Literature DB >> 21522431

2-Meth-oxy-anilinium 3-hy-droxy-2,4,6-trinitro-phenolate.

Doraisamyraja Kalaivani, Rangasamy Malarvizhi, Kaliyaperumal Thanigaimani, Packianathan Thomas Muthiah.   

Abstract

The cation and anion of the title mol-ecular salt, C(7)H(10)NO(+)·C(6)H(2)N(3)O(8) (-), are linked via an N-H⋯O hydrogen bond. An intra-molecular O-H⋯O hydrogen bond is also found in the anion. In the crystal, the anions self-assemble via O-H⋯O hydrogen bonds, forming a C(9) supra-molecular chain the b axis. Further inter-molecular N-H⋯O inter-actions also occur.

Entities:  

Year:  2011        PMID： 21522431      PMCID： PMC3052155          DOI： 10.1107/S1600536811005708

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


Related literature

For crystalline metal complexes of styphnic acid, see: Cui et al. (2008 ▶); Orbovic & Codoceo (2008 ▶); Zheng et al. (2006a ▶,b ▶); Zhu & Xiao (2009 ▶). For crystalline adducts of styphnic acid with organic bases, see: Abashev et al. (2001 ▶); Liu et al. (2008 ▶); Tenishev et al. (2002 ▶); For related mol­ecular salts, see: Kalaivani & Malarvizhi (2010 ▶); Vogel (1978 ▶).

Experimental

Crystal data

C7H10NO+·C6H2N3O8 − M = 368.27 Monoclinic, a = 10.6957 (4) Å b = 17.8368 (5) Å c = 8.0527 (3) Å β = 91.991 (2)° V = 1535.34 (9) Å3 Z = 4 Mo Kα radiation μ = 0.14 mm−1 T = 293 K 0.22 × 0.18 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.978, T max = 0.988 19208 measured reflections 4930 independent reflections 3539 reflections with I > 2σ(I) R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.050 wR(F 2) = 0.142 S = 1.04 4930 reflections 238 parameters H-atom parameters constrained Δρmax = 0.45 e Å−3 Δρmin = −0.40 e Å−3 Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005708/bv2174sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005708/bv2174Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C7H10NO+·C6H2N3O8−F(000) = 760
Mr = 368.27Dx = 1.593 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4930 reflections
a = 10.6957 (4) Åθ = 1.9–31.8°
b = 17.8368 (5) ŵ = 0.14 mm−1
c = 8.0527 (3) ÅT = 293 K
β = 91.991 (2)°Prism, colourless
V = 1535.34 (9) Å30.22 × 0.18 × 0.12 mm
Z = 4
Bruker SMART APEXII CCD area-detector diffractometer4930 independent reflections
Radiation source: fine-focus sealed tube3539 reflections with I > 2σ(I)
graphiteRint = 0.028
φ and ω scansθmax = 31.8°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)h = −15→15
Tmin = 0.978, Tmax = 0.988k = −25→26
19208 measured reflectionsl = −11→11
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0626P)2 + 0.4547P] where P = (Fo2 + 2Fc2)/3
4930 reflections(Δ/σ)max < 0.001
238 parametersΔρmax = 0.45 e Å−3
0 restraintsΔρmin = −0.40 e Å−3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.
xyzUiso*/Ueq
O1−0.00430 (12)0.14533 (7)0.45345 (16)0.0536 (4)
N10.18296 (12)0.21738 (7)0.59909 (15)0.0366 (3)
C10.08388 (13)0.26071 (8)0.51522 (17)0.0344 (4)
C2−0.01386 (14)0.22085 (9)0.43872 (19)0.0400 (4)
C3−0.10912 (16)0.26008 (12)0.3561 (2)0.0529 (6)
C4−0.10434 (19)0.33740 (12)0.3498 (3)0.0592 (6)
C5−0.0059 (2)0.37645 (11)0.4229 (3)0.0580 (6)
C60.08921 (16)0.33785 (9)0.5076 (2)0.0450 (5)
C7−0.1013 (2)0.10034 (13)0.3781 (3)0.0712 (8)
O20.30956 (10)0.18764 (5)0.31638 (13)0.0372 (3)
O30.18239 (12)0.01420 (9)0.30014 (18)0.0662 (5)
O40.26170 (13)0.05325 (8)0.53302 (15)0.0569 (4)
O50.43465 (12)−0.06180 (6)0.30043 (17)0.0508 (4)
O60.64034 (12)−0.08887 (6)0.14078 (16)0.0519 (4)
O70.76246 (12)0.00182 (7)0.07391 (18)0.0585 (4)
O80.63270 (16)0.25143 (8)0.0819 (3)0.0929 (7)
O90.46083 (14)0.28678 (7)0.1770 (3)0.0813 (7)
N20.26692 (12)0.04141 (7)0.38421 (16)0.0376 (4)
N30.66485 (12)−0.02118 (7)0.12862 (16)0.0405 (4)
N40.53537 (12)0.23793 (7)0.14816 (19)0.0428 (4)
C80.39391 (12)0.14238 (7)0.27345 (16)0.0299 (3)
C90.38107 (13)0.06399 (7)0.30251 (17)0.0323 (4)
C100.46368 (14)0.00851 (7)0.26041 (18)0.0346 (4)
C110.57235 (13)0.03198 (8)0.17977 (18)0.0346 (4)
C120.59200 (13)0.10722 (8)0.14638 (18)0.0353 (4)
C130.50678 (13)0.16065 (7)0.19047 (17)0.0326 (4)
H1A0.233600.198700.524000.0550*
H1B0.149300.180000.655600.0550*
H1C0.226400.247000.668900.0550*
H3−0.175800.234500.305300.0630*
H4−0.168700.363600.295100.0710*
H5A−0.003300.428500.415600.0700*
H60.155700.363700.558500.0540*
H7A−0.179800.112900.425100.1070*
H7B−0.083200.048300.397900.1070*
H7C−0.105800.109600.260600.1070*
H50.49030−0.090100.271600.0760*
H120.664000.121700.093300.0420*
U11U22U33U12U13U23
O10.0559 (7)0.0422 (6)0.0617 (8)−0.0173 (5)−0.0108 (6)−0.0007 (5)
N10.0394 (6)0.0344 (6)0.0360 (6)−0.0046 (5)0.0009 (5)−0.0036 (5)
C10.0349 (7)0.0371 (7)0.0316 (6)−0.0025 (5)0.0071 (5)−0.0028 (5)
C20.0382 (7)0.0448 (8)0.0372 (7)−0.0080 (6)0.0054 (6)−0.0011 (6)
C30.0390 (8)0.0708 (12)0.0487 (9)−0.0041 (8)−0.0011 (7)0.0013 (8)
C40.0530 (10)0.0678 (12)0.0567 (11)0.0164 (9)0.0010 (9)0.0078 (9)
C50.0692 (12)0.0435 (9)0.0616 (11)0.0104 (8)0.0064 (10)0.0029 (8)
C60.0491 (9)0.0380 (8)0.0484 (9)−0.0038 (6)0.0070 (7)−0.0043 (6)
C70.0722 (13)0.0657 (12)0.0750 (14)−0.0377 (11)−0.0093 (11)−0.0021 (10)
O20.0427 (5)0.0302 (5)0.0391 (5)0.0093 (4)0.0059 (4)0.0036 (4)
O30.0518 (7)0.0849 (10)0.0619 (9)−0.0254 (7)0.0013 (6)−0.0089 (7)
O40.0685 (8)0.0630 (8)0.0397 (6)−0.0072 (6)0.0112 (6)0.0038 (5)
O50.0551 (7)0.0250 (5)0.0729 (8)0.0048 (5)0.0093 (6)0.0032 (5)
O60.0591 (7)0.0340 (6)0.0626 (8)0.0103 (5)0.0011 (6)−0.0118 (5)
O70.0470 (7)0.0551 (7)0.0744 (9)0.0086 (6)0.0155 (6)−0.0091 (6)
O80.0737 (10)0.0508 (8)0.1580 (18)−0.0022 (7)0.0568 (11)0.0234 (10)
O90.0604 (8)0.0281 (6)0.1575 (17)0.0013 (6)0.0329 (10)0.0079 (8)
N20.0429 (7)0.0294 (5)0.0407 (7)−0.0008 (5)0.0036 (5)0.0046 (5)
N30.0436 (7)0.0376 (6)0.0400 (7)0.0088 (5)−0.0023 (5)−0.0090 (5)
N40.0378 (6)0.0310 (6)0.0595 (8)−0.0029 (5)0.0004 (6)0.0055 (5)
C80.0339 (6)0.0269 (6)0.0286 (6)0.0017 (5)−0.0021 (5)−0.0003 (4)
C90.0346 (6)0.0269 (6)0.0353 (7)0.0002 (5)0.0018 (5)0.0003 (5)
C100.0407 (7)0.0257 (6)0.0371 (7)0.0021 (5)−0.0037 (6)−0.0022 (5)
C110.0355 (7)0.0317 (6)0.0363 (7)0.0059 (5)−0.0017 (5)−0.0052 (5)
C120.0326 (6)0.0359 (7)0.0373 (7)0.0010 (5)−0.0003 (5)−0.0026 (5)
C130.0338 (6)0.0262 (6)0.0375 (7)−0.0012 (5)−0.0020 (5)0.0002 (5)
O1—C21.356 (2)C1—C61.379 (2)
O1—C71.430 (3)C2—C31.387 (2)
O2—C81.2676 (16)C3—C41.381 (3)
O3—N21.2119 (19)C4—C51.377 (3)
O4—N21.2200 (18)C5—C61.388 (3)
O5—C101.3342 (17)C3—H30.9300
O6—N31.2401 (17)C4—H40.9300
O7—N31.2183 (18)C5—H5A0.9300
O8—N41.210 (2)C6—H60.9300
O9—N41.2090 (19)C7—H7C0.9600
O5—H50.8200C7—H7A0.9600
N1—C11.4583 (19)C7—H7B0.9600
N1—H1C0.8900C8—C131.4374 (19)
N1—H1A0.8900C8—C91.4251 (18)
N1—H1B0.8900C9—C101.3769 (19)
N2—C91.4634 (19)C10—C111.414 (2)
N3—C111.4408 (19)C11—C121.386 (2)
N4—C131.4550 (18)C12—C131.3739 (19)
C1—C21.390 (2)C12—H120.9300
O1···N12.6221 (18)N3···C10iii3.3846 (19)
O1···C4i3.415 (3)N4···O22.9496 (17)
O2···C13.2183 (17)N3···H52.5400
O2···N1ii2.7569 (16)C1···O23.2183 (17)
O2···C6ii3.397 (2)C1···C3i3.511 (2)
O2···O43.0189 (17)C2···C3i3.562 (2)
O2···O92.6703 (19)C3···C2ii3.562 (2)
O2···N12.7408 (16)C3···O8xi3.365 (3)
O2···N22.7068 (15)C3···C1ii3.511 (2)
O2···N42.9496 (17)C4···O1ii3.415 (3)
O3···O53.0194 (18)C6···O7ix3.402 (2)
O3···O7iii3.103 (2)C6···O2i3.397 (2)
O4···N13.0974 (19)C7···O7xii3.311 (3)
O4···O23.0189 (17)C7···O4v3.324 (3)
O4···C11iv3.2443 (19)C10···N3iii3.3846 (19)
O4···C7v3.324 (3)C11···C11iii3.431 (2)
O4···N3iv2.8670 (18)C11···O4iv3.2443 (19)
O4···O6iv2.8654 (18)C12···O6iii3.3512 (19)
O5···N32.9560 (18)C13···O6iii3.3074 (19)
O5···O62.6311 (18)C3···H7C2.7900
O5···O9vi2.9263 (17)C3···H7A2.7900
O5···N22.6733 (17)C5···H7Ci2.9700
O5···O33.0194 (18)C5···H1Bii2.9400
O6···O9vi2.890 (2)C6···H1Bii2.9500
O6···C13iii3.3074 (19)C7···H32.5800
O6···C12iii3.3512 (19)C8···H6ii3.0300
O6···O52.6311 (18)C8···H1A2.8700
O6···O4iv2.8654 (18)C8···H1Cii2.7800
O7···C6vi3.402 (2)H1A···O12.7600
O7···O3iii3.103 (2)H1A···O9i2.7000
O7···C7vii3.311 (3)H1A···O21.8900
O8···C3viii3.365 (3)H1A···O42.6100
O9···O6ix2.890 (2)H1A···C82.8700
O9···O5ix2.9263 (17)H1B···C5i2.9400
O9···N1ii3.017 (2)H1B···C6i2.9500
O9···O22.6703 (19)H1B···O42.7600
O1···H1A2.7600H1B···O12.3500
O1···H1B2.3500H1C···H62.3800
O2···H1Cii1.8700H1C···O9i2.5800
O2···H1A1.8900H1C···C8i2.7800
O2···H6ii2.7600H1C···O2i1.8700
O3···H7Bv2.9100H3···H7A2.3700
O3···H4x2.8000H3···H7C2.3800
O4···H1B2.7600H3···O8xii2.7000
O4···H7Bv2.7000H3···C72.5800
O4···H1A2.6100H4···O3xiii2.8000
O6···H6vi2.8800H5···N32.5400
O6···H51.9500H5···O9vi2.2900
O7···H7Cvii2.7900H5···O61.9500
O7···H122.3900H5A···O7ix2.8900
O7···H6vi2.8400H6···H1C2.3800
O7···H5Avi2.8900H6···O6ix2.8800
O8···H3vii2.7000H6···O7ix2.8400
O8···H122.3400H6···O2i2.7600
O9···H1Aii2.7000H6···C8i3.0300
O9···H5ix2.2900H7A···H32.3700
O9···H1Cii2.5800H7A···C32.7900
N1···O9i3.017 (2)H7B···O4v2.7000
N1···O22.7408 (16)H7B···O3v2.9100
N1···O12.6221 (18)H7C···O7xii2.7900
N1···O43.0974 (19)H7C···H32.3800
N1···O2i2.7569 (16)H7C···C5ii2.9700
N2···O52.6733 (17)H7C···C32.7900
N2···O22.7068 (15)H12···O72.3900
N3···O4iv2.8670 (18)H12···O82.3400
N3···O52.9560 (18)
C2—O1—C7117.97 (14)C5—C4—H4119.00
C10—O5—H5109.00C6—C5—H5A120.00
H1B—N1—H1C109.00C4—C5—H5A120.00
C1—N1—H1B109.00C5—C6—H6120.00
C1—N1—H1A109.00C1—C6—H6120.00
H1A—N1—H1C110.00O1—C7—H7C109.00
C1—N1—H1C109.00O1—C7—H7B109.00
H1A—N1—H1B109.00H7B—C7—H7C109.00
O4—N2—C9117.47 (13)H7A—C7—H7B110.00
O3—N2—C9118.49 (13)H7A—C7—H7C110.00
O3—N2—O4124.01 (14)O1—C7—H7A109.00
O6—N3—C11117.97 (12)O2—C8—C9120.43 (12)
O7—N3—C11119.17 (12)C9—C8—C13112.71 (11)
O6—N3—O7122.86 (13)O2—C8—C13126.84 (12)
O8—N4—O9121.62 (15)N2—C9—C10117.74 (12)
O9—N4—C13119.50 (14)C8—C9—C10126.76 (13)
O8—N4—C13118.86 (13)N2—C9—C8115.50 (11)
C2—C1—C6121.49 (14)O5—C10—C11126.23 (13)
N1—C1—C6121.27 (13)C9—C10—C11116.42 (12)
N1—C1—C2117.21 (13)O5—C10—C9117.35 (13)
C1—C2—C3118.89 (15)N3—C11—C12118.13 (12)
O1—C2—C1114.58 (13)C10—C11—C12120.54 (13)
O1—C2—C3126.53 (15)N3—C11—C10121.33 (12)
C2—C3—C4119.60 (17)C11—C12—C13121.00 (13)
C3—C4—C5121.20 (19)N4—C13—C12116.74 (12)
C4—C5—C6119.71 (18)C8—C13—C12122.57 (12)
C1—C6—C5119.10 (16)N4—C13—C8120.69 (12)
C4—C3—H3120.00C11—C12—H12119.00
C2—C3—H3120.00C13—C12—H12120.00
C3—C4—H4119.00
C7—O1—C2—C1179.98 (15)C3—C4—C5—C6−1.4 (3)
C7—O1—C2—C3−0.4 (2)C4—C5—C6—C10.8 (3)
O4—N2—C9—C10105.00 (16)O2—C8—C9—C10178.89 (14)
O3—N2—C9—C8102.38 (16)C13—C8—C9—C100.3 (2)
O4—N2—C9—C8−75.60 (17)O2—C8—C13—N40.7 (2)
O3—N2—C9—C10−77.02 (18)C9—C8—C13—N4179.16 (13)
O7—N3—C11—C10−173.12 (14)C13—C8—C9—N2−179.01 (12)
O6—N3—C11—C12−171.69 (14)O2—C8—C13—C12−178.89 (14)
O7—N3—C11—C127.5 (2)C9—C8—C13—C12−0.44 (19)
O6—N3—C11—C107.7 (2)O2—C8—C9—N2−0.45 (19)
O8—N4—C13—C8178.25 (17)N2—C9—C10—O5−1.3 (2)
O9—N4—C13—C8−3.1 (2)C8—C9—C10—C11−0.1 (2)
O8—N4—C13—C12−2.1 (2)N2—C9—C10—C11179.24 (12)
O9—N4—C13—C12176.54 (18)C8—C9—C10—O5179.33 (14)
N1—C1—C6—C5178.46 (16)C9—C10—C11—N3−179.46 (13)
C2—C1—C6—C50.6 (2)C9—C10—C11—C12−0.1 (2)
N1—C1—C2—C3−179.29 (13)O5—C10—C11—C12−179.44 (15)
C6—C1—C2—O1178.32 (14)O5—C10—C11—N31.2 (2)
N1—C1—C2—O10.41 (19)C10—C11—C12—C130.0 (2)
C6—C1—C2—C3−1.4 (2)N3—C11—C12—C13179.36 (13)
C1—C2—C3—C40.8 (2)C11—C12—C13—N4−179.30 (13)
O1—C2—C3—C4−178.90 (17)C11—C12—C13—C80.3 (2)
C2—C3—C4—C50.6 (3)
D—H···AD—HH···AD···AD—H···A
N1—H1A···O20.891.892.7408 (16)158
N1—H1C···O2i0.891.872.7569 (16)177
N1—H1C···O9i0.892.583.017 (2)111
O5—H5···O60.821.952.6311 (18)140
O5—H5···N30.822.542.9560 (18)112
O5—H5···O9vi0.822.292.9263 (17)135
C12—H12···O80.932.342.663 (2)100
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1A⋯O20.891.892.7408 (16)158
N1—H1C⋯O2i0.891.872.7569 (16)177
O5—H5⋯O60.821.952.6311 (18)140
O5—H5⋯O9ii0.822.292.9263 (17)135

Symmetry codes: (i) ; (ii) .

  4 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.  First-principles study of electronic, absorption, and thermodynamic properties of crystalline styphnic acid and its metal salts.

Authors:  Weihua Zhu; Heming Xiao
Journal:  J Phys Chem B       Date:  2009-07-30       Impact factor: 2.991

3.  Morpholinium styphnate.

Authors:  D Kalaivani; R Malarvizhi
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-10-02

4.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  4 in total
  2 in total

1.  Crystal structure and thermal behaviour of pyridinium styphnate.

Authors:  Selvarasu Muthulakshmi; Doraisamyraja Kalaivani
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-01-03

2.  Crystal structure of 1,10-phenanthrolinium 3-hy-droxy-2,4,6-tri-nitro-phenolate.

Authors:  Selvarasu Muthulakshmi; Doraisamyraja Kalaivani
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-06-13
  2 in total

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