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
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).