3-Amino-1-(4-fluoro­phen­yl)-8-meth­oxy-1H-benzo[f]chromene-2-carbonitrile

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

doi:10.1107/S160053681300545X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 4| April 2013| Pages o476-o477

doi:10.1107/S160053681300545X

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3-Amino-1-(4-fluorophenyl)-8-methoxy-1H-benzo[f]chromene-2-carbonitrile

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

^aChemistry Department, Faculty of Science, King Khalid University, Abha 61413, PO Box 9004, Saudi Arabia, ^bChemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, 11884, Egypt, ^cPharmaceutical Chemistry Department, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^dDrug Exploration & Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^eApplied Organic Chemistry Department, National Research Center, Dokki 12622, Cairo, Egypt, ^fDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^gChemistry 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 25 February 2013; online 2 March 2013)

The title compound, C₂₁H₁₅FN₂O₂, features an approximately planar 1H-benzo[f]chromene fused-ring system (r.m.s. deviation for the 14 non-H atoms = 0.052 Å), with the fluorobenzene ring being almost perpendicular to this [dihedral angle = 85.30 (7) °]. The furan ring has a flattened half-chair conformation, with the methine C atom deviating by 0.132 (2) Å from the plane of the remaining atoms (r.m.s. deviation = 0.0107 Å). In the crystal, inversion dimers are formed via pairs of amine–cyano N—H⋯N hydrogen bonds. The dimers are connected into a three-dimensional architecture by C—H⋯N(cyano), C—H⋯π and π–π [intercentroid distance = 3.6671 (10) Å] interactions.

Related literature

For background and various applications of benzo- and naphthopyran- derivatives, see: Bonsignore et al. (1993 ); Hafez et al. (1987 ). For background to the chemistry and biological activity of 4H-pyran derivatives, see: El-Agrody et al. (2011 ); Sabry et al. (2011 ). For related structures, see: Wang et al. (2008 ); Shekhar et al. (2012 ); Amr et al. (2013 ).

Experimental

Crystal data

C₂₁H₁₅FN₂O₂
M_r = 346.35
Triclinic, $[P \overline 1]$
a = 8.9672 (7) Å
b = 10.4365 (8) Å
c = 10.9058 (8) Å
α = 103.063 (7)°
β = 106.859 (7)°
γ = 111.399 (8)°
V = 844.01 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.10 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 = 0.722, T_max = 1.000
7109 measured reflections
3902 independent reflections
2716 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.138
S = 1.05
3902 reflections
244 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C4,C9,C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2ⁱ	0.89 (2)	2.16 (2)	3.043 (2)	170.0 (18)
C19—H19⋯N2ⁱⁱ	0.93	2.51	3.259 (3)	138
C11—H11⋯Cg1ⁱⁱⁱ	0.98	2.90	3.7084 (17)	141
C14—H14C⋯Cg1^iv	0.96	2.92	3.772 (3)	148
Symmetry codes: (i) -x+2, -y+1, -z+2; (ii) -x+1, -y+1, -z+2; (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y+2, -z+1.

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/S160053681300545X/hb7047sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681300545X/hb7047Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681300545X/hb7047Isup3.cml

checkCIF report

Comment top

Benzo- and naphthopyran-derivatives can possess biological and pharmacological activities, such as anti-coagulant, spasmolytic, diuretic, anti-cancer and anti-anaphylactin activities (Bonsignore et al., 1993). Some of these compounds can also be employed as cosmetics, pigments and as potential biodegradable agrochemicals (Hafez, et al., 1987). Derivatives of 4H-pyran are also known to exhibit biological activities (El-Agrody et al., 2011; Sabry et al., 2011), and form the focus of on-going studies of their chemistry. In this connection, herein, the crystal and molecular structure of the title compound, (I), is described.

In (I), Fig. 1, the 14 non-hydrogen atoms of the 1H-benzo[f]chromene fused-ring system are co-planar with a r.m.s. deviation of the fitted atoms = 0.052 Å. The maximum deviations are 0.136 (2) Å for the methine-C11 atom and -0.052 (2) Å for the aromatic-C7 atom. This implies that the furan ring is approximately planar as borne out by the observation that the methine-C11 atom lies only 0.132 (2) Å above the plane of the remaining atoms (r.m.s. deviation = 0.0107 Å), indicating a flattened half-chair conformation. The fluorobenzene ring is approximately perpendicular to the 1H-benzo[f]chromene residue, forming a dihedral angle of 85.30 (7)°. The methoxy group is co-planar with the ring to which it is attached as seen in the value of the C14—O2—C6—C5 torsion angle of 0.5 (3)°. The structure described here resembles very closely those of the 4-bromo (Wang et al., 2008) and 2-CF₃ (Shekhar et al., 2012) derivatives of the parent compound, as well as that of the 7-methoxy analogue (Amr et al., 2013).

Hydrogen bonding features in the crystal packing whereby 12-membered {···HNC₃N}₂ synthons formed by centrosymmetrically related molecules arise from the formation of amine-N—H···N(cyano) hydrogen bonds, Table 1. These are connected into a three-dimensional architecture by C—H···N2(cyano), C—H···π and π—π [inter-centroid distance for (O1,C1,C10–C13)···(C4–C9)ⁱ = 3.6671 (10) Å, inter-planar angle = 4.19 (8)° for i: 1 - x, 1 - y, 1 - z] interactions, Fig. 2 and Table 1. The second amine-H2 atom does not participate in a significant intermolecular interaction.

Related literature top

For background and various applications of benzo- and naphthopyran- derivatives, see: Bonsignore et al. (1993); Hafez et al. (1987). For background to the chemistry and biological activity of 4H-pyran derivatives, see: El-Agrody et al. (2011); Sabry et al. (2011). For related structures, see: Wang et al. (2008); Shekhar et al. (2012); Amr et al. (2013).

Experimental top

A solution of 6-bromo-2-naphthol (0.01 mol) in EtOH (30 ml) was treated with α-cyano-p-fluorocinnamonitrile (0.01 mol) and piperidine (0.5 ml). The reaction mixture was heated until complete precipitation occurred corresponding to a reaction time of 60 min. The solid product which formed was collected by filtration and recrystallized from ethanol to give the title compound, (I), in the form of light brown prisms; M.pt: 529–530 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 displacement ellipsoids at the 35% probability level.
	Fig. 2. A view in projection down the b axis of the crystal packing in (I). The N—H···N, C—H···N, C—H···π and π–π interactions are shown as blue, orange, purple and brown dashed lines, respectively.

3-Amino-1-(4-fluorophenyl)-8-methoxy-1H-benzo[f]chromene-2-carbonitrile top

Crystal data top

C₂₁H₁₅FN₂O₂	Z = 2
M_r = 346.35	F(000) = 360
Triclinic, P1	D_x = 1.363 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9672 (7) Å	Cell parameters from 2078 reflections
b = 10.4365 (8) Å	θ = 3.2–27.5°
c = 10.9058 (8) Å	µ = 0.10 mm⁻¹
α = 103.063 (7)°	T = 295 K
β = 106.859 (7)°	Prism, light-brown
γ = 111.399 (8)°	0.30 × 0.20 × 0.10 mm
V = 844.01 (11) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3902 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2716 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.023
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 3.2°
ω scan	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −13→12
T_min = 0.722, T_max = 1.000	l = −14→13
7109 measured reflections

Refinement top

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)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.138	w = 1/[σ²(F_o²) + (0.0568P)² + 0.1033P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3902 reflections	Δρ_max = 0.20 e Å⁻³
244 parameters	Δρ_min = −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: 0.031 (4)

Crystal data top

C₂₁H₁₅FN₂O₂	γ = 111.399 (8)°
M_r = 346.35	V = 844.01 (11) Å³
Triclinic, P1	Z = 2
a = 8.9672 (7) Å	Mo Kα radiation
b = 10.4365 (8) Å	µ = 0.10 mm⁻¹
c = 10.9058 (8) Å	T = 295 K
α = 103.063 (7)°	0.30 × 0.20 × 0.10 mm
β = 106.859 (7)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3902 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2716 reflections with I > 2σ(I)
T_min = 0.722, T_max = 1.000	R_int = 0.023
7109 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.20 e Å⁻³
3902 reflections	Δρ_min = −0.16 e Å⁻³
244 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	0.65107 (18)	1.02622 (15)	1.19074 (13)	0.0888 (4)
O1	0.93475 (14)	0.70759 (13)	0.65915 (12)	0.0489 (3)
O2	0.08769 (17)	0.77609 (16)	0.33736 (14)	0.0685 (4)
N1	1.0769 (2)	0.62403 (19)	0.79544 (18)	0.0538 (4)
N2	0.8096 (2)	0.4809 (2)	0.97164 (18)	0.0655 (5)
C1	0.7901 (2)	0.72705 (17)	0.59527 (16)	0.0416 (4)
C2	0.8067 (2)	0.7931 (2)	0.49837 (18)	0.0511 (4)
H2A	0.9069	0.8184	0.4806	0.061*
C3	0.6756 (2)	0.8201 (2)	0.43063 (18)	0.0518 (4)
H3	0.6879	0.8664	0.3681	0.062*
C4	0.5202 (2)	0.77860 (17)	0.45373 (15)	0.0428 (4)
C5	0.3816 (2)	0.80453 (18)	0.38152 (17)	0.0489 (4)
H5	0.3935	0.8522	0.3199	0.059*
C6	0.2310 (2)	0.75979 (19)	0.40231 (17)	0.0493 (4)
C7	0.2135 (2)	0.6892 (2)	0.49622 (17)	0.0503 (4)
H7	0.1100	0.6585	0.5094	0.060*
C8	0.3452 (2)	0.66482 (18)	0.56843 (16)	0.0444 (4)
H8	0.3307	0.6182	0.6305	0.053*
C9	0.50492 (19)	0.70961 (16)	0.55037 (15)	0.0391 (4)
C10	0.64573 (19)	0.68629 (16)	0.62547 (15)	0.0370 (3)
C11	0.63936 (18)	0.62664 (16)	0.73856 (15)	0.0370 (3)
H11	0.5315	0.5327	0.7006	0.044*
C12	0.79503 (19)	0.59719 (16)	0.78873 (15)	0.0396 (4)
C13	0.93049 (19)	0.63973 (17)	0.75081 (16)	0.0411 (4)
C14	0.0952 (3)	0.8443 (3)	0.2389 (2)	0.0773 (6)
H14A	−0.0123	0.8498	0.2013	0.116*
H14B	0.1107	0.7867	0.1661	0.116*
H14C	0.1921	0.9424	0.2829	0.116*
C15	0.63823 (18)	0.73347 (16)	0.85967 (15)	0.0376 (3)
C16	0.7538 (2)	0.88289 (19)	0.91135 (18)	0.0509 (4)
H16	0.8299	0.9174	0.8704	0.061*
C17	0.7591 (3)	0.9820 (2)	1.0222 (2)	0.0614 (5)
H17	0.8370	1.0825	1.0558	0.074*
C18	0.6474 (2)	0.9291 (2)	1.08140 (18)	0.0567 (5)
C19	0.5336 (2)	0.7830 (2)	1.03607 (19)	0.0614 (5)
H19	0.4600	0.7495	1.0792	0.074*
C20	0.5293 (2)	0.6848 (2)	0.92405 (17)	0.0507 (4)
H20	0.4517	0.5844	0.8918	0.061*
C21	0.80450 (19)	0.53183 (18)	0.88874 (17)	0.0453 (4)
H1	1.096 (3)	0.588 (2)	0.861 (2)	0.065 (6)*
H2	1.158 (3)	0.672 (2)	0.772 (2)	0.063 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.1109 (10)	0.0868 (9)	0.0662 (8)	0.0463 (7)	0.0490 (7)	0.0064 (7)
O1	0.0466 (6)	0.0623 (7)	0.0539 (7)	0.0294 (5)	0.0262 (5)	0.0343 (6)
O2	0.0705 (8)	0.0905 (10)	0.0680 (9)	0.0550 (8)	0.0249 (7)	0.0441 (8)
N1	0.0463 (9)	0.0631 (10)	0.0626 (10)	0.0293 (7)	0.0230 (7)	0.0338 (8)
N2	0.0573 (9)	0.0839 (12)	0.0741 (11)	0.0350 (8)	0.0293 (8)	0.0542 (10)
C1	0.0456 (8)	0.0443 (9)	0.0396 (8)	0.0234 (7)	0.0177 (7)	0.0188 (7)
C2	0.0538 (10)	0.0611 (11)	0.0502 (10)	0.0272 (8)	0.0289 (8)	0.0301 (9)
C3	0.0615 (10)	0.0584 (11)	0.0460 (9)	0.0287 (8)	0.0257 (8)	0.0306 (8)
C4	0.0527 (9)	0.0411 (9)	0.0357 (8)	0.0234 (7)	0.0165 (7)	0.0155 (7)
C5	0.0637 (11)	0.0474 (10)	0.0396 (9)	0.0299 (8)	0.0178 (8)	0.0203 (7)
C6	0.0575 (10)	0.0528 (10)	0.0426 (9)	0.0345 (8)	0.0152 (8)	0.0176 (8)
C7	0.0516 (9)	0.0617 (11)	0.0456 (9)	0.0328 (8)	0.0210 (8)	0.0210 (8)
C8	0.0515 (9)	0.0515 (10)	0.0376 (8)	0.0281 (7)	0.0201 (7)	0.0194 (7)
C9	0.0466 (8)	0.0376 (8)	0.0320 (8)	0.0205 (6)	0.0146 (6)	0.0115 (6)
C10	0.0445 (8)	0.0350 (8)	0.0318 (7)	0.0190 (6)	0.0153 (6)	0.0124 (6)
C11	0.0380 (8)	0.0355 (8)	0.0364 (8)	0.0154 (6)	0.0142 (6)	0.0157 (6)
C12	0.0442 (8)	0.0377 (8)	0.0383 (8)	0.0195 (6)	0.0159 (6)	0.0168 (7)
C13	0.0443 (8)	0.0390 (8)	0.0399 (8)	0.0205 (7)	0.0150 (7)	0.0156 (7)
C14	0.0899 (15)	0.0878 (16)	0.0666 (13)	0.0557 (13)	0.0184 (11)	0.0427 (12)
C15	0.0386 (8)	0.0412 (8)	0.0351 (8)	0.0187 (6)	0.0145 (6)	0.0181 (6)
C16	0.0589 (10)	0.0453 (10)	0.0502 (10)	0.0188 (8)	0.0305 (8)	0.0192 (8)
C17	0.0745 (12)	0.0440 (10)	0.0576 (11)	0.0199 (9)	0.0313 (10)	0.0123 (9)
C18	0.0660 (11)	0.0633 (12)	0.0422 (9)	0.0335 (9)	0.0254 (8)	0.0117 (9)
C19	0.0593 (11)	0.0734 (13)	0.0491 (10)	0.0220 (9)	0.0328 (9)	0.0195 (9)
C20	0.0501 (9)	0.0492 (10)	0.0450 (9)	0.0129 (7)	0.0224 (7)	0.0172 (8)
C21	0.0399 (8)	0.0488 (9)	0.0491 (9)	0.0212 (7)	0.0159 (7)	0.0234 (8)

Geometric parameters (Å, º) top

F1—C18	1.362 (2)	C8—C9	1.423 (2)
O1—C13	1.3508 (19)	C8—H8	0.9300
O1—C1	1.3933 (18)	C9—C10	1.428 (2)
O2—C6	1.3665 (19)	C10—C11	1.508 (2)
O2—C14	1.419 (2)	C11—C12	1.513 (2)
N1—C13	1.345 (2)	C11—C15	1.529 (2)
N1—H1	0.89 (2)	C11—H11	0.9800
N1—H2	0.87 (2)	C12—C13	1.351 (2)
N2—C21	1.146 (2)	C12—C21	1.410 (2)
C1—C10	1.369 (2)	C14—H14A	0.9600
C1—C2	1.400 (2)	C14—H14B	0.9600
C2—C3	1.356 (2)	C14—H14C	0.9600
C2—H2A	0.9300	C15—C20	1.379 (2)
C3—C4	1.416 (2)	C15—C16	1.381 (2)
C3—H3	0.9300	C16—C17	1.379 (2)
C4—C9	1.415 (2)	C16—H16	0.9300
C4—C5	1.418 (2)	C17—C18	1.363 (3)
C5—C6	1.364 (2)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.357 (3)
C6—C7	1.402 (2)	C19—C20	1.387 (2)
C7—C8	1.361 (2)	C19—H19	0.9300
C7—H7	0.9300	C20—H20	0.9300

C13—O1—C1	118.99 (12)	C10—C11—C15	111.81 (12)
C6—O2—C14	117.43 (15)	C12—C11—C15	109.77 (12)
C13—N1—H1	120.1 (13)	C10—C11—H11	108.5
C13—N1—H2	114.8 (13)	C12—C11—H11	108.5
H1—N1—H2	123.1 (19)	C15—C11—H11	108.5
C10—C1—O1	122.98 (14)	C13—C12—C21	118.53 (14)
C10—C1—C2	123.20 (15)	C13—C12—C11	123.71 (14)
O1—C1—C2	113.82 (13)	C21—C12—C11	117.57 (13)
C3—C2—C1	119.46 (15)	N1—C13—O1	110.25 (14)
C3—C2—H2A	120.3	N1—C13—C12	127.35 (16)
C1—C2—H2A	120.3	O1—C13—C12	122.39 (14)
C2—C3—C4	120.94 (16)	O2—C14—H14A	109.5
C2—C3—H3	119.5	O2—C14—H14B	109.5
C4—C3—H3	119.5	H14A—C14—H14B	109.5
C9—C4—C5	120.25 (15)	O2—C14—H14C	109.5
C9—C4—C3	118.64 (15)	H14A—C14—H14C	109.5
C5—C4—C3	121.11 (16)	H14B—C14—H14C	109.5
C6—C5—C4	120.17 (16)	C20—C15—C16	118.03 (15)
C6—C5—H5	119.9	C20—C15—C11	121.98 (14)
C4—C5—H5	119.9	C16—C15—C11	119.93 (13)
O2—C6—C5	125.58 (17)	C17—C16—C15	121.56 (16)
O2—C6—C7	114.43 (15)	C17—C16—H16	119.2
C5—C6—C7	119.99 (15)	C15—C16—H16	119.2
C8—C7—C6	121.13 (16)	C18—C17—C16	118.34 (17)
C8—C7—H7	119.4	C18—C17—H17	120.8
C6—C7—H7	119.4	C16—C17—H17	120.8
C7—C8—C9	120.94 (16)	C19—C18—F1	118.80 (17)
C7—C8—H8	119.5	C19—C18—C17	122.38 (16)
C9—C8—H8	119.5	F1—C18—C17	118.82 (17)
C4—C9—C10	120.40 (14)	C18—C19—C20	118.59 (16)
C4—C9—C8	117.51 (14)	C18—C19—H19	120.7
C10—C9—C8	122.09 (15)	C20—C19—H19	120.7
C1—C10—C9	117.30 (14)	C15—C20—C19	121.09 (16)
C1—C10—C11	121.40 (14)	C15—C20—H20	119.5
C9—C10—C11	121.23 (13)	C19—C20—H20	119.5
C10—C11—C12	109.72 (12)	N2—C21—C12	177.89 (18)

C13—O1—C1—C10	3.0 (2)	C8—C9—C10—C11	−6.2 (2)
C13—O1—C1—C2	−177.54 (13)	C1—C10—C11—C12	−9.55 (19)
C10—C1—C2—C3	0.5 (3)	C9—C10—C11—C12	173.70 (12)
O1—C1—C2—C3	−179.02 (15)	C1—C10—C11—C15	112.49 (15)
C1—C2—C3—C4	−1.7 (3)	C9—C10—C11—C15	−64.26 (17)
C2—C3—C4—C9	0.7 (3)	C10—C11—C12—C13	9.0 (2)
C2—C3—C4—C5	−179.04 (16)	C15—C11—C12—C13	−114.21 (16)
C9—C4—C5—C6	−1.6 (2)	C10—C11—C12—C21	−176.02 (13)
C3—C4—C5—C6	178.06 (15)	C15—C11—C12—C21	60.74 (17)
C14—O2—C6—C5	0.5 (3)	C1—O1—C13—N1	176.64 (13)
C14—O2—C6—C7	−178.87 (16)	C1—O1—C13—C12	−3.7 (2)
C4—C5—C6—O2	−178.78 (15)	C21—C12—C13—N1	1.8 (3)
C4—C5—C6—C7	0.6 (3)	C11—C12—C13—N1	176.66 (15)
O2—C6—C7—C8	179.82 (15)	C21—C12—C13—O1	−177.78 (14)
C5—C6—C7—C8	0.4 (3)	C11—C12—C13—O1	−2.9 (2)
C6—C7—C8—C9	−0.3 (3)	C10—C11—C15—C20	137.00 (15)
C5—C4—C9—C10	−178.61 (13)	C12—C11—C15—C20	−100.99 (17)
C3—C4—C9—C10	1.7 (2)	C10—C11—C15—C16	−45.73 (19)
C5—C4—C9—C8	1.6 (2)	C12—C11—C15—C16	76.27 (18)
C3—C4—C9—C8	−178.05 (14)	C20—C15—C16—C17	−1.3 (3)
C7—C8—C9—C4	−0.7 (2)	C11—C15—C16—C17	−178.64 (16)
C7—C8—C9—C10	179.57 (14)	C15—C16—C17—C18	0.4 (3)
O1—C1—C10—C9	−178.74 (13)	C16—C17—C18—C19	0.8 (3)
C2—C1—C10—C9	1.8 (2)	C16—C17—C18—F1	−179.78 (17)
O1—C1—C10—C11	4.4 (2)	F1—C18—C19—C20	179.49 (17)
C2—C1—C10—C11	−175.07 (14)	C17—C18—C19—C20	−1.1 (3)
C4—C9—C10—C1	−2.9 (2)	C16—C15—C20—C19	1.0 (3)
C8—C9—C10—C1	176.87 (14)	C11—C15—C20—C19	178.28 (16)
C4—C9—C10—C11	174.03 (13)	C18—C19—C20—C15	0.2 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C4,C9,C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2ⁱ	0.89 (2)	2.16 (2)	3.043 (2)	170.0 (18)
C19—H19···N2ⁱⁱ	0.93	2.51	3.259 (3)	138
C11—H11···Cg1ⁱⁱⁱ	0.98	2.90	3.7084 (17)	141
C14—H14C···Cg1^iv	0.96	2.92	3.772 (3)	148

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₅FN₂O₂
M_r	346.35
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	8.9672 (7), 10.4365 (8), 10.9058 (8)
α, β, γ (°)	103.063 (7), 106.859 (7), 111.399 (8)
V (Å³)	844.01 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
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	0.722, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7109, 3902, 2716
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.138, 1.05
No. of reflections	3902
No. of parameters	244
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.16

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 is the centroid of the C1–C4,C9,C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2ⁱ	0.89 (2)	2.16 (2)	3.043 (2)	170.0 (18)
C19—H19···N2ⁱⁱ	0.93	2.51	3.259 (3)	138
C11—H11···Cg1ⁱⁱⁱ	0.98	2.90	3.7084 (17)	141
C14—H14C···Cg1^iv	0.96	2.92	3.772 (3)	148

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+2, −z+1.

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

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Volume 69| Part 4| April 2013| Pages o476-o477

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