Morpholinium styphnate.

In the title mol-ecular salt (systematic name: morpholinium 3-hy-droxy-2,4,6-trinitro-phenolate), C(4)H(10)NO(+)·C(6)H(2)N(3)O(8) (-), two of the nitro groups of the anion are close to parallel with the plane of the benzene ring [dihedral angles = 3.46 (9) and 11.60 (10)°] and one is almost perpendicular [dihedral angle = 82.23 (8)°]. An intra-molecular O-H⋯O hydrogen bond occurs in the anion. The morpholinium cation has a slightly distorted chair conformation. In the crystal, the components are linked by simple N-H⋯O and trifurcated N-H⋯(O,O,O) hydrogen bonds.

Related literature

For related mol­ecular salts, see: Radha et al. (1987 ▶).

Experimental

Crystal data

C4H10NO+·C6H2N3O8 −

M = 332.24

Triclinic,

a = 7.680 (5) Å

b = 7.973 (5) Å

c = 11.852 (5) Å

α = 94.785 (5)°

β = 99.016 (5)°

γ = 108.188 (5)°

V = 674.1 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.15 mm−1

T = 293 K

0.30 × 0.16 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.957, T max = 0.977

16214 measured reflections

3841 independent reflections

2944 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.157

S = 1.06

3841 reflections

225 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.77 e Å−3

Δρmin = −0.38 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038304/hb5640sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038304/hb5640Isup2.hkl

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

C4H10NO+·C6H2N3O8−	Z = 2
Mr = 332.24	F(000) = 344
Triclinic, P1	Dx = 1.637 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.680 (5) Å	Cell parameters from 5851 reflections
b = 7.973 (5) Å	θ = 1.8–29.8°
c = 11.852 (5) Å	µ = 0.15 mm−1
α = 94.785 (5)°	T = 293 K
β = 99.016 (5)°	Prism, yellow
γ = 108.188 (5)°	0.30 × 0.16 × 0.16 mm
V = 674.1 (7) Å3

Bruker Kappa APEXII CCD diffractometer	3841 independent reflections
Radiation source: fine-focus sealed tube	2944 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω and φ scan	θmax = 29.8°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −10→10
Tmin = 0.957, Tmax = 0.977	k = −11→11
16214 measured reflections	l = −16→16

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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.157	w = 1/[σ2(Fo2) + (0.0867P)2 + 0.1583P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
3841 reflections	Δρmax = 0.77 e Å−3
225 parameters	Δρmin = −0.38 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.049 (7)

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
C1	0.48003 (18)	0.27015 (18)	−0.13460 (12)	0.0293 (3)
C2	0.31234 (18)	0.11938 (18)	−0.14972 (11)	0.0287 (3)
C3	0.24207 (17)	0.02930 (17)	−0.06486 (12)	0.0270 (3)
C4	0.33875 (18)	0.09746 (17)	0.05024 (11)	0.0274 (3)
C5	0.49948 (18)	0.24441 (18)	0.07302 (12)	0.0288 (3)
C6	0.57105 (17)	0.32628 (17)	−0.01487 (12)	0.0278 (3)
C7	0.7665 (3)	0.2429 (2)	−0.41273 (15)	0.0457 (4)
H7A	0.7022	0.1253	−0.3954	0.055*
H7B	0.8644	0.2344	−0.4533	0.055*
C8	0.6313 (3)	0.3086 (3)	−0.48707 (15)	0.0497 (4)
H8A	0.5789	0.2278	−0.5589	0.060*
H8B	0.5298	0.3097	−0.4479	0.060*
C9	0.7903 (3)	0.6028 (3)	−0.40700 (17)	0.0536 (5)
H9A	0.6880	0.6021	−0.3681	0.064*
H9B	0.8454	0.7225	−0.4244	0.064*
C10	0.9345 (2)	0.5533 (2)	−0.32858 (15)	0.0453 (4)
H10A	1.0405	0.5600	−0.3652	0.054*
H10B	0.9784	0.6355	−0.2571	0.054*
N1	0.74511 (16)	0.47391 (16)	0.01785 (11)	0.0332 (3)
N2	0.21517 (18)	0.0548 (2)	−0.26913 (11)	0.0398 (3)
N3	0.27441 (17)	0.01490 (17)	0.14458 (11)	0.0352 (3)
N4	0.84911 (19)	0.36922 (19)	−0.30416 (11)	0.0373 (3)
O1	0.81876 (17)	0.54823 (17)	−0.05681 (12)	0.0544 (4)
O2	0.81128 (17)	0.52044 (18)	0.12078 (11)	0.0533 (3)
O3	0.1114 (3)	0.1265 (3)	−0.31268 (14)	0.0847 (6)
O4	0.2437 (3)	−0.0695 (3)	−0.31820 (14)	0.0838 (6)
O5	0.14855 (16)	−0.13353 (15)	0.12339 (10)	0.0440 (3)
O6	0.3436 (2)	0.0883 (2)	0.24304 (10)	0.0587 (4)
O7	0.53339 (16)	0.33703 (18)	−0.21939 (10)	0.0463 (3)
O8	0.08817 (14)	−0.11441 (14)	−0.09399 (10)	0.0371 (3)
O9	0.7206 (2)	0.4823 (2)	−0.51108 (10)	0.0534 (3)
H4A	0.762 (3)	0.371 (3)	−0.2657 (19)	0.053 (6)*
H4B	0.931 (3)	0.333 (3)	−0.2646 (18)	0.047 (5)*
H5	0.562 (3)	0.285 (3)	0.1470 (19)	0.048 (5)*
H8	0.079 (4)	−0.160 (3)	−0.026 (2)	0.069 (7)*

	U11	U22	U33	U12	U13	U23
C1	0.0251 (6)	0.0320 (6)	0.0319 (7)	0.0093 (5)	0.0077 (5)	0.0079 (5)
C2	0.0269 (6)	0.0312 (6)	0.0266 (6)	0.0088 (5)	0.0033 (5)	0.0025 (5)
C3	0.0242 (6)	0.0244 (6)	0.0323 (7)	0.0082 (5)	0.0050 (5)	0.0033 (5)
C4	0.0273 (6)	0.0269 (6)	0.0288 (6)	0.0088 (5)	0.0066 (5)	0.0067 (5)
C5	0.0273 (6)	0.0283 (6)	0.0297 (7)	0.0090 (5)	0.0030 (5)	0.0033 (5)
C6	0.0221 (5)	0.0250 (6)	0.0352 (7)	0.0065 (5)	0.0045 (5)	0.0049 (5)
C7	0.0533 (9)	0.0447 (9)	0.0365 (8)	0.0164 (7)	0.0019 (7)	0.0028 (7)
C8	0.0473 (9)	0.0627 (11)	0.0332 (8)	0.0175 (8)	−0.0039 (7)	0.0003 (7)
C9	0.0680 (12)	0.0471 (10)	0.0506 (10)	0.0233 (9)	0.0134 (9)	0.0136 (8)
C10	0.0451 (9)	0.0448 (9)	0.0385 (8)	0.0042 (7)	0.0080 (7)	0.0061 (7)
N1	0.0245 (5)	0.0284 (6)	0.0452 (7)	0.0076 (4)	0.0049 (5)	0.0047 (5)
N2	0.0351 (6)	0.0491 (8)	0.0297 (6)	0.0079 (5)	0.0050 (5)	0.0014 (5)
N3	0.0343 (6)	0.0384 (6)	0.0337 (6)	0.0106 (5)	0.0084 (5)	0.0124 (5)
N4	0.0343 (6)	0.0486 (8)	0.0272 (6)	0.0108 (6)	0.0046 (5)	0.0101 (5)
O1	0.0419 (6)	0.0498 (7)	0.0578 (8)	−0.0079 (5)	0.0139 (6)	0.0147 (6)
O2	0.0385 (6)	0.0535 (7)	0.0484 (7)	−0.0044 (5)	−0.0036 (5)	−0.0010 (6)
O3	0.0871 (12)	0.1311 (16)	0.0459 (8)	0.0682 (12)	−0.0171 (8)	−0.0025 (9)
O4	0.1088 (14)	0.0908 (13)	0.0509 (9)	0.0491 (11)	−0.0020 (9)	−0.0255 (8)
O5	0.0432 (6)	0.0382 (6)	0.0473 (7)	0.0038 (5)	0.0130 (5)	0.0167 (5)
O6	0.0635 (8)	0.0691 (9)	0.0290 (6)	0.0013 (7)	0.0071 (5)	0.0107 (6)
O7	0.0364 (6)	0.0621 (8)	0.0379 (6)	0.0070 (5)	0.0117 (5)	0.0204 (5)
O8	0.0320 (5)	0.0316 (5)	0.0389 (6)	−0.0003 (4)	0.0047 (4)	0.0040 (4)
O9	0.0640 (8)	0.0711 (9)	0.0337 (6)	0.0321 (7)	0.0077 (5)	0.0185 (6)

C1—O7	1.2426 (17)	C8—H8B	0.9700
C1—C2	1.4356 (19)	C9—O9	1.416 (2)
C1—C6	1.446 (2)	C9—C10	1.503 (3)
C2—C3	1.3665 (19)	C9—H9A	0.9700
C2—N2	1.4603 (19)	C9—H9B	0.9700
C3—O8	1.3378 (17)	C10—N4	1.482 (2)
C3—C4	1.4194 (19)	C10—H10A	0.9700
C4—C5	1.3817 (19)	C10—H10B	0.9700
C4—N3	1.4214 (17)	N1—O1	1.2203 (17)
C5—C6	1.3719 (19)	N1—O2	1.2233 (18)
C5—H5	0.91 (2)	N2—O3	1.197 (2)
C6—N1	1.4498 (18)	N2—O4	1.203 (2)
C7—N4	1.484 (2)	N3—O6	1.2184 (18)
C7—C8	1.502 (3)	N3—O5	1.2482 (18)
C7—H7A	0.9700	N4—H4A	0.87 (2)
C7—H7B	0.9700	N4—H4B	0.86 (2)
C8—O9	1.416 (3)	O8—H8	0.91 (3)
C8—H8A	0.9700
O7—C1—C2	120.48 (13)	O9—C9—C10	111.16 (15)
O7—C1—C6	126.99 (13)	O9—C9—H9A	109.4
C2—C1—C6	112.53 (11)	C10—C9—H9A	109.4
C3—C2—C1	126.43 (12)	O9—C9—H9B	109.4
C3—C2—N2	118.38 (12)	C10—C9—H9B	109.4
C1—C2—N2	115.13 (12)	H9A—C9—H9B	108.0
O8—C3—C2	119.07 (12)	N4—C10—C9	108.79 (14)
O8—C3—C4	124.16 (12)	N4—C10—H10A	109.9
C2—C3—C4	116.77 (12)	C9—C10—H10A	109.9
C5—C4—C3	120.65 (12)	N4—C10—H10B	109.9
C5—C4—N3	118.42 (12)	C9—C10—H10B	109.9
C3—C4—N3	120.92 (12)	H10A—C10—H10B	108.3
C6—C5—C4	120.95 (13)	O1—N1—O2	122.51 (13)
C6—C5—H5	119.1 (13)	O1—N1—C6	119.61 (13)
C4—C5—H5	119.9 (13)	O2—N1—C6	117.88 (12)
C5—C6—C1	122.56 (12)	O3—N2—O4	123.56 (16)
C5—C6—N1	116.61 (13)	O3—N2—C2	118.88 (15)
C1—C6—N1	120.83 (12)	O4—N2—C2	117.55 (15)
N4—C7—C8	109.05 (15)	O6—N3—O5	121.80 (13)
N4—C7—H7A	109.9	O6—N3—C4	119.89 (13)
C8—C7—H7A	109.9	O5—N3—C4	118.30 (13)
N4—C7—H7B	109.9	C10—N4—C7	110.99 (13)
C8—C7—H7B	109.9	C10—N4—H4A	107.0 (14)
H7A—C7—H7B	108.3	C7—N4—H4A	109.7 (14)
O9—C8—C7	111.04 (15)	C10—N4—H4B	110.8 (14)
O9—C8—H8A	109.4	C7—N4—H4B	107.9 (14)
C7—C8—H8A	109.4	H4A—N4—H4B	110.4 (19)
O9—C8—H8B	109.4	C3—O8—H8	103.0 (16)
C7—C8—H8B	109.4	C8—O9—C9	109.86 (13)
H8A—C8—H8B	108.0
O7—C1—C2—C3	177.37 (14)	C2—C1—C6—N1	178.50 (11)
C6—C1—C2—C3	−2.0 (2)	N4—C7—C8—O9	57.88 (19)
O7—C1—C2—N2	0.1 (2)	O9—C9—C10—N4	−58.2 (2)
C6—C1—C2—N2	−179.23 (12)	C5—C6—N1—O1	177.61 (13)
C1—C2—C3—O8	−176.85 (13)	C1—C6—N1—O1	−2.3 (2)
N2—C2—C3—O8	0.29 (19)	C5—C6—N1—O2	−3.30 (19)
C1—C2—C3—C4	3.7 (2)	C1—C6—N1—O2	176.81 (13)
N2—C2—C3—C4	−179.14 (12)	C3—C2—N2—O3	99.3 (2)
O8—C3—C4—C5	178.49 (12)	C1—C2—N2—O3	−83.3 (2)
C2—C3—C4—C5	−2.12 (19)	C3—C2—N2—O4	−80.3 (2)
O8—C3—C4—N3	−0.6 (2)	C1—C2—N2—O4	97.2 (2)
C2—C3—C4—N3	178.84 (12)	C5—C4—N3—O6	10.8 (2)
C3—C4—C5—C6	−1.0 (2)	C3—C4—N3—O6	−170.13 (14)
N3—C4—C5—C6	178.09 (12)	C5—C4—N3—O5	−168.37 (13)
C4—C5—C6—C1	2.8 (2)	C3—C4—N3—O5	10.7 (2)
C4—C5—C6—N1	−177.07 (12)	C9—C10—N4—C7	54.78 (19)
O7—C1—C6—C5	179.29 (14)	C8—C7—N4—C10	−54.73 (19)
C2—C1—C6—C5	−1.38 (19)	C7—C8—O9—C9	−61.7 (2)
O7—C1—C6—N1	−0.8 (2)	C10—C9—O9—C8	62.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···O5	0.91 (3)	1.75 (3)	2.571 (2)	149 (2)
N4—H4A···O7	0.87 (2)	1.87 (2)	2.715 (2)	164 (2)
N4—H4B···O2i	0.86 (2)	2.31 (2)	2.962 (2)	132.4 (17)
N4—H4B···O5ii	0.86 (2)	2.42 (2)	2.967 (2)	121.5 (17)
N4—H4B···O3iii	0.86 (2)	2.54 (2)	3.206 (3)	134.3 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8⋯O5	0.91 (3)	1.75 (3)	2.571 (2)	149 (2)
N4—H4A⋯O7	0.87 (2)	1.87 (2)	2.715 (2)	164 (2)
N4—H4B⋯O2i	0.86 (2)	2.31 (2)	2.962 (2)	132.4 (17)
N4—H4B⋯O5ii	0.86 (2)	2.42 (2)	2.967 (2)	121.5 (17)
N4—H4B⋯O3iii	0.86 (2)	2.54 (2)	3.206 (3)	134.3 (17)

Symmetry codes: (i) ; (ii) ; (iii) .