4-Di­methyl­amino­pyridinium–4-nitro­phenolate–4-nitro­phenol (1/1/1)

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.

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

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

Crystal data

C7H11N2^+·C6H4NO3^−·C6H5NO3	Dx = 1.444 Mg m^−3
Mr = 400.39	Melting point = 397–399 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 701 reflections
a = 6.4168 (16) Å	θ = 3.0–22.4°
b = 11.505 (3) Å	µ = 0.11 mm^−1
c = 24.943 (6) Å	T = 120 K
V = 1841.4 (8) Å^3	Block, yellow
Z = 4	0.20 × 0.15 × 0.11 mm
F(000) = 840

Data collection

Bruker Proteum M diffractometer	1940 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
Graphite monochromator	θmax = 27.2°, θmin = 3.0°
Detector resolution: 8 pixels mm^-1	h = −8→7
ω scans	k = −13→14
12716 measured reflections	l = −19→32
2355 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	Only H-atom coordinates refined
wR(F^2) = 0.065	w = 1/[σ^2(Fo^2) + (0.0196P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
2355 reflections	Δρmax = 0.21 e Å^−3
322 parameters	Δρmin = −0.23 e Å^−3
0 restraints	Absolute structure: see text
Primary atom site location: structure-invariant direct methods

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	1.0102 (4)	0.40032 (19)	0.10916 (11)	0.0164 (6)
C2	0.9035 (4)	0.3887 (2)	0.15773 (11)	0.0172 (6)
H2	0.964 (4)	0.420 (2)	0.1908 (10)	0.021*
C3	0.7124 (4)	0.3332 (2)	0.15938 (11)	0.0182 (6)
H3	0.633 (4)	0.325 (2)	0.1913 (10)	0.022*
C4	0.6291 (4)	0.28918 (19)	0.11242 (11)	0.0167 (5)
C5	0.7332 (4)	0.2983 (2)	0.06407 (10)	0.0177 (6)
H5	0.673 (4)	0.2655 (19)	0.0315 (10)	0.021*
C6	0.9221 (4)	0.3539 (2)	0.06265 (11)	0.0182 (6)
H6	0.991 (4)	0.360 (2)	0.0295 (10)	0.022*
N1	0.4296 (3)	0.22926 (16)	0.11386 (9)	0.0191 (5)
O1	0.3371 (3)	0.22048 (15)	0.15696 (7)	0.0245 (5)
O2	0.3602 (3)	0.18813 (15)	0.07160 (7)	0.0260 (5)
O3	1.1924 (3)	0.45552 (14)	0.10424 (7)	0.0206 (4)
H3A	1.233 (4)	0.489 (2)	0.1348 (10)	0.025*
C7	0.5138 (4)	0.6133 (2)	0.17538 (10)	0.0157 (6)
C8	0.6243 (4)	0.6686 (2)	0.21712 (11)	0.0186 (6)
H8	0.564 (4)	0.666 (2)	0.2531 (11)	0.022*
C9	0.8140 (4)	0.7203 (2)	0.20867 (11)	0.0198 (6)
H9	0.884 (4)	0.7571 (19)	0.2360 (10)	0.024*
C10	0.8989 (4)	0.7203 (2)	0.15761 (11)	0.0191 (6)
C11	0.7922 (4)	0.6704 (2)	0.11505 (11)	0.0208 (6)
H11	0.851 (4)	0.674 (2)	0.0800 (10)	0.025*
C12	0.6013 (4)	0.6190 (2)	0.12368 (11)	0.0196 (6)
H12	0.527 (4)	0.586 (2)	0.0954 (9)	0.023*
N2	1.0953 (4)	0.77729 (18)	0.14847 (10)	0.0262 (6)
O4	1.1652 (3)	0.78165 (16)	0.10213 (8)	0.0344 (5)
O5	1.1863 (3)	0.82166 (15)	0.18709 (9)	0.0319 (5)
O6	0.3358 (2)	0.56023 (14)	0.18473 (6)	0.0187 (4)
C13	0.2362 (4)	0.48782 (19)	0.39764 (10)	0.0166 (6)
C14	0.4094 (4)	0.4535 (2)	0.36665 (10)	0.0168 (6)
H14	0.525 (4)	0.4144 (19)	0.3818 (10)	0.020*
C15	0.4117 (4)	0.4743 (2)	0.31302 (10)	0.0180 (6)
H15	0.531 (4)	0.454 (2)	0.2914 (9)	0.022*
C16	0.0836 (4)	0.5595 (2)	0.31613 (11)	0.0187 (6)
H16	−0.029 (4)	0.598 (2)	0.2977 (9)	0.022*
C17	0.0701 (4)	0.5419 (2)	0.36979 (10)	0.0177 (6)
H17	−0.049 (4)	0.5652 (19)	0.3878 (10)	0.021*
C18	0.0504 (5)	0.5046 (3)	0.48304 (12)	0.0303 (7)
H18C	−0.011 (5)	0.576 (2)	0.4674 (11)	0.036*
H18A	0.096 (4)	0.521 (2)	0.5196 (11)	0.036*
H18B	−0.053 (5)	0.446 (2)	0.4809 (11)	0.036*
C19	0.3943 (5)	0.4040 (3)	0.47754 (12)	0.0294 (7)
H19C	0.531 (5)	0.448 (2)	0.4735 (11)	0.035*
H19A	0.413 (4)	0.326 (2)	0.4603 (11)	0.035*
H19B	0.354 (4)	0.395 (2)	0.5140 (11)	0.035*
N3	0.2522 (3)	0.52632 (18)	0.28787 (9)	0.0187 (5)
H3B	0.265 (4)	0.542 (2)	0.2528 (10)	0.022*
N4	0.2305 (3)	0.46993 (19)	0.45077 (8)	0.0215 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0149 (13)	0.0136 (12)	0.0208 (14)	0.0014 (10)	0.0000 (12)	−0.0001 (12)
C2	0.0190 (14)	0.0164 (13)	0.0162 (14)	0.0014 (11)	−0.0048 (13)	−0.0011 (12)
C3	0.0220 (15)	0.0155 (12)	0.0171 (14)	0.0032 (12)	0.0032 (13)	0.0007 (12)
C4	0.0138 (13)	0.0145 (11)	0.0219 (14)	0.0001 (10)	−0.0015 (12)	0.0016 (12)
C5	0.0206 (15)	0.0176 (14)	0.0150 (14)	0.0007 (11)	−0.0057 (12)	−0.0008 (12)
C6	0.0190 (15)	0.0216 (14)	0.0139 (14)	0.0034 (12)	0.0032 (12)	−0.0015 (12)
N1	0.0169 (11)	0.0185 (10)	0.0219 (12)	0.0012 (9)	−0.0015 (11)	0.0031 (11)
O1	0.0204 (11)	0.0309 (10)	0.0222 (10)	−0.0028 (9)	0.0011 (9)	0.0067 (9)
O2	0.0224 (11)	0.0323 (11)	0.0232 (10)	−0.0083 (9)	−0.0034 (9)	−0.0034 (9)
O3	0.0197 (9)	0.0266 (10)	0.0156 (10)	−0.0054 (8)	−0.0010 (8)	−0.0039 (9)
C7	0.0151 (13)	0.0131 (12)	0.0188 (14)	0.0011 (11)	0.0010 (11)	0.0011 (11)
C8	0.0229 (15)	0.0180 (13)	0.0149 (13)	0.0000 (12)	−0.0007 (12)	0.0014 (12)
C9	0.0190 (14)	0.0155 (13)	0.0248 (16)	−0.0017 (12)	−0.0095 (13)	0.0030 (12)
C10	0.0122 (13)	0.0135 (12)	0.0315 (16)	−0.0003 (11)	−0.0003 (13)	0.0062 (13)
C11	0.0211 (14)	0.0204 (13)	0.0209 (15)	0.0006 (11)	0.0072 (13)	0.0026 (13)
C12	0.0199 (15)	0.0214 (13)	0.0175 (14)	0.0002 (12)	−0.0012 (13)	−0.0020 (12)
N2	0.0165 (12)	0.0179 (11)	0.0440 (16)	0.0016 (10)	0.0004 (12)	0.0062 (12)
O4	0.0242 (11)	0.0350 (11)	0.0440 (14)	−0.0036 (9)	0.0101 (11)	0.0080 (11)
O5	0.0203 (11)	0.0263 (10)	0.0492 (13)	−0.0051 (9)	−0.0092 (11)	−0.0004 (10)
O6	0.0175 (10)	0.0226 (9)	0.0161 (9)	−0.0043 (8)	0.0000 (8)	−0.0004 (8)
C13	0.0169 (13)	0.0143 (11)	0.0187 (15)	−0.0045 (10)	−0.0008 (11)	−0.0007 (11)
C14	0.0144 (13)	0.0148 (13)	0.0211 (14)	−0.0001 (11)	−0.0033 (11)	0.0011 (11)
C15	0.0162 (14)	0.0166 (12)	0.0211 (15)	−0.0015 (11)	0.0040 (12)	−0.0021 (12)
C16	0.0175 (14)	0.0157 (12)	0.0231 (15)	−0.0014 (12)	−0.0054 (13)	0.0018 (12)
C17	0.0129 (13)	0.0185 (13)	0.0218 (15)	0.0010 (11)	0.0029 (11)	−0.0002 (12)
C18	0.0265 (18)	0.046 (2)	0.0181 (15)	0.0041 (15)	0.0026 (13)	−0.0004 (15)
C19	0.0325 (18)	0.0341 (17)	0.0215 (16)	0.0044 (15)	−0.0047 (15)	0.0024 (14)
N3	0.0220 (12)	0.0195 (11)	0.0146 (11)	−0.0021 (10)	0.0017 (10)	0.0028 (10)
N4	0.0188 (12)	0.0294 (12)	0.0165 (11)	0.0014 (11)	−0.0012 (9)	0.0017 (10)

Geometric parameters (Å, º)

C1—O3	1.336 (3)	C11—H11	0.95 (2)
C1—C6	1.397 (3)	C12—H12	0.93 (2)
C1—C2	1.398 (3)	N2—O5	1.236 (3)
C2—C3	1.384 (4)	N2—O4	1.241 (3)
C2—H2	0.98 (2)	C13—N4	1.342 (3)
C3—C4	1.383 (3)	C13—C14	1.410 (3)
C3—H3	0.95 (2)	C13—C17	1.416 (3)
C4—C5	1.383 (4)	C14—C15	1.359 (3)
C4—N1	1.454 (3)	C14—H14	0.94 (2)
C5—C6	1.371 (4)	C15—N3	1.342 (3)
C5—H5	0.97 (2)	C15—H15	0.96 (2)
C6—H6	0.94 (2)	C16—N3	1.346 (3)
N1—O1	1.232 (3)	C16—C17	1.356 (3)
N1—O2	1.238 (3)	C16—H16	0.97 (3)
O3—H3A	0.89 (2)	C17—H17	0.93 (2)
C7—O6	1.316 (3)	C18—N4	1.464 (4)
C7—C12	1.408 (4)	C18—H18C	0.99 (3)
C7—C8	1.411 (3)	C18—H18A	0.98 (3)
C8—C9	1.371 (4)	C18—H18B	0.95 (3)
C8—H8	0.98 (3)	C19—N4	1.458 (4)
C9—C10	1.385 (4)	C19—H19C	1.02 (3)
C9—H9	0.92 (2)	C19—H19A	1.01 (3)
C10—C11	1.388 (4)	C19—H19B	0.95 (3)
C10—N2	1.439 (3)	N3—H3B	0.90 (2)
C11—C12	1.377 (3)
O3—C1—C6	117.4 (2)	C11—C12—H12	120.8 (15)
O3—C1—C2	123.6 (2)	C7—C12—H12	118.0 (15)
C6—C1—C2	119.0 (2)	O5—N2—O4	122.6 (2)
C3—C2—C1	120.3 (2)	O5—N2—C10	118.6 (2)
C3—C2—H2	119.7 (15)	O4—N2—C10	118.8 (2)
C1—C2—H2	120.0 (15)	N4—C13—C14	121.3 (2)
C4—C3—C2	119.1 (2)	N4—C13—C17	122.1 (2)
C4—C3—H3	117.8 (16)	C14—C13—C17	116.6 (2)
C2—C3—H3	123.1 (16)	C15—C14—C13	119.9 (2)
C5—C4—C3	121.6 (2)	C15—C14—H14	118.0 (15)
C5—C4—N1	118.9 (2)	C13—C14—H14	122.1 (15)
C3—C4—N1	119.5 (2)	N3—C15—C14	122.0 (2)
C6—C5—C4	119.0 (2)	N3—C15—H15	116.9 (14)
C6—C5—H5	120.5 (15)	C14—C15—H15	121.1 (14)
C4—C5—H5	120.5 (15)	N3—C16—C17	121.7 (2)
C5—C6—C1	121.0 (2)	N3—C16—H16	118.9 (15)
C5—C6—H6	118.1 (16)	C17—C16—H16	119.3 (15)
C1—C6—H6	120.9 (16)	C16—C17—C13	120.1 (2)
O1—N1—O2	122.6 (2)	C16—C17—H17	119.3 (15)
O1—N1—C4	119.0 (2)	C13—C17—H17	120.6 (15)
O2—N1—C4	118.5 (2)	N4—C18—H18C	109.0 (17)
C1—O3—H3A	112.3 (17)	N4—C18—H18A	109.2 (16)
O6—C7—C12	122.0 (2)	H18C—C18—H18A	109 (2)
O6—C7—C8	121.0 (2)	N4—C18—H18B	109.3 (17)
C12—C7—C8	117.0 (2)	H18C—C18—H18B	106 (2)
C9—C8—C7	121.9 (2)	H18A—C18—H18B	114 (2)
C9—C8—H8	120.2 (15)	N4—C19—H19C	108.6 (15)
C7—C8—H8	117.9 (15)	N4—C19—H19A	110.8 (16)
C8—C9—C10	119.4 (2)	H19C—C19—H19A	107 (2)
C8—C9—H9	121.4 (16)	N4—C19—H19B	107.7 (17)
C10—C9—H9	119.2 (16)	H19C—C19—H19B	113 (2)
C9—C10—C11	120.6 (2)	H19A—C19—H19B	110 (2)
C9—C10—N2	119.3 (2)	C15—N3—C16	119.7 (2)
C11—C10—N2	120.0 (2)	C15—N3—H3B	118.3 (16)
C12—C11—C10	119.8 (3)	C16—N3—H3B	121.9 (16)
C12—C11—H11	121.0 (16)	C13—N4—C19	120.8 (2)
C10—C11—H11	119.2 (16)	C13—N4—C18	121.5 (2)
C11—C12—C7	121.2 (3)	C19—N4—C18	117.3 (2)
O3—C1—C2—C3	178.1 (2)	N2—C10—C11—C12	−178.1 (2)
C6—C1—C2—C3	−0.7 (3)	C10—C11—C12—C7	−1.6 (4)
C1—C2—C3—C4	0.1 (4)	O6—C7—C12—C11	−177.1 (2)
C2—C3—C4—C5	0.7 (4)	C8—C7—C12—C11	3.7 (4)
C2—C3—C4—N1	179.2 (2)	C9—C10—N2—O5	2.2 (3)
C3—C4—C5—C6	−1.0 (4)	C11—C10—N2—O5	179.5 (2)
N1—C4—C5—C6	−179.5 (2)	C9—C10—N2—O4	−176.6 (2)
C4—C5—C6—C1	0.4 (4)	C11—C10—N2—O4	0.7 (3)
O3—C1—C6—C5	−178.5 (2)	N4—C13—C14—C15	−179.1 (2)
C2—C1—C6—C5	0.4 (4)	C17—C13—C14—C15	0.8 (4)
C5—C4—N1—O1	179.6 (2)	C13—C14—C15—N3	−0.5 (4)
C3—C4—N1—O1	1.1 (3)	N3—C16—C17—C13	0.2 (4)
C5—C4—N1—O2	0.2 (3)	N4—C13—C17—C16	179.2 (2)
C3—C4—N1—O2	−178.3 (2)	C14—C13—C17—C16	−0.7 (4)
O6—C7—C8—C9	177.3 (2)	C14—C15—N3—C16	0.0 (4)
C12—C7—C8—C9	−3.5 (4)	C17—C16—N3—C15	0.1 (4)
C7—C8—C9—C10	1.1 (4)	C14—C13—N4—C19	−6.1 (4)
C8—C9—C10—C11	1.1 (4)	C17—C13—N4—C19	174.0 (2)
C8—C9—C10—N2	178.3 (2)	C14—C13—N4—C18	−179.5 (2)
C9—C10—C11—C12	−0.9 (4)	C17—C13—N4—C18	0.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1	0.95 (2)	2.40 (2)	2.735 (3)	100.1 (17)
C5—H5···O2	0.97 (2)	2.42 (2)	2.715 (3)	97.2 (16)
C8—H8···N3	0.98 (3)	2.71 (2)	3.391 (3)	126.9 (18)
C9—H9···O5	0.92 (2)	2.41 (3)	2.712 (3)	99.3 (18)
C11—H11···O4	0.95 (2)	2.43 (2)	2.733 (3)	98.2 (17)
N3—H3B···O6	0.90 (2)	1.77 (3)	2.657 (3)	169 (2)
C2—H2···O6^i	0.98 (2)	2.88 (2)	3.470 (3)	119.2 (17)
O3—H3A···O6^i	0.89 (2)	1.63 (3)	2.516 (2)	171 (3)
C6—H6···O2^ii	0.94 (2)	2.71 (2)	3.407 (3)	131 (2)
C5—H5···O2^ii	0.97 (2)	2.89 (2)	3.484 (3)	120.5 (18)
C8—H8···O1^iii	0.98 (3)	2.41 (3)	3.206 (3)	138.0 (19)
C12—H12···O3^iv	0.93 (2)	2.63 (2)	3.265 (3)	126.0 (18)
C14—H14···O4^v	0.94 (2)	2.54 (2)	3.459 (3)	164 (2)
C14—H14···O5^v	0.94 (2)	2.74 (2)	3.291 (3)	117.6 (18)
C15—H15···O5^v	0.96 (2)	2.43 (2)	3.120 (3)	128.3 (18)
C14—H14···N2^v	0.94 (2)	3.00 (2)	3.788 (3)	141.8 (18)
C17—H17···O1^vi	0.93 (2)	2.80 (2)	3.390 (3)	122.3 (18)
C17—H17···O2^vi	0.93 (2)	2.65 (2)	3.548 (3)	164.1 (19)
C18—H18C···O2^vi	0.99 (3)	2.76 (3)	3.641 (4)	148 (2)
C16—H16···O1^vi	0.97 (3)	2.68 (2)	3.342 (3)	126.5 (18)
C19—H19B···O3^vii	0.95 (3)	2.85 (3)	3.593 (4)	136 (2)
C19—H19B···O4^vii	0.95 (3)	2.99 (3)	3.790 (4)	142 (2)
C18—H18A···O3^vii	0.98 (3)	2.52 (3)	3.475 (4)	164 (2)
C18—H18B···O4^viii	0.95 (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) x−1, y, z; (v) −x+2, y−1/2, −z+1/2; (vi) −x, y+1/2, −z+1/2; (vii) −x+3/2, −y+1, z+1/2; (viii) −x+1, y−1/2, −z+1/2.