data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Jason Micklefield'
_publ_contact_author_address     
;
School of Chemistry and Manchester Interdisciplinary Biocentre
The University of Manchester
131 Princess Street
Manchester
M1 7DN
UNITED KINGDOM
;

_publ_contact_author_email       J.MICKLEFIELD@MANCHESTER.AC.UK

_publ_section_title              
;
Synthesis and DNA/RNA hybridisation properties of
mixed sequence pyrrolidine-amide oligonucleotide mimics
;
_publ_requested_category         FO
loop_
_publ_author_name
'Jason Micklefield'
'Jordi Morral'
"Adam O'Rourke"
'T. H. Samuel Tan'
'Roberta J. Worthington'

data_j
_database_code_depnum_ccdc_archive 'CCDC 624250'

_audit_creation_date             2006-11-02T12:59:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C23 H29 N7 O4, CH4O, H2O'
_chemical_formula_sum            'C24 H35 N7 O6'
_chemical_formula_weight         517.59
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.7564(9)
_cell_length_b                   13.3948(9)
_cell_length_c                   25.589(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2658.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1862
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      25.028
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9721
_exptl_absorpt_correction_T_max  0.9972

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      0.911275E-1
_diffrn_orient_matrix_ub_12      -0.520964E-1
_diffrn_orient_matrix_ub_13      0.46096E-2
_diffrn_orient_matrix_ub_21      -0.598519E-1
_diffrn_orient_matrix_ub_22      -0.434556E-1
_diffrn_orient_matrix_ub_23      -0.260238E-1
_diffrn_orient_matrix_ub_31      0.688142E-1
_diffrn_orient_matrix_ub_32      0.311624E-1
_diffrn_orient_matrix_ub_33      -0.287875E-1
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.1129
_diffrn_reflns_av_unetI/netI     0.1866
_diffrn_reflns_number            7393
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         24.96
_diffrn_reflns_theta_full        24.96
_diffrn_measured_fraction_theta_full 0.9
_diffrn_measured_fraction_theta_max 0.9
_reflns_number_total             3846
_reflns_number_gt                1657
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0989P)^2^+7.4677P] where P=(Fo^2^+2Fc^2^)/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_number_reflns         3846
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2379
_refine_ls_R_factor_gt           0.0956
_refine_ls_wR_factor_ref         0.3014
_refine_ls_wR_factor_gt          0.2102
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_restrained_S_all      1.02
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   4(5)
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.07

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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
C2 C 0.7496(10) 0.2590(6) 0.4047(3) 0.062(2) Uani 1 1 d . . .
C4 C 0.8565(9) 0.4157(5) 0.3847(3) 0.052(2) Uani 1 1 d . . .
C5 C 0.7116(8) 0.4400(5) 0.3566(3) 0.054(2) Uani 1 1 d . . .
H5 H 0.7005 0.5031 0.3399 0.065 Uiso 1 1 calc R . .
C6 C 0.5844(9) 0.3699(5) 0.3536(3) 0.051(2) Uani 1 1 d . . .
H6 H 0.4839 0.3835 0.3336 0.062 Uiso 1 1 calc R . .
C9 C 1.0132(10) 0.5788(6) 0.3700(3) 0.065(3) Uani 1 1 d . . .
C11 C 1.1785(8) 0.6324(5) 0.3853(3) 0.047(2) Uani 1 1 d . . .
C12 C 1.3255(9) 0.5886(6) 0.4072(3) 0.062(2) Uani 1 1 d . . .
H12 H 1.3284 0.5186 0.413 0.075 Uiso 1 1 calc R . .
C13 C 1.4683(9) 0.6471(6) 0.4206(3) 0.054(2) Uani 1 1 d . . .
H13 H 1.5675 0.6173 0.4358 0.064 Uiso 1 1 calc R . .
C14 C 1.4633(9) 0.7486(6) 0.4117(3) 0.050(2) Uani 1 1 d . . .
C15 C 1.3172(9) 0.7915(6) 0.3906(3) 0.055(2) Uani 1 1 d . . .
H15 H 1.3126 0.8619 0.3865 0.066 Uiso 1 1 calc R . .
C16 C 1.1776(9) 0.7347(6) 0.3755(3) 0.053(2) Uani 1 1 d . . .
H16 H 1.0819 0.765 0.3585 0.064 Uiso 1 1 calc R . .
C17 C 1.6190(9) 0.8126(6) 0.4273(3) 0.060(2) Uani 1 1 d . . .
C18 C 1.5598(10) 0.9051(6) 0.4590(3) 0.068(3) Uani 1 1 d . . .
H18A H 1.5053 0.8832 0.4916 0.101 Uiso 1 1 calc R . .
H18B H 1.4767 0.9436 0.4383 0.101 Uiso 1 1 calc R . .
H18C H 1.6599 0.947 0.467 0.101 Uiso 1 1 calc R . .
C19 C 1.7544(10) 0.7566(6) 0.4594(3) 0.067(3) Uani 1 1 d . . .
H19A H 1.7024 0.7331 0.4921 0.101 Uiso 1 1 calc R . .
H19B H 1.8505 0.8016 0.4674 0.101 Uiso 1 1 calc R . .
H19C H 1.7969 0.6993 0.4394 0.101 Uiso 1 1 calc R . .
C20 C 1.7049(10) 0.8496(6) 0.3766(3) 0.066(3) Uani 1 1 d . . .
H20A H 1.8063 0.89 0.3853 0.1 Uiso 1 1 calc R . .
H20B H 1.6227 0.8903 0.3568 0.1 Uiso 1 1 calc R . .
H20C H 1.7404 0.7922 0.3554 0.1 Uiso 1 1 calc R . .
C22 C 0.4175(9) 0.1402(6) 0.2873(3) 0.061(2) Uani 1 1 d . . .
H22 H 0.3293 0.0876 0.28 0.074 Uiso 1 1 calc R . .
C23 C 0.5125(10) 0.1173(5) 0.3387(3) 0.060(2) Uani 1 1 d . . .
H23A H 0.6386 0.1155 0.3328 0.072 Uiso 1 1 calc R . .
H23B H 0.4758 0.0516 0.3525 0.072 Uiso 1 1 calc R . .
C24 C 0.4665(8) 0.2012(5) 0.3782(3) 0.051(2) Uani 1 1 d . . .
H24 H 0.4454 0.1737 0.414 0.061 Uiso 1 1 calc R . .
C25 C 0.3000(9) 0.2404(6) 0.3535(3) 0.064(3) Uani 1 1 d . . .
H25A H 0.2011 0.1971 0.3627 0.077 Uiso 1 1 calc R . .
H25B H 0.2754 0.3092 0.3655 0.077 Uiso 1 1 calc R . .
C26 C 0.5362(9) 0.1528(6) 0.2401(3) 0.061(2) Uani 1 1 d . . .
H26A H 0.5853 0.087 0.2307 0.074 Uiso 1 1 calc R . .
H26B H 0.4675 0.1768 0.21 0.074 Uiso 1 1 calc R . .
C27 C 0.1784(10) 0.2598(5) 0.2656(3) 0.066(3) Uani 1 1 d . . .
H27A H 0.0747 0.2303 0.2821 0.079 Uiso 1 1 calc R . .
H27B H 0.1925 0.2297 0.2305 0.079 Uiso 1 1 calc R . .
C31 C 0.1566(9) 0.3696(6) 0.2607(3) 0.056(2) Uani 1 1 d . . .
C34 C 0.0040(10) 0.4971(5) 0.2152(3) 0.066(3) Uani 1 1 d . . .
H34A H -0.0259 0.5295 0.2483 0.099 Uiso 1 1 calc R . .
H34B H -0.0908 0.5055 0.1903 0.099 Uiso 1 1 calc R . .
H34C H 0.1088 0.5276 0.2009 0.099 Uiso 1 1 calc R . .
O7 O 0.7694(7) 0.1748(4) 0.4254(2) 0.0691(17) Uani 1 1 d . . .
O10 O 0.9094(6) 0.6111(4) 0.3392(2) 0.0701(18) Uani 1 1 d . . .
O32 O 0.2304(6) 0.4334(4) 0.2857(2) 0.0657(17) Uani 1 1 d . . .
O33 O 0.0338(6) 0.3909(4) 0.2241(2) 0.0653(17) Uani 1 1 d . . .
O35 O 0.2092(7) 0.3628(4) 0.4653(2) 0.0807(19) Uani 1 1 d . . .
N1 N 0.5992(7) 0.2802(4) 0.3789(2) 0.0523(19) Uani 1 1 d . . .
N3 N 0.8807(8) 0.3288(5) 0.4079(2) 0.058(2) Uani 1 1 d . . .
N8 N 0.9959(8) 0.4830(4) 0.3923(2) 0.0553(19) Uani 1 1 d . . .
H8 H 1.0797 0.463 0.413 0.066 Uiso 1 1 calc R . .
N21 N 0.3309(7) 0.2386(4) 0.2977(2) 0.0524(18) Uani 1 1 d . . .
N28 N 0.6819(8) 0.2255(4) 0.2502(2) 0.061(2) Uani 1 1 d . . .
N29 N 0.6428(8) 0.3110(5) 0.2378(2) 0.059(2) Uani 1 1 d . . .
N30 N 0.6197(8) 0.3946(5) 0.2268(3) 0.069(2) Uani 1 1 d . . .
C36 C 0.6463(16) 0.4240(9) 0.5088(5) 0.025(3) Uiso 0.460(6) 1 d P A 1
H36A H 0.5858 0.4778 0.5271 0.037 Uiso 0.460(6) 1 calc PR A 1
H36B H 0.6118 0.4238 0.4719 0.037 Uiso 0.460(6) 1 calc PR A 1
H36C H 0.771 0.4348 0.5112 0.037 Uiso 0.460(6) 1 calc PR A 1
O37 O 0.605(2) 0.3348(12) 0.5309(7) 0.135(6) Uiso 0.460(6) 1 d P A 1
H37 H 0.5902 0.3425 0.5632 0.202 Uiso 0.460(6) 1 calc PR A 1
C36B C 0.593(2) 0.4865(11) 0.5426(6) 0.069(5) Uiso 0.540(6) 1 d P A 2
H36D H 0.4904 0.5094 0.524 0.104 Uiso 0.540(6) 1 calc PR A 2
H36E H 0.6502 0.4339 0.5223 0.104 Uiso 0.540(6) 1 calc PR A 2
H36F H 0.6731 0.5427 0.5472 0.104 Uiso 0.540(6) 1 calc PR A 2
O37B O 0.5530(16) 0.4545(9) 0.5843(5) 0.100(4) Uiso 0.540(6) 1 d P A 2
H37B H 0.6413 0.4347 0.6002 0.151 Uiso 0.540(6) 1 calc PR A 2
H35A H 0.217 0.369 0.5152 0.1 Uiso 1 1 d . . .
H35B H 0.0779 0.3082 0.4662 0.1 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C2 0.061(5) 0.070(5) 0.056(5) 0.011(4) 0.008(4) -0.006(5)
C4 0.056(5) 0.055(5) 0.044(4) 0.000(4) 0.002(4) -0.003(4)
C5 0.041(4) 0.052(5) 0.069(5) 0.001(4) -0.009(4) -0.002(4)
C6 0.049(4) 0.061(5) 0.044(4) -0.011(4) -0.002(3) -0.002(4)
C9 0.055(5) 0.066(6) 0.074(6) 0.005(5) 0.009(4) 0.012(5)
C11 0.041(4) 0.055(5) 0.043(4) -0.001(4) -0.006(3) -0.001(4)
C12 0.054(5) 0.051(5) 0.082(6) 0.005(4) 0.005(4) 0.015(4)
C13 0.044(4) 0.075(5) 0.041(4) 0.005(4) 0.003(4) 0.004(4)
C14 0.038(4) 0.065(5) 0.048(4) 0.001(4) 0.004(3) -0.017(4)
C15 0.046(4) 0.074(5) 0.044(4) -0.004(4) -0.006(4) 0.008(4)
C16 0.042(4) 0.071(5) 0.047(4) 0.008(4) -0.003(4) 0.004(4)
C17 0.036(4) 0.078(6) 0.066(5) -0.010(4) 0.006(4) 0.014(4)
C18 0.064(5) 0.088(6) 0.051(5) -0.004(4) 0.011(4) -0.015(5)
C19 0.057(5) 0.080(6) 0.065(5) 0.010(4) 0.001(4) -0.027(5)
C20 0.068(5) 0.082(6) 0.049(5) 0.011(4) 0.005(4) -0.006(5)
C22 0.054(5) 0.049(5) 0.082(6) 0.008(4) -0.013(4) -0.007(4)
C23 0.060(5) 0.058(5) 0.061(5) 0.001(4) -0.004(4) -0.002(4)
C24 0.034(4) 0.065(5) 0.053(4) 0.000(4) 0.005(3) -0.016(4)
C25 0.055(5) 0.060(5) 0.077(6) 0.008(4) 0.007(4) -0.001(5)
C26 0.061(5) 0.061(5) 0.062(5) 0.008(4) -0.006(4) 0.007(5)
C27 0.058(5) 0.053(5) 0.088(6) 0.000(5) -0.007(5) -0.003(4)
C31 0.054(4) 0.051(5) 0.061(5) 0.001(4) 0.000(4) -0.003(4)
C34 0.069(5) 0.045(5) 0.084(6) 0.014(5) -0.007(5) -0.002(4)
O7 0.074(4) 0.074(4) 0.059(3) 0.015(3) -0.004(3) -0.012(3)
O10 0.063(3) 0.071(4) 0.076(4) 0.018(3) -0.014(3) -0.008(3)
O32 0.067(3) 0.051(3) 0.079(4) -0.007(3) -0.016(3) -0.006(3)
O33 0.067(3) 0.069(4) 0.061(3) -0.002(3) -0.004(3) 0.002(3)
O35 0.090(4) 0.084(4) 0.067(4) 0.017(3) -0.001(3) -0.003(4)
N1 0.041(3) 0.057(4) 0.060(4) -0.004(3) -0.007(3) 0.005(3)
N3 0.061(4) 0.058(4) 0.056(4) 0.011(3) -0.003(3) -0.003(4)
N8 0.061(4) 0.047(4) 0.058(4) 0.002(3) -0.011(3) 0.001(3)
N21 0.050(4) 0.061(4) 0.046(4) 0.005(3) -0.001(3) 0.003(3)
N28 0.056(4) 0.056(4) 0.072(5) 0.002(3) -0.001(4) 0.018(4)
N29 0.051(4) 0.079(5) 0.048(4) -0.008(4) -0.011(3) 0.011(4)
N30 0.058(4) 0.063(5) 0.086(5) 0.010(4) -0.004(4) 0.000(4)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 O7 1.256(8) . ?
C2 N1 1.369(9) . ?
C2 N3 1.384(9) . ?
C4 N3 1.320(9) . ?
C4 C5 1.373(9) . ?
C4 N8 1.422(9) . ?
C5 C6 1.364(9) . ?
C5 H5 0.95 . ?
C6 N1 1.370(9) . ?
C6 H6 0.95 . ?
C9 O10 1.207(9) . ?
C9 N8 1.410(9) . ?
C9 C11 1.521(10) . ?
C11 C12 1.399(9) . ?
C11 C16 1.394(10) . ?
C12 C13 1.400(10) . ?
C12 H12 0.95 . ?
C13 C14 1.379(10) . ?
C13 H13 0.95 . ?
C14 C15 1.381(9) . ?
C14 C17 1.533(10) . ?
C15 C16 1.379(10) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C17 C19 1.529(10) . ?
C17 C20 1.541(10) . ?
C17 C18 1.550(10) . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C22 N21 1.503(9) . ?
C22 C26 1.526(10) . ?
C22 C23 1.540(10) . ?
C22 H22 1 . ?
C23 C24 1.553(10) . ?
C23 H23A 0.99 . ?
C23 H23B 0.99 . ?
C24 N1 1.477(9) . ?
C24 C25 1.531(10) . ?
C24 H24 1 . ?
C25 N21 1.449(9) . ?
C25 H25A 0.99 . ?
C25 H25B 0.99 . ?
C26 N28 1.514(9) . ?
C26 H26A 0.99 . ?
C26 H26B 0.99 . ?
C27 N21 1.468(9) . ?
C27 C31 1.486(10) . ?
C27 H27A 0.99 . ?
C27 H27B 0.99 . ?
C31 O32 1.211(8) . ?
C31 O33 1.365(8) . ?
C34 O33 1.459(8) . ?
C34 H34A 0.98 . ?
C34 H34B 0.98 . ?
C34 H34C 0.98 . ?
O35 H35A 1.282(5) . ?
O35 H35B 1.254(6) . ?
N8 H8 0.88 . ?
N28 N29 1.228(8) . ?
N29 N30 1.168(8) . ?
C36 O37 1.361(19) . ?
C36 H36A 0.98 . ?
C36 H36B 0.98 . ?
C36 H36C 0.98 . ?
O37 H37 0.84 . ?
C36B O37B 1.193(18) . ?
C36B H36D 0.98 . ?
C36B H36E 0.98 . ?
C36B H36F 0.98 . ?
O37B H37B 0.84 . ?

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
O7 C2 N1 119.6(7) . . ?
O7 C2 N3 119.4(7) . . ?
N1 C2 N3 121.0(7) . . ?
N3 C4 C5 124.2(7) . . ?
N3 C4 N8 112.9(6) . . ?
C5 C4 N8 122.9(6) . . ?
C6 C5 C4 117.2(7) . . ?
C6 C5 H5 121.4 . . ?
C4 C5 H5 121.4 . . ?
C5 C6 N1 121.1(6) . . ?
C5 C6 H6 119.5 . . ?
N1 C6 H6 119.5 . . ?
O10 C9 N8 121.8(7) . . ?
O10 C9 C11 124.1(7) . . ?
N8 C9 C11 113.9(6) . . ?
C12 C11 C16 119.2(6) . . ?
C12 C11 C9 126.3(7) . . ?
C16 C11 C9 114.4(6) . . ?
C11 C12 C13 120.6(7) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 119.2(7) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 119.9(7) . . ?
C13 C14 C17 119.0(6) . . ?
C15 C14 C17 121.1(7) . . ?
C16 C15 C14 121.7(7) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C11 119.2(7) . . ?
C15 C16 H16 120.4 . . ?
C11 C16 H16 120.4 . . ?
C19 C17 C14 114.0(6) . . ?
C19 C17 C20 108.3(6) . . ?
C14 C17 C20 107.5(6) . . ?
C19 C17 C18 108.3(6) . . ?
C14 C17 C18 110.5(6) . . ?
C20 C17 C18 108.1(6) . . ?
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 . . ?
N21 C22 C26 108.2(6) . . ?
N21 C22 C23 103.7(6) . . ?
C26 C22 C23 114.2(6) . . ?
N21 C22 H22 110.2 . . ?
C26 C22 H22 110.2 . . ?
C23 C22 H22 110.2 . . ?
C22 C23 C24 107.6(6) . . ?
C22 C23 H23A 110.2 . . ?
C24 C23 H23A 110.2 . . ?
C22 C23 H23B 110.2 . . ?
C24 C23 H23B 110.2 . . ?
H23A C23 H23B 108.5 . . ?
N1 C24 C25 110.3(6) . . ?
N1 C24 C23 111.5(6) . . ?
C25 C24 C23 100.0(6) . . ?
N1 C24 H24 111.5 . . ?
C25 C24 H24 111.5 . . ?
C23 C24 H24 111.5 . . ?
N21 C25 C24 105.2(6) . . ?
N21 C25 H25A 110.7 . . ?
C24 C25 H25A 110.7 . . ?
N21 C25 H25B 110.7 . . ?
C24 C25 H25B 110.7 . . ?
H25A C25 H25B 108.8 . . ?
N28 C26 C22 112.8(6) . . ?
N28 C26 H26A 109 . . ?
C22 C26 H26A 109 . . ?
N28 C26 H26B 109 . . ?
C22 C26 H26B 109 . . ?
H26A C26 H26B 107.8 . . ?
N21 C27 C31 109.3(6) . . ?
N21 C27 H27A 109.8 . . ?
C31 C27 H27A 109.8 . . ?
N21 C27 H27B 109.8 . . ?
C31 C27 H27B 109.8 . . ?
H27A C27 H27B 108.3 . . ?
O32 C31 O33 123.0(7) . . ?
O32 C31 C27 126.8(7) . . ?
O33 C31 C27 110.1(6) . . ?
O33 C34 H34A 109.5 . . ?
O33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C31 O33 C34 114.9(6) . . ?
H35A O35 H35B 93.3(4) . . ?
C2 N1 C6 118.8(6) . . ?
C2 N1 C24 116.8(6) . . ?
C6 N1 C24 124.4(6) . . ?
C4 N3 C2 117.7(6) . . ?
C9 N8 C4 126.4(6) . . ?
C9 N8 H8 116.8 . . ?
C4 N8 H8 116.8 . . ?
C25 N21 C27 114.5(6) . . ?
C25 N21 C22 105.3(6) . . ?
C27 N21 C22 115.5(6) . . ?
N29 N28 C26 111.8(6) . . ?
N30 N29 N28 174.3(7) . . ?
O37B C36B H36D 109.5 . . ?
O37B C36B H36E 109.5 . . ?
H36D C36B H36E 109.5 . . ?
O37B C36B H36F 109.5 . . ?
H36D C36B H36F 109.5 . . ?
H36E C36B H36F 109.5 . . ?
C36B O37B H37B 109.5 . . ?

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 C4 C5 C6 1.2(11) . . . . ?
N8 C4 C5 C6 -177.8(6) . . . . ?
C4 C5 C6 N1 1.9(10) . . . . ?
O10 C9 C11 C12 -159.1(8) . . . . ?
N8 C9 C11 C12 16.7(10) . . . . ?
O10 C9 C11 C16 20.3(11) . . . . ?
N8 C9 C11 C16 -163.9(6) . . . . ?
C16 C11 C12 C13 2.0(10) . . . . ?
C9 C11 C12 C13 -178.5(7) . . . . ?
C11 C12 C13 C14 -0.6(11) . . . . ?
C12 C13 C14 C15 1.3(10) . . . . ?
C12 C13 C14 C17 179.0(6) . . . . ?
C13 C14 C15 C16 -3.6(10) . . . . ?
C17 C14 C15 C16 178.8(6) . . . . ?
C14 C15 C16 C11 5.0(10) . . . . ?
C12 C11 C16 C15 -4.2(10) . . . . ?
C9 C11 C16 C15 176.3(6) . . . . ?
C13 C14 C17 C19 -8.9(9) . . . . ?
C15 C14 C17 C19 168.7(6) . . . . ?
C13 C14 C17 C20 111.1(7) . . . . ?
C15 C14 C17 C20 -71.2(8) . . . . ?
C13 C14 C17 C18 -131.2(7) . . . . ?
C15 C14 C17 C18 46.5(9) . . . . ?
N21 C22 C23 C24 3.5(7) . . . . ?
C26 C22 C23 C24 121.1(7) . . . . ?
C22 C23 C24 N1 -95.8(7) . . . . ?
C22 C23 C24 C25 20.8(7) . . . . ?
N1 C24 C25 N21 78.4(7) . . . . ?
C23 C24 C25 N21 -39.1(7) . . . . ?
N21 C22 C26 N28 64.2(7) . . . . ?
C23 C22 C26 N28 -50.7(8) . . . . ?
N21 C27 C31 O32 -12.2(11) . . . . ?
N21 C27 C31 O33 169.9(6) . . . . ?
O32 C31 O33 C34 3.2(10) . . . . ?
C27 C31 O33 C34 -178.8(6) . . . . ?
O7 C2 N1 C6 -175.7(6) . . . . ?
N3 C2 N1 C6 3.8(10) . . . . ?
O7 C2 N1 C24 1.1(10) . . . . ?
N3 C2 N1 C24 -179.3(6) . . . . ?
C5 C6 N1 C2 -4.3(10) . . . . ?
C5 C6 N1 C24 179.1(6) . . . . ?
C25 C24 N1 C2 173.6(6) . . . . ?
C23 C24 N1 C2 -76.2(8) . . . . ?
C25 C24 N1 C6 -9.8(9) . . . . ?
C23 C24 N1 C6 100.4(7) . . . . ?
C5 C4 N3 C2 -1.7(11) . . . . ?
N8 C4 N3 C2 177.5(6) . . . . ?
O7 C2 N3 C4 178.6(7) . . . . ?
N1 C2 N3 C4 -0.9(10) . . . . ?
O10 C9 N8 C4 -3.5(12) . . . . ?
C11 C9 N8 C4 -179.4(6) . . . . ?
N3 C4 N8 C9 175.9(7) . . . . ?
C5 C4 N8 C9 -5.0(11) . . . . ?
C24 C25 N21 C27 171.6(6) . . . . ?
C24 C25 N21 C22 43.6(7) . . . . ?
C31 C27 N21 C25 84.1(8) . . . . ?
C31 C27 N21 C22 -153.3(6) . . . . ?
C26 C22 N21 C25 -150.2(6) . . . . ?
C23 C22 N21 C25 -28.5(7) . . . . ?
C26 C22 N21 C27 82.5(7) . . . . ?
C23 C22 N21 C27 -155.9(6) . . . . ?
C22 C26 N28 N29 -91.0(7) . . . . ?
C26 N28 N29 N30 -173(7) . . . . ?