Ethyl 4-(3-hydroxy-phen-yl)-2,7,7-trimethyl-5-oxo-1,4,5,6,7,8-hexa-hydro-quinoline-3-carboxyl-ate.

In the mol-ecular structure of the title compound, C(21)H(25)NO(4), the dihydro-pyridine ring adopts a flattened boat conformation while the cyclo-hexenone ring is in an envelope conformation. In the crystal structure, mol-ecules are linked into a two-dimensional network parallel to (10) by N-H⋯O and O-H⋯O hydrogen bonds. The network is generated by R(4) (4)(30) and R(4) (4)(34) graph-set motifs.

Related literature

For general background to oxoquinoline derivatives, see: Baba (1997 ▶); Baba et al. (1997 ▶,1998 ▶); Koga et al. (1980 ▶); Qi et al. (2007 ▶). For a related structure, see: Czaun et al. (2002 ▶); For graph-set motifs, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C21H25NO4

M = 355.42

Monoclinic,

a = 10.8721 (4) Å

b = 16.1255 (7) Å

c = 11.0856 (4) Å

β = 100.682 (2)°

V = 1909.83 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.26 × 0.15 × 0.12 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.93, T max = 0.95

14667 measured reflections

3163 independent reflections

2137 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.115

S = 1.02

3163 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809039877/ci2916sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039877/ci2916Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H25NO4	F(000) = 760
Mr = 355.42	Dx = 1.236 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5123 reflections
a = 10.8721 (4) Å	θ = 2.0–30.0°
b = 16.1255 (7) Å	µ = 0.09 mm−1
c = 11.0856 (4) Å	T = 296 K
β = 100.682 (2)°	Prism, yellow
V = 1909.83 (13) Å3	0.26 × 0.15 × 0.12 mm
Z = 4

Bruker Kappa APEXII area-detector diffractometer	3163 independent reflections
Radiation source: fine-focus sealed tube	2137 reflections with I > 2σ(I)
graphite	Rint = 0.041
ω and φ scans	θmax = 24.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −12→12
Tmin = 0.93, Tmax = 0.95	k = −18→17
14667 measured reflections	l = −11→12

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.048P)2 + 0.4479P] where P = (Fo2 + 2Fc2)/3
3163 reflections	(Δ/σ)max = 0.001
236 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

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
O9A	1.01275 (14)	0.04777 (9)	0.71484 (12)	0.0559 (4)
O6A	1.21908 (13)	0.29658 (10)	0.59297 (11)	0.0577 (4)
O9B	0.84079 (15)	−0.01070 (9)	0.60571 (13)	0.0618 (4)
O8C	0.72595 (19)	0.37790 (12)	0.71929 (17)	0.0969 (7)
H8C	0.7098	0.4009	0.7804	0.145*
N1	0.85621 (15)	0.18610 (10)	0.34959 (13)	0.0444 (4)
H1	0.7990	0.1933	0.2857	0.053*
C7	1.03735 (16)	0.23880 (11)	0.47694 (14)	0.0346 (4)
C2	0.95697 (17)	0.23874 (11)	0.36798 (15)	0.0365 (4)
C8	1.01637 (17)	0.18488 (12)	0.58296 (15)	0.0376 (5)
H8	1.0962	0.1583	0.6176	0.045*
C9	0.92188 (17)	0.11633 (11)	0.53752 (15)	0.0368 (4)
C6	1.14473 (17)	0.29327 (12)	0.49410 (15)	0.0394 (5)
C10	0.84203 (17)	0.12208 (12)	0.42851 (15)	0.0384 (5)
C9A	0.91749 (19)	0.04511 (13)	0.61867 (17)	0.0433 (5)
C4	1.04698 (18)	0.37054 (12)	0.29899 (16)	0.0435 (5)
C8B	0.8704 (2)	0.28573 (13)	0.65967 (17)	0.0509 (6)
H8B	0.8260	0.2893	0.5796	0.061*
C3	0.97318 (19)	0.29188 (13)	0.26167 (15)	0.0471 (5)
H3A	0.8913	0.3068	0.2159	0.057*
H3B	1.0157	0.2600	0.2075	0.057*
C5	1.16617 (19)	0.34564 (14)	0.38772 (17)	0.0537 (6)
H5A	1.2199	0.3154	0.3424	0.064*
H5B	1.2103	0.3956	0.4196	0.064*
C8A	0.97467 (19)	0.23549 (12)	0.68484 (15)	0.0421 (5)
C10A	0.7372 (2)	0.06394 (14)	0.37939 (18)	0.0536 (6)
H10A	0.7707	0.0101	0.3675	0.080*
H10B	0.6924	0.0845	0.3024	0.080*
H10C	0.6813	0.0600	0.4368	0.080*
C8F	1.0398 (2)	0.23138 (15)	0.80510 (17)	0.0608 (6)
H8F	1.1111	0.1986	0.8241	0.073*
C8C	0.8307 (2)	0.33082 (14)	0.7515 (2)	0.0608 (6)
C9B	1.0157 (2)	−0.01484 (16)	0.8081 (2)	0.0682 (7)
H91B	1.0250	−0.0694	0.7740	0.082*
H92B	0.9384	−0.0139	0.8400	0.082*
C4A	1.0813 (2)	0.41285 (15)	0.18658 (18)	0.0673 (7)
H41A	1.1279	0.4625	0.2115	0.101*
H42A	1.0063	0.4268	0.1298	0.101*
H43A	1.1313	0.3759	0.1477	0.101*
C8E	0.9988 (3)	0.27565 (18)	0.8960 (2)	0.0777 (8)
H8E	1.0422	0.2714	0.9763	0.093*
C8D	0.8956 (3)	0.32578 (17)	0.8710 (2)	0.0717 (8)
H8D	0.8697	0.3559	0.9333	0.086*
C4B	0.9704 (3)	0.43009 (15)	0.3613 (2)	0.0796 (8)
H41B	1.0181	0.4796	0.3844	0.119*
H42B	0.9502	0.4043	0.4332	0.119*
H43B	0.8947	0.4440	0.3056	0.119*
C9C	1.1234 (3)	0.0034 (2)	0.9074 (2)	0.0993 (11)
H91C	1.1276	−0.0374	0.9710	0.149*
H92C	1.1130	0.0574	0.9407	0.149*
H93C	1.1993	0.0022	0.8749	0.149*

	U11	U22	U33	U12	U13	U23
O9A	0.0679 (10)	0.0550 (9)	0.0430 (7)	0.0030 (7)	0.0057 (7)	0.0178 (7)
O6A	0.0501 (9)	0.0749 (11)	0.0390 (7)	−0.0106 (8)	−0.0157 (7)	0.0038 (7)
O9B	0.0681 (11)	0.0521 (10)	0.0667 (10)	−0.0076 (8)	0.0164 (8)	0.0124 (8)
O8C	0.1049 (15)	0.1028 (16)	0.0858 (13)	0.0344 (13)	0.0246 (11)	−0.0337 (11)
N1	0.0460 (10)	0.0493 (10)	0.0313 (8)	−0.0099 (8)	−0.0099 (7)	0.0028 (8)
C7	0.0365 (10)	0.0380 (11)	0.0272 (9)	0.0017 (8)	0.0006 (7)	−0.0014 (8)
C2	0.0402 (11)	0.0380 (11)	0.0286 (9)	−0.0024 (9)	−0.0005 (8)	−0.0028 (8)
C8	0.0390 (11)	0.0427 (11)	0.0282 (9)	0.0027 (9)	−0.0011 (8)	0.0036 (8)
C9	0.0438 (11)	0.0356 (11)	0.0325 (9)	0.0021 (9)	0.0107 (8)	−0.0012 (8)
C6	0.0375 (11)	0.0456 (12)	0.0312 (9)	0.0008 (9)	−0.0034 (8)	−0.0018 (9)
C10	0.0438 (11)	0.0374 (11)	0.0338 (9)	−0.0024 (9)	0.0068 (8)	−0.0046 (9)
C9A	0.0479 (12)	0.0432 (12)	0.0418 (11)	0.0067 (10)	0.0160 (10)	0.0002 (9)
C4	0.0519 (12)	0.0440 (12)	0.0312 (9)	−0.0051 (10)	−0.0009 (9)	0.0020 (9)
C8B	0.0619 (14)	0.0548 (14)	0.0351 (10)	0.0008 (11)	0.0063 (10)	−0.0091 (10)
C3	0.0542 (13)	0.0540 (13)	0.0282 (9)	−0.0119 (10)	−0.0052 (9)	0.0032 (9)
C5	0.0508 (13)	0.0627 (14)	0.0429 (11)	−0.0151 (11)	−0.0037 (10)	0.0060 (10)
C8A	0.0538 (13)	0.0429 (12)	0.0285 (9)	−0.0071 (10)	0.0046 (8)	−0.0019 (8)
C10A	0.0579 (14)	0.0541 (14)	0.0472 (11)	−0.0153 (11)	0.0058 (10)	−0.0075 (10)
C8F	0.0772 (16)	0.0680 (15)	0.0326 (11)	−0.0053 (13)	−0.0016 (10)	−0.0034 (11)
C8C	0.0738 (16)	0.0540 (15)	0.0586 (14)	−0.0031 (13)	0.0229 (12)	−0.0155 (12)
C9B	0.0835 (18)	0.0674 (16)	0.0571 (13)	0.0206 (13)	0.0220 (13)	0.0296 (12)
C4A	0.0850 (18)	0.0689 (16)	0.0438 (12)	−0.0258 (14)	0.0008 (11)	0.0110 (11)
C8E	0.109 (2)	0.089 (2)	0.0303 (11)	−0.0111 (18)	0.0015 (13)	−0.0135 (12)
C8D	0.101 (2)	0.0724 (18)	0.0468 (13)	−0.0194 (16)	0.0261 (14)	−0.0260 (13)
C4B	0.117 (2)	0.0556 (16)	0.0675 (15)	0.0266 (15)	0.0204 (15)	0.0067 (13)
C9C	0.0805 (19)	0.148 (3)	0.0679 (16)	0.0255 (19)	0.0092 (15)	0.0560 (19)

O9A—C9A	1.342 (2)	C3—H3A	0.97
O9A—C9B	1.442 (2)	C3—H3B	0.97
O6A—C6	1.237 (2)	C5—H5A	0.97
O9B—C9A	1.217 (2)	C5—H5B	0.97
O8C—C8C	1.361 (3)	C8A—C8F	1.390 (3)
O8C—H8C	0.82	C10A—H10A	0.96
N1—C2	1.371 (2)	C10A—H10B	0.96
N1—C10	1.380 (2)	C10A—H10C	0.96
N1—H1	0.86	C8F—C8E	1.374 (3)
C7—C2	1.353 (2)	C8F—H8F	0.93
C7—C6	1.445 (3)	C8C—C8D	1.383 (3)
C7—C8	1.513 (2)	C9B—C9C	1.480 (3)
C2—C3	1.494 (3)	C9B—H91B	0.97
C8—C9	1.529 (3)	C9B—H92B	0.97
C8—C8A	1.529 (3)	C4A—H41A	0.96
C8—H8	0.98	C4A—H42A	0.96
C9—C10	1.354 (2)	C4A—H43A	0.96
C9—C9A	1.465 (3)	C8E—C8D	1.369 (4)
C6—C5	1.503 (3)	C8E—H8E	0.93
C10—C10A	1.498 (3)	C8D—H8D	0.93
C4—C3	1.517 (3)	C4B—H41B	0.96
C4—C4B	1.518 (3)	C4B—H42B	0.96
C4—C4A	1.526 (3)	C4B—H43B	0.96
C4—C5	1.528 (3)	C9C—H91C	0.96
C8B—C8A	1.379 (3)	C9C—H92C	0.96
C8B—C8C	1.383 (3)	C9C—H93C	0.96
C8B—H8B	0.93
C9A—O9A—C9B	117.31 (17)	C4—C5—H5B	108.6
C8C—O8C—H8C	109.5	H5A—C5—H5B	107.6
C2—N1—C10	123.30 (14)	C8B—C8A—C8F	118.38 (19)
C2—N1—H1	118.4	C8B—C8A—C8	120.62 (15)
C10—N1—H1	118.4	C8F—C8A—C8	120.99 (19)
C2—C7—C6	119.35 (16)	C10—C10A—H10A	109.5
C2—C7—C8	121.84 (17)	C10—C10A—H10B	109.5
C6—C7—C8	118.79 (14)	H10A—C10A—H10B	109.5
C7—C2—N1	119.95 (17)	C10—C10A—H10C	109.5
C7—C2—C3	123.56 (17)	H10A—C10A—H10C	109.5
N1—C2—C3	116.47 (14)	H10B—C10A—H10C	109.5
C7—C8—C9	110.38 (14)	C8E—C8F—C8A	120.1 (2)
C7—C8—C8A	112.04 (15)	C8E—C8F—H8F	120.0
C9—C8—C8A	110.86 (15)	C8A—C8F—H8F	120.0
C7—C8—H8	107.8	O8C—C8C—C8B	117.4 (2)
C9—C8—H8	107.8	O8C—C8C—C8D	122.5 (2)
C8A—C8—H8	107.8	C8B—C8C—C8D	120.1 (2)
C10—C9—C9A	120.87 (17)	O9A—C9B—C9C	107.7 (2)
C10—C9—C8	121.66 (16)	O9A—C9B—H91B	110.2
C9A—C9—C8	117.43 (15)	C9C—C9B—H91B	110.2
O6A—C6—C7	121.49 (17)	O9A—C9B—H92B	110.2
O6A—C6—C5	120.01 (17)	C9C—C9B—H92B	110.2
C7—C6—C5	118.50 (14)	H91B—C9B—H92B	108.5
C9—C10—N1	119.23 (16)	C4—C4A—H41A	109.5
C9—C10—C10A	126.89 (18)	C4—C4A—H42A	109.5
N1—C10—C10A	113.86 (15)	H41A—C4A—H42A	109.5
O9B—C9A—O9A	121.89 (18)	C4—C4A—H43A	109.5
O9B—C9A—C9	127.35 (18)	H41A—C4A—H43A	109.5
O9A—C9A—C9	110.76 (17)	H42A—C4A—H43A	109.5
C3—C4—C4B	110.26 (19)	C8D—C8E—C8F	121.6 (2)
C3—C4—C4A	110.37 (15)	C8D—C8E—H8E	119.2
C4B—C4—C4A	109.04 (18)	C8F—C8E—H8E	119.2
C3—C4—C5	107.36 (16)	C8E—C8D—C8C	118.8 (2)
C4B—C4—C5	110.14 (17)	C8E—C8D—H8D	120.6
C4A—C4—C5	109.66 (17)	C8C—C8D—H8D	120.6
C8A—C8B—C8C	121.09 (19)	C4—C4B—H41B	109.5
C8A—C8B—H8B	119.5	C4—C4B—H42B	109.5
C8C—C8B—H8B	119.5	H41B—C4B—H42B	109.5
C2—C3—C4	113.47 (14)	C4—C4B—H43B	109.5
C2—C3—H3A	108.9	H41B—C4B—H43B	109.5
C4—C3—H3A	108.9	H42B—C4B—H43B	109.5
C2—C3—H3B	108.9	C9B—C9C—H91C	109.5
C4—C3—H3B	108.9	C9B—C9C—H92C	109.5
H3A—C3—H3B	107.7	H91C—C9C—H92C	109.5
C6—C5—C4	114.60 (16)	C9B—C9C—H93C	109.5
C6—C5—H5A	108.6	H91C—C9C—H93C	109.5
C4—C5—H5A	108.6	H92C—C9C—H93C	109.5
C6—C5—H5B	108.6
C6—C7—C2—N1	178.61 (17)	C10—C9—C9A—O9A	173.47 (17)
C8—C7—C2—N1	−3.0 (3)	C8—C9—C9A—O9A	−8.8 (2)
C6—C7—C2—C3	0.7 (3)	C7—C2—C3—C4	−26.3 (3)
C8—C7—C2—C3	179.07 (17)	N1—C2—C3—C4	155.73 (17)
C10—N1—C2—C7	−11.5 (3)	C4B—C4—C3—C2	−70.4 (2)
C10—N1—C2—C3	166.61 (17)	C4A—C4—C3—C2	169.08 (18)
C2—C7—C8—C9	17.0 (2)	C5—C4—C3—C2	49.6 (2)
C6—C7—C8—C9	−164.56 (16)	O6A—C6—C5—C4	−150.90 (19)
C2—C7—C8—C8A	−107.0 (2)	C7—C6—C5—C4	30.1 (3)
C6—C7—C8—C8A	71.4 (2)	C3—C4—C5—C6	−52.3 (2)
C7—C8—C9—C10	−19.7 (2)	C4B—C4—C5—C6	67.8 (2)
C8A—C8—C9—C10	105.08 (19)	C4A—C4—C5—C6	−172.20 (18)
C7—C8—C9—C9A	162.58 (16)	C8C—C8B—C8A—C8F	−0.2 (3)
C8A—C8—C9—C9A	−72.7 (2)	C8C—C8B—C8A—C8	179.03 (19)
C2—C7—C6—O6A	178.46 (18)	C7—C8—C8A—C8B	55.7 (2)
C8—C7—C6—O6A	0.0 (3)	C9—C8—C8A—C8B	−68.1 (2)
C2—C7—C6—C5	−2.5 (3)	C7—C8—C8A—C8F	−125.0 (2)
C8—C7—C6—C5	179.01 (17)	C9—C8—C8A—C8F	111.2 (2)
C9A—C9—C10—N1	−174.18 (17)	C8B—C8A—C8F—C8E	1.0 (3)
C8—C9—C10—N1	8.1 (3)	C8—C8A—C8F—C8E	−178.3 (2)
C9A—C9—C10—C10A	4.3 (3)	C8A—C8B—C8C—O8C	−179.0 (2)
C8—C9—C10—C10A	−173.38 (18)	C8A—C8B—C8C—C8D	−0.2 (4)
C2—N1—C10—C9	8.7 (3)	C9A—O9A—C9B—C9C	−176.61 (19)
C2—N1—C10—C10A	−169.93 (18)	C8A—C8F—C8E—C8D	−1.3 (4)
C9B—O9A—C9A—O9B	−4.7 (3)	C8F—C8E—C8D—C8C	0.8 (4)
C9B—O9A—C9A—C9	175.31 (17)	O8C—C8C—C8D—C8E	178.7 (2)
C10—C9—C9A—O9B	−6.5 (3)	C8B—C8C—C8D—C8E	0.0 (4)
C8—C9—C9A—O9B	171.30 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O8C—H8C···O9Bi	0.82	2.05	2.835 (2)	162
N1—H1···O6Aii	0.86	2.16	2.970 (2)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8C—H8C⋯O9Bi	0.82	2.05	2.835 (2)	162
N1—H1⋯O6Aii	0.86	2.16	2.970 (2)	157

Symmetry codes: (i) ; (ii) .