3,3-Dieth­oxy-5-fluoro-2,3-dihydro-1H-indol-2-one

Bari, A.; Al-Obaid, A.M.; Saeed, A.S.; Ng, S.W.

doi:10.1107/S1600536812001857

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o487

doi:10.1107/S1600536812001857

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3,3-Diethoxy-5-fluoro-2,3-dihydro-1H-indol-2-one

Ahmed Bari,^a Abdulrahman M. Al-Obaid,^a Ali Syed Saeed ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 8 January 2012; accepted 15 January 2012; online 21 January 2012)

The title ketal, C₁₂H₁₄FNO₃, crystallized with two independent molecules in the asymmetric unit. In each molecule the fused ring system is essentially planar [maximum deviations of 0.0169 (11) and 0.0402 (13) Å]. The molecules are each hydrogen bonded across a center of inversion into a dimer; adjacent dimers are linked by another N—H⋯O hydrogen bond, forming a chain running along [100].

Related literature

For 3,3-dimethoxyindolin-2-one, see: De & Kitagawa (1991 ).

Experimental

Crystal data

C₁₂H₁₄FNO₃
M_r = 239.24
Triclinic, $[P \overline 1]$
a = 9.3218 (6) Å
b = 9.4320 (5) Å
c = 14.1544 (8) Å
α = 100.475 (5)°
β = 104.453 (5)°
γ = 90.238 (5)°
V = 1183.43 (12) Å³
Z = 4
Cu Kα radiation
μ = 0.90 mm⁻¹
T = 100 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 = 0.773, T_max = 0.915
8022 measured reflections
4661 independent reflections
4067 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.100
S = 1.04
4661 reflections
315 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4	0.85 (2)	2.30 (2)	3.010 (2)	142 (2)
N1—H1⋯O1ⁱ	0.85 (2)	2.34 (2)	3.043 (1)	141 (2)
N2—H2⋯O1ⁱⁱ	0.87 (2)	2.28 (2)	3.002 (2)	140 (2)
N2—H2⋯O4ⁱⁱⁱ	0.87 (2)	2.33 (2)	3.057 (2)	142 (2)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x-1, y, z; (iii) -x+1, -y+1, -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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812001857/xu5445sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812001857/xu5445Isup2.hkl

checkCIF report

Comment top

The parent compound, isatin, forms a ketal, 3,3-dimethoxyindolin-2-one (De & Kitagawa, 1991). The present compound, which has a fluorine atom in the ring, is expected to possess improved pharmaceutical activity. Fluorine-substituted C₁₂H₁₄FNO₃ (Scheme I) exists as two independent molecules (Fig. 1) whose fused-rings are both planar. The molecules are each hydrogen-bonded across a center-of-inversion into a dimer; adjacent dimers are linked by another N–H···O hydrogen bond to form a chain running along [1 0 0] (Table 1).

Related literature top

For 3,3-dimethoxyindolin-2-one, see: De & Kitagawa (1991).

Experimental top

5-Fluoroisatin (1 mol) was heated under reflux for 3 h in ethanol (20 ml) in the presence of few drops of glacial acetic acid. The solvent was removed under reduced pressure and the product was crystallized from ethanol to yield the title compound (C₁₂H₁₄FNO₃) as light brown crystals.

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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the two molecules of C₁₂H₁₄FNO₃ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

3,3-Diethoxy-5-fluoro-2,3-dihydro-1H-indol-2-one top

Crystal data top

C₁₂H₁₄FNO₃	Z = 4
M_r = 239.24	F(000) = 504
Triclinic, P1	D_x = 1.343 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 9.3218 (6) Å	Cell parameters from 3789 reflections
b = 9.4320 (5) Å	θ = 3.3–74.1°
c = 14.1544 (8) Å	µ = 0.90 mm⁻¹
α = 100.475 (5)°	T = 100 K
β = 104.453 (5)°	Prism, light brown
γ = 90.238 (5)°	0.30 × 0.20 × 0.10 mm
V = 1183.43 (12) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4661 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	4067 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.018
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.3°, θ_min = 3.3°
ω scan	h = −11→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −11→10
T_min = 0.773, T_max = 0.915	l = −16→17
8022 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0505P)² + 0.3265P] where P = (F_o² + 2F_c²)/3
4661 reflections	(Δ/σ)_max = 0.001
315 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₂H₁₄FNO₃	γ = 90.238 (5)°
M_r = 239.24	V = 1183.43 (12) Å³
Triclinic, P1	Z = 4
a = 9.3218 (6) Å	Cu Kα radiation
b = 9.4320 (5) Å	µ = 0.90 mm⁻¹
c = 14.1544 (8) Å	T = 100 K
α = 100.475 (5)°	0.30 × 0.20 × 0.10 mm
β = 104.453 (5)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4661 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	4067 reflections with I > 2σ(I)
T_min = 0.773, T_max = 0.915	R_int = 0.018
8022 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.26 e Å⁻³
4661 reflections	Δρ_min = −0.23 e Å⁻³
315 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
F1	0.65631 (10)	0.87322 (9)	0.07446 (6)	0.0377 (2)
F2	0.13605 (10)	−0.08585 (10)	0.06203 (8)	0.0442 (2)
O1	1.11315 (10)	0.49565 (10)	0.42494 (7)	0.0253 (2)
O2	1.15077 (10)	0.75706 (10)	0.32386 (7)	0.0233 (2)
O3	1.10671 (10)	0.52344 (9)	0.22746 (6)	0.0221 (2)
O4	0.61151 (10)	0.46293 (10)	0.42320 (7)	0.0253 (2)
O5	0.60229 (10)	0.32961 (9)	0.22563 (6)	0.0223 (2)
O6	0.64294 (10)	0.14599 (10)	0.31984 (7)	0.0244 (2)
N1	0.87973 (12)	0.57806 (12)	0.37342 (8)	0.0241 (2)
H1	0.838 (2)	0.544 (2)	0.4122 (14)	0.040 (5)*
N2	0.37762 (13)	0.35119 (12)	0.37406 (9)	0.0253 (2)
H2	0.3385 (19)	0.410 (2)	0.4141 (14)	0.037 (5)*
C1	0.80501 (14)	0.65008 (13)	0.29789 (10)	0.0234 (3)
C2	0.65810 (15)	0.68508 (15)	0.27701 (12)	0.0307 (3)
H2A	0.5932	0.6589	0.3139	0.037*
C3	0.60863 (16)	0.76044 (16)	0.19961 (12)	0.0336 (3)
H3	0.5084	0.7864	0.1825	0.040*
C4	0.70630 (16)	0.79666 (15)	0.14840 (10)	0.0290 (3)
C5	0.85398 (15)	0.76166 (14)	0.16810 (9)	0.0243 (3)
H5	0.9187	0.7882	0.1312	0.029*
C6	0.90179 (14)	0.68592 (13)	0.24451 (9)	0.0211 (3)
C7	1.05296 (14)	0.63435 (13)	0.28796 (9)	0.0200 (3)
C8	1.02300 (14)	0.56035 (13)	0.37198 (9)	0.0210 (3)
C9	1.30237 (15)	0.73120 (17)	0.37099 (11)	0.0310 (3)
H9A	1.3449	0.6631	0.3246	0.037*
H9B	1.3064	0.6893	0.4308	0.037*
C10	1.38741 (17)	0.87367 (18)	0.39909 (14)	0.0429 (4)
H10A	1.4911	0.8606	0.4316	0.064*
H10B	1.3441	0.9401	0.4449	0.064*
H10C	1.3828	0.9138	0.3393	0.064*
C11	1.13018 (16)	0.55704 (15)	0.13718 (10)	0.0278 (3)
H11A	1.1812	0.6536	0.1504	0.033*
H11B	1.0341	0.5572	0.0877	0.033*
C12	1.22457 (18)	0.44256 (17)	0.09873 (11)	0.0343 (3)
H12A	1.2436	0.4623	0.0372	0.051*
H12B	1.1725	0.3477	0.0854	0.051*
H12C	1.3190	0.4432	0.1485	0.051*
C13	0.29953 (15)	0.24155 (14)	0.29679 (10)	0.0251 (3)
C14	0.15128 (16)	0.19850 (16)	0.27473 (12)	0.0335 (3)
H14	0.0885	0.2433	0.3136	0.040*
C15	0.09679 (16)	0.08786 (16)	0.19405 (13)	0.0376 (4)
H15	−0.0049	0.0563	0.1762	0.045*
C16	0.19158 (16)	0.02415 (15)	0.14008 (12)	0.0329 (3)
C17	0.34117 (15)	0.06529 (14)	0.16144 (11)	0.0269 (3)
H17	0.4041	0.0188	0.1233	0.032*
C18	0.39400 (14)	0.17753 (13)	0.24116 (10)	0.0227 (3)
C19	0.54709 (14)	0.25080 (13)	0.28508 (9)	0.0208 (3)
C20	0.52002 (14)	0.36945 (14)	0.37073 (9)	0.0215 (3)
C21	0.62215 (17)	0.24781 (15)	0.13397 (10)	0.0303 (3)
H21A	0.5248	0.2208	0.0857	0.036*
H21B	0.6731	0.1584	0.1459	0.036*
C22	0.7143 (2)	0.34170 (18)	0.09427 (13)	0.0470 (5)
H22A	0.7305	0.2890	0.0318	0.071*
H22B	0.8101	0.3680	0.1427	0.071*
H22C	0.6624	0.4294	0.0824	0.071*
C23	0.79515 (15)	0.19686 (16)	0.36725 (11)	0.0313 (3)
H23A	0.7992	0.2752	0.4250	0.038*
H23B	0.8400	0.2349	0.3199	0.038*
C24	0.87762 (17)	0.07179 (18)	0.40046 (12)	0.0370 (3)
H24A	0.9812	0.1032	0.4336	0.055*
H24B	0.8740	−0.0045	0.3427	0.055*
H24C	0.8318	0.0346	0.4469	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0425 (5)	0.0345 (5)	0.0326 (5)	0.0107 (4)	−0.0018 (4)	0.0134 (4)
F2	0.0342 (5)	0.0300 (5)	0.0570 (6)	−0.0055 (4)	0.0041 (4)	−0.0101 (4)
O1	0.0267 (5)	0.0309 (5)	0.0204 (4)	0.0060 (4)	0.0067 (4)	0.0089 (4)
O2	0.0220 (5)	0.0228 (4)	0.0236 (4)	−0.0025 (3)	0.0037 (4)	0.0036 (4)
O3	0.0279 (5)	0.0230 (4)	0.0174 (4)	0.0047 (4)	0.0085 (3)	0.0049 (3)
O4	0.0269 (5)	0.0275 (5)	0.0203 (4)	0.0006 (4)	0.0056 (4)	0.0019 (4)
O5	0.0273 (5)	0.0219 (4)	0.0191 (4)	0.0002 (3)	0.0088 (3)	0.0033 (3)
O6	0.0222 (5)	0.0231 (5)	0.0284 (5)	0.0053 (4)	0.0053 (4)	0.0076 (4)
N1	0.0245 (6)	0.0258 (6)	0.0255 (6)	0.0037 (4)	0.0105 (5)	0.0084 (4)
N2	0.0263 (6)	0.0246 (6)	0.0273 (6)	0.0024 (4)	0.0121 (5)	0.0035 (5)
C1	0.0248 (6)	0.0194 (6)	0.0256 (6)	0.0021 (5)	0.0058 (5)	0.0040 (5)
C2	0.0252 (7)	0.0271 (7)	0.0417 (8)	0.0041 (5)	0.0104 (6)	0.0089 (6)
C3	0.0258 (7)	0.0292 (7)	0.0430 (8)	0.0060 (6)	0.0028 (6)	0.0076 (6)
C4	0.0342 (7)	0.0222 (6)	0.0264 (7)	0.0051 (5)	−0.0012 (5)	0.0064 (5)
C5	0.0296 (7)	0.0203 (6)	0.0211 (6)	0.0006 (5)	0.0038 (5)	0.0030 (5)
C6	0.0227 (6)	0.0184 (6)	0.0199 (6)	0.0008 (5)	0.0030 (5)	0.0012 (5)
C7	0.0222 (6)	0.0203 (6)	0.0168 (6)	0.0003 (5)	0.0048 (5)	0.0022 (5)
C8	0.0242 (6)	0.0208 (6)	0.0177 (6)	0.0007 (5)	0.0062 (5)	0.0013 (5)
C9	0.0219 (7)	0.0384 (8)	0.0309 (7)	−0.0031 (6)	0.0012 (5)	0.0097 (6)
C10	0.0292 (8)	0.0405 (9)	0.0497 (10)	−0.0086 (7)	0.0063 (7)	−0.0099 (7)
C11	0.0370 (7)	0.0313 (7)	0.0189 (6)	0.0080 (6)	0.0109 (5)	0.0091 (5)
C12	0.0458 (9)	0.0385 (8)	0.0258 (7)	0.0144 (7)	0.0183 (6)	0.0112 (6)
C13	0.0264 (7)	0.0205 (6)	0.0307 (7)	0.0026 (5)	0.0096 (5)	0.0075 (5)
C14	0.0270 (7)	0.0260 (7)	0.0507 (9)	0.0022 (5)	0.0166 (6)	0.0062 (6)
C15	0.0245 (7)	0.0268 (7)	0.0599 (10)	−0.0023 (6)	0.0109 (7)	0.0037 (7)
C16	0.0303 (7)	0.0208 (6)	0.0422 (8)	−0.0020 (5)	0.0036 (6)	0.0002 (6)
C17	0.0272 (7)	0.0213 (6)	0.0319 (7)	0.0032 (5)	0.0070 (5)	0.0053 (5)
C18	0.0229 (6)	0.0199 (6)	0.0269 (6)	0.0031 (5)	0.0066 (5)	0.0079 (5)
C19	0.0225 (6)	0.0210 (6)	0.0198 (6)	0.0034 (5)	0.0060 (5)	0.0058 (5)
C20	0.0241 (6)	0.0236 (6)	0.0189 (6)	0.0049 (5)	0.0065 (5)	0.0076 (5)
C21	0.0411 (8)	0.0278 (7)	0.0224 (6)	−0.0042 (6)	0.0136 (6)	−0.0016 (5)
C22	0.0753 (12)	0.0366 (9)	0.0373 (9)	−0.0098 (8)	0.0369 (9)	−0.0035 (7)
C23	0.0218 (7)	0.0320 (7)	0.0373 (8)	0.0046 (5)	0.0028 (6)	0.0053 (6)
C24	0.0309 (8)	0.0417 (9)	0.0378 (8)	0.0095 (6)	0.0021 (6)	0.0152 (7)

Geometric parameters (Å, º) top

F1—C4	1.3667 (16)	C10—H10A	0.9800
F2—C16	1.3631 (16)	C10—H10B	0.9800
O1—C8	1.2233 (16)	C10—H10C	0.9800
O2—C7	1.4054 (15)	C11—C12	1.5065 (19)
O2—C9	1.4467 (16)	C11—H11A	0.9900
O3—C7	1.4041 (14)	C11—H11B	0.9900
O3—C11	1.4378 (15)	C12—H12A	0.9800
O4—C20	1.2231 (16)	C12—H12B	0.9800
O5—C19	1.4021 (15)	C12—H12C	0.9800
O5—C21	1.4387 (15)	C13—C14	1.3806 (19)
O6—C19	1.4080 (15)	C13—C18	1.3920 (18)
O6—C23	1.4477 (16)	C14—C15	1.387 (2)
N1—C8	1.3514 (17)	C14—H14	0.9500
N1—C1	1.4093 (17)	C15—C16	1.378 (2)
N1—H1	0.850 (19)	C15—H15	0.9500
N2—C20	1.3513 (17)	C16—C17	1.389 (2)
N2—C13	1.4074 (18)	C17—C18	1.3858 (19)
N2—H2	0.868 (19)	C17—H17	0.9500
C1—C2	1.3816 (19)	C18—C19	1.5143 (17)
C1—C6	1.3892 (18)	C19—C20	1.5645 (17)
C2—C3	1.397 (2)	C21—C22	1.501 (2)
C2—H2A	0.9500	C21—H21A	0.9900
C3—C4	1.374 (2)	C21—H21B	0.9900
C3—H3	0.9500	C22—H22A	0.9800
C4—C5	1.388 (2)	C22—H22B	0.9800
C5—C6	1.3862 (18)	C22—H22C	0.9800
C5—H5	0.9500	C23—C24	1.494 (2)
C6—C7	1.5109 (17)	C23—H23A	0.9900
C7—C8	1.5638 (17)	C23—H23B	0.9900
C9—C10	1.494 (2)	C24—H24A	0.9800
C9—H9A	0.9900	C24—H24B	0.9800
C9—H9B	0.9900	C24—H24C	0.9800

C7—O2—C9	115.97 (10)	C11—C12—H12B	109.5
C7—O3—C11	116.02 (10)	H12A—C12—H12B	109.5
C19—O5—C21	115.78 (10)	C11—C12—H12C	109.5
C19—O6—C23	115.62 (10)	H12A—C12—H12C	109.5
C8—N1—C1	111.67 (11)	H12B—C12—H12C	109.5
C8—N1—H1	124.2 (12)	C14—C13—C18	122.18 (13)
C1—N1—H1	124.0 (12)	C14—C13—N2	127.65 (13)
C20—N2—C13	111.84 (11)	C18—C13—N2	110.17 (11)
C20—N2—H2	122.1 (12)	C13—C14—C15	117.98 (14)
C13—N2—H2	125.4 (12)	C13—C14—H14	121.0
C2—C1—C6	122.39 (13)	C15—C14—H14	121.0
C2—C1—N1	127.41 (12)	C16—C15—C14	119.40 (13)
C6—C1—N1	110.20 (11)	C16—C15—H15	120.3
C1—C2—C3	117.46 (13)	C14—C15—H15	120.3
C1—C2—H2A	121.3	F2—C16—C15	118.37 (13)
C3—C2—H2A	121.3	F2—C16—C17	118.15 (13)
C4—C3—C2	119.40 (13)	C15—C16—C17	123.48 (14)
C4—C3—H3	120.3	C18—C17—C16	116.68 (13)
C2—C3—H3	120.3	C18—C17—H17	121.7
F1—C4—C3	118.38 (13)	C16—C17—H17	121.7
F1—C4—C5	117.76 (13)	C17—C18—C13	120.27 (12)
C3—C4—C5	123.85 (13)	C17—C18—C19	131.42 (12)
C6—C5—C4	116.34 (13)	C13—C18—C19	108.30 (11)
C6—C5—H5	121.8	O5—C19—O6	113.37 (10)
C4—C5—H5	121.8	O5—C19—C18	116.90 (10)
C5—C6—C1	120.55 (12)	O6—C19—C18	107.38 (10)
C5—C6—C7	130.95 (12)	O5—C19—C20	103.75 (9)
C1—C6—C7	108.46 (11)	O6—C19—C20	113.04 (10)
O3—C7—O2	113.26 (10)	C18—C19—C20	101.92 (10)
O3—C7—C6	116.93 (10)	O4—C20—N2	126.88 (12)
O2—C7—C6	107.15 (10)	O4—C20—C19	125.53 (11)
O3—C7—C8	103.67 (9)	N2—C20—C19	107.57 (11)
O2—C7—C8	113.47 (10)	O5—C21—C22	107.26 (11)
C6—C7—C8	101.94 (10)	O5—C21—H21A	110.3
O1—C8—N1	126.69 (12)	C22—C21—H21A	110.3
O1—C8—C7	125.62 (11)	O5—C21—H21B	110.3
N1—C8—C7	107.67 (10)	C22—C21—H21B	110.3
O2—C9—C10	107.04 (12)	H21A—C21—H21B	108.5
O2—C9—H9A	110.3	C21—C22—H22A	109.5
C10—C9—H9A	110.3	C21—C22—H22B	109.5
O2—C9—H9B	110.3	H22A—C22—H22B	109.5
C10—C9—H9B	110.3	C21—C22—H22C	109.5
H9A—C9—H9B	108.6	H22A—C22—H22C	109.5
C9—C10—H10A	109.5	H22B—C22—H22C	109.5
C9—C10—H10B	109.5	O6—C23—C24	107.58 (12)
H10A—C10—H10B	109.5	O6—C23—H23A	110.2
C9—C10—H10C	109.5	C24—C23—H23A	110.2
H10A—C10—H10C	109.5	O6—C23—H23B	110.2
H10B—C10—H10C	109.5	C24—C23—H23B	110.2
O3—C11—C12	107.09 (11)	H23A—C23—H23B	108.5
O3—C11—H11A	110.3	C23—C24—H24A	109.5
C12—C11—H11A	110.3	C23—C24—H24B	109.5
O3—C11—H11B	110.3	H24A—C24—H24B	109.5
C12—C11—H11B	110.3	C23—C24—H24C	109.5
H11A—C11—H11B	108.6	H24A—C24—H24C	109.5
C11—C12—H12A	109.5	H24B—C24—H24C	109.5

C8—N1—C1—C2	179.41 (13)	C20—N2—C13—C14	−176.79 (14)
C8—N1—C1—C6	−1.50 (15)	C20—N2—C13—C18	2.93 (15)
C6—C1—C2—C3	−0.6 (2)	C18—C13—C14—C15	−0.2 (2)
N1—C1—C2—C3	178.38 (13)	N2—C13—C14—C15	179.54 (14)
C1—C2—C3—C4	−0.2 (2)	C13—C14—C15—C16	0.8 (2)
C2—C3—C4—F1	−178.54 (13)	C14—C15—C16—F2	179.01 (14)
C2—C3—C4—C5	0.6 (2)	C14—C15—C16—C17	−0.5 (2)
F1—C4—C5—C6	179.04 (11)	F2—C16—C17—C18	179.93 (12)
C3—C4—C5—C6	−0.1 (2)	C15—C16—C17—C18	−0.6 (2)
C4—C5—C6—C1	−0.75 (18)	C16—C17—C18—C13	1.27 (19)
C4—C5—C6—C7	−177.98 (12)	C16—C17—C18—C19	−179.51 (13)
C2—C1—C6—C5	1.1 (2)	C14—C13—C18—C17	−0.9 (2)
N1—C1—C6—C5	−178.01 (11)	N2—C13—C18—C17	179.32 (12)
C2—C1—C6—C7	178.93 (12)	C14—C13—C18—C19	179.68 (13)
N1—C1—C6—C7	−0.22 (14)	N2—C13—C18—C19	−0.06 (14)
C11—O3—C7—O2	−62.62 (14)	C21—O5—C19—O6	63.57 (14)
C11—O3—C7—C6	62.73 (14)	C21—O5—C19—C18	−62.18 (15)
C11—O3—C7—C8	173.97 (10)	C21—O5—C19—C20	−173.44 (10)
C9—O2—C7—O3	−50.93 (14)	C23—O6—C19—O5	50.91 (14)
C9—O2—C7—C6	178.63 (10)	C23—O6—C19—C18	−178.41 (11)
C9—O2—C7—C8	66.91 (14)	C23—O6—C19—C20	−66.80 (14)
C5—C6—C7—O3	−68.73 (17)	C17—C18—C19—O5	66.09 (18)
C1—C6—C7—O3	113.78 (12)	C13—C18—C19—O5	−114.61 (12)
C5—C6—C7—O2	59.62 (17)	C17—C18—C19—O6	−62.58 (17)
C1—C6—C7—O2	−117.87 (11)	C13—C18—C19—O6	116.72 (11)
C5—C6—C7—C8	179.04 (13)	C17—C18—C19—C20	178.39 (13)
C1—C6—C7—C8	1.55 (13)	C13—C18—C19—C20	−2.31 (13)
C1—N1—C8—O1	−176.06 (12)	C13—N2—C20—O4	174.25 (12)
C1—N1—C8—C7	2.48 (14)	C13—N2—C20—C19	−4.36 (14)
O3—C7—C8—O1	54.27 (15)	O5—C19—C20—O4	−52.78 (15)
O2—C7—C8—O1	−69.00 (16)	O6—C19—C20—O4	70.43 (15)
C6—C7—C8—O1	176.13 (12)	C18—C19—C20—O4	−174.63 (12)
O3—C7—C8—N1	−124.28 (11)	O5—C19—C20—N2	125.86 (11)
O2—C7—C8—N1	112.44 (12)	O6—C19—C20—N2	−110.93 (12)
C6—C7—C8—N1	−2.42 (13)	C18—C19—C20—N2	4.01 (12)
C7—O2—C9—C10	177.52 (12)	C19—O5—C21—C22	−166.65 (13)
C7—O3—C11—C12	164.91 (11)	C19—O6—C23—C24	178.89 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.85 (2)	2.30 (2)	3.010 (2)	142 (2)
N1—H1···O1ⁱ	0.85 (2)	2.34 (2)	3.043 (1)	141 (2)
N2—H2···O1ⁱⁱ	0.87 (2)	2.28 (2)	3.002 (2)	140 (2)
N2—H2···O4ⁱⁱⁱ	0.87 (2)	2.33 (2)	3.057 (2)	142 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₄FNO₃
M_r	239.24
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.3218 (6), 9.4320 (5), 14.1544 (8)
α, β, γ (°)	100.475 (5), 104.453 (5), 90.238 (5)
V (Å³)	1183.43 (12)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.90
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	0.773, 0.915
No. of measured, independent and observed [I > 2σ(I)] reflections	8022, 4661, 4067
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.100, 1.04
No. of reflections	4661
No. of parameters	315
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.23

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.85 (2)	2.30 (2)	3.010 (2)	142 (2)
N1—H1···O1ⁱ	0.85 (2)	2.34 (2)	3.043 (1)	141 (2)
N2—H2···O1ⁱⁱ	0.87 (2)	2.28 (2)	3.002 (2)	140 (2)
N2—H2···O4ⁱⁱⁱ	0.87 (2)	2.33 (2)	3.057 (2)	142 (2)

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

Acknowledgements

We thank the Research Center of Pharmacy, King Saud University (project No. 080149) and the Ministry of Higher Education of Malaysia (grant No. UM·C/HIR/MOHE/SC/12) for supporting this study.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
De, A. & Kitagawa, Y. (1991). Acta Cryst. C47, 2384–2386. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar