rac-Diethyl 5-oxo-2-[(2,4,4-trimethyl­pentan-2-yl)amino]-4,5-dihydro­pyrano[3,2-c]chromene-3,4-dicarboxyl­ate

Inglebert, S.A.; Sethusankar, K.; Arun, Y.; Perumal, P.T.

doi:10.1107/S1600536811051786

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o112

doi:10.1107/S1600536811051786

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rac-Diethyl 5-oxo-2-[(2,4,4-trimethylpentan-2-yl)amino]-4,5-dihydropyrano[3,2-c]chromene-3,4-dicarboxylate

S. Antony Inglebert,^a K. Sethusankar,^b ^* Yuvaraj Arun ^c and Paramasivam T. Perumal ^c

^aDepartment of Physics, Sri Ram Engineering College, Chennai 602 024, India, ^bDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and ^cOrganic Chemistry Division, Central Leather Research Institute, Adyar, Chennai 600 020, India
^*Correspondence e-mail: ksethusankar@yahoo.co.in

(Received 22 October 2011; accepted 1 December 2011; online 14 December 2011)

The title compound, C₂₆H₃₃NO₇, comprises a racemic mixture of asymmetric molecules containing one stereogenic centre. The dihedral angle between the mean planes of the fused pyran ring and the coumarin ring system is 8.12 (14)°. The molecular structure features a short N—H⋯O contact, which generates an S(6) ring motif. The crystal packing are stabilized by C—H⋯O interactions.

Related literature

For a related structure, see: Inglebert et al. (2011 ). For general background and applications of coumarin derivatives, see: Griffiths et al. (1995 ); Yu et al. (2006 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₆H₃₃NO₇
M_r = 471.53
Orthorhombic, P n a 2₁
a = 11.6910 (17) Å
b = 18.786 (3) Å
c = 11.7305 (15) Å
V = 2576.3 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.974, T_max = 0.983
10574 measured reflections
3699 independent reflections
2668 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.148
S = 1.09
3699 reflections
314 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O6	0.86	1.99	2.659 (4)	135
C2—H2⋯O6ⁱ	0.93	2.47	3.252 (5)	141
C4—H4⋯O4ⁱⁱ	0.93	2.43	3.306 (5)	157
Symmetry codes: (i) x, y, z-1; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811051786/rk2310sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811051786/rk2310Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811051786/rk2310Isup3.cml

checkCIF report

Comment top

Coumarin and its derivatives have been extensively used in industrial products as dyes/laser materials, photosensitizers, pestisides, in pharmacology and in enzymology as biological probes. The photophysical and spectroscopic properties of the coumarin derivatives can be readily modified by the introduction of substituents in parent coumarin, converting themselves into more useful products and more flexibility to fit well in various applications (Griffiths et al., 1995; Yu et al., 2006).

In the title compound, C₂₆H₃₃NO₇, the coumarin ring system is attached to a pyran ring, two diethyl carboxylates and the mean plane of tri methyl pentan amine group. The coumarin ring system is almost planar with a maximum deviation of -0.011 (4)Å for C8 atom and minimal puckering. Total puckering amplitude of coumarin ring system is 0.016 (4)Å. The coumarin ring system (O1/C1-C9) makes a dihedral angle of 8.12 (14)° with the pyran ring (O3/C7/C8/C10-C12). The coumarin ring system forms dihedral angles of 55.83 (15)° and 16.80 (9)° with the ethyl carboxylates (C13/O4/O5/C14/C15) and (C10/O6/O7/C17/C18) respectively. Likewise the pyran ring forms dihedral angles of 65.08 (18)° and 9.83 (11)° with the ethyl carboxylates (C13/O4/O5/C14/C15) and (C10/O6/O7/C17/C18) respectively. The dihedral angle between two ethyl carboxylate group is 72.93 (15)°.

The molecule is chiral with an asymmetric center (atom C10) present in the pyran ring. The nitrogen atom N1 deviates by -0.1146 (31)° from the pyran ring and carbon atom the C21 deviates by 1.8344 (37)° and 1.0411 (36)° from the mean plane of the butyl and pyran ring. The title compound exhibits structural similarities with a previously reported structure (Inglebert et al., 2011).

The molecular structure features a short intramolecular N1–H1···O6 contact, which generates an S(6) ring motif (Bernstein et al., 1995). The hydrogen bond is bifurcated, with oxygen O5 being simultaneously donated to two equivalent H atoms, forming one intramolecular (N1–H1···O6) and one intermolecular (C2–H2···O6ⁱ) hydrogen bonds. The crystal packing is further stabilized by C4–H4···O4ⁱⁱ intermolecular hydrogen bonds (Table 1). The symmetry codes: (i) x, y, -1+z; (ii) 3/2-x, 1/2+y, -1/2+ z.

Related literature top

For a related structure, see: Inglebert et al. (2011). For general background and applications of coumarin derivatives, see: Griffiths et al. (1995); Yu et al. (2006). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

To a magnetically stirred solution of 4-hydroxy coumarin (0.162 g, 1.0 mmol) and diethyl acetylenedicarboxylate (0.170 g, 1.0 mmol) in CH₃CN (10 ml) was added a solution of 1,1,3,3-tetra methylbutyl isocynaide (0.139 g, 1.0 mmol) at room temperature over 5 min. The mixture was then stirred for 24 h. After completion of the reaction, the solvent was removed under vacuum and the solid residue was washed with n-hexane and crystallized from CH₂Cl₂/n-hexane(1/2) to give product as white crystals (0.396 g, 84%).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The part of molecular structure of the title compound, showing the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability level. H atoms are present as small spheres of arbitary radius.
	Fig. 2. The packing structure of the title compound viewed along the a axis. Figure shows that intermolecular C–H···O and intramolecular N–H···O interactions as dashed lines. H atoms have omited for clarity.

rac-Diethyl 5-oxo-2-[(2,4,4-trimethylpentan-2-yl)amino]- 4,5-dihydropyrano[3,2-c]chromene-3,4-dicarboxylate top

Crystal data top

C₂₆H₃₃NO₇	F(000) = 1008
M_r = 471.53	D_x = 1.216 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3699 reflections
a = 11.6910 (17) Å	θ = 2.1–24.7°
b = 18.786 (3) Å	µ = 0.09 mm⁻¹
c = 11.7305 (15) Å	T = 295 K
V = 2576.3 (6) Å³	Block, colourless
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3699 independent reflections
Radiation source: fine-focus sealed tube	2668 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ω and ϕ scans	θ_max = 24.7°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −13→12
T_min = 0.974, T_max = 0.983	k = −22→21
10574 measured reflections	l = −13→8

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.078P)² + 0.3187P] where P = (F_o² + 2F_c²)/3
3699 reflections	(Δ/σ)_max < 0.001
314 parameters	Δρ_max = 0.31 e Å⁻³
1 restraint	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₆H₃₃NO₇	V = 2576.3 (6) Å³
M_r = 471.53	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 11.6910 (17) Å	µ = 0.09 mm⁻¹
b = 18.786 (3) Å	T = 295 K
c = 11.7305 (15) Å	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3699 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2668 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.983	R_int = 0.040
10574 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	1 restraint
wR(F²) = 0.148	H-atom parameters constrained
S = 1.09	Δρ_max = 0.31 e Å⁻³
3699 reflections	Δρ_min = −0.25 e Å⁻³
314 parameters

Special details top

Geometry. All s.u.'s (except the s.u.'s 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 > 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
C1	0.6377 (3)	−0.0116 (2)	0.3451 (3)	0.0508 (10)
C2	0.6418 (4)	0.0147 (3)	0.2347 (4)	0.0644 (12)
H2	0.6107	−0.0109	0.1743	0.077*
C3	0.6927 (4)	0.0791 (3)	0.2170 (4)	0.0755 (14)
H3	0.6946	0.0975	0.1435	0.091*
C4	0.7414 (4)	0.1179 (3)	0.3041 (4)	0.0683 (13)
H4	0.7766	0.1614	0.2894	0.082*
C5	0.7370 (3)	0.0910 (2)	0.4138 (3)	0.0541 (10)
H5	0.7691	0.1167	0.4736	0.065*
C6	0.6849 (3)	0.02601 (18)	0.4351 (3)	0.0423 (9)
C7	0.6755 (3)	−0.00743 (18)	0.5456 (3)	0.0394 (8)
C8	0.6263 (3)	−0.07045 (18)	0.5616 (3)	0.0395 (8)
C9	0.5766 (3)	−0.1081 (2)	0.4650 (4)	0.0538 (10)
C10	0.6226 (3)	−0.10563 (18)	0.6758 (3)	0.0427 (8)
H10	0.5457	−0.1252	0.6872	0.051*
C11	0.6445 (3)	−0.05068 (18)	0.7671 (3)	0.0385 (8)
C12	0.6961 (3)	0.01298 (17)	0.7433 (3)	0.0402 (8)
C13	0.7083 (4)	−0.1669 (2)	0.6807 (4)	0.0573 (10)
C14	0.9084 (5)	−0.1933 (3)	0.6863 (6)	0.108 (2)
H14A	0.9755	−0.1771	0.6450	0.129*
H14B	0.8860	−0.2391	0.6553	0.129*
C15	0.9368 (6)	−0.2013 (4)	0.8074 (7)	0.123 (2)
H15A	0.9581	−0.1559	0.8383	0.184*
H15B	0.9994	−0.2340	0.8155	0.184*
H15C	0.8714	−0.2192	0.8478	0.184*
C16	0.6163 (3)	−0.06638 (19)	0.8839 (3)	0.0493 (9)
C17	0.5375 (5)	−0.1526 (3)	1.0102 (4)	0.0780 (14)
H17A	0.5140	−0.1114	1.0541	0.094*
H17B	0.4738	−0.1857	1.0074	0.094*
C18	0.6319 (7)	−0.1854 (4)	1.0635 (7)	0.147 (3)
H18A	0.6500	−0.2289	1.0245	0.221*
H18B	0.6133	−0.1957	1.1415	0.221*
H18C	0.6966	−0.1540	1.0608	0.221*
C19	0.7794 (3)	0.13287 (19)	0.8039 (3)	0.0497 (9)
C20	0.6949 (3)	0.1798 (2)	0.7392 (5)	0.0683 (12)
H20A	0.6810	0.1598	0.6652	0.102*
H20B	0.7262	0.2268	0.7310	0.102*
H20C	0.6242	0.1824	0.7807	0.102*
C21	0.8934 (3)	0.13309 (19)	0.7391 (4)	0.0559 (10)
H21A	0.9180	0.1824	0.7360	0.067*
H21B	0.8756	0.1195	0.6614	0.067*
C22	0.7911 (5)	0.1623 (2)	0.9242 (4)	0.0801 (15)
H22A	0.7166	0.1721	0.9547	0.120*
H22B	0.8352	0.2054	0.9224	0.120*
H22C	0.8290	0.1279	0.9715	0.120*
C23	1.0000 (4)	0.0895 (3)	0.7732 (5)	0.0871 (16)
C24	1.0869 (5)	0.1021 (5)	0.6791 (9)	0.166 (3)
H24A	1.1541	0.0742	0.6936	0.249*
H24B	1.1070	0.1517	0.6770	0.249*
H24C	1.0545	0.0885	0.6071	0.249*
C25	1.0573 (6)	0.1221 (5)	0.8796 (8)	0.177 (4)
H25A	1.1344	0.1050	0.8856	0.266*
H25B	1.0152	0.1086	0.9465	0.266*
H25C	1.0579	0.1731	0.8730	0.266*
C26	0.9782 (6)	0.0111 (3)	0.7841 (11)	0.197 (5)
H26A	0.9416	−0.0060	0.7161	0.295*
H26B	0.9297	0.0024	0.8486	0.295*
H26C	1.0496	−0.0133	0.7944	0.295*
O1	0.5851 (3)	−0.07650 (15)	0.3600 (2)	0.0612 (7)
O2	0.5283 (3)	−0.16455 (17)	0.4702 (3)	0.0809 (9)
O3	0.7213 (2)	0.03244 (13)	0.6328 (2)	0.0469 (6)
O4	0.6857 (3)	−0.22770 (16)	0.6899 (4)	0.0995 (12)
O5	0.8155 (3)	−0.14240 (16)	0.6705 (3)	0.0857 (11)
O6	0.6299 (3)	−0.02675 (14)	0.9658 (2)	0.0674 (8)
O7	0.5678 (3)	−0.13089 (14)	0.8956 (2)	0.0648 (8)
N1	0.7291 (3)	0.06126 (16)	0.8183 (3)	0.0531 (8)
H1	0.7195	0.0488	0.8881	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.047 (2)	0.065 (3)	0.041 (2)	0.0145 (19)	0.0032 (19)	0.0016 (19)
C2	0.061 (3)	0.097 (3)	0.035 (2)	0.022 (2)	0.000 (2)	0.005 (2)
C3	0.080 (3)	0.104 (4)	0.043 (3)	0.029 (3)	0.017 (2)	0.026 (3)
C4	0.069 (3)	0.079 (3)	0.057 (3)	0.013 (2)	0.019 (2)	0.029 (3)
C5	0.057 (2)	0.060 (2)	0.046 (3)	0.004 (2)	0.0088 (19)	0.0084 (19)
C6	0.0436 (19)	0.050 (2)	0.034 (2)	0.0126 (17)	0.0063 (16)	0.0075 (17)
C7	0.0359 (19)	0.0484 (19)	0.034 (2)	0.0050 (16)	0.0016 (16)	−0.0002 (17)
C8	0.0358 (19)	0.0450 (19)	0.038 (2)	0.0029 (16)	−0.0019 (16)	0.0002 (15)
C9	0.062 (3)	0.055 (2)	0.045 (2)	0.004 (2)	−0.012 (2)	−0.003 (2)
C10	0.044 (2)	0.045 (2)	0.038 (2)	−0.0045 (16)	−0.0007 (17)	0.0013 (15)
C11	0.0355 (18)	0.0477 (19)	0.032 (2)	−0.0039 (16)	0.0013 (15)	0.0071 (15)
C12	0.0406 (19)	0.0470 (19)	0.033 (2)	−0.0018 (16)	−0.0018 (18)	0.0036 (17)
C13	0.076 (3)	0.046 (2)	0.050 (2)	0.003 (2)	−0.001 (2)	0.0082 (18)
C14	0.097 (4)	0.095 (4)	0.131 (5)	0.052 (3)	0.024 (4)	0.031 (4)
C15	0.109 (5)	0.119 (5)	0.140 (6)	0.028 (4)	−0.011 (4)	0.025 (4)
C16	0.055 (2)	0.051 (2)	0.042 (2)	−0.0062 (18)	0.0017 (19)	0.0048 (18)
C17	0.092 (4)	0.078 (3)	0.063 (3)	−0.022 (3)	0.001 (3)	0.022 (2)
C18	0.143 (6)	0.158 (7)	0.140 (7)	0.025 (5)	−0.016 (5)	0.066 (6)
C19	0.053 (2)	0.047 (2)	0.049 (2)	−0.0072 (18)	0.0023 (19)	−0.0012 (17)
C20	0.059 (3)	0.058 (2)	0.088 (3)	0.001 (2)	0.007 (3)	0.004 (2)
C21	0.051 (2)	0.053 (2)	0.064 (3)	−0.0103 (17)	−0.010 (2)	0.0040 (19)
C22	0.100 (4)	0.075 (3)	0.065 (3)	−0.033 (3)	0.003 (3)	−0.015 (2)
C23	0.056 (3)	0.080 (3)	0.126 (5)	−0.003 (2)	−0.016 (3)	0.011 (3)
C24	0.068 (4)	0.217 (9)	0.214 (9)	0.036 (5)	0.029 (5)	0.018 (7)
C25	0.116 (6)	0.229 (9)	0.188 (9)	0.017 (6)	−0.090 (6)	−0.013 (8)
C26	0.086 (4)	0.079 (4)	0.425 (17)	0.010 (3)	−0.060 (7)	0.042 (7)
O1	0.0684 (18)	0.0741 (19)	0.0410 (17)	−0.0001 (15)	−0.0120 (14)	−0.0039 (14)
O2	0.103 (2)	0.0674 (18)	0.072 (2)	−0.0260 (18)	−0.026 (2)	−0.0017 (17)
O3	0.0557 (15)	0.0522 (14)	0.0328 (14)	−0.0126 (12)	0.0012 (12)	0.0036 (12)
O4	0.109 (3)	0.0437 (17)	0.145 (3)	0.0013 (18)	−0.018 (2)	0.0142 (18)
O5	0.065 (2)	0.0698 (18)	0.122 (3)	0.0217 (17)	0.0166 (19)	0.0305 (18)
O6	0.096 (2)	0.0688 (17)	0.0373 (17)	−0.0171 (16)	0.0010 (16)	0.0005 (14)
O7	0.0885 (19)	0.0589 (16)	0.0470 (17)	−0.0158 (15)	0.0058 (15)	0.0127 (13)
N1	0.067 (2)	0.0570 (19)	0.0351 (17)	−0.0181 (16)	−0.0014 (16)	−0.0014 (15)

Geometric parameters (Å, º) top

C1—O1	1.377 (5)	C16—O7	1.345 (4)
C1—C6	1.385 (5)	C17—C18	1.409 (8)
C1—C2	1.386 (6)	C17—O7	1.449 (5)
C2—C3	1.364 (6)	C17—H17A	0.9700
C2—H2	0.9300	C17—H17B	0.9700
C3—C4	1.378 (7)	C18—H18A	0.9600
C3—H3	0.9300	C18—H18B	0.9600
C4—C5	1.383 (6)	C18—H18C	0.9600
C4—H4	0.9300	C19—N1	1.478 (5)
C5—C6	1.388 (5)	C19—C22	1.522 (6)
C5—H5	0.9300	C19—C20	1.526 (6)
C6—C7	1.445 (5)	C19—C21	1.535 (6)
C7—C8	1.329 (4)	C20—H20A	0.9600
C7—O3	1.376 (4)	C20—H20B	0.9600
C8—C9	1.457 (5)	C20—H20C	0.9600
C8—C10	1.494 (5)	C21—C23	1.543 (6)
C9—O2	1.203 (4)	C21—H21A	0.9700
C9—O1	1.372 (5)	C21—H21B	0.9700
C10—C11	1.509 (5)	C22—H22A	0.9600
C10—C13	1.528 (5)	C22—H22B	0.9600
C10—H10	0.9800	C22—H22C	0.9600
C11—C12	1.368 (5)	C23—C26	1.500 (8)
C11—C16	1.440 (5)	C23—C24	1.520 (10)
C12—N1	1.321 (5)	C23—C25	1.543 (10)
C12—O3	1.378 (4)	C24—H24A	0.9600
C13—O4	1.177 (4)	C24—H24B	0.9600
C13—O5	1.340 (5)	C24—H24C	0.9600
C14—O5	1.459 (5)	C25—H25A	0.9600
C14—C15	1.467 (9)	C25—H25B	0.9600
C14—H14A	0.9700	C25—H25C	0.9600
C14—H14B	0.9700	C26—H26A	0.9600
C15—H15A	0.9600	C26—H26B	0.9600
C15—H15B	0.9600	C26—H26C	0.9600
C15—H15C	0.9600	N1—H1	0.8600
C16—O6	1.226 (5)

O1—C1—C6	122.2 (3)	H17A—C17—H17B	108.2
O1—C1—C2	116.7 (4)	C17—C18—H18A	109.5
C6—C1—C2	121.1 (4)	C17—C18—H18B	109.5
C3—C2—C1	118.2 (4)	H18A—C18—H18B	109.5
C3—C2—H2	120.9	C17—C18—H18C	109.5
C1—C2—H2	120.9	H18A—C18—H18C	109.5
C2—C3—C4	122.5 (4)	H18B—C18—H18C	109.5
C2—C3—H3	118.8	N1—C19—C22	105.1 (3)
C4—C3—H3	118.8	N1—C19—C20	109.0 (3)
C3—C4—C5	118.7 (4)	C22—C19—C20	108.1 (4)
C3—C4—H4	120.6	N1—C19—C21	113.9 (3)
C5—C4—H4	120.6	C22—C19—C21	112.3 (4)
C4—C5—C6	120.4 (4)	C20—C19—C21	108.3 (3)
C4—C5—H5	119.8	C19—C20—H20A	109.5
C6—C5—H5	119.8	C19—C20—H20B	109.5
C1—C6—C5	119.1 (4)	H20A—C20—H20B	109.5
C1—C6—C7	115.6 (3)	C19—C20—H20C	109.5
C5—C6—C7	125.3 (3)	H20A—C20—H20C	109.5
C8—C7—O3	123.2 (3)	H20B—C20—H20C	109.5
C8—C7—C6	123.1 (3)	C19—C21—C23	124.8 (4)
O3—C7—C6	113.6 (3)	C19—C21—H21A	106.1
C7—C8—C9	119.7 (3)	C23—C21—H21A	106.1
C7—C8—C10	122.2 (3)	C19—C21—H21B	106.1
C9—C8—C10	118.1 (3)	C23—C21—H21B	106.1
O2—C9—O1	117.4 (4)	H21A—C21—H21B	106.3
O2—C9—C8	125.2 (4)	C19—C22—H22A	109.5
O1—C9—C8	117.4 (3)	C19—C22—H22B	109.5
C8—C10—C11	109.2 (3)	H22A—C22—H22B	109.5
C8—C10—C13	110.3 (3)	C19—C22—H22C	109.5
C11—C10—C13	112.2 (3)	H22A—C22—H22C	109.5
C8—C10—H10	108.3	H22B—C22—H22C	109.5
C11—C10—H10	108.3	C26—C23—C24	109.2 (7)
C13—C10—H10	108.3	C26—C23—C21	114.0 (4)
C12—C11—C16	118.3 (3)	C24—C23—C21	105.6 (5)
C12—C11—C10	121.9 (3)	C26—C23—C25	113.2 (7)
C16—C11—C10	119.8 (3)	C24—C23—C25	103.6 (6)
N1—C12—C11	126.4 (3)	C21—C23—C25	110.5 (5)
N1—C12—O3	112.4 (3)	C23—C24—H24A	109.5
C11—C12—O3	121.2 (3)	C23—C24—H24B	109.5
O4—C13—O5	123.5 (4)	H24A—C24—H24B	109.5
O4—C13—C10	126.0 (4)	C23—C24—H24C	109.5
O5—C13—C10	110.5 (3)	H24A—C24—H24C	109.5
O5—C14—C15	111.0 (5)	H24B—C24—H24C	109.5
O5—C14—H14A	109.4	C23—C25—H25A	109.5
C15—C14—H14A	109.4	C23—C25—H25B	109.5
O5—C14—H14B	109.4	H25A—C25—H25B	109.5
C15—C14—H14B	109.4	C23—C25—H25C	109.5
H14A—C14—H14B	108.0	H25A—C25—H25C	109.5
C14—C15—H15A	109.5	H25B—C25—H25C	109.5
C14—C15—H15B	109.5	C23—C26—H26A	109.5
H15A—C15—H15B	109.5	C23—C26—H26B	109.5
C14—C15—H15C	109.5	H26A—C26—H26B	109.5
H15A—C15—H15C	109.5	C23—C26—H26C	109.5
H15B—C15—H15C	109.5	H26A—C26—H26C	109.5
O6—C16—O7	121.4 (3)	H26B—C26—H26C	109.5
O6—C16—C11	126.3 (3)	C9—O1—C1	122.0 (3)
O7—C16—C11	112.2 (3)	C7—O3—C12	118.1 (2)
C18—C17—O7	110.1 (5)	C13—O5—C14	117.3 (4)
C18—C17—H17A	109.6	C16—O7—C17	116.9 (3)
O7—C17—H17A	109.6	C12—N1—C19	131.7 (3)
C18—C17—H17B	109.6	C12—N1—H1	114.2
O7—C17—H17B	109.6	C19—N1—H1	114.2

O1—C1—C2—C3	179.6 (3)	C10—C11—C12—O3	5.9 (5)
C6—C1—C2—C3	−0.6 (6)	C8—C10—C13—O4	−114.4 (5)
C1—C2—C3—C4	1.1 (6)	C11—C10—C13—O4	123.6 (5)
C2—C3—C4—C5	−1.0 (6)	C8—C10—C13—O5	64.3 (4)
C3—C4—C5—C6	0.3 (6)	C11—C10—C13—O5	−57.7 (4)
O1—C1—C6—C5	179.8 (3)	C12—C11—C16—O6	3.1 (6)
C2—C1—C6—C5	0.0 (5)	C10—C11—C16—O6	179.8 (4)
O1—C1—C6—C7	0.1 (5)	C12—C11—C16—O7	−179.0 (3)
C2—C1—C6—C7	−179.7 (3)	C10—C11—C16—O7	−2.3 (5)
C4—C5—C6—C1	0.1 (5)	N1—C19—C21—C23	−55.7 (5)
C4—C5—C6—C7	179.8 (3)	C22—C19—C21—C23	63.6 (5)
C1—C6—C7—C8	0.8 (5)	C20—C19—C21—C23	−177.1 (4)
C5—C6—C7—C8	−178.9 (3)	C19—C21—C23—C26	55.6 (8)
C1—C6—C7—O3	−178.7 (3)	C19—C21—C23—C24	175.4 (5)
C5—C6—C7—O3	1.7 (5)	C19—C21—C23—C25	−73.2 (6)
O3—C7—C8—C9	178.0 (3)	O2—C9—O1—C1	179.3 (3)
C6—C7—C8—C9	−1.4 (5)	C8—C9—O1—C1	−0.3 (5)
O3—C7—C8—C10	−3.7 (5)	C6—C1—O1—C9	−0.3 (5)
C6—C7—C8—C10	176.9 (3)	C2—C1—O1—C9	179.5 (4)
C7—C8—C9—O2	−178.4 (4)	C8—C7—O3—C12	−12.7 (4)
C10—C8—C9—O2	3.2 (6)	C6—C7—O3—C12	166.8 (3)
C7—C8—C9—O1	1.1 (5)	N1—C12—O3—C7	−169.8 (3)
C10—C8—C9—O1	−177.3 (3)	C11—C12—O3—C7	11.3 (4)
C7—C8—C10—C11	18.6 (4)	O4—C13—O5—C14	−7.9 (7)
C9—C8—C10—C11	−163.1 (3)	C10—C13—O5—C14	173.3 (4)
C7—C8—C10—C13	−105.2 (4)	C15—C14—O5—C13	−84.9 (6)
C9—C8—C10—C13	73.2 (4)	O6—C16—O7—C17	−2.9 (5)
C8—C10—C11—C12	−19.6 (4)	C11—C16—O7—C17	179.0 (4)
C13—C10—C11—C12	103.0 (4)	C18—C17—O7—C16	−86.8 (6)
C8—C10—C11—C16	163.8 (3)	C11—C12—N1—C19	−176.2 (3)
C13—C10—C11—C16	−73.6 (4)	O3—C12—N1—C19	4.9 (5)
C16—C11—C12—N1	3.8 (5)	C22—C19—N1—C12	176.9 (4)
C10—C11—C12—N1	−172.9 (3)	C20—C19—N1—C12	61.3 (5)
C16—C11—C12—O3	−177.4 (3)	C21—C19—N1—C12	−59.8 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O6	0.86	1.99	2.659 (4)	135
C2—H2···O6ⁱ	0.93	2.47	3.252 (5)	141
C4—H4···O4ⁱⁱ	0.93	2.43	3.306 (5)	157

Symmetry codes: (i) x, y, z−1; (ii) −x+3/2, y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₆H₃₃NO₇
M_r	471.53
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	295
a, b, c (Å)	11.6910 (17), 18.786 (3), 11.7305 (15)
V (Å³)	2576.3 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.974, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	10574, 3699, 2668
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.588

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.148, 1.09
No. of reflections	3699
No. of parameters	314
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.25

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (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—H1···O6	0.86	1.99	2.659 (4)	135
C2—H2···O6ⁱ	0.93	2.47	3.252 (5)	141.2
C4—H4···O4ⁱⁱ	0.93	2.43	3.306 (5)	157.3

Symmetry codes: (i) x, y, z−1; (ii) −x+3/2, y+1/2, z−1/2.

Acknowledgements

The authors gratefully acknowledge Dr Babu Varghese, SAIF, IIT, Chennai, India, for the X-ray intensity data collection and Dr V. Murugan, Head of the Physics Department, RKM Vivekananda College, Chennai, India, for providing facilities in the department to carry out this work.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Griffiths, J., Millar, V. & Bahra, G. S. (1995). Dyes Pigm. 28, 327–339. CrossRef CAS Web of Science Google Scholar
Inglebert, S. A., Sethusankar, K., Arun, Y. & Perumal, P. T. (2011). Acta Cryst. E67, o2955. 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
Yu, T.-Z., Zhao, Y.-L. & Fan, D.-W. (2006). J. Mol. Struct. 791, 18-22. Web of Science CSD CrossRef CAS Google Scholar

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

rac-Di­ethyl 5-oxo-2-[(2,4,4-tri­methyl­pentan-2-yl)amino]-4,5-di­hydro­pyrano[3,2-c]chromene-3,4-di­carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

rac-Diethyl 5-oxo-2-[(2,4,4-trimethylpentan-2-yl)amino]-4,5-dihydropyrano[3,2-c]chromene-3,4-dicarboxylate