4-[3-(4-Pyrid­yl)prop­yl]pyridinium trihydrogen pyromellitate

The title salt, C₁₃H₁₅N₂⁺·C₁₀H₅O₈⁻, manifests hydrogen-bonded one-dimensional chains parallel to the crystallographic b-axis direction, consisting of alternating monoprotonated 1,3-di-4-pyridylpropane mol­ecules and singly deprotonated pyromellitic acid anions. The chains inter­act via C—H...O hydrogen bonds to form two-dimensional layers parallel to the bc plane, which in turn stack to establish the three-dimensional crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.049
• wR factor = 0.141
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.772     0.970
            Tmin(prime) and Tmax expected:      0.948     0.966
            RR(prime) =      0.811
            Please check that your absorption correction is appropriate.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.81
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C17    -   C23    ...       1.53 Ang.

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Crystal Maker (Palmer, 2005); software used to prepare material for publication: SHELXL97.

4-[3-(4-Pyridyl)propyl]pyridinium trihydrogen pyromellitate

Crystal data

C13H15N2^+·C10H5O8^−	F(000) = 944
Mr = 452.41	Dx = 1.493 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 20817 reflections
a = 4.3743 (7) Å	θ = 2.1–28.3°
b = 39.127 (6) Å	µ = 0.11 mm^−1
c = 11.897 (2) Å	T = 173 K
β = 98.609 (3)°	Block, yellow
V = 2013.3 (5) Å^3	0.46 × 0.32 × 0.30 mm
Z = 4

Data collection

Bruker SMART 1K diffractometer	4818 independent reflections
Radiation source: fine-focus sealed tube	2944 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
Tmin = 0.772, Tmax = 0.970	k = −52→52
20817 measured reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.065P)^2 + 0.3571P] where P = (Fo^2 + 2Fc^2)/3
4818 reflections	(Δ/σ)max < 0.001
304 parameters	Δρmax = 0.47 e Å^−3
0 restraints	Δρmin = −0.49 e Å^−3

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	0.3725 (5)	0.27583 (5)	0.02835 (19)	0.0301 (5)
H1A	0.4282	0.2699	−0.0434	0.036*
C2	0.1815 (5)	0.30346 (5)	0.03708 (18)	0.0288 (5)
H2	0.1057	0.3165	−0.0286	0.035*
C3	0.1000 (4)	0.31222 (5)	0.14157 (17)	0.0241 (4)
C4	0.2106 (5)	0.29200 (5)	0.23499 (18)	0.0285 (5)
H4A	0.1550	0.2970	0.3074	0.034*
C5	0.4014 (5)	0.26468 (5)	0.22205 (18)	0.0303 (5)
H5	0.4781	0.2510	0.2859	0.036*
C6	−0.0816 (5)	0.34379 (5)	0.15710 (19)	0.0274 (5)
H6A	−0.2191	0.3396	0.2147	0.033*
H6B	−0.2119	0.3499	0.0845	0.033*
C7	0.1414 (4)	0.37327 (4)	0.19605 (17)	0.0231 (4)
H7A	0.2821	0.3663	0.2653	0.028*
H7B	0.2688	0.3783	0.1359	0.028*
C8	−0.0333 (5)	0.40558 (5)	0.22141 (18)	0.0259 (4)
H8A	−0.1792	0.4122	0.1531	0.031*
H8B	−0.1545	0.4009	0.2837	0.031*
C9	0.1877 (4)	0.43416 (5)	0.25501 (17)	0.0232 (4)
C10	0.3241 (5)	0.43892 (5)	0.36719 (18)	0.0284 (5)
H10	0.2730	0.4241	0.4248	0.034*
C11	0.5325 (5)	0.46499 (5)	0.39533 (18)	0.0303 (5)
H11	0.6237	0.4683	0.4722	0.036*
C12	0.4859 (5)	0.48164 (5)	0.20454 (18)	0.0274 (5)
H12	0.5448	0.4966	0.1486	0.033*
C13	0.2774 (5)	0.45587 (5)	0.17292 (18)	0.0271 (4)
H13	0.1943	0.4528	0.0951	0.033*
C14	0.2462 (4)	0.14159 (5)	0.10372 (16)	0.0242 (4)
C15	0.0937 (5)	0.15626 (5)	0.18872 (17)	0.0242 (4)
C16	0.0593 (5)	0.13634 (5)	0.28250 (17)	0.0254 (4)
H16	−0.0434	0.1463	0.3394	0.030*
C17	0.1642 (4)	0.10295 (5)	0.29929 (16)	0.0241 (4)
C18	0.3172 (4)	0.08817 (5)	0.21479 (16)	0.0237 (4)
C19	0.3505 (5)	0.10808 (5)	0.12051 (16)	0.0250 (4)
H19	0.4519	0.0981	0.0634	0.030*
C20	0.4634 (5)	0.05296 (5)	0.21640 (18)	0.0269 (5)
C21	0.3257 (5)	0.15754 (5)	−0.00473 (17)	0.0289 (5)
C22	−0.0525 (5)	0.19153 (5)	0.19017 (19)	0.0300 (5)
C23	0.0884 (5)	0.08726 (5)	0.40946 (17)	0.0291 (5)
N1	0.4795 (4)	0.25735 (4)	0.12010 (15)	0.0287 (4)
N2	0.6064 (4)	0.48573 (4)	0.31388 (15)	0.0274 (4)
H2N	0.744 (6)	0.5039 (6)	0.3330 (19)	0.041*
O1	0.1975 (4)	0.18638 (4)	−0.04229 (13)	0.0391 (4)
H1	0.0665	0.1923	−0.0011	0.059*
O2	0.5104 (4)	0.14344 (4)	−0.05626 (13)	0.0429 (4)
O3	−0.1051 (5)	0.20327 (4)	0.28074 (14)	0.0508 (5)
O4	−0.1236 (4)	0.20711 (4)	0.09496 (13)	0.0376 (4)
H4	−0.2354	0.2241	0.1038	0.056*
O5	−0.0933 (4)	0.10178 (4)	0.46125 (13)	0.0429 (4)
O6	0.2178 (4)	0.05863 (4)	0.44683 (13)	0.0369 (4)
H6	0.3283	0.0513	0.4001	0.055*
O7	0.5271 (4)	0.03713 (4)	0.30926 (13)	0.0383 (4)
O8	0.5271 (4)	0.04109 (4)	0.12517 (12)	0.0381 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0317 (11)	0.0274 (11)	0.0318 (12)	0.0005 (9)	0.0067 (9)	−0.0037 (9)
C2	0.0310 (11)	0.0256 (11)	0.0293 (12)	−0.0001 (9)	0.0023 (9)	0.0015 (9)
C3	0.0195 (9)	0.0198 (10)	0.0320 (12)	−0.0031 (8)	0.0004 (8)	−0.0019 (8)
C4	0.0311 (11)	0.0264 (11)	0.0279 (12)	−0.0008 (9)	0.0040 (9)	−0.0014 (9)
C5	0.0348 (12)	0.0248 (11)	0.0294 (12)	0.0009 (9)	−0.0012 (9)	0.0039 (9)
C6	0.0225 (10)	0.0216 (10)	0.0379 (12)	−0.0002 (8)	0.0033 (9)	−0.0031 (9)
C7	0.0208 (9)	0.0184 (10)	0.0310 (11)	0.0000 (8)	0.0066 (8)	−0.0005 (8)
C8	0.0235 (10)	0.0188 (10)	0.0362 (12)	−0.0003 (8)	0.0074 (9)	−0.0023 (8)
C9	0.0203 (9)	0.0178 (9)	0.0324 (12)	0.0026 (7)	0.0070 (8)	−0.0019 (8)
C10	0.0331 (11)	0.0253 (11)	0.0281 (11)	−0.0005 (9)	0.0087 (9)	0.0017 (9)
C11	0.0344 (12)	0.0284 (11)	0.0281 (12)	−0.0016 (9)	0.0049 (9)	−0.0029 (9)
C12	0.0295 (11)	0.0225 (10)	0.0294 (12)	−0.0019 (8)	0.0016 (9)	0.0038 (8)
C13	0.0294 (11)	0.0234 (10)	0.0277 (11)	−0.0007 (8)	0.0015 (9)	0.0001 (8)
C14	0.0266 (10)	0.0232 (10)	0.0221 (10)	0.0017 (8)	0.0013 (8)	−0.0011 (8)
C15	0.0267 (10)	0.0204 (10)	0.0247 (11)	0.0029 (8)	0.0010 (8)	−0.0018 (8)
C16	0.0263 (10)	0.0254 (10)	0.0245 (11)	0.0042 (8)	0.0041 (8)	−0.0021 (8)
C17	0.0261 (10)	0.0235 (10)	0.0218 (10)	−0.0002 (8)	0.0004 (8)	−0.0010 (8)
C18	0.0242 (10)	0.0212 (10)	0.0240 (11)	0.0024 (8)	−0.0016 (8)	−0.0010 (8)
C19	0.0280 (10)	0.0246 (10)	0.0219 (11)	0.0038 (8)	0.0027 (8)	−0.0027 (8)
C20	0.0284 (11)	0.0211 (10)	0.0292 (12)	0.0028 (8)	−0.0015 (9)	−0.0019 (9)
C21	0.0345 (12)	0.0265 (11)	0.0254 (11)	0.0021 (9)	0.0035 (9)	−0.0005 (9)
C22	0.0336 (12)	0.0219 (11)	0.0342 (13)	0.0044 (9)	0.0045 (10)	−0.0014 (9)
C23	0.0342 (12)	0.0299 (12)	0.0224 (11)	−0.0010 (9)	0.0018 (9)	−0.0009 (9)
N1	0.0288 (9)	0.0217 (9)	0.0351 (11)	−0.0003 (7)	0.0029 (8)	−0.0007 (7)
N2	0.0262 (9)	0.0206 (9)	0.0348 (11)	−0.0017 (7)	0.0023 (8)	−0.0023 (7)
O1	0.0473 (10)	0.0371 (9)	0.0342 (9)	0.0115 (7)	0.0103 (7)	0.0120 (7)
O2	0.0601 (11)	0.0383 (9)	0.0343 (9)	0.0099 (8)	0.0199 (8)	0.0028 (7)
O3	0.0858 (14)	0.0323 (9)	0.0373 (10)	0.0226 (9)	0.0195 (9)	−0.0011 (7)
O4	0.0482 (10)	0.0274 (8)	0.0366 (9)	0.0168 (7)	0.0042 (7)	0.0028 (7)
O5	0.0592 (11)	0.0402 (9)	0.0334 (9)	0.0065 (8)	0.0206 (8)	0.0033 (7)
O6	0.0459 (10)	0.0347 (9)	0.0302 (9)	0.0059 (7)	0.0064 (7)	0.0085 (7)
O7	0.0510 (10)	0.0293 (8)	0.0334 (9)	0.0150 (7)	0.0026 (7)	0.0065 (7)
O8	0.0537 (10)	0.0294 (8)	0.0301 (9)	0.0173 (7)	0.0021 (7)	−0.0046 (7)

Geometric parameters (Å, º)

C1—N1	1.334 (3)	C12—C13	1.374 (3)
C1—C2	1.380 (3)	C12—H12	0.9500
C1—H1A	0.9500	C13—H13	0.9500
C2—C3	1.387 (3)	C14—C19	1.393 (3)
C2—H2	0.9500	C14—C15	1.414 (3)
C3—C4	1.391 (3)	C14—C21	1.520 (3)
C3—C6	1.495 (3)	C15—C16	1.387 (3)
C4—C5	1.379 (3)	C15—C22	1.522 (3)
C4—H4A	0.9500	C16—C17	1.389 (3)
C5—N1	1.339 (3)	C16—H16	0.9500
C5—H5	0.9500	C17—C18	1.412 (3)
C6—C7	1.537 (3)	C17—C23	1.528 (3)
C6—H6A	0.9900	C18—C19	1.391 (3)
C6—H6B	0.9900	C18—C20	1.518 (3)
C7—C8	1.531 (3)	C19—H19	0.9500
C7—H7A	0.9900	C20—O8	1.250 (2)
C7—H7B	0.9900	C20—O7	1.261 (2)
C8—C9	1.493 (3)	C21—O2	1.217 (2)
C8—H8A	0.9900	C21—O1	1.309 (2)
C8—H8B	0.9900	C22—O3	1.225 (3)
C9—C10	1.390 (3)	C22—O4	1.283 (3)
C9—C13	1.394 (3)	C23—O5	1.217 (2)
C10—C11	1.376 (3)	C23—O6	1.303 (2)
C10—H10	0.9500	N2—H2N	0.94 (2)
C11—N2	1.340 (3)	O1—H1	0.8400
C11—H11	0.9500	O4—H4	0.8400
C12—N2	1.338 (3)	O6—H6	0.8400
N1—C1—C2	120.3 (2)	N2—C12—H12	119.9
N1—C1—H1A	119.8	C13—C12—H12	119.9
C2—C1—H1A	119.8	C12—C13—C9	120.01 (19)
C1—C2—C3	120.1 (2)	C12—C13—H13	120.0
C1—C2—H2	120.0	C9—C13—H13	120.0
C3—C2—H2	120.0	C19—C14—C15	117.33 (18)
C2—C3—C4	118.07 (18)	C19—C14—C21	113.38 (17)
C2—C3—C6	121.85 (18)	C15—C14—C21	129.26 (17)
C4—C3—C6	119.93 (19)	C16—C15—C14	117.82 (17)
C5—C4—C3	119.72 (19)	C16—C15—C22	113.82 (17)
C5—C4—H4A	120.1	C14—C15—C22	128.33 (18)
C3—C4—H4A	120.1	C15—C16—C17	124.80 (18)
N1—C5—C4	120.51 (19)	C15—C16—H16	117.6
N1—C5—H5	119.7	C17—C16—H16	117.6
C4—C5—H5	119.7	C16—C17—C18	117.65 (18)
C3—C6—C7	109.41 (15)	C16—C17—C23	113.07 (17)
C3—C6—H6A	109.8	C18—C17—C23	129.27 (18)
C7—C6—H6A	109.8	C19—C18—C17	117.57 (17)
C3—C6—H6B	109.8	C19—C18—C20	115.06 (17)
C7—C6—H6B	109.8	C17—C18—C20	127.32 (17)
H6A—C6—H6B	108.2	C18—C19—C14	124.83 (18)
C8—C7—C6	111.49 (15)	C18—C19—H19	117.6
C8—C7—H7A	109.3	C14—C19—H19	117.6
C6—C7—H7A	109.3	O8—C20—O7	121.98 (18)
C8—C7—H7B	109.3	O8—C20—C18	118.34 (18)
C6—C7—H7B	109.3	O7—C20—C18	119.63 (17)
H7A—C7—H7B	108.0	O2—C21—O1	120.11 (19)
C9—C8—C7	110.43 (16)	O2—C21—C14	119.67 (18)
C9—C8—H8A	109.6	O1—C21—C14	120.22 (18)
C7—C8—H8A	109.6	O3—C22—O4	123.10 (19)
C9—C8—H8B	109.6	O3—C22—C15	119.00 (19)
C7—C8—H8B	109.6	O4—C22—C15	117.87 (18)
H8A—C8—H8B	108.1	O5—C23—O6	120.80 (19)
C10—C9—C13	117.74 (18)	O5—C23—C17	119.26 (18)
C10—C9—C8	121.65 (18)	O6—C23—C17	119.94 (18)
C13—C9—C8	120.50 (18)	C1—N1—C5	121.27 (18)
C11—C10—C9	120.41 (19)	C12—N2—C11	121.90 (19)
C11—C10—H10	119.8	C12—N2—H2N	118.1 (14)
C9—C10—H10	119.8	C11—N2—H2N	120.0 (14)
N2—C11—C10	119.7 (2)	C21—O1—H1	109.5
N2—C11—H11	120.1	C22—O4—H4	109.5
C10—C11—H11	120.1	C23—O6—H6	109.5
N2—C12—C13	120.17 (19)
N1—C1—C2—C3	0.1 (3)	C23—C17—C18—C19	178.57 (19)
C1—C2—C3—C4	−1.4 (3)	C16—C17—C18—C20	177.14 (18)
C1—C2—C3—C6	174.17 (18)	C23—C17—C18—C20	−4.0 (3)
C2—C3—C4—C5	1.5 (3)	C17—C18—C19—C14	0.5 (3)
C6—C3—C4—C5	−174.12 (18)	C20—C18—C19—C14	−177.26 (18)
C3—C4—C5—N1	−0.4 (3)	C15—C14—C19—C18	−0.4 (3)
C2—C3—C6—C7	−93.1 (2)	C21—C14—C19—C18	177.70 (19)
C4—C3—C6—C7	82.3 (2)	C19—C18—C20—O8	−18.2 (3)
C3—C6—C7—C8	−175.93 (17)	C17—C18—C20—O8	164.24 (19)
C6—C7—C8—C9	−177.97 (17)	C19—C18—C20—O7	159.20 (19)
C7—C8—C9—C10	−87.2 (2)	C17—C18—C20—O7	−18.3 (3)
C7—C8—C9—C13	89.1 (2)	C19—C14—C21—O2	−12.5 (3)
C13—C9—C10—C11	2.1 (3)	C15—C14—C21—O2	165.3 (2)
C8—C9—C10—C11	178.46 (19)	C19—C14—C21—O1	167.87 (19)
C9—C10—C11—N2	−0.6 (3)	C15—C14—C21—O1	−14.3 (3)
N2—C12—C13—C9	0.8 (3)	C16—C15—C22—O3	20.4 (3)
C10—C9—C13—C12	−2.2 (3)	C14—C15—C22—O3	−161.9 (2)
C8—C9—C13—C12	−178.62 (18)	C16—C15—C22—O4	−157.46 (19)
C19—C14—C15—C16	0.1 (3)	C14—C15—C22—O4	20.3 (3)
C21—C14—C15—C16	−177.7 (2)	C16—C17—C23—O5	12.2 (3)
C19—C14—C15—C22	−177.56 (19)	C18—C17—C23—O5	−166.7 (2)
C21—C14—C15—C22	4.7 (3)	C16—C17—C23—O6	−167.82 (18)
C14—C15—C16—C17	0.1 (3)	C18—C17—C23—O6	13.2 (3)
C22—C15—C16—C17	178.06 (18)	C2—C1—N1—C5	1.1 (3)
C15—C16—C17—C18	0.1 (3)	C4—C5—N1—C1	−0.9 (3)
C15—C16—C17—C23	−179.02 (19)	C13—C12—N2—C11	0.8 (3)
C16—C17—C18—C19	−0.3 (3)	C10—C11—N2—C12	−0.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O8^i	0.94 (2)	1.79 (2)	2.728 (2)	174 (2)
O1—H1···O4	0.84	1.62	2.446 (2)	168
O4—H4···N1^ii	0.84	1.83	2.669 (2)	173
O6—H6···O7	0.84	1.58	2.425 (2)	178

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) x−1, y, z.