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The title compound, C17H14F3N3O2·2C2H5OH, was synthesized by the reaction of 4-chloro-6,7-dimethoxy­quinazoline and 3-(triflurometh­yl)aniline at 580 W in a domestic microwave oven and obtained in 93% yield. The bond lengths and angles are normal. Inter­molecular N—H...O, O—H...N and O—H...O hydrogen bonds and π–π stacking inter­actions between the quinazoline rings of neighbouring mol­ecules stabilize the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029521/cv6573sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029521/cv6573Isup2.hkl
Contains datablock I

CCDC reference: 287540

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.063
  • wR factor = 0.186
  • Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C1
Author Response: 'see _publ_section_exptl_refinement'

Alert level B PLAT223_ALERT_4_B Large Solvent/Anion H Ueq(max)/Ueq(min) ... 4.40 Ratio
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C20 PLAT301_ALERT_3_C Main Residue Disorder ......................... 11.00 Perc.
1 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Recently, epidermal growth factor receptor (EGFR) has became one of the significant target proteins in medicinal developments (Arteaga, 2002), since its excess always leads to a variety of vicious tumors and cancers. Among the small molecular inhibitors of EGFR, 4-anilinoquinazoline derivatives are clinically affirmed to be one of the most effective compounds (Hou et al., 2002). The results of QSAR [please define] research indicate that electron-donating groups at the 6,7-positions will improve their effect of EGFR inhibition (Alexander et al., 1996). We report here the synthesis and crystal structure of 6,7-dimethoxy-N-[3-(trifluoromethyl)phenyl]quinazolin-4-amine diethanol solvate, (I).

The title compound (Fig. 1) contains a 6,7-dimethoxy-N-[3-(trifluoromethyl)phenyl]quinazolin-4-amine molecule, which has normal bond lengths and angles (Table 1), and two ethanol solvent molecules in the asymmetric unit. The quinazoline bicycle and non-fused benzene ring make a dihedral angle of 43.2 (1)°. Interestingly, atoms N3, C6, C8 and H3 are almost coplanar, with an r.m.s. deviation of 0.026 (8) Å, in spite of steric hindrance between the quinazoline bicycle and non-fused benzene ring.

The solvent molecules play an imporant role in the crystal formation, participating in a number of hydrogen bonds with the quinazolin-4-amine molecules (Table 2). These hydrogen bonds stabilize the crystal packing (Fig. 2) along with ππ stacking interactions between the quinazoline bicycles of neighbouring molecules; the interplanar distance to the symmetry-related bicycle at (1 − x, 2 − y, 2 − z) is 3.356 (8) Å.

Experimental top

At room temperature, basic alumina (2 g) was added to the solution of 4-chloro-6,7-dimethoxyquinazoline (1 mmol) and 3-(trifluromethyl)aniline (1 mmol) in ether (10 ml). After removal of ether, the solid was poured into an open vessel and irradiated for 3 min at 580 W in a domestic microwave oven. After cooling to room temperature, ethanol (15 ml) was added and the filtrate was concentrated on a rotary evaporator. The residue was isolated on silica column chromatography with CH2Cl2–Et2O (5:3 (v/v) as the eluent in 93% yield. Suitable crystals were obtained by evaporation of an ethanol–water (1:1 (v/v) mixed solution (m.p. 442–443 K). 1H NMR (CDCl3): δ 4.01(s, 3H), 4.03(s, 3H), 7.08 (s, 1H), 7.27 (d, 1H, J = 7.5 Hz), 7.38–7.50 (m, 2H), 7.51 (t, 1H, J = 8.0 Hz), 8.70 (s, 1H). IR (KBr, ν cm−1): 3448, 2925, 2851, 1625, 1584, 1516, 1449, 1332, 1242, 1166, 1123, 1069, 993, 793, 700. [No assignments?] Analysys calculated for C21H26F3N3O4: C 57.14, H 5.94, N 9.52%; found C 57.39, H 5.78, N 9.67%.

Refinement top

All H atoms were initially located in a difference Fourier map. All methyl H atoms were then constrained to an ideal geometry, with C—H distances of 0.96 Å and Uiso(H) = 1.5Ueq(C), but each group was allowed to rotate freely about the C—C bond. The aromatic and hydroxyl H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93 Å, O—H = 0.82 Å, and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O). The amine H atom was refined isotropically. The CF3 group is disordered and the major and minor orientations had refined occupancies of 0.70 (1) and 0.30 (1), respectively. The atomic displacement parameters of one ethanol solvent molecule (O2/C20/C21) are essentialy higher than those of the another solvent molecule indicating a possible partial disorder of the former residue.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. View of (I), showing the atom-labelling scheme and displacement ellipsoids at the 40% probability level. The two ethanol solvent molecules and the minor component of the disordered CF3 group have been omitted for clarity. H atoms are represented by circles of arbitrary size.
[Figure 2] Fig. 2. The molecular packing, showing the hydrogen-bonding interactions (dashed lines). C-bound H atoms have been omitted for clarity.
6,7-Dimethoxy-N-[3-(trifluoromethyl)phenyl]quinazolin-4-amine diethanol solvate top
Crystal data top
C17H14F3N3O2·2C2H6OZ = 2
Mr = 441.45F(000) = 464
Triclinic, P1Dx = 1.296 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 8.7035 (7) ÅCell parameters from 4851 reflections
b = 9.7426 (8) Åθ = 2.3–27.4°
c = 14.5212 (9) ŵ = 0.11 mm1
α = 70.652 (4)°T = 293 K
β = 89.493 (1)°Prism, colourless
γ = 77.484 (3)°0.48 × 0.35 × 0.30 mm
V = 1131.52 (15) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3972 independent reflections
Radiation source: fine-focus sealed tube3264 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
Detector resolution: 10.00 pixels mm-1θmax = 25.2°, θmin = 2.7°
ω scansh = 1010
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1111
Tmin = 0.956, Tmax = 0.969l = 1717
8371 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.186 w = 1/[σ2(Fo2) + (0.0909P)2 + 0.4785P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
3972 reflectionsΔρmax = 0.48 e Å3
318 parametersΔρmin = 0.44 e Å3
1 restraintExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.028 (5)
Crystal data top
C17H14F3N3O2·2C2H6Oγ = 77.484 (3)°
Mr = 441.45V = 1131.52 (15) Å3
Triclinic, P1Z = 2
a = 8.7035 (7) ÅMo Kα radiation
b = 9.7426 (8) ŵ = 0.11 mm1
c = 14.5212 (9) ÅT = 293 K
α = 70.652 (4)°0.48 × 0.35 × 0.30 mm
β = 89.493 (1)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3972 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
3264 reflections with I > 2σ(I)
Tmin = 0.956, Tmax = 0.969Rint = 0.058
8371 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0631 restraint
wR(F2) = 0.186H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.48 e Å3
3972 reflectionsΔρmin = 0.44 e Å3
318 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
xyzUiso*/UeqOcc. (<1)
F10.7956 (18)1.1988 (8)0.5196 (3)0.141 (3)0.70 (1)
F20.6710 (13)1.4053 (17)0.5227 (5)0.190 (4)0.70 (1)
F30.9098 (12)1.3693 (14)0.4876 (4)0.135 (2)0.70 (1)
F40.6741 (18)1.293 (3)0.5270 (6)0.101 (4)0.30 (1)
F50.806 (4)1.447 (2)0.4958 (10)0.134 (6)0.30 (1)
F60.904 (3)1.225 (4)0.5040 (11)0.172 (8)0.30 (1)
O10.7600 (2)0.7994 (2)0.76731 (13)0.0582 (5)
H10.67800.84470.73330.087*
O20.4877 (3)0.0125 (3)0.67879 (15)0.0821 (7)
H20.45500.00920.72650.123*
O30.6792 (2)0.46377 (16)1.04799 (12)0.0502 (4)
O40.5632 (2)0.46490 (17)1.21001 (12)0.0518 (5)
N10.7886 (2)0.99377 (19)0.88304 (13)0.0395 (4)
N20.7267 (2)1.09648 (19)1.00527 (13)0.0413 (4)
N30.6201 (2)0.9674 (2)1.15294 (13)0.0431 (5)
C10.8089 (5)1.3093 (4)0.5458 (2)0.0796 (10)
C20.8574 (3)1.2672 (3)0.65184 (18)0.0516 (6)
C30.9497 (3)1.3455 (3)0.6821 (2)0.0554 (7)
H3A0.98561.42240.63670.066*
C40.9874 (3)1.3076 (3)0.78075 (19)0.0501 (6)
H41.04911.35970.80200.060*
C50.9346 (3)1.1931 (2)0.84838 (17)0.0429 (5)
H50.96181.16790.91470.052*
C60.8406 (2)1.1152 (2)0.81778 (15)0.0377 (5)
C70.8017 (3)1.1530 (3)0.71864 (16)0.0443 (5)
H70.73881.10220.69720.053*
C80.7366 (2)0.9820 (2)0.97349 (15)0.0355 (5)
C90.6690 (3)1.0821 (2)1.09306 (17)0.0449 (5)
H90.66261.16311.11440.054*
C100.6334 (2)0.8466 (2)1.12255 (15)0.0371 (5)
C110.6932 (2)0.8473 (2)1.03202 (14)0.0354 (5)
C120.7106 (3)0.7172 (2)1.00538 (15)0.0378 (5)
H120.75190.71630.94630.045*
C130.6668 (3)0.5935 (2)1.06613 (16)0.0401 (5)
C140.6028 (3)0.5942 (2)1.15710 (16)0.0407 (5)
C150.5870 (2)0.7185 (2)1.18374 (15)0.0400 (5)
H150.54520.71851.24290.048*
C160.4843 (4)0.4622 (3)1.2966 (2)0.0707 (8)
H16A0.54870.48591.33990.106*
H16B0.46530.36451.32840.106*
H16C0.38550.53451.28000.106*
C170.7427 (4)0.4592 (3)0.9577 (2)0.0596 (7)
H17A0.67910.53730.90430.089*
H17B0.74290.36420.95130.089*
H17C0.84870.47290.95690.089*
C180.8826 (4)0.7693 (4)0.7066 (2)0.0742 (9)
H18A0.88000.85800.65030.089*
H18B0.86720.69040.68340.089*
C191.0339 (5)0.7244 (6)0.7615 (4)0.1117 (14)
H19A1.05690.80840.77460.168*
H19B1.11450.68870.72400.168*
H19C1.03060.64620.82210.168*
C200.3602 (7)0.0100 (10)0.6132 (4)0.166 (3)
H20A0.27550.02930.64870.199*
H20B0.39270.04220.56740.199*
C210.3045 (13)0.1710 (11)0.5599 (7)0.360 (11)
H21A0.29670.22470.60510.541*
H21B0.20270.18920.52740.541*
H21C0.37770.20400.51230.541*
H30.774 (3)0.931 (3)0.8559 (17)0.039 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.283 (11)0.122 (4)0.050 (2)0.117 (7)0.011 (5)0.026 (2)
F20.187 (8)0.237 (8)0.073 (3)0.083 (7)0.052 (4)0.038 (5)
F30.198 (7)0.179 (6)0.0533 (19)0.127 (6)0.049 (3)0.019 (4)
F40.099 (7)0.146 (10)0.044 (4)0.059 (8)0.011 (5)0.006 (7)
F50.227 (18)0.099 (8)0.059 (6)0.091 (10)0.015 (9)0.029 (6)
F60.180 (15)0.27 (3)0.084 (9)0.029 (14)0.029 (8)0.092 (14)
O10.0680 (12)0.0589 (11)0.0526 (10)0.0151 (9)0.0071 (8)0.0247 (9)
O20.0687 (13)0.1167 (19)0.0594 (12)0.0012 (12)0.0036 (10)0.0404 (13)
O30.0704 (11)0.0303 (8)0.0531 (9)0.0187 (7)0.0103 (8)0.0139 (7)
O40.0618 (10)0.0391 (9)0.0501 (9)0.0192 (7)0.0123 (8)0.0045 (7)
N10.0543 (11)0.0289 (9)0.0380 (10)0.0154 (8)0.0037 (8)0.0111 (8)
N20.0517 (11)0.0317 (9)0.0419 (10)0.0118 (8)0.0009 (8)0.0127 (8)
N30.0500 (11)0.0407 (10)0.0405 (10)0.0096 (8)0.0016 (8)0.0166 (8)
C10.102 (3)0.084 (2)0.0486 (16)0.041 (2)0.0122 (18)0.0052 (16)
C20.0573 (14)0.0475 (13)0.0469 (13)0.0174 (11)0.0133 (11)0.0085 (10)
C30.0569 (15)0.0422 (13)0.0614 (15)0.0200 (11)0.0157 (12)0.0049 (11)
C40.0442 (13)0.0416 (12)0.0658 (15)0.0175 (10)0.0058 (11)0.0150 (11)
C50.0397 (11)0.0378 (11)0.0499 (12)0.0110 (9)0.0005 (9)0.0113 (9)
C60.0396 (11)0.0273 (10)0.0433 (11)0.0064 (8)0.0048 (9)0.0091 (8)
C70.0490 (13)0.0425 (12)0.0430 (12)0.0165 (10)0.0058 (10)0.0128 (10)
C80.0384 (11)0.0299 (10)0.0362 (10)0.0075 (8)0.0027 (8)0.0087 (8)
C90.0554 (13)0.0369 (12)0.0471 (13)0.0109 (10)0.0007 (10)0.0198 (10)
C100.0379 (11)0.0350 (11)0.0365 (11)0.0064 (8)0.0037 (8)0.0105 (9)
C110.0373 (11)0.0316 (10)0.0355 (11)0.0083 (8)0.0022 (8)0.0085 (8)
C120.0452 (12)0.0325 (10)0.0368 (10)0.0118 (9)0.0028 (9)0.0114 (8)
C130.0443 (12)0.0303 (10)0.0444 (12)0.0099 (9)0.0003 (9)0.0098 (9)
C140.0399 (11)0.0353 (11)0.0413 (11)0.0119 (9)0.0009 (9)0.0033 (9)
C150.0395 (11)0.0438 (12)0.0342 (11)0.0095 (9)0.0022 (9)0.0099 (9)
C160.092 (2)0.0610 (17)0.0565 (16)0.0338 (16)0.0249 (15)0.0066 (13)
C170.090 (2)0.0387 (12)0.0617 (15)0.0255 (13)0.0187 (14)0.0252 (11)
C180.081 (2)0.076 (2)0.0655 (18)0.0034 (16)0.0129 (16)0.0332 (16)
C190.073 (2)0.120 (4)0.131 (4)0.002 (2)0.007 (2)0.043 (3)
C200.113 (4)0.312 (10)0.105 (4)0.030 (5)0.007 (3)0.122 (6)
C210.275 (12)0.52 (2)0.199 (9)0.227 (14)0.129 (9)0.201 (12)
Geometric parameters (Å, º) top
F1—C11.282 (6)C6—C71.388 (3)
F2—C11.320 (7)C7—H70.9300
F3—C11.307 (6)C8—C111.434 (3)
F4—C11.263 (10)C9—H90.9300
F5—C11.293 (12)C10—C111.408 (3)
F6—C11.326 (15)C10—C151.410 (3)
O1—C181.421 (3)C11—C121.421 (3)
O1—H10.8200C12—C131.365 (3)
O2—C201.400 (6)C12—H120.9300
O2—H20.8200C13—C141.431 (3)
O3—C131.357 (3)C14—C151.368 (3)
O3—C171.428 (3)C15—H150.9300
O4—C141.356 (3)C16—H16A0.9600
O4—C161.423 (3)C16—H16B0.9600
N1—C81.362 (3)C16—H16C0.9600
N1—C61.409 (3)C17—H17A0.9600
N1—H30.86 (3)C17—H17B0.9600
N2—C81.328 (3)C17—H17C0.9600
N2—C91.341 (3)C18—C191.448 (5)
N3—C91.319 (3)C18—H18A0.9700
N3—C101.371 (3)C18—H18B0.9700
C1—C21.494 (4)C19—H19A0.9600
C2—C31.384 (4)C19—H19B0.9600
C2—C71.387 (3)C19—H19C0.9600
C3—C41.379 (4)C20—C211.472 (14)
C3—H3A0.9300C20—H20A0.9700
C4—C51.382 (3)C20—H20B0.9700
C4—H40.9300C21—H21A0.9600
C5—C61.393 (3)C21—H21B0.9600
C5—H50.9300C21—H21C0.9600
C18—O1—H1109.5C11—C12—H12119.8
C20—O2—H2109.5O3—C13—C12125.0 (2)
C13—O3—C17116.34 (17)O3—C13—C14114.84 (18)
C14—O4—C16117.31 (19)C12—C13—C14120.12 (19)
C8—N1—C6126.92 (18)O4—C14—C15126.0 (2)
C8—N1—H3119.6 (16)O4—C14—C13114.12 (19)
C6—N1—H3112.5 (16)C15—C14—C13119.93 (19)
C8—N2—C9116.79 (18)C14—C15—C10120.8 (2)
C9—N3—C10115.86 (19)C14—C15—H15119.6
F4—C1—C2115.8 (5)C10—C15—H15119.6
F1—C1—C2114.1 (3)O4—C16—H16A109.5
F5—C1—C2113.6 (7)O4—C16—H16B109.5
F3—C1—C2113.4 (4)H16A—C16—H16B109.5
F2—C1—C2111.1 (4)O4—C16—H16C109.5
F6—C1—C2111.5 (8)H16A—C16—H16C109.5
C3—C2—C7121.3 (2)H16B—C16—H16C109.5
C3—C2—C1120.3 (2)O3—C17—H17A109.5
C7—C2—C1118.4 (2)O3—C17—H17B109.5
C4—C3—C2118.9 (2)H17A—C17—H17B109.5
C4—C3—H3A120.5O3—C17—H17C109.5
C2—C3—H3A120.5H17A—C17—H17C109.5
C3—C4—C5120.7 (2)H17B—C17—H17C109.5
C3—C4—H4119.7O1—C18—C19109.8 (3)
C5—C4—H4119.7O1—C18—H18A109.7
C4—C5—C6120.3 (2)C19—C18—H18A109.7
C4—C5—H5119.8O1—C18—H18B109.7
C6—C5—H5119.8C19—C18—H18B109.7
C7—C6—C5119.3 (2)H18A—C18—H18B108.2
C7—C6—N1117.83 (19)C18—C19—H19A109.5
C5—C6—N1122.8 (2)C18—C19—H19B109.5
C2—C7—C6119.5 (2)H19A—C19—H19B109.5
C2—C7—H7120.3C18—C19—H19C109.5
C6—C7—H7120.3H19A—C19—H19C109.5
N2—C8—N1118.91 (18)H19B—C19—H19C109.5
N2—C8—C11121.48 (19)O2—C20—C21109.3 (6)
N1—C8—C11119.60 (18)O2—C20—H20A109.8
N3—C9—N2128.16 (19)C21—C20—H20A109.8
N3—C9—H9115.9O2—C20—H20B109.8
N2—C9—H9115.9C21—C20—H20B109.8
N3—C10—C11121.51 (19)H20A—C20—H20B108.3
N3—C10—C15119.12 (19)C20—C21—H21A109.5
C11—C10—C15119.37 (19)C20—C21—H21B109.5
C10—C11—C12119.45 (18)H21A—C21—H21B109.5
C10—C11—C8116.13 (18)C20—C21—H21C109.5
C12—C11—C8124.40 (19)H21A—C21—H21C109.5
C13—C12—C11120.3 (2)H21B—C21—H21C109.5
C13—C12—H12119.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H3···O10.86 (3)2.12 (3)2.965 (3)169 (2)
O2—H2···N3i0.821.932.745 (3)173
O1—H1···O2ii0.821.902.690 (3)162
Symmetry codes: (i) x+1, y+1, z+2; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC17H14F3N3O2·2C2H6O
Mr441.45
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.7035 (7), 9.7426 (8), 14.5212 (9)
α, β, γ (°)70.652 (4), 89.493 (1), 77.484 (3)
V3)1131.52 (15)
Z2
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.48 × 0.35 × 0.30
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.956, 0.969
No. of measured, independent and
observed [I > 2σ(I)] reflections
8371, 3972, 3264
Rint0.058
(sin θ/λ)max1)0.598
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.186, 1.08
No. of reflections3972
No. of parameters318
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.48, 0.44

Computer programs: RAPID-AUTO (Rigaku, 1998), RAPID-AUTO, CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.

Selected geometric parameters (Å, º) top
F1—C11.282 (6)N1—H30.86 (3)
F2—C11.320 (7)N2—C81.328 (3)
F3—C11.307 (6)N2—C91.341 (3)
N1—C81.362 (3)N3—C91.319 (3)
N1—C61.409 (3)N3—C101.371 (3)
C13—O3—C17116.34 (17)C9—N3—C10115.86 (19)
C14—O4—C16117.31 (19)F1—C1—C2114.1 (3)
C8—N1—C6126.92 (18)F3—C1—C2113.4 (4)
C8—N1—H3119.6 (16)F2—C1—C2111.1 (4)
C6—N1—H3112.5 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H3···O10.86 (3)2.12 (3)2.965 (3)169 (2)
O2—H2···N3i0.821.932.745 (3)173
O1—H1···O2ii0.821.902.690 (3)162
Symmetry codes: (i) x+1, y+1, z+2; (ii) x, y+1, z.
 

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