#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/57/2225721.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_2225721
loop_
_publ_author_name
'Shibata, Hiroki'
'Mizuguchi, Jin'
_publ_section_title
;
 (2,6-Bis{5-amino-3-tert-butyl-4-[(3-methyl-1,2,4-thiadiazol-5-yl)diazenyl]-1H-pyrazol-1-yl}-4-oxo-1,4-dihydro-1,3,5-triazin-1-ido)methanol(phenol)sodium
 phenol tetrasolvate
;
_journal_coeditor_code           SJ2750
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m463
_journal_page_last               m464
_journal_paper_doi               10.1107/S160053681001086X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac
'[Na(C23 H28 N17 O1 S2) (C H4 O) (C6 H6 O)], 4C6 H6 O'
_chemical_formula_moiety         'C30 H38 N17 Na O3 S2, 4(C6 H6 O)'
_chemical_formula_sum            'C54 H62 N17 Na O7 S2'
_chemical_formula_weight         1148.30
_chemical_name_systematic
;
(2,6-Bis{5-amino-3-tert-butyl-4-[(3-methyl-1,2,4-thiadiazol-5-
yl)diazenyl]-1H-pyrazol-1-yl}-4-oxo-1,4-dihydro-1,3,5-triazin-1-
ido)methanol(phenol)sodium phenol tetrasolvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                114.1030(10)
_cell_angle_beta                 96.5800(10)
_cell_angle_gamma                95.6500(10)
_cell_formula_units_Z            2
_cell_length_a                   8.38964(15)
_cell_length_b                   18.8780(3)
_cell_length_c                   20.4060(4)
_cell_measurement_reflns_used    26974
_cell_measurement_temperature    93.1
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      4.2
_cell_volume                     2892.84(9)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction
'CrystalStructure (Rigaku/MSC & Rigaku, 2006)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material
'CrystalStructure (Rigaku/MSC & Rigaku, 2006)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      93.1
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            32979
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_exptl_absorpt_coefficient_mu    1.455
_exptl_absorpt_correction_T_max  0.748
_exptl_absorpt_correction_T_min  0.345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(ABSCOR; Higashi, 1995)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1208.00
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.66
_refine_diff_density_min         -0.47
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     819
_refine_ls_number_reflns         10340
_refine_ls_number_restraints     156
_refine_ls_R_factor_gt           0.0638
_refine_ls_shift/su_max          0.0010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1010P)²+2.2948P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1961
_reflns_number_gt                7267
_reflns_number_total             10340
_reflns_threshold_expression     F²>2σ(F²)
_cod_data_source_file            sj2750.cif
_cod_data_source_block           I
_cod_original_cell_volume        2892.83(9)
_cod_original_formula_sum        'C54 H62 N17 Na O7 S2 '
_cod_database_code               2225721
_cod_database_fobs_code          2225721
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,-Y,-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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 1.47119(10) 0.92371(4) 0.62076(4) 0.0412(2) Uani d . 1 . .
S S2 -0.01553(10) 0.09004(5) 0.26699(4) 0.0442(2) Uani d . 1 . .
Na Na1 0.70228(15) 0.50735(7) 0.35073(6) 0.0382(3) Uani d . 1 B .
O O1 0.8097(3) 0.48489(11) 0.65787(10) 0.0342(5) Uani d . 1 . .
O O2 0.8888(3) 0.45383(13) 0.26640(11) 0.0428(5) Uani d . 1 . .
H H2O 0.9806 0.4741 0.2926 0.051 Uiso calc R 1 A 1
O O3 1.8364(3) 1.11563(15) 0.72119(14) 0.0583(7) Uani d . 1 . .
H H3O 1.7553 1.0805 0.7099 0.070 Uiso calc R 1 . .
O O4 -0.3653(3) -0.08841(19) 0.18027(15) 0.0843(11) Uani d . 1 . .
H H4O -0.2885 -0.0683 0.2158 0.101 Uiso calc R 1 . .
O O6 1.2701(9) 1.3726(4) 0.9187(4) 0.104(2) Uani d P 0.50 . .
H H6O 1.2690 1.3365 0.9328 0.124 Uiso calc R 0.50 . .
O O7 0.3015(6) 0.1073(2) 0.5196(2) 0.0435(11) Uani d P 0.50 . .
H H7O 0.2190 0.0895 0.4867 0.052 Uiso calc R 0.50 . .
O O8 0.4989(3) 0.57323(15) 0.32562(14) 0.0543(7) Uani d . 1 . .
H H8O 0.4084 0.5590 0.3341 0.065 Uiso calc R 1 B .
N N1 1.5988(3) 0.98531(15) 0.69533(16) 0.0435(7) Uani d . 1 . .
N N2 1.4734(3) 0.89848(15) 0.73354(15) 0.0423(6) Uani d . 1 . .
N N3 1.2860(3) 0.80306(14) 0.63605(14) 0.0389(6) Uani d . 1 . .
N N4 1.2247(3) 0.78470(14) 0.56894(14) 0.0367(6) Uani d . 1 B .
N N5 0.9211(3) 0.62032(14) 0.45304(13) 0.0359(6) Uani d . 1 . .
N N6 0.9431(3) 0.61113(13) 0.51868(13) 0.0318(6) Uani d . 1 B .
N N7 0.7394(3) 0.50109(14) 0.46751(13) 0.0322(6) Uani d . 1 . .
N N8 0.6688(3) 0.43844(14) 0.54359(13) 0.0329(6) Uani d . 1 . .
N N9 0.8837(3) 0.54727(14) 0.58893(13) 0.0321(6) Uani d . 1 . .
N N10 0.5377(3) 0.39052(14) 0.42586(13) 0.0333(6) Uani d . 1 . .
N N11 0.5108(3) 0.39071(15) 0.35605(13) 0.0349(6) Uani d . 1 B .
N N12 0.2410(3) 0.22050(14) 0.33247(13) 0.0354(6) Uani d . 1 B .
N N13 0.2218(3) 0.19251(14) 0.38056(13) 0.0356(6) Uani d . 1 . .
N N14 -0.1125(4) 0.01872(16) 0.28168(16) 0.0488(7) Uani d . 1 . .
N N15 0.0696(3) 0.08488(14) 0.38837(14) 0.0373(6) Uani d . 1 . .
N N16 1.1016(3) 0.67754(15) 0.63825(13) 0.0378(6) Uani d . 1 . .
H H16N 1.0588 0.6422 0.6517 0.045 Uiso calc R 1 . .
H H16M 1.1748 0.7174 0.6692 0.045 Uiso calc R 1 . .
N N17 0.4406(3) 0.31137(15) 0.48461(13) 0.0369(6) Uani d . 1 . .
H H17N 0.5025 0.3423 0.5266 0.044 Uiso calc R 1 B .
H H17M 0.3762 0.2695 0.4805 0.044 Uiso calc R 1 . .
C C1 1.6865(5) 1.0074(2) 0.8222(2) 0.0545(9) Uani d . 1 . .
H H1A 1.7624 1.0501 0.8219 0.082 Uiso calc R 1 . .
H H1B 1.7478 0.9715 0.8344 0.082 Uiso calc R 1 . .
H H1C 1.6169 1.0293 0.8586 0.082 Uiso calc R 1 . .
C C2 1.5832(4) 0.96327(19) 0.74835(19) 0.0444(8) Uani d . 1 . .
C C3 1.4027(4) 0.87033(17) 0.66531(18) 0.0386(7) Uani d . 1 . .
C C4 1.1104(4) 0.71951(16) 0.53837(16) 0.0345(7) Uani d . 1 . .
C C5 1.0559(4) 0.67071(16) 0.57146(16) 0.0320(7) Uani d . 1 B .
C C6 1.0198(4) 0.68461(16) 0.46545(17) 0.0361(7) Uani d . 1 B .
C C7 0.8499(4) 0.54981(16) 0.52534(16) 0.0310(6) Uani d . 1 B .
C C8 0.7878(4) 0.49012(16) 0.59835(16) 0.0314(6) Uani d . 1 B .
C C9 0.6561(4) 0.44673(17) 0.48198(15) 0.0310(6) Uani d . 1 B .
C C10 0.4443(4) 0.32788(17) 0.42756(16) 0.0333(7) Uani d . 1 B .
C C11 0.3520(4) 0.28622(17) 0.35716(16) 0.0349(7) Uani d . 1 . .
C C12 0.3997(4) 0.32902(18) 0.31600(16) 0.0353(7) Uani d . 1 B .
C C13 0.1050(4) 0.12619(17) 0.35169(16) 0.0346(7) Uani d . 1 . .
C C14 -0.0544(4) 0.02450(18) 0.34631(18) 0.0400(7) Uani d . 1 . .
C C15 -0.1193(5) -0.0316(2) 0.3746(2) 0.0545(9) Uani d . 1 . .
H H15A -0.2214 -0.0631 0.3432 0.082 Uiso calc R 1 . .
H H15B -0.1393 -0.0023 0.4243 0.082 Uiso calc R 1 . .
H H15C -0.0401 -0.0663 0.3750 0.082 Uiso calc R 1 . .
C C16 1.0319(5) 0.71468(17) 0.40775(17) 0.0436(8) Uani d . 1 . .
C C17 1.2056(5) 0.7151(2) 0.3907(2) 0.0552(10) Uani d . 1 B .
H H17A 1.2826 0.7492 0.4351 0.083 Uiso calc R 1 . .
H H17B 1.2140 0.7348 0.3534 0.083 Uiso calc R 1 . .
H H17C 1.2310 0.6615 0.3727 0.083 Uiso calc R 1 . .
C C18 0.9917(6) 0.79872(19) 0.4363(2) 0.0580(10) Uani d . 1 B .
H H18A 0.8826 0.7986 0.4490 0.087 Uiso calc R 1 . .
H H18B 0.9957 0.8179 0.3984 0.087 Uiso calc R 1 . .
H H18C 1.0713 0.8332 0.4796 0.087 Uiso calc R 1 . .
C C19 0.9102(5) 0.6628(2) 0.33927(19) 0.0579(11) Uani d . 1 B .
H H19A 0.9341 0.6090 0.3205 0.087 Uiso calc R 1 . .
H H19B 0.9181 0.6830 0.3023 0.087 Uiso calc R 1 . .
H H19C 0.8000 0.6631 0.3508 0.087 Uiso calc R 1 . .
C C20 0.3341(4) 0.30941(19) 0.23735(16) 0.0389(7) Uani d . 1 . .
C C21 0.3634(6) 0.2270(2) 0.18819(19) 0.0658(12) Uani d . 1 B .
H H21A 0.4805 0.2268 0.1893 0.099 Uiso calc R 1 . .
H H21B 0.3097 0.2122 0.1381 0.099 Uiso calc R 1 . .
H H21C 0.3189 0.1893 0.2057 0.099 Uiso calc R 1 . .
C C22 0.4140(5) 0.3709(2) 0.21546(19) 0.0547(10) Uani d . 1 B .
H H22A 0.3912 0.4229 0.2468 0.082 Uiso calc R 1 . .
H H22B 0.3703 0.3579 0.1646 0.082 Uiso calc R 1 . .
H H22C 0.5317 0.3714 0.2210 0.082 Uiso calc R 1 . .
C C23 0.1522(4) 0.3110(2) 0.22894(17) 0.0441(8) Uani d . 1 B .
H H23A 0.0976 0.2701 0.2403 0.066 Uiso calc R 1 . .
H H23B 0.1101 0.3013 0.1787 0.066 Uiso calc R 1 . .
H H23C 0.1317 0.3625 0.2624 0.066 Uiso calc R 1 . .
C C24 0.9025(5) 0.43178(19) 0.19536(13) 0.0392(13) Uani d PGU 0.786(6) B 1
C C25 0.8044(4) 0.36536(19) 0.14096(16) 0.0517(13) Uani d PGU 0.786(6) B 1
H H25 0.7270 0.3347 0.1533 0.062 Uiso calc PR 0.786(6) B 1
C C26 0.8195(4) 0.34377(19) 0.06846(14) 0.0626(15) Uani d PGU 0.786(6) B 1
H H26 0.7525 0.2984 0.0313 0.075 Uiso calc PR 0.786(6) B 1
C C27 0.9327(5) 0.3886(2) 0.05035(16) 0.0588(15) Uani d PGU 0.786(6) B 1
H H27 0.9431 0.3739 0.0008 0.071 Uiso calc PR 0.786(6) B 1
C C28 1.0308(5) 0.4550(2) 0.1048(2) 0.0534(15) Uani d PGU 0.786(6) B 1
H H28 1.1081 0.4857 0.0924 0.064 Uiso calc PR 0.786(6) B 1
C C29 1.0156(5) 0.47662(17) 0.1773(2) 0.0456(14) Uani d PGU 0.786(6) B 1
H H29 1.0827 0.5220 0.2144 0.055 Uiso calc PR 0.786(6) B 1
C C24A 0.9176(15) 0.4523(8) 0.1933(5) 0.033(4) Uani d PGU 0.214(6) B 2
C C25A 0.7821(11) 0.4243(8) 0.1384(5) 0.045(4) Uani d PGU 0.214(6) B 2
H H25A 0.6774 0.4145 0.1493 0.054 Uiso calc PR 0.214(6) B 2
C C26A 0.7998(12) 0.4108(7) 0.0676(5) 0.050(4) Uani d PGU 0.214(6) B 2
H H26A 0.7072 0.3917 0.0300 0.060 Uiso calc PR 0.214(6) B 2
C C27A 0.9531(15) 0.4252(7) 0.0516(6) 0.044(4) Uani d PGU 0.214(6) B 2
H H27A 0.9652 0.4160 0.0032 0.053 Uiso calc PR 0.214(6) B 2
C C28A 1.0885(11) 0.4532(8) 0.1065(8) 0.037(4) Uani d PGU 0.214(6) B 2
H H28A 1.1933 0.4631 0.0956 0.044 Uiso calc PR 0.214(6) B 2
C C29A 1.0708(12) 0.4667(8) 0.1773(7) 0.032(4) Uani d PGU 0.214(6) B 2
H H29A 1.1634 0.4858 0.2148 0.039 Uiso calc PR 0.214(6) B 2
C C30 1.7987(5) 1.1878(2) 0.7660(2) 0.0549(10) Uani d . 1 . .
C C31 1.9181(6) 1.2527(2) 0.7902(2) 0.0623(11) Uani d . 1 . .
H H31 2.0216 1.2477 0.7756 0.075 Uiso calc R 1 . .
C C32 1.8840(7) 1.3265(2) 0.8368(2) 0.0718(14) Uani d . 1 . .
H H32 1.9667 1.3712 0.8550 0.086 Uiso calc R 1 . .
C C33 1.7335(8) 1.3350(3) 0.8566(3) 0.0808(15) Uani d . 1 . .
H H33 1.7113 1.3853 0.8871 0.097 Uiso calc R 1 . .
C C34 1.6159(7) 1.2702(3) 0.8321(3) 0.0838(15) Uani d . 1 . .
H H34 1.5117 1.2755 0.8458 0.101 Uiso calc R 1 . .
C C35 1.6479(6) 1.1958(3) 0.7868(3) 0.0762(13) Uani d . 1 . .
H H35 1.5659 1.1510 0.7703 0.091 Uiso calc R 1 . .
C C36 -0.3128(4) -0.1420(2) 0.1217(2) 0.0550(10) Uani d . 1 . .
C C37 -0.4253(5) -0.1824(3) 0.0581(2) 0.0708(13) Uani d . 1 . .
H H37 -0.5345 -0.1729 0.0567 0.085 Uiso calc R 1 . .
C C38 -0.3786(5) -0.2362(2) -0.0028(2) 0.0577(10) Uani d . 1 . .
H H38 -0.4548 -0.2624 -0.0467 0.069 Uiso calc R 1 . .
C C39 -0.2229(5) -0.2522(2) -0.00060(18) 0.0497(9) Uani d . 1 . .
H H39 -0.1909 -0.2896 -0.0426 0.060 Uiso calc R 1 . .
C C40 -0.1127(5) -0.2129(2) 0.06386(18) 0.0479(8) Uani d . 1 . .
H H40 -0.0050 -0.2242 0.0661 0.057 Uiso calc R 1 . .
C C41 -0.1577(4) -0.15748(19) 0.12469(18) 0.0435(8) Uani d . 1 . .
H H41 -0.0810 -0.1303 0.1684 0.052 Uiso calc R 1 . .
O O5 1.2733(5) 0.8315(3) 0.8091(3) 0.0608(12) Uani d PU 0.750(5) C 3
H H5O 1.3243 0.8554 0.7891 0.073 Uiso calc PR 0.750(5) C 3
C C42 1.2431(6) 0.8841(2) 0.87364(18) 0.0589(16) Uani d PGU 0.750(5) C 3
C C43 1.1592(6) 0.85495(18) 0.9146(2) 0.0800(19) Uani d PGU 0.750(5) C 3
H H43 1.1281 0.7998 0.8978 0.096 Uiso calc PR 0.750(5) C 3
C C44 1.1207(7) 0.9064(3) 0.9800(2) 0.107(2) Uani d PGU 0.750(5) C 3
H H44 1.0633 0.8864 1.0080 0.128 Uiso calc PR 0.750(5) C 3
C C45 1.1662(7) 0.9870(2) 1.0046(2) 0.115(3) Uani d PGU 0.750(5) C 3
H H45 1.1399 1.0221 1.0493 0.138 Uiso calc PR 0.750(5) C 3
C C46 1.2501(7) 1.01619(17) 0.9636(2) 0.103(2) Uani d PGU 0.750(5) C 3
H H46 1.2812 1.0713 0.9804 0.123 Uiso calc PR 0.750(5) C 3
C C47 1.2886(5) 0.9648(2) 0.8982(2) 0.0742(17) Uani d PGU 0.750(5) C 3
H H47 1.3460 0.9847 0.8702 0.089 Uiso calc PR 0.750(5) C 3
O O5A 1.2908(14) 0.7925(7) 0.7733(6) 0.046(3) Uani d PU 0.250(5) C 4
H H5OA 1.3261 0.8288 0.7624 0.055 Uiso calc PR 0.250(5) C 4
C C42A 1.2674(13) 0.8238(6) 0.8441(4) 0.042(3) Uani d PGU 0.250(5) C 4
C C43A 1.2089(12) 0.7696(5) 0.8690(4) 0.044(3) Uani d PGU 0.250(5) C 4
H H43A 1.1923 0.7149 0.8380 0.053 Uiso calc PR 0.250(5) C 4
C C44A 1.1747(12) 0.7953(6) 0.9394(5) 0.059(4) Uani d PGU 0.250(5) C 4
H H44A 1.1347 0.7583 0.9564 0.070 Uiso calc PR 0.250(5) C 4
C C45A 1.1989(14) 0.8753(7) 0.9848(4) 0.072(4) Uani d PGU 0.250(5) C 4
H H45A 1.1755 0.8929 1.0329 0.086 Uiso calc PR 0.250(5) C 4
C C46A 1.2575(14) 0.9295(5) 0.9598(5) 0.073(4) Uani d PGU 0.250(5) C 4
H H46A 1.2741 0.9841 0.9909 0.088 Uiso calc PR 0.250(5) C 4
C C47A 1.2917(14) 0.9038(5) 0.8895(6) 0.059(4) Uani d PGU 0.250(5) C 4
H H47A 1.3317 0.9408 0.8724 0.071 Uiso calc PR 0.250(5) C 4
C C48 1.3808(7) 1.4337(3) 0.9641(5) 0.107(2) Uani d . 1 . .
C C49 1.3945(9) 1.4900(4) 0.9377(4) 0.123(2) Uani d . 1 . .
H H49 1.3234 1.4847 0.8957 0.148 Uiso calc R 1 . .
C C50 1.4826(9) 1.4444(4) 1.0249(4) 0.119(2) Uani d . 1 . .
H H50 1.4705 1.4057 1.0433 0.143 Uiso calc R 1 . .
C C51 0.3909(5) 0.0526(2) 0.5112(2) 0.0512(9) Uani d . 1 . .
C C52 0.3499(5) -0.0221(2) 0.4556(2) 0.0505(9) Uani d . 1 . .
H H52 0.2458 -0.0376 0.4256 0.061 Uiso calc R 1 . .
C C53 0.4588(5) -0.0747(2) 0.4431(2) 0.0511(9) Uani d . 1 . .
H H53 0.4315 -0.1254 0.4036 0.061 Uiso calc R 1 . .
C C54 0.4742(6) 0.5906(4) 0.2625(3) 0.0928(18) Uani d . 1 B .
H H54A 0.5798 0.6023 0.2497 0.139 Uiso calc R 1 . .
H H54B 0.4180 0.6363 0.2738 0.139 Uiso calc R 1 . .
H H54C 0.4083 0.5451 0.2213 0.139 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.031 0.018
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Na Na 0.135 0.124
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.049 0.032
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.333 0.557
;
International Tables for Crystallography
(1992, 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_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 S1 C3 . . 90.98(15) ?
N14 S2 C13 . . 90.84(15) ?
O8 Na1 N7 . . 118.62(9) ?
O8 Na1 O2 . . 121.65(9) ?
N7 Na1 O2 . . 119.57(9) ?
O8 Na1 N11 . . 97.59(9) ?
N7 Na1 N11 . . 65.51(8) y
O2 Na1 N11 . . 109.37(9) ?
O8 Na1 N5 . . 104.19(9) ?
N7 Na1 N5 . . 65.04(8) y
O2 Na1 N5 . . 96.00(9) ?
N11 Na1 N5 . . 130.53(8) ?
C24 O2 C24A . . 15.1(6) ?
C24 O2 Na1 . . 140.8(2) ?
C24A O2 Na1 . . 136.1(5) ?
C24 O2 H2O . . 109.5 ?
C24A O2 H2O . . 102.3 ?
Na1 O2 H2O . . 103.0 ?
C30 O3 H3O . . 109.5 ?
C36 O4 H4O . . 109.5 ?
C48 O6 H6O . . 109.5 ?
C51 O7 H7O . . 109.5 ?
C54 O8 Na1 . . 125.3(2) ?
C54 O8 H8O . . 109.5 ?
Na1 O8 H8O . . 113.0 ?
C2 N1 S1 . . 109.0(2) ?
C3 N2 C2 . . 108.6(3) ?
N4 N3 C3 . . 112.2(3) ?
N3 N4 C4 . . 114.1(3) ?
C6 N5 N6 . . 105.8(2) ?
C6 N5 Na1 . . 142.0(2) ?
N6 N5 Na1 . . 112.22(17) ?
C5 N6 C7 . . 127.7(2) ?
C5 N6 N5 . . 111.5(2) ?
C7 N6 N5 . . 120.7(2) ?
C9 N7 C7 . . 111.0(2) ?
C9 N7 Na1 . . 124.4(2) ?
C7 N7 Na1 . . 124.62(19) ?
C9 N8 C8 . . 115.5(3) ?
C7 N9 C8 . . 115.9(3) ?
C10 N10 C9 . . 127.2(2) ?
C10 N10 N11 . . 111.7(2) ?
C9 N10 N11 . . 120.9(2) ?
C12 N11 N10 . . 105.4(2) ?
C12 N11 Na1 . . 142.8(2) ?
N10 N11 Na1 . . 111.76(17) ?
N13 N12 C11 . . 114.4(3) ?
N12 N13 C13 . . 111.0(2) ?
C14 N14 S2 . . 110.1(2) ?
C13 N15 C14 . . 108.6(3) ?
C5 N16 H16N . . 120.0 ?
C5 N16 H16M . . 120.0 ?
H16N N16 H16M . . 120.0 ?
C10 N17 H17N . . 120.0 ?
C10 N17 H17M . . 120.0 ?
H17N N17 H17M . . 120.0 ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
N1 C2 N2 . . 118.1(3) ?
N1 C2 C1 . . 120.9(3) ?
N2 C2 C1 . . 120.9(3) ?
N2 C3 N3 . . 120.1(3) ?
N2 C3 S1 . . 113.2(2) ?
N3 C3 S1 . . 126.7(3) ?
N4 C4 C5 . . 127.1(3) ?
N4 C4 C6 . . 127.4(3) ?
C5 C4 C6 . . 105.5(3) ?
N16 C5 N6 . . 125.1(3) ?
N16 C5 C4 . . 129.2(3) ?
N6 C5 C4 . . 105.7(2) ?
N5 C6 C4 . . 111.5(3) ?
N5 C6 C16 . . 121.9(3) ?
C4 C6 C16 . . 126.5(3) ?
N9 C7 N7 . . 128.1(3) ?
N9 C7 N6 . . 114.7(3) ?
N7 C7 N6 . . 117.2(2) ?
O1 C8 N8 . . 119.3(3) ?
O1 C8 N9 . . 119.8(3) ?
N8 C8 N9 . . 120.9(3) ?
N8 C9 N7 . . 128.5(3) ?
N8 C9 N10 . . 114.1(3) ?
N7 C9 N10 . . 117.4(3) ?
N17 C10 N10 . . 126.4(3) ?
N17 C10 C11 . . 127.6(3) ?
N10 C10 C11 . . 105.9(3) ?
N12 C11 C10 . . 127.9(3) ?
N12 C11 C12 . . 126.4(3) ?
C10 C11 C12 . . 105.7(3) ?
N11 C12 C11 . . 111.3(3) ?
N11 C12 C20 . . 121.8(3) ?
C11 C12 C20 . . 126.9(3) ?
N15 C13 N13 . . 122.4(3) ?
N15 C13 S2 . . 112.6(2) ?
N13 C13 S2 . . 125.0(2) ?
N14 C14 N15 . . 117.9(3) ?
N14 C14 C15 . . 122.0(3) ?
N15 C14 C15 . . 120.1(3) ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C6 C16 C19 . . 110.0(3) ?
C6 C16 C17 . . 109.3(3) ?
C19 C16 C17 . . 110.3(3) ?
C6 C16 C18 . . 109.1(3) ?
C19 C16 C18 . . 108.6(3) ?
C17 C16 C18 . . 109.7(3) ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C16 C18 H18A . . 109.5 ?
C16 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C16 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C16 C19 H19A . . 109.5 ?
C16 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C16 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C12 C20 C23 . . 109.1(2) ?
C12 C20 C22 . . 110.1(3) ?
C23 C20 C22 . . 108.0(3) ?
C12 C20 C21 . . 109.8(3) ?
C23 C20 C21 . . 108.8(3) ?
C22 C20 C21 . . 111.0(3) ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C20 C22 H22A . . 109.5 ?
C20 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C20 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C20 C23 H23A . . 109.5 ?
C20 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C20 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
O2 C24 C25 . . 120.7(3) ?
O2 C24 C29 . . 119.3(3) ?
C25 C24 C29 . . 120.0 ?
C24 C25 C26 . . 120.0 ?
C24 C25 H25 . . 120.0 ?
C26 C25 H25 . . 120.0 ?
C27 C26 C25 . . 120.0 ?
C27 C26 H26 . . 120.0 ?
C25 C26 H26 . . 120.0 ?
C26 C27 C28 . . 120.0 ?
C26 C27 H27 . . 120.0 ?
C28 C27 H27 . . 120.0 ?
C29 C28 C27 . . 120.0 ?
C29 C28 H28 . . 120.0 ?
C27 C28 H28 . . 120.0 ?
C28 C29 C24 . . 120.0 ?
C28 C29 H29 . . 120.0 ?
C24 C29 H29 . . 120.0 ?
C25A C24A C29A . . 120.0 ?
C25A C24A O2 . . 115.8(8) ?
C29A C24A O2 . . 123.6(7) ?
C24A C25A C26A . . 120.0 ?
C24A C25A H25A . . 120.0 ?
C26A C25A H25A . . 120.0 ?
C27A C26A C25A . . 120.0 ?
C27A C26A H26A . . 120.0 ?
C25A C26A H26A . . 120.0 ?
C28A C27A C26A . . 120.0 ?
C28A C27A H27A . . 120.0 ?
C26A C27A H27A . . 120.0 ?
C27A C28A C29A . . 120.0 ?
C27A C28A H28A . . 120.0 ?
C29A C28A H28A . . 120.0 ?
C28A C29A C24A . . 120.0 ?
C28A C29A H29A . . 120.0 ?
C24A C29A H29A . . 120.0 ?
C31 C30 C35 . . 120.1(4) ?
C31 C30 O3 . . 117.6(4) ?
C35 C30 O3 . . 122.3(4) ?
C30 C31 C32 . . 118.8(5) ?
C30 C31 H31 . . 120.6 ?
C32 C31 H31 . . 120.6 ?
C33 C32 C31 . . 121.3(4) ?
C33 C32 H32 . . 119.3 ?
C31 C32 H32 . . 119.3 ?
C34 C33 C32 . . 119.2(5) ?
C34 C33 H33 . . 120.4 ?
C32 C33 H33 . . 120.4 ?
C33 C34 C35 . . 120.5(5) ?
C33 C34 H34 . . 119.8 ?
C35 C34 H34 . . 119.8 ?
C30 C35 C34 . . 120.0(5) ?
C30 C35 H35 . . 120.0 ?
C34 C35 H35 . . 120.0 ?
C41 C36 O4 . . 122.4(3) ?
C41 C36 C37 . . 120.2(3) ?
O4 C36 C37 . . 117.4(3) ?
C38 C37 C36 . . 119.9(4) ?
C38 C37 H37 . . 120.1 ?
C36 C37 H37 . . 120.1 ?
C39 C38 C37 . . 120.5(4) ?
C39 C38 H38 . . 119.8 ?
C37 C38 H38 . . 119.8 ?
C38 C39 C40 . . 119.0(3) ?
C38 C39 H39 . . 120.5 ?
C40 C39 H39 . . 120.5 ?
C41 C40 C39 . . 120.8(3) ?
C41 C40 H40 . . 119.6 ?
C39 C40 H40 . . 119.6 ?
C36 C41 C40 . . 119.5(3) ?
C36 C41 H41 . . 120.2 ?
C40 C41 H41 . . 120.2 ?
C42 O5 H5O . . 109.5 ?
O5 C42 C43 . . 117.6(3) ?
O5 C42 C47 . . 122.4(3) ?
C43 C42 C47 . . 120.0 ?
C42 C43 C44 . . 120.0 ?
C42 C43 H43 . . 120.0 ?
C44 C43 H43 . . 120.0 ?
C43 C44 C45 . . 120.0 ?
C43 C44 H44 . . 120.0 ?
C45 C44 H44 . . 120.0 ?
C46 C45 C44 . . 120.0 ?
C46 C45 H45 . . 120.0 ?
C44 C45 H45 . . 120.0 ?
C45 C46 C47 . . 120.0 ?
C45 C46 H46 . . 120.0 ?
C47 C46 H46 . . 120.0 ?
C46 C47 C42 . . 120.0 ?
C46 C47 H47 . . 120.0 ?
C42 C47 H47 . . 120.0 ?
C42A O5A H5OA . . 109.5 ?
O5A C42A C43A . . 115.2(8) ?
O5A C42A C47A . . 124.7(8) ?
C43A C42A C47A . . 120.0 ?
C42A C43A C44A . . 120.0 ?
C42A C43A H43A . . 120.0 ?
C44A C43A H43A . . 120.0 ?
C43A C44A C45A . . 120.0 ?
C43A C44A H44A . . 120.0 ?
C45A C44A H44A . . 120.0 ?
C44A C45A C46A . . 120.0 ?
C44A C45A H45A . . 120.0 ?
C46A C45A H45A . . 120.0 ?
C47A C46A C45A . . 120.0 ?
C47A C46A H46A . . 120.0 ?
C45A C46A H46A . . 120.0 ?
C46A C47A C42A . . 120.0 ?
C46A C47A H47A . . 120.0 ?
C42A C47A H47A . . 120.0 ?
O6 C48 C50 . . 130.8(7) ?
O6 C48 C49 . . 109.8(8) ?
C50 C48 C49 . . 119.1(6) ?
C48 C49 C50 . 2_887 117.7(7) ?
C48 C49 H49 . . 121.1 ?
C50 C49 H49 2_887 . 121.1 ?
C48 C50 C49 . 2_887 123.2(7) ?
C48 C50 H50 . . 118.4 ?
C49 C50 H50 2_887 . 118.4 ?
O7 C51 C52 . . 122.9(4) ?
O7 C51 C53 . 2_656 116.9(4) ?
C52 C51 C53 . 2_656 119.9(3) ?
C51 C52 C53 . . 120.6(4) ?
C51 C52 H52 . . 119.7 ?
C53 C52 H52 . . 119.7 ?
C52 C53 C51 . 2_656 119.5(4) ?
C52 C53 H53 . . 120.3 ?
C51 C53 H53 2_656 . 120.3 ?
O8 C54 H54A . . 109.5 ?
O8 C54 H54B . . 109.5 ?
H54A C54 H54B . . 109.5 ?
O8 C54 H54C . . 109.5 ?
H54A C54 H54C . . 109.5 ?
H54B C54 H54C . . 109.5 ?
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
S1 N1 . 1.659(3) ?
S1 C3 . 1.711(3) ?
S2 N14 . 1.654(3) ?
S2 C13 . 1.725(3) ?
Na1 O8 . 2.336(3) y
Na1 N7 . 2.420(3) y
Na1 O2 . 2.437(2) y
Na1 N11 . 2.642(3) y
Na1 N5 . 2.644(3) y
O1 C8 . 1.253(3) ?
O2 C24 . 1.357(3) ?
O2 C24A . 1.528(10) ?
O2 H2O . 0.8400 ?
O3 C30 . 1.388(4) ?
O3 H3O . 0.8400 ?
O4 C36 . 1.367(4) ?
O4 H4O . 0.8400 ?
O6 C48 . 1.330(9) ?
O6 H6O . 0.8400 ?
O7 C51 . 1.301(5) ?
O7 H7O . 0.8400 ?
O8 C54 . 1.452(5) ?
O8 H8O . 0.8400 ?
N1 C2 . 1.323(4) ?
N2 C3 . 1.310(4) ?
N2 C2 . 1.360(4) ?
N3 N4 . 1.295(4) y
N3 C3 . 1.389(4) ?
N4 C4 . 1.351(4) ?
N5 C6 . 1.314(4) ?
N5 N6 . 1.413(3) ?
N6 C5 . 1.374(4) ?
N6 C7 . 1.394(4) ?
N7 C9 . 1.335(4) ?
N7 C7 . 1.339(4) ?
N8 C9 . 1.323(4) ?
N8 C8 . 1.363(4) ?
N9 C7 . 1.317(4) ?
N9 C8 . 1.372(4) ?
N10 C10 . 1.368(4) ?
N10 C9 . 1.401(4) ?
N10 N11 . 1.418(3) ?
N11 C12 . 1.314(4) ?
N12 N13 . 1.308(3) y
N12 C11 . 1.347(4) ?
N13 C13 . 1.378(4) ?
N14 C14 . 1.309(4) ?
N15 C13 . 1.318(4) ?
N15 C14 . 1.372(4) ?
N16 C5 . 1.322(4) ?
N16 H16N . 0.8800 ?
N16 H16M . 0.8800 ?
N17 C10 . 1.325(4) ?
N17 H17N . 0.8800 ?
N17 H17M . 0.8800 ?
C1 C2 . 1.500(5) ?
C1 H1A . 0.9800 ?
C1 H1B . 0.9800 ?
C1 H1C . 0.9800 ?
C4 C5 . 1.418(4) ?
C4 C6 . 1.438(4) ?
C6 C16 . 1.510(4) ?
C10 C11 . 1.408(4) ?
C11 C12 . 1.444(4) ?
C12 C20 . 1.513(4) ?
C14 C15 . 1.486(5) ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 C19 . 1.520(5) ?
C16 C17 . 1.537(5) ?
C16 C18 . 1.538(4) ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
C20 C23 . 1.521(4) ?
C20 C22 . 1.528(5) ?
C20 C21 . 1.531(4) ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C21 H21C . 0.9800 ?
C22 H22A . 0.9800 ?
C22 H22B . 0.9800 ?
C22 H22C . 0.9800 ?
C23 H23A . 0.9800 ?
C23 H23B . 0.9800 ?
C23 H23C . 0.9800 ?
C24 C25 . 1.3900 ?
C24 C29 . 1.3900 ?
C25 C26 . 1.3900 ?
C25 H25 . 0.9500 ?
C26 C27 . 1.3900 ?
C26 H26 . 0.9500 ?
C27 C28 . 1.3900 ?
C27 H27 . 0.9500 ?
C28 C29 . 1.3900 ?
C28 H28 . 0.9500 ?
C29 H29 . 0.9500 ?
C24A C25A . 1.3900 ?
C24A C29A . 1.3900 ?
C25A C26A . 1.3900 ?
C25A H25A . 0.9500 ?
C26A C27A . 1.3900 ?
C26A H26A . 0.9500 ?
C27A C28A . 1.3900 ?
C27A H27A . 0.9500 ?
C28A C29A . 1.3900 ?
C28A H28A . 0.9500 ?
C29A H29A . 0.9500 ?
C30 C31 . 1.378(5) ?
C30 C35 . 1.382(6) ?
C31 C32 . 1.410(6) ?
C31 H31 . 0.9500 ?
C32 C33 . 1.374(7) ?
C32 H32 . 0.9500 ?
C33 C34 . 1.367(7) ?
C33 H33 . 0.9500 ?
C34 C35 . 1.403(6) ?
C34 H34 . 0.9500 ?
C35 H35 . 0.9500 ?
C36 C41 . 1.361(5) ?
C36 C37 . 1.388(5) ?
C37 C38 . 1.374(5) ?
C37 H37 . 0.9500 ?
C38 C39 . 1.369(5) ?
C38 H38 . 0.9500 ?
C39 C40 . 1.387(5) ?
C39 H39 . 0.9500 ?
C40 C41 . 1.379(4) ?
C40 H40 . 0.9500 ?
C41 H41 . 0.9500 ?
O5 C42 . 1.358(5) ?
O5 H5O . 0.8400 ?
C42 C43 . 1.3900 ?
C42 C47 . 1.3900 ?
C43 C44 . 1.3900 ?
C43 H43 . 0.9500 ?
C44 C45 . 1.3900 ?
C44 H44 . 0.9500 ?
C45 C46 . 1.3900 ?
C45 H45 . 0.9500 ?
C46 C47 . 1.3900 ?
C46 H46 . 0.9500 ?
C47 H47 . 0.9500 ?
O5A C42A . 1.365(12) ?
O5A H5OA . 0.8400 ?
C42A C43A . 1.3900 ?
C42A C47A . 1.3900 ?
C43A C44A . 1.3900 ?
C43A H43A . 0.9500 ?
C44A C45A . 1.3900 ?
C44A H44A . 0.9500 ?
C45A C46A . 1.3900 ?
C45A H45A . 0.9500 ?
C46A C47A . 1.3900 ?
C46A H46A . 0.9500 ?
C47A H47A . 0.9500 ?
C48 C50 . 1.353(9) ?
C48 C49 . 1.374(9) ?
C49 C50 2_887 1.405(8) ?
C49 H49 . 0.9500 ?
C50 C49 2_887 1.405(8) ?
C50 H50 . 0.9500 ?
C51 C52 . 1.380(5) ?
C51 C53 2_656 1.394(5) ?
C52 C53 . 1.382(5) ?
C52 H52 . 0.9500 ?
C53 C51 2_656 1.394(5) ?
C53 H53 . 0.9500 ?
C54 H54A . 0.9800 ?
C54 H54B . 0.9800 ?
C54 H54C . 0.9800 ?
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
O2 H2O O1 . . 2_766 0.840 1.8444 2.682(2) 174.59 y
O3 H3O N1 . . . 0.840 2.013 2.835(3) 165.8 y
O4 H4O N14 . . . 0.840 1.987 2.757(3) 152.0 y
O5 H5O N2 . . . 0.840 2.095 2.926(6) 170.1 y
O5A H5OA N2 . . . 0.840 2.021 2.831(14) 161.7 y
O7 H7O N15 . . . 0.840 2.205 2.975(5) 152.3 y
O8 H8O O1 . . 2_666 0.840 1.986 2.822(3) 173.15 y
N16 H16M N3 . . . 0.880 2.164 2.719(4) 120.5 y
N16 H16N N9 . . . 0.880 2.047 2.660(3) 125.9 y
N17 H17M N13 . . . 0.880 2.134 2.705(2) 122.0 y
N17 H17N N8 . . . 0.880 2.059 2.661(3) 124.7 y
