Supporting information
CCDC references: 138560; 138561; 138562; 138563; 138564; 138565
For all compounds, data collection: CAD4, Enraf-Nonius, 1984; cell refinement: CAD4, Enraf-Nonius, 1984; data reduction: MolEN, C.K. Fair, Enraf-Nonius, 1990; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: ORTEPII, (Johnson, 1976) for a1; ORTEPII, Johnson, 1976 for a2; ORTEPII (Johnson, 1976) for a3, a4, a5, a6. Software used to prepare material for publication: PARST (Nardelli, 1983, 1995), SHELXL97 (Sheldrick, 1997) for a1, a2, a3; PARST (Nardelli, 1983; 1995),SHELXL97 (Sheldrick, 1997) for a4; PARST (Nardelli, 1983; 1995), SHELXL97 (Sheldrick, 1997) for a5; PARST (Nardelli, 1983;1995),SHELXL97 (Sheldrick, 1997) for a6.
C11H8N4O | F(000) = 440 |
Mr = 212.21 | Dx = 1.287 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 7.196 (3) Å | θ = 7–12° |
b = 14.125 (2) Å | µ = 0.09 mm−1 |
c = 10.862 (2) Å | T = 293 K |
β = 97.34 (3)° | Needle, pale yellow |
V = 1095.0 (5) Å3 | 0.43 × 0.12 × 0.10 mm |
Z = 4 |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.030 |
Radiation source: fine-focus sealed tube | θmax = 27.0°, θmin = 2.4° |
Graphite monochromator | h = 0→9 |
ω/2θ scans | k = 0→18 |
2556 measured reflections | l = −13→13 |
2366 independent reflections | 3 standard reflections every 120 min |
1102 reflections with I > 2σ(I) | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.063 | All H-atom parameters refined |
wR(F2) = 0.169 | w = 1/[σ2(Fo2) + (0.0852P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.95 | (Δ/σ)max = 0.029 |
2366 reflections | Δρmax = 0.18 e Å−3 |
178 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.002 (3) |
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 | ||
O1 | 0.0782 (3) | −0.24978 (15) | 0.34765 (19) | 0.0696 (7) | |
N1 | −0.1995 (3) | −0.10435 (16) | −0.0056 (2) | 0.0475 (6) | |
N2 | −0.1416 (3) | −0.10652 (14) | 0.11385 (18) | 0.0441 (6) | |
N3 | −0.0347 (5) | −0.3376 (2) | 0.0472 (3) | 0.1024 (12) | |
N4 | −0.5340 (4) | 0.2995 (2) | −0.2765 (3) | 0.0941 (11) | |
C1 | −0.0035 (4) | −0.1809 (2) | 0.3003 (3) | 0.0533 (7) | |
C2 | −0.0725 (4) | −0.18337 (18) | 0.1674 (2) | 0.0458 (7) | |
C3 | −0.0398 (7) | −0.0954 (3) | 0.3737 (4) | 0.0759 (11) | |
C4 | −0.0517 (4) | −0.2703 (2) | 0.1023 (3) | 0.0620 (9) | |
C5 | −0.2681 (3) | −0.02011 (17) | −0.0613 (2) | 0.0397 (6) | |
C6 | −0.3343 (4) | −0.0211 (2) | −0.1863 (3) | 0.0540 (8) | |
C7 | −0.4039 (4) | 0.0608 (2) | −0.2437 (3) | 0.0571 (8) | |
C8 | −0.4068 (4) | 0.14297 (19) | −0.1751 (3) | 0.0514 (7) | |
C9 | −0.3401 (4) | 0.1431 (2) | −0.0501 (3) | 0.0520 (7) | |
C10 | −0.2693 (4) | 0.06204 (18) | 0.0077 (3) | 0.0457 (7) | |
C11 | −0.4784 (4) | 0.2298 (2) | −0.2325 (3) | 0.0679 (9) | |
H1 | −0.201 (3) | −0.1529 (18) | −0.045 (2) | 0.038 (7)* | |
H31 | 0.037 (6) | −0.093 (3) | 0.446 (4) | 0.129 (16)* | |
H32 | −0.030 (5) | −0.038 (3) | 0.326 (4) | 0.108 (13)* | |
H33 | −0.167 (8) | −0.094 (4) | 0.389 (5) | 0.18 (2)* | |
H6 | −0.333 (3) | −0.0763 (18) | −0.238 (2) | 0.047 (7)* | |
H7 | −0.453 (4) | 0.0597 (17) | −0.326 (3) | 0.052 (8)* | |
H9 | −0.345 (4) | 0.1941 (19) | −0.014 (3) | 0.053 (9)* | |
H10 | −0.231 (4) | 0.0627 (19) | 0.097 (3) | 0.076 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0827 (15) | 0.0651 (13) | 0.0577 (13) | 0.0121 (12) | −0.0030 (10) | 0.0168 (11) |
N1 | 0.0633 (16) | 0.0372 (14) | 0.0392 (13) | 0.0006 (11) | −0.0035 (10) | −0.0018 (11) |
N2 | 0.0449 (13) | 0.0438 (12) | 0.0428 (13) | −0.0032 (10) | 0.0021 (9) | 0.0065 (10) |
N3 | 0.171 (3) | 0.0585 (18) | 0.069 (2) | 0.021 (2) | −0.0155 (19) | −0.0086 (16) |
N4 | 0.104 (2) | 0.082 (2) | 0.096 (2) | 0.0215 (18) | 0.0064 (18) | 0.0364 (18) |
C1 | 0.0556 (18) | 0.0551 (18) | 0.0485 (18) | 0.0004 (14) | 0.0042 (13) | 0.0113 (14) |
C2 | 0.0507 (17) | 0.0442 (15) | 0.0420 (15) | 0.0011 (13) | 0.0037 (12) | 0.0037 (12) |
C3 | 0.106 (4) | 0.069 (2) | 0.050 (2) | 0.013 (2) | 0.000 (2) | −0.0050 (18) |
C4 | 0.086 (2) | 0.0459 (17) | 0.0508 (18) | 0.0064 (16) | −0.0056 (15) | 0.0052 (14) |
C5 | 0.0412 (15) | 0.0373 (13) | 0.0400 (14) | −0.0051 (11) | 0.0027 (11) | 0.0036 (11) |
C6 | 0.067 (2) | 0.0461 (16) | 0.0452 (16) | −0.0052 (14) | −0.0062 (13) | 0.0006 (14) |
C7 | 0.0599 (19) | 0.0632 (19) | 0.0441 (17) | −0.0023 (15) | −0.0089 (13) | 0.0099 (15) |
C8 | 0.0447 (16) | 0.0538 (17) | 0.0553 (18) | 0.0021 (13) | 0.0049 (13) | 0.0146 (14) |
C9 | 0.0585 (19) | 0.0414 (17) | 0.058 (2) | −0.0004 (14) | 0.0132 (14) | −0.0008 (14) |
C10 | 0.0521 (17) | 0.0443 (15) | 0.0405 (15) | −0.0007 (12) | 0.0052 (12) | 0.0014 (13) |
C11 | 0.061 (2) | 0.066 (2) | 0.077 (2) | 0.0056 (16) | 0.0062 (16) | 0.0225 (17) |
O1—C1 | 1.216 (3) | C3—H33 | 0.95 (5) |
N1—N2 | 1.311 (3) | C5—C6 | 1.380 (3) |
N1—C5 | 1.396 (3) | C5—C10 | 1.382 (3) |
N1—H1 | 0.81 (2) | C6—C7 | 1.378 (4) |
N2—C2 | 1.300 (3) | C6—H6 | 0.96 (2) |
N3—C4 | 1.139 (4) | C7—C8 | 1.381 (4) |
N4—C11 | 1.144 (4) | C7—H7 | 0.92 (3) |
C1—C2 | 1.465 (4) | C8—C9 | 1.380 (4) |
C1—C3 | 1.489 (5) | C8—C11 | 1.441 (4) |
C2—C4 | 1.434 (4) | C9—C10 | 1.373 (4) |
C3—H31 | 0.90 (4) | C9—H9 | 0.82 (3) |
C3—H32 | 0.96 (4) | C10—H10 | 0.98 (3) |
N2—N1—C5 | 119.9 (2) | C6—C5—N1 | 118.4 (2) |
N2—N1—H1 | 118.8 (18) | C10—C5—N1 | 120.4 (2) |
C5—N1—H1 | 121.1 (18) | C7—C6—C5 | 119.8 (3) |
C2—N2—N1 | 121.1 (2) | C7—C6—H6 | 116.7 (15) |
O1—C1—C2 | 118.8 (3) | C5—C6—H6 | 123.5 (15) |
O1—C1—C3 | 122.1 (3) | C6—C7—C8 | 119.4 (3) |
C2—C1—C3 | 119.1 (3) | C6—C7—H7 | 119.8 (16) |
N2—C2—C4 | 123.5 (2) | C8—C7—H7 | 120.7 (16) |
N2—C2—C1 | 118.9 (2) | C7—C8—C9 | 120.3 (3) |
C4—C2—C1 | 117.5 (2) | C7—C8—C11 | 120.7 (3) |
C1—C3—H31 | 112 (3) | C9—C8—C11 | 119.0 (3) |
C1—C3—H32 | 111 (2) | C10—C9—C8 | 120.7 (3) |
H31—C3—H32 | 111 (4) | C10—C9—H9 | 123 (2) |
C1—C3—H33 | 111 (3) | C8—C9—H9 | 116 (2) |
H31—C3—H33 | 110 (4) | C9—C10—C5 | 118.7 (3) |
H32—C3—H33 | 102 (4) | C9—C10—H10 | 119.3 (17) |
N3—C4—C2 | 177.7 (3) | C5—C10—H10 | 121.9 (17) |
C6—C5—C10 | 121.1 (2) | N4—C11—C8 | 178.9 (4) |
C11H11N3O | F(000) = 424 |
Mr = 201.23 | Dx = 1.238 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 7.052 (2) Å | θ = 7–13° |
b = 13.211 (2) Å | µ = 0.08 mm−1 |
c = 11.996 (2) Å | T = 293 K |
β = 104.96 (2)° | Prism, yellow |
V = 1079.7 (4) Å3 | 0.52 × 0.21 × 0.20 mm |
Z = 4 |
Enraf-Nonius CAD.4 diffractometer | Rint = 0.020 |
Radiation source: fine-focus sealed tube | θmax = 28.0°, θmin = 2.3° |
Graphite monochromator | h = 0→9 |
ω/2θ scans | k = 0→17 |
2804 measured reflections | l = −15→15 |
2595 independent reflections | 3 standard reflections every 120 min |
1814 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.045 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.140 | All H-atom parameters refined |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0786P)2 + 0.0758P] where P = (Fo2 + 2Fc2)/3 |
2595 reflections | (Δ/σ)max = 0.004 |
180 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
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 | ||
O1 | 0.55541 (18) | 0.24559 (8) | 0.33934 (9) | 0.0639 (3) | |
N1 | 0.26532 (16) | 0.09213 (8) | −0.00410 (9) | 0.0410 (3) | |
N2 | 0.34472 (15) | 0.08998 (8) | 0.10647 (9) | 0.0401 (3) | |
N3 | 0.4054 (3) | 0.34512 (12) | 0.06338 (14) | 0.0890 (6) | |
C1 | 0.4932 (2) | 0.16810 (10) | 0.28849 (12) | 0.0467 (3) | |
C2 | 0.40903 (19) | 0.17286 (10) | 0.16307 (11) | 0.0427 (3) | |
C3 | 0.4951 (3) | 0.06939 (15) | 0.34793 (16) | 0.0644 (5) | |
C4 | 0.4058 (2) | 0.26981 (12) | 0.10833 (13) | 0.0550 (4) | |
C5 | 0.20080 (17) | 0.00155 (9) | −0.06422 (10) | 0.0380 (3) | |
C6 | 0.1240 (2) | 0.00591 (11) | −0.18243 (12) | 0.0458 (3) | |
C7 | 0.0637 (2) | −0.08170 (12) | −0.24403 (13) | 0.0508 (4) | |
C8 | 0.0768 (2) | −0.17477 (11) | −0.18892 (14) | 0.0492 (4) | |
C9 | 0.1516 (2) | −0.17712 (11) | −0.07061 (14) | 0.0522 (4) | |
C10 | 0.2144 (2) | −0.09033 (10) | −0.00734 (12) | 0.0460 (3) | |
C11 | 0.0101 (3) | −0.27041 (15) | −0.2564 (2) | 0.0730 (5) | |
H1 | 0.241 (2) | 0.1493 (14) | −0.0427 (15) | 0.053 (4)* | |
H31 | 0.556 (4) | 0.0762 (19) | 0.422 (3) | 0.115 (8)* | |
H32 | 0.537 (4) | 0.016 (2) | 0.312 (3) | 0.126 (10)* | |
H33 | 0.374 (5) | 0.038 (2) | 0.343 (3) | 0.150 (12)* | |
H6 | 0.109 (3) | 0.0698 (15) | −0.2203 (17) | 0.071 (5)* | |
H7 | 0.018 (2) | −0.0754 (12) | −0.3304 (15) | 0.060 (5)* | |
H9 | 0.160 (3) | −0.2426 (15) | −0.0319 (16) | 0.072 (5)* | |
H10 | 0.258 (2) | −0.0921 (12) | 0.0721 (15) | 0.051 (4)* | |
H111 | −0.096 (4) | −0.301 (2) | −0.237 (2) | 0.123 (10)* | |
H112 | −0.019 (5) | −0.262 (3) | −0.343 (3) | 0.159 (12)* | |
H113 | 0.120 (6) | −0.316 (3) | −0.246 (3) | 0.162 (13)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0801 (8) | 0.0540 (6) | 0.0472 (6) | −0.0052 (5) | −0.0024 (5) | −0.0146 (5) |
N1 | 0.0467 (6) | 0.0350 (6) | 0.0367 (6) | −0.0011 (4) | 0.0022 (4) | −0.0004 (4) |
N2 | 0.0386 (5) | 0.0409 (6) | 0.0378 (5) | −0.0008 (4) | 0.0043 (4) | −0.0041 (4) |
N3 | 0.1216 (15) | 0.0551 (9) | 0.0683 (10) | −0.0136 (9) | −0.0154 (9) | 0.0099 (7) |
C1 | 0.0482 (7) | 0.0468 (7) | 0.0412 (7) | −0.0010 (6) | 0.0048 (6) | −0.0071 (6) |
C2 | 0.0446 (7) | 0.0396 (7) | 0.0401 (7) | −0.0012 (5) | 0.0039 (5) | −0.0039 (5) |
C3 | 0.0811 (12) | 0.0594 (10) | 0.0456 (9) | −0.0099 (9) | 0.0037 (8) | 0.0034 (7) |
C4 | 0.0638 (9) | 0.0433 (8) | 0.0469 (8) | −0.0059 (6) | −0.0055 (6) | −0.0062 (6) |
C5 | 0.0382 (6) | 0.0359 (6) | 0.0378 (6) | −0.0001 (5) | 0.0062 (5) | −0.0035 (5) |
C6 | 0.0514 (8) | 0.0422 (7) | 0.0390 (7) | −0.0013 (6) | 0.0030 (5) | 0.0007 (5) |
C7 | 0.0516 (8) | 0.0556 (9) | 0.0409 (7) | −0.0024 (6) | 0.0039 (6) | −0.0097 (6) |
C8 | 0.0425 (7) | 0.0456 (7) | 0.0586 (8) | −0.0032 (6) | 0.0116 (6) | −0.0155 (6) |
C9 | 0.0595 (9) | 0.0348 (7) | 0.0617 (9) | 0.0018 (6) | 0.0144 (7) | 0.0002 (6) |
C10 | 0.0556 (8) | 0.0400 (7) | 0.0395 (7) | 0.0029 (6) | 0.0070 (6) | 0.0012 (5) |
C11 | 0.0734 (12) | 0.0553 (10) | 0.0899 (14) | −0.0145 (9) | 0.0206 (11) | −0.0350 (10) |
O1—C1 | 1.2142 (17) | C5—C10 | 1.3836 (18) |
N1—N2 | 1.3001 (15) | C6—C7 | 1.3800 (19) |
N1—C5 | 1.4105 (16) | C6—H6 | 0.951 (19) |
N1—H1 | 0.880 (19) | C7—C8 | 1.388 (2) |
N2—C2 | 1.3063 (16) | C7—H7 | 1.006 (17) |
N3—C4 | 1.131 (2) | C8—C9 | 1.381 (2) |
C1—C2 | 1.4693 (18) | C8—C11 | 1.509 (2) |
C1—C3 | 1.485 (2) | C9—C10 | 1.3832 (19) |
C2—C4 | 1.437 (2) | C9—H9 | 0.976 (19) |
C3—H31 | 0.89 (3) | C10—H10 | 0.923 (16) |
C3—H32 | 0.92 (3) | C11—H111 | 0.93 (3) |
C3—H33 | 0.93 (3) | C11—H112 | 1.01 (4) |
C5—C6 | 1.3823 (18) | C11—H113 | 0.96 (4) |
N2—N1—C5 | 120.02 (11) | C7—C6—H6 | 120.4 (12) |
N2—N1—H1 | 122.0 (11) | C5—C6—H6 | 119.6 (12) |
C5—N1—H1 | 117.8 (11) | C6—C7—C8 | 120.97 (13) |
N1—N2—C2 | 120.82 (11) | C6—C7—H7 | 117.0 (10) |
O1—C1—C2 | 118.46 (13) | C8—C7—H7 | 121.9 (10) |
O1—C1—C3 | 122.82 (13) | C9—C8—C7 | 118.05 (12) |
C2—C1—C3 | 118.71 (12) | C9—C8—C11 | 121.07 (15) |
N2—C2—C4 | 123.17 (12) | C7—C8—C11 | 120.87 (16) |
N2—C2—C1 | 119.39 (12) | C8—C9—C10 | 121.91 (13) |
C4—C2—C1 | 117.42 (11) | C8—C9—H9 | 118.0 (11) |
C1—C3—H31 | 109.7 (17) | C10—C9—H9 | 120.1 (11) |
C1—C3—H32 | 114.5 (18) | C9—C10—C5 | 119.01 (13) |
H31—C3—H32 | 115 (2) | C9—C10—H10 | 121.3 (10) |
C1—C3—H33 | 117.5 (19) | C5—C10—H10 | 119.5 (10) |
H31—C3—H33 | 108 (2) | C8—C11—H111 | 113.1 (17) |
H32—C3—H33 | 92 (2) | C8—C11—H112 | 114 (2) |
N3—C4—C2 | 178.37 (19) | H111—C11—H112 | 110 (3) |
C6—C5—C10 | 120.09 (12) | C8—C11—H113 | 109 (2) |
C6—C5—N1 | 118.58 (11) | H111—C11—H113 | 111 (3) |
C10—C5—N1 | 121.33 (11) | H112—C11—H113 | 98 (3) |
C7—C6—C5 | 119.96 (13) |
C12H11N3O2 | F(000) = 480 |
Mr = 229.24 | Dx = 1.336 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 8.638 (3) Å | θ = 8–12° |
b = 10.841 (2) Å | µ = 0.09 mm−1 |
c = 12.208 (2) Å | T = 293 K |
β = 94.69 (2)° | Prism, yellow |
V = 1139.4 (5) Å3 | 0.28 × 0.19 × 0.14 mm |
Z = 4 |
Enraf-Nonius CAD4 diffractometer | Rint = 0.012 |
Radiation source: fine-focus sealed tube | θmax = 28.0°, θmin = 2.5° |
Graphite monochromator | h = 0→11 |
ω/2θ scans | k = 0→14 |
2921 measured reflections | l = −16→16 |
2741 independent reflections | 3 standard reflections every 120 min |
1735 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.053 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.155 | All H-atom parameters refined |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0888P)2] where P = (Fo2 + 2Fc2)/3 |
2741 reflections | (Δ/σ)max = 0.013 |
198 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
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 | ||
O1 | 0.15747 (17) | 0.04192 (14) | 0.43980 (12) | 0.0601 (4) | |
O2 | −0.50189 (17) | 0.83438 (13) | 0.65804 (11) | 0.0556 (4) | |
N1 | −0.07426 (18) | 0.36408 (14) | 0.60706 (13) | 0.0407 (4) | |
N2 | −0.05251 (16) | 0.29449 (13) | 0.52129 (12) | 0.0386 (4) | |
N3 | 0.1989 (2) | 0.14192 (19) | 0.71043 (17) | 0.0700 (6) | |
C1 | 0.0631 (2) | 0.12560 (17) | 0.43237 (15) | 0.0436 (4) | |
C2 | 0.0419 (2) | 0.20171 (16) | 0.52987 (14) | 0.0399 (4) | |
C3 | −0.0324 (4) | 0.1540 (3) | 0.3294 (2) | 0.0621 (6) | |
C4 | 0.1307 (2) | 0.16739 (18) | 0.63113 (16) | 0.0465 (5) | |
C5 | −0.17546 (19) | 0.46556 (15) | 0.59488 (14) | 0.0358 (4) | |
C6 | −0.2475 (2) | 0.49876 (17) | 0.49332 (14) | 0.0402 (4) | |
C7 | −0.3452 (2) | 0.59993 (17) | 0.48727 (14) | 0.0402 (4) | |
C8 | −0.37382 (19) | 0.66866 (15) | 0.57949 (13) | 0.0358 (4) | |
C9 | −0.2998 (2) | 0.63279 (18) | 0.67998 (15) | 0.0464 (5) | |
C10 | −0.2017 (2) | 0.53268 (18) | 0.68853 (15) | 0.0479 (5) | |
C11 | −0.4779 (2) | 0.77824 (16) | 0.57467 (14) | 0.0394 (4) | |
C12 | −0.5520 (3) | 0.8214 (2) | 0.46668 (18) | 0.0533 (5) | |
H1 | −0.027 (2) | 0.3500 (18) | 0.6757 (18) | 0.045 (5)* | |
H31 | −0.034 (3) | 0.236 (3) | 0.312 (2) | 0.096 (10)* | |
H32 | 0.003 (3) | 0.113 (3) | 0.276 (3) | 0.095 (10)* | |
H33 | −0.137 (4) | 0.129 (3) | 0.339 (3) | 0.094 (10)* | |
H6 | −0.237 (2) | 0.449 (2) | 0.4332 (18) | 0.054 (6)* | |
H7 | −0.396 (2) | 0.6161 (17) | 0.4197 (16) | 0.037 (5)* | |
H9 | −0.316 (2) | 0.678 (2) | 0.7466 (18) | 0.054 (6)* | |
H10 | −0.146 (2) | 0.511 (2) | 0.7592 (18) | 0.054 (6)* | |
H121 | −0.623 (3) | 0.888 (3) | 0.483 (2) | 0.089 (9)* | |
H122 | −0.602 (4) | 0.751 (4) | 0.429 (3) | 0.121 (12)* | |
H123 | −0.472 (4) | 0.853 (3) | 0.421 (3) | 0.095 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0648 (9) | 0.0540 (9) | 0.0628 (9) | 0.0206 (7) | 0.0127 (7) | −0.0020 (7) |
O2 | 0.0718 (9) | 0.0512 (8) | 0.0440 (7) | 0.0127 (7) | 0.0056 (6) | −0.0082 (6) |
N1 | 0.0476 (9) | 0.0387 (8) | 0.0359 (8) | 0.0038 (6) | 0.0033 (6) | −0.0003 (6) |
N2 | 0.0419 (8) | 0.0337 (7) | 0.0411 (8) | −0.0007 (6) | 0.0084 (6) | 0.0002 (6) |
N3 | 0.0756 (13) | 0.0719 (13) | 0.0596 (11) | 0.0039 (11) | −0.0127 (10) | 0.0021 (10) |
C1 | 0.0490 (10) | 0.0387 (9) | 0.0442 (10) | 0.0025 (8) | 0.0097 (8) | 0.0010 (8) |
C2 | 0.0407 (9) | 0.0366 (9) | 0.0426 (9) | −0.0004 (7) | 0.0039 (7) | 0.0038 (7) |
C3 | 0.0875 (19) | 0.0529 (14) | 0.0448 (12) | 0.0121 (13) | −0.0012 (11) | −0.0029 (10) |
C4 | 0.0446 (10) | 0.0437 (10) | 0.0509 (11) | 0.0013 (8) | 0.0026 (8) | −0.0003 (8) |
C5 | 0.0388 (9) | 0.0311 (8) | 0.0380 (8) | −0.0011 (7) | 0.0062 (7) | 0.0004 (7) |
C6 | 0.0487 (10) | 0.0389 (9) | 0.0332 (9) | −0.0006 (8) | 0.0045 (7) | −0.0031 (8) |
C7 | 0.0454 (10) | 0.0426 (10) | 0.0320 (9) | −0.0001 (8) | −0.0005 (7) | −0.0004 (7) |
C8 | 0.0378 (8) | 0.0347 (8) | 0.0349 (8) | −0.0027 (7) | 0.0031 (6) | −0.0009 (7) |
C9 | 0.0586 (12) | 0.0455 (10) | 0.0351 (9) | 0.0092 (9) | 0.0044 (8) | −0.0039 (8) |
C10 | 0.0617 (12) | 0.0503 (11) | 0.0313 (9) | 0.0095 (9) | 0.0004 (8) | 0.0005 (8) |
C11 | 0.0416 (9) | 0.0364 (9) | 0.0406 (9) | −0.0033 (7) | 0.0051 (7) | −0.0030 (7) |
C12 | 0.0567 (12) | 0.0539 (12) | 0.0483 (11) | 0.0151 (11) | −0.0023 (9) | 0.0028 (10) |
O1—C1 | 1.218 (2) | C5—C10 | 1.389 (2) |
O2—C11 | 1.218 (2) | C6—C7 | 1.382 (3) |
N1—N2 | 1.316 (2) | C6—H6 | 0.92 (2) |
N1—C5 | 1.406 (2) | C7—C8 | 1.389 (2) |
N1—H1 | 0.92 (2) | C7—H7 | 0.918 (19) |
N2—C2 | 1.294 (2) | C8—C9 | 1.392 (2) |
N3—C4 | 1.126 (3) | C8—C11 | 1.488 (2) |
C1—C2 | 1.472 (3) | C9—C10 | 1.376 (3) |
C1—C3 | 1.479 (3) | C9—H9 | 0.97 (2) |
C2—C4 | 1.449 (3) | C10—H10 | 0.98 (2) |
C3—H31 | 0.91 (3) | C11—C12 | 1.493 (3) |
C3—H32 | 0.86 (3) | C12—H121 | 0.97 (3) |
C3—H33 | 0.96 (3) | C12—H122 | 0.97 (4) |
C5—C6 | 1.388 (2) | C12—H123 | 0.98 (3) |
N2—N1—C5 | 119.50 (15) | C5—C6—H6 | 119.5 (13) |
N2—N1—H1 | 123.4 (12) | C6—C7—C8 | 122.06 (17) |
C5—N1—H1 | 117.1 (12) | C6—C7—H7 | 116.3 (11) |
C2—N2—N1 | 120.74 (15) | C8—C7—H7 | 121.5 (11) |
O1—C1—C2 | 118.97 (17) | C7—C8—C9 | 117.73 (16) |
O1—C1—C3 | 122.81 (19) | C7—C8—C11 | 122.90 (16) |
C2—C1—C3 | 118.22 (18) | C9—C8—C11 | 119.37 (15) |
N2—C2—C4 | 123.70 (17) | C10—C9—C8 | 121.54 (17) |
N2—C2—C1 | 119.33 (16) | C10—C9—H9 | 117.8 (12) |
C4—C2—C1 | 116.97 (16) | C8—C9—H9 | 120.7 (12) |
C1—C3—H31 | 113.1 (18) | C9—C10—C5 | 119.46 (17) |
C1—C3—H32 | 109 (2) | C9—C10—H10 | 120.5 (13) |
H31—C3—H32 | 109 (3) | C5—C10—H10 | 120.0 (13) |
C1—C3—H33 | 107.6 (19) | O2—C11—C8 | 120.63 (16) |
H31—C3—H33 | 108 (3) | O2—C11—C12 | 119.43 (17) |
H32—C3—H33 | 110 (3) | C8—C11—C12 | 119.93 (16) |
N3—C4—C2 | 179.2 (2) | C11—C12—H121 | 106.5 (17) |
C6—C5—C10 | 120.51 (16) | C11—C12—H122 | 108 (2) |
C6—C5—N1 | 121.79 (15) | H121—C12—H122 | 114 (3) |
C10—C5—N1 | 117.70 (16) | C11—C12—H123 | 109.8 (18) |
C7—C6—C5 | 118.72 (16) | H121—C12—H123 | 110 (2) |
C7—C6—H6 | 121.5 (13) | H122—C12—H123 | 108 (3) |
C11H11N3O2 | F(000) = 456 |
Mr = 217.23 | Dx = 1.258 Mg m−3 |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 25 reflections |
a = 15.236 (2) Å | θ = 9–14° |
b = 6.618 (1) Å | µ = 0.09 mm−1 |
c = 11.379 (1) Å | T = 293 K |
V = 1147.4 (3) Å3 | Prism, yellow |
Z = 4 | 0.52 × 0.33 × 0.26 mm |
Enraf-Nonius CAD-4 diffractometer | θmax = 28.0°, θmin = 2.2° |
Radiation source: fine-focus sealed tube | h = 0→20 |
Graphite monochromator | k = 0→8 |
1488 measured reflections | l = 0→14 |
1488 independent reflections | 3 standard reflections every 120 min |
881 reflections with I > 2σ(I) | intensity decay: none |
Rint = 0.000 |
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)] = 0.050 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.146 | All H-atom parameters refined |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0846P)2 + 0.008P] where P = (Fo2 + 2Fc2)/3 |
1488 reflections | (Δ/σ)max = 0.033 |
126 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
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 | ||
O1 | 0.02844 (17) | 0.2500 | 0.52530 (14) | 0.1259 (9) | |
O2 | 0.10460 (9) | 0.2500 | −0.07118 (13) | 0.0741 (5) | |
N1 | 0.01796 (10) | 0.2500 | 0.12454 (12) | 0.0520 (4) | |
N2 | −0.02023 (11) | 0.2500 | 0.22601 (12) | 0.0562 (4) | |
N3 | 0.19437 (18) | 0.2500 | 0.3077 (3) | 0.1285 (11) | |
C1 | −0.0167 (2) | 0.2500 | 0.43685 (17) | 0.0918 (9) | |
C2 | 0.02668 (15) | 0.2500 | 0.32217 (16) | 0.0679 (6) | |
C3 | −0.1145 (3) | 0.2500 | 0.4402 (3) | 0.1226 (13) | |
C4 | 0.1208 (2) | 0.2500 | 0.3184 (2) | 0.0844 (7) | |
C5 | −0.03075 (11) | 0.2500 | 0.02026 (14) | 0.0467 (4) | |
C6 | 0.01596 (12) | 0.2500 | −0.08446 (15) | 0.0524 (5) | |
C7 | −0.02834 (17) | 0.2500 | −0.19033 (16) | 0.0684 (6) | |
C8 | −0.11815 (18) | 0.2500 | −0.1906 (2) | 0.0828 (7) | |
C9 | −0.16428 (15) | 0.2500 | −0.0879 (2) | 0.0846 (7) | |
C10 | −0.12069 (13) | 0.2500 | 0.01847 (19) | 0.0637 (6) | |
C11 | 0.1568 (2) | 0.2500 | −0.1752 (3) | 0.1109 (11) | |
H1 | 0.0738 (14) | 0.2500 | 0.126 (2) | 0.066 (6)* | |
H7 | 0.0030 (16) | 0.2500 | −0.259 (3) | 0.097 (8)* | |
H8 | −0.1486 (18) | 0.2500 | −0.268 (3) | 0.109 (8)* | |
H9 | −0.2260 (17) | 0.2500 | −0.086 (2) | 0.098 (8)* | |
H10 | −0.1503 (14) | 0.2500 | 0.087 (2) | 0.078 (6)* | |
H111 | 0.209 (3) | 0.2500 | −0.134 (4) | 0.155 (16)* | |
H112 | 0.1502 (16) | 0.373 (5) | −0.223 (3) | 0.166 (11)* | |
H32 | −0.137 (2) | 0.369 (6) | 0.421 (4) | 0.25 (2)* | |
H31 | −0.134 (3) | 0.2500 | 0.509 (5) | 0.197 (19)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.209 (3) | 0.1296 (17) | 0.0391 (9) | 0.000 | −0.0195 (11) | 0.000 |
O2 | 0.0643 (9) | 0.0989 (11) | 0.0591 (8) | 0.000 | 0.0149 (7) | 0.000 |
N1 | 0.0537 (9) | 0.0672 (10) | 0.0350 (7) | 0.000 | −0.0024 (6) | 0.000 |
N2 | 0.0737 (10) | 0.0602 (9) | 0.0347 (8) | 0.000 | −0.0010 (6) | 0.000 |
N3 | 0.0952 (17) | 0.169 (3) | 0.122 (2) | 0.000 | −0.0555 (15) | 0.000 |
C1 | 0.157 (3) | 0.0848 (17) | 0.0336 (10) | 0.000 | −0.0043 (14) | 0.000 |
C2 | 0.0953 (15) | 0.0702 (13) | 0.0382 (10) | 0.000 | −0.0127 (10) | 0.000 |
C3 | 0.147 (3) | 0.157 (4) | 0.0637 (17) | 0.000 | 0.0389 (19) | 0.000 |
C4 | 0.1013 (19) | 0.0942 (18) | 0.0576 (13) | 0.000 | −0.0382 (13) | 0.000 |
C5 | 0.0554 (10) | 0.0510 (10) | 0.0337 (8) | 0.000 | −0.0038 (7) | 0.000 |
C6 | 0.0629 (10) | 0.0533 (11) | 0.0409 (9) | 0.000 | 0.0037 (8) | 0.000 |
C7 | 0.1068 (18) | 0.0667 (13) | 0.0316 (9) | 0.000 | 0.0036 (11) | 0.000 |
C8 | 0.0987 (18) | 0.1020 (18) | 0.0476 (12) | 0.000 | −0.0288 (12) | 0.000 |
C9 | 0.0670 (13) | 0.111 (2) | 0.0752 (14) | 0.000 | −0.0240 (12) | 0.000 |
C10 | 0.0555 (11) | 0.0851 (15) | 0.0504 (11) | 0.000 | 0.0003 (9) | 0.000 |
C11 | 0.093 (2) | 0.154 (3) | 0.086 (2) | 0.000 | 0.0430 (19) | 0.000 |
O1—C1 | 1.219 (3) | C5—C10 | 1.370 (3) |
O2—C6 | 1.359 (2) | C5—C6 | 1.388 (2) |
O2—C11 | 1.426 (3) | C6—C7 | 1.381 (3) |
N1—N2 | 1.2930 (19) | C7—C8 | 1.368 (4) |
N1—C5 | 1.400 (2) | C7—H7 | 0.91 (3) |
N1—H1 | 0.85 (2) | C8—C9 | 1.364 (4) |
N2—C2 | 1.307 (2) | C8—H8 | 1.00 (3) |
N3—C4 | 1.128 (4) | C9—C10 | 1.380 (3) |
C1—C2 | 1.463 (3) | C9—H9 | 0.94 (2) |
C1—C3 | 1.491 (6) | C10—H10 | 0.90 (2) |
C2—C4 | 1.434 (4) | C11—H111 | 0.93 (4) |
C3—H32 | 0.89 (4) | C11—H112 | 0.99 (3) |
C3—H31 | 0.83 (6) | ||
C6—O2—C11 | 117.5 (2) | O2—C6—C7 | 125.65 (18) |
N2—N1—C5 | 121.23 (15) | O2—C6—C5 | 114.46 (15) |
N2—N1—H1 | 116.0 (15) | C7—C6—C5 | 119.89 (19) |
C5—N1—H1 | 122.8 (15) | C8—C7—C6 | 119.4 (2) |
N1—N2—C2 | 120.10 (19) | C8—C7—H7 | 121.4 (17) |
O1—C1—C2 | 118.8 (3) | C6—C7—H7 | 119.2 (17) |
O1—C1—C3 | 122.9 (3) | C9—C8—C7 | 120.9 (2) |
C2—C1—C3 | 118.3 (2) | C9—C8—H8 | 121.3 (16) |
N2—C2—C4 | 121.45 (19) | C7—C8—H8 | 117.8 (17) |
N2—C2—C1 | 120.0 (2) | C8—C9—C10 | 120.2 (2) |
C4—C2—C1 | 118.5 (2) | C8—C9—H9 | 122.0 (16) |
C1—C3—H32 | 112 (2) | C10—C9—H9 | 117.7 (16) |
C1—C3—H31 | 112 (3) | C5—C10—C9 | 119.6 (2) |
H32—C3—H31 | 95 (3) | C5—C10—H10 | 119.2 (14) |
N3—C4—C2 | 175.5 (3) | C9—C10—H10 | 121.2 (14) |
C10—C5—C6 | 120.00 (17) | O2—C11—H111 | 93 (3) |
C10—C5—N1 | 122.87 (16) | O2—C11—H112 | 113.8 (17) |
C6—C5—N1 | 117.13 (15) | H111—C11—H112 | 112 (2) |
C12H11N3O2 | Z = 2 |
Mr = 229.24 | F(000) = 240 |
Triclinic, P1 | Dx = 1.275 Mg m−3 Dm = 0 Mg m−3 Dm measured by not measured |
a = 6.878 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.241 (1) Å | Cell parameters from 25 reflections |
c = 11.395 (1) Å | θ = 8–13° |
α = 105.21 (1)° | µ = 0.09 mm−1 |
β = 96.62 (2)° | T = 293 K |
γ = 102.92 (2)° | Prism, yellow |
V = 597.0 (2) Å3 | 0.62 × 0.26 × 0.12 mm |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.012 |
Radiation source: fine-focus sealed tube | θmax = 28.0°, θmin = 2.7° |
Graphite monochromator | h = 0→9 |
ω/2θ scans | k = −10→10 |
3007 measured reflections | l = −15→14 |
2860 independent reflections | 3 standard reflections every 120 min |
1963 reflections with I > 2σ(I) |
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)] = 0.049 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.150 | All H-atom parameters refined |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0876P)2 + 0.0213P] where P = (Fo2 + 2Fc2)/3 |
2860 reflections | (Δ/σ)max = 0.005 |
198 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
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 | ||
O1 | 0.2577 (3) | −0.0215 (2) | 0.53703 (11) | 0.0987 (5) | |
O2 | 0.23578 (17) | −0.29952 (13) | −0.04881 (10) | 0.0580 (3) | |
N1 | 0.24747 (16) | −0.02907 (14) | 0.13378 (10) | 0.0421 (3) | |
N2 | 0.25454 (17) | 0.05167 (15) | 0.25018 (10) | 0.0465 (3) | |
N3 | 0.2365 (3) | −0.3601 (2) | 0.27239 (17) | 0.0935 (6) | |
C1 | 0.2617 (3) | 0.0588 (3) | 0.46217 (15) | 0.0695 (5) | |
C2 | 0.2517 (2) | −0.0332 (2) | 0.33163 (13) | 0.0521 (3) | |
C3 | 0.2763 (6) | 0.2483 (4) | 0.4977 (2) | 0.1011 (8) | |
C4 | 0.2417 (3) | −0.2159 (2) | 0.30019 (14) | 0.0613 (4) | |
C5 | 0.25261 (17) | 0.06358 (16) | 0.04689 (11) | 0.0388 (3) | |
C6 | 0.25152 (17) | −0.02450 (16) | −0.07770 (11) | 0.0405 (3) | |
C7 | 0.2615 (2) | 0.0742 (2) | −0.16154 (14) | 0.0514 (4) | |
C8 | 0.2683 (2) | 0.2480 (2) | −0.12429 (16) | 0.0605 (4) | |
C9 | 0.2645 (2) | 0.3294 (2) | −0.00314 (16) | 0.0577 (4) | |
C10 | 0.2573 (2) | 0.23906 (18) | 0.08260 (15) | 0.0487 (3) | |
C11 | 0.2386 (2) | −0.21298 (18) | −0.12026 (12) | 0.0457 (3) | |
C12 | 0.2270 (4) | −0.3009 (3) | −0.25512 (17) | 0.0714 (5) | |
H1 | 0.238 (2) | −0.147 (2) | 0.1044 (15) | 0.054 (4)* | |
H31 | 0.346 (5) | 0.303 (4) | 0.574 (3) | 0.152 (11)* | |
H32 | 0.153 (7) | 0.267 (5) | 0.469 (4) | 0.197 (17)* | |
H33 | 0.328 (6) | 0.304 (5) | 0.448 (4) | 0.173 (15)* | |
H7 | 0.258 (3) | 0.017 (2) | −0.2454 (19) | 0.062 (5)* | |
H8 | 0.276 (3) | 0.311 (3) | −0.1830 (19) | 0.083 (6)* | |
H9 | 0.267 (3) | 0.440 (3) | 0.0181 (19) | 0.077 (5)* | |
H10 | 0.255 (3) | 0.297 (2) | 0.1640 (19) | 0.066 (5)* | |
H121 | 0.209 (4) | −0.418 (4) | −0.266 (3) | 0.128 (10)* | |
H122 | 0.352 (5) | −0.252 (3) | −0.287 (3) | 0.131 (9)* | |
H123 | 0.121 (5) | −0.297 (4) | −0.302 (3) | 0.134 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.1422 (14) | 0.1223 (12) | 0.0429 (7) | 0.0386 (10) | 0.0243 (7) | 0.0375 (8) |
O2 | 0.0786 (7) | 0.0496 (6) | 0.0565 (6) | 0.0267 (5) | 0.0179 (5) | 0.0233 (5) |
N1 | 0.0522 (6) | 0.0446 (6) | 0.0369 (6) | 0.0171 (5) | 0.0126 (4) | 0.0191 (4) |
N2 | 0.0499 (6) | 0.0544 (6) | 0.0390 (6) | 0.0159 (5) | 0.0095 (4) | 0.0178 (5) |
N3 | 0.1372 (17) | 0.0686 (10) | 0.0806 (12) | 0.0276 (10) | 0.0196 (11) | 0.0320 (9) |
C1 | 0.0836 (12) | 0.0891 (12) | 0.0404 (8) | 0.0272 (9) | 0.0132 (7) | 0.0223 (8) |
C2 | 0.0595 (8) | 0.0617 (8) | 0.0401 (7) | 0.0176 (6) | 0.0102 (6) | 0.0219 (6) |
C3 | 0.161 (3) | 0.0886 (16) | 0.0496 (11) | 0.0465 (16) | 0.0117 (14) | 0.0057 (11) |
C4 | 0.0780 (11) | 0.0668 (10) | 0.0463 (8) | 0.0174 (8) | 0.0113 (7) | 0.0304 (7) |
C5 | 0.0376 (6) | 0.0456 (6) | 0.0409 (6) | 0.0143 (5) | 0.0104 (5) | 0.0219 (5) |
C6 | 0.0386 (6) | 0.0496 (7) | 0.0410 (6) | 0.0152 (5) | 0.0105 (5) | 0.0221 (5) |
C7 | 0.0544 (8) | 0.0664 (9) | 0.0440 (8) | 0.0195 (6) | 0.0135 (6) | 0.0296 (7) |
C8 | 0.0686 (9) | 0.0658 (9) | 0.0659 (9) | 0.0220 (7) | 0.0167 (7) | 0.0461 (8) |
C9 | 0.0652 (9) | 0.0476 (8) | 0.0723 (10) | 0.0216 (7) | 0.0182 (7) | 0.0300 (7) |
C10 | 0.0522 (8) | 0.0480 (7) | 0.0534 (8) | 0.0184 (6) | 0.0151 (6) | 0.0211 (6) |
C11 | 0.0446 (7) | 0.0506 (7) | 0.0464 (7) | 0.0160 (5) | 0.0116 (5) | 0.0181 (6) |
C12 | 0.0976 (15) | 0.0627 (11) | 0.0476 (9) | 0.0160 (10) | 0.0161 (9) | 0.0089 (7) |
O1—C1 | 1.208 (2) | C5—C6 | 1.4132 (18) |
O2—C11 | 1.2141 (15) | C6—C7 | 1.4058 (17) |
N1—N2 | 1.3085 (16) | C6—C11 | 1.4795 (18) |
N1—C5 | 1.3990 (15) | C7—C8 | 1.372 (2) |
N1—H1 | 0.924 (16) | C7—H7 | 0.94 (2) |
N2—C2 | 1.3001 (17) | C8—C9 | 1.373 (2) |
N3—C4 | 1.137 (2) | C8—H8 | 0.95 (2) |
C1—C2 | 1.468 (2) | C9—C10 | 1.374 (2) |
C1—C3 | 1.484 (3) | C9—H9 | 0.87 (2) |
C2—C4 | 1.437 (2) | C10—H10 | 0.93 (2) |
C3—H31 | 0.89 (4) | C11—C12 | 1.501 (2) |
C3—H32 | 0.93 (4) | C12—H121 | 0.92 (3) |
C3—H33 | 0.87 (4) | C12—H122 | 1.01 (3) |
C5—C10 | 1.3875 (18) | C12—H123 | 0.86 (3) |
N2—N1—C5 | 119.81 (11) | C5—C6—C11 | 122.19 (11) |
N2—N1—H1 | 123.4 (10) | C8—C7—C6 | 121.33 (14) |
C5—N1—H1 | 116.8 (10) | C8—C7—H7 | 120.4 (10) |
C2—N2—N1 | 120.15 (12) | C6—C7—H7 | 118.3 (10) |
O1—C1—C2 | 119.22 (17) | C7—C8—C9 | 120.18 (13) |
O1—C1—C3 | 122.18 (17) | C7—C8—H8 | 119.4 (12) |
C2—C1—C3 | 118.60 (16) | C9—C8—H8 | 120.5 (12) |
N2—C2—C4 | 122.81 (13) | C8—C9—C10 | 120.67 (14) |
N2—C2—C1 | 119.74 (14) | C8—C9—H9 | 118.5 (13) |
C4—C2—C1 | 117.44 (13) | C10—C9—H9 | 120.8 (13) |
C1—C3—H31 | 112 (2) | C9—C10—C5 | 119.95 (14) |
C1—C3—H32 | 110 (3) | C9—C10—H10 | 119.3 (11) |
H31—C3—H32 | 123 (3) | C5—C10—H10 | 120.8 (11) |
C1—C3—H33 | 115 (3) | O2—C11—C6 | 121.63 (12) |
H31—C3—H33 | 108 (3) | O2—C11—C12 | 118.79 (14) |
H32—C3—H33 | 87 (3) | C6—C11—C12 | 119.58 (13) |
N3—C4—C2 | 177.98 (18) | C11—C12—H121 | 107.8 (18) |
C10—C5—N1 | 120.38 (12) | C11—C12—H122 | 112.6 (16) |
C10—C5—C6 | 120.60 (12) | H121—C12—H122 | 111 (2) |
N1—C5—C6 | 119.02 (11) | C11—C12—H123 | 113 (2) |
C7—C6—C5 | 117.24 (12) | H121—C12—H123 | 103 (2) |
C7—C6—C11 | 120.57 (12) | H122—C12—H123 | 109 (2) |
C10H8N4O3 | F(000) = 480 |
Mr = 232.20 | Dx = 1.443 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 7.184 (1) Å | θ = 9–13° |
b = 19.491 (2) Å | µ = 0.11 mm−1 |
c = 8.084 (1) Å | T = 293 K |
β = 109.27 (1)° | Prism, orange |
V = 1068.5 (2) Å3 | 0.60 × 0.26 × 0.21 mm |
Z = 4 |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.025 |
Radiation source: fine-focus sealed tube | θmax = 28.0°, θmin = 2.1° |
Graphite monochromator | h = 0→9 |
ω/2θ scans | k = 0→25 |
2750 measured reflections | l = −10→10 |
2580 independent reflections | 3 standard reflections every 120 min |
1996 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.040 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.117 | All H-atom parameters refined |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0591P)2 + 0.1463P] where P = (Fo2 + 2Fc2)/3 |
2580 reflections | (Δ/σ)max = 0.002 |
186 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
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 | ||
O1 | −0.01208 (19) | 0.29010 (5) | −0.29443 (15) | 0.0624 (3) | |
O3 | 0.2797 (2) | −0.02195 (6) | 0.48349 (14) | 0.0682 (4) | |
O2 | 0.2401 (2) | 0.07871 (6) | 0.37349 (14) | 0.0736 (4) | |
N1 | 0.17042 (16) | 0.09605 (5) | 0.03822 (14) | 0.0363 (2) | |
N2 | 0.12301 (15) | 0.12882 (5) | −0.11270 (13) | 0.0353 (2) | |
N3 | 0.0215 (3) | 0.25581 (7) | 0.1420 (2) | 0.0710 (4) | |
N4 | 0.26505 (18) | 0.01702 (6) | 0.36236 (14) | 0.0451 (3) | |
C1 | 0.0209 (2) | 0.22906 (7) | −0.29076 (18) | 0.0439 (3) | |
C2 | 0.06635 (19) | 0.19232 (6) | −0.12169 (16) | 0.0376 (3) | |
C3 | 0.0150 (4) | 0.18849 (10) | −0.4473 (2) | 0.0637 (5) | |
C4 | 0.0427 (2) | 0.22907 (7) | 0.02465 (19) | 0.0449 (3) | |
C5 | 0.23043 (17) | 0.02783 (6) | 0.04526 (15) | 0.0320 (2) | |
C6 | 0.28031 (18) | −0.01077 (6) | 0.20023 (15) | 0.0347 (3) | |
C7 | 0.3447 (2) | −0.07831 (7) | 0.20570 (18) | 0.0405 (3) | |
C8 | 0.3568 (2) | −0.10876 (7) | 0.05646 (19) | 0.0445 (3) | |
C9 | 0.3024 (2) | −0.07186 (7) | −0.09862 (18) | 0.0423 (3) | |
C10 | 0.24042 (19) | −0.00492 (6) | −0.10542 (16) | 0.0365 (3) | |
H1 | 0.182 (2) | 0.1171 (8) | 0.135 (2) | 0.047 (4)* | |
H31 | −0.026 (4) | 0.2161 (14) | −0.546 (3) | 0.106 (8)* | |
H32 | −0.064 (4) | 0.1475 (15) | −0.460 (3) | 0.108 (8)* | |
H33 | 0.134 (5) | 0.1682 (15) | −0.434 (3) | 0.121 (10)* | |
H7 | 0.378 (2) | −0.1019 (8) | 0.313 (2) | 0.054 (4)* | |
H8 | 0.402 (2) | −0.1554 (8) | 0.059 (2) | 0.047 (4)* | |
H9 | 0.305 (2) | −0.0934 (8) | −0.201 (2) | 0.054 (4)* | |
H10 | 0.204 (2) | 0.0200 (8) | −0.209 (2) | 0.044 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0807 (8) | 0.0374 (6) | 0.0700 (7) | 0.0076 (5) | 0.0260 (6) | 0.0155 (5) |
O3 | 0.0986 (10) | 0.0708 (8) | 0.0422 (6) | 0.0060 (7) | 0.0329 (6) | 0.0121 (5) |
O2 | 0.1245 (12) | 0.0544 (7) | 0.0429 (6) | 0.0252 (7) | 0.0292 (7) | −0.0041 (5) |
N1 | 0.0465 (6) | 0.0299 (5) | 0.0329 (5) | 0.0027 (4) | 0.0134 (4) | −0.0008 (4) |
N2 | 0.0371 (5) | 0.0309 (5) | 0.0382 (5) | −0.0004 (4) | 0.0125 (4) | 0.0027 (4) |
N3 | 0.0995 (12) | 0.0542 (8) | 0.0650 (9) | 0.0077 (8) | 0.0349 (8) | −0.0097 (7) |
N4 | 0.0529 (7) | 0.0487 (7) | 0.0338 (5) | 0.0052 (5) | 0.0143 (5) | 0.0007 (5) |
C1 | 0.0451 (7) | 0.0378 (7) | 0.0498 (8) | 0.0013 (5) | 0.0169 (6) | 0.0101 (5) |
C2 | 0.0401 (6) | 0.0312 (6) | 0.0419 (6) | −0.0006 (5) | 0.0142 (5) | 0.0008 (5) |
C3 | 0.0920 (14) | 0.0570 (10) | 0.0468 (8) | 0.0085 (10) | 0.0292 (9) | 0.0095 (8) |
C4 | 0.0534 (8) | 0.0318 (6) | 0.0495 (8) | 0.0033 (6) | 0.0168 (6) | 0.0003 (5) |
C5 | 0.0323 (6) | 0.0292 (5) | 0.0348 (6) | −0.0009 (4) | 0.0115 (5) | −0.0002 (4) |
C6 | 0.0364 (6) | 0.0353 (6) | 0.0330 (6) | −0.0006 (5) | 0.0121 (5) | −0.0002 (5) |
C7 | 0.0431 (7) | 0.0351 (6) | 0.0434 (7) | 0.0018 (5) | 0.0146 (5) | 0.0079 (5) |
C8 | 0.0493 (8) | 0.0298 (6) | 0.0571 (8) | 0.0037 (5) | 0.0211 (6) | −0.0001 (5) |
C9 | 0.0488 (7) | 0.0368 (6) | 0.0444 (7) | −0.0008 (5) | 0.0197 (6) | −0.0081 (5) |
C10 | 0.0414 (6) | 0.0352 (6) | 0.0343 (6) | −0.0006 (5) | 0.0143 (5) | −0.0007 (5) |
O1—C1 | 1.2115 (17) | C3—H32 | 0.96 (3) |
O3—N4 | 1.2161 (15) | C3—H33 | 0.91 (3) |
O2—N4 | 1.2233 (16) | C5—C10 | 1.3979 (16) |
N1—N2 | 1.3184 (14) | C5—C6 | 1.4027 (16) |
N1—C5 | 1.3931 (15) | C6—C7 | 1.3912 (17) |
N1—H1 | 0.864 (17) | C7—C8 | 1.3727 (19) |
N2—C2 | 1.2974 (15) | C7—H7 | 0.943 (17) |
N3—C4 | 1.1360 (19) | C8—C9 | 1.385 (2) |
N4—C6 | 1.4554 (16) | C8—H8 | 0.963 (16) |
C1—C2 | 1.4808 (18) | C9—C10 | 1.3738 (18) |
C1—C3 | 1.481 (2) | C9—H9 | 0.936 (17) |
C2—C4 | 1.4403 (18) | C10—H10 | 0.928 (16) |
C3—H31 | 0.93 (3) | ||
N2—N1—C5 | 118.83 (10) | N3—C4—C2 | 177.40 (16) |
N2—N1—H1 | 121.8 (11) | N1—C5—C10 | 120.29 (11) |
C5—N1—H1 | 118.8 (11) | N1—C5—C6 | 122.19 (11) |
C2—N2—N1 | 119.64 (10) | C10—C5—C6 | 117.51 (11) |
O3—N4—O2 | 122.04 (12) | C7—C6—C5 | 121.34 (11) |
O3—N4—C6 | 118.72 (12) | C7—C6—N4 | 116.53 (11) |
O2—N4—C6 | 119.24 (11) | C5—C6—N4 | 122.12 (11) |
O1—C1—C2 | 118.64 (13) | C8—C7—C6 | 119.87 (12) |
O1—C1—C3 | 123.58 (14) | C8—C7—H7 | 122.0 (10) |
C2—C1—C3 | 117.78 (13) | C6—C7—H7 | 118.2 (10) |
N2—C2—C4 | 123.25 (11) | C7—C8—C9 | 119.35 (12) |
N2—C2—C1 | 118.86 (11) | C7—C8—H8 | 120.4 (9) |
C4—C2—C1 | 117.89 (11) | C9—C8—H8 | 120.3 (9) |
C1—C3—H31 | 109.7 (16) | C10—C9—C8 | 121.36 (12) |
C1—C3—H32 | 112.7 (15) | C10—C9—H9 | 119.4 (10) |
H31—C3—H32 | 112 (2) | C8—C9—H9 | 119.2 (10) |
C1—C3—H33 | 111.8 (17) | C9—C10—C5 | 120.53 (12) |
H31—C3—H33 | 112 (2) | C9—C10—H10 | 121.7 (9) |
H32—C3—H33 | 98 (2) | C5—C10—H10 | 117.8 (9) |