3,5-Bis(2,4-dinitro-phen-yl)-4-nitro-1H-pyrazole acetone monosolvate.

The title structure, C(15)H(7)N(7)O(10)·C(3)H(6)O, was prepared by penta-nitration of 3,5-diphenyl-1H-pyrazole. The proton attached to a pyrazole N atom forms a hydrogen bond with the O atom of the acetone solvent mol-ecule, owing to the NO(2) enhanced acidity of the proton. The NO(2) group on the phenyl C atom is twisted by 33.9 (2)° from coplanarity with the ring in order to avoid a short intra-molecular O⋯O contact with an O atom of an adjacent pyrazole-bonded NO(2) group.

Related literature

For the nitration of 1H-pyrazole, see: Maresca et al. (1997 ▶). For the crystal structure of 3,5-diphenyl-1H-pyrazole, which shows a hydrogen-bonded tetra­meric structure, see: Raptis et al. (1993 ▶). For a crystallographic and ab initio study of 1H-pyrazoles, see: Foces-Foces et al. (2000 ▶).

Experimental

Crystal data

C15H7N7O10·C3H6O

M = 503.35

Monoclinic,

a = 14.886 (10) Å

b = 7.678 (5) Å

c = 19.801 (13) Å

β = 104.944 (9)°

V = 2187 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 298 K

0.31 × 0.19 × 0.18 mm

Data collection

Bruker SMART 1K CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.836, T max = 0.977

15182 measured reflections

5041 independent reflections

2703 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.202

S = 1.03

5041 reflections

332 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812001146/qk2027sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001146/qk2027Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812001146/qk2027Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536812001146/qk2027Isup4.cml

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

C15H7N7O10·C3H6O	F(000) = 1032
Mr = 503.35	Dx = 1.529 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5811 reflections
a = 14.886 (10) Å	θ = 2.1–27.1°
b = 7.678 (5) Å	µ = 0.13 mm−1
c = 19.801 (13) Å	T = 298 K
β = 104.944 (9)°	Polygon, colourless
V = 2187 (2) Å3	0.31 × 0.19 × 0.18 mm
Z = 4

Bruker SMART 1K CCD diffractometer	5041 independent reflections
Radiation source: fine-focus sealed tube	2703 reflections with I > 2σ(I)
graphite	Rint = 0.068
φ and ω scans	θmax = 28.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −19→18
Tmin = 0.836, Tmax = 0.977	k = −10→8
15182 measured reflections	l = −25→25

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)] = 0.064	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.202	w = 1/[σ2(Fo2) + (0.0696P)2 + 1.6838P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.005
5041 reflections	Δρmax = 0.27 e Å−3
332 parameters	Δρmin = −0.27 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0141 (17)

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.

	x	y	z	Uiso*/Ueq
O1	0.47956 (18)	−0.0956 (4)	0.26917 (13)	0.0968 (10)
O2	0.59247 (15)	−0.0052 (4)	0.22802 (11)	0.0746 (7)
O3	0.55406 (17)	−0.1803 (3)	0.08688 (13)	0.0730 (7)
O4	0.70324 (18)	−0.1641 (3)	0.12926 (15)	0.0868 (8)
O5	0.82468 (17)	0.3068 (4)	0.00361 (16)	0.0910 (9)
O6	0.7904 (2)	0.5619 (4)	0.03522 (18)	0.1034 (10)
O7	0.3592 (2)	−0.3312 (4)	0.12047 (15)	0.0919 (8)
O8	0.2556 (2)	−0.5123 (4)	0.13596 (16)	0.1052 (10)
O9	0.0670 (4)	−0.3824 (9)	0.2888 (3)	0.205 (3)
O10	0.0655 (3)	−0.1292 (9)	0.3325 (2)	0.187 (3)
O11	0.13846 (15)	0.4236 (3)	0.49406 (14)	0.0766 (7)
N1	0.38256 (16)	0.1537 (3)	0.05753 (13)	0.0565 (6)
N2	0.31564 (17)	0.0836 (4)	0.08520 (13)	0.0575 (7)
N3	0.0923 (3)	−0.2335 (10)	0.2962 (2)	0.1284 (19)
N4	0.2938 (2)	−0.3698 (4)	0.14388 (16)	0.0764 (8)
N5	0.6270 (2)	−0.1003 (3)	0.10191 (14)	0.0612 (7)
N6	0.77797 (18)	0.4055 (4)	0.02940 (16)	0.0678 (7)
N7	0.50947 (19)	−0.0255 (4)	0.22360 (13)	0.0632 (7)
C1	0.46197 (19)	0.1219 (4)	0.10473 (14)	0.0471 (6)
C2	0.44426 (18)	0.0326 (4)	0.16222 (14)	0.0490 (7)
C3	0.34937 (19)	0.0095 (4)	0.14748 (14)	0.0509 (7)
C4	0.54864 (18)	0.1890 (4)	0.09021 (13)	0.0471 (6)
C5	0.62536 (19)	0.0882 (4)	0.08719 (14)	0.0480 (6)
C6	0.70118 (19)	0.1549 (4)	0.06789 (15)	0.0531 (7)
H6	0.7512	0.0847	0.0656	0.064*
C7	0.69967 (19)	0.3305 (4)	0.05218 (15)	0.0521 (7)
C8	0.6277 (2)	0.4380 (4)	0.05695 (16)	0.0563 (7)
H8	0.6295	0.5564	0.0474	0.068*
C9	0.5529 (2)	0.3668 (4)	0.07611 (15)	0.0535 (7)
H9	0.5041	0.4388	0.0798	0.064*
C10	0.2870 (2)	−0.0633 (5)	0.18751 (15)	0.0578 (8)
C11	0.2586 (2)	−0.2379 (5)	0.18530 (16)	0.0624 (8)
C12	0.1955 (2)	−0.2936 (6)	0.22124 (18)	0.0798 (11)
H12	0.1764	−0.4093	0.2193	0.096*
C13	0.1618 (2)	−0.1736 (7)	0.25983 (19)	0.0853 (13)
C14	0.1888 (3)	−0.0032 (7)	0.2649 (2)	0.0913 (13)
H14	0.1658	0.0744	0.2924	0.110*
C15	0.2510 (3)	0.0513 (6)	0.2283 (2)	0.0812 (11)
H15	0.2694	0.1674	0.2310	0.097*
C16	0.0075 (3)	0.2910 (6)	0.4196 (2)	0.0893 (12)
H16A	0.0173	0.3761	0.3867	0.134*
H16B	−0.0549	0.3008	0.4244	0.134*
H16C	0.0168	0.1764	0.4032	0.134*
C17	0.0743 (2)	0.3214 (4)	0.48844 (18)	0.0609 (8)
C18	0.0603 (3)	0.2265 (6)	0.5498 (2)	0.0834 (11)
H18A	0.0700	0.1042	0.5444	0.125*
H18B	−0.0019	0.2454	0.5536	0.125*
H18C	0.1038	0.2681	0.5913	0.125*
H2A	0.256 (2)	0.082 (5)	0.0567 (18)	0.075 (11)*

	U11	U22	U33	U12	U13	U23
O1	0.0783 (17)	0.142 (3)	0.0701 (16)	−0.0068 (17)	0.0195 (13)	0.0425 (16)
O2	0.0506 (13)	0.108 (2)	0.0623 (13)	0.0001 (12)	0.0096 (10)	0.0091 (12)
O3	0.0783 (16)	0.0507 (13)	0.1029 (18)	−0.0055 (12)	0.0467 (14)	−0.0059 (12)
O4	0.0821 (17)	0.0677 (16)	0.114 (2)	0.0257 (14)	0.0310 (15)	0.0248 (14)
O5	0.0710 (16)	0.0891 (19)	0.131 (2)	0.0153 (14)	0.0578 (16)	0.0194 (17)
O6	0.100 (2)	0.0686 (18)	0.162 (3)	−0.0261 (16)	0.069 (2)	−0.0075 (18)
O7	0.108 (2)	0.0742 (18)	0.106 (2)	−0.0130 (16)	0.0497 (18)	−0.0134 (15)
O8	0.124 (2)	0.0762 (19)	0.103 (2)	−0.0379 (18)	0.0081 (18)	−0.0121 (15)
O9	0.189 (5)	0.263 (7)	0.197 (5)	−0.123 (5)	0.111 (4)	0.003 (4)
O10	0.159 (4)	0.299 (7)	0.145 (4)	−0.057 (4)	0.116 (3)	−0.024 (4)
O11	0.0555 (13)	0.0701 (15)	0.0989 (18)	−0.0122 (12)	0.0104 (12)	0.0034 (13)
N1	0.0487 (13)	0.0669 (16)	0.0573 (14)	0.0051 (12)	0.0197 (11)	0.0084 (12)
N2	0.0440 (13)	0.0720 (18)	0.0573 (14)	0.0031 (12)	0.0145 (12)	0.0073 (12)
N3	0.082 (3)	0.223 (6)	0.088 (3)	−0.044 (3)	0.036 (2)	0.024 (3)
N4	0.085 (2)	0.069 (2)	0.0689 (18)	−0.0151 (17)	0.0088 (16)	0.0013 (15)
N5	0.0655 (17)	0.0499 (15)	0.0749 (17)	0.0105 (14)	0.0305 (14)	0.0040 (12)
N6	0.0544 (15)	0.069 (2)	0.0849 (19)	−0.0030 (14)	0.0275 (14)	0.0056 (15)
N7	0.0565 (15)	0.0789 (19)	0.0539 (14)	−0.0019 (13)	0.0134 (12)	0.0097 (13)
C1	0.0482 (15)	0.0452 (15)	0.0502 (14)	0.0015 (12)	0.0168 (12)	−0.0008 (11)
C2	0.0481 (15)	0.0528 (17)	0.0472 (14)	0.0007 (12)	0.0143 (12)	0.0030 (12)
C3	0.0504 (16)	0.0543 (17)	0.0508 (15)	0.0001 (13)	0.0182 (12)	0.0013 (12)
C4	0.0461 (14)	0.0479 (15)	0.0485 (14)	0.0028 (12)	0.0140 (12)	−0.0001 (11)
C5	0.0493 (15)	0.0420 (15)	0.0543 (15)	0.0060 (12)	0.0163 (12)	0.0016 (12)
C6	0.0470 (15)	0.0532 (17)	0.0608 (17)	0.0090 (13)	0.0167 (13)	0.0000 (13)
C7	0.0443 (15)	0.0521 (17)	0.0617 (17)	−0.0024 (13)	0.0171 (13)	−0.0002 (13)
C8	0.0584 (17)	0.0437 (15)	0.0699 (18)	0.0006 (14)	0.0224 (15)	−0.0004 (13)
C9	0.0545 (16)	0.0461 (16)	0.0637 (17)	0.0062 (13)	0.0221 (14)	0.0014 (13)
C10	0.0495 (16)	0.070 (2)	0.0552 (16)	−0.0024 (15)	0.0162 (13)	0.0050 (14)
C11	0.0522 (17)	0.075 (2)	0.0559 (17)	−0.0110 (16)	0.0071 (14)	0.0053 (15)
C12	0.064 (2)	0.103 (3)	0.067 (2)	−0.030 (2)	0.0062 (17)	0.015 (2)
C13	0.058 (2)	0.140 (4)	0.062 (2)	−0.020 (2)	0.0228 (17)	0.011 (2)
C14	0.078 (3)	0.129 (4)	0.080 (3)	−0.006 (3)	0.044 (2)	−0.004 (2)
C15	0.079 (2)	0.093 (3)	0.085 (2)	−0.003 (2)	0.047 (2)	−0.007 (2)
C16	0.071 (2)	0.094 (3)	0.094 (3)	−0.009 (2)	0.006 (2)	−0.009 (2)
C17	0.0443 (16)	0.0538 (18)	0.084 (2)	0.0033 (14)	0.0152 (15)	−0.0014 (15)
C18	0.070 (2)	0.090 (3)	0.094 (3)	−0.002 (2)	0.028 (2)	0.006 (2)

O1—N7	1.228 (3)	C4—C9	1.398 (4)
O2—N7	1.226 (3)	C5—C6	1.380 (4)
O3—N5	1.216 (3)	C6—C7	1.382 (4)
O4—N5	1.226 (3)	C6—H6	0.9300
O5—N6	1.225 (4)	C7—C8	1.375 (4)
O6—N6	1.216 (4)	C8—C9	1.378 (4)
O7—N4	1.218 (4)	C8—H8	0.9300
O8—N4	1.224 (4)	C9—H9	0.9300
O9—N3	1.200 (8)	C10—C15	1.391 (5)
O10—N3	1.209 (7)	C10—C11	1.402 (5)
O11—C17	1.219 (4)	C11—C12	1.385 (5)
N1—C1	1.327 (4)	C12—C13	1.372 (6)
N1—N2	1.365 (3)	C12—H12	0.9300
N2—C3	1.333 (4)	C13—C14	1.365 (6)
N2—H2A	0.92 (3)	C14—C15	1.380 (5)
N3—C13	1.480 (5)	C14—H14	0.9300
N4—C11	1.481 (5)	C15—H15	0.9300
N5—C5	1.476 (4)	C16—C17	1.484 (5)
N6—C7	1.471 (4)	C16—H16A	0.9600
N7—C2	1.418 (4)	C16—H16B	0.9600
C1—C2	1.411 (4)	C16—H16C	0.9600
C1—C4	1.485 (4)	C17—C18	1.477 (5)
C2—C3	1.378 (4)	C18—H18A	0.9600
C3—C10	1.478 (4)	C18—H18B	0.9600
C4—C5	1.394 (4)	C18—H18C	0.9600
C1—N1—N2	104.7 (2)	C7—C8—C9	118.7 (3)
C3—N2—N1	113.6 (2)	C7—C8—H8	120.7
C3—N2—H2A	130 (2)	C9—C8—H8	120.7
N1—N2—H2A	116 (2)	C8—C9—C4	121.6 (3)
O9—N3—O10	124.3 (5)	C8—C9—H9	119.2
O9—N3—C13	118.2 (6)	C4—C9—H9	119.2
O10—N3—C13	117.5 (6)	C15—C10—C11	117.7 (3)
O7—N4—O8	124.0 (4)	C15—C10—C3	117.4 (3)
O7—N4—C11	118.4 (3)	C11—C10—C3	124.8 (3)
O8—N4—C11	117.6 (3)	C12—C11—C10	121.2 (4)
O3—N5—O4	125.0 (3)	C12—C11—N4	117.2 (3)
O3—N5—C5	118.6 (3)	C10—C11—N4	121.6 (3)
O4—N5—C5	116.4 (3)	C13—C12—C11	118.2 (4)
O6—N6—O5	124.1 (3)	C13—C12—H12	120.9
O6—N6—C7	118.1 (3)	C11—C12—H12	120.9
O5—N6—C7	117.7 (3)	C14—C13—C12	122.9 (3)
O2—N7—O1	123.6 (3)	C14—C13—N3	119.5 (5)
O2—N7—C2	118.4 (2)	C12—C13—N3	117.7 (5)
O1—N7—C2	118.0 (3)	C13—C14—C15	118.4 (4)
N1—C1—C2	109.9 (2)	C13—C14—H14	120.8
N1—C1—C4	117.4 (2)	C15—C14—H14	120.8
C2—C1—C4	132.7 (2)	C14—C15—C10	121.6 (4)
C3—C2—C1	106.6 (2)	C14—C15—H15	119.2
C3—C2—N7	125.4 (3)	C10—C15—H15	119.2
C1—C2—N7	128.0 (3)	C17—C16—H16A	109.5
N2—C3—C2	105.2 (2)	C17—C16—H16B	109.5
N2—C3—C10	121.2 (3)	H16A—C16—H16B	109.5
C2—C3—C10	133.4 (3)	C17—C16—H16C	109.5
C5—C4—C9	117.0 (3)	H16A—C16—H16C	109.5
C5—C4—C1	125.3 (3)	H16B—C16—H16C	109.5
C9—C4—C1	117.7 (2)	O11—C17—C18	121.1 (3)
C6—C5—C4	122.9 (3)	O11—C17—C16	120.6 (3)
C6—C5—N5	116.5 (2)	C18—C17—C16	118.4 (3)
C4—C5—N5	120.6 (2)	C17—C18—H18A	109.5
C5—C6—C7	117.2 (3)	C17—C18—H18B	109.5
C5—C6—H6	121.4	H18A—C18—H18B	109.5
C7—C6—H6	121.4	C17—C18—H18C	109.5
C8—C7—C6	122.5 (3)	H18A—C18—H18C	109.5
C8—C7—N6	118.6 (3)	H18B—C18—H18C	109.5
C6—C7—N6	118.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O11i	0.92 (3)	1.87 (4)	2.786 (4)	177 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O11i	0.92 (3)	1.87 (4)	2.786 (4)	177 (3)

Symmetry code: (i) .