#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/90/2229098.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_2229098
loop_
_publ_author_name
'Akkurt, Mehmet'
'Çelik, Ísmail'
'Demir, Hale'
'Özkırımlı, Sumru'
'Büyükgüngör, Orhan'
_publ_section_title
;
 N-[5-Methyl-2-(2-nitrophenyl)-4-oxo-1,3-thiazolidin-3-yl]pyridine-3-carboxamide
 monohydrate
;
_journal_coeditor_code           IM2255
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o293
_journal_page_last               o294
_journal_paper_doi               10.1107/S1600536811000481
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H14 N4 O4 S, H2 O'
_chemical_formula_moiety         'C16 H14 N4 O4 S, H2 O'
_chemical_formula_sum            'C16 H16 N4 O5 S'
_chemical_formula_weight         376.40
_chemical_name_systematic
;
N-[5-Methyl-2-(2-nitrophenyl)-4-oxo-1,3-thiazolidin-3-yl]pyridine-3-
carboxamide monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                92.957(4)
_cell_angle_beta                 104.176(4)
_cell_angle_gamma                116.792(4)
_cell_formula_units_Z            2
_cell_length_a                   8.1399(4)
_cell_length_b                   8.4106(4)
_cell_length_c                   15.0274(7)
_cell_measurement_reflns_used    15771
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.03
_cell_measurement_theta_min      2.76
_cell_volume                     874.66(8)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11714
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.76
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.899
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.550
_exptl_crystal_size_min          0.490
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.269
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3963
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0434
_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)+(0.0570P)²+0.1358P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1212
_reflns_number_gt                3192
_reflns_number_total             3963
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2255.cif
_cod_data_source_block           I
_cod_database_code               2229098
_cod_database_fobs_code          2229098
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.56133(7) 0.45061(8) 0.61403(3) 0.0699(2) Uani . . 1.000
O O1 0.7192(5) 0.2528(4) 0.38302(13) 0.1562(12) Uani . . 1.000
O O2 0.7900(2) 0.4795(3) 0.48092(11) 0.0856(6) Uani . . 1.000
O O3A 0.7493(19) 0.5809(14) 0.8800(8) 0.091(3) Uani . . 0.531(9)
O O4 1.1251(2) 0.84381(17) 0.77262(11) 0.0811(5) Uani . . 1.000
N N1 0.7598(3) 0.3251(3) 0.46237(12) 0.0771(6) Uani . . 1.000
N N2 0.84041(19) 0.50765(19) 0.76035(9) 0.0551(4) Uani . . 1.000
N N3 1.0289(2) 0.56998(19) 0.81531(10) 0.0563(4) Uani . . 1.000
N N4 1.6987(2) 0.9892(2) 0.90983(13) 0.0741(6) Uani . . 1.000
C C1 0.7803(3) 0.2246(3) 0.53763(13) 0.0645(6) Uani . . 1.000
C C2 0.7799(4) 0.0637(3) 0.5129(2) 0.0927(9) Uani . . 1.000
C C3 0.7969(4) -0.0385(4) 0.5785(3) 0.1087(13) Uani . . 1.000
C C4 0.8097(4) 0.0165(3) 0.6687(2) 0.0947(10) Uani . . 1.000
C C5 0.8058(3) 0.1748(3) 0.69268(15) 0.0707(7) Uani . . 1.000
C C6 0.7942(2) 0.2861(2) 0.62885(12) 0.0539(5) Uani . . 1.000
C C7 0.7962(2) 0.4616(2) 0.65973(11) 0.0527(5) Uani . . 1.000
C C8A 0.5297(5) 0.4937(9) 0.7236(2) 0.0587(13) Uani . . 0.531(9)
C C9A 0.7153(13) 0.5370(11) 0.7958(6) 0.0610(19) Uani . . 0.531(9)
C C10A 0.3540(12) 0.3317(16) 0.7341(6) 0.126(4) Uani . . 0.531(9)
C C11 1.1625(3) 0.7433(2) 0.81826(12) 0.0567(5) Uani . . 1.000
C C12 1.3603(2) 0.7956(2) 0.87999(12) 0.0529(5) Uani . . 1.000
C C13 1.3975(3) 0.7257(3) 0.95825(13) 0.0648(6) Uani . . 1.000
C C14 1.5852(3) 0.7867(3) 1.01129(15) 0.0738(7) Uani . . 1.000
C C15 1.7293(3) 0.9187(3) 0.98500(15) 0.0681(6) Uani . . 1.000
C C16 1.5163(3) 0.9272(2) 0.85835(14) 0.0679(6) Uani . . 1.000
C C8B 0.5041(6) 0.3820(10) 0.7244(3) 0.0592(16) Uani . . 0.469(9)
C C9B 0.7003(12) 0.4774(11) 0.7995(6) 0.0513(16) Uani . . 0.469(9)
C C10B 0.3623(15) 0.4314(15) 0.7441(7) 0.093(3) Uani . . 0.469(9)
O O3B 0.7218(17) 0.5168(14) 0.8810(8) 0.076(2) Uani . . 0.469(9)
O OW1 0.0315(2) 0.3195(2) 0.93103(12) 0.0931(6) Uani . . 1.000
H H4 0.82100 -0.05310 0.71360 0.1130 Uiso calc R 1.000
H H7 0.89160 0.56040 0.63860 0.0630 Uiso calc R 1.000
H H8A 0.50960 0.60000 0.72670 0.0710 Uiso calc . 0.531(9)
H H5 0.81110 0.20840 0.75370 0.0850 Uiso calc R 1.000
H H10B 0.33860 0.35480 0.79400 0.1890 Uiso calc . 0.531(9)
H H10C 0.37100 0.22610 0.72940 0.1890 Uiso calc . 0.531(9)
H H13 1.29640 0.63760 0.97530 0.0780 Uiso calc R 1.000
H H14 1.61340 0.73910 1.06390 0.0890 Uiso calc R 1.000
H H15 1.85600 0.96150 1.02190 0.0820 Uiso calc R 1.000
H H16 1.49240 0.97470 0.80510 0.0810 Uiso calc R 1.000
H H10A 0.24130 0.31160 0.68570 0.1890 Uiso calc . 0.531(9)
H HN1 1.048(3) 0.499(2) 0.8508(13) 0.062(5) Uiso . . 1.000
H H2 0.76800 0.02530 0.45140 0.1110 Uiso calc R 1.000
H H3 0.79980 -0.14520 0.56220 0.1300 Uiso calc R 1.000
H H8B 0.45250 0.25050 0.71860 0.0710 Uiso calc . 0.469(9)
H H10D 0.24250 0.36760 0.69470 0.1400 Uiso calc . 0.469(9)
H H10E 0.41040 0.55960 0.74800 0.1400 Uiso calc . 0.469(9)
H H10F 0.34190 0.39900 0.80230 0.1400 Uiso calc . 0.469(9)
H HW1 0.078(4) 0.355(4) 0.9872(13) 0.120(11) Uiso . . 1.000
H HW2 -0.068(3) 0.230(3) 0.924(2) 0.126(11) Uiso . . 1.000
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'
S S 0.1246 0.1234 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 21 3 0.2497
-9 -23 -2 0.2640
3 -6 29 0.3322
-28 1 24 0.2027
18 -25 3 0.3465
7 19 13 0.3283
-13 -16 19 0.2950
1 -9 13 0.3469
10 9 -25 0.3600
-28 -17 25 0.2549
-5 -9 25 0.3395
-24 17 3 0.2214
10 -8 21 0.4233
-15 24 19 0.2769
2 -2 7 0.3837
-7 -2 30 0.3234
-19 14 22 0.2652
7 -16 20 0.3459
-4 29 25 0.2751
5 -21 9 0.3474
7 24 5 0.2829
2 2 -3 0.2861
-19 0 -13 0.4042
-5 1 -10 0.4851
18 -14 -13 0.2997
11 -17 -24 0.3000
11 -13 -8 0.3306
5 -11 27 0.3254
4 -8 -29 0.4362
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
C7 S1 C8A . . . 96.72(17) no
C7 S1 C8B . . . 89.56(19) no
HW1 OW1 HW2 . . . 105(3) no
O1 N1 C1 . . . 118.6(2) no
O2 N1 C1 . . . 120.00(17) no
O1 N1 O2 . . . 121.4(2) no
N3 N2 C9A . . . 119.9(4) no
N3 N2 C9B . . . 120.7(4) no
N3 N2 C7 . . . 118.23(15) no
C7 N2 C9B . . . 120.9(4) no
C7 N2 C9A . . . 119.4(4) no
N2 N3 C11 . . . 118.67(16) no
C15 N4 C16 . . . 117.28(18) no
C11 N3 HN1 . . . 124.9(14) no
N2 N3 HN1 . . . 115.9(14) no
N1 C1 C2 . . . 116.4(2) no
N1 C1 C6 . . . 121.7(2) no
C2 C1 C6 . . . 121.9(2) no
C1 C2 C3 . . . 120.1(3) no
C2 C3 C4 . . . 119.8(3) no
C3 C4 C5 . . . 120.0(3) no
C4 C5 C6 . . . 122.3(2) no
C5 C6 C7 . . . 120.07(16) no
C1 C6 C7 . . . 124.04(16) no
C1 C6 C5 . . . 115.89(18) no
N2 C7 C6 . . . 113.13(13) no
S1 C7 N2 . . . 103.61(12) no
S1 C7 C6 . . . 112.56(12) no
C9A C8A C10A . . . 114.1(6) no
S1 C8A C9A . . . 106.0(5) no
S1 C8A C10A . . . 109.8(5) no
C9B C8B C10B . . . 113.3(7) no
S1 C8B C10B . . . 112.3(5) no
S1 C8B C9B . . . 104.0(5) no
N2 C9A C8A . . . 113.7(6) no
O3A C9A C8A . . . 124.5(12) no
O3A C9A N2 . . . 121.6(11) no
O3B C9B C8B . . . 124.1(11) no
N2 C9B C8B . . . 109.7(6) no
O3B C9B N2 . . . 126.2(11) no
O4 C11 N3 . . . 122.8(2) no
N3 C11 C12 . . . 113.92(16) no
O4 C11 C12 . . . 123.26(16) no
C11 C12 C16 . . . 117.92(16) no
C13 C12 C16 . . . 117.71(19) no
C11 C12 C13 . . . 124.34(17) no
C12 C13 C14 . . . 119.5(2) no
C13 C14 C15 . . . 118.5(2) no
N4 C15 C14 . . . 123.6(2) no
N4 C16 C12 . . . 123.38(17) no
C3 C2 H2 . . . 120.00 no
C1 C2 H2 . . . 120.00 no
C2 C3 H3 . . . 120.00 no
C4 C3 H3 . . . 120.00 no
C3 C4 H4 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C6 C5 H5 . . . 119.00 no
C4 C5 H5 . . . 119.00 no
N2 C7 H7 . . . 109.00 no
C6 C7 H7 . . . 109.00 no
S1 C7 H7 . . . 109.00 no
S1 C8A H8A . . . 109.00 no
C10A C8A H8A . . . 109.00 no
C9A C8A H8A . . . 109.00 no
C9B C8B H8B . . . 109.00 no
C10B C8B H8B . . . 109.00 no
S1 C8B H8B . . . 109.00 no
H10A C10A H10B . . . 109.00 no
C8A C10A H10C . . . 109.00 no
C8A C10A H10B . . . 110.00 no
H10A C10A H10C . . . 109.00 no
H10B C10A H10C . . . 109.00 no
C8A C10A H10A . . . 110.00 no
C8B C10B H10D . . . 109.00 no
C8B C10B H10E . . . 109.00 no
H10D C10B H10F . . . 110.00 no
H10D C10B H10E . . . 109.00 no
H10E C10B H10F . . . 110.00 no
C8B C10B H10F . . . 109.00 no
C14 C13 H13 . . . 120.00 no
C12 C13 H13 . . . 120.00 no
C13 C14 H14 . . . 121.00 no
C15 C14 H14 . . . 121.00 no
N4 C15 H15 . . . 118.00 no
C14 C15 H15 . . . 118.00 no
N4 C16 H16 . . . 118.00 no
C12 C16 H16 . . . 118.00 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
S1 C7 . . 1.8238(19) no
S1 C8A . . 1.772(4) no
S1 C8B . . 1.880(5) no
O1 N1 . . 1.205(3) no
O2 N1 . . 1.211(3) no
O3A C9A . . 1.226(14) no
O3B C9B . . 1.201(15) no
O4 C11 . . 1.211(2) no
OW1 HW1 . . 0.813(19) no
OW1 HW2 . . 0.80(2) no
N1 C1 . . 1.468(3) no
N2 N3 . . 1.386(2) no
N2 C7 . . 1.454(2) no
N2 C9A . . 1.364(11) no
N2 C9B . . 1.339(10) no
N3 C11 . . 1.360(2) no
N4 C16 . . 1.331(3) no
N4 C15 . . 1.324(3) no
N3 HN1 . . 0.861(18) no
C1 C6 . . 1.399(3) no
C1 C2 . . 1.383(4) no
C2 C3 . . 1.363(5) no
C3 C4 . . 1.373(5) no
C4 C5 . . 1.378(4) no
C5 C6 . . 1.390(3) no
C6 C7 . . 1.516(2) no
C8A C9A . . 1.501(11) no
C8A C10A . . 1.518(14) no
C8B C10B . . 1.476(15) no
C8B C9B . . 1.529(11) no
C11 C12 . . 1.495(3) no
C12 C16 . . 1.384(3) no
C12 C13 . . 1.370(3) no
C13 C14 . . 1.374(4) no
C14 C15 . . 1.365(3) no
C2 H2 . . 0.9300 no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C7 H7 . . 0.9800 no
C8A H8A . . 0.9800 no
C8B H8B . . 0.9800 no
C10A H10B . . 0.9600 no
C10A H10C . . 0.9600 no
C10A H10A . . 0.9600 no
C10B H10F . . 0.9600 no
C10B H10E . . 0.9600 no
C10B H10D . . 0.9600 no
C13 H13 . . 0.9300 no
C14 H14 . . 0.9300 no
C15 H15 . . 0.9300 no
C16 H16 . . 0.9300 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S1 O2 2.999(2) . . no
S1 N1 3.466(2) . . no
S1 S1 3.5774(7) . 2_666 no
S1 O2 3.188(2) . 2_666 no
O1 O4 3.150(4) . 2_766 no
O1 C11 3.389(3) . 2_766 no
OW1 C13 3.286(3) . 1_455 no
OW1 N4 2.803(2) . 1_345 no
OW1 O3A 2.806(12) . 2_667 no
OW1 N3 2.804(2) . 1_455 no
OW1 O3B 2.870(12) . 2_667 no
O2 C7 2.688(2) . . no
O2 S1 3.188(2) . 2_666 no
O2 N1 3.123(3) . 2_766 no
O2 S1 2.999(2) . . no
O2 O2 3.177(3) . 2_766 no
O2 C1 3.348(3) . 2_766 no
O3A C15 3.266(13) . 1_455 no
O3A C11 3.400(16) . . no
O3A C14 3.420(15) . 1_455 no
O3A OW1 2.806(12) . 2_667 no
O3A N3 2.720(16) . . no
O3B OW1 2.870(12) . 2_667 no
O3B C13 3.288(11) . 2_767 no
O3B N3 2.769(15) . . no
O4 C7 3.136(2) . . no
O4 C9A 3.288(10) . . no
O4 O1 3.150(4) . 2_766 no
O4 N2 2.689(2) . . no
O1 H10E 2.8800 . 2_666 no
O1 H8A 2.9200 . 2_666 no
O1 H2 2.3600 . . no
OW1 H5 2.6600 . 1_455 no
OW1 H13 2.4800 . 1_455 no
OW1 HN1 1.958(17) . 1_455 no
O2 H7 2.2600 . . no
O3A H10B 2.8900 . . no
O3A H13 2.9000 . 2_767 no
O3A HW1 2.02(2) . 2_667 no
O3B H10F 2.7000 . . no
O3B HN1 2.87(3) . . no
O3B H13 2.5800 . 2_767 no
O3B HW1 2.09(3) . 2_667 no
O4 H7 2.6300 . . no
O4 H16 2.5800 . . no
N1 S1 3.466(2) . . no
N1 O2 3.123(3) . 2_766 no
N2 O4 2.689(2) . . no
N3 O3B 2.769(15) . . no
N3 OW1 2.804(2) . 1_655 no
N3 O3A 2.720(16) . . no
N3 C5 3.167(3) . . no
N4 OW1 2.803(2) . 1_765 no
N1 H7 2.8700 . . no
N2 H5 2.4100 . . no
N3 H13 2.6500 . . no
N3 H5 2.7000 . . no
N4 HW2 2.01(2) . 1_765 no
C1 O2 3.348(3) . 2_766 no
C5 C9B 3.466(10) . . no
C5 N3 3.167(3) . . no
C7 O2 2.688(2) . . no
C7 O4 3.136(2) . . no
C9A O4 3.288(10) . . no
C9B C5 3.466(10) . . no
C11 O3A 3.400(16) . . no
C11 O1 3.389(3) . 2_766 no
C12 C14 3.586(3) . 2_877 no
C12 C15 3.496(3) . 2_877 no
C13 O3B 3.288(11) . 2_767 no
C13 OW1 3.286(3) . 1_655 no
C14 C12 3.586(3) . 2_877 no
C14 C16 3.523(3) . 2_877 no
C14 O3A 3.420(15) . 1_655 no
C15 C12 3.496(3) . 2_877 no
C15 O3A 3.266(13) . 1_655 no
C16 C14 3.523(3) . 2_877 no
C5 HN1 3.026(17) . . no
C9B H5 2.9000 . . no
C10A H14 3.0900 . 2_767 no
C11 H7 2.8500 . . no
C12 H10E 2.9600 . 1_655 no
C13 HN1 2.62(2) . . no
C15 H15 3.0900 . 2_977 no
C15 HW2 2.74(2) . 1_765 no
C16 H10E 3.0700 . 1_655 no
C16 HW2 3.04(3) . 1_765 no
HN1 OW1 1.958(17) . 1_655 no
HN1 C5 3.026(17) . . no
HN1 H5 2.4100 . . no
HN1 HW1 2.45(3) . 1_655 no
HN1 HW2 2.46(3) . 1_655 no
HN1 O3B 2.87(3) . . no
HN1 H13 2.1800 . . no
HN1 C13 2.62(2) . . no
H2 O1 2.3600 . . no
HW1 H13 2.2900 . 1_455 no
HW1 O3B 2.09(2) . 2_667 no
HW1 O3A 2.02(2) . 2_667 no
HW1 HN1 2.45(3) . 1_455 no
HW2 C16 3.04(3) . 1_345 no
HW2 N4 2.01(2) . 1_345 no
HW2 C15 2.74(2) . 1_345 no
HW2 H5 2.4700 . 1_455 no
HW2 HN1 2.46(3) . 1_455 no
H5 HN1 2.4100 . . no
H5 HW2 2.4700 . 1_655 no
H5 OW1 2.6600 . 1_655 no
H5 N2 2.4100 . . no
H5 C9B 2.9000 . . no
H5 N3 2.7000 . . no
H7 O2 2.2600 . . no
H7 O4 2.6300 . . no
H7 C11 2.8500 . . no
H7 N1 2.8700 . . no
H8A O1 2.9200 . 2_666 no
H10B O3A 2.8900 . . no
H10B H14 2.3200 . 2_767 no
H10E C12 2.9600 . 1_455 no
H10E O1 2.8800 . 2_666 no
H10E C16 3.0700 . 1_455 no
H10F H14 2.4100 . 2_767 no
H10F O3B 2.7000 . . no
H13 OW1 2.4800 . 1_655 no
H13 N3 2.6500 . . no
H13 HN1 2.1800 . . no
H13 HW1 2.2900 . 1_655 no
H13 O3A 2.9000 . 2_767 no
H13 O3B 2.5800 . 2_767 no
H14 C10A 3.0900 . 2_767 no
H14 H10B 2.3200 . 2_767 no
H14 H10F 2.4100 . 2_767 no
H15 C15 3.0900 . 2_977 no
H15 H15 2.4000 . 2_977 no
H16 O4 2.5800 . . no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_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
N3 HN1 OW1 1_655 0.86(2) 1.96(2) 2.804(2) 167(2) yes
OW1 HW1 O3A 2_667 0.81(2) 2.02(2) 2.8060(10) 163(4) yes
OW1 HW2 N4 1_345 0.80(2) 2.01(2) 2.803(2) 173(3) yes
C5 H5 N2 . 0.9300 2.4100 2.794(3) 104.00 no
C7 H7 O2 . 0.9800 2.2600 2.688(2) 105.00 no
C13 H13 OW1 1_655 0.9300 2.4800 3.286(3) 145.00 no
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8A S1 C7 C6 . . . . 120.0(2) no
C7 S1 C8A C10A . . . . -117.5(5) no
C7 S1 C8A C9A . . . . 6.1(5) no
C8A S1 C7 N2 . . . . -2.6(2) no
O1 N1 C1 C6 . . . . -168.9(3) no
O1 N1 C1 C2 . . . . 9.5(4) no
O2 N1 C1 C2 . . . . -168.0(3) no
O2 N1 C1 C6 . . . . 13.7(4) no
C9A N2 N3 C11 . . . . -86.1(5) no
N3 N2 C7 S1 . . . . -164.40(12) no
C7 N2 N3 C11 . . . . 75.9(2) no
C9A N2 C7 C6 . . . . -124.5(4) no
C9A N2 C7 S1 . . . . -2.3(4) no
N3 N2 C7 C6 . . . . 73.41(19) no
C7 N2 C9A C8A . . . . 7.4(8) no
N3 N2 C9A O3A . . . . -16.3(11) no
C7 N2 C9A O3A . . . . -178.0(8) no
N3 N2 C9A C8A . . . . 169.1(4) no
N2 N3 C11 C12 . . . . 179.78(15) no
N2 N3 C11 O4 . . . . -2.4(3) no
C16 N4 C15 C14 . . . . 0.6(3) no
C15 N4 C16 C12 . . . . 0.4(3) no
N1 C1 C6 C5 . . . . 177.7(2) no
N1 C1 C6 C7 . . . . -2.1(3) no
C6 C1 C2 C3 . . . . -1.2(5) no
C2 C1 C6 C5 . . . . -0.6(4) no
N1 C1 C2 C3 . . . . -179.5(3) no
C2 C1 C6 C7 . . . . 179.7(2) no
C1 C2 C3 C4 . . . . 1.6(5) no
C2 C3 C4 C5 . . . . -0.2(5) no
C3 C4 C5 C6 . . . . -1.7(5) no
C4 C5 C6 C1 . . . . 2.0(4) no
C4 C5 C6 C7 . . . . -178.2(2) no
C5 C6 C7 N2 . . . . 8.9(3) no
C1 C6 C7 S1 . . . . 71.6(2) no
C5 C6 C7 S1 . . . . -108.16(19) no
C1 C6 C7 N2 . . . . -171.39(19) no
C10A C8A C9A N2 . . . . 112.4(7) no
S1 C8A C9A N2 . . . . -8.5(7) no
C10A C8A C9A O3A . . . . -62.0(12) no
S1 C8A C9A O3A . . . . 177.1(9) no
N3 C11 C12 C13 . . . . -30.2(3) no
O4 C11 C12 C13 . . . . 152.0(2) no
O4 C11 C12 C16 . . . . -26.0(3) no
N3 C11 C12 C16 . . . . 151.82(18) no
C16 C12 C13 C14 . . . . -0.4(3) no
C11 C12 C16 N4 . . . . 177.67(18) no
C11 C12 C13 C14 . . . . -178.5(2) no
C13 C12 C16 N4 . . . . -0.5(3) no
C12 C13 C14 C15 . . . . 1.3(3) no
C13 C14 C15 N4 . . . . -1.4(4) no
