3-Amino-1-(4-fluoro-phen-yl)-7-meth-oxy-1H-benzo[f]chromene-2-carbonitrile.

In the title compound, C21H15FN2O2, the furan ring has a flattened half-chair conformation [the methine C atom lies 0.136 (2) Å above the C5 plane which has an r.m.s. deviation of 0.0229 Å]. Overall, the 1H-benzo[f]chromene fused-ring system approximates a plane (r.m.s. deviation of the 14 non-H atoms = 0.049 Å). The fluoro-benzene ring is almost perpendicular to this plane [dihedral angle = 89.58 (8)°]. Zigzag supra-molecular tapes along the b axis are the most notable feature of the crystal packing. This arises through an alternating sequence of 12-membered {⋯HNC3N}2 and eight-membered {⋯HNCO}2 synthons. These are connected into a three-dimensional architecture by π-π [inter-centroid distance for centrosymmetrically related fluoro-benzene rings = 3.5181 (10) Å] and C-H⋯π inter-actions.

Related literature

For a related structure and background to 4H-chromene derivatives, see: El-Agrody et al. (2013 ▶). For related structures, see: Wang et al. (2008 ▶); Shekhar et al. (2012 ▶);

Experimental

Crystal data

C21H15FN2O2

M = 346.35

Triclinic,

a = 8.7798 (9) Å

b = 9.6329 (6) Å

c = 10.9130 (11) Å

α = 77.074 (7)°

β = 68.414 (10)°

γ = 87.083 (7)°

V = 835.99 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.30 × 0.30 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.821, T max = 1.000

7587 measured reflections

3868 independent reflections

2569 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.145

S = 1.02

3868 reflections

244 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.16 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/S1600536813005473/hb7049sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005473/hb7049Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005473/hb7049Isup3.cml

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

C21H15FN2O2	Z = 2
Mr = 346.35	F(000) = 360
Triclinic, P1	Dx = 1.376 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7798 (9) Å	Cell parameters from 1958 reflections
b = 9.6329 (6) Å	θ = 3.1–27.5°
c = 10.9130 (11) Å	µ = 0.10 mm−1
α = 77.074 (7)°	T = 295 K
β = 68.414 (10)°	Prism, light-brown
γ = 87.083 (7)°	0.30 × 0.30 × 0.10 mm
V = 835.99 (13) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	3868 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2569 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.029
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 3.1°
ω scan	h = −8→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −12→12
Tmin = 0.821, Tmax = 1.000	l = −13→14
7587 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.145	w = 1/[σ2(Fo2) + (0.0577P)2 + 0.1106P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3868 reflections	Δρmax = 0.19 e Å−3
244 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (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	0.2857 (2)	0.90095 (14)	1.15726 (13)	0.0943 (5)
O1	0.77412 (14)	0.54184 (11)	0.57793 (13)	0.0452 (3)
O2	−0.11449 (16)	0.62729 (15)	0.84385 (16)	0.0692 (5)
N1	0.97391 (19)	0.70744 (19)	0.49939 (18)	0.0537 (5)
H1	1.020 (3)	0.790 (2)	0.492 (2)	0.078 (7)*
H2	1.030 (3)	0.633 (3)	0.480 (2)	0.080 (7)*
N2	0.7893 (2)	1.04350 (16)	0.51621 (19)	0.0677 (6)
C1	0.6096 (2)	0.49698 (16)	0.62727 (16)	0.0366 (4)
C2	0.5869 (2)	0.35217 (16)	0.63298 (17)	0.0414 (4)
H2A	0.6766	0.2958	0.6040	0.050*
C3	0.4316 (2)	0.29574 (17)	0.68165 (17)	0.0446 (4)
H3	0.4156	0.1996	0.6869	0.054*
C4	0.2945 (2)	0.38016 (17)	0.72431 (17)	0.0414 (4)
C5	0.1313 (3)	0.3245 (2)	0.7744 (2)	0.0564 (5)
H5	0.1133	0.2285	0.7807	0.068*
C6	0.0011 (3)	0.4075 (2)	0.8134 (2)	0.0633 (6)
H6	−0.1047	0.3681	0.8469	0.076*
C7	0.0254 (2)	0.5534 (2)	0.8034 (2)	0.0513 (5)
C8	0.1808 (2)	0.61196 (18)	0.75438 (18)	0.0441 (4)
H8	0.1957	0.7089	0.7465	0.053*
C9	0.3190 (2)	0.52689 (16)	0.71562 (16)	0.0372 (4)
C10	0.4828 (2)	0.58616 (15)	0.66581 (15)	0.0343 (4)
C11	0.51257 (19)	0.74259 (15)	0.65506 (16)	0.0351 (4)
H11	0.4541	0.7977	0.6002	0.042*
C12	0.6944 (2)	0.78082 (15)	0.58154 (16)	0.0373 (4)
C13	0.8109 (2)	0.68330 (16)	0.55414 (17)	0.0392 (4)
C14	−0.0958 (3)	0.7740 (2)	0.8413 (3)	0.0734 (7)
H14A	−0.2018	0.8130	0.8766	0.110*
H14B	−0.0391	0.8247	0.7500	0.110*
H14C	−0.0338	0.7832	0.8957	0.110*
C15	0.44924 (19)	0.78420 (15)	0.79176 (16)	0.0370 (4)
C16	0.3506 (2)	0.89994 (17)	0.8121 (2)	0.0509 (5)
H16	0.3206	0.9516	0.7421	0.061*
C17	0.2955 (3)	0.9403 (2)	0.9351 (2)	0.0634 (6)
H17	0.2295	1.0183	0.9483	0.076*
C18	0.3407 (3)	0.8624 (2)	1.0362 (2)	0.0575 (6)
C19	0.4377 (3)	0.7473 (2)	1.02070 (19)	0.0548 (5)
H19	0.4670	0.6963	1.0913	0.066*
C20	0.4910 (2)	0.70854 (18)	0.89766 (17)	0.0454 (4)
H20	0.5564	0.6299	0.8858	0.054*
C21	0.7466 (2)	0.92564 (17)	0.54616 (18)	0.0441 (4)

	U11	U22	U33	U12	U13	U23
F1	0.1272 (14)	0.0935 (10)	0.0578 (8)	0.0132 (9)	−0.0173 (8)	−0.0393 (7)
O1	0.0329 (7)	0.0349 (6)	0.0654 (8)	0.0018 (5)	−0.0135 (6)	−0.0140 (5)
O2	0.0339 (7)	0.0678 (9)	0.1011 (12)	−0.0024 (6)	−0.0146 (8)	−0.0258 (8)
N1	0.0325 (9)	0.0453 (9)	0.0791 (12)	−0.0011 (7)	−0.0103 (8)	−0.0220 (8)
N2	0.0572 (11)	0.0378 (9)	0.0939 (14)	−0.0085 (7)	−0.0128 (10)	−0.0095 (8)
C1	0.0352 (9)	0.0358 (8)	0.0379 (9)	−0.0014 (6)	−0.0123 (7)	−0.0075 (6)
C2	0.0444 (10)	0.0335 (8)	0.0458 (10)	0.0038 (7)	−0.0160 (8)	−0.0093 (7)
C3	0.0556 (12)	0.0310 (8)	0.0483 (10)	−0.0068 (7)	−0.0209 (9)	−0.0059 (7)
C4	0.0446 (10)	0.0375 (9)	0.0418 (9)	−0.0071 (7)	−0.0171 (8)	−0.0043 (7)
C5	0.0511 (12)	0.0434 (10)	0.0715 (13)	−0.0151 (8)	−0.0205 (10)	−0.0060 (9)
C6	0.0401 (11)	0.0596 (12)	0.0834 (15)	−0.0168 (9)	−0.0165 (11)	−0.0085 (10)
C7	0.0355 (10)	0.0569 (11)	0.0599 (12)	−0.0041 (8)	−0.0149 (9)	−0.0125 (9)
C8	0.0373 (10)	0.0430 (9)	0.0520 (11)	−0.0034 (7)	−0.0156 (8)	−0.0107 (7)
C9	0.0376 (9)	0.0387 (9)	0.0361 (9)	−0.0049 (7)	−0.0151 (7)	−0.0060 (6)
C10	0.0355 (9)	0.0332 (8)	0.0346 (8)	−0.0020 (6)	−0.0130 (7)	−0.0074 (6)
C11	0.0303 (8)	0.0328 (8)	0.0418 (9)	0.0004 (6)	−0.0130 (7)	−0.0076 (6)
C12	0.0353 (9)	0.0321 (8)	0.0420 (9)	−0.0023 (6)	−0.0114 (7)	−0.0076 (7)
C13	0.0361 (9)	0.0343 (8)	0.0459 (10)	−0.0027 (7)	−0.0122 (8)	−0.0104 (7)
C14	0.0436 (12)	0.0753 (15)	0.1080 (19)	0.0078 (10)	−0.0225 (12)	−0.0435 (13)
C15	0.0321 (8)	0.0325 (8)	0.0435 (9)	−0.0049 (6)	−0.0092 (7)	−0.0095 (7)
C16	0.0594 (12)	0.0367 (9)	0.0555 (11)	0.0048 (8)	−0.0190 (9)	−0.0122 (8)
C17	0.0748 (16)	0.0451 (11)	0.0654 (14)	0.0113 (9)	−0.0140 (11)	−0.0251 (9)
C18	0.0646 (14)	0.0588 (12)	0.0443 (11)	−0.0064 (10)	−0.0069 (10)	−0.0220 (9)
C19	0.0575 (13)	0.0618 (12)	0.0440 (11)	−0.0024 (9)	−0.0169 (9)	−0.0110 (9)
C20	0.0409 (10)	0.0473 (10)	0.0469 (10)	0.0013 (7)	−0.0142 (8)	−0.0115 (8)
C21	0.0345 (9)	0.0397 (9)	0.0531 (10)	−0.0008 (7)	−0.0099 (8)	−0.0106 (7)

F1—C18	1.359 (2)	C8—C9	1.414 (2)
O1—C13	1.3613 (18)	C8—H8	0.9300
O1—C1	1.3966 (19)	C9—C10	1.434 (2)
O2—C7	1.365 (2)	C10—C11	1.514 (2)
O2—C14	1.424 (2)	C11—C12	1.521 (2)
N1—C13	1.343 (2)	C11—C15	1.526 (2)
N1—H1	0.89 (2)	C11—H11	0.9800
N1—H2	0.87 (2)	C12—C13	1.349 (2)
N2—C21	1.151 (2)	C12—C21	1.414 (2)
C1—C10	1.369 (2)	C14—H14A	0.9600
C1—C2	1.403 (2)	C14—H14B	0.9600
C2—C3	1.360 (2)	C14—H14C	0.9600
C2—H2A	0.9300	C15—C20	1.382 (2)
C3—C4	1.409 (3)	C15—C16	1.383 (2)
C3—H3	0.9300	C16—C17	1.387 (3)
C4—C5	1.418 (2)	C16—H16	0.9300
C4—C9	1.417 (2)	C17—C18	1.363 (3)
C5—C6	1.352 (3)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.366 (3)
C6—C7	1.405 (3)	C19—C20	1.380 (2)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.369 (2)	C20—H20	0.9300
C13—O1—C1	118.63 (12)	C10—C11—C15	113.09 (12)
C7—O2—C14	117.06 (15)	C12—C11—C15	110.77 (13)
C13—N1—H1	122.0 (15)	C10—C11—H11	107.8
C13—N1—H2	114.6 (16)	C12—C11—H11	107.8
H1—N1—H2	123 (2)	C15—C11—H11	107.8
C10—C1—O1	123.09 (14)	C13—C12—C21	117.59 (15)
C10—C1—C2	123.33 (16)	C13—C12—C11	123.60 (13)
O1—C1—C2	113.58 (14)	C21—C12—C11	118.71 (14)
C3—C2—C1	118.86 (16)	N1—C13—C12	127.20 (15)
C3—C2—H2A	120.6	N1—C13—O1	110.29 (14)
C1—C2—H2A	120.6	C12—C13—O1	122.50 (15)
C2—C3—C4	121.27 (15)	O2—C14—H14A	109.5
C2—C3—H3	119.4	O2—C14—H14B	109.5
C4—C3—H3	119.4	H14A—C14—H14B	109.5
C3—C4—C5	122.50 (16)	O2—C14—H14C	109.5
C3—C4—C9	119.31 (16)	H14A—C14—H14C	109.5
C5—C4—C9	118.18 (17)	H14B—C14—H14C	109.5
C6—C5—C4	121.72 (17)	C20—C15—C16	118.34 (16)
C6—C5—H5	119.1	C20—C15—C11	120.85 (15)
C4—C5—H5	119.1	C16—C15—C11	120.80 (16)
C5—C6—C7	120.09 (18)	C15—C16—C17	121.12 (19)
C5—C6—H6	120.0	C15—C16—H16	119.4
C7—C6—H6	120.0	C17—C16—H16	119.4
O2—C7—C8	124.64 (17)	C18—C17—C16	118.26 (18)
O2—C7—C6	115.14 (17)	C18—C17—H17	120.9
C8—C7—C6	120.21 (18)	C16—C17—H17	120.9
C7—C8—C9	120.80 (16)	F1—C18—C19	119.1 (2)
C7—C8—H8	119.6	F1—C18—C17	118.35 (19)
C9—C8—H8	119.6	C19—C18—C17	122.58 (18)
C8—C9—C4	118.98 (15)	C18—C19—C20	118.36 (19)
C8—C9—C10	121.54 (15)	C18—C19—H19	120.8
C4—C9—C10	119.47 (15)	C20—C19—H19	120.8
C1—C10—C9	117.74 (14)	C15—C20—C19	121.33 (17)
C1—C10—C11	121.65 (14)	C15—C20—H20	119.3
C9—C10—C11	120.61 (14)	C19—C20—H20	119.3
C10—C11—C12	109.49 (13)	N2—C21—C12	179.4 (2)
C13—O1—C1—C10	−6.8 (2)	C4—C9—C10—C11	179.82 (14)
C13—O1—C1—C2	172.96 (14)	C1—C10—C11—C12	7.1 (2)
C10—C1—C2—C3	−1.4 (3)	C9—C10—C11—C12	−172.08 (14)
O1—C1—C2—C3	178.88 (15)	C1—C10—C11—C15	−116.92 (17)
C1—C2—C3—C4	0.8 (3)	C9—C10—C11—C15	63.9 (2)
C2—C3—C4—C5	179.49 (17)	C10—C11—C12—C13	−11.2 (2)
C2—C3—C4—C9	0.3 (3)	C15—C11—C12—C13	114.20 (18)
C3—C4—C5—C6	−179.2 (2)	C10—C11—C12—C21	172.48 (15)
C9—C4—C5—C6	0.0 (3)	C15—C11—C12—C21	−62.1 (2)
C4—C5—C6—C7	0.7 (4)	C21—C12—C13—N1	1.9 (3)
C14—O2—C7—C8	−3.6 (3)	C11—C12—C13—N1	−174.45 (18)
C14—O2—C7—C6	177.17 (19)	C21—C12—C13—O1	−176.76 (15)
C5—C6—C7—O2	179.2 (2)	C11—C12—C13—O1	6.9 (3)
C5—C6—C7—C8	−0.1 (3)	C1—O1—C13—N1	−176.14 (15)
O2—C7—C8—C9	179.56 (18)	C1—O1—C13—C12	2.7 (2)
C6—C7—C8—C9	−1.2 (3)	C10—C11—C15—C20	51.2 (2)
C7—C8—C9—C4	1.9 (3)	C12—C11—C15—C20	−72.18 (18)
C7—C8—C9—C10	−179.13 (17)	C10—C11—C15—C16	−129.82 (17)
C3—C4—C9—C8	177.90 (16)	C12—C11—C15—C16	106.85 (18)
C5—C4—C9—C8	−1.3 (3)	C20—C15—C16—C17	0.5 (3)
C3—C4—C9—C10	−1.1 (2)	C11—C15—C16—C17	−178.57 (17)
C5—C4—C9—C10	179.75 (16)	C15—C16—C17—C18	−0.2 (3)
O1—C1—C10—C9	−179.64 (14)	C16—C17—C18—F1	−179.39 (18)
C2—C1—C10—C9	0.6 (3)	C16—C17—C18—C19	0.1 (3)
O1—C1—C10—C11	1.1 (3)	F1—C18—C19—C20	179.25 (17)
C2—C1—C10—C11	−178.59 (15)	C17—C18—C19—C20	−0.2 (3)
C8—C9—C10—C1	−178.36 (16)	C16—C15—C20—C19	−0.6 (3)
C4—C9—C10—C1	0.6 (2)	C11—C15—C20—C19	178.43 (16)
C8—C9—C10—C11	0.9 (3)	C18—C19—C20—C15	0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2i	0.89 (2)	2.34 (3)	3.189 (2)	160 (2)
N1—H2···O1ii	0.87 (2)	2.36 (3)	3.219 (2)	169 (2)
C19—H19···Cg1iii	0.93	2.90	3.831 (2)	174

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C15–CC20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2i	0.89 (2)	2.34 (3)	3.189 (2)	160 (2)
N1—H2⋯O1ii	0.87 (2)	2.36 (3)	3.219 (2)	169 (2)
C19—H19⋯Cg1iii	0.93	2.90	3.831 (2)	174

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