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In the title compound, C6H16N+·C7H3N2O6·0.5C6H6O2, the asymmetric unit contains one cation, one anion and one-half of the neutral mol­ecule. The dihydroxybenzene molecule lies on a centre of inversion. Inter­molecular O—H...O and N—H...O hydrogen bonds are effective in the stabilization of the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807002218/hk2186sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807002218/hk2186Isup2.hkl
Contains datablock I

CCDC reference: 636690

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.064
  • wR factor = 0.227
  • Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.53 PLAT223_ALERT_4_C Large Solvent/Anion H Ueq(max)/Ueq(min) ... 3.56 Ratio PLAT231_ALERT_4_C Hirshfeld Test (Solvent) C13 - C14 .. 5.93 su PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N3 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C15 - C16 ... 1.42 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Triethylammonium 3,5-dinitrobenzoate 1,4-dihydroxybenzene hemisolvate top
Crystal data top
C6H16N+·C7H3N2O6·0.5C6H6O2F(000) = 780
Mr = 368.37Dx = 1.306 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2292 reflections
a = 10.8033 (13) Åθ = 2.5–21.5°
b = 13.7485 (16) ŵ = 0.10 mm1
c = 13.3250 (16) ÅT = 291 K
β = 108.863 (2)°Block, white
V = 1872.9 (4) Å30.28 × 0.20 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
4291 independent reflections
Radiation source: fine-focus sealed tube2170 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
φ and ω scansθmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.972, Tmax = 0.980k = 1717
16350 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.227H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.1033P)2 + 0.4311P]
where P = (Fo2 + 2Fc2)/3
4291 reflections(Δ/σ)max < 0.001
239 parametersΔρmax = 0.58 e Å3
0 restraintsΔρmin = 0.23 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
O10.31714 (19)0.99013 (16)0.64577 (16)0.0774 (6)
O20.2369 (2)0.9681 (2)0.77725 (17)0.0980 (8)
O30.1102 (3)0.8337 (2)0.30694 (19)0.1102 (9)
O40.0857 (3)0.7826 (2)0.26660 (19)0.1152 (10)
O50.3020 (2)0.7756 (2)0.5331 (2)0.1039 (8)
O60.2417 (2)0.8826 (2)0.6553 (3)0.1098 (9)
O70.8494 (2)1.12302 (17)0.07697 (18)0.0902 (7)
H70.82851.09640.12420.135*
N10.2249 (2)0.8362 (2)0.5848 (2)0.0762 (7)
N20.0119 (3)0.8175 (2)0.3282 (2)0.0800 (7)
N30.4755 (2)0.92164 (16)0.21939 (18)0.0626 (6)
H3N0.54420.95530.26340.075*
C10.1038 (3)0.82458 (19)0.4588 (2)0.0626 (7)
H10.17560.79430.41060.075*
C20.1045 (2)0.85240 (18)0.5573 (2)0.0571 (6)
C30.0009 (2)0.89563 (18)0.6316 (2)0.0575 (6)
H30.00330.91310.69780.069*
C40.1134 (2)0.91260 (17)0.6058 (2)0.0544 (6)
C50.1161 (3)0.88692 (18)0.5061 (2)0.0574 (6)
H50.19050.89880.48730.069*
C60.0081 (3)0.84359 (19)0.4348 (2)0.0602 (7)
C70.2317 (3)0.9606 (2)0.6837 (2)0.0636 (7)
C80.9248 (3)1.0601 (2)0.0401 (2)0.0654 (7)
C90.9562 (3)0.9676 (2)0.0804 (2)0.0689 (8)
H90.92680.94560.13470.083*
C101.0307 (3)0.9083 (2)0.0403 (2)0.0718 (8)
H101.05160.84600.06770.086*
C110.4259 (5)0.7570 (3)0.1336 (4)0.1362 (18)
H11A0.36070.74560.16690.204*
H11B0.46680.69650.12660.204*
H11C0.38560.78480.06460.204*
C120.5274 (3)0.8259 (2)0.2003 (3)0.0891 (10)
H12A0.57080.79540.26820.107*
H12B0.59270.83670.16580.107*
C130.4277 (4)0.8862 (5)0.3809 (4)0.178 (3)
H13A0.47990.82910.38410.267*
H13B0.35650.87100.40660.267*
H13C0.48070.93640.42420.267*
C140.3749 (4)0.9206 (4)0.2692 (3)0.1119 (14)
H14A0.30430.87810.22960.134*
H14B0.33950.98560.26790.134*
C150.4038 (6)1.0783 (4)0.1220 (4)0.160 (2)
H15A0.33801.08590.15560.240*
H15B0.37321.10610.05220.240*
H15C0.48241.11070.16330.240*
C160.4299 (4)0.9778 (3)0.1144 (3)0.1099 (13)
H16A0.49650.97160.08040.132*
H16B0.35110.94710.06840.132*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0597 (12)0.0938 (15)0.0752 (13)0.0247 (11)0.0170 (10)0.0143 (11)
O20.0828 (15)0.143 (2)0.0702 (14)0.0406 (14)0.0279 (12)0.0388 (14)
O30.125 (2)0.146 (2)0.0686 (15)0.0353 (18)0.0435 (15)0.0065 (15)
O40.108 (2)0.148 (3)0.0704 (15)0.0208 (17)0.0025 (14)0.0315 (15)
O50.0623 (13)0.117 (2)0.126 (2)0.0308 (13)0.0213 (13)0.0138 (16)
O60.0777 (16)0.119 (2)0.149 (2)0.0010 (14)0.0587 (16)0.0370 (19)
O70.0993 (17)0.0963 (17)0.0728 (15)0.0087 (14)0.0248 (12)0.0063 (12)
N10.0463 (13)0.0775 (17)0.100 (2)0.0028 (12)0.0169 (13)0.0016 (15)
N20.097 (2)0.0825 (18)0.0527 (14)0.0100 (15)0.0130 (14)0.0004 (13)
N30.0511 (12)0.0647 (14)0.0684 (14)0.0064 (10)0.0143 (11)0.0107 (11)
C10.0559 (16)0.0543 (15)0.0634 (17)0.0036 (12)0.0005 (12)0.0034 (12)
C20.0434 (13)0.0532 (14)0.0699 (17)0.0034 (11)0.0115 (12)0.0038 (12)
C30.0539 (15)0.0534 (15)0.0631 (16)0.0032 (11)0.0159 (12)0.0038 (12)
C40.0513 (14)0.0502 (14)0.0577 (15)0.0012 (11)0.0121 (11)0.0004 (11)
C50.0561 (15)0.0560 (15)0.0580 (15)0.0041 (12)0.0153 (12)0.0035 (12)
C60.0686 (17)0.0560 (15)0.0503 (15)0.0008 (13)0.0115 (12)0.0053 (12)
C70.0530 (16)0.0664 (17)0.0674 (18)0.0062 (13)0.0141 (13)0.0120 (14)
C80.0665 (17)0.0742 (19)0.0489 (14)0.0079 (14)0.0096 (13)0.0095 (13)
C90.079 (2)0.0745 (19)0.0497 (15)0.0143 (15)0.0151 (14)0.0004 (14)
C100.085 (2)0.0652 (18)0.0570 (16)0.0090 (15)0.0113 (15)0.0018 (14)
C110.133 (4)0.084 (3)0.157 (4)0.007 (2)0.002 (3)0.046 (3)
C120.073 (2)0.078 (2)0.114 (3)0.0010 (17)0.0261 (19)0.0239 (19)
C130.086 (3)0.317 (9)0.136 (4)0.029 (4)0.043 (3)0.120 (5)
C140.075 (2)0.157 (4)0.108 (3)0.008 (2)0.035 (2)0.010 (3)
C150.205 (6)0.096 (3)0.136 (4)0.003 (4)0.003 (4)0.031 (3)
C160.120 (3)0.113 (3)0.076 (2)0.023 (2)0.003 (2)0.005 (2)
Geometric parameters (Å, º) top
O1—C71.254 (3)C8—C91.379 (4)
O2—C71.234 (3)C8—C10i1.379 (4)
O3—N21.205 (4)C9—C101.370 (4)
O4—N21.207 (3)C9—H90.9300
O5—N11.221 (3)C10—C8i1.379 (4)
O6—N11.198 (3)C10—H100.9300
O7—C81.382 (4)C11—C121.503 (5)
O7—H70.8200C11—H11A0.9600
N1—C21.478 (4)C11—H11B0.9600
N2—C61.478 (4)C11—H11C0.9600
N3—C141.445 (4)C12—H12A0.9700
N3—C121.485 (4)C12—H12B0.9700
N3—C161.533 (4)C13—C141.489 (6)
N3—H3N0.9100C13—H13A0.9600
C1—C21.370 (4)C13—H13B0.9600
C1—C61.372 (4)C13—H13C0.9600
C1—H10.9300C14—H14A0.9700
C2—C31.379 (4)C14—H14B0.9700
C3—C41.385 (4)C15—C161.420 (6)
C3—H30.9300C15—H15A0.9600
C4—C51.384 (4)C15—H15B0.9600
C4—C71.513 (4)C15—H15C0.9600
C5—C61.380 (4)C16—H16A0.9700
C5—H50.9300C16—H16B0.9700
C8—O7—H7109.5C9—C10—C8i120.8 (3)
O6—N1—O5123.9 (3)C9—C10—H10119.6
O6—N1—C2118.8 (3)C8i—C10—H10119.6
O5—N1—C2117.2 (3)C12—C11—H11A109.5
O3—N2—O4123.7 (3)C12—C11—H11B109.5
O3—N2—C6118.8 (3)H11A—C11—H11B109.5
O4—N2—C6117.4 (3)C12—C11—H11C109.5
C14—N3—C12116.9 (3)H11A—C11—H11C109.5
C14—N3—C16110.9 (3)H11B—C11—H11C109.5
C12—N3—C16108.5 (3)N3—C12—C11114.6 (3)
C14—N3—H3N106.7N3—C12—H12A108.6
C12—N3—H3N106.7C11—C12—H12A108.6
C16—N3—H3N106.7N3—C12—H12B108.6
C2—C1—C6116.7 (2)C11—C12—H12B108.6
C2—C1—H1121.7H12A—C12—H12B107.6
C6—C1—H1121.7C14—C13—H13A109.5
C1—C2—C3123.3 (3)C14—C13—H13B109.5
C1—C2—N1118.2 (2)H13A—C13—H13B109.5
C3—C2—N1118.4 (3)C14—C13—H13C109.5
C2—C3—C4118.8 (3)H13A—C13—H13C109.5
C2—C3—H3120.6H13B—C13—H13C109.5
C4—C3—H3120.6N3—C14—C13111.1 (3)
C5—C4—C3119.2 (2)N3—C14—H14A109.4
C5—C4—C7119.6 (2)C13—C14—H14A109.4
C3—C4—C7121.1 (2)N3—C14—H14B109.4
C6—C5—C4119.7 (3)C13—C14—H14B109.4
C6—C5—H5120.2H14A—C14—H14B108.0
C4—C5—H5120.2C16—C15—H15A109.5
C1—C6—C5122.3 (3)C16—C15—H15B109.5
C1—C6—N2118.6 (3)H15A—C15—H15B109.5
C5—C6—N2119.1 (3)C16—C15—H15C109.5
O2—C7—O1125.5 (3)H15A—C15—H15C109.5
O2—C7—C4118.8 (3)H15B—C15—H15C109.5
O1—C7—C4115.6 (2)C15—C16—N3115.9 (4)
C9—C8—C10i119.3 (3)C15—C16—H16A108.3
C9—C8—O7122.5 (3)N3—C16—H16A108.3
C10i—C8—O7118.2 (3)C15—C16—H16B108.3
C10—C9—C8119.9 (3)N3—C16—H16B108.3
C10—C9—H9120.0H16A—C16—H16B107.4
C8—C9—H9120.0
C6—C1—C2—C31.4 (4)O4—N2—C6—C11.7 (4)
C6—C1—C2—N1178.0 (2)O3—N2—C6—C50.9 (4)
O6—N1—C2—C1159.3 (3)O4—N2—C6—C5177.7 (3)
O5—N1—C2—C120.5 (4)C5—C4—C7—O2167.8 (3)
O6—N1—C2—C320.1 (4)C3—C4—C7—O213.5 (4)
O5—N1—C2—C3160.2 (3)C5—C4—C7—O112.4 (4)
C1—C2—C3—C40.4 (4)C3—C4—C7—O1166.2 (2)
N1—C2—C3—C4178.9 (2)C10i—C8—C9—C100.1 (5)
C2—C3—C4—C50.8 (4)O7—C8—C9—C10179.7 (3)
C2—C3—C4—C7179.4 (2)C8—C9—C10—C8i0.1 (5)
C3—C4—C5—C61.0 (4)C14—N3—C12—C1157.5 (5)
C7—C4—C5—C6179.7 (2)C16—N3—C12—C1168.8 (4)
C2—C1—C6—C51.1 (4)C12—N3—C14—C1367.6 (5)
C2—C1—C6—N2178.2 (2)C16—N3—C14—C13167.3 (4)
C4—C5—C6—C10.0 (4)C14—N3—C16—C1563.4 (5)
C4—C5—C6—N2179.4 (2)C12—N3—C16—C15166.9 (4)
O3—N2—C6—C1179.7 (3)
Symmetry code: (i) x+2, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7—H7···O2ii0.821.902.717 (3)174
N3—H3N···O1ii0.911.762.668 (3)175
Symmetry code: (ii) x+1, y+2, z+1.
 

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