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The mol­ecule of title compound, C12H14ClNO3, has an L-shaped conformation, with the methyl propanoate unit at the base. The mol­ecules are linked via O—H...N hydrogen bonds into infinite chains of graph-set motif C(6) running along the b axis. In addition, the structure is further stabilized by C—H...O, C—H...Cl and C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806010646/ob2007sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806010646/ob2007Isup2.hkl
Contains datablock I

CCDC reference: 605141

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.038
  • wR factor = 0.110
  • Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H9B .. O3 .. 2.65 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H11A .. CG1 .. 3.08 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 0 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Methyl 3-(2-chloro-5-ethyl-3-pyridinyl)-3-hydroxy-2- methylenepropanoate top
Crystal data top
C12H14ClNO3F(000) = 536
Mr = 255.69Dx = 1.396 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.5383 (15) ÅCell parameters from 8559 reflections
b = 10.9564 (16) Åθ = 2.7–27.9°
c = 11.0465 (16) ŵ = 0.31 mm1
β = 107.534 (2)°T = 273 K
V = 1216.2 (3) Å3Needle, colourless
Z = 40.22 × 0.18 × 0.16 mm
Data collection top
Bruker SMART Apex CCD
diffractometer
2601 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 28.0°, θmin = 2.0°
ω scansh = 1313
13476 measured reflectionsk = 1414
2858 independent reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0659P)2 + 0.2604P]
where P = (Fo2 + 2Fc2)/3
2858 reflections(Δ/σ)max < 0.001
157 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.19 e Å3
Special details top

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
C10.38886 (14)0.08377 (13)0.38382 (13)0.0438 (3)
H10.31000.04910.38880.053*
C20.43346 (12)0.18944 (12)0.45221 (12)0.0373 (3)
C30.55255 (12)0.23798 (11)0.44385 (11)0.0336 (3)
H30.58640.30830.48940.040*
C40.62226 (11)0.18419 (10)0.36930 (10)0.0306 (2)
C50.56483 (12)0.07867 (11)0.30461 (11)0.0343 (3)
C60.74526 (11)0.24316 (11)0.34959 (11)0.0318 (2)
H60.80340.17730.33800.038*
C70.82380 (11)0.31776 (11)0.46360 (11)0.0345 (3)
C80.90393 (12)0.25279 (12)0.58077 (12)0.0373 (3)
C90.98082 (16)0.06139 (16)0.67093 (15)0.0557 (4)
H9A1.07130.08960.69660.084*
H9B0.97840.02320.64770.084*
H9C0.94400.07100.74000.084*
C100.82837 (15)0.43869 (14)0.46391 (15)0.0513 (4)
H10A0.88010.48000.53530.062*
H10B0.77980.48220.39270.062*
C110.36115 (14)0.24967 (14)0.53564 (15)0.0487 (3)
H11A0.40670.22810.62310.058*
H11B0.36870.33740.52820.058*
C120.21641 (18)0.2187 (2)0.5086 (2)0.0695 (5)
H12A0.16990.23720.42150.104*
H12B0.17940.26570.56310.104*
H12C0.20740.13330.52370.104*
Cl10.64013 (4)0.00461 (3)0.20393 (3)0.04954 (14)
N10.45332 (11)0.02826 (11)0.31045 (11)0.0420 (3)
O10.70766 (9)0.31269 (9)0.23601 (8)0.0403 (2)
H1A0.65090.36270.23930.061*
O30.96461 (12)0.30231 (11)0.67789 (10)0.0578 (3)
O40.90360 (9)0.13196 (9)0.56315 (9)0.0430 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0399 (6)0.0453 (7)0.0475 (7)0.0116 (5)0.0152 (5)0.0070 (6)
C20.0360 (6)0.0397 (6)0.0362 (6)0.0021 (5)0.0107 (5)0.0018 (5)
C30.0355 (6)0.0318 (6)0.0321 (5)0.0022 (4)0.0083 (4)0.0031 (4)
C40.0322 (5)0.0298 (5)0.0273 (5)0.0014 (4)0.0050 (4)0.0015 (4)
C50.0394 (6)0.0315 (6)0.0308 (5)0.0007 (4)0.0087 (4)0.0021 (4)
C60.0322 (5)0.0314 (5)0.0317 (5)0.0026 (4)0.0092 (4)0.0013 (4)
C70.0295 (5)0.0361 (6)0.0378 (6)0.0016 (4)0.0100 (4)0.0020 (5)
C80.0305 (5)0.0433 (7)0.0374 (6)0.0030 (5)0.0091 (5)0.0029 (5)
C90.0506 (8)0.0599 (9)0.0501 (8)0.0114 (7)0.0055 (6)0.0156 (7)
C100.0550 (8)0.0374 (7)0.0561 (8)0.0052 (6)0.0086 (7)0.0047 (6)
C110.0470 (8)0.0520 (8)0.0528 (8)0.0056 (6)0.0237 (6)0.0096 (6)
C120.0500 (9)0.0790 (12)0.0873 (13)0.0042 (8)0.0325 (9)0.0164 (10)
Cl10.0589 (2)0.0442 (2)0.0495 (2)0.00094 (14)0.02234 (17)0.01462 (13)
N10.0438 (6)0.0389 (6)0.0424 (6)0.0080 (4)0.0115 (5)0.0078 (5)
O10.0441 (5)0.0431 (5)0.0353 (5)0.0058 (4)0.0143 (4)0.0086 (4)
O30.0585 (6)0.0604 (7)0.0433 (6)0.0077 (5)0.0017 (5)0.0095 (5)
O40.0432 (5)0.0416 (5)0.0389 (5)0.0058 (4)0.0041 (4)0.0033 (4)
Geometric parameters (Å, º) top
C1—N11.3490 (18)C8—O31.2004 (16)
C1—C21.3850 (19)C8—O41.3380 (17)
C1—H10.9300C9—O41.4470 (16)
C2—C31.3915 (17)C9—H9A0.9600
C2—C111.5129 (18)C9—H9B0.9600
C3—C41.3891 (16)C9—H9C0.9600
C3—H30.9300C10—H10A0.9300
C4—C51.3975 (16)C10—H10B0.9300
C4—C61.5216 (16)C11—C121.502 (2)
C5—N11.3175 (17)C11—H11A0.9700
C5—Cl11.7484 (12)C11—H11B0.9700
C6—O11.4184 (14)C12—H12A0.9600
C6—C71.5202 (16)C12—H12B0.9600
C6—H60.9800C12—H12C0.9600
C7—C101.326 (2)O1—H1A0.8200
C7—C81.4954 (17)
N1—C1—C2123.71 (12)O4—C8—C7111.66 (10)
N1—C1—H1118.1O4—C9—H9A109.5
C2—C1—H1118.1O4—C9—H9B109.5
C1—C2—C3116.61 (12)H9A—C9—H9B109.5
C1—C2—C11123.13 (12)O4—C9—H9C109.5
C3—C2—C11120.24 (11)H9A—C9—H9C109.5
C4—C3—C2121.73 (11)H9B—C9—H9C109.5
C4—C3—H3119.1C7—C10—H10A120.0
C2—C3—H3119.1C7—C10—H10B120.0
C3—C4—C5115.42 (11)H10A—C10—H10B120.0
C3—C4—C6122.01 (10)C12—C11—C2116.60 (13)
C5—C4—C6122.31 (10)C12—C11—H11A108.1
N1—C5—C4125.24 (11)C2—C11—H11A108.1
N1—C5—Cl1114.77 (9)C12—C11—H11B108.1
C4—C5—Cl1119.97 (9)C2—C11—H11B108.1
O1—C6—C7112.42 (10)H11A—C11—H11B107.3
O1—C6—C4109.37 (9)C11—C12—H12A109.5
C7—C6—C4112.60 (9)C11—C12—H12B109.5
O1—C6—H6107.4H12A—C12—H12B109.5
C7—C6—H6107.4C11—C12—H12C109.5
C4—C6—H6107.4H12A—C12—H12C109.5
C10—C7—C8117.57 (12)H12B—C12—H12C109.5
C10—C7—C6123.35 (12)C5—N1—C1117.28 (11)
C8—C7—C6119.06 (11)C6—O1—H1A109.5
O3—C8—O4123.68 (13)C8—O4—C9115.65 (11)
O3—C8—C7124.63 (13)
N1—C1—C2—C30.8 (2)C4—C6—C7—C10108.49 (14)
N1—C1—C2—C11179.08 (13)O1—C6—C7—C8162.43 (10)
C1—C2—C3—C40.88 (19)C4—C6—C7—C873.49 (13)
C11—C2—C3—C4179.25 (12)C10—C7—C8—O35.4 (2)
C2—C3—C4—C50.28 (17)C6—C7—C8—O3176.46 (12)
C2—C3—C4—C6174.02 (11)C10—C7—C8—O4172.55 (12)
C3—C4—C5—N10.56 (18)C6—C7—C8—O45.58 (15)
C6—C4—C5—N1174.83 (11)C1—C2—C11—C1220.9 (2)
C3—C4—C5—Cl1178.16 (9)C3—C2—C11—C12160.84 (15)
C6—C4—C5—Cl13.88 (16)C4—C5—N1—C10.7 (2)
C3—C4—C6—O194.59 (13)Cl1—C5—N1—C1178.07 (10)
C5—C4—C6—O179.31 (13)C2—C1—N1—C50.0 (2)
C3—C4—C6—C731.16 (15)O3—C8—O4—C90.90 (19)
C5—C4—C6—C7154.94 (11)C7—C8—O4—C9178.88 (11)
O1—C6—C7—C1015.59 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···N1i0.822.112.8627 (15)153
C9—H9B···O3ii0.962.653.256 (2)121
C6—H6···Cl10.982.683.0942 (13)106
C10—H10B···O10.932.502.8164 (18)100
C11—H11A···Cg1iii0.973.083.836136
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+2, y1/2, z+3/2; (iii) x, y1/2, z1/2.
 

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