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Within and between mol­ecules of the title compound, C7H11N2+·C6H5NO3·C6H4NO3, there are C—H...O, C—H...N, O—H...O and N—H...O interactions, which generate rings of graph-set motifs S(5), R12(5), R12(6), R12(7) and R21(4). The supramolecular aggregation is completed by the presence of three different π–π interactions and short van der Waals contacts.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803016179/ob6278sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803016179/ob6278Isup2.hkl
Contains datablock I

CCDC reference: 221708

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.041
  • wR factor = 0.065
  • Data-to-parameter ratio = 7.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.16 From the CIF: _reflns_number_total 2355 Count of symmetry unique reflns 2363 Completeness (_total/calc) 99.66% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

4-Dimethylaminopyridinium 4-nitrophenolate/4-nitrophenol top
Crystal data top
C7H11N2+·C6H4NO3·C6H5NO3Dx = 1.444 Mg m3
Mr = 400.39Melting point = 397–399 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 701 reflections
a = 6.4168 (16) Åθ = 3.0–22.4°
b = 11.505 (3) ŵ = 0.11 mm1
c = 24.943 (6) ÅT = 120 K
V = 1841.4 (8) Å3Block, yellow
Z = 40.20 × 0.15 × 0.11 mm
F(000) = 840
Data collection top
Bruker Proteum M
diffractometer
1940 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.048
Graphite monochromatorθmax = 27.2°, θmin = 3.0°
Detector resolution: 8 pixels mm-1h = 87
ω scansk = 1314
12716 measured reflectionsl = 1932
2355 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041Only H-atom coordinates refined
wR(F2) = 0.065 w = 1/[σ2(Fo2) + (0.0196P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
2355 reflectionsΔρmax = 0.21 e Å3
322 parametersΔρmin = 0.23 e Å3
0 restraintsAbsolute structure: see text
Primary atom site location: structure-invariant direct methods
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C11.0102 (4)0.40032 (19)0.10916 (11)0.0164 (6)
C20.9035 (4)0.3887 (2)0.15773 (11)0.0172 (6)
H20.964 (4)0.420 (2)0.1908 (10)0.021*
C30.7124 (4)0.3332 (2)0.15938 (11)0.0182 (6)
H30.633 (4)0.325 (2)0.1913 (10)0.022*
C40.6291 (4)0.28918 (19)0.11242 (11)0.0167 (5)
C50.7332 (4)0.2983 (2)0.06407 (10)0.0177 (6)
H50.673 (4)0.2655 (19)0.0315 (10)0.021*
C60.9221 (4)0.3539 (2)0.06265 (11)0.0182 (6)
H60.991 (4)0.360 (2)0.0295 (10)0.022*
N10.4296 (3)0.22926 (16)0.11386 (9)0.0191 (5)
O10.3371 (3)0.22048 (15)0.15696 (7)0.0245 (5)
O20.3602 (3)0.18813 (15)0.07160 (7)0.0260 (5)
O31.1924 (3)0.45552 (14)0.10424 (7)0.0206 (4)
H3A1.233 (4)0.489 (2)0.1348 (10)0.025*
C70.5138 (4)0.6133 (2)0.17538 (10)0.0157 (6)
C80.6243 (4)0.6686 (2)0.21712 (11)0.0186 (6)
H80.564 (4)0.666 (2)0.2531 (11)0.022*
C90.8140 (4)0.7203 (2)0.20867 (11)0.0198 (6)
H90.884 (4)0.7571 (19)0.2360 (10)0.024*
C100.8989 (4)0.7203 (2)0.15761 (11)0.0191 (6)
C110.7922 (4)0.6704 (2)0.11505 (11)0.0208 (6)
H110.851 (4)0.674 (2)0.0800 (10)0.025*
C120.6013 (4)0.6190 (2)0.12368 (11)0.0196 (6)
H120.527 (4)0.586 (2)0.0954 (9)0.023*
N21.0953 (4)0.77729 (18)0.14847 (10)0.0262 (6)
O41.1652 (3)0.78165 (16)0.10213 (8)0.0344 (5)
O51.1863 (3)0.82166 (15)0.18709 (9)0.0319 (5)
O60.3358 (2)0.56023 (14)0.18473 (6)0.0187 (4)
C130.2362 (4)0.48782 (19)0.39764 (10)0.0166 (6)
C140.4094 (4)0.4535 (2)0.36665 (10)0.0168 (6)
H140.525 (4)0.4144 (19)0.3818 (10)0.020*
C150.4117 (4)0.4743 (2)0.31302 (10)0.0180 (6)
H150.531 (4)0.454 (2)0.2914 (9)0.022*
C160.0836 (4)0.5595 (2)0.31613 (11)0.0187 (6)
H160.029 (4)0.598 (2)0.2977 (9)0.022*
C170.0701 (4)0.5419 (2)0.36979 (10)0.0177 (6)
H170.049 (4)0.5652 (19)0.3878 (10)0.021*
C180.0504 (5)0.5046 (3)0.48304 (12)0.0303 (7)
H18C0.011 (5)0.576 (2)0.4674 (11)0.036*
H18A0.096 (4)0.521 (2)0.5196 (11)0.036*
H18B0.053 (5)0.446 (2)0.4809 (11)0.036*
C190.3943 (5)0.4040 (3)0.47754 (12)0.0294 (7)
H19C0.531 (5)0.448 (2)0.4735 (11)0.035*
H19A0.413 (4)0.326 (2)0.4603 (11)0.035*
H19B0.354 (4)0.395 (2)0.5140 (11)0.035*
N30.2522 (3)0.52632 (18)0.28787 (9)0.0187 (5)
H3B0.265 (4)0.542 (2)0.2528 (10)0.022*
N40.2305 (3)0.46993 (19)0.45077 (8)0.0215 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0149 (13)0.0136 (12)0.0208 (14)0.0014 (10)0.0000 (12)0.0001 (12)
C20.0190 (14)0.0164 (13)0.0162 (14)0.0014 (11)0.0048 (13)0.0011 (12)
C30.0220 (15)0.0155 (12)0.0171 (14)0.0032 (12)0.0032 (13)0.0007 (12)
C40.0138 (13)0.0145 (11)0.0219 (14)0.0001 (10)0.0015 (12)0.0016 (12)
C50.0206 (15)0.0176 (14)0.0150 (14)0.0007 (11)0.0057 (12)0.0008 (12)
C60.0190 (15)0.0216 (14)0.0139 (14)0.0034 (12)0.0032 (12)0.0015 (12)
N10.0169 (11)0.0185 (10)0.0219 (12)0.0012 (9)0.0015 (11)0.0031 (11)
O10.0204 (11)0.0309 (10)0.0222 (10)0.0028 (9)0.0011 (9)0.0067 (9)
O20.0224 (11)0.0323 (11)0.0232 (10)0.0083 (9)0.0034 (9)0.0034 (9)
O30.0197 (9)0.0266 (10)0.0156 (10)0.0054 (8)0.0010 (8)0.0039 (9)
C70.0151 (13)0.0131 (12)0.0188 (14)0.0011 (11)0.0010 (11)0.0011 (11)
C80.0229 (15)0.0180 (13)0.0149 (13)0.0000 (12)0.0007 (12)0.0014 (12)
C90.0190 (14)0.0155 (13)0.0248 (16)0.0017 (12)0.0095 (13)0.0030 (12)
C100.0122 (13)0.0135 (12)0.0315 (16)0.0003 (11)0.0003 (13)0.0062 (13)
C110.0211 (14)0.0204 (13)0.0209 (15)0.0006 (11)0.0072 (13)0.0026 (13)
C120.0199 (15)0.0214 (13)0.0175 (14)0.0002 (12)0.0012 (13)0.0020 (12)
N20.0165 (12)0.0179 (11)0.0440 (16)0.0016 (10)0.0004 (12)0.0062 (12)
O40.0242 (11)0.0350 (11)0.0440 (14)0.0036 (9)0.0101 (11)0.0080 (11)
O50.0203 (11)0.0263 (10)0.0492 (13)0.0051 (9)0.0092 (11)0.0004 (10)
O60.0175 (10)0.0226 (9)0.0161 (9)0.0043 (8)0.0000 (8)0.0004 (8)
C130.0169 (13)0.0143 (11)0.0187 (15)0.0045 (10)0.0008 (11)0.0007 (11)
C140.0144 (13)0.0148 (13)0.0211 (14)0.0001 (11)0.0033 (11)0.0011 (11)
C150.0162 (14)0.0166 (12)0.0211 (15)0.0015 (11)0.0040 (12)0.0021 (12)
C160.0175 (14)0.0157 (12)0.0231 (15)0.0014 (12)0.0054 (13)0.0018 (12)
C170.0129 (13)0.0185 (13)0.0218 (15)0.0010 (11)0.0029 (11)0.0002 (12)
C180.0265 (18)0.046 (2)0.0181 (15)0.0041 (15)0.0026 (13)0.0004 (15)
C190.0325 (18)0.0341 (17)0.0215 (16)0.0044 (15)0.0047 (15)0.0024 (14)
N30.0220 (12)0.0195 (11)0.0146 (11)0.0021 (10)0.0017 (10)0.0028 (10)
N40.0188 (12)0.0294 (12)0.0165 (11)0.0014 (11)0.0012 (9)0.0017 (10)
Geometric parameters (Å, º) top
C1—O31.336 (3)C11—H110.95 (2)
C1—C61.397 (3)C12—H120.93 (2)
C1—C21.398 (3)N2—O51.236 (3)
C2—C31.384 (4)N2—O41.241 (3)
C2—H20.98 (2)C13—N41.342 (3)
C3—C41.383 (3)C13—C141.410 (3)
C3—H30.95 (2)C13—C171.416 (3)
C4—C51.383 (4)C14—C151.359 (3)
C4—N11.454 (3)C14—H140.94 (2)
C5—C61.371 (4)C15—N31.342 (3)
C5—H50.97 (2)C15—H150.96 (2)
C6—H60.94 (2)C16—N31.346 (3)
N1—O11.232 (3)C16—C171.356 (3)
N1—O21.238 (3)C16—H160.97 (3)
O3—H3A0.89 (2)C17—H170.93 (2)
C7—O61.316 (3)C18—N41.464 (4)
C7—C121.408 (4)C18—H18C0.99 (3)
C7—C81.411 (3)C18—H18A0.98 (3)
C8—C91.371 (4)C18—H18B0.95 (3)
C8—H80.98 (3)C19—N41.458 (4)
C9—C101.385 (4)C19—H19C1.02 (3)
C9—H90.92 (2)C19—H19A1.01 (3)
C10—C111.388 (4)C19—H19B0.95 (3)
C10—N21.439 (3)N3—H3B0.90 (2)
C11—C121.377 (3)
O3—C1—C6117.4 (2)C11—C12—H12120.8 (15)
O3—C1—C2123.6 (2)C7—C12—H12118.0 (15)
C6—C1—C2119.0 (2)O5—N2—O4122.6 (2)
C3—C2—C1120.3 (2)O5—N2—C10118.6 (2)
C3—C2—H2119.7 (15)O4—N2—C10118.8 (2)
C1—C2—H2120.0 (15)N4—C13—C14121.3 (2)
C4—C3—C2119.1 (2)N4—C13—C17122.1 (2)
C4—C3—H3117.8 (16)C14—C13—C17116.6 (2)
C2—C3—H3123.1 (16)C15—C14—C13119.9 (2)
C5—C4—C3121.6 (2)C15—C14—H14118.0 (15)
C5—C4—N1118.9 (2)C13—C14—H14122.1 (15)
C3—C4—N1119.5 (2)N3—C15—C14122.0 (2)
C6—C5—C4119.0 (2)N3—C15—H15116.9 (14)
C6—C5—H5120.5 (15)C14—C15—H15121.1 (14)
C4—C5—H5120.5 (15)N3—C16—C17121.7 (2)
C5—C6—C1121.0 (2)N3—C16—H16118.9 (15)
C5—C6—H6118.1 (16)C17—C16—H16119.3 (15)
C1—C6—H6120.9 (16)C16—C17—C13120.1 (2)
O1—N1—O2122.6 (2)C16—C17—H17119.3 (15)
O1—N1—C4119.0 (2)C13—C17—H17120.6 (15)
O2—N1—C4118.5 (2)N4—C18—H18C109.0 (17)
C1—O3—H3A112.3 (17)N4—C18—H18A109.2 (16)
O6—C7—C12122.0 (2)H18C—C18—H18A109 (2)
O6—C7—C8121.0 (2)N4—C18—H18B109.3 (17)
C12—C7—C8117.0 (2)H18C—C18—H18B106 (2)
C9—C8—C7121.9 (2)H18A—C18—H18B114 (2)
C9—C8—H8120.2 (15)N4—C19—H19C108.6 (15)
C7—C8—H8117.9 (15)N4—C19—H19A110.8 (16)
C8—C9—C10119.4 (2)H19C—C19—H19A107 (2)
C8—C9—H9121.4 (16)N4—C19—H19B107.7 (17)
C10—C9—H9119.2 (16)H19C—C19—H19B113 (2)
C9—C10—C11120.6 (2)H19A—C19—H19B110 (2)
C9—C10—N2119.3 (2)C15—N3—C16119.7 (2)
C11—C10—N2120.0 (2)C15—N3—H3B118.3 (16)
C12—C11—C10119.8 (3)C16—N3—H3B121.9 (16)
C12—C11—H11121.0 (16)C13—N4—C19120.8 (2)
C10—C11—H11119.2 (16)C13—N4—C18121.5 (2)
C11—C12—C7121.2 (3)C19—N4—C18117.3 (2)
O3—C1—C2—C3178.1 (2)N2—C10—C11—C12178.1 (2)
C6—C1—C2—C30.7 (3)C10—C11—C12—C71.6 (4)
C1—C2—C3—C40.1 (4)O6—C7—C12—C11177.1 (2)
C2—C3—C4—C50.7 (4)C8—C7—C12—C113.7 (4)
C2—C3—C4—N1179.2 (2)C9—C10—N2—O52.2 (3)
C3—C4—C5—C61.0 (4)C11—C10—N2—O5179.5 (2)
N1—C4—C5—C6179.5 (2)C9—C10—N2—O4176.6 (2)
C4—C5—C6—C10.4 (4)C11—C10—N2—O40.7 (3)
O3—C1—C6—C5178.5 (2)N4—C13—C14—C15179.1 (2)
C2—C1—C6—C50.4 (4)C17—C13—C14—C150.8 (4)
C5—C4—N1—O1179.6 (2)C13—C14—C15—N30.5 (4)
C3—C4—N1—O11.1 (3)N3—C16—C17—C130.2 (4)
C5—C4—N1—O20.2 (3)N4—C13—C17—C16179.2 (2)
C3—C4—N1—O2178.3 (2)C14—C13—C17—C160.7 (4)
O6—C7—C8—C9177.3 (2)C14—C15—N3—C160.0 (4)
C12—C7—C8—C93.5 (4)C17—C16—N3—C150.1 (4)
C7—C8—C9—C101.1 (4)C14—C13—N4—C196.1 (4)
C8—C9—C10—C111.1 (4)C17—C13—N4—C19174.0 (2)
C8—C9—C10—N2178.3 (2)C14—C13—N4—C18179.5 (2)
C9—C10—C11—C120.9 (4)C17—C13—N4—C180.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O10.95 (2)2.40 (2)2.735 (3)100.1 (17)
C5—H5···O20.97 (2)2.42 (2)2.715 (3)97.2 (16)
C8—H8···N30.98 (3)2.71 (2)3.391 (3)126.9 (18)
C9—H9···O50.92 (2)2.41 (3)2.712 (3)99.3 (18)
C11—H11···O40.95 (2)2.43 (2)2.733 (3)98.2 (17)
N3—H3B···O60.90 (2)1.77 (3)2.657 (3)169 (2)
C2—H2···O6i0.98 (2)2.88 (2)3.470 (3)119.2 (17)
O3—H3A···O6i0.89 (2)1.63 (3)2.516 (2)171 (3)
C6—H6···O2ii0.94 (2)2.71 (2)3.407 (3)131 (2)
C5—H5···O2ii0.97 (2)2.89 (2)3.484 (3)120.5 (18)
C8—H8···O1iii0.98 (3)2.41 (3)3.206 (3)138.0 (19)
C12—H12···O3iv0.93 (2)2.63 (2)3.265 (3)126.0 (18)
C14—H14···O4v0.94 (2)2.54 (2)3.459 (3)164 (2)
C14—H14···O5v0.94 (2)2.74 (2)3.291 (3)117.6 (18)
C15—H15···O5v0.96 (2)2.43 (2)3.120 (3)128.3 (18)
C14—H14···N2v0.94 (2)3.00 (2)3.788 (3)141.8 (18)
C17—H17···O1vi0.93 (2)2.80 (2)3.390 (3)122.3 (18)
C17—H17···O2vi0.93 (2)2.65 (2)3.548 (3)164.1 (19)
C18—H18C···O2vi0.99 (3)2.76 (3)3.641 (4)148 (2)
C16—H16···O1vi0.97 (3)2.68 (2)3.342 (3)126.5 (18)
C19—H19B···O3vii0.95 (3)2.85 (3)3.593 (4)136 (2)
C19—H19B···O4vii0.95 (3)2.99 (3)3.790 (4)142 (2)
C18—H18A···O3vii0.98 (3)2.52 (3)3.475 (4)164 (2)
C18—H18B···O4viii0.95 (3)2.90 (3)3.607 (4)133 (2)
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, y+1/2, z; (iii) x+1, y+1/2, z+1/2; (iv) x1, y, z; (v) x+2, y1/2, z+1/2; (vi) x, y+1/2, z+1/2; (vii) x+3/2, y+1, z+1/2; (viii) x+1, y1/2, z+1/2.
 

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