##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2013-05-13
_journal_date_accepted     2013-05-20
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      6
_journal_page_first     o957
_journal_page_last     o958
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813013949
_journal_coeditor_code     SU2602
loop_
    _publ_contact_author_name
    _publ_contact_author_address
    _publ_contact_author_email
    'Dr. M. NizamMohideen'
;
Department of Physics
The New College (Autonomous)
Chennai 600 014
Tamil Nadu, India
;
 'mnizam_new@yahoo.in'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '91-9841459257'
_publ_section_title
;
<i>L</i>-Histidinium dipicrate dihydrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'M. Sethuram' .
;
Department of Chemistry,
Sri Ramakrishna Mission Vidyalaya College of Arts and Science,
Coimbatore 641 020,
Tamil Nadu, India
;
    'M. V. Rajasekharan' .
;
School of Chemistry
University of Hyderabad
Hyderabad 500 046
Andhra Pradesh, India
;
    'M. Dhandapani' .
;
Department of Chemistry
Sri Ramakrishna Mission Vidyalaya College of Arts and Science
Coimbatore 641 020
Tamil Nadu, India
;
    'G. Amirthaganesan' .
;
Department of Chemistry,
Sri Ramakrishna Mission Vidyalaya College of Arts and Science,
Coimbatore 641 020
Tamil Nadu, India
;
    'NizamMohideen, M.' .
;
Department of Physics
The New College (Autonomous)
Chennai 600 014
India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
<i>L</i>-Histidinium dipicrate dihydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C6 H11 N3 O2 2+, 2(C6 H2 N3 O7 -), 2(H2 O)'
_chemical_formula_sum     'C18 H19 N9 O18'
_chemical_formula_iupac     'C6 H11 N3 O2 2+, 2C6 H2 N3 O7 -, 2H2 O'
_chemical_formula_weight     649.42
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21'
_symmetry_space_group_name_Hall     'P 2yb'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     6.6060(4)
_cell_length_b     25.7003(13)
_cell_length_c     7.9627(5)
_cell_angle_alpha     90.00
_cell_angle_beta     107.532(7)
_cell_angle_gamma     90.00
_cell_volume     1289.08(13)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     5817
_cell_measurement_theta_min     2.4
_cell_measurement_theta_max     31.1
_cell_measurement_temperature     293(2)
_exptl_crystal_description     square
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.673
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     668
_exptl_absorpt_coefficient_mu     0.152
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2004)'
_exptl_absorpt_correction_T_min     0.9702
_exptl_absorpt_correction_T_max     0.9850
_exptl_special_details     ?
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Bruker Kappa APEXII CCD
;
_diffrn_measurement_method     '\w and \f scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     5817
_diffrn_reflns_av_R_equivalents     0.0200
_diffrn_reflns_av_sigmaI/netI     0.0337
_diffrn_reflns_theta_min     2.80
_diffrn_reflns_theta_max     28.88
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.865
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -26
_diffrn_reflns_limit_k_max     34
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     9
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     2982
_reflns_number_gt     2560
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0491
_refine_ls_R_factor_gt     0.0392
_refine_ls_wR_factor_gt     0.0820
_refine_ls_wR_factor_ref     0.0883
_refine_ls_goodness_of_fit_ref     1.085
_refine_ls_restrained_S_all     1.084
_refine_ls_number_reflns     2982
_refine_ls_number_parameters     439
_refine_ls_number_restraints     7
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+0.2411P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.212
_refine_diff_density_min     -0.183
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0095(12)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
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'
_computing_data_collection     'APEX2 (Bruker, 2004)'
_computing_cell_refinement     'APEX2 and SAINT (Bruker, 2004)'
_computing_data_reduction     'SAINT and XPREP (Bruker, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
 'ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae <i>et al.</i>, 2008)'
_computing_publication_material
                                'WinGX (Farrugia, 2012) and PLATON (Spek, 2009)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 1.1170(5) -0.00275(12) 1.2736(5) 0.0774(11) Uani d . 1 1 . .
    O O2 0.8469(5) -0.04330(11) 1.3342(4) 0.0566(8) Uani d . 1 1 . .
    H H2 0.9346 -0.0664 1.3719 0.085 Uiso calc R 1 1 . .
    O O3 0.9237(4) 0.37442(9) 0.5194(3) 0.0366(6) Uani d . 1 1 . .
    O O4 1.1711(5) 0.33930(12) 1.0182(3) 0.0618(9) Uani d . 1 1 . .
    O O5 0.9113(6) 0.38681(13) 0.8677(4) 0.0659(9) Uani d . 1 1 . .
    O O6 1.0105(5) 0.15561(11) 0.8787(3) 0.0527(7) Uani d . 1 1 . .
    O O7 0.9511(5) 0.13208(10) 0.6075(3) 0.0507(7) Uani d . 1 1 . .
    O O8 0.9119(4) 0.26246(10) 0.1693(3) 0.0456(6) Uani d . 1 1 . .
    O O9 0.7415(5) 0.33288(10) 0.1914(3) 0.0489(7) Uani d . 1 1 . .
    O O10 0.5060(4) 0.11319(9) 0.8159(3) 0.0379(6) Uani d . 1 1 . .
    O O11 0.4555(4) 0.23048(10) 1.1305(3) 0.0443(6) Uani d . 1 1 . .
    O O12 0.6326(5) 0.16004(10) 1.1346(3) 0.0505(7) Uani d . 1 1 . .
    O O13 0.4413(5) 0.35254(9) 0.6731(4) 0.0529(7) Uani d . 1 1 . .
    O O14 0.3963(5) 0.32377(10) 0.4098(3) 0.0522(7) Uani d . 1 1 . .
    O O15 0.2242(5) 0.14022(12) 0.3056(3) 0.0565(8) Uani d . 1 1 . .
    O O16 0.4623(6) 0.09005(11) 0.4743(4) 0.0668(9) Uani d . 1 1 . .
    N N1 0.8717(5) 0.07237(10) 1.0875(4) 0.0354(6) Uani d . 1 1 . .
    H H1A 0.7843 0.0987 1.0431 0.053 Uiso calc R 1 1 . .
    H H1B 0.8912 0.0535 1.0000 0.053 Uiso calc R 1 1 . .
    H H1C 0.9959 0.0848 1.1535 0.053 Uiso calc R 1 1 . .
    N N2 0.4952(5) 0.00857(12) 0.7727(4) 0.0380(7) Uani d . 1 1 . .
    N N3 0.4987(6) -0.07402(13) 0.7471(5) 0.0590(10) Uani d . 1 1 . .
    H H3 0.4956 -0.1045 0.7020 0.071 Uiso calc R 1 1 . .
    N N4 1.0229(5) 0.34810(12) 0.8865(4) 0.0388(7) Uani d . 1 1 . .
    N N5 0.9722(4) 0.16635(11) 0.7214(4) 0.0353(7) Uani d . 1 1 . .
    N N6 0.8457(5) 0.29442(11) 0.2552(3) 0.0322(6) Uani d . 1 1 . .
    N N7 0.5317(4) 0.19734(11) 1.0568(3) 0.0312(6) Uani d . 1 1 . .
    N N8 0.4235(4) 0.31696(11) 0.5679(4) 0.0315(6) Uani d . 1 1 . .
    N N9 0.3649(5) 0.13122(11) 0.4434(3) 0.0364(7) Uani d . 1 1 . .
    C C1 0.9350(6) -0.00520(14) 1.2718(5) 0.0423(9) Uani d . 1 1 . .
    C C2 0.7771(6) 0.03902(13) 1.1981(4) 0.0344(7) Uani d . 1 1 . .
    C C3 0.5503(5) 0.02145(14) 1.0983(4) 0.0365(8) Uani d . 1 1 . .
    H H3A 0.4943 0.0022 1.1793 0.044 Uiso calc R 1 1 . .
    H H3B 0.4629 0.0522 1.0624 0.044 Uiso calc R 1 1 . .
    C C4 0.5280(5) -0.01146(13) 0.9395(4) 0.0331(7) Uani d . 1 1 . .
    C C5 0.4757(6) -0.03046(16) 0.6596(5) 0.0493(10) Uani d . 1 1 . .
    C C6 0.5283(7) -0.06396(16) 0.9212(5) 0.0504(10) Uani d . 1 1 . .
    C C7 0.9258(5) 0.32737(12) 0.5650(4) 0.0256(6) Uani d . 1 1 . .
    C C8 0.9775(5) 0.30948(13) 0.7450(4) 0.0283(7) Uani d . 1 1 . .
    C C9 0.9939(5) 0.25863(13) 0.7963(4) 0.0275(7) Uani d . 1 1 . .
    H H9 1.0308 0.2500 0.9151 0.033 Uiso calc R 1 1 . .
    C C10 0.9549(5) 0.22013(12) 0.6693(4) 0.0265(6) Uani d . 1 1 . .
    C C11 0.9070(4) 0.23282(12) 0.4924(4) 0.0259(6) Uani d . 1 1 . .
    H H11 0.8856 0.2068 0.4077 0.031 Uiso calc R 1 1 . .
    C C12 0.8915(5) 0.28421(11) 0.4435(4) 0.0235(6) Uani d . 1 1 . .
    C C13 0.4825(5) 0.15872(12) 0.7585(4) 0.0260(6) Uani d . 1 1 . .
    C C14 0.5012(5) 0.20440(12) 0.8692(4) 0.0232(6) Uani d . 1 1 . .
    C C15 0.4816(5) 0.25485(12) 0.8099(4) 0.0246(6) Uani d . 1 1 . .
    H H15 0.4977 0.2825 0.8884 0.030 Uiso calc R 1 1 . .
    C C16 0.4375(5) 0.26384(12) 0.6310(4) 0.0237(6) Uani d . 1 1 . .
    C C17 0.3974(4) 0.22294(12) 0.5116(4) 0.0247(6) Uani d . 1 1 . .
    H H17 0.3562 0.2293 0.3910 0.030 Uiso calc R 1 1 . .
    C C18 0.4195(5) 0.17329(12) 0.5740(4) 0.0249(6) Uani d . 1 1 . .
    O O17W 1.0107(7) 0.43238(13) 0.2418(5) 0.0724(10) Uani d D 1 1 . .
    O O18W 1.0051(8) 0.03423(14) 0.8230(5) 0.0779(11) Uani d D 1 1 . .
    H H17A 1.006(14) 0.415(3) 0.150(7) 0.18(4) Uiso d D 1 1 . .
    H H17B 1.04(2) 0.411(3) 0.325(9) 0.31(7) Uiso d D 1 1 . .
    H H18A 1.001(9) 0.0022(8) 0.808(7) 0.086(19) Uiso d D 1 1 . .
    H H18B 0.977(15) 0.049(2) 0.726(5) 0.19(4) Uiso d D 1 1 . .
    H H2A 0.763(6) 0.0623(16) 1.296(5) 0.039(10) Uiso d . 1 1 . .
    H H6 0.539(7) -0.0916(19) 0.999(6) 0.064(13) Uiso d . 1 1 . .
    H H5 0.455(7) -0.029(2) 0.536(6) 0.068(13) Uiso d . 1 1 . .
    H H2B 0.479(7) 0.0432(19) 0.751(5) 0.053(12) Uiso d . 1 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    O1 0.0441(17) 0.047(2) 0.123(3) 0.0016(14) -0.0029(17) 0.0338(19)
    O2 0.0723(19) 0.0389(16) 0.0567(16) 0.0113(15) 0.0166(14) 0.0245(13)
    O3 0.0544(15) 0.0211(12) 0.0300(11) -0.0025(11) 0.0064(10) -0.0010(9)
    O4 0.083(2) 0.0564(19) 0.0295(13) -0.0121(17) -0.0084(13) -0.0061(13)
    O5 0.096(2) 0.0489(19) 0.0517(16) 0.0160(18) 0.0213(15) -0.0173(14)
    O6 0.0750(19) 0.0426(16) 0.0386(14) -0.0024(14) 0.0143(13) 0.0187(12)
    O7 0.0717(19) 0.0268(14) 0.0524(16) -0.0034(14) 0.0168(13) 0.0001(13)
    O8 0.0684(17) 0.0436(16) 0.0298(12) -0.0007(14) 0.0225(12) -0.0067(11)
    O9 0.0775(19) 0.0295(13) 0.0292(12) 0.0062(13) 0.0000(12) 0.0058(10)
    O10 0.0591(16) 0.0204(12) 0.0299(12) 0.0018(11) 0.0070(11) 0.0016(9)
    O11 0.0660(16) 0.0427(15) 0.0298(12) 0.0072(13) 0.0229(12) -0.0033(11)
    O12 0.080(2) 0.0350(14) 0.0269(12) 0.0154(14) 0.0007(12) 0.0059(11)
    O13 0.079(2) 0.0174(13) 0.0575(16) 0.0002(13) 0.0135(14) -0.0002(12)
    O14 0.081(2) 0.0376(15) 0.0368(13) 0.0005(15) 0.0155(13) 0.0172(12)
    O15 0.0706(19) 0.0514(18) 0.0320(13) -0.0160(15) -0.0078(12) -0.0063(12)
    O16 0.112(3) 0.0364(17) 0.0446(16) 0.0147(18) 0.0118(17) -0.0133(13)
    N1 0.0395(15) 0.0194(14) 0.0404(16) -0.0002(12) 0.0017(12) 0.0029(11)
    N2 0.0445(17) 0.0244(15) 0.0380(16) -0.0015(14) 0.0019(13) -0.0004(13)
    N3 0.082(3) 0.0247(17) 0.058(2) -0.0058(18) 0.0021(18) -0.0120(15)
    N4 0.0573(19) 0.0330(18) 0.0281(14) -0.0092(15) 0.0158(13) -0.0041(12)
    N5 0.0356(15) 0.0281(16) 0.0416(16) -0.0027(13) 0.0110(12) 0.0070(13)
    N6 0.0444(16) 0.0279(15) 0.0219(13) -0.0078(13) 0.0066(11) -0.0031(11)
    N7 0.0428(16) 0.0261(15) 0.0220(13) -0.0012(13) 0.0056(11) -0.0016(11)
    N8 0.0286(14) 0.0255(15) 0.0399(15) -0.0017(12) 0.0096(11) 0.0060(12)
    N9 0.0547(18) 0.0253(15) 0.0290(14) -0.0073(14) 0.0122(13) -0.0055(12)
    C1 0.048(2) 0.0270(19) 0.0382(19) -0.0013(17) -0.0072(16) 0.0034(15)
    C2 0.0470(19) 0.0246(17) 0.0274(15) 0.0004(15) 0.0048(14) 0.0022(13)
    C3 0.0412(18) 0.0329(18) 0.0341(17) 0.0030(16) 0.0097(14) 0.0045(14)
    C4 0.0338(16) 0.0230(16) 0.0377(17) -0.0032(14) 0.0037(13) 0.0027(14)
    C5 0.058(2) 0.038(2) 0.043(2) -0.0062(19) 0.0018(18) -0.0087(18)
    C6 0.064(3) 0.031(2) 0.045(2) -0.0083(19) 0.0001(19) 0.0019(18)
    C7 0.0269(15) 0.0258(16) 0.0221(14) -0.0025(13) 0.0046(11) -0.0039(12)
    C8 0.0311(16) 0.0290(17) 0.0248(15) -0.0051(14) 0.0081(12) -0.0064(13)
    C9 0.0295(15) 0.0314(18) 0.0224(14) -0.0003(14) 0.0090(12) 0.0034(13)
    C10 0.0251(14) 0.0234(16) 0.0313(15) -0.0005(13) 0.0088(11) 0.0038(12)
    C11 0.0254(14) 0.0262(16) 0.0263(14) -0.0033(13) 0.0082(11) -0.0041(12)
    C12 0.0288(15) 0.0187(14) 0.0213(14) -0.0009(12) 0.0051(11) -0.0007(11)
    C13 0.0275(15) 0.0248(16) 0.0251(15) 0.0014(13) 0.0070(12) -0.0005(13)
    C14 0.0267(14) 0.0246(16) 0.0176(14) 0.0022(13) 0.0057(11) 0.0006(11)
    C15 0.0256(14) 0.0233(15) 0.0239(14) 0.0018(13) 0.0057(11) -0.0023(12)
    C16 0.0229(14) 0.0202(15) 0.0276(15) 0.0015(12) 0.0072(11) 0.0048(12)
    C17 0.0254(14) 0.0274(17) 0.0215(14) -0.0005(13) 0.0074(11) 0.0027(12)
    C18 0.0270(15) 0.0252(16) 0.0215(15) -0.0004(13) 0.0058(12) -0.0030(11)
    O17W 0.126(3) 0.0397(18) 0.0615(19) -0.0171(19) 0.043(2) -0.0111(15)
    O18W 0.125(3) 0.043(2) 0.085(3) 0.009(2) 0.060(2) 0.0001(18)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 C1 . 1.199(5) ?
    O2 C1 . 1.311(5) ?
    O2 H2 . 0.8200 ?
    O3 C7 . 1.261(4) ?
    O4 N4 . 1.220(4) ?
    O5 N4 . 1.220(4) ?
    O6 N5 . 1.232(4) ?
    O7 N5 . 1.242(4) ?
    O8 N6 . 1.230(4) ?
    O9 N6 . 1.224(4) ?
    O10 C13 . 1.249(4) ?
    O11 N7 . 1.225(3) ?
    O12 N7 . 1.224(4) ?
    O13 N8 . 1.222(4) ?
    O14 N8 . 1.230(4) ?
    O15 N9 . 1.228(4) ?
    O16 N9 . 1.224(4) ?
    N1 C2 . 1.494(4) ?
    N1 H1A . 0.8900 ?
    N1 H1B . 0.8900 ?
    N1 H1C . 0.8900 ?
    N2 C5 . 1.328(5) ?
    N2 C4 . 1.380(4) ?
    N2 H2B . 0.91(5) ?
    N3 C5 . 1.303(5) ?
    N3 C6 . 1.365(5) ?
    N3 H3 . 0.8600 ?
    N4 C8 . 1.463(4) ?
    N5 C10 . 1.438(4) ?
    N6 C12 . 1.461(4) ?
    N7 C14 . 1.457(4) ?
    N8 C16 . 1.448(4) ?
    N9 C18 . 1.468(4) ?
    C1 C2 . 1.534(5) ?
    C2 C3 . 1.537(5) ?
    C2 H2A . 1.01(4) ?
    C3 C4 . 1.491(5) ?
    C3 H3A . 0.9700 ?
    C3 H3B . 0.9700 ?
    C4 C6 . 1.357(5) ?
    C5 H5 . 0.96(5) ?
    C6 H6 . 0.93(5) ?
    C7 C12 . 1.444(4) ?
    C7 C8 . 1.445(4) ?
    C8 C9 . 1.363(5) ?
    C9 C10 . 1.383(4) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.387(4) ?
    C11 C12 . 1.372(4) ?
    C11 H11 . 0.9300 ?
    C13 C14 . 1.451(4) ?
    C13 C18 . 1.450(4) ?
    C14 C15 . 1.373(4) ?
    C15 C16 . 1.385(4) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.388(4) ?
    C17 C18 . 1.361(4) ?
    C17 H17 . 0.9300 ?
    O17W H17A . 0.84(2) ?
    O17W H17B . 0.84(2) ?
    O18W H18A . 0.83(2) ?
    O18W H18B . 0.83(2) ?
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
    C1 O2 H2 . . 109.5 ?
    C2 N1 H1A . . 109.5 ?
    C2 N1 H1B . . 109.5 ?
    H1A N1 H1B . . 109.5 ?
    C2 N1 H1C . . 109.5 ?
    H1A N1 H1C . . 109.5 ?
    H1B N1 H1C . . 109.5 ?
    C5 N2 C4 . . 109.0(3) ?
    C5 N2 H2B . . 129(3) ?
    C4 N2 H2B . . 121(3) ?
    C5 N3 C6 . . 109.8(3) ?
    C5 N3 H3 . . 125.1 ?
    C6 N3 H3 . . 125.1 ?
    O5 N4 O4 . . 123.7(3) ?
    O5 N4 C8 . . 118.8(3) ?
    O4 N4 C8 . . 117.5(3) ?
    O6 N5 O7 . . 121.8(3) ?
    O7 N5 O7 1 . 0.0(3) ?
    O6 N5 C10 . . 118.9(3) ?
    O7 N5 C10 . . 119.3(3) ?
    O9 N6 O8 . . 123.9(3) ?
    O9 N6 C12 . . 119.2(3) ?
    O8 N6 C12 . . 116.9(3) ?
    O12 N7 O11 . . 122.8(3) ?
    O12 N7 C14 . . 120.2(3) ?
    O11 N7 C14 . . 117.0(3) ?
    O13 N8 O14 . . 123.4(3) ?
    O13 N8 C16 . . 119.0(3) ?
    O14 N8 C16 . . 117.6(3) ?
    O16 N9 O15 . . 123.6(3) ?
    O16 N9 C18 . . 119.5(3) ?
    O15 N9 C18 . . 116.9(3) ?
    O1 C1 O2 . . 126.3(4) ?
    O1 C1 C2 . . 121.9(3) ?
    O2 C1 C2 . . 111.7(3) ?
    N1 C2 C1 . . 107.1(3) ?
    N1 C2 C3 . . 112.3(3) ?
    C1 C2 C3 . . 115.1(3) ?
    N1 C2 H2A . . 105(2) ?
    C1 C2 H2A . . 111(2) ?
    C3 C2 H2A . . 106(2) ?
    C4 C3 C2 . . 115.9(3) ?
    C4 C3 H3A . . 108.3 ?
    C2 C3 H3A . . 108.3 ?
    C4 C3 H3B . . 108.3 ?
    C2 C3 H3B . . 108.3 ?
    H3A C3 H3B . . 107.4 ?
    C6 C4 N2 . . 105.8(3) ?
    C6 C4 C3 . . 130.7(3) ?
    N2 C4 C3 . . 123.5(3) ?
    N3 C5 N2 . . 108.3(4) ?
    N3 C5 H5 . . 124(3) ?
    N2 C5 H5 . . 128(3) ?
    C4 C6 N3 . . 107.0(4) ?
    C4 C6 H6 . . 134(3) ?
    N3 C6 H6 . . 119(3) ?
    O3 C7 C12 . . 123.9(3) ?
    O3 C7 C8 . . 124.7(3) ?
    C12 C7 C8 . . 111.3(3) ?
    C9 C8 C7 . . 125.1(3) ?
    C9 C8 N4 . . 116.1(3) ?
    C7 C8 N4 . . 118.7(3) ?
    C8 C9 C10 . . 119.1(3) ?
    C8 C9 H9 . . 120.4 ?
    C10 C9 H9 . . 120.4 ?
    C9 C10 C11 . . 120.7(3) ?
    C9 C10 N5 . . 119.7(3) ?
    C11 C10 N5 . . 119.6(3) ?
    C12 C11 C10 . . 119.3(3) ?
    C12 C11 H11 . . 120.3 ?
    C10 C11 H11 . . 120.3 ?
    C11 C12 C7 . . 124.5(3) ?
    C11 C12 N6 . . 116.0(3) ?
    C7 C12 N6 . . 119.4(3) ?
    O10 C13 C14 . . 123.9(3) ?
    O10 C13 C18 . . 125.4(3) ?
    C14 C13 C18 . . 110.6(3) ?
    C15 C14 C13 . . 125.0(2) ?
    C15 C14 N7 . . 116.1(3) ?
    C13 C14 N7 . . 118.8(3) ?
    C14 C15 C16 . . 118.7(3) ?
    C14 C15 H15 . . 120.6 ?
    C16 C15 H15 . . 120.6 ?
    C15 C16 C17 . . 121.1(3) ?
    C15 C16 N8 . . 119.1(3) ?
    C17 C16 N8 . . 119.8(3) ?
    C18 C17 C16 . . 118.8(3) ?
    C18 C17 H17 . . 120.6 ?
    C16 C17 H17 . . 120.6 ?
    C17 C18 C13 . . 125.4(3) ?
    C17 C18 N9 . . 117.1(2) ?
    C13 C18 N9 . . 117.5(3) ?
    H17A O17W H17B . . 106(3) ?
    H18A O18W H18B . . 109(3) ?
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
    O1 C1 C2 N1 . . . . 17.5(5) ?
    O2 C1 C2 N1 . . . . -164.4(3) ?
    O1 C1 C2 C3 . . . . 143.1(4) ?
    O2 C1 C2 C3 . . . . -38.8(4) ?
    N1 C2 C3 C4 . . . . 62.2(4) ?
    C1 C2 C3 C4 . . . . -60.7(4) ?
    C5 N2 C4 C6 . . . . 0.3(4) ?
    C5 N2 C4 C3 . . . . -178.1(3) ?
    C2 C3 C4 C6 . . . . 92.6(5) ?
    C2 C3 C4 N2 . . . . -89.5(4) ?
    C6 N3 C5 N2 . . . . 1.7(5) ?
    C4 N2 C5 N3 . . . . -1.2(5) ?
    N2 C4 C6 N3 . . . . 0.7(4) ?
    C3 C4 C6 N3 . . . . 179.0(4) ?
    C5 N3 C6 C4 . . . . -1.5(5) ?
    O3 C7 C8 C9 . . . . -175.4(3) ?
    C12 C7 C8 C9 . . . . 0.4(4) ?
    O3 C7 C8 N4 . . . . 2.6(5) ?
    C12 C7 C8 N4 . . . . 178.4(3) ?
    O5 N4 C8 C9 . . . . -139.3(3) ?
    O4 N4 C8 C9 . . . . 40.2(4) ?
    O5 N4 C8 C7 . . . . 42.6(5) ?
    O4 N4 C8 C7 . . . . -138.0(3) ?
    C7 C8 C9 C10 . . . . -1.4(5) ?
    N4 C8 C9 C10 . . . . -179.4(3) ?
    C8 C9 C10 C11 . . . . 2.2(4) ?
    C8 C9 C10 N5 . . . . 179.8(3) ?
    O6 N5 C10 C9 . . . . 3.9(4) ?
    O7 N5 C10 C9 . . . . -175.1(3) ?
    O6 N5 C10 C11 . . . . -178.5(3) ?
    O7 N5 C10 C11 . . . . 2.5(4) ?
    C9 C10 C11 C12 . . . . -2.2(4) ?
    N5 C10 C11 C12 . . . . -179.7(3) ?
    C10 C11 C12 C7 . . . . 1.2(5) ?
    C10 C11 C12 N6 . . . . 178.6(2) ?
    O3 C7 C12 C11 . . . . 175.6(3) ?
    C8 C7 C12 C11 . . . . -0.3(4) ?
    O3 C7 C12 N6 . . . . -1.7(5) ?
    C8 C7 C12 N6 . . . . -177.6(3) ?
    O9 N6 C12 C11 . . . . 148.0(3) ?
    O8 N6 C12 C11 . . . . -30.3(4) ?
    O9 N6 C12 C7 . . . . -34.5(4) ?
    O8 N6 C12 C7 . . . . 147.2(3) ?
    O10 C13 C14 C15 . . . . 178.2(3) ?
    C18 C13 C14 C15 . . . . -5.6(4) ?
    O10 C13 C14 N7 . . . . -5.3(5) ?
    C18 C13 C14 N7 . . . . 170.9(2) ?
    O12 N7 C14 C15 . . . . -150.2(3) ?
    O11 N7 C14 C15 . . . . 28.7(4) ?
    O12 N7 C14 C13 . . . . 33.0(4) ?
    O11 N7 C14 C13 . . . . -148.1(3) ?
    C13 C14 C15 C16 . . . . 1.0(5) ?
    N7 C14 C15 C16 . . . . -175.5(2) ?
    C14 C15 C16 C17 . . . . 4.9(4) ?
    C14 C15 C16 N8 . . . . -178.0(3) ?
    O13 N8 C16 C15 . . . . -3.4(4) ?
    O14 N8 C16 C15 . . . . 175.9(3) ?
    O13 N8 C16 C17 . . . . 173.8(3) ?
    O14 N8 C16 C17 . . . . -6.9(4) ?
    C15 C16 C17 C18 . . . . -5.4(4) ?
    N8 C16 C17 C18 . . . . 177.5(3) ?
    C16 C17 C18 C13 . . . . 0.1(5) ?
    C16 C17 C18 N9 . . . . 176.9(3) ?
    O10 C13 C18 C17 . . . . -178.8(3) ?
    C14 C13 C18 C17 . . . . 5.1(4) ?
    O10 C13 C18 N9 . . . . 4.4(5) ?
    C14 C13 C18 N9 . . . . -171.8(3) ?
    O16 N9 C18 C17 . . . . 147.2(3) ?
    O15 N9 C18 C17 . . . . -31.3(4) ?
    O16 N9 C18 C13 . . . . -35.7(4) ?
    O15 N9 C18 C13 . . . . 145.8(3) ?
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
    N1 H1A O10 1 0.89 2.19 2.909(3) 138
    N1 H1A O12 1 0.89 2.11 2.841(4) 139
    N1 H1B O18W 1 0.89 1.85 2.700(5) 158
    N1 H1C O15 1_656 0.89 2.16 3.007(4) 159
    N2 H2B O10 1 0.91(5) 1.86(5) 2.709(4) 154(4)
    N2 H2B O16 1 0.91(5) 2.49(4) 3.125(4) 128(3)
    N3 H3 O9 2_646 0.86 2.56 2.992(5) 112
    N3 H3 O14 2_646 0.86 2.25 3.077(4) 160
    O2 H2 O3 2_747 0.82 1.86 2.657(3) 165
    O17W H17A O5 1_554 0.84(2) 2.27(3) 3.082(4) 162(9)
    O17W H17B O3 1 0.84(2) 2.14(8) 2.864(4) 144(12)
    O18W H18A O17W 2_746 0.83(2) 1.83(2) 2.664(5) 176(5)
    O18W H18B O7 1 0.83(2) 2.32(4) 3.005(5) 140(6)
    C3 H3B O10 1 0.97 2.59 3.210(4) 122
    C9 H9 O8 1_556 0.93 2.40 3.177(4) 141
    C17 H17 O11 1_554 0.93 2.36 3.177(3) 147
_iucr_refine_instructions_details
;
TITL SETHURAM in P2(1)
CELL  0.71073   6.6060  25.7003   7.9627   90.000  107.532   90.000
ZERR     2.00   0.0004   0.0013   0.0005    0.000    0.007    0.000
LATT  -1
SYMM  - X, 1/2 + Y, - Z
SFAC  C    H    N    O
UNIT  36   38   18   36
MERG 3
DFIX     0.830   0.020 O17W H17A
DFIX     0.830   0.020 O17W H17B
DFIX     1.350   0.020 H17A H17B
DFIX     0.830   0.020 O18W H18A
DFIX     0.830   0.020 O18W H18B
DFIX     1.350   0.020 H18A H18B
EQIV $1 x, y, z
HTAB N1 O10_$1
HTAB N1 O12_$1
HTAB N1 O18W_$1
EQIV $2 1+x,y,1+z
HTAB N1 O15_$2
HTAB N2 O10_$1
HTAB N2 O16_$1
EQIV $3 1-x,-1/2+y,1-z
HTAB N3 O9_$3
HTAB N3 O14_$3
EQIV $4 2-x,-1/2+y,2-z
HTAB O2 O3_$4
EQIV $5 x,y,-1+z
HTAB O17W O5_$5
HTAB O17W O3_$1
EQIV $6 2-x,-1/2+y,1-z
HTAB O18W O17W_$6
HTAB O18W O7_$1
HTAB C3 O10_$1
EQIV $7 x,y,1+z
HTAB C9 O8_$7
HTAB C17 O11_$5
FMAP   2
PLAN   20
SIZE 0.10  0.15  0.20
ACTA    50.00
BOND $H
CONF
L.S.   15
WGHT    0.034100    0.241100
EXTI    0.009456
FVAR       5.28264
O1    4    1.116964   -0.002750    1.273551    11.00000    0.04410    0.04665 =
         0.12294    0.03383   -0.00290    0.00161
O2    4    0.846883   -0.043298    1.334205    11.00000    0.07231    0.03887 =
         0.05666    0.02450    0.01658    0.01134
AFIX  83
H2    2    0.934557   -0.066372    1.371870    11.00000   -1.50000
AFIX   0
O3    4    0.923721    0.374425    0.519431    11.00000    0.05438    0.02115 =
         0.03002   -0.00105    0.00642   -0.00251
O4    4    1.171070    0.339304    1.018159    11.00000    0.08287    0.05637 =
         0.02948   -0.00612   -0.00839   -0.01212
O5    4    0.911300    0.386806    0.867730    11.00000    0.09629    0.04890 =
         0.05172   -0.01727    0.02129    0.01601
O6    4    1.010524    0.155609    0.878749    11.00000    0.07505    0.04261 =
         0.03858    0.01871    0.01429   -0.00245
O7    4    0.951125    0.132082    0.607469    11.00000    0.07171    0.02679 =
         0.05236    0.00011    0.01676   -0.00339
O8    4    0.911856    0.262464    0.169297    11.00000    0.06837    0.04362 =
         0.02983   -0.00675    0.02252   -0.00068
O9    4    0.741549    0.332876    0.191412    11.00000    0.07747    0.02951 =
         0.02920    0.00581    0.00000    0.00615
O10   4    0.506037    0.113189    0.815939    11.00000    0.05906    0.02040 =
         0.02994    0.00163    0.00701    0.00177
O11   4    0.455496    0.230483    1.130500    11.00000    0.06599    0.04267 =
         0.02980   -0.00329    0.02288    0.00720
O12   4    0.632553    0.160036    1.134616    11.00000    0.07960    0.03498 =
         0.02693    0.00587    0.00075    0.01544
O13   4    0.441293    0.352539    0.673142    11.00000    0.07914    0.01742 =
         0.05746   -0.00024    0.01354    0.00024
O14   4    0.396323    0.323770    0.409797    11.00000    0.08071    0.03762 =
         0.03681    0.01716    0.01553    0.00049
O15   4    0.224198    0.140225    0.305620    11.00000    0.07057    0.05143 =
         0.03196   -0.00626   -0.00782   -0.01598
O16   4    0.462263    0.090048    0.474333    11.00000    0.11170    0.03639 =
         0.04465   -0.01326    0.01180    0.01471
N1    3    0.871717    0.072373    1.087489    11.00000    0.03954    0.01939 =
         0.04040    0.00287    0.00168   -0.00016
AFIX  33
H1A   2    0.784337    0.098676    1.043127    11.00000   -1.50000
H1B   2    0.891225    0.053474    0.999984    11.00000   -1.50000
H1C   2    0.995925    0.084835    1.153463    11.00000   -1.50000
AFIX   0
N2    3    0.495248    0.008570    0.772660    11.00000    0.04452    0.02439 =
         0.03801   -0.00041    0.00193   -0.00150
N3    3    0.498678   -0.074016    0.747143    11.00000    0.08190    0.02466 =
         0.05778   -0.01201    0.00208   -0.00580
AFIX  43
H3    2    0.495646   -0.104515    0.702013    11.00000   -1.20000
AFIX   0
N4    3    1.022940    0.348102    0.886528    11.00000    0.05726    0.03302 =
         0.02808   -0.00408    0.01578   -0.00915
N5    3    0.972192    0.166348    0.721413    11.00000    0.03558    0.02814 =
         0.04165    0.00695    0.01103   -0.00270
N6    3    0.845739    0.294423    0.255244    11.00000    0.04444    0.02794 =
         0.02193   -0.00307    0.00656   -0.00778
N7    3    0.531730    0.197340    1.056794    11.00000    0.04275    0.02612 =
         0.02197   -0.00156    0.00561   -0.00122
N8    3    0.423542    0.316963    0.567915    11.00000    0.02863    0.02550 =
         0.03992    0.00595    0.00962   -0.00172
N9    3    0.364901    0.131220    0.443431    11.00000    0.05468    0.02531 =
         0.02896   -0.00546    0.01222   -0.00731
C1    1    0.935032   -0.005196    1.271772    11.00000    0.04826    0.02703 =
         0.03820    0.00340   -0.00719   -0.00126
C2    1    0.777138    0.039019    1.198114    11.00000    0.04702    0.02455 =
         0.02736    0.00221    0.00485    0.00040
C3    1    0.550303    0.021446    1.098348    11.00000    0.04120    0.03295 =
         0.03415    0.00447    0.00970    0.00303
AFIX  23
H3A   2    0.494274    0.002193    1.179284    11.00000   -1.20000
H3B   2    0.462860    0.052205    1.062416    11.00000   -1.20000
AFIX   0
C4    1    0.528019   -0.011460    0.939540    11.00000    0.03382    0.02301 =
         0.03774    0.00274    0.00369   -0.00319
C5    1    0.475720   -0.030465    0.659597    11.00000    0.05803    0.03846 =
         0.04258   -0.00873    0.00183   -0.00625
C6    1    0.528260   -0.063965    0.921213    11.00000    0.06397    0.03090 =
         0.04549    0.00193    0.00009   -0.00825
C7    1    0.925834    0.327374    0.564966    11.00000    0.02694    0.02578 =
         0.02211   -0.00391    0.00463   -0.00255
C8    1    0.977484    0.309479    0.745038    11.00000    0.03106    0.02901 =
         0.02475   -0.00637    0.00814   -0.00506
C9    1    0.993866    0.258634    0.796274    11.00000    0.02948    0.03137 =
         0.02241    0.00343    0.00896   -0.00027
AFIX  43
H9    2    1.030764    0.249970    0.915072    11.00000   -1.20000
AFIX   0
C10   1    0.954893    0.220130    0.669270    11.00000    0.02509    0.02338 =
         0.03134    0.00375    0.00879   -0.00055
C11   1    0.907000    0.232824    0.492356    11.00000    0.02545    0.02617 =
         0.02631   -0.00413    0.00822   -0.00328
AFIX  43
H11   2    0.885577    0.206777    0.407716    11.00000   -1.20000
AFIX   0
C12   1    0.891549    0.284207    0.443488    11.00000    0.02881    0.01873 =
         0.02126   -0.00070    0.00512   -0.00092
C13   1    0.482473    0.158721    0.758491    11.00000    0.02752    0.02484 =
         0.02513   -0.00053    0.00704    0.00135
C14   1    0.501182    0.204402    0.869179    11.00000    0.02668    0.02460 =
         0.01759    0.00059    0.00572    0.00217
C15   1    0.481636    0.254853    0.809899    11.00000    0.02555    0.02325 =
         0.02390   -0.00231    0.00574    0.00178
AFIX  43
H15   2    0.497741    0.282459    0.888352    11.00000   -1.20000
AFIX   0
C16   1    0.437468    0.263841    0.630994    11.00000    0.02293    0.02020 =
         0.02759    0.00482    0.00717    0.00147
C17   1    0.397410    0.222941    0.511559    11.00000    0.02538    0.02744 =
         0.02153    0.00270    0.00739   -0.00047
AFIX  43
H17   2    0.356215    0.229349    0.391031    11.00000   -1.20000
AFIX   0
C18   1    0.419514    0.173290    0.574042    11.00000    0.02701    0.02522 =
         0.02148   -0.00301    0.00578   -0.00044
O17W  4    1.010663    0.432385    0.241793    11.00000    0.12582    0.03974 =
         0.06154   -0.01106    0.04310   -0.01708
O18W  4    1.005129    0.034225    0.823017    11.00000    0.12501    0.04256 =
         0.08495    0.00013    0.06022    0.00905
H17A  2    1.006183    0.415406    0.150010    11.00000    0.17984
H17B  2    1.040449    0.410617    0.324659    11.00000    0.31271
H18A  2    1.001492    0.002207    0.807771    11.00000    0.08645
H18B  2    0.976971    0.049044    0.726242    11.00000    0.18907
H2A   2    0.762970    0.062339    1.295902    11.00000    0.03922
H6    2    0.539047   -0.091627    0.998984    11.00000    0.06394
H5    2    0.455124   -0.028621    0.535635    11.00000    0.06772
H2B   2    0.479216    0.043225    0.751489    11.00000    0.05307
HKLF 4
REM  SETHURAM in P2(1)
REM R1 =  0.0392 for   2560 Fo > 4sig(Fo)  and  0.0491 for all   2982 data
REM    439 parameters refined using      7 restraints
END
;