#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/87/2228799.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2228799
loop_
_publ_author_name
'Jenkinson, S. F.'
'Oña, N.'
'Romero, A.'
'Fleet, G. W. J.'
'Thompson, A. L.'
'Pino-González, M. S.'
_publ_section_title
;
 6-Azido-3-O-benzyl-6-deoxy-N,N-diethyl-1,2-O-isopropylidene-<small>D</small>-glycero-α-<small>D</small>-gluco-heptofuranuronamide
;
_journal_coeditor_code           LH5169
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o38
_journal_page_last               o39
_journal_paper_doi               10.1107/S1600536810048944
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C21 H30 N4 O6'
_chemical_formula_moiety         'C21 H30 N4 O6'
_chemical_formula_sum            'C21 H30 N4 O6'
_chemical_formula_weight         434.49
_chemical_name_systematic
;
6-Azido-3-O-benzyl-6-deoxy-N,N-diethyl-1,2-O-
isopropylidene-D-glycero-α-D-gluco-
heptofuranuronamide
;
_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
_cell_angle_alpha                90
_cell_angle_beta                 97.0347(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0478(4)
_cell_length_b                   10.5547(3)
_cell_length_c                   16.5552(6)
_cell_measurement_reflns_used    4645
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     2262.75(13)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15625
_diffrn_reflns_theta_full        25.840
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_min         5.103
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(DENZO/SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.44
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9618
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         5408
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.002720
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[σ²(F²) + (0.04P)² + 1.43P], where P=[max(Fo²,0) + 2Fc²]/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1216
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1216
_reflns_number_gt                4270
_reflns_number_total             5408
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5169.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2228799
_cod_database_fobs_code          2228799
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z
loop_
_atom_site_type_symbol
_atom_site_label
_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_disorder_assembly
_atom_site_disorder_group
O O1 0.64815(18) 0.4052(2) 0.70138(14) 0.0323 Uani 1.0000 . .
C C2 0.6244(3) 0.5362(3) 0.7050(2) 0.0326 Uani 1.0000 . .
O O3 0.52450(18) 0.5540(3) 0.72847(14) 0.0375 Uani 1.0000 . .
C C4 0.4683(3) 0.6383(4) 0.6712(2) 0.0391 Uani 1.0000 . .
O O5 0.50934(17) 0.6130(3) 0.59658(14) 0.0358 Uani 1.0000 . .
C C6 0.6160(2) 0.5864(4) 0.6164(2) 0.0325 Uani 1.0000 . .
C C7 0.6459(2) 0.4740(3) 0.5665(2) 0.0298 Uani 1.0000 . .
C C8 0.6189(2) 0.3632(3) 0.61879(18) 0.0282 Uani 1.0000 . .
C C9 0.6733(2) 0.2397(3) 0.60611(19) 0.0293 Uani 1.0000 . .
O O10 0.64964(17) 0.1992(2) 0.52424(13) 0.0330 Uani 1.0000 . .
C C11 0.6496(2) 0.1379(3) 0.6682(2) 0.0308 Uani 1.0000 . .
N N12 0.6996(2) 0.0157(3) 0.6550(2) 0.0429 Uani 1.0000 . .
N N13 0.6700(3) -0.0417(3) 0.5909(2) 0.0477 Uani 1.0000 . .
N N14 0.6530(4) -0.1082(4) 0.5375(3) 0.0697 Uani 1.0000 . .
C C15 0.5332(2) 0.1219(3) 0.6642(2) 0.0329 Uani 1.0000 . .
O O16 0.48494(19) 0.0876(3) 0.59857(15) 0.0420 Uani 1.0000 . .
N N17 0.4860(2) 0.1522(4) 0.72949(19) 0.0511 Uani 1.0000 . .
C C18 0.5406(3) 0.1803(5) 0.8104(2) 0.0490 Uani 1.0000 . .
C C19 0.5848(4) 0.0643(5) 0.8548(3) 0.0700 Uani 1.0000 . .
C C20 0.3693(4) 0.1677(7) 0.7180(3) 0.0828 Uani 1.0000 . .
C C21 0.3191(5) 0.0650(7) 0.7556(5) 0.1107 Uani 1.0000 . .
O O23 0.75398(16) 0.4753(2) 0.56203(14) 0.0328 Uani 1.0000 . .
C C24 0.7781(3) 0.5480(4) 0.4939(2) 0.0465 Uani 1.0000 . .
C C25 0.8930(3) 0.5551(4) 0.4966(2) 0.0357 Uani 1.0000 . .
C C26 0.9436(3) 0.4845(4) 0.4428(2) 0.0437 Uani 1.0000 . .
C C27 1.0507(3) 0.4893(4) 0.4466(3) 0.0477 Uani 1.0000 . .
C C28 1.1072(3) 0.5638(4) 0.5032(3) 0.0470 Uani 1.0000 . .
C C29 1.0577(3) 0.6343(4) 0.5561(2) 0.0462 Uani 1.0000 . .
C C30 0.9513(3) 0.6311(4) 0.5530(2) 0.0431 Uani 1.0000 . .
C C31 0.3567(3) 0.6015(5) 0.6614(2) 0.0568 Uani 1.0000 . .
C C32 0.4884(4) 0.7751(4) 0.6964(3) 0.0572 Uani 1.0000 . .
O O33 0.85567(16) 0.4425(2) 0.97984(13) 0.0306 Uani 1.0000 . .
C C34 0.8314(2) 0.4732(3) 0.89580(18) 0.0263 Uani 1.0000 . .
C C35 0.8804(2) 0.5994(3) 0.87875(19) 0.0262 Uani 1.0000 . .
O O36 0.85475(16) 0.6307(2) 0.79389(13) 0.0281 Uani 1.0000 . .
C C37 0.8626(2) 0.7634(3) 0.7846(2) 0.0291 Uani 1.0000 . .
O O38 0.95612(18) 0.7968(3) 0.75537(14) 0.0387 Uani 1.0000 . .
C C39 1.0141(2) 0.8790(3) 0.8134(2) 0.0312 Uani 1.0000 . .
O O40 0.97597(16) 0.8530(2) 0.88876(13) 0.0313 Uani 1.0000 . .
C C41 0.8693(2) 0.8217(3) 0.8702(2) 0.0283 Uani 1.0000 . .
C C42 0.8428(2) 0.7125(3) 0.92412(19) 0.0266 Uani 1.0000 . .
O O43 0.73311(15) 0.7062(2) 0.92145(13) 0.0308 Uani 1.0000 . .
C C44 0.6988(2) 0.7753(4) 0.9865(2) 0.0413 Uani 1.0000 . .
C C45 0.5827(2) 0.7846(3) 0.9760(2) 0.0314 Uani 1.0000 . .
C C46 0.5195(3) 0.7125(4) 0.9202(2) 0.0397 Uani 1.0000 . .
C C47 0.4129(3) 0.7252(4) 0.9147(2) 0.0467 Uani 1.0000 . .
C C48 0.3685(3) 0.8093(5) 0.9639(2) 0.0484 Uani 1.0000 . .
C C49 0.4308(3) 0.8828(4) 1.0175(3) 0.0500 Uani 1.0000 . .
C C50 0.5372(3) 0.8715(4) 1.0240(2) 0.0425 Uani 1.0000 . .
C C53 1.1262(3) 0.8427(4) 0.8215(2) 0.0446 Uani 1.0000 . .
C C54 0.9960(3) 1.0157(3) 0.7890(2) 0.0430 Uani 1.0000 . .
C C56 0.8605(2) 0.3683(3) 0.83931(19) 0.0276 Uani 1.0000 . .
N N57 0.8102(2) 0.2462(3) 0.85459(18) 0.0352 Uani 1.0000 . .
N N58 0.8394(2) 0.1915(3) 0.91974(19) 0.0373 Uani 1.0000 . .
N N59 0.8557(3) 0.1267(3) 0.9747(2) 0.0522 Uani 1.0000 . .
C C69 0.9774(2) 0.3514(3) 0.84793(19) 0.0283 Uani 1.0000 . .
O O61 1.02124(16) 0.3219(3) 0.91594(13) 0.0351 Uani 1.0000 . .
N N62 1.0296(2) 0.3696(3) 0.78426(16) 0.0290 Uani 1.0000 . .
C C63 0.9861(3) 0.4068(3) 0.70130(19) 0.0329 Uani 1.0000 . .
C C67 1.1427(2) 0.3516(4) 0.7969(2) 0.0373 Uani 1.0000 . .
C C68 1.1979(3) 0.4704(5) 0.8269(3) 0.0514 Uani 1.0000 . .
C C60 0.9706(3) 0.2938(4) 0.6450(2) 0.0424 Uani 1.0000 . .
H H21 0.6795 0.5814 0.7411 0.0413 Uiso 1.0000 . .
H H61 0.6595 0.6608 0.6102 0.0413 Uiso 1.0000 . .
H H71 0.6058 0.4710 0.5120 0.0371 Uiso 1.0000 . .
H H81 0.5427 0.3517 0.6105 0.0355 Uiso 1.0000 . .
H H91 0.7502 0.2565 0.6153 0.0370 Uiso 1.0000 . .
H H111 0.6786 0.1682 0.7219 0.0400 Uiso 1.0000 . .
H H181 0.4892 0.2173 0.8431 0.0635 Uiso 1.0000 . .
H H182 0.5959 0.2426 0.8051 0.0631 Uiso 1.0000 . .
H H192 0.6168 0.0864 0.9086 0.1080 Uiso 1.0000 . .
H H191 0.5289 0.0039 0.8588 0.1082 Uiso 1.0000 . .
H H193 0.6370 0.0263 0.8254 0.1083 Uiso 1.0000 . .
H H202 0.3507 0.2449 0.7451 0.0996 Uiso 1.0000 . .
H H201 0.3400 0.1775 0.6607 0.0987 Uiso 1.0000 . .
H H211 0.2434 0.0744 0.7441 0.1711 Uiso 1.0000 . .
H H212 0.3432 0.0626 0.8148 0.1714 Uiso 1.0000 . .
H H213 0.3425 -0.0108 0.7288 0.1713 Uiso 1.0000 . .
H H242 0.7502 0.6334 0.4980 0.0610 Uiso 1.0000 . .
H H241 0.7465 0.5100 0.4427 0.0610 Uiso 1.0000 . .
H H261 0.9034 0.4324 0.4038 0.0557 Uiso 1.0000 . .
H H271 1.0850 0.4414 0.4092 0.0598 Uiso 1.0000 . .
H H281 1.1810 0.5652 0.5047 0.0609 Uiso 1.0000 . .
H H291 1.0965 0.6855 0.5947 0.0577 Uiso 1.0000 . .
H H301 0.9178 0.6804 0.5901 0.0536 Uiso 1.0000 . .
H H312 0.3196 0.6568 0.6209 0.0900 Uiso 1.0000 . .
H H311 0.3303 0.6102 0.7125 0.0902 Uiso 1.0000 . .
H H313 0.3496 0.5153 0.6438 0.0898 Uiso 1.0000 . .
H H322 0.4522 0.8297 0.6550 0.0915 Uiso 1.0000 . .
H H321 0.4641 0.7893 0.7485 0.0911 Uiso 1.0000 . .
H H323 0.5634 0.7908 0.7003 0.0914 Uiso 1.0000 . .
H H341 0.7558 0.4841 0.8852 0.0312 Uiso 1.0000 . .
H H351 0.9560 0.5943 0.8920 0.0324 Uiso 1.0000 . .
H H371 0.8030 0.7976 0.7487 0.0365 Uiso 1.0000 . .
H H411 0.8236 0.8951 0.8718 0.0377 Uiso 1.0000 . .
H H421 0.8789 0.7177 0.9801 0.0315 Uiso 1.0000 . .
H H442 0.7240 0.7335 1.0401 0.0541 Uiso 1.0000 . .
H H441 0.7271 0.8618 0.9869 0.0547 Uiso 1.0000 . .
H H461 0.5489 0.6538 0.8859 0.0497 Uiso 1.0000 . .
H H471 0.3707 0.6747 0.8759 0.0575 Uiso 1.0000 . .
H H481 0.2945 0.8160 0.9609 0.0622 Uiso 1.0000 . .
H H491 0.4014 0.9433 1.0501 0.0603 Uiso 1.0000 . .
H H501 0.5802 0.9223 1.0620 0.0551 Uiso 1.0000 . .
H H532 1.1655 0.9019 0.8600 0.0722 Uiso 1.0000 . .
H H531 1.1339 0.7567 0.8419 0.0727 Uiso 1.0000 . .
H H533 1.1517 0.8476 0.7682 0.0720 Uiso 1.0000 . .
H H541 1.0285 1.0712 0.8310 0.0684 Uiso 1.0000 . .
H H543 1.0243 1.0320 0.7386 0.0679 Uiso 1.0000 . .
H H542 0.9224 1.0313 0.7813 0.0679 Uiso 1.0000 . .
H H561 0.8352 0.3934 0.7826 0.0362 Uiso 1.0000 . .
H H632 1.0367 0.4644 0.6817 0.0422 Uiso 1.0000 . .
H H631 0.9207 0.4513 0.7039 0.0420 Uiso 1.0000 . .
H H671 1.1587 0.2815 0.8359 0.0484 Uiso 1.0000 . .
H H672 1.1632 0.3294 0.7432 0.0481 Uiso 1.0000 . .
H H683 1.2715 0.4572 0.8302 0.0791 Uiso 1.0000 . .
H H682 1.1808 0.4894 0.8820 0.0790 Uiso 1.0000 . .
H H681 1.1772 0.5395 0.7892 0.0790 Uiso 1.0000 . .
H H603 0.9415 0.3234 0.5905 0.0673 Uiso 1.0000 . .
H H602 1.0366 0.2524 0.6431 0.0672 Uiso 1.0000 . .
H H601 0.9232 0.2353 0.6685 0.0672 Uiso 1.0000 . .
H H331 0.9169 0.4160 0.9902 0.0479 Uiso 1.0000 . .
H H101 0.5900 0.1659 0.5196 0.0518 Uiso 1.0000 . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 'International Tables Vol C 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_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 C8 . . . 107.8(2) no
O1 C2 O3 . . . 110.7(3) no
O1 C2 C6 . . . 106.5(3) no
O3 C2 C6 . . . 104.7(2) no
O1 C2 H21 . . . 110.3 no
O3 C2 H21 . . . 113.0 no
C6 C2 H21 . . . 111.4 no
C2 O3 C4 . . . 108.3(2) no
O3 C4 O5 . . . 103.9(3) no
O3 C4 C31 . . . 108.8(3) no
O5 C4 C31 . . . 108.7(3) no
O3 C4 C32 . . . 110.6(3) no
O5 C4 C32 . . . 110.2(3) no
C31 C4 C32 . . . 114.2(4) no
C4 O5 C6 . . . 107.3(2) no
C2 C6 O5 . . . 103.9(3) no
C2 C6 C7 . . . 104.6(3) no
O5 C6 C7 . . . 109.7(3) no
C2 C6 H61 . . . 113.5 no
O5 C6 H61 . . . 112.4 no
C7 C6 H61 . . . 112.2 no
C6 C7 C8 . . . 101.5(3) no
C6 C7 O23 . . . 110.0(3) no
C8 C7 O23 . . . 109.7(3) no
C6 C7 H71 . . . 112.3 no
C8 C7 H71 . . . 111.2 no
O23 C7 H71 . . . 111.7 no
C7 C8 O1 . . . 104.5(3) no
C7 C8 C9 . . . 116.0(3) no
O1 C8 C9 . . . 108.8(2) no
C7 C8 H81 . . . 108.2 no
O1 C8 H81 . . . 108.2 no
C9 C8 H81 . . . 110.8 no
C8 C9 O10 . . . 110.0(3) no
C8 C9 C11 . . . 111.8(3) no
O10 C9 C11 . . . 112.8(3) no
C8 C9 H91 . . . 107.6 no
O10 C9 H91 . . . 107.0 no
C11 C9 H91 . . . 107.3 no
C9 O10 H101 . . . 107.6 no
C9 C11 N12 . . . 112.4(3) no
C9 C11 C15 . . . 109.2(3) no
N12 C11 C15 . . . 110.8(3) no
C9 C11 H111 . . . 106.9 no
N12 C11 H111 . . . 107.0 no
C15 C11 H111 . . . 110.5 no
C11 N12 N13 . . . 117.1(3) no
N12 N13 N14 . . . 169.4(4) no
C11 C15 O16 . . . 117.8(3) no
C11 C15 N17 . . . 119.4(3) no
O16 C15 N17 . . . 122.7(3) no
C15 N17 C18 . . . 124.1(3) no
C15 N17 C20 . . . 118.4(3) no
C18 N17 C20 . . . 117.3(3) no
N17 C18 C19 . . . 113.2(4) no
N17 C18 H181 . . . 106.9 no
C19 C18 H181 . . . 107.4 no
N17 C18 H182 . . . 109.3 no
C19 C18 H182 . . . 110.2 no
H181 C18 H182 . . . 109.8 no
C18 C19 H192 . . . 110.5 no
C18 C19 H191 . . . 108.6 no
H192 C19 H191 . . . 109.7 no
C18 C19 H193 . . . 110.0 no
H192 C19 H193 . . . 108.1 no
H191 C19 H193 . . . 109.9 no
N17 C20 C21 . . . 111.4(6) no
N17 C20 H202 . . . 109.5 no
C21 C20 H202 . . . 106.1 no
N17 C20 H201 . . . 113.3 no
C21 C20 H201 . . . 110.6 no
H202 C20 H201 . . . 105.5 no
C20 C21 H211 . . . 109.7 no
C20 C21 H212 . . . 109.8 no
H211 C21 H212 . . . 112.4 no
C20 C21 H213 . . . 103.5 no
H211 C21 H213 . . . 110.7 no
H212 C21 H213 . . . 110.3 no
C7 O23 C24 . . . 111.2(2) no
O23 C24 C25 . . . 108.6(3) no
O23 C24 H242 . . . 108.7 no
C25 C24 H242 . . . 109.4 no
O23 C24 H241 . . . 110.6 no
C25 C24 H241 . . . 111.1 no
H242 C24 H241 . . . 108.4 no
C24 C25 C26 . . . 120.5(4) no
C24 C25 C30 . . . 120.9(4) no
C26 C25 C30 . . . 118.6(3) no
C25 C26 C27 . . . 120.3(4) no
C25 C26 H261 . . . 118.6 no
C27 C26 H261 . . . 121.1 no
C26 C27 C28 . . . 120.4(4) no
C26 C27 H271 . . . 120.0 no
C28 C27 H271 . . . 119.6 no
C27 C28 C29 . . . 119.6(4) no
C27 C28 H281 . . . 118.8 no
C29 C28 H281 . . . 121.6 no
C28 C29 C30 . . . 120.9(4) no
C28 C29 H291 . . . 119.4 no
C30 C29 H291 . . . 119.7 no
C25 C30 C29 . . . 120.3(4) no
C25 C30 H301 . . . 119.6 no
C29 C30 H301 . . . 120.1 no
C4 C31 H312 . . . 108.3 no
C4 C31 H311 . . . 109.3 no
H312 C31 H311 . . . 110.4 no
C4 C31 H313 . . . 109.7 no
H312 C31 H313 . . . 109.9 no
H311 C31 H313 . . . 109.2 no
C4 C32 H322 . . . 108.6 no
C4 C32 H321 . . . 109.2 no
H322 C32 H321 . . . 110.6 no
C4 C32 H323 . . . 108.4 no
H322 C32 H323 . . . 109.8 no
H321 C32 H323 . . . 110.2 no
C34 O33 H331 . . . 111.4 no
O33 C34 C35 . . . 109.5(2) no
O33 C34 C56 . . . 113.0(3) no
C35 C34 C56 . . . 112.4(2) no
O33 C34 H341 . . . 107.2 no
C35 C34 H341 . . . 107.4 no
C56 C34 H341 . . . 107.0 no
C34 C35 O36 . . . 109.2(2) no
C34 C35 C42 . . . 115.3(2) no
O36 C35 C42 . . . 104.5(3) no
C34 C35 H351 . . . 110.1 no
O36 C35 H351 . . . 109.6 no
C42 C35 H351 . . . 107.9 no
C35 O36 C37 . . . 108.8(2) no
O36 C37 O38 . . . 111.2(3) no
O36 C37 C41 . . . 107.0(3) no
O38 C37 C41 . . . 105.2(2) no
O36 C37 H371 . . . 111.4 no
O38 C37 H371 . . . 110.7 no
C41 C37 H371 . . . 111.1 no
C37 O38 C39 . . . 109.2(2) no
O38 C39 O40 . . . 104.9(2) no
O38 C39 C53 . . . 109.5(3) no
O40 C39 C53 . . . 108.2(3) no
O38 C39 C54 . . . 110.2(3) no
O40 C39 C54 . . . 110.9(3) no
C53 C39 C54 . . . 112.7(3) no
C39 O40 C41 . . . 106.9(2) no
C37 C41 O40 . . . 103.6(2) no
C37 C41 C42 . . . 104.2(3) no
O40 C41 C42 . . . 109.5(2) no
C37 C41 H411 . . . 112.1 no
O40 C41 H411 . . . 113.1 no
C42 C41 H411 . . . 113.5 no
C41 C42 C35 . . . 101.2(2) no
C41 C42 O43 . . . 108.3(2) no
C35 C42 O43 . . . 109.3(2) no
C41 C42 H421 . . . 113.1 no
C35 C42 H421 . . . 111.2 no
O43 C42 H421 . . . 113.1 no
C42 O43 C44 . . . 111.2(2) no
O43 C44 C45 . . . 110.7(3) no
O43 C44 H442 . . . 110.1 no
C45 C44 H442 . . . 110.2 no
O43 C44 H441 . . . 109.2 no
C45 C44 H441 . . . 108.2 no
H442 C44 H441 . . . 108.5 no
C44 C45 C46 . . . 123.2(3) no
C44 C45 C50 . . . 118.0(3) no
C46 C45 C50 . . . 118.8(3) no
C45 C46 C47 . . . 119.9(4) no
C45 C46 H461 . . . 120.3 no
C47 C46 H461 . . . 119.8 no
C46 C47 C48 . . . 120.9(4) no
C46 C47 H471 . . . 118.7 no
C48 C47 H471 . . . 120.5 no
C47 C48 C49 . . . 119.3(3) no
C47 C48 H481 . . . 120.5 no
C49 C48 H481 . . . 120.3 no
C48 C49 C50 . . . 120.8(4) no
C48 C49 H491 . . . 120.2 no
C50 C49 H491 . . . 119.1 no
C45 C50 C49 . . . 120.4(4) no
C45 C50 H501 . . . 119.2 no
C49 C50 H501 . . . 120.4 no
C39 C53 H532 . . . 108.6 no
C39 C53 H531 . . . 109.1 no
H532 C53 H531 . . . 110.1 no
C39 C53 H533 . . . 109.8 no
H532 C53 H533 . . . 109.9 no
H531 C53 H533 . . . 109.3 no
C39 C54 H541 . . . 110.3 no
C39 C54 H543 . . . 109.6 no
H541 C54 H543 . . . 109.4 no
C39 C54 H542 . . . 108.6 no
H541 C54 H542 . . . 109.4 no
H543 C54 H542 . . . 109.4 no
C34 C56 N57 . . . 112.2(3) no
C34 C56 C69 . . . 110.4(3) no
N57 C56 C69 . . . 110.0(3) no
C34 C56 H561 . . . 107.8 no
N57 C56 H561 . . . 106.9 no
C69 C56 H561 . . . 109.5 no
C56 N57 N58 . . . 117.2(3) no
N57 N58 N59 . . . 169.2(4) no
C56 C69 O61 . . . 117.4(3) no
C56 C69 N62 . . . 120.7(3) no
O61 C69 N62 . . . 121.9(3) no
C69 N62 C63 . . . 126.7(3) no
C69 N62 C67 . . . 117.9(3) no
C63 N62 C67 . . . 115.5(3) no
N62 C63 C60 . . . 111.8(3) no
N62 C63 H632 . . . 106.0 no
C60 C63 H632 . . . 109.2 no
N62 C63 H631 . . . 109.0 no
C60 C63 H631 . . . 110.7 no
H632 C63 H631 . . . 110.0 no
N62 C67 C68 . . . 111.7(3) no
N62 C67 H671 . . . 108.5 no
C68 C67 H671 . . . 110.7 no
N62 C67 H672 . . . 106.3 no
C68 C67 H672 . . . 108.9 no
H671 C67 H672 . . . 110.6 no
C67 C68 H683 . . . 109.4 no
C67 C68 H682 . . . 108.8 no
H683 C68 H682 . . . 108.2 no
C67 C68 H681 . . . 109.2 no
H683 C68 H681 . . . 109.9 no
H682 C68 H681 . . . 111.3 no
C63 C60 H603 . . . 108.8 no
C63 C60 H602 . . . 108.8 no
H603 C60 H602 . . . 111.0 no
C63 C60 H601 . . . 107.1 no
H603 C60 H601 . . . 111.7 no
H602 C60 H601 . . . 109.3 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . . 1.420(4) no
O1 C8 . . 1.444(4) no
C2 O3 . . 1.418(4) no
C2 C6 . . 1.551(5) no
C2 H21 . . 0.999 no
O3 C4 . . 1.435(4) no
C4 O5 . . 1.430(4) no
C4 C31 . . 1.496(5) no
C4 C32 . . 1.517(6) no
O5 C6 . . 1.419(4) no
C6 C7 . . 1.523(5) no
C6 H61 . . 0.981 no
C7 C8 . . 1.521(5) no
C7 O23 . . 1.422(4) no
C7 H71 . . 0.987 no
C8 C9 . . 1.511(5) no
C8 H81 . . 0.994 no
C9 O10 . . 1.419(4) no
C9 C11 . . 1.545(4) no
C9 H91 . . 1.011 no
O10 H101 . . 0.848 no
C11 N12 . . 1.474(5) no
C11 C15 . . 1.522(4) no
C11 H111 . . 0.977 no
N12 N13 . . 1.241(5) no
N13 N14 . . 1.129(5) no
C15 O16 . . 1.241(4) no
C15 N17 . . 1.346(5) no
N17 C18 . . 1.469(5) no
N17 C20 . . 1.520(6) no
C18 C19 . . 1.506(7) no
C18 H181 . . 0.992 no
C18 H182 . . 0.988 no
C19 H192 . . 0.965 no
C19 H191 . . 0.978 no
C19 H193 . . 0.970 no
C20 C21 . . 1.446(9) no
C20 H202 . . 0.975 no
C20 H201 . . 0.984 no
C21 H211 . . 0.988 no
C21 H212 . . 0.993 no
C21 H213 . . 0.982 no
O23 C24 . . 1.431(4) no
C24 C25 . . 1.497(5) no
C24 H242 . . 0.978 no
C24 H241 . . 0.982 no
C25 C26 . . 1.388(5) no
C25 C30 . . 1.387(5) no
C26 C27 . . 1.392(6) no
C26 H261 . . 0.955 no
C27 C28 . . 1.368(6) no
C27 H271 . . 0.952 no
C28 C29 . . 1.370(6) no
C28 H281 . . 0.960 no
C29 C30 . . 1.383(5) no
C29 H291 . . 0.937 no
C30 H301 . . 0.951 no
C31 H312 . . 0.972 no
C31 H311 . . 0.957 no
C31 H313 . . 0.956 no
C32 H322 . . 0.972 no
C32 H321 . . 0.968 no
C32 H323 . . 0.986 no
O33 C34 . . 1.426(4) no
O33 H331 . . 0.844 no
C34 C35 . . 1.518(5) no
C34 C56 . . 1.527(5) no
C34 H341 . . 0.987 no
C35 O36 . . 1.442(4) no
C35 C42 . . 1.523(5) no
C35 H351 . . 0.986 no
O36 C37 . . 1.415(4) no
C37 O38 . . 1.411(4) no
C37 C41 . . 1.538(5) no
C37 H371 . . 0.987 no
O38 C39 . . 1.437(4) no
C39 O40 . . 1.426(4) no
C39 C53 . . 1.503(5) no
C39 C54 . . 1.509(5) no
O40 C41 . . 1.427(4) no
C41 C42 . . 1.524(5) no
C41 H411 . . 0.980 no
C42 O43 . . 1.429(3) no
C42 H421 . . 0.989 no
O43 C44 . . 1.417(4) no
C44 C45 . . 1.506(4) no
C44 H442 . . 1.010 no
C44 H441 . . 0.985 no
C45 C46 . . 1.388(5) no
C45 C50 . . 1.393(5) no
C46 C47 . . 1.390(5) no
C46 H461 . . 0.952 no
C47 C48 . . 1.379(6) no
C47 H471 . . 0.955 no
C48 C49 . . 1.369(6) no
C48 H481 . . 0.963 no
C49 C50 . . 1.384(5) no
C49 H491 . . 0.946 no
C50 H501 . . 0.955 no
C53 H532 . . 0.990 no
C53 H531 . . 0.970 no
C53 H533 . . 0.981 no
C54 H541 . . 0.967 no
C54 H543 . . 0.969 no
C54 H542 . . 0.966 no
C56 N57 . . 1.482(4) no
C56 C69 . . 1.524(4) no
C56 H561 . . 0.992 no
N57 N58 . . 1.241(4) no
N58 N59 . . 1.137(4) no
C69 O61 . . 1.239(4) no
C69 N62 . . 1.338(4) no
N62 C63 . . 1.474(4) no
N62 C67 . . 1.476(4) no
C63 C60 . . 1.512(5) no
C63 H632 . . 0.981 no
C63 H631 . . 0.980 no
C67 C68 . . 1.501(6) no
C67 H671 . . 0.988 no
C67 H672 . . 0.987 no
C68 H683 . . 0.965 no
C68 H682 . . 0.986 no
C68 H681 . . 0.976 no
C60 H603 . . 0.986 no
C60 H602 . . 0.971 no
C60 H601 . . 0.988 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H21 O36 . . . 1.00 2.40 3.333(5) 155 no
C7 H71 O16 . . 2_656 0.99 2.39 3.268(5) 147 no
C18 H182 O1 . . . 0.99 2.58 3.388(5) 139 no
C31 H312 O10 . . 2_656 0.97 2.52 3.233(5) 130 no
C42 H421 O61 . . 2_757 0.99 2.31 3.216(5) 152 no
O33 H331 O40 . . 2_747 0.84 2.39 3.046(5) 135 yes
O33 H331 O61 . . . 0.84 2.18 2.822(5) 133 no
O10 H101 O5 . . 2_646 0.85 2.25 2.849(5) 127 yes
O10 H101 O16 . . . 0.85 2.17 2.858(5) 138 no
