Dimethyl 2,6-dimethyl-4-phenyl-pyridine-3,5-dicarboxyl-ate.

In the title compound, C(17)H(17)NO(4), the dihedral angle between the benzene and pyridine rings is 75.51 (4)°. The benzene and pyridine rings are both approximately planar (r.m.s. deviations of 0.0040 and 0.0083 Å, respectively), indicating that the pyridine N atom is not protonated. The crystal structure is stabilized by weak inter-molecular C-H⋯O and C-H⋯N inter-actions.

Related literature

For the biological activity of pyridine derivatives, see: Lopez-Alarcon et al. (2004 ▶). For related structures, see: Rowan et al. (1996 ▶, 1997 ▶); Lou et al. (2010 ▶). For the sythesis, see: Debache et al. (2008 ▶). For the use of pyridine-type ligands in catalysis models, see: Roodt et al. (2011 ▶); van der Westhuizen et al. (2010 ▶) For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H17NO4

M = 299.32

Monoclinic,

a = 16.0732 (4) Å

b = 7.2497 (2) Å

c = 13.1339 (3) Å

β = 91.003 (1)°

V = 1530.20 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.42 × 0.36 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.962, T max = 0.984

26541 measured reflections

3782 independent reflections

3132 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.114

S = 1.05

3782 reflections

203 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT-Plus (Bruker, 2008 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811049865/fk2046sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049865/fk2046Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811049865/fk2046Isup3.cml

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

C17H17NO4	F(000) = 632
Mr = 299.32	Dx = 1.299 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.0732 (4) Å	Cell parameters from 6764 reflections
b = 7.2497 (2) Å	θ = 3.1–28.2°
c = 13.1339 (3) Å	µ = 0.09 mm−1
β = 91.003 (1)°	T = 100 K
V = 1530.20 (7) Å3	Plate, colourless
Z = 4	0.42 × 0.36 × 0.18 mm

Bruker APEXII CCD diffractometer	3132 reflections with I > 2σ(I)
graphite	Rint = 0.036
φ and ω scans	θmax = 28.3°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −19→21
Tmin = 0.962, Tmax = 0.984	k = −9→9
26541 measured reflections	l = −17→16
3782 independent reflections

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)] = 0.042	Hydrogen site location: geom and difmap
wR(F2) = 0.114	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0581P)2 + 0.5155P] where P = (Fo2 + 2Fc2)/3
3782 reflections	(Δ/σ)max = 0.001
203 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Experimental. The intensity data was collected on a Bruker X8 ApexII 4 K Kappa CCD diffractometer using an exposure time of 10 s/frame. A total of 1659 frames were collected with a frame width of 0.5° covering up to θ = 28.26° with 99.9% completeness accomplished.

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
C1	0.31920 (7)	−0.26904 (16)	0.51421 (9)	0.0155 (2)
C2	0.32461 (7)	−0.11146 (15)	0.57614 (9)	0.0143 (2)
C3	0.25177 (7)	−0.02892 (15)	0.61091 (8)	0.0135 (2)
C4	0.17589 (7)	−0.11187 (15)	0.58352 (9)	0.0143 (2)
C5	0.17515 (7)	−0.27106 (16)	0.52304 (9)	0.0151 (2)
C6	0.39463 (8)	−0.36532 (18)	0.47394 (11)	0.0233 (3)
H6A	0.4141	−0.4576	0.5234	0.035*
H6B	0.4388	−0.2748	0.4627	0.035*
H6C	0.3802	−0.4263	0.4094	0.035*
C7	0.09654 (8)	−0.37102 (17)	0.49311 (10)	0.0209 (3)
H7A	0.1002	−0.413	0.4224	0.031*
H7B	0.049	−0.2875	0.4995	0.031*
H7C	0.0892	−0.4777	0.5379	0.031*
C8	0.25268 (7)	0.13135 (15)	0.68224 (9)	0.0140 (2)
C9	0.27156 (7)	0.30990 (16)	0.65095 (9)	0.0176 (2)
H9	0.2869	0.3325	0.5826	0.021*
C10	0.26785 (8)	0.45503 (16)	0.71995 (9)	0.0196 (3)
H10	0.28	0.5769	0.6982	0.023*
C11	0.24653 (7)	0.42316 (17)	0.82023 (9)	0.0188 (3)
H11	0.2441	0.5229	0.867	0.023*
C12	0.22882 (8)	0.24556 (18)	0.85221 (9)	0.0213 (3)
H12	0.2148	0.2232	0.9211	0.026*
C13	0.23166 (8)	0.10024 (17)	0.78347 (9)	0.0188 (3)
H13	0.2192	−0.0213	0.8055	0.023*
C14	0.09598 (7)	−0.02242 (16)	0.61348 (9)	0.0168 (2)
C15	−0.02859 (8)	−0.0577 (2)	0.70350 (13)	0.0324 (3)
H15A	−0.0238	0.0649	0.7345	0.049*
H15B	−0.0548	−0.1425	0.7514	0.049*
H15C	−0.0627	−0.0498	0.6411	0.049*
C16	0.40794 (7)	−0.03409 (16)	0.60534 (9)	0.0163 (2)
C17	0.53414 (8)	−0.0953 (2)	0.69408 (12)	0.0314 (3)
H17A	0.568	−0.0971	0.6327	0.047*
H17B	0.5573	−0.1822	0.7442	0.047*
H17C	0.5344	0.0293	0.723	0.047*
N1	0.24576 (6)	−0.34462 (13)	0.48819 (7)	0.0154 (2)
O1	0.07254 (6)	0.12423 (12)	0.58103 (8)	0.0250 (2)
O2	0.05370 (6)	−0.12553 (12)	0.67903 (7)	0.0227 (2)
O3	0.43443 (6)	0.11142 (12)	0.57660 (8)	0.0236 (2)
O4	0.44906 (6)	−0.14856 (13)	0.66776 (7)	0.0255 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0148 (5)	0.0143 (5)	0.0174 (5)	−0.0007 (4)	0.0027 (4)	0.0020 (4)
C2	0.0138 (5)	0.0132 (5)	0.0159 (5)	−0.0015 (4)	0.0001 (4)	0.0024 (4)
C3	0.0154 (5)	0.0111 (5)	0.0139 (5)	−0.0003 (4)	0.0003 (4)	0.0026 (4)
C4	0.0141 (5)	0.0131 (5)	0.0158 (5)	0.0002 (4)	0.0002 (4)	0.0020 (4)
C5	0.0150 (5)	0.0136 (5)	0.0166 (5)	−0.0012 (4)	−0.0008 (4)	0.0017 (4)
C6	0.0168 (6)	0.0202 (6)	0.0331 (7)	−0.0010 (5)	0.0066 (5)	−0.0062 (5)
C7	0.0157 (6)	0.0183 (6)	0.0286 (7)	−0.0023 (5)	−0.0019 (5)	−0.0055 (5)
C8	0.0126 (5)	0.0137 (5)	0.0157 (5)	−0.0002 (4)	−0.0015 (4)	−0.0002 (4)
C9	0.0213 (6)	0.0154 (6)	0.0162 (5)	−0.0018 (4)	0.0009 (4)	0.0014 (4)
C10	0.0232 (6)	0.0131 (5)	0.0223 (6)	−0.0020 (5)	−0.0023 (5)	0.0001 (5)
C11	0.0183 (6)	0.0181 (6)	0.0197 (6)	0.0012 (4)	−0.0024 (5)	−0.0056 (4)
C12	0.0261 (6)	0.0228 (6)	0.0151 (5)	−0.0013 (5)	0.0012 (5)	−0.0001 (5)
C13	0.0232 (6)	0.0153 (5)	0.0179 (6)	−0.0022 (5)	0.0001 (5)	0.0024 (4)
C14	0.0142 (5)	0.0155 (5)	0.0207 (6)	−0.0016 (4)	−0.0015 (4)	−0.0030 (4)
C15	0.0200 (7)	0.0269 (7)	0.0508 (9)	0.0028 (5)	0.0155 (6)	0.0014 (6)
C16	0.0135 (5)	0.0167 (6)	0.0189 (6)	0.0001 (4)	0.0020 (4)	−0.0020 (4)
C17	0.0180 (6)	0.0337 (8)	0.0422 (8)	−0.0033 (5)	−0.0109 (6)	0.0044 (6)
N1	0.0169 (5)	0.0133 (5)	0.0160 (5)	−0.0006 (4)	0.0007 (4)	0.0009 (4)
O1	0.0198 (5)	0.0183 (4)	0.0368 (5)	0.0049 (3)	0.0015 (4)	0.0042 (4)
O2	0.0173 (4)	0.0203 (4)	0.0308 (5)	0.0013 (3)	0.0084 (4)	0.0020 (4)
O3	0.0174 (4)	0.0173 (4)	0.0361 (5)	−0.0043 (3)	0.0001 (4)	0.0031 (4)
O4	0.0178 (4)	0.0254 (5)	0.0330 (5)	−0.0043 (4)	−0.0084 (4)	0.0081 (4)

C1—N1	1.3402 (15)	C9—H9	0.95
C1—C2	1.4042 (16)	C10—C11	1.3861 (17)
C1—C6	1.5032 (16)	C10—H10	0.95
C2—C3	1.3986 (15)	C11—C12	1.3854 (18)
C2—C16	1.4958 (16)	C11—H11	0.95
C3—C4	1.4011 (15)	C12—C13	1.3887 (17)
C3—C8	1.4924 (15)	C12—H12	0.95
C4—C5	1.4009 (16)	C13—H13	0.95
C4—C14	1.4977 (16)	C14—O1	1.2034 (15)
C5—N1	1.3417 (15)	C14—O2	1.3350 (15)
C5—C7	1.5030 (16)	C15—O2	1.4524 (15)
C6—H6A	0.98	C15—H15A	0.98
C6—H6B	0.98	C15—H15B	0.98
C6—H6C	0.98	C15—H15C	0.98
C7—H7A	0.98	C16—O3	1.2009 (15)
C7—H7B	0.98	C16—O4	1.3338 (15)
C7—H7C	0.98	C17—O4	1.4568 (15)
C8—C9	1.3932 (16)	C17—H17A	0.98
C8—C13	1.3959 (16)	C17—H17B	0.98
C9—C10	1.3906 (17)	C17—H17C	0.98
N1—C1—C2	121.72 (10)	C11—C10—C9	120.48 (11)
N1—C1—C6	115.63 (10)	C11—C10—H10	119.8
C2—C1—C6	122.64 (11)	C9—C10—H10	119.8
C3—C2—C1	119.57 (10)	C12—C11—C10	119.90 (11)
C3—C2—C16	120.45 (10)	C12—C11—H11	120
C1—C2—C16	119.98 (10)	C10—C11—H11	120
C2—C3—C4	117.54 (10)	C11—C12—C13	119.92 (11)
C2—C3—C8	122.61 (10)	C11—C12—H12	120
C4—C3—C8	119.62 (10)	C13—C12—H12	120
C5—C4—C3	119.86 (10)	C12—C13—C8	120.52 (11)
C5—C4—C14	120.45 (10)	C12—C13—H13	119.7
C3—C4—C14	119.57 (10)	C8—C13—H13	119.7
N1—C5—C4	121.47 (10)	O1—C14—O2	124.29 (11)
N1—C5—C7	115.56 (10)	O1—C14—C4	123.65 (11)
C4—C5—C7	122.97 (10)	O2—C14—C4	112.06 (10)
C1—C6—H6A	109.5	O2—C15—H15A	109.5
C1—C6—H6B	109.5	O2—C15—H15B	109.5
H6A—C6—H6B	109.5	H15A—C15—H15B	109.5
C1—C6—H6C	109.5	O2—C15—H15C	109.5
H6A—C6—H6C	109.5	H15A—C15—H15C	109.5
H6B—C6—H6C	109.5	H15B—C15—H15C	109.5
C5—C7—H7A	109.5	O3—C16—O4	124.40 (11)
C5—C7—H7B	109.5	O3—C16—C2	124.73 (11)
H7A—C7—H7B	109.5	O4—C16—C2	110.87 (10)
C5—C7—H7C	109.5	O4—C17—H17A	109.5
H7A—C7—H7C	109.5	O4—C17—H17B	109.5
H7B—C7—H7C	109.5	H17A—C17—H17B	109.5
C9—C8—C13	119.26 (11)	O4—C17—H17C	109.5
C9—C8—C3	122.55 (10)	H17A—C17—H17C	109.5
C13—C8—C3	118.18 (10)	H17B—C17—H17C	109.5
C10—C9—C8	119.91 (11)	C1—N1—C5	119.80 (10)
C10—C9—H9	120	C14—O2—C15	115.40 (10)
C8—C9—H9	120	C16—O4—C17	115.72 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···O3i	0.98	2.42	3.3825 (15)	167.
C7—H7B···O1ii	0.98	2.5	3.3826 (15)	149.
C13—H13···N1iii	0.95	2.62	3.2701 (16)	126.
C15—H15A···O2iv	0.98	2.56	3.5187 (17)	165.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6B⋯O3i	0.98	2.42	3.3825 (15)	167
C7—H7B⋯O1ii	0.98	2.5	3.3826 (15)	149
C13—H13⋯N1iii	0.95	2.62	3.2701 (16)	126
C15—H15A⋯O2iv	0.98	2.56	3.5187 (17)	165

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .