Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805029521/cv6573sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805029521/cv6573Isup2.hkl |
CCDC reference: 287540
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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%.
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.
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.
C17H14F3N3O2·2C2H6O | Z = 2 |
Mr = 441.45 | F(000) = 464 |
Triclinic, P1 | Dx = 1.296 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 8.7035 (7) Å | Cell parameters from 4851 reflections |
b = 9.7426 (8) Å | θ = 2.3–27.4° |
c = 14.5212 (9) Å | µ = 0.11 mm−1 |
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 |
Rigaku R-AXIS RAPID diffractometer | 3972 independent reflections |
Radiation source: fine-focus sealed tube | 3264 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
Detector resolution: 10.00 pixels mm-1 | θmax = 25.2°, θmin = 2.7° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −11→11 |
Tmin = 0.956, Tmax = 0.969 | l = −17→17 |
8371 measured reflections |
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)] = 0.063 | H 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 reflections | Δρmax = 0.48 e Å−3 |
318 parameters | Δρmin = −0.44 e Å−3 |
1 restraint | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.028 (5) |
C17H14F3N3O2·2C2H6O | γ = 77.484 (3)° |
Mr = 441.45 | V = 1131.52 (15) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.7035 (7) Å | Mo Kα radiation |
b = 9.7426 (8) Å | µ = 0.11 mm−1 |
c = 14.5212 (9) Å | T = 293 K |
α = 70.652 (4)° | 0.48 × 0.35 × 0.30 mm |
β = 89.493 (1)° |
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 = 0.969 | Rint = 0.058 |
8371 measured reflections |
R[F2 > 2σ(F2)] = 0.063 | 1 restraint |
wR(F2) = 0.186 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.48 e Å−3 |
3972 reflections | Δρmin = −0.44 e Å−3 |
318 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
F1 | 0.7956 (18) | 1.1988 (8) | 0.5196 (3) | 0.141 (3) | 0.70 (1) |
F2 | 0.6710 (13) | 1.4053 (17) | 0.5227 (5) | 0.190 (4) | 0.70 (1) |
F3 | 0.9098 (12) | 1.3693 (14) | 0.4876 (4) | 0.135 (2) | 0.70 (1) |
F4 | 0.6741 (18) | 1.293 (3) | 0.5270 (6) | 0.101 (4) | 0.30 (1) |
F5 | 0.806 (4) | 1.447 (2) | 0.4958 (10) | 0.134 (6) | 0.30 (1) |
F6 | 0.904 (3) | 1.225 (4) | 0.5040 (11) | 0.172 (8) | 0.30 (1) |
O1 | 0.7600 (2) | 0.7994 (2) | 0.76731 (13) | 0.0582 (5) | |
H1 | 0.6780 | 0.8447 | 0.7333 | 0.087* | |
O2 | 0.4877 (3) | −0.0125 (3) | 0.67879 (15) | 0.0821 (7) | |
H2 | 0.4550 | 0.0092 | 0.7265 | 0.123* | |
O3 | 0.6792 (2) | 0.46377 (16) | 1.04799 (12) | 0.0502 (4) | |
O4 | 0.5632 (2) | 0.46490 (17) | 1.21001 (12) | 0.0518 (5) | |
N1 | 0.7886 (2) | 0.99377 (19) | 0.88304 (13) | 0.0395 (4) | |
N2 | 0.7267 (2) | 1.09648 (19) | 1.00527 (13) | 0.0413 (4) | |
N3 | 0.6201 (2) | 0.9674 (2) | 1.15294 (13) | 0.0431 (5) | |
C1 | 0.8089 (5) | 1.3093 (4) | 0.5458 (2) | 0.0796 (10) | |
C2 | 0.8574 (3) | 1.2672 (3) | 0.65184 (18) | 0.0516 (6) | |
C3 | 0.9497 (3) | 1.3455 (3) | 0.6821 (2) | 0.0554 (7) | |
H3A | 0.9856 | 1.4224 | 0.6367 | 0.066* | |
C4 | 0.9874 (3) | 1.3076 (3) | 0.78075 (19) | 0.0501 (6) | |
H4 | 1.0491 | 1.3597 | 0.8020 | 0.060* | |
C5 | 0.9346 (3) | 1.1931 (2) | 0.84838 (17) | 0.0429 (5) | |
H5 | 0.9618 | 1.1679 | 0.9147 | 0.052* | |
C6 | 0.8406 (2) | 1.1152 (2) | 0.81778 (15) | 0.0377 (5) | |
C7 | 0.8017 (3) | 1.1530 (3) | 0.71864 (16) | 0.0443 (5) | |
H7 | 0.7388 | 1.1022 | 0.6972 | 0.053* | |
C8 | 0.7366 (2) | 0.9820 (2) | 0.97349 (15) | 0.0355 (5) | |
C9 | 0.6690 (3) | 1.0821 (2) | 1.09306 (17) | 0.0449 (5) | |
H9 | 0.6626 | 1.1631 | 1.1144 | 0.054* | |
C10 | 0.6334 (2) | 0.8466 (2) | 1.12255 (15) | 0.0371 (5) | |
C11 | 0.6932 (2) | 0.8473 (2) | 1.03202 (14) | 0.0354 (5) | |
C12 | 0.7106 (3) | 0.7172 (2) | 1.00538 (15) | 0.0378 (5) | |
H12 | 0.7519 | 0.7163 | 0.9463 | 0.045* | |
C13 | 0.6668 (3) | 0.5935 (2) | 1.06613 (16) | 0.0401 (5) | |
C14 | 0.6028 (3) | 0.5942 (2) | 1.15710 (16) | 0.0407 (5) | |
C15 | 0.5870 (2) | 0.7185 (2) | 1.18374 (15) | 0.0400 (5) | |
H15 | 0.5452 | 0.7185 | 1.2429 | 0.048* | |
C16 | 0.4843 (4) | 0.4622 (3) | 1.2966 (2) | 0.0707 (8) | |
H16A | 0.5487 | 0.4859 | 1.3399 | 0.106* | |
H16B | 0.4653 | 0.3645 | 1.3284 | 0.106* | |
H16C | 0.3855 | 0.5345 | 1.2800 | 0.106* | |
C17 | 0.7427 (4) | 0.4592 (3) | 0.9577 (2) | 0.0596 (7) | |
H17A | 0.6791 | 0.5373 | 0.9043 | 0.089* | |
H17B | 0.7429 | 0.3642 | 0.9513 | 0.089* | |
H17C | 0.8487 | 0.4729 | 0.9569 | 0.089* | |
C18 | 0.8826 (4) | 0.7693 (4) | 0.7066 (2) | 0.0742 (9) | |
H18A | 0.8800 | 0.8580 | 0.6503 | 0.089* | |
H18B | 0.8672 | 0.6904 | 0.6834 | 0.089* | |
C19 | 1.0339 (5) | 0.7244 (6) | 0.7615 (4) | 0.1117 (14) | |
H19A | 1.0569 | 0.8084 | 0.7746 | 0.168* | |
H19B | 1.1145 | 0.6887 | 0.7240 | 0.168* | |
H19C | 1.0306 | 0.6462 | 0.8221 | 0.168* | |
C20 | 0.3602 (7) | 0.0100 (10) | 0.6132 (4) | 0.166 (3) | |
H20A | 0.2755 | −0.0293 | 0.6487 | 0.199* | |
H20B | 0.3927 | −0.0422 | 0.5674 | 0.199* | |
C21 | 0.3045 (13) | 0.1710 (11) | 0.5599 (7) | 0.360 (11) | |
H21A | 0.2967 | 0.2247 | 0.6051 | 0.541* | |
H21B | 0.2027 | 0.1892 | 0.5274 | 0.541* | |
H21C | 0.3777 | 0.2040 | 0.5123 | 0.541* | |
H3 | 0.774 (3) | 0.931 (3) | 0.8559 (17) | 0.039 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.283 (11) | 0.122 (4) | 0.050 (2) | −0.117 (7) | 0.011 (5) | −0.026 (2) |
F2 | 0.187 (8) | 0.237 (8) | 0.073 (3) | 0.083 (7) | −0.052 (4) | −0.038 (5) |
F3 | 0.198 (7) | 0.179 (6) | 0.0533 (19) | −0.127 (6) | 0.049 (3) | −0.019 (4) |
F4 | 0.099 (7) | 0.146 (10) | 0.044 (4) | −0.059 (8) | −0.011 (5) | 0.006 (7) |
F5 | 0.227 (18) | 0.099 (8) | 0.059 (6) | −0.091 (10) | −0.015 (9) | 0.029 (6) |
F6 | 0.180 (15) | 0.27 (3) | 0.084 (9) | −0.029 (14) | 0.029 (8) | −0.092 (14) |
O1 | 0.0680 (12) | 0.0589 (11) | 0.0526 (10) | −0.0151 (9) | 0.0071 (8) | −0.0247 (9) |
O2 | 0.0687 (13) | 0.1167 (19) | 0.0594 (12) | −0.0012 (12) | 0.0036 (10) | −0.0404 (13) |
O3 | 0.0704 (11) | 0.0303 (8) | 0.0531 (9) | −0.0187 (7) | 0.0103 (8) | −0.0139 (7) |
O4 | 0.0618 (10) | 0.0391 (9) | 0.0501 (9) | −0.0192 (7) | 0.0123 (8) | −0.0045 (7) |
N1 | 0.0543 (11) | 0.0289 (9) | 0.0380 (10) | −0.0154 (8) | 0.0037 (8) | −0.0111 (8) |
N2 | 0.0517 (11) | 0.0317 (9) | 0.0419 (10) | −0.0118 (8) | 0.0009 (8) | −0.0127 (8) |
N3 | 0.0500 (11) | 0.0407 (10) | 0.0405 (10) | −0.0096 (8) | 0.0016 (8) | −0.0166 (8) |
C1 | 0.102 (3) | 0.084 (2) | 0.0486 (16) | −0.041 (2) | 0.0122 (18) | −0.0052 (16) |
C2 | 0.0573 (14) | 0.0475 (13) | 0.0469 (13) | −0.0174 (11) | 0.0133 (11) | −0.0085 (10) |
C3 | 0.0569 (15) | 0.0422 (13) | 0.0614 (15) | −0.0200 (11) | 0.0157 (12) | −0.0049 (11) |
C4 | 0.0442 (13) | 0.0416 (12) | 0.0658 (15) | −0.0175 (10) | 0.0058 (11) | −0.0150 (11) |
C5 | 0.0397 (11) | 0.0378 (11) | 0.0499 (12) | −0.0110 (9) | 0.0005 (9) | −0.0113 (9) |
C6 | 0.0396 (11) | 0.0273 (10) | 0.0433 (11) | −0.0064 (8) | 0.0048 (9) | −0.0091 (8) |
C7 | 0.0490 (13) | 0.0425 (12) | 0.0430 (12) | −0.0165 (10) | 0.0058 (10) | −0.0128 (10) |
C8 | 0.0384 (11) | 0.0299 (10) | 0.0362 (10) | −0.0075 (8) | −0.0027 (8) | −0.0087 (8) |
C9 | 0.0554 (13) | 0.0369 (12) | 0.0471 (13) | −0.0109 (10) | 0.0007 (10) | −0.0198 (10) |
C10 | 0.0379 (11) | 0.0350 (11) | 0.0365 (11) | −0.0064 (8) | −0.0037 (8) | −0.0105 (9) |
C11 | 0.0373 (11) | 0.0316 (10) | 0.0355 (11) | −0.0083 (8) | −0.0022 (8) | −0.0085 (8) |
C12 | 0.0452 (12) | 0.0325 (10) | 0.0368 (10) | −0.0118 (9) | 0.0028 (9) | −0.0114 (8) |
C13 | 0.0443 (12) | 0.0303 (10) | 0.0444 (12) | −0.0099 (9) | −0.0003 (9) | −0.0098 (9) |
C14 | 0.0399 (11) | 0.0353 (11) | 0.0413 (11) | −0.0119 (9) | −0.0009 (9) | −0.0033 (9) |
C15 | 0.0395 (11) | 0.0438 (12) | 0.0342 (11) | −0.0095 (9) | 0.0022 (9) | −0.0099 (9) |
C16 | 0.092 (2) | 0.0610 (17) | 0.0565 (16) | −0.0338 (16) | 0.0249 (15) | −0.0066 (13) |
C17 | 0.090 (2) | 0.0387 (12) | 0.0617 (15) | −0.0255 (13) | 0.0187 (14) | −0.0252 (11) |
C18 | 0.081 (2) | 0.076 (2) | 0.0655 (18) | −0.0034 (16) | 0.0129 (16) | −0.0332 (16) |
C19 | 0.073 (2) | 0.120 (4) | 0.131 (4) | 0.002 (2) | 0.007 (2) | −0.043 (3) |
C20 | 0.113 (4) | 0.312 (10) | 0.105 (4) | −0.030 (5) | 0.007 (3) | −0.122 (6) |
C21 | 0.275 (12) | 0.52 (2) | 0.199 (9) | 0.227 (14) | −0.129 (9) | −0.201 (12) |
F1—C1 | 1.282 (6) | C6—C7 | 1.388 (3) |
F2—C1 | 1.320 (7) | C7—H7 | 0.9300 |
F3—C1 | 1.307 (6) | C8—C11 | 1.434 (3) |
F4—C1 | 1.263 (10) | C9—H9 | 0.9300 |
F5—C1 | 1.293 (12) | C10—C11 | 1.408 (3) |
F6—C1 | 1.326 (15) | C10—C15 | 1.410 (3) |
O1—C18 | 1.421 (3) | C11—C12 | 1.421 (3) |
O1—H1 | 0.8200 | C12—C13 | 1.365 (3) |
O2—C20 | 1.400 (6) | C12—H12 | 0.9300 |
O2—H2 | 0.8200 | C13—C14 | 1.431 (3) |
O3—C13 | 1.357 (3) | C14—C15 | 1.368 (3) |
O3—C17 | 1.428 (3) | C15—H15 | 0.9300 |
O4—C14 | 1.356 (3) | C16—H16A | 0.9600 |
O4—C16 | 1.423 (3) | C16—H16B | 0.9600 |
N1—C8 | 1.362 (3) | C16—H16C | 0.9600 |
N1—C6 | 1.409 (3) | C17—H17A | 0.9600 |
N1—H3 | 0.86 (3) | C17—H17B | 0.9600 |
N2—C8 | 1.328 (3) | C17—H17C | 0.9600 |
N2—C9 | 1.341 (3) | C18—C19 | 1.448 (5) |
N3—C9 | 1.319 (3) | C18—H18A | 0.9700 |
N3—C10 | 1.371 (3) | C18—H18B | 0.9700 |
C1—C2 | 1.494 (4) | C19—H19A | 0.9600 |
C2—C3 | 1.384 (4) | C19—H19B | 0.9600 |
C2—C7 | 1.387 (3) | C19—H19C | 0.9600 |
C3—C4 | 1.379 (4) | C20—C21 | 1.472 (14) |
C3—H3A | 0.9300 | C20—H20A | 0.9700 |
C4—C5 | 1.382 (3) | C20—H20B | 0.9700 |
C4—H4 | 0.9300 | C21—H21A | 0.9600 |
C5—C6 | 1.393 (3) | C21—H21B | 0.9600 |
C5—H5 | 0.9300 | C21—H21C | 0.9600 |
C18—O1—H1 | 109.5 | C11—C12—H12 | 119.8 |
C20—O2—H2 | 109.5 | O3—C13—C12 | 125.0 (2) |
C13—O3—C17 | 116.34 (17) | O3—C13—C14 | 114.84 (18) |
C14—O4—C16 | 117.31 (19) | C12—C13—C14 | 120.12 (19) |
C8—N1—C6 | 126.92 (18) | O4—C14—C15 | 126.0 (2) |
C8—N1—H3 | 119.6 (16) | O4—C14—C13 | 114.12 (19) |
C6—N1—H3 | 112.5 (16) | C15—C14—C13 | 119.93 (19) |
C8—N2—C9 | 116.79 (18) | C14—C15—C10 | 120.8 (2) |
C9—N3—C10 | 115.86 (19) | C14—C15—H15 | 119.6 |
F4—C1—C2 | 115.8 (5) | C10—C15—H15 | 119.6 |
F1—C1—C2 | 114.1 (3) | O4—C16—H16A | 109.5 |
F5—C1—C2 | 113.6 (7) | O4—C16—H16B | 109.5 |
F3—C1—C2 | 113.4 (4) | H16A—C16—H16B | 109.5 |
F2—C1—C2 | 111.1 (4) | O4—C16—H16C | 109.5 |
F6—C1—C2 | 111.5 (8) | H16A—C16—H16C | 109.5 |
C3—C2—C7 | 121.3 (2) | H16B—C16—H16C | 109.5 |
C3—C2—C1 | 120.3 (2) | O3—C17—H17A | 109.5 |
C7—C2—C1 | 118.4 (2) | O3—C17—H17B | 109.5 |
C4—C3—C2 | 118.9 (2) | H17A—C17—H17B | 109.5 |
C4—C3—H3A | 120.5 | O3—C17—H17C | 109.5 |
C2—C3—H3A | 120.5 | H17A—C17—H17C | 109.5 |
C3—C4—C5 | 120.7 (2) | H17B—C17—H17C | 109.5 |
C3—C4—H4 | 119.7 | O1—C18—C19 | 109.8 (3) |
C5—C4—H4 | 119.7 | O1—C18—H18A | 109.7 |
C4—C5—C6 | 120.3 (2) | C19—C18—H18A | 109.7 |
C4—C5—H5 | 119.8 | O1—C18—H18B | 109.7 |
C6—C5—H5 | 119.8 | C19—C18—H18B | 109.7 |
C7—C6—C5 | 119.3 (2) | H18A—C18—H18B | 108.2 |
C7—C6—N1 | 117.83 (19) | C18—C19—H19A | 109.5 |
C5—C6—N1 | 122.8 (2) | C18—C19—H19B | 109.5 |
C2—C7—C6 | 119.5 (2) | H19A—C19—H19B | 109.5 |
C2—C7—H7 | 120.3 | C18—C19—H19C | 109.5 |
C6—C7—H7 | 120.3 | H19A—C19—H19C | 109.5 |
N2—C8—N1 | 118.91 (18) | H19B—C19—H19C | 109.5 |
N2—C8—C11 | 121.48 (19) | O2—C20—C21 | 109.3 (6) |
N1—C8—C11 | 119.60 (18) | O2—C20—H20A | 109.8 |
N3—C9—N2 | 128.16 (19) | C21—C20—H20A | 109.8 |
N3—C9—H9 | 115.9 | O2—C20—H20B | 109.8 |
N2—C9—H9 | 115.9 | C21—C20—H20B | 109.8 |
N3—C10—C11 | 121.51 (19) | H20A—C20—H20B | 108.3 |
N3—C10—C15 | 119.12 (19) | C20—C21—H21A | 109.5 |
C11—C10—C15 | 119.37 (19) | C20—C21—H21B | 109.5 |
C10—C11—C12 | 119.45 (18) | H21A—C21—H21B | 109.5 |
C10—C11—C8 | 116.13 (18) | C20—C21—H21C | 109.5 |
C12—C11—C8 | 124.40 (19) | H21A—C21—H21C | 109.5 |
C13—C12—C11 | 120.3 (2) | H21B—C21—H21C | 109.5 |
C13—C12—H12 | 119.8 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H3···O1 | 0.86 (3) | 2.12 (3) | 2.965 (3) | 169 (2) |
O2—H2···N3i | 0.82 | 1.93 | 2.745 (3) | 173 |
O1—H1···O2ii | 0.82 | 1.90 | 2.690 (3) | 162 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C17H14F3N3O2·2C2H6O |
Mr | 441.45 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 1131.52 (15) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.48 × 0.35 × 0.30 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.956, 0.969 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8371, 3972, 3264 |
Rint | 0.058 |
(sin θ/λ)max (Å−1) | 0.598 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.186, 1.08 |
No. of reflections | 3972 |
No. of parameters | 318 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 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.
F1—C1 | 1.282 (6) | N1—H3 | 0.86 (3) |
F2—C1 | 1.320 (7) | N2—C8 | 1.328 (3) |
F3—C1 | 1.307 (6) | N2—C9 | 1.341 (3) |
N1—C8 | 1.362 (3) | N3—C9 | 1.319 (3) |
N1—C6 | 1.409 (3) | N3—C10 | 1.371 (3) |
C13—O3—C17 | 116.34 (17) | C9—N3—C10 | 115.86 (19) |
C14—O4—C16 | 117.31 (19) | F1—C1—C2 | 114.1 (3) |
C8—N1—C6 | 126.92 (18) | F3—C1—C2 | 113.4 (4) |
C8—N1—H3 | 119.6 (16) | F2—C1—C2 | 111.1 (4) |
C6—N1—H3 | 112.5 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H3···O1 | 0.86 (3) | 2.12 (3) | 2.965 (3) | 169 (2) |
O2—H2···N3i | 0.82 | 1.93 | 2.745 (3) | 173 |
O1—H1···O2ii | 0.82 | 1.90 | 2.690 (3) | 162 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x, y+1, z. |
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 π–π 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.