Acetonyltriphenyl-phospho-nium nitrate.

Crystals of the title salt, C(21)H(20)OP(+)·NO(3) (-), are composed of acetonyltriphenyl-phospho-nium cations and nitrate anions that mainly inter-act through electrostatic forces. The P atom in the cation has a slightly distorted tetra-hedral environment, with C-P-C angles ranging from 104.79 (7) to 112.59 (6)°. The sum of O-N-O angles of the nitrate anion is 359.99°, reflecting its trigonal-planar character. C-H⋯O hydrogen bonds help to consolidate the crystal packing.

Related literature

For crystal structures containing triphenyl­phospho­nium moieties, see: van der Sluis & Spek (1990 ▶); Boys et al. (1995 ▶); Zhang et al. (2004 ▶); Evans (2010 ▶); Kavitha et al. (2012 ▶).

Experimental

Crystal data

C21H20OP+·NO3 −

M = 381.4

Monoclinic,

a = 14.0928 (5) Å

b = 12.6455 (3) Å

c = 21.2684 (6) Å

β = 90.667 (2)°

V = 3790.00 (19) Å3

Z = 8

Cu Kα radiation

μ = 1.51 mm−1

T = 120 K

0.19 × 0.18 × 0.12 mm

Data collection

Agilent Xcalibur diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) ▶ T min = 0.271, T max = 1

22035 measured reflections

3389 independent reflections

2969 reflections with I > 3σ(I)

R int = 0.040

Refinement

R[F 2 > 3σ(F 2)] = 0.033

wR(F 2) = 0.094

S = 1.63

3389 reflections

250 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813002110/wm2713sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002110/wm2713Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813002110/wm2713Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H20OP+·NO3−	F(000) = 1600
Mr = 381.4	Dx = 1.336 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -C 2yc	Cell parameters from 12744 reflections
a = 14.0928 (5) Å	θ = 4.2–67.0°
b = 12.6455 (3) Å	µ = 1.51 mm−1
c = 21.2684 (6) Å	T = 120 K
β = 90.667 (2)°	Polygon, colourless
V = 3790.00 (19) Å3	0.19 × 0.18 × 0.12 mm
Z = 8

Agilent Xcalibur diffractometer	3389 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2969 reflections with I > 3σ(I)
Mirror monochromator	Rint = 0.040
Detector resolution: 10.3784 pixels mm-1	θmax = 67.1°, θmin = 4.2°
ω scans	h = −16→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −15→15
Tmin = 0.271, Tmax = 1	l = −25→24
22035 measured reflections

Refinement on F2	74 constraints
R[F2 > 2σ(F2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.094	Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0016I2)
S = 1.63	(Δ/σ)max = 0.015
3389 reflections	Δρmax = 0.27 e Å−3
250 parameters	Δρmin = −0.24 e Å−3
2 restraints

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

	x	y	z	Uiso*/Ueq
P1	0.77023 (2)	0.09776 (3)	0.113631 (14)	0.01755 (11)
O1	0.93221 (8)	−0.03291 (9)	0.16541 (5)	0.0296 (3)
O2	0.22566 (11)	0.26725 (9)	0.14746 (5)	0.0446 (4)
O3	0.30174 (9)	0.15360 (10)	0.20579 (6)	0.0406 (4)
O4	0.14881 (9)	0.15797 (11)	0.20713 (5)	0.0401 (4)
N1	0.22509 (10)	0.19384 (10)	0.18695 (5)	0.0268 (4)
C1	0.83285 (10)	0.21866 (11)	0.13029 (6)	0.0194 (4)
C2	0.81834 (10)	0.03489 (11)	0.04539 (6)	0.0206 (4)
C3	0.86270 (11)	−0.04050 (11)	0.19812 (6)	0.0227 (4)
C4	0.88403 (11)	−0.05841 (13)	−0.06351 (6)	0.0295 (5)
C5	0.76868 (10)	0.00921 (11)	0.18002 (6)	0.0208 (4)
C6	0.97263 (12)	0.31195 (13)	0.16513 (8)	0.0333 (5)
C7	0.59222 (11)	0.16606 (11)	0.14808 (7)	0.0258 (4)
C8	0.49814 (12)	0.19171 (12)	0.13750 (8)	0.0323 (5)
C9	0.64745 (10)	0.12851 (11)	0.09836 (6)	0.0214 (4)
C10	0.79251 (12)	−0.06863 (12)	0.03122 (6)	0.0275 (4)
C11	0.45787 (12)	0.17953 (13)	0.07799 (9)	0.0361 (5)
C12	0.91054 (11)	0.04412 (13)	−0.04893 (6)	0.0277 (4)
C13	0.87750 (11)	0.09150 (12)	0.00565 (6)	0.0229 (4)
C14	0.83609 (12)	0.40906 (12)	0.12938 (7)	0.0286 (5)
C15	0.92558 (11)	0.21760 (12)	0.15421 (7)	0.0267 (4)
C16	0.78818 (11)	0.31533 (11)	0.11762 (6)	0.0231 (4)
C17	0.51200 (13)	0.14219 (13)	0.02899 (8)	0.0353 (5)
C18	0.92784 (13)	0.40728 (13)	0.15289 (8)	0.0323 (5)
C19	0.82556 (13)	−0.11492 (13)	−0.02360 (7)	0.0320 (5)
C20	0.86235 (13)	−0.09946 (13)	0.25901 (7)	0.0314 (5)
C21	0.60690 (11)	0.11658 (12)	0.03874 (7)	0.0279 (4)
H1c4	0.90622	−0.090662	−0.101466	0.0354*
H1c5	0.7458 (12)	0.0463 (12)	0.2162 (5)	0.025*
H3c5	0.7248 (10)	−0.0467 (10)	0.1703 (8)	0.025*
H1c6	1.036543	0.311308	0.18125	0.04*
H1c7	0.619748	0.173886	0.189322	0.0309*
H1c8	0.460415	0.218052	0.171378	0.0387*
H1c10	0.7523	−0.107678	0.058995	0.033*
H1c11	0.392337	0.197082	0.070905	0.0433*
H1c12	0.951668	0.082514	−0.076422	0.0333*
H1c13	0.895387	0.162776	0.015848	0.0275*
H1c14	0.8054	0.475496	0.121157	0.0343*
H1c15	0.956584	0.151559	0.163037	0.032*
H1c16	0.724642	0.316673	0.100864	0.0277*
H1c17	0.483862	0.133891	−0.012037	0.0424*
H1c18	0.96073	0.472515	0.160779	0.0387*
H1c19	0.807881	−0.186217	−0.033893	0.0384*
H1c20	0.808354	−0.145686	0.260001	0.0377*
H2c20	0.919458	−0.140447	0.262926	0.0377*
H3c20	0.85903	−0.050131	0.293224	0.0377*
H1c21	0.64433	0.090806	0.004569	0.0334*

	U11	U22	U33	U12	U13	U23
P1	0.0193 (2)	0.01481 (19)	0.01853 (19)	0.00064 (12)	0.00178 (13)	−0.00047 (11)
O1	0.0281 (6)	0.0311 (6)	0.0297 (5)	0.0062 (4)	0.0058 (4)	0.0063 (4)
O2	0.0793 (10)	0.0237 (6)	0.0305 (6)	−0.0097 (6)	−0.0068 (6)	0.0070 (5)
O3	0.0302 (7)	0.0460 (7)	0.0457 (6)	−0.0026 (6)	0.0044 (5)	0.0129 (5)
O4	0.0328 (7)	0.0494 (8)	0.0381 (6)	0.0049 (6)	0.0030 (5)	0.0117 (5)
N1	0.0398 (8)	0.0197 (6)	0.0210 (6)	−0.0021 (5)	−0.0003 (5)	−0.0017 (4)
C1	0.0231 (7)	0.0170 (7)	0.0183 (6)	−0.0006 (5)	0.0028 (5)	−0.0008 (5)
C2	0.0220 (7)	0.0207 (7)	0.0191 (6)	0.0039 (5)	0.0000 (5)	0.0000 (5)
C3	0.0291 (8)	0.0157 (7)	0.0232 (6)	0.0018 (5)	0.0018 (5)	−0.0002 (5)
C4	0.0296 (8)	0.0387 (9)	0.0200 (6)	0.0109 (7)	−0.0019 (5)	−0.0057 (6)
C5	0.0254 (7)	0.0178 (7)	0.0195 (6)	0.0000 (5)	0.0041 (5)	0.0004 (5)
C6	0.0291 (9)	0.0282 (8)	0.0424 (8)	−0.0048 (7)	−0.0080 (6)	0.0019 (6)
C7	0.0238 (8)	0.0194 (7)	0.0342 (7)	−0.0016 (6)	0.0030 (6)	−0.0029 (6)
C8	0.0248 (8)	0.0221 (8)	0.0502 (9)	−0.0009 (6)	0.0068 (7)	−0.0014 (6)
C9	0.0207 (7)	0.0156 (7)	0.0280 (7)	−0.0028 (5)	−0.0001 (5)	0.0015 (5)
C10	0.0369 (9)	0.0225 (7)	0.0233 (7)	−0.0015 (6)	0.0032 (6)	−0.0020 (6)
C11	0.0211 (8)	0.0266 (8)	0.0604 (10)	−0.0010 (6)	−0.0050 (7)	0.0088 (7)
C12	0.0246 (8)	0.0372 (9)	0.0216 (6)	0.0068 (6)	0.0031 (5)	0.0044 (6)
C13	0.0226 (7)	0.0237 (8)	0.0226 (6)	0.0040 (6)	0.0002 (5)	0.0028 (5)
C14	0.0339 (9)	0.0175 (7)	0.0344 (7)	−0.0005 (6)	0.0013 (6)	0.0012 (6)
C15	0.0257 (8)	0.0209 (7)	0.0334 (7)	0.0011 (6)	−0.0021 (6)	0.0021 (6)
C16	0.0246 (8)	0.0211 (7)	0.0236 (6)	0.0012 (6)	0.0010 (5)	0.0007 (5)
C17	0.0311 (9)	0.0330 (9)	0.0415 (9)	−0.0042 (7)	−0.0112 (7)	0.0095 (7)
C18	0.0363 (9)	0.0219 (8)	0.0385 (8)	−0.0078 (6)	−0.0032 (7)	−0.0008 (6)
C19	0.0422 (10)	0.0263 (8)	0.0274 (7)	0.0034 (7)	−0.0024 (6)	−0.0078 (6)
C20	0.0351 (9)	0.0307 (9)	0.0284 (7)	0.0008 (7)	0.0002 (6)	0.0089 (6)
C21	0.0292 (8)	0.0256 (8)	0.0288 (7)	−0.0017 (6)	−0.0027 (6)	0.0041 (6)

P1—C1	1.7984 (14)	C7—H1c7	0.96
P1—C2	1.7947 (13)	C8—C11	1.390 (2)
P1—C5	1.8024 (13)	C8—H1c8	0.96
P1—C9	1.7992 (15)	C9—C21	1.393 (2)
O1—C3	1.2120 (18)	C10—C19	1.390 (2)
O2—N1	1.2520 (16)	C10—H1c10	0.96
O3—N1	1.2554 (18)	C11—C17	1.382 (2)
O4—N1	1.2475 (18)	C11—H1c11	0.96
C1—C15	1.397 (2)	C12—C13	1.391 (2)
C1—C16	1.400 (2)	C12—H1c12	0.96
C2—C10	1.391 (2)	C13—H1c13	0.96
C2—C13	1.392 (2)	C14—C16	1.385 (2)
C3—C5	1.512 (2)	C14—C18	1.381 (2)
C3—C20	1.494 (2)	C14—H1c14	0.96
C4—C12	1.383 (2)	C15—H1c15	0.96
C4—C19	1.388 (2)	C16—H1c16	0.96
C4—H1c4	0.96	C17—C21	1.389 (2)
C5—H1c5	0.960 (13)	C17—H1c17	0.96
C5—H3c5	0.960 (13)	C18—H1c18	0.96
C6—C15	1.383 (2)	C19—H1c19	0.96
C6—C18	1.384 (2)	C20—H1c20	0.96
C6—H1c6	0.96	C20—H2c20	0.96
C7—C8	1.381 (2)	C20—H3c20	0.96
C7—C9	1.403 (2)	C21—H1c21	0.96
C1—P1—C2	110.29 (6)	C2—C10—C19	119.26 (14)
C1—P1—C5	112.59 (6)	C2—C10—H1c10	120.37
C1—P1—C9	108.70 (6)	C19—C10—H1c10	120.37
C2—P1—C5	111.49 (6)	C8—C11—C17	120.10 (16)
C2—P1—C9	108.74 (6)	C8—C11—H1c11	119.95
C5—P1—C9	104.79 (7)	C17—C11—H1c11	119.95
O2—N1—O3	120.16 (14)	C4—C12—C13	119.91 (14)
O2—N1—O4	120.84 (14)	C4—C12—H1c12	120.05
O3—N1—O4	118.99 (12)	C13—C12—H1c12	120.05
P1—C1—C15	121.23 (11)	C2—C13—C12	119.58 (14)
P1—C1—C16	119.07 (11)	C2—C13—H1c13	120.21
C15—C1—C16	119.69 (13)	C12—C13—H1c13	120.21
P1—C2—C10	119.46 (11)	C16—C14—C18	120.24 (14)
P1—C2—C13	119.85 (11)	C16—C14—H1c14	119.88
C10—C2—C13	120.63 (13)	C18—C14—H1c14	119.88
O1—C3—C5	122.18 (12)	C1—C15—C6	119.83 (14)
O1—C3—C20	123.22 (14)	C1—C15—H1c15	120.08
C5—C3—C20	114.60 (12)	C6—C15—H1c15	120.08
C12—C4—C19	120.40 (14)	C1—C16—C14	119.68 (14)
C12—C4—H1c4	119.8	C1—C16—H1c16	120.16
C19—C4—H1c4	119.8	C14—C16—H1c16	120.16
P1—C5—C3	116.05 (10)	C11—C17—C21	120.40 (16)
P1—C5—H1c5	109.4 (8)	C11—C17—H1c17	119.8
P1—C5—H3c5	107.6 (9)	C21—C17—H1c17	119.8
C3—C5—H1c5	107.5 (9)	C6—C18—C14	120.35 (15)
C3—C5—H3c5	108.0 (8)	C6—C18—H1c18	119.82
H1c5—C5—H3c5	108.1 (13)	C14—C18—H1c18	119.82
C15—C6—C18	120.20 (16)	C4—C19—C10	120.22 (15)
C15—C6—H1c6	119.9	C4—C19—H1c19	119.89
C18—C6—H1c6	119.9	C10—C19—H1c19	119.89
C8—C7—C9	119.78 (14)	C3—C20—H1c20	109.47
C8—C7—H1c7	120.11	C3—C20—H2c20	109.47
C9—C7—H1c7	120.11	C3—C20—H3c20	109.47
C7—C8—C11	120.24 (15)	H1c20—C20—H2c20	109.47
C7—C8—H1c8	119.88	H1c20—C20—H3c20	109.47
C11—C8—H1c8	119.88	H2c20—C20—H3c20	109.47
P1—C9—C7	118.54 (11)	C9—C21—C17	119.65 (14)
P1—C9—C21	121.64 (11)	C9—C21—H1c21	120.17
C7—C9—C21	119.83 (14)	C17—C21—H1c21	120.17

D—H···A	D—H	H···A	D···A	D—H···A
C5—H1c5···O3i	0.960 (13)	2.252 (13)	3.2053 (18)	172.1 (12)
C5—H3c5···O2ii	0.960 (13)	2.403 (12)	3.1936 (18)	139.4 (11)
C7—H1c7···O3i	0.96	2.49	3.4365 (19)	167.90
C8—H1c8···O3	0.96	2.50	3.177 (2)	127.75
C10—H1c10···O2ii	0.96	2.49	3.3706 (19)	152.50
C15—H1c15···O1	0.96	2.36	3.1780 (19)	142.99

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H1c5⋯O3i	0.960 (13)	2.252 (13)	3.2053 (18)	172.1 (12)
C5—H3c5⋯O2ii	0.960 (13)	2.403 (12)	3.1936 (18)	139.4 (11)
C7—H1c7⋯O3i	0.96	2.49	3.4365 (19)	167.90
C8—H1c8⋯O3	0.96	2.50	3.177 (2)	127.75
C10—H1c10⋯O2ii	0.96	2.49	3.3706 (19)	152.50
C15—H1c15⋯O1	0.96	2.36	3.1780 (19)	142.99

Symmetry codes: (i) ; (ii) .