#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/28/4112863.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4112863
loop_
_publ_author_name
'Anxin Wu'
'Pritam Mukhopadhyay'
'Arindam Chakraborty'
'James C. Fettinger'
'Lyle Isaacs'
_publ_section_title
;
 Molecular Clips Form Isostructural Dimeric Aggregates from Benzene to
 Water
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10035
_journal_page_last               10043
_journal_paper_doi               10.1021/ja0486972
_journal_volume                  126
_journal_year                    2004
_chemical_formula_moiety         'C52.15 H54.30 N12 O17'
_chemical_formula_sum            'C52.15 H54.3 N12 O17'
_chemical_formula_weight         1121.18
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.5020(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.2117(7)
_cell_length_b                   15.3609(5)
_cell_length_c                   17.3442(6)
_cell_measurement_reflns_used    8419
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.535
_cell_measurement_theta_min      2.351
_cell_volume                     5010.1(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            44821
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.9867
_exptl_absorpt_correction_T_min  0.9682
_exptl_absorpt_correction_type   'empirical, SADABS (multi-scan)'
_exptl_absorpt_process_details   'Blessing,R.H.(1995).Acta Cryst.,A51,33-38.'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_meas      0
_exptl_crystal_description       Block
_exptl_crystal_F_000             2349
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     753
_refine_ls_number_reflns         11486
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0865P)²+0.2511P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1426
_refine_ls_wR_factor_ref         0.1595
_reflns_number_gt                7274
_reflns_number_total             11486
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0486972si20040307_015733.cif
_cod_data_source_block           Compound2
_cod_original_formula_sum        'C52.15 H54.30 N12 O17'
_cod_database_code               4112863
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'
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 0.35984(12) 0.35154(14) 0.49357(12) 0.0329(5) Uani 1 1 d . . .
H1A H 0.3260 0.3097 0.4559 0.039 Uiso 1 1 calc R . .
H1B H 0.4083 0.3347 0.4978 0.039 Uiso 1 1 calc R . .
C1A C 0.41177(10) 0.37875(13) 0.64727(12) 0.0285(4) Uani 1 1 d . . .
C1B C 0.47878(11) 0.32042(13) 0.67203(13) 0.0333(5) Uani 1 1 d . . .
C1C C 0.59466(13) 0.30357(17) 0.77560(19) 0.0548(7) Uani 1 1 d . . .
H1CA H 0.5866 0.2461 0.7964 0.066 Uiso 1 1 calc R . .
H1CB H 0.6154 0.2942 0.7326 0.066 Uiso 1 1 calc R . .
C1D C 0.64340(17) 0.3555(2) 0.8439(2) 0.0915(12) Uani 1 1 d . . .
H1DA H 0.6892 0.3255 0.8676 0.137 Uiso 1 1 calc R . .
H1DB H 0.6230 0.3632 0.8868 0.137 Uiso 1 1 calc R . .
H1DC H 0.6505 0.4126 0.8230 0.137 Uiso 1 1 calc R . .
N1 N 0.35533(9) 0.34494(11) 0.57556(10) 0.0301(4) Uani 1 1 d . . .
O1A O 0.48455(9) 0.25828(10) 0.63310(10) 0.0479(4) Uani 1 1 d . . .
O1B O 0.52676(8) 0.35127(10) 0.74006(10) 0.0426(4) Uani 1 1 d . . .
C2 C 0.29134(11) 0.34741(13) 0.58485(12) 0.0319(5) Uani 1 1 d . . .
C2A C 0.37689(10) 0.38584(12) 0.71483(11) 0.0269(4) Uani 1 1 d . . .
C2B C 0.40577(10) 0.31832(13) 0.78489(12) 0.0294(4) Uani 1 1 d . . .
C2C C 0.41100(13) 0.16652(14) 0.81052(14) 0.0406(5) Uani 1 1 d . . .
H2CA H 0.3878 0.1729 0.8515 0.049 Uiso 1 1 calc R . .
H2CB H 0.4631 0.1652 0.8406 0.049 Uiso 1 1 calc R . .
C2D C 0.38694(13) 0.08474(15) 0.76216(14) 0.0434(5) Uani 1 1 d . . .
H2DA H 0.3990 0.0348 0.8000 0.065 Uiso 1 1 calc R . .
H2DB H 0.4106 0.0788 0.7222 0.065 Uiso 1 1 calc R . .
H2DC H 0.3353 0.0868 0.7325 0.065 Uiso 1 1 calc R . .
N2 N 0.30179(8) 0.36973(10) 0.66602(9) 0.0271(4) Uani 1 1 d . . .
O2 O 0.23378(8) 0.33162(11) 0.53069(9) 0.0437(4) Uani 1 1 d . . .
O2A O 0.43477(9) 0.33508(10) 0.85681(9) 0.0449(4) Uani 1 1 d . . .
O2B O 0.39163(8) 0.23922(9) 0.75222(8) 0.0332(3) Uani 1 1 d . . .
C3 C 0.25102(10) 0.34183(13) 0.70271(12) 0.0296(4) Uani 1 1 d . . .
H3A H 0.2119 0.3100 0.6603 0.036 Uiso 1 1 calc R . .
H3B H 0.2750 0.3007 0.7483 0.036 Uiso 1 1 calc R . .
C3A C 0.25660(10) 0.46295(12) 0.80848(11) 0.0260(4) Uani 1 1 d . . .
C3B C 0.29255(10) 0.40438(14) 0.88533(12) 0.0312(4) Uani 1 1 d . . .
C3C C 0.37031(18) 0.4055(2) 1.02642(17) 0.0861(12) Uani 1 1 d . . .
H3CA H 0.3450 0.4097 1.0655 0.103 Uiso 1 1 calc R . .
H3CB H 0.3742 0.3432 1.0141 0.103 Uiso 1 1 calc R . .
C3D C 0.44006(15) 0.4425(2) 1.06348(19) 0.0689(8) Uani 1 1 d . . .
H3DA H 0.4662 0.4123 1.1155 0.103 Uiso 1 1 calc R . .
H3DB H 0.4360 0.5045 1.0747 0.103 Uiso 1 1 calc R . .
H3DC H 0.4657 0.4362 1.0255 0.103 Uiso 1 1 calc R . .
N3 N 0.22084(8) 0.41195(10) 0.73489(9) 0.0282(4) Uani 1 1 d . . .
O3A O 0.28557(9) 0.32700(10) 0.88418(9) 0.0440(4) Uani 1 1 d . . .
O3B O 0.32992(9) 0.45217(11) 0.94943(9) 0.0486(4) Uani 1 1 d . . .
C4 C 0.14918(10) 0.43000(13) 0.69949(12) 0.0308(4) Uani 1 1 d . . .
C4A C 0.19341(11) 0.52010(13) 0.81516(12) 0.0294(4) Uani 1 1 d . . .
C4B C 0.18467(14) 0.51670(16) 0.90011(15) 0.0433(6) Uani 1 1 d . A .
C4C C 0.1635(5) 0.4293(4) 1.0017(5) 0.0793(17) Uani 0.61 1 d PD A 2
H4CA H 0.2058 0.4576 1.0427 0.095 Uiso 0.61 1 calc PR A 2
H4CB H 0.1208 0.4600 1.0028 0.095 Uiso 0.61 1 calc PR A 2
C4D C 0.1612(4) 0.3489(5) 1.0230(5) 0.100(2) Uiso 0.61 1 d PD A 2
H4DA H 0.1569 0.3467 1.0774 0.150 Uiso 0.61 1 calc PR A 2
H4DB H 0.2049 0.3191 1.0257 0.150 Uiso 0.61 1 calc PR A 2
H4DC H 0.1201 0.3201 0.9819 0.150 Uiso 0.61 1 calc PR A 2
C4E C 0.1277(11) 0.4209(19) 0.9751(14) 0.126(12) Uiso 0.25 1 d PD A 1
H4E1 H 0.1169 0.3578 0.9696 0.151 Uiso 0.25 1 calc PR A 1
H4E2 H 0.1638 0.4291 1.0314 0.151 Uiso 0.25 1 calc PR A 1
C4F C 0.0721(9) 0.4565(9) 0.9771(8) 0.095(5) Uiso 0.25 1 d PD A 1
H4F1 H 0.0717 0.5181 0.9622 0.142 Uiso 0.25 1 calc PR A 1
H4F2 H 0.0712 0.4516 1.0330 0.142 Uiso 0.25 1 calc PR A 1
H4F3 H 0.0302 0.4274 0.9375 0.142 Uiso 0.25 1 calc PR A 1
C4G C 0.1654(9) 0.4347(9) 1.0011(8) 0.0793(17) Uani 0.15 1 d PRD A 3
H4G1 H 0.1703 0.4945 1.0237 0.095 Uiso 0.15 1 calc PR A 3
H4G2 H 0.1184 0.4124 0.9974 0.095 Uiso 0.15 1 calc PR A 3
C4H C 0.2112(10) 0.3895(13) 1.0497(12) 0.060(5) Uiso 0.15 1 d PD A 3
H4H1 H 0.1920 0.3608 1.0874 0.090 Uiso 0.15 1 calc PR A 3
H4H2 H 0.2518 0.4259 1.0817 0.090 Uiso 0.15 1 calc PR A 3
H4H3 H 0.2267 0.3454 1.0191 0.090 Uiso 0.15 1 calc PR A 3
N4 N 0.13189(9) 0.48575(11) 0.74987(11) 0.0326(4) Uani 1 1 d . . .
O4 O 0.10849(8) 0.40035(10) 0.63430(9) 0.0410(4) Uani 1 1 d . . .
O4A O 0.19409(14) 0.57828(13) 0.94436(12) 0.0776(7) Uani 1 1 d . . .
O4B O 0.16687(11) 0.43883(12) 0.91621(12) 0.0602(5) Uani 1 1 d D . .
C5 C 0.06223(11) 0.52824(14) 0.72201(15) 0.0390(5) Uani 1 1 d . . .
H5A H 0.0523 0.5471 0.7713 0.047 Uiso 1 1 calc R . .
H5B H 0.0255 0.4851 0.6918 0.047 Uiso 1 1 calc R . .
C5A C 0.05580(11) 0.60588(13) 0.66667(13) 0.0333(5) Uani 1 1 d . . .
C6 C 0.00188(12) 0.61061(15) 0.58753(14) 0.0396(5) Uani 1 1 d . . .
C6A C -0.09173(12) 0.50733(15) 0.58997(15) 0.0416(5) Uani 1 1 d . . .
C6B C -0.14463(11) 0.44137(15) 0.53901(14) 0.0387(5) Uani 1 1 d . . .
C6C C -0.19155(12) 0.45706(17) 0.45973(14) 0.0454(6) Uani 1 1 d . . .
H6CA H -0.1897 0.5102 0.4326 0.054 Uiso 1 1 calc R . .
C6D C -0.24128(13) 0.39466(18) 0.42018(15) 0.0508(6) Uani 1 1 d . . .
H6DA H -0.2743 0.4073 0.3661 0.061 Uiso 1 1 calc R . .
C6E C -0.19934(14) 0.30278(17) 0.52880(16) 0.0531(7) Uani 1 1 d . . .
H6EA H -0.2006 0.2475 0.5529 0.064 Uiso 1 1 calc R . .
C6F C -0.14917(13) 0.36209(17) 0.57506(15) 0.0484(6) Uani 1 1 d . . .
H6FA H -0.1186 0.3490 0.6301 0.058 Uiso 1 1 calc R . .
N6 N -0.04939(10) 0.54294(12) 0.55382(12) 0.0428(5) Uani 1 1 d . . .
H6A H -0.0537 0.5227 0.5048 0.051 Uiso 1 1 calc R . .
N6D N -0.24591(12) 0.31768(15) 0.45313(13) 0.0534(5) Uani 1 1 d . . .
O6A O -0.08692(9) 0.52365(12) 0.66118(11) 0.0525(4) Uani 1 1 d . . .
C7 C -0.00093(14) 0.68152(16) 0.53689(15) 0.0494(6) Uani 1 1 d . . .
H7A H -0.0370 0.6839 0.4832 0.059 Uiso 1 1 calc R . .
C8 C 0.04717(15) 0.74807(17) 0.56268(15) 0.0528(7) Uani 1 1 d . . .
H8A H 0.0446 0.7959 0.5269 0.063 Uiso 1 1 calc R . .
C9 C 0.09986(13) 0.74549(14) 0.64155(14) 0.0414(5) Uani 1 1 d . B .
C9A C 0.10410(11) 0.67479(13) 0.69349(13) 0.0330(5) Uani 1 1 d . . .
C9B C 0.1560(3) 0.8769(3) 0.6206(2) 0.0719(11) Uani 0.82 1 d PD B 1
H9BA H 0.1917 0.9190 0.6532 0.108 Uiso 0.82 1 calc PR B 1
H9BB H 0.1105 0.9067 0.5929 0.108 Uiso 0.82 1 calc PR B 1
H9BC H 0.1717 0.8503 0.5788 0.108 Uiso 0.82 1 calc PR B 1
C9C C 0.1898(8) 0.8364(12) 0.6390(10) 0.055(4) Uiso 0.18 1 d PD B 2
H9C1 H 0.2187 0.8849 0.6705 0.083 Uiso 0.18 1 calc PR B 2
H9C2 H 0.1628 0.8554 0.5822 0.083 Uiso 0.18 1 calc PR B 2
H9C3 H 0.2209 0.7878 0.6380 0.083 Uiso 0.18 1 calc PR B 2
O9 O 0.14745(11) 0.81214(11) 0.67297(10) 0.0592(5) Uani 1 1 d D . .
C10 C 0.16020(11) 0.67756(13) 0.78046(13) 0.0321(4) Uani 1 1 d . . .
H10A H 0.1860 0.7336 0.7879 0.039 Uiso 1 1 calc R . .
H10B H 0.1360 0.6760 0.8208 0.039 Uiso 1 1 calc R . .
N10 N 0.21192(9) 0.60667(10) 0.79953(10) 0.0292(4) Uani 1 1 d . . .
C11 C 0.27674(10) 0.61239(13) 0.79284(11) 0.0279(4) Uani 1 1 d . . .
N11 N 0.30439(8) 0.52848(10) 0.79875(10) 0.0277(4) Uani 1 1 d . . .
O11 O 0.30583(8) 0.67811(9) 0.78381(9) 0.0362(3) Uani 1 1 d . . .
C12 C 0.37888(10) 0.51510(13) 0.81214(12) 0.0286(4) Uani 1 1 d . . .
H12A H 0.4003 0.4784 0.8621 0.034 Uiso 1 1 calc R . .
H12B H 0.4032 0.5722 0.8238 0.034 Uiso 1 1 calc R . .
N12 N 0.39278(9) 0.47457(10) 0.74380(10) 0.0277(4) Uani 1 1 d . . .
C13 C 0.42103(10) 0.52235(13) 0.69540(12) 0.0286(4) Uani 1 1 d . . .
N13 N 0.43059(9) 0.46757(11) 0.63859(10) 0.0292(4) Uani 1 1 d . . .
O13 O 0.43586(8) 0.59911(9) 0.70359(9) 0.0384(4) Uani 1 1 d . . .
C14 C 0.45358(11) 0.49549(14) 0.57170(12) 0.0321(4) Uani 1 1 d . . .
H14A H 0.4853 0.4506 0.5630 0.039 Uiso 1 1 calc R . .
H14B H 0.4811 0.5502 0.5881 0.039 Uiso 1 1 calc R . .
C14A C 0.39163(11) 0.50995(14) 0.49189(12) 0.0317(4) Uani 1 1 d . . .
C15 C 0.37950(12) 0.59206(14) 0.45548(13) 0.0361(5) Uani 1 1 d . . .
C15A C 0.40972(14) 0.74335(15) 0.47701(17) 0.0519(6) Uani 1 1 d . . .
H15A H 0.4505 0.7806 0.5067 0.078 Uiso 1 1 calc R . .
H15B H 0.3710 0.7551 0.4969 0.078 Uiso 1 1 calc R . .
H15C H 0.3935 0.7556 0.4175 0.078 Uiso 1 1 calc R . .
O15 O 0.43042(8) 0.65379(10) 0.49160(10) 0.0449(4) Uani 1 1 d . . .
C16 C 0.31875(12) 0.60749(16) 0.38512(14) 0.0415(5) Uani 1 1 d . . .
H16A H 0.3110 0.6633 0.3597 0.050 Uiso 1 1 calc R . .
C17 C 0.27015(12) 0.54159(15) 0.35275(14) 0.0405(5) Uani 1 1 d . . .
H17A H 0.2282 0.5529 0.3061 0.049 Uiso 1 1 calc R . .
C18 C 0.28186(11) 0.45876(14) 0.38764(13) 0.0347(5) Uani 1 1 d . . .
C18A C 0.34369(11) 0.44165(14) 0.45620(12) 0.0312(4) Uani 1 1 d . . .
C18B C 0.18862(12) 0.37929(17) 0.27758(15) 0.0454(6) Uani 1 1 d . . .
C18C C 0.12598(12) 0.31922(17) 0.26093(15) 0.0448(6) Uani 1 1 d . . .
C18D C 0.06959(15) 0.3278(2) 0.18627(17) 0.0693(9) Uani 1 1 d . . .
H18A H 0.0717 0.3685 0.1460 0.083 Uiso 1 1 calc R . .
C18E C 0.01057(16) 0.2767(3) 0.17119(19) 0.0768(10) Uani 1 1 d . . .
H18B H -0.0279 0.2843 0.1199 0.092 Uiso 1 1 calc R . .
C18F C 0.05778(15) 0.20893(19) 0.2930(2) 0.0641(8) Uani 1 1 d . . .
H18C H 0.0547 0.1663 0.3312 0.077 Uiso 1 1 calc R . .
C18G C 0.11969(14) 0.25817(17) 0.31494(18) 0.0565(7) Uani 1 1 d . . .
H18D H 0.1571 0.2494 0.3669 0.068 Uiso 1 1 calc R . .
N18 N 0.22948(10) 0.39219(13) 0.35772(11) 0.0404(4) Uani 1 1 d . . .
H18E H 0.2234 0.3568 0.3945 0.048 Uiso 1 1 calc R . .
N18E N 0.00353(12) 0.21737(17) 0.22313(16) 0.0644(7) Uani 1 1 d . . .
O18A O 0.19953(11) 0.41513(14) 0.22012(11) 0.0657(6) Uani 1 1 d . . .
O21 O -0.0406(3) 0.4552(4) 0.8283(4) 0.142(2) Uani 0.60 1 d P C 4
O31 O 0.017(3) 0.502(4) 0.928(4) 0.19(2) Uiso 0.10 1 d P D 4
O41 O -0.0005(10) 0.5354(11) 0.9714(11) 0.182(6) Uiso 0.15 1 d P . 4
O32 O -0.0005(10) 0.5354(11) 0.9714(11) 0.182(6) Uiso 0.15 1 d P E 5
H32 H 0.0247 0.4904 0.9852 0.273 Uiso 0.15 1 calc PR E 5
C32 C 0.003(4) 0.569(5) 0.897(4) 0.25(3) Uiso 0.15 1 d P E 5
H32A H 0.0292 0.6244 0.9084 0.371 Uiso 0.15 1 calc PR E 5
H32B H -0.0451 0.5790 0.8566 0.371 Uiso 0.15 1 calc PR E 5
H32C H 0.0277 0.5275 0.8739 0.371 Uiso 0.15 1 calc PR E 5
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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
N1 C1 C18A 113.56(17) .
N1 C1 H1A 108.9 .
C18A C1 H1A 108.9 .
N1 C1 H1B 108.9 .
C18A C1 H1B 108.9 .
H1A C1 H1B 107.7 .
N13 C1A N1 114.03(16) .
N13 C1A C1B 109.86(16) .
N1 C1A C1B 111.47(16) .
N13 C1A C2A 102.69(15) .
N1 C1A C2A 103.78(15) .
C1B C1A C2A 114.70(15) .
O1A C1B O1B 127.0(2) .
O1A C1B C1A 124.08(19) .
O1B C1B C1A 108.90(17) .
C1D C1C O1B 108.2(2) .
C1D C1C H1CA 110.0 .
O1B C1C H1CA 110.0 .
C1D C1C H1CB 110.0 .
O1B C1C H1CB 110.0 .
H1CA C1C H1CB 108.4 .
C1C C1D H1DA 109.5 .
C1C C1D H1DB 109.5 .
H1DA C1D H1DB 109.5 .
C1C C1D H1DC 109.5 .
H1DA C1D H1DC 109.5 .
H1DB C1D H1DC 109.5 .
C2 N1 C1A 111.93(16) .
C2 N1 C1 120.94(17) .
C1A N1 C1 120.18(17) .
C1B O1B C1C 117.65(18) .
O2 C2 N1 125.57(19) .
O2 C2 N2 125.2(2) .
N1 C2 N2 109.21(17) .
N12 C2A N2 114.29(15) .
N12 C2A C2B 112.87(15) .
N2 C2A C2B 110.81(16) .
N12 C2A C1A 102.72(15) .
N2 C2A C1A 102.11(14) .
C2B C2A C1A 113.34(15) .
O2A C2B O2B 126.10(19) .
O2A C2B C2A 125.24(18) .
O2B C2B C2A 108.65(16) .
O2B C2C C2D 107.80(17) .
O2B C2C H2CA 110.1 .
C2D C2C H2CA 110.1 .
O2B C2C H2CB 110.1 .
C2D C2C H2CB 110.1 .
H2CA C2C H2CB 108.5 .
C2C C2D H2DA 109.5 .
C2C C2D H2DB 109.5 .
H2DA C2D H2DB 109.5 .
C2C C2D H2DC 109.5 .
H2DA C2D H2DC 109.5 .
H2DB C2D H2DC 109.5 .
C2 N2 C3 120.06(16) .
C2 N2 C2A 111.63(16) .
C3 N2 C2A 123.02(15) .
C2B O2B C2C 116.33(15) .
N3 C3 N2 114.44(16) .
N3 C3 H3A 108.7 .
N2 C3 H3A 108.7 .
N3 C3 H3B 108.7 .
N2 C3 H3B 108.7 .
H3A C3 H3B 107.6 .
N3 C3A N11 114.41(16) .
N3 C3A C3B 111.70(15) .
N11 C3A C3B 112.42(15) .
N3 C3A C4A 102.05(14) .
N11 C3A C4A 102.29(15) .
C3B C3A C4A 113.20(16) .
O3A C3B O3B 126.61(19) .
O3A C3B C3A 123.16(18) .
O3B C3B C3A 110.23(17) .
C3D C3C O3B 109.9(2) .
C3D C3C H3CA 109.7 .
O3B C3C H3CA 109.7 .
C3D C3C H3CB 109.7 .
O3B C3C H3CB 109.7 .
H3CA C3C H3CB 108.2 .
C3C C3D H3DA 109.5 .
C3C C3D H3DB 109.5 .
H3DA C3D H3DB 109.5 .
C3C C3D H3DC 109.5 .
H3DA C3D H3DC 109.5 .
H3DB C3D H3DC 109.5 .
C4 N3 C3A 112.83(16) .
C4 N3 C3 120.05(16) .
C3A N3 C3 126.80(15) .
C3B O3B C3C 116.8(2) .
O4 C4 N4 126.05(19) .
O4 C4 N3 125.5(2) .
N4 C4 N3 108.46(16) .
N10 C4A N4 113.64(16) .
N10 C4A C4B 109.87(17) .
N4 C4A C4B 111.66(18) .
N10 C4A C3A 103.08(16) .
N4 C4A C3A 103.04(15) .
C4B C4A C3A 115.22(16) .
O4A C4B O4B 125.5(2) .
O4A C4B C4A 122.7(2) .
O4B C4B C4A 111.7(2) .
C4D C4C O4B 113.0(6) .
C4D C4C H4CA 109.0 .
O4B C4C H4CA 109.0 .
C4D C4C H4CB 109.0 .
O4B C4C H4CB 109.0 .
H4CA C4C H4CB 107.8 .
C4C C4D H4DA 109.5 .
C4C C4D H4DB 109.5 .
H4DA C4D H4DB 109.5 .
C4C C4D H4DC 109.5 .
H4DA C4D H4DC 109.5 .
H4DB C4D H4DC 109.5 .
C4F C4E O4B 128.7(19) .
C4F C4E H4E1 105.1 .
O4B C4E H4E1 105.1 .
C4F C4E H4E2 105.1 .
O4B C4E H4E2 105.1 .
H4E1 C4E H4E2 105.9 .
C4E C4F H4F1 109.5 .
C4E C4F H4F2 109.5 .
H4F1 C4F H4F2 109.5 .
C4E C4F H4F3 109.5 .
H4F1 C4F H4F3 109.5 .
H4F2 C4F H4F3 109.5 .
C4H C4G O4B 115.2(15) .
C4H C4G H4G1 108.5 .
O4B C4G H4G1 108.5 .
C4H C4G H4G2 108.5 .
O4B C4G H4G2 108.5 .
H4G1 C4G H4G2 107.5 .
C4G C4H H4H1 109.5 .
C4G C4H H4H2 109.5 .
H4H1 C4H H4H2 109.5 .
C4G C4H H4H3 109.5 .
H4H1 C4H H4H3 109.5 .
H4H2 C4H H4H3 109.5 .
C4 N4 C4A 112.67(16) .
C4 N4 C5 120.80(17) .
C4A N4 C5 123.02(17) .
C4B O4B C4G 111.0(6) .
C4B O4B C4C 114.3(3) .
C4G O4B C4C 3.3(7) .
C4B O4B C4E 123.9(11) .
C4G O4B C4E 29.2(11) .
C4C O4B C4E 27.1(10) .
N4 C5 C5A 114.28(18) .
N4 C5 H5A 108.7 .
C5A C5 H5A 108.7 .
N4 C5 H5B 108.7 .
C5A C5 H5B 108.7 .
H5A C5 H5B 107.6 .
C9A C5A C6 118.8(2) .
C9A C5A C5 120.03(19) .
C6 C5A C5 121.2(2) .
C7 C6 C5A 119.7(2) .
C7 C6 N6 117.1(2) .
C5A C6 N6 123.1(2) .
O6A C6A N6 123.7(2) .
O6A C6A C6B 120.4(2) .
N6 C6A C6B 115.9(2) .
C6C C6B C6F 118.0(2) .
C6C C6B C6A 123.4(2) .
C6F C6B C6A 118.5(2) .
C6B C6C C6D 119.1(2) .
C6B C6C H6CA 120.5 .
C6D C6C H6CA 120.5 .
N6D C6D C6C 123.9(2) .
N6D C6D H6DA 118.0 .
C6C C6D H6DA 118.0 .
N6D C6E C6F 124.4(2) .
N6D C6E H6EA 117.8 .
C6F C6E H6EA 117.8 .
C6E C6F C6B 118.2(2) .
C6E C6F H6FA 120.9 .
C6B C6F H6FA 120.9 .
C6A N6 C6 126.3(2) .
C6A N6 H6A 116.9 .
C6 N6 H6A 116.9 .
C6E N6D C6D 116.3(2) .
C8 C7 C6 121.4(2) .
C8 C7 H7A 119.3 .
C6 C7 H7A 119.3 .
C7 C8 C9 119.7(2) .
C7 C8 H8A 120.1 .
C9 C8 H8A 120.1 .
O9 C9 C8 122.7(2) .
O9 C9 C9A 117.15(19) .
C8 C9 C9A 120.1(2) .
C9 C9A C5A 120.31(19) .
C9 C9A C10 117.81(19) .
C5A C9A C10 121.82(19) .
O9 C9B H9BA 109.5 .
O9 C9B H9BB 109.5 .
H9BA C9B H9BB 109.5 .
O9 C9B H9BC 109.5 .
H9BA C9B H9BC 109.5 .
H9BB C9B H9BC 109.5 .
O9 C9C H9C1 109.5 .
O9 C9C H9C2 109.5 .
H9C1 C9C H9C2 109.5 .
O9 C9C H9C3 109.5 .
H9C1 C9C H9C3 109.5 .
H9C2 C9C H9C3 109.5 .
C9C O9 C9 122.2(8) .
C9C O9 C9B 38.8(8) .
C9 O9 C9B 120.5(2) .
N10 C10 C9A 114.55(16) .
N10 C10 H10A 108.6 .
C9A C10 H10A 108.6 .
N10 C10 H10B 108.6 .
C9A C10 H10B 108.6 .
H10A C10 H10B 107.6 .
C11 N10 C4A 113.72(16) .
C11 N10 C10 124.35(17) .
C4A N10 C10 121.30(17) .
O11 C11 N10 126.55(18) .
O11 C11 N11 125.58(19) .
N10 C11 N11 107.87(16) .
C11 N11 C3A 112.66(16) .
C11 N11 C12 120.48(16) .
C3A N11 C12 125.47(16) .
N11 C12 N12 115.42(15) .
N11 C12 H12A 108.4 .
N12 C12 H12A 108.4 .
N11 C12 H12B 108.4 .
N12 C12 H12B 108.4 .
H12A C12 H12B 107.5 .
C13 N12 C2A 112.13(16) .
C13 N12 C12 120.83(16) .
C2A N12 C12 126.96(16) .
O13 C13 N13 126.22(19) .
O13 C13 N12 125.69(19) .
N13 C13 N12 108.07(17) .
C13 N13 C1A 113.37(16) .
C13 N13 C14 124.27(17) .
C1A N13 C14 122.27(16) .
N13 C14 C14A 111.95(17) .
N13 C14 H14A 109.2 .
C14A C14 H14A 109.2 .
N13 C14 H14B 109.2 .
C14A C14 H14B 109.2 .
H14A C14 H14B 107.9 .
C15 C14A C18A 119.83(18) .
C15 C14A C14 120.03(18) .
C18A C14A C14 120.06(18) .
O15 C15 C14A 116.22(18) .
O15 C15 C16 123.6(2) .
C14A C15 C16 120.1(2) .
O15 C15A H15A 109.5 .
O15 C15A H15B 109.5 .
H15A C15A H15B 109.5 .
O15 C15A H15C 109.5 .
H15A C15A H15C 109.5 .
H15B C15A H15C 109.5 .
C15 O15 C15A 117.50(18) .
C17 C16 C15 119.8(2) .
C17 C16 H16A 120.1 .
C15 C16 H16A 120.1 .
C16 C17 C18 120.8(2) .
C16 C17 H17A 119.6 .
C18 C17 H17A 119.6 .
C17 C18 C18A 119.88(19) .
C17 C18 N18 120.82(19) .
C18A C18 N18 119.18(19) .
C18 C18A C14A 119.35(19) .
C18 C18A C1 121.45(19) .
C14A C18A C1 119.20(18) .
O18A C18B N18 123.2(2) .
O18A C18B C18C 120.5(2) .
N18 C18B C18C 116.3(2) .
C18G C18C C18D 117.2(2) .
C18G C18C C18B 124.9(2) .
C18D C18C C18B 117.9(3) .
C18E C18D C18C 119.0(3) .
C18E C18D H18A 120.5 .
C18C C18D H18A 120.5 .
N18E C18E C18D 124.5(3) .
N18E C18E H18B 117.7 .
C18D C18E H18B 117.7 .
N18E C18F C18G 124.4(3) .
N18E C18F H18C 117.8 .
C18G C18F H18C 117.8 .
C18C C18G C18F 119.1(3) .
C18C C18G H18D 120.4 .
C18F C18G H18D 120.4 .
C18B N18 C18 125.0(2) .
C18B N18 H18E 117.5 .
C18 N18 H18E 117.5 .
C18F N18E C18E 115.8(3) .
O31 O41 O41 101(4) 3_567
H32A C32 H32B 109.5 .
H32A C32 H32C 109.5 .
H32B C32 H32C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.461(3) .
C1 C18A 1.512(3) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C1A N13 1.439(3) .
C1A N1 1.442(2) .
C1A C1B 1.548(3) .
C1A C2A 1.577(3) .
C1B O1A 1.199(2) .
C1B O1B 1.311(3) .
C1C C1D 1.468(4) .
C1C O1B 1.476(3) .
C1C H1CA 0.9900 .
C1C H1CB 0.9900 .
C1D H1DA 0.9800 .
C1D H1DB 0.9800 .
C1D H1DC 0.9800 .
N1 C2 1.361(3) .
C2 O2 1.222(2) .
C2 N2 1.388(3) .
C2A N12 1.447(2) .
C2A N2 1.463(2) .
C2A C2B 1.540(3) .
C2B O2A 1.196(2) .
C2B O2B 1.327(2) .
C2C O2B 1.460(2) .
C2C C2D 1.490(3) .
C2C H2CA 0.9900 .
C2C H2CB 0.9900 .
C2D H2DA 0.9800 .
C2D H2DB 0.9800 .
C2D H2DC 0.9800 .
N2 C3 1.456(3) .
C3 N3 1.447(3) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C3A N3 1.445(2) .
C3A N11 1.447(2) .
C3A C3B 1.551(3) .
C3A C4A 1.589(3) .
C3B O3A 1.196(2) .
C3B O3B 1.315(2) .
C3C C3D 1.435(4) .
C3C O3B 1.471(3) .
C3C H3CA 0.9900 .
C3C H3CB 0.9900 .
C3D H3DA 0.9800 .
C3D H3DB 0.9800 .
C3D H3DC 0.9800 .
N3 C4 1.378(2) .
C4 O4 1.217(2) .
C4 N4 1.357(3) .
C4A N10 1.434(3) .
C4A N4 1.440(3) .
C4A C4B 1.548(3) .
C4B O4A 1.189(3) .
C4B O4B 1.308(3) .
C4C C4D 1.296(9) .
C4C O4B 1.515(5) .
C4C H4CA 0.9900 .
C4C H4CB 0.9900 .
C4D H4DA 0.9800 .
C4D H4DB 0.9800 .
C4D H4DC 0.9800 .
C4E C4F 1.260(17) .
C4E O4B 1.530(15) .
C4E H4E1 0.9900 .
C4E H4E2 0.9900 .
C4F H4F1 0.9800 .
C4F H4F2 0.9800 .
C4F H4F3 0.9800 .
C4G C4H 1.215(16) .
C4G O4B 1.485(12) .
C4G H4G1 0.9900 .
C4G H4G2 0.9900 .
C4H H4H1 0.9800 .
C4H H4H2 0.9800 .
C4H H4H3 0.9800 .
N4 C5 1.464(3) .
C5 C5A 1.506(3) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C5A C9A 1.399(3) .
C5A C6 1.407(3) .
C6 C7 1.387(3) .
C6 N6 1.433(3) .
C6A O6A 1.229(3) .
C6A N6 1.348(3) .
C6A C6B 1.503(3) .
C6B C6C 1.376(3) .
C6B C6F 1.387(3) .
C6C C6D 1.376(3) .
C6C H6CA 0.9500 .
C6D N6D 1.331(3) .
C6D H6DA 0.9500 .
C6E N6D 1.325(3) .
C6E C6F 1.380(3) .
C6E H6EA 0.9500 .
C6F H6FA 0.9500 .
N6 H6A 0.8800 .
C7 C8 1.368(3) .
C7 H7A 0.9500 .
C8 C9 1.393(3) .
C8 H8A 0.9500 .
C9 O9 1.373(3) .
C9 C9A 1.394(3) .
C9A C10 1.520(3) .
C9B O9 1.400(4) .
C9B H9BA 0.9800 .
C9B H9BB 0.9800 .
C9B H9BC 0.9800 .
C9C O9 1.260(13) .
C9C H9C1 0.9800 .
C9C H9C2 0.9800 .
C9C H9C3 0.9800 .
C10 N10 1.461(2) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
N10 C11 1.360(3) .
C11 O11 1.207(2) .
C11 N11 1.394(2) .
N11 C12 1.451(2) .
C12 N12 1.455(2) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
N12 C13 1.386(3) .
C13 O13 1.212(2) .
C13 N13 1.362(3) .
N13 C14 1.463(3) .
C14 C14A 1.504(3) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C14A C15 1.391(3) .
C14A C18A 1.408(3) .
C15 O15 1.370(3) .
C15 C16 1.398(3) .
C15A O15 1.433(3) .
C15A H15A 0.9800 .
C15A H15B 0.9800 .
C15A H15C 0.9800 .
C16 C17 1.379(3) .
C16 H16A 0.9500 .
C17 C18 1.391(3) .
C17 H17A 0.9500 .
C18 C18A 1.398(3) .
C18 N18 1.426(3) .
C18B O18A 1.227(3) .
C18B N18 1.346(3) .
C18B C18C 1.507(3) .
C18C C18G 1.364(4) .
C18C C18D 1.382(4) .
C18D C18E 1.371(4) .
C18D H18A 0.9500 .
C18E N18E 1.325(4) .
C18E H18B 0.9500 .
C18F N18E 1.309(4) .
C18F C18G 1.391(4) .
C18F H18C 0.9500 .
C18G H18D 0.9500 .
N18 H18E 0.8800 .
O31 O41 1.07(6) .
O41 O41 1.47(3) 3_567
C32 H32A 0.9800 .
C32 H32B 0.9800 .
C32 H32C 0.9800 .
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 H6A O4 0.88 2.55 3.158(2) 127.3 3_566
N18 H18E O2 0.88 2.33 3.112(2) 148.6 .
