2-Carboxy­quinolinium chloride monohydrate

In the title compound, C₁₀H₈NO₂⁺·Cl⁻·H₂O, all bond lengths and angles are within normal ranges. The 2-carboxy­quinolinium cation is essentially planar. Inter­molecular O—H...O, O—H...Cl and N—H...Cl hydrogen bonds stabilize the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.094
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ...     522.50 Ang-3
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) .        200 Ang.
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)        3000 Deg.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C10 H8 N O2

   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

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: COLLECT (Nonius, 2002); cell refinement: DIRAX (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

2-Carboxyquinolinium chloride monohydrate

Crystal data

C10H8NO2^+·Cl^−·H2O	Z = 2
Mr = 227.64	F(000) = 236
Triclinic, P1	Dx = 1.447 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.120 (2) Å	Cell parameters from 7191 reflections
b = 8.470 (2) Å	θ = 4.0–27.5°
c = 9.165 (2) Å	µ = 0.35 mm^−1
α = 106.33 (3)°	T = 173 K
β = 105.68 (3)°	Block, colourless
γ = 109.41 (3)°	0.25 × 0.20 × 0.05 mm
V = 522.5 (2) Å^3

Data collection

Nonius KappaCCD diffractometer	2382 independent reflections
Radiation source: fine-focus sealed tube	1717 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
ω and φ scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.917, Tmax = 0.983	k = −10→10
7192 measured reflections	l = −11→11

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0428P)^2 + 0.0555P] where P = (Fo^2 + 2Fc^2)/3
2382 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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
Cl1	0.29104 (6)	0.59859 (6)	0.33730 (6)	0.03654 (16)
O1	0.07401 (18)	0.24083 (17)	0.66603 (15)	0.0362 (3)
H1	0.1647	0.3124	0.6541	0.054*
N1	−0.04389 (19)	0.24014 (19)	1.00984 (17)	0.0270 (3)
H1A	0.0393	0.3533	1.0793	0.032*
C1	−0.0549 (2)	0.1816 (2)	0.8547 (2)	0.0278 (4)
O2	0.18510 (18)	0.47290 (17)	0.91777 (16)	0.0372 (3)
C2	−0.1839 (2)	0.0022 (2)	0.7393 (2)	0.0334 (4)
H2A	−0.1926	−0.0399	0.6286	0.040*
O3	0.3316 (2)	0.4383 (2)	0.6038 (2)	0.0476 (4)
H1W	0.314 (3)	0.477 (3)	0.533 (3)	0.056 (8)*
H2W	0.434 (4)	0.414 (3)	0.621 (3)	0.069 (8)*
C3	−0.2974 (3)	−0.1114 (3)	0.7901 (2)	0.0351 (4)
H3A	−0.3856	−0.2332	0.7129	0.042*
C4	−0.4002 (2)	−0.1641 (3)	1.0121 (2)	0.0347 (4)
H4A	−0.4872	−0.2881	0.9401	0.042*
C5	−0.3855 (3)	−0.0949 (3)	1.1710 (3)	0.0385 (5)
H5A	−0.4627	−0.1712	1.2086	0.046*
C6	−0.2559 (2)	0.0906 (3)	1.2816 (2)	0.0370 (5)
H6A	−0.2481	0.1364	1.3918	0.044*
C7	−0.1426 (2)	0.2034 (3)	1.2309 (2)	0.0324 (4)
H7A	−0.0566	0.3270	1.3049	0.039*
C8	−0.2863 (2)	−0.0519 (2)	0.9536 (2)	0.0296 (4)
C9	−0.1553 (2)	0.1336 (2)	1.0673 (2)	0.0273 (4)
C10	0.0821 (2)	0.3167 (2)	0.8158 (2)	0.0287 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0301 (2)	0.0377 (3)	0.0349 (3)	0.0096 (2)	0.00931 (19)	0.0154 (2)
O1	0.0363 (7)	0.0382 (7)	0.0337 (7)	0.0126 (6)	0.0175 (6)	0.0157 (6)
N1	0.0237 (7)	0.0238 (7)	0.0284 (8)	0.0079 (6)	0.0078 (6)	0.0096 (6)
C1	0.0276 (8)	0.0276 (9)	0.0305 (10)	0.0139 (8)	0.0103 (8)	0.0141 (8)
O2	0.0383 (7)	0.0297 (7)	0.0376 (8)	0.0074 (6)	0.0173 (6)	0.0129 (6)
C2	0.0339 (10)	0.0309 (10)	0.0302 (10)	0.0123 (8)	0.0111 (8)	0.0099 (8)
O3	0.0398 (9)	0.0652 (11)	0.0541 (10)	0.0245 (8)	0.0255 (8)	0.0384 (9)
C3	0.0328 (9)	0.0254 (9)	0.0368 (11)	0.0086 (8)	0.0096 (8)	0.0081 (8)
C4	0.0276 (9)	0.0290 (10)	0.0460 (12)	0.0094 (8)	0.0122 (8)	0.0196 (9)
C5	0.0293 (9)	0.0441 (12)	0.0499 (13)	0.0148 (9)	0.0177 (9)	0.0295 (10)
C6	0.0302 (9)	0.0482 (12)	0.0350 (11)	0.0167 (9)	0.0128 (8)	0.0210 (9)
C7	0.0256 (9)	0.0341 (10)	0.0316 (10)	0.0100 (8)	0.0082 (8)	0.0123 (8)
C8	0.0243 (8)	0.0286 (9)	0.0359 (10)	0.0128 (8)	0.0091 (8)	0.0146 (8)
C9	0.0212 (8)	0.0290 (9)	0.0331 (10)	0.0115 (7)	0.0085 (7)	0.0164 (8)
C10	0.0279 (9)	0.0309 (10)	0.0309 (10)	0.0154 (8)	0.0108 (8)	0.0155 (8)

Geometric parameters (Å, º)

O1—C10	1.315 (2)	C3—C8	1.407 (3)
O1—H1	0.8400	C3—H3A	0.9500
N1—C1	1.335 (2)	C4—C5	1.363 (3)
N1—C9	1.376 (2)	C4—C8	1.420 (3)
N1—H1A	0.8800	C4—H4A	0.9500
C1—C2	1.402 (3)	C5—C6	1.426 (3)
C1—C10	1.507 (3)	C5—H5A	0.9500
O2—C10	1.213 (2)	C6—C7	1.368 (3)
C2—C3	1.373 (3)	C6—H6A	0.9500
C2—H2A	0.9500	C7—C9	1.409 (2)
O3—H1W	0.81 (3)	C7—H7A	0.9500
O3—H2W	0.91 (3)	C8—C9	1.433 (3)
C10—O1—H1	109.5	C4—C5—H5A	119.5
C1—N1—C9	123.70 (15)	C6—C5—H5A	119.5
C1—N1—H1A	118.2	C7—C6—C5	120.72 (18)
C9—N1—H1A	118.2	C7—C6—H6A	119.6
N1—C1—C2	120.52 (16)	C5—C6—H6A	119.6
N1—C1—C10	116.07 (15)	C6—C7—C9	119.04 (17)
C2—C1—C10	123.38 (17)	C6—C7—H7A	120.5
C3—C2—C1	118.40 (17)	C9—C7—H7A	120.5
C3—C2—H2A	120.8	C3—C8—C4	123.77 (16)
C1—C2—H2A	120.8	C3—C8—C9	118.36 (16)
H1W—O3—H2W	114 (2)	C4—C8—C9	117.86 (17)
C2—C3—C8	121.67 (16)	N1—C9—C7	121.60 (15)
C2—C3—H3A	119.2	N1—C9—C8	117.31 (16)
C8—C3—H3A	119.2	C7—C9—C8	121.09 (16)
C5—C4—C8	120.34 (17)	O2—C10—O1	127.67 (16)
C5—C4—H4A	119.8	O2—C10—C1	120.79 (16)
C8—C4—H4A	119.8	O1—C10—C1	111.52 (15)
C4—C5—C6	120.94 (17)
C9—N1—C1—C2	−0.5 (3)	C1—N1—C9—C7	−178.01 (17)
C9—N1—C1—C10	−178.60 (15)	C1—N1—C9—C8	1.7 (2)
N1—C1—C2—C3	−0.3 (3)	C6—C7—C9—N1	−179.48 (17)
C10—C1—C2—C3	177.64 (17)	C6—C7—C9—C8	0.8 (3)
C1—C2—C3—C8	−0.2 (3)	C3—C8—C9—N1	−2.1 (2)
C8—C4—C5—C6	−0.1 (3)	C4—C8—C9—N1	179.14 (15)
C4—C5—C6—C7	−0.2 (3)	C3—C8—C9—C7	177.63 (17)
C5—C6—C7—C9	−0.1 (3)	C4—C8—C9—C7	−1.1 (3)
C2—C3—C8—C4	−179.91 (18)	N1—C1—C10—O2	−5.2 (3)
C2—C3—C8—C9	1.4 (3)	C2—C1—C10—O2	176.74 (18)
C5—C4—C8—C3	−177.91 (18)	N1—C1—C10—O1	173.52 (15)
C5—C4—C8—C9	0.8 (3)	C2—C1—C10—O1	−4.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1^i	0.88	2.43	3.256 (3)	157
O3—H1W···Cl1	0.81 (3)	2.30 (3)	3.105 (2)	175 (2)
O1—H1···O3	0.84	1.69	2.521 (2)	173
O3—H2W···Cl1^ii	0.91 (3)	2.20 (3)	3.101 (2)	170 (2)

Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y+1, −z+1.