# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2008
data_global
_journal_name_full Chem.Commun.
_journal_coden_Cambridge 0182
_journal_volume ?
_journal_page_first ?
_journal_year ?
_publ_contact_author_name 'Lyle Isaacs'
_publ_contact_author_email LISAACS@UMD.EDU
_publ_section_title
;
Tetrameric Molecular Bowl Assembled from Glycoluril
Building Blocks
;
loop_
_publ_author_name
'Lyle Isaacs.'
'Meng Gao.'
'Xianggao Meng.'
'Neng-Fang She.'
'An-Xin Wu.'
# Attachment '051104CM.cif'
data_051104cm
_database_code_depnum_ccdc_archive 'CCDC 671165'
_audit_update_record
;
2008-03-01 # Formatted by publCIF
;
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C34 H28 N4 O6, 1.6(H2 O)'
_chemical_formula_sum 'C34 H31.2 N4 O7.6 '
_chemical_formula_weight 617.40
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Tetragonal
_symmetry_space_group_name_H-M 'P 4/n'
_symmetry_space_group_name_Hall '-P 4a'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y+1/2, x, z'
'y, -x+1/2, z'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y-1/2, -x, -z'
'-y, x-1/2, -z'
_cell_length_a 27.2293(7)
_cell_length_b 27.2293(7)
_cell_length_c 8.7855(4)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 6513.9(4)
_cell_formula_units_Z 8
_cell_measurement_temperature 292(2)
_cell_measurement_reflns_used 4726
_cell_measurement_theta_min 2.37
_cell_measurement_theta_max 19.09
_exptl_crystal_description needle
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.08
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.200
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 2592
_exptl_absorpt_coefficient_mu 0.090
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 292(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 61089
_diffrn_reflns_av_R_equivalents 0.1657
_diffrn_reflns_av_sigmaI/netI 0.0993
_diffrn_reflns_limit_h_min -32
_diffrn_reflns_limit_h_max 32
_diffrn_reflns_limit_k_min -32
_diffrn_reflns_limit_k_max 32
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_limit_l_max 10
_diffrn_reflns_theta_min 2.37
_diffrn_reflns_theta_max 25.00
_reflns_number_total 5726
_reflns_number_gt 2861
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker SMART'
_computing_cell_refinement 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_refine_special_details
;
Refinement of 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.
During the refinement, carbon bound H-atoms were located at the geometrical
positions and their thermal parameters were set 1.2 or 1.5 times of their
carrier atoms, whereas H-atoms attached to N atoms were found from the
difference Fourier maps with two constraints of N-H=0.86(1)\%A and U~iso~(H)
= 1.2 U~eq~(N). In the refinement, five separate larger residual peaks (within
1.2-2.0 e/\%A^3^) were crystallographically assigned to water molecules. One
was located at the general position, two lying on the 4-fold axis and the
other two on the 2-fold axis in space group P4/n. Further refinement results
in several short contacts between them. So the contribution of the solvent
molecules to the diffraction pattern was subtracted using the SQUEEZE
procedure of PLATON (Spek, 2003). The result indicated that the
solvent-accessible void in the unit cell has a volume of 799.8\%A^3^
(consisting of about 12.3% percent of the crystal volume, equally distributed
across four cavities). The residual electron-density count amounted to 134 e
per unit cell, corresponding to nearly 13 molecules of H~2~O (the content of
each of the four cavities per unit cell being equivalent about 3.2 molecules
of H~2~O, i.e. every molecule of 1 being distributed 1.6 water
molecules.
;
_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^)+(0.0912P)^2^] 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 SHELXL
_refine_ls_extinction_coef 0.0013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 5726
_refine_ls_number_parameters 406
_refine_ls_number_restraints 2
_refine_ls_R_factor_all 0.1366
_refine_ls_R_factor_gt 0.0685
_refine_ls_wR_factor_ref 0.1810
_refine_ls_wR_factor_gt 0.1603
_refine_ls_goodness_of_fit_ref 0.927
_refine_ls_restrained_S_all 0.927
_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 0.13627(15) 0.59914(16) 1.4712(5) 0.0968(13) Uani 1 1 d . . .
H1 H 0.1456 0.5677 1.5011 0.116 Uiso 1 1 calc R . .
C2 C 0.16179(16) 0.6396(2) 1.5276(6) 0.1151(17) Uani 1 1 d . . .
H2 H 0.1876 0.6349 1.5952 0.138 Uiso 1 1 calc R . .
C3 C 0.14951(17) 0.68540(19) 1.4854(5) 0.1042(14) Uani 1 1 d . . .
H3 H 0.1665 0.7123 1.5239 0.125 Uiso 1 1 calc R . .
C4 C 0.11204(18) 0.69184(16) 1.3861(7) 0.1233(18) Uani 1 1 d . . .
H4 H 0.1037 0.7233 1.3542 0.148 Uiso 1 1 calc R . .
C5 C 0.08631(16) 0.65224(15) 1.3322(6) 0.1097(15) Uani 1 1 d . . .
H5 H 0.0602 0.6575 1.2659 0.132 Uiso 1 1 calc R . .
C6 C 0.09809(12) 0.60482(12) 1.3734(4) 0.0609(8) Uani 1 1 d . . .
C7 C 0.07172(12) 0.56348(13) 1.3176(4) 0.0616(9) Uani 1 1 d . . .
C8 C 0.05184(12) 0.52742(13) 1.2727(3) 0.0595(9) Uani 1 1 d . . .
C9 C 0.03039(11) 0.48169(11) 1.2196(4) 0.0536(8) Uani 1 1 d . . .
C10 C 0.04701(10) 0.45913(10) 1.0868(3) 0.0479(7) Uani 1 1 d . . .
C11 C -0.00661(12) 0.45898(14) 1.3060(4) 0.0687(9) Uani 1 1 d . . .
H11 H -0.0181 0.4740 1.3942 0.082 Uiso 1 1 calc R . .
C12 C 0.02672(10) 0.41470(11) 1.0399(3) 0.0523(8) Uani 1 1 d . . .
C13 C -0.02585(12) 0.41503(14) 1.2617(4) 0.0697(9) Uani 1 1 d . . .
H13 H -0.0502 0.4004 1.3203 0.084 Uiso 1 1 calc R . .
C14 C -0.00976(11) 0.39191(12) 1.1311(4) 0.0574(8) Uani 1 1 d . . .
C15 C -0.02993(11) 0.34486(15) 1.0910(4) 0.0669(9) Uani 1 1 d . . .
C16 C -0.04699(12) 0.30564(15) 1.0636(4) 0.0689(9) Uani 1 1 d . . .
C17 C -0.06650(12) 0.25835(13) 1.0273(4) 0.0664(9) Uani 1 1 d . . .
C18 C -0.04762(14) 0.23134(16) 0.9087(5) 0.0797(11) Uani 1 1 d . . .
H18 H -0.0221 0.2441 0.8507 0.096 Uiso 1 1 calc R . .
C19 C -0.06596(19) 0.18590(19) 0.8752(6) 0.1037(14) Uani 1 1 d . . .
H19 H -0.0530 0.1678 0.7948 0.124 Uiso 1 1 calc R . .
C20 C -0.1039(2) 0.16711(18) 0.9619(8) 0.1209(18) Uani 1 1 d . . .
H20 H -0.1168 0.1363 0.9395 0.145 Uiso 1 1 calc R . .
C21 C -0.12217(19) 0.1934(2) 1.0790(7) 0.1238(17) Uani 1 1 d . . .
H21 H -0.1477 0.1805 1.1365 0.149 Uiso 1 1 calc R . .
C22 C -0.10409(15) 0.23824(15) 1.1146(5) 0.0963(13) Uani 1 1 d . . .
H22 H -0.1167 0.2555 1.1970 0.116 Uiso 1 1 calc R . .
C23 C 0.08544(11) 0.48469(11) 0.9907(3) 0.0557(8) Uani 1 1 d . . .
H23A H 0.0703 0.4944 0.8953 0.067 Uiso 1 1 calc R . .
H23B H 0.0954 0.5145 1.0429 0.067 Uiso 1 1 calc R . .
C24 C 0.04211(11) 0.38988(11) 0.8926(3) 0.0584(8) Uani 1 1 d . . .
H24A H 0.0240 0.3594 0.8826 0.070 Uiso 1 1 calc R . .
H24B H 0.0328 0.4108 0.8081 0.070 Uiso 1 1 calc R . .
C25 C 0.16864(12) 0.45446(12) 1.0552(4) 0.0546(8) Uani 1 1 d . . .
C26 C 0.11418(14) 0.33645(13) 0.9226(4) 0.0637(9) Uani 1 1 d . . .
C27 C 0.12966(10) 0.41728(10) 0.8470(3) 0.0472(7) Uani 1 1 d . . .
C28 C 0.12212(11) 0.43661(13) 0.6846(3) 0.0560(8) Uani 1 1 d . . .
C29 C 0.11824(17) 0.41054(16) 0.4278(4) 0.0945(13) Uani 1 1 d . . .
H29A H 0.0874 0.4274 0.4102 0.113 Uiso 1 1 calc R . .
H29B H 0.1447 0.4322 0.3971 0.113 Uiso 1 1 calc R . .
C30 C 0.1199(3) 0.3671(2) 0.3405(5) 0.160(3) Uani 1 1 d . . .
H30A H 0.1481 0.3482 0.3690 0.240 Uiso 1 1 calc R . .
H30B H 0.1219 0.3753 0.2344 0.240 Uiso 1 1 calc R . .
H30C H 0.0907 0.3482 0.3586 0.240 Uiso 1 1 calc R . .
C31 C 0.18001(11) 0.39061(11) 0.8777(4) 0.0551(8) Uani 1 1 d . . .
C32 C 0.21626(12) 0.38862(15) 0.7475(4) 0.0658(9) Uani 1 1 d . . .
C33 C 0.26015(18) 0.4346(2) 0.5638(6) 0.1309(18) Uani 1 1 d . . .
H33A H 0.2932 0.4299 0.6021 0.157 Uiso 1 1 calc R . .
H33B H 0.2532 0.4088 0.4907 0.157 Uiso 1 1 calc R . .
C34 C 0.2558(2) 0.4824(2) 0.4916(6) 0.161(2) Uani 1 1 d . . .
H34A H 0.2244 0.4849 0.4423 0.242 Uiso 1 1 calc R . .
H34B H 0.2814 0.4862 0.4176 0.242 Uiso 1 1 calc R . .
H34C H 0.2586 0.5077 0.5673 0.242 Uiso 1 1 calc R . .
N1 N 0.12920(8) 0.45626(8) 0.9565(3) 0.0485(6) Uani 1 1 d . . .
N2 N 0.09396(8) 0.37928(8) 0.8810(3) 0.0500(6) Uani 1 1 d . . .
N3 N 0.19887(9) 0.41780(10) 1.0043(3) 0.0619(7) Uani 1 1 d D . .
H3A H 0.2296(5) 0.4192(12) 1.024(4) 0.074 Uiso 1 1 d D . .
N4 N 0.16387(11) 0.34163(10) 0.9171(4) 0.0776(9) Uani 1 1 d D . .
H4A H 0.1872(9) 0.3232(11) 0.947(4) 0.093 Uiso 1 1 d D . .
O1 O 0.17471(8) 0.48041(8) 1.1637(3) 0.0680(6) Uani 1 1 d . . .
O2 O 0.09201(10) 0.29966(9) 0.9599(3) 0.0953(9) Uani 1 1 d . . .
O3 O 0.11635(9) 0.47818(9) 0.6504(3) 0.0845(8) Uani 1 1 d . . .
O4 O 0.12304(8) 0.39879(8) 0.5881(2) 0.0667(6) Uani 1 1 d . . .
O5 O 0.23441(10) 0.35176(11) 0.7020(3) 0.1020(9) Uani 1 1 d . . .
O6 O 0.22450(8) 0.43254(10) 0.6905(3) 0.0815(7) Uani 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
C1 0.084(3) 0.084(3) 0.123(4) 0.027(3) -0.023(3) -0.005(2)
C2 0.090(3) 0.118(4) 0.137(4) 0.040(3) -0.050(3) -0.025(3)
C3 0.108(4) 0.101(4) 0.104(3) -0.011(3) -0.023(3) -0.021(3)
C4 0.120(4) 0.070(3) 0.180(5) -0.015(3) -0.063(4) 0.005(3)
C5 0.103(3) 0.075(3) 0.150(4) -0.016(3) -0.061(3) 0.013(3)
C6 0.058(2) 0.067(2) 0.057(2) 0.0008(17) 0.0001(17) 0.0041(18)
C7 0.066(2) 0.063(2) 0.056(2) -0.0070(18) 0.0066(17) 0.0085(19)
C8 0.057(2) 0.073(2) 0.0486(19) -0.0008(18) 0.0063(16) 0.0200(19)
C9 0.0474(18) 0.059(2) 0.055(2) -0.0014(17) -0.0006(16) 0.0085(15)
C10 0.0423(16) 0.0504(18) 0.0511(19) 0.0035(15) 0.0015(14) 0.0061(14)
C11 0.063(2) 0.086(3) 0.057(2) -0.0081(19) 0.0102(17) 0.007(2)
C12 0.0461(18) 0.060(2) 0.0506(19) 0.0017(16) 0.0000(15) 0.0040(15)
C13 0.057(2) 0.084(3) 0.069(2) 0.004(2) 0.0142(18) -0.0107(19)
C14 0.0454(18) 0.070(2) 0.056(2) 0.0023(17) 0.0038(16) -0.0073(16)
C15 0.049(2) 0.085(3) 0.067(2) 0.001(2) 0.0028(17) -0.006(2)
C16 0.056(2) 0.078(3) 0.072(2) 0.008(2) 0.0078(18) 0.000(2)
C17 0.057(2) 0.069(2) 0.073(2) 0.003(2) -0.0005(19) -0.0045(18)
C18 0.075(2) 0.087(3) 0.077(3) 0.001(2) -0.012(2) 0.008(2)
C19 0.101(4) 0.098(4) 0.112(4) -0.016(3) -0.037(3) 0.030(3)
C20 0.123(4) 0.069(3) 0.170(6) -0.012(3) -0.050(4) -0.004(3)
C21 0.114(4) 0.090(4) 0.168(5) 0.010(4) 0.011(4) -0.034(3)
C22 0.100(3) 0.080(3) 0.109(3) -0.004(2) 0.026(3) -0.022(2)
C23 0.0558(19) 0.0498(18) 0.062(2) -0.0007(15) 0.0060(16) 0.0040(15)
C24 0.054(2) 0.067(2) 0.054(2) -0.0032(16) -0.0012(16) -0.0102(16)
C25 0.057(2) 0.058(2) 0.0484(19) 0.0031(17) 0.0104(17) -0.0059(17)
C26 0.077(3) 0.050(2) 0.065(2) 0.0000(17) 0.0102(19) 0.0016(19)
C27 0.0503(17) 0.0450(17) 0.0463(18) 0.0017(14) 0.0044(14) 0.0022(14)
C28 0.057(2) 0.060(2) 0.051(2) 0.0044(18) 0.0051(15) 0.0096(17)
C29 0.136(4) 0.109(3) 0.038(2) 0.013(2) -0.011(2) 0.011(3)
C30 0.310(8) 0.121(4) 0.049(3) -0.008(3) -0.015(4) -0.020(4)
C31 0.0557(19) 0.057(2) 0.0526(19) -0.0005(16) 0.0031(16) 0.0099(16)
C32 0.056(2) 0.079(3) 0.063(2) -0.011(2) -0.0002(17) 0.014(2)
C33 0.107(4) 0.178(5) 0.107(4) 0.021(4) 0.062(3) 0.000(3)
C34 0.187(6) 0.177(6) 0.119(4) 0.025(4) 0.053(4) -0.049(5)
N1 0.0464(14) 0.0469(14) 0.0524(15) -0.0050(12) 0.0002(12) 0.0027(11)
N2 0.0511(15) 0.0464(15) 0.0524(15) 0.0033(12) 0.0050(12) 0.0008(12)
N3 0.0463(15) 0.0818(19) 0.0575(17) -0.0083(15) -0.0038(14) 0.0100(16)
N4 0.071(2) 0.0538(19) 0.108(2) 0.0177(16) -0.0026(18) 0.0168(15)
O1 0.0744(15) 0.0752(15) 0.0545(14) -0.0124(12) 0.0030(11) -0.0102(12)
O2 0.111(2) 0.0504(14) 0.125(2) 0.0113(14) 0.0174(17) -0.0092(14)
O3 0.118(2) 0.0668(16) 0.0685(16) 0.0217(13) 0.0170(14) 0.0245(14)
O4 0.0871(16) 0.0706(15) 0.0425(13) 0.0051(12) -0.0042(11) 0.0018(12)
O5 0.0917(19) 0.106(2) 0.108(2) -0.0320(17) 0.0191(16) 0.0293(16)
O6 0.0740(16) 0.0967(19) 0.0737(17) 0.0075(14) 0.0234(13) 0.0006(14)
_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 C6 1.357(5) . ?
C1 C2 1.394(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.343(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.354(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.422(5) . ?
C7 C8 1.189(4) . ?
C8 C9 1.452(5) . ?
C9 C10 1.394(4) . ?
C9 C11 1.405(4) . ?
C10 C12 1.393(4) . ?
C10 C23 1.514(4) . ?
C11 C13 1.363(4) . ?
C11 H11 0.9300 . ?
C12 C14 1.419(4) . ?
C12 C24 1.519(4) . ?
C13 C14 1.380(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.438(5) . ?
C15 C16 1.189(5) . ?
C16 C17 1.429(5) . ?
C17 C18 1.375(5) . ?
C17 C22 1.391(5) . ?
C18 C19 1.367(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.382(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.348(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.353(6) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 N1 1.452(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 N2 1.445(3) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 O1 1.198(3) . ?
C25 N3 1.369(4) . ?
C25 N1 1.381(4) . ?
C26 O2 1.215(4) . ?
C26 N2 1.341(4) . ?
C26 N4 1.361(4) . ?
C27 N1 1.433(3) . ?
C27 N2 1.451(3) . ?
C27 C28 1.535(4) . ?
C27 C31 1.575(4) . ?
C28 O3 1.182(3) . ?
C28 O4 1.334(4) . ?
C29 C30 1.411(6) . ?
C29 O4 1.451(4) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 N3 1.431(4) . ?
C31 N4 1.446(4) . ?
C31 C32 1.512(4) . ?
C32 O5 1.188(4) . ?
C32 O6 1.316(4) . ?
C33 C34 1.453(7) . ?
C33 O6 1.478(5) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
N3 H3A 0.855(10) . ?
N4 H4A 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
C6 C1 C2 121.1(4) . . ?
C6 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C3 C2 C1 120.8(4) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 119.1(4) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 121.8(4) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 116.8(3) . . ?
C1 C6 C7 121.0(3) . . ?
C5 C6 C7 122.2(3) . . ?
C8 C7 C6 176.5(3) . . ?
C7 C8 C9 176.4(3) . . ?
C10 C9 C11 119.4(3) . . ?
C10 C9 C8 121.1(3) . . ?
C11 C9 C8 119.5(3) . . ?
C12 C10 C9 120.1(3) . . ?
C12 C10 C23 120.6(3) . . ?
C9 C10 C23 119.2(3) . . ?
C13 C11 C9 120.5(3) . . ?
C13 C11 H11 119.8 . . ?
C9 C11 H11 119.8 . . ?
C10 C12 C14 119.4(3) . . ?
C10 C12 C24 122.0(3) . . ?
C14 C12 C24 118.7(3) . . ?
C11 C13 C14 121.1(3) . . ?
C11 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C12 119.5(3) . . ?
C13 C14 C15 119.3(3) . . ?
C12 C14 C15 121.2(3) . . ?
C16 C15 C14 177.4(4) . . ?
C15 C16 C17 178.4(4) . . ?
C18 C17 C22 118.8(4) . . ?
C18 C17 C16 120.8(3) . . ?
C22 C17 C16 120.3(3) . . ?
C19 C18 C17 120.7(4) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 119.3(5) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 120.0(5) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 121.4(5) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C21 C22 C17 119.7(4) . . ?
C21 C22 H22 120.2 . . ?
C17 C22 H22 120.2 . . ?
N1 C23 C10 115.9(2) . . ?
N1 C23 H23A 108.3 . . ?
C10 C23 H23A 108.3 . . ?
N1 C23 H23B 108.3 . . ?
C10 C23 H23B 108.3 . . ?
H23A C23 H23B 107.4 . . ?
N2 C24 C12 114.7(2) . . ?
N2 C24 H24A 108.6 . . ?
C12 C24 H24A 108.6 . . ?
N2 C24 H24B 108.6 . . ?
C12 C24 H24B 108.6 . . ?
H24A C24 H24B 107.6 . . ?
O1 C25 N3 127.4(3) . . ?
O1 C25 N1 125.9(3) . . ?
N3 C25 N1 106.7(3) . . ?
O2 C26 N2 125.9(3) . . ?
O2 C26 N4 126.1(3) . . ?
N2 C26 N4 108.0(3) . . ?
N1 C27 N2 112.6(2) . . ?
N1 C27 C28 111.7(2) . . ?
N2 C27 C28 110.3(2) . . ?
N1 C27 C31 103.6(2) . . ?
N2 C27 C31 102.7(2) . . ?
C28 C27 C31 115.7(2) . . ?
O3 C28 O4 125.5(3) . . ?
O3 C28 C27 125.6(3) . . ?
O4 C28 C27 108.9(3) . . ?
C30 C29 O4 109.9(3) . . ?
C30 C29 H29A 109.7 . . ?
O4 C29 H29A 109.7 . . ?
C30 C29 H29B 109.7 . . ?
O4 C29 H29B 109.7 . . ?
H29A C29 H29B 108.2 . . ?
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 . . ?
N3 C31 N4 113.6(3) . . ?
N3 C31 C32 111.9(3) . . ?
N4 C31 C32 110.3(3) . . ?
N3 C31 C27 101.9(2) . . ?
N4 C31 C27 101.6(2) . . ?
C32 C31 C27 117.1(3) . . ?
O5 C32 O6 124.7(3) . . ?
O5 C32 C31 123.8(4) . . ?
O6 C32 C31 111.5(3) . . ?
C34 C33 O6 108.0(4) . . ?
C34 C33 H33A 110.1 . . ?
O6 C33 H33A 110.1 . . ?
C34 C33 H33B 110.1 . . ?
O6 C33 H33B 110.1 . . ?
H33A C33 H33B 108.4 . . ?
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 . . ?
C25 N1 C27 112.9(2) . . ?
C25 N1 C23 121.8(2) . . ?
C27 N1 C23 122.8(2) . . ?
C26 N2 C24 123.8(3) . . ?
C26 N2 C27 113.7(2) . . ?
C24 N2 C27 121.8(2) . . ?
C25 N3 C31 114.6(3) . . ?
C25 N3 H3A 119(2) . . ?
C31 N3 H3A 122(2) . . ?
C26 N4 C31 114.0(3) . . ?
C26 N4 H4A 132(3) . . ?
C31 N4 H4A 113(3) . . ?
C28 O4 C29 116.4(3) . . ?
C32 O6 C33 115.6(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
C6 C1 C2 C3 -0.6(7) . . . . ?
C1 C2 C3 C4 -0.5(8) . . . . ?
C2 C3 C4 C5 1.5(8) . . . . ?
C3 C4 C5 C6 -1.6(8) . . . . ?
C2 C1 C6 C5 0.6(6) . . . . ?
C2 C1 C6 C7 -179.2(4) . . . . ?
C4 C5 C6 C1 0.5(7) . . . . ?
C4 C5 C6 C7 -179.8(4) . . . . ?
C11 C9 C10 C12 0.6(4) . . . . ?
C8 C9 C10 C12 178.5(3) . . . . ?
C11 C9 C10 C23 177.6(3) . . . . ?
C8 C9 C10 C23 -4.5(4) . . . . ?
C10 C9 C11 C13 0.6(5) . . . . ?
C8 C9 C11 C13 -177.3(3) . . . . ?
C9 C10 C12 C14 -2.1(4) . . . . ?
C23 C10 C12 C14 -179.1(3) . . . . ?
C9 C10 C12 C24 177.3(3) . . . . ?
C23 C10 C12 C24 0.4(4) . . . . ?
C9 C11 C13 C14 -0.3(5) . . . . ?
C11 C13 C14 C12 -1.3(5) . . . . ?
C11 C13 C14 C15 178.1(3) . . . . ?
C10 C12 C14 C13 2.5(4) . . . . ?
C24 C12 C14 C13 -177.0(3) . . . . ?
C10 C12 C14 C15 -176.9(3) . . . . ?
C24 C12 C14 C15 3.7(4) . . . . ?
C22 C17 C18 C19 1.2(5) . . . . ?
C16 C17 C18 C19 179.3(3) . . . . ?
C17 C18 C19 C20 0.0(6) . . . . ?
C18 C19 C20 C21 -0.5(7) . . . . ?
C19 C20 C21 C22 -0.1(8) . . . . ?
C20 C21 C22 C17 1.3(8) . . . . ?
C18 C17 C22 C21 -1.8(6) . . . . ?
C16 C17 C22 C21 -179.9(4) . . . . ?
C12 C10 C23 N1 -57.0(4) . . . . ?
C9 C10 C23 N1 126.0(3) . . . . ?
C10 C12 C24 N2 57.4(4) . . . . ?
C14 C12 C24 N2 -123.1(3) . . . . ?
N1 C27 C28 O3 -0.3(4) . . . . ?
N2 C27 C28 O3 125.7(3) . . . . ?
C31 C27 C28 O3 -118.4(3) . . . . ?
N1 C27 C28 O4 179.8(2) . . . . ?
N2 C27 C28 O4 -54.2(3) . . . . ?
C31 C27 C28 O4 61.7(3) . . . . ?
N1 C27 C31 N3 2.3(3) . . . . ?
N2 C27 C31 N3 -115.0(2) . . . . ?
C28 C27 C31 N3 124.8(3) . . . . ?
N1 C27 C31 N4 119.7(2) . . . . ?
N2 C27 C31 N4 2.4(3) . . . . ?
C28 C27 C31 N4 -117.7(3) . . . . ?
N1 C27 C31 C32 -120.1(3) . . . . ?
N2 C27 C31 C32 122.6(3) . . . . ?
C28 C27 C31 C32 2.4(4) . . . . ?
N3 C31 C32 O5 116.3(4) . . . . ?
N4 C31 C32 O5 -11.1(5) . . . . ?
C27 C31 C32 O5 -126.6(3) . . . . ?
N3 C31 C32 O6 -64.5(3) . . . . ?
N4 C31 C32 O6 168.1(3) . . . . ?
C27 C31 C32 O6 52.6(4) . . . . ?
O1 C25 N1 C27 -173.9(3) . . . . ?
N3 C25 N1 C27 6.3(3) . . . . ?
O1 C25 N1 C23 -11.6(4) . . . . ?
N3 C25 N1 C23 168.6(2) . . . . ?
N2 C27 N1 C25 104.8(3) . . . . ?
C28 C27 N1 C25 -130.5(2) . . . . ?
C31 C27 N1 C25 -5.3(3) . . . . ?
N2 C27 N1 C23 -57.3(3) . . . . ?
C28 C27 N1 C23 67.4(3) . . . . ?
C31 C27 N1 C23 -167.4(2) . . . . ?
C10 C23 N1 C25 -85.6(3) . . . . ?
C10 C23 N1 C27 74.9(3) . . . . ?
O2 C26 N2 C24 8.0(5) . . . . ?
N4 C26 N2 C24 -171.4(3) . . . . ?
O2 C26 N2 C27 178.2(3) . . . . ?
N4 C26 N2 C27 -1.2(4) . . . . ?
C12 C24 N2 C26 92.7(3) . . . . ?
C12 C24 N2 C27 -76.7(3) . . . . ?
N1 C27 N2 C26 -111.6(3) . . . . ?
C28 C27 N2 C26 123.0(3) . . . . ?
C31 C27 N2 C26 -0.9(3) . . . . ?
N1 C27 N2 C24 58.8(3) . . . . ?
C28 C27 N2 C24 -66.6(3) . . . . ?
C31 C27 N2 C24 169.5(2) . . . . ?
O1 C25 N3 C31 175.6(3) . . . . ?
N1 C25 N3 C31 -4.7(3) . . . . ?
N4 C31 N3 C25 -107.1(3) . . . . ?
C32 C31 N3 C25 127.3(3) . . . . ?
C27 C31 N3 C25 1.4(3) . . . . ?
O2 C26 N4 C31 -176.3(3) . . . . ?
N2 C26 N4 C31 3.1(4) . . . . ?
N3 C31 N4 C26 105.2(3) . . . . ?
C32 C31 N4 C26 -128.3(3) . . . . ?
C27 C31 N4 C26 -3.5(4) . . . . ?
O3 C28 O4 C29 2.3(5) . . . . ?
C27 C28 O4 C29 -177.8(3) . . . . ?
C30 C29 O4 C28 -180.0(4) . . . . ?
O5 C32 O6 C33 -1.7(5) . . . . ?
C31 C32 O6 C33 179.1(3) . . . . ?
C34 C33 O6 C32 166.3(4) . . . . ?
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
C23 H23A O3 0.97 2.53 3.111(4) 118.5 .
C29 H29B O1 0.97 2.57 3.372(5) 140.3 1_554
N3 H3A O2 0.855(10) 2.011(19) 2.785(4) 150(3) 4
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max 0.314
_refine_diff_density_min -0.335
_refine_diff_density_rms 0.096
# Attachment '060712dm.cif'
data_060712dm
_database_code_depnum_ccdc_archive 'CCDC 671166'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety ?
_chemical_formula_sum 'C37 H35 N5 O7'
_chemical_formula_weight 661.70
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Triclinic
_symmetry_space_group_name_H-M P-1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 9.3165(8)
_cell_length_b 13.5731(12)
_cell_length_c 14.2720(13)
_cell_angle_alpha 87.817(2)
_cell_angle_beta 72.737(2)
_cell_angle_gamma 85.808(2)
_cell_volume 1718.6(3)
_cell_formula_units_Z 2
_cell_measurement_temperature 292(2)
_cell_measurement_reflns_used 3737
_cell_measurement_theta_min 0.00
_cell_measurement_theta_max 0.00
_exptl_crystal_description plate
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.04
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.279
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 696
_exptl_absorpt_coefficient_mu 0.090
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min 0.9735
_exptl_absorpt_correction_T_max 0.9964
_exptl_absorpt_process_details ?
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 292(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'CCD area detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 11983
_diffrn_reflns_av_R_equivalents 0.0219
_diffrn_reflns_av_sigmaI/netI 0.0392
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_theta_min 2.10
_diffrn_reflns_theta_max 26.00
_reflns_number_total 6665
_reflns_number_gt 4408
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker SMART'
_computing_cell_refinement 'Bruker SMART'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Bruker SHELXTL'
_computing_publication_material 'Bruker SHELXTL'
_refine_special_details
;
Refinement of 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^)+(0.0992P)^2^+0.0000P] 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 constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 6665
_refine_ls_number_parameters 445
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0864
_refine_ls_R_factor_gt 0.0581
_refine_ls_wR_factor_ref 0.1747
_refine_ls_wR_factor_gt 0.1592
_refine_ls_goodness_of_fit_ref 1.044
_refine_ls_restrained_S_all 1.044
_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 0.1628(3) 0.39943(19) 0.99704(19) 0.0737(7) Uani 1 1 d . . .
H1 H 0.1136 0.4148 0.9498 0.088 Uiso 1 1 calc R . .
C2 C 0.0820(3) 0.3703(2) 1.0896(2) 0.0891(8) Uani 1 1 d . . .
H2 H -0.0215 0.3655 1.1048 0.107 Uiso 1 1 calc R . .
C3 C 0.1532(4) 0.3483(2) 1.15946(19) 0.0848(8) Uani 1 1 d . . .
H3 H 0.0977 0.3296 1.2224 0.102 Uiso 1 1 calc R . .
C4 C 0.3063(3) 0.35377(19) 1.13740(18) 0.0778(7) Uani 1 1 d . . .
H4 H 0.3545 0.3379 1.1850 0.093 Uiso 1 1 calc R . .
C5 C 0.3882(3) 0.38271(16) 1.04465(16) 0.0625(6) Uani 1 1 d . . .
H5 H 0.4918 0.3866 1.0298 0.075 Uiso 1 1 calc R . .
C6 C 0.3173(2) 0.40603(14) 0.97345(15) 0.0531(5) Uani 1 1 d . . .
C7 C 0.3990(2) 0.43760(15) 0.87703(16) 0.0564(5) Uani 1 1 d . . .
C8 C 0.4630(2) 0.46761(15) 0.79647(16) 0.0545(5) Uani 1 1 d . . .
C9 C 0.5408(2) 0.50563(14) 0.70080(14) 0.0490(5) Uani 1 1 d . . .
C10 C 0.6937(2) 0.47982(16) 0.66030(16) 0.0591(5) Uani 1 1 d . . .
H10 H 0.7437 0.4379 0.6951 0.071 Uiso 1 1 calc R . .
C11 C 0.7706(2) 0.51519(17) 0.57051(17) 0.0620(6) Uani 1 1 d . . .
H11 H 0.8726 0.4970 0.5446 0.074 Uiso 1 1 calc R . .
C12 C 0.6985(2) 0.57885(14) 0.51600(14) 0.0512(5) Uani 1 1 d . . .
C13 C 0.5439(2) 0.60602(13) 0.55572(13) 0.0447(5) Uani 1 1 d . . .
C14 C 0.4654(2) 0.56915(13) 0.64863(13) 0.0444(5) Uani 1 1 d . . .
C15 C 0.7818(2) 0.61320(15) 0.42118(16) 0.0554(5) Uani 1 1 d . . .
C16 C 0.8515(2) 0.64178(16) 0.34172(17) 0.0610(6) Uani 1 1 d . . .
C17 C 0.9326(3) 0.68118(18) 0.24781(16) 0.0624(6) Uani 1 1 d . . .
C18 C 0.8872(4) 0.7734(2) 0.2187(2) 0.0954(9) Uani 1 1 d . . .
H18 H 0.8044 0.8082 0.2602 0.114 Uiso 1 1 calc R . .
C19 C 0.9617(5) 0.8152(3) 0.1294(2) 0.1286(14) Uani 1 1 d . . .
H19 H 0.9292 0.8775 0.1113 0.154 Uiso 1 1 calc R . .
C20 C 1.0811(5) 0.7659(4) 0.0690(3) 0.1213(14) Uani 1 1 d . . .
H20 H 1.1304 0.7942 0.0087 0.146 Uiso 1 1 calc R . .
C21 C 1.1321(3) 0.6738(4) 0.0945(2) 0.1072(12) Uani 1 1 d . . .
H21 H 1.2163 0.6409 0.0524 0.129 Uiso 1 1 calc R . .
C22 C 1.0552(3) 0.6296(2) 0.18555(18) 0.0797(8) Uani 1 1 d . . .
H22 H 1.0868 0.5669 0.2031 0.096 Uiso 1 1 calc R . .
C23 C 0.4650(2) 0.67185(13) 0.49660(13) 0.0479(5) Uani 1 1 d . . .
H23A H 0.5372 0.6877 0.4343 0.057 Uiso 1 1 calc R . .
H23B H 0.3876 0.6358 0.4829 0.057 Uiso 1 1 calc R . .
C24 C 0.2987(2) 0.59615(13) 0.69242(15) 0.0498(5) Uani 1 1 d . . .
H24A H 0.2451 0.5723 0.6499 0.060 Uiso 1 1 calc R . .
H24B H 0.2636 0.5625 0.7555 0.060 Uiso 1 1 calc R . .
C25 C 0.3070(2) 0.75073(15) 0.77519(14) 0.0496(5) Uani 1 1 d . . .
C26 C 0.4491(2) 0.85523(14) 0.51895(14) 0.0471(5) Uani 1 1 d . . .
C27 C 0.2571(2) 0.76706(13) 0.62581(13) 0.0447(5) Uani 1 1 d . . .
C28 C 0.1256(2) 0.74965(15) 0.58530(14) 0.0511(5) Uani 1 1 d . . .
C29 C -0.0176(4) 0.8201(3) 0.4849(3) 0.1103(12) Uani 1 1 d . . .
H29A H -0.0236 0.7524 0.4675 0.132 Uiso 1 1 calc R . .
H29B H 0.0035 0.8602 0.4253 0.132 Uiso 1 1 calc R . .
C30 C -0.1615(5) 0.8554(4) 0.5527(4) 0.1679(19) Uani 1 1 d . . .
H30A H -0.1882 0.8110 0.6082 0.252 Uiso 1 1 calc R . .
H30B H -0.2380 0.8581 0.5199 0.252 Uiso 1 1 calc R . .
H30C H -0.1528 0.9201 0.5744 0.252 Uiso 1 1 calc R . .
C31 C 0.2582(2) 0.87269(13) 0.66582(14) 0.0480(5) Uani 1 1 d . . .
C32 C 0.1080(3) 0.93292(16) 0.69717(15) 0.0583(6) Uani 1 1 d . . .
C33 C -0.1420(4) 0.9282(3) 0.8056(3) 0.1252(13) Uani 1 1 d . . .
H33A H -0.1489 0.9951 0.7801 0.150 Uiso 1 1 calc R . .
H33B H -0.2241 0.8934 0.7965 0.150 Uiso 1 1 calc R . .
C34 C -0.1541(6) 0.9304(4) 0.9092(3) 0.183(2) Uani 1 1 d . . .
H34A H -0.1562 0.8641 0.9354 0.275 Uiso 1 1 calc R . .
H34B H -0.2452 0.9676 0.9432 0.275 Uiso 1 1 calc R . .
H34C H -0.0691 0.9609 0.9175 0.275 Uiso 1 1 calc R . .
N1 N 0.26085(17) 0.70239(11) 0.70619(11) 0.0454(4) Uani 1 1 d . . .
N2 N 0.39608(17) 0.76351(11) 0.54459(11) 0.0462(4) Uani 1 1 d . . .
N3 N 0.3078(2) 0.84856(12) 0.75081(12) 0.0582(5) Uani 1 1 d . . .
H3A H 0.3353 0.8920 0.7832 0.070 Uiso 1 1 calc R . .
N4 N 0.36523(19) 0.91967(12) 0.58657(12) 0.0567(5) Uani 1 1 d . . .
H4A H 0.3751 0.9823 0.5825 0.068 Uiso 1 1 calc R . .
O1 O 0.33943(18) 0.71094(12) 0.84427(10) 0.0672(4) Uani 1 1 d . . .
O2 O 0.55345(16) 0.87426(10) 0.44653(10) 0.0593(4) Uani 1 1 d . . .
O3 O 0.05952(18) 0.67610(12) 0.59850(13) 0.0746(5) Uani 1 1 d . . .
O4 O 0.1043(2) 0.82473(12) 0.52916(13) 0.0817(5) Uani 1 1 d . . .
O5 O 0.0927(2) 1.01835(12) 0.67868(14) 0.0871(6) Uani 1 1 d . . .
O6 O 0.00275(18) 0.87811(12) 0.75191(13) 0.0837(5) Uani 1 1 d . . .
O7 O 0.3952(3) 0.00579(19) 0.84241(19) 0.1302(9) Uani 1 1 d . . .
N5 N 0.5502(3) 0.12989(19) 0.8048(2) 0.1090(8) Uani 1 1 d . . .
C37 C 0.4848(5) 0.0550(3) 0.7841(3) 0.1138(11) Uani 1 1 d . . .
H37 H 0.5095 0.0380 0.7184 0.137 Uiso 1 1 calc R . .
C35 C 0.5193(5) 0.1556(3) 0.9061(3) 0.176(2) Uani 1 1 d . . .
H35A H 0.4241 0.1929 0.9273 0.264 Uiso 1 1 d R . .
H35B H 0.5973 0.1946 0.9131 0.264 Uiso 1 1 d R . .
H35C H 0.5160 0.0964 0.9456 0.264 Uiso 1 1 d R . .
C36 C 0.6536(6) 0.1881(3) 0.7284(4) 0.170(2) Uani 1 1 d . . .
H36A H 0.6779 0.1551 0.6668 0.255 Uiso 1 1 calc R . .
H36B H 0.7442 0.1950 0.7459 0.255 Uiso 1 1 calc R . .
H36C H 0.6062 0.2523 0.7225 0.255 Uiso 1 1 calc R . .
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
C1 0.0603(15) 0.0897(18) 0.0733(16) 0.0124(13) -0.0225(13) -0.0134(13)
C2 0.0663(17) 0.106(2) 0.088(2) 0.0112(16) -0.0102(15) -0.0224(15)
C3 0.098(2) 0.0880(19) 0.0564(15) 0.0099(13) -0.0006(15) -0.0282(16)
C4 0.103(2) 0.0786(17) 0.0566(14) 0.0123(12) -0.0291(14) -0.0186(15)
C5 0.0641(14) 0.0660(14) 0.0608(14) 0.0078(11) -0.0233(11) -0.0109(11)
C6 0.0584(13) 0.0460(11) 0.0542(12) 0.0087(9) -0.0158(10) -0.0069(9)
C7 0.0590(13) 0.0520(12) 0.0588(13) 0.0093(10) -0.0191(11) -0.0056(10)
C8 0.0590(13) 0.0493(12) 0.0572(13) 0.0077(10) -0.0210(11) -0.0035(10)
C9 0.0533(12) 0.0460(11) 0.0483(11) 0.0028(9) -0.0155(9) -0.0072(9)
C10 0.0543(13) 0.0640(13) 0.0597(13) 0.0078(11) -0.0197(11) -0.0009(10)
C11 0.0432(12) 0.0704(14) 0.0703(15) -0.0003(12) -0.0138(11) -0.0018(10)
C12 0.0510(12) 0.0469(11) 0.0520(12) -0.0035(9) -0.0074(10) -0.0108(9)
C13 0.0505(12) 0.0376(10) 0.0464(11) -0.0016(8) -0.0133(9) -0.0096(8)
C14 0.0478(11) 0.0387(10) 0.0453(10) -0.0008(8) -0.0103(9) -0.0081(8)
C15 0.0537(12) 0.0521(12) 0.0559(13) -0.0061(10) -0.0074(11) -0.0085(10)
C16 0.0595(14) 0.0607(13) 0.0583(14) -0.0086(11) -0.0077(11) -0.0115(11)
C17 0.0628(14) 0.0704(15) 0.0498(12) -0.0061(11) -0.0065(11) -0.0181(12)
C18 0.130(3) 0.0724(18) 0.0653(16) -0.0009(13) 0.0025(16) -0.0184(17)
C19 0.195(4) 0.099(2) 0.074(2) 0.0101(18) -0.007(2) -0.046(3)
C20 0.137(3) 0.152(4) 0.067(2) -0.004(2) -0.002(2) -0.071(3)
C21 0.0596(17) 0.190(4) 0.0649(19) -0.041(2) 0.0028(14) -0.028(2)
C22 0.0564(15) 0.118(2) 0.0635(15) -0.0215(14) -0.0136(13) -0.0020(14)
C23 0.0539(12) 0.0458(11) 0.0419(10) 0.0000(8) -0.0094(9) -0.0096(9)
C24 0.0540(12) 0.0413(10) 0.0509(11) 0.0097(8) -0.0104(9) -0.0089(9)
C25 0.0467(11) 0.0541(12) 0.0451(11) 0.0018(9) -0.0101(9) -0.0015(9)
C26 0.0508(12) 0.0420(10) 0.0500(11) 0.0088(9) -0.0161(10) -0.0121(9)
C27 0.0489(11) 0.0403(10) 0.0435(10) 0.0062(8) -0.0113(9) -0.0073(8)
C28 0.0515(12) 0.0510(12) 0.0515(12) 0.0061(9) -0.0157(10) -0.0098(10)
C29 0.122(3) 0.120(3) 0.128(3) 0.042(2) -0.095(2) -0.034(2)
C30 0.103(3) 0.231(5) 0.203(5) 0.011(4) -0.101(3) 0.005(3)
C31 0.0535(12) 0.0409(10) 0.0488(11) 0.0018(8) -0.0136(9) -0.0060(9)
C32 0.0676(15) 0.0473(12) 0.0559(13) 0.0039(10) -0.0132(11) 0.0002(10)
C33 0.076(2) 0.122(3) 0.141(3) 0.014(2) 0.013(2) 0.0296(19)
C34 0.206(5) 0.160(4) 0.118(3) -0.003(3) 0.045(3) 0.024(4)
N1 0.0498(9) 0.0413(8) 0.0439(9) 0.0073(7) -0.0119(7) -0.0067(7)
N2 0.0494(9) 0.0414(8) 0.0439(9) 0.0059(7) -0.0070(7) -0.0097(7)
N3 0.0745(12) 0.0494(10) 0.0579(10) -0.0040(8) -0.0292(9) -0.0078(9)
N4 0.0640(11) 0.0378(9) 0.0607(10) 0.0043(8) -0.0049(9) -0.0131(8)
O1 0.0802(11) 0.0746(10) 0.0498(9) 0.0048(8) -0.0263(8) 0.0030(8)
O2 0.0616(9) 0.0523(8) 0.0573(9) 0.0108(7) -0.0057(7) -0.0167(7)
O3 0.0720(11) 0.0682(10) 0.0951(12) 0.0164(9) -0.0391(9) -0.0273(9)
O4 0.0966(13) 0.0749(11) 0.0965(12) 0.0336(10) -0.0627(11) -0.0266(9)
O5 0.0931(13) 0.0503(10) 0.1061(14) 0.0098(9) -0.0161(11) 0.0092(9)
O6 0.0598(10) 0.0720(11) 0.0965(13) 0.0193(9) 0.0065(9) 0.0087(8)
O7 0.171(3) 0.1054(17) 0.1190(18) -0.0180(14) -0.0399(17) -0.0472(17)
N5 0.125(2) 0.0794(16) 0.135(2) -0.0114(16) -0.0542(18) -0.0136(15)
C37 0.142(3) 0.093(2) 0.125(3) -0.010(2) -0.065(3) -0.018(2)
C35 0.175(4) 0.165(4) 0.175(4) -0.092(4) -0.013(3) -0.052(3)
C36 0.206(5) 0.138(4) 0.186(4) 0.068(3) -0.081(4) -0.078(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.371(4) . ?
C1 C6 1.387(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.366(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.427(3) . ?
C7 C8 1.199(3) . ?
C8 C9 1.439(3) . ?
C9 C10 1.393(3) . ?
C9 C14 1.402(3) . ?
C10 C11 1.358(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.406(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.409(3) . ?
C12 C15 1.426(3) . ?
C13 C14 1.404(2) . ?
C13 C23 1.505(3) . ?
C14 C24 1.515(3) . ?
C15 C16 1.193(3) . ?
C16 C17 1.434(3) . ?
C17 C18 1.381(4) . ?
C17 C22 1.383(3) . ?
C18 C19 1.380(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.340(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.380(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.418(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 N2 1.455(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 N1 1.466(2) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 O1 1.211(2) . ?
C25 N3 1.360(3) . ?
C25 N1 1.388(2) . ?
C26 O2 1.225(2) . ?
C26 N4 1.350(3) . ?
C26 N2 1.369(2) . ?
C27 N1 1.425(2) . ?
C27 N2 1.458(2) . ?
C27 C28 1.537(3) . ?
C27 C31 1.565(2) . ?
C28 O3 1.191(2) . ?
C28 O4 1.312(2) . ?
C29 O4 1.460(3) . ?
C29 C30 1.461(5) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 N4 1.432(2) . ?
C31 N3 1.440(3) . ?
C31 C32 1.521(3) . ?
C32 O5 1.187(2) . ?
C32 O6 1.316(3) . ?
C33 C34 1.451(6) . ?
C33 O6 1.469(3) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
N3 H3A 0.8600 . ?
N4 H4A 0.8600 . ?
O7 C37 1.209(4) . ?
N5 C37 1.309(4) . ?
N5 C35 1.439(5) . ?
N5 C36 1.472(5) . ?
C37 H37 0.9300 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.4(2) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.4(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 118.9(2) . . ?
C5 C6 C7 121.6(2) . . ?
C1 C6 C7 119.4(2) . . ?
C8 C7 C6 177.1(2) . . ?
C7 C8 C9 178.6(2) . . ?
C10 C9 C14 119.72(18) . . ?
C10 C9 C8 119.34(19) . . ?
C14 C9 C8 120.93(18) . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 121.1(2) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C13 119.11(18) . . ?
C11 C12 C15 119.65(19) . . ?
C13 C12 C15 121.23(19) . . ?
C14 C13 C12 119.39(18) . . ?
C14 C13 C23 121.23(17) . . ?
C12 C13 C23 119.36(17) . . ?
C9 C14 C13 119.98(17) . . ?
C9 C14 C24 119.58(16) . . ?
C13 C14 C24 120.43(17) . . ?
C16 C15 C12 179.9(2) . . ?
C15 C16 C17 177.1(2) . . ?
C18 C17 C22 118.9(2) . . ?
C18 C17 C16 119.1(2) . . ?
C22 C17 C16 122.0(2) . . ?
C19 C18 C17 121.6(3) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C20 C19 C18 119.8(4) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 121.2(3) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C22 119.5(3) . . ?
C20 C21 H21 120.3 . . ?
C22 C21 H21 120.3 . . ?
C17 C22 C21 119.0(3) . . ?
C17 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
N2 C23 C13 114.04(15) . . ?
N2 C23 H23A 108.7 . . ?
C13 C23 H23A 108.7 . . ?
N2 C23 H23B 108.7 . . ?
C13 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
N1 C24 C14 114.10(15) . . ?
N1 C24 H24A 108.7 . . ?
C14 C24 H24A 108.7 . . ?
N1 C24 H24B 108.7 . . ?
C14 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
O1 C25 N3 127.4(2) . . ?
O1 C25 N1 124.92(19) . . ?
N3 C25 N1 107.64(17) . . ?
O2 C26 N4 126.78(17) . . ?
O2 C26 N2 125.24(18) . . ?
N4 C26 N2 107.97(16) . . ?
N1 C27 N2 114.44(16) . . ?
N1 C27 C28 112.40(15) . . ?
N2 C27 C28 108.52(15) . . ?
N1 C27 C31 104.19(14) . . ?
N2 C27 C31 100.87(13) . . ?
C28 C27 C31 116.02(16) . . ?
O3 C28 O4 125.37(19) . . ?
O3 C28 C27 124.56(19) . . ?
O4 C28 C27 109.93(16) . . ?
O4 C29 C30 110.9(3) . . ?
O4 C29 H29A 109.5 . . ?
C30 C29 H29A 109.5 . . ?
O4 C29 H29B 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 108.1 . . ?
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 . . ?
N4 C31 N3 115.11(16) . . ?
N4 C31 C32 111.78(16) . . ?
N3 C31 C32 109.20(16) . . ?
N4 C31 C27 102.92(14) . . ?
N3 C31 C27 100.67(14) . . ?
C32 C31 C27 116.81(16) . . ?
O5 C32 O6 126.0(2) . . ?
O5 C32 C31 123.8(2) . . ?
O6 C32 C31 110.08(18) . . ?
C34 C33 O6 109.7(3) . . ?
C34 C33 H33A 109.7 . . ?
O6 C33 H33A 109.7 . . ?
C34 C33 H33B 109.7 . . ?
O6 C33 H33B 109.7 . . ?
H33A C33 H33B 108.2 . . ?
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 . . ?
C25 N1 C27 110.59(15) . . ?
C25 N1 C24 119.35(16) . . ?
C27 N1 C24 121.38(15) . . ?
C26 N2 C23 125.36(16) . . ?
C26 N2 C27 112.20(15) . . ?
C23 N2 C27 122.42(14) . . ?
C25 N3 C31 113.76(16) . . ?
C25 N3 H3A 123.1 . . ?
C31 N3 H3A 123.1 . . ?
C26 N4 C31 112.89(15) . . ?
C26 N4 H4A 123.6 . . ?
C31 N4 H4A 123.6 . . ?
C28 O4 C29 116.92(19) . . ?
C32 O6 C33 117.8(2) . . ?
C37 N5 C35 118.5(3) . . ?
C37 N5 C36 122.3(3) . . ?
C35 N5 C36 119.3(3) . . ?
O7 C37 N5 126.0(4) . . ?
O7 C37 H37 117.0 . . ?
N5 C37 H37 117.0 . . ?
N5 C35 H35A 109.5 . . ?
N5 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
N5 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N5 C36 H36A 109.5 . . ?
N5 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N5 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 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
C6 C1 C2 C3 0.5(4) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C5 C6 C7 179.1(2) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
C2 C1 C6 C7 -179.3(2) . . . . ?
C5 C6 C7 C8 -129(4) . . . . ?
C1 C6 C7 C8 50(5) . . . . ?
C6 C7 C8 C9 68(12) . . . . ?
C7 C8 C9 C10 88(10) . . . . ?
C7 C8 C9 C14 -91(10) . . . . ?
C14 C9 C10 C11 -0.3(3) . . . . ?
C8 C9 C10 C11 -179.44(19) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 C13 0.0(3) . . . . ?
C10 C11 C12 C15 -178.84(19) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C15 C12 C13 C14 178.89(16) . . . . ?
C11 C12 C13 C23 -178.33(17) . . . . ?
C15 C12 C13 C23 0.5(3) . . . . ?
C10 C9 C14 C13 0.3(3) . . . . ?
C8 C9 C14 C13 179.49(16) . . . . ?
C10 C9 C14 C24 179.31(17) . . . . ?
C8 C9 C14 C24 -1.5(3) . . . . ?
C12 C13 C14 C9 -0.2(2) . . . . ?
C23 C13 C14 C9 178.12(16) . . . . ?
C12 C13 C14 C24 -179.20(16) . . . . ?
C23 C13 C14 C24 -0.8(2) . . . . ?
C11 C12 C15 C16 96(100) . . . . ?
C13 C12 C15 C16 -82(100) . . . . ?
C12 C15 C16 C17 136(100) . . . . ?
C15 C16 C17 C18 -23(5) . . . . ?
C15 C16 C17 C22 157(5) . . . . ?
C22 C17 C18 C19 -0.4(4) . . . . ?
C16 C17 C18 C19 179.5(3) . . . . ?
C17 C18 C19 C20 0.0(5) . . . . ?
C18 C19 C20 C21 -0.5(6) . . . . ?
C19 C20 C21 C22 1.3(5) . . . . ?
C18 C17 C22 C21 1.1(4) . . . . ?
C16 C17 C22 C21 -178.8(2) . . . . ?
C20 C21 C22 C17 -1.6(4) . . . . ?
C14 C13 C23 N2 60.2(2) . . . . ?
C12 C13 C23 N2 -121.41(18) . . . . ?
C9 C14 C24 N1 120.86(18) . . . . ?
C13 C14 C24 N1 -60.2(2) . . . . ?
N1 C27 C28 O3 -19.6(3) . . . . ?
N2 C27 C28 O3 108.0(2) . . . . ?
C31 C27 C28 O3 -139.4(2) . . . . ?
N1 C27 C28 O4 164.57(17) . . . . ?
N2 C27 C28 O4 -67.8(2) . . . . ?
C31 C27 C28 O4 44.8(2) . . . . ?
N1 C27 C31 N4 135.69(16) . . . . ?
N2 C27 C31 N4 16.80(18) . . . . ?
C28 C27 C31 N4 -100.19(18) . . . . ?
N1 C27 C31 N3 16.59(18) . . . . ?
N2 C27 C31 N3 -102.30(16) . . . . ?
C28 C27 C31 N3 140.71(16) . . . . ?
N1 C27 C31 C32 -101.45(19) . . . . ?
N2 C27 C31 C32 139.65(17) . . . . ?
C28 C27 C31 C32 22.7(2) . . . . ?
N4 C31 C32 O5 -19.3(3) . . . . ?
N3 C31 C32 O5 109.2(2) . . . . ?
C27 C31 C32 O5 -137.5(2) . . . . ?
N4 C31 C32 O6 164.60(17) . . . . ?
N3 C31 C32 O6 -66.9(2) . . . . ?
C27 C31 C32 O6 46.4(2) . . . . ?
O1 C25 N1 C27 -169.84(19) . . . . ?
N3 C25 N1 C27 10.5(2) . . . . ?
O1 C25 N1 C24 -21.7(3) . . . . ?
N3 C25 N1 C24 158.66(16) . . . . ?
N2 C27 N1 C25 92.02(18) . . . . ?
C28 C27 N1 C25 -143.60(16) . . . . ?
C31 C27 N1 C25 -17.2(2) . . . . ?
N2 C27 N1 C24 -55.4(2) . . . . ?
C28 C27 N1 C24 69.0(2) . . . . ?
C31 C27 N1 C24 -164.57(15) . . . . ?
C14 C24 N1 C25 -67.5(2) . . . . ?
C14 C24 N1 C27 77.2(2) . . . . ?
O2 C26 N2 C23 7.3(3) . . . . ?
N4 C26 N2 C23 -173.37(17) . . . . ?
O2 C26 N2 C27 -171.25(18) . . . . ?
N4 C26 N2 C27 8.1(2) . . . . ?
C13 C23 N2 C26 106.7(2) . . . . ?
C13 C23 N2 C27 -74.9(2) . . . . ?
N1 C27 N2 C26 -126.90(17) . . . . ?
C28 C27 N2 C26 106.67(17) . . . . ?
C31 C27 N2 C26 -15.7(2) . . . . ?
N1 C27 N2 C23 54.5(2) . . . . ?
C28 C27 N2 C23 -71.9(2) . . . . ?
C31 C27 N2 C23 165.73(16) . . . . ?
O1 C25 N3 C31 -177.96(19) . . . . ?
N1 C25 N3 C31 1.7(2) . . . . ?
N4 C31 N3 C25 -121.39(18) . . . . ?
C32 C31 N3 C25 111.94(19) . . . . ?
C27 C31 N3 C25 -11.5(2) . . . . ?
O2 C26 N4 C31 -176.13(19) . . . . ?
N2 C26 N4 C31 4.5(2) . . . . ?
N3 C31 N4 C26 94.6(2) . . . . ?
C32 C31 N4 C26 -140.05(18) . . . . ?
C27 C31 N4 C26 -13.9(2) . . . . ?
O3 C28 O4 C29 4.5(4) . . . . ?
C27 C28 O4 C29 -179.7(2) . . . . ?
C30 C29 O4 C28 84.5(4) . . . . ?
O5 C32 O6 C33 -8.2(4) . . . . ?
C31 C32 O6 C33 167.7(2) . . . . ?
C34 C33 O6 C32 -106.5(4) . . . . ?
C35 N5 C37 O7 2.5(6) . . . . ?
C36 N5 C37 O7 -177.5(4) . . . . ?
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
N3 H3A O7 0.86 1.98 2.833(3) 171.6 1_565
N4 H4A O2 0.86 2.09 2.936(2) 167.5 2_676
C3 H3 O3 0.93 2.54 3.452(3) 165.9 2_567
C29 H29B O5 0.97 2.47 3.333(3) 147.8 2_576
C30 H30B O2 0.96 2.46 3.417(4) 175.3 1_455
C24 H24A O3 0.97 2.41 3.041(3) 121.9 .
_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full 26.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max 0.259
_refine_diff_density_min -0.159
_refine_diff_density_rms 0.043