rac-Dimethyl 2-(tert-butyl­amino)-5-oxo-4,5-dihydro­pyrano[3,2-c]chromene-3,4-dicarboxyl­ate

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

doi:10.1107/S1600536811041493

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2955

doi:10.1107/S1600536811041493

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rac-Dimethyl 2-(tert-butylamino)-5-oxo-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

^aPhysics Department, 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 600020, India
^*Correspondence e-mail: ksethusankar@yahoo.co.in

(Received 13 September 2011; accepted 8 October 2011; online 12 October 2011)

The title compound, C₂₀H₂₁NO₇, is asymmetric with a chiral centre located in the pyran ring and crystallizes as a racemate. The molecular framework is somewhat bent; the coumarin moiety and the pyran ring are inclined by 7.85 (5)°. The molecular structure is characterized by an intramolecular N—H⋯O hydrogen bond, which generates an S(6) ring motif, and the crystal packing is stabilized by intermolecular C—H⋯O hydrogen bonds. The 3-carboxylate O atom is involved in both of them, having a bifurcated character.

Related literature

For the biological and pharmacological activity of coumarin and its derivatives, see: Borges et al. (2005 ); Gursoy & Karali (2003 ); Moffett (1964 ). For a related structure, see: Fun et al. (2011 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₀H₂₁NO₇
M_r = 387.38
Monoclinic, P 2₁ /n
a = 10.0907 (2) Å
b = 16.3943 (4) Å
c = 11.8266 (2) Å
β = 107.941 (1)°
V = 1861.34 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.969, T_max = 0.979
27295 measured reflections
6688 independent reflections
4069 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.158
S = 1.00
6688 reflections
258 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5	0.86	1.97	2.6602 (16)	136
C19—H19B⋯O5ⁱ	0.96	2.49	3.4469 (19)	174
Symmetry code: (i) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536811041493/ld2028sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811041493/ld2028Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811041493/ld2028Isup3.cml

checkCIF report

Comment top

The coumarin and its derivatives, comprising many of the plant-derived compounds, display a wide range of biological activities such as antiviral, anti-inflammatory, anti-bacterial (Gursoy & Karali et al., 2003), anti-fungal (Moffett et al. 1964), anticoagulant, and anti-proliferative. Some coumarin derivatives have been shown to be potential anti-HIV agents, antibiotics and antioxidants as well as flavour compounds(Borges et al., 2005).

The title compound C₂₀H₂₁NO₇ consists of a coumarin ring system fused with a pyran ring. The coumarin ring system is almost planar, with the C9 atom having a maximum deviation of only 0.0495 (15) Å. The coumarin ring system (O1/C1—C9) makes dihedral angles of 81.43 (7)° and 7.67 (5)° with the methyl carboxylates(C13/O3/O4/C14) and (C15/C16/O5/O6), respectively. The pyran ring forms dihedral angles of 88.77 (7)° and 2.95 (6)° with these two methyl carboxylates.

The X-ray crystal structure determination shows that the compound crystallizes as a racemate - the molecule has an asymmetric carbon atom C10. The title compound exhibits structural similarities with a previously reported related structure (Fun et al., 2011).

The molecular structure is stabilized by an intramolecular N—H···O (Table 1) hydrogen bond which generates an S(6) ring motif (Bernstein et al., 1995). The crystal packing is stabilized by intermolecular C—H···O hydrogen bonds. The carboxylate atom O5 is a bifurcated hydrogen acceptor - from the neighbouring tert-butyl group and from the amino group.

Related literature top

For the biological and pharmacological activity of coumarin and its derivatives, see: Borges et al. (2005); Gursoy & Karali (2003); Moffett (1964). For a related structure, see: Fun et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

To a stirred solution of 4-hydroxy coumarin (0.162 g, 1.0 mmol) and dimethyl acetylenedicarboxylate (0.142 g, 1.0 mmol) in CH₃CN (10 ml), a solution of tert-butyl isocynaide (0.083 g, 1.0 mmol) was added 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 re-crystallized from CH₂Cl₂/n-hexane(1:2) to give product as colourless crystals (0.337 g, 87%).

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 molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability level. H atoms are presented as small spheres of arbitary radius.
	Fig. 2. The packing arrangement of the title compound viewed down c axis, showing formation of hydrogen bond. Dashed lines indicate the intramolecular N—H···O and intermolecular C—H···O interactions.

rac-Dimethyl 2-(tert-butylamino)-5-oxo-4,5- dihydropyrano[3,2-c]chromene-3,4-dicarboxylate top

Crystal data top

C₂₀H₂₁NO₇	F(000) = 816
M_r = 387.38	D_x = 1.382 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6688 reflections
a = 10.0907 (2) Å	θ = 2.2–32.5°
b = 16.3943 (4) Å	µ = 0.11 mm⁻¹
c = 11.8266 (2) Å	T = 293 K
β = 107.941 (1)°	Block, colourless
V = 1861.34 (7) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	6688 independent reflections
Radiation source: fine-focus sealed tube	4069 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω and ϕ scans	θ_max = 32.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −15→15
T_min = 0.969, T_max = 0.979	k = −24→24
27295 measured reflections	l = −17→17

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0737P)² + 0.294P] where P = (F_o² + 2F_c²)/3
6688 reflections	(Δ/σ)_max < 0.001
258 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₀H₂₁NO₇	V = 1861.34 (7) Å³
M_r = 387.38	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.0907 (2) Å	µ = 0.11 mm⁻¹
b = 16.3943 (4) Å	T = 293 K
c = 11.8266 (2) Å	0.30 × 0.25 × 0.20 mm
β = 107.941 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	6688 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	4069 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.979	R_int = 0.030
27295 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 1.00	Δρ_max = 0.26 e Å⁻³
6688 reflections	Δρ_min = −0.21 e Å⁻³
258 parameters

Special details top

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
C1	0.60272 (14)	0.10657 (9)	0.40846 (13)	0.0459 (3)
C2	0.68858 (16)	0.12542 (11)	0.52188 (14)	0.0574 (4)
H2	0.7055	0.1794	0.5462	0.069*
C3	0.74773 (16)	0.06267 (13)	0.59709 (15)	0.0632 (5)
H3	0.8049	0.0745	0.6735	0.076*
C4	0.72413 (16)	−0.01784 (12)	0.56175 (14)	0.0593 (4)
H4	0.7647	−0.0595	0.6143	0.071*
C5	0.64022 (15)	−0.03630 (10)	0.44824 (13)	0.0489 (3)
H5	0.6253	−0.0904	0.4241	0.059*
C6	0.57782 (13)	0.02628 (8)	0.36981 (12)	0.0405 (3)
C7	0.48651 (12)	0.01446 (7)	0.25070 (11)	0.0371 (3)
C8	0.42265 (13)	0.07696 (7)	0.18224 (11)	0.0373 (3)
C9	0.44864 (15)	0.15958 (8)	0.22674 (13)	0.0458 (3)
C10	0.32265 (12)	0.06565 (7)	0.06042 (11)	0.0364 (2)
H10	0.3468	0.1037	0.0060	0.044*
C11	0.33327 (13)	−0.02048 (7)	0.01863 (11)	0.0364 (3)
C12	0.40362 (13)	−0.08012 (7)	0.09507 (11)	0.0376 (3)
C13	0.17418 (13)	0.08403 (7)	0.06189 (12)	0.0385 (3)
C14	−0.03365 (16)	0.15297 (11)	−0.03895 (17)	0.0615 (4)
H14A	−0.0825	0.1019	−0.0530	0.092*
H14B	−0.0695	0.1878	−0.1067	0.092*
H14C	−0.0464	0.1786	0.0299	0.092*
C15	0.26488 (14)	−0.04112 (8)	−0.10362 (12)	0.0416 (3)
C16	0.11252 (17)	0.00960 (12)	−0.28374 (14)	0.0625 (4)
H16A	0.1604	−0.0203	−0.3291	0.094*
H16B	0.0811	0.0608	−0.3221	0.094*
H16C	0.0339	−0.0214	−0.2785	0.094*
C17	0.48307 (18)	−0.22850 (8)	0.13618 (14)	0.0519 (4)
C18	0.4116 (3)	−0.24776 (12)	0.2283 (2)	0.0821 (6)
H18A	0.4305	−0.2051	0.2867	0.123*
H18B	0.4460	−0.2986	0.2662	0.123*
H18C	0.3129	−0.2517	0.1904	0.123*
C19	0.6380 (2)	−0.21543 (11)	0.19263 (19)	0.0730 (5)
H19A	0.6809	−0.2064	0.1316	0.109*
H19B	0.6783	−0.2628	0.2380	0.109*
H19C	0.6532	−0.1688	0.2441	0.109*
C20	0.4601 (3)	−0.29789 (10)	0.04631 (19)	0.0820 (6)
H20A	0.3621	−0.3074	0.0117	0.123*
H20B	0.5041	−0.3465	0.0857	0.123*
H20C	0.4998	−0.2834	−0.0150	0.123*
O1	0.54122 (11)	0.17100 (6)	0.33794 (10)	0.0537 (3)
O2	0.39422 (14)	0.21939 (6)	0.17376 (11)	0.0651 (3)
O3	0.12113 (11)	0.05152 (7)	0.12744 (10)	0.0568 (3)
O4	0.11235 (10)	0.13887 (6)	−0.01951 (10)	0.0539 (3)
O5	0.25835 (12)	−0.10881 (7)	−0.14909 (9)	0.0559 (3)
O6	0.20492 (12)	0.02410 (6)	−0.16718 (9)	0.0545 (3)
O7	0.47008 (10)	−0.06485 (5)	0.21316 (8)	0.0433 (2)
N1	0.41676 (14)	−0.15701 (7)	0.06458 (11)	0.0503 (3)
H1	0.3803	−0.1670	−0.0100	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0359 (6)	0.0521 (8)	0.0470 (7)	−0.0020 (5)	0.0088 (5)	−0.0071 (6)
C2	0.0439 (7)	0.0686 (10)	0.0542 (9)	−0.0058 (7)	0.0069 (7)	−0.0172 (8)
C3	0.0413 (7)	0.0934 (13)	0.0470 (8)	0.0027 (8)	0.0019 (6)	−0.0133 (9)
C4	0.0445 (8)	0.0835 (12)	0.0447 (8)	0.0112 (8)	0.0060 (6)	0.0050 (8)
C5	0.0423 (7)	0.0580 (8)	0.0429 (7)	0.0057 (6)	0.0080 (6)	0.0036 (6)
C6	0.0318 (5)	0.0473 (7)	0.0406 (7)	0.0012 (5)	0.0087 (5)	0.0000 (5)
C7	0.0345 (6)	0.0359 (6)	0.0396 (6)	−0.0013 (5)	0.0094 (5)	−0.0007 (5)
C8	0.0356 (6)	0.0333 (6)	0.0412 (6)	−0.0016 (5)	0.0090 (5)	−0.0004 (5)
C9	0.0456 (7)	0.0386 (6)	0.0497 (8)	−0.0015 (5)	0.0096 (6)	−0.0031 (6)
C10	0.0377 (6)	0.0314 (5)	0.0384 (6)	−0.0020 (4)	0.0092 (5)	0.0047 (5)
C11	0.0375 (6)	0.0330 (5)	0.0381 (6)	−0.0017 (4)	0.0108 (5)	0.0002 (5)
C12	0.0398 (6)	0.0333 (6)	0.0400 (6)	−0.0025 (5)	0.0127 (5)	0.0004 (5)
C13	0.0383 (6)	0.0323 (6)	0.0417 (7)	−0.0004 (5)	0.0074 (5)	0.0020 (5)
C14	0.0401 (7)	0.0598 (9)	0.0757 (11)	0.0082 (7)	0.0047 (7)	0.0113 (8)
C15	0.0404 (6)	0.0427 (7)	0.0416 (7)	−0.0055 (5)	0.0126 (5)	0.0008 (5)
C16	0.0517 (8)	0.0845 (12)	0.0422 (8)	−0.0023 (8)	0.0013 (6)	0.0040 (8)
C17	0.0706 (9)	0.0321 (6)	0.0569 (9)	0.0052 (6)	0.0255 (7)	0.0088 (6)
C18	0.1131 (17)	0.0600 (10)	0.0932 (15)	0.0014 (11)	0.0612 (14)	0.0179 (10)
C19	0.0713 (11)	0.0536 (9)	0.0914 (14)	0.0189 (8)	0.0212 (10)	0.0255 (9)
C20	0.1286 (19)	0.0364 (8)	0.0855 (14)	0.0102 (10)	0.0396 (13)	−0.0010 (8)
O1	0.0546 (6)	0.0424 (5)	0.0553 (6)	−0.0035 (4)	0.0039 (5)	−0.0106 (5)
O2	0.0781 (8)	0.0363 (5)	0.0692 (8)	0.0051 (5)	0.0054 (6)	−0.0007 (5)
O3	0.0503 (6)	0.0632 (7)	0.0625 (7)	0.0087 (5)	0.0255 (5)	0.0193 (5)
O4	0.0411 (5)	0.0509 (6)	0.0659 (7)	0.0077 (4)	0.0108 (5)	0.0225 (5)
O5	0.0677 (7)	0.0489 (6)	0.0474 (6)	−0.0022 (5)	0.0121 (5)	−0.0104 (5)
O6	0.0598 (6)	0.0511 (6)	0.0417 (5)	−0.0015 (5)	−0.0002 (5)	0.0038 (4)
O7	0.0514 (5)	0.0332 (4)	0.0405 (5)	0.0023 (4)	0.0074 (4)	0.0026 (4)
N1	0.0667 (8)	0.0336 (5)	0.0473 (7)	0.0054 (5)	0.0127 (6)	−0.0004 (5)

Geometric parameters (Å, º) top

C1—O1	1.3703 (18)	C13—O4	1.3245 (15)
C1—C2	1.389 (2)	C14—O4	1.4380 (18)
C1—C6	1.3905 (19)	C14—H14A	0.9600
C2—C3	1.371 (3)	C14—H14B	0.9600
C2—H2	0.9300	C14—H14C	0.9600
C3—C4	1.383 (3)	C15—O5	1.2261 (16)
C3—H3	0.9300	C15—O6	1.3395 (17)
C4—C5	1.382 (2)	C16—O6	1.4262 (18)
C4—H4	0.9300	C16—H16A	0.9600
C5—C6	1.3962 (19)	C16—H16B	0.9600
C5—H5	0.9300	C16—H16C	0.9600
C6—C7	1.4392 (18)	C17—N1	1.4797 (18)
C7—C8	1.3415 (17)	C17—C18	1.514 (2)
C7—O7	1.3674 (15)	C17—C19	1.514 (3)
C8—C9	1.4474 (18)	C17—C20	1.525 (2)
C8—C10	1.4942 (17)	C18—H18A	0.9600
C9—O2	1.2016 (17)	C18—H18B	0.9600
C9—O1	1.3714 (18)	C18—H18C	0.9600
C10—C11	1.5107 (17)	C19—H19A	0.9600
C10—C13	1.5335 (17)	C19—H19B	0.9600
C10—H10	0.9800	C19—H19C	0.9600
C11—C12	1.3719 (17)	C20—H20A	0.9600
C11—C15	1.4375 (18)	C20—H20B	0.9600
C12—N1	1.3288 (16)	C20—H20C	0.9600
C12—O7	1.3733 (16)	N1—H1	0.8600
C13—O3	1.1948 (16)

O1—C1—C2	116.55 (14)	H14A—C14—H14B	109.5
O1—C1—C6	121.84 (12)	O4—C14—H14C	109.5
C2—C1—C6	121.59 (14)	H14A—C14—H14C	109.5
C3—C2—C1	118.49 (16)	H14B—C14—H14C	109.5
C3—C2—H2	120.8	O5—C15—O6	121.50 (13)
C1—C2—H2	120.8	O5—C15—C11	126.77 (13)
C2—C3—C4	121.35 (15)	O6—C15—C11	111.74 (11)
C2—C3—H3	119.3	O6—C16—H16A	109.5
C4—C3—H3	119.3	O6—C16—H16B	109.5
C5—C4—C3	119.97 (16)	H16A—C16—H16B	109.5
C5—C4—H4	120.0	O6—C16—H16C	109.5
C3—C4—H4	120.0	H16A—C16—H16C	109.5
C4—C5—C6	120.02 (15)	H16B—C16—H16C	109.5
C4—C5—H5	120.0	N1—C17—C18	110.21 (14)
C6—C5—H5	120.0	N1—C17—C19	111.32 (12)
C1—C6—C5	118.57 (13)	C18—C17—C19	111.62 (16)
C1—C6—C7	116.46 (12)	N1—C17—C20	104.32 (13)
C5—C6—C7	124.96 (13)	C18—C17—C20	110.02 (15)
C8—C7—O7	122.87 (11)	C19—C17—C20	109.10 (16)
C8—C7—C6	122.11 (12)	C17—C18—H18A	109.5
O7—C7—C6	115.02 (11)	C17—C18—H18B	109.5
C7—C8—C9	119.72 (12)	H18A—C18—H18B	109.5
C7—C8—C10	122.91 (11)	C17—C18—H18C	109.5
C9—C8—C10	117.36 (11)	H18A—C18—H18C	109.5
O2—C9—O1	117.10 (12)	H18B—C18—H18C	109.5
O2—C9—C8	124.86 (13)	C17—C19—H19A	109.5
O1—C9—C8	118.04 (12)	C17—C19—H19B	109.5
C8—C10—C11	109.67 (10)	H19A—C19—H19B	109.5
C8—C10—C13	109.67 (10)	C17—C19—H19C	109.5
C11—C10—C13	110.81 (10)	H19A—C19—H19C	109.5
C8—C10—H10	108.9	H19B—C19—H19C	109.5
C11—C10—H10	108.9	C17—C20—H20A	109.5
C13—C10—H10	108.9	C17—C20—H20B	109.5
C12—C11—C15	119.05 (11)	H20A—C20—H20B	109.5
C12—C11—C10	121.68 (11)	C17—C20—H20C	109.5
C15—C11—C10	119.25 (11)	H20A—C20—H20C	109.5
N1—C12—C11	124.89 (12)	H20B—C20—H20C	109.5
N1—C12—O7	112.99 (11)	C1—O1—C9	121.69 (11)
C11—C12—O7	122.12 (11)	C13—O4—C14	117.09 (12)
O3—C13—O4	124.71 (12)	C15—O6—C16	117.20 (12)
O3—C13—C10	123.67 (11)	C7—O7—C12	118.42 (10)
O4—C13—C10	111.61 (11)	C12—N1—C17	131.41 (13)
O4—C14—H14A	109.5	C12—N1—H1	114.3
O4—C14—H14B	109.5	C17—N1—H1	114.3

O1—C1—C2—C3	177.39 (13)	C13—C10—C11—C15	69.62 (14)
C6—C1—C2—C3	−1.0 (2)	C15—C11—C12—N1	1.5 (2)
C1—C2—C3—C4	0.4 (2)	C10—C11—C12—N1	179.80 (12)
C2—C3—C4—C5	0.5 (3)	C15—C11—C12—O7	−179.35 (11)
C3—C4—C5—C6	−0.8 (2)	C10—C11—C12—O7	−1.03 (18)
O1—C1—C6—C5	−177.67 (12)	C8—C10—C13—O3	−54.74 (16)
C2—C1—C6—C5	0.6 (2)	C11—C10—C13—O3	66.48 (17)
O1—C1—C6—C7	1.41 (19)	C8—C10—C13—O4	126.41 (12)
C2—C1—C6—C7	179.72 (13)	C11—C10—C13—O4	−112.38 (12)
C4—C5—C6—C1	0.3 (2)	C12—C11—C15—O5	2.2 (2)
C4—C5—C6—C7	−178.70 (13)	C10—C11—C15—O5	−176.18 (13)
C1—C6—C7—C8	−3.39 (18)	C12—C11—C15—O6	−178.03 (11)
C5—C6—C7—C8	175.63 (13)	C10—C11—C15—O6	3.61 (16)
C1—C6—C7—O7	176.64 (11)	C2—C1—O1—C9	−176.45 (13)
C5—C6—C7—O7	−4.34 (18)	C6—C1—O1—C9	1.9 (2)
O7—C7—C8—C9	−178.01 (11)	O2—C9—O1—C1	176.14 (13)
C6—C7—C8—C9	2.02 (19)	C8—C9—O1—C1	−3.3 (2)
O7—C7—C8—C10	2.75 (19)	O3—C13—O4—C14	−7.5 (2)
C6—C7—C8—C10	−177.22 (11)	C10—C13—O4—C14	171.38 (12)
C7—C8—C9—O2	−178.08 (14)	O5—C15—O6—C16	11.0 (2)
C10—C8—C9—O2	1.2 (2)	C11—C15—O6—C16	−168.79 (12)
C7—C8—C9—O1	1.36 (19)	C8—C7—O7—C12	10.56 (18)
C10—C8—C9—O1	−179.36 (11)	C6—C7—O7—C12	−169.47 (10)
C7—C8—C10—C11	−13.49 (16)	N1—C12—O7—C7	167.98 (11)
C9—C8—C10—C11	167.26 (11)	C11—C12—O7—C7	−11.28 (17)
C7—C8—C10—C13	108.41 (13)	C11—C12—N1—C17	−177.04 (14)
C9—C8—C10—C13	−70.84 (14)	O7—C12—N1—C17	3.7 (2)
C8—C10—C11—C12	12.52 (16)	C18—C17—N1—C12	61.5 (2)
C13—C10—C11—C12	−108.70 (13)	C19—C17—N1—C12	−62.9 (2)
C8—C10—C11—C15	−169.16 (10)	C20—C17—N1—C12	179.60 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5	0.86	1.97	2.6602 (16)	136
C19—H19B···O5ⁱ	0.96	2.49	3.4469 (19)	174

Symmetry code: (i) x+1/2, −y−1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₁NO₇
M_r	387.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.0907 (2), 16.3943 (4), 11.8266 (2)
β (°)	107.941 (1)
V (Å³)	1861.34 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
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	0.969, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	27295, 6688, 4069
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.158, 1.00
No. of reflections	6688
No. of parameters	258
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.21

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···O5	0.86	1.97	2.6602 (16)	136
C19—H19B···O5ⁱ	0.96	2.49	3.4469 (19)	174.2

Symmetry code: (i) x+1/2, −y−1/2, z+1/2.

Acknowledgements

SAIB and KS thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the X-ray intensity data collection and Dr V. Murugan, Head of the Physics Department, 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
Borges, F., Roleria, F., Milhazes, N., Santana, L. & Uriarte, E. (2005). Curr. Med. Chem. 12, 887–916. Web of Science CrossRef PubMed CAS 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
Fun, H.-K., Sripisut, T., Laphookhieo, S. & Chantrapromma, S. (2011). Acta Cryst. E67, o422–o423. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gursoy, A. & Karali, N. (2003). Turk. J. Chem. 27, 545–552. Google Scholar
Moffett, R. B. (1964). J. Med. Chem. 7, 446–449. CrossRef PubMed CAS Web of Science 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

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Volume 67| Part 11| November 2011| Page o2955

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

rac-Di­methyl 2-(tert-butyl­amino)-5-oxo-4,5-di­hydro­pyrano[3,2-c]chromene-3,4-di­carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

rac-Dimethyl 2-(tert-butylamino)-5-oxo-4,5-dihydropyrano[3,2-c]chromene-3,4-dicarboxylate