N-[3-Chloro-4-(3-fluoro­benz­yloxy)phen­yl]-6-iodo­quinazolin-4-amine

Cai, Z.-Q.; Liu, J.-G.; Zhou, W.-W.; Li, Y.-L.

doi:10.1107/S1600536810021847

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1810

doi:10.1107/S1600536810021847

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N-[3-Chloro-4-(3-fluorobenzyloxy)phenyl]-6-iodoquinazolin-4-amine

Zhi-Qiang Cai,^a Jing-Guo Liu,^a,^b Wei-Wei Zhou ^a,^b and Yi-Liang Li ^a ^*

^aTianjin Key Laboratory of Drug Design and Discovery, Tianjin Institute of Pharmaceutical Research, Tianjin 300193, People's Republic of China, and ^bFaculty of Pharmacy, GuangXi Traditional Chinese Medical University, Nanning 530001, People's Republic of China
^*Correspondence e-mail: langyil@sina.com

(Received 21 May 2010; accepted 8 June 2010; online 26 June 2010)

In the title molecule, C₂₁H₁₄ClFIN₃O, the bicyclic ring system has a twisted conformation; the two fused rings form a dihedral angle of 4.5 (1)°. The dihedral angles between the fused ring system and the benzene rings are 27.3 (6) and 5.3 (5)° while the dihedral angle between the benzene rings is 22.0 (5)°. In the crystal structure, weak intermolecular N—H⋯N hydrogen bonds link the molecules into chains propagating in [100]. A short intermolecular distance of 3.806 (3) Å between the centroids of the fluorobenzene and iodobenzene rings suggests the existence of π–π stacking interactions.

Related literature

For a related structure, see: Calestani et al. (2001 ). The title compound is an important intermediate in the synthesis of the anticancer agent lapatinib, see: Kimberly et al. (2006 ).

Experimental

Crystal data

C₂₁H₁₄ClFIN₃O
M_r = 505.70
Orthorhombic, P c a 2₁
a = 13.128 (3) Å
b = 7.6293 (15) Å
c = 18.898 (4) Å
V = 1892.8 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.86 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.06 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.707, T_max = 0.897
11905 measured reflections
3183 independent reflections
2510 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.067
S = 1.01
3183 reflections
258 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.24 e Å⁻³
Δρ_min = −0.70 e Å⁻³
Absolute structure: Flack (1983 ), 1433 Friedel pairs
Flack parameter: −0.039 (19)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H21⋯N3ⁱ	0.81 (6)	2.39 (6)	3.128 (6)	151 (6)
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+1, z]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021847/cv2724sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021847/cv2724Isup2.hkl

checkCIF report

Comment top

The title compound (I) is an important intermediate in the preparation of anticancer agent lapatinib (Kimberly et al., 2006). Herein, the synthesis and the crystal structure of (I) are reported.

In (I) (Fig. 1), all bond lengths and angles are normal and comparable with those observed in the related compound (Calestani et al., 2001). The bicycle quinazoline system has a twisted conformation - two fused rings form a dihedral angle of 4.5 (1)°. In the crystal structure, weak intermolecular N—H···N hydrogen bonds (Table 1) link molecules into chains propagated in direction [100]. Short intermolecular distance of 3.806 (3) Å between the centroids of aromatic rings suggests an existence of π-π interactions.

Related literature top

For a related structure, see: Calestani et al. (2001). The title compound is an important intermediate in the synthesis of the anticancer agent lapatinib, see: Kimberly et al. (2006).

Experimental top

2-Chloro-4-(6-iodo-quinazolin-4-ylamino)-phenol (10 mmol) in acetone (5 ml) was added to a stirred mixture of anhydrous potassium carbonate (20 mmol) and 1-Chloromethyl-3-fluoro-benzene (10 mmol) in dry acetone (25 ml). It was stirred at room temperature for 6 h. Upon completion reaction mixture was diluted with water, extracted with dichloromethane and concentrated. Recrystallization from ethyl acetate afforded title compound in 89% yield as yellow crystal: 1H NMR (DMSO-d6): 9.82 (1H, s, NH), 8.94(1H, s, ArH), 8.60(1H, s, ArH), 8.08(1H, dd, ArH), 8.01(1H, d ArH), 7.72 (1H, dd ArH), 7.49(1H, d ArH), 7.43 (1H, dd ArH), 7.19 (3H, m ArH), 7.14 (1H, t ArH), 5.24(2H, s CH2).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The structure of C₂₁H₁₄ClFIN₃O with atom-labelling scheme and ellipsoids drawn at the 50% probability level.

N-[3-Chloro-4-(3-fluorobenzyloxy)phenyl]-6-iodoquinazolin-4-amine top

Crystal data top

C₂₁H₁₄ClFIN₃O	F(000) = 992
M_r = 505.70	D_x = 1.775 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 7022 reflections
a = 13.128 (3) Å	θ = 1.1–27.9°
b = 7.6293 (15) Å	µ = 1.86 mm⁻¹
c = 18.898 (4) Å	T = 113 K
V = 1892.8 (7) Å³	Prism, colourless
Z = 4	0.20 × 0.18 × 0.06 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3183 independent reflections
Radiation source: fine-focus sealed tube	2510 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Detector resolution: 14.63 pixels mm^-1	θ_max = 25.0°, θ_min = 3.1°
ω scan	h = −15→15
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −8→9
T_min = 0.707, T_max = 0.897	l = −21→22
11905 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.030	w = 1/[σ²(F_o²) + (0.0292P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.067	(Δ/σ)_max = 0.001
S = 1.01	Δρ_max = 1.24 e Å⁻³
3183 reflections	Δρ_min = −0.70 e Å⁻³
258 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0309 (8)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1433 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.039 (19)

Crystal data top

C₂₁H₁₄ClFIN₃O	V = 1892.8 (7) Å³
M_r = 505.70	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 13.128 (3) Å	µ = 1.86 mm⁻¹
b = 7.6293 (15) Å	T = 113 K
c = 18.898 (4) Å	0.20 × 0.18 × 0.06 mm

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3183 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2510 reflections with I > 2σ(I)
T_min = 0.707, T_max = 0.897	R_int = 0.045
11905 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.067	Δρ_max = 1.24 e Å⁻³
S = 1.01	Δρ_min = −0.70 e Å⁻³
3183 reflections	Absolute structure: Flack (1983), 1433 Friedel pairs
258 parameters	Absolute structure parameter: −0.039 (19)
1 restraint

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
I1	0.299873 (18)	−0.00631 (3)	0.50844 (4)	0.01983 (11)
Cl1	0.28694 (8)	1.26802 (14)	0.25075 (8)	0.0248 (3)
F1	0.0085 (3)	1.7039 (4)	0.0746 (2)	0.0538 (10)
O1	0.0946 (2)	1.1497 (4)	0.19493 (17)	0.0220 (8)
N1	0.2954 (3)	0.6395 (5)	0.3538 (2)	0.0165 (9)
N2	0.4616 (3)	0.7425 (5)	0.3551 (2)	0.0185 (10)
N3	0.6006 (3)	0.5682 (5)	0.3991 (2)	0.0173 (9)
C1	0.0028 (5)	1.4220 (8)	0.1242 (3)	0.0289 (14)
H1	0.0727	1.4259	0.1319	0.035*
C2	−0.0476 (4)	1.5583 (9)	0.0935 (3)	0.0288 (16)
C3	−0.1501 (5)	1.5661 (7)	0.0807 (3)	0.0336 (14)
H3	−0.1804	1.6640	0.0603	0.040*
C4	−0.2058 (4)	1.4207 (7)	0.0999 (3)	0.0290 (13)
H4	−0.2756	1.4188	0.0914	0.035*
C5	−0.1602 (3)	1.2779 (6)	0.1315 (3)	0.0225 (12)
H5	−0.1995	1.1821	0.1449	0.027*
C6	−0.0549 (4)	1.2766 (6)	0.1433 (3)	0.0171 (12)
C7	−0.0070 (3)	1.1135 (6)	0.1729 (3)	0.0201 (11)
H7A	−0.0466	1.0720	0.2129	0.024*
H7B	−0.0066	1.0223	0.1371	0.024*
C8	0.1419 (4)	1.0178 (5)	0.2308 (3)	0.0177 (11)
C9	0.1065 (4)	0.8496 (6)	0.2378 (3)	0.0193 (11)
H9	0.0455	0.8177	0.2163	0.023*
C10	0.1605 (4)	0.7262 (6)	0.2767 (2)	0.0210 (12)
H10	0.1359	0.6121	0.2797	0.025*
C11	0.2503 (3)	0.7694 (6)	0.3110 (2)	0.0138 (10)
C12	0.2883 (4)	0.9387 (7)	0.3038 (3)	0.0175 (11)
H12	0.3480	0.9709	0.3268	0.021*
C13	0.2365 (4)	1.0605 (5)	0.2618 (3)	0.0168 (11)
C14	0.3949 (3)	0.6194 (6)	0.3725 (2)	0.0158 (10)
C15	0.5600 (4)	0.7107 (7)	0.3715 (3)	0.0202 (13)
H15	0.6052	0.8015	0.3620	0.024*
C16	0.5303 (4)	0.4390 (8)	0.4183 (3)	0.0164 (13)
C17	0.5680 (4)	0.2842 (6)	0.4475 (3)	0.0209 (12)
H17	0.6380	0.2679	0.4516	0.025*
C18	0.5028 (3)	0.1559 (6)	0.4703 (2)	0.0179 (10)
H18	0.5282	0.0517	0.4887	0.022*
C19	0.3977 (3)	0.1828 (5)	0.4656 (2)	0.0156 (10)
C20	0.3593 (3)	0.3317 (5)	0.4348 (3)	0.0170 (11)
H20	0.2893	0.3468	0.4307	0.020*
C21	0.4254 (4)	0.4606 (6)	0.4094 (3)	0.0158 (11)
H21	0.260 (5)	0.555 (7)	0.363 (4)	0.05 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.01930 (17)	0.01590 (15)	0.02429 (18)	−0.00277 (13)	0.0006 (2)	0.00282 (15)
Cl1	0.0276 (6)	0.0170 (6)	0.0299 (8)	−0.0025 (5)	−0.0030 (7)	0.0048 (5)
F1	0.065 (2)	0.034 (2)	0.062 (3)	−0.0141 (18)	−0.011 (2)	0.0118 (17)
O1	0.0168 (18)	0.0207 (18)	0.029 (2)	0.0031 (15)	−0.0055 (17)	0.0074 (15)
N1	0.013 (2)	0.014 (2)	0.022 (3)	−0.0002 (18)	0.0021 (18)	0.0039 (17)
N2	0.013 (2)	0.021 (2)	0.021 (3)	0.0003 (17)	0.0004 (17)	0.0033 (18)
N3	0.014 (2)	0.017 (2)	0.021 (3)	0.002 (2)	0.002 (2)	0.0030 (18)
C1	0.028 (3)	0.025 (3)	0.034 (4)	0.002 (3)	0.000 (3)	0.001 (3)
C2	0.046 (5)	0.022 (3)	0.019 (4)	−0.009 (3)	−0.007 (3)	0.001 (3)
C3	0.052 (4)	0.027 (3)	0.022 (3)	0.024 (3)	−0.013 (3)	−0.006 (2)
C4	0.035 (3)	0.033 (3)	0.019 (3)	0.010 (3)	−0.004 (2)	−0.005 (2)
C5	0.021 (3)	0.027 (3)	0.018 (3)	0.004 (2)	−0.005 (2)	0.001 (2)
C6	0.024 (3)	0.017 (3)	0.010 (3)	0.003 (2)	−0.003 (2)	0.004 (2)
C7	0.018 (3)	0.021 (3)	0.022 (3)	−0.001 (2)	−0.001 (2)	0.003 (2)
C8	0.015 (3)	0.022 (3)	0.016 (3)	0.008 (2)	0.002 (2)	0.005 (2)
C9	0.015 (2)	0.022 (3)	0.021 (3)	−0.003 (2)	−0.003 (2)	−0.002 (2)
C10	0.030 (3)	0.013 (2)	0.021 (3)	0.001 (2)	0.002 (2)	0.0024 (19)
C11	0.014 (2)	0.016 (2)	0.012 (3)	0.004 (2)	0.000 (2)	0.0000 (18)
C12	0.012 (3)	0.028 (3)	0.013 (3)	0.005 (2)	0.001 (2)	−0.002 (2)
C13	0.017 (3)	0.0134 (19)	0.020 (3)	−0.004 (2)	0.004 (2)	0.001 (3)
C14	0.013 (2)	0.017 (2)	0.017 (3)	0.002 (2)	0.001 (2)	−0.0035 (19)
C15	0.015 (3)	0.019 (3)	0.027 (4)	−0.003 (2)	0.005 (2)	0.004 (2)
C16	0.018 (3)	0.012 (3)	0.019 (4)	0.002 (2)	0.007 (2)	0.002 (2)
C17	0.019 (3)	0.021 (3)	0.022 (3)	0.003 (2)	0.000 (2)	−0.001 (2)
C18	0.020 (3)	0.015 (2)	0.019 (3)	0.005 (2)	−0.001 (2)	0.003 (2)
C19	0.017 (3)	0.014 (2)	0.016 (3)	−0.004 (2)	0.001 (2)	0.0003 (19)
C20	0.015 (3)	0.022 (3)	0.015 (3)	0.000 (2)	−0.003 (2)	−0.003 (2)
C21	0.013 (3)	0.019 (3)	0.016 (3)	−0.003 (2)	−0.001 (2)	0.0007 (19)

Geometric parameters (Å, º) top

I1—C19	2.094 (4)	C7—H7A	0.9700
Cl1—C13	1.729 (4)	C7—H7B	0.9700
F1—C2	1.380 (7)	C8—C9	1.372 (6)
O1—C8	1.363 (5)	C8—C13	1.411 (8)
O1—C7	1.425 (5)	C9—C10	1.389 (6)
N1—C14	1.362 (5)	C9—H9	0.9300
N1—C11	1.408 (6)	C10—C11	1.386 (6)
N1—H21	0.81 (6)	C10—H10	0.9300
N2—C14	1.326 (6)	C11—C12	1.392 (7)
N2—C15	1.350 (6)	C12—C13	1.398 (8)
N3—C15	1.318 (6)	C12—H12	0.9300
N3—C16	1.399 (7)	C14—C21	1.454 (7)
C1—C2	1.363 (9)	C15—H15	0.9300
C1—C6	1.391 (7)	C16—C17	1.395 (7)
C1—H1	0.9300	C16—C21	1.397 (7)
C2—C3	1.368 (8)	C17—C18	1.370 (6)
C3—C4	1.377 (9)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.398 (6)
C4—C5	1.380 (7)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.373 (6)
C5—C6	1.400 (6)	C20—C21	1.396 (7)
C5—H5	0.9300	C20—H20	0.9300
C6—C7	1.502 (6)

C8—O1—C7	115.4 (4)	C11—C10—C9	121.4 (4)
C14—N1—C11	129.1 (4)	C11—C10—H10	119.3
C14—N1—H21	114 (5)	C9—C10—H10	119.3
C11—N1—H21	116 (5)	C10—C11—C12	118.6 (4)
C14—N2—C15	116.6 (4)	C10—C11—N1	117.3 (4)
C15—N3—C16	114.6 (4)	C12—C11—N1	124.0 (4)
C2—C1—C6	117.0 (6)	C11—C12—C13	119.9 (5)
C2—C1—H1	121.5	C11—C12—H12	120.0
C6—C1—H1	121.5	C13—C12—H12	120.0
C1—C2—C3	125.9 (6)	C12—C13—C8	120.7 (4)
C1—C2—F1	117.7 (5)	C12—C13—Cl1	119.4 (4)
C3—C2—F1	116.4 (6)	C8—C13—Cl1	119.9 (4)
C2—C3—C4	116.2 (6)	N2—C14—N1	119.3 (4)
C2—C3—H3	121.9	N2—C14—C21	121.8 (4)
C4—C3—H3	121.9	N1—C14—C21	118.9 (4)
C3—C4—C5	121.3 (5)	N3—C15—N2	128.8 (5)
C3—C4—H4	119.4	N3—C15—H15	115.6
C5—C4—H4	119.4	N2—C15—H15	115.6
C4—C5—C6	120.2 (5)	C17—C16—C21	119.8 (5)
C4—C5—H5	119.9	C17—C16—N3	117.7 (5)
C6—C5—H5	119.9	C21—C16—N3	122.4 (5)
C1—C6—C5	119.4 (5)	C18—C17—C16	120.5 (5)
C1—C6—C7	122.0 (5)	C18—C17—H17	119.8
C5—C6—C7	118.5 (4)	C16—C17—H17	119.8
O1—C7—C6	109.9 (4)	C17—C18—C19	119.5 (4)
O1—C7—H7A	109.7	C17—C18—H18	120.2
C6—C7—H7A	109.7	C19—C18—H18	120.2
O1—C7—H7B	109.7	C20—C19—C18	120.7 (4)
C6—C7—H7B	109.7	C20—C19—I1	120.6 (3)
H7A—C7—H7B	108.2	C18—C19—I1	118.7 (3)
O1—C8—C9	125.8 (5)	C19—C20—C21	120.1 (4)
O1—C8—C13	115.9 (4)	C19—C20—H20	120.0
C9—C8—C13	118.3 (4)	C21—C20—H20	120.0
C8—C9—C10	120.8 (5)	C20—C21—C16	119.2 (5)
C8—C9—H9	119.6	C20—C21—C14	125.4 (4)
C10—C9—H9	119.6	C16—C21—C14	115.3 (5)

C6—C1—C2—C3	1.0 (10)	O1—C8—C13—Cl1	−1.9 (7)
C6—C1—C2—F1	179.6 (5)	C9—C8—C13—Cl1	177.0 (4)
C1—C2—C3—C4	−1.1 (10)	C15—N2—C14—N1	−176.3 (5)
F1—C2—C3—C4	−179.8 (5)	C15—N2—C14—C21	1.9 (7)
C2—C3—C4—C5	1.3 (8)	C11—N1—C14—N2	6.6 (7)
C3—C4—C5—C6	−1.4 (8)	C11—N1—C14—C21	−171.6 (5)
C2—C1—C6—C5	−1.0 (8)	C16—N3—C15—N2	−5.0 (8)
C2—C1—C6—C7	175.8 (5)	C14—N2—C15—N3	4.3 (8)
C4—C5—C6—C1	1.2 (8)	C15—N3—C16—C17	179.7 (5)
C4—C5—C6—C7	−175.6 (5)	C15—N3—C16—C21	−0.6 (8)
C8—O1—C7—C6	172.2 (4)	C21—C16—C17—C18	−2.7 (8)
C1—C6—C7—O1	15.5 (7)	N3—C16—C17—C18	177.1 (5)
C5—C6—C7—O1	−167.8 (4)	C16—C17—C18—C19	−1.6 (7)
C7—O1—C8—C9	10.2 (7)	C17—C18—C19—C20	3.9 (7)
C7—O1—C8—C13	−171.0 (4)	C17—C18—C19—I1	−175.0 (4)
O1—C8—C9—C10	−178.9 (4)	C18—C19—C20—C21	−1.8 (7)
C13—C8—C9—C10	2.3 (8)	I1—C19—C20—C21	177.0 (4)
C8—C9—C10—C11	1.7 (7)	C19—C20—C21—C16	−2.5 (8)
C9—C10—C11—C12	−2.5 (7)	C19—C20—C21—C14	176.7 (5)
C9—C10—C11—N1	175.0 (4)	C17—C16—C21—C20	4.7 (8)
C14—N1—C11—C10	154.4 (5)	N3—C16—C21—C20	−175.1 (5)
C14—N1—C11—C12	−28.3 (8)	C17—C16—C21—C14	−174.5 (5)
C10—C11—C12—C13	−0.7 (7)	N3—C16—C21—C14	5.7 (8)
N1—C11—C12—C13	−178.0 (5)	N2—C14—C21—C20	174.4 (5)
C11—C12—C13—C8	4.7 (8)	N1—C14—C21—C20	−7.4 (8)
C11—C12—C13—Cl1	−177.7 (4)	N2—C14—C21—C16	−6.4 (7)
O1—C8—C13—C12	175.6 (5)	N1—C14—C21—C16	171.8 (5)
C9—C8—C13—C12	−5.5 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H21···N3ⁱ	0.81 (6)	2.39 (6)	3.128 (6)	151 (6)

Symmetry code: (i) x−1/2, −y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₄ClFIN₃O
M_r	505.70
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	113
a, b, c (Å)	13.128 (3), 7.6293 (15), 18.898 (4)
V (Å³)	1892.8 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.86
Crystal size (mm)	0.20 × 0.18 × 0.06

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.707, 0.897
No. of measured, independent and observed [I > 2σ(I)] reflections	11905, 3183, 2510
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.067, 1.01
No. of reflections	3183
No. of parameters	258
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.24, −0.70
Absolute structure	Flack (1983), 1433 Friedel pairs
Absolute structure parameter	−0.039 (19)

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H21···N3ⁱ	0.81 (6)	2.39 (6)	3.128 (6)	151 (6)

Symmetry code: (i) x−1/2, −y+1, z.

Acknowledgements

The authors thank the State Key Laboratory of Elemento-organic Chemistry, Nankai University, for the X-ray data collection.

References

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