Dimethyl 4-(3-hydroxy­phen­yl)-2,6-dimethyl-1,4-dihydro­pyridine-3,5-dicarboxyl­ate

Rajesh, K.; Vijayakumar, V.; Narasimhamurthy, T.; Suresh, J.; Tiekink, E.R.T.

doi:10.1107/S1600536810011268

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o985

doi:10.1107/S1600536810011268

Open

access

Dimethyl 4-(3-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

K. Rajesh,^a V. Vijayakumar,^a ‡ T. Narasimhamurthy,^b J. Suresh ^c and Edward R. T. Tiekink ^d ^*

^aOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India, ^bMaterials Research Centre, Indian Institute of Science, Bengaluru 560 012, India, ^cThe Madura College (Autonomous), Madurai 625 011, India, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 24 March 2010; accepted 24 March 2010; online 31 March 2010)

The 1,4-dihydropyridine ring in the title compound, C₁₇H₁₉NO₅, has a flattened-boat conformation, and the benzene ring is almost orthogonal to it [dihedral angle = 82.98 (12)°]. The hydroxy group is disordered over two positions in a 0.780 (4):0.220 (4) ratio. In the crystal, hydrogen-bonding interactions of the type N_a—H⋯O_c and O_h—H⋯O_c (a = amine, c = carbonyl and h = hydroxy) link the molecules 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_r = 317.33
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.140
S = 0.96
2831 reflections
226 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

The title compound, (I), was determined as a part of an on-going study of Hantzsch 1,4-dihydropyridines which are notable for their biological activity (Rathore et al., 2009; Reddy et al., 2010).

The 1,4-dihydropyridine ring in (I), Fig. 1, has a flattened-boat conformation with the N1 [0.105 (4) Å] and C3 [0.267 (4) Å] atoms lying above the least-squares plane through the C1,C2,C4, and C5 atoms r.m.s. deviation = 0.0048 Å]. The ring puckering parameters (Cremer & Pople, 1975)are Q = 0.221 (2) Å, θ = 107.0 (5) °, and ϕ₂ = 357.1 (6) °. The aryl ring is orthogonal to the 1,4-dihydropyridine ring, with the dihedral angle between their respective least-squares planes being 82.98 (12) °.

The crystal structure features significant hydrogen bonding interactions, Table 1. The N_amine–H···O_carbonyl interactions lead to chains with glide symmetry along the c axis. O_hydroxyl–H···O_carbonyl hydrogen bonds exist normal to the chain resulting in a three-dimensional network, Fig. 2. As noted in the Experimental, the hydroxyl group is disordered over two positions so that the above description pertains to the major component of the structure only. The minor component of the disorder allows for the formation of O_hydroxy–H···O_hydroxy hydrogen bonds, Table 1, to provide addiotnal cohesion to the crystal packing.

Related literature top

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 top

Dimethyl 1,4-dihydro-4-(3-hydroxyphenyl)-2,6-dimethylpyridine-3,5-dicarboxylate was prepared according to Hantzsch pyridine synthesis (Rathore et al., 2009). To a mixture of 3-hydroxybenzaldehyde (1.221 g, 10 mmol), methyl acetoacetate (2.26 ml, 20 mmol) and ammonium acetate (0.771 g, 10 mmol) in ethanol (10 ml) was added and heated over water bath for about 15 minutes with shaking to ensure thorough mixing. After 15 min, the reaction mixture was kept aside for two days. The solid that separated out was filtered and washed with an ethanol/diethyl ether mixture (1:4). The purity of the crude product was checked through TLC and recrystallized from an ethanol/chloroform mixture (3:2) to yield colourless blocks of (I). Yield: 77%, m. pt. 500–501 K.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 35% probability level. For reasons of clarity, only the major component of the disorder is shown.
	Fig. 2. A view of the unit cell content of (I) shown in projection down the b axis. The N–H···O hydrogen bonds (blue dashed lines) link molecules into supramolecular chains along the c axis. These are connected into the three-dimensional network by O–H···O hydrogen bonds (orange dashed lines), largely obscured in the figure. Colour code: O, red; N, blue; C, grey; and H, green.

Dimethyl 4-(3-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate top

Crystal data top

C₁₇H₁₉NO₅	F(000) = 672
M_r = 317.33	D_x = 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

Data collection top

Bruker SMART APEX CCD diffractometer	2831 independent reflections
Radiation source: fine-focus sealed tube	1777 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −12→12
T_min = 0.646, T_max = 0.746	k = −12→12
25465 measured reflections	l = −17→17

Refinement top

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(F_o²) + (0.060P)² + 0.9343P] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max < 0.001
2831 reflections	Δρ_max = 0.20 e Å⁻³
226 parameters	Δρ_min = −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)

Crystal data top

C₁₇H₁₉NO₅	V = 1601.98 (19) Å³
M_r = 317.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.4863 (7) Å	µ = 0.10 mm⁻¹
b = 10.4091 (7) Å	T = 293 K
c = 14.8702 (11) Å	0.17 × 0.14 × 0.11 mm
β = 99.259 (4)°

Data collection top

Bruker SMART APEX CCD diffractometer	2831 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	1777 reflections with I > 2σ(I)
T_min = 0.646, T_max = 0.746	R_int = 0.063
25465 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	6 restraints
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Δρ_max = 0.20 e Å⁻³
2831 reflections	Δρ_min = −0.30 e Å⁻³
226 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z+1/2; (ii) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₉NO₅
M_r	317.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.4863 (7), 10.4091 (7), 14.8702 (11)
β (°)	99.259 (4)
V (Å³)	1601.98 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.17 × 0.14 × 0.11

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.646, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	25465, 2831, 1777
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.140, 0.96
No. of reflections	2831
No. of parameters	226
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.30

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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)

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

Footnotes

‡Additional correspondence author, e-mail: kvpsvijayakumar@gmail.com.

Acknowledgements

VV is grateful to the DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (1998). SADABS. Bruker AXS Inc., Maddison, Wisconsin, USA. Google Scholar
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Rathore, R. S., Reddy, B. P., Vijayakumar, V., Ragavan, R. V. & Narasimhamurthy, T. (2009). Acta Cryst. B65, 375–381. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Reddy, P. B., Vijayakumar, V., Sarveswari, S., Narasimhamurthy, T. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o658–o659. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). publCIF. In preparation. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o985

doi:10.1107/S1600536810011268

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di­methyl 4-(3-hy­droxy­phen­yl)-2,6-di­methyl-1,4-di­hydro­pyridine-3,5-di­carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

Dimethyl 4-(3-hydroxyphenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate