Literature DB >> 21588711

5-Carb-oxy-2,4-dihy-droxy-anilinium chloride.

Syeda Sohaila Naz, Nazar Ul Islam, M Nawaz Tahir.   

Abstract

In the title salt, C(7)H(8)NO(4) (+)·Cl(-), the organic group is planar with an r.m.s. deviation of 0.0265 Å. An S(6) ring motif is formed due to an intra-molecular O-H⋯O hydrogen bond. The compound consists of dimers due to inter-molecular O-H⋯O hydrogen bonds with an R(2) (2)(8) ring motif. The dimers are inter-linked through strong N-H⋯Cl and O-H⋯Cl hydrogen bonds, resulting in a three-dimensional polymeric network.

Entities:  

Year:  2010        PMID： 21588711      PMCID： PMC3007849          DOI： 10.1107/S1600536810033337

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


Related literature

For related structures, see: Bendjeddou et al. (2009 ▶); Dobson & Gerkin (1998 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C7H8NO4 +·Cl− M = 205.59 Monoclinic, a = 5.0667 (3) Å b = 28.4071 (13) Å c = 6.3966 (3) Å β = 97.649 (3)° V = 912.47 (8) Å3 Z = 4 Mo Kα radiation μ = 0.40 mm−1 T = 296 K 0.28 × 0.18 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.926, T max = 0.935 7094 measured reflections 1635 independent reflections 1108 reflections with I > 2σ(I) R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.044 wR(F 2) = 0.098 S = 1.01 1635 reflections 128 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.23 e Å−3 Δρmin = −0.22 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033337/si2289sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033337/si2289Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C7H8NO4+·Cl−F(000) = 424
Mr = 205.59Dx = 1.497 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1108 reflections
a = 5.0667 (3) Åθ = 2.9–25.2°
b = 28.4071 (13) ŵ = 0.40 mm−1
c = 6.3966 (3) ÅT = 296 K
β = 97.649 (3)°Prism, light green
V = 912.47 (8) Å30.28 × 0.18 × 0.16 mm
Z = 4
Bruker Kappa APEXII CCD diffractometer1635 independent reflections
Radiation source: fine-focus sealed tube1108 reflections with I > 2σ(I)
graphiteRint = 0.052
Detector resolution: 8.10 pixels mm-1θmax = 25.2°, θmin = 2.9°
ω scansh = −5→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −34→32
Tmin = 0.926, Tmax = 0.935l = −7→7
7094 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.01w = 1/[σ2(Fo2) + (0.036P)2 + 0.4226P] where P = (Fo2 + 2Fc2)/3
1635 reflections(Δ/σ)max < 0.001
128 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.22 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 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.
xyzUiso*/Ueq
O10.8567 (5)0.05383 (8)−0.1244 (4)0.0527 (8)
O20.7828 (4)0.01248 (8)0.1583 (3)0.0553 (8)
O30.4286 (5)0.04378 (8)0.3905 (4)0.0620 (10)
O40.0113 (4)0.18833 (7)0.1726 (3)0.0498 (8)
N10.2950 (5)0.19898 (8)−0.1420 (4)0.0404 (8)
C10.7367 (6)0.04694 (11)0.0429 (5)0.0420 (11)
C20.5471 (5)0.08321 (10)0.0823 (4)0.0373 (10)
C30.4020 (6)0.08012 (10)0.2540 (5)0.0404 (10)
C40.2197 (6)0.11460 (10)0.2882 (5)0.0415 (11)
C50.1841 (6)0.15295 (10)0.1561 (4)0.0366 (10)
C60.3332 (6)0.15690 (10)−0.0114 (4)0.0343 (9)
C70.5084 (6)0.12258 (10)−0.0495 (4)0.0376 (10)
Cl10.75184 (16)0.19834 (3)0.56278 (12)0.0476 (3)
H10.974 (7)0.0328 (12)−0.131 (5)0.0632*
H1A0.139930.19710−0.225190.0485*
H1B0.426490.20130−0.220800.0485*
H1C0.295150.22425−0.059700.0485*
H30.543 (7)0.0264 (13)0.342 (5)0.0743*
H40.121360.111860.400410.0498*
H4A−0.063 (6)0.1874 (11)0.284 (5)0.0597*
H70.602910.12534−0.164020.0451*
U11U22U33U12U13U23
O10.0541 (15)0.0463 (15)0.0613 (14)0.0190 (11)0.0212 (13)0.0073 (11)
O20.0518 (14)0.0443 (14)0.0728 (15)0.0160 (12)0.0189 (12)0.0144 (12)
O30.0706 (18)0.0536 (16)0.0664 (16)0.0192 (13)0.0267 (14)0.0218 (13)
O40.0599 (15)0.0434 (14)0.0525 (13)0.0153 (12)0.0311 (12)0.0053 (10)
N10.0393 (14)0.0373 (15)0.0483 (14)0.0049 (12)0.0195 (12)0.0009 (12)
C10.0349 (18)0.0375 (18)0.0538 (19)0.0028 (15)0.0067 (16)0.0026 (16)
C20.0321 (16)0.0322 (17)0.0480 (18)0.0030 (14)0.0073 (14)0.0010 (14)
C30.0410 (18)0.0357 (18)0.0453 (18)0.0028 (15)0.0085 (15)0.0084 (14)
C40.0448 (19)0.0414 (19)0.0415 (17)−0.0006 (16)0.0179 (15)0.0034 (15)
C50.0361 (18)0.0348 (18)0.0406 (16)−0.0005 (14)0.0116 (14)−0.0047 (14)
C60.0343 (16)0.0297 (17)0.0409 (16)0.0009 (13)0.0125 (14)0.0028 (13)
C70.0346 (17)0.0381 (18)0.0417 (16)0.0014 (14)0.0115 (14)−0.0018 (14)
Cl10.0500 (5)0.0494 (5)0.0480 (4)0.0043 (4)0.0240 (4)0.0048 (4)
O1—C11.314 (4)N1—H1C0.8900
O2—C11.230 (4)C1—C21.453 (4)
O3—C31.347 (4)C2—C71.399 (4)
O4—C51.346 (4)C2—C31.403 (4)
O1—H10.85 (3)C3—C41.384 (4)
O3—H30.85 (4)C4—C51.376 (4)
O4—H4A0.85 (3)C5—C61.395 (4)
N1—C61.456 (4)C6—C71.362 (4)
N1—H1A0.8900C4—H40.9300
N1—H1B0.8900C7—H70.9300
Cl1···N1i3.176 (3)C1···C1vi3.580 (4)
Cl1···N1ii3.124 (3)C1···O2vi3.245 (4)
Cl1···C7i3.622 (3)C1···O2v3.357 (4)
Cl1···O4iii2.985 (2)C1···C4iii3.335 (4)
Cl1···N1iv3.217 (2)C2···C4iii3.598 (4)
Cl1···H4Aiii2.15 (3)C3···C1viii3.587 (4)
Cl1···H1Aii2.2400C4···C2viii3.598 (4)
Cl1···H1Bi2.2900C4···C1viii3.335 (4)
Cl1···H1Civ2.3500C7···O4iii3.322 (4)
Cl1···H7i2.8800C7···Cl1ix3.622 (3)
O1···O2v2.653 (3)C1···H1v2.72 (3)
O2···O32.632 (3)C1···H32.34 (3)
O2···C1vi3.245 (4)H1···O2v1.81 (3)
O2···O1v2.653 (3)H1···C1v2.72 (3)
O2···C1v3.357 (4)H1···H1v2.50 (5)
O3···O3vii2.899 (3)H1A···Cl1x2.2400
O3···O22.632 (3)H1A···O42.7200
O4···N12.642 (3)H1B···H72.3500
O4···Cl1viii2.985 (2)H1B···Cl1ix2.2900
O4···C7viii3.322 (4)H1C···O42.4300
O1···H72.4000H1C···Cl1xi2.3500
O2···H31.84 (3)H3···C12.34 (3)
O2···H1v1.81 (3)H3···O21.84 (3)
O3···H3vii2.62 (3)H3···H3vii2.60 (5)
O4···H1C2.4300H3···O3vii2.62 (3)
O4···H1A2.7200H4···H4A2.4200
N1···Cl1ix3.176 (3)H4A···H42.4200
N1···Cl1x3.124 (3)H4A···Cl1viii2.15 (3)
N1···O42.642 (3)H7···Cl1ix2.8800
N1···Cl1xi3.217 (2)H7···O12.4000
C1···C3iii3.587 (4)H7···H1B2.3500
C1—O1—H1110 (2)O3—C3—C4116.8 (3)
C3—O3—H3103 (2)C2—C3—C4120.7 (3)
C5—O4—H4A114 (2)O3—C3—C2122.5 (3)
C6—N1—H1C109.00C3—C4—C5120.0 (3)
H1A—N1—H1B109.00C4—C5—C6119.7 (3)
C6—N1—H1A109.00O4—C5—C6115.1 (2)
C6—N1—H1B109.00O4—C5—C4125.2 (3)
H1B—N1—H1C109.00N1—C6—C5117.5 (3)
H1A—N1—H1C109.00N1—C6—C7121.7 (2)
O1—C1—C2115.1 (3)C5—C6—C7120.8 (3)
O1—C1—O2122.4 (3)C2—C7—C6120.5 (3)
O2—C1—C2122.5 (3)C3—C4—H4120.00
C1—C2—C7120.4 (2)C5—C4—H4120.00
C3—C2—C7118.4 (3)C2—C7—H7120.00
C1—C2—C3121.2 (3)C6—C7—H7120.00
O1—C1—C2—C3179.2 (3)O3—C3—C4—C5179.4 (3)
O1—C1—C2—C7−1.8 (4)C2—C3—C4—C5−1.6 (5)
O2—C1—C2—C3−1.2 (5)C3—C4—C5—O4179.3 (3)
O2—C1—C2—C7177.8 (3)C3—C4—C5—C6−0.2 (4)
C1—C2—C3—O3−0.2 (4)O4—C5—C6—N12.6 (4)
C1—C2—C3—C4−179.2 (3)O4—C5—C6—C7−177.7 (3)
C7—C2—C3—O3−179.2 (3)C4—C5—C6—N1−177.8 (3)
C7—C2—C3—C41.8 (4)C4—C5—C6—C71.9 (4)
C1—C2—C7—C6−179.2 (3)N1—C6—C7—C2178.0 (3)
C3—C2—C7—C6−0.2 (4)C5—C6—C7—C2−1.7 (4)
D—H···AD—HH···AD···AD—H···A
O1—H1···O2v0.85 (3)1.81 (3)2.653 (3)177 (4)
N1—H1A···Cl1x0.892.243.124 (3)176
N1—H1B···Cl1ix0.892.293.176 (3)173
N1—H1C···Cl1xi0.892.353.217 (2)163
O3—H3···O20.85 (4)1.84 (3)2.632 (3)154 (3)
O4—H4A···Cl1viii0.85 (3)2.15 (3)2.985 (2)170 (3)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1—H1⋯O2i0.85 (3)1.81 (3)2.653 (3)177 (4)
N1—H1A⋯Cl1ii0.892.243.124 (3)176
N1—H1B⋯Cl1iii0.892.293.176 (3)173
N1—H1C⋯Cl1iv0.892.353.217 (2)163
O3—H3⋯O20.85 (4)1.84 (3)2.632 (3)154 (3)
O4—H4A⋯Cl1v0.85 (3)2.15 (3)2.985 (2)170 (3)

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

  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.  Bis(3-carboxy-anilinum) bis-(perchlorate) monohydrate.

Authors:  Lamia Bendjeddou; Aouatef Cherouana; Nasreddine Hadjadj; Slimane Dahaoui; Claude Lecomte
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-07-04

3.  5-ammoniosalicylic acid chloride monohydrate.

Authors:  A J Dobson; R E Gerkin
Journal:  Acta Crystallogr C       Date:  1998-11-15       Impact factor: 1.172

4.  Structure validation in chemical crystallography.

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

1.  5-Carb-oxy-2,4-dihy-droxy-anilinium chloride dihydrate.

Authors:  Syeda Sohaila Naz; Nazar Ul Islam; M Nawaz Tahir
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-01-08
  1 in total

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