N′-[3-Cyano-4-(4-fluoro­phen­yl)-6-meth­oxy-4H-benzo[h]chromen-2-yl]-N,N-dimethyl­methanimidamide

Al-dies, A.M.; Al-Omar, M.A.; Amr, A.E.-G.E.; El-Agrody, A.M.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536813005503

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 4| April 2013| Pages o482-o483

doi:10.1107/S1600536813005503

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N′-[3-Cyano-4-(4-fluorophenyl)-6-methoxy-4H-benzo[h]chromen-2-yl]-N,N-dimethylmethanimidamide

Al-anood M. Al-dies,^a Mohamed A. Al-Omar,^b,^c Abd El-Galil E. Amr,^c,^d ‡ Ahmed M. El-Agrody,^a Seik Weng Ng ^e,^f and Edward R. T. Tiekink ^e ^*

^aChemistry Department, Faculty of Science, King Khalid University, Abha 61413, PO Box 9004, Saudi Arabia, ^bPharmaceutical Chemistry Department, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^cDrug Exploration & Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^dApplied Organic Chemistry Department, National Research Center, Dokki 12622, Cairo, Egypt, ^eDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^fChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 25 February 2013; accepted 26 February 2013; online 2 March 2013)

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) dimethylmethanimidamide substituent is coplanar [dihedral angle = 1.96 (12)°]. In the crystal, centrosymmetric dimeric aggregates arise from C—H⋯N interactions, and these are connected into supramolecular layers in the ab plane by C—H⋯π and π–π [intercentroid (central C₆ ring)⋯(outer C₆ ring)ⁱ distance = 3.8564 (14) Å] interactions.

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_r = 401.43
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.058
wR(F²) = 0.179
S = 1.04
4745 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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) -x+1, -y+1, -z+1; (ii) x, y-1, z; (iii) x+1, y, z.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813005503/hg5296sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813005503/hg5296Isup3.cml

checkCIF report

Comment top

Benzochromene derivatives have recently received intensified interest due to their synthetic (El-Agrody et al., 2011; Sabry et al., 2011) and pharmaceutical importance (Kidwai et al., 2010; Singh et al., 2010; Vukovic et al., 2010). In continuation of our interest in the chemical and pharmacological properties of 4H-chromene and fused 4H-chromene derivatives (Abd-El-Aziz et al., 2007), the X-ray crystal structure of the title compound, (I), was determined.

In (I), Fig. 1, the 4H-pyran ring approximates a half-chair conformation with the methine-C11 atom lying 0.257 (3) Å out of the least-squares plane defined by the remaining atoms (O1,C1,C10,C12 and C13) which have a r.m.s. deviation of 0.0295 Å. Despite this, the 14 non-hydrogen atoms comprising the 4H-benzo[h]chromene fused ring system approximate a plane with a r.m.s. deviation of 0.081 Å. The benzene ring is approximately perpendicular to this plane, forming a dihedral angle of 76.18 (10)°. The atoms (N1,N2,C14–C16) comprising the dimethylmethanimidamide residue are planar (r.m.s. deviation = 0.033 Å) and this is co-planar with the 4H-benzo[h]chromene residue; dihedral angle = 1.96 (12)°. Finally, the methoxy group is co-planar with the ring to which it is connected as manifested in the C24—O2—C8—C9 torsion angle of 3.7 (3)°. The overall structure resembles closely that reported recently for the parent amine (Al-Dies et al., 2012).

In the crystal packing, C—H···N interactions, Table 1, lead to centrosymmetric dimeric aggregates. These are linked into layers in the ab plane by C—H···π, Table 1, and π—π [inter-centroid (C1,C2,C7–C10)···(C2—C7)ⁱ distance = 3.8564 (14) Å, angle of inclination = 0.07 (11)° for i: 1 - x, -y, 1 - z] interactions, Fig. 2.

Related literature top

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 top

A mixture of 2-amino-4-(4-fluorophenyl)-6-methoxy-4H-benzo[h]chromene-3-carbonitrile (0.01 mol), dimethylformamide-dipentylacetal (DMF-DPA) (0.01 mol) and benzene (30 ml) was refluxed for 3 h. The solvent was removed under reduced pressure and the resulting solid was recrystallized from benzene to give the title compound; M.pt: 513–514 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 35% probability level.
	Fig. 2. View in projection down the b axis of the crystal packing in (I). The C—H···N, C—H···π and π—π interactions are shown as blue, orange and purple dashed lines, respectively.

N'-[3-Cyano-4-(4-fluorophenyl)-6-methoxy-4H-benzo[h]chromen-2-yl]-N,N-dimethylmethanimidamide top

Crystal data top

C₂₄H₂₀FN₃O₂	Z = 2
M_r = 401.43	F(000) = 420
Triclinic, P1	D_x = 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

Data collection top

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	R_int = 0.034
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.9°
ω scan	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −14→10
T_min = 0.982, T_max = 1.000	l = −15→15
9814 measured reflections

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.179	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0687P)² + 0.1794P] where P = (F_o² + 2F_c²)/3
4745 reflections	(Δ/σ)_max < 0.001
273 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₄H₂₀FN₃O₂	γ = 75.946 (9)°
M_r = 401.43	V = 1025.85 (18) Å³
Triclinic, P1	Z = 2
a = 8.8438 (8) Å	Mo Kα radiation
b = 11.0887 (12) Å	µ = 0.09 mm⁻¹
c = 11.8001 (13) Å	T = 295 K
α = 66.054 (10)°	0.30 × 0.20 × 0.10 mm
β = 83.684 (8)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4745 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2729 reflections with I > 2σ(I)
T_min = 0.982, T_max = 1.000	R_int = 0.034
9814 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.179	H-atom parameters constrained
S = 1.04	Δρ_max = 0.20 e Å⁻³
4745 reflections	Δρ_min = −0.24 e Å⁻³
273 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1; (ii) x, y−1, z; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₀FN₃O₂
M_r	401.43
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	8.8438 (8), 11.0887 (12), 11.8001 (13)
α, β, γ (°)	66.054 (10), 83.684 (8), 75.946 (9)
V (Å³)	1025.85 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.982, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9814, 4745, 2729
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.179, 1.04
No. of reflections	4745
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.24

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1; (ii) x, y−1, z; (iii) x+1, y, z.

Footnotes

‡Additional correspondence author, e-mail: aamr1963@yahoo.com.

Acknowledgements

The authors extend their appreciation to the Deanship of Scientific Research at King Saud University for funding this work through the research group project No. RGP-VPP-099. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).

References

Abd-El-Aziz, A. S., Mohamed, H. M., Mohammed, S., Zahid, S., Ata, A., Bedair, A. H., El-Agrody, A. M. & Harvey, P. D. (2007). J. Heterocycl. Chem. 44, 1287–1301. CAS Google Scholar
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
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Volume 69| Part 4| April 2013| Pages o482-o483

doi:10.1107/S1600536813005503

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

N′-[3-Cyano-4-(4-fluoro­phen­yl)-6-meth­­oxy-4H-benzo[h]chromen-2-yl]-N,N-di­methyl­methanimidamide

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Experimental

Crystal data

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organic compounds

N′-[3-Cyano-4-(4-fluorophenyl)-6-methoxy-4H-benzo[h]chromen-2-yl]-N,N-dimethylmethanimidamide