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In the title compound, C15H17NO6, the formation of an intramolecular O—H...O resonance-assisted hydrogen bond extends the delocalization of the electronic system beyond the two quinoline fused rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803016192/bt6304sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803016192/bt6304Isup2.hkl
Contains datablock I

CCDC reference: 221709

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.041
  • wR factor = 0.116
  • Data-to-parameter ratio = 14.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 30.39 From the CIF: _reflns_number_total 3978 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 4253 Completeness (_total/calc) 93.53% Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: SMART-NT (Bruker, 1998); cell refinement: SMART-NT; data reduction: SAINT-NT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL-NT (Bruker, 1998).

3-ethoxycarbonyl-4-hydroxy-6-methoxymethyleneoxy-1-methyl-2-quinolone top
Crystal data top
C15H17NO6F(000) = 648
Mr = 307.30Dx = 1.445 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 755 reflections
a = 11.558 (3) Åθ = 13.7–24.3°
b = 10.476 (2) ŵ = 0.11 mm1
c = 11.750 (2) ÅT = 100 K
β = 98.823 (3)°Irregular shape, colourless
V = 1405.9 (5) Å30.36 × 0.26 × 0.18 mm
Z = 4
Data collection top
Bruker SMART 1K CCD
diffractometer
2908 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
Graphite monochromatorθmax = 30.4°, θmin = 1.8°
ω scansh = 1615
16953 measured reflectionsk = 1414
3978 independent reflectionsl = 1616
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)] = 0.041Hydrogen site location: difference Fourier map
wR(F2) = 0.116All H-atom parameters refined
S = 1.01 w = 1/[σ2(Fo2) + (0.0632P)2 + 0.3584P]
where P = (Fo2 + 2Fc2)/3
3978 reflections(Δ/σ)max < 0.001
267 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.29 e Å3
Special details top

Experimental. The data collection nominally covered a full sphere of reciprocal space, by a combination of 5 sets of ω scans each set at different φ and/or 2θ angles and each scan (20 s exposure) covering 0.3° in ω. Crystal to detector distance 4.51 cm.

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
N10.10217 (9)0.49877 (10)0.31837 (9)0.0167 (2)
C20.17015 (11)0.41122 (12)0.36837 (10)0.0170 (2)
C30.10626 (11)0.31269 (12)0.44051 (10)0.0162 (2)
C4A0.08094 (10)0.39480 (12)0.39502 (10)0.0159 (2)
C40.01511 (11)0.30558 (12)0.45308 (10)0.0156 (2)
C50.20385 (11)0.38476 (12)0.40468 (10)0.0172 (2)
H50.2407 (14)0.3171 (16)0.4490 (13)0.020 (4)*
C60.26489 (11)0.47201 (13)0.34883 (11)0.0185 (3)
C70.20362 (12)0.56976 (13)0.28376 (11)0.0204 (3)
H70.2476 (16)0.6305 (16)0.2434 (15)0.030 (4)*
C8A0.01903 (10)0.49094 (12)0.32839 (10)0.0162 (2)
C80.08353 (11)0.57944 (13)0.27316 (11)0.0192 (3)
H80.0435 (14)0.6471 (16)0.2291 (14)0.024 (4)*
C90.16595 (11)0.21633 (12)0.50186 (10)0.0172 (2)
O100.28169 (8)0.22102 (9)0.48625 (8)0.0201 (2)
C110.34014 (12)0.12130 (14)0.54398 (12)0.0219 (3)
H11B0.2986 (14)0.1111 (15)0.6211 (14)0.021 (4)*
H11A0.4156 (15)0.1570 (16)0.5453 (13)0.023 (4)*
C120.34791 (13)0.00083 (14)0.47535 (13)0.0259 (3)
H12C0.3935 (16)0.0134 (17)0.3985 (16)0.031 (4)*
H12B0.3837 (16)0.0683 (18)0.5173 (15)0.034 (5)*
H12A0.2683 (17)0.0352 (18)0.4637 (15)0.035 (5)*
O130.11068 (8)0.13483 (9)0.56458 (8)0.0225 (2)
O140.07756 (8)0.21692 (9)0.51637 (8)0.0200 (2)
H140.025 (2)0.172 (2)0.5492 (18)0.051 (6)*
O150.27786 (8)0.42042 (10)0.35004 (8)0.0245 (2)
C160.16336 (12)0.60044 (13)0.24695 (12)0.0202 (3)
H16C0.1358 (15)0.6839 (17)0.2792 (14)0.025 (4)*
H16B0.2440 (17)0.5932 (17)0.2538 (15)0.032 (5)*
H16A0.1508 (14)0.5914 (16)0.1674 (14)0.023 (4)*
O170.38414 (8)0.47260 (9)0.35095 (8)0.0215 (2)
C180.45109 (12)0.37448 (13)0.41508 (12)0.0218 (3)
H18B0.4336 (14)0.3724 (15)0.4930 (14)0.019 (4)*
H18A0.5313 (15)0.4014 (16)0.4119 (14)0.026 (4)*
O190.42767 (8)0.25349 (9)0.36709 (8)0.0225 (2)
C200.46905 (14)0.23784 (16)0.25916 (13)0.0278 (3)
H20C0.4628 (15)0.1462 (18)0.2392 (15)0.028 (4)*
H20B0.4212 (17)0.2879 (18)0.2002 (16)0.034 (5)*
H20A0.552 (2)0.2680 (19)0.2675 (17)0.045 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0153 (5)0.0181 (5)0.0166 (5)0.0004 (4)0.0021 (4)0.0023 (4)
C20.0154 (6)0.0192 (6)0.0161 (5)0.0016 (4)0.0019 (4)0.0008 (4)
C30.0160 (6)0.0165 (6)0.0162 (5)0.0010 (4)0.0031 (4)0.0002 (4)
C4A0.0161 (6)0.0159 (6)0.0158 (5)0.0012 (4)0.0031 (4)0.0010 (4)
C40.0165 (6)0.0155 (6)0.0146 (5)0.0002 (4)0.0018 (4)0.0010 (4)
C50.0161 (6)0.0171 (6)0.0182 (5)0.0003 (5)0.0024 (4)0.0003 (5)
C60.0142 (6)0.0214 (6)0.0200 (6)0.0018 (5)0.0032 (4)0.0023 (5)
C70.0206 (6)0.0206 (6)0.0206 (6)0.0032 (5)0.0056 (5)0.0012 (5)
C8A0.0154 (6)0.0175 (6)0.0157 (5)0.0013 (4)0.0021 (4)0.0022 (4)
C80.0188 (6)0.0198 (6)0.0191 (6)0.0000 (5)0.0033 (5)0.0025 (5)
C90.0150 (6)0.0193 (6)0.0172 (5)0.0021 (5)0.0027 (4)0.0013 (4)
O100.0148 (4)0.0218 (5)0.0239 (4)0.0023 (3)0.0040 (3)0.0041 (4)
C110.0156 (6)0.0264 (7)0.0243 (6)0.0024 (5)0.0047 (5)0.0078 (5)
C120.0226 (7)0.0257 (7)0.0286 (7)0.0062 (6)0.0012 (5)0.0047 (6)
O130.0172 (5)0.0234 (5)0.0264 (5)0.0014 (4)0.0022 (4)0.0073 (4)
O140.0159 (4)0.0199 (5)0.0241 (5)0.0000 (4)0.0026 (3)0.0059 (4)
O150.0138 (4)0.0290 (5)0.0300 (5)0.0002 (4)0.0006 (4)0.0086 (4)
C160.0178 (6)0.0201 (6)0.0224 (6)0.0016 (5)0.0021 (5)0.0046 (5)
O170.0137 (4)0.0215 (5)0.0298 (5)0.0016 (3)0.0051 (4)0.0039 (4)
C180.0157 (6)0.0249 (7)0.0243 (6)0.0017 (5)0.0013 (5)0.0019 (5)
O190.0190 (5)0.0223 (5)0.0269 (5)0.0005 (4)0.0057 (4)0.0030 (4)
C200.0247 (7)0.0289 (8)0.0311 (7)0.0017 (6)0.0085 (6)0.0001 (6)
Geometric parameters (Å, º) top
O13—C91.2392 (16)C9—O101.3230 (15)
C9—C31.4721 (17)O10—C111.4657 (15)
C3—C41.3899 (17)C11—C121.508 (2)
C4—O141.3312 (15)C11—H11B0.964 (16)
N1—C8A1.3901 (16)C11—H11A0.951 (17)
N1—C21.3948 (16)C12—H12C0.984 (18)
N1—C161.4686 (16)C12—H12B0.988 (19)
C2—O151.2342 (15)C12—H12A1.016 (19)
C2—C31.4619 (17)O14—H140.90 (2)
C4A—C8A1.4027 (17)C16—H16C0.986 (18)
C4A—C51.4116 (17)C16—H16B0.95 (2)
C4A—C41.4412 (17)C16—H16A0.972 (16)
C5—C61.3805 (18)O17—C181.4298 (16)
C5—H50.941 (17)C18—O191.3968 (17)
C6—O171.3747 (15)C18—H18B0.967 (16)
C6—C71.4030 (19)C18—H18A0.975 (17)
C7—C81.3782 (19)O19—C201.4318 (17)
C7—H70.981 (18)C20—H20C0.988 (18)
C8A—C81.4088 (17)C20—H20B0.971 (19)
C8—H80.955 (17)C20—H20A1.00 (2)
C8A—N1—C2123.44 (10)O10—C11—C12110.57 (11)
C8A—N1—C16118.81 (10)O10—C11—H11B108.4 (9)
C2—N1—C16117.68 (10)C12—C11—H11B112.9 (10)
O15—C2—N1119.57 (11)O10—C11—H11A102.5 (10)
O15—C2—C3124.23 (11)C12—C11—H11A111.3 (10)
N1—C2—C3116.19 (10)H11B—C11—H11A110.7 (13)
C4—C3—C2120.75 (11)C11—C12—H12C110.0 (10)
C4—C3—C9116.90 (11)C11—C12—H12B109.6 (10)
C2—C3—C9122.35 (11)H12C—C12—H12B111.0 (15)
C8A—C4A—C5121.29 (11)C11—C12—H12A113.1 (11)
C8A—C4A—C4117.95 (11)H12C—C12—H12A107.3 (14)
C5—C4A—C4120.76 (11)H12B—C12—H12A105.7 (15)
O14—C4—C3123.28 (11)C4—O14—H14104.7 (14)
O14—C4—C4A115.88 (11)N1—C16—H16C108.9 (10)
C3—C4—C4A120.83 (11)N1—C16—H16B106.7 (11)
C6—C5—C4A119.59 (12)H16C—C16—H16B107.5 (14)
C6—C5—H5122.7 (10)N1—C16—H16A110.4 (10)
C4A—C5—H5117.7 (10)H16C—C16—H16A111.7 (14)
O17—C6—C5125.34 (12)H16B—C16—H16A111.5 (14)
O17—C6—C7115.31 (11)C6—O17—C18117.80 (10)
C5—C6—C7119.36 (12)O19—C18—O17112.57 (11)
C8—C7—C6121.34 (12)O19—C18—H18B107.8 (9)
C8—C7—H7119.9 (11)O17—C18—H18B109.8 (9)
C6—C7—H7118.7 (11)O19—C18—H18A111.9 (10)
N1—C8A—C4A120.72 (11)O17—C18—H18A102.3 (10)
N1—C8A—C8121.31 (11)H18B—C18—H18A112.4 (13)
C4A—C8A—C8117.97 (11)C18—O19—C20113.02 (11)
C7—C8—C8A120.44 (12)O19—C20—H20C107.4 (10)
C7—C8—H8120.1 (10)O19—C20—H20B109.8 (11)
C8A—C8—H8119.5 (10)H20C—C20—H20B110.1 (14)
O13—C9—O10121.74 (11)O19—C20—H20A108.9 (12)
O13—C9—C3121.75 (11)H20C—C20—H20A111.3 (15)
O10—C9—C3116.51 (11)H20B—C20—H20A109.4 (16)
C9—O10—C11115.93 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O14—H14···O130.90 (2)1.65 (2)2.4844 (14)153 (2)
Bond distances (Å) within the RAHB fragment and their expected values (Bürgi &amp; Dunitz, 1994) top
BondThis workExpected
O13—C9a1.2392 (16)1.199 (9)
C9—C3a1.4721 (17)1.488 (14)
C3—C4b1.3899 (17)1.340 (13)
C4—O14c1.3312 (15)1.362 (15)
Expected values in the fragments: (a) CC-C(O)-O-C*; (b) CC-CO; (c) Car-OH.
 

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