#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/24/2202495.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···π and
 π--π interactions
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1383
_journal_page_last               o1386
_journal_paper_doi               10.1107/S1600536803018178
_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       ω
_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      ?
_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/[σ²(Fo²)+(0.0204P)²] where P=(Fo²+2Fc²)/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>2σ(I)
_cod_data_source_file            ci6263.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_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_enum 1527 2010-12-29 10:47:43Z saulius 

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.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               2202495
_cod_database_fobs_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_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_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_site_symmetry_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)
