Dimethyl 4-(3-hydroxy-phen-yl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxyl-ate.

The 1,4-dihydro-pyridine ring in the title compound, C(17)H(19)NO(5), has a flattened-boat conformation, and the benzene ring is almost orthogonal to it [dihedral angle = 82.98 (12)°]. The hydr-oxy group is disordered over two positions in a 0.780 (4):0.220 (4) ratio. In the crystal, hydrogen-bonding inter-actions of the type N(a)-H⋯O(c) and O(h)-H⋯O(c) (a = amine, c = carbonyl and h = hydr-oxy) link the mol-ecules into a three-dimensional network.

Related literature

For further synthetic details, general background to this work and related structures, see: Rathore et al. (2009 ▶); Reddy et al. (2010 ▶). For ring conformations, see: Cremer & Pople, (1975 ▶).

Experimental

Crystal data

C17H19NO5

M = 317.33

Monoclinic,

a = 10.4863 (7) Å

b = 10.4091 (7) Å

c = 14.8702 (11) Å

β = 99.259 (4)°

V = 1601.98 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.17 × 0.14 × 0.11 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.646, T max = 0.746

25465 measured reflections

2831 independent reflections

1777 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.140

S = 0.96

2831 reflections

226 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011268/hb5373sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011268/hb5373Isup2.hkl

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

C17H19NO5	F(000) = 672
Mr = 317.33	Dx = 1.316 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 250 reflections
a = 10.4863 (7) Å	θ = 2.0–25.0°
b = 10.4091 (7) Å	µ = 0.10 mm−1
c = 14.8702 (11) Å	T = 293 K
β = 99.259 (4)°	Block, colourless
V = 1601.98 (19) Å3	0.17 × 0.14 × 0.11 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2831 independent reflections
Radiation source: fine-focus sealed tube	1777 reflections with I > 2σ(I)
graphite	Rint = 0.063
ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −12→12
Tmin = 0.646, Tmax = 0.746	k = −12→12
25465 measured reflections	l = −17→17

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)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.060P)2 + 0.9343P] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max < 0.001
2831 reflections	Δρmax = 0.20 e Å−3
226 parameters	Δρmin = −0.30 e Å−3
6 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: 0.0061 (15)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
O1	1.00543 (18)	0.26412 (19)	0.30899 (11)	0.0533 (5)
O2	1.1268 (2)	0.1391 (2)	0.41024 (13)	0.0691 (7)
O3	0.69399 (19)	0.57282 (18)	0.39888 (12)	0.0550 (6)
O4	0.6633 (2)	0.5861 (2)	0.54328 (14)	0.0695 (7)
N1	0.9365 (2)	0.2976 (2)	0.61286 (13)	0.0415 (6)
H1N	0.963 (2)	0.277 (2)	0.6689 (9)	0.050*
C1	1.0040 (2)	0.2429 (2)	0.55046 (15)	0.0363 (6)
C2	0.9694 (2)	0.2726 (2)	0.46116 (15)	0.0334 (6)
C3	0.8480 (2)	0.3508 (2)	0.42852 (15)	0.0343 (6)
H3	0.8676	0.4112	0.3820	0.041*
C4	0.8074 (2)	0.4287 (2)	0.50609 (16)	0.0343 (6)
C5	0.8478 (2)	0.3961 (2)	0.59392 (16)	0.0366 (6)
C6	1.1099 (3)	0.1549 (3)	0.59385 (18)	0.0516 (7)
H6A	1.0901	0.0683	0.5742	0.077*
H6B	1.1169	0.1596	0.6589	0.077*
H6C	1.1902	0.1805	0.5762	0.077*
C7	1.0337 (2)	0.2271 (3)	0.38735 (17)	0.0402 (6)
C8	1.1905 (4)	0.0913 (4)	0.3373 (2)	0.0949 (14)
H8A	1.1286	0.0481	0.2929	0.142*
H8B	1.2574	0.0322	0.3618	0.142*
H8C	1.2276	0.1619	0.3090	0.142*
C9	0.7183 (2)	0.5346 (2)	0.47692 (17)	0.0397 (6)
C10	0.5688 (3)	0.6853 (3)	0.5194 (2)	0.0778 (11)
H10A	0.6094	0.7591	0.4975	0.117*
H10B	0.5318	0.7086	0.5721	0.117*
H10C	0.5020	0.6544	0.4725	0.117*
C11	0.8128 (3)	0.4554 (3)	0.67894 (17)	0.0533 (8)
H11A	0.8503	0.5396	0.6873	0.080*
H11B	0.8453	0.4027	0.7305	0.080*
H11C	0.7206	0.4619	0.6732	0.080*
C12	0.7382 (2)	0.2639 (2)	0.38472 (16)	0.0370 (6)
C13	0.6625 (3)	0.2969 (3)	0.30306 (18)	0.0482 (7)
H13	0.6791	0.3728	0.2740	0.058*
O5	0.4875 (3)	0.2541 (3)	0.1858 (2)	0.0789 (10)	0.780 (4)
H5O	0.437 (4)	0.196 (4)	0.167 (4)	0.118*	0.780 (4)
C14	0.5613 (3)	0.2175 (3)	0.2637 (2)	0.0558 (8)	0.780 (4)
C15	0.5379 (3)	0.1037 (3)	0.3039 (2)	0.0558 (8)	0.780 (4)
H15	0.4727	0.0493	0.2765	0.067*	0.780 (4)
C16	0.6119 (3)	0.0712 (3)	0.3850 (2)	0.0583 (8)	0.780 (4)
H16	0.5955	−0.0055	0.4131	0.070*	0.780 (4)
O5'	0.5794 (11)	−0.0300 (9)	0.4212 (6)	0.0789 (10)	0.220 (4)
H5O'	0.528 (13)	−0.059 (12)	0.379 (6)	0.118*	0.220 (4)
C14'	0.5613 (3)	0.2175 (3)	0.2637 (2)	0.0558 (8)	0.220 (4)
H14'	0.5096	0.2422	0.2097	0.067*	0.220 (4)
C15'	0.5379 (3)	0.1037 (3)	0.3039 (2)	0.0558 (8)	0.220 (4)
H15'	0.4727	0.0493	0.2765	0.067*	0.220 (4)
C16'	0.6119 (3)	0.0712 (3)	0.3850 (2)	0.0583 (8)	0.220 (4)
C17	0.7108 (3)	0.1501 (3)	0.42606 (19)	0.0475 (7)
H17	0.7591	0.1265	0.4817	0.057*

	U11	U22	U33	U12	U13	U23
O1	0.0573 (12)	0.0738 (14)	0.0294 (10)	−0.0004 (10)	0.0084 (9)	−0.0038 (9)
O2	0.0645 (14)	0.0967 (17)	0.0491 (12)	0.0339 (13)	0.0186 (10)	0.0002 (11)
O3	0.0681 (14)	0.0489 (12)	0.0436 (12)	0.0142 (10)	−0.0044 (9)	0.0045 (9)
O4	0.0840 (16)	0.0704 (14)	0.0561 (13)	0.0429 (13)	0.0169 (11)	0.0036 (11)
N1	0.0538 (14)	0.0458 (13)	0.0250 (11)	0.0107 (11)	0.0064 (10)	0.0065 (9)
C1	0.0368 (14)	0.0382 (14)	0.0340 (13)	−0.0006 (11)	0.0061 (11)	0.0011 (11)
C2	0.0348 (13)	0.0363 (14)	0.0290 (12)	−0.0031 (11)	0.0046 (10)	−0.0005 (10)
C3	0.0391 (14)	0.0368 (14)	0.0265 (12)	0.0012 (11)	0.0033 (10)	0.0021 (10)
C4	0.0370 (14)	0.0317 (13)	0.0340 (13)	−0.0001 (11)	0.0052 (11)	−0.0003 (10)
C5	0.0439 (15)	0.0335 (14)	0.0336 (13)	−0.0018 (12)	0.0096 (11)	−0.0001 (10)
C6	0.0528 (17)	0.0592 (18)	0.0409 (15)	0.0145 (14)	0.0020 (13)	0.0068 (13)
C7	0.0349 (14)	0.0493 (16)	0.0361 (15)	−0.0055 (13)	0.0048 (11)	−0.0050 (12)
C8	0.080 (3)	0.144 (4)	0.066 (2)	0.048 (3)	0.030 (2)	−0.015 (2)
C9	0.0432 (15)	0.0337 (14)	0.0404 (15)	0.0006 (12)	0.0010 (12)	−0.0036 (12)
C10	0.081 (2)	0.070 (2)	0.083 (2)	0.038 (2)	0.015 (2)	−0.0006 (19)
C11	0.074 (2)	0.0536 (18)	0.0348 (15)	0.0107 (15)	0.0149 (14)	−0.0015 (12)
C12	0.0357 (14)	0.0392 (15)	0.0353 (13)	0.0072 (12)	0.0032 (11)	−0.0059 (11)
C13	0.0542 (17)	0.0432 (16)	0.0429 (15)	0.0026 (13)	−0.0057 (13)	−0.0051 (12)
O5	0.089 (2)	0.0661 (19)	0.0653 (18)	−0.0201 (15)	−0.0358 (16)	0.0042 (14)
C14	0.0505 (18)	0.062 (2)	0.0482 (17)	0.0063 (15)	−0.0117 (14)	−0.0169 (15)
C15	0.0447 (17)	0.0486 (18)	0.071 (2)	−0.0035 (14)	0.0014 (15)	−0.0187 (15)
C16	0.0500 (18)	0.0465 (18)	0.078 (2)	−0.0044 (14)	0.0081 (16)	−0.0033 (15)
O5'	0.089 (2)	0.0661 (19)	0.0653 (18)	−0.0201 (15)	−0.0358 (16)	0.0042 (14)
C14'	0.0505 (18)	0.062 (2)	0.0482 (17)	0.0063 (15)	−0.0117 (14)	−0.0169 (15)
C15'	0.0447 (17)	0.0486 (18)	0.071 (2)	−0.0035 (14)	0.0014 (15)	−0.0187 (15)
C16'	0.0500 (18)	0.0465 (18)	0.078 (2)	−0.0044 (14)	0.0081 (16)	−0.0033 (15)
C17	0.0426 (16)	0.0487 (17)	0.0487 (16)	−0.0018 (13)	−0.0003 (13)	0.0022 (13)

O1—C7	1.218 (3)	C10—H10B	0.9600
O2—C7	1.342 (3)	C10—H10C	0.9600
O2—C8	1.450 (4)	C11—H11A	0.9600
O3—C9	1.214 (3)	C11—H11B	0.9600
O4—C9	1.333 (3)	C11—H11C	0.9600
O4—C10	1.436 (3)	C12—C13	1.383 (3)
N1—C1	1.377 (3)	C12—C17	1.386 (4)
N1—C5	1.382 (3)	C13—C14'	1.397 (4)
N1—H1N	0.862 (10)	C13—C14	1.397 (4)
C1—C2	1.355 (3)	C13—H13	0.9300
C1—C6	1.502 (3)	O5—C14	1.341 (4)
C2—C7	1.456 (3)	O5—H5O	0.827 (10)
C2—C3	1.523 (3)	C14—C15	1.366 (4)
C3—C12	1.526 (3)	C15—C16	1.367 (4)
C3—C4	1.525 (3)	C15—H15	0.9300
C3—H3	0.9800	C16—C17	1.385 (4)
C4—C5	1.350 (3)	C16—H16	0.9300
C4—C9	1.465 (3)	O5'—C16'	1.255 (8)
C5—C11	1.505 (3)	O5'—H5O'	0.820 (11)
C6—H6A	0.9600	C14'—C15'	1.366 (4)
C6—H6B	0.9600	C14'—H14'	0.9300
C6—H6C	0.9600	C15'—C16'	1.367 (4)
C8—H8A	0.9600	C15'—H15'	0.9300
C8—H8B	0.9600	C16'—C17	1.385 (4)
C8—H8C	0.9600	C17—H17	0.9300
C10—H10A	0.9600
C7—O2—C8	116.6 (2)	H10A—C10—H10B	109.5
C9—O4—C10	118.0 (2)	O4—C10—H10C	109.5
C1—N1—C5	124.8 (2)	H10A—C10—H10C	109.5
C1—N1—H1N	115.4 (18)	H10B—C10—H10C	109.5
C5—N1—H1N	118.9 (18)	C5—C11—H11A	109.5
C2—C1—N1	118.7 (2)	C5—C11—H11B	109.5
C2—C1—C6	128.5 (2)	H11A—C11—H11B	109.5
N1—C1—C6	112.8 (2)	C5—C11—H11C	109.5
C1—C2—C7	125.5 (2)	H11A—C11—H11C	109.5
C1—C2—C3	120.8 (2)	H11B—C11—H11C	109.5
C7—C2—C3	113.5 (2)	C13—C12—C17	118.1 (2)
C2—C3—C12	110.69 (19)	C13—C12—C3	121.0 (2)
C2—C3—C4	111.33 (18)	C17—C12—C3	120.9 (2)
C12—C3—C4	110.8 (2)	C12—C13—C14'	120.7 (3)
C2—C3—H3	108.0	C12—C13—C14	120.7 (3)
C12—C3—H3	108.0	C12—C13—H13	119.6
C4—C3—H3	108.0	C14'—C13—H13	119.6
C5—C4—C9	124.2 (2)	C14—C13—H13	119.6
C5—C4—C3	121.0 (2)	C14—O5—H5O	109 (4)
C9—C4—C3	114.7 (2)	O5—C14—C15	120.4 (3)
C4—C5—N1	118.7 (2)	O5—C14—C13	119.2 (3)
C4—C5—C11	128.9 (2)	C15—C14—C13	120.5 (3)
N1—C5—C11	112.4 (2)	C16—C15—C14	118.9 (3)
C1—C6—H6A	109.5	C16—C15—H15	120.5
C1—C6—H6B	109.5	C14—C15—H15	120.5
H6A—C6—H6B	109.5	C15—C16—C17	121.4 (3)
C1—C6—H6C	109.5	C15—C16—H16	119.3
H6A—C6—H6C	109.5	C17—C16—H16	119.3
H6B—C6—H6C	109.5	C16'—O5'—H5O'	100 (8)
O1—C7—O2	120.9 (2)	C15'—C14'—C13	120.5 (3)
O1—C7—C2	123.2 (2)	C15'—C14'—H14'	119.8
O2—C7—C2	115.9 (2)	C13—C14'—H14'	119.8
O2—C8—H8A	109.5	C16'—C15'—C14'	118.9 (3)
O2—C8—H8B	109.5	C16'—C15'—H15'	120.5
H8A—C8—H8B	109.5	C14'—C15'—H15'	120.5
O2—C8—H8C	109.5	O5'—C16'—C15'	115.5 (5)
H8A—C8—H8C	109.5	O5'—C16'—C17	123.0 (5)
H8B—C8—H8C	109.5	C15'—C16'—C17	121.4 (3)
O3—C9—O4	121.8 (2)	C16'—C17—C12	120.3 (3)
O3—C9—C4	123.7 (2)	C16—C17—C12	120.3 (3)
O4—C9—C4	114.5 (2)	C16'—C17—H17	119.8
O4—C10—H10A	109.5	C16—C17—H17	119.8
O4—C10—H10B	109.5	C12—C17—H17	119.8
C5—N1—C1—C2	−10.3 (4)	C5—C4—C9—O3	171.2 (3)
C5—N1—C1—C6	169.9 (2)	C3—C4—C9—O3	−11.8 (4)
N1—C1—C2—C7	177.5 (2)	C5—C4—C9—O4	−9.6 (4)
C6—C1—C2—C7	−2.6 (4)	C3—C4—C9—O4	167.4 (2)
N1—C1—C2—C3	−7.7 (4)	C2—C3—C12—C13	−134.6 (2)
C6—C1—C2—C3	172.1 (2)	C4—C3—C12—C13	101.4 (3)
C1—C2—C3—C12	−102.0 (3)	C2—C3—C12—C17	45.9 (3)
C7—C2—C3—C12	73.3 (3)	C4—C3—C12—C17	−78.0 (3)
C1—C2—C3—C4	21.7 (3)	C17—C12—C13—C14'	0.1 (4)
C7—C2—C3—C4	−163.0 (2)	C3—C12—C13—C14'	−179.4 (2)
C2—C3—C4—C5	−20.8 (3)	C17—C12—C13—C14	0.1 (4)
C12—C3—C4—C5	102.9 (3)	C3—C12—C13—C14	−179.4 (2)
C2—C3—C4—C9	162.1 (2)	C12—C13—C14—O5	178.1 (3)
C12—C3—C4—C9	−74.3 (3)	C12—C13—C14—C15	−2.0 (4)
C9—C4—C5—N1	−177.2 (2)	O5—C14—C15—C16	−177.6 (3)
C3—C4—C5—N1	5.9 (4)	C13—C14—C15—C16	2.4 (4)
C9—C4—C5—C11	0.6 (4)	C14—C15—C16—C17	−1.0 (5)
C3—C4—C5—C11	−176.2 (3)	C12—C13—C14'—C15'	−2.0 (4)
C1—N1—C5—C4	11.2 (4)	C13—C14'—C15'—C16'	2.4 (4)
C1—N1—C5—C11	−167.0 (2)	C14'—C15'—C16'—O5'	175.2 (7)
C8—O2—C7—O1	−0.2 (4)	C14'—C15'—C16'—C17	−1.0 (5)
C8—O2—C7—C2	179.1 (3)	O5'—C16'—C17—C12	−176.8 (7)
C1—C2—C7—O1	−174.1 (2)	C15'—C16'—C17—C12	−0.9 (4)
C3—C2—C7—O1	10.8 (3)	C15—C16—C17—C12	−0.9 (4)
C1—C2—C7—O2	6.6 (4)	C13—C12—C17—C16'	1.3 (4)
C3—C2—C7—O2	−168.4 (2)	C3—C12—C17—C16'	−179.2 (2)
C10—O4—C9—O3	2.8 (4)	C13—C12—C17—C16	1.3 (4)
C10—O4—C9—C4	−176.3 (2)	C3—C12—C17—C16	−179.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1i	0.862 (10)	2.103 (14)	2.960 (3)	172.8 (19)
O5—H5o···O3ii	0.827 (10)	2.01 (5)	2.828 (4)	170 (6)
O5'—H5o'···O5ii	0.820 (11)	2.17 (12)	2.778 (10)	132 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O1i	0.86 (1)	2.10 (1)	2.960 (3)	173 (2)
O5—H5o⋯O3ii	0.83 (1)	2.01 (5)	2.828 (4)	170 (6)
O5′—H5o’⋯O5ii	0.82 (1)	2.17 (12)	2.778 (10)	132 (1)

Symmetry codes: (i) ; (ii) .