#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/28/2232850.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_2232850
loop_
_publ_author_name
'Mu, Xiao-Gang'
'Wang, Xuan-Jun'
'Zhang, Youzhi'
'Gou, Xiaoli'
'Li, Xia'
_publ_section_title
;
 1-Methylhydrazinium picrate
;
_journal_coeditor_code           LH5375
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3378
_journal_paper_doi               10.1107/S1600536811048677
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C H7 N2 +, C6 H2 N3 O7 -'
_chemical_formula_moiety         'C H7 N2 +, C6 H2 N3 O7 -'
_chemical_formula_sum            'C7 H9 N5 O7'
_chemical_formula_weight         275.19
_chemical_name_common
;
1-Methylhydrazinium picrate
;
_chemical_name_systematic
;
1-Methylhydrazinium 2,4,6-trinitrophenolate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 110.526(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.766(3)
_cell_length_b                   6.785(2)
_cell_length_c                   14.420(4)
_cell_measurement_reflns_used    1614
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.10
_cell_measurement_theta_min      2.77
_cell_volume                     1078.1(5)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5196
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         1.93
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_T_max  0.9794
_exptl_absorpt_correction_T_min  0.9519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.257
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0370
_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)+(0.0537P)²+0.1530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1025
_reflns_number_gt                1562
_reflns_number_total             1907
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5375.cif
_cod_data_source_block           I
_cod_original_cell_volume        1078.0(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2232850
_cod_database_fobs_code          2232850
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_symmetry_multiplicity
N N1 0.52167(12) 0.1473(2) 0.41558(10) 0.0358(4) Uani d . 1 1
N N2 0.31795(13) 0.0736(2) 0.04968(10) 0.0359(4) Uani d . 1 1
N N3 0.08521(12) 0.1090(2) 0.26709(11) 0.0353(4) Uani d . 1 1
N N4 0.26648(12) 0.1526(2) 0.69636(10) 0.0335(4) Uani d . 1 1
H H4A 0.3278 0.0814 0.6943 0.040 Uiso d R 1 1
H H4B 0.2808 0.2764 0.7014 0.040 Uiso d R 1 1
N N5 0.24219(13) 0.0849(2) 0.78250(11) 0.0361(4) Uani d . 1 1
H H5A 0.1824 0.1576 0.7857 0.043 Uiso d R 1 1
H H5B 0.3089 0.1102 0.8361 0.043 Uiso d R 1 1
O O1 0.50471(11) 0.2240(2) 0.48615(9) 0.0523(4) Uani d . 1 1
O O2 0.62224(11) 0.0934(3) 0.41872(10) 0.0575(4) Uani d . 1 1
O O3 0.53492(10) 0.09419(19) 0.22096(8) 0.0365(3) Uani d . 1 1
O O4 0.39264(12) 0.1642(3) 0.02613(10) 0.0612(5) Uani d . 1 1
O O5 0.23853(12) -0.0268(2) -0.00860(9) 0.0536(4) Uani d . 1 1
O O6 -0.00559(11) 0.0933(2) 0.19306(11) 0.0578(4) Uani d . 1 1
O O7 0.08063(12) 0.1317(2) 0.34954(11) 0.0568(4) Uani d . 1 1
C C1 0.41718(13) 0.1197(2) 0.32599(11) 0.0268(4) Uani d . 1 1
C C2 0.43426(14) 0.1013(2) 0.23195(12) 0.0266(4) Uani d . 1 1
C C3 0.31911(14) 0.0895(2) 0.15092(11) 0.0275(4) Uani d . 1 1
C C4 0.20832(14) 0.0859(2) 0.16195(12) 0.0281(4) Uani d . 1 1
H H4 0.1377 0.0719 0.1070 0.034 Uiso calc R 1 1
C C5 0.20249(14) 0.1034(2) 0.25554(12) 0.0274(4) Uani d . 1 1
C C6 0.30624(14) 0.1220(2) 0.33767(12) 0.0285(4) Uani d . 1 1
H H6 0.3013 0.1359 0.4003 0.034 Uiso calc R 1 1
C C8 0.16207(17) 0.1100(3) 0.60533(14) 0.0435(5) Uani d . 1 1
H H8A 0.1426 -0.0278 0.6032 0.065 Uiso calc R 1 1
H H8B 0.1825 0.1437 0.5484 0.065 Uiso calc R 1 1
H H8C 0.0933 0.1862 0.6052 0.065 Uiso calc R 1 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 N1 O2 122.36(14)
O1 N1 C1 117.56(14)
O2 N1 C1 120.08(14)
O4 N2 O5 122.94(15)
O4 N2 C3 119.25(15)
O5 N2 C3 117.77(14)
O7 N3 O6 122.63(15)
O7 N3 C5 119.05(14)
O6 N3 C5 118.31(15)
N5 N4 C8 110.36(14)
N5 N4 H4A 105.5
C8 N4 H4A 107.4
N5 N4 H4B 109.4
C8 N4 H4B 110.2
H4A N4 H4B 113.8
N4 N5 H5A 105.7
N4 N5 H5B 107.5
H5A N5 H5B 108.8
C6 C1 C2 124.55(14)
C6 C1 N1 115.77(14)
C2 C1 N1 119.61(14)
O3 C2 C1 124.91(14)
O3 C2 C3 123.77(15)
C1 C2 C3 111.31(13)
C4 C3 C2 124.57(15)
C4 C3 N2 116.12(14)
C2 C3 N2 119.28(14)
C3 C4 C5 119.24(15)
C3 C4 H4 120.4
C5 C4 H4 120.4
C6 C5 C4 121.05(14)
C6 C5 N3 119.50(15)
C4 C5 N3 119.41(14)
C1 C6 C5 119.20(15)
C1 C6 H6 120.4
C5 C6 H6 120.4
N4 C8 H8A 109.5
N4 C8 H8B 109.5
H8A C8 H8B 109.5
N4 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 O1 1.2200(18)
N1 O2 1.2240(18)
N1 C1 1.450(2)
N2 O4 1.2143(19)
N2 O5 1.2216(19)
N2 C3 1.459(2)
N3 O7 1.2186(19)
N3 O6 1.2217(19)
N3 C5 1.447(2)
N4 N5 1.4439(19)
N4 C8 1.478(2)
N4 H4A 0.8777
N4 H4B 0.8546
N5 H5A 0.8732
N5 H5B 0.9046
O3 C2 1.2498(19)
C1 C6 1.374(2)
C1 C2 1.444(2)
C2 C3 1.448(2)
C3 C4 1.368(2)
C4 C5 1.380(2)
C4 H4 0.9300
C5 C6 1.376(2)
C6 H6 0.9300
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
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
N4 H4A O3 3_656 0.88 2.03 2.7807(19) 142.3
N4 H4A O2 3_656 0.88 2.25 2.963(2) 137.8
N4 H4B N5 2_556 0.85 2.13 2.954(2) 160.8
N5 H5A O3 4_566 0.87 2.36 3.156(2) 151.1
N5 H5B O4 1_556 0.90 2.59 3.377(2) 145.6
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 N1 C1 C6 -20.3(2)
O2 N1 C1 C6 159.30(16)
O1 N1 C1 C2 156.85(16)
O2 N1 C1 C2 -23.5(2)
C6 C1 C2 O3 -178.15(16)
N1 C1 C2 O3 4.9(2)
C6 C1 C2 C3 1.2(2)
N1 C1 C2 C3 -175.74(14)
O3 C2 C3 C4 176.18(16)
C1 C2 C3 C4 -3.1(2)
O3 C2 C3 N2 -1.7(2)
C1 C2 C3 N2 178.99(14)
O4 N2 C3 C4 144.66(17)
O5 N2 C3 C4 -33.1(2)
O4 N2 C3 C2 -37.3(2)
O5 N2 C3 C2 144.91(16)
C2 C3 C4 C5 3.1(3)
N2 C3 C4 C5 -178.99(14)
C3 C4 C5 C6 -0.8(2)
C3 C4 C5 N3 177.12(15)
O7 N3 C5 C6 0.6(2)
O6 N3 C5 C6 179.60(15)
O7 N3 C5 C4 -177.37(15)
O6 N3 C5 C4 1.7(2)
C2 C1 C6 C5 0.8(2)
N1 C1 C6 C5 177.81(14)
C4 C5 C6 C1 -1.1(2)
N3 C5 C6 C1 -178.97(15)
