#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/54/2015440.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_2015440
loop_
_publ_author_name
'Yüce, Süheyla'
'Albayrak, Çiǧdem'
'Odabas̨oǧlu, Mustafa'
'Büyükgüngör, Orhan'
_publ_section_title
;(Z)-6-{[1,3-Dihydroxy-2-(hydroxymethyl)propan-2-yliminio]methyl}-2-ethoxyphenolate,
 (Z)-6-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yliminio]methyl}-4-nitratocyclohexa-2,4-dienone
 monohydrate and
 (R,E)-2-[(1-hydroxybutan-2-ylimino)methyl]phenol
;
_journal_coeditor_code           HJ1092
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o389
_journal_page_last               o393
_journal_paper_doi               10.1107/S0108270106017252
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C11 H14 N2 O6, H2 O'
_chemical_formula_moiety         'C11 H14 N2 O6, H2 O'
_chemical_formula_sum            'C11 H16 N2 O7'
_chemical_formula_weight         288.26
_chemical_name_systematic
;
(Z)-6-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yliminio]methyl}-
4-nitratocyclohexa-2,4-dienone monohydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.518(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.9205(11)
_cell_length_b                   10.7034(6)
_cell_length_c                   7.2308(5)
_cell_measurement_reflns_used    11553
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.83
_cell_measurement_theta_min      1.9
_cell_volume                     1291.52(14)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'Ortep-3 for windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'Stoe IPDS-II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_sigmaI/netI    0.0472
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11553
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.26
_diffrn_standards_interval_time  <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_correction_T_min  0.9552
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.252
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.322
_refine_ls_extinction_coef       0.053(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         2877
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0623P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1068
_reflns_number_gt                1898
_reflns_number_total             2877
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hj1092.cif
_cod_data_source_block           II
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2015440
_cod_database_fobs_code          2015440
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C C1 0.14865(9) 0.67746(12) 0.3596(2) 0.0316(3) Uani d . 1
C C2 0.18202(9) 0.79887(14) 0.3327(2) 0.0341(4) Uani d . 1
C C3 0.12911(11) 0.90282(15) 0.3381(3) 0.0405(4) Uani d . 1
C C4 0.05203(11) 0.88724(15) 0.3619(3) 0.0400(4) Uani d . 1
C C5 0.02170(9) 0.76740(14) 0.3870(2) 0.0352(4) Uani d . 1
C C6 0.06965(9) 0.66455(14) 0.3869(2) 0.0344(4) Uani d . 1
C C7 0.19745(9) 0.56849(14) 0.3731(2) 0.0332(4) Uani d . 1
C C8 0.33033(9) 0.46906(13) 0.3950(2) 0.0319(3) Uani d . 1
C C9 0.28957(9) 0.34190(14) 0.3605(3) 0.0389(4) Uani d . 1
H H9A 0.2485 0.3327 0.4386 0.047 Uiso calc R 1
H H9B 0.2644 0.3347 0.2303 0.047 Uiso calc R 1
C C10 0.36916(9) 0.48493(14) 0.6009(2) 0.0364(4) Uani d . 1
H H10A 0.4121 0.4246 0.6311 0.044 Uiso calc R 1
H H10B 0.3923 0.5679 0.6189 0.044 Uiso calc R 1
C C11 0.39198(10) 0.48684(15) 0.2657(3) 0.0421(4) Uani d . 1
H H11A 0.4368 0.4305 0.3020 0.051 Uiso calc R 1
H H11B 0.3680 0.4679 0.1375 0.051 Uiso calc R 1
N N1 0.27144(8) 0.57004(12) 0.3532(2) 0.0331(3) Uani d . 1
N N2 -0.05935(8) 0.75260(14) 0.4191(2) 0.0435(4) Uani d . 1
O O1 0.25388(7) 0.81207(10) 0.30752(19) 0.0454(3) Uani d . 1
O O2 -0.10117(8) 0.84614(14) 0.4203(3) 0.0681(5) Uani d . 1
O O3 -0.08391(8) 0.64744(13) 0.4466(2) 0.0622(4) Uani d . 1
O O4 0.34854(7) 0.24826(10) 0.40463(19) 0.0483(3) Uani d . 1
H H4A 0.3276 0.1792 0.3879 0.072 Uiso calc R 1
O O5 0.31300(7) 0.46812(10) 0.72336(17) 0.0419(3) Uani d . 1
H H5A 0.2769 0.5196 0.6989 0.063 Uiso calc R 1
O O6 0.41917(8) 0.61161(11) 0.2783(2) 0.0506(4) Uani d . 1
O O7 0.48561(10) 0.68839(15) -0.0087(3) 0.0630(4) Uani d D 1
H H1 0.2918(12) 0.640(2) 0.327(3) 0.051(6) Uiso d . 1
H H2 0.1488(13) 0.982(2) 0.319(3) 0.065(6) Uiso d . 1
H H3 0.0153(12) 0.952(2) 0.360(3) 0.058(6) Uiso d . 1
H H4 0.0493(12) 0.5849(18) 0.410(3) 0.050(5) Uiso d . 1
H H5 0.1737(10) 0.4898(17) 0.408(3) 0.040(5) Uiso d . 1
H H6 0.4431(16) 0.632(2) 0.183(4) 0.076(8) Uiso d . 1
H H7A 0.4601(15) 0.747(2) -0.062(4) 0.082(9) Uiso d D 1
H H7B 0.5317(12) 0.714(3) 0.030(4) 0.098(10) Uiso d D 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C7 118.00(13) ?
C6 C1 C2 121.04(13) ?
C7 C1 C2 120.79(14) ?
O1 C2 C3 122.44(14) ?
O1 C2 C1 121.75(13) y
C3 C2 C1 115.82(14) ?
C4 C3 C2 121.82(15) ?
C4 C3 H2 120.5(14) ?
C2 C3 H2 117.7(14) ?
C3 C4 C5 120.63(15) ?
C3 C4 H3 124.0(13) ?
C5 C4 H3 115.4(13) ?
C6 C5 C4 120.36(15) ?
C6 C5 N2 119.57(14) y
C4 C5 N2 120.04(14) ?
C5 C6 C1 120.31(14) ?
C5 C6 H4 119.6(12) ?
C1 C6 H4 120.1(12) ?
N1 C7 C1 123.18(14) y
N1 C7 H5 119.1(10) ?
C1 C7 H5 117.5(10) ?
N1 C8 C11 106.98(13) y
N1 C8 C9 110.47(12) y
C11 C8 C9 110.33(13) ?
N1 C8 C10 106.61(12) y
C11 C8 C10 110.78(13) ?
C9 C8 C10 111.51(13) ?
O4 C9 C8 108.19(12) ?
O4 C9 H9A 110.1 ?
C8 C9 H9A 110.1 ?
O4 C9 H9B 110.1 ?
C8 C9 H9B 110.1 ?
H9A C9 H9B 108.4 ?
O5 C10 C8 111.68(13) ?
O5 C10 H10A 109.3 ?
C8 C10 H10A 109.3 ?
O5 C10 H10B 109.3 ?
C8 C10 H10B 109.3 ?
H10A C10 H10B 107.9 ?
O6 C11 C8 109.13(13) ?
O6 C11 H11A 109.9 ?
C8 C11 H11A 109.9 ?
O6 C11 H11B 109.9 ?
C8 C11 H11B 109.9 ?
H11A C11 H11B 108.3 ?
C7 N1 C8 127.51(13) ?
C7 N1 H1 118.1(13) ?
C8 N1 H1 113.8(13) ?
O2 N2 O3 122.43(16) ?
O2 N2 C5 118.55(15) ?
O3 N2 C5 119.01(14) ?
C9 O4 H4A 109.5 ?
C10 O5 H5A 109.5 ?
C11 O6 H6 111.4(16) ?
H7A O7 H7B 107(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 1.390(2) ?
C1 C7 1.423(2) ?
C1 C2 1.443(2) ?
C2 O1 1.2666(19) ?
C2 C3 1.433(2) ?
C3 C4 1.354(3) ?
C3 H2 0.93(2) ?
C4 C5 1.404(2) ?
C4 H3 0.93(2) ?
C5 C6 1.368(2) ?
C5 N2 1.437(2) y
C6 H4 0.94(2) ?
C7 N1 1.284(2) y
C7 H5 0.983(18) ?
C8 N1 1.4673(18) y
C8 C11 1.524(2) ?
C8 C9 1.528(2) ?
C8 C10 1.534(2) ?
C9 O4 1.4131(18) ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 O5 1.414(2) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C11 O6 1.4105(19) ?
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
N1 H1 0.86(2) ?
N2 O2 1.2269(19) ?
N2 O3 1.227(2) ?
O4 H4A 0.8200 ?
O5 H5A 0.8200 ?
O6 H6 0.88(3) ?
O7 H7A 0.819(17) ?
O7 H7B 0.829(18) ?
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
O4 H4A O5 4_565 0.82 1.97 2.6801(15) 145.1
O5 H5A O1 4_576 0.82 2.03 2.6661(15) 134.2
O7 H7A O6 4_575 0.819(17) 1.961(18) 2.765(2) 167(3)
O7 H7B O4 2_655 0.829(18) 2.037(19) 2.855(2) 169(3)
N1 H1 O1 . 0.86(2) 1.95(2) 2.6221(17) 134.6(18)
O6 H6 O7 . 0.88(3) 1.77(3) 2.649(2) 173(2)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 O1 -179.94(16) ?
C7 C1 C2 O1 4.9(2) ?
C6 C1 C2 C3 0.6(2) ?
C7 C1 C2 C3 -174.57(15) ?
O1 C2 C3 C4 178.85(17) ?
C1 C2 C3 C4 -1.7(3) ?
C2 C3 C4 C5 1.6(3) ?
C3 C4 C5 C6 -0.3(3) ?
C3 C4 C5 N2 177.69(17) ?
C4 C5 C6 C1 -0.8(2) ?
N2 C5 C6 C1 -178.79(15) ?
C7 C1 C6 C5 175.90(15) ?
C2 C1 C6 C5 0.6(2) ?
C6 C1 C7 N1 -178.96(16) y
C2 C1 C7 N1 -3.6(3) ?
N1 C8 C9 O4 -179.39(14) y
C11 C8 C9 O4 62.53(18) ?
C10 C8 C9 O4 -61.02(17) ?
N1 C8 C10 O5 64.27(15) ?
C11 C8 C10 O5 -179.68(12) ?
C9 C8 C10 O5 -56.38(16) ?
N1 C8 C11 O6 50.34(17) ?
C9 C8 C11 O6 170.55(13) ?
C10 C8 C11 O6 -65.48(17) ?
C1 C7 N1 C8 168.79(15) ?
C11 C8 N1 C7 152.37(16) ?
C9 C8 N1 C7 32.3(2) ?
C10 C8 N1 C7 -89.06(19) y
C6 C5 N2 O2 179.38(17) ?
C4 C5 N2 O2 1.4(3) ?
C6 C5 N2 O3 0.3(2) ?
C4 C5 N2 O3 -177.72(16) ?
