3-Amino-1-(4-fluoro­phen­yl)-7-meth­oxy-1H-benzo[f]chromene-2-carbonitrile

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

doi:10.1107/S1600536813005473

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 4| April 2013| Pages o478-o479

doi:10.1107/S1600536813005473

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3-Amino-1-(4-fluorophenyl)-7-methoxy-1H-benzo[f]chromene-2-carbonitrile

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

^aDrug Exploration & Development Chair (DEDC), College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^bApplied Organic Chemistry Department, National Research Center, Dokki 12622, Cairo, Egypt, ^cChemistry Department, Faculty of Science, King Khalid University, Abha 61413, PO Box 9004, Saudi Arabia, ^dChemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, 11884, Egypt, ^ePharmaceutical Chemistry Department, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^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)

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 fluorobenzene ring is almost perpendicular to this plane [dihedral angle = 89.58 (8)°]. Zigzag supramolecular 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 [intercentroid distance for centrosymmetrically related fluorobenzene rings = 3.5181 (10) Å] and C—H⋯π interactions.

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_r = 346.35
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.052
wR(F²) = 0.145
S = 1.02
3868 reflections
244 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.16 e Å⁻³

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) -x+2, -y+2, -z+1; (ii) -x+2, -y+1, -z+1; (iii) -x+1, -y+1, -z+2.

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/S1600536813005473/hb7049sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536813005473/hb7049Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of 4H-Chromene derivatives (El-Agrody et al., 2013), the crystal and molecular structure of the title compound, (I), is described herein.

In (I), Fig. 1, the furan ring has a flattened half-chair conformation with the methine-C11 atom lying only 0.136 (2) Å above the plane of the remaining atoms (r.m.s. deviation = 0.0229 Å). In fact, 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 = 0.049 Å. The maximum deviations are 0.068 (2) Å for the aforementioned methine-C11 atom and -0.107 (2) Å for the adjacent C12 atom. The fluorobenzene ring is perpendicular to the 1H-benzo[f]chromene residue, forming a dihedral angle of 89.58 (8)°. The methoxy group is co-planar with the ring to which it is attached as manifested in the C14—O2—C7—C6 torsion angle of 177.17 (19)°. 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 8-methoxy analogue (El-Agrody et al., 2013).

In the crystal packing, zigzag tapes are formed along the b axis via an alternating sequence of 12-membered {···HNC₃N}₂, arising from amine-N—H···N(cyano) hydrogen bonds, and eight-membered {···HNCO}₂, arising from amine-N—H···O(furan) hydrogen bonds, synthons, Fig. 2 and Table 1. These are connected into a layer in the ab plane by π—π interactions occurring between centrosymmetrically related fluorobenzene rings [inter-centroid distance = 3.5181 (10) Å for symmetry operation: 1 - x, 1 - y, 1 - z]. Layers are connected along the c axis by C—H···π interactions where both the donor atom and acceptor-π system are derived from fluorobenzene rings, Fig. 3 and Table 1, highlighting the key role this residue plays in consolidating the crystal structure of (I).

Related literature top

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 top

A solution of 7-methoxy-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 (reaction time: 60 min). The solid product which formed was collected by filtration and recrystallized from ethanol to give the title compound, (I), as light-brown prisms; M.pt: 533–534 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 of the supramolecular zigzag tape along the b axis in (I). The N—H···N and N—H···O hydrogen bonds are shown as blue and orange dashed lines, respectively.
	Fig. 3. A view in projection down the a axis of the crystal packing in (I). The N—H···N, N—H···O, C—H···π and π—π interactions are shown as blue, orange, brown and purple dashed lines, respectively.

3-Amino-1-(4-fluorophenyl)-7-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 = 1.376 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

Data collection top

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	R_int = 0.029
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 3.1°
ω scan	h = −8→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −12→12
T_min = 0.821, T_max = 1.000	l = −13→14
7587 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)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.145	w = 1/[σ²(F_o²) + (0.0577P)² + 0.1106P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3868 reflections	Δρ_max = 0.19 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: 0.011 (3)

Crystal data top

C₂₁H₁₅FN₂O₂	γ = 87.083 (7)°
M_r = 346.35	V = 835.99 (13) Å³
Triclinic, P1	Z = 2
a = 8.7798 (9) Å	Mo Kα radiation
b = 9.6329 (6) Å	µ = 0.10 mm⁻¹
c = 10.9130 (11) Å	T = 295 K
α = 77.074 (7)°	0.30 × 0.30 × 0.10 mm
β = 68.414 (10)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3868 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2569 reflections with I > 2σ(I)
T_min = 0.821, T_max = 1.000	R_int = 0.029
7587 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.19 e Å⁻³
3868 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	0.2857 (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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+2, −z+1; (ii) −x+2, −y+1, −z+1; (iii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₅FN₂O₂
M_r	346.35
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	8.7798 (9), 9.6329 (6), 10.9130 (11)
α, β, γ (°)	77.074 (7), 68.414 (10), 87.083 (7)
V (Å³)	835.99 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.30 × 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	0.821, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7587, 3868, 2569
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.145, 1.02
No. of reflections	3868
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)	0.19, −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 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) −x+2, −y+2, −z+1; (ii) −x+2, −y+1, −z+1; (iii) −x+1, −y+1, −z+2.

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

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
El-Agrody, A. M., Al-Omar, M. A., Amr, A. E.-G. E., Ng, S. W. & Tiekink, E. R. T. (2013). Acta Cryst. E69, o476–o477. CSD CrossRef IUCr Journals Google Scholar
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Volume 69| Part 4| April 2013| Pages o478-o479

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