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The title mol­ecule, C16H19ClN2O2, contains three planar fragments, i.e. the quinoline system (A), the butyl­amino group (B) and the carboxyl group (C). Angles A/B and A/C are 9.1 (2) and 79.08 (4)°, respectively. The alternation of the bond lengths in the quinoline bicycle correlates with literature data.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801002276/om6000sup1.cif
Contains datablocks ukrb, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801002276/om6000Isup2.hkl
Contains datablock I

CCDC reference: 159862

Key indicators

  • Single-crystal X-ray study
  • T = 290 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.038
  • wR factor = 0.072
  • Data-to-parameter ratio = 20.3

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 32.50 From the CIF: _reflns_number_total 5401 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 5895 Completeness (_total/calc) 91.62% Alert C: < 95% complete WEIGH_01 Alert C Extra text has been found in the _refine_ls_weighting_scheme field. This should be in the _refine_ls_weighting_details field. Weighting scheme given as calc w = 1/[\s^2^(Fo^2^)+(0.0213P)^2^] wher Weighting scheme identified as calc
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Comment top

During investigation of the reaction of the ethyl 2,4-dichloroquinoline-3-carboxylate with nucleophilic reagents, it was found that this compound reacts with sodium acetate giving ethyl chloro-2-oxo-1,2-dihydroquinoline-3-carboxylate, as identified in previous work (Ukrainets et al., 1995). However, X-ray diffraction analysis has shown the product of this reaction to be ethyl 4-butylamino-2-chloroquinoline-3-carboxylate, (I), the structure of which is presented here.

The quinoline fragment of (I) (Fig. 1) is planar within 0.02 Å. The Cl atom lies in the plane of the quinoline bicycle. The carboxyl group is rotated by 79.08 (4)° with respect to the quinoline fragment [the C2—C3—C11—O1 and C2—C3—C11—O2 torsion angles are 95.7 (1) and -81.7 (1)°, respectively]. The non-H atoms of the butylamine fragment are coplanar within 0.03 Å and this plane is rotated by 9.1 (2)° with respect to the quinoline fragment. This rotation may be caused by sterical repulsion between the H5 and H2 atoms, [the distance is 2.05 (2) Å and the sum of the van der Waals radii is 2.32 Å].

A noticeable altering of the C—C (C—N) bonds is observed within the quinoline fragment, i.e. the N1—C2, C3—C4, C5—C6 and C7—C8 bonds are shorter and the remaining bonds are longer than the mean value for aromatic C—C bonds (1.387 Å; Bürgi & Dunitz, 1994). Such peculiarity is observed also for other quinoline-containing structures (Merlino, 1968; Blackburn et al., 1996; Chiang et al., 1991; Gdaniec et al., 1980; Gdaniec & Dziembowska, 1980; Ahmet et al., 1995).

Experimental top

Crystals Of (I) suitable for X-ray study were grown via the slow evaporation of an alcohol solution.

Computing details top

Data collection: P3 (Siemens, 1989); cell refinement: P3; data reduction: XDISK (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1991); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. Numbering scheme and displacement ellipsoids for the title compound (50% probability level).
Ethyl 4-butylamino-2-chloroquinoline-3-carboxylate top
Crystal data top
C16H19ClN2O2Z = 2
Mr = 306.78F(000) = 324
Triclinic, P1Dx = 1.252 Mg m3
a = 8.174 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.760 (2) ÅCell parameters from 34 reflections
c = 11.793 (2) Åθ = 13.0–15.0°
α = 75.68 (2)°µ = 0.24 mm1
β = 85.77 (2)°T = 290 K
γ = 84.98 (2)°Elongated prism, colourless
V = 813.9 (3) Å30.45 × 0.40 × 0.25 mm
Data collection top
Siemens P3/PC
diffractometer
2629 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.054
Graphite monochromatorθmax = 32.5°, θmin = 2.6°
2θ/θ scansh = 1212
Absorption correction: integration
(XPREP; Siemens, 1991)
k = 1213
Tmin = 0.887, Tmax = 0.945l = 016
5630 measured reflections2 standard reflections every 98 reflections
5401 independent reflections intensity decay: 2%
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) = 0.072All H-atom parameters refined
S = 0.91Calculated w = 1/[σ2(Fo2) + (0.0213P)2]
where P Fo2 + 2Fc2)/3
5401 reflections(Δ/σ)max = 0.004
266 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.12 e Å3
Crystal data top
C16H19ClN2O2γ = 84.98 (2)°
Mr = 306.78V = 813.9 (3) Å3
Triclinic, P1Z = 2
a = 8.174 (2) ÅMo Kα radiation
b = 8.760 (2) ŵ = 0.24 mm1
c = 11.793 (2) ÅT = 290 K
α = 75.68 (2)°0.45 × 0.40 × 0.25 mm
β = 85.77 (2)°
Data collection top
Siemens P3/PC
diffractometer
2629 reflections with I > 2σ(I)
Absorption correction: integration
(XPREP; Siemens, 1991)
Rint = 0.054
Tmin = 0.887, Tmax = 0.9452 standard reflections every 98 reflections
5630 measured reflections intensity decay: 2%
5401 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.072All H-atom parameters refined
S = 0.91Δρmax = 0.16 e Å3
5401 reflectionsΔρmin = 0.12 e Å3
266 parameters
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
Cl0.20162 (4)0.98652 (4)0.24489 (3)0.07096 (12)
O10.20045 (9)1.33894 (9)0.00641 (6)0.05635 (19)
O20.27630 (9)1.10167 (9)0.03311 (7)0.0587 (2)
N10.47002 (12)1.06376 (11)0.31648 (9)0.0627 (3)
N20.62956 (12)1.34534 (11)0.01449 (8)0.0530 (2)
H20.7000 (15)1.4088 (14)0.0113 (10)0.061 (4)*
C20.38731 (13)1.08497 (12)0.22257 (10)0.0532 (3)
C30.42293 (12)1.18078 (11)0.10861 (9)0.0465 (2)
C40.57246 (12)1.25672 (11)0.09154 (9)0.0451 (2)
C50.82293 (14)1.30977 (14)0.18926 (11)0.0576 (3)
H50.8732 (18)1.3749 (16)0.1111 (13)0.092 (4)*
C60.90714 (17)1.29150 (16)0.28872 (12)0.0694 (4)
H61.0072 (17)1.3371 (15)0.2798 (11)0.080 (4)*
C70.84734 (18)1.19940 (17)0.39820 (12)0.0770 (4)
H70.9145 (18)1.1846 (16)0.4762 (13)0.093 (4)*
C80.70454 (17)1.12669 (17)0.40473 (12)0.0736 (4)
H80.6632 (16)1.0618 (16)0.4762 (12)0.081 (4)*
C90.67037 (12)1.23801 (12)0.19318 (9)0.0484 (2)
C100.61297 (14)1.14314 (13)0.30363 (9)0.0554 (3)
C110.29028 (13)1.21703 (12)0.02152 (9)0.0470 (2)
C120.14099 (17)1.12234 (18)0.11241 (12)0.0653 (3)
H12A0.0506 (15)1.1733 (13)0.0874 (10)0.054 (3)*
H12B0.1237 (16)1.0045 (16)0.1172 (11)0.078 (4)*
C130.1858 (2)1.2243 (2)0.23279 (13)0.0756 (4)
H13A0.1045 (18)1.2162 (16)0.2767 (12)0.077 (4)*
H13B0.2164 (17)1.3356 (18)0.2354 (11)0.085 (4)*
H13C0.286 (2)1.182 (2)0.2805 (15)0.121 (6)*
C140.56709 (14)1.35805 (14)0.12989 (9)0.0508 (3)
H14A0.4591 (13)1.4221 (12)0.1463 (9)0.046 (3)*
H14B0.5537 (14)1.2513 (14)0.1419 (9)0.060 (3)*
C150.68606 (15)1.44280 (16)0.22687 (9)0.0541 (3)
H15A0.8029 (16)1.3858 (14)0.2212 (10)0.065 (3)*
H15B0.7020 (14)1.5484 (14)0.2090 (10)0.065 (3)*
C160.62432 (18)1.4644 (2)0.34979 (11)0.0687 (4)
H16A0.5100 (18)1.5119 (16)0.3564 (11)0.085 (4)*
H16B0.6149 (17)1.3585 (17)0.3620 (12)0.084 (4)*
C170.7371 (3)1.5599 (3)0.44524 (14)0.1050 (7)
H17A0.702 (2)1.562 (2)0.5198 (16)0.111 (6)*
H17B0.734 (2)1.676 (2)0.4333 (16)0.135 (8)*
H17C0.839 (3)1.519 (3)0.4462 (18)0.150 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.05774 (18)0.0738 (2)0.0736 (2)0.02914 (15)0.00097 (15)0.00451 (15)
O10.0517 (4)0.0541 (4)0.0622 (5)0.0045 (4)0.0050 (4)0.0112 (4)
O20.0577 (5)0.0558 (5)0.0672 (5)0.0107 (4)0.0080 (4)0.0197 (4)
N10.0593 (6)0.0682 (6)0.0530 (6)0.0196 (5)0.0014 (5)0.0044 (4)
N20.0556 (5)0.0605 (6)0.0424 (5)0.0207 (5)0.0017 (4)0.0064 (4)
C20.0498 (6)0.0449 (6)0.0604 (7)0.0139 (5)0.0015 (5)0.0016 (5)
C30.0439 (5)0.0431 (5)0.0522 (6)0.0069 (4)0.0021 (5)0.0112 (4)
C40.0449 (5)0.0439 (5)0.0458 (5)0.0074 (4)0.0026 (4)0.0095 (4)
C50.0504 (6)0.0614 (7)0.0572 (7)0.0141 (5)0.0064 (5)0.0027 (5)
C60.0592 (7)0.0781 (9)0.0691 (8)0.0209 (7)0.0131 (6)0.0063 (6)
C70.0741 (9)0.0896 (10)0.0631 (8)0.0226 (7)0.0227 (7)0.0008 (7)
C80.0723 (9)0.0863 (9)0.0532 (7)0.0200 (7)0.0097 (7)0.0070 (7)
C90.0452 (5)0.0475 (6)0.0496 (6)0.0053 (4)0.0006 (5)0.0062 (5)
C100.0548 (6)0.0590 (7)0.0476 (6)0.0125 (5)0.0018 (5)0.0013 (5)
C110.0425 (5)0.0440 (6)0.0532 (6)0.0128 (5)0.0042 (5)0.0077 (5)
C120.0585 (8)0.0732 (9)0.0689 (8)0.0187 (7)0.0060 (6)0.0206 (7)
C130.0761 (10)0.0935 (11)0.0632 (9)0.0269 (8)0.0073 (8)0.0219 (8)
C140.0479 (6)0.0570 (7)0.0478 (6)0.0138 (5)0.0041 (5)0.0118 (5)
C150.0495 (6)0.0698 (8)0.0450 (6)0.0175 (6)0.0047 (5)0.0151 (5)
C160.0642 (8)0.0930 (10)0.0503 (7)0.0269 (7)0.0040 (6)0.0148 (7)
C170.1080 (16)0.164 (2)0.0427 (8)0.0602 (15)0.0041 (9)0.0089 (10)
Geometric parameters (Å, º) top
Cl—C21.7818 (11)C8—H80.950 (14)
O1—C111.2245 (13)C9—C101.4318 (15)
O2—C111.3425 (13)C12—C131.517 (2)
O2—C121.4712 (15)C12—H12A0.898 (11)
N1—C21.3057 (14)C12—H12B1.070 (13)
N1—C101.3914 (14)C13—H13A0.889 (14)
N2—C41.3715 (13)C13—H13B1.020 (15)
N2—C141.4638 (15)C13—H13C1.054 (19)
N2—H20.843 (12)C14—C151.5321 (15)
C2—C31.4222 (14)C14—H14A1.008 (11)
C3—C41.4202 (14)C14—H14B0.996 (12)
C3—C111.5080 (15)C15—C161.5322 (17)
C4—C91.4579 (15)C15—H15A1.037 (13)
C5—C61.3719 (18)C15—H15B1.020 (12)
C5—C91.4376 (15)C16—C171.527 (2)
C5—H51.034 (15)C16—H16A0.990 (14)
C6—C71.4203 (19)C16—H16B0.984 (14)
C6—H60.929 (13)C17—H17A0.941 (18)
C7—C81.3662 (18)C17—H17B1.059 (19)
C7—H71.080 (14)C17—H17C0.88 (2)
C8—C101.4250 (17)
C11—O2—C12117.34 (10)O2—C12—H12A112.4 (7)
C2—N1—C10116.14 (9)C13—C12—H12A104.4 (7)
C4—N2—C14127.57 (9)O2—C12—H12B103.6 (7)
C4—N2—H2115.5 (8)C13—C12—H12B110.8 (7)
C14—N2—H2116.4 (8)H12A—C12—H12B114.2 (10)
N1—C2—C3128.43 (10)C12—C13—H13A104.6 (9)
N1—C2—Cl114.37 (8)C12—C13—H13B116.1 (8)
C3—C2—Cl117.13 (9)H13A—C13—H13B116.9 (12)
C4—C3—C2116.56 (10)C12—C13—H13C117.0 (10)
C4—C3—C11124.01 (9)H13A—C13—H13C99.7 (12)
C2—C3—C11118.59 (9)H13B—C13—H13C101.9 (12)
N2—C4—C3123.84 (10)N2—C14—C15110.43 (9)
N2—C4—C9118.58 (9)N2—C14—H14A115.9 (6)
C3—C4—C9117.57 (9)C15—C14—H14A103.6 (6)
C6—C5—C9120.92 (11)N2—C14—H14B110.6 (6)
C6—C5—H5118.2 (8)C15—C14—H14B108.6 (6)
C9—C5—H5120.9 (8)H14A—C14—H14B107.3 (9)
C5—C6—C7120.99 (12)C16—C15—C14112.80 (9)
C5—C6—H6116.8 (8)C16—C15—H15A110.6 (7)
C7—C6—H6122.1 (8)C14—C15—H15A111.4 (6)
C8—C7—C6119.68 (13)C16—C15—H15B111.8 (7)
C8—C7—H7119.5 (8)C14—C15—H15B106.4 (6)
C6—C7—H7120.8 (8)H15A—C15—H15B103.5 (9)
C7—C8—C10121.11 (12)C17—C16—C15112.46 (12)
C7—C8—H8121.6 (8)C17—C16—H16A110.1 (8)
C10—C8—H8117.2 (8)C15—C16—H16A112.5 (8)
C10—C9—C5117.51 (10)C17—C16—H16B111.1 (8)
C10—C9—C4118.84 (9)C15—C16—H16B107.4 (8)
C5—C9—C4123.65 (9)H16A—C16—H16B102.9 (11)
N1—C10—C8117.95 (10)C16—C17—H17A110.2 (10)
N1—C10—C9122.30 (10)C16—C17—H17B108.4 (11)
C8—C10—C9119.75 (10)H17A—C17—H17B110.5 (14)
O1—C11—O2123.84 (10)C16—C17—H17C113.7 (15)
O1—C11—C3122.10 (10)H17A—C17—H17C104.0 (17)
O2—C11—C3114.01 (9)H17B—C17—H17C110.0 (18)
O2—C12—C13111.68 (11)
C10—N1—C2—C30.99 (18)C3—C4—C9—C5179.12 (11)
C10—N1—C2—Cl177.85 (9)C2—N1—C10—C8178.32 (12)
N1—C2—C3—C44.10 (18)C2—N1—C10—C92.31 (17)
Cl—C2—C3—C4179.10 (8)C7—C8—C10—N1179.04 (13)
N1—C2—C3—C11165.82 (11)C7—C8—C10—C90.3 (2)
Cl—C2—C3—C1110.98 (14)C5—C9—C10—N1177.68 (11)
C14—N2—C4—C310.77 (18)C4—C9—C10—N12.29 (17)
C14—N2—C4—C9168.94 (10)C5—C9—C10—C81.68 (17)
C2—C3—C4—N2175.99 (10)C4—C9—C10—C8178.35 (11)
C11—C3—C4—N214.70 (17)C12—O2—C11—O12.17 (14)
C2—C3—C4—C93.73 (14)C12—O2—C11—C3175.19 (9)
C11—C3—C4—C9165.58 (10)C4—C3—C11—O173.37 (14)
C9—C5—C6—C70.9 (2)C2—C3—C11—O195.74 (12)
C5—C6—C7—C80.5 (2)C4—C3—C11—O2109.21 (11)
C6—C7—C8—C100.8 (2)C2—C3—C11—O281.67 (12)
C6—C5—C9—C101.95 (18)C11—O2—C12—C1382.83 (15)
C6—C5—C9—C4178.08 (11)C4—N2—C14—C15168.83 (11)
N2—C4—C9—C10178.82 (10)N2—C14—C15—C16178.15 (12)
C3—C4—C9—C100.92 (15)C14—C15—C16—C17175.63 (17)
N2—C4—C9—C51.15 (16)

Experimental details

Crystal data
Chemical formulaC16H19ClN2O2
Mr306.78
Crystal system, space groupTriclinic, P1
Temperature (K)290
a, b, c (Å)8.174 (2), 8.760 (2), 11.793 (2)
α, β, γ (°)75.68 (2), 85.77 (2), 84.98 (2)
V3)813.9 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.45 × 0.40 × 0.25
Data collection
DiffractometerSiemens P3/PC
diffractometer
Absorption correctionIntegration
(XPREP; Siemens, 1991)
Tmin, Tmax0.887, 0.945
No. of measured, independent and
observed [I > 2σ(I)] reflections
5630, 5401, 2629
Rint0.054
(sin θ/λ)max1)0.756
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.072, 0.91
No. of reflections5401
No. of parameters266
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.16, 0.12

Computer programs: P3 (Siemens, 1989), P3, XDISK (Siemens, 1991), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1991), SHELXL97.

Selected geometric parameters (Å, º) top
Cl—C21.7818 (11)C4—C91.4579 (15)
O1—C111.2245 (13)C5—C61.3719 (18)
O2—C111.3425 (13)C5—C91.4376 (15)
O2—C121.4712 (15)C6—C71.4203 (19)
N1—C21.3057 (14)C7—C81.3662 (18)
N1—C101.3914 (14)C8—C101.4250 (17)
N2—C41.3715 (13)C9—C101.4318 (15)
N2—C141.4638 (15)C12—C131.517 (2)
C2—C31.4222 (14)C14—C151.5321 (15)
C3—C41.4202 (14)C15—C161.5322 (17)
C3—C111.5080 (15)C16—C171.527 (2)
C11—O2—C12117.34 (10)C7—C8—C10121.11 (12)
C2—N1—C10116.14 (9)C10—C9—C5117.51 (10)
C4—N2—C14127.57 (9)C10—C9—C4118.84 (9)
N1—C2—C3128.43 (10)C5—C9—C4123.65 (9)
N1—C2—Cl114.37 (8)N1—C10—C8117.95 (10)
C3—C2—Cl117.13 (9)N1—C10—C9122.30 (10)
C4—C3—C2116.56 (10)C8—C10—C9119.75 (10)
C4—C3—C11124.01 (9)O1—C11—O2123.84 (10)
C2—C3—C11118.59 (9)O1—C11—C3122.10 (10)
N2—C4—C3123.84 (10)O2—C11—C3114.01 (9)
N2—C4—C9118.58 (9)O2—C12—C13111.68 (11)
C3—C4—C9117.57 (9)N2—C14—C15110.43 (9)
C6—C5—C9120.92 (11)C16—C15—C14112.80 (9)
C5—C6—C7120.99 (12)C17—C16—C15112.46 (12)
C8—C7—C6119.68 (13)
 

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