#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/38/2223884.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_2223884
loop_
_publ_author_name
'Jasinski, Jerry P.'
'Butcher, Ray J.'
'Swamy, M. T.'
'Yathirajan, H. S.'
'Ramesha, A. R.'
_publ_section_title
;
 1-(2-Methyl-5-nitrophenyl)guanidinium picrate
;
_journal_coeditor_code           KP2228
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2788
_journal_page_last               o2789
_journal_paper_doi               10.1107/S1600536809037647
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C8 H11 N4 O2 +, C6 H2 N3 O7 -'
_chemical_formula_moiety         'C8 H11 N4 O2 +, C6 H2 N3 O7 -'
_chemical_formula_sum            'C14 H13 N7 O9'
_chemical_formula_weight         423.31
_chemical_name_common
;
1-(2-methyl-5-nitrophenyl)guanidinium picrate
;
_chemical_name_systematic
;
1-(2-methyl-5-nitrophenyl)guanidinium 2,4,6-trinitrophenolate
;
_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                84.257(10)
_cell_angle_beta                 74.497(11)
_cell_angle_gamma                77.559(11)
_cell_formula_units_Z            2
_cell_length_a                   7.1318(10)
_cell_length_b                   10.6239(13)
_cell_length_c                   11.9564(13)
_cell_measurement_reflns_used    3632
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      73.7576
_cell_measurement_theta_min      4.2569
_cell_volume                     851.58(19)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type
;
Oxford Xcalibur diffractometer with Ruby (Gemini Cu) detector
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6248
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         73.90
_diffrn_reflns_theta_min         4.27
_diffrn_standards_decay_%        2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.225
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis Pro; Oxford Diffraction, 2009)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.289
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3344
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0696P)²+0.2349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1181
_reflns_number_gt                2761
_reflns_number_total             3344
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp2228.cif
_cod_data_source_block           I
_cod_original_cell_volume        851.58(18)
_cod_database_code               2223884
_cod_database_fobs_code          2223884
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
O O1A 0.6186(2) 0.42327(13) 1.18314(12) 0.0358(3) Uani d . 1 . .
O O2A 0.5417(2) 0.62511(13) 1.13392(12) 0.0383(3) Uani d . 1 . .
N N1A 0.6304(2) 0.51540(14) 1.11228(13) 0.0261(3) Uani d . 1 . .
N N2A 0.9515(2) 0.68299(13) 0.73199(12) 0.0228(3) Uani d . 1 . .
H H2AA 1.0452 0.7222 0.7376 0.027 Uiso calc R 1 . .
N N3A 0.7069(2) 0.67430(13) 0.64072(12) 0.0236(3) Uani d . 1 . .
H H3AB 0.6416 0.7048 0.5877 0.028 Uiso calc R 1 . .
H H3AC 0.6762 0.6076 0.6865 0.028 Uiso calc R 1 . .
N N4A 0.8981(2) 0.82883(13) 0.58308(12) 0.0225(3) Uani d . 1 . .
H H4AA 0.8336 0.8600 0.5299 0.027 Uiso calc R 1 . .
H H4AB 0.9943 0.8644 0.5909 0.027 Uiso calc R 1 . .
C C1A 1.0118(2) 0.44934(16) 0.77518(15) 0.0229(3) Uani d . 1 . .
C C2A 0.9141(2) 0.57363(15) 0.80935(14) 0.0208(3) Uani d . 1 . .
C C3A 0.7870(2) 0.59582(16) 0.91843(14) 0.0221(3) Uani d . 1 . .
H H3AA 0.7204 0.6807 0.9400 0.026 Uiso calc R 1 . .
C C4A 0.7597(2) 0.49070(16) 0.99526(14) 0.0225(3) Uani d . 1 . .
C C5A 0.8533(2) 0.36602(16) 0.96653(15) 0.0246(4) Uani d . 1 . .
H H5AA 0.8327 0.2956 1.0208 0.029 Uiso calc R 1 . .
C C6A 0.9788(3) 0.34633(16) 0.85597(15) 0.0254(4) Uani d . 1 . .
H H6AA 1.0437 0.2610 0.8347 0.030 Uiso calc R 1 . .
C C7A 1.1495(3) 0.42731(18) 0.65702(16) 0.0298(4) Uani d . 1 . .
H H7AA 1.0824 0.4706 0.5979 0.045 Uiso calc R 1 . .
H H7AB 1.1880 0.3345 0.6445 0.045 Uiso calc R 1 . .
H H7AC 1.2682 0.4624 0.6513 0.045 Uiso calc R 1 . .
C C8A 0.8505(2) 0.72837(15) 0.65149(14) 0.0202(3) Uani d . 1 . .
O O1B 0.59719(17) 0.85654(11) 0.47353(10) 0.0254(3) Uani d . 1 . .
O O21B 0.84884(19) 1.00632(12) 0.36978(12) 0.0319(3) Uani d . 1 . .
O O22B 0.7546(2) 1.15265(12) 0.24729(12) 0.0324(3) Uani d . 1 . .
O O41B 0.3034(2) 1.09649(12) 0.03718(11) 0.0318(3) Uani d . 1 . .
O O42B 0.1500(3) 0.93647(15) 0.08197(15) 0.0518(5) Uani d . 1 . .
O O61B 0.2382(2) 0.64362(13) 0.39470(12) 0.0351(3) Uani d . 1 . .
O O62B 0.3584(2) 0.69013(14) 0.52904(12) 0.0353(3) Uani d . 1 . .
N N2B 0.7376(2) 1.05245(13) 0.30647(12) 0.0236(3) Uani d . 1 . .
N N4B 0.2629(2) 1.00057(14) 0.09892(13) 0.0292(3) Uani d . 1 . .
N N6B 0.3236(2) 0.71124(14) 0.43296(12) 0.0243(3) Uani d . 1 . .
C C1B 0.5286(2) 0.88544(15) 0.38719(14) 0.0206(3) Uani d . 1 . .
C C2B 0.5836(2) 0.98569(15) 0.29955(14) 0.0211(3) Uani d . 1 . .
C C3B 0.4980(2) 1.02404(16) 0.20829(14) 0.0224(3) Uani d . 1 . .
H H3BA 0.5364 1.0924 0.1555 0.027 Uiso calc R 1 . .
C C4B 0.3543(3) 0.96112(16) 0.19447(14) 0.0237(3) Uani d . 1 . .
C C5B 0.3011(2) 0.85874(16) 0.26861(14) 0.0230(3) Uani d . 1 . .
H H5BA 0.2080 0.8137 0.2554 0.028 Uiso calc R 1 . .
C C6B 0.3831(2) 0.82270(15) 0.36097(14) 0.0217(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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2A N1A O1A . . 123.73(15) ?
O2A N1A C4A . . 118.54(14) ?
O1A N1A C4A . . 117.73(15) ?
C8A N2A C2A . . 123.28(13) ?
C8A N2A H2AA . . 118.4 ?
C2A N2A H2AA . . 118.4 ?
C8A N3A H3AB . . 120.0 ?
C8A N3A H3AC . . 120.0 ?
H3AB N3A H3AC . . 120.0 ?
C8A N4A H4AA . . 120.0 ?
C8A N4A H4AB . . 120.0 ?
H4AA N4A H4AB . . 120.0 ?
C2A C1A C6A . . 117.73(16) ?
C2A C1A C7A . . 121.12(15) ?
C6A C1A C7A . . 121.14(16) ?
C3A C2A C1A . . 121.89(14) ?
C3A C2A N2A . . 118.23(15) ?
C1A C2A N2A . . 119.82(15) ?
C2A C3A C4A . . 118.15(15) ?
C2A C3A H3AA . . 120.9 ?
C4A C3A H3AA . . 120.9 ?
C5A C4A C3A . . 122.45(16) ?
C5A C4A N1A . . 119.67(14) ?
C3A C4A N1A . . 117.86(15) ?
C4A C5A C6A . . 118.22(15) ?
C4A C5A H5AA . . 120.9 ?
C6A C5A H5AA . . 120.9 ?
C5A C6A C1A . . 121.56(16) ?
C5A C6A H6AA . . 119.2 ?
C1A C6A H6AA . . 119.2 ?
C1A C7A H7AA . . 109.5 ?
C1A C7A H7AB . . 109.5 ?
H7AA C7A H7AB . . 109.5 ?
C1A C7A H7AC . . 109.5 ?
H7AA C7A H7AC . . 109.5 ?
H7AB C7A H7AC . . 109.5 ?
N3A C8A N4A . . 120.59(14) ?
N3A C8A N2A . . 120.75(14) ?
N4A C8A N2A . . 118.67(14) ?
O22B N2B O21B . . 122.00(13) ?
O22B N2B C2B . . 118.56(13) ?
O21B N2B C2B . . 119.43(13) ?
O42B N4B O41B . . 122.85(15) ?
O42B N4B C4B . . 118.43(14) ?
O41B N4B C4B . . 118.72(14) ?
O61B N6B O62B . . 122.78(14) ?
O61B N6B C6B . . 117.97(14) ?
O62B N6B C6B . . 119.25(13) ?
O1B C1B C2B . . 124.20(14) ?
O1B C1B C6B . . 124.04(15) ?
C2B C1B C6B . . 111.76(14) ?
C3B C2B N2B . . 116.04(14) ?
C3B C2B C1B . . 124.33(14) ?
N2B C2B C1B . . 119.63(14) ?
C2B C3B C4B . . 118.92(15) ?
C2B C3B H3BA . . 120.5 ?
C4B C3B H3BA . . 120.5 ?
C5B C4B C3B . . 121.16(15) ?
C5B C4B N4B . . 119.33(14) ?
C3B C4B N4B . . 119.48(14) ?
C6B C5B C4B . . 119.76(15) ?
C6B C5B H5BA . . 120.1 ?
C4B C5B H5BA . . 120.1 ?
C5B C6B C1B . . 123.85(15) ?
C5B C6B N6B . . 116.32(14) ?
C1B C6B N6B . . 119.79(14) ?
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
O1A N1A . 1.2306(19) ?
O2A N1A . 1.217(2) ?
N1A C4A . 1.468(2) ?
N2A C8A . 1.344(2) ?
N2A C2A . 1.4363(19) ?
N2A H2AA . 0.8800 ?
N3A C8A . 1.317(2) ?
N3A H3AB . 0.8800 ?
N3A H3AC . 0.8800 ?
N4A C8A . 1.325(2) ?
N4A H4AA . 0.8800 ?
N4A H4AB . 0.8800 ?
C1A C2A . 1.398(2) ?
C1A C6A . 1.401(2) ?
C1A C7A . 1.497(2) ?
C2A C3A . 1.384(2) ?
C3A C4A . 1.386(2) ?
C3A H3AA . 0.9500 ?
C4A C5A . 1.381(2) ?
C5A C6A . 1.391(2) ?
C5A H5AA . 0.9500 ?
C6A H6AA . 0.9500 ?
C7A H7AA . 0.9800 ?
C7A H7AB . 0.9800 ?
C7A H7AC . 0.9800 ?
O1B C1B . 1.241(2) ?
O21B N2B . 1.2334(18) ?
O22B N2B . 1.2278(18) ?
O41B N4B . 1.2364(19) ?
O42B N4B . 1.227(2) ?
O61B N6B . 1.2250(19) ?
O62B N6B . 1.2280(19) ?
N2B C2B . 1.4534(19) ?
N4B C4B . 1.445(2) ?
N6B C6B . 1.463(2) ?
C1B C2B . 1.457(2) ?
C1B C6B . 1.460(2) ?
C2B C3B . 1.374(2) ?
C3B C4B . 1.390(2) ?
C3B H3BA . 0.9500 ?
C4B C5B . 1.385(2) ?
C5B C6B . 1.368(2) ?
C5B H5BA . 0.9500 ?
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
N2A H2AA O22B 2_776 0.88 2.20 3.0737(18) 171.3
N3A H3AB O1B . 0.88 2.03 2.7866(18) 143.0
N3A H3AB O62B . 0.88 2.35 3.0882(18) 141.8
N3A H3AC O1A 2_667 0.88 2.32 2.9808(19) 131.5
N4A H4AA O1B . 0.88 1.98 2.7499(18) 144.7
N4A H4AA O21B . 0.88 2.34 3.0683(19) 140.7
N4A H4AB O21B 2_776 0.88 2.11 2.9572(18) 162.7
C3A H3AA O41B 2_676 0.95 2.37 3.262(2) 155.3
C7A H7AB O1B 2_766 0.98 2.56 3.447(2) 151.0
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
C6A C1A C2A C3A . . . . -0.7(2) ?
C7A C1A C2A C3A . . . . -179.70(15) ?
C6A C1A C2A N2A . . . . 176.60(13) ?
C7A C1A C2A N2A . . . . -2.4(2) ?
C8A N2A C2A C3A . . . . -94.78(19) ?
C8A N2A C2A C1A . . . . 87.8(2) ?
C1A C2A C3A C4A . . . . 0.8(2) ?
N2A C2A C3A C4A . . . . -176.51(13) ?
C2A C3A C4A C5A . . . . -0.3(2) ?
C2A C3A C4A N1A . . . . 177.78(13) ?
O2A N1A C4A C5A . . . . -176.41(15) ?
O1A N1A C4A C5A . . . . 3.7(2) ?
O2A N1A C4A C3A . . . . 5.4(2) ?
O1A N1A C4A C3A . . . . -174.45(14) ?
C3A C4A C5A C6A . . . . -0.3(2) ?
N1A C4A C5A C6A . . . . -178.34(14) ?
C4A C5A C6A C1A . . . . 0.4(2) ?
C2A C1A C6A C5A . . . . 0.1(2) ?
C7A C1A C6A C5A . . . . 179.07(15) ?
C2A N2A C8A N3A . . . . 1.0(2) ?
C2A N2A C8A N4A . . . . -179.04(15) ?
O22B N2B C2B C3B . . . . 14.1(2) ?
O21B N2B C2B C3B . . . . -164.83(15) ?
O22B N2B C2B C1B . . . . -165.51(15) ?
O21B N2B C2B C1B . . . . 15.6(2) ?
O1B C1B C2B C3B . . . . -175.27(16) ?
C6B C1B C2B C3B . . . . 4.9(2) ?
O1B C1B C2B N2B . . . . 4.3(3) ?
C6B C1B C2B N2B . . . . -175.56(14) ?
N2B C2B C3B C4B . . . . 177.91(15) ?
C1B C2B C3B C4B . . . . -2.5(3) ?
C2B C3B C4B C5B . . . . -2.0(3) ?
C2B C3B C4B N4B . . . . 179.95(15) ?
O42B N4B C4B C5B . . . . -4.7(3) ?
O41B N4B C4B C5B . . . . 176.06(16) ?
O42B N4B C4B C3B . . . . 173.45(18) ?
O41B N4B C4B C3B . . . . -5.8(3) ?
C3B C4B C5B C6B . . . . 3.5(3) ?
N4B C4B C5B C6B . . . . -178.40(15) ?
C4B C5B C6B C1B . . . . -0.7(3) ?
C4B C5B C6B N6B . . . . -178.21(15) ?
O1B C1B C6B C5B . . . . 176.90(16) ?
C2B C1B C6B C5B . . . . -3.2(2) ?
O1B C1B C6B N6B . . . . -5.6(2) ?
C2B C1B C6B N6B . . . . 174.21(14) ?
O61B N6B C6B C5B . . . . 13.8(2) ?
O62B N6B C6B C5B . . . . -165.22(16) ?
O61B N6B C6B C1B . . . . -163.84(16) ?
O62B N6B C6B C1B . . . . 17.1(2) ?
