Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the title crystal structure, C9H14O3·H2O, the water mol­ecule accepts a hydrogen bond from the carboxyl group [O...O = 2.6004 (13) Å and O—H...O = 163°], while donating hydrogen bonds to the ketone [O...O = 2.8193 (14) Å and O—H...O = 178 (2)°] and the acid carbonyl groups [O...O = 2.8010 (14) Å and O—H...O = 174 (2)°]. This creates a network of hydrogen bonds confined within a continuous flat ribbon two mol­ecules in width and extending in the [101] direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807004795/lh2301sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807004795/lh2301Isup2.hkl
Contains datablock I

CCDC reference: 640412

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.031
  • wR factor = 0.086
  • Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 64.88 Deg.
Author Response: diffrn reflns theta full (too) Low...64.9\%. (Alert level A) and resolution (too) low [sin\q/\l < 0.6] (Alert level C): this problem has arisen because initially we were told by the manufacturer of our newly installed Bruker Smart Apex2 unit that we should be able to collect our small-molecule data down to only 0.85\%A resolution and have enough data (with copper K\a radiation). However, this yields a \q max. of ca. 64.9\%, less than the 67\% required by Acta. Since the crystals are no longer available, we are strapped with the current amount of data.
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.93
Author Response: diffrn_measured_fraction_theta_full Low 0.93. (Alert level A): this problem necessarily arose because we collected data out to only 0.85\%A resolution (with copper K\a radiation) as per manufacturer's instructions. However, this yields only 93% of the theoretical data. Since the crystals are no longer available, we are strapped with the current amount of data.

Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 64.90 From the CIF: _diffrn_reflns_theta_full 64.88 From the CIF: _reflns_number_total 1524 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 1638 Completeness (_total/calc) 93.04% THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5874 PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.93 PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6]..... 64.90 Deg. PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 2.92 Sigma PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 H2 O
2 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 6 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

3-(4-Oxocyclohexyl)propionic acid monohydrate top
Crystal data top
C9H14O3·H2OZ = 2
Mr = 188.22F(000) = 204
Triclinic, P1Dx = 1.291 Mg m3
Hall symbol: -P 1Melting point: 326 K
a = 7.4636 (2) ÅCu Kα radiation, λ = 1.54178 Å
b = 7.9944 (3) ÅCell parameters from 3199 reflections
c = 8.4817 (3) Åθ = 5.5–64.9°
α = 90.852 (2)°µ = 0.84 mm1
β = 106.903 (1)°T = 100 K
γ = 90.778 (2)°Block, colourless
V = 484.08 (3) Å30.22 × 0.17 × 0.08 mm
Data collection top
Bruker SMART CCD APEX-II area-detector
diffractometer
1524 independent reflections
Radiation source: fine-focus sealed tube1402 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.010
φ and ω scansθmax = 64.9°, θmin = 5.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 88
Tmin = 0.869, Tmax = 0.941k = 99
3199 measured reflectionsl = 99
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.086 w = 1/[σ2(Fo2) + (0.0441P)2 + 0.1704P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
1524 reflectionsΔρmax = 0.22 e Å3
128 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0038 (13)
Special details top

Experimental. crystal mounted on Cryo-loop using Paratone-N

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
O10.43881 (12)0.20680 (11)0.05401 (10)0.0239 (3)
C10.32314 (17)0.19412 (16)0.39011 (15)0.0193 (3)
H1A0.34940.07770.43120.023*
O20.10888 (13)0.46580 (11)0.74499 (11)0.0250 (3)
C20.17108 (17)0.18539 (16)0.22356 (15)0.0199 (3)
H2A0.13580.30040.18650.024*
H2B0.05840.12780.23710.024*
O30.09635 (13)0.25624 (12)0.73677 (11)0.0251 (3)
H30.12900.31880.80360.038*
C30.23702 (18)0.09181 (17)0.09093 (15)0.0215 (3)
H3A0.25340.02780.11920.026*
H3B0.14010.09910.01680.026*
C40.41831 (18)0.16404 (15)0.07739 (15)0.0200 (3)
O40.25491 (15)0.41010 (13)0.93165 (12)0.0274 (3)
H4A0.204 (3)0.445 (3)1.025 (3)0.051 (6)*
H4B0.353 (3)0.343 (3)0.940 (3)0.061 (6)*
C50.57229 (18)0.17934 (18)0.23759 (16)0.0240 (3)
H5A0.68020.24180.22020.029*
H5B0.61480.06640.27640.029*
C60.50335 (18)0.27070 (17)0.36871 (15)0.0227 (3)
H6A0.60260.26850.47550.027*
H6B0.48150.38920.33770.027*
C70.26440 (18)0.29753 (16)0.51985 (15)0.0213 (3)
H7A0.36990.30220.62260.026*
H7B0.24080.41340.48040.026*
C80.09139 (18)0.23090 (17)0.55953 (15)0.0221 (3)
H8A0.01530.22940.45760.026*
H8B0.11340.11400.59630.026*
C90.03898 (17)0.33118 (16)0.69024 (15)0.0200 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0269 (5)0.0263 (5)0.0204 (5)0.0005 (4)0.0100 (4)0.0007 (4)
C10.0210 (6)0.0182 (7)0.0183 (6)0.0011 (5)0.0050 (5)0.0007 (5)
O20.0279 (5)0.0217 (5)0.0261 (5)0.0028 (4)0.0095 (4)0.0053 (4)
C20.0186 (6)0.0218 (7)0.0194 (6)0.0016 (5)0.0060 (5)0.0014 (5)
O30.0285 (5)0.0250 (5)0.0245 (5)0.0042 (4)0.0126 (4)0.0037 (4)
C30.0225 (6)0.0230 (7)0.0186 (6)0.0028 (5)0.0058 (5)0.0023 (5)
C40.0236 (7)0.0160 (7)0.0219 (7)0.0016 (5)0.0090 (5)0.0009 (5)
O40.0306 (6)0.0311 (6)0.0229 (5)0.0069 (4)0.0123 (4)0.0040 (4)
C50.0193 (6)0.0312 (8)0.0220 (7)0.0010 (5)0.0068 (5)0.0021 (5)
C60.0206 (7)0.0268 (7)0.0190 (6)0.0038 (5)0.0035 (5)0.0004 (5)
C70.0231 (7)0.0206 (7)0.0193 (6)0.0025 (5)0.0050 (5)0.0021 (5)
C80.0236 (7)0.0212 (7)0.0207 (6)0.0026 (5)0.0058 (5)0.0027 (5)
C90.0198 (6)0.0201 (7)0.0182 (6)0.0017 (5)0.0027 (5)0.0022 (5)
Geometric parameters (Å, º) top
O1—C41.2212 (16)C4—C51.5051 (17)
C1—C61.5296 (17)O4—H4A0.82 (2)
C1—C71.5329 (17)O4—H4B0.92 (2)
C1—C21.5334 (16)C5—C61.5343 (18)
C1—H1A1.0000C5—H5A0.9900
O2—C91.2145 (16)C5—H5B0.9900
C2—C31.5409 (17)C6—H6A0.9900
C2—H2A0.9900C6—H6B0.9900
C2—H2B0.9900C7—C81.5178 (18)
O3—C91.3257 (16)C7—H7A0.9900
O3—H30.8400C7—H7B0.9900
C3—C41.4995 (18)C8—C91.5031 (17)
C3—H3A0.9900C8—H8A0.9900
C3—H3B0.9900C8—H8B0.9900
C6—C1—C7108.81 (10)C6—C5—H5A109.5
C6—C1—C2109.86 (10)C4—C5—H5B109.5
C7—C1—C2112.53 (10)C6—C5—H5B109.5
C6—C1—H1A108.5H5A—C5—H5B108.1
C7—C1—H1A108.5C1—C6—C5113.24 (11)
C2—C1—H1A108.5C1—C6—H6A108.9
C1—C2—C3112.02 (10)C5—C6—H6A108.9
C1—C2—H2A109.2C1—C6—H6B108.9
C3—C2—H2A109.2C5—C6—H6B108.9
C1—C2—H2B109.2H6A—C6—H6B107.7
C3—C2—H2B109.2C8—C7—C1114.59 (11)
H2A—C2—H2B107.9C8—C7—H7A108.6
C9—O3—H3109.5C1—C7—H7A108.6
C4—C3—C2111.33 (10)C8—C7—H7B108.6
C4—C3—H3A109.4C1—C7—H7B108.6
C2—C3—H3A109.4H7A—C7—H7B107.6
C4—C3—H3B109.4C9—C8—C7113.83 (11)
C2—C3—H3B109.4C9—C8—H8A108.8
H3A—C3—H3B108.0C7—C8—H8A108.8
O1—C4—C3122.31 (11)C9—C8—H8B108.8
O1—C4—C5122.78 (12)C7—C8—H8B108.8
C3—C4—C5114.91 (11)H8A—C8—H8B107.7
H4A—O4—H4B105.5 (19)O2—C9—O3123.78 (12)
C4—C5—C6110.62 (10)O2—C9—C8124.54 (12)
C4—C5—H5A109.5O3—C9—C8111.67 (11)
C6—C1—C2—C354.55 (14)C2—C1—C6—C554.85 (14)
C7—C1—C2—C3175.95 (11)C4—C5—C6—C152.71 (15)
C1—C2—C3—C453.28 (14)C6—C1—C7—C8177.37 (10)
C2—C3—C4—O1127.88 (12)C2—C1—C7—C860.63 (15)
C2—C3—C4—C552.22 (14)C1—C7—C8—C9178.43 (10)
O1—C4—C5—C6128.61 (13)C7—C8—C9—O29.84 (18)
C3—C4—C5—C651.49 (15)C7—C8—C9—O3171.43 (10)
C7—C1—C6—C5178.45 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O40.841.782.6004 (13)163
O4—H4A···O2i0.82 (2)1.99 (2)2.8010 (14)174 (2)
O4—H4B···O1ii0.92 (2)1.90 (2)2.8193 (14)178 (2)
Symmetry codes: (i) x, y+1, z+2; (ii) x1, y, z+1.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

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