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

Fun, H.-K.; Quah, C.K.; Reddy, B.P.; Sarveswari, S.; Vijayakumar, V.

doi:10.1107/S1600536809033364

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Pages o2255-o2256

doi:10.1107/S1600536809033364

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

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § B. Palakshi Reddy,^b S. Sarveswari ^b and V. Vijayakumar ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bOrganic Chemistry Division, School of Science and Humanities, VIT University, Vellore 632 014, India
^*Correspondence e-mail: hkfun@usm.my

(Received 20 August 2009; accepted 21 August 2009; online 26 August 2009)

In the title molecule, C₁₉H₂₃NO₅, the dihedral angle formed by the benzene ring and the planar part of the dihydropyridine ring is 83.52 (5)°. The dihydropyridine ring adopts a flattened boat conformation. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, generating chains running parallel to [100]. The crystal structure is consolidated by C—H⋯O contacts.

Related literature

For general background to Hantzsch 1,4-dihydropyridines (1,4-DHPS), see: Gaudio et al. (1994 ); Bocker & Guengerich (1986 ); Gordeev et al. (1996 ); Sunkel et al. (1992 ); Vo et al. (1995 ); Cooper et al. (1992 ). For a related structure, see: Fun et al. (2009 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For geometric analysis, see: Cremer & Pople (1975 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₉H₂₃NO₅
M_r = 345.38
Triclinic, $[P \overline 1]$
a = 7.4108 (1) Å
b = 9.7459 (2) Å
c = 12.3359 (2) Å
α = 87.412 (1)°
β = 86.244 (1)°
γ = 76.402 (1)°
V = 863.72 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.39 × 0.33 × 0.19 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.963, T_max = 0.982
26880 measured reflections
4579 independent reflections
3972 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.099
S = 1.05
4579 reflections
235 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O4ⁱ	0.854 (15)	2.230 (15)	3.0710 (11)	168.0 (13)
C4—H4A⋯O1ⁱⁱ	0.93	2.58	3.5104 (12)	174
C15—H15A⋯O1ⁱⁱⁱ	0.96	2.60	3.5500 (14)	172
C19—H19B⋯O4ⁱ	0.96	2.57	3.4677 (12)	155
Symmetry codes: (i) x+1, y, z; (ii) -x, -y+1, -z; (iii) x+1, y-1, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809033364/tk2529sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809033364/tk2529Isup2.hkl

checkCIF report

Comment top

Hantzsch 1,4-dihydropyridines (1,4-DHPS) are biologically active compounds which include various vasodilator, anti-hypertensive, bronchodilator, hepatoprotective, anti-tumor, anti-mutagenic, geroprotective, and anti-diabetic agents (Gaudio et al., 1994). Nifedipine, Nitrendipine and Nimodipine have found commercial utility as calcium channel blockers (Bocker & Guengerich, 1986; Gordeev et al., 1996). For the treatment of congestive heart failure, a number of DHP calcium antagonists have been introduced (Sunkel et al., 1992; Vo et al., 1995). Some DHPs have been introduced as neuroprotectants and cognition enhancers. In addition, a number of DHPs with platelet anti-aggregatory activity have also been discovered (Cooper et al., 1992).

The geometric parameters in (I), Fig. 1, are comparable to those in a closely related structure (Fun et al., 2009). The benzene ring (C1—C6) and dihydropyridine ring (C7—C11/N1) are nearly perpendicular as seen in the angle of 83.52 (5)° between their least-squares planes. The dihydropyridine ring adopts a flattened boat conformation with puckering parameters (Cremer & Pople, 1975) Q = 0.2688 (10) Å; Θ = 73.7 (2)° and ϕ = 183.6 (2)°, with atoms N1 and C7 deviating by 0.125 (1) and 0.172 (1) Å, respectively, from the mean plane of the dihydropyridine ring.

In the solid-state (Fig. 2), the molecules are linked via N1—H1N1···O4 hydrogen bonds (Table 1) to generate supramolecular chains running parallel to the [1 0 0] direction. The O4 atom also participates in a C19—H19B···O4 contact to generate, along with the N1—H1N1···O4 hydrogen bond, a R₂¹(6) ring motif (Bernstein et al., 1995); Fig. 2. Molecules are further consolidated by intermolecular C—H···O interactions (Table 1).

Related literature top

For general background to Hantzsch 1,4-dihydropyridines (1,4-DHPS), see: Gaudio et al. (1994); Bocker & Guengerich (1986); Gordeev et al. (1996); Sunkel et al. (1992); Vo et al. (1995); Cooper et al. (1992). For a related structure, see: Fun et al. (2009). For hydrogen-bond motifs, see: Bernstein et al. (1995). For geometric analysis, see: Cremer & Pople (1975). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

Compound (I) was prepared according to the Hantzsch pyridine synthesis. A mixture of 4-ethoxybenzaldehyde (10 mmol), methylacetoacetate (20 mmol) and ammonium acetate (10 mmol) were heated at 353 K for 3 h (monitored by TLC). After completion of the reaction, the mixture was cooled to room temperature and kept for 2 days to get the solid product. The solid was extracted using diethyl ether and the mother liquors kept for crystallization. The purity of the crude product was checked through TLC and recrystallized using acetone and ether; M.p. 403–405 K. IR (KBr): υ: 3361, 2985, 2948, 1682, 1652, 1485, 1235 cm^-1.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The crystal packing of (I), viewed along the b axis, showing the R₂¹(6) ring motifs. The dashed lines indicate N-H···O hydrogen bonds and C-H···O contacts.

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

Crystal data top

C₁₉H₂₃NO₅	Z = 2
M_r = 345.38	F(000) = 368
Triclinic, P1	D_x = 1.328 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4108 (1) Å	Cell parameters from 9914 reflections
b = 9.7459 (2) Å	θ = 2.7–37.4°
c = 12.3359 (2) Å	µ = 0.10 mm⁻¹
α = 87.412 (1)°	T = 100 K
β = 86.244 (1)°	Block, colourless
γ = 76.402 (1)°	0.39 × 0.33 × 0.19 mm
V = 863.72 (3) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4579 independent reflections
Radiation source: fine-focus sealed tube	3972 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 29.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→9
T_min = 0.963, T_max = 0.982	k = −13→13
26880 measured reflections	l = −16→16

Refinement top

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0475P)² + 0.2882P] where P = (F_o² + 2F_c²)/3
4579 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₉H₂₃NO₅	γ = 76.402 (1)°
M_r = 345.38	V = 863.72 (3) Å³
Triclinic, P1	Z = 2
a = 7.4108 (1) Å	Mo Kα radiation
b = 9.7459 (2) Å	µ = 0.10 mm⁻¹
c = 12.3359 (2) Å	T = 100 K
α = 87.412 (1)°	0.39 × 0.33 × 0.19 mm
β = 86.244 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4579 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3972 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.982	R_int = 0.026
26880 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.38 e Å⁻³
4579 reflections	Δρ_min = −0.23 e Å⁻³
235 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

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

	x	y	z	U_iso*/U_eq
O1	0.19861 (10)	0.60173 (8)	0.03818 (6)	0.01954 (16)
O2	0.44712 (10)	−0.06125 (8)	0.22047 (7)	0.02351 (17)
O3	0.75904 (10)	−0.12488 (7)	0.20146 (6)	0.01800 (15)
O4	0.12920 (9)	0.26642 (8)	0.49547 (6)	0.01857 (16)
O5	0.28689 (10)	0.36872 (8)	0.60451 (6)	0.01980 (16)
N1	0.78173 (11)	0.17632 (9)	0.43091 (7)	0.01522 (17)
C1	0.47641 (14)	0.38112 (11)	0.24725 (8)	0.0186 (2)
H1A	0.5811	0.3780	0.2858	0.022*
C2	0.42251 (14)	0.49057 (11)	0.17125 (9)	0.0205 (2)
H2A	0.4905	0.5593	0.1594	0.025*
C3	0.26590 (13)	0.49643 (10)	0.11306 (8)	0.01547 (19)
C4	0.16801 (13)	0.39106 (10)	0.12993 (8)	0.01699 (19)
H4A	0.0646	0.3934	0.0904	0.020*
C5	0.22500 (13)	0.28219 (10)	0.20605 (8)	0.01653 (19)
H5A	0.1593	0.2118	0.2163	0.020*
C6	0.37885 (12)	0.27631 (10)	0.26738 (7)	0.01368 (18)
C7	0.43800 (12)	0.16185 (10)	0.35541 (7)	0.01319 (17)
H7A	0.3410	0.1087	0.3666	0.016*
C8	0.61931 (12)	0.05947 (10)	0.32117 (7)	0.01377 (18)
C9	0.78381 (13)	0.07461 (10)	0.35543 (8)	0.01377 (18)
C10	0.62373 (13)	0.24334 (10)	0.49089 (8)	0.01427 (18)
C11	0.45520 (12)	0.22955 (10)	0.46159 (7)	0.01390 (18)
C12	0.28242 (15)	0.72105 (11)	0.03018 (9)	0.0222 (2)
H12A	0.4125	0.6916	0.0059	0.027*
H12B	0.2744	0.7636	0.1004	0.027*
C13	0.17764 (17)	0.82565 (13)	−0.05091 (10)	0.0293 (3)
H13A	0.2306	0.9067	−0.0585	0.044*
H13B	0.0494	0.8544	−0.0258	0.044*
H13C	0.1863	0.7823	−0.1200	0.044*
C14	0.59716 (13)	−0.04608 (10)	0.24493 (8)	0.01548 (18)
C15	0.73788 (15)	−0.22168 (12)	0.12099 (9)	0.0234 (2)
H15A	0.8579	−0.2777	0.0980	0.035*
H15B	0.6800	−0.1695	0.0596	0.035*
H15C	0.6617	−0.2824	0.1517	0.035*
C16	0.27731 (13)	0.28733 (10)	0.52057 (8)	0.01461 (18)
C17	0.11161 (14)	0.43650 (12)	0.65823 (9)	0.0214 (2)
H17A	0.1336	0.4930	0.7155	0.032*
H17B	0.0500	0.3659	0.6882	0.032*
H17C	0.0348	0.4957	0.6067	0.032*
C18	0.97650 (13)	−0.00902 (10)	0.32325 (8)	0.01687 (19)
H18A	1.0010	0.0034	0.2465	0.025*
H18B	0.9854	−0.1073	0.3408	0.025*
H18C	1.0659	0.0235	0.3619	0.025*
C19	0.66430 (13)	0.32411 (11)	0.58374 (8)	0.01801 (19)
H19A	0.5904	0.4192	0.5801	0.027*
H19B	0.7937	0.3254	0.5792	0.027*
H19C	0.6347	0.2793	0.6513	0.027*
H1N1	0.886 (2)	0.1880 (15)	0.4495 (12)	0.027 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0198 (4)	0.0181 (3)	0.0215 (4)	−0.0055 (3)	−0.0063 (3)	0.0054 (3)
O2	0.0157 (3)	0.0248 (4)	0.0319 (4)	−0.0066 (3)	−0.0035 (3)	−0.0084 (3)
O3	0.0157 (3)	0.0167 (3)	0.0220 (4)	−0.0044 (3)	0.0005 (3)	−0.0051 (3)
O4	0.0112 (3)	0.0236 (4)	0.0213 (4)	−0.0047 (3)	−0.0010 (3)	−0.0018 (3)
O5	0.0128 (3)	0.0258 (4)	0.0209 (4)	−0.0040 (3)	0.0011 (3)	−0.0073 (3)
N1	0.0099 (4)	0.0184 (4)	0.0181 (4)	−0.0042 (3)	−0.0022 (3)	−0.0015 (3)
C1	0.0154 (4)	0.0212 (5)	0.0214 (5)	−0.0075 (4)	−0.0074 (4)	0.0029 (4)
C2	0.0202 (5)	0.0200 (5)	0.0244 (5)	−0.0104 (4)	−0.0067 (4)	0.0040 (4)
C3	0.0153 (4)	0.0158 (4)	0.0144 (4)	−0.0017 (3)	−0.0015 (3)	−0.0002 (3)
C4	0.0142 (4)	0.0197 (5)	0.0178 (4)	−0.0043 (3)	−0.0046 (3)	−0.0001 (4)
C5	0.0149 (4)	0.0169 (4)	0.0194 (5)	−0.0066 (3)	−0.0033 (3)	0.0003 (4)
C6	0.0120 (4)	0.0144 (4)	0.0143 (4)	−0.0021 (3)	−0.0012 (3)	−0.0013 (3)
C7	0.0100 (4)	0.0144 (4)	0.0158 (4)	−0.0038 (3)	−0.0021 (3)	0.0000 (3)
C8	0.0120 (4)	0.0135 (4)	0.0159 (4)	−0.0034 (3)	−0.0009 (3)	0.0008 (3)
C9	0.0128 (4)	0.0130 (4)	0.0154 (4)	−0.0033 (3)	−0.0008 (3)	0.0019 (3)
C10	0.0132 (4)	0.0149 (4)	0.0147 (4)	−0.0033 (3)	−0.0016 (3)	0.0013 (3)
C11	0.0115 (4)	0.0152 (4)	0.0151 (4)	−0.0034 (3)	−0.0009 (3)	0.0004 (3)
C12	0.0249 (5)	0.0192 (5)	0.0238 (5)	−0.0078 (4)	−0.0035 (4)	0.0042 (4)
C13	0.0284 (6)	0.0243 (5)	0.0333 (6)	−0.0047 (4)	−0.0020 (5)	0.0120 (5)
C14	0.0149 (4)	0.0138 (4)	0.0178 (4)	−0.0040 (3)	−0.0009 (3)	0.0012 (3)
C15	0.0231 (5)	0.0214 (5)	0.0270 (5)	−0.0065 (4)	0.0003 (4)	−0.0093 (4)
C16	0.0130 (4)	0.0157 (4)	0.0147 (4)	−0.0028 (3)	−0.0011 (3)	0.0023 (3)
C17	0.0153 (5)	0.0247 (5)	0.0229 (5)	−0.0019 (4)	0.0026 (4)	−0.0055 (4)
C18	0.0112 (4)	0.0172 (4)	0.0221 (5)	−0.0029 (3)	−0.0012 (3)	−0.0005 (4)
C19	0.0135 (4)	0.0222 (5)	0.0192 (5)	−0.0050 (3)	−0.0033 (3)	−0.0033 (4)

Geometric parameters (Å, º) top

O1—C3	1.3745 (11)	C8—C9	1.3580 (13)
O1—C12	1.4384 (13)	C8—C14	1.4686 (13)
O2—C14	1.2143 (12)	C9—C18	1.5062 (13)
O3—C14	1.3551 (11)	C10—C11	1.3605 (12)
O3—C15	1.4403 (12)	C10—C19	1.5033 (13)
O4—C16	1.2237 (11)	C11—C16	1.4651 (13)
O5—C16	1.3479 (12)	C12—C13	1.5100 (15)
O5—C17	1.4443 (12)	C12—H12A	0.9700
N1—C10	1.3841 (12)	C12—H12B	0.9700
N1—C9	1.3872 (12)	C13—H13A	0.9600
N1—H1N1	0.852 (15)	C13—H13B	0.9600
C1—C6	1.3888 (13)	C13—H13C	0.9600
C1—C2	1.3909 (14)	C15—H15A	0.9600
C1—H1A	0.9300	C15—H15B	0.9600
C2—C3	1.3928 (13)	C15—H15C	0.9600
C2—H2A	0.9300	C17—H17A	0.9600
C3—C4	1.3912 (14)	C17—H17B	0.9600
C4—C5	1.3919 (13)	C17—H17C	0.9600
C4—H4A	0.9300	C18—H18A	0.9600
C5—C6	1.3978 (12)	C18—H18B	0.9600
C5—H5A	0.9300	C18—H18C	0.9600
C6—C7	1.5293 (12)	C19—H19A	0.9600
C7—C11	1.5188 (13)	C19—H19B	0.9600
C7—C8	1.5207 (12)	C19—H19C	0.9600
C7—H7A	0.9800

C3—O1—C12	117.11 (8)	O1—C12—C13	107.30 (9)
C14—O3—C15	114.71 (8)	O1—C12—H12A	110.3
C16—O5—C17	116.10 (8)	C13—C12—H12A	110.3
C10—N1—C9	123.78 (8)	O1—C12—H12B	110.3
C10—N1—H1N1	117.3 (10)	C13—C12—H12B	110.3
C9—N1—H1N1	118.0 (10)	H12A—C12—H12B	108.5
C6—C1—C2	122.08 (9)	C12—C13—H13A	109.5
C6—C1—H1A	119.0	C12—C13—H13B	109.5
C2—C1—H1A	119.0	H13A—C13—H13B	109.5
C1—C2—C3	119.51 (9)	C12—C13—H13C	109.5
C1—C2—H2A	120.2	H13A—C13—H13C	109.5
C3—C2—H2A	120.2	H13B—C13—H13C	109.5
O1—C3—C4	116.37 (8)	O2—C14—O3	121.92 (9)
O1—C3—C2	124.04 (9)	O2—C14—C8	123.53 (9)
C4—C3—C2	119.58 (9)	O3—C14—C8	114.53 (8)
C3—C4—C5	119.90 (9)	O3—C15—H15A	109.5
C3—C4—H4A	120.1	O3—C15—H15B	109.5
C5—C4—H4A	120.1	H15A—C15—H15B	109.5
C4—C5—C6	121.45 (9)	O3—C15—H15C	109.5
C4—C5—H5A	119.3	H15A—C15—H15C	109.5
C6—C5—H5A	119.3	H15B—C15—H15C	109.5
C1—C6—C5	117.45 (9)	O4—C16—O5	121.62 (9)
C1—C6—C7	120.24 (8)	O4—C16—C11	123.31 (9)
C5—C6—C7	122.30 (8)	O5—C16—C11	115.06 (8)
C11—C7—C8	110.84 (7)	O5—C17—H17A	109.5
C11—C7—C6	109.88 (7)	O5—C17—H17B	109.5
C8—C7—C6	111.28 (7)	H17A—C17—H17B	109.5
C11—C7—H7A	108.2	O5—C17—H17C	109.5
C8—C7—H7A	108.2	H17A—C17—H17C	109.5
C6—C7—H7A	108.2	H17B—C17—H17C	109.5
C9—C8—C14	125.40 (9)	C9—C18—H18A	109.5
C9—C8—C7	120.71 (8)	C9—C18—H18B	109.5
C14—C8—C7	113.77 (8)	H18A—C18—H18B	109.5
C8—C9—N1	118.66 (8)	C9—C18—H18C	109.5
C8—C9—C18	127.97 (9)	H18A—C18—H18C	109.5
N1—C9—C18	113.36 (8)	H18B—C18—H18C	109.5
C11—C10—N1	118.71 (8)	C10—C19—H19A	109.5
C11—C10—C19	127.90 (9)	C10—C19—H19B	109.5
N1—C10—C19	113.39 (8)	H19A—C19—H19B	109.5
C10—C11—C16	124.96 (9)	C10—C19—H19C	109.5
C10—C11—C7	120.47 (8)	H19A—C19—H19C	109.5
C16—C11—C7	114.33 (8)	H19B—C19—H19C	109.5

C6—C1—C2—C3	0.06 (16)	C10—N1—C9—C18	−164.68 (8)
C12—O1—C3—C4	171.89 (9)	C9—N1—C10—C11	−12.56 (14)
C12—O1—C3—C2	−7.98 (14)	C9—N1—C10—C19	167.12 (9)
C1—C2—C3—O1	178.41 (9)	N1—C10—C11—C16	176.37 (8)
C1—C2—C3—C4	−1.46 (15)	C19—C10—C11—C16	−3.25 (16)
O1—C3—C4—C5	−178.70 (9)	N1—C10—C11—C7	−9.52 (13)
C2—C3—C4—C5	1.18 (15)	C19—C10—C11—C7	170.86 (9)
C3—C4—C5—C6	0.51 (15)	C8—C7—C11—C10	26.43 (12)
C2—C1—C6—C5	1.58 (15)	C6—C7—C11—C10	−96.98 (10)
C2—C1—C6—C7	−177.17 (9)	C8—C7—C11—C16	−158.87 (8)
C4—C5—C6—C1	−1.86 (15)	C6—C7—C11—C16	77.72 (10)
C4—C5—C6—C7	176.86 (9)	C3—O1—C12—C13	−176.21 (9)
C1—C6—C7—C11	51.88 (11)	C15—O3—C14—O2	2.92 (14)
C5—C6—C7—C11	−126.81 (9)	C15—O3—C14—C8	−175.86 (8)
C1—C6—C7—C8	−71.27 (11)	C9—C8—C14—O2	176.04 (10)
C5—C6—C7—C8	110.05 (10)	C7—C8—C14—O2	−7.83 (14)
C11—C7—C8—C9	−24.86 (12)	C9—C8—C14—O3	−5.20 (14)
C6—C7—C8—C9	97.74 (10)	C7—C8—C14—O3	170.92 (8)
C11—C7—C8—C14	158.81 (8)	C17—O5—C16—O4	−3.79 (13)
C6—C7—C8—C14	−78.58 (10)	C17—O5—C16—C11	175.00 (8)
C14—C8—C9—N1	−177.70 (8)	C10—C11—C16—O4	−175.82 (9)
C7—C8—C9—N1	6.43 (13)	C7—C11—C16—O4	9.75 (13)
C14—C8—C9—C18	0.95 (16)	C10—C11—C16—O5	5.42 (14)
C7—C8—C9—C18	−174.92 (9)	C7—C11—C16—O5	−169.02 (8)
C10—N1—C9—C8	14.15 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O4ⁱ	0.854 (15)	2.230 (15)	3.0710 (11)	168.0 (13)
C4—H4A···O1ⁱⁱ	0.93	2.58	3.5104 (12)	174
C15—H15A···O1ⁱⁱⁱ	0.96	2.60	3.5500 (14)	172
C19—H19B···O4ⁱ	0.96	2.57	3.4677 (12)	155

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

Experimental details

Crystal data
Chemical formula	C₁₉H₂₃NO₅
M_r	345.38
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.4108 (1), 9.7459 (2), 12.3359 (2)
α, β, γ (°)	87.412 (1), 86.244 (1), 76.402 (1)
V (Å³)	863.72 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.39 × 0.33 × 0.19

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.963, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	26880, 4579, 3972
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.099, 1.05
No. of reflections	4579
No. of parameters	235
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.23

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O4ⁱ	0.854 (15)	2.230 (15)	3.0710 (11)	168.0 (13)
C4—H4A···O1ⁱⁱ	0.93	2.58	3.5104 (12)	174
C15—H15A···O1ⁱⁱⁱ	0.96	2.60	3.5500 (14)	172
C19—H19B···O4ⁱ	0.96	2.57	3.4677 (12)	155

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

HKF and CKQ thank Universiti Sains Malaysia (USM) for a Research University Golden Goose Grant (No. 1001/PFIZIK/811012). CKQ thanks USM for a Research Fellowship. VV is grateful to DST–India for funding through the Young Scientist Scheme (Fast Track Proposal).

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