Ethyl 4-chloro-2-oxo-1,2,5,6,7,8-hexa­hydro­quinoline-3-carboxyl­ate

In the title compound, C₁₂H₁₄ClNO₃, the aliphatic ring of the hexa­hydro­quinoline system adopts a half-chair conformation while the ethyl carboxyl­ate substituent is inclined to the hexa­hydro­quinoline ring system by 85.1 (2)°. In the crystal, a pair of N–H...O hydrogen bonds form an inversion dimer. The structure is further stabilized by C—H...O and C—H...Cl hydrogen bonds, forming a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.044
• wR factor = 0.101
• Data-to-parameter ratio = 19.5

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.84 Report
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11A     ..O2       .       2.70 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7B      ..CL1      .       2.85 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      4.455 Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        143 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          9 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SIR2004 (Burla et al., 2007); program(s) used to refine structure: OLEX2 (Dolomanov et al., 2009); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF(Westrip, 2010).

Ethyl 4-chloro-2-oxo-1,2,5,6,7,8-hexahydroquinoline-3-carboxylate

Crystal data

C12H14ClNO3	F(000) = 536
Mr = 255.69	Dx = 1.476 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.7323 (3) Å	Cell parameters from 5245 reflections
b = 9.2537 (5) Å	θ = 2.4–28.8°
c = 21.6899 (12) Å	µ = 0.33 mm^−1
β = 91.168 (5)°	T = 100 K
V = 1150.30 (11) Å^3	Block, translucent intense colourless
Z = 4	0.32 × 0.23 × 0.09 mm

Data collection

Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, AtlasS2 diffractometer	3017 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	2676 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.032
Detector resolution: 5.1980 pixels mm^-1	θmax = 29.4°, θmin = 1.9°
ω scans	h = −7→7
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2015)	k = −12→11
Tmin = 0.773, Tmax = 1.000	l = −29→29
13970 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.101	w = 1/[σ^2(Fo^2) + (0.0349P)^2 + 1.0951P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
3017 reflections	Δρmax = 0.86 e Å^−3
155 parameters	Δρmin = −0.30 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.75996 (7)	0.62470 (5)	0.40163 (2)	0.01866 (12)
O1	0.0556 (2)	0.94748 (14)	0.42371 (5)	0.0162 (3)
O2	0.4402 (2)	0.87426 (15)	0.31021 (6)	0.0240 (3)
O3	0.2426 (2)	0.66734 (14)	0.32599 (5)	0.0162 (3)
N1	0.2608 (2)	0.87959 (15)	0.51040 (6)	0.0124 (3)
H1	0.169504	0.931850	0.532114	0.015*
C1	0.2208 (3)	0.87798 (18)	0.44748 (7)	0.0129 (3)
C2	0.3831 (3)	0.79147 (18)	0.41342 (7)	0.0130 (3)
C3	0.5600 (3)	0.72128 (18)	0.44430 (7)	0.0133 (3)
C4	0.5911 (3)	0.72343 (18)	0.50944 (7)	0.0123 (3)
C5	0.4335 (3)	0.80509 (18)	0.54128 (7)	0.0117 (3)
C6	0.4387 (3)	0.81981 (19)	0.61038 (7)	0.0145 (3)
H6A	0.281068	0.811392	0.625398	0.017*
H6B	0.496584	0.915069	0.621399	0.017*
C7	0.5925 (3)	0.7056 (2)	0.64185 (8)	0.0235 (4)
H7A	0.623150	0.732936	0.684420	0.028*
H7B	0.512014	0.613363	0.641614	0.028*
C8	0.8206 (3)	0.6912 (2)	0.60853 (8)	0.0226 (4)
H8A	0.920094	0.622654	0.630360	0.027*
H8B	0.899644	0.783933	0.608639	0.027*
C9	0.7836 (3)	0.64067 (19)	0.54209 (7)	0.0152 (3)
H9A	0.927464	0.652904	0.519912	0.018*
H9B	0.745109	0.538585	0.541940	0.018*
C10	0.3596 (3)	0.78524 (19)	0.34424 (7)	0.0141 (3)
C11	0.2272 (3)	0.6444 (2)	0.25915 (7)	0.0189 (4)
H11A	0.374809	0.608271	0.244386	0.023*
H11B	0.192908	0.734998	0.238396	0.023*
C12	0.0378 (4)	0.5373 (3)	0.24549 (9)	0.0325 (5)
H12A	0.024954	0.522164	0.201769	0.049*
H12B	−0.107534	0.573636	0.260352	0.049*
H12C	0.074284	0.447459	0.265581	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.01586 (19)	0.0218 (2)	0.0184 (2)	0.00599 (16)	0.00289 (14)	−0.00607 (16)
O1	0.0162 (5)	0.0169 (6)	0.0154 (5)	0.0053 (5)	−0.0006 (4)	−0.0014 (5)
O2	0.0338 (7)	0.0209 (7)	0.0173 (6)	−0.0080 (6)	0.0019 (5)	0.0014 (5)
O3	0.0198 (6)	0.0169 (6)	0.0118 (5)	−0.0038 (5)	0.0012 (4)	−0.0031 (5)
N1	0.0122 (6)	0.0118 (7)	0.0132 (6)	0.0027 (5)	0.0022 (5)	−0.0027 (5)
C1	0.0121 (7)	0.0123 (8)	0.0143 (7)	−0.0018 (6)	0.0009 (5)	−0.0020 (6)
C2	0.0138 (7)	0.0123 (8)	0.0131 (7)	−0.0008 (6)	0.0018 (5)	−0.0019 (6)
C3	0.0117 (7)	0.0105 (8)	0.0178 (7)	−0.0011 (6)	0.0041 (6)	−0.0038 (6)
C4	0.0106 (7)	0.0101 (8)	0.0161 (7)	−0.0012 (6)	0.0007 (5)	−0.0004 (6)
C5	0.0109 (7)	0.0095 (8)	0.0147 (7)	−0.0017 (6)	0.0005 (5)	0.0000 (6)
C6	0.0138 (7)	0.0168 (9)	0.0131 (7)	0.0011 (6)	0.0012 (5)	−0.0013 (6)
C7	0.0257 (9)	0.0263 (10)	0.0185 (8)	0.0054 (8)	0.0005 (7)	0.0019 (7)
C8	0.0214 (8)	0.0276 (11)	0.0188 (8)	0.0083 (8)	−0.0026 (6)	0.0018 (7)
C9	0.0135 (7)	0.0130 (8)	0.0190 (8)	0.0020 (6)	0.0007 (6)	0.0001 (6)
C10	0.0129 (7)	0.0148 (8)	0.0148 (7)	0.0024 (6)	0.0007 (5)	−0.0024 (6)
C11	0.0247 (8)	0.0211 (10)	0.0108 (7)	−0.0028 (7)	0.0009 (6)	−0.0031 (6)
C12	0.0376 (11)	0.0428 (14)	0.0168 (8)	−0.0178 (10)	−0.0057 (8)	−0.0007 (9)

Geometric parameters (Å, º)

Cl1—C3	1.7357 (16)	C6—H6B	0.9700
O1—C1	1.248 (2)	C6—C7	1.528 (2)
O2—C10	1.205 (2)	C7—H7A	0.9700
O3—C10	1.336 (2)	C7—H7B	0.9700
O3—C11	1.4660 (19)	C7—C8	1.513 (3)
N1—H1	0.8600	C8—H8A	0.9700
N1—C1	1.379 (2)	C8—H8B	0.9700
N1—C5	1.370 (2)	C8—C9	1.526 (2)
C1—C2	1.442 (2)	C9—H9A	0.9700
C2—C3	1.367 (2)	C9—H9B	0.9700
C2—C10	1.505 (2)	C11—H11A	0.9700
C3—C4	1.421 (2)	C11—H11B	0.9700
C4—C5	1.375 (2)	C11—C12	1.495 (3)
C4—C9	1.508 (2)	C12—H12A	0.9600
C5—C6	1.505 (2)	C12—H12B	0.9600
C6—H6A	0.9700	C12—H12C	0.9600
C10—O3—C11	115.52 (13)	C8—C7—H7A	109.6
C1—N1—H1	117.2	C8—C7—H7B	109.6
C5—N1—H1	117.2	C7—C8—H8A	109.2
C5—N1—C1	125.60 (13)	C7—C8—H8B	109.2
O1—C1—N1	120.85 (14)	C7—C8—C9	111.90 (15)
O1—C1—C2	124.52 (14)	H8A—C8—H8B	107.9
N1—C1—C2	114.64 (14)	C9—C8—H8A	109.2
C1—C2—C10	119.09 (14)	C9—C8—H8B	109.2
C3—C2—C1	119.48 (14)	C4—C9—C8	111.98 (14)
C3—C2—C10	121.38 (14)	C4—C9—H9A	109.2
C2—C3—Cl1	118.33 (12)	C4—C9—H9B	109.2
C2—C3—C4	123.88 (14)	C8—C9—H9A	109.2
C4—C3—Cl1	117.80 (12)	C8—C9—H9B	109.2
C3—C4—C9	122.42 (14)	H9A—C9—H9B	107.9
C5—C4—C3	115.89 (14)	O2—C10—O3	124.98 (15)
C5—C4—C9	121.69 (14)	O2—C10—C2	123.85 (16)
N1—C5—C4	120.45 (14)	O3—C10—C2	111.15 (14)
N1—C5—C6	116.16 (13)	O3—C11—H11A	109.9
C4—C5—C6	123.39 (14)	O3—C11—H11B	109.9
C5—C6—H6A	109.1	O3—C11—C12	108.71 (14)
C5—C6—H6B	109.1	H11A—C11—H11B	108.3
C5—C6—C7	112.44 (14)	C12—C11—H11A	109.9
H6A—C6—H6B	107.8	C12—C11—H11B	109.9
C7—C6—H6A	109.1	C11—C12—H12A	109.5
C7—C6—H6B	109.1	C11—C12—H12B	109.5
C6—C7—H7A	109.6	C11—C12—H12C	109.5
C6—C7—H7B	109.6	H12A—C12—H12B	109.5
H7A—C7—H7B	108.2	H12A—C12—H12C	109.5
C8—C7—C6	110.10 (15)	H12B—C12—H12C	109.5
Cl1—C3—C4—C5	177.91 (12)	C3—C4—C5—N1	−0.7 (2)
Cl1—C3—C4—C9	−2.6 (2)	C3—C4—C5—C6	179.81 (15)
O1—C1—C2—C3	179.14 (16)	C3—C4—C9—C8	164.73 (16)
O1—C1—C2—C10	1.5 (2)	C4—C5—C6—C7	−15.1 (2)
N1—C1—C2—C3	−0.8 (2)	C5—N1—C1—O1	178.55 (15)
N1—C1—C2—C10	−178.38 (14)	C5—N1—C1—C2	−1.5 (2)
N1—C5—C6—C7	165.33 (15)	C5—C4—C9—C8	−15.8 (2)
C1—N1—C5—C4	2.3 (2)	C5—C6—C7—C8	44.9 (2)
C1—N1—C5—C6	−178.14 (15)	C6—C7—C8—C9	−62.2 (2)
C1—C2—C3—Cl1	−177.15 (12)	C7—C8—C9—C4	46.6 (2)
C1—C2—C3—C4	2.4 (3)	C9—C4—C5—N1	179.79 (15)
C1—C2—C10—O2	83.9 (2)	C9—C4—C5—C6	0.3 (2)
C1—C2—C10—O3	−97.36 (17)	C10—O3—C11—C12	−163.49 (16)
C2—C3—C4—C5	−1.6 (2)	C10—C2—C3—Cl1	0.4 (2)
C2—C3—C4—C9	177.91 (16)	C10—C2—C3—C4	179.91 (15)
C3—C2—C10—O2	−93.6 (2)	C11—O3—C10—O2	3.7 (2)
C3—C2—C10—O3	85.09 (19)	C11—O3—C10—C2	−174.97 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.86	1.97	2.8280 (17)	176
C6—H6B···O2^ii	0.97	2.47	3.379 (2)	155
C8—H8B···O1^ii	0.97	2.60	3.492 (2)	153
C11—H11A···O2^iii	0.97	2.70	3.502 (2)	141
C7—H7B···Cl1^iv	0.97	2.85	3.7731 (19)	160

Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1, −y+2, −z+1; (iii) −x+1, y−1/2, −z+1/2; (iv) −x+1, −y+1, −z+1.