N'-[3-Cyano-4-(4-fluoro-phen-yl)-6-meth-oxy-4H-benzo[h]chromen-2-yl]-N,N-dimethyl-methanimidamide.

In the title compound, C24H20FN3O2, despite the 4H-pyran ring having a flattened half-chair conformation [the methine C atom lies 0.257 (3) Å above the plane of the remaining atoms with an r.m.s. deviation of 0.0295 Å], the 14 non-H atoms of the 4H-benzo[h]chromene residue are approximately coplanar (r.m.s. deviation = 0.081 Å). The benzene ring is nearly perpendicular to this plane [dihedral angle = 76.18 (10)°], but the planar (r.m.s. deviation = 0.033 Å) dimethyl-methanimidamide substituent is coplanar [dihedral angle = 1.96 (12)°]. In the crystal, centrosymmetric dimeric aggregates arise from C-H⋯N inter-actions, and these are connected into supra-molecular layers in the ab plane by C-H⋯π and π-π [inter-centroid (central C6 ring)⋯(outer C6 ring)(i) distance = 3.8564 (14) Å] inter-actions.

Related literature

For background to synthetic aspects of benzochromene derivatives, see: El-Agrody et al. (2011 ▶); Sabry et al. (2011 ▶). For biological inter­est in these derivatives, see: Kidwai et al. (2010 ▶); Singh et al. (2010 ▶); Vukovic et al. (2010 ▶); Abd-El-Aziz et al. (2007 ▶). For a closely related structure, see: Al-Dies et al. (2012 ▶).

Experimental

Crystal data

C24H20FN3O2

M = 401.43

Triclinic,

a = 8.8438 (8) Å

b = 11.0887 (12) Å

c = 11.8001 (13) Å

α = 66.054 (10)°

β = 83.684 (8)°

γ = 75.946 (9)°

V = 1025.85 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.30 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.982, T max = 1.000

9814 measured reflections

4745 independent reflections

2729 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.179

S = 1.04

4745 reflections

273 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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 DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813005503/hg5296sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005503/hg5296Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005503/hg5296Isup3.cml

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

C24H20FN3O2	Z = 2
Mr = 401.43	F(000) = 420
Triclinic, P1	Dx = 1.300 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8438 (8) Å	Cell parameters from 2074 reflections
b = 11.0887 (12) Å	θ = 2.9–27.5°
c = 11.8001 (13) Å	µ = 0.09 mm−1
α = 66.054 (10)°	T = 295 K
β = 83.684 (8)°	Prism, light-brown
γ = 75.946 (9)°	0.30 × 0.20 × 0.10 mm
V = 1025.85 (18) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	4745 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2729 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.034
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.9°
ω scan	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −14→10
Tmin = 0.982, Tmax = 1.000	l = −15→15
9814 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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0687P)2 + 0.1794P] where P = (Fo2 + 2Fc2)/3
4745 reflections	(Δ/σ)max < 0.001
273 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.24 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
F1	0.10342 (19)	0.85738 (18)	0.04207 (18)	0.1067 (7)
O1	0.71783 (15)	0.23009 (15)	0.24647 (13)	0.0480 (4)
O2	0.17217 (17)	0.07626 (18)	0.46549 (17)	0.0682 (5)
N1	0.91690 (18)	0.34311 (18)	0.21651 (16)	0.0462 (4)
N2	1.1331 (2)	0.2837 (2)	0.10802 (18)	0.0584 (5)
N3	0.8000 (2)	0.5769 (2)	0.3565 (2)	0.0720 (6)
C1	0.5773 (2)	0.1989 (2)	0.30364 (19)	0.0406 (5)
C2	0.5430 (2)	0.0847 (2)	0.29533 (19)	0.0429 (5)
C3	0.6411 (3)	0.0088 (2)	0.2340 (2)	0.0520 (6)
H3	0.7331	0.0337	0.1965	0.062*
C4	0.6024 (3)	−0.1006 (3)	0.2292 (2)	0.0659 (7)
H4	0.6684	−0.1499	0.1887	0.079*
C5	0.4646 (3)	−0.1394 (3)	0.2847 (3)	0.0698 (7)
H5	0.4393	−0.2142	0.2806	0.084*
C6	0.3676 (3)	−0.0688 (3)	0.3445 (2)	0.0617 (7)
H6	0.2766	−0.0962	0.3815	0.074*
C7	0.4025 (2)	0.0459 (2)	0.3515 (2)	0.0476 (5)
C8	0.3038 (2)	0.1228 (2)	0.4135 (2)	0.0484 (5)
C9	0.3424 (2)	0.2318 (2)	0.4185 (2)	0.0463 (5)
H9	0.2769	0.2803	0.4599	0.056*
C10	0.4819 (2)	0.2725 (2)	0.36114 (18)	0.0407 (5)
C11	0.5173 (2)	0.3992 (2)	0.36151 (18)	0.0408 (5)
H11	0.5020	0.3962	0.4461	0.049*
C12	0.6864 (2)	0.4009 (2)	0.32420 (19)	0.0418 (5)
C13	0.7733 (2)	0.3255 (2)	0.26505 (19)	0.0421 (5)
C14	0.9972 (2)	0.2654 (2)	0.1639 (2)	0.0515 (6)
H14	0.9582	0.1941	0.1654	0.062*
C15	1.2168 (3)	0.2017 (4)	0.0420 (3)	0.0856 (9)
H15A	1.1658	0.1296	0.0559	0.128*
H15B	1.3218	0.1644	0.0714	0.128*
H15C	1.2183	0.2568	−0.0452	0.128*
C16	1.1981 (3)	0.3944 (3)	0.1012 (3)	0.0690 (7)
H16A	1.1416	0.4334	0.1569	0.103*
H16B	1.1899	0.4618	0.0181	0.103*
H16C	1.3057	0.3612	0.1243	0.103*
C17	0.7526 (2)	0.4977 (2)	0.3405 (2)	0.0510 (6)
C18	0.4058 (2)	0.5249 (2)	0.27590 (19)	0.0415 (5)
C19	0.4420 (3)	0.5885 (2)	0.1521 (2)	0.0554 (6)
H19	0.5369	0.5554	0.1211	0.066*
C20	0.3412 (3)	0.6998 (3)	0.0731 (3)	0.0704 (7)
H20	0.3675	0.7421	−0.0100	0.084*
C21	0.2032 (3)	0.7458 (3)	0.1193 (3)	0.0668 (7)
C22	0.1591 (3)	0.6859 (3)	0.2398 (3)	0.0699 (8)
H22	0.0621	0.7186	0.2684	0.084*
C23	0.2623 (2)	0.5750 (2)	0.3191 (2)	0.0582 (6)
H23	0.2349	0.5338	0.4021	0.070*
C24	0.0645 (3)	0.1533 (3)	0.5229 (3)	0.0758 (8)
H24A	−0.0230	0.1117	0.5552	0.114*
H24B	0.0291	0.2434	0.4628	0.114*
H24C	0.1147	0.1566	0.5893	0.114*

	U11	U22	U33	U12	U13	U23
F1	0.0857 (11)	0.0803 (13)	0.1207 (16)	0.0159 (9)	−0.0371 (10)	−0.0162 (11)
O1	0.0466 (8)	0.0539 (10)	0.0540 (9)	−0.0222 (7)	0.0144 (6)	−0.0293 (8)
O2	0.0510 (9)	0.0675 (12)	0.0898 (13)	−0.0299 (8)	0.0205 (8)	−0.0305 (10)
N1	0.0380 (9)	0.0529 (11)	0.0474 (11)	−0.0126 (8)	0.0044 (7)	−0.0191 (9)
N2	0.0426 (10)	0.0811 (15)	0.0584 (13)	−0.0176 (10)	0.0095 (8)	−0.0347 (11)
N3	0.0654 (13)	0.0720 (16)	0.0951 (18)	−0.0265 (12)	0.0034 (11)	−0.0440 (14)
C1	0.0399 (10)	0.0404 (12)	0.0400 (11)	−0.0130 (9)	0.0035 (8)	−0.0129 (9)
C2	0.0453 (11)	0.0383 (12)	0.0425 (12)	−0.0096 (9)	−0.0024 (9)	−0.0127 (9)
C3	0.0568 (13)	0.0457 (13)	0.0532 (14)	−0.0128 (10)	0.0043 (10)	−0.0195 (11)
C4	0.0809 (17)	0.0533 (16)	0.0714 (18)	−0.0162 (13)	0.0074 (13)	−0.0337 (14)
C5	0.0837 (18)	0.0531 (16)	0.088 (2)	−0.0263 (14)	0.0006 (15)	−0.0366 (15)
C6	0.0595 (14)	0.0521 (15)	0.0765 (18)	−0.0246 (12)	−0.0003 (12)	−0.0214 (13)
C7	0.0485 (11)	0.0408 (12)	0.0518 (13)	−0.0144 (9)	−0.0039 (9)	−0.0131 (10)
C8	0.0395 (11)	0.0485 (13)	0.0529 (14)	−0.0165 (10)	0.0048 (9)	−0.0129 (11)
C9	0.0431 (11)	0.0435 (12)	0.0502 (13)	−0.0122 (9)	0.0076 (9)	−0.0170 (10)
C10	0.0413 (10)	0.0396 (12)	0.0387 (11)	−0.0126 (9)	0.0038 (8)	−0.0118 (9)
C11	0.0445 (10)	0.0427 (12)	0.0382 (11)	−0.0139 (9)	0.0063 (8)	−0.0181 (10)
C12	0.0420 (10)	0.0402 (12)	0.0466 (12)	−0.0128 (9)	0.0008 (9)	−0.0187 (10)
C13	0.0406 (10)	0.0442 (12)	0.0412 (12)	−0.0156 (9)	−0.0003 (8)	−0.0130 (10)
C14	0.0428 (11)	0.0607 (15)	0.0544 (14)	−0.0161 (10)	0.0038 (10)	−0.0246 (12)
C15	0.0602 (15)	0.122 (3)	0.096 (2)	−0.0189 (16)	0.0195 (14)	−0.071 (2)
C16	0.0544 (14)	0.083 (2)	0.0708 (18)	−0.0321 (13)	0.0091 (12)	−0.0245 (15)
C17	0.0471 (12)	0.0516 (14)	0.0571 (14)	−0.0153 (10)	0.0027 (10)	−0.0225 (12)
C18	0.0415 (10)	0.0388 (11)	0.0484 (13)	−0.0139 (9)	0.0070 (9)	−0.0204 (10)
C19	0.0500 (12)	0.0555 (15)	0.0540 (15)	−0.0084 (11)	0.0060 (10)	−0.0182 (12)
C20	0.0670 (16)	0.0658 (18)	0.0583 (16)	−0.0065 (13)	−0.0052 (12)	−0.0077 (14)
C21	0.0595 (15)	0.0540 (16)	0.0779 (19)	−0.0032 (12)	−0.0184 (13)	−0.0176 (14)
C22	0.0443 (13)	0.0620 (17)	0.100 (2)	−0.0003 (12)	0.0017 (13)	−0.0358 (16)
C23	0.0546 (13)	0.0544 (15)	0.0657 (16)	−0.0128 (11)	0.0142 (11)	−0.0268 (13)
C24	0.0433 (13)	0.091 (2)	0.094 (2)	−0.0241 (13)	0.0203 (13)	−0.0373 (18)

F1—C21	1.368 (3)	C10—C11	1.514 (3)
O1—C13	1.368 (2)	C11—C12	1.514 (3)
O1—C1	1.398 (2)	C11—C18	1.531 (3)
O2—C8	1.369 (2)	C11—H11	0.9800
O2—C24	1.424 (3)	C12—C13	1.350 (3)
N1—C14	1.293 (3)	C12—C17	1.425 (3)
N1—C13	1.359 (2)	C14—H14	0.9300
N2—C14	1.325 (3)	C15—H15A	0.9600
N2—C16	1.448 (3)	C15—H15B	0.9600
N2—C15	1.450 (3)	C15—H15C	0.9600
N3—C17	1.146 (3)	C16—H16A	0.9600
C1—C10	1.352 (3)	C16—H16B	0.9600
C1—C2	1.414 (3)	C16—H16C	0.9600
C2—C3	1.409 (3)	C18—C19	1.380 (3)
C2—C7	1.420 (3)	C18—C23	1.387 (3)
C3—C4	1.361 (3)	C19—C20	1.379 (3)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.396 (3)	C20—C21	1.350 (4)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.355 (3)	C21—C22	1.361 (4)
C5—H5	0.9300	C22—C23	1.390 (3)
C6—C7	1.415 (3)	C22—H22	0.9300
C6—H6	0.9300	C23—H23	0.9300
C7—C8	1.424 (3)	C24—H24A	0.9600
C8—C9	1.358 (3)	C24—H24B	0.9600
C9—C10	1.422 (3)	C24—H24C	0.9600
C9—H9	0.9300
C13—O1—C1	118.87 (16)	C17—C12—C11	118.11 (18)
C8—O2—C24	116.89 (18)	C12—C13—N1	122.48 (19)
C14—N1—C13	119.91 (19)	C12—C13—O1	121.15 (17)
C14—N2—C16	121.1 (2)	N1—C13—O1	116.32 (18)
C14—N2—C15	121.8 (2)	N1—C14—N2	122.4 (2)
C16—N2—C15	116.9 (2)	N1—C14—H14	118.8
C10—C1—O1	122.70 (18)	N2—C14—H14	118.8
C10—C1—C2	122.93 (18)	N2—C15—H15A	109.5
O1—C1—C2	114.36 (18)	N2—C15—H15B	109.5
C3—C2—C1	123.11 (18)	H15A—C15—H15B	109.5
C3—C2—C7	119.0 (2)	N2—C15—H15C	109.5
C1—C2—C7	117.87 (19)	H15A—C15—H15C	109.5
C4—C3—C2	120.6 (2)	H15B—C15—H15C	109.5
C4—C3—H3	119.7	N2—C16—H16A	109.5
C2—C3—H3	119.7	N2—C16—H16B	109.5
C3—C4—C5	120.6 (2)	H16A—C16—H16B	109.5
C3—C4—H4	119.7	N2—C16—H16C	109.5
C5—C4—H4	119.7	H16A—C16—H16C	109.5
C6—C5—C4	120.4 (2)	H16B—C16—H16C	109.5
C6—C5—H5	119.8	N3—C17—C12	177.0 (2)
C4—C5—H5	119.8	C19—C18—C23	117.9 (2)
C5—C6—C7	121.1 (2)	C19—C18—C11	121.06 (18)
C5—C6—H6	119.4	C23—C18—C11	121.02 (19)
C7—C6—H6	119.4	C18—C19—C20	121.8 (2)
C6—C7—C2	118.3 (2)	C18—C19—H19	119.1
C6—C7—C8	122.9 (2)	C20—C19—H19	119.1
C2—C7—C8	118.84 (19)	C21—C20—C19	118.4 (3)
C9—C8—O2	124.9 (2)	C21—C20—H20	120.8
C9—C8—C7	120.82 (18)	C19—C20—H20	120.8
O2—C8—C7	114.24 (19)	C20—C21—C22	122.8 (2)
C8—C9—C10	120.8 (2)	C20—C21—F1	118.8 (3)
C8—C9—H9	119.6	C22—C21—F1	118.4 (2)
C10—C9—H9	119.6	C21—C22—C23	118.4 (2)
C1—C10—C9	118.72 (19)	C21—C22—H22	120.8
C1—C10—C11	121.56 (17)	C23—C22—H22	120.8
C9—C10—C11	119.67 (18)	C18—C23—C22	120.8 (2)
C10—C11—C12	108.81 (16)	C18—C23—H23	119.6
C10—C11—C18	110.34 (16)	C22—C23—H23	119.6
C12—C11—C18	112.23 (16)	O2—C24—H24A	109.5
C10—C11—H11	108.5	O2—C24—H24B	109.5
C12—C11—H11	108.5	H24A—C24—H24B	109.5
C18—C11—H11	108.5	O2—C24—H24C	109.5
C13—C12—C17	117.84 (18)	H24A—C24—H24C	109.5
C13—C12—C11	123.71 (18)	H24B—C24—H24C	109.5
C13—O1—C1—C10	10.3 (3)	C9—C10—C11—C12	166.21 (18)
C13—O1—C1—C2	−170.25 (17)	C1—C10—C11—C18	107.5 (2)
C10—C1—C2—C3	179.1 (2)	C9—C10—C11—C18	−70.2 (2)
O1—C1—C2—C3	−0.4 (3)	C10—C11—C12—C13	18.4 (3)
C10—C1—C2—C7	−0.7 (3)	C18—C11—C12—C13	−104.0 (2)
O1—C1—C2—C7	179.76 (17)	C10—C11—C12—C17	−168.54 (18)
C1—C2—C3—C4	179.8 (2)	C18—C11—C12—C17	69.1 (2)
C7—C2—C3—C4	−0.4 (3)	C17—C12—C13—N1	−3.0 (3)
C2—C3—C4—C5	0.2 (4)	C11—C12—C13—N1	170.10 (18)
C3—C4—C5—C6	−0.2 (4)	C17—C12—C13—O1	179.69 (18)
C4—C5—C6—C7	0.4 (4)	C11—C12—C13—O1	−7.2 (3)
C5—C6—C7—C2	−0.6 (4)	C14—N1—C13—C12	178.0 (2)
C5—C6—C7—C8	−179.9 (2)	C14—N1—C13—O1	−4.6 (3)
C3—C2—C7—C6	0.6 (3)	C1—O1—C13—C12	−8.2 (3)
C1—C2—C7—C6	−179.56 (19)	C1—O1—C13—N1	174.29 (17)
C3—C2—C7—C8	179.9 (2)	C13—N1—C14—N2	175.5 (2)
C1—C2—C7—C8	−0.2 (3)	C16—N2—C14—N1	−1.0 (4)
C24—O2—C8—C9	3.7 (3)	C15—N2—C14—N1	−175.6 (2)
C24—O2—C8—C7	−176.6 (2)	C10—C11—C18—C19	−89.7 (2)
C6—C7—C8—C9	179.6 (2)	C12—C11—C18—C19	31.8 (3)
C2—C7—C8—C9	0.3 (3)	C10—C11—C18—C23	87.5 (2)
C6—C7—C8—O2	−0.1 (3)	C12—C11—C18—C23	−151.0 (2)
C2—C7—C8—O2	−179.39 (18)	C23—C18—C19—C20	1.1 (4)
O2—C8—C9—C10	−179.8 (2)	C11—C18—C19—C20	178.4 (2)
C7—C8—C9—C10	0.5 (3)	C18—C19—C20—C21	−0.6 (4)
O1—C1—C10—C9	−178.99 (17)	C19—C20—C21—C22	−0.8 (4)
C2—C1—C10—C9	1.6 (3)	C19—C20—C21—F1	179.0 (2)
O1—C1—C10—C11	3.3 (3)	C20—C21—C22—C23	1.7 (4)
C2—C1—C10—C11	−176.16 (18)	F1—C21—C22—C23	−178.2 (2)
C8—C9—C10—C1	−1.4 (3)	C19—C18—C23—C22	−0.2 (3)
C8—C9—C10—C11	176.33 (19)	C11—C18—C23—C22	−177.5 (2)
C1—C10—C11—C12	−16.1 (3)	C21—C22—C23—C18	−1.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···N3i	0.93	2.62	3.542 (3)	171
C5—H5···Cg1ii	0.93	2.79	3.670 (3)	159
C15—H15B···Cg2iii	0.96	2.93	3.732 (3)	142
C16—H16C···Cg3iii	0.96	2.91	3.589 (3)	129

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C18–C23, C2–C7 and C1,C2,C7–C10 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23⋯N3i	0.93	2.62	3.542 (3)	171
C5—H5⋯Cg1ii	0.93	2.79	3.670 (3)	159
C15—H15B⋯Cg2iii	0.96	2.93	3.732 (3)	142
C16—H16C⋯Cg3iii	0.96	2.91	3.589 (3)	129

Symmetry codes: (i) ; (ii) ; (iii) .