#------------------------------------------------------------------------------
#$Date: 2019-12-25 22:52:58 +0200 (Wed, 25 Dec 2019) $
#$Revision: 245964 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/15/2311536.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_2311536
loop_
_publ_author_name
'Liu, Ling-Li'
_publ_section_title
;
 Stoichiometric and polymorphic salt of imidazolium picrate monohydrate.
;
_journal_coeditor_code           LH5861
_journal_issue                   'Pt 12'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              1885
_journal_page_last               1888
_journal_paper_doi               10.1107/S2056989017016401
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C3 H5 N2 +, C6 H2 N3 O7 -, H2 O'
_chemical_formula_moiety         'C3 H5 N2 +, C6 H2 N3 O7 -, H2 O'
_chemical_formula_sum            'C9 H9 N5 O8'
_chemical_formula_weight         315.21
_chemical_name_systematic
;
1H-Imidazol-3-ium 2,4,6-trinitrophenolate monohydrate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.577(11)
_cell_length_b                   3.5533(18)
_cell_length_c                   16.096(8)
_cell_measurement_reflns_used    4015
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.17
_cell_measurement_theta_min      2.27
_cell_volume                     1234.1(11)
_computing_cell_refinement
;
SAINT (Bruker, 2001)
;
_computing_data_collection
;
APEX2 (Bruker, 2001)
;
_computing_data_reduction
;
SAINT (Bruker, 2001)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11664
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.974
_diffrn_reflns_theta_min         1.888
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.9971
_exptl_absorpt_correction_T_min  0.9374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2001)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_description       needle
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.220
_refine_ls_abs_structure_details
;
Flack x determined using 1456 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.4(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3837
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0346
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0494P)²+0.0144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0863
_reflns_number_gt                3367
_reflns_number_total             3837
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lh5861sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1234.0(11)
_cod_database_code               2311536
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.942
_shelx_estimated_absorpt_t_max   0.997
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
C C1 0.67480(9) -0.0182(6) 0.64727(12) 0.0122(3) Uani d 1
C C2 0.72241(9) 0.0454(6) 0.70899(11) 0.0125(4) Uani d 1
C C3 0.78154(9) 0.1698(6) 0.69303(11) 0.0131(4) Uani d 1
H H3 0.8106 0.2010 0.7368 0.016 Uiso calc 1
C C4 0.79782(9) 0.2488(6) 0.61128(12) 0.0128(3) Uani d 1
C C5 0.75625(8) 0.1917(6) 0.54609(12) 0.0133(4) Uani d 1
H H5 0.7681 0.2377 0.4902 0.016 Uiso calc 1
C C6 0.69788(9) 0.0674(6) 0.56500(12) 0.0125(3) Uani d 1
C C8 0.48877(9) 0.4718(7) 0.77357(13) 0.0172(4) Uani d 1
H H8 0.4715 0.4535 0.7194 0.021 Uiso calc 1
C C9 0.46050(9) 0.3770(7) 0.84591(13) 0.0181(4) Uani d 1
H H9 0.4197 0.2809 0.8522 0.022 Uiso calc 1
N N1 0.70790(8) -0.0342(5) 0.79547(11) 0.0143(3) Uani d 1
N N2 0.85824(8) 0.4007(5) 0.59405(11) 0.0150(3) Uani d 1
N N3 0.65576(8) 0.0095(5) 0.49511(11) 0.0149(3) Uani d 1
C C7 0.55452(10) 0.5801(7) 0.87530(13) 0.0172(4) Uani d 1
H H7 0.5908 0.6495 0.9049 0.021 Uiso calc 1
N N4 0.50257(9) 0.4472(6) 0.90866(12) 0.0170(3) Uani d 1
H H4 0.4957(14) 0.398(9) 0.9649(19) 0.020 Uiso d 1
N N5 0.54696(8) 0.5991(5) 0.79335(11) 0.0157(3) Uani d 1
H H5A 0.5763(13) 0.682(8) 0.7586(18) 0.019 Uiso d 1
O O1 0.62270(6) -0.1576(5) 0.66176(9) 0.0156(3) Uani d 1
O O4 0.89440(7) 0.4486(5) 0.65267(10) 0.0226(3) Uani d 1
O O5 0.87159(7) 0.4829(5) 0.52189(10) 0.0226(4) Uani d 1
O O8 0.50725(7) 0.6717(6) 0.57776(10) 0.0214(3) Uani d 1
H H8A 0.4849(16) 0.841(10) 0.594(2) 0.032 Uiso d 1
H H8B 0.5441(17) 0.745(10) 0.595(2) 0.032 Uiso d 1
O O2 0.74665(8) -0.1992(5) 0.83731(10) 0.0227(4) Uani d 1
O O3 0.65759(7) 0.0718(5) 0.82223(10) 0.0219(3) Uani d 1
O O6 0.60348(7) 0.1417(5) 0.50023(10) 0.0222(4) Uani d 1
O O7 0.67538(7) -0.1656(5) 0.43500(9) 0.0211(3) Uani 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
O1 C1 C2 124.91(18)
O1 C1 C6 124.28(17)
C2 C1 C6 110.56(16)
C3 C2 C1 125.53(17)
C3 C2 N1 116.18(16)
C1 C2 N1 118.28(17)
C2 C3 C4 118.43(17)
C2 C3 H3 120.8
C4 C3 H3 120.8
C3 C4 C5 121.33(17)
C3 C4 N2 119.15(17)
C5 C4 N2 119.50(17)
C6 C5 C4 118.12(17)
C6 C5 H5 120.9
C4 C5 H5 120.9
C5 C6 C1 126.00(17)
C5 C6 N3 116.53(17)
C1 C6 N3 117.46(16)
C9 C8 N5 107.10(19)
C9 C8 H8 126.4
N5 C8 H8 126.4
C8 C9 N4 106.69(18)
C8 C9 H9 126.7
N4 C9 H9 126.7
O2 N1 O3 123.96(18)
O2 N1 C2 118.23(17)
O3 N1 C2 117.81(17)
O5 N2 O4 122.65(17)
O5 N2 C4 118.87(17)
O4 N2 C4 118.47(16)
O6 N3 O7 124.46(18)
O6 N3 C6 117.85(18)
O7 N3 C6 117.69(17)
N4 C7 N5 108.37(19)
N4 C7 H7 125.8
N5 C7 H7 125.8
C7 N4 C9 108.85(19)
C7 N4 H4 126.4(19)
C9 N4 H4 124.7(19)
C7 N5 C8 108.99(18)
C7 N5 H5A 123.3(18)
C8 N5 H5A 127.7(18)
H8A O8 H8B 102(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.250(2)
C1 C2 1.447(3)
C1 C6 1.447(3)
C2 C3 1.374(3)
C2 N1 1.455(3)
C3 C4 1.391(3)
C3 H3 0.9500
C4 C5 1.395(3)
C4 N2 1.438(3)
C5 C6 1.369(3)
C5 H5 0.9500
C6 N3 1.461(3)
C8 C9 1.357(3)
C8 N5 1.372(3)
C8 H8 0.9500
C9 N4 1.381(3)
C9 H9 0.9500
N1 O2 1.223(2)
N1 O3 1.227(2)
N2 O5 1.232(2)
N2 O4 1.236(2)
N3 O6 1.225(2)
N3 O7 1.226(3)
C7 N4 1.329(3)
C7 N5 1.331(3)
C7 H7 0.9500
N4 H4 0.93(3)
N5 H5A 0.89(3)
O8 H8A 0.82(4)
O8 H8B 0.88(4)
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
N4 H4 O8 2_665 0.93(3) 1.83(3) 2.763(3) 172(3) y
N5 H5A O1 1_565 0.89(3) 1.94(3) 2.812(2) 165(3) y
N5 H5A O3 1_565 0.89(3) 2.46(3) 2.956(3) 116(2) y
O8 H8A O4 4_465 0.82(4) 2.29(4) 3.034(2) 151(3) y
O8 H8B O1 1_565 0.88(4) 2.04(4) 2.899(2) 165(3) y
O8 H8B O6 1_565 0.88(4) 2.44(4) 2.943(3) 117(3) y
C5 H5 O2 3_654 0.95 2.49 3.383(3) 156.5 y
C7 H7 O5 3_655 0.95 2.37 3.187(3) 144.2 y
C7 H7 O3 1_565 0.95 2.47 2.955(3) 111.6 y
C8 H8 O4 4_455 0.95 2.44 3.188(3) 135.3 y
C8 H8 O8 . 0.95 2.53 3.255(3) 133.4 y
C9 H9 O7 2_655 0.95 2.48 3.349(3) 152.0 y
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
O1 C1 C2 C3 174.4(2)
C6 C1 C2 C3 0.0(3)
O1 C1 C2 N1 -4.3(3)
C6 C1 C2 N1 -178.67(19)
C1 C2 C3 C4 1.1(3)
N1 C2 C3 C4 179.82(18)
C2 C3 C4 C5 -2.3(3)
C2 C3 C4 N2 176.28(19)
C3 C4 C5 C6 2.3(3)
N2 C4 C5 C6 -176.28(19)
C4 C5 C6 C1 -1.1(3)
C4 C5 C6 N3 -179.77(19)
O1 C1 C6 C5 -174.5(2)
C2 C1 C6 C5 0.0(3)
O1 C1 C6 N3 4.2(3)
C2 C1 C6 N3 178.65(18)
N5 C8 C9 N4 -0.3(3)
C3 C2 N1 O2 -42.2(3)
C1 C2 N1 O2 136.7(2)
C3 C2 N1 O3 137.2(2)
C1 C2 N1 O3 -44.0(3)
C3 C4 N2 O5 -177.4(2)
C5 C4 N2 O5 1.2(3)
C3 C4 N2 O4 1.5(3)
C5 C4 N2 O4 -179.89(19)
C5 C6 N3 O6 -132.1(2)
C1 C6 N3 O6 49.1(3)
C5 C6 N3 O7 47.3(3)
C1 C6 N3 O7 -131.5(2)
N5 C7 N4 C9 0.3(3)
C8 C9 N4 C7 0.0(3)
N4 C7 N5 C8 -0.6(3)
C9 C8 N5 C7 0.6(3)
