Buy article online - an online subscription or single-article purchase is required to access this article.
In the title crystal structure, C
9H
14O
3·H
2O, 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
CCDC reference: 640412
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (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
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·H2O | Z = 2 |
Mr = 188.22 | F(000) = 204 |
Triclinic, P1 | Dx = 1.291 Mg m−3 |
Hall symbol: -P 1 | Melting point: 326 K |
a = 7.4636 (2) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 7.9944 (3) Å | Cell parameters from 3199 reflections |
c = 8.4817 (3) Å | θ = 5.5–64.9° |
α = 90.852 (2)° | µ = 0.84 mm−1 |
β = 106.903 (1)° | T = 100 K |
γ = 90.778 (2)° | Block, colourless |
V = 484.08 (3) Å3 | 0.22 × 0.17 × 0.08 mm |
Data collection top
Bruker SMART CCD APEX-II area-detector diffractometer | 1524 independent reflections |
Radiation source: fine-focus sealed tube | 1402 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.010 |
φ and ω scans | θmax = 64.9°, θmin = 5.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −8→8 |
Tmin = 0.869, Tmax = 0.941 | k = −9→9 |
3199 measured reflections | l = −9→9 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.031 | H 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 reflections | Δρmax = 0.22 e Å−3 |
128 parameters | Δρmin = −0.18 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.43881 (12) | 0.20680 (11) | −0.05401 (10) | 0.0239 (3) | |
C1 | 0.32314 (17) | 0.19412 (16) | 0.39011 (15) | 0.0193 (3) | |
H1A | 0.3494 | 0.0777 | 0.4312 | 0.023* | |
O2 | 0.10888 (13) | 0.46580 (11) | 0.74499 (11) | 0.0250 (3) | |
C2 | 0.17108 (17) | 0.18539 (16) | 0.22356 (15) | 0.0199 (3) | |
H2A | 0.1358 | 0.3004 | 0.1865 | 0.024* | |
H2B | 0.0584 | 0.1278 | 0.2371 | 0.024* | |
O3 | −0.09635 (13) | 0.25624 (12) | 0.73677 (11) | 0.0251 (3) | |
H3 | −0.1290 | 0.3188 | 0.8036 | 0.038* | |
C3 | 0.23702 (18) | 0.09181 (17) | 0.09093 (15) | 0.0215 (3) | |
H3A | 0.2534 | −0.0278 | 0.1192 | 0.026* | |
H3B | 0.1401 | 0.0991 | −0.0168 | 0.026* | |
C4 | 0.41831 (18) | 0.16404 (15) | 0.07739 (15) | 0.0200 (3) | |
O4 | −0.25491 (15) | 0.41010 (13) | 0.93165 (12) | 0.0274 (3) | |
H4A | −0.204 (3) | 0.445 (3) | 1.025 (3) | 0.051 (6)* | |
H4B | −0.353 (3) | 0.343 (3) | 0.940 (3) | 0.061 (6)* | |
C5 | 0.57229 (18) | 0.17934 (18) | 0.23759 (16) | 0.0240 (3) | |
H5A | 0.6802 | 0.2418 | 0.2202 | 0.029* | |
H5B | 0.6148 | 0.0664 | 0.2764 | 0.029* | |
C6 | 0.50335 (18) | 0.27070 (17) | 0.36871 (15) | 0.0227 (3) | |
H6A | 0.6026 | 0.2685 | 0.4755 | 0.027* | |
H6B | 0.4815 | 0.3892 | 0.3377 | 0.027* | |
C7 | 0.26440 (18) | 0.29753 (16) | 0.51985 (15) | 0.0213 (3) | |
H7A | 0.3699 | 0.3022 | 0.6226 | 0.026* | |
H7B | 0.2408 | 0.4134 | 0.4804 | 0.026* | |
C8 | 0.09139 (18) | 0.23090 (17) | 0.55953 (15) | 0.0221 (3) | |
H8A | −0.0153 | 0.2294 | 0.4576 | 0.026* | |
H8B | 0.1134 | 0.1140 | 0.5963 | 0.026* | |
C9 | 0.03898 (17) | 0.33118 (16) | 0.69024 (15) | 0.0200 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0269 (5) | 0.0263 (5) | 0.0204 (5) | −0.0005 (4) | 0.0100 (4) | 0.0007 (4) |
C1 | 0.0210 (6) | 0.0182 (7) | 0.0183 (6) | −0.0011 (5) | 0.0050 (5) | 0.0007 (5) |
O2 | 0.0279 (5) | 0.0217 (5) | 0.0261 (5) | −0.0028 (4) | 0.0095 (4) | −0.0053 (4) |
C2 | 0.0186 (6) | 0.0218 (7) | 0.0194 (6) | −0.0016 (5) | 0.0060 (5) | −0.0014 (5) |
O3 | 0.0285 (5) | 0.0250 (5) | 0.0245 (5) | −0.0042 (4) | 0.0126 (4) | −0.0037 (4) |
C3 | 0.0225 (6) | 0.0230 (7) | 0.0186 (6) | −0.0028 (5) | 0.0058 (5) | −0.0023 (5) |
C4 | 0.0236 (7) | 0.0160 (7) | 0.0219 (7) | 0.0016 (5) | 0.0090 (5) | −0.0009 (5) |
O4 | 0.0306 (6) | 0.0311 (6) | 0.0229 (5) | −0.0069 (4) | 0.0123 (4) | −0.0040 (4) |
C5 | 0.0193 (6) | 0.0312 (8) | 0.0220 (7) | −0.0010 (5) | 0.0068 (5) | 0.0021 (5) |
C6 | 0.0206 (7) | 0.0268 (7) | 0.0190 (6) | −0.0038 (5) | 0.0035 (5) | −0.0004 (5) |
C7 | 0.0231 (7) | 0.0206 (7) | 0.0193 (6) | −0.0025 (5) | 0.0050 (5) | −0.0021 (5) |
C8 | 0.0236 (7) | 0.0212 (7) | 0.0207 (6) | −0.0026 (5) | 0.0058 (5) | −0.0027 (5) |
C9 | 0.0198 (6) | 0.0201 (7) | 0.0182 (6) | 0.0017 (5) | 0.0027 (5) | 0.0022 (5) |
Geometric parameters (Å, º) top
O1—C4 | 1.2212 (16) | C4—C5 | 1.5051 (17) |
C1—C6 | 1.5296 (17) | O4—H4A | 0.82 (2) |
C1—C7 | 1.5329 (17) | O4—H4B | 0.92 (2) |
C1—C2 | 1.5334 (16) | C5—C6 | 1.5343 (18) |
C1—H1A | 1.0000 | C5—H5A | 0.9900 |
O2—C9 | 1.2145 (16) | C5—H5B | 0.9900 |
C2—C3 | 1.5409 (17) | C6—H6A | 0.9900 |
C2—H2A | 0.9900 | C6—H6B | 0.9900 |
C2—H2B | 0.9900 | C7—C8 | 1.5178 (18) |
O3—C9 | 1.3257 (16) | C7—H7A | 0.9900 |
O3—H3 | 0.8400 | C7—H7B | 0.9900 |
C3—C4 | 1.4995 (18) | C8—C9 | 1.5031 (17) |
C3—H3A | 0.9900 | C8—H8A | 0.9900 |
C3—H3B | 0.9900 | C8—H8B | 0.9900 |
| | | |
C6—C1—C7 | 108.81 (10) | C6—C5—H5A | 109.5 |
C6—C1—C2 | 109.86 (10) | C4—C5—H5B | 109.5 |
C7—C1—C2 | 112.53 (10) | C6—C5—H5B | 109.5 |
C6—C1—H1A | 108.5 | H5A—C5—H5B | 108.1 |
C7—C1—H1A | 108.5 | C1—C6—C5 | 113.24 (11) |
C2—C1—H1A | 108.5 | C1—C6—H6A | 108.9 |
C1—C2—C3 | 112.02 (10) | C5—C6—H6A | 108.9 |
C1—C2—H2A | 109.2 | C1—C6—H6B | 108.9 |
C3—C2—H2A | 109.2 | C5—C6—H6B | 108.9 |
C1—C2—H2B | 109.2 | H6A—C6—H6B | 107.7 |
C3—C2—H2B | 109.2 | C8—C7—C1 | 114.59 (11) |
H2A—C2—H2B | 107.9 | C8—C7—H7A | 108.6 |
C9—O3—H3 | 109.5 | C1—C7—H7A | 108.6 |
C4—C3—C2 | 111.33 (10) | C8—C7—H7B | 108.6 |
C4—C3—H3A | 109.4 | C1—C7—H7B | 108.6 |
C2—C3—H3A | 109.4 | H7A—C7—H7B | 107.6 |
C4—C3—H3B | 109.4 | C9—C8—C7 | 113.83 (11) |
C2—C3—H3B | 109.4 | C9—C8—H8A | 108.8 |
H3A—C3—H3B | 108.0 | C7—C8—H8A | 108.8 |
O1—C4—C3 | 122.31 (11) | C9—C8—H8B | 108.8 |
O1—C4—C5 | 122.78 (12) | C7—C8—H8B | 108.8 |
C3—C4—C5 | 114.91 (11) | H8A—C8—H8B | 107.7 |
H4A—O4—H4B | 105.5 (19) | O2—C9—O3 | 123.78 (12) |
C4—C5—C6 | 110.62 (10) | O2—C9—C8 | 124.54 (12) |
C4—C5—H5A | 109.5 | O3—C9—C8 | 111.67 (11) |
| | | |
C6—C1—C2—C3 | 54.55 (14) | C2—C1—C6—C5 | −54.85 (14) |
C7—C1—C2—C3 | 175.95 (11) | C4—C5—C6—C1 | 52.71 (15) |
C1—C2—C3—C4 | −53.28 (14) | C6—C1—C7—C8 | −177.37 (10) |
C2—C3—C4—O1 | −127.88 (12) | C2—C1—C7—C8 | 60.63 (15) |
C2—C3—C4—C5 | 52.22 (14) | C1—C7—C8—C9 | 178.43 (10) |
O1—C4—C5—C6 | 128.61 (13) | C7—C8—C9—O2 | 9.84 (18) |
C3—C4—C5—C6 | −51.49 (15) | C7—C8—C9—O3 | −171.43 (10) |
C7—C1—C6—C5 | −178.45 (10) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O4 | 0.84 | 1.78 | 2.6004 (13) | 163 |
O4—H4A···O2i | 0.82 (2) | 1.99 (2) | 2.8010 (14) | 174 (2) |
O4—H4B···O1ii | 0.92 (2) | 1.90 (2) | 2.8193 (14) | 178 (2) |
Symmetry codes: (i) −x, −y+1, −z+2; (ii) x−1, 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.