Download citation
Download citation
link to html
The structure of quinoline N-oxide dihydrate, C9H7NO·2H2O, has been determined from X-ray powder diffraction data, using grid search technique and a bond-restrained Rietveld refinement. The structure features an interesting system of co-operative hydrogen bonds, which apparently involves all four `active' H atoms, and is based on the infinite chains formed by two alternating symmetry-independent water mol­ecules. The chains are further interlinked through two more symmetry-independent hydrogen bonds which make use of the N-oxide O atom as hydrogen-bond acceptor.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802012564/ya6107sup1.cif
Contains datablocks I, global

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S1600536802012564/ya6107Isup2.rtv
Contains datablock I

CCDC reference: 193774

Key indicators

  • Powder X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.009 Å
  • H-atom completeness 64%
  • R factor = 0.000
  • wR factor = 0.000
  • Data-to-parameter ratio = 0.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_202 Alert C Isotropic non-H Atoms in Anion/Solvent = 2 General Notes
FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C9 H11 N1 O3 Atom count from the _atom_site data: C9 H7 N1 O3 CELLZ_01 From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C9 H11 N O3 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 36.00 36.00 0.00 H 44.00 28.00 16.00 N 4.00 4.00 0.00 O 12.00 12.00 0.00 Difference between formula and atom_site contents detected. WARNING: H atoms missing from atom site list. Is this intentional? CHEMW_03 From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_weight 181.19 TEST: Calculate formula weight from _atom_site_* atom mass num sum O 16.00 3.00 48.00 N 14.01 1.00 14.01 C 12.01 9.00 108.10 H 1.01 7.00 7.06 Calculated formula weight 177.16 The ratio of given/expected molecular weight as calculated from the _atom_site* data lies outside the range 0.99 <> 1.01
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: local program; data reduction: local program; program(s) used to solve structure: MRIA (Zlokazov & Chernyshev, 1992); program(s) used to refine structure: MRIA; molecular graphics: PCMODEL (Version 7.0) [Reference?]; software used to prepare material for publication: MRIA and PARST (Nardelli, 1983).

(I) top
Crystal data top
C9H7NO·2H2OF(000) = 384
Mr = 181.19Dx = 1.285 Mg m3
Monoclinic, P21/nMelting point: 51(1) K
a = 9.484 (3) ÅCu Kα radiation, λ = 1.5418 Å
b = 16.235 (5) ÅT = 293 K
c = 6.907 (2) ÅParticle morphology: no specific habit
β = 118.25 (2)°light grey
V = 936.8 (5) Å3flat_sheet, 12 × 12 mm
Z = 4
Data collection top
X-ray powder
diffractometer DRON-4.07
Data collection mode: reflection
Radiation source: BSV-28, line-focus sealed tubeScan method: step
Pyrolitic graphite crystal monochromator2θmin = 10°, 2θmax = 60°, 2θstep = 0.02°
Specimen mounting: The powder was sprinkled on the sample holder.
Refinement top
Refinement on Inet126 parameters
Least-squares matrix: full with fixed elements per cycle1 constraint
Rp = 0.028H atoms treated by a mixture of independent and constrained refinement
Rwp = 0.040Weighting scheme based on measured s.u.'s
Rexp = 0.012(Δ/σ)max = 0.02
2501 data pointsBackground function: Chebyshev polynomial up to the 5th order'
Profile function: split-type pseudo-Voigt (Toraya, 1986)Preferred orientation correction: Spherical harmonics expansion (Ahtee et al., 1989) up to the 6th order.
Special details top

Experimental. specimen was rotated in its plane

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.0298 (9)0.0533 (3)0.2292 (13)0.143 (4)*
C20.2676 (5)0.0249 (3)0.0699 (6)0.056 (3)*
C30.0121 (8)0.0980 (3)0.2405 (11)0.100 (3)*
C40.2258 (6)0.0126 (3)0.3986 (9)0.080 (4)*
C50.2409 (11)0.1629 (5)0.4134 (15)0.160 (4)*
O60.0141 (6)0.2410 (3)0.2452 (9)0.119 (2)*
C70.1906 (6)0.0485 (3)0.1189 (9)0.102 (3)*
C80.1796 (8)0.0981 (3)0.1177 (11)0.158 (4)*
C90.0664 (6)0.0207 (3)0.2929 (9)0.099 (4)*
C100.3182 (7)0.0853 (4)0.4675 (11)0.150 (3)*
N110.0828 (6)0.1714 (3)0.3009 (9)0.144 (3)*
H10.02000.10400.27020.051*
H20.37970.02790.01540.051*
H40.27610.03790.44230.051*
H50.30490.21060.45620.051*
H70.25140.09860.08300.051*
H80.23430.14750.08090.051*
H100.42960.08160.54470.051*
OW10.0545 (3)0.2796 (2)0.5565 (4)0.039 (2)*
OW20.1435 (5)0.2862 (2)0.0136 (7)0.118 (2)*
Geometric parameters (Å, º) top
O6—N111.269 (7)C3—C81.403 (9)
N11—C31.431 (7)C4—C91.338 (7)
N11—C51.33 (1)C4—C101.412 (8)
O6—OW12.601 (7)C5—C101.42 (1)
O6—OW22.705 (8)C1—H10.92
OW1—OW2i2.660 (9)C2—H20.94
OW1—OW2ii2.875 (9)C8—H80.92
C1—C71.346 (9)C4—H40.92
C1—C91.445 (8)C10—H100.93
C2—C71.354 (7)C5—H50.94
C2—C81.399 (7)C7—H70.94
C3—N11—O6119.4 (5)C7—C1—H1120
C5—N11—O6123.0 (7)C7—C2—H2121
C3—N11—C5117.6 (7)C8—C2—H2118
N11—C5—C10123.1 (8)C9—C4—H4123
C5—C10—C4119.6 (6)C10—C4—H4119
C10—C4—C9117.6 (6)N11—C5—H5119
C4—C9—C3123.2 (6)C10—C5—H5118
C9—C1—C7120.5 (6)C1—C7—H7119
C1—C7—C2121.7 (5)C2—C7—H7120
C7—C2—C8119.8 (5)C2—C8—H8119
C2—C8—C3121.3 (6)C3—C8—H8120
C8—C3—C9117.6 (6)C4—C10—H10120
C3—C9—C1118.6 (4)C5—C10—H10121
C9—C1—H1119
Symmetry codes: (i) x, y, z+1; (ii) x1/2, y+1/2, z+1/2.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds