#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:37:26 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178399 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/21/4022194.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_4022194
loop_
_publ_author_name
'Stephen Hanessian'
'Dougal J. Ritson'
_publ_section_title
;
 Structure-Based Organic Synthesis of a Tricyclic N-Malayamycin Analogue
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9807
_journal_page_last               9817
_journal_paper_doi               10.1021/jo061904r
_journal_volume                  71
_journal_year                    2006
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_sum            'C13 H20 N4 O8'
_chemical_formula_weight         360.33
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 94.85(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.3388(14)
_cell_length_b                   5.1216(14)
_cell_length_c                   15.230(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      20.00
_cell_volume                     803.6(3)
_computing_cell_refinement       'CAD4 Program (Nonius 1989)'
_computing_data_collection       'CAD4 Program (Nonius 1989)'
_computing_data_reduction        'Local Program'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  Enraf-Nonius-CAD4
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_av_sigmaI/netI    0.0399
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15131
_diffrn_reflns_theta_full        69.94
_diffrn_reflns_theta_max         69.94
_diffrn_reflns_theta_min         2.91
_diffrn_standards_decay_%        -0.23
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.072
_exptl_absorpt_correction_T_max  0.9300
_exptl_absorpt_correction_T_min  0.5800
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'No absorption correction applied'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), XXXX Friedel Pairs'
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_coef       0.029(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3023
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0617
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1127P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1752
_refine_ls_wR_factor_ref         0.1848
_reflns_number_gt                2311
_reflns_number_total             3023
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo061904rsi20060922_043407.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (42
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (64
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (96 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4022194
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
O1 O 0.8581(3) 0.1904(5) 0.21189(18) 0.0668(8) Uani 1 1 d . . .
O2 O 1.1253(4) 0.4271(10) 0.2762(3) 0.1074(14) Uani 1 1 d . . .
H2 H 1.1774 0.5407 0.2932 0.161 Uiso 1 1 calc R . .
O3 O 0.9533(6) 0.5622(8) 0.4056(2) 0.1241(18) Uani 1 1 d . D .
O5 O 1.02504(19) 0.8032(5) 0.06489(15) 0.0511(6) Uani 1 1 d . . .
O6 O 0.6229(2) 1.0606(6) -0.0402(2) 0.0732(9) Uani 1 1 d . . .
N1 N 0.8231(2) 0.9201(6) 0.0126(2) 0.0500(7) Uani 1 1 d . . .
H1 H 0.8575 1.0411 -0.0170 0.060 Uiso 1 1 calc R . .
N2 N 0.6418(3) 0.7018(7) 0.0504(3) 0.0698(10) Uani 1 1 d . . .
H2A H 0.5592 0.6773 0.0463 0.084 Uiso 1 1 calc R . .
C1 C 0.9348(4) 0.3878(8) 0.1717(3) 0.0572(9) Uani 1 1 d . . .
H1A H 0.9990 0.3027 0.1375 0.069 Uiso 1 1 calc R . .
C2 C 1.0059(5) 0.5424(9) 0.2492(3) 0.0771(14) Uani 1 1 d . . .
H2C H 1.0160 0.7269 0.2341 0.092 Uiso 1 1 calc R . .
C3 C 0.9091(6) 0.5069(9) 0.3162(3) 0.0805(14) Uani 1 1 d . . .
H3A H 0.8323 0.6137 0.2994 0.097 Uiso 1 1 calc R . .
C4 C 0.8732(5) 0.2238(8) 0.3068(3) 0.0682(11) Uani 1 1 d . D .
H4A H 0.9468 0.1178 0.3308 0.082 Uiso 1 1 calc R . .
C5 C 0.7568(5) 0.1571(10) 0.3549(3) 0.0865(15) Uani 1 1 d D . .
H5A H 0.7338 -0.0283 0.3504 0.104 Uiso 0.34 1 calc PR A 1
H5B H 0.7412 -0.0316 0.3527 0.104 Uiso 0.33 1 calc PR A 2
H5C H 0.7615 -0.0336 0.3592 0.104 Uiso 0.33 1 calc PR A 3
C6 C 0.7911(5) 0.2450(8) 0.4506(2) 0.102(2) Uani 1 1 d D C .
H6A H 0.8575 0.1247 0.4765 0.122 Uiso 0.46 1 calc PR B 1
H6B H 0.8460 0.1170 0.4839 0.122 Uiso 0.28 1 calc PR B 2
H6C H 0.8511 0.1197 0.4809 0.122 Uiso 0.26 1 calc PR B 3
C7 C 0.8488(5) 0.5245(8) 0.4590(2) 0.148(4) Uani 1 1 d R . .
H7A H 0.7810 0.6503 0.4423 0.177 Uiso 1 1 calc R . .
H7B H 0.8791 0.5567 0.5201 0.177 Uiso 1 1 calc R . .
C10 C 0.9066(3) 0.7619(6) 0.0634(2) 0.0451(7) Uani 1 1 d . . .
C11 C 0.8472(3) 0.5588(7) 0.1116(2) 0.0514(8) Uani 1 1 d . . .
C12 C 0.7185(4) 0.5384(8) 0.1022(3) 0.0627(10) Uani 1 1 d . . .
H12 H 0.6793 0.4065 0.1325 0.075 Uiso 1 1 calc R . .
C13 C 0.6905(3) 0.9036(8) 0.0045(3) 0.0573(9) Uani 1 1 d . . .
O41 O 0.6972(11) 0.275(3) 0.5126(6) 0.088(2) Uani 0.46 1 d PD C 1
C81 C 0.6371(17) 0.033(4) 0.5327(10) 0.101(5) Uani 0.46 1 d PD C 1
H81A H 0.6074 -0.0537 0.4790 0.152 Uiso 0.46 1 calc PR C 1
H81B H 0.5646 0.0669 0.5666 0.152 Uiso 0.46 1 calc PR C 1
H81C H 0.6989 -0.0751 0.5662 0.152 Uiso 0.46 1 calc PR C 1
O42 O 0.6732(17) 0.300(5) 0.4924(10) 0.088(2) Uani 0.28 1 d PD C 2
C82 C 0.604(2) 0.061(7) 0.501(2) 0.101(5) Uani 0.28 1 d PD C 2
H82A H 0.5690 0.0029 0.4437 0.152 Uiso 0.28 1 calc PR C 2
H82B H 0.5339 0.0885 0.5376 0.152 Uiso 0.28 1 calc PR C 2
H82C H 0.6614 -0.0699 0.5270 0.152 Uiso 0.28 1 calc PR C 2
O43 O 0.6438(13) 0.169(3) 0.4660(7) 0.088(2) Uani 0.26 1 d PD C 3
C83 C 0.647(3) 0.141(7) 0.5587(13) 0.101(5) Uani 0.26 1 d PD C 3
H83A H 0.6580 0.3098 0.5859 0.152 Uiso 0.26 1 calc PR C 3
H83B H 0.7186 0.0307 0.5789 0.152 Uiso 0.26 1 calc PR C 3
H83C H 0.5675 0.0646 0.5740 0.152 Uiso 0.26 1 calc PR C 3
N31 N 0.6572(14) 0.323(3) 0.3150(14) 0.076(2) Uani 0.34 1 d PD D 1
H31 H 0.6649 0.4903 0.3120 0.092 Uiso 0.34 1 calc PR D 1
C71 C 0.557(2) 0.202(3) 0.285(2) 0.075(3) Uani 0.34 1 d PD D 1
O71 O 0.5239(13) -0.023(2) 0.2628(11) 0.093(3) Uani 0.34 1 d PD D 1
N41 N 0.4514(19) 0.358(5) 0.2510(17) 0.125(6) Uani 0.34 1 d PD D 1
H41A H 0.3849 0.2868 0.2229 0.188 Uiso 0.34 1 calc PR D 1
H41B H 0.4536 0.5244 0.2588 0.188 Uiso 0.34 1 calc PR D 1
N32 N 0.6423(12) 0.292(2) 0.3269(16) 0.076(2) Uani 0.33 1 d PD D 2
H32 H 0.6289 0.4557 0.3357 0.092 Uiso 0.33 1 calc PR D 2
C72 C 0.5593(19) 0.133(3) 0.285(2) 0.075(3) Uani 0.33 1 d PD D 2
O72 O 0.5687(16) -0.119(3) 0.2873(14) 0.093(3) Uani 0.33 1 d PD D 2
N42 N 0.4577(18) 0.261(6) 0.2380(16) 0.125(6) Uani 0.33 1 d PD D 2
H42A H 0.3981 0.1727 0.2085 0.188 Uiso 0.33 1 calc PR D 2
H42B H 0.4545 0.4287 0.2381 0.188 Uiso 0.33 1 calc PR D 2
N33 N 0.6296(13) 0.201(3) 0.3021(11) 0.076(2) Uani 0.33 1 d PD D 3
H33 H 0.6016 0.3590 0.2980 0.092 Uiso 0.33 1 calc PR D 3
C73 C 0.5625(16) 0.034(4) 0.2646(13) 0.075(3) Uani 0.33 1 d PD D 3
O73 O 0.5600(14) -0.221(2) 0.2612(12) 0.093(3) Uani 0.33 1 d PD D 3
N43 N 0.4535(14) 0.106(5) 0.2043(10) 0.125(6) Uani 0.33 1 d PD D 3
H43A H 0.4356 0.2679 0.1947 0.188 Uiso 0.33 1 calc PR D 3
H43B H 0.4062 -0.0133 0.1779 0.188 Uiso 0.33 1 calc PR D 3
O51 O 1.2140(15) 0.923(5) 0.3127(13) 0.094(3) Uani 0.30 1 d P . .
O52 O 0.3569(15) 0.633(4) 0.2117(11) 0.094(3) Uani 0.22 1 d P . .
O53 O 1.249(3) 0.904(8) 0.331(2) 0.094(3) Uani 0.20 1 d P . .
O54 O 0.274(2) -0.047(5) 0.1411(16) 0.094(3) Uani 0.16 1 d P . .
O55 O 0.221(3) -0.017(7) 0.203(2) 0.094(3) Uani 0.12 1 d P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 O1 C1 . 108.7(3) y
C2 O2 H2 . 109.5 ?
C7 O3 C3 . 108.8(5) y
C13 N1 C10 . 126.3(3) y
C13 N1 H1 . 116.9 ?
C10 N1 H1 . 116.9 ?
C12 N2 C13 . 122.7(3) y
C12 N2 H2A . 118.6 ?
C13 N2 H2A . 118.6 ?
O1 C1 C11 . 109.7(3) y
O1 C1 C2 . 106.0(3) y
C11 C1 C2 . 112.7(3) y
O1 C1 H1A . 109.5 ?
C11 C1 H1A . 109.5 ?
C2 C1 H1A . 109.5 ?
O2 C2 C3 . 111.8(4) y
O2 C2 C1 . 110.9(4) y
C3 C2 C1 . 98.9(4) y
O2 C2 H2C . 111.5 ?
C3 C2 H2C . 111.5 ?
C1 C2 H2C . 111.5 ?
O3 C3 C2 . 116.5(5) y
O3 C3 C4 . 109.9(4) y
C2 C3 C4 . 103.1(4) y
O3 C3 H3A . 109 ?
C2 C3 H3A . 109 ?
C4 C3 H3A . 109 ?
O1 C4 C5 . 115.9(4) y
O1 C4 C3 . 102.4(3) y
C5 C4 C3 . 112.1(4) y
O1 C4 H4A . 108.7 ?
C5 C4 H4A . 108.7 ?
C3 C4 H4A . 108.7 ?
N32 C5 N31 . 11.80(15) y
N32 C5 N33 . 23.9(8) y
N31 C5 N33 . 27.9(7) y
N32 C5 C4 . 115.4(9) y
N31 C5 C4 . 103.6(1) y
N33 C5 C4 . 114.0(8) y
N32 C5 C6 . 105.30(11) y
N31 C5 C6 . 109.2(9) y
N33 C5 C6 . 125.9(8) y
C4 C5 C6 . 105.4(4) y
N32 C5 H5A . 105.3 ?
N31 C5 H5A . 112.7 ?
N33 C5 H5A . 84.9 ?
C4 C5 H5A . 112.7 ?
C6 C5 H5A . 112.7 ?
N32 C5 H5B . 110.1 ?
N31 C5 H5B . 117.5 ?
N33 C5 H5B . 89.7 ?
C4 C5 H5B . 110.1 ?
C6 C5 H5B . 110.1 ?
H5A C5 H5B . 4.9 ?
N32 C5 H5C . 123.2 ?
N31 C5 H5C . 130.7 ?
N33 C5 H5C . 102.8 ?
C4 C5 H5C . 102.8 ?
C6 C5 H5C . 102.8 ?
H5A C5 H5C . 18 ?
H5B C5 H5C . 13.2 ?
O41 C6 O42 . 16.0(1) y
O41 C6 C5 . 123.1(7) y
O42 C6 C5 . 109.7(9) y
O41 C6 C7 . 97.1(6) y
O42 C6 C7 . 96.7(1) y
C5 C6 C7 . 113.9(2) y
O41 C6 O43 . 38.8(7) y
O42 C6 O43 . 30.8(1) y
C5 C6 O43 . 85.5(6) y
C7 C6 O43 . 125.0(6) y
O41 C6 H6A . 107.2 ?
O42 C6 H6A . 122.1 ?
C5 C6 H6A . 107.2 ?
C7 C6 H6A . 107.2 ?
O43 C6 H6A . 115.4 ?
O41 C6 H6B . 97.3 ?
O42 C6 H6B . 111.9 ?
C5 C6 H6B . 111.9 ?
C7 C6 H6B . 111.9 ?
O43 C6 H6B . 106 ?
H6A C6 H6B . 10.3 ?
O41 C6 H6C . 101.4 ?
O42 C6 H6C . 116.2 ?
C5 C6 H6C . 110 ?
C7 C6 H6C . 110 ?
O43 C6 H6C . 110 ?
H6A C6 H6C . 6 ?
H6B C6 H6C . 4.3 ?
O3 C7 C6 . 112.6(2) y
O3 C7 H7A . 109.1 ?
C6 C7 H7A . 109.1 ?
O3 C7 H7B . 109.1 ?
C6 C7 H7B . 109.1 ?
H7A C7 H7B . 107.8 ?
O5 C10 N1 . 118.8(3) y
O5 C10 C11 . 125.2(3) y
N1 C10 C11 . 116.0(3) y
C12 C11 C10 . 117.9(4) y
C12 C11 C1 . 124.2(3) y
C10 C11 C1 . 117.9(3) y
C11 C12 N2 . 122.9(3) y
C11 C12 H12 . 118.6 ?
N2 C12 H12 . 118.6 ?
O6 C13 N2 . 124.0(3) y
O6 C13 N1 . 121.8(4) y
N2 C13 N1 . 114.2(3) y
C6 O41 C81 . 112.4(9) y
C82 O42 C6 . 108.80(14) y
O42 C82 H82A . 109.5 ?
O42 C82 H82B . 109.5 ?
H82A C82 H82B . 109.5 ?
O42 C82 H82C . 109.5 ?
H82A C82 H82C . 109.5 ?
H82B C82 H82C . 109.5 ?
C83 O43 C6 . 103.00(13) y
C71 N31 C5 . 113.70(13) y
C71 N31 H31 . 123.1 ?
C5 N31 H31 . 123.1 ?
O71 C71 N31 . 139.00(16) y
O71 C71 N41 . 104.00(15) y
N31 C71 N41 . 116.10(16) y
C71 N41 O52 . 162(2) y
C71 N41 H41A . 120 ?
O52 N41 H41A . 77.1 ?
C71 N41 H41B . 120 ?
O52 N41 H41B . 43.4 ?
H41A N41 H41B . 120 ?
C72 N32 C5 . 109.80(13) y
C72 N32 H32 . 125.1 ?
C5 N32 H32 . 125.1 ?
O72 C72 N32 . 124.60(13) y
O72 C72 N42 . 122.50(17) y
N32 C72 N42 . 113.00(15) y
C72 N42 H42A . 120 ?
C72 N42 H42B . 120 ?
H42A N42 H42B . 120 ?
C73 N33 C5 . 126.00(15) y
C73 N33 H33 . 117 ?
C5 N33 H33 . 117 ?
N33 C73 O73 . 137.00(16) y
N33 C73 N43 . 120.40(18) y
O73 C73 N43 . 102.60(16) y
C73 N43 H43A . 120 ?
C73 N43 H43B . 120 ?
H43A N43 H43B . 120 ?
O54 O55 O51 1_445 148(3) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 . 1.451(5) y
O1 C1 . 1.452(4) y
O2 C2 . 1.399(7) y
O2 H2 . 0.82 ?
O3 C7 . 1.420(6) y
O3 C3 . 1.427(6) y
O5 C10 . 1.241(3) y
O6 C13 . 1.232(5) y
N1 C13 . 1.368(4) y
N1 C10 . 1.373(4) y
N1 H1 . 0.86 ?
N2 C12 . 1.359(5) y
N2 C13 . 1.368(5) y
N2 H2a . 0.86 ?
C1 C11 . 1.512(5) y
C1 C2 . 1.553(6) y
C1 H1a . 0.98 ?
C2 C3 . 1.500(6) y
C2 H2c . 0.98 ?
C3 C4 . 1.501(6) y
C3 H3a . 0.98 ?
C4 C5 . 1.500(6) y
C4 H4a . 0.98 ?
C5 N32 . 1.406(13) y
C5 N31 . 1.431(13) y
C5 N33 . 1.499(13) y
C5 C6 . 1.538(7) y
C5 H5a . 0.98 ?
C5 H5b . 0.98 ?
C5 H5c . 0.98 ?
C6 O41 . 1.420(9) y
C6 O42 . 1.450(14) y
C6 C7 . 1.5521 y
C6 O43 . 1.609(14) y
C6 H6a . 0.98 ?
C6 H6b . 0.98 ?
C6 H6c . 0.98 ?
C7 H7a . 0.97 ?
C7 H7b . 0.97 ?
C10 C11 . 1.440(5) y
C11 C12 . 1.330(5) y
C12 H12 . 0.93 ?
O41 C81 . 1.430(13) y
C81 H81a . 0.96 ?
C81 H81b . 0.96 ?
C81 H81c . 0.96 ?
O42 C82 . 1.430(17) y
C82 H82a . 0.96 ?
C82 H82b . 0.96 ?
C82 H82c . 0.96 ?
O43 C83 . 1.416(17) y
C83 H83a . 0.96 ?
C83 H83b . 0.96 ?
C83 H83c . 0.96 ?
N31 C71 . 1.263(16) y
N31 H31 . 0.86 ?
C71 O71 . 1.239(18) y
C71 N41 . 1.412(16) y
N41 O52 . 1.79(3) y
N41 H41a . 0.86 ?
N41 H41b . 0.86 ?
N32 C72 . 1.310(16) y
N32 H32 . 0.86 ?
C72 O72 . 1.292(17) y
C72 N42 . 1.388(16) y
N42 H42a . 0.86 ?
N42 H42b . 0.86 ?
N33 C73 . 1.212(16) y
N33 H33 . 0.86 ?
C73 O73 . 1.31(2) y
C73 N43 . 1.441(16) y
N43 H43a . 0.86 ?
N43 H43b . 0.86 ?
O51 O55 1_665 1.71(4) y
O54 O55 . 1.13(3) y
O55 O51 1_445 1.71(4) y
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
O2 H2 O53 0.82 2.06 2.85(4) 159.6 .
O2 H2 O51 0.82 2.01 2.74(3) 148 .
N1 H1 O5 0.86 1.99 2.832(4) 165.9 2_755
N2 H2A O6 0.86 1.97 2.823(4) 170.6 2_645
N41 H41B O71 0.86 2.43 3.26(3) 162.4 1_565
N41 H41A O55 0.86 2.3 3.10(4) 154.4 .
N41 H41A O54 0.86 2.36 3.16(3) 154.9 .
N32 H32 O72 0.86 2.37 3.154(18) 152.7 1_565
N42 H42A O54 0.86 1.94 2.80(3) 175.5 .
N42 H42A O55 0.86 2.07 2.84(4) 149.7 .
N33 H33 O73 0.86 2.26 3.098(19) 166.3 1_565
N43 H43A O52 0.86 2.07 2.88(4) 159.1 .
N43 H43B O52 0.86 1.96 2.62(3) 133 1_545
N43 H43B O55 0.86 1.98 2.48(3) 116 .
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_publ_flag
C4 O1 C1 C11 -119.2(3) y
C4 O1 C1 C2 2.7(4) y
O1 C1 C2 O2 88.9(4) y
C11 C1 C2 O2 -151.0(3) y
O1 C1 C2 C3 -28.6(4) y
C11 C1 C2 C3 91.4(4) y
C7 O3 C3 C2 178.6(4) y
C7 O3 C3 C4 -64.7(6) y
O2 C2 C3 O3 47.0(6) y
C1 C2 C3 O3 163.9(4) y
O2 C2 C3 C4 -73.4(5) y
C1 C2 C3 C4 43.5(5) y
C1 O1 C4 C5 146.9(4) y
C1 O1 C4 C3 24.6(5) y
O3 C3 C4 O1 -168.3(4) y
C2 C3 C4 O1 -43.5(5) y
O3 C3 C4 C5 66.9(7) y
C2 C3 C4 C5 -168.3(4) y
O1 C4 C5 N32 -56.5(1) y
C3 C4 C5 N32 60.40(11) y
O1 C4 C5 N31 -57.6(8) y
C3 C4 C5 N31 59.3(8) y
O1 C4 C5 N33 -30.2(8) y
C3 C4 C5 N33 86.8(9) y
O1 C4 C5 C6 -172.3(3) y
C3 C4 C5 C6 -55.3(5) y
N32 C5 C6 O41 41.8(1) y
N31 C5 C6 O41 53.50(11) y
N33 C5 C6 O41 28.10(11) y
C4 C5 C6 O41 164.3(7) y
N32 C5 C6 O42 32.20(13) y
N31 C5 C6 O42 43.90(14) y
N33 C5 C6 O42 18.50(13) y
C4 C5 C6 O42 154.70(11) y
N32 C5 C6 C7 -74.9(7) y
N31 C5 C6 C7 -63.2(9) y
N33 C5 C6 C7 -88.6(8) y
C4 C5 C6 C7 47.5(4) y
N32 C5 C6 O43 51.5(8) y
N31 C5 C6 O43 63.2(1) y
N33 C5 C6 O43 37.8(1) y
C4 C5 C6 O43 174.0(6) y
C3 O3 C7 C6 57.1(4) y
O41 C6 C7 O3 178.0(6) y
O42 C6 C7 O3 -165.9(8) y
C5 C6 C7 O3 -50.9(3) y
O43 C6 C7 O3 -152.7(7) y
C13 N1 C10 O5 -179.1(3) y
C13 N1 C10 C11 0.6(5) y
O5 C10 C11 C12 -179.4(3) y
N1 C10 C11 C12 1.0(5) y
O5 C10 C11 C1 2.5(5) y
N1 C10 C11 C1 -177.2(3) y
O1 C1 C11 C12 3.9(5) y
C2 C1 C11 C12 -113.9(4) y
O1 C1 C11 C10 -178.0(3) y
C2 C1 C11 C10 64.1(4) y
C10 C11 C12 N2 -0.8(6) y
C1 C11 C12 N2 177.2(3) y
C13 N2 C12 C11 -1.0(6) y
C12 N2 C13 O6 -177.0(4) y
C12 N2 C13 N1 2.4(5) y
C10 N1 C13 O6 177.2(4) y
C10 N1 C13 N2 -2.3(5) y
O42 C6 O41 C81 100(6) y
C5 C6 O41 C81 64.80(12) y
C7 C6 O41 C81 -170.5(1) y
O43 C6 O41 C81 49.30(14) y
O41 C6 O42 C82 -83(6) y
C5 C6 O42 C82 66.80(18) y
C7 C6 O42 C82 -174.80(16) y
O43 C6 O42 C82 26.70(15) y
O41 C6 O43 C83 -32.20(17) y
O42 C6 O43 C83 -57(2) y
C5 C6 O43 C83 160.80(17) y
C7 C6 O43 C83 -83.10(17) y
N32 C5 N31 C71 -51(6) y
N33 C5 N31 C71 9(3) y
C4 C5 N31 C71 125(2) y
C6 C5 N31 C71 -123(2) y
C5 N31 C71 O71 -18(7) y
C5 N31 C71 N41 175(3) y
O71 C71 N41 O52 -159(7) y
N31 C71 N41 O52 13(10) y
N31 C5 N32 C72 114(8) y
N33 C5 N32 C72 17(3) y
C4 C5 N32 C72 109(2) y
C6 C5 N32 C72 -135(2) y
C5 N32 C72 O72 14(5) y
C5 N32 C72 N42 -166(3) y
N32 C5 N33 C73 -160(5) y
N31 C5 N33 C73 174(4) y
C4 C5 N33 C73 101.00(19) y
C6 C5 N33 C73 -125.90(19) y
C5 N33 C73 O73 9(4) y
C5 N33 C73 N43 -169.70(16) y
