Crystal structure of isobutyl 4-(2-chloro­phen­yl)-5-cyano-6-{(E)-[(di­methyl­amino)­methyl­idene]amino}-2-methyl-4H-pyran-3-carboxyl­ate

Mohandas, T.; Kumar, C.U.; Devi, S.A.; Prakasam, B.A.; Sakthivel, P.; Vidhyasagar, T.

doi:10.1107/S2056989015000079

organic compounds

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ISSN: 2056-9890

Volume 71| Part 2| February 2015| Pages o101-o102

doi:10.1107/S2056989015000079

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Crystal structure of isobutyl 4-(2-chlorophenyl)-5-cyano-6-{(E)-[(dimethylamino)methylidene]amino}-2-methyl-4H-pyran-3-carboxylate

T. Mohandas,^a C. Udhaya Kumar,^b S. Aruna Devi,^c B. Arul Prakasam,^b P. Sakthivel ^d ^* and T. Vidhyasagar ^b

^aDepartment of Physics, Shri Angalamman College of Engineering and Technology, Siruganoor, Tiruchirappalli, India, ^bDepartment of Chemistry, Annamalai University, Annamalainagar, Chidambaram, India, ^cDepartment of chemistry, Urumu Dhanalakshmi College, Tiruchirappalli, 620 019, India, and ^dDepartment of Physics, Urumu Dhanalakshmi College, Tiruchirappalli, 620 019, India
^*Correspondence e-mail: sakthi2udc@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 15 December 2014; accepted 3 January 2015; online 10 January 2015)

In the title compound, C₂₁H₂₄ClN₃O₃, the dihedral angle between the pyran ring (r.m.s. deviation = 0.037 Å) and the chlorobenzene ring is 88.56 (14)°. In the crystal, the molecules are linked by C—H⋯O interactions, generating C(7) (001) chains.

Keywords: crystal structure; pyran derivative; C—H⋯O interactions.

CCDC reference: 1041846

1. Related literature

For the biological activities of pyran derivatives, see: Kitamura et al. (2006 ); Tangmouo et al. (2006 ); Cocco et al. (2003 ). For related structures, see: Park et al. (2012a ,b ).

2. Experimental

2.1. Crystal data

C₂₁H₂₄ClN₃O₃
M_r = 401.88
Monoclinic, P 2₁ /c
a = 15.6836 (16) Å
b = 15.2523 (13) Å
c = 9.3283 (8) Å
β = 105.016 (2)°
V = 2155.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 293 K
0.28 × 0.26 × 0.25 mm

2.2. Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.985, T_max = 0.989
28118 measured reflections
5524 independent reflections
3062 reflections with I > 2σ(I)
R_int = 0.037

2.3. Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.217
S = 1.00
5524 reflections
258 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O2ⁱ	0.93	2.46	3.3368	157
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1041846

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015000079/hb7341sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015000079/hb7341Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015000079/hb7341Isup3.cml

checkCIF report

Comment top

2-Amino-4H-Pyran derivatives are an important class of heterocycles, which have considerable interest due to their useful biological properties including antimicrobial (Kitamura et al. 2006), antifungal (Tangmouo et al. 2006) and cancer therapy (Cocco et al. 2003).

The torsion angles of C8/C11/O3/C12 and N1/N2/C4/C5 are -178.75° and 177.08° respectively.

The bond distances and bond angles in the title compound agree very well with the corresponding values reported in closely related compound. (Park et al.2012(a,b)).

The crystal packing features C17—H17···O2 hydrogen bonds, which generate C(7)chains running parallel to the c axis.

Related literature top

For the biological activities of pyran derivatives, see: Kitamura et al. (2006); Tangmouo et al. (2006); Cocco et al. (2003). For related structures, see: Park et al. (2012a,b).

Experimental top

Isobutyl 6-amino-4-(2-chlorophenyl)-5-cyano-2-methyl-4H-pyran-3-carboxylate (1 mmol) and K₂CO₃ (1.2 equivalent) were stirred in dry DMF for 15 min in ice cold condition. Then, benzene-1,3,5-tricarbonyl trichloride (1 mmol) was added and stirred for an additional 25 min. After completion of the reaction, addition of water (50 ml), resulted the precipitate which was collected by filtration and washed with a large portion of cold water. The crude product thus collected was recrystallized from ethanol to yield colourless blocks.

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 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); 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 displacement ellipsoids drawn at 30% probability level.
	Fig. 2. Part of crystal packing of the title compound showing the formation of C(7) chains running parallel to c axis.

Isobutyl 4-(2-chlorophenyl)-5-cyano-6-{(E)-[(dimethylamino)methylidene]amino}-2-methyl-4H-pyran-3-carboxylate top

Crystal data top

C₂₁H₂₄ClN₃O₃	F(000) = 848
M_r = 401.88	D_x = 1.239 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.6836 (16) Å	Cell parameters from 3064 reflections
b = 15.2523 (13) Å	θ = 1.3–29.7°
c = 9.3283 (8) Å	µ = 0.20 mm⁻¹
β = 105.016 (2)°	T = 293 K
V = 2155.2 (3) Å³	Block, colourless
Z = 4	0.28 × 0.26 × 0.25 mm

Data collection top

Bruker APEXII CCD diffractometer	5524 independent reflections
Radiation source: fine-focus sealed tube	3062 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ω & ϕ scans	θ_max = 29.7°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −21→21
T_min = 0.985, T_max = 0.989	k = −20→20
28118 measured reflections	l = −12→12

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.217	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.1039P)² + 1.1568P] where P = (F_o² + 2F_c²)/3
5524 reflections	(Δ/σ)_max = 0.033
258 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₂₁H₂₄ClN₃O₃	V = 2155.2 (3) Å³
M_r = 401.88	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.6836 (16) Å	µ = 0.20 mm⁻¹
b = 15.2523 (13) Å	T = 293 K
c = 9.3283 (8) Å	0.28 × 0.26 × 0.25 mm
β = 105.016 (2)°

Data collection top

Bruker APEXII CCD diffractometer	5524 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3062 reflections with I > 2σ(I)
T_min = 0.985, T_max = 0.989	R_int = 0.037
28118 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.217	H-atom parameters constrained
S = 1.00	Δρ_max = 0.60 e Å⁻³
5524 reflections	Δρ_min = −0.44 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	0.3162 (2)	0.1810 (2)	−0.0790 (4)	0.0762 (10)
H1A	0.3371	0.2362	−0.0339	0.114*
H1B	0.2546	0.1748	−0.0843	0.114*
H1C	0.3247	0.1788	−0.1772	0.114*
C2	0.3449 (2)	0.0213 (2)	−0.0425 (4)	0.0722 (10)
H2A	0.3928	−0.0015	−0.0779	0.108*
H2B	0.2918	0.0208	−0.1216	0.108*
H2C	0.3370	−0.0145	0.0378	0.108*
C3	0.42724 (17)	0.12629 (16)	0.1321 (3)	0.0441 (6)
H3	0.4394	0.1840	0.1629	0.053*
C4	0.53764 (16)	0.08439 (15)	0.3322 (3)	0.0380 (5)
C5	0.58829 (15)	0.02517 (15)	0.4233 (3)	0.0381 (5)
C6	0.57139 (17)	−0.06580 (16)	0.3917 (3)	0.0439 (6)
C7	0.66429 (15)	0.04929 (15)	0.5534 (3)	0.0378 (5)
H7	0.6549	0.0220	0.6432	0.045*
C8	0.66744 (16)	0.14771 (16)	0.5739 (3)	0.0406 (6)
C9	0.61304 (16)	0.20215 (16)	0.4809 (3)	0.0421 (6)
C10	0.6059 (2)	0.29947 (17)	0.4866 (4)	0.0579 (8)
H10A	0.6089	0.3174	0.5864	0.087*
H10B	0.5506	0.3179	0.4222	0.087*
H10C	0.6535	0.3258	0.4548	0.087*
C11	0.73241 (19)	0.18383 (19)	0.7044 (3)	0.0515 (7)
C12	0.8380 (2)	0.1463 (3)	0.9286 (3)	0.0742 (10)
H12A	0.8175	0.1997	0.9652	0.089*
H12B	0.8411	0.1013	1.0032	0.089*
C13	0.9252 (3)	0.1612 (4)	0.9120 (5)	0.1227 (19)
H13	0.9204	0.2177	0.8606	0.147*
C14	0.9880 (3)	0.1800 (5)	1.0641 (6)	0.164 (3)
H14A	0.9900	0.1300	1.1275	0.246*
H14B	0.9674	0.2301	1.1074	0.246*
H14C	1.0461	0.1915	1.0527	0.246*
C15	0.9634 (3)	0.1055 (4)	0.8250 (6)	0.134 (2)
H15A	0.9610	0.0459	0.8571	0.202*
H15B	1.0238	0.1221	0.8361	0.202*
H15C	0.9314	0.1105	0.7226	0.202*
C16	0.74957 (16)	0.01276 (16)	0.5256 (3)	0.0393 (5)
C17	0.78475 (18)	0.0516 (2)	0.4190 (3)	0.0512 (7)
H17	0.7585	0.1019	0.3706	0.061*
C18	0.8583 (2)	0.0169 (3)	0.3838 (4)	0.0713 (9)
H18	0.8814	0.0440	0.3129	0.086*
C19	0.8970 (2)	−0.0578 (3)	0.4536 (4)	0.0779 (11)
H19	0.9457	−0.0817	0.4284	0.094*
C20	0.8647 (2)	−0.0972 (2)	0.5595 (4)	0.0667 (9)
H20	0.8911	−0.1477	0.6068	0.080*
C21	0.79209 (18)	−0.06106 (17)	0.5962 (3)	0.0473 (6)
N1	0.36500 (16)	0.11034 (14)	0.0093 (3)	0.0509 (6)
N2	0.47213 (14)	0.06290 (13)	0.2112 (2)	0.0424 (5)
N3	0.56164 (18)	−0.13952 (16)	0.3724 (3)	0.0672 (7)
O1	0.55106 (12)	0.17257 (11)	0.3586 (2)	0.0477 (5)
O2	0.74819 (18)	0.26007 (15)	0.7309 (3)	0.0899 (9)
O3	0.77370 (14)	0.11992 (14)	0.7944 (2)	0.0611 (6)
Cl	0.75622 (6)	−0.11215 (5)	0.73714 (9)	0.0711 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.081 (2)	0.0587 (19)	0.072 (2)	0.0163 (17)	−0.0101 (18)	0.0144 (16)
C2	0.082 (2)	0.0533 (18)	0.065 (2)	−0.0039 (16)	−0.0092 (17)	−0.0108 (15)
C3	0.0434 (14)	0.0369 (12)	0.0510 (15)	−0.0010 (11)	0.0101 (12)	0.0006 (11)
C4	0.0383 (12)	0.0324 (11)	0.0448 (13)	−0.0027 (10)	0.0137 (11)	−0.0002 (10)
C5	0.0380 (12)	0.0329 (12)	0.0443 (13)	−0.0017 (10)	0.0122 (10)	−0.0007 (10)
C6	0.0420 (13)	0.0377 (13)	0.0485 (14)	0.0014 (11)	0.0054 (11)	0.0003 (11)
C7	0.0397 (13)	0.0356 (12)	0.0376 (12)	−0.0014 (10)	0.0091 (10)	0.0011 (10)
C8	0.0416 (13)	0.0394 (13)	0.0425 (13)	−0.0029 (10)	0.0143 (11)	−0.0086 (11)
C9	0.0432 (13)	0.0375 (12)	0.0475 (14)	−0.0029 (10)	0.0155 (11)	−0.0062 (11)
C10	0.0623 (18)	0.0346 (13)	0.077 (2)	0.0009 (12)	0.0180 (16)	−0.0100 (13)
C11	0.0519 (16)	0.0524 (16)	0.0514 (15)	−0.0016 (13)	0.0155 (13)	−0.0158 (13)
C12	0.067 (2)	0.103 (3)	0.0459 (17)	−0.0102 (19)	0.0028 (15)	−0.0148 (18)
C13	0.073 (3)	0.203 (6)	0.083 (3)	−0.002 (3)	0.003 (2)	−0.047 (3)
C14	0.078 (3)	0.288 (9)	0.105 (4)	−0.023 (4)	−0.012 (3)	−0.078 (5)
C15	0.090 (3)	0.197 (6)	0.117 (4)	0.002 (4)	0.027 (3)	−0.057 (4)
C16	0.0407 (13)	0.0389 (12)	0.0366 (12)	−0.0036 (10)	0.0067 (10)	−0.0060 (10)
C17	0.0481 (15)	0.0588 (17)	0.0477 (15)	−0.0009 (13)	0.0142 (12)	0.0013 (13)
C18	0.0573 (19)	0.102 (3)	0.0607 (19)	−0.0026 (19)	0.0263 (16)	−0.0055 (19)
C19	0.0530 (19)	0.107 (3)	0.076 (2)	0.0185 (19)	0.0200 (17)	−0.019 (2)
C20	0.0556 (18)	0.068 (2)	0.070 (2)	0.0194 (15)	0.0043 (16)	−0.0088 (17)
C21	0.0467 (14)	0.0450 (14)	0.0462 (14)	0.0031 (11)	0.0049 (11)	−0.0036 (11)
N1	0.0532 (13)	0.0436 (12)	0.0497 (13)	0.0018 (10)	0.0022 (11)	0.0034 (10)
N2	0.0418 (11)	0.0361 (11)	0.0463 (12)	−0.0006 (9)	0.0059 (9)	0.0008 (9)
N3	0.0719 (17)	0.0366 (13)	0.0837 (19)	−0.0026 (12)	0.0030 (14)	−0.0057 (12)
O1	0.0537 (11)	0.0324 (9)	0.0525 (10)	−0.0020 (8)	0.0056 (8)	0.0006 (8)
O2	0.0990 (19)	0.0523 (13)	0.0964 (18)	−0.0006 (12)	−0.0142 (15)	−0.0325 (12)
O3	0.0618 (12)	0.0690 (14)	0.0450 (11)	−0.0063 (10)	0.0002 (9)	−0.0074 (10)
Cl	0.0811 (6)	0.0592 (5)	0.0707 (5)	0.0063 (4)	0.0155 (4)	0.0217 (4)

Geometric parameters (Å, º) top

C1—N1	1.448 (4)	C11—O2	1.201 (3)
C1—H1A	0.9600	C11—O3	1.339 (4)
C1—H1B	0.9600	C12—C13	1.433 (6)
C1—H1C	0.9600	C12—O3	1.447 (3)
C2—N1	1.449 (4)	C12—H12A	0.9700
C2—H2A	0.9600	C12—H12B	0.9700
C2—H2B	0.9600	C13—C15	1.411 (7)
C2—H2C	0.9600	C13—C14	1.531 (6)
C3—N2	1.306 (3)	C13—H13	0.9800
C3—N1	1.321 (3)	C14—H14A	0.9600
C3—H3	0.9300	C14—H14B	0.9600
C4—C5	1.349 (3)	C14—H14C	0.9600
C4—N2	1.355 (3)	C15—H15A	0.9600
C4—O1	1.374 (3)	C15—H15B	0.9600
C5—C6	1.429 (3)	C15—H15C	0.9600
C5—C7	1.510 (3)	C16—C21	1.385 (4)
C6—N3	1.143 (3)	C16—C17	1.389 (4)
C7—C8	1.513 (3)	C17—C18	1.385 (4)
C7—C16	1.532 (3)	C17—H17	0.9300
C7—H7	0.9800	C18—C19	1.373 (5)
C8—C9	1.337 (4)	C18—H18	0.9300
C8—C11	1.476 (4)	C19—C20	1.361 (5)
C9—O1	1.370 (3)	C19—H19	0.9300
C9—C10	1.491 (4)	C20—C21	1.385 (4)
C10—H10A	0.9600	C20—H20	0.9300
C10—H10B	0.9600	C21—Cl	1.742 (3)
C10—H10C	0.9600

N1—C1—H1A	109.5	C13—C12—H12B	108.5
N1—C1—H1B	109.5	O3—C12—H12B	108.5
H1A—C1—H1B	109.5	H12A—C12—H12B	107.5
N1—C1—H1C	109.5	C15—C13—C12	121.7 (5)
H1A—C1—H1C	109.5	C15—C13—C14	112.2 (5)
H1B—C1—H1C	109.5	C12—C13—C14	109.4 (4)
N1—C2—H2A	109.5	C15—C13—H13	103.8
N1—C2—H2B	109.5	C12—C13—H13	103.8
H2A—C2—H2B	109.5	C14—C13—H13	103.8
N1—C2—H2C	109.5	C13—C14—H14A	109.5
H2A—C2—H2C	109.5	C13—C14—H14B	109.5
H2B—C2—H2C	109.5	H14A—C14—H14B	109.5
N2—C3—N1	121.5 (2)	C13—C14—H14C	109.5
N2—C3—H3	119.2	H14A—C14—H14C	109.5
N1—C3—H3	119.2	H14B—C14—H14C	109.5
C5—C4—N2	124.0 (2)	C13—C15—H15A	109.5
C5—C4—O1	120.3 (2)	C13—C15—H15B	109.5
N2—C4—O1	115.7 (2)	H15A—C15—H15B	109.5
C4—C5—C6	118.2 (2)	C13—C15—H15C	109.5
C4—C5—C7	123.8 (2)	H15A—C15—H15C	109.5
C6—C5—C7	117.9 (2)	H15B—C15—H15C	109.5
N3—C6—C5	176.4 (3)	C21—C16—C17	117.1 (2)
C5—C7—C8	109.67 (19)	C21—C16—C7	123.3 (2)
C5—C7—C16	108.51 (19)	C17—C16—C7	119.5 (2)
C8—C7—C16	112.41 (19)	C18—C17—C16	121.1 (3)
C5—C7—H7	108.7	C18—C17—H17	119.5
C8—C7—H7	108.7	C16—C17—H17	119.5
C16—C7—H7	108.7	C19—C18—C17	119.9 (3)
C9—C8—C11	119.4 (2)	C19—C18—H18	120.1
C9—C8—C7	122.7 (2)	C17—C18—H18	120.1
C11—C8—C7	117.9 (2)	C20—C19—C18	120.5 (3)
C8—C9—O1	122.2 (2)	C20—C19—H19	119.7
C8—C9—C10	129.5 (2)	C18—C19—H19	119.7
O1—C9—C10	108.3 (2)	C19—C20—C21	119.2 (3)
C9—C10—H10A	109.5	C19—C20—H20	120.4
C9—C10—H10B	109.5	C21—C20—H20	120.4
H10A—C10—H10B	109.5	C20—C21—C16	122.1 (3)
C9—C10—H10C	109.5	C20—C21—Cl	117.1 (2)
H10A—C10—H10C	109.5	C16—C21—Cl	120.8 (2)
H10B—C10—H10C	109.5	C3—N1—C1	121.2 (2)
O2—C11—O3	122.4 (3)	C3—N1—C2	120.6 (2)
O2—C11—C8	126.3 (3)	C1—N1—C2	118.1 (2)
O3—C11—C8	111.3 (2)	C3—N2—C4	118.2 (2)
C13—C12—O3	114.9 (3)	C9—O1—C4	120.97 (19)
C13—C12—H12A	108.5	C11—O3—C12	117.1 (3)
O3—C12—H12A	108.5

N2—C4—C5—C6	−0.7 (4)	C5—C7—C16—C17	72.4 (3)
O1—C4—C5—C6	179.6 (2)	C8—C7—C16—C17	−49.1 (3)
N2—C4—C5—C7	176.7 (2)	C21—C16—C17—C18	1.0 (4)
O1—C4—C5—C7	−3.0 (4)	C7—C16—C17—C18	−175.6 (3)
C4—C5—C6—N3	175 (5)	C16—C17—C18—C19	0.7 (5)
C7—C5—C6—N3	−3 (5)	C17—C18—C19—C20	−1.2 (5)
C4—C5—C7—C8	6.1 (3)	C18—C19—C20—C21	0.0 (5)
C6—C5—C7—C8	−176.4 (2)	C19—C20—C21—C16	1.8 (5)
C4—C5—C7—C16	−117.0 (3)	C19—C20—C21—Cl	−177.8 (3)
C6—C5—C7—C16	60.5 (3)	C17—C16—C21—C20	−2.3 (4)
C5—C7—C8—C9	−4.2 (3)	C7—C16—C21—C20	174.2 (2)
C16—C7—C8—C9	116.6 (3)	C17—C16—C21—Cl	177.3 (2)
C5—C7—C8—C11	174.5 (2)	C7—C16—C21—Cl	−6.3 (3)
C16—C7—C8—C11	−64.7 (3)	N2—C3—N1—C1	−179.2 (3)
C11—C8—C9—O1	−179.6 (2)	N2—C3—N1—C2	−0.5 (4)
C7—C8—C9—O1	−0.9 (4)	N1—C3—N2—C4	177.1 (2)
C11—C8—C9—C10	−0.3 (4)	C5—C4—N2—C3	179.5 (2)
C7—C8—C9—C10	178.4 (3)	O1—C4—N2—C3	−0.8 (3)
C9—C8—C11—O2	−7.4 (5)	C8—C9—O1—C4	5.0 (4)
C7—C8—C11—O2	173.9 (3)	C10—C9—O1—C4	−174.5 (2)
C9—C8—C11—O3	172.5 (2)	C5—C4—O1—C9	−3.0 (3)
C7—C8—C11—O3	−6.3 (3)	N2—C4—O1—C9	177.3 (2)
O3—C12—C13—C15	−41.0 (7)	O2—C11—O3—C12	1.1 (4)
O3—C12—C13—C14	−174.6 (5)	C8—C11—O3—C12	−178.7 (2)
C5—C7—C16—C21	−104.0 (3)	C13—C12—O3—C11	−86.1 (5)
C8—C7—C16—C21	134.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2ⁱ	0.93	2.46	3.3368	157

Symmetry code: (i) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2ⁱ	0.93	2.46	3.3368	157

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

The authors thank Dr Babu Varghese, Senior Scientific Officer SAIF, IIT Madras, India, for carrying out the data collection.

References

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Volume 71| Part 2| February 2015| Pages o101-o102

doi:10.1107/S2056989015000079

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

Crystal structure of iso­butyl 4-(2-chloro­phen­yl)-5-cyano-6-{(E)-[(di­methyl­amino)­methyl­­idene]amino}-2-methyl-4H-pyran-3-carboxyl­ate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of isobutyl 4-(2-chlorophenyl)-5-cyano-6-{(E)-[(dimethylamino)methylidene]amino}-2-methyl-4H-pyran-3-carboxylate