4-Aza-1-azoniabicyclo[2.2.2]octane 2,4-dinitro­benzoate

In the title compound, C₆H₁₃N₂⁺·C₇H₃N₂O₆⁻, the 1-azonia-4-azabicyclo[2.2.2]octane cation acts as a donor in inter­molecular N—H...O hydrogen bonds. Beside the electrostatic inter­actions, the crystal structure is also stabilized by C—H...O hydrogen bonds to give a three-dimensional mol­ecular network.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.001 Å
• R factor = 0.028
• wR factor = 0.073
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level C
HYDTR01_ALERT_1_C  The hydrogen treatment should only be one of the following
            keywords
            *  refall
            *  refxyz
            *  refU
            *  noref
            *  undef
            *  constr
            *  none
            *  mixed
            Hydrogen treatment given as ref
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.78 mm
PLAT430_ALERT_2_C Short Inter D...A Contact  O2     ..  N2      ..       2.89 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           35.00
           From the CIF: _reflns_number_total               3163
           Count of symmetry unique reflns         3164
           Completeness (_total/calc)             99.97%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

1,4-Diazoniabicyclo[2.2.2]octanium 2,4-dinitrobenzoate

Crystal data

C6H13N2^+·C7H3N2O6^−	Dx = 1.541 Mg m^−3
Mr = 324.30	Melting point = 470–472 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5876 reflections
a = 12.7934 (2) Å	θ = 3.4–37.5°
b = 5.9310 (1) Å	µ = 0.12 mm^−1
c = 18.4255 (3) Å	T = 100 K
V = 1398.08 (4) Å^3	Block, pale yellow
Z = 4	0.78 × 0.49 × 0.32 mm
F(000) = 680

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	3163 independent reflections
Radiation source: fine-focus sealed tube	3059 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 8.33 pixels mm^-1	θmax = 35.0°, θmin = 2.2°
ω scans	h = −20→16
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→9
Tmin = 0.866, Tmax = 0.961	l = −29→29
22351 measured reflections

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.074	Only H-atom coordinates refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0531P)^2 + 0.0611P] where P = (Fo^2 + 2Fc^2)/3
3163 reflections	(Δ/σ)max = 0.001
272 parameters	Δρmax = 0.38 e Å^−3
1 restraint	Δρmin = −0.20 e Å^−3

Special details

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
O1	0.70816 (7)	0.55141 (13)	0.81397 (4)	0.01773 (14)
O2	0.75508 (6)	0.62581 (14)	0.92492 (5)	0.01817 (14)
O3	0.42066 (7)	0.87763 (14)	1.04597 (5)	0.01993 (15)
O4	0.31681 (7)	0.59749 (18)	1.06862 (5)	0.02477 (17)
O5	0.56036 (7)	0.07157 (17)	0.77150 (5)	0.02313 (17)
O6	0.69465 (6)	0.06193 (12)	0.84995 (4)	0.01534 (13)
N1	0.69196 (6)	0.55892 (13)	0.87967 (5)	0.01193 (13)
N2	0.38970 (7)	0.68478 (16)	1.03551 (5)	0.01623 (15)
N3	0.80720 (6)	0.95745 (13)	0.73151 (4)	0.01132 (13)
N4	0.93206 (7)	0.99116 (14)	0.62511 (5)	0.01304 (13)
C1	0.58959 (7)	0.48386 (15)	0.90580 (4)	0.01014 (13)
C2	0.53934 (7)	0.62187 (15)	0.95528 (5)	0.01212 (14)
C3	0.44277 (7)	0.54895 (16)	0.98026 (5)	0.01278 (14)
C4	0.39651 (8)	0.35091 (17)	0.95660 (6)	0.01510 (16)
C5	0.44942 (7)	0.21883 (16)	0.90599 (5)	0.01405 (15)
C6	0.54780 (7)	0.28163 (14)	0.87994 (5)	0.01090 (13)
C7	0.60588 (7)	0.12529 (15)	0.82847 (5)	0.01209 (14)
C8	0.82625 (8)	1.20190 (15)	0.71523 (5)	0.01507 (15)
C9	0.89978 (8)	1.21654 (15)	0.64906 (5)	0.01477 (15)
C10	0.90791 (8)	0.84348 (17)	0.75040 (5)	0.01373 (15)
C11	0.98365 (8)	0.87487 (17)	0.68571 (6)	0.01679 (17)
C12	0.75912 (8)	0.84707 (17)	0.66670 (5)	0.01487 (15)
C13	0.83852 (9)	0.86372 (18)	0.60345 (5)	0.01724 (17)
H12B	0.6963 (18)	0.924 (4)	0.6560 (15)	0.033 (5)*
H12A	0.7473 (15)	0.696 (3)	0.6808 (11)	0.022 (4)*
H9B	0.9660 (17)	1.299 (4)	0.6643 (12)	0.027 (5)*
H11B	1.0407 (17)	0.962 (4)	0.7020 (13)	0.026 (5)*
H10B	0.8939 (16)	0.690 (3)	0.7595 (11)	0.021 (4)*
H13B	0.8028 (16)	0.936 (4)	0.5641 (13)	0.028 (5)*
H5	0.4172 (16)	0.085 (3)	0.8909 (12)	0.023 (4)*
H10A	0.9345 (16)	0.910 (3)	0.7950 (10)	0.019 (4)*
H2	0.5666 (15)	0.756 (3)	0.9695 (11)	0.022 (4)*
H13A	0.8616 (16)	0.716 (3)	0.5880 (11)	0.025 (4)*
H9A	0.8629 (14)	1.284 (3)	0.6091 (10)	0.015 (4)*
H4	0.3337 (15)	0.309 (4)	0.9753 (11)	0.020 (4)*
H8B	0.7574 (17)	1.268 (4)	0.7061 (13)	0.028 (5)*
H11A	1.0039 (15)	0.725 (3)	0.6675 (12)	0.028 (5)*
H8A	0.8585 (17)	1.266 (4)	0.7577 (11)	0.026 (5)*
H1N3	0.7634 (18)	0.957 (4)	0.7685 (12)	0.026 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0220 (4)	0.0156 (3)	0.0156 (3)	−0.0034 (3)	0.0083 (3)	−0.0015 (2)
O2	0.0118 (3)	0.0196 (3)	0.0231 (3)	−0.0017 (2)	−0.0040 (3)	−0.0023 (3)
O3	0.0231 (4)	0.0195 (3)	0.0172 (3)	0.0079 (3)	0.0003 (3)	−0.0030 (3)
O4	0.0193 (4)	0.0336 (4)	0.0214 (4)	0.0040 (3)	0.0106 (3)	0.0007 (3)
O5	0.0176 (4)	0.0316 (4)	0.0202 (3)	0.0011 (3)	−0.0039 (3)	−0.0128 (3)
O6	0.0138 (3)	0.0171 (3)	0.0152 (3)	0.0044 (2)	0.0004 (2)	0.0000 (2)
N1	0.0105 (3)	0.0102 (3)	0.0151 (3)	0.0004 (2)	0.0017 (2)	−0.0001 (2)
N2	0.0148 (3)	0.0218 (4)	0.0121 (3)	0.0071 (3)	0.0017 (3)	0.0003 (3)
N3	0.0103 (3)	0.0122 (3)	0.0115 (3)	0.0003 (2)	0.0008 (2)	0.0003 (2)
N4	0.0128 (3)	0.0125 (3)	0.0138 (3)	−0.0002 (2)	0.0018 (2)	0.0008 (2)
C1	0.0085 (3)	0.0120 (3)	0.0099 (3)	0.0003 (2)	0.0006 (2)	0.0004 (2)
C2	0.0118 (3)	0.0137 (3)	0.0108 (3)	0.0019 (3)	0.0006 (3)	−0.0010 (3)
C3	0.0111 (3)	0.0165 (4)	0.0108 (3)	0.0036 (3)	0.0024 (3)	0.0002 (3)
C4	0.0109 (3)	0.0184 (4)	0.0160 (4)	0.0007 (3)	0.0028 (3)	0.0009 (3)
C5	0.0113 (3)	0.0151 (4)	0.0158 (4)	−0.0012 (3)	0.0018 (3)	−0.0008 (3)
C6	0.0093 (3)	0.0121 (3)	0.0113 (3)	0.0008 (3)	0.0002 (2)	0.0003 (3)
C7	0.0116 (3)	0.0113 (3)	0.0134 (3)	−0.0011 (3)	0.0018 (3)	−0.0013 (3)
C8	0.0177 (4)	0.0105 (3)	0.0170 (4)	0.0016 (3)	0.0033 (3)	−0.0002 (3)
C9	0.0155 (4)	0.0120 (3)	0.0168 (4)	0.0001 (3)	0.0032 (3)	0.0022 (3)
C10	0.0117 (3)	0.0159 (4)	0.0136 (3)	0.0022 (3)	−0.0005 (3)	0.0025 (3)
C11	0.0117 (4)	0.0192 (4)	0.0194 (4)	0.0033 (3)	0.0027 (3)	0.0052 (3)
C12	0.0118 (3)	0.0187 (4)	0.0141 (4)	−0.0029 (3)	−0.0008 (3)	0.0001 (3)
C13	0.0187 (4)	0.0198 (4)	0.0132 (3)	−0.0058 (3)	0.0018 (3)	−0.0028 (3)

Geometric parameters (Å, º)

O1—N1	1.2290 (11)	C4—C5	1.3934 (14)
O2—N1	1.2267 (11)	C4—H4	0.91 (2)
O3—N2	1.2257 (13)	C5—C6	1.3976 (12)
O4—N2	1.2287 (13)	C5—H5	0.93 (2)
O5—C7	1.2420 (12)	C6—C7	1.5203 (13)
O6—C7	1.2600 (12)	C8—C9	1.5424 (14)
N1—C1	1.4647 (12)	C8—H8B	0.98 (2)
N2—C3	1.4651 (12)	C8—H8A	0.96 (2)
N3—C12	1.4943 (13)	C9—H9B	1.02 (2)
N3—C10	1.4961 (12)	C9—H9A	0.962 (18)
N3—C8	1.5004 (12)	C10—C11	1.5474 (14)
N3—H1N3	0.88 (2)	C10—H10B	0.94 (2)
N4—C9	1.4670 (13)	C10—H10A	0.974 (19)
N4—C11	1.4690 (13)	C11—H11B	0.95 (2)
N4—C13	1.4707 (13)	C11—H11A	0.98 (2)
C1—C2	1.3836 (12)	C12—C13	1.5492 (14)
C1—C6	1.3970 (12)	C12—H12B	0.95 (2)
C2—C3	1.3876 (13)	C12—H12A	0.95 (2)
C2—H2	0.905 (19)	C13—H13B	0.96 (2)
C3—C4	1.3856 (14)	C13—H13A	0.97 (2)
O2—N1—O1	124.77 (9)	N3—C8—C9	108.15 (7)
O2—N1—C1	117.61 (8)	N3—C8—H8B	106.1 (13)
O1—N1—C1	117.62 (8)	C9—C8—H8B	112.9 (14)
O3—N2—O4	124.09 (9)	N3—C8—H8A	106.7 (12)
O3—N2—C3	118.20 (9)	C9—C8—H8A	111.0 (13)
O4—N2—C3	117.71 (9)	H8B—C8—H8A	111.6 (19)
C12—N3—C10	110.03 (7)	N4—C9—C8	110.99 (7)
C12—N3—C8	109.30 (7)	N4—C9—H9B	106.6 (12)
C10—N3—C8	110.07 (8)	C8—C9—H9B	108.4 (13)
C12—N3—H1N3	110.8 (15)	N4—C9—H9A	106.8 (11)
C10—N3—H1N3	111.5 (14)	C8—C9—H9A	109.2 (10)
C8—N3—H1N3	105.0 (14)	H9B—C9—H9A	114.8 (17)
C9—N4—C11	109.01 (8)	N3—C10—C11	107.80 (7)
C9—N4—C13	108.72 (8)	N3—C10—H10B	108.3 (13)
C11—N4—C13	109.31 (8)	C11—C10—H10B	111.8 (12)
C2—C1—C6	123.71 (8)	N3—C10—H10A	108.2 (12)
C2—C1—N1	116.88 (8)	C11—C10—H10A	112.5 (12)
C6—C1—N1	119.41 (7)	H10B—C10—H10A	108.1 (17)
C1—C2—C3	116.60 (8)	N4—C11—C10	111.14 (8)
C1—C2—H2	122.0 (13)	N4—C11—H11B	109.3 (14)
C3—C2—H2	121.4 (12)	C10—C11—H11B	107.7 (14)
C4—C3—C2	122.70 (8)	N4—C11—H11A	106.4 (13)
C4—C3—N2	119.13 (8)	C10—C11—H11A	108.6 (12)
C2—C3—N2	118.15 (9)	H11B—C11—H11A	113.7 (17)
C3—C4—C5	118.66 (9)	N3—C12—C13	107.66 (8)
C3—C4—H4	119.4 (13)	N3—C12—H12B	107.7 (16)
C5—C4—H4	121.9 (13)	C13—C12—H12B	111.6 (16)
C4—C5—C6	121.17 (9)	N3—C12—H12A	105.2 (12)
C4—C5—H5	117.4 (13)	C13—C12—H12A	111.8 (12)
C6—C5—H5	121.4 (13)	H12B—C12—H12A	112.4 (19)
C1—C6—C5	117.15 (8)	N4—C13—C12	111.23 (8)
C1—C6—C7	123.33 (8)	N4—C13—H13B	111.4 (13)
C5—C6—C7	119.46 (8)	C12—C13—H13B	106.6 (13)
O5—C7—O6	127.71 (9)	N4—C13—H13A	107.3 (13)
O5—C7—C6	117.03 (8)	C12—C13—H13A	111.4 (12)
O6—C7—C6	115.24 (8)	H13B—C13—H13A	109.0 (19)
O2—N1—C1—C2	46.61 (11)	C4—C5—C6—C7	176.09 (9)
O1—N1—C1—C2	−133.02 (9)	C1—C6—C7—O5	−126.08 (10)
O2—N1—C1—C6	−133.76 (9)	C5—C6—C7—O5	56.86 (12)
O1—N1—C1—C6	46.61 (12)	C1—C6—C7—O6	55.29 (12)
C6—C1—C2—C3	0.88 (13)	C5—C6—C7—O6	−121.77 (10)
N1—C1—C2—C3	−179.51 (8)	C12—N3—C8—C9	−59.22 (10)
C1—C2—C3—C4	−1.22 (14)	C10—N3—C8—C9	61.73 (10)
C1—C2—C3—N2	176.89 (8)	C11—N4—C9—C8	−57.84 (10)
O3—N2—C3—C4	−166.49 (9)	C13—N4—C9—C8	61.23 (10)
O4—N2—C3—C4	13.63 (14)	N3—C8—C9—N4	−2.80 (11)
O3—N2—C3—C2	15.33 (13)	C12—N3—C10—C11	62.73 (10)
O4—N2—C3—C2	−164.55 (9)	C8—N3—C10—C11	−57.78 (10)
C2—C3—C4—C5	0.40 (15)	C9—N4—C11—C10	61.87 (10)
N2—C3—C4—C5	−177.70 (9)	C13—N4—C11—C10	−56.84 (11)
C3—C4—C5—C6	0.84 (14)	N3—C10—C11—N4	−3.73 (11)
C2—C1—C6—C5	0.28 (13)	C10—N3—C12—C13	−58.73 (10)
N1—C1—C6—C5	−179.33 (8)	C8—N3—C12—C13	62.25 (10)
C2—C1—C6—C7	−176.85 (8)	C9—N4—C13—C12	−57.91 (11)
N1—C1—C6—C7	3.55 (13)	C11—N4—C13—C12	60.98 (11)
C4—C5—C6—C1	−1.15 (13)	N3—C12—C13—N4	−3.09 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···O6^i	0.88 (2)	1.85 (2)	2.6870 (11)	158 (2)
C5—H5···O2^ii	0.94 (2)	2.50 (2)	3.2375 (12)	135 (2)
C9—H9A···O4^iii	0.96 (2)	2.52 (2)	3.3304 (14)	142 (1)
C9—H9B···O5^iv	1.02 (2)	2.44 (2)	3.2999 (13)	142 (2)

Symmetry codes: (i) x, y+1, z; (ii) x−1/2, −y+1/2, z; (iii) −x+1, −y+2, z−1/2; (iv) x+1/2, −y+3/2, z.