4,4′,4′′-(1,3,5-Triazine-2,4,6-tri­yl)tripyridinium trinitrate

Zhu, S.-R.; Chen, W.-D.; Zhao, H.-J.; Shao, M.; Li, M.-X.

doi:10.1107/S160053680604431X

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4,4′,4′′-(1,3,5-Triazine-2,4,6-triyl)tripyridinium trinitrate

S.-R. Zhu, W.-D. Chen, H.-J. Zhao, M. Shao and M.-X. Li

Reaction of 2,4,6-tris(4-pyridyl)-1,3,5-triazine (tpt) with excess nitric acid in an aqueous solution affords the title compound, C₁₈H₁₅N₆³⁺·3NO₃⁻. The torsion angles between adjacent aromatic rings are much larger than those of neutral tpt. All three pyridine N atoms are protonated.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680604431X/ac2048sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680604431X/ac2048Isup2.hkl Contains datablock I

CCDC reference: 640236

checkCIF report

Key indicators

Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.003 Å
R factor = 0.033
wR factor = 0.082
Data-to-parameter ratio = 6.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.80
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N7
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N8
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N9

Alert level G
REFLT03_ALERT_4_G 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.
           From the CIF: _diffrn_reflns_theta_max           27.50
           From the CIF: _reflns_number_total               2300
           Count of symmetry unique reflns         2312
           Completeness (_total/calc)             99.48%
           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

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

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

Computing details top

Data collection: APEX2 (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.

4,4',4''-(1,3,5-Triazine-2,4,6-triyl)tripyridinium trinitrate top

Crystal data top

C₁₈H₁₅N₆³⁺·3NO₃⁻	F(000) = 1032
M_r = 501.39	D_x = 1.657 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 9.8940 (12) Å	Cell parameters from 2778 reflections
b = 21.637 (3) Å	θ = 2.4–27.1°
c = 9.9734 (12) Å	µ = 0.14 mm⁻¹
β = 109.671 (1)°	T = 273 K
V = 2010.4 (4) Å³	Rhomb, pale_brown
Z = 4	0.40 × 0.20 × 0.20 mm

Data collection top

Bruker APEX-II area-detector diffractometer	2300 independent reflections
Radiation source: fine-focus sealed tube	2078 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→12
T_min = 0.948, T_max = 0.973	k = −28→27
6240 measured reflections	l = −12→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.082	w = 1/[σ²(F_o²) + (0.0501P)² + 0.2046P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2300 reflections	Δρ_max = 0.21 e Å⁻³
338 parameters	Δρ_min = −0.21 e Å⁻³
2 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0040 (6)

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

	x	y	z	U_iso*/U_eq
C1	0.7969 (2)	0.76683 (10)	0.0970 (2)	0.0245 (5)
C2	0.7684 (2)	0.86961 (10)	0.0974 (2)	0.0244 (5)
C3	0.8598 (2)	0.81840 (10)	0.3040 (2)	0.0240 (5)
C4	0.9157 (3)	0.81854 (10)	0.4621 (2)	0.0243 (5)
C5	0.9556 (3)	0.87405 (10)	0.5364 (2)	0.0287 (5)
H5	0.9484	0.9112	0.4876	0.034*
C6	1.0056 (3)	0.87302 (13)	0.6829 (3)	0.0357 (6)
H6	1.0329	0.9095	0.7342	0.043*
C7	0.9785 (3)	0.76513 (12)	0.6828 (3)	0.0361 (6)
H7	0.9869	0.7288	0.7347	0.043*
C8	0.9289 (3)	0.76342 (11)	0.5362 (3)	0.0314 (5)
H8	0.9047	0.7261	0.4880	0.038*
C9	0.7775 (2)	0.70777 (10)	0.0144 (2)	0.0236 (5)
C10	0.7965 (3)	0.65085 (10)	0.0827 (3)	0.0303 (5)
H10	0.8307	0.6484	0.1816	0.036*
C11	0.7637 (3)	0.59791 (11)	0.0007 (3)	0.0358 (6)
H11	0.7726	0.5594	0.0441	0.043*
C12	0.7053 (3)	0.65594 (12)	−0.2084 (3)	0.0381 (6)
H12	0.6767	0.6568	−0.3073	0.046*
C13	0.7330 (3)	0.71033 (11)	−0.1331 (3)	0.0312 (5)
H13	0.7222	0.7481	−0.1800	0.037*
C14	0.7142 (3)	0.92783 (9)	0.0180 (2)	0.0259 (5)
C15	0.6278 (3)	0.92505 (11)	−0.1242 (3)	0.0341 (6)
H15	0.6087	0.8874	−0.1720	0.041*
C16	0.5708 (3)	0.97917 (13)	−0.1930 (3)	0.0403 (6)
H16	0.5123	0.9783	−0.2881	0.048*
C17	0.6828 (3)	1.03675 (11)	0.0123 (3)	0.0367 (6)
H17	0.6997	1.0751	0.0570	0.044*
C18	0.7437 (3)	0.98466 (10)	0.0863 (3)	0.0308 (5)
H18	0.8038	0.9873	0.1807	0.037*
H4A	1.048 (4)	0.8167 (18)	0.841 (5)	0.071 (12)*
H5A	0.696 (4)	0.5691 (17)	−0.204 (4)	0.062 (10)*
H6A	0.558 (4)	1.0645 (15)	−0.179 (3)	0.047 (9)*
N1	0.8492 (2)	0.76378 (8)	0.2383 (2)	0.0264 (4)
N2	0.7533 (2)	0.81794 (8)	0.0208 (2)	0.0266 (4)
N3	0.8226 (2)	0.87272 (8)	0.23940 (19)	0.0263 (4)
N4	1.0145 (3)	0.81930 (11)	0.7506 (2)	0.0386 (5)
N5	0.7191 (3)	0.60213 (10)	−0.1409 (3)	0.0381 (5)
N6	0.5996 (3)	1.03253 (10)	−0.1234 (3)	0.0387 (5)
N7	0.3805 (2)	0.91123 (9)	0.0212 (2)	0.0331 (5)
N8	0.6079 (2)	0.80094 (9)	0.5292 (2)	0.0297 (4)
N9	0.0472 (3)	0.04132 (9)	0.5145 (2)	0.0331 (4)
O1	0.3186 (3)	0.87619 (10)	−0.0780 (2)	0.0583 (6)
O2	0.3768 (2)	0.96804 (9)	0.0031 (2)	0.0492 (5)
O3	0.4505 (3)	0.88892 (9)	0.1404 (2)	0.0573 (6)
O4	0.5819 (3)	0.83154 (9)	0.4186 (2)	0.0490 (6)
O5	0.6594 (3)	0.82693 (8)	0.6469 (2)	0.0498 (6)
O6	0.5829 (2)	0.74439 (8)	0.5232 (2)	0.0428 (5)
O7	0.0043 (3)	0.00839 (9)	0.4068 (2)	0.0511 (6)
O8	0.0252 (3)	0.09767 (8)	0.5067 (2)	0.0505 (5)
O9	0.1116 (3)	0.01682 (9)	0.6336 (2)	0.0508 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0300 (11)	0.0189 (10)	0.0229 (11)	0.0003 (9)	0.0066 (9)	−0.0023 (9)
C2	0.0303 (12)	0.0190 (10)	0.0222 (11)	0.0022 (9)	0.0068 (9)	0.0011 (8)
C3	0.0291 (12)	0.0204 (11)	0.0214 (11)	−0.0009 (9)	0.0071 (9)	0.0002 (8)
C4	0.0272 (11)	0.0237 (11)	0.0190 (11)	0.0024 (9)	0.0037 (9)	0.0011 (9)
C5	0.0344 (13)	0.0249 (11)	0.0230 (12)	0.0003 (10)	0.0047 (10)	−0.0002 (9)
C6	0.0415 (14)	0.0370 (13)	0.0238 (12)	−0.0026 (11)	0.0045 (10)	−0.0059 (10)
C7	0.0450 (15)	0.0343 (13)	0.0260 (13)	0.0060 (12)	0.0080 (11)	0.0099 (10)
C8	0.0408 (14)	0.0244 (11)	0.0264 (13)	0.0002 (10)	0.0079 (11)	0.0015 (10)
C9	0.0280 (11)	0.0182 (10)	0.0222 (11)	0.0016 (8)	0.0053 (9)	−0.0021 (8)
C10	0.0364 (13)	0.0212 (11)	0.0307 (13)	0.0028 (10)	0.0080 (10)	0.0011 (10)
C11	0.0421 (14)	0.0189 (11)	0.0440 (16)	0.0038 (10)	0.0113 (12)	−0.0018 (10)
C12	0.0493 (16)	0.0324 (13)	0.0278 (14)	0.0005 (11)	0.0067 (12)	−0.0086 (10)
C13	0.0410 (13)	0.0236 (11)	0.0260 (13)	0.0011 (10)	0.0073 (10)	−0.0026 (9)
C14	0.0348 (12)	0.0210 (10)	0.0214 (11)	0.0029 (9)	0.0089 (9)	0.0021 (9)
C15	0.0470 (14)	0.0306 (12)	0.0224 (12)	0.0074 (11)	0.0088 (11)	0.0018 (9)
C16	0.0495 (16)	0.0433 (15)	0.0251 (14)	0.0124 (12)	0.0085 (12)	0.0126 (11)
C17	0.0429 (15)	0.0226 (11)	0.0465 (16)	0.0028 (10)	0.0174 (13)	0.0049 (11)
C18	0.0376 (13)	0.0214 (11)	0.0313 (14)	0.0009 (10)	0.0090 (11)	0.0003 (9)
N1	0.0367 (11)	0.0204 (9)	0.0187 (9)	0.0007 (8)	0.0047 (8)	0.0007 (7)
N2	0.0367 (11)	0.0193 (9)	0.0193 (10)	0.0007 (8)	0.0036 (8)	−0.0006 (7)
N3	0.0365 (11)	0.0207 (9)	0.0185 (10)	−0.0008 (8)	0.0049 (8)	0.0003 (7)
N4	0.0451 (13)	0.0503 (14)	0.0158 (10)	0.0010 (11)	0.0040 (9)	0.0009 (10)
N5	0.0437 (13)	0.0259 (11)	0.0412 (14)	−0.0013 (9)	0.0097 (10)	−0.0135 (10)
N6	0.0446 (13)	0.0279 (11)	0.0464 (15)	0.0130 (10)	0.0190 (11)	0.0182 (10)
N7	0.0388 (11)	0.0260 (10)	0.0328 (11)	−0.0023 (9)	0.0098 (9)	−0.0065 (9)
N8	0.0375 (11)	0.0252 (9)	0.0237 (10)	−0.0018 (9)	0.0069 (8)	−0.0034 (8)
N9	0.0453 (12)	0.0257 (9)	0.0277 (10)	−0.0055 (9)	0.0116 (9)	−0.0041 (9)
O1	0.0785 (16)	0.0408 (11)	0.0368 (12)	−0.0042 (11)	−0.0056 (11)	−0.0105 (9)
O2	0.0620 (13)	0.0272 (9)	0.0537 (14)	0.0045 (9)	0.0134 (10)	−0.0009 (9)
O3	0.0818 (17)	0.0391 (11)	0.0328 (12)	−0.0066 (11)	−0.0048 (11)	0.0016 (9)
O4	0.0817 (16)	0.0318 (10)	0.0225 (10)	−0.0141 (9)	0.0032 (9)	0.0024 (7)
O5	0.0841 (16)	0.0344 (10)	0.0239 (10)	−0.0056 (10)	0.0087 (10)	−0.0085 (8)
O6	0.0655 (14)	0.0240 (8)	0.0330 (10)	−0.0057 (9)	0.0087 (9)	−0.0004 (8)
O7	0.0789 (16)	0.0358 (10)	0.0295 (11)	−0.0085 (10)	0.0065 (10)	−0.0098 (8)
O8	0.0728 (15)	0.0285 (9)	0.0422 (11)	0.0018 (9)	0.0087 (10)	−0.0029 (9)
O9	0.0856 (16)	0.0334 (10)	0.0256 (10)	−0.0018 (10)	0.0083 (10)	−0.0008 (8)

Geometric parameters (Å, º) top

C1—N2	1.329 (3)	C12—C13	1.373 (3)
C1—N1	1.329 (3)	C12—H12	0.930
C1—C9	1.497 (3)	C13—H13	0.930
C2—N2	1.334 (3)	C14—C18	1.388 (3)
C2—N3	1.336 (3)	C14—C15	1.390 (3)
C2—C14	1.488 (3)	C15—C16	1.378 (3)
C3—N3	1.331 (3)	C15—H15	0.930
C3—N1	1.338 (3)	C16—N6	1.328 (4)
C3—C4	1.485 (3)	C16—H16	0.930
C4—C8	1.386 (3)	C17—N6	1.329 (4)
C4—C5	1.397 (3)	C17—C18	1.371 (3)
C5—C6	1.376 (3)	C17—H17	0.930
C5—H5	0.930	C18—H18	0.930
C6—N4	1.332 (4)	N4—H4A	0.85 (4)
C6—H6	0.930	N5—H5A	0.93 (4)
C7—N4	1.340 (4)	N6—H6A	0.90 (3)
C7—C8	1.377 (4)	N7—O1	1.233 (3)
C7—H7	0.930	N7—O2	1.241 (3)
C8—H8	0.930	N7—O3	1.254 (3)
C9—C13	1.387 (3)	N8—O4	1.237 (3)
C9—C10	1.389 (3)	N8—O5	1.246 (3)
C10—C11	1.381 (3)	N8—O6	1.245 (2)
C10—H10	0.930	N9—O8	1.236 (3)
C11—N5	1.333 (4)	N9—O7	1.239 (3)
C11—H11	0.930	N9—O9	1.260 (3)
C12—N5	1.328 (3)

N2—C1—N1	125.68 (19)	C9—C13—H13	120.7
N2—C1—C9	116.02 (19)	C18—C14—C15	119.7 (2)
N1—C1—C9	118.22 (19)	C18—C14—C2	120.7 (2)
N2—C2—N3	125.23 (19)	C15—C14—C2	119.6 (2)
N2—C2—C14	116.98 (19)	C16—C15—C14	118.6 (2)
N3—C2—C14	117.73 (18)	C16—C15—H15	120.7
N3—C3—N1	125.4 (2)	C14—C15—H15	120.7
N3—C3—C4	117.09 (19)	N6—C16—C15	119.9 (3)
N1—C3—C4	117.5 (2)	N6—C16—H16	120.0
C8—C4—C5	119.8 (2)	C15—C16—H16	120.0
C8—C4—C3	120.0 (2)	N6—C17—C18	120.1 (2)
C5—C4—C3	120.2 (2)	N6—C17—H17	120.0
C6—C5—C4	119.1 (2)	C18—C17—H17	120.0
C6—C5—H5	120.5	C17—C18—C14	118.8 (2)
C4—C5—H5	120.5	C17—C18—H18	120.6
N4—C6—C5	119.4 (2)	C14—C18—H18	120.6
N4—C6—H6	120.3	C1—N1—C3	114.44 (18)
C5—C6—H6	120.3	C1—N2—C2	114.68 (19)
N4—C7—C8	119.9 (2)	C3—N3—C2	114.53 (18)
N4—C7—H7	120.1	C6—N4—C7	123.2 (2)
C8—C7—H7	120.1	C6—N4—H4A	122 (3)
C7—C8—C4	118.6 (2)	C7—N4—H4A	115 (3)
C7—C8—H8	120.7	C12—N5—C11	122.5 (2)
C4—C8—H8	120.7	C12—N5—H5A	112 (2)
C13—C9—C10	119.8 (2)	C11—N5—H5A	126 (2)
C13—C9—C1	119.0 (2)	C16—N6—C17	122.9 (2)
C10—C9—C1	121.1 (2)	C16—N6—H6A	112 (2)
C11—C10—C9	118.6 (2)	C17—N6—H6A	125 (2)
C11—C10—H10	120.7	O1—N7—O2	120.7 (2)
C9—C10—H10	120.7	O1—N7—O3	119.4 (2)
N5—C11—C10	119.9 (2)	O2—N7—O3	119.9 (2)
N5—C11—H11	120.1	O4—N8—O5	119.7 (2)
C10—C11—H11	120.1	O4—N8—O6	120.3 (2)
N5—C12—C13	120.4 (2)	O5—N8—O6	120.0 (2)
N5—C12—H12	119.8	O8—N9—O7	120.7 (2)
C13—C12—H12	119.8	O8—N9—O9	119.8 (2)
C12—C13—C9	118.7 (2)	O7—N9—O9	119.5 (2)
C12—C13—H13	120.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···O4ⁱ	0.90 (3)	2.43 (3)	2.984 (3)	120 (3)
N5—H5A···O9ⁱⁱ	0.93 (4)	1.92 (4)	2.826 (3)	165 (3)
N4—H4A···O8ⁱⁱⁱ	0.85 (4)	2.54 (4)	3.095 (3)	124 (3)
N4—H4A···O6^iv	0.85 (4)	2.18 (4)	2.917 (3)	145 (4)

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

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