#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2202495.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_2202495
loop_
_publ_author_name
'Vembu, Nagarajan'
'Nallu, Maruthai'
'Spencer, Elinor C.'
'Howard, Judith A. K.'
_publ_section_title
;
 4-Dimethylaminopyridinium 2,4-dinitrophenolate: supramolecular
 aggregation through N---H···O,
 C---H···O, C---H···\p and
 \p--\p interactions
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1383
_journal_page_last               o1386
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C7 H11 N2 + , C6 H3 N2 O5 -'
_chemical_formula_moiety         'C7 H11 N2 + , C6 H3 N2 O5 -'
_chemical_formula_sum            'C13 H14 N4 O5'
_chemical_formula_weight         306.28
_chemical_melting_point          433.0(10)
_chemical_name_systematic
;
4-Dimethylaminopyridinium 2,4-dinitrophenolate
;
_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
_audit_creation_method           SHELXL97
_cell_angle_alpha                96.916(3)
_cell_angle_beta                 92.630(3)
_cell_angle_gamma                101.618(3)
_cell_formula_units_Z            2
_cell_length_a                   7.7246(9)
_cell_length_b                   8.1665(10)
_cell_length_c                   10.8838(13)
_cell_measurement_reflns_used    763
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.025
_cell_measurement_theta_min      2.569
_cell_volume                     665.88(14)
_computing_cell_refinement       SMART-NT
_computing_data_collection       'SMART-NT (Bruker, 1998)'
_computing_data_reduction        'SAINT-NT (Bruker, 1998)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Proteum M'
_diffrn_measurement_method       \w
_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  0.037
_diffrn_reflns_av_sigmaI/netI    0.082
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3781
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.57
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.798
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2332
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.798
_refine_ls_R_factor_all          0.075
_refine_ls_R_factor_gt           0.037
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0204P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.062
_refine_ls_wR_factor_ref         0.067
_reflns_number_gt                1444
_reflns_number_total             2332
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    ci6263.cif
_[local]_cod_data_source_block   I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '432-434' was changed to '433.0(10)'
- the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Triclinic' changed to
'triclinic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2202495
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
C1 0.2278(2) 0.8980(2) -0.05184(18) 0.0163(5) Uani d 1 C
C2 0.2907(2) 1.0056(2) 0.06227(19) 0.0163(5) Uani d 1 C
C3 0.3875(2) 0.9562(2) 0.1562(2) 0.0169(5) Uani d 1 C
H3 0.427(2) 1.031(2) 0.2309(18) 0.020 Uiso d 1 H
C4 0.4256(2) 0.7976(2) 0.14274(19) 0.0168(5) Uani d 1 C
C5 0.3647(2) 0.6838(2) 0.03448(19) 0.0182(5) Uani d 1 C
H5 0.390(2) 0.571(2) 0.0307(17) 0.022 Uiso d 1 H
C6 0.2715(3) 0.7336(2) -0.0571(2) 0.0195(5) Uani d 1 C
H6 0.234(2) 0.658(2) -0.1317(18) 0.023 Uiso d 1 H
N1 0.2543(2) 1.17279(19) 0.08717(17) 0.0195(4) Uani d 1 N
N2 0.5283(2) 0.7486(2) 0.24042(17) 0.0223(4) Uani d 1 N
O1 0.14054(17) 0.93398(15) -0.14207(13) 0.0216(4) Uani d 1 O
O2 0.20170(18) 1.23992(16) 0.00035(13) 0.0255(4) Uani d 1 O
O3 0.27575(18) 1.24511(16) 0.19526(13) 0.0281(4) Uani d 1 O
O4 0.57560(18) 0.84841(17) 0.33730(14) 0.0280(4) Uani d 1 O
O5 0.56493(18) 0.60752(17) 0.22452(13) 0.0294(4) Uani d 1 O
C7 1.0031(2) 0.3307(2) 0.7855(2) 0.0188(5) Uani d 1 C
H7 1.062(2) 0.389(2) 0.8654(18) 0.023 Uiso d 1 H
C8 0.9177(3) 0.4063(2) 0.7045(2) 0.0190(5) Uani d 1 C
H8 0.911(2) 0.523(2) 0.7243(17) 0.023 Uiso d 1 H
C9 0.8367(2) 0.3143(2) 0.59059(19) 0.0170(5) Uani d 1 C
C10 0.8427(3) 0.1406(2) 0.5708(2) 0.0195(5) Uani d 1 C
H10 0.785(2) 0.068(2) 0.4972(18) 0.023 Uiso d 1 H
C11 0.9318(2) 0.0739(3) 0.65571(19) 0.0195(5) Uani d 1 C
H11 0.941(2) -0.046(2) 0.6486(17) 0.023 Uiso d 1 H
C12 0.6621(3) 0.2839(3) 0.3938(2) 0.0262(5) Uani d 1 C
H12C 0.622(2) 0.363(2) 0.3424(19) 0.031 Uiso d 1 H
H12B 0.558(3) 0.199(2) 0.4179(19) 0.031 Uiso d 1 H
H12A 0.739(2) 0.223(2) 0.3481(18) 0.031 Uiso d 1 H
C13 0.7444(3) 0.5630(3) 0.5297(2) 0.0252(6) Uani d 1 C
H13A 0.689(2) 0.597(2) 0.451(2) 0.030 Uiso d 1 H
H13B 0.672(2) 0.581(2) 0.5953(19) 0.030 Uiso d 1 H
H13C 0.861(3) 0.641(2) 0.5534(19) 0.030 Uiso d 1 H
N3 1.0129(2) 0.1677(2) 0.76077(16) 0.0200(4) Uani d 1 N
H3A 1.071(3) 0.117(2) 0.8151(19) 0.024 Uiso d 1 H
N4 0.7571(2) 0.38617(19) 0.50494(15) 0.0203(4) Uani d 1 N
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
C1 0.0136(11) 0.0202(11) 0.0155(12) 0.0024(9) 0.0026(10) 0.0054(10)
C2 0.0167(11) 0.0146(10) 0.0183(13) 0.0041(8) 0.0035(10) 0.0028(9)
C3 0.0141(11) 0.0195(11) 0.0153(12) 0.0001(9) 0.0032(10) 0.0004(9)
C4 0.0147(11) 0.0197(11) 0.0174(12) 0.0040(9) 0.0008(10) 0.0075(9)
C5 0.0183(11) 0.0169(11) 0.0209(13) 0.0050(9) 0.0032(10) 0.0052(10)
C6 0.0217(12) 0.0166(11) 0.0186(13) 0.0023(9) 0.0004(10) -0.0004(10)
N1 0.0183(9) 0.0205(9) 0.0203(11) 0.0053(7) 0.0016(8) 0.0022(9)
N2 0.0199(10) 0.0223(10) 0.0258(12) 0.0037(8) 0.0021(9) 0.0084(9)
O1 0.0244(8) 0.0209(7) 0.0197(9) 0.0064(6) -0.0049(7) 0.0034(7)
O2 0.0344(9) 0.0213(8) 0.0230(9) 0.0106(6) -0.0042(7) 0.0058(7)
O3 0.0386(9) 0.0256(8) 0.0193(9) 0.0121(7) -0.0036(8) -0.0071(7)
O4 0.0315(9) 0.0317(8) 0.0199(9) 0.0077(7) -0.0057(7) 0.0012(7)
O5 0.0343(9) 0.0242(8) 0.0331(10) 0.0123(7) -0.0030(8) 0.0093(7)
C7 0.0179(12) 0.0194(11) 0.0179(12) 0.0020(9) 0.0002(10) 0.0016(10)
C8 0.0197(11) 0.0176(11) 0.0197(13) 0.0042(9) 0.0024(10) 0.0015(10)
C9 0.0145(11) 0.0205(11) 0.0165(12) 0.0034(9) 0.0027(10) 0.0046(10)
C10 0.0204(12) 0.0221(12) 0.0159(13) 0.0047(9) 0.0012(10) 0.0011(10)
C11 0.0203(12) 0.0217(11) 0.0175(13) 0.0064(9) 0.0046(10) 0.0019(10)
C12 0.0326(14) 0.0317(14) 0.0158(13) 0.0129(11) -0.0038(11) 0.0003(11)
C13 0.0300(14) 0.0229(12) 0.0251(15) 0.0119(10) -0.0005(12) 0.0030(11)
N3 0.0175(10) 0.0236(10) 0.0207(11) 0.0066(7) 0.0000(8) 0.0071(8)
N4 0.0262(10) 0.0205(9) 0.0149(10) 0.0076(8) -0.0004(9) 0.0015(8)
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
O1 C1 C2 126.52(18) ?
O1 C1 C6 119.97(17) ?
C2 C1 C6 113.51(17) ?
C3 C2 C1 122.66(18) ?
C3 C2 N1 115.55(18) ?
C1 C2 N1 121.79(17) ?
C4 C3 C2 120.04(19) ?
C4 C3 H3 119.5(10) ?
C2 C3 H3 120.4(10) ?
C3 C4 C5 120.46(19) ?
C3 C4 N2 119.48(18) ?
C5 C4 N2 120.06(18) ?
C6 C5 C4 119.05(19) ?
C6 C5 H5 123.3(10) ?
C4 C5 H5 117.6(10) ?
C5 C6 C1 124.26(19) ?
C5 C6 H6 118.9(11) ?
C1 C6 H6 116.8(11) ?
O3 N1 O2 121.66(16) y
O3 N1 C2 118.94(17) y
O2 N1 C2 119.40(17) y
O5 N2 O4 122.57(17) y
O5 N2 C4 118.19(17) y
O4 N2 C4 119.24(17) y
N3 C7 C8 121.3(2) ?
N3 C7 H7 115.0(10) ?
C8 C7 H7 123.6(10) ?
C7 C8 C9 120.33(19) ?
C7 C8 H8 120.2(11) ?
C9 C8 H8 119.4(11) ?
N4 C9 C8 122.37(17) ?
N4 C9 C10 121.13(18) ?
C8 C9 C10 116.50(18) ?
C11 C10 C9 119.7(2) ?
C11 C10 H10 118.9(10) ?
C9 C10 H10 121.3(10) ?
N3 C11 C10 121.7(2) ?
N3 C11 H11 113.9(10) ?
C10 C11 H11 124.4(10) ?
N4 C12 H12C 106.5(11) ?
N4 C12 H12B 109.8(11) ?
H12C C12 H12B 111.5(15) ?
N4 C12 H12A 110.8(11) ?
H12C C12 H12A 109.9(17) ?
H12B C12 H12A 108.3(15) ?
N4 C13 H13A 108.9(11) ?
N4 C13 H13B 111.4(12) ?
H13A C13 H13B 107.9(16) ?
N4 C13 H13C 113.2(11) ?
H13A C13 H13C 108.7(17) ?
H13B C13 H13C 106.5(17) ?
C7 N3 C11 120.24(19) y
C7 N3 H3A 121.3(12) ?
C11 N3 H3A 118.4(12) ?
C9 N4 C12 120.52(17) y
C9 N4 C13 120.30(17) y
C12 N4 C13 118.69(17) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.262(2) y
C1 C2 1.435(3) ?
C1 C6 1.444(2) ?
C2 C3 1.385(3) ?
C2 N1 1.445(2) y
C3 C4 1.378(2) ?
C3 H3 0.954(17) ?
C4 C5 1.408(3) ?
C4 N2 1.440(2) y
C5 C6 1.352(3) ?
C5 H5 0.977(17) ?
C6 H6 0.954(17) ?
N1 O3 1.2393(19) y
N1 O2 1.240(2) y
N2 O5 1.2354(18) y
N2 O4 1.2438(19) y
C7 N3 1.344(2) y
C7 C8 1.355(3) ?
C7 H7 0.983(18) ?
C8 C9 1.417(3) ?
C8 H8 0.968(17) ?
C9 N4 1.347(2) y
C9 C10 1.420(3) ?
C10 C11 1.356(3) ?
C10 H10 0.968(17) ?
C11 N3 1.348(2) y
C11 H11 0.989(17) ?
C12 N4 1.459(3) y
C12 H12C 0.990(19) ?
C12 H12B 1.02(2) ?
C12 H12A 0.968(19) ?
C13 N4 1.461(3) y
C13 H13A 1.03(2) ?
C13 H13B 0.94(2) ?
C13 H13C 0.993(18) ?
N3 H3A 0.913(19) ?
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
C3 H3 O3 . 0.954(17) 2.350(16) 2.665(2) 98.6(12) y
C3 H3 O4 . 0.954(17) 2.421(17) 2.728(3) 98.3(11) y
C5 H5 O5 . 0.977(17) 2.406(17) 2.732(2) 98.8(11) y
C12 H12C O5 . 0.990(19) 2.60(2) 3.576(3) 170.0(14) y
C13 H13A O4 . 1.03(2) 2.78(2) 3.697(3) 147.9(14) y
C13 H13A O5 . 1.03(2) 2.62(2) 3.628(3) 164.5(14) y
C12 H12C O3 1_545 0.990(19) 2.972(18) 3.541(3) 117.6(13) y
C12 H12B O4 1_545 1.02(2) 2.920(18) 3.457(3) 113.6(13) y
C10 H10 O4 1_545 0.968(17) 2.585(18) 3.533(2) 166.3(15) y
C5 H5 O2 1_545 0.977(17) 2.772(17) 3.558(2) 137.9(13) y
C11 H11 O1 1_646 0.989(17) 2.731(17) 3.126(2) 104.3(11) y
C7 H7 O2 1_646 0.983(18) 2.369(17) 2.986(3) 120.2(12) y
N3 H3A O1 1_646 0.913(19) 1.791(19) 2.624(2) 150.4(17) y
N3 H3A O2 1_646 0.913(19) 2.238(19) 2.865(2) 125.4(15) y
C8 H8 O3 2_676 0.968(17) 2.688(18) 3.555(2) 149.3(14) y
C13 H13B O3 2_676 0.94(2) 2.51(2) 3.233(3) 133.8(14) y
C12 H12B O4 2_666 1.02(2) 2.94(2) 3.683(3) 130.3(13) y
C11 H11 O3 2_666 0.989(17) 2.858(18) 3.401(3) 115.3(13) y
C12 H12A O1 2_665 0.968(19) 2.74(2) 3.646(3) 156.1(15) y
C13 H13C Cg1 2_766 0.993(18) 3.22(2) 3.745(2) 114.4(14) 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 -179.3(2)
C6 C1 C2 C3 1.5(3)
O1 C1 C2 N1 1.6(3)
C6 C1 C2 N1 -177.59(17)
C1 C2 C3 C4 -0.6(3)
N1 C2 C3 C4 178.51(16)
C2 C3 C4 C5 -0.9(3)
C2 C3 C4 N2 179.21(19)
C3 C4 C5 C6 1.4(3)
N2 C4 C5 C6 -178.7(2)
C4 C5 C6 C1 -0.4(3)
O1 C1 C6 C5 179.8(2)
C2 C1 C6 C5 -1.0(3)
C3 C2 N1 O3 -15.2(3)
C1 C2 N1 O3 163.95(17)
C3 C2 N1 O2 165.18(18)
C1 C2 N1 O2 -15.7(3)
C3 C4 N2 O5 -177.97(17)
C5 C4 N2 O5 2.1(3)
C3 C4 N2 O4 2.5(3)
C5 C4 N2 O4 -177.40(18)
N3 C7 C8 C9 -0.2(3)
C7 C8 C9 N4 -177.1(2)
C7 C8 C9 C10 3.2(3)
N4 C9 C10 C11 176.5(2)
C8 C9 C10 C11 -3.8(3)
C9 C10 C11 N3 1.4(3)
C8 C7 N3 C11 -2.4(3)
C10 C11 N3 C7 1.8(3)
C8 C9 N4 C12 -174.7(2)
C10 C9 N4 C12 5.0(3)
C8 C9 N4 C13 -2.9(3)
C10 C9 N4 C13 176.84(19)