3-Phenyl­pyrazolium nitrate

The title compound, C₉H₉N₂⁺·NO₃⁻, is composed of discrete 3-phenyl­pyrazolium cations and nitrate anions. The crystal packing is stabilized by N—H...O and C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.082
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O1     ..  O1      ..       2.62 Ang.

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

   0 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
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 1990).

3-Phenylpyrazolium nitrate

Crystal data

C9H9N2^+·NO3^−	F(000) = 864
Mr = 207.19	Dx = 1.462 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5297 reflections
a = 16.8447 (16) Å	θ = 3.7–27.2°
b = 13.392 (2) Å	µ = 0.11 mm^−1
c = 8.3779 (8) Å	T = 100 K
β = 95.211 (8)°	Plate, colourless
V = 1882.2 (4) Å^3	0.22 × 0.16 × 0.12 mm
Z = 8

Data collection

Stoe IPDS-II two-circle diffractometer	1502 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.058
Graphite monochromator	θmax = 27.3°, θmin = 3.9°
ω scans	h = −21→21
8471 measured reflections	k = −14→17
2106 independent reflections	l = −10→10

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	w = 1/[σ^2(Fo^2) + (0.0427P)^2] where P = (Fo^2 + 2Fc^2)/3
2106 reflections	(Δ/σ)max < 0.001
144 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

Experimental. ;

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
N1	0.05985 (7)	0.33038 (9)	0.09262 (15)	0.0215 (3)
O1	0.03373 (6)	0.41499 (8)	0.04439 (15)	0.0307 (3)
O2	0.12049 (6)	0.32889 (8)	0.19301 (13)	0.0279 (3)
O3	0.02765 (6)	0.25275 (8)	0.04050 (15)	0.0296 (3)
C1	0.20509 (8)	0.58032 (11)	0.33199 (17)	0.0195 (3)
C2	0.19243 (8)	0.68312 (11)	0.31445 (18)	0.0218 (3)
H2	0.2252	0.7351	0.3612	0.026*
C3	0.12284 (8)	0.69398 (11)	0.21563 (18)	0.0225 (3)
H3	0.0987	0.7556	0.1824	0.027*
N4	0.09514 (7)	0.60337 (10)	0.17463 (16)	0.0226 (3)
H4	0.0523 (12)	0.5891 (16)	0.106 (2)	0.040 (5)*
N5	0.14466 (6)	0.53404 (9)	0.24530 (14)	0.0201 (3)
H5	0.1356 (10)	0.4681 (15)	0.225 (2)	0.028 (4)*
C11	0.26969 (8)	0.52521 (11)	0.42300 (16)	0.0194 (3)
C12	0.33958 (8)	0.57661 (11)	0.47614 (18)	0.0233 (3)
H12	0.3446	0.6456	0.4529	0.028*
C13	0.40151 (8)	0.52643 (13)	0.56284 (19)	0.0267 (3)
H13	0.4487	0.5615	0.5993	0.032*
C14	0.39499 (8)	0.42575 (12)	0.59653 (19)	0.0269 (3)
H14	0.4376	0.3919	0.6558	0.032*
C15	0.32599 (9)	0.37452 (12)	0.54338 (19)	0.0249 (3)
H15	0.3215	0.3054	0.5663	0.030*
C16	0.26333 (8)	0.42382 (11)	0.45666 (17)	0.0222 (3)
H16	0.2163	0.3883	0.4205	0.027*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0208 (5)	0.0164 (6)	0.0268 (6)	0.0004 (5)	−0.0010 (4)	0.0019 (5)
O1	0.0318 (5)	0.0167 (6)	0.0403 (7)	0.0021 (4)	−0.0136 (5)	0.0023 (5)
O2	0.0267 (5)	0.0221 (5)	0.0325 (6)	0.0009 (4)	−0.0103 (4)	0.0030 (5)
O3	0.0270 (5)	0.0168 (5)	0.0435 (7)	−0.0025 (4)	−0.0055 (5)	−0.0009 (5)
C1	0.0197 (6)	0.0201 (7)	0.0190 (7)	−0.0014 (5)	0.0029 (5)	−0.0007 (6)
C2	0.0237 (6)	0.0180 (8)	0.0235 (7)	−0.0002 (5)	0.0007 (5)	−0.0019 (5)
C3	0.0239 (6)	0.0183 (7)	0.0250 (8)	0.0023 (5)	0.0008 (5)	0.0000 (6)
N4	0.0200 (5)	0.0210 (7)	0.0261 (7)	0.0023 (5)	−0.0025 (5)	0.0019 (5)
N5	0.0194 (5)	0.0175 (6)	0.0230 (6)	0.0009 (5)	−0.0007 (4)	−0.0002 (5)
C11	0.0190 (6)	0.0220 (7)	0.0174 (7)	0.0017 (5)	0.0031 (5)	−0.0016 (6)
C12	0.0221 (6)	0.0219 (8)	0.0257 (8)	−0.0002 (5)	0.0009 (6)	−0.0021 (6)
C13	0.0211 (6)	0.0306 (8)	0.0279 (8)	0.0017 (6)	−0.0015 (5)	−0.0048 (7)
C14	0.0255 (7)	0.0309 (9)	0.0237 (8)	0.0082 (6)	−0.0005 (6)	0.0007 (6)
C15	0.0311 (7)	0.0198 (7)	0.0240 (7)	0.0050 (6)	0.0037 (6)	0.0022 (6)
C16	0.0227 (6)	0.0227 (8)	0.0211 (8)	−0.0007 (5)	0.0018 (5)	−0.0010 (6)

Geometric parameters (Å, º)

N1—O3	1.2340 (16)	N5—H5	0.91 (2)
N1—O2	1.2630 (16)	C11—C16	1.393 (2)
N1—O1	1.2683 (16)	C11—C12	1.4010 (19)
C1—N5	1.3466 (18)	C12—C13	1.389 (2)
C1—C2	1.399 (2)	C12—H12	0.9500
C1—C11	1.4696 (19)	C13—C14	1.384 (2)
C2—C3	1.380 (2)	C13—H13	0.9500
C2—H2	0.9500	C14—C15	1.388 (2)
C3—N4	1.334 (2)	C14—H14	0.9500
C3—H3	0.9500	C15—C16	1.392 (2)
N4—N5	1.3486 (16)	C15—H15	0.9500
N4—H4	0.90 (2)	C16—H16	0.9500
O3—N1—O2	121.69 (12)	C16—C11—C12	119.51 (13)
O3—N1—O1	120.75 (12)	C16—C11—C1	121.84 (12)
O2—N1—O1	117.54 (12)	C12—C11—C1	118.64 (13)
N5—C1—C2	107.21 (12)	C13—C12—C11	119.86 (14)
N5—C1—C11	122.44 (13)	C13—C12—H12	120.1
C2—C1—C11	130.35 (13)	C11—C12—H12	120.1
C3—C2—C1	106.25 (13)	C14—C13—C12	120.54 (14)
C3—C2—H2	126.9	C14—C13—H13	119.7
C1—C2—H2	126.9	C12—C13—H13	119.7
N4—C3—C2	108.47 (13)	C13—C14—C15	119.73 (14)
N4—C3—H3	125.8	C13—C14—H14	120.1
C2—C3—H3	125.8	C15—C14—H14	120.1
C3—N4—N5	108.99 (12)	C14—C15—C16	120.40 (14)
C3—N4—H4	126.7 (14)	C14—C15—H15	119.8
N5—N4—H4	124.2 (14)	C16—C15—H15	119.8
C1—N5—N4	109.08 (12)	C15—C16—C11	119.95 (13)
C1—N5—H5	130.7 (11)	C15—C16—H16	120.0
N4—N5—H5	120.1 (11)	C11—C16—H16	120.0
N5—C1—C2—C3	0.20 (17)	C2—C1—C11—C12	−15.4 (2)
C11—C1—C2—C3	179.80 (14)	C16—C11—C12—C13	−0.5 (2)
C1—C2—C3—N4	−0.40 (17)	C1—C11—C12—C13	179.81 (14)
C2—C3—N4—N5	0.46 (17)	C11—C12—C13—C14	0.4 (2)
C2—C1—N5—N4	0.07 (16)	C12—C13—C14—C15	−0.1 (2)
C11—C1—N5—N4	−179.57 (12)	C13—C14—C15—C16	−0.1 (2)
C3—N4—N5—C1	−0.33 (16)	C14—C15—C16—C11	−0.1 (2)
N5—C1—C11—C16	−15.5 (2)	C12—C11—C16—C15	0.4 (2)
C2—C1—C11—C16	164.97 (15)	C1—C11—C16—C15	−179.96 (14)
N5—C1—C11—C12	164.17 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1	0.90 (2)	2.40 (2)	2.9019 (17)	115.0 (16)
N4—H4···O1^i	0.90 (2)	1.83 (2)	2.7233 (16)	169 (2)
N5—H5···O2	0.91 (2)	1.90 (2)	2.8060 (17)	177.0 (17)
N5—H5···O1	0.91 (2)	2.297 (18)	2.8802 (16)	121.7 (14)
C16—H16···O2	0.95	2.51	3.3643 (17)	149

Symmetry code: (i) −x, −y+1, −z.