2-Amino-4-(4-fluoro­phen­yl)-6-meth­oxy-4H-benzo[h]chromene-3-carbonitrile

Al-Dies, A.-A.M.; Amr, A.-G.E.; El-Agrody, A.M.; Chia, T.S.; Fun, H.-K.

doi:10.1107/S1600536812023021

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1934-o1935

doi:10.1107/S1600536812023021

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2-Amino-4-(4-fluorophenyl)-6-methoxy-4H-benzo[h]chromene-3-carbonitrile

Al-Anood M. Al-Dies,^a Abdel-Galil E. Amr,^b,^c Ahmed M. El-Agrody,^a Tze Shyang Chia ^d and Hoong-Kun Fun ^d ^*‡

^aChemistry Department, Faculty of Science, King Khalid University, 9004 Abha, Saudi Arabia, ^bDrug Exploration & Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^cApplied Organic Chemistry Department, National Research Center, Dokki 12622, Cairo, Egypt, and ^dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 13 May 2012; accepted 20 May 2012; online 31 May 2012)

In the title molecule, C₂₁H₁₅FN₂O₂, the dihedral angle between the fluoro-substituted benzene ring and the mean plane of the 4H-benzo[h]chromene ring system [maximum deviation = 0.109 (2) Å] is 83.35 (7)°. The pyran ring adopts a slight sofa conformation with the tertiary C(H) atom forming the flap. The methoxy group is slightly twisted from the attached benzene ring of the 4H-benzo[h]chromene moiety [C—O—C—C = −4.3 (3)°]. In the crystal, molecules are linked by intermolecular N—H⋯N hydrogen bonds into infinite wave-like chains along the b axis. The crystal packing is further stabilized by π–π interactions [centroid–centroid distance = 3.7713 (9) Å].

Related literature

For the synthesis of 4H-chromene derivatives, see: Sayed et al. (2000 ); Bedair et al. (2001 ); El-Agrody et al. (2000 , 2002 ). For the chemical and pharmacological properties of 4H-chromene and fused 4H-chromene derivatives, see: El-Agrody et al. (2000); Abd-El-Aziz et al. (2004 , 2007 ); Sabry et al. (2011 ). For ring puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₁H₁₅FN₂O₂
M_r = 346.35
Monoclinic, P 2₁ /c
a = 12.6336 (4) Å
b = 11.9333 (3) Å
c = 12.0471 (4) Å
β = 113.581 (2)°
V = 1664.56 (9) Å³
Z = 4
Cu Kα radiation
μ = 0.81 mm⁻¹
T = 296 K
0.88 × 0.68 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.537, T_max = 0.953
11390 measured reflections
3199 independent reflections
2770 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.132
S = 1.05
3199 reflections
245 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H2N1⋯N2ⁱ	0.89 (2)	2.17 (2)	3.054 (2)	175 (2)
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812023021/lh5476sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812023021/lh5476Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812023021/lh5476Isup3.cml

checkCIF report

Comment top

In our previous work, we have reported the synthesis of 4H-chromene derivatives using α-cyanocinnamonitriles and ethyl α-cyanocinnamates (Sayed et al., 2000; Bedair et al., 2001; El-Agrody et al., 2000, 2002), study of their characterization and evaluation of their antimicrobial and antitumor activities. In continuation of our interest in the chemical and pharmacological properties of 4H-chromene and fused 4H-chromene derivatives (El-Agrody et al., 2000; Abd-El-Aziz et al., 2004, 2007; Sabry et al., 2011), we report herein the crystal structure of the title compound.

The asymmetric unit of the title compound is shown in Fig. 1. The fluoro-substituted benzene ring (C14–C19) is approximately perpendicular to the 4H-benzo[h]chromene ring system [O1/C1–C13, maximum deviation = 0.109 (2) Å at atom C3] as indicated by the dihedral angle of 83.35 (7)°. The pyran ring (O1/C1–C5) adopts slight sofa conformation [puckering parameters (Cremer & Pople, 1975), Q = 0.0980 (16) Å, θ = 69.5 (9)° and ϕ = 167.7 (10)°] with C3 as the flap atom. The methoxy group (C20/O2) is slightly twisted from the attached benzene ring (C4–C6/C11–C13) of the 4H-benzo[h]chromene moiety with torsion angle C20—O2—C12—C13 of -4.3 (3)°.

In the crystal (Fig. 2), molecules are linked by intermolecular N1—H2N1···N2ⁱ hydrogen bonds (Table 1) into infinite wave-like chains along b axis. The crystal packing is further stabilized by π–π interaction with Cg1-Cg1 distance of 3.7713 (9) Å, where Cg1 is the centroid of O1/C1–C5 ring [symmetry code: 1-x, 1-y, -z].

Related literature top

For the synthesis of 4H-chromene derivatives, see: Sayed et al. (2000); Bedair et al. (2001); El-Agrody et al. (2000, 2002). For the chemical and pharmacological properties of 4H-chromene and fused 4H-chromene derivatives, see: El-Agrody et al. (2000); Abd-El-Aziz et al. (2004, 2007); Sabry et al. (2011). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

A solution of 4-methoxy-1-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 (reaction time: 60 min). The solid product formed was collected by filtration and recrystallized from ethanol to give the title compound. M.p.: 493–494 K.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. The dashed lines represent the hydrogen bonds. For clarity, hydrogen atoms not involved in hydrogen bonding have been omitted.

2-Amino-4-(4-fluorophenyl)-6-methoxy-4H-benzo[h]chromene- 3-carbonitrile top

Crystal data top

C₂₁H₁₅FN₂O₂	F(000) = 720
M_r = 346.35	D_x = 1.382 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 3014 reflections
a = 12.6336 (4) Å	θ = 3.8–71.5°
b = 11.9333 (3) Å	µ = 0.81 mm⁻¹
c = 12.0471 (4) Å	T = 296 K
β = 113.581 (2)°	Plate, yellow
V = 1664.56 (9) Å³	0.88 × 0.68 × 0.06 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3199 independent reflections
Radiation source: fine-focus sealed tube	2770 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 71.9°, θ_min = 3.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
T_min = 0.537, T_max = 0.953	k = −12→14
11390 measured reflections	l = −12→14

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)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.132	w = 1/[σ²(F_o²) + (0.0702P)² + 0.3162P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3199 reflections	Δρ_max = 0.22 e Å⁻³
245 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0030 (5)

Crystal data top

C₂₁H₁₅FN₂O₂	V = 1664.56 (9) Å³
M_r = 346.35	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 12.6336 (4) Å	µ = 0.81 mm⁻¹
b = 11.9333 (3) Å	T = 296 K
c = 12.0471 (4) Å	0.88 × 0.68 × 0.06 mm
β = 113.581 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3199 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2770 reflections with I > 2σ(I)
T_min = 0.537, T_max = 0.953	R_int = 0.035
11390 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.22 e Å⁻³
3199 reflections	Δρ_min = −0.21 e Å⁻³
245 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	1.08340 (11)	0.92571 (13)	0.19221 (15)	0.0946 (5)
O1	0.59888 (10)	0.46944 (9)	0.14761 (10)	0.0507 (3)
O2	0.85128 (13)	0.37355 (11)	−0.12356 (13)	0.0677 (4)
N1	0.52279 (14)	0.57508 (14)	0.24812 (14)	0.0569 (4)
N2	0.58458 (15)	0.85793 (13)	0.21110 (16)	0.0666 (4)
C1	0.58225 (13)	0.57477 (13)	0.17674 (13)	0.0442 (3)
C2	0.62297 (13)	0.66625 (13)	0.13969 (13)	0.0439 (3)
C3	0.68193 (12)	0.66037 (12)	0.05215 (13)	0.0416 (3)
H3A	0.6274	0.6888	−0.0262	0.050*
C4	0.70666 (12)	0.53883 (12)	0.03481 (12)	0.0412 (3)
C5	0.66493 (12)	0.45325 (12)	0.07952 (13)	0.0422 (3)
C6	0.68132 (12)	0.33927 (13)	0.05802 (13)	0.0437 (3)
C7	0.63629 (15)	0.24988 (14)	0.10278 (16)	0.0541 (4)
H7A	0.5972	0.2650	0.1522	0.065*
C8	0.64953 (19)	0.14210 (15)	0.07431 (19)	0.0656 (5)
H8A	0.6191	0.0841	0.1040	0.079*
C9	0.70845 (18)	0.11761 (15)	0.00090 (19)	0.0683 (5)
H9A	0.7161	0.0435	−0.0187	0.082*
C10	0.75491 (17)	0.20137 (15)	−0.04230 (17)	0.0592 (4)
H10A	0.7947	0.1839	−0.0904	0.071*
C11	0.74309 (13)	0.31434 (13)	−0.01470 (14)	0.0466 (4)
C12	0.78985 (14)	0.40492 (14)	−0.05799 (14)	0.0490 (4)
C13	0.77181 (13)	0.51312 (13)	−0.03431 (14)	0.0469 (4)
H13A	0.8026	0.5710	−0.0638	0.056*
C14	0.79036 (13)	0.73268 (12)	0.09176 (13)	0.0433 (3)
C15	0.80585 (16)	0.80610 (15)	0.01145 (16)	0.0573 (4)
H15A	0.7487	0.8125	−0.0664	0.069*
C16	0.90543 (18)	0.87111 (17)	0.04453 (19)	0.0682 (5)
H16A	0.9157	0.9203	−0.0102	0.082*
C17	0.98691 (16)	0.86051 (16)	0.15903 (19)	0.0629 (5)
C18	0.97531 (16)	0.78960 (18)	0.24158 (19)	0.0675 (5)
H18A	1.0327	0.7844	0.3194	0.081*
C19	0.87556 (15)	0.72490 (15)	0.20702 (16)	0.0567 (4)
H19A	0.8663	0.6758	0.2624	0.068*
C20	0.8921 (2)	0.46109 (19)	−0.1767 (2)	0.0726 (6)
H20A	0.9294	0.4291	−0.2248	0.109*
H20B	0.9463	0.5066	−0.1139	0.109*
H20C	0.8282	0.5064	−0.2271	0.109*
C21	0.60126 (14)	0.77220 (13)	0.17819 (14)	0.0479 (4)
H2N1	0.4932 (18)	0.510 (2)	0.2566 (19)	0.065 (6)*
H1N1	0.4912 (19)	0.642 (2)	0.251 (2)	0.073 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0660 (7)	0.0911 (9)	0.1290 (11)	−0.0335 (7)	0.0416 (7)	−0.0317 (8)
O1	0.0622 (7)	0.0378 (6)	0.0650 (7)	−0.0010 (5)	0.0391 (5)	−0.0020 (5)
O2	0.0845 (9)	0.0567 (8)	0.0838 (9)	0.0070 (6)	0.0566 (7)	−0.0061 (6)
N1	0.0703 (9)	0.0447 (8)	0.0724 (9)	−0.0022 (7)	0.0461 (8)	−0.0035 (7)
N2	0.0771 (10)	0.0491 (9)	0.0787 (10)	0.0032 (7)	0.0364 (8)	−0.0149 (7)
C1	0.0464 (7)	0.0404 (8)	0.0472 (8)	0.0021 (6)	0.0202 (6)	−0.0029 (6)
C2	0.0450 (7)	0.0399 (8)	0.0486 (8)	0.0018 (6)	0.0206 (6)	−0.0025 (6)
C3	0.0441 (7)	0.0378 (7)	0.0420 (7)	0.0014 (6)	0.0162 (6)	0.0007 (6)
C4	0.0429 (7)	0.0383 (7)	0.0411 (7)	0.0010 (5)	0.0155 (6)	−0.0019 (6)
C5	0.0444 (7)	0.0390 (7)	0.0440 (7)	0.0017 (6)	0.0185 (6)	−0.0025 (6)
C6	0.0433 (7)	0.0392 (8)	0.0443 (7)	0.0030 (6)	0.0131 (6)	−0.0014 (6)
C7	0.0605 (9)	0.0427 (8)	0.0615 (9)	0.0019 (7)	0.0269 (8)	0.0031 (7)
C8	0.0794 (12)	0.0396 (9)	0.0821 (12)	0.0006 (8)	0.0366 (10)	0.0040 (8)
C9	0.0804 (13)	0.0379 (9)	0.0857 (13)	0.0083 (8)	0.0322 (10)	−0.0052 (9)
C10	0.0653 (10)	0.0477 (9)	0.0664 (10)	0.0085 (8)	0.0283 (8)	−0.0084 (8)
C11	0.0460 (8)	0.0428 (8)	0.0471 (8)	0.0058 (6)	0.0146 (6)	−0.0042 (6)
C12	0.0494 (8)	0.0503 (9)	0.0499 (8)	0.0046 (7)	0.0227 (6)	−0.0053 (7)
C13	0.0506 (8)	0.0447 (8)	0.0488 (8)	−0.0014 (6)	0.0234 (6)	−0.0021 (6)
C14	0.0455 (7)	0.0367 (7)	0.0509 (8)	0.0004 (6)	0.0227 (6)	−0.0051 (6)
C15	0.0639 (10)	0.0539 (10)	0.0538 (9)	−0.0093 (8)	0.0232 (8)	0.0002 (7)
C16	0.0781 (13)	0.0595 (11)	0.0786 (12)	−0.0178 (9)	0.0434 (11)	−0.0029 (9)
C17	0.0534 (9)	0.0539 (10)	0.0883 (13)	−0.0127 (8)	0.0357 (9)	−0.0207 (9)
C18	0.0507 (10)	0.0709 (12)	0.0684 (11)	−0.0004 (8)	0.0107 (8)	−0.0124 (9)
C19	0.0566 (9)	0.0543 (10)	0.0550 (9)	−0.0006 (7)	0.0180 (7)	0.0028 (7)
C20	0.0858 (14)	0.0711 (13)	0.0848 (13)	−0.0002 (10)	0.0591 (12)	−0.0052 (10)
C21	0.0510 (8)	0.0442 (9)	0.0516 (8)	−0.0004 (6)	0.0237 (7)	−0.0039 (7)

Geometric parameters (Å, º) top

F1—C17	1.364 (2)	C8—C9	1.396 (3)
O1—C1	1.3440 (18)	C8—H8A	0.9300
O1—C5	1.3979 (18)	C9—C10	1.364 (3)
O2—C12	1.3627 (19)	C9—H9A	0.9300
O2—C20	1.425 (2)	C10—C11	1.411 (2)
N1—C1	1.349 (2)	C10—H10A	0.9300
N1—H2N1	0.89 (2)	C11—C12	1.427 (2)
N1—H1N1	0.90 (2)	C12—C13	1.361 (2)
N2—C21	1.147 (2)	C13—H13A	0.9300
C1—C2	1.356 (2)	C14—C15	1.376 (2)
C2—C21	1.411 (2)	C14—C19	1.378 (2)
C2—C3	1.517 (2)	C15—C16	1.394 (3)
C3—C4	1.516 (2)	C15—H15A	0.9300
C3—C14	1.525 (2)	C16—C17	1.357 (3)
C3—H3A	0.9800	C16—H16A	0.9300
C4—C5	1.356 (2)	C17—C18	1.358 (3)
C4—C13	1.419 (2)	C18—C19	1.392 (3)
C5—C6	1.415 (2)	C18—H18A	0.9300
C6—C7	1.413 (2)	C19—H19A	0.9300
C6—C11	1.418 (2)	C20—H20A	0.9600
C7—C8	1.359 (3)	C20—H20B	0.9600
C7—H7A	0.9300	C20—H20C	0.9600

C1—O1—C5	118.35 (12)	C9—C10—H10A	119.7
C12—O2—C20	116.83 (14)	C11—C10—H10A	119.7
C1—N1—H2N1	115.9 (14)	C10—C11—C6	118.83 (15)
C1—N1—H1N1	113.3 (15)	C10—C11—C12	122.65 (15)
H2N1—N1—H1N1	124.2 (19)	C6—C11—C12	118.51 (14)
O1—C1—N1	110.73 (14)	C13—C12—O2	124.33 (15)
O1—C1—C2	123.18 (13)	C13—C12—C11	120.91 (14)
N1—C1—C2	126.07 (15)	O2—C12—C11	114.76 (14)
C1—C2—C21	117.63 (13)	C12—C13—C4	120.87 (15)
C1—C2—C3	123.24 (13)	C12—C13—H13A	119.6
C21—C2—C3	118.96 (13)	C4—C13—H13A	119.6
C4—C3—C2	109.01 (12)	C15—C14—C19	118.55 (15)
C4—C3—C14	112.07 (12)	C15—C14—C3	120.19 (14)
C2—C3—C14	112.70 (12)	C19—C14—C3	121.25 (14)
C4—C3—H3A	107.6	C14—C15—C16	121.29 (17)
C2—C3—H3A	107.6	C14—C15—H15A	119.4
C14—C3—H3A	107.6	C16—C15—H15A	119.4
C5—C4—C13	118.64 (14)	C17—C16—C15	118.01 (18)
C5—C4—C3	122.12 (13)	C17—C16—H16A	121.0
C13—C4—C3	119.19 (13)	C15—C16—H16A	121.0
C4—C5—O1	123.18 (13)	C16—C17—C18	122.84 (17)
C4—C5—C6	122.86 (14)	C16—C17—F1	118.04 (19)
O1—C5—C6	113.93 (13)	C18—C17—F1	119.11 (19)
C7—C6—C5	123.01 (14)	C17—C18—C19	118.47 (17)
C7—C6—C11	118.83 (14)	C17—C18—H18A	120.8
C5—C6—C11	118.13 (14)	C19—C18—H18A	120.8
C8—C7—C6	120.61 (17)	C14—C19—C18	120.84 (17)
C8—C7—H7A	119.7	C14—C19—H19A	119.6
C6—C7—H7A	119.7	C18—C19—H19A	119.6
C7—C8—C9	120.59 (18)	O2—C20—H20A	109.5
C7—C8—H8A	119.7	O2—C20—H20B	109.5
C9—C8—H8A	119.7	H20A—C20—H20B	109.5
C10—C9—C8	120.56 (16)	O2—C20—H20C	109.5
C10—C9—H9A	119.7	H20A—C20—H20C	109.5
C8—C9—H9A	119.7	H20B—C20—H20C	109.5
C9—C10—C11	120.55 (17)	N2—C21—C2	179.06 (19)

C5—O1—C1—N1	−176.40 (13)	C9—C10—C11—C12	−179.82 (17)
C5—O1—C1—C2	2.4 (2)	C7—C6—C11—C10	1.6 (2)
O1—C1—C2—C21	−178.96 (14)	C5—C6—C11—C10	−176.68 (14)
N1—C1—C2—C21	−0.3 (2)	C7—C6—C11—C12	−179.03 (14)
O1—C1—C2—C3	5.8 (2)	C5—C6—C11—C12	2.7 (2)
N1—C1—C2—C3	−175.55 (15)	C20—O2—C12—C13	−4.3 (3)
C1—C2—C3—C4	−10.64 (19)	C20—O2—C12—C11	175.28 (16)
C21—C2—C3—C4	174.21 (13)	C10—C11—C12—C13	176.76 (16)
C1—C2—C3—C14	−135.72 (15)	C6—C11—C12—C13	−2.6 (2)
C21—C2—C3—C14	49.13 (18)	C10—C11—C12—O2	−2.8 (2)
C2—C3—C4—C5	8.57 (19)	C6—C11—C12—O2	177.82 (14)
C14—C3—C4—C5	134.03 (14)	O2—C12—C13—C4	179.97 (14)
C2—C3—C4—C13	−173.90 (12)	C11—C12—C13—C4	0.4 (2)
C14—C3—C4—C13	−48.44 (17)	C5—C4—C13—C12	1.6 (2)
C13—C4—C5—O1	−179.35 (13)	C3—C4—C13—C12	−176.02 (14)
C3—C4—C5—O1	−1.8 (2)	C4—C3—C14—C15	106.56 (16)
C13—C4—C5—C6	−1.4 (2)	C2—C3—C14—C15	−130.03 (15)
C3—C4—C5—C6	176.10 (13)	C4—C3—C14—C19	−72.26 (18)
C1—O1—C5—C4	−4.4 (2)	C2—C3—C14—C19	51.14 (19)
C1—O1—C5—C6	177.49 (12)	C19—C14—C15—C16	0.4 (3)
C4—C5—C6—C7	−178.91 (15)	C3—C14—C15—C16	−178.43 (16)
O1—C5—C6—C7	−0.8 (2)	C14—C15—C16—C17	−0.4 (3)
C4—C5—C6—C11	−0.7 (2)	C15—C16—C17—C18	0.1 (3)
O1—C5—C6—C11	177.36 (12)	C15—C16—C17—F1	−178.75 (17)
C5—C6—C7—C8	176.61 (16)	C16—C17—C18—C19	0.1 (3)
C11—C6—C7—C8	−1.6 (2)	F1—C17—C18—C19	178.99 (16)
C6—C7—C8—C9	0.4 (3)	C15—C14—C19—C18	−0.2 (3)
C7—C8—C9—C10	0.8 (3)	C3—C14—C19—C18	178.68 (15)
C8—C9—C10—C11	−0.7 (3)	C17—C18—C19—C14	−0.1 (3)
C9—C10—C11—C6	−0.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2N1···N2ⁱ	0.89 (2)	2.17 (2)	3.054 (2)	175 (2)

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₅FN₂O₂
M_r	346.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.6336 (4), 11.9333 (3), 12.0471 (4)
β (°)	113.581 (2)
V (Å³)	1664.56 (9)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.81
Crystal size (mm)	0.88 × 0.68 × 0.06

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.537, 0.953
No. of measured, independent and observed [I > 2σ(I)] reflections	11390, 3199, 2770
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.132, 1.05
No. of reflections	3199
No. of parameters	245
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.21

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2N1···N2ⁱ	0.89 (2)	2.17 (2)	3.054 (2)	175 (2)

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of a research fellowship. The authors extend their appreciation to the Deanship of Scientific Research at King Saud University for funding the work through the research group project No. RGP-VPP-172.

References

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