2-Amino-7,7-dimethyl-5-oxo-4-[3-(trifluoro-meth-yl)phen-yl]-5,6,7,8-tetra-hydro-4H-chromene-3-carbonitrile.

In the title mol-ecule, C19H17F3N2O2, the fused cyclo-hexene and pyran rings adopt sofa and flattened boat conformations, respectively. The four essentially planar atoms of the pyran ring [maximum deviation = 0.008 (2) Å] form a dihedral angle of 88.13 (9)° with the benzene ring. The F atoms of the trifluoro-methyl group were refined as disordered over three sets of sites in a 0.507 (7):0.330 (7):0.163 (3) ratio. In the crystal, mol-ecules are connected into inversion dimers via pairs of N-H⋯N hydrogen bonds and these dimers are further linked by N-H⋯O hydrogen bonds into a two-dimensional network parallel to (100).

Related literature

For the biological activity of 4H-pyran derivatives, see: Bhattacharyya et al.(2012 ▶); Khaksar et al. (2012 ▶); Fotouhi et al. (2007 ▶). For related structures, see: Wang (2011 ▶); Anthal et al. (2012 ▶); Kant et al. (2013 ▶). For ring conformations, see: Duax & Norton (1975 ▶).

Experimental

Crystal data

C19H17F3N2O2

M = 362.35

Monoclinic,

a = 23.7543 (6) Å

b = 9.3871 (2) Å

c = 15.8857 (4) Å

β = 94.704 (2)°

V = 3530.33 (15) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.766, T max = 1.000

40937 measured reflections

3467 independent reflections

2538 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.126

S = 1.03

3467 reflections

258 parameters

10 restraints

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813004522/lh5585sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004522/lh5585Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813004522/lh5585Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H17F3N2O2	F(000) = 1504
Mr = 362.35	Dx = 1.363 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 18267 reflections
a = 23.7543 (6) Å	θ = 3.4–29.1°
b = 9.3871 (2) Å	µ = 0.11 mm−1
c = 15.8857 (4) Å	T = 293 K
β = 94.704 (2)°	Block, colorless
V = 3530.33 (15) Å3	0.3 × 0.2 × 0.2 mm
Z = 8

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3467 independent reflections
Radiation source: fine-focus sealed tube	2538 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.4°
ω scans	h = −29→29
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −11→11
Tmin = 0.766, Tmax = 1.000	l = −19→19
40937 measured reflections

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) = 0.126	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0389P)2 + 5.1587P] where P = (Fo2 + 2Fc2)/3
3467 reflections	(Δ/σ)max = 0.001
258 parameters	Δρmax = 0.26 e Å−3
10 restraints	Δρmin = −0.32 e Å−3

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
O1	0.08902 (7)	0.55303 (15)	1.02901 (8)	0.0401 (4)
C2	0.06233 (9)	0.6806 (2)	1.01297 (12)	0.0324 (5)
O2	0.06995 (8)	0.41341 (18)	0.74350 (9)	0.0506 (5)
C3	0.04766 (9)	0.7238 (2)	0.93258 (12)	0.0308 (5)
C4	0.06583 (9)	0.6445 (2)	0.85626 (12)	0.0319 (5)
H4	0.0335	0.6405	0.8138	0.038*
C4A	0.08096 (9)	0.4945 (2)	0.88253 (12)	0.0313 (5)
C5	0.08182 (9)	0.3842 (2)	0.81766 (13)	0.0358 (5)
C6	0.09581 (11)	0.2348 (2)	0.84666 (15)	0.0431 (6)
H6A	0.1117	0.1836	0.8011	0.052*
H6B	0.0612	0.1869	0.8588	0.052*
C7	0.13766 (10)	0.2287 (2)	0.92539 (14)	0.0394 (5)
C8	0.11327 (11)	0.3177 (2)	0.99442 (14)	0.0402 (6)
H8A	0.0821	0.2663	1.0161	0.048*
H8B	0.1421	0.3309	1.0407	0.048*
C8A	0.09300 (9)	0.4593 (2)	0.96338 (13)	0.0319 (5)
C9	0.11372 (10)	0.7223 (2)	0.81771 (12)	0.0337 (5)
C10	0.16874 (10)	0.7180 (2)	0.85477 (13)	0.0377 (5)
H10	0.1772	0.6617	0.9023	0.045*
C11	0.21092 (11)	0.7965 (3)	0.82186 (15)	0.0454 (6)
C12	0.19901 (13)	0.8810 (3)	0.75148 (17)	0.0575 (7)
H12	0.2275	0.9335	0.7292	0.069*
C13	0.14458 (14)	0.8865 (3)	0.71472 (16)	0.0636 (8)
H13	0.1360	0.9440	0.6677	0.076*
C14	0.10264 (11)	0.8071 (3)	0.74738 (14)	0.0498 (7)
H14	0.0661	0.8107	0.7214	0.060*
C15	0.26941 (13)	0.7941 (4)	0.8631 (2)	0.0643 (8)
C19	0.01734 (9)	0.8518 (2)	0.91848 (12)	0.0328 (5)
N20	−0.00772 (9)	0.9545 (2)	0.90387 (12)	0.0495 (6)
N21	0.05451 (9)	0.7470 (2)	1.08480 (11)	0.0446 (5)
H21A	0.0381	0.8288	1.0839	0.054*
H21B	0.0658	0.7083	1.1323	0.054*
C22	0.19433 (11)	0.2886 (3)	0.90370 (18)	0.0583 (7)
H22A	0.1887	0.3805	0.8779	0.088*
H22B	0.2109	0.2254	0.8652	0.088*
H22C	0.2190	0.2975	0.9544	0.088*
C23	0.14521 (13)	0.0752 (3)	0.95659 (17)	0.0592 (8)
H23A	0.1580	0.0171	0.9122	0.089*
H23B	0.1098	0.0395	0.9727	0.089*
H23C	0.1726	0.0727	1.0044	0.089*
F1A	0.2811 (5)	0.8968 (12)	0.9208 (6)	0.089 (2)	0.507 (7)
F2A	0.2806 (3)	0.6766 (7)	0.9151 (5)	0.0813 (17)	0.507 (7)
F3A	0.3113 (2)	0.7874 (11)	0.8116 (4)	0.091 (2)	0.507 (7)
F1B	0.2694 (8)	0.861 (2)	0.9364 (9)	0.089 (2)	0.330 (7)
F2B	0.2877 (5)	0.6587 (9)	0.8792 (8)	0.0813 (17)	0.330 (7)
F3B	0.3049 (4)	0.8668 (14)	0.8182 (7)	0.091 (2)	0.330 (7)
F1C	0.2904 (6)	0.9254 (11)	0.8551 (10)	0.089 (2)	0.163 (3)
F2C	0.2730 (6)	0.7466 (19)	0.9427 (6)	0.0813 (17)	0.163 (3)
F3C	0.2982 (6)	0.7011 (16)	0.8215 (10)	0.091 (2)	0.163 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0604 (11)	0.0333 (8)	0.0262 (7)	0.0141 (7)	0.0006 (7)	−0.0023 (6)
C2	0.0373 (13)	0.0274 (10)	0.0326 (11)	0.0049 (9)	0.0042 (9)	−0.0011 (9)
O2	0.0679 (12)	0.0506 (10)	0.0325 (9)	0.0070 (9)	−0.0012 (8)	−0.0119 (8)
C3	0.0333 (12)	0.0291 (10)	0.0299 (11)	0.0049 (9)	0.0027 (8)	−0.0011 (8)
C4	0.0365 (13)	0.0338 (11)	0.0246 (10)	0.0056 (9)	−0.0024 (8)	−0.0015 (8)
C4A	0.0303 (12)	0.0325 (11)	0.0311 (11)	0.0007 (9)	0.0023 (8)	−0.0036 (9)
C5	0.0316 (12)	0.0403 (12)	0.0358 (12)	−0.0004 (10)	0.0042 (9)	−0.0079 (10)
C6	0.0495 (15)	0.0323 (12)	0.0480 (13)	−0.0001 (11)	0.0073 (11)	−0.0114 (10)
C7	0.0436 (14)	0.0307 (11)	0.0450 (13)	0.0061 (10)	0.0101 (10)	−0.0006 (10)
C8	0.0524 (15)	0.0311 (11)	0.0377 (12)	0.0061 (11)	0.0075 (10)	0.0026 (10)
C8A	0.0344 (13)	0.0288 (11)	0.0328 (11)	0.0009 (9)	0.0055 (9)	−0.0025 (9)
C9	0.0438 (14)	0.0323 (11)	0.0255 (10)	0.0066 (10)	0.0057 (9)	−0.0034 (9)
C10	0.0438 (14)	0.0376 (12)	0.0322 (11)	0.0059 (10)	0.0058 (10)	0.0014 (10)
C11	0.0484 (15)	0.0464 (14)	0.0431 (13)	0.0029 (12)	0.0151 (11)	−0.0079 (11)
C12	0.063 (2)	0.0597 (17)	0.0531 (16)	−0.0032 (14)	0.0267 (14)	0.0068 (13)
C13	0.078 (2)	0.0712 (19)	0.0429 (15)	0.0045 (16)	0.0142 (14)	0.0259 (14)
C14	0.0539 (17)	0.0607 (16)	0.0345 (13)	0.0068 (13)	0.0022 (11)	0.0116 (12)
C15	0.0492 (18)	0.077 (2)	0.0679 (19)	−0.0027 (16)	0.0137 (14)	0.0023 (17)
C19	0.0381 (13)	0.0354 (12)	0.0248 (10)	0.0012 (10)	0.0023 (9)	−0.0033 (9)
N20	0.0636 (15)	0.0412 (12)	0.0423 (11)	0.0166 (11)	−0.0040 (10)	−0.0042 (9)
N21	0.0708 (15)	0.0362 (10)	0.0270 (9)	0.0175 (10)	0.0058 (9)	−0.0005 (8)
C22	0.0380 (15)	0.0703 (18)	0.0675 (17)	0.0098 (14)	0.0094 (12)	0.0119 (15)
C23	0.080 (2)	0.0344 (13)	0.0647 (17)	0.0141 (13)	0.0142 (15)	−0.0008 (12)
F1A	0.061 (5)	0.119 (6)	0.085 (3)	−0.017 (3)	−0.006 (3)	−0.031 (5)
F2A	0.057 (3)	0.098 (3)	0.089 (5)	0.029 (2)	0.005 (3)	−0.004 (3)
F3A	0.0386 (17)	0.154 (7)	0.0855 (18)	0.008 (3)	0.0329 (12)	0.012 (4)
F1B	0.061 (5)	0.119 (6)	0.085 (3)	−0.017 (3)	−0.006 (3)	−0.031 (5)
F2B	0.057 (3)	0.098 (3)	0.089 (5)	0.029 (2)	0.005 (3)	−0.004 (3)
F3B	0.0386 (17)	0.154 (7)	0.0855 (18)	0.008 (3)	0.0329 (12)	0.012 (4)
F1C	0.061 (5)	0.119 (6)	0.085 (3)	−0.017 (3)	−0.006 (3)	−0.031 (5)
F2C	0.057 (3)	0.098 (3)	0.089 (5)	0.029 (2)	0.005 (3)	−0.004 (3)
F3C	0.0386 (17)	0.154 (7)	0.0855 (18)	0.008 (3)	0.0329 (12)	0.012 (4)

O1—C2	1.369 (2)	C11—C12	1.381 (4)
O1—C8A	1.373 (2)	C11—C15	1.487 (4)
C2—N21	1.327 (3)	C12—C13	1.375 (4)
C2—C3	1.358 (3)	C12—H12	0.9300
O2—C5	1.220 (3)	C13—C14	1.379 (4)
C3—C19	1.409 (3)	C13—H13	0.9300
C3—C4	1.515 (3)	C14—H14	0.9300
C4—C4A	1.504 (3)	C15—F3C	1.320 (8)
C4—C9	1.522 (3)	C15—F1B	1.321 (8)
C4—H4	0.9800	C15—F3B	1.336 (7)
C4A—C8A	1.334 (3)	C15—F2C	1.337 (8)
C4A—C5	1.462 (3)	C15—F3A	1.339 (5)
C5—C6	1.505 (3)	C15—F1C	1.340 (8)
C6—C7	1.534 (3)	C15—F1A	1.344 (5)
C6—H6A	0.9700	C15—F2B	1.360 (7)
C6—H6B	0.9700	C15—F2A	1.389 (5)
C7—C22	1.524 (3)	C19—N20	1.147 (3)
C7—C23	1.529 (3)	N21—H21A	0.8600
C7—C8	1.530 (3)	N21—H21B	0.8600
C8—C8A	1.484 (3)	C22—H22A	0.9600
C8—H8A	0.9700	C22—H22B	0.9600
C8—H8B	0.9700	C22—H22C	0.9600
C9—C14	1.379 (3)	C23—H23A	0.9600
C9—C10	1.389 (3)	C23—H23B	0.9600
C10—C11	1.380 (3)	C23—H23C	0.9600
C10—H10	0.9300
C2—O1—C8A	118.60 (15)	C9—C14—C13	121.4 (2)
N21—C2—C3	128.71 (19)	C9—C14—H14	119.3
N21—C2—O1	110.26 (17)	C13—C14—H14	119.3
C3—C2—O1	121.03 (18)	F3C—C15—F1B	142.4 (12)
C2—C3—C19	119.51 (18)	F3C—C15—F3B	72.2 (8)
C2—C3—C4	122.53 (18)	F1B—C15—F3B	105.9 (9)
C19—C3—C4	117.84 (17)	F3C—C15—F2C	104.9 (10)
C4A—C4—C3	108.37 (16)	F3B—C15—F2C	132.9 (9)
C4A—C4—C9	113.05 (18)	F1B—C15—F3A	127.9 (8)
C3—C4—C9	110.95 (17)	F2C—C15—F3A	124.6 (7)
C4A—C4—H4	108.1	F3C—C15—F1C	110.4 (10)
C3—C4—H4	108.1	F1B—C15—F1C	71.1 (10)
C9—C4—H4	108.1	F2C—C15—F1C	113.6 (10)
C8A—C4A—C5	119.27 (19)	F3A—C15—F1C	71.6 (8)
C8A—C4A—C4	121.77 (18)	F3C—C15—F1A	136.9 (9)
C5—C4A—C4	118.96 (17)	F3B—C15—F1A	83.9 (6)
O2—C5—C4A	120.4 (2)	F2C—C15—F1A	66.4 (10)
O2—C5—C6	122.18 (19)	F3A—C15—F1A	109.1 (5)
C4A—C5—C6	117.37 (18)	F1B—C15—F2B	107.4 (12)
C5—C6—C7	113.39 (18)	F3B—C15—F2B	111.8 (7)
C5—C6—H6A	108.9	F2C—C15—F2B	61.1 (8)
C7—C6—H6A	108.9	F3A—C15—F2B	80.2 (5)
C5—C6—H6B	108.9	F1C—C15—F2B	139.6 (8)
C7—C6—H6B	108.9	F1A—C15—F2B	119.8 (9)
H6A—C6—H6B	107.7	F3C—C15—F2A	72.0 (8)
C22—C7—C23	109.8 (2)	F1B—C15—F2A	82.3 (11)
C22—C7—C8	110.7 (2)	F3B—C15—F2A	128.6 (6)
C23—C7—C8	108.87 (19)	F3A—C15—F2A	102.1 (4)
C22—C7—C6	109.1 (2)	F1C—C15—F2A	137.0 (7)
C23—C7—C6	110.5 (2)	F1A—C15—F2A	98.3 (7)
C8—C7—C6	107.79 (19)	F3C—C15—C11	107.1 (7)
C8A—C8—C7	112.50 (18)	F1B—C15—C11	108.2 (9)
C8A—C8—H8A	109.1	F3B—C15—C11	111.4 (6)
C7—C8—H8A	109.1	F2C—C15—C11	114.0 (7)
C8A—C8—H8B	109.1	F3A—C15—C11	116.4 (4)
C7—C8—H8B	109.1	F1C—C15—C11	106.6 (6)
H8A—C8—H8B	107.8	F1A—C15—C11	115.0 (6)
C4A—C8A—O1	123.33 (18)	F2B—C15—C11	111.7 (6)
C4A—C8A—C8	125.43 (19)	F2A—C15—C11	113.6 (4)
O1—C8A—C8	111.23 (17)	N20—C19—C3	177.4 (2)
C14—C9—C10	118.1 (2)	C2—N21—H21A	120.0
C14—C9—C4	120.2 (2)	C2—N21—H21B	120.0
C10—C9—C4	121.58 (18)	H21A—N21—H21B	120.0
C11—C10—C9	120.7 (2)	C7—C22—H22A	109.5
C11—C10—H10	119.6	C7—C22—H22B	109.5
C9—C10—H10	119.6	H22A—C22—H22B	109.5
C10—C11—C12	120.4 (2)	C7—C22—H22C	109.5
C10—C11—C15	120.4 (2)	H22A—C22—H22C	109.5
C12—C11—C15	119.2 (2)	H22B—C22—H22C	109.5
C13—C12—C11	119.2 (2)	C7—C23—H23A	109.5
C13—C12—H12	120.4	C7—C23—H23B	109.5
C11—C12—H12	120.4	H23A—C23—H23B	109.5
C12—C13—C14	120.2 (2)	C7—C23—H23C	109.5
C12—C13—H13	119.9	H23A—C23—H23C	109.5
C14—C13—H13	119.9	H23B—C23—H23C	109.5
C8A—O1—C2—N21	170.12 (19)	C7—C8—C8A—O1	−159.98 (19)
C8A—O1—C2—C3	−9.9 (3)	C4A—C4—C9—C14	138.3 (2)
N21—C2—C3—C19	−3.7 (4)	C3—C4—C9—C14	−99.8 (2)
O1—C2—C3—C19	176.4 (2)	C4A—C4—C9—C10	−46.0 (3)
N21—C2—C3—C4	172.3 (2)	C3—C4—C9—C10	76.0 (2)
O1—C2—C3—C4	−7.7 (3)	C14—C9—C10—C11	0.0 (3)
C2—C3—C4—C4A	21.0 (3)	C4—C9—C10—C11	−175.90 (19)
C19—C3—C4—C4A	−163.03 (19)	C9—C10—C11—C12	0.2 (3)
C2—C3—C4—C9	−103.7 (2)	C9—C10—C11—C15	178.5 (2)
C19—C3—C4—C9	72.3 (2)	C10—C11—C12—C13	0.3 (4)
C3—C4—C4A—C8A	−19.2 (3)	C15—C11—C12—C13	−178.1 (3)
C9—C4—C4A—C8A	104.2 (2)	C11—C12—C13—C14	−0.8 (4)
C3—C4—C4A—C5	160.06 (18)	C10—C9—C14—C13	−0.5 (4)
C9—C4—C4A—C5	−76.5 (2)	C4—C9—C14—C13	175.4 (2)
C8A—C4A—C5—O2	178.7 (2)	C12—C13—C14—C9	0.9 (4)
C4—C4A—C5—O2	−0.7 (3)	C10—C11—C15—F3C	97.7 (9)
C8A—C4A—C5—C6	0.7 (3)	C12—C11—C15—F3C	−83.9 (9)
C4—C4A—C5—C6	−178.6 (2)	C10—C11—C15—F1B	−69.1 (11)
O2—C5—C6—C7	149.3 (2)	C12—C11—C15—F1B	109.3 (10)
C4A—C5—C6—C7	−32.8 (3)	C10—C11—C15—F3B	174.8 (7)
C5—C6—C7—C22	−65.0 (3)	C12—C11—C15—F3B	−6.8 (8)
C5—C6—C7—C23	174.1 (2)	C10—C11—C15—F2C	−17.9 (10)
C5—C6—C7—C8	55.3 (3)	C12—C11—C15—F2C	160.5 (9)
C22—C7—C8—C8A	71.6 (3)	C10—C11—C15—F3A	138.6 (6)
C23—C7—C8—C8A	−167.6 (2)	C12—C11—C15—F3A	−43.0 (6)
C6—C7—C8—C8A	−47.7 (3)	C10—C11—C15—F1C	−144.1 (8)
C5—C4A—C8A—O1	−174.82 (19)	C12—C11—C15—F1C	34.3 (9)
C4—C4A—C8A—O1	4.5 (3)	C10—C11—C15—F1A	−91.9 (6)
C5—C4A—C8A—C8	6.5 (3)	C12—C11—C15—F1A	86.5 (6)
C4—C4A—C8A—C8	−174.2 (2)	C10—C11—C15—F2B	49.0 (7)
C2—O1—C8A—C4A	11.7 (3)	C12—C11—C15—F2B	−132.6 (6)
C2—O1—C8A—C8	−169.41 (19)	C10—C11—C15—F2A	20.3 (5)
C7—C8—C8A—C4A	18.8 (3)	C12—C11—C15—F2A	−161.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21A···N20i	0.86	2.17	3.025 (3)	171
N21—H21B···O2ii	0.86	2.10	2.934 (2)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N21—H21A⋯N20i	0.86	2.17	3.025 (3)	171
N21—H21B⋯O2ii	0.86	2.10	2.934 (2)	163

Symmetry codes: (i) ; (ii) .