




Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536813014050/lh5607sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536813014050/lh5607Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536813014050/lh5607Isup3.cml |
CCDC reference: 955117
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.032
- wR factor = 0.093
- Data-to-parameter ratio = 13.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.595 84
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in the CIF ? PLAT007_ALERT_5_G Note: Number of Unrefined Donor-H Atoms ........ 2 PLAT154_ALERT_1_G The su's on the Cell Angles are Equal .......... 0.00200 Deg. PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K PLAT793_ALERT_4_G The Model has Chirality at C10A (Verify) .... R PLAT793_ALERT_4_G The Model has Chirality at C10B (Verify) .... S PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still 66 %
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 8 ALERT level G = General information/check it is not something unexpected 3 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 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
A mixture of 2-chloroquinoline-3-carbaldehyde (0.1 g, 0.52 mmol), methyl acrylate (0.071 ml, 0.78 mmol), and DABCO (0.017 g, 0.15 mmol), was kept at room temperature for 7 days. After completion of the reaction (indicated by TLC), the reaction mixture was extracted with ethylacetate (3 τimes 15 ml). The combined organic layer subsequently washed with dil.HCl and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure. The crude product was obtained and purified by column chromatography eluting with 8% ethylacetate in hexane afforded the alcohol methyl 2-((2-chloroquinolin-3-yl)(hydroxy)methyl)acrylate as a colourless solid. X-ray quality crystals were obtained by slow evaporation of a solution of the title compound in ethylacetate.
Hydrogen atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93-0.98 Å, O—H = 0.82° and Uiso(H) = 1.5Ueq(C) for methyl and hydroxyl H atoms and 1.2Ueq(C) for other H atoms.
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
C14H12ClNO3 | Z = 4 |
Mr = 277.70 | F(000) = 576 |
Triclinic, P1 | Dx = 1.423 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.2614 (4) Å | Cell parameters from 4551 reflections |
b = 11.0309 (4) Å | θ = 2.0–25.0° |
c = 13.8161 (6) Å | µ = 0.30 mm−1 |
α = 102.557 (2)° | T = 293 K |
β = 100.646 (2)° | Block, colourless |
γ = 103.704 (2)° | 0.35 × 0.30 × 0.25 mm |
V = 1296.29 (9) Å3 |
Bruker SMART APEXII diffractometer | 3767 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.022 |
Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
ω and ϕ scans | h = −11→10 |
14402 measured reflections | k = −12→13 |
4466 independent reflections | l = −16→16 |
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)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0462P)2 + 0.4048P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
4466 reflections | Δρmax = 0.29 e Å−3 |
344 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0040 (11) |
C14H12ClNO3 | γ = 103.704 (2)° |
Mr = 277.70 | V = 1296.29 (9) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.2614 (4) Å | Mo Kα radiation |
b = 11.0309 (4) Å | µ = 0.30 mm−1 |
c = 13.8161 (6) Å | T = 293 K |
α = 102.557 (2)° | 0.35 × 0.30 × 0.25 mm |
β = 100.646 (2)° |
Bruker SMART APEXII diffractometer | 3767 reflections with I > 2σ(I) |
14402 measured reflections | Rint = 0.022 |
4466 independent reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.29 e Å−3 |
4466 reflections | Δρmin = −0.25 e Å−3 |
344 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1A | 0.14491 (5) | 0.05724 (5) | 0.40164 (4) | 0.05417 (16) | |
O1A | 0.36327 (14) | −0.23933 (11) | 0.28015 (10) | 0.0504 (3) | |
H1A | 0.3051 | −0.3109 | 0.2473 | 0.076* | |
O2A | 0.05490 (17) | −0.36860 (13) | 0.16879 (12) | 0.0655 (4) | |
O3A | −0.03759 (16) | −0.26279 (14) | 0.06395 (11) | 0.0626 (4) | |
N1A | 0.42615 (15) | 0.19802 (13) | 0.45982 (10) | 0.0356 (3) | |
C1A | 0.33952 (18) | 0.08303 (15) | 0.40781 (12) | 0.0338 (4) | |
C2A | 0.58039 (18) | 0.22445 (15) | 0.46705 (12) | 0.0342 (4) | |
C3A | 0.6764 (2) | 0.35052 (17) | 0.51704 (13) | 0.0443 (4) | |
H3A | 0.6352 | 0.4153 | 0.5445 | 0.053* | |
C4A | 0.8297 (2) | 0.37743 (19) | 0.52515 (15) | 0.0520 (5) | |
H4A | 0.8929 | 0.4611 | 0.5583 | 0.062* | |
C5A | 0.8944 (2) | 0.2818 (2) | 0.48466 (15) | 0.0521 (5) | |
H5A | 0.9999 | 0.3017 | 0.4921 | 0.062* | |
C6A | 0.8037 (2) | 0.16025 (19) | 0.43468 (14) | 0.0456 (4) | |
H6A | 0.8474 | 0.0973 | 0.4073 | 0.055* | |
C7A | 0.64369 (18) | 0.12781 (16) | 0.42366 (12) | 0.0350 (4) | |
C8A | 0.54251 (18) | 0.00498 (16) | 0.36909 (12) | 0.0356 (4) | |
H8A | 0.5817 | −0.0604 | 0.3401 | 0.043* | |
C9A | 0.38875 (18) | −0.02014 (15) | 0.35779 (12) | 0.0321 (3) | |
C10A | 0.27692 (18) | −0.14936 (15) | 0.29730 (12) | 0.0352 (4) | |
H10A | 0.2067 | −0.1775 | 0.3385 | 0.042* | |
C11A | 0.18355 (18) | −0.14703 (15) | 0.19609 (12) | 0.0368 (4) | |
C12A | 0.2087 (2) | −0.05086 (19) | 0.15361 (15) | 0.0547 (5) | |
H12A | 0.1496 | −0.0596 | 0.0889 | 0.066* | |
H12B | 0.2855 | 0.0259 | 0.1883 | 0.066* | |
C13A | 0.0617 (2) | −0.27074 (17) | 0.14275 (14) | 0.0433 (4) | |
C14A | −0.1553 (3) | −0.3815 (2) | 0.00547 (18) | 0.0770 (7) | |
H14A | −0.2208 | −0.3645 | −0.0494 | 0.116* | |
H14B | −0.2151 | −0.4134 | 0.0493 | 0.116* | |
H14C | −0.1082 | −0.4451 | −0.0223 | 0.116* | |
Cl1B | 0.34205 (5) | 0.35070 (5) | 0.27784 (4) | 0.05394 (16) | |
N1B | 0.52758 (16) | 0.22798 (12) | 0.21855 (10) | 0.0386 (3) | |
O1B | 0.71157 (13) | 0.63179 (11) | 0.42717 (8) | 0.0422 (3) | |
H1B | 0.7063 | 0.7033 | 0.4560 | 0.063* | |
O2B | 0.45974 (15) | 0.56659 (12) | 0.12824 (10) | 0.0530 (3) | |
O3B | 0.59711 (17) | 0.75707 (12) | 0.11953 (9) | 0.0553 (4) | |
C1B | 0.51958 (18) | 0.34408 (15) | 0.25490 (12) | 0.0342 (4) | |
C2B | 0.66394 (19) | 0.21585 (15) | 0.19986 (12) | 0.0357 (4) | |
C3B | 0.6778 (2) | 0.09090 (17) | 0.16220 (14) | 0.0482 (5) | |
H3B | 0.5944 | 0.0184 | 0.1500 | 0.058* | |
C4B | 0.8116 (3) | 0.07581 (18) | 0.14373 (16) | 0.0560 (5) | |
H4B | 0.8196 | −0.0072 | 0.1191 | 0.067* | |
C5B | 0.9382 (3) | 0.1835 (2) | 0.16113 (18) | 0.0607 (6) | |
H5B | 1.0297 | 0.1717 | 0.1483 | 0.073* | |
C6B | 0.9281 (2) | 0.30528 (18) | 0.19672 (16) | 0.0532 (5) | |
H6B | 1.0125 | 0.3764 | 0.2074 | 0.064* | |
C7B | 0.79075 (19) | 0.32456 (15) | 0.21766 (13) | 0.0369 (4) | |
C8B | 0.77249 (18) | 0.44774 (15) | 0.25652 (12) | 0.0364 (4) | |
H8B | 0.8541 | 0.5215 | 0.2686 | 0.044* | |
C9B | 0.63788 (17) | 0.46076 (14) | 0.27667 (11) | 0.0316 (3) | |
C10B | 0.62325 (18) | 0.59300 (14) | 0.32479 (12) | 0.0328 (4) | |
H10B | 0.5155 | 0.5844 | 0.3250 | 0.039* | |
C11B | 0.67326 (18) | 0.68846 (14) | 0.26558 (12) | 0.0335 (4) | |
C12B | 0.7998 (2) | 0.78554 (17) | 0.29927 (15) | 0.0470 (4) | |
H12C | 0.8246 | 0.8416 | 0.2595 | 0.056* | |
H12D | 0.8646 | 0.7982 | 0.3629 | 0.056* | |
C13B | 0.5651 (2) | 0.66278 (15) | 0.16500 (13) | 0.0375 (4) | |
C14B | 0.4924 (3) | 0.7379 (2) | 0.02265 (16) | 0.0765 (7) | |
H14D | 0.5241 | 0.8104 | −0.0041 | 0.115* | |
H14E | 0.3909 | 0.7304 | 0.0321 | 0.115* | |
H14F | 0.4924 | 0.6599 | −0.0246 | 0.115* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1A | 0.0291 (2) | 0.0501 (3) | 0.0697 (3) | 0.00871 (19) | 0.0111 (2) | −0.0073 (2) |
O1A | 0.0485 (7) | 0.0334 (6) | 0.0626 (8) | 0.0161 (6) | 0.0061 (6) | 0.0011 (6) |
O2A | 0.0628 (9) | 0.0374 (8) | 0.0763 (10) | −0.0048 (6) | 0.0039 (8) | 0.0076 (7) |
O3A | 0.0484 (8) | 0.0571 (9) | 0.0545 (8) | −0.0067 (6) | −0.0094 (7) | 0.0015 (7) |
N1A | 0.0342 (7) | 0.0321 (7) | 0.0354 (7) | 0.0073 (6) | 0.0065 (6) | 0.0029 (6) |
C1A | 0.0290 (8) | 0.0363 (9) | 0.0329 (8) | 0.0085 (7) | 0.0059 (7) | 0.0052 (7) |
C2A | 0.0332 (9) | 0.0356 (9) | 0.0300 (8) | 0.0054 (7) | 0.0042 (7) | 0.0093 (7) |
C3A | 0.0472 (11) | 0.0356 (9) | 0.0436 (10) | 0.0040 (8) | 0.0095 (8) | 0.0079 (8) |
C4A | 0.0425 (11) | 0.0462 (11) | 0.0518 (11) | −0.0086 (9) | 0.0031 (9) | 0.0129 (9) |
C5A | 0.0308 (9) | 0.0623 (13) | 0.0565 (12) | 0.0009 (9) | 0.0039 (8) | 0.0225 (10) |
C6A | 0.0335 (9) | 0.0544 (11) | 0.0499 (11) | 0.0135 (8) | 0.0089 (8) | 0.0166 (9) |
C7A | 0.0326 (8) | 0.0394 (9) | 0.0323 (8) | 0.0097 (7) | 0.0046 (7) | 0.0122 (7) |
C8A | 0.0359 (9) | 0.0357 (9) | 0.0355 (9) | 0.0129 (7) | 0.0089 (7) | 0.0075 (7) |
C9A | 0.0322 (8) | 0.0316 (8) | 0.0301 (8) | 0.0085 (7) | 0.0063 (6) | 0.0057 (6) |
C10A | 0.0358 (9) | 0.0288 (8) | 0.0383 (9) | 0.0085 (7) | 0.0101 (7) | 0.0042 (7) |
C11A | 0.0329 (9) | 0.0328 (9) | 0.0377 (9) | 0.0039 (7) | 0.0079 (7) | 0.0024 (7) |
C12A | 0.0561 (12) | 0.0461 (11) | 0.0455 (11) | −0.0004 (9) | −0.0049 (9) | 0.0104 (9) |
C13A | 0.0383 (10) | 0.0398 (10) | 0.0422 (10) | 0.0030 (8) | 0.0108 (8) | −0.0001 (8) |
C14A | 0.0527 (13) | 0.0717 (15) | 0.0651 (14) | −0.0098 (11) | −0.0082 (11) | −0.0158 (12) |
Cl1B | 0.0352 (2) | 0.0458 (3) | 0.0787 (4) | 0.0054 (2) | 0.0187 (2) | 0.0156 (2) |
N1B | 0.0413 (8) | 0.0290 (7) | 0.0403 (8) | 0.0030 (6) | 0.0077 (6) | 0.0087 (6) |
O1B | 0.0493 (7) | 0.0388 (7) | 0.0343 (6) | 0.0170 (6) | 0.0034 (5) | 0.0026 (5) |
O2B | 0.0555 (8) | 0.0369 (7) | 0.0473 (7) | 0.0006 (6) | −0.0073 (6) | 0.0035 (6) |
O3B | 0.0787 (10) | 0.0391 (7) | 0.0404 (7) | 0.0100 (7) | 0.0008 (6) | 0.0144 (6) |
C1B | 0.0328 (8) | 0.0326 (9) | 0.0348 (9) | 0.0054 (7) | 0.0058 (7) | 0.0110 (7) |
C2B | 0.0450 (10) | 0.0278 (8) | 0.0326 (8) | 0.0078 (7) | 0.0078 (7) | 0.0093 (7) |
C3B | 0.0625 (12) | 0.0281 (9) | 0.0502 (11) | 0.0083 (8) | 0.0157 (9) | 0.0068 (8) |
C4B | 0.0755 (14) | 0.0349 (10) | 0.0615 (13) | 0.0233 (10) | 0.0231 (11) | 0.0080 (9) |
C5B | 0.0591 (13) | 0.0498 (12) | 0.0796 (15) | 0.0261 (10) | 0.0275 (11) | 0.0107 (11) |
C6B | 0.0438 (11) | 0.0393 (10) | 0.0747 (14) | 0.0113 (8) | 0.0193 (10) | 0.0088 (9) |
C7B | 0.0401 (9) | 0.0314 (8) | 0.0385 (9) | 0.0105 (7) | 0.0092 (7) | 0.0085 (7) |
C8B | 0.0337 (9) | 0.0264 (8) | 0.0430 (9) | 0.0032 (7) | 0.0061 (7) | 0.0065 (7) |
C9B | 0.0330 (8) | 0.0287 (8) | 0.0307 (8) | 0.0065 (7) | 0.0044 (7) | 0.0090 (6) |
C10B | 0.0308 (8) | 0.0291 (8) | 0.0348 (9) | 0.0074 (6) | 0.0047 (7) | 0.0051 (7) |
C11B | 0.0350 (9) | 0.0252 (8) | 0.0367 (9) | 0.0089 (7) | 0.0063 (7) | 0.0033 (7) |
C12B | 0.0444 (10) | 0.0370 (10) | 0.0510 (11) | 0.0017 (8) | 0.0039 (8) | 0.0124 (8) |
C13B | 0.0450 (10) | 0.0274 (8) | 0.0376 (9) | 0.0121 (8) | 0.0072 (8) | 0.0047 (7) |
C14B | 0.115 (2) | 0.0619 (14) | 0.0432 (12) | 0.0268 (14) | −0.0072 (12) | 0.0172 (10) |
Cl1A—C1A | 1.7396 (16) | Cl1B—C1B | 1.7459 (17) |
O1A—C10A | 1.4228 (19) | N1B—C1B | 1.295 (2) |
O1A—H1A | 0.8200 | N1B—C2B | 1.366 (2) |
O2A—C13A | 1.202 (2) | O1B—C10B | 1.4130 (18) |
O3A—C13A | 1.322 (2) | O1B—H1B | 0.8200 |
O3A—C14A | 1.447 (2) | O2B—C13B | 1.195 (2) |
N1A—C1A | 1.295 (2) | O3B—C13B | 1.331 (2) |
N1A—C2A | 1.369 (2) | O3B—C14B | 1.441 (2) |
C1A—C9A | 1.415 (2) | C1B—C9B | 1.410 (2) |
C2A—C3A | 1.404 (2) | C2B—C7B | 1.406 (2) |
C2A—C7A | 1.410 (2) | C2B—C3B | 1.408 (2) |
C3A—C4A | 1.358 (3) | C3B—C4B | 1.351 (3) |
C3A—H3A | 0.9300 | C3B—H3B | 0.9300 |
C4A—C5A | 1.397 (3) | C4B—C5B | 1.399 (3) |
C4A—H4A | 0.9300 | C4B—H4B | 0.9300 |
C5A—C6A | 1.353 (3) | C5B—C6B | 1.358 (3) |
C5A—H5A | 0.9300 | C5B—H5B | 0.9300 |
C6A—C7A | 1.410 (2) | C6B—C7B | 1.409 (2) |
C6A—H6A | 0.9300 | C6B—H6B | 0.9300 |
C7A—C8A | 1.406 (2) | C7B—C8B | 1.410 (2) |
C8A—C9A | 1.357 (2) | C8B—C9B | 1.359 (2) |
C8A—H8A | 0.9300 | C8B—H8B | 0.9300 |
C9A—C10A | 1.505 (2) | C9B—C10B | 1.514 (2) |
C10A—C11A | 1.511 (2) | C10B—C11B | 1.509 (2) |
C10A—H10A | 0.9800 | C10B—H10B | 0.9800 |
C11A—C12A | 1.315 (3) | C11B—C12B | 1.313 (2) |
C11A—C13A | 1.485 (2) | C11B—C13B | 1.481 (2) |
C12A—H12A | 0.9300 | C12B—H12C | 0.9300 |
C12A—H12B | 0.9300 | C12B—H12D | 0.9300 |
C14A—H14A | 0.9600 | C14B—H14D | 0.9600 |
C14A—H14B | 0.9600 | C14B—H14E | 0.9600 |
C14A—H14C | 0.9600 | C14B—H14F | 0.9600 |
C10A—O1A—H1A | 109.5 | C1B—N1B—C2B | 117.42 (14) |
C13A—O3A—C14A | 116.51 (17) | C10B—O1B—H1B | 109.5 |
C1A—N1A—C2A | 117.75 (14) | C13B—O3B—C14B | 115.36 (15) |
N1A—C1A—C9A | 126.31 (15) | N1B—C1B—C9B | 126.51 (15) |
N1A—C1A—Cl1A | 115.01 (12) | N1B—C1B—Cl1B | 114.43 (12) |
C9A—C1A—Cl1A | 118.68 (12) | C9B—C1B—Cl1B | 119.06 (12) |
N1A—C2A—C3A | 119.28 (15) | N1B—C2B—C7B | 121.77 (14) |
N1A—C2A—C7A | 121.07 (14) | N1B—C2B—C3B | 119.00 (15) |
C3A—C2A—C7A | 119.64 (15) | C7B—C2B—C3B | 119.23 (16) |
C4A—C3A—C2A | 119.69 (18) | C4B—C3B—C2B | 120.34 (18) |
C4A—C3A—H3A | 120.2 | C4B—C3B—H3B | 119.8 |
C2A—C3A—H3A | 120.2 | C2B—C3B—H3B | 119.8 |
C3A—C4A—C5A | 121.23 (17) | C3B—C4B—C5B | 120.76 (17) |
C3A—C4A—H4A | 119.4 | C3B—C4B—H4B | 119.6 |
C5A—C4A—H4A | 119.4 | C5B—C4B—H4B | 119.6 |
C6A—C5A—C4A | 120.03 (17) | C6B—C5B—C4B | 120.30 (19) |
C6A—C5A—H5A | 120.0 | C6B—C5B—H5B | 119.9 |
C4A—C5A—H5A | 120.0 | C4B—C5B—H5B | 119.9 |
C5A—C6A—C7A | 120.83 (18) | C5B—C6B—C7B | 120.46 (18) |
C5A—C6A—H6A | 119.6 | C5B—C6B—H6B | 119.8 |
C7A—C6A—H6A | 119.6 | C7B—C6B—H6B | 119.8 |
C8A—C7A—C6A | 123.60 (16) | C2B—C7B—C8B | 117.38 (15) |
C8A—C7A—C2A | 117.83 (15) | C2B—C7B—C6B | 118.91 (15) |
C6A—C7A—C2A | 118.54 (15) | C8B—C7B—C6B | 123.71 (16) |
C9A—C8A—C7A | 121.35 (15) | C9B—C8B—C7B | 121.30 (15) |
C9A—C8A—H8A | 119.3 | C9B—C8B—H8B | 119.3 |
C7A—C8A—H8A | 119.3 | C7B—C8B—H8B | 119.3 |
C8A—C9A—C1A | 115.59 (14) | C8B—C9B—C1B | 115.61 (14) |
C8A—C9A—C10A | 122.69 (14) | C8B—C9B—C10B | 120.66 (14) |
C1A—C9A—C10A | 121.72 (14) | C1B—C9B—C10B | 123.64 (14) |
O1A—C10A—C9A | 107.26 (13) | O1B—C10B—C11B | 112.74 (13) |
O1A—C10A—C11A | 109.72 (13) | O1B—C10B—C9B | 106.54 (12) |
C9A—C10A—C11A | 113.64 (13) | C11B—C10B—C9B | 111.38 (13) |
O1A—C10A—H10A | 108.7 | O1B—C10B—H10B | 108.7 |
C9A—C10A—H10A | 108.7 | C11B—C10B—H10B | 108.7 |
C11A—C10A—H10A | 108.7 | C9B—C10B—H10B | 108.7 |
C12A—C11A—C13A | 121.29 (16) | C12B—C11B—C13B | 122.74 (16) |
C12A—C11A—C10A | 125.54 (15) | C12B—C11B—C10B | 123.77 (15) |
C13A—C11A—C10A | 113.06 (14) | C13B—C11B—C10B | 113.50 (13) |
C11A—C12A—H12A | 120.0 | C11B—C12B—H12C | 120.0 |
C11A—C12A—H12B | 120.0 | C11B—C12B—H12D | 120.0 |
H12A—C12A—H12B | 120.0 | H12C—C12B—H12D | 120.0 |
O2A—C13A—O3A | 123.47 (17) | O2B—C13B—O3B | 123.36 (15) |
O2A—C13A—C11A | 122.95 (17) | O2B—C13B—C11B | 123.22 (15) |
O3A—C13A—C11A | 113.58 (16) | O3B—C13B—C11B | 113.42 (14) |
O3A—C14A—H14A | 109.5 | O3B—C14B—H14D | 109.5 |
O3A—C14A—H14B | 109.5 | O3B—C14B—H14E | 109.5 |
H14A—C14A—H14B | 109.5 | H14D—C14B—H14E | 109.5 |
O3A—C14A—H14C | 109.5 | O3B—C14B—H14F | 109.5 |
H14A—C14A—H14C | 109.5 | H14D—C14B—H14F | 109.5 |
H14B—C14A—H14C | 109.5 | H14E—C14B—H14F | 109.5 |
C2A—N1A—C1A—C9A | 0.7 (2) | C2B—N1B—C1B—C9B | 0.6 (2) |
C2A—N1A—C1A—Cl1A | −179.69 (11) | C2B—N1B—C1B—Cl1B | −179.34 (11) |
C1A—N1A—C2A—C3A | 175.82 (15) | C1B—N1B—C2B—C7B | −0.9 (2) |
C1A—N1A—C2A—C7A | −3.1 (2) | C1B—N1B—C2B—C3B | 178.77 (15) |
N1A—C2A—C3A—C4A | 179.57 (16) | N1B—C2B—C3B—C4B | −179.50 (17) |
C7A—C2A—C3A—C4A | −1.5 (2) | C7B—C2B—C3B—C4B | 0.2 (3) |
C2A—C3A—C4A—C5A | 0.0 (3) | C2B—C3B—C4B—C5B | −0.3 (3) |
C3A—C4A—C5A—C6A | 1.2 (3) | C3B—C4B—C5B—C6B | −0.2 (3) |
C4A—C5A—C6A—C7A | −0.7 (3) | C4B—C5B—C6B—C7B | 0.7 (3) |
C5A—C6A—C7A—C8A | 177.30 (17) | N1B—C2B—C7B—C8B | 0.4 (2) |
C5A—C6A—C7A—C2A | −0.8 (3) | C3B—C2B—C7B—C8B | −179.26 (15) |
N1A—C2A—C7A—C8A | 2.6 (2) | N1B—C2B—C7B—C6B | −179.98 (16) |
C3A—C2A—C7A—C8A | −176.31 (15) | C3B—C2B—C7B—C6B | 0.3 (2) |
N1A—C2A—C7A—C6A | −179.18 (15) | C5B—C6B—C7B—C2B | −0.8 (3) |
C3A—C2A—C7A—C6A | 1.9 (2) | C5B—C6B—C7B—C8B | 178.76 (19) |
C6A—C7A—C8A—C9A | −177.76 (16) | C2B—C7B—C8B—C9B | 0.5 (2) |
C2A—C7A—C8A—C9A | 0.4 (2) | C6B—C7B—C8B—C9B | −179.11 (17) |
C7A—C8A—C9A—C1A | −2.5 (2) | C7B—C8B—C9B—C1B | −0.8 (2) |
C7A—C8A—C9A—C10A | 178.19 (15) | C7B—C8B—C9B—C10B | 176.02 (14) |
N1A—C1A—C9A—C8A | 2.1 (2) | N1B—C1B—C9B—C8B | 0.3 (2) |
Cl1A—C1A—C9A—C8A | −177.49 (12) | Cl1B—C1B—C9B—C8B | −179.82 (12) |
N1A—C1A—C9A—C10A | −178.61 (16) | N1B—C1B—C9B—C10B | −176.42 (15) |
Cl1A—C1A—C9A—C10A | 1.8 (2) | Cl1B—C1B—C9B—C10B | 3.5 (2) |
C8A—C9A—C10A—O1A | 14.0 (2) | C8B—C9B—C10B—O1B | −70.40 (18) |
C1A—C9A—C10A—O1A | −165.25 (14) | C1B—C9B—C10B—O1B | 106.14 (16) |
C8A—C9A—C10A—C11A | −107.46 (17) | C8B—C9B—C10B—C11B | 52.92 (19) |
C1A—C9A—C10A—C11A | 73.3 (2) | C1B—C9B—C10B—C11B | −130.54 (15) |
O1A—C10A—C11A—C12A | −109.7 (2) | O1B—C10B—C11B—C12B | 10.6 (2) |
C9A—C10A—C11A—C12A | 10.4 (2) | C9B—C10B—C11B—C12B | −109.15 (18) |
O1A—C10A—C11A—C13A | 66.52 (18) | O1B—C10B—C11B—C13B | −169.19 (12) |
C9A—C10A—C11A—C13A | −173.42 (13) | C9B—C10B—C11B—C13B | 71.10 (17) |
C14A—O3A—C13A—O2A | −2.5 (3) | C14B—O3B—C13B—O2B | 1.8 (3) |
C14A—O3A—C13A—C11A | 177.18 (17) | C14B—O3B—C13B—C11B | −178.39 (16) |
C12A—C11A—C13A—O2A | 164.7 (2) | C12B—C11B—C13B—O2B | 170.78 (18) |
C10A—C11A—C13A—O2A | −11.7 (2) | C10B—C11B—C13B—O2B | −9.5 (2) |
C12A—C11A—C13A—O3A | −15.0 (3) | C12B—C11B—C13B—O3B | −9.0 (2) |
C10A—C11A—C13A—O3A | 168.60 (15) | C10B—C11B—C13B—O3B | 170.72 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O2A | 0.82 | 2.24 | 2.8372 (19) | 130 |
O1B—H1B···Cl1Ai | 0.82 | 2.79 | 3.5040 (12) | 147 |
O1B—H1B···N1Ai | 0.82 | 2.16 | 2.8609 (17) | 144 |
C5A—H5A···O1Bii | 0.93 | 2.56 | 3.451 (2) | 162 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C14H12ClNO3 |
Mr | 277.70 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.2614 (4), 11.0309 (4), 13.8161 (6) |
α, β, γ (°) | 102.557 (2), 100.646 (2), 103.704 (2) |
V (Å3) | 1296.29 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.30 |
Crystal size (mm) | 0.35 × 0.30 × 0.25 |
Data collection | |
Diffractometer | Bruker SMART APEXII diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14402, 4466, 3767 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.093, 1.03 |
No. of reflections | 4466 |
No. of parameters | 344 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.25 |
Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
O1A—H1A···O2A | 0.82 | 2.24 | 2.8372 (19) | 129.8 |
O1B—H1B···Cl1Ai | 0.82 | 2.79 | 3.5040 (12) | 147.4 |
O1B—H1B···N1Ai | 0.82 | 2.16 | 2.8609 (17) | 144.0 |
C5A—H5A···O1Bii | 0.93 | 2.56 | 3.451 (2) | 161.5 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1. |
The quinoline ring is found in compounds with antifungal (Biavatti et al., 2002), antibacterial (Towers et al., 1981) and anticancer (Shen et al., 1999) properties. Quinoline derivatives have been used for their luminescent properties as organic light-emitting diode (OLED) materials (Montes et al., 2006). Methyl acrylate is an ingredient used in many fragrances and decorative cosmetics (Bhatia et al., 2007; Sharma, 2011). In view of the potential importance of the title compound its crystal structure is presented herein.
The asymmetric unit of the title compound contains the two independent molecules, A and B (Fig. 1). The dihedral angle between the mean plane of methyl ester unit (C13/C14/O2/O3, r.m.s deviation = -0.051 Å for A and -0.016 Å for B) and the chloroquilonin ring system (C1—C9/N1/Cl1, r.m.s deviation = 0.023 Å for A and -0.014 Å for B) is 63.5 (1)° in molecule A and 78.6 (1)° in molecule B. The main difference between the two independent molecules is reflected in the O1—C10—C11—C12 torsion angle which is -109.7 (2)° in molecule A and 10.6 (2)° in molecule B.
The methyl ester moiety adopts an extended conformation as reflected by the torsion angles for C11—C13—C14—O3 = 177.7 (2)° in A and 178.4 (1)° in B. The extended conformation is supported by the fact that the bond angles involving the carbonyl O atoms are invariably expanded (Dunitz & Schweizer, 1982). The significant difference in the bond lengths of the C13—O3 = 1.322 (3) Å (A) 1.331 (3) Å (B) versus C14—O3 = 1.447 (3) Å (A) and 1.447 (2) Å (B) can be attributed to a partial contribution from the O-–C═O+–C resonance structure of the O2—C13—O3—C14 group (Merlino, 1971). This feature, commonly observed in the carboxylic ester group of these substituents in various compounds has been shown to give average values of 1.340 Å and 1.447 Å respectively for these bonds (Varghese et al., 1986).
In the crystal molecule A and B are linked into pairs via bifurcated O—H···(N,Cl) hydrogen bonds (Fig. 2) and a weak C—H···O hydrogen bond links pairs of molecules into chains along [100].