.25387(10) 0.43980(9) 0.27614(6) 0.0210(2) Uani 1 1 d . . .
O1 O 0.48494(8) 0.82607(8) 0.16149(5) 0.0237(2) Uani 1 1 d . . .
O2 O 0.14240(8) 0.52195(8) 0.17011(5) 0.0283(2) Uani 1 1 d . . .
O3 O 0.25308(9) 0.35244(8) 0.41708(5) 0.0269(2) Uani 1 1 d . . .
O4 O 0.19937(8) 0.16167(7) 0.36953(4) 0.02144(19) Uani 1 1 d . . .
H4 H 0.2300(14) 0.6828(13) 0.1322(8) 0.024(4) Uiso 1 1 d . . .
H5 H 0.3274(15) 0.4374(14) 0.3039(8) 0.032(4) Uiso 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
C1 N3 1.4946(14) . ?
C1 C2 1.5190(17) . ?
C1 C3 1.5238(17) . ?
C1 C4 1.5375(15) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 O1 1.2323(13) . ?
C4 N4 1.3338(15) . ?
C5 N4 1.4633(14) . ?
C5 C7 1.5264(16) . ?
C5 C6 1.5320(16) . ?
C5 C8 1.5516(15) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 O2 1.2270(13) . ?
C8 N5 1.3359(15) . ?
C9 N5 1.4707(14) . ?
C9 C11 1.5258(17) . ?
C9 C10 1.5346(17) . ?
C9 C12 1.5361(16) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O3 1.2039(14) . ?
C12 O4 1.3297(14) . ?
C13 O4 1.4843(13) . ?
C13 C16 1.5120(18) . ?
C13 C14 1.5156(18) . ?
C13 C15 1.5190(17) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N1 N2 1.1275(16) . ?
N2 N3 1.2250(14) . ?
N4 H4 0.856(14) . ?
N5 H5 0.849(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C1 C2 110.70(9) . . ?
N3 C1 C3 109.58(10) . . ?
C2 C1 C3 111.95(10) . . ?
N3 C1 C4 107.03(9) . . ?
C2 C1 C4 108.75(9) . . ?
C3 C1 C4 108.69(9) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C4 N4 124.57(10) . . ?
O1 C4 C1 118.47(10) . . ?
N4 C4 C1 116.96(9) . . ?
N4 C5 C7 110.25(9) . . ?
N4 C5 C6 110.28(10) . . ?
C7 C5 C6 111.91(10) . . ?
N4 C5 C8 104.56(8) . . ?
C7 C5 C8 110.74(10) . . ?
C6 C5 C8 108.84(9) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 N5 124.58(11) . . ?
O2 C8 C5 120.66(10) . . ?
N5 C8 C5 114.76(9) . . ?
N5 C9 C11 110.08(10) . . ?
N5 C9 C10 111.81(10) . . ?
C11 C9 C10 111.28(10) . . ?
N5 C9 C12 104.89(9) . . ?
C11 C9 C12 113.46(10) . . ?
C10 C9 C12 105.08(10) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 O4 126.12(11) . . ?
O3 C12 C9 122.67(10) . . ?
O4 C12 C9 111.11(9) . . ?
O4 C13 C16 109.08(9) . . ?
O4 C13 C14 101.94(9) . . ?
C16 C13 C14 111.14(11) . . ?
O4 C13 C15 110.72(10) . . ?
C16 C13 C15 112.06(11) . . ?
C14 C13 C15 111.44(11) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 N2 N3 173.23(14) . . ?
N2 N3 C1 114.57(10) . . ?
C4 N4 C5 125.45(10) . . ?
C4 N4 H4 119.4(9) . . ?
C5 N4 H4 115.1(9) . . ?
C8 N5 C9 125.50(10) . . ?
C8 N5 H5 118.9(10) . . ?
C9 N5 H5 113.9(10) . . ?
C12 O4 C13 121.35(9) . . ?

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
N3 C1 C4 O1 -177.68(10) . . . . ?
C2 C1 C4 O1 62.69(13) . . . . ?
C3 C1 C4 O1 -59.41(14) . . . . ?
N3 C1 C4 N4 2.36(14) . . . . ?
C2 C1 C4 N4 -117.27(11) . . . . ?
C3 C1 C4 N4 120.63(11) . . . . ?
N4 C5 C8 O2 5.04(15) . . . . ?
C7 C5 C8 O2 123.77(12) . . . . ?
C6 C5 C8 O2 -112.80(12) . . . . ?
N4 C5 C8 N5 -175.23(10) . . . . ?
C7 C5 C8 N5 -56.50(13) . . . . ?
C6 C5 C8 N5 66.93(13) . . . . ?
N5 C9 C12 O3 35.56(15) . . . . ?
C11 C9 C12 O3 155.75(12) . . . . ?
C10 C9 C12 O3 -82.47(14) . . . . ?
N5 C9 C12 O4 -147.79(10) . . . . ?
C11 C9 C12 O4 -27.61(14) . . . . ?
C10 C9 C12 O4 94.18(11) . . . . ?
N1 N2 N3 C1 176.5(16) . . . . ?
C2 C1 N3 N2 -52.41(15) . . . . ?
C3 C1 N3 N2 71.54(14) . . . . ?
C4 C1 N3 N2 -170.78(11) . . . . ?
O1 C4 N4 C5 1.75(19) . . . . ?
C1 C4 N4 C5 -178.29(10) . . . . ?
C7 C5 N4 C4 60.55(15) . . . . ?
C6 C5 N4 C4 -63.53(14) . . . . ?
C8 C5 N4 C4 179.62(11) . . . . ?
O2 C8 N5 C9 6.6(2) . . . . ?
C5 C8 N5 C9 -173.10(10) . . . . ?
C11 C9 N5 C8 66.70(15) . . . . ?
C10 C9 N5 C8 -57.54(16) . . . . ?
C12 C9 N5 C8 -170.90(11) . . . . ?
O3 C12 O4 C13 6.67(17) . . . . ?
C9 C12 O4 C13 -169.83(9) . . . . ?
C16 C13 O4 C12 63.58(13) . . . . ?
C14 C13 O4 C12 -178.82(10) . . . . ?
C15 C13 O4 C12 -60.18(14) . . . . ?

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
N4 H4 O2 0.856(14) 2.099(14) 2.5731(13) 114.4(11) .
N4 H4 N3 0.856(14) 2.159(14) 2.5916(13) 111.0(11) .
N5 H5 O1 0.849(15) 2.282(15) 3.0237(12) 146.0(13) 2_645

_diffrn_measured_fraction_theta_max 0.904
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 984591'
#######################################################################
#
#                 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_s3770ma
#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------# 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H36 N6 O5'
_chemical_formula_weight         440.55

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                   11.2952(7)
_cell_length_b                   12.9363(9)
_cell_length_c                   18.6722(12)
_cell_angle_alpha                108.580(3)
_cell_angle_beta                 96.720(3)
_cell_angle_gamma                104.173(3)
_cell_volume                     2450.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9962
_cell_measurement_theta_min      3.72
_cell_measurement_theta_max      72.30

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.653006
_exptl_absorpt_correction_T_max  0.8761
_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_reflns_number            20090
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0636
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         72.36
_reflns_number_total             9107
_reflns_number_gt                8334
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0652P)²+3.5754P] 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_number_reflns         9107
_refine_ls_number_parameters     605
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_ref         0.1897
_refine_ls_wR_factor_gt          0.1838
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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 0.5083(2) 0.7438(2) 0.20307(15) 0.0251(5) Uani 1 1 d . . .
C2 C 0.5457(3) 0.8359(2) 0.16779(19) 0.0341(6) Uani 1 1 d . . .
H2A H 0.5277 0.7999 0.1113 0.051 Uiso 1 1 calc R . .
H2B H 0.6352 0.8762 0.1868 0.051 Uiso 1 1 calc R . .
H2C H 0.4980 0.8904 0.1827 0.051 Uiso 1 1 calc R . .
C3 C 0.5278(4) 0.7990(3) 0.29097(19) 0.0458(8) Uani 1 1 d . . .
H3A H 0.4756 0.8499 0.3035 0.069 Uiso 1 1 calc R . .
H3B H 0.6159 0.8431 0.3129 0.069 Uiso 1 1 calc R . .
H3C H 0.5044 0.7392 0.3129 0.069 Uiso 1 1 calc R . .
C4 C 0.5928(2) 0.6661(2) 0.18333(15) 0.0242(5) Uani 1 1 d . . .
C5 C 0.6090(2) 0.4751(2) 0.11124(14) 0.0213(5) Uani 1 1 d . . .
C6 C 0.6751(3) 0.5119(3) 0.05262(17) 0.0359(7) Uani 1 1 d . . .
H6A H 0.6127 0.5049 0.0088 0.054 Uiso 1 1 calc R . .
H6B H 0.7272 0.4628 0.0341 0.054 Uiso 1 1 calc R . .
H6C H 0.7277 0.5915 0.0772 0.054 Uiso 1 1 calc R . .
C7 C 0.5159(3) 0.3556(2) 0.07193(16) 0.0300(6) Uani 1 1 d . . .
H7A H 0.4718 0.3343 0.1097 0.045 Uiso 1 1 calc R . .
H7B H 0.5608 0.3005 0.0512 0.045 Uiso 1 1 calc R . .
H7C H 0.4554 0.3552 0.0296 0.045 Uiso 1 1 calc R . .
C8 C 0.7081(2) 0.4694(2) 0.17307(14) 0.0200(5) Uani 1 1 d . . .
C9 C 0.7830(2) 0.4997(2) 0.30908(14) 0.0212(5) Uani 1 1 d . . .
C10 C 0.7880(2) 0.3801(2) 0.30080(15) 0.0255(5) Uani 1 1 d . . .
H10A H 0.7067 0.3342 0.3034 0.038 Uiso 1 1 calc R . .
H10B H 0.8525 0.3848 0.3427 0.038 Uiso 1 1 calc R . .
H10C H 0.8081 0.3442 0.2509 0.038 Uiso 1 1 calc R . .
C11 C 0.7449(3) 0.5559(2) 0.38493(14) 0.0272(5) Uani 1 1 d . . .
H11A H 0.7418 0.6326 0.3891 0.041 Uiso 1 1 calc R . .
H11B H 0.8063 0.5615 0.4287 0.041 Uiso 1 1 calc R . .
H11C H 0.6624 0.5094 0.3854 0.041 Uiso 1 1 calc R . .
C12 C 0.9123(2) 0.5776(2) 0.31212(14) 0.0227(5) Uani 1 1 d . . .
C13 C 1.0291(2) 0.7621(2) 0.30696(15) 0.0249(5) Uani 1 1 d . . .
C14 C 1.1032(3) 0.7250(3) 0.24487(17) 0.0355(6) Uani 1 1 d . . .
H14A H 1.1242 0.6566 0.2467 0.053 Uiso 1 1 calc R . .
H14B H 1.1803 0.7868 0.2544 0.053 Uiso 1 1 calc R . .
H14C H 1.0527 0.7078 0.1938 0.053 Uiso 1 1 calc R . .
C15 C 0.9942(3) 0.8680(2) 0.30361(18) 0.0330(6) Uani 1 1 d . . .
H15A H 0.9468 0.8511 0.2517 0.049 Uiso 1 1 calc R . .
H15B H 1.0705 0.9316 0.3154 0.049 Uiso 1 1 calc R . .
H15C H 0.9431 0.8891 0.3416 0.049 Uiso 1 1 calc R . .
C16 C 1.1113(2) 0.7949(2) 0.38704(15) 0.0257(5) Uani 1 1 d . . .
C17 C 1.0988(3) 0.8372(3) 0.52318(16) 0.0348(6) Uani 1 1 d . . .
C18 C 0.9867(3) 0.8364(3) 0.56096(18) 0.0397(7) Uani 1 1 d . . .
H18A H 0.9492 0.8937 0.5529 0.060 Uiso 1 1 calc R . .
H18B H 1.0136 0.8545 0.6165 0.060 Uiso 1 1 calc R . .
H18C H 0.9248 0.7606 0.5378 0.060 Uiso 1 1 calc R . .
C19 C 1.1562(3) 0.7469(3) 0.5305(2) 0.0502(8) Uani 1 1 d . . .
H19A H 1.0927 0.6719 0.5083 0.075 Uiso 1 1 calc R . .
H19B H 1.1887 0.7632 0.5852 0.075 Uiso 1 1 calc R . .
H19C H 1.2247 0.7467 0.5028 0.075 Uiso 1 1 calc R . .
C20 C 1.1918(3) 0.9566(3) 0.55445(18) 0.0399(7) Uani 1 1 d . . .
H20A H 1.2646 0.9556 0.5307 0.060 Uiso 1 1 calc R . .
H20B H 1.2186 0.9809 0.6107 0.060 Uiso 1 1 calc R . .
H20C H 1.1521 1.0100 0.5421 0.060 Uiso 1 1 calc R . .
C21 C -0.1794(2) 0.1027(2) 0.12805(15) 0.0256(5) Uani 1 1 d . . .
C22 C -0.2114(3) -0.0195(2) 0.06993(17) 0.0333(6) Uani 1 1 d . . .
H22A H -0.2918 -0.0652 0.0740 0.050 Uiso 1 1 calc R . .
H22B H -0.1460 -0.0532 0.0812 0.050 Uiso 1 1 calc R . .
H22C H -0.2170 -0.0182 0.0175 0.050 Uiso 1 1 calc R . .
C23 C -0.1639(3) 0.1055(2) 0.21115(17) 0.0356(7) Uani 1 1 d . . .
H23A H -0.1369 0.1851 0.2471 0.053 Uiso 1 1 calc R . .
H23B H -0.1009 0.0684 0.2206 0.053 Uiso 1 1 calc R . .
H23C H -0.2438 0.0650 0.2190 0.053 Uiso 1 1 calc R . .
C24 C -0.0552(2) 0.1727(2) 0.11835(14) 0.0215(5) Uani 1 1 d . . .
C25 C 0.0594(2) 0.3377(2) 0.08956(14) 0.0196(5) Uani 1 1 d . . .
C26 C 0.0359(2) 0.4466(2) 0.08430(15) 0.0246(5) Uani 1 1 d . . .
H26A H -0.0381 0.4263 0.0437 0.037 Uiso 1 1 calc R . .
H26B H 0.1086 0.4913 0.0719 0.037 Uiso 1 1 calc R . .
H26C H 0.0220 0.4919 0.1339 0.037 Uiso 1 1 calc R . .
C27 C 0.0820(3) 0.2663(2) 0.01220(15) 0.0283(6) Uani 1 1 d . . .
H27A H 0.0948 0.1956 0.0155 0.042 Uiso 1 1 calc R . .
H27B H 0.1563 0.3103 0.0006 0.042 Uiso 1 1 calc R . .
H27C H 0.0092 0.2475 -0.0290 0.042 Uiso 1 1 calc R . .
C28 C 0.1773(2) 0.37341(19) 0.15366(14) 0.0185(5) Uani 1 1 d . . .
C29 C 0.2622(2) 0.4199(2) 0.29186(14) 0.0211(5) Uani 1 1 d . . .
C30 C 0.2044(3) 0.4046(2) 0.35976(15) 0.0275(6) Uani 1 1 d . . .
H30A H 0.1538 0.4567 0.3738 0.041 Uiso 1 1 calc R . .
H30B H 0.2711 0.4219 0.4042 0.041 Uiso 1 1 calc R . .
H30C H 0.1514 0.3256 0.3445 0.041 Uiso 1 1 calc R . .
C31 C 0.3419(2) 0.5429(2) 0.31304(15) 0.0257(5) Uani 1 1 d . . .
H31A H 0.3710 0.5529 0.2675 0.039 Uiso 1 1 calc R . .
H31B H 0.4141 0.5606 0.3543 0.039 Uiso 1 1 calc R . .
H31C H 0.2921 0.5945 0.3309 0.039 Uiso 1 1 calc R . .
C32 C 0.3430(2) 0.3376(2) 0.27383(13) 0.0207(5) Uani 1 1 d . . .
C33 C 0.3423(2) 0.1373(2) 0.21890(14) 0.0230(5) Uani 1 1 d . . .
C34 C 0.2404(3) 0.0219(2) 0.19097(17) 0.0316(6) Uani 1 1 d . . .
H34A H 0.1927 0.0187 0.2312 0.047 Uiso 1 1 calc R . .
H34B H 0.2792 -0.0399 0.1801 0.047 Uiso 1 1 calc R . .
H34C H 0.1843 0.0130 0.1438 0.047 Uiso 1 1 calc R . .
C35 C 0.4205(3) 0.1427(2) 0.15848(15) 0.0291(6) Uani 1 1 d . . .
H35A H 0.3679 0.1388 0.1115 0.044 Uiso 1 1 calc R . .
H35B H 0.4552 0.0783 0.1464 0.044 Uiso 1 1 calc R . .
H35C H 0.4888 0.2146 0.1787 0.044 Uiso 1 1 calc R . .
C36 C 0.4282(2) 0.1492(2) 0.29374(15) 0.0237(5) Uani 1 1 d . . .
C37 C 0.4420(3) 0.1945(3) 0.43205(16) 0.0338(6) Uani 1 1 d . . .
C38 C 0.4855(3) 0.0941(3) 0.43648(18) 0.0385(7) Uani 1 1 d . . .
H38A H 0.4132 0.0258 0.4208 0.058 Uiso 1 1 calc R . .
H38B H 0.5280 0.1114 0.4897 0.058 Uiso 1 1 calc R . .
H38C H 0.5434 0.0804 0.4019 0.058 Uiso 1 1 calc R . .
C39 C 0.5458(3) 0.3052(3) 0.45554(18) 0.0418(7) Uani 1 1 d . . .
H39A H 0.6048 0.2960 0.4212 0.063 Uiso 1 1 calc R . .
H39B H 0.5894 0.3259 0.5090 0.063 Uiso 1 1 calc R . .
H39C H 0.5105 0.3658 0.4517 0.063 Uiso 1 1 calc R . .
C40 C 0.3438(4) 0.2096(4) 0.47969(19) 0.0496(9) Uani 1 1 d . . .
H40A H 0.3148 0.2734 0.4757 0.074 Uiso 1 1 calc R . .
H40B H 0.3798 0.2258 0.5339 0.074 Uiso 1 1 calc R . .
H40C H 0.2731 0.1394 0.4603 0.074 Uiso 1 1 calc R . .
N1 N 0.2410(2) 0.7200(2) 0.08963(16) 0.0396(6) Uani 1 1 d . . .
N2 N 0.3108(2) 0.70180(18) 0.12912(13) 0.0260(5) Uani 1 1 d . . .
N3 N 0.3752(2) 0.67289(19) 0.17225(14) 0.0280(5) Uani 1 1 d . . .
N4 N 0.53806(19) 0.55375(18) 0.14505(12) 0.0197(4) Uani 1 1 d . . .
N5 N 0.69077(19) 0.49742(17) 0.24582(12) 0.0192(4) Uani 1 1 d . . .
N6 N 0.9135(2) 0.67238(19) 0.29626(13) 0.0246(5) Uani 1 1 d . . .
N7 N -0.4005(3) 0.1073(3) -0.00723(17) 0.0541(8) Uani 1 1 d . . .
N8 N -0.3382(2) 0.1268(2) 0.05081(14) 0.0322(5) Uani 1 1 d . . .
N9 N -0.2800(2) 0.1561(2) 0.11748(13) 0.0289(5) Uani 1 1 d . . .
N10 N -0.05048(19) 0.27218(17) 0.10810(12) 0.0190(4) Uani 1 1 d . . .
N11 N 0.1587(2) 0.38736(18) 0.22583(12) 0.0197(4) Uani 1 1 d . . .
N12 N 0.2802(2) 0.22676(18) 0.23468(12) 0.0215(4) Uani 1 1 d . . .
O1 O 0.70610(17) 0.71028(17) 0.20283(13) 0.0364(5) Uani 1 1 d . . .
O2 O 0.79859(16) 0.43996(16) 0.15443(10) 0.0257(4) Uani 1 1 d . . .
O3 O 1.00854(17) 0.55842(17) 0.33449(11) 0.0296(4) Uani 1 1 d . . .
O4 O 1.22312(17) 0.8168(2) 0.39818(13) 0.0388(5) Uani 1 1 d . . .
O5 O 1.04221(16) 0.80555(17) 0.44126(10) 0.0290(4) Uani 1 1 d . . .
O6 O 0.03539(17) 0.13636(15) 0.12113(11) 0.0281(4) Uani 1 1 d . . .
O7 O 0.28127(15) 0.39002(15) 0.13839(10) 0.0232(4) Uani 1 1 d . . .
O8 O 0.45556(16) 0.37135(15) 0.30026(10) 0.0261(4) Uani 1 1 d . . .
O9 O 0.52914(18) 0.13461(18) 0.29525(11) 0.0322(4) Uani 1 1 d . . .
O10 O 0.37045(18) 0.16885(16) 0.35312(10) 0.0281(4) Uani 1 1 d . . .
H11 H 0.088(3) 0.380(2) 0.2321(17) 0.018(7) Uiso 1 1 d . . .
H12 H 0.210(3) 0.208(3) 0.2139(18) 0.021(7) Uiso 1 1 d . . .
H10 H -0.114(3) 0.296(3) 0.1085(18) 0.029(8) Uiso 1 1 d . . .
H4 H 0.461(3) 0.524(2) 0.1397(15) 0.011(6) Uiso 1 1 d . . .
H5 H 0.622(3) 0.500(3) 0.2541(18) 0.026(8) Uiso 1 1 d . . .
H6 H 0.845(3) 0.679(3) 0.276(2) 0.037(9) Uiso 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
C1 N3 1.490(3) . ?
C1 C3 1.531(4) . ?
C1 C2 1.533(3) . ?
C1 C4 1.540(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 O1 1.224(3) . ?
C4 N4 1.342(3) . ?
C5 N4 1.478(3) . ?
C5 C6 1.526(3) . ?
C5 C7 1.528(4) . ?
C5 C8 1.543(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 O2 1.225(3) . ?
C8 N5 1.341(3) . ?
C9 N5 1.468(3) . ?
C9 C10 1.521(3) . ?
C9 C11 1.536(3) . ?
C9 C12 1.542(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O3 1.228(3) . ?
C12 N6 1.348(3) . ?
C13 N6 1.463(3) . ?
C13 C14 1.531(4) . ?
C13 C15 1.533(4) . ?
C13 C16 1.535(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 O4 1.202(3) . ?
C16 O5 1.342(3) . ?
C17 O5 1.470(3) . ?
C17 C19 1.501(5) . ?
C17 C18 1.520(4) . ?
C17 C20 1.522(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 N9 1.491(3) . ?
C21 C23 1.529(4) . ?
C21 C22 1.531(4) . ?
C21 C24 1.537(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 O6 1.229(3) . ?
C24 N10 1.349(3) . ?
C25 N10 1.467(3) . ?
C25 C26 1.526(3) . ?
C25 C27 1.535(3) . ?
C25 C28 1.546(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 O7 1.225(3) . ?
C28 N11 1.350(3) . ?
C29 N11 1.468(3) . ?
C29 C31 1.521(3) . ?
C29 C30 1.537(3) . ?
C29 C32 1.549(3) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 O8 1.223(3) . ?
C32 N12 1.344(3) . ?
C33 N12 1.465(3) . ?
C33 C35 1.520(4) . ?
C33 C34 1.532(4) . ?
C33 C36 1.546(3) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 O9 1.199(3) . ?
C36 O10 1.338(3) . ?
C37 O10 1.488(3) . ?
C37 C39 1.509(5) . ?
C37 C40 1.512(4) . ?
C37 C38 1.518(4) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
N1 N2 1.134(3) . ?
N2 N3 1.227(3) . ?
N4 H4 0.84(3) . ?
N5 H5 0.82(3) . ?
N6 H6 0.86(4) . ?
N7 N8 1.137(4) . ?
N8 N9 1.230(3) . ?
N10 H10 0.85(3) . ?
N11 H11 0.81(3) . ?
N12 H12 0.78(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C1 C3 108.0(2) . . ?
N3 C1 C2 112.6(2) . . ?
C3 C1 C2 110.3(2) . . ?
N3 C1 C4 109.1(2) . . ?
C3 C1 C4 109.6(2) . . ?
C2 C1 C4 107.4(2) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C4 N4 123.6(2) . . ?
O1 C4 C1 118.3(2) . . ?
N4 C4 C1 118.2(2) . . ?
N4 C5 C6 110.6(2) . . ?
N4 C5 C7 107.5(2) . . ?
C6 C5 C7 110.3(2) . . ?
N4 C5 C8 112.41(19) . . ?
C6 C5 C8 108.3(2) . . ?
C7 C5 C8 107.7(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 N5 122.6(2) . . ?
O2 C8 C5 119.5(2) . . ?
N5 C8 C5 117.9(2) . . ?
N5 C9 C10 111.5(2) . . ?
N5 C9 C11 107.14(19) . . ?
C10 C9 C11 110.7(2) . . ?
N5 C9 C12 109.69(19) . . ?
C10 C9 C12 111.0(2) . . ?
C11 C9 C12 106.6(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 N6 122.5(2) . . ?
O3 C12 C9 121.0(2) . . ?
N6 C12 C9 116.2(2) . . ?
N6 C13 C14 111.9(2) . . ?
N6 C13 C15 108.0(2) . . ?
C14 C13 C15 109.7(2) . . ?
N6 C13 C16 110.1(2) . . ?
C14 C13 C16 109.2(2) . . ?
C15 C13 C16 107.8(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 O5 126.3(2) . . ?
O4 C16 C13 122.9(2) . . ?
O5 C16 C13 110.5(2) . . ?
O5 C17 C19 108.2(3) . . ?
O5 C17 C18 102.4(2) . . ?
C19 C17 C18 111.7(3) . . ?
O5 C17 C20 110.7(2) . . ?
C19 C17 C20 113.1(3) . . ?
C18 C17 C20 110.2(3) . . ?
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 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N9 C21 C23 106.0(2) . . ?
N9 C21 C22 112.1(2) . . ?
C23 C21 C22 111.3(2) . . ?
N9 C21 C24 110.8(2) . . ?
C23 C21 C24 108.6(2) . . ?
C22 C21 C24 108.0(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O6 C24 N10 123.1(2) . . ?
O6 C24 C21 118.7(2) . . ?
N10 C24 C21 118.3(2) . . ?
N10 C25 C26 108.49(19) . . ?
N10 C25 C27 110.0(2) . . ?
C26 C25 C27 109.9(2) . . ?
N10 C25 C28 111.21(18) . . ?
C26 C25 C28 107.78(19) . . ?
C27 C25 C28 109.45(19) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O7 C28 N11 123.0(2) . . ?
O7 C28 C25 120.4(2) . . ?
N11 C28 C25 116.6(2) . . ?
N11 C29 C31 111.01(19) . . ?
N11 C29 C30 107.2(2) . . ?
C31 C29 C30 110.6(2) . . ?
N11 C29 C32 110.39(19) . . ?
C31 C29 C32 110.6(2) . . ?
C30 C29 C32 106.86(19) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O8 C32 N12 122.8(2) . . ?
O8 C32 C29 121.0(2) . . ?
N12 C32 C29 115.9(2) . . ?
N12 C33 C35 111.7(2) . . ?
N12 C33 C34 107.5(2) . . ?
C35 C33 C34 110.4(2) . . ?
N12 C33 C36 110.3(2) . . ?
C35 C33 C36 108.6(2) . . ?
C34 C33 C36 108.2(2) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
O9 C36 O10 126.0(2) . . ?
O9 C36 C33 123.1(2) . . ?
O10 C36 C33 110.8(2) . . ?
O10 C37 C39 108.9(2) . . ?
O10 C37 C40 101.6(2) . . ?
C39 C37 C40 110.4(3) . . ?
O10 C37 C38 111.1(2) . . ?
C39 C37 C38 114.2(3) . . ?
C40 C37 C38 109.9(3) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C37 C39 H39A 109.5 . . ?
C37 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C37 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C37 C40 H40A 109.5 . . ?
C37 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C37 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
N1 N2 N3 172.9(3) . . ?
N2 N3 C1 117.0(2) . . ?
C4 N4 C5 122.4(2) . . ?
C4 N4 H4 121.4(18) . . ?
C5 N4 H4 116.1(18) . . ?
C8 N5 C9 121.7(2) . . ?
C8 N5 H5 119(2) . . ?
C9 N5 H5 118(2) . . ?
C12 N6 C13 122.6(2) . . ?
C12 N6 H6 120(2) . . ?
C13 N6 H6 117(2) . . ?
N7 N8 N9 172.0(3) . . ?
N8 N9 C21 116.1(2) . . ?
C24 N10 C25 121.9(2) . . ?
C24 N10 H10 120(2) . . ?
C25 N10 H10 118(2) . . ?
C28 N11 C29 122.2(2) . . ?
C28 N11 H11 117(2) . . ?
C29 N11 H11 120(2) . . ?
C32 N12 C33 122.4(2) . . ?
C32 N12 H12 121(2) . . ?
C33 N12 H12 116(2) . . ?
C16 O5 C17 121.4(2) . . ?
C36 O10 C37 119.0(2) . . ?

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
N3 C1 C4 O1 178.5(2) . . . . ?
C3 C1 C4 O1 -63.5(3) . . . . ?
C2 C1 C4 O1 56.2(3) . . . . ?
N3 C1 C4 N4 -0.9(3) . . . . ?
C3 C1 C4 N4 117.0(3) . . . . ?
C2 C1 C4 N4 -123.2(2) . . . . ?
N4 C5 C8 O2 -156.4(2) . . . . ?
C6 C5 C8 O2 -33.8(3) . . . . ?
C7 C5 C8 O2 85.5(3) . . . . ?
N4 C5 C8 N5 23.6(3) . . . . ?
C6 C5 C8 N5 146.1(2) . . . . ?
C7 C5 C8 N5 -94.6(3) . . . . ?
N5 C9 C12 O3 -149.1(2) . . . . ?
C10 C9 C12 O3 -25.4(3) . . . . ?
C11 C9 C12 O3 95.2(3) . . . . ?
N5 C9 C12 N6 37.1(3) . . . . ?
C10 C9 C12 N6 160.8(2) . . . . ?
C11 C9 C12 N6 -78.6(3) . . . . ?
N6 C13 C16 O4 141.5(3) . . . . ?
C14 C13 C16 O4 18.3(4) . . . . ?
C15 C13 C16 O4 -100.9(3) . . . . ?
N6 C13 C16 O5 -44.4(3) . . . . ?
C14 C13 C16 O5 -167.6(2) . . . . ?
C15 C13 C16 O5 73.2(3) . . . . ?
N9 C21 C24 O6 -176.0(2) . . . . ?
C23 C21 C24 O6 67.9(3) . . . . ?
C22 C21 C24 O6 -52.9(3) . . . . ?
N9 C21 C24 N10 4.8(3) . . . . ?
C23 C21 C24 N10 -111.3(3) . . . . ?
C22 C21 C24 N10 127.9(2) . . . . ?
N10 C25 C28 O7 153.3(2) . . . . ?
C26 C25 C28 O7 -87.9(3) . . . . ?
C27 C25 C28 O7 31.5(3) . . . . ?
N10 C25 C28 N11 -28.3(3) . . . . ?
C26 C25 C28 N11 90.5(2) . . . . ?
C27 C25 C28 N11 -150.0(2) . . . . ?
N11 C29 C32 O8 147.2(2) . . . . ?
C31 C29 C32 O8 24.0(3) . . . . ?
C30 C29 C32 O8 -96.5(3) . . . . ?
N11 C29 C32 N12 -39.3(3) . . . . ?
C31 C29 C32 N12 -162.5(2) . . . . ?
C30 C29 C32 N12 77.0(3) . . . . ?
N12 C33 C36 O9 -140.3(3) . . . . ?
C35 C33 C36 O9 -17.6(3) . . . . ?
C34 C33 C36 O9 102.3(3) . . . . ?
N12 C33 C36 O10 44.4(3) . . . . ?
C35 C33 C36 O10 167.1(2) . . . . ?
C34 C33 C36 O10 -73.0(3) . . . . ?
N1 N2 N3 C1 -173(2) . . . . ?
C3 C1 N3 N2 116.0(3) . . . . ?
C2 C1 N3 N2 -6.0(3) . . . . ?
C4 C1 N3 N2 -125.1(2) . . . . ?
O1 C4 N4 C5 -10.5(4) . . . . ?
C1 C4 N4 C5 168.9(2) . . . . ?
C6 C5 N4 C4 -58.9(3) . . . . ?
C7 C5 N4 C4 -179.4(2) . . . . ?
C8 C5 N4 C4 62.3(3) . . . . ?
O2 C8 N5 C9 2.9(4) . . . . ?
C5 C8 N5 C9 -177.1(2) . . . . ?
C10 C9 N5 C8 -69.0(3) . . . . ?
C11 C9 N5 C8 169.8(2) . . . . ?
C12 C9 N5 C8 54.4(3) . . . . ?
O3 C12 N6 C13 -2.2(4) . . . . ?
C9 C12 N6 C13 171.5(2) . . . . ?
C14 C13 N6 C12 73.4(3) . . . . ?
C15 C13 N6 C12 -165.7(2) . . . . ?
C16 C13 N6 C12 -48.3(3) . . . . ?
N7 N8 N9 C21 175(2) . . . . ?
C23 C21 N9 N8 -154.4(2) . . . . ?
C22 C21 N9 N8 -32.8(3) . . . . ?
C24 C21 N9 N8 87.9(3) . . . . ?
O6 C24 N10 C25 8.0(4) . . . . ?
C21 C24 N10 C25 -172.9(2) . . . . ?
C26 C25 N10 C24 -178.3(2) . . . . ?
C27 C25 N10 C24 61.5(3) . . . . ?
C28 C25 N10 C24 -59.9(3) . . . . ?
O7 C28 N11 C29 -2.2(4) . . . . ?
C25 C28 N11 C29 179.4(2) . . . . ?
C31 C29 N11 C28 69.9(3) . . . . ?
C30 C29 N11 C28 -169.1(2) . . . . ?
C32 C29 N11 C28 -53.1(3) . . . . ?
O8 C32 N12 C33 -1.5(4) . . . . ?
C29 C32 N12 C33 -174.8(2) . . . . ?
C35 C33 N12 C32 -71.8(3) . . . . ?
C34 C33 N12 C32 166.9(2) . . . . ?
C36 C33 N12 C32 49.1(3) . . . . ?
O4 C16 O5 C17 -5.8(4) . . . . ?
C13 C16 O5 C17 -179.6(2) . . . . ?
C19 C17 O5 C16 -60.9(3) . . . . ?
C18 C17 O5 C16 -179.0(2) . . . . ?
C20 C17 O5 C16 63.6(3) . . . . ?
O9 C36 O10 C37 10.9(4) . . . . ?
C33 C36 O10 C37 -173.9(2) . . . . ?
C39 C37 O10 C36 63.8(3) . . . . ?
C40 C37 O10 C36 -179.6(2) . . . . ?
C38 C37 O10 C36 -62.8(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
N6 H6 O1 0.86(4) 2.15(4) 2.987(3) 164(3) .
N5 H5 O8 0.82(3) 2.61(3) 3.212(3) 132(3) .
N4 H4 O7 0.84(3) 2.31(3) 3.107(3) 157(2) .
N10 H10 O2 0.85(3) 2.29(3) 3.054(3) 149(3) 1_455
N12 H12 O6 0.78(3) 2.25(3) 2.996(3) 162(3) .

_diffrn_measured_fraction_theta_max 0.941
_diffrn_reflns_theta_full        66.60
_diffrn_measured_fraction_theta_full 0.957
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.072
_database_code_depnum_ccdc_archive 'CCDC 984589'
#######################################################################
#
#                 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_s3792ma
#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------# 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H30 N6 O5'
_chemical_formula_weight         398.47

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   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   13.6156(4)
_cell_length_b                   10.7583(3)
_cell_length_c                   15.9339(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.8690(10)
_cell_angle_gamma                90.00
_cell_volume                     2117.58(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8261
_cell_measurement_theta_min      4.11
_cell_measurement_theta_max      72.14

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7305
_exptl_absorpt_correction_T_max  0.9195
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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_reflns_number            11781
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.12
_diffrn_reflns_theta_max         72.23
_reflns_number_total             4094
_reflns_number_gt                3853
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0501P)²+0.7610P] 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_number_reflns         4094
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0995
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 1.04464(9) 0.09718(12) 0.16801(8) 0.0222(3) Uani 1 1 d . . .
C2 C 1.14830(10) 0.11892(13) 0.15477(9) 0.0300(3) Uani 1 1 d . . .
H2A H 1.2103 0.1232 0.2153 0.045 Uiso 1 1 calc R . .
H2B H 1.1423 0.1972 0.1215 0.045 Uiso 1 1 calc R . .
H2C H 1.1587 0.0502 0.1189 0.045 Uiso 1 1 calc R . .
C3 C 0.94542(10) 0.08614(15) 0.07527(9) 0.0331(3) Uani 1 1 d . . .
H3A H 0.9507 0.0097 0.0439 0.050 Uiso 1 1 calc R . .
H3B H 0.9424 0.1581 0.0365 0.050 Uiso 1 1 calc R . .
H3C H 0.8797 0.0835 0.0860 0.050 Uiso 1 1 calc R . .
C4 C 1.02959(9) 0.20895(11) 0.22083(8) 0.0204(2) Uani 1 1 d . . .
C5 C 1.04718(9) 0.29716(10) 0.36842(7) 0.0187(2) Uani 1 1 d . . .
C6 C 1.03897(10) 0.24575(12) 0.45477(8) 0.0249(3) Uani 1 1 d . . .
H6A H 0.9702 0.2013 0.4367 0.037 Uiso 1 1 calc R . .
H6B H 1.0422 0.3145 0.4962 0.037 Uiso 1 1 calc R . .
H6C H 1.0992 0.1885 0.4868 0.037 Uiso 1 1 calc R . .
C7 C 1.15527(9) 0.36364(13) 0.39462(10) 0.0307(3) Uani 1 1 d . . .
H7A H 1.2147 0.3042 0.4232 0.046 Uiso 1 1 calc R . .
H7B H 1.1623 0.4306 0.4385 0.046 Uiso 1 1 calc R . .
H7C H 1.1581 0.3987 0.3389 0.046 Uiso 1 1 calc R . .
C8 C 0.95363(9) 0.38996(10) 0.32073(7) 0.0164(2) Uani 1 1 d . . .
C9 C 0.75724(8) 0.42096(10) 0.24326(7) 0.0161(2) Uani 1 1 d . . .
C10 C 0.65757(9) 0.33851(12) 0.19459(8) 0.0229(2) Uani 1 1 d . . .
H10A H 0.6675 0.2874 0.1479 0.034 Uiso 1 1 calc R . .
H10B H 0.5933 0.3909 0.1646 0.034 Uiso 1 1 calc R . .
H10C H 0.6481 0.2845 0.2401 0.034 Uiso 1 1 calc R . .
C11 C 0.74608(10) 0.49396(12) 0.32122(8) 0.0240(3) Uani 1 1 d . . .
H11A H 0.7404 0.4358 0.3663 0.036 Uiso 1 1 calc R . .
H11B H 0.6809 0.5457 0.2955 0.036 Uiso 1 1 calc R . .
H11C H 0.8098 0.5471 0.3518 0.036 Uiso 1 1 calc R . .
C12 C 0.76169(8) 0.51041(10) 0.16931(7) 0.0157(2) Uani 1 1 d . . .
C13 C 0.82360(9) 0.54508(11) 0.04723(7) 0.0189(2) Uani 1 1 d . . .
C14 C 0.91201(10) 0.64138(12) 0.09568(9) 0.0263(3) Uani 1 1 d . . .
H14A H 0.8882 0.6981 0.1316 0.040 Uiso 1 1 calc R . .
H14B H 0.9260 0.6887 0.0493 0.040 Uiso 1 1 calc R . .
H14C H 0.9785 0.5990 0.1372 0.040 Uiso 1 1 calc R . .
C15 C 0.85542(11) 0.46106(12) -0.01524(9) 0.0265(3) Uani 1 1 d . . .
H15A H 0.9227 0.4171 0.0224 0.040 Uiso 1 1 calc R . .
H15B H 0.8662 0.5119 -0.0617 0.040 Uiso 1 1 calc R . .
H15C H 0.7977 0.4005 -0.0463 0.040 Uiso 1 1 calc R . .
C16 C 0.71370(9) 0.60167(10) -0.01599(7) 0.0180(2) Uani 1 1 d . . .
C17 C 0.62461(11) 0.78243(13) -0.09610(11) 0.0344(3) Uani 1 1 d . . .
H17A H 0.5781 0.7226 -0.1420 0.052 Uiso 1 1 calc R . .
H17B H 0.6430 0.8507 -0.1277 0.052 Uiso 1 1 calc R . .
H17C H 0.5863 0.8156 -0.0609 0.052 Uiso 1 1 calc R . .
N1 N 1.13584(13) -0.19203(14) 0.19223(13) 0.0569(4) Uani 1 1 d . . .
N2 N 1.09785(9) -0.10497(11) 0.20594(9) 0.0339(3) Uani 1 1 d . . .
N3 N 1.05259(10) -0.01667(10) 0.22404(8) 0.0322(3) Uani 1 1 d . . .
N4 N 1.03959(7) 0.19116(9) 0.30732(6) 0.0181(2) Uani 1 1 d . . .
N5 N 0.85320(7) 0.34047(9) 0.27927(6) 0.01495(19) Uani 1 1 d . . .
N6 N 0.80809(8) 0.46606(9) 0.11569(6) 0.0178(2) Uani 1 1 d . . .
O1 O 1.01035(7) 0.31068(9) 0.18229(6) 0.0286(2) Uani 1 1 d . . .
O2 O 0.97008(6) 0.50194(8) 0.32321(6) 0.02347(19) Uani 1 1 d . . .
O3 O 0.71634(6) 0.61207(7) 0.15521(5) 0.02027(18) Uani 1 1 d . . .
O4 O 0.63144(7) 0.54245(8) -0.05107(6) 0.0264(2) Uani 1 1 d . . .
O5 O 0.72289(7) 0.72101(8) -0.03364(6) 0.0266(2) Uani 1 1 d . . .
H4 H 1.0544(12) 0.1200(16) 0.3314(10) 0.023(4) Uiso 1 1 d . . .
H5 H 0.8432(12) 0.2657(16) 0.2890(10) 0.021(3) Uiso 1 1 d . . .
H6 H 0.8497(13) 0.4062(15) 0.1345(11) 0.024(4) Uiso 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
C1 N3 1.4926(16) . ?
C1 C4 1.5301(16) . ?
C1 C2 1.5302(16) . ?
C1 C3 1.5310(16) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 O1 1.2282(15) . ?
C4 N4 1.3404(15) . ?
C5 N4 1.4746(14) . ?
C5 C7 1.5280(16) . ?
C5 C6 1.5300(16) . ?
C5 C8 1.5435(15) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 O2 1.2229(14) . ?
C8 N5 1.3528(14) . ?
C9 N5 1.4682(13) . ?
C9 C11 1.5302(15) . ?
C9 C10 1.5313(15) . ?
C9 C12 1.5422(14) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O3 1.2293(14) . ?
C12 N6 1.3457(14) . ?
C13 N6 1.4666(14) . ?
C13 C14 1.5286(16) . ?
C13 C16 1.5351(15) . ?
C13 C15 1.5357(16) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 O4 1.2026(14) . ?
C16 O5 1.3314(14) . ?
C17 O5 1.4483(15) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N1 N2 1.1348(19) . ?
N2 N3 1.2308(17) . ?
N4 H4 0.842(17) . ?
N5 H5 0.841(17) . ?
N6 H6 0.827(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C1 C4 107.98(9) . . ?
N3 C1 C2 111.64(10) . . ?
C4 C1 C2 107.48(10) . . ?
N3 C1 C3 109.04(11) . . ?
C4 C1 C3 108.90(10) . . ?
C2 C1 C3 111.68(10) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C4 N4 123.33(11) . . ?
O1 C4 C1 118.36(10) . . ?
N4 C4 C1 118.30(10) . . ?
N4 C5 C7 109.54(9) . . ?
N4 C5 C6 107.62(9) . . ?
C7 C5 C6 110.47(10) . . ?
N4 C5 C8 111.16(8) . . ?
C7 C5 C8 109.41(9) . . ?
C6 C5 C8 108.62(9) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 N5 122.50(10) . . ?
O2 C8 C5 121.28(10) . . ?
N5 C8 C5 116.18(9) . . ?
N5 C9 C11 111.18(9) . . ?
N5 C9 C10 108.04(9) . . ?
C11 C9 C10 109.82(9) . . ?
N5 C9 C12 110.62(8) . . ?
C11 C9 C12 110.45(9) . . ?
C10 C9 C12 106.60(8) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 N6 122.22(10) . . ?
O3 C12 C9 121.11(9) . . ?
N6 C12 C9 116.35(9) . . ?
N6 C13 C14 110.26(9) . . ?
N6 C13 C16 108.21(9) . . ?
C14 C13 C16 113.95(10) . . ?
N6 C13 C15 108.00(9) . . ?
C14 C13 C15 110.45(10) . . ?
C16 C13 C15 105.72(9) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 O5 124.38(10) . . ?
O4 C16 C13 123.72(10) . . ?
O5 C16 C13 111.64(9) . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 N2 N3 174.80(16) . . ?
N2 N3 C1 114.25(11) . . ?
C4 N4 C5 121.13(10) . . ?
C4 N4 H4 120.0(10) . . ?
C5 N4 H4 117.7(10) . . ?
C8 N5 C9 120.62(9) . . ?
C8 N5 H5 119.7(10) . . ?
C9 N5 H5 116.7(10) . . ?
C12 N6 C13 121.31(9) . . ?
C12 N6 H6 118.6(11) . . ?
C13 N6 H6 115.5(11) . . ?
C16 O5 C17 116.32(10) . . ?

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
N3 C1 C4 O1 -172.76(11) . . . . ?
C2 C1 C4 O1 66.66(14) . . . . ?
C3 C1 C4 O1 -54.50(14) . . . . ?
N3 C1 C4 N4 8.15(14) . . . . ?
C2 C1 C4 N4 -112.43(12) . . . . ?
C3 C1 C4 N4 126.42(11) . . . . ?
N4 C5 C8 O2 -134.32(11) . . . . ?
C7 C5 C8 O2 -13.21(15) . . . . ?
C6 C5 C8 O2 107.46(12) . . . . ?
N4 C5 C8 N5 47.82(12) . . . . ?
C7 C5 C8 N5 168.93(10) . . . . ?
C6 C5 C8 N5 -70.41(12) . . . . ?
N5 C9 C12 O3 -152.41(10) . . . . ?
C11 C9 C12 O3 -28.89(14) . . . . ?
C10 C9 C12 O3 90.36(12) . . . . ?
N5 C9 C12 N6 33.98(12) . . . . ?
C11 C9 C12 N6 157.50(9) . . . . ?
C10 C9 C12 N6 -83.24(11) . . . . ?
N6 C13 C16 O4 -47.66(14) . . . . ?
C14 C13 C16 O4 -170.69(11) . . . . ?
C15 C13 C16 O4 67.83(13) . . . . ?
N6 C13 C16 O5 138.04(9) . . . . ?
C14 C13 C16 O5 15.02(13) . . . . ?
C15 C13 C16 O5 -106.46(11) . . . . ?
N1 N2 N3 C1 -159.7(18) . . . . ?
C4 C1 N3 N2 -158.11(11) . . . . ?
C2 C1 N3 N2 -40.17(15) . . . . ?
C3 C1 N3 N2 83.71(14) . . . . ?
O1 C4 N4 C5 -10.97(17) . . . . ?
C1 C4 N4 C5 168.06(9) . . . . ?
C7 C5 N4 C4 -69.00(13) . . . . ?
C6 C5 N4 C4 170.87(10) . . . . ?
C8 C5 N4 C4 52.04(13) . . . . ?
O2 C8 N5 C9 -6.41(16) . . . . ?
C5 C8 N5 C9 171.43(9) . . . . ?
C11 C9 N5 C8 -63.55(12) . . . . ?
C10 C9 N5 C8 175.88(9) . . . . ?
C12 C9 N5 C8 59.54(12) . . . . ?
O3 C12 N6 C13 10.63(16) . . . . ?
C9 C12 N6 C13 -175.84(9) . . . . ?
C14 C13 N6 C12 71.03(13) . . . . ?
C16 C13 N6 C12 -54.21(13) . . . . ?
C15 C13 N6 C12 -168.21(10) . . . . ?
O4 C16 O5 C17 3.12(17) . . . . ?
C13 C16 O5 C17 177.37(10) . . . . ?

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
N4 H4 O4 0.842(17) 2.451(17) 3.2555(13) 160.1(14) 4_666
N5 H5 O3 0.841(17) 2.187(16) 2.9758(12) 156.1(14) 2_645
N6 H6 O1 0.827(17) 2.240(17) 3.0077(13) 154.6(14) .

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        66.60
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.059
_database_code_depnum_ccdc_archive 'CCDC 984590'
#######################################################################
#
#                 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_s3888ma
#------------------  SECTION 2. COMPOUND(S) DETAILS -------------------------# 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H39 N7 O7'
_chemical_formula_weight         501.59

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                   11.3347(4)
_cell_length_b                   16.1397(5)
_cell_length_c                   16.8748(6)
_cell_angle_alpha                62.527(2)
_cell_angle_beta                 85.251(2)
_cell_angle_gamma                81.446(2)
_cell_volume                     2708.10(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6803
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      70.28

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.747956
_exptl_absorpt_correction_T_max  0.8925
_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_reflns_number            16634
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         70.27
_reflns_number_total             9674
_reflns_number_gt                8118
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0676P)²+1.0044P] 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_number_reflns         9674
_refine_ls_number_parameters     697
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1245
_refine_ls_wR_factor_gt          0.1158
_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 0.77867(15) 0.09064(13) 0.33372(12) 0.0235(4) Uani 1 1 d . . .
C2 C 0.7663(2) -0.00917(15) 0.35258(18) 0.0430(5) Uani 1 1 d . . .
H2A H 0.7917 -0.0179 0.2997 0.065 Uiso 1 1 calc R . .
H2B H 0.6827 -0.0203 0.3671 0.065 Uiso 1 1 calc R . .
H2C H 0.8164 -0.0538 0.4031 0.065 Uiso 1 1 calc R . .
C3 C 0.73736(17) 0.10781(16) 0.41424(12) 0.0327(4) Uani 1 1 d . . .
H3A H 0.7861 0.0640 0.4660 0.049 Uiso 1 1 calc R . .
H3B H 0.6534 0.0977 0.4280 0.049 Uiso 1 1 calc R . .
H3C H 0.7462 0.1727 0.4003 0.049 Uiso 1 1 calc R . .
C4 C 0.70013(14) 0.16107(12) 0.25517(11) 0.0169(3) Uani 1 1 d . . .
C5 C 0.68114(14) 0.29919(12) 0.10913(11) 0.0189(3) Uani 1 1 d . . .
C6 C 0.75980(16) 0.37529(14) 0.05010(12) 0.0270(4) Uani 1 1 d . . .
H6A H 0.7905 0.4007 0.0859 0.040 Uiso 1 1 calc R . .
H6B H 0.7125 0.4260 0.0011 0.040 Uiso 1 1 calc R . .
H6C H 0.8267 0.3478 0.0256 0.040 Uiso 1 1 calc R . .
C7 C 0.63462(17) 0.25650(15) 0.05590(12) 0.0273(4) Uani 1 1 d . . .
H7A H 0.7020 0.2265 0.0342 0.041 Uiso 1 1 calc R . .
H7B H 0.5892 0.3062 0.0050 0.041 Uiso 1 1 calc R . .
H7C H 0.5827 0.2094 0.0943 0.041 Uiso 1 1 calc R . .
C8 C 0.57632(14) 0.34749(11) 0.14322(11) 0.0162(3) Uani 1 1 d . . .
C9 C 0.51377(15) 0.41851(12) 0.24328(12) 0.0197(3) Uani 1 1 d . . .
C10 C 0.55689(16) 0.40682(15) 0.33168(14) 0.0281(4) Uani 1 1 d . . .
H10A H 0.5695 0.3398 0.3741 0.042 Uiso 1 1 calc R . .
H10B H 0.4967 0.4395 0.3561 0.042 Uiso 1 1 calc R . .
H10C H 0.6321 0.4337 0.3216 0.042 Uiso 1 1 calc R . .
C11 C 0.50449(18) 0.52133(13) 0.17202(15) 0.0319(4) Uani 1 1 d . . .
H11A H 0.5810 0.5452 0.1663 0.048 Uiso 1 1 calc R . .
H11B H 0.4419 0.5589 0.1895 0.048 Uiso 1 1 calc R . .
H11C H 0.4847 0.5257 0.1146 0.048 Uiso 1 1 calc R . .
C12 C 0.39071(14) 0.38233(12) 0.26487(11) 0.0166(3) Uani 1 1 d . . .
C13 C 0.28563(14) 0.23988(11) 0.32565(11) 0.0158(3) Uani 1 1 d . . .
C14 C 0.32833(15) 0.13550(12) 0.35348(12) 0.0212(3) Uani 1 1 d . . .
H14A H 0.3687 0.1289 0.3027 0.032 Uiso 1 1 calc R . .
H14B H 0.2596 0.1000 0.3725 0.032 Uiso 1 1 calc R . .
H14C H 0.3840 0.1109 0.4030 0.032 Uiso 1 1 calc R . .
C15 C 0.22477(15) 0.25049(12) 0.40519(11) 0.0206(3) Uani 1 1 d . . .
H15A H 0.2798 0.2225 0.4554 0.031 Uiso 1 1 calc R . .
H15B H 0.1531 0.2184 0.4228 0.031 Uiso 1 1 calc R . .
H15C H 0.2023 0.3174 0.3885 0.031 Uiso 1 1 calc R . .
C16 C 0.19729(14) 0.27209(11) 0.24947(11) 0.0156(3) Uani 1 1 d . . .
C17 C 0.17661(15) 0.31638(13) 0.09133(11) 0.0206(3) Uani 1 1 d . . .
C18 C 0.08634(16) 0.40405(13) 0.06407(12) 0.0233(4) Uani 1 1 d . . .
H18A H 0.0269 0.3944 0.1122 0.035 Uiso 1 1 calc R . .
H18B H 0.0465 0.4165 0.0096 0.035 Uiso 1 1 calc R . .
H18C H 0.1274 0.4579 0.0528 0.035 Uiso 1 1 calc R . .
C19 C 0.26494(17) 0.32554(17) 0.01453(13) 0.0320(4) Uani 1 1 d . . .
H19A H 0.3026 0.3830 -0.0056 0.048 Uiso 1 1 calc R . .
H19B H 0.2222 0.3287 -0.0352 0.048 Uiso 1 1 calc R . .
H19C H 0.3264 0.2708 0.0354 0.048 Uiso 1 1 calc R . .
C20 C 0.11235(15) 0.23064(13) 0.11297(13) 0.0236(4) Uani 1 1 d . . .
C21 C 0.1343(2) 0.06649(18) 0.1663(2) 0.0565(8) Uani 1 1 d . . .
H21A H 0.0618 0.0589 0.2037 0.085 Uiso 1 1 calc R . .
H21B H 0.1932 0.0109 0.1952 0.085 Uiso 1 1 calc R . .
H21C H 0.1147 0.0736 0.1078 0.085 Uiso 1 1 calc R . .
C22 C 1.13211(15) 0.78085(13) 0.38985(11) 0.0206(3) Uani 1 1 d . . .
C23 C 1.0735(2) 0.8416(2) 0.43267(17) 0.0446(6) Uani 1 1 d . . .
H23A H 1.1171 0.8267 0.4863 0.067 Uiso 1 1 calc R . .
H23B H 0.9906 0.8291 0.4491 0.067 Uiso 1 1 calc R . .
H23C H 1.0748 0.9081 0.3902 0.067 Uiso 1 1 calc R . .
C24 C 1.1413(3) 0.67712(17) 0.45603(15) 0.0482(6) Uani 1 1 d . . .
H24A H 1.1834 0.6398 0.4278 0.072 Uiso 1 1 calc R . .
H24B H 1.0610 0.6589 0.4747 0.072 Uiso 1 1 calc R . .
H24C H 1.1854 0.6657 0.5084 0.072 Uiso 1 1 calc R . .
C25 C 1.05707(15) 0.79668(11) 0.31177(11) 0.0171(3) Uani 1 1 d . . .
C26 C 1.04955(14) 0.82774(12) 0.15533(11) 0.0180(3) Uani 1 1 d . . .
C27 C 0.96055(17) 0.91727(13) 0.11974(12) 0.0253(4) Uani 1 1 d . . .
H27A H 0.9038 0.9155 0.1674 0.038 Uiso 1 1 calc R . .
H27B H 0.9173 0.9216 0.0698 0.038 Uiso 1 1 calc R . .
H27C H 1.0034 0.9722 0.0992 0.038 Uiso 1 1 calc R . .
C28 C 1.14302(16) 0.82957(14) 0.08376(11) 0.0254(4) Uani 1 1 d . . .
H28A H 1.1861 0.8842 0.0647 0.038 Uiso 1 1 calc R . .
H28B H 1.1033 0.8338 0.0324 0.038 Uiso 1 1 calc R . .
H28C H 1.1995 0.7718 0.1085 0.038 Uiso 1 1 calc R . .
C29 C 0.98261(14) 0.74211(12) 0.18034(10) 0.0160(3) Uani 1 1 d . . .
C30 C 0.98439(14) 0.57128(12) 0.26496(11) 0.0183(3) Uani 1 1 d . . .
C31 C 1.04571(15) 0.49369(12) 0.34960(13) 0.0238(4) Uani 1 1 d . . .
H31A H 1.1313 0.4838 0.3374 0.036 Uiso 1 1 calc R . .
H31B H 1.0113 0.4351 0.3680 0.036 Uiso 1 1 calc R . .
H31C H 1.0337 0.5125 0.3975 0.036 Uiso 1 1 calc R . .
C32 C 1.00699(16) 0.54647(14) 0.18733(13) 0.0259(4) Uani 1 1 d . . .
H32A H 0.9703 0.5983 0.1332 0.039 Uiso 1 1 calc R . .
H32B H 0.9720 0.4890 0.2019 0.039 Uiso 1 1 calc R . .
H32C H 1.0931 0.5362 0.1771 0.039 Uiso 1 1 calc R . .
C33 C 0.84999(14) 0.57909(12) 0.28965(11) 0.0170(3) Uani 1 1 d . . .
C34 C 0.69382(14) 0.64453(12) 0.36684(11) 0.0174(3) Uani 1 1 d . . .
C35 C 0.65701(15) 0.55051(13) 0.43684(12) 0.0229(4) Uani 1 1 d . . .
H35A H 0.6604 0.5074 0.4103 0.034 Uiso 1 1 calc R . .
H35B H 0.5754 0.5604 0.4579 0.034 Uiso 1 1 calc R . .
H35C H 0.7115 0.5233 0.4873 0.034 Uiso 1 1 calc R . .
C36 C 0.69781(15) 0.70933(13) 0.40983(12) 0.0226(4) Uani 1 1 d . . .
H36A H 0.7572 0.6806 0.4572 0.034 Uiso 1 1 calc R . .
H36B H 0.6192 0.7187 0.4354 0.034 Uiso 1 1 calc R . .
H36C H 0.7196 0.7702 0.3644 0.034 Uiso 1 1 calc R . .
C37 C 0.59998(14) 0.69668(12) 0.29270(11) 0.0188(3) Uani 1 1 d . . .
C38 C 0.56004(15) 0.82108(12) 0.14016(11) 0.0202(3) Uani 1 1 d . . .
C39 C 0.63700(16) 0.88790(13) 0.06550(12) 0.0264(4) Uani 1 1 d . . .
H39A H 0.6800 0.9199 0.0891 0.040 Uiso 1 1 calc R . .
H39B H 0.5857 0.9347 0.0167 0.040 Uiso 1 1 calc R . .
H39C H 0.6945 0.8517 0.0430 0.040 Uiso 1 1 calc R . .
C40 C 0.49060(16) 0.77184(13) 0.10485(12) 0.0234(4) Uani 1 1 d . . .
H40A H 0.5464 0.7316 0.0859 0.035 Uiso 1 1 calc R . .
H40B H 0.4432 0.8190 0.0538 0.035 Uiso 1 1 calc R . .
H40C H 0.4374 0.7332 0.1521 0.035 Uiso 1 1 calc R . .
C41 C 0.47272(15) 0.88201(13) 0.17240(12) 0.0218(4) Uani 1 1 d . . .
C42 C 0.4582(2) 0.98407(17) 0.23823(18) 0.0410(5) Uani 1 1 d . . .
H42A H 0.4520 1.0447 0.1843 0.062 Uiso 1 1 calc R . .
H42B H 0.4968 0.9895 0.2852 0.062 Uiso 1 1 calc R . .
H42C H 0.3782 0.9660 0.2586 0.062 Uiso 1 1 calc R . .
N1 N 1.04264(14) 0.07412(12) 0.41822(11) 0.0295(4) Uani 1 1 d . . .
N2 N 0.97210(13) 0.08987(10) 0.36798(10) 0.0217(3) Uani 1 1 d . . .
N3 N 0.90498(13) 0.10902(13) 0.30636(11) 0.0302(4) Uani 1 1 d . . .
N4 N 0.75189(12) 0.22652(10) 0.18471(9) 0.0172(3) Uani 1 1 d . . .
N5 N 0.59920(12) 0.36116(10) 0.21293(10) 0.0166(3) Uani 1 1 d . . .
N6 N 0.39197(12) 0.28922(10) 0.29519(9) 0.0149(3) Uani 1 1 d . . .
N7 N 0.24607(12) 0.29946(10) 0.16755(9) 0.0183(3) Uani 1 1 d . . .
N8 N 1.39987(16) 0.78977(19) 0.45141(13) 0.0496(6) Uani 1 1 d . . .
N9 N 1.32534(14) 0.79556(14) 0.40773(11) 0.0340(4) Uani 1 1 d . . .
N10 N 1.25184(14) 0.80766(15) 0.35262(11) 0.0356(4) Uani 1 1 d . . .
N11 N 1.11261(13) 0.81666(10) 0.23285(9) 0.0172(3) Uani 1 1 d . . .
N12 N 1.03323(12) 0.65898(10) 0.24204(9) 0.0156(3) Uani 1 1 d . . .
N13 N 0.81457(12) 0.63330(10) 0.33059(9) 0.0156(3) Uani 1 1 d . . .
N14 N 0.64044(13) 0.75422(11) 0.21183(10) 0.0199(3) Uani 1 1 d . . .
O1 O 0.59160(10) 0.15694(8) 0.26167(8) 0.0193(2) Uani 1 1 d . . .
O2 O 0.47971(10) 0.37417(9) 0.10574(8) 0.0204(2) Uani 1 1 d . . .
O3 O 0.29986(11) 0.43623(8) 0.26079(9) 0.0229(3) Uani 1 1 d . . .
O4 O 0.09057(10) 0.26307(8) 0.26506(8) 0.0203(2) Uani 1 1 d . . .
O5 O 0.01295(11) 0.23586(10) 0.08994(10) 0.0292(3) Uani 1 1 d . . .
O6 O 0.18336(12) 0.14957(10) 0.15472(12) 0.0376(4) Uani 1 1 d . . .
O7 O 0.95027(11) 0.78680(9) 0.32473(8) 0.0216(3) Uani 1 1 d . . .
O8 O 0.88935(10) 0.75155(9) 0.14289(8) 0.0195(2) Uani 1 1 d . . .
O9 O 0.78477(11) 0.53157(9) 0.27790(9) 0.0246(3) Uani 1 1 d . . .
O10 O 0.49282(11) 0.69176(10) 0.31095(8) 0.0250(3) Uani 1 1 d . . .
O11 O 0.36941(11) 0.90585(9) 0.15205(9) 0.0240(3) Uani 1 1 d . . .
O12 O 0.52833(12) 0.91325(11) 0.21849(11) 0.0367(4) Uani 1 1 d . . .
O13 O 0.84055(12) 0.33884(11) 0.28979(11) 0.0319(3) Uani 1 1 d . . .
H13A H 0.914(3) 0.319(2) 0.2849(19) 0.048 Uiso 1 1 d . . .
H13B H 0.840(3) 0.397(2) 0.2856(19) 0.048 Uiso 1 1 d . . .
O14 O 0.28509(12) 0.61015(11) 0.29680(11) 0.0342(3) Uani 1 1 d . . .
H14D H 0.344(3) 0.631(2) 0.301(2) 0.051 Uiso 1 1 d . . .
H14E H 0.303(3) 0.564(2) 0.284(2) 0.051 Uiso 1 1 d . . .
H4 H 0.827(2) 0.2249(16) 0.1827(15) 0.025(5) Uiso 1 1 d . . .
H5 H 0.665(2) 0.3465(15) 0.2316(14) 0.018(5) Uiso 1 1 d . . .
H6 H 0.453(2) 0.2589(16) 0.2913(15) 0.022(5) Uiso 1 1 d . . .
H7 H 0.321(2) 0.3109(16) 0.1564(15) 0.026(5) Uiso 1 1 d . . .
H11 H 1.187(2) 0.8204(16) 0.2284(15) 0.025(5) Uiso 1 1 d . . .
H12 H 1.101(2) 0.6532(14) 0.2586(14) 0.016(5) Uiso 1 1 d . . .
H13 H 0.8624(19) 0.6670(14) 0.3330(13) 0.013(5) Uiso 1 1 d . . .
H14 H 0.714(2) 0.7539(16) 0.1997(15) 0.025(5) Uiso 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
C1 N3 1.497(2) . ?
C1 C2 1.518(3) . ?
C1 C4 1.532(2) . ?
C1 C3 1.532(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 O1 1.235(2) . ?
C4 N4 1.336(2) . ?
C5 N4 1.468(2) . ?
C5 C7 1.522(2) . ?
C5 C6 1.531(2) . ?
C5 C8 1.541(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 O2 1.228(2) . ?
C8 N5 1.344(2) . ?
C9 N5 1.465(2) . ?
C9 C10 1.528(3) . ?
C9 C11 1.529(2) . ?
C9 C12 1.543(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O3 1.230(2) . ?
C12 N6 1.344(2) . ?
C13 N6 1.4685(19) . ?
C13 C15 1.527(2) . ?
C13 C14 1.536(2) . ?
C13 C16 1.539(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 O4 1.232(2) . ?
C16 N7 1.340(2) . ?
C17 N7 1.459(2) . ?
C17 C18 1.519(2) . ?
C17 C19 1.535(2) . ?
C17 C20 1.539(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 O5 1.201(2) . ?
C20 O6 1.337(2) . ?
C21 O6 1.452(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 N10 1.485(2) . ?
C22 C24 1.518(3) . ?
C22 C23 1.518(2) . ?
C22 C25 1.528(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 O7 1.233(2) . ?
C25 N11 1.341(2) . ?
C26 N11 1.468(2) . ?
C26 C27 1.527(2) . ?
C26 C28 1.532(2) . ?
C26 C29 1.544(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 O8 1.230(2) . ?
C29 N12 1.340(2) . ?
C30 N12 1.467(2) . ?
C30 C32 1.530(2) . ?
C30 C31 1.532(2) . ?
C30 C33 1.548(2) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 O9 1.228(2) . ?
C33 N13 1.346(2) . ?
C34 N13 1.4731(19) . ?
C34 C35 1.525(2) . ?
C34 C36 1.530(2) . ?
C34 C37 1.545(2) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 O10 1.233(2) . ?
C37 N14 1.337(2) . ?
C38 N14 1.464(2) . ?
C38 C40 1.519(2) . ?
C38 C39 1.535(2) . ?
C38 C41 1.535(2) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 O11 1.203(2) . ?
C41 O12 1.339(2) . ?
C42 O12 1.445(2) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
N1 N2 1.129(2) . ?
N2 N3 1.233(2) . ?
N4 H4 0.84(2) . ?
N5 H5 0.79(2) . ?
N6 H6 0.80(2) . ?
N7 H7 0.89(2) . ?
N8 N9 1.132(3) . ?
N9 N10 1.229(2) . ?
N11 H11 0.85(2) . ?
N12 H12 0.82(2) . ?
N13 H13 0.84(2) . ?
N14 H14 0.84(3) . ?
O13 H13A 0.86(3) . ?
O13 H13B 0.90(3) . ?
O14 H14D 0.82(3) . ?
O14 H14E 0.85(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C1 C2 109.16(16) . . ?
N3 C1 C4 106.97(14) . . ?
C2 C1 C4 109.99(16) . . ?
N3 C1 C3 112.33(16) . . ?
C2 C1 C3 111.16(18) . . ?
C4 C1 C3 107.12(15) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C4 N4 123.28(15) . . ?
O1 C4 C1 118.42(15) . . ?
N4 C4 C1 118.23(14) . . ?
N4 C5 C7 110.57(15) . . ?
N4 C5 C6 108.55(14) . . ?
C7 C5 C6 110.71(15) . . ?
N4 C5 C8 109.98(13) . . ?
C7 C5 C8 110.18(14) . . ?
C6 C5 C8 106.76(14) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 N5 123.18(15) . . ?
O2 C8 C5 120.73(15) . . ?
N5 C8 C5 116.05(14) . . ?
N5 C9 C10 108.34(14) . . ?
N5 C9 C11 109.27(14) . . ?
C10 C9 C11 111.33(15) . . ?
N5 C9 C12 111.23(13) . . ?
C10 C9 C12 105.31(13) . . ?
C11 C9 C12 111.29(15) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 N6 123.67(15) . . ?
O3 C12 C9 120.18(15) . . ?
N6 C12 C9 115.89(14) . . ?
N6 C13 C15 111.46(13) . . ?
N6 C13 C14 106.65(13) . . ?
C15 C13 C14 109.59(14) . . ?
N6 C13 C16 111.79(13) . . ?
C15 C13 C16 111.01(13) . . ?
C14 C13 C16 106.08(13) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 N7 122.69(15) . . ?
O4 C16 C13 121.19(14) . . ?
N7 C16 C13 115.65(13) . . ?
N7 C17 C18 111.65(14) . . ?
N7 C17 C19 107.39(14) . . ?
C18 C17 C19 111.02(15) . . ?
N7 C17 C20 110.31(15) . . ?
C18 C17 C20 109.87(14) . . ?
C19 C17 C20 106.44(15) . . ?
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 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O5 C20 O6 123.73(17) . . ?
O5 C20 C17 124.12(17) . . ?
O6 C20 C17 111.97(15) . . ?
O6 C21 H21A 109.5 . . ?
O6 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O6 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N10 C22 C24 110.44(18) . . ?
N10 C22 C23 110.80(17) . . ?
C24 C22 C23 111.15(19) . . ?
N10 C22 C25 106.90(13) . . ?
C24 C22 C25 107.90(16) . . ?
C23 C22 C25 109.51(15) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O7 C25 N11 123.07(16) . . ?
O7 C25 C22 119.03(14) . . ?
N11 C25 C22 117.83(14) . . ?
N11 C26 C27 111.12(14) . . ?
N11 C26 C28 107.92(13) . . ?
C27 C26 C28 111.12(14) . . ?
N11 C26 C29 110.55(13) . . ?
C27 C26 C29 109.16(14) . . ?
C28 C26 C29 106.88(14) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O8 C29 N12 123.16(15) . . ?
O8 C29 C26 120.36(15) . . ?
N12 C29 C26 116.45(14) . . ?
N12 C30 C32 109.51(14) . . ?
N12 C30 C31 108.09(14) . . ?
C32 C30 C31 110.82(15) . . ?
N12 C30 C33 111.14(13) . . ?
C32 C30 C33 111.55(14) . . ?
C31 C30 C33 105.62(13) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O9 C33 N13 123.91(15) . . ?
O9 C33 C30 119.90(14) . . ?
N13 C33 C30 115.94(14) . . ?
N13 C34 C35 111.73(13) . . ?
N13 C34 C36 106.38(13) . . ?
C35 C34 C36 109.59(14) . . ?
N13 C34 C37 112.30(13) . . ?
C35 C34 C37 111.14(14) . . ?
C36 C34 C37 105.35(13) . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O10 C37 N14 122.80(16) . . ?
O10 C37 C34 120.41(15) . . ?
N14 C37 C34 116.38(14) . . ?
N14 C38 C40 111.98(15) . . ?
N14 C38 C39 107.22(14) . . ?
C40 C38 C39 110.54(15) . . ?
N14 C38 C41 110.66(14) . . ?
C40 C38 C41 109.57(14) . . ?
C39 C38 C41 106.72(14) . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C38 C40 H40A 109.5 . . ?
C38 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C38 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
O11 C41 O12 123.87(16) . . ?
O11 C41 C38 124.21(16) . . ?
O12 C41 C38 111.60(15) . . ?
O12 C42 H42A 109.5 . . ?
O12 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
O12 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
N1 N2 N3 173.07(18) . . ?
N2 N3 C1 115.26(15) . . ?
C4 N4 C5 121.12(14) . . ?
C4 N4 H4 119.5(15) . . ?
C5 N4 H4 119.3(15) . . ?
C8 N5 C9 121.56(14) . . ?
C8 N5 H5 118.6(16) . . ?
C9 N5 H5 118.7(16) . . ?
C12 N6 C13 124.42(14) . . ?
C12 N6 H6 118.5(16) . . ?
C13 N6 H6 116.7(16) . . ?
C16 N7 C17 121.77(14) . . ?
C16 N7 H7 121.6(15) . . ?
C17 N7 H7 116.5(15) . . ?
N8 N9 N10 173.1(2) . . ?
N9 N10 C22 115.28(15) . . ?
C25 N11 C26 121.82(14) . . ?
C25 N11 H11 118.9(15) . . ?
C26 N11 H11 119.2(15) . . ?
C29 N12 C30 121.45(14) . . ?
C29 N12 H12 120.6(14) . . ?
C30 N12 H12 116.0(14) . . ?
C33 N13 C34 125.38(14) . . ?
C33 N13 H13 118.8(14) . . ?
C34 N13 H13 115.6(14) . . ?
C37 N14 C38 122.15(14) . . ?
C37 N14 H14 121.3(16) . . ?
C38 N14 H14 116.5(16) . . ?
C20 O6 C21 114.96(16) . . ?
C41 O12 C42 115.60(15) . . ?
H13A O13 H13B 106(3) . . ?
H14D O14 H14E 112(3) . . ?

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
N3 C1 C4 O1 177.71(15) . . . . ?
C2 C1 C4 O1 59.3(2) . . . . ?
C3 C1 C4 O1 -61.7(2) . . . . ?
N3 C1 C4 N4 -5.2(2) . . . . ?
C2 C1 C4 N4 -123.63(18) . . . . ?
C3 C1 C4 N4 115.44(17) . . . . ?
N4 C5 C8 O2 -145.14(15) . . . . ?
C7 C5 C8 O2 -23.0(2) . . . . ?
C6 C5 C8 O2 97.27(18) . . . . ?
N4 C5 C8 N5 37.29(19) . . . . ?
C7 C5 C8 N5 159.43(15) . . . . ?
C6 C5 C8 N5 -80.30(17) . . . . ?
N5 C9 C12 O3 -154.54(15) . . . . ?
C10 C9 C12 O3 88.32(19) . . . . ?
C11 C9 C12 O3 -32.4(2) . . . . ?
N5 C9 C12 N6 31.2(2) . . . . ?
C10 C9 C12 N6 -85.99(17) . . . . ?
C11 C9 C12 N6 153.25(15) . . . . ?
N6 C13 C16 O4 -156.88(15) . . . . ?
C15 C13 C16 O4 -31.7(2) . . . . ?
C14 C13 C16 O4 87.24(18) . . . . ?
N6 C13 C16 N7 30.71(19) . . . . ?
C15 C13 C16 N7 155.85(14) . . . . ?
C14 C13 C16 N7 -85.17(16) . . . . ?
N7 C17 C20 O5 141.18(18) . . . . ?
C18 C17 C20 O5 17.7(2) . . . . ?
C19 C17 C20 O5 -102.6(2) . . . . ?
N7 C17 C20 O6 -43.5(2) . . . . ?
C18 C17 C20 O6 -166.98(15) . . . . ?
C19 C17 C20 O6 72.73(19) . . . . ?
N10 C22 C25 O7 -173.94(16) . . . . ?
C24 C22 C25 O7 67.3(2) . . . . ?
C23 C22 C25 O7 -53.8(2) . . . . ?
N10 C22 C25 N11 9.0(2) . . . . ?
C24 C22 C25 N11 -109.78(19) . . . . ?
C23 C22 C25 N11 129.11(19) . . . . ?
N11 C26 C29 O8 149.13(14) . . . . ?
C27 C26 C29 O8 26.6(2) . . . . ?
C28 C26 C29 O8 -93.67(17) . . . . ?
N11 C26 C29 N12 -32.53(19) . . . . ?
C27 C26 C29 N12 -155.06(14) . . . . ?
C28 C26 C29 N12 84.68(16) . . . . ?
N12 C30 C33 O9 152.46(16) . . . . ?
C32 C30 C33 O9 29.9(2) . . . . ?
C31 C30 C33 O9 -90.56(19) . . . . ?
N12 C30 C33 N13 -33.1(2) . . . . ?
C32 C30 C33 N13 -155.62(15) . . . . ?
C31 C30 C33 N13 83.90(17) . . . . ?
N13 C34 C37 O10 161.90(15) . . . . ?
C35 C34 C37 O10 35.9(2) . . . . ?
C36 C34 C37 O10 -82.71(19) . . . . ?
N13 C34 C37 N14 -25.2(2) . . . . ?
C35 C34 C37 N14 -151.23(15) . . . . ?
C36 C34 C37 N14 90.15(17) . . . . ?
N14 C38 C41 O11 -141.42(18) . . . . ?
C40 C38 C41 O11 -17.5(2) . . . . ?
C39 C38 C41 O11 102.2(2) . . . . ?
N14 C38 C41 O12 44.9(2) . . . . ?
C40 C38 C41 O12 168.84(16) . . . . ?
C39 C38 C41 O12 -71.45(19) . . . . ?
N1 N2 N3 C1 172.5(15) . . . . ?
C2 C1 N3 N2 -90.1(2) . . . . ?
C4 C1 N3 N2 150.94(17) . . . . ?
C3 C1 N3 N2 33.7(2) . . . . ?
O1 C4 N4 C5 0.1(2) . . . . ?
C1 C4 N4 C5 -176.84(15) . . . . ?
C7 C5 N4 C4 -70.91(19) . . . . ?
C6 C5 N4 C4 167.46(15) . . . . ?
C8 C5 N4 C4 51.0(2) . . . . ?
O2 C8 N5 C9 -6.8(2) . . . . ?
C5 C8 N5 C9 170.68(14) . . . . ?
C10 C9 N5 C8 170.86(14) . . . . ?
C11 C9 N5 C8 -67.68(19) . . . . ?
C12 C9 N5 C8 55.6(2) . . . . ?
O3 C12 N6 C13 1.3(3) . . . . ?
C9 C12 N6 C13 175.34(14) . . . . ?
C15 C13 N6 C12 -60.8(2) . . . . ?
C14 C13 N6 C12 179.61(15) . . . . ?
C16 C13 N6 C12 64.1(2) . . . . ?
O4 C16 N7 C17 -2.9(3) . . . . ?
C13 C16 N7 C17 169.35(14) . . . . ?
C18 C17 N7 C16 70.0(2) . . . . ?
C19 C17 N7 C16 -168.11(16) . . . . ?
C20 C17 N7 C16 -52.5(2) . . . . ?
N8 N9 N10 C22 -167(2) . . . . ?
C24 C22 N10 N9 -60.2(3) . . . . ?
C23 C22 N10 N9 63.5(3) . . . . ?
C25 C22 N10 N9 -177.28(18) . . . . ?
O7 C25 N11 C26 -0.4(2) . . . . ?
C22 C25 N11 C26 176.49(14) . . . . ?
C27 C26 N11 C25 69.50(19) . . . . ?
C28 C26 N11 C25 -168.44(15) . . . . ?
C29 C26 N11 C25 -51.9(2) . . . . ?
O8 C29 N12 C30 4.3(2) . . . . ?
C26 C29 N12 C30 -173.97(13) . . . . ?
C32 C30 N12 C29 70.73(19) . . . . ?
C31 C30 N12 C29 -168.44(14) . . . . ?
C33 C30 N12 C29 -52.97(19) . . . . ?
O9 C33 N13 C34 -0.3(3) . . . . ?
C30 C33 N13 C34 -174.54(14) . . . . ?
C35 C34 N13 C33 58.3(2) . . . . ?
C36 C34 N13 C33 177.83(16) . . . . ?
C37 C34 N13 C33 -67.4(2) . . . . ?
O10 C37 N14 C38 4.5(3) . . . . ?
C34 C37 N14 C38 -168.17(15) . . . . ?
C40 C38 N14 C37 -70.1(2) . . . . ?
C39 C38 N14 C37 168.46(15) . . . . ?
C41 C38 N14 C37 52.4(2) . . . . ?
O5 C20 O6 C21 3.5(3) . . . . ?
C17 C20 O6 C21 -171.9(2) . . . . ?
O11 C41 O12 C42 -4.1(3) . . . . ?
C38 C41 O12 C42 169.66(18) . . . . ?

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
N12 H12 O14 0.82(2) 2.15(2) 2.953(2) 167(2) 1_655
N11 H11 O11 0.85(2) 2.57(2) 3.3439(19) 152(2) 1_655
N14 H14 O8 0.84(3) 2.14(3) 2.9634(18) 167(2) .
N13 H13 O7 0.84(2) 2.25(2) 3.0653(18) 165.0(18) .
N5 H5 O13 0.79(2) 2.25(2) 3.026(2) 165(2) .
N4 H4 O5 0.84(2) 2.50(2) 3.2346(19) 146(2) 1_655
N4 H4 N3 0.84(2) 2.20(2) 2.615(2) 110.1(18) .
N7 H7 O2 0.89(2) 2.12(2) 2.9811(18) 165(2) .
N6 H6 O1 0.80(2) 2.30(2) 3.0763(18) 163(2) .
O14 H14E O3 0.85(3) 2.28(3) 3.113(2) 165(3) .
O14 H14D O10 0.82(3) 2.12(3) 2.940(2) 177(3) .
O13 H13B O9 0.90(3) 2.12(3) 2.9959(19) 164(3) .
O13 H13A O4 0.86(3) 2.13(3) 2.9908(18) 173(3) 1_655

_diffrn_measured_fraction_theta_max 0.937
_diffrn_reflns_theta_full        66.60
_diffrn_measured_fraction_theta_full 0.950
_refine_diff_density_max         1.287
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 984592'
