Literature DB >> 21587978

1-Hydroxy-4-aza-1-azoniabicyclo[2.2.2]octane picrate.

Abstract

In the crystal structure of the title compound, C(6)H(13)N(2)O(+)·C(6)H(2)N(3)O(7) (-), the anions and cations are linked by O-H⋯O, C-H⋯O and C-H⋯N hydrogen bonds into a three-dimensional network. The O atoms of a nitro group of the picrate anion are disordered over two positions of equal occupancy.

Entities: Chemical Disease Species

Year: 2010 PMID： 21587978 PMCID： PMC3006718 DOI： 10.1107/S1600536810023597

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the dielectric properties of N-protonated compounds, see: Szafranski & Katrusiak (2008 ▶); Katrusiak & Szafranski (1999 ▶); Chen et al. (2009 ▶); Mihailovic et al. (1990 ▶).

Experimental

Crystal data

C6H13N2O+·C6H2N3O7 − M = 357.29 Monoclinic, a = 11.521 (2) Å b = 19.230 (4) Å c = 6.9921 (14) Å β = 98.73 (3)° V = 1531.2 (5) Å3 Z = 4 Mo Kα radiation μ = 0.13 mm−1 T = 293 K 0.3 × 0.25 × 0.2 mm

Data collection

Rigaku Mercury2 diffractometer Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.176, T max = 0.298 15623 measured reflections 3495 independent reflections 2111 reflections with I > 2σ(I) R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.056 wR(F 2) = 0.176 S = 0.83 3495 reflections 249 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.18 e Å−3 Δρmin = −0.17 e Å−3 Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97. Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536810023597/rz2465sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810023597/rz2465Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₆H₁₃N₂O⁺·C₆H₂N₃O₇⁻	F(000) = 744
M_r = 357.29	D_x = 1.550 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5732 reflections
a = 11.521 (2) Å	θ = 3.8–27.5°
b = 19.230 (4) Å	µ = 0.13 mm⁻¹
c = 6.9921 (14) Å	T = 293 K
β = 98.73 (3)°	Prism, yellow
V = 1531.2 (5) Å³	0.3 × 0.25 × 0.2 mm
Z = 4

Rigaku Mercury2 diffractometer	3495 independent reflections
Radiation source: fine-focus sealed tube	2111 reflections with I > 2σ(I)
graphite	R_int = 0.064
CCD Profile fitting scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −14→14
T_min = 0.176, T_max = 0.298	k = −24→24
15623 measured reflections	l = −9→9

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)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.176	w = 1/[σ²(F_o²) + (0.0905P)² + 1.2925P] where P = (F_o² + 2F_c²)/3
S = 0.83	(Δ/σ)_max < 0.001
3495 reflections	Δρ_max = 0.18 e Å⁻³
249 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (2)

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	U_iso*/U_eq	Occ. (<1)
C1	0.30226 (19)	0.18175 (13)	0.6927 (3)	0.0374 (5)
C2	0.3052 (2)	0.25659 (13)	0.7118 (3)	0.0395 (6)
C3	0.2105 (2)	0.29629 (13)	0.7377 (3)	0.0413 (6)
H3	0.2160	0.3445	0.7403	0.050*
C4	0.1062 (2)	0.26361 (13)	0.7599 (3)	0.0392 (6)
C5	0.0965 (2)	0.19198 (14)	0.7588 (3)	0.0403 (6)
H5	0.0271	0.1706	0.7794	0.048*
C6	0.1917 (2)	0.15287 (13)	0.7266 (3)	0.0387 (5)
C7	0.6393 (2)	0.10824 (17)	0.9188 (4)	0.0584 (8)
H7A	0.6286	0.0821	1.0335	0.070*
H7B	0.5852	0.1472	0.9055	0.070*
C8	0.7660 (3)	0.1343 (2)	0.9351 (6)	0.0926 (13)
H8A	0.7658	0.1847	0.9319	0.111*
H8B	0.8091	0.1198	1.0587	0.111*
C9	0.6332 (2)	0.10287 (15)	0.5683 (4)	0.0510 (7)
H9A	0.5798	0.1421	0.5511	0.061*
H9B	0.6177	0.0734	0.4547	0.061*
C10	0.7612 (3)	0.1282 (2)	0.5971 (6)	0.0763 (10)
H10A	0.8001	0.1093	0.4951	0.092*
H10B	0.7619	0.1785	0.5862	0.092*
C11	0.7006 (2)	0.00311 (16)	0.7672 (5)	0.0630 (8)
H11A	0.6863	−0.0269	0.6545	0.076*
H11B	0.6907	−0.0240	0.8806	0.076*
C12	0.8254 (3)	0.03364 (19)	0.7890 (7)	0.0869 (12)
H12A	0.8693	0.0186	0.9114	0.104*
H12B	0.8649	0.0156	0.6864	0.104*
N1	0.41469 (19)	0.29372 (12)	0.6998 (3)	0.0490 (6)
N2	0.00623 (19)	0.30586 (13)	0.7894 (3)	0.0510 (6)
N3	0.1777 (2)	0.07762 (13)	0.7258 (4)	0.0558 (6)
N4	0.61729 (16)	0.06299 (10)	0.7448 (3)	0.0406 (5)
N5	0.8256 (2)	0.10837 (14)	0.7815 (4)	0.0641 (7)
O1	0.50786 (17)	0.26560 (12)	0.7614 (4)	0.0752 (7)
O2	0.40780 (19)	0.35263 (11)	0.6338 (3)	0.0678 (6)
O3	0.0149 (2)	0.36879 (12)	0.7812 (4)	0.0798 (7)
O4	−0.08245 (17)	0.27652 (12)	0.8233 (3)	0.0684 (6)
O5	0.0766 (4)	0.0514 (3)	0.6742 (11)	0.0852 (18)	0.50
O6	0.2617 (12)	0.0371 (7)	0.7403 (19)	0.066 (2)	0.50
O5'	0.1080 (6)	0.0591 (3)	0.8345 (12)	0.100 (2)	0.50
O6'	0.2427 (13)	0.0432 (7)	0.670 (2)	0.109 (5)	0.50
O7	0.38528 (15)	0.14793 (9)	0.6419 (3)	0.0523 (5)
O8	0.50320 (16)	0.03390 (10)	0.7282 (3)	0.0545 (5)
H1	0.457 (3)	0.0704 (19)	0.712 (5)	0.081 (11)*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0312 (12)	0.0454 (13)	0.0352 (12)	0.0040 (10)	0.0038 (9)	0.0017 (10)
C2	0.0347 (13)	0.0486 (14)	0.0352 (12)	−0.0032 (10)	0.0054 (10)	−0.0010 (10)
C3	0.0445 (14)	0.0450 (14)	0.0329 (12)	0.0040 (11)	0.0011 (10)	−0.0022 (10)
C4	0.0326 (12)	0.0512 (15)	0.0335 (12)	0.0090 (10)	0.0038 (9)	−0.0019 (10)
C5	0.0312 (12)	0.0570 (15)	0.0329 (12)	0.0011 (11)	0.0055 (9)	0.0020 (11)
C6	0.0351 (12)	0.0457 (14)	0.0356 (12)	0.0018 (10)	0.0068 (9)	0.0032 (10)
C7	0.0515 (17)	0.073 (2)	0.0507 (16)	−0.0038 (14)	0.0083 (13)	−0.0132 (14)
C8	0.061 (2)	0.121 (3)	0.095 (3)	−0.024 (2)	0.0081 (19)	−0.046 (2)
C9	0.0486 (15)	0.0561 (16)	0.0494 (15)	−0.0041 (12)	0.0104 (12)	0.0049 (13)
C10	0.0558 (19)	0.083 (2)	0.094 (3)	−0.0133 (17)	0.0259 (18)	0.020 (2)
C11	0.0495 (17)	0.0467 (16)	0.092 (2)	0.0080 (13)	0.0076 (15)	0.0077 (15)
C12	0.0439 (18)	0.071 (2)	0.144 (4)	0.0117 (16)	0.0082 (19)	0.012 (2)
N1	0.0454 (13)	0.0509 (14)	0.0521 (13)	−0.0051 (10)	0.0120 (10)	−0.0065 (11)
N2	0.0424 (13)	0.0605 (15)	0.0482 (13)	0.0137 (11)	0.0005 (10)	−0.0046 (11)
N3	0.0387 (12)	0.0511 (14)	0.0797 (17)	0.0007 (11)	0.0161 (12)	0.0093 (13)
N4	0.0302 (10)	0.0398 (11)	0.0521 (12)	−0.0012 (8)	0.0069 (8)	0.0013 (9)
N5	0.0356 (12)	0.0671 (17)	0.0889 (19)	−0.0035 (11)	0.0072 (12)	−0.0048 (14)
O1	0.0361 (11)	0.0724 (15)	0.115 (2)	−0.0041 (10)	0.0032 (11)	−0.0038 (13)
O2	0.0672 (14)	0.0541 (13)	0.0866 (16)	−0.0109 (10)	0.0263 (11)	0.0066 (11)
O3	0.0601 (14)	0.0561 (14)	0.123 (2)	0.0194 (11)	0.0128 (13)	−0.0058 (13)
O4	0.0412 (11)	0.0803 (15)	0.0881 (16)	0.0105 (10)	0.0235 (10)	−0.0057 (12)
O5	0.039 (3)	0.054 (3)	0.163 (6)	−0.011 (2)	0.018 (3)	−0.014 (4)
O6	0.046 (3)	0.047 (3)	0.104 (5)	0.004 (2)	0.008 (3)	0.015 (3)
O5'	0.080 (4)	0.072 (4)	0.160 (6)	0.005 (3)	0.059 (4)	0.040 (4)
O6'	0.086 (8)	0.051 (6)	0.204 (15)	−0.005 (5)	0.071 (9)	−0.045 (8)
O7	0.0383 (10)	0.0505 (11)	0.0712 (13)	0.0069 (8)	0.0187 (9)	0.0019 (9)
O8	0.0354 (10)	0.0458 (11)	0.0828 (14)	−0.0078 (8)	0.0108 (9)	0.0026 (10)

C1—O7	1.252 (3)	C10—N5	1.438 (4)
C1—C6	1.442 (3)	C10—H10A	0.9700
C1—C2	1.445 (4)	C10—H10B	0.9700
C2—C3	1.365 (3)	C11—N4	1.492 (3)
C2—N1	1.463 (3)	C11—C12	1.540 (4)
C3—C4	1.386 (3)	C11—H11A	0.9700
C3—H3	0.9300	C11—H11B	0.9700
C4—C5	1.382 (4)	C12—N5	1.438 (4)
C4—N2	1.450 (3)	C12—H12A	0.9700
C5—C6	1.376 (3)	C12—H12B	0.9700
C5—H5	0.9300	N1—O1	1.221 (3)
C6—N3	1.456 (3)	N1—O2	1.221 (3)
C7—N4	1.486 (3)	N2—O3	1.216 (3)
C7—C8	1.531 (4)	N2—O4	1.222 (3)
C7—H7A	0.9700	N3—O6'	1.114 (14)
C7—H7B	0.9700	N3—O6	1.235 (13)
C8—N5	1.447 (5)	N3—O5'	1.239 (6)
C8—H8A	0.9700	N3—O5	1.271 (5)
C8—H8B	0.9700	N4—O8	1.417 (2)
C9—N4	1.488 (3)	O5—O5'	1.134 (8)
C9—C10	1.537 (4)	O6—O6'	0.52 (2)
C9—H9A	0.9700	O8—H1	0.88 (3)
C9—H9B	0.9700

O7—C1—C6	125.4 (2)	N4—C11—C12	107.0 (2)
O7—C1—C2	122.4 (2)	N4—C11—H11A	110.3
C6—C1—C2	112.1 (2)	C12—C11—H11A	110.3
C3—C2—C1	124.1 (2)	N4—C11—H11B	110.3
C3—C2—N1	116.6 (2)	C12—C11—H11B	110.3
C1—C2—N1	119.3 (2)	H11A—C11—H11B	108.6
C2—C3—C4	119.0 (2)	N5—C12—C11	112.6 (3)
C2—C3—H3	120.5	N5—C12—H12A	109.1
C4—C3—H3	120.5	C11—C12—H12A	109.1
C5—C4—C3	121.5 (2)	N5—C12—H12B	109.1
C5—C4—N2	119.6 (2)	C11—C12—H12B	109.1
C3—C4—N2	118.9 (2)	H12A—C12—H12B	107.8
C6—C5—C4	118.7 (2)	O1—N1—O2	123.2 (2)
C6—C5—H5	120.7	O1—N1—C2	118.9 (2)
C4—C5—H5	120.7	O2—N1—C2	117.8 (2)
C5—C6—C1	124.2 (2)	O3—N2—O4	123.1 (2)
C5—C6—N3	117.0 (2)	O3—N2—C4	118.6 (2)
C1—C6—N3	118.8 (2)	O4—N2—C4	118.3 (2)
N4—C7—C8	107.1 (2)	O6'—N3—O5'	125.3 (8)
N4—C7—H7A	110.3	O6—N3—O5'	110.0 (7)
C8—C7—H7A	110.3	O6'—N3—O5	107.5 (9)
N4—C7—H7B	110.3	O6—N3—O5	116.5 (8)
C8—C7—H7B	110.3	O5'—N3—O5	53.7 (4)
H7A—C7—H7B	108.5	O6'—N3—C6	120.9 (8)
N5—C8—C7	112.7 (3)	O6—N3—C6	122.9 (7)
N5—C8—H8A	109.0	O5'—N3—C6	111.4 (4)
C7—C8—H8A	109.0	O5—N3—C6	119.4 (3)
N5—C8—H8B	109.0	O8—N4—C7	109.82 (19)
C7—C8—H8B	109.0	O8—N4—C9	111.43 (18)
H8A—C8—H8B	107.8	C7—N4—C9	110.5 (2)
N4—C9—C10	106.9 (2)	O8—N4—C11	106.12 (19)
N4—C9—H9A	110.3	C7—N4—C11	109.8 (2)
C10—C9—H9A	110.3	C9—N4—C11	109.0 (2)
N4—C9—H9B	110.3	C12—N5—C10	107.1 (3)
C10—C9—H9B	110.3	C12—N5—C8	108.3 (3)
H9A—C9—H9B	108.6	C10—N5—C8	109.6 (3)
N5—C10—C9	112.8 (2)	O5'—O5—N3	61.7 (4)
N5—C10—H10A	109.0	O6'—O6—N3	64 (3)
C9—C10—H10A	109.0	O5—O5'—N3	64.6 (4)
N5—C10—H10B	109.0	O6—O6'—N3	91 (3)
C9—C10—H10B	109.0	N4—O8—H1	103 (2)
H10A—C10—H10B	107.8

D—H···A	D—H	H···A	D···A	D—H···A
O8—H1···O7	0.88 (3)	1.74 (4)	2.602 (3)	167 (3)
O8—H1···O6'	0.88 (3)	2.50 (4)	2.973 (15)	115 (3)
C7—H7B···O1	0.97	2.59	3.486 (4)	153
C9—H9A···O7	0.97	2.42	3.102 (3)	127
C5—H5···N5ⁱ	0.93	2.61	3.536 (3)	171
C11—H11A···O6'ⁱⁱ	0.97	2.54	3.342 (15)	139
C12—H12A···O5'ⁱⁱⁱ	0.97	2.31	3.176 (9)	149
C12—H12B···O5^iv	0.97	2.55	3.137 (7)	119

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H1⋯O7	0.88 (3)	1.74 (4)	2.602 (3)	167 (3)
O8—H1⋯O6′	0.88 (3)	2.50 (4)	2.973 (15)	115 (3)
C7—H7B⋯O1	0.97	2.59	3.486 (4)	153
C9—H9A⋯O7	0.97	2.42	3.102 (3)	127
C5—H5⋯N5ⁱ	0.93	2.61	3.536 (3)	171
C11—H11A⋯O6′ⁱⁱ	0.97	2.54	3.342 (15)	139
C12—H12A⋯O5′ⁱⁱⁱ	0.97	2.31	3.176 (9)	149
C12—H12B⋯O5^iv	0.97	2.55	3.137 (7)	119

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

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Giant dielectric anisotropy and relaxor ferroelectricity induced by proton transfers in NH+...N-bonded supramolecular aggregates.

Authors: Marek Szafrański; Andrzej Katrusiak
Journal: J Phys Chem B Date: 2008-05-09 Impact factor: 2.991

2 in total