Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054487/at2452sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054487/at2452Isup2.hkl |
CCDC reference: 635803
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.057
- wR factor = 0.143
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C19 - C20 .. 8.60 su
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.26 Ratio PLAT220_ALERT_2_C Large Non-Solvent N Ueq(max)/Ueq(min) ... 2.65 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for N4 - C21 .. 5.39 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C6 - C7 .. 6.18 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for N4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT432_ALERT_2_C Short Inter X...Y Contact O3A .. C9 .. 2.99 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 7
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT793_ALERT_1_G Check the Absolute Configuration of C8 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C8A = ... R
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 8 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was prepared according to the literature method of Bi et al. (2007). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethyl acetate solution at room temperature over a period of five days.
All H atoms were located in difference Fourier maps and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å, and with Uiso(H) = 1.2 Ueq(C) H atoms.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C21H15FN4O3 | Z = 4 |
Mr = 390.37 | F(000) = 808 |
Triclinic, P1 | Dx = 1.401 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.6707 (10) Å | Cell parameters from 3056 reflections |
b = 10.762 (1) Å | θ = 2.4–21.2° |
c = 17.2223 (17) Å | µ = 0.10 mm−1 |
α = 81.199 (2)° | T = 293 K |
β = 72.270 (2)° | Plate, yellow |
γ = 81.439 (2)° | 0.30 × 0.23 × 0.09 mm |
V = 1850.6 (3) Å3 |
Siemens SMART 1000 CCD area detector diffractometer | 7131 independent reflections |
Radiation source: fine-focus sealed tube | 4047 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.0°, θmin = 1.9° |
ω scans | h = −13→8 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −13→10 |
Tmin = 0.970, Tmax = 0.991 | l = −21→21 |
10479 measured reflections |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0553P)2 + 0.1218P] where P = (Fo2 + 2Fc2)/3 |
7131 reflections | (Δ/σ)max < 0.001 |
523 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C21H15FN4O3 | γ = 81.439 (2)° |
Mr = 390.37 | V = 1850.6 (3) Å3 |
Triclinic, P1 | Z = 4 |
a = 10.6707 (10) Å | Mo Kα radiation |
b = 10.762 (1) Å | µ = 0.10 mm−1 |
c = 17.2223 (17) Å | T = 293 K |
α = 81.199 (2)° | 0.30 × 0.23 × 0.09 mm |
β = 72.270 (2)° |
Siemens SMART 1000 CCD area detector diffractometer | 7131 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 4047 reflections with I > 2σ(I) |
Tmin = 0.970, Tmax = 0.991 | Rint = 0.023 |
10479 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.19 e Å−3 |
7131 reflections | Δρmin = −0.17 e Å−3 |
523 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 | ||
O2A | 0.39562 (16) | 0.09554 (16) | 0.41047 (10) | 0.0512 (4) | |
O3A | 0.47972 (17) | 0.13222 (18) | 0.27434 (11) | 0.0621 (5) | |
N1A | 0.1189 (2) | 0.1451 (2) | 0.51728 (12) | 0.0512 (5) | |
O1A | 0.40691 (19) | −0.13192 (18) | 0.35481 (12) | 0.0706 (6) | |
C16A | 0.4876 (3) | 0.1366 (2) | 0.34208 (16) | 0.0480 (6) | |
C11A | 0.0596 (2) | 0.3109 (2) | 0.58218 (16) | 0.0525 (7) | |
N2A | 0.0131 (2) | 0.2112 (2) | 0.49600 (13) | 0.0585 (6) | |
C8A | 0.2799 (2) | 0.0603 (2) | 0.39568 (15) | 0.0493 (6) | |
H8AA | 0.2414 | 0.1311 | 0.3641 | 0.059* | |
N3A | −0.0237 (2) | 0.3117 (2) | 0.53464 (15) | 0.0642 (6) | |
C17A | 0.5965 (2) | 0.1878 (2) | 0.35919 (15) | 0.0460 (6) | |
C7A | 0.3126 (3) | −0.0571 (3) | 0.34981 (16) | 0.0528 (7) | |
C18A | 0.5934 (3) | 0.2156 (2) | 0.43539 (16) | 0.0556 (7) | |
H18A | 0.5215 | 0.1998 | 0.4810 | 0.067* | |
C5A | 0.1187 (3) | 0.0127 (3) | 0.29250 (17) | 0.0615 (8) | |
H5AA | 0.1014 | 0.0867 | 0.3174 | 0.074* | |
F1A | −0.0079 (2) | −0.1344 (2) | 0.16306 (12) | 0.1072 (7) | |
C10A | 0.1511 (2) | 0.2044 (2) | 0.57143 (15) | 0.0479 (6) | |
C6A | 0.2225 (3) | −0.0757 (2) | 0.30273 (15) | 0.0512 (7) | |
C9A | 0.1824 (3) | 0.0321 (2) | 0.47910 (16) | 0.0580 (7) | |
H9AA | 0.1151 | −0.0143 | 0.4733 | 0.070* | |
H9AB | 0.2285 | −0.0216 | 0.5147 | 0.070* | |
C4A | 0.0404 (3) | −0.0073 (3) | 0.24585 (19) | 0.0719 (9) | |
H4AA | −0.0290 | 0.0525 | 0.2389 | 0.086* | |
C21A | 0.7059 (3) | 0.2135 (3) | 0.29363 (18) | 0.0681 (8) | |
H21A | 0.7067 | 0.1961 | 0.2422 | 0.082* | |
C1A | 0.2441 (3) | −0.1856 (3) | 0.26559 (17) | 0.0652 (8) | |
H1AA | 0.3126 | −0.2467 | 0.2724 | 0.078* | |
N4A | 0.8100 (3) | 0.2616 (3) | 0.29966 (17) | 0.0844 (8) | |
C3A | 0.0671 (3) | −0.1165 (3) | 0.21022 (18) | 0.0712 (9) | |
C19A | 0.6996 (3) | 0.2675 (3) | 0.4422 (2) | 0.0651 (8) | |
H19A | 0.7000 | 0.2890 | 0.4924 | 0.078* | |
C15A | 0.2475 (3) | 0.1752 (3) | 0.61255 (17) | 0.0621 (8) | |
H15A | 0.3081 | 0.1033 | 0.6051 | 0.074* | |
C20A | 0.8048 (3) | 0.2870 (3) | 0.3736 (2) | 0.0742 (9) | |
H20A | 0.8768 | 0.3201 | 0.3793 | 0.089* | |
C2A | 0.1669 (3) | −0.2064 (3) | 0.21896 (19) | 0.0751 (9) | |
H2AB | 0.1827 | −0.2803 | 0.1940 | 0.090* | |
C12A | 0.0621 (3) | 0.3950 (3) | 0.63594 (19) | 0.0727 (9) | |
H12A | 0.0020 | 0.4672 | 0.6438 | 0.087* | |
C14A | 0.2474 (3) | 0.2590 (3) | 0.66453 (18) | 0.0749 (9) | |
H14A | 0.3102 | 0.2439 | 0.6932 | 0.090* | |
C34 | 0.1558 (3) | 0.3666 (3) | 0.67605 (19) | 0.0808 (10) | |
H34A | 0.1594 | 0.4206 | 0.7125 | 0.097* | |
O2 | 0.18536 (17) | 0.34784 (17) | 0.12407 (10) | 0.0577 (5) | |
O1 | 0.15018 (19) | 0.31998 (18) | 0.28409 (11) | 0.0650 (5) | |
F1 | 0.53088 (17) | 0.56755 (17) | 0.41166 (10) | 0.0858 (5) | |
C6 | 0.3252 (2) | 0.4266 (2) | 0.28601 (15) | 0.0448 (6) | |
N1 | 0.4293 (2) | 0.2424 (2) | 0.04113 (13) | 0.0565 (6) | |
C5 | 0.4421 (3) | 0.4800 (2) | 0.24456 (15) | 0.0545 (7) | |
H5A | 0.4736 | 0.4836 | 0.1877 | 0.065* | |
C3 | 0.4628 (3) | 0.5216 (3) | 0.36979 (17) | 0.0571 (7) | |
O3 | 0.0886 (2) | 0.5393 (2) | 0.15805 (13) | 0.0801 (6) | |
C8 | 0.2941 (2) | 0.3699 (3) | 0.15120 (15) | 0.0532 (7) | |
H8A | 0.3282 | 0.4500 | 0.1239 | 0.064* | |
C16 | 0.0848 (3) | 0.4427 (3) | 0.13211 (16) | 0.0590 (7) | |
C1 | 0.2796 (3) | 0.4238 (2) | 0.37101 (15) | 0.0536 (7) | |
H1A | 0.2015 | 0.3889 | 0.3995 | 0.064* | |
C7 | 0.2485 (3) | 0.3702 (2) | 0.24472 (16) | 0.0499 (7) | |
N2 | 0.5100 (2) | 0.3179 (2) | −0.01670 (15) | 0.0690 (7) | |
C9 | 0.3984 (3) | 0.2588 (3) | 0.12730 (15) | 0.0615 (8) | |
H9A | 0.4784 | 0.2721 | 0.1390 | 0.074* | |
H9B | 0.3668 | 0.1821 | 0.1604 | 0.074* | |
C4 | 0.5110 (3) | 0.5272 (3) | 0.28666 (17) | 0.0600 (7) | |
H4A | 0.5893 | 0.5624 | 0.2590 | 0.072* | |
C10 | 0.3852 (3) | 0.1612 (3) | 0.00545 (16) | 0.0570 (7) | |
C17 | −0.0236 (3) | 0.4136 (3) | 0.10463 (16) | 0.0646 (8) | |
C2 | 0.3481 (3) | 0.4716 (3) | 0.41365 (16) | 0.0588 (7) | |
H2B | 0.3174 | 0.4699 | 0.4704 | 0.071* | |
N3 | 0.5184 (3) | 0.2877 (3) | −0.08884 (15) | 0.0767 (8) | |
C11 | 0.4422 (3) | 0.1907 (3) | −0.07776 (17) | 0.0641 (8) | |
C18 | −0.0262 (4) | 0.3000 (4) | 0.0795 (2) | 0.1011 (12) | |
H18B | 0.0442 | 0.2376 | 0.0795 | 0.121* | |
C21 | −0.1282 (3) | 0.5052 (4) | 0.10457 (19) | 0.0964 (12) | |
H21B | −0.1291 | 0.5831 | 0.1219 | 0.116* | |
C12 | 0.4186 (4) | 0.1241 (4) | −0.1343 (2) | 0.0943 (12) | |
H12B | 0.4570 | 0.1421 | −0.1905 | 0.113* | |
N4 | −0.2318 (4) | 0.4816 (6) | 0.0788 (2) | 0.1501 (18) | |
C15 | 0.3031 (3) | 0.0657 (3) | 0.0367 (2) | 0.0856 (10) | |
H15B | 0.2657 | 0.0461 | 0.0928 | 0.103* | |
C13 | 0.3367 (4) | 0.0316 (5) | −0.1036 (3) | 0.1182 (16) | |
H13A | 0.3176 | −0.0134 | −0.1398 | 0.142* | |
C20 | −0.2216 (6) | 0.3631 (8) | 0.0530 (3) | 0.146 (3) | |
H20B | −0.2883 | 0.3459 | 0.0331 | 0.176* | |
C14 | 0.2805 (4) | 0.0020 (4) | −0.0195 (3) | 0.1170 (15) | |
H14B | 0.2261 | −0.0628 | −0.0012 | 0.140* | |
C19 | −0.1251 (5) | 0.2755 (5) | 0.0551 (3) | 0.1293 (18) | |
H19B | −0.1254 | 0.1965 | 0.0396 | 0.155* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2A | 0.0482 (11) | 0.0598 (12) | 0.0476 (10) | −0.0126 (9) | −0.0118 (9) | −0.0095 (8) |
O3A | 0.0595 (12) | 0.0841 (14) | 0.0464 (11) | −0.0101 (10) | −0.0189 (9) | −0.0090 (10) |
N1A | 0.0438 (13) | 0.0532 (14) | 0.0574 (14) | −0.0048 (11) | −0.0114 (11) | −0.0157 (11) |
O1A | 0.0702 (14) | 0.0612 (13) | 0.0848 (15) | 0.0125 (11) | −0.0307 (11) | −0.0234 (11) |
C16A | 0.0487 (16) | 0.0478 (16) | 0.0467 (16) | −0.0022 (12) | −0.0131 (14) | −0.0070 (12) |
C11A | 0.0412 (15) | 0.0570 (18) | 0.0563 (16) | −0.0048 (13) | −0.0043 (13) | −0.0181 (13) |
N2A | 0.0462 (14) | 0.0699 (16) | 0.0617 (15) | −0.0075 (12) | −0.0149 (12) | −0.0144 (12) |
C8A | 0.0421 (15) | 0.0527 (16) | 0.0558 (16) | −0.0070 (12) | −0.0137 (13) | −0.0134 (13) |
N3A | 0.0520 (15) | 0.0661 (17) | 0.0741 (16) | −0.0007 (12) | −0.0150 (13) | −0.0192 (13) |
C17A | 0.0428 (15) | 0.0439 (15) | 0.0513 (15) | −0.0023 (12) | −0.0152 (13) | −0.0049 (12) |
C7A | 0.0485 (17) | 0.0496 (17) | 0.0569 (17) | −0.0028 (14) | −0.0094 (14) | −0.0106 (13) |
C18A | 0.0538 (17) | 0.0585 (18) | 0.0563 (17) | −0.0077 (14) | −0.0176 (14) | −0.0075 (13) |
C5A | 0.0561 (18) | 0.0599 (19) | 0.074 (2) | −0.0049 (15) | −0.0195 (16) | −0.0258 (15) |
F1A | 0.1093 (16) | 0.1380 (18) | 0.1016 (15) | −0.0357 (13) | −0.0512 (13) | −0.0319 (13) |
C10A | 0.0431 (15) | 0.0533 (17) | 0.0476 (15) | −0.0129 (13) | −0.0088 (12) | −0.0078 (12) |
C6A | 0.0487 (16) | 0.0480 (16) | 0.0565 (16) | −0.0082 (13) | −0.0092 (13) | −0.0140 (13) |
C9A | 0.0505 (17) | 0.0536 (17) | 0.0683 (19) | −0.0106 (13) | −0.0067 (14) | −0.0192 (14) |
C4A | 0.059 (2) | 0.079 (2) | 0.084 (2) | −0.0080 (16) | −0.0262 (17) | −0.0186 (18) |
C21A | 0.058 (2) | 0.089 (2) | 0.0608 (19) | −0.0156 (17) | −0.0179 (16) | −0.0089 (16) |
C1A | 0.069 (2) | 0.0535 (18) | 0.075 (2) | −0.0069 (15) | −0.0175 (16) | −0.0217 (15) |
N4A | 0.0597 (17) | 0.114 (2) | 0.084 (2) | −0.0296 (16) | −0.0209 (15) | −0.0053 (17) |
C3A | 0.069 (2) | 0.091 (3) | 0.065 (2) | −0.0268 (19) | −0.0231 (17) | −0.0172 (18) |
C19A | 0.071 (2) | 0.0580 (19) | 0.078 (2) | −0.0090 (16) | −0.0361 (19) | −0.0124 (16) |
C15A | 0.0603 (19) | 0.0616 (19) | 0.0675 (19) | −0.0084 (14) | −0.0234 (16) | −0.0048 (15) |
C20A | 0.064 (2) | 0.068 (2) | 0.102 (3) | −0.0192 (16) | −0.041 (2) | 0.0037 (19) |
C2A | 0.085 (2) | 0.067 (2) | 0.082 (2) | −0.0195 (19) | −0.0213 (19) | −0.0316 (17) |
C12A | 0.060 (2) | 0.073 (2) | 0.083 (2) | −0.0047 (16) | −0.0072 (17) | −0.0351 (18) |
C14A | 0.069 (2) | 0.098 (3) | 0.068 (2) | −0.0207 (19) | −0.0296 (17) | −0.0106 (19) |
C34 | 0.078 (2) | 0.095 (3) | 0.075 (2) | −0.021 (2) | −0.0118 (19) | −0.0384 (19) |
O2 | 0.0588 (12) | 0.0638 (12) | 0.0590 (11) | 0.0043 (10) | −0.0273 (10) | −0.0222 (9) |
O1 | 0.0639 (13) | 0.0782 (14) | 0.0583 (12) | −0.0212 (11) | −0.0179 (10) | −0.0111 (10) |
F1 | 0.0943 (13) | 0.1025 (14) | 0.0828 (12) | −0.0319 (10) | −0.0438 (11) | −0.0190 (10) |
C6 | 0.0481 (16) | 0.0450 (15) | 0.0453 (15) | −0.0041 (12) | −0.0173 (13) | −0.0101 (12) |
N1 | 0.0498 (14) | 0.0728 (16) | 0.0466 (13) | −0.0011 (12) | −0.0121 (11) | −0.0150 (12) |
C5 | 0.0596 (18) | 0.0615 (18) | 0.0427 (15) | −0.0092 (14) | −0.0119 (14) | −0.0094 (13) |
C3 | 0.0638 (19) | 0.0563 (18) | 0.0631 (19) | −0.0077 (15) | −0.0319 (16) | −0.0142 (14) |
O3 | 0.0834 (15) | 0.0709 (15) | 0.0931 (16) | 0.0114 (12) | −0.0342 (13) | −0.0319 (12) |
C8 | 0.0544 (17) | 0.0633 (18) | 0.0486 (15) | −0.0025 (14) | −0.0221 (13) | −0.0158 (13) |
C16 | 0.0591 (19) | 0.068 (2) | 0.0495 (16) | 0.0007 (16) | −0.0164 (14) | −0.0126 (15) |
C1 | 0.0526 (17) | 0.0604 (18) | 0.0480 (16) | −0.0104 (13) | −0.0110 (13) | −0.0101 (13) |
C7 | 0.0506 (17) | 0.0494 (16) | 0.0492 (16) | −0.0005 (13) | −0.0143 (14) | −0.0086 (13) |
N2 | 0.0590 (16) | 0.0821 (19) | 0.0634 (17) | −0.0071 (14) | −0.0114 (14) | −0.0141 (14) |
C9 | 0.0636 (19) | 0.077 (2) | 0.0457 (16) | 0.0067 (15) | −0.0206 (14) | −0.0165 (14) |
C4 | 0.0548 (18) | 0.0674 (19) | 0.0613 (18) | −0.0196 (14) | −0.0154 (15) | −0.0084 (15) |
C10 | 0.0533 (18) | 0.0668 (19) | 0.0485 (16) | 0.0036 (15) | −0.0096 (14) | −0.0201 (14) |
C17 | 0.0519 (19) | 0.093 (2) | 0.0476 (16) | −0.0052 (17) | −0.0169 (14) | −0.0018 (16) |
C2 | 0.067 (2) | 0.070 (2) | 0.0422 (15) | −0.0093 (16) | −0.0165 (15) | −0.0134 (14) |
N3 | 0.0768 (19) | 0.091 (2) | 0.0516 (16) | −0.0022 (16) | −0.0080 (14) | −0.0053 (14) |
C11 | 0.0580 (19) | 0.082 (2) | 0.0498 (17) | 0.0051 (17) | −0.0124 (15) | −0.0186 (16) |
C18 | 0.090 (3) | 0.120 (3) | 0.116 (3) | −0.023 (2) | −0.055 (2) | −0.019 (3) |
C21 | 0.057 (2) | 0.154 (4) | 0.071 (2) | 0.013 (2) | −0.0203 (18) | −0.008 (2) |
C12 | 0.093 (3) | 0.132 (4) | 0.060 (2) | 0.008 (2) | −0.020 (2) | −0.040 (2) |
N4 | 0.068 (2) | 0.273 (6) | 0.095 (3) | −0.013 (3) | −0.024 (2) | 0.018 (3) |
C15 | 0.088 (3) | 0.085 (3) | 0.075 (2) | −0.023 (2) | 0.0029 (19) | −0.0255 (19) |
C13 | 0.103 (3) | 0.155 (4) | 0.112 (4) | −0.006 (3) | −0.027 (3) | −0.081 (3) |
C20 | 0.089 (4) | 0.275 (9) | 0.093 (4) | −0.074 (5) | −0.041 (3) | 0.008 (4) |
C14 | 0.107 (3) | 0.113 (3) | 0.133 (4) | −0.034 (2) | −0.003 (3) | −0.065 (3) |
C19 | 0.099 (3) | 0.162 (5) | 0.168 (5) | −0.046 (3) | −0.077 (3) | −0.034 (3) |
O2A—C16A | 1.346 (3) | O2—C16 | 1.356 (3) |
O2A—C8A | 1.447 (3) | O2—C8 | 1.438 (3) |
O3A—C16A | 1.204 (3) | O1—C7 | 1.215 (3) |
N1A—C10A | 1.356 (3) | F1—C3 | 1.352 (3) |
N1A—N2A | 1.360 (3) | C6—C1 | 1.392 (3) |
N1A—C9A | 1.449 (3) | C6—C5 | 1.393 (3) |
O1A—C7A | 1.208 (3) | C6—C7 | 1.476 (3) |
C16A—C17A | 1.479 (3) | N1—C10 | 1.351 (3) |
C11A—N3A | 1.378 (3) | N1—N2 | 1.353 (3) |
C11A—C10A | 1.387 (3) | N1—C9 | 1.451 (3) |
C11A—C12A | 1.399 (3) | C5—C4 | 1.369 (3) |
N2A—N3A | 1.305 (3) | C5—H5A | 0.9300 |
C8A—C9A | 1.513 (3) | C3—C4 | 1.361 (4) |
C8A—C7A | 1.532 (3) | C3—C2 | 1.366 (4) |
C8A—H8AA | 0.9800 | O3—C16 | 1.204 (3) |
C17A—C18A | 1.380 (3) | C8—C9 | 1.521 (3) |
C17A—C21A | 1.383 (4) | C8—C7 | 1.534 (3) |
C7A—C6A | 1.485 (3) | C8—H8A | 0.9800 |
C18A—C19A | 1.378 (3) | C16—C17 | 1.465 (4) |
C18A—H18A | 0.9300 | C1—C2 | 1.376 (3) |
C5A—C4A | 1.380 (3) | C1—H1A | 0.9300 |
C5A—C6A | 1.385 (3) | N2—N3 | 1.305 (3) |
C5A—H5AA | 0.9300 | C9—H9A | 0.9700 |
F1A—C3A | 1.352 (3) | C9—H9B | 0.9700 |
C10A—C15A | 1.392 (3) | C4—H4A | 0.9300 |
C6A—C1A | 1.386 (3) | C10—C11 | 1.383 (4) |
C9A—H9AA | 0.9700 | C10—C15 | 1.388 (4) |
C9A—H9AB | 0.9700 | C17—C18 | 1.365 (4) |
C4A—C3A | 1.361 (4) | C17—C21 | 1.374 (4) |
C4A—H4AA | 0.9300 | C2—H2B | 0.9300 |
C21A—N4A | 1.330 (3) | N3—C11 | 1.373 (4) |
C21A—H21A | 0.9300 | C11—C12 | 1.394 (4) |
C1A—C2A | 1.374 (4) | C18—C19 | 1.323 (4) |
C1A—H1AA | 0.9300 | C18—H18B | 0.9300 |
N4A—C20A | 1.326 (4) | C21—N4 | 1.378 (5) |
C3A—C2A | 1.356 (4) | C21—H21B | 0.9300 |
C19A—C20A | 1.374 (4) | C12—C13 | 1.360 (5) |
C19A—H19A | 0.9300 | C12—H12B | 0.9300 |
C15A—C14A | 1.364 (4) | N4—C20 | 1.392 (7) |
C15A—H15A | 0.9300 | C15—C14 | 1.362 (4) |
C20A—H20A | 0.9300 | C15—H15B | 0.9300 |
C2A—H2AB | 0.9300 | C13—C14 | 1.395 (6) |
C12A—C34 | 1.355 (4) | C13—H13A | 0.9300 |
C12A—H12A | 0.9300 | C20—C19 | 1.294 (7) |
C14A—C34 | 1.397 (4) | C20—H20B | 0.9300 |
C14A—H14A | 0.9300 | C14—H14B | 0.9300 |
C34—H34A | 0.9300 | C19—H19B | 0.9300 |
C16A—O2A—C8A | 114.21 (19) | C16—O2—C8 | 115.0 (2) |
C10A—N1A—N2A | 110.4 (2) | C1—C6—C5 | 118.4 (2) |
C10A—N1A—C9A | 130.2 (2) | C1—C6—C7 | 118.1 (2) |
N2A—N1A—C9A | 119.4 (2) | C5—C6—C7 | 123.4 (2) |
O3A—C16A—O2A | 122.4 (2) | C10—N1—N2 | 110.3 (2) |
O3A—C16A—C17A | 124.3 (2) | C10—N1—C9 | 129.4 (2) |
O2A—C16A—C17A | 113.2 (2) | N2—N1—C9 | 120.3 (2) |
N3A—C11A—C10A | 109.1 (2) | C4—C5—C6 | 120.7 (2) |
N3A—C11A—C12A | 130.9 (3) | C4—C5—H5A | 119.7 |
C10A—C11A—C12A | 120.0 (3) | C6—C5—H5A | 119.7 |
N3A—N2A—N1A | 108.8 (2) | F1—C3—C4 | 118.9 (3) |
O2A—C8A—C9A | 106.4 (2) | F1—C3—C2 | 117.8 (2) |
O2A—C8A—C7A | 111.9 (2) | C4—C3—C2 | 123.3 (2) |
C9A—C8A—C7A | 109.5 (2) | O2—C8—C9 | 104.8 (2) |
O2A—C8A—H8AA | 109.7 | O2—C8—C7 | 109.3 (2) |
C9A—C8A—H8AA | 109.7 | C9—C8—C7 | 110.3 (2) |
C7A—C8A—H8AA | 109.7 | O2—C8—H8A | 110.7 |
N2A—N3A—C11A | 107.7 (2) | C9—C8—H8A | 110.7 |
C18A—C17A—C21A | 118.3 (3) | C7—C8—H8A | 110.7 |
C18A—C17A—C16A | 124.2 (2) | O3—C16—O2 | 122.1 (3) |
C21A—C17A—C16A | 117.4 (2) | O3—C16—C17 | 125.5 (3) |
O1A—C7A—C6A | 122.6 (2) | O2—C16—C17 | 112.4 (3) |
O1A—C7A—C8A | 119.8 (2) | C2—C1—C6 | 121.2 (3) |
C6A—C7A—C8A | 117.6 (2) | C2—C1—H1A | 119.4 |
C19A—C18A—C17A | 118.3 (3) | C6—C1—H1A | 119.4 |
C19A—C18A—H18A | 120.9 | O1—C7—C6 | 120.8 (2) |
C17A—C18A—H18A | 120.9 | O1—C7—C8 | 118.6 (2) |
C4A—C5A—C6A | 121.0 (3) | C6—C7—C8 | 120.5 (2) |
C4A—C5A—H5AA | 119.5 | N3—N2—N1 | 108.5 (2) |
C6A—C5A—H5AA | 119.5 | N1—C9—C8 | 112.3 (2) |
N1A—C10A—C11A | 104.1 (2) | N1—C9—H9A | 109.1 |
N1A—C10A—C15A | 133.0 (2) | C8—C9—H9A | 109.1 |
C11A—C10A—C15A | 122.9 (2) | N1—C9—H9B | 109.1 |
C5A—C6A—C1A | 117.9 (2) | C8—C9—H9B | 109.1 |
C5A—C6A—C7A | 123.2 (2) | H9A—C9—H9B | 107.9 |
C1A—C6A—C7A | 118.9 (2) | C3—C4—C5 | 118.7 (3) |
N1A—C9A—C8A | 113.0 (2) | C3—C4—H4A | 120.7 |
N1A—C9A—H9AA | 109.0 | C5—C4—H4A | 120.7 |
C8A—C9A—H9AA | 109.0 | N1—C10—C11 | 104.6 (3) |
N1A—C9A—H9AB | 109.0 | N1—C10—C15 | 133.0 (3) |
C8A—C9A—H9AB | 109.0 | C11—C10—C15 | 122.5 (3) |
H9AA—C9A—H9AB | 107.8 | C18—C17—C21 | 118.4 (3) |
C3A—C4A—C5A | 118.5 (3) | C18—C17—C16 | 123.2 (3) |
C3A—C4A—H4AA | 120.8 | C21—C17—C16 | 118.3 (3) |
C5A—C4A—H4AA | 120.8 | C3—C2—C1 | 117.8 (2) |
N4A—C21A—C17A | 124.0 (3) | C3—C2—H2B | 121.1 |
N4A—C21A—H21A | 118.0 | C1—C2—H2B | 121.1 |
C17A—C21A—H21A | 118.0 | N2—N3—C11 | 108.1 (2) |
C2A—C1A—C6A | 121.6 (3) | N3—C11—C10 | 108.5 (3) |
C2A—C1A—H1AA | 119.2 | N3—C11—C12 | 131.0 (3) |
C6A—C1A—H1AA | 119.2 | C10—C11—C12 | 120.5 (3) |
C20A—N4A—C21A | 116.5 (3) | C19—C18—C17 | 122.3 (4) |
F1A—C3A—C2A | 119.0 (3) | C19—C18—H18B | 118.8 |
F1A—C3A—C4A | 118.3 (3) | C17—C18—H18B | 118.8 |
C2A—C3A—C4A | 122.8 (3) | C17—C21—N4 | 120.0 (4) |
C20A—C19A—C18A | 118.9 (3) | C17—C21—H21B | 120.0 |
C20A—C19A—H19A | 120.6 | N4—C21—H21B | 120.0 |
C18A—C19A—H19A | 120.6 | C13—C12—C11 | 116.9 (4) |
C14A—C15A—C10A | 115.7 (3) | C13—C12—H12B | 121.6 |
C14A—C15A—H15A | 122.2 | C11—C12—H12B | 121.6 |
C10A—C15A—H15A | 122.2 | C21—N4—C20 | 116.2 (5) |
N4A—C20A—C19A | 124.0 (3) | C14—C15—C10 | 116.3 (3) |
N4A—C20A—H20A | 118.0 | C14—C15—H15B | 121.9 |
C19A—C20A—H20A | 118.0 | C10—C15—H15B | 121.9 |
C3A—C2A—C1A | 118.3 (3) | C12—C13—C14 | 122.2 (4) |
C3A—C2A—H2AB | 120.9 | C12—C13—H13A | 118.9 |
C1A—C2A—H2AB | 120.9 | C14—C13—H13A | 118.9 |
C34—C12A—C11A | 117.1 (3) | C19—C20—N4 | 124.0 (5) |
C34—C12A—H12A | 121.4 | C19—C20—H20B | 118.0 |
C11A—C12A—H12A | 121.4 | N4—C20—H20B | 118.0 |
C15A—C14A—C34 | 122.1 (3) | C15—C14—C13 | 121.7 (4) |
C15A—C14A—H14A | 119.0 | C15—C14—H14B | 119.1 |
C34—C14A—H14A | 119.0 | C13—C14—H14B | 119.1 |
C12A—C34—C14A | 122.2 (3) | C20—C19—C18 | 119.0 (5) |
C12A—C34—H34A | 118.9 | C20—C19—H19B | 120.5 |
C14A—C34—H34A | 118.9 | C18—C19—H19B | 120.5 |
C8A—O2A—C16A—O3A | −7.0 (3) | C1—C6—C5—C4 | 0.7 (4) |
C8A—O2A—C16A—C17A | 172.41 (19) | C7—C6—C5—C4 | −177.9 (2) |
C10A—N1A—N2A—N3A | 0.2 (3) | C16—O2—C8—C9 | −173.9 (2) |
C9A—N1A—N2A—N3A | −176.9 (2) | C16—O2—C8—C7 | 67.8 (3) |
C16A—O2A—C8A—C9A | −173.48 (19) | C8—O2—C16—O3 | 1.9 (4) |
C16A—O2A—C8A—C7A | 67.0 (3) | C8—O2—C16—C17 | −179.1 (2) |
N1A—N2A—N3A—C11A | −0.2 (3) | C5—C6—C1—C2 | −0.4 (4) |
C10A—C11A—N3A—N2A | 0.1 (3) | C7—C6—C1—C2 | 178.3 (2) |
C12A—C11A—N3A—N2A | −178.9 (3) | C1—C6—C7—O1 | −1.8 (4) |
O3A—C16A—C17A—C18A | 166.8 (2) | C5—C6—C7—O1 | 176.8 (2) |
O2A—C16A—C17A—C18A | −12.6 (3) | C1—C6—C7—C8 | −179.7 (2) |
O3A—C16A—C17A—C21A | −10.7 (4) | C5—C6—C7—C8 | −1.1 (4) |
O2A—C16A—C17A—C21A | 169.9 (2) | O2—C8—C7—O1 | 20.1 (3) |
O2A—C8A—C7A—O1A | 25.2 (3) | C9—C8—C7—O1 | −94.7 (3) |
C9A—C8A—C7A—O1A | −92.5 (3) | O2—C8—C7—C6 | −162.0 (2) |
O2A—C8A—C7A—C6A | −156.8 (2) | C9—C8—C7—C6 | 83.3 (3) |
C9A—C8A—C7A—C6A | 85.5 (3) | C10—N1—N2—N3 | 0.3 (3) |
C21A—C17A—C18A—C19A | −0.1 (4) | C9—N1—N2—N3 | −177.7 (2) |
C16A—C17A—C18A—C19A | −177.5 (2) | C10—N1—C9—C8 | −99.2 (3) |
N2A—N1A—C10A—C11A | −0.2 (3) | N2—N1—C9—C8 | 78.4 (3) |
C9A—N1A—C10A—C11A | 176.6 (2) | O2—C8—C9—N1 | 53.2 (3) |
N2A—N1A—C10A—C15A | 178.4 (3) | C7—C8—C9—N1 | 170.8 (2) |
C9A—N1A—C10A—C15A | −4.8 (5) | F1—C3—C4—C5 | 179.7 (2) |
N3A—C11A—C10A—N1A | 0.0 (3) | C2—C3—C4—C5 | −0.3 (4) |
C12A—C11A—C10A—N1A | 179.2 (2) | C6—C5—C4—C3 | −0.4 (4) |
N3A—C11A—C10A—C15A | −178.7 (2) | N2—N1—C10—C11 | −0.3 (3) |
C12A—C11A—C10A—C15A | 0.4 (4) | C9—N1—C10—C11 | 177.5 (2) |
C4A—C5A—C6A—C1A | −0.9 (4) | N2—N1—C10—C15 | 179.2 (3) |
C4A—C5A—C6A—C7A | 177.8 (3) | C9—N1—C10—C15 | −3.0 (5) |
O1A—C7A—C6A—C5A | −176.1 (3) | O3—C16—C17—C18 | −176.7 (3) |
C8A—C7A—C6A—C5A | 6.0 (4) | O2—C16—C17—C18 | 4.4 (4) |
O1A—C7A—C6A—C1A | 2.6 (4) | O3—C16—C17—C21 | 3.0 (4) |
C8A—C7A—C6A—C1A | −175.3 (2) | O2—C16—C17—C21 | −175.9 (3) |
C10A—N1A—C9A—C8A | −94.4 (3) | F1—C3—C2—C1 | −179.4 (2) |
N2A—N1A—C9A—C8A | 82.2 (3) | C4—C3—C2—C1 | 0.6 (4) |
O2A—C8A—C9A—N1A | 74.7 (3) | C6—C1—C2—C3 | −0.2 (4) |
C7A—C8A—C9A—N1A | −164.2 (2) | N1—N2—N3—C11 | −0.2 (3) |
C6A—C5A—C4A—C3A | 0.3 (5) | N2—N3—C11—C10 | 0.0 (3) |
C18A—C17A—C21A—N4A | 1.3 (4) | N2—N3—C11—C12 | −179.4 (3) |
C16A—C17A—C21A—N4A | 178.9 (3) | N1—C10—C11—N3 | 0.2 (3) |
C5A—C6A—C1A—C2A | 1.0 (4) | C15—C10—C11—N3 | −179.4 (3) |
C7A—C6A—C1A—C2A | −177.8 (3) | N1—C10—C11—C12 | 179.7 (3) |
C17A—C21A—N4A—C20A | −1.0 (5) | C15—C10—C11—C12 | 0.1 (4) |
C5A—C4A—C3A—F1A | −178.5 (3) | C21—C17—C18—C19 | 0.1 (6) |
C5A—C4A—C3A—C2A | 0.3 (5) | C16—C17—C18—C19 | 179.8 (4) |
C17A—C18A—C19A—C20A | −1.3 (4) | C18—C17—C21—N4 | −0.6 (5) |
N1A—C10A—C15A—C14A | −178.7 (3) | C16—C17—C21—N4 | 179.7 (3) |
C11A—C10A—C15A—C14A | −0.4 (4) | N3—C11—C12—C13 | −179.9 (4) |
C21A—N4A—C20A—C19A | −0.5 (5) | C10—C11—C12—C13 | 0.8 (5) |
C18A—C19A—C20A—N4A | 1.6 (5) | C17—C21—N4—C20 | −0.7 (6) |
F1A—C3A—C2A—C1A | 178.6 (3) | N1—C10—C15—C14 | −179.9 (3) |
C4A—C3A—C2A—C1A | −0.2 (5) | C11—C10—C15—C14 | −0.4 (5) |
C6A—C1A—C2A—C3A | −0.4 (5) | C11—C12—C13—C14 | −1.2 (6) |
N3A—C11A—C12A—C34 | 178.5 (3) | C21—N4—C20—C19 | 2.7 (8) |
C10A—C11A—C12A—C34 | −0.4 (4) | C10—C15—C14—C13 | 0.0 (6) |
C10A—C15A—C14A—C34 | 0.4 (4) | C12—C13—C14—C15 | 0.9 (7) |
C11A—C12A—C34—C14A | 0.4 (5) | N4—C20—C19—C18 | −3.2 (9) |
C15A—C14A—C34—C12A | −0.4 (5) | C17—C18—C19—C20 | 1.7 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···Cg2 | 0.93 | 2.84 | 3.654 (2) | 147 |
C8A—H8AA···O1 | 0.98 | 2.52 | 3.499 (3) | 177 |
C5A—H5AA···O1 | 0.93 | 2.58 | 3.350 (4) | 140 |
C9A—H9AA···N2Ai | 0.97 | 2.59 | 3.483 (4) | 153 |
C2A—H2AB···O3ii | 0.93 | 2.55 | 3.374 (4) | 148 |
C9—H9A···O3A | 0.97 | 2.58 | 2.992 (3) | 106 |
C9—H9B···O3A | 0.97 | 2.55 | 2.992 (3) | 108 |
C18—H18B···O2 | 0.93 | 2.40 | 2.734 (5) | 101 |
C20—H20B···N2iii | 0.93 | 2.62 | 3.545 (7) | 174 |
C21A—H21A···O3A | 0.93 | 2.49 | 2.812 (4) | 100 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x, y−1, z; (iii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C21H15FN4O3 |
Mr | 390.37 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 10.6707 (10), 10.762 (1), 17.2223 (17) |
α, β, γ (°) | 81.199 (2), 72.270 (2), 81.439 (2) |
V (Å3) | 1850.6 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.30 × 0.23 × 0.09 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD area detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.970, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10479, 7131, 4047 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.143, 1.00 |
No. of reflections | 7131 |
No. of parameters | 523 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.17 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···Cg2 | 0.93 | 2.838 | 3.654 (2) | 147.21 |
C8A—H8AA···O1 | 0.98 | 2.520 | 3.499 (3) | 177.12 |
C5A—H5AA···O1 | 0.93 | 2.582 | 3.350 (4) | 140.20 |
C9A—H9AA···N2Ai | 0.97 | 2.592 | 3.483 (4) | 152.67 |
C2A—H2AB···O3ii | 0.93 | 2.547 | 3.374 (4) | 148.15 |
C9—H9A···O3A | 0.97 | 2.577 | 2.992 (3) | 105.96 |
C9—H9B···O3A | 0.97 | 2.553 | 2.992 (3) | 107.56 |
C18—H18B···O2 | 0.93 | 2.404 | 2.734 (5) | 100.66 |
C20—H20B···N2iii | 0.93 | 2.618 | 3.545 (7) | 174.22 |
C21A—H21A···O3A | 0.93 | 2.492 | 2.812 (4) | 100.35 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x, y−1, z; (iii) x−1, y, z. |
Recently we have reported the structure of 3-(1H-benzotriazol-1-yl)-1-(4-fluorophenyl)-1-oxopropan-2-yl 2,4-dichlorobenzoate (II) (Bi et al., 2007). As part of our ongoing studies on new triazole compounds with higher bioactivity, the title compound, (I), was synthesized and its structure is shown here.
The asymmetric unit of (I) contains two molecules A and B (Fig. 1). All bond lengths and angles are within normal ranges (Allen et al., 1987) and are comparable with those in the related compound, (II). The benzotriazole units, N1—N3/C10/C15 and N1A—N3A/C10A/C15A, are essentially planar, with dihedral angles of 0.29 (2) and 1.13 (1)°, respectively. The dihedral angles between rings A(C1—C6), B(N4/C17—C21), C(C1A—C6A) and D(N4A/C17A—C21A) are A/B = 78.97 (2)° and C/D = 72.49 (1)°. The dihedral angles between the benzotriazole units E(N1—N3/C10—C15) and F(N1A—N3A/C10A—C15A) and A, B, C and D are E/A = 22.29 (1)°, E/B = 89.41 (2)°, F/C = 6.24 (1)° and F/D = 69.53 (1)°, respectively. Intramolecular C18—H18B···O2 and C21A—H21A···O3A interactions (Table 2) result in the information of two five-numbered rings.
In the crystal structure, molecules are linked into infinite chains along the b axis by C—H···O intermolecular hydrogen bonds (Table 2). The chains are also linked by C—H···N interactions along a axis (Table 2). The packing is further stabilized by C—H···π interactions (Table 2).