Crystal structure of isobutyl 4-(2-chloro-phen-yl)-5-cyano-6-{(E)-[(di-methyl-amino)-methyl-idene]amino}-2-methyl-4H-pyran-3-carboxyl-ate.

In the title compound, C21H24ClN3O3, the dihedral angle between the pyran ring (r.m.s. deviation = 0.037 Å) and the chloro-benzene ring is 88.56 (14)°. In the crystal, the mol-ecules are linked by C-H⋯O inter-actions, generating C(7) (001) chains.

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 ▸).

Experimental

Crystal data

C21H24ClN3O3

M = 401.88

Monoclinic,

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

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

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.217

S = 1.00

5524 reflections

258 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.44 e Å−3

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 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015000079/hb7341sup1.cif

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

Click here for additional data file.

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

Click here for additional data file.

. DOI: 10.1107/S2056989015000079/hb7341fig1.tif

The mol­ecular structure of the title compound with displacement ellipsoids drawn at 30% probability level.

Click here for additional data file.

c . DOI: 10.1107/S2056989015000079/hb7341fig2.tif

Part of crystal packing of the title compound showing the formation of C(7) chains running parallel to c axis.

CCDC reference: 1041846

Additional supporting information: crystallographic information; 3D view; checkCIF report

C21H24ClN3O3	F(000) = 848
Mr = 401.88	Dx = 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

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

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(Fo2) + (0.1039P)2 + 1.1568P] where P = (Fo2 + 2Fc2)/3
5524 reflections	(Δ/σ)max = 0.033
258 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C17H17O2i	0.93	2.46	3.3368	157

Symmetry code: (i) .