Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520614001152/eb5029sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L1sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L3sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L4sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L5sup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L6sup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L7sup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L8sup8.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L11sup9.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L1unmergedsup10.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L3unmergedsup11.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L4unmergedsup12.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L5unmergedsup13.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L6unmergedsup14.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L7unmergedsup15.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L8unmergedsup16.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L11unmergedsup17.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520614001152/eb5029sup18.pdf |
Crystal data, data collection and structure refinement details are summarized in Table 1.
Data collection: COLLECT (Hooft, R.W.W., 1998) for L1, L3, L5, L6; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) for L4, L11; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) for L7, L8. Cell refinement: DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998) for L1, L3, L5, L6; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) for L4, L11; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) for L7, L8. Data reduction: DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998) for L1, L3, L5, L6; CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) for L4, L11; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) for L7, L8. Program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007) for L1, L3, L5, L6; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) for L4; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 for L7, L11; SHELXD, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 for L8. Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) for L1, L3, L5, L6; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 for L4; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 for L7, L8, L11. Molecular graphics: OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009) for L1, L3, L5, L6; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. for L4, L7, L8, L11. Software used to prepare material for publication: WinGX (Farrugia, 1998) for L1, L3, L5, L6; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. for L4, L7, L8, L11.
C13H10N4 | F(000) = 928 |
Mr = 222.25 | Dx = 1.364 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 39537 reflections |
a = 22.6348 (5) Å | θ = 2.9–27.5° |
b = 5.8250 (1) Å | µ = 0.09 mm−1 |
c = 17.8421 (4) Å | T = 120 K |
β = 113.007 (1)° | Block, colourless |
V = 2165.32 (8) Å3 | 0.34 × 0.23 × 0.20 mm |
Z = 8 |
Bruker-Nonius CCD camera on κ-goniostat diffractometer | 4956 independent reflections |
Radiation source: Bruker Nonius FR591 Rotating Anode | 4405 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 2.9° |
ϕ & ω scans to fill the asymmetric unit | h = −29→29 |
Absorption correction: multi-scan SADABS 2007/2 (Sheldrick, G.M., 2007) | k = −7→6 |
Tmin = 0.971, Tmax = 0.983 | l = −23→20 |
35200 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.0526P)2 + 0.5754P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
4956 reflections | Δρmax = 0.27 e Å−3 |
309 parameters | Δρmin = −0.35 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: 0.033 (2) |
C13H10N4 | V = 2165.32 (8) Å3 |
Mr = 222.25 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 22.6348 (5) Å | µ = 0.09 mm−1 |
b = 5.8250 (1) Å | T = 120 K |
c = 17.8421 (4) Å | 0.34 × 0.23 × 0.20 mm |
β = 113.007 (1)° |
Bruker-Nonius CCD camera on κ-goniostat diffractometer | 4956 independent reflections |
Absorption correction: multi-scan SADABS 2007/2 (Sheldrick, G.M., 2007) | 4405 reflections with I > 2σ(I) |
Tmin = 0.971, Tmax = 0.983 | Rint = 0.057 |
35200 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.27 e Å−3 |
4956 reflections | Δρmin = −0.35 e Å−3 |
309 parameters |
Experimental. SADABS was used to perform the Absorption correction Estimated minimum and maximum transmission: 0.6494 0.7456 The given Tmin and Tmax were generated using the SHELX SIZE command |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | ||
C1 | 0.07886 (7) | 0.2174 (3) | −0.01624 (10) | 0.0207 (3) | |
H1 | 0.0847 | 0.0556 | −0.0136 | 0.025* | |
C2 | 0.11370 (8) | 0.3780 (3) | 0.03988 (10) | 0.0207 (3) | |
C3 | 0.16646 (8) | 0.3450 (3) | 0.11954 (10) | 0.0211 (3) | |
C4 | 0.18296 (8) | 0.5191 (3) | 0.17764 (11) | 0.0242 (4) | |
H4 | 0.1626 | 0.6648 | 0.1652 | 0.029* | |
C5 | 0.23002 (8) | 0.4744 (3) | 0.25434 (11) | 0.0276 (4) | |
H5 | 0.2420 | 0.5889 | 0.2955 | 0.033* | |
C6 | 0.25929 (8) | 0.2604 (3) | 0.26986 (11) | 0.0263 (4) | |
H6 | 0.2912 | 0.2245 | 0.3219 | 0.032* | |
C7 | 0.24073 (8) | 0.1002 (3) | 0.20739 (11) | 0.0257 (4) | |
H7 | 0.2617 | −0.0447 | 0.2178 | 0.031* | |
C8 | −0.01622 (7) | 0.2653 (3) | −0.14985 (9) | 0.0198 (3) | |
C9 | −0.03706 (8) | 0.4117 (3) | −0.21675 (10) | 0.0225 (3) | |
H9 | −0.0180 | 0.5586 | −0.2137 | 0.027* | |
C10 | −0.08616 (8) | 0.3396 (3) | −0.28803 (11) | 0.0261 (4) | |
H10 | −0.1011 | 0.4380 | −0.3341 | 0.031* | |
C11 | −0.11352 (8) | 0.1245 (3) | −0.29233 (11) | 0.0277 (4) | |
H11 | −0.1470 | 0.0756 | −0.3414 | 0.033* | |
C12 | −0.09199 (8) | −0.0197 (3) | −0.22483 (11) | 0.0249 (4) | |
H12 | −0.1107 | −0.1672 | −0.2281 | 0.030* | |
C13 | −0.04348 (8) | 0.0499 (3) | −0.15298 (10) | 0.0214 (3) | |
H13 | −0.0291 | −0.0477 | −0.1066 | 0.026* | |
N1 | 0.08924 (7) | 0.5912 (2) | 0.01212 (9) | 0.0240 (3) | |
N2 | 0.04099 (7) | 0.5688 (2) | −0.05851 (9) | 0.0233 (3) | |
N3 | 0.03426 (6) | 0.3409 (2) | −0.07632 (8) | 0.0199 (3) | |
N4 | 0.19505 (7) | 0.1371 (2) | 0.13310 (9) | 0.0241 (3) | |
C21 | 0.57059 (7) | 0.2865 (3) | 0.09585 (9) | 0.0207 (3) | |
H21 | 0.5773 | 0.4478 | 0.0986 | 0.025* | |
C22 | 0.60466 (8) | 0.1210 (3) | 0.07479 (10) | 0.0209 (3) | |
C23 | 0.65878 (7) | 0.1470 (3) | 0.04927 (10) | 0.0205 (3) | |
C24 | 0.67754 (8) | −0.0357 (3) | 0.01264 (10) | 0.0234 (4) | |
H24 | 0.6566 | −0.1802 | 0.0054 | 0.028* | |
C25 | 0.72751 (8) | −0.0009 (3) | −0.01287 (11) | 0.0271 (4) | |
H25 | 0.7411 | −0.1215 | −0.0383 | 0.032* | |
C26 | 0.75731 (8) | 0.2115 (3) | −0.00089 (11) | 0.0275 (4) | |
H26 | 0.7915 | 0.2399 | −0.0179 | 0.033* | |
C27 | 0.73577 (8) | 0.3812 (3) | 0.03657 (11) | 0.0261 (4) | |
H27 | 0.7564 | 0.5264 | 0.0449 | 0.031* | |
C28 | 0.47567 (7) | 0.2492 (3) | 0.13615 (9) | 0.0198 (3) | |
C29 | 0.44870 (8) | 0.4638 (3) | 0.11137 (10) | 0.0217 (3) | |
H29 | 0.4628 | 0.5583 | 0.0782 | 0.026* | |
C30 | 0.40055 (8) | 0.5388 (3) | 0.13592 (10) | 0.0237 (4) | |
H30 | 0.3820 | 0.6862 | 0.1198 | 0.028* | |
C31 | 0.37951 (8) | 0.3996 (3) | 0.18367 (11) | 0.0263 (4) | |
H31 | 0.3464 | 0.4510 | 0.1997 | 0.032* | |
C32 | 0.40712 (8) | 0.1847 (3) | 0.20791 (10) | 0.0254 (4) | |
H32 | 0.3926 | 0.0895 | 0.2405 | 0.030* | |
C33 | 0.45560 (8) | 0.1081 (3) | 0.18493 (10) | 0.0225 (3) | |
H33 | 0.4748 | −0.0379 | 0.2021 | 0.027* | |
N21 | 0.57889 (7) | −0.0893 (2) | 0.07871 (9) | 0.0236 (3) | |
N22 | 0.53075 (7) | −0.0610 (2) | 0.10136 (9) | 0.0234 (3) | |
N23 | 0.52527 (6) | 0.1679 (2) | 0.11189 (8) | 0.0198 (3) | |
N24 | 0.68751 (7) | 0.3542 (2) | 0.06206 (9) | 0.0234 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0231 (8) | 0.0175 (8) | 0.0222 (8) | 0.0020 (6) | 0.0096 (7) | 0.0011 (6) |
C2 | 0.0227 (8) | 0.0194 (8) | 0.0217 (8) | −0.0001 (6) | 0.0107 (7) | −0.0009 (6) |
C3 | 0.0202 (7) | 0.0219 (8) | 0.0225 (8) | −0.0021 (6) | 0.0098 (7) | 0.0001 (6) |
C4 | 0.0252 (8) | 0.0207 (8) | 0.0264 (9) | −0.0004 (6) | 0.0095 (7) | −0.0020 (7) |
C5 | 0.0272 (9) | 0.0280 (9) | 0.0251 (9) | −0.0042 (7) | 0.0075 (7) | −0.0062 (7) |
C6 | 0.0215 (8) | 0.0304 (9) | 0.0241 (9) | −0.0021 (7) | 0.0058 (7) | 0.0008 (7) |
C7 | 0.0220 (8) | 0.0220 (8) | 0.0312 (10) | 0.0004 (6) | 0.0084 (7) | 0.0023 (7) |
C8 | 0.0199 (7) | 0.0202 (8) | 0.0211 (8) | 0.0003 (6) | 0.0098 (7) | −0.0020 (6) |
C9 | 0.0238 (8) | 0.0198 (8) | 0.0247 (9) | 0.0011 (6) | 0.0103 (7) | 0.0022 (6) |
C10 | 0.0251 (8) | 0.0293 (9) | 0.0224 (8) | 0.0039 (7) | 0.0076 (7) | 0.0038 (7) |
C11 | 0.0215 (8) | 0.0326 (10) | 0.0250 (9) | −0.0006 (7) | 0.0046 (7) | −0.0044 (7) |
C12 | 0.0231 (8) | 0.0210 (8) | 0.0319 (9) | −0.0015 (6) | 0.0121 (7) | −0.0035 (7) |
C13 | 0.0221 (8) | 0.0194 (8) | 0.0231 (8) | 0.0019 (6) | 0.0092 (7) | 0.0020 (6) |
N1 | 0.0259 (7) | 0.0204 (7) | 0.0254 (8) | −0.0016 (6) | 0.0096 (6) | −0.0003 (5) |
N2 | 0.0277 (7) | 0.0155 (7) | 0.0257 (8) | −0.0014 (5) | 0.0094 (6) | −0.0009 (5) |
N3 | 0.0227 (7) | 0.0169 (6) | 0.0201 (7) | −0.0009 (5) | 0.0082 (6) | −0.0007 (5) |
N4 | 0.0234 (7) | 0.0237 (7) | 0.0254 (8) | 0.0004 (6) | 0.0097 (6) | −0.0013 (6) |
C21 | 0.0227 (8) | 0.0182 (8) | 0.0189 (8) | −0.0030 (6) | 0.0056 (7) | −0.0001 (6) |
C22 | 0.0229 (8) | 0.0191 (8) | 0.0180 (8) | −0.0004 (6) | 0.0049 (7) | 0.0006 (6) |
C23 | 0.0200 (7) | 0.0203 (8) | 0.0181 (8) | 0.0013 (6) | 0.0040 (6) | 0.0022 (6) |
C24 | 0.0250 (8) | 0.0197 (8) | 0.0237 (8) | −0.0008 (6) | 0.0074 (7) | 0.0004 (6) |
C25 | 0.0258 (8) | 0.0277 (9) | 0.0281 (9) | 0.0041 (7) | 0.0111 (8) | 0.0015 (7) |
C26 | 0.0204 (8) | 0.0308 (9) | 0.0297 (9) | 0.0024 (7) | 0.0082 (7) | 0.0074 (7) |
C27 | 0.0201 (8) | 0.0229 (8) | 0.0295 (9) | −0.0022 (6) | 0.0033 (7) | 0.0039 (7) |
C28 | 0.0192 (7) | 0.0199 (7) | 0.0184 (8) | −0.0030 (6) | 0.0054 (6) | −0.0023 (6) |
C29 | 0.0231 (7) | 0.0201 (8) | 0.0187 (8) | −0.0039 (6) | 0.0049 (7) | 0.0003 (6) |
C30 | 0.0221 (8) | 0.0180 (8) | 0.0261 (9) | −0.0004 (6) | 0.0039 (7) | −0.0014 (6) |
C31 | 0.0220 (8) | 0.0295 (9) | 0.0273 (9) | −0.0009 (7) | 0.0094 (7) | −0.0025 (7) |
C32 | 0.0247 (8) | 0.0281 (9) | 0.0229 (9) | −0.0034 (7) | 0.0088 (7) | 0.0041 (7) |
C33 | 0.0244 (8) | 0.0203 (8) | 0.0203 (8) | −0.0020 (6) | 0.0061 (7) | 0.0012 (6) |
N21 | 0.0271 (7) | 0.0196 (7) | 0.0233 (8) | −0.0005 (6) | 0.0092 (6) | 0.0010 (5) |
N22 | 0.0275 (7) | 0.0169 (7) | 0.0252 (8) | −0.0006 (5) | 0.0097 (6) | −0.0001 (5) |
N23 | 0.0233 (7) | 0.0152 (6) | 0.0200 (7) | −0.0017 (5) | 0.0074 (6) | −0.0001 (5) |
N24 | 0.0213 (7) | 0.0200 (7) | 0.0239 (7) | −0.0008 (5) | 0.0036 (6) | 0.0007 (5) |
C1—N3 | 1.357 (2) | C21—N23 | 1.357 (2) |
C1—C2 | 1.372 (2) | C21—C22 | 1.375 (2) |
C1—H1 | 0.9500 | C21—H21 | 0.9500 |
C2—N1 | 1.371 (2) | C22—N21 | 1.371 (2) |
C2—C3 | 1.469 (2) | C22—C23 | 1.472 (2) |
C3—N4 | 1.350 (2) | C23—N24 | 1.348 (2) |
C3—C4 | 1.393 (2) | C23—C24 | 1.399 (2) |
C4—C5 | 1.391 (2) | C24—C25 | 1.389 (2) |
C4—H4 | 0.9500 | C24—H24 | 0.9500 |
C5—C6 | 1.388 (3) | C25—C26 | 1.385 (3) |
C5—H5 | 0.9500 | C25—H25 | 0.9500 |
C6—C7 | 1.387 (2) | C26—C27 | 1.384 (3) |
C6—H6 | 0.9500 | C26—H26 | 0.9500 |
C7—N4 | 1.342 (2) | C27—N24 | 1.347 (2) |
C7—H7 | 0.9500 | C27—H27 | 0.9500 |
C8—C13 | 1.389 (2) | C28—C29 | 1.386 (2) |
C8—C9 | 1.391 (2) | C28—C33 | 1.396 (2) |
C8—N3 | 1.431 (2) | C28—N23 | 1.433 (2) |
C9—C10 | 1.387 (2) | C29—C30 | 1.394 (2) |
C9—H9 | 0.9500 | C29—H29 | 0.9500 |
C10—C11 | 1.386 (2) | C30—C31 | 1.388 (2) |
C10—H10 | 0.9500 | C30—H30 | 0.9500 |
C11—C12 | 1.391 (3) | C31—C32 | 1.390 (2) |
C11—H11 | 0.9500 | C31—H31 | 0.9500 |
C12—C13 | 1.383 (2) | C32—C33 | 1.387 (2) |
C12—H12 | 0.9500 | C32—H32 | 0.9500 |
C13—H13 | 0.9500 | C33—H33 | 0.9500 |
N1—N2 | 1.312 (2) | N21—N22 | 1.3123 (19) |
N2—N3 | 1.3601 (18) | N22—N23 | 1.3585 (18) |
N3—C1—C2 | 104.64 (14) | N23—C21—C22 | 104.57 (14) |
N3—C1—H1 | 127.7 | N23—C21—H21 | 127.7 |
C2—C1—H1 | 127.7 | C22—C21—H21 | 127.7 |
N1—C2—C1 | 108.56 (14) | N21—C22—C21 | 108.49 (14) |
N1—C2—C3 | 121.96 (14) | N21—C22—C23 | 122.00 (14) |
C1—C2—C3 | 129.41 (15) | C21—C22—C23 | 129.49 (15) |
N4—C3—C4 | 123.34 (16) | N24—C23—C24 | 123.09 (15) |
N4—C3—C2 | 116.28 (14) | N24—C23—C22 | 116.38 (14) |
C4—C3—C2 | 120.33 (15) | C24—C23—C22 | 120.52 (14) |
C5—C4—C3 | 118.40 (16) | C25—C24—C23 | 118.47 (16) |
C5—C4—H4 | 120.8 | C25—C24—H24 | 120.8 |
C3—C4—H4 | 120.8 | C23—C24—H24 | 120.8 |
C6—C5—C4 | 119.10 (16) | C26—C25—C24 | 119.30 (16) |
C6—C5—H5 | 120.5 | C26—C25—H25 | 120.3 |
C4—C5—H5 | 120.5 | C24—C25—H25 | 120.3 |
C7—C6—C5 | 118.23 (16) | C27—C26—C25 | 118.04 (16) |
C7—C6—H6 | 120.9 | C27—C26—H26 | 121.0 |
C5—C6—H6 | 120.9 | C25—C26—H26 | 121.0 |
N4—C7—C6 | 124.08 (16) | N24—C27—C26 | 124.41 (16) |
N4—C7—H7 | 118.0 | N24—C27—H27 | 117.8 |
C6—C7—H7 | 118.0 | C26—C27—H27 | 117.8 |
C13—C8—C9 | 121.53 (15) | C29—C28—C33 | 121.33 (15) |
C13—C8—N3 | 119.84 (14) | C29—C28—N23 | 120.10 (14) |
C9—C8—N3 | 118.63 (14) | C33—C28—N23 | 118.57 (14) |
C10—C9—C8 | 118.84 (16) | C28—C29—C30 | 118.90 (15) |
C10—C9—H9 | 120.6 | C28—C29—H29 | 120.5 |
C8—C9—H9 | 120.6 | C30—C29—H29 | 120.5 |
C11—C10—C9 | 120.33 (16) | C31—C30—C29 | 120.52 (15) |
C11—C10—H10 | 119.8 | C31—C30—H30 | 119.7 |
C9—C10—H10 | 119.8 | C29—C30—H30 | 119.7 |
C10—C11—C12 | 120.00 (16) | C30—C31—C32 | 119.76 (16) |
C10—C11—H11 | 120.0 | C30—C31—H31 | 120.1 |
C12—C11—H11 | 120.0 | C32—C31—H31 | 120.1 |
C13—C12—C11 | 120.54 (16) | C33—C32—C31 | 120.60 (16) |
C13—C12—H12 | 119.7 | C33—C32—H32 | 119.7 |
C11—C12—H12 | 119.7 | C31—C32—H32 | 119.7 |
C12—C13—C8 | 118.76 (15) | C32—C33—C28 | 118.88 (15) |
C12—C13—H13 | 120.6 | C32—C33—H33 | 120.6 |
C8—C13—H13 | 120.6 | C28—C33—H33 | 120.6 |
N2—N1—C2 | 108.92 (13) | N22—N21—C22 | 108.94 (13) |
N1—N2—N3 | 107.24 (12) | N21—N22—N23 | 107.32 (13) |
C1—N3—N2 | 110.63 (13) | C21—N23—N22 | 110.68 (13) |
C1—N3—C8 | 129.94 (14) | C21—N23—C28 | 129.91 (14) |
N2—N3—C8 | 119.41 (13) | N22—N23—C28 | 119.41 (13) |
C7—N4—C3 | 116.82 (15) | C27—N24—C23 | 116.67 (14) |
N3—C1—C2—N1 | −0.01 (17) | N23—C21—C22—N21 | 0.09 (17) |
N3—C1—C2—C3 | 176.83 (15) | N23—C21—C22—C23 | 178.42 (16) |
N1—C2—C3—N4 | −166.85 (15) | N21—C22—C23—N24 | −168.14 (14) |
C1—C2—C3—N4 | 16.7 (3) | C21—C22—C23—N24 | 13.7 (3) |
N1—C2—C3—C4 | 15.7 (2) | N21—C22—C23—C24 | 12.9 (2) |
C1—C2—C3—C4 | −160.72 (17) | C21—C22—C23—C24 | −165.23 (17) |
N4—C3—C4—C5 | −1.9 (3) | N24—C23—C24—C25 | −1.0 (2) |
C2—C3—C4—C5 | 175.32 (15) | C22—C23—C24—C25 | 177.90 (15) |
C3—C4—C5—C6 | 0.8 (3) | C23—C24—C25—C26 | 0.4 (2) |
C4—C5—C6—C7 | 0.8 (3) | C24—C25—C26—C27 | 0.2 (3) |
C5—C6—C7—N4 | −1.6 (3) | C25—C26—C27—N24 | −0.2 (3) |
C13—C8—C9—C10 | −0.1 (2) | C33—C28—C29—C30 | 0.0 (2) |
N3—C8—C9—C10 | −179.73 (14) | N23—C28—C29—C30 | −179.95 (14) |
C8—C9—C10—C11 | −0.4 (2) | C28—C29—C30—C31 | −0.7 (2) |
C9—C10—C11—C12 | 0.3 (3) | C29—C30—C31—C32 | 0.7 (3) |
C10—C11—C12—C13 | 0.3 (3) | C30—C31—C32—C33 | 0.1 (3) |
C11—C12—C13—C8 | −0.7 (2) | C31—C32—C33—C28 | −0.8 (2) |
C9—C8—C13—C12 | 0.7 (2) | C29—C28—C33—C32 | 0.8 (2) |
N3—C8—C13—C12 | −179.70 (14) | N23—C28—C33—C32 | −179.30 (14) |
C1—C2—N1—N2 | −0.03 (18) | C21—C22—N21—N22 | −0.16 (18) |
C3—C2—N1—N2 | −177.15 (14) | C23—C22—N21—N22 | −178.63 (14) |
C2—N1—N2—N3 | 0.06 (17) | C22—N21—N22—N23 | 0.15 (17) |
C2—C1—N3—N2 | 0.05 (17) | C22—C21—N23—N22 | 0.00 (17) |
C2—C1—N3—C8 | −178.43 (15) | C22—C21—N23—C28 | −179.46 (15) |
N1—N2—N3—C1 | −0.07 (17) | N21—N22—N23—C21 | −0.10 (17) |
N1—N2—N3—C8 | 178.59 (13) | N21—N22—N23—C28 | 179.42 (13) |
C13—C8—N3—C1 | 28.4 (2) | C29—C28—N23—C21 | 30.2 (2) |
C9—C8—N3—C1 | −151.93 (16) | C33—C28—N23—C21 | −149.71 (16) |
C13—C8—N3—N2 | −149.95 (15) | C29—C28—N23—N22 | −149.22 (15) |
C9—C8—N3—N2 | 29.7 (2) | C33—C28—N23—N22 | 30.9 (2) |
C6—C7—N4—C3 | 0.6 (2) | C26—C27—N24—C23 | −0.3 (2) |
C4—C3—N4—C7 | 1.2 (2) | C24—C23—N24—C27 | 0.9 (2) |
C2—C3—N4—C7 | −176.13 (14) | C22—C23—N24—C27 | −178.02 (14) |
C13H9FN4 | F(000) = 496 |
Mr = 240.24 | Dx = 1.452 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 12628 reflections |
a = 12.2031 (3) Å | θ = 2.9–27.5° |
b = 7.9798 (2) Å | µ = 0.10 mm−1 |
c = 11.6329 (3) Å | T = 120 K |
β = 104.043 (2)° | Block, colourless |
V = 1098.94 (5) Å3 | 0.60 × 0.58 × 0.40 mm |
Z = 4 |
Bruker-Nonius CCD camera on κ-goniostat diffractometer | 2510 independent reflections |
Radiation source: Bruker Nonius FR591 Rotating Anode | 2228 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ϕ & ω scans to fill the asymmetric unit | h = −15→15 |
Absorption correction: multi-scan SADABS 2007/2 (Sheldrick, G.M., 2007) | k = −10→10 |
Tmin = 0.940, Tmax = 0.960 | l = −14→15 |
13725 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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.035P)2 + 0.5185P] where P = (Fo2 + 2Fc2)/3 |
2510 reflections | (Δ/σ)max < 0.001 |
163 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C13H9FN4 | V = 1098.94 (5) Å3 |
Mr = 240.24 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.2031 (3) Å | µ = 0.10 mm−1 |
b = 7.9798 (2) Å | T = 120 K |
c = 11.6329 (3) Å | 0.60 × 0.58 × 0.40 mm |
β = 104.043 (2)° |
Bruker-Nonius CCD camera on κ-goniostat diffractometer | 2510 independent reflections |
Absorption correction: multi-scan SADABS 2007/2 (Sheldrick, G.M., 2007) | 2228 reflections with I > 2σ(I) |
Tmin = 0.940, Tmax = 0.960 | Rint = 0.031 |
13725 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.26 e Å−3 |
2510 reflections | Δρmin = −0.23 e Å−3 |
163 parameters |
Experimental. SADABS was used to perform the Absorption correction Estimated minimum and maximum transmission: 0.6346 0.7456 The given Tmin and Tmax were generated using the SHELX SIZE command |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | ||
C1 | 0.07126 (9) | 0.68437 (14) | 0.02975 (10) | 0.0172 (2) | |
C2 | 0.09543 (10) | 0.64013 (15) | −0.07707 (10) | 0.0195 (2) | |
H2 | 0.0471 | 0.6752 | −0.1499 | 0.023* | |
C3 | 0.19055 (10) | 0.54448 (16) | −0.07679 (10) | 0.0216 (3) | |
H3 | 0.2083 | 0.5129 | −0.1489 | 0.026* | |
C4 | 0.25856 (10) | 0.49649 (15) | 0.03077 (11) | 0.0211 (3) | |
C5 | 0.23515 (10) | 0.53617 (16) | 0.13772 (10) | 0.0231 (3) | |
H5 | 0.2832 | 0.4990 | 0.2102 | 0.028* | |
C6 | 0.14010 (10) | 0.63142 (15) | 0.13718 (10) | 0.0213 (3) | |
H6 | 0.1221 | 0.6604 | 0.2096 | 0.026* | |
C7 | −0.10673 (9) | 0.84006 (14) | −0.06520 (10) | 0.0187 (2) | |
H7 | −0.1094 | 0.8258 | −0.1469 | 0.022* | |
C8 | −0.18276 (10) | 0.92393 (14) | −0.01644 (10) | 0.0188 (2) | |
C9 | −0.28701 (10) | 1.01073 (14) | −0.07681 (10) | 0.0193 (2) | |
C10 | −0.35449 (10) | 1.09363 (16) | −0.01403 (11) | 0.0247 (3) | |
H10 | −0.3342 | 1.0958 | 0.0701 | 0.030* | |
C11 | −0.45169 (11) | 1.17277 (17) | −0.07651 (13) | 0.0287 (3) | |
H11 | −0.4992 | 1.2300 | −0.0358 | 0.034* | |
C12 | −0.47890 (10) | 1.16740 (16) | −0.19944 (12) | 0.0278 (3) | |
H12 | −0.5450 | 1.2208 | −0.2446 | 0.033* | |
C13 | −0.40682 (11) | 1.08175 (17) | −0.25425 (12) | 0.0269 (3) | |
H13 | −0.4255 | 1.0781 | −0.3384 | 0.032* | |
N1 | −0.02727 (8) | 0.78225 (12) | 0.02857 (8) | 0.0175 (2) | |
N2 | −0.05257 (9) | 0.82826 (14) | 0.13177 (9) | 0.0233 (2) | |
N3 | −0.14679 (9) | 0.91435 (14) | 0.10410 (9) | 0.0239 (2) | |
N4 | −0.31256 (9) | 1.00390 (13) | −0.19595 (9) | 0.0230 (2) | |
F1 | 0.35306 (6) | 0.40439 (10) | 0.03134 (7) | 0.0304 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0174 (5) | 0.0178 (5) | 0.0160 (5) | −0.0038 (4) | 0.0033 (4) | −0.0004 (4) |
C2 | 0.0205 (6) | 0.0235 (6) | 0.0136 (5) | −0.0049 (5) | 0.0027 (4) | 0.0004 (4) |
C3 | 0.0222 (6) | 0.0254 (6) | 0.0183 (5) | −0.0047 (5) | 0.0070 (4) | −0.0024 (5) |
C4 | 0.0182 (5) | 0.0213 (6) | 0.0238 (6) | −0.0004 (5) | 0.0047 (4) | −0.0014 (5) |
C5 | 0.0248 (6) | 0.0249 (6) | 0.0172 (6) | 0.0008 (5) | 0.0005 (5) | 0.0008 (5) |
C6 | 0.0255 (6) | 0.0238 (6) | 0.0139 (5) | −0.0009 (5) | 0.0036 (4) | −0.0014 (4) |
C7 | 0.0205 (6) | 0.0208 (5) | 0.0142 (5) | −0.0028 (5) | 0.0029 (4) | 0.0011 (4) |
C8 | 0.0214 (6) | 0.0178 (5) | 0.0168 (5) | −0.0044 (4) | 0.0041 (4) | −0.0002 (4) |
C9 | 0.0197 (5) | 0.0179 (5) | 0.0201 (6) | −0.0050 (4) | 0.0044 (4) | 0.0004 (4) |
C10 | 0.0257 (6) | 0.0257 (6) | 0.0241 (6) | −0.0019 (5) | 0.0086 (5) | −0.0016 (5) |
C11 | 0.0232 (6) | 0.0267 (6) | 0.0377 (7) | −0.0002 (5) | 0.0105 (5) | −0.0049 (6) |
C12 | 0.0204 (6) | 0.0231 (6) | 0.0362 (7) | −0.0007 (5) | −0.0001 (5) | −0.0009 (5) |
C13 | 0.0253 (6) | 0.0277 (6) | 0.0243 (6) | 0.0000 (5) | −0.0005 (5) | 0.0005 (5) |
N1 | 0.0208 (5) | 0.0193 (5) | 0.0122 (4) | −0.0026 (4) | 0.0033 (3) | −0.0003 (4) |
N2 | 0.0268 (5) | 0.0290 (5) | 0.0140 (5) | 0.0030 (4) | 0.0046 (4) | −0.0024 (4) |
N3 | 0.0270 (5) | 0.0271 (5) | 0.0169 (5) | 0.0023 (4) | 0.0039 (4) | −0.0011 (4) |
N4 | 0.0231 (5) | 0.0259 (5) | 0.0185 (5) | 0.0004 (4) | 0.0023 (4) | 0.0001 (4) |
F1 | 0.0241 (4) | 0.0372 (4) | 0.0296 (4) | 0.0076 (3) | 0.0056 (3) | −0.0022 (3) |
C1—C2 | 1.3906 (15) | C8—C9 | 1.4689 (16) |
C1—C6 | 1.3916 (16) | C8—N3 | 1.3660 (15) |
C1—N1 | 1.4310 (15) | C9—C10 | 1.3932 (17) |
C2—H2 | 0.9500 | C9—N4 | 1.3458 (15) |
C2—C3 | 1.3886 (17) | C10—H10 | 0.9500 |
C3—H3 | 0.9500 | C10—C11 | 1.3841 (18) |
C3—C4 | 1.3773 (17) | C11—H11 | 0.9500 |
C4—C5 | 1.3792 (17) | C11—C12 | 1.388 (2) |
C4—F1 | 1.3662 (14) | C12—H12 | 0.9500 |
C5—H5 | 0.9500 | C12—C13 | 1.3854 (19) |
C5—C6 | 1.3854 (17) | C13—H13 | 0.9500 |
C6—H6 | 0.9500 | C13—N4 | 1.3381 (16) |
C7—H7 | 0.9500 | N1—N2 | 1.3605 (13) |
C7—C8 | 1.3733 (17) | N2—N3 | 1.3107 (15) |
C7—N1 | 1.3527 (14) | ||
C2—C1—C6 | 120.84 (11) | N3—C8—C9 | 122.85 (11) |
C2—C1—N1 | 119.34 (10) | C10—C9—C8 | 121.78 (11) |
C6—C1—N1 | 119.81 (10) | N4—C9—C8 | 115.51 (10) |
C1—C2—H2 | 120.1 | N4—C9—C10 | 122.71 (11) |
C3—C2—C1 | 119.73 (11) | C9—C10—H10 | 120.6 |
C3—C2—H2 | 120.1 | C11—C10—C9 | 118.79 (12) |
C2—C3—H3 | 120.9 | C11—C10—H10 | 120.6 |
C4—C3—C2 | 118.29 (11) | C10—C11—H11 | 120.4 |
C4—C3—H3 | 120.9 | C10—C11—C12 | 119.15 (12) |
C3—C4—C5 | 123.00 (11) | C12—C11—H11 | 120.4 |
F1—C4—C3 | 118.41 (11) | C11—C12—H12 | 121.0 |
F1—C4—C5 | 118.59 (10) | C13—C12—C11 | 118.00 (12) |
C4—C5—H5 | 120.7 | C13—C12—H12 | 121.0 |
C4—C5—C6 | 118.57 (11) | C12—C13—H13 | 118.0 |
C6—C5—H5 | 120.7 | N4—C13—C12 | 124.02 (12) |
C1—C6—H6 | 120.2 | N4—C13—H13 | 118.0 |
C5—C6—C1 | 119.54 (11) | C7—N1—C1 | 129.06 (10) |
C5—C6—H6 | 120.2 | C7—N1—N2 | 110.35 (10) |
C8—C7—H7 | 127.6 | N2—N1—C1 | 120.59 (9) |
N1—C7—H7 | 127.6 | N3—N2—N1 | 107.35 (9) |
N1—C7—C8 | 104.89 (10) | N2—N3—C8 | 109.01 (10) |
C7—C8—C9 | 128.74 (11) | C13—N4—C9 | 117.32 (11) |
N3—C8—C7 | 108.40 (10) |
C13H9ClN4 | F(000) = 1056 |
Mr = 256.69 | Dx = 1.477 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 16.0000 (11) Å | Cell parameters from 7275 reflections |
b = 5.9258 (2) Å | θ = 3.1–27.5° |
c = 24.3829 (17) Å | µ = 0.32 mm−1 |
β = 93.109 (8)° | T = 120 K |
V = 2308.4 (2) Å3 | Block, colourless |
Z = 8 | 0.36 × 0.12 × 0.06 mm |
Rigaku R-AXIS SPIDER IP diffractometer | 2636 independent reflections |
Radiation source: Sealed X-Ray tube | 1654 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
Detector resolution: 10 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
profile data from oscillation ω–scans | h = −20→20 |
Absorption correction: multi-scan CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) | k = −7→6 |
Tmin = 0.608, Tmax = 1.000 | l = −31→31 |
11996 measured reflections |
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0776P)2] where P = (Fo2 + 2Fc2)/3 |
2636 reflections | (Δ/σ)max < 0.001 |
163 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.46 e Å−3 |
C13H9ClN4 | V = 2308.4 (2) Å3 |
Mr = 256.69 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 16.0000 (11) Å | µ = 0.32 mm−1 |
b = 5.9258 (2) Å | T = 120 K |
c = 24.3829 (17) Å | 0.36 × 0.12 × 0.06 mm |
β = 93.109 (8)° |
Rigaku R-AXIS SPIDER IP diffractometer | 2636 independent reflections |
Absorption correction: multi-scan CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) | 1654 reflections with I > 2σ(I) |
Tmin = 0.608, Tmax = 1.000 | Rint = 0.050 |
11996 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.25 e Å−3 |
2636 reflections | Δρmin = −0.46 e Å−3 |
163 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 | ||
Cl1 | 0.46583 (4) | 0.73367 (10) | 0.32948 (2) | 0.0400 (2) | |
N1 | 0.81166 (11) | 0.3764 (3) | 0.65649 (7) | 0.0331 (4) | |
N8 | 0.67605 (12) | 0.0050 (3) | 0.57198 (8) | 0.0334 (4) | |
N9 | 0.63176 (12) | 0.0605 (3) | 0.52701 (8) | 0.0336 (5) | |
N10 | 0.64080 (11) | 0.2865 (3) | 0.51988 (7) | 0.0269 (4) | |
C2 | 0.86138 (15) | 0.3720 (4) | 0.70229 (9) | 0.0368 (5) | |
H2 | 0.8930 | 0.5001 | 0.7109 | 0.044* | |
C3 | 0.86908 (15) | 0.1908 (4) | 0.73758 (9) | 0.0362 (5) | |
H3 | 0.9049 | 0.1967 | 0.7689 | 0.043* | |
C4 | 0.82221 (14) | 0.0005 (4) | 0.72520 (9) | 0.0358 (5) | |
H4 | 0.8251 | −0.1241 | 0.7484 | 0.043* | |
C5 | 0.77106 (14) | −0.0028 (4) | 0.67803 (9) | 0.0344 (5) | |
H5 | 0.7395 | −0.1302 | 0.6687 | 0.041* | |
C6 | 0.76725 (14) | 0.1877 (3) | 0.64441 (9) | 0.0290 (5) | |
C7 | 0.71381 (13) | 0.1947 (3) | 0.59369 (9) | 0.0274 (5) | |
C11 | 0.69147 (13) | 0.3742 (3) | 0.56060 (8) | 0.0278 (5) | |
H11 | 0.7077 | 0.5240 | 0.5652 | 0.033* | |
C12 | 0.59896 (12) | 0.3934 (3) | 0.47387 (8) | 0.0267 (5) | |
C13 | 0.62574 (13) | 0.6034 (3) | 0.45686 (8) | 0.0288 (5) | |
H13 | 0.6710 | 0.6734 | 0.4754 | 0.035* | |
C14 | 0.58504 (14) | 0.7085 (3) | 0.41235 (9) | 0.0301 (5) | |
H14 | 0.6027 | 0.8492 | 0.4006 | 0.036* | |
C15 | 0.51758 (13) | 0.6012 (4) | 0.38542 (8) | 0.0303 (5) | |
C16 | 0.49039 (14) | 0.3917 (4) | 0.40234 (9) | 0.0320 (5) | |
H16 | 0.4452 | 0.3217 | 0.3837 | 0.038* | |
C17 | 0.53063 (13) | 0.2880 (3) | 0.44687 (9) | 0.0297 (5) | |
H17 | 0.5123 | 0.1484 | 0.4589 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0384 (4) | 0.0445 (4) | 0.0364 (4) | −0.0038 (3) | −0.0039 (2) | 0.0032 (2) |
N1 | 0.0349 (11) | 0.0312 (10) | 0.0330 (11) | −0.0047 (8) | 0.0006 (8) | 0.0007 (8) |
N8 | 0.0359 (11) | 0.0268 (9) | 0.0370 (11) | −0.0022 (8) | −0.0010 (8) | −0.0006 (8) |
N9 | 0.0369 (11) | 0.0226 (9) | 0.0411 (11) | −0.0038 (8) | 0.0005 (9) | −0.0004 (8) |
N10 | 0.0296 (10) | 0.0219 (9) | 0.0296 (10) | −0.0028 (7) | 0.0048 (7) | −0.0027 (7) |
C2 | 0.0371 (13) | 0.0328 (12) | 0.0401 (13) | −0.0074 (10) | −0.0001 (10) | −0.0019 (10) |
C3 | 0.0360 (13) | 0.0410 (13) | 0.0314 (13) | 0.0025 (11) | 0.0010 (10) | 0.0011 (10) |
C4 | 0.0429 (14) | 0.0315 (12) | 0.0331 (12) | 0.0027 (10) | 0.0037 (10) | 0.0053 (10) |
C5 | 0.0383 (13) | 0.0282 (12) | 0.0370 (13) | −0.0019 (10) | 0.0052 (10) | 0.0013 (9) |
C6 | 0.0302 (12) | 0.0277 (12) | 0.0297 (12) | −0.0004 (9) | 0.0061 (9) | −0.0018 (9) |
C7 | 0.0263 (11) | 0.0258 (11) | 0.0306 (11) | −0.0037 (9) | 0.0046 (9) | −0.0013 (9) |
C11 | 0.0301 (12) | 0.0240 (11) | 0.0295 (11) | −0.0060 (9) | 0.0032 (9) | −0.0023 (9) |
C12 | 0.0261 (11) | 0.0247 (11) | 0.0298 (12) | 0.0005 (9) | 0.0050 (9) | −0.0050 (9) |
C13 | 0.0292 (12) | 0.0250 (11) | 0.0325 (12) | −0.0029 (9) | 0.0032 (9) | −0.0048 (9) |
C14 | 0.0321 (12) | 0.0261 (11) | 0.0324 (12) | −0.0041 (9) | 0.0057 (9) | −0.0013 (9) |
C15 | 0.0301 (12) | 0.0321 (12) | 0.0290 (11) | −0.0003 (9) | 0.0043 (9) | −0.0043 (9) |
C16 | 0.0288 (12) | 0.0315 (12) | 0.0357 (12) | −0.0074 (9) | 0.0023 (9) | −0.0075 (10) |
C17 | 0.0277 (12) | 0.0266 (11) | 0.0353 (13) | −0.0037 (9) | 0.0045 (9) | −0.0027 (9) |
Cl1—C15 | 1.743 (2) | C5—C6 | 1.395 (3) |
N1—C2 | 1.336 (3) | C6—C7 | 1.465 (3) |
N1—C6 | 1.349 (3) | C7—C11 | 1.371 (3) |
N8—N9 | 1.315 (3) | C11—H11 | 0.9300 |
N8—C7 | 1.369 (3) | C12—C13 | 1.387 (3) |
N9—N10 | 1.359 (2) | C12—C17 | 1.393 (3) |
N10—C11 | 1.351 (3) | C13—H13 | 0.9300 |
N10—C12 | 1.423 (3) | C13—C14 | 1.383 (3) |
C2—H2 | 0.9300 | C14—H14 | 0.9300 |
C2—C3 | 1.377 (3) | C14—C15 | 1.387 (3) |
C3—H3 | 0.9300 | C15—C16 | 1.385 (3) |
C3—C4 | 1.379 (3) | C16—H16 | 0.9300 |
C4—H4 | 0.9300 | C16—C17 | 1.377 (3) |
C4—C5 | 1.375 (3) | C17—H17 | 0.9300 |
C5—H5 | 0.9300 | ||
C2—N1—C6 | 116.68 (19) | C11—C7—C6 | 129.8 (2) |
N9—N8—C7 | 108.87 (17) | N10—C11—C7 | 105.12 (18) |
N8—N9—N10 | 107.28 (17) | N10—C11—H11 | 127.4 |
N9—N10—C12 | 119.36 (17) | C7—C11—H11 | 127.4 |
C11—N10—N9 | 110.41 (17) | C13—C12—N10 | 119.68 (18) |
C11—N10—C12 | 130.23 (17) | C13—C12—C17 | 120.54 (19) |
N1—C2—H2 | 117.7 | C17—C12—N10 | 119.77 (19) |
N1—C2—C3 | 124.5 (2) | C12—C13—H13 | 120.0 |
C3—C2—H2 | 117.7 | C14—C13—C12 | 119.92 (19) |
C2—C3—H3 | 120.9 | C14—C13—H13 | 120.0 |
C2—C3—C4 | 118.1 (2) | C13—C14—H14 | 120.5 |
C4—C3—H3 | 120.9 | C13—C14—C15 | 119.09 (19) |
C3—C4—H4 | 120.4 | C15—C14—H14 | 120.5 |
C5—C4—C3 | 119.1 (2) | C14—C15—Cl1 | 119.23 (17) |
C5—C4—H4 | 120.4 | C16—C15—Cl1 | 119.53 (17) |
C4—C5—H5 | 120.5 | C16—C15—C14 | 121.2 (2) |
C4—C5—C6 | 119.0 (2) | C15—C16—H16 | 120.2 |
C6—C5—H5 | 120.5 | C17—C16—C15 | 119.6 (2) |
N1—C6—C5 | 122.5 (2) | C17—C16—H16 | 120.2 |
N1—C6—C7 | 115.94 (19) | C12—C17—H17 | 120.2 |
C5—C6—C7 | 121.6 (2) | C16—C17—C12 | 119.60 (19) |
N8—C7—C6 | 121.89 (19) | C16—C17—H17 | 120.2 |
N8—C7—C11 | 108.32 (19) | ||
Cl1—C15—C16—C17 | −179.30 (16) | C4—C5—C6—N1 | −0.3 (3) |
N1—C2—C3—C4 | −0.3 (4) | C4—C5—C6—C7 | −179.9 (2) |
N1—C6—C7—N8 | 169.32 (19) | C5—C6—C7—N8 | −11.1 (3) |
N1—C6—C7—C11 | −11.4 (3) | C5—C6—C7—C11 | 168.2 (2) |
N8—N9—N10—C11 | 0.2 (2) | C6—N1—C2—C3 | −0.8 (3) |
N8—N9—N10—C12 | −179.86 (16) | C6—C7—C11—N10 | −179.4 (2) |
N8—C7—C11—N10 | 0.0 (2) | C7—N8—N9—N10 | −0.2 (2) |
N9—N8—C7—C6 | 179.56 (18) | C11—N10—C12—C13 | 18.8 (3) |
N9—N8—C7—C11 | 0.1 (2) | C11—N10—C12—C17 | −160.1 (2) |
N9—N10—C11—C7 | −0.1 (2) | C12—N10—C11—C7 | 179.96 (19) |
N9—N10—C12—C13 | −161.09 (19) | C12—C13—C14—C15 | 0.1 (3) |
N9—N10—C12—C17 | 20.0 (3) | C13—C12—C17—C16 | 1.2 (3) |
N10—C12—C13—C14 | −179.67 (18) | C13—C14—C15—Cl1 | 179.72 (14) |
N10—C12—C17—C16 | −179.92 (18) | C13—C14—C15—C16 | 0.1 (3) |
C2—N1—C6—C5 | 1.1 (3) | C14—C15—C16—C17 | 0.3 (3) |
C2—N1—C6—C7 | −179.30 (18) | C15—C16—C17—C12 | −0.9 (3) |
C2—C3—C4—C5 | 1.1 (3) | C17—C12—C13—C14 | −0.7 (3) |
C3—C4—C5—C6 | −0.8 (3) |
C14H12N4 | F(000) = 248 |
Mr = 236.28 | Dx = 1.341 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 17303 reflections |
a = 5.7797 (5) Å | θ = 2.9–27.5° |
b = 6.7414 (4) Å | µ = 0.08 mm−1 |
c = 15.0259 (12) Å | T = 120 K |
β = 92.359 (4)° | Block, colourless |
V = 584.96 (8) Å3 | 0.38 × 0.12 × 0.10 mm |
Z = 2 |
Bruker-Nonius CCD camera on κ-goniostat diffractometer | 2622 independent reflections |
Radiation source: Bruker Nonius FR591 Rotating Anode | 2042 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.3° |
ϕ & ω scans to fill the asymmetric unit | h = −7→7 |
Absorption correction: multi-scan SADABS 2007/2 (Sheldrick, G.M., 2007) | k = −8→8 |
Tmin = 0.969, Tmax = 0.992 | l = −19→19 |
9647 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.124 | w = 1/[σ2(Fo2) + (0.0694P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
2622 reflections | Δρmax = 0.17 e Å−3 |
165 parameters | Δρmin = −0.18 e Å−3 |
1 restraint | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.047 (8) |
C14H12N4 | V = 584.96 (8) Å3 |
Mr = 236.28 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 5.7797 (5) Å | µ = 0.08 mm−1 |
b = 6.7414 (4) Å | T = 120 K |
c = 15.0259 (12) Å | 0.38 × 0.12 × 0.10 mm |
β = 92.359 (4)° |
Bruker-Nonius CCD camera on κ-goniostat diffractometer | 2622 independent reflections |
Absorption correction: multi-scan SADABS 2007/2 (Sheldrick, G.M., 2007) | 2042 reflections with I > 2σ(I) |
Tmin = 0.969, Tmax = 0.992 | Rint = 0.056 |
9647 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 1 restraint |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.17 e Å−3 |
2622 reflections | Δρmin = −0.18 e Å−3 |
165 parameters |
Experimental. SADABS was used to perform the Absorption correction Estimated minimum and maximum transmission: 0.5177 0.7456 The given Tmin and Tmax were generated using the SHELX SIZE command |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | ||
C1 | 0.7152 (4) | 0.7358 (3) | 0.18589 (13) | 0.0263 (5) | |
C2 | 0.9309 (4) | 0.6565 (3) | 0.20725 (14) | 0.0295 (5) | |
H2 | 1.0340 | 0.7218 | 0.2485 | 0.035* | |
C3 | 0.9947 (4) | 0.4795 (3) | 0.16742 (14) | 0.0307 (5) | |
H3 | 1.1424 | 0.4243 | 0.1824 | 0.037* | |
C4 | 0.8491 (4) | 0.3815 (3) | 0.10649 (13) | 0.0285 (5) | |
C5 | 0.6324 (4) | 0.4656 (3) | 0.08594 (14) | 0.0331 (5) | |
H5 | 0.5290 | 0.4010 | 0.0446 | 0.040* | |
C6 | 0.5658 (4) | 0.6421 (3) | 0.12498 (14) | 0.0320 (5) | |
H6 | 0.4186 | 0.6983 | 0.1100 | 0.038* | |
C7 | 0.9249 (4) | 0.1921 (3) | 0.06262 (14) | 0.0360 (6) | |
H7A | 0.9863 | 0.2228 | 0.0044 | 0.054* | |
H7B | 0.7920 | 0.1026 | 0.0547 | 0.054* | |
H7C | 1.0455 | 0.1279 | 0.1003 | 0.054* | |
C8 | 0.7622 (4) | 1.0476 (3) | 0.27842 (13) | 0.0270 (5) | |
H8 | 0.9242 | 1.0491 | 0.2920 | 0.032* | |
C9 | 0.6011 (4) | 1.1810 (3) | 0.30500 (13) | 0.0277 (5) | |
C10 | 0.6295 (4) | 1.3623 (3) | 0.35857 (14) | 0.0282 (5) | |
C11 | 0.4514 (4) | 1.5010 (3) | 0.36158 (15) | 0.0331 (5) | |
H11 | 0.3085 | 1.4789 | 0.3296 | 0.040* | |
C12 | 0.4854 (4) | 1.6720 (4) | 0.41189 (15) | 0.0395 (6) | |
H12 | 0.3677 | 1.7699 | 0.4144 | 0.047* | |
C13 | 0.6950 (4) | 1.6958 (4) | 0.45822 (15) | 0.0422 (6) | |
H13 | 0.7241 | 1.8107 | 0.4935 | 0.051* | |
C14 | 0.8611 (4) | 1.5505 (4) | 0.45245 (15) | 0.0412 (6) | |
H14 | 1.0037 | 1.5690 | 0.4851 | 0.049* | |
N1 | 0.6415 (3) | 0.9134 (3) | 0.22877 (11) | 0.0268 (4) | |
N2 | 0.4112 (3) | 0.9609 (3) | 0.22484 (13) | 0.0349 (5) | |
N3 | 0.3881 (3) | 1.1240 (3) | 0.27119 (12) | 0.0356 (5) | |
N4 | 0.8353 (3) | 1.3853 (3) | 0.40398 (11) | 0.0345 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0255 (11) | 0.0259 (11) | 0.0276 (10) | −0.0023 (9) | 0.0029 (9) | 0.0025 (9) |
C2 | 0.0248 (11) | 0.0292 (12) | 0.0342 (11) | 0.0000 (9) | −0.0020 (9) | −0.0041 (9) |
C3 | 0.0267 (11) | 0.0326 (12) | 0.0328 (11) | −0.0002 (10) | 0.0011 (9) | 0.0029 (9) |
C4 | 0.0310 (12) | 0.0281 (12) | 0.0266 (10) | −0.0018 (10) | 0.0047 (9) | 0.0025 (9) |
C5 | 0.0313 (12) | 0.0378 (13) | 0.0299 (12) | −0.0038 (10) | −0.0017 (9) | −0.0070 (9) |
C6 | 0.0266 (11) | 0.0383 (13) | 0.0309 (11) | 0.0001 (10) | −0.0022 (9) | 0.0001 (10) |
C7 | 0.0405 (14) | 0.0345 (13) | 0.0328 (12) | 0.0012 (11) | 0.0009 (10) | −0.0035 (9) |
C8 | 0.0244 (11) | 0.0292 (12) | 0.0274 (11) | −0.0008 (9) | −0.0006 (8) | 0.0026 (9) |
C9 | 0.0261 (11) | 0.0275 (11) | 0.0295 (11) | 0.0003 (9) | 0.0021 (8) | 0.0025 (9) |
C10 | 0.0288 (11) | 0.0295 (12) | 0.0269 (10) | −0.0002 (9) | 0.0080 (8) | 0.0026 (9) |
C11 | 0.0338 (12) | 0.0352 (14) | 0.0309 (11) | 0.0052 (11) | 0.0059 (9) | 0.0045 (10) |
C12 | 0.0455 (15) | 0.0337 (13) | 0.0404 (13) | 0.0039 (11) | 0.0152 (11) | −0.0005 (10) |
C13 | 0.0444 (15) | 0.0403 (14) | 0.0427 (14) | −0.0046 (12) | 0.0117 (12) | −0.0088 (11) |
C14 | 0.0415 (14) | 0.0439 (15) | 0.0385 (13) | −0.0035 (12) | 0.0064 (10) | −0.0102 (11) |
N1 | 0.0211 (9) | 0.0281 (10) | 0.0312 (9) | 0.0007 (7) | 0.0001 (7) | 0.0002 (8) |
N2 | 0.0228 (10) | 0.0367 (11) | 0.0450 (11) | 0.0043 (8) | −0.0017 (8) | −0.0039 (8) |
N3 | 0.0274 (10) | 0.0362 (11) | 0.0432 (11) | 0.0025 (8) | −0.0006 (8) | −0.0053 (9) |
N4 | 0.0334 (11) | 0.0366 (11) | 0.0337 (10) | −0.0011 (9) | 0.0032 (8) | −0.0034 (8) |
C1—C2 | 1.382 (3) | C8—C9 | 1.366 (3) |
C1—C6 | 1.385 (3) | C8—H8 | 0.9500 |
C1—N1 | 1.433 (3) | C9—N3 | 1.367 (3) |
C2—C3 | 1.391 (3) | C9—C10 | 1.469 (3) |
C2—H2 | 0.9500 | C10—N4 | 1.356 (3) |
C3—C4 | 1.386 (3) | C10—C11 | 1.393 (3) |
C3—H3 | 0.9500 | C11—C12 | 1.388 (3) |
C4—C5 | 1.398 (3) | C11—H11 | 0.9500 |
C4—C7 | 1.510 (3) | C12—C13 | 1.382 (4) |
C5—C6 | 1.388 (3) | C12—H12 | 0.9500 |
C5—H5 | 0.9500 | C13—C14 | 1.377 (3) |
C6—H6 | 0.9500 | C13—H13 | 0.9500 |
C7—H7A | 0.9800 | C14—N4 | 1.336 (3) |
C7—H7B | 0.9800 | C14—H14 | 0.9500 |
C7—H7C | 0.9800 | N1—N2 | 1.368 (2) |
C8—N1 | 1.349 (3) | N2—N3 | 1.311 (3) |
C2—C1—C6 | 120.6 (2) | C9—C8—H8 | 127.5 |
C2—C1—N1 | 120.08 (19) | C8—C9—N3 | 108.68 (19) |
C6—C1—N1 | 119.30 (19) | C8—C9—C10 | 130.2 (2) |
C1—C2—C3 | 119.0 (2) | N3—C9—C10 | 121.09 (19) |
C1—C2—H2 | 120.5 | N4—C10—C11 | 122.8 (2) |
C3—C2—H2 | 120.5 | N4—C10—C9 | 116.55 (18) |
C4—C3—C2 | 121.9 (2) | C11—C10—C9 | 120.7 (2) |
C4—C3—H3 | 119.0 | C12—C11—C10 | 119.2 (2) |
C2—C3—H3 | 119.0 | C12—C11—H11 | 120.4 |
C3—C4—C5 | 117.82 (19) | C10—C11—H11 | 120.4 |
C3—C4—C7 | 120.8 (2) | C13—C12—C11 | 118.2 (2) |
C5—C4—C7 | 121.3 (2) | C13—C12—H12 | 120.9 |
C6—C5—C4 | 121.1 (2) | C11—C12—H12 | 120.9 |
C6—C5—H5 | 119.5 | C14—C13—C12 | 119.0 (2) |
C4—C5—H5 | 119.5 | C14—C13—H13 | 120.5 |
C1—C6—C5 | 119.6 (2) | C12—C13—H13 | 120.5 |
C1—C6—H6 | 120.2 | N4—C14—C13 | 124.4 (2) |
C5—C6—H6 | 120.2 | N4—C14—H14 | 117.8 |
C4—C7—H7A | 109.5 | C13—C14—H14 | 117.8 |
C4—C7—H7B | 109.5 | C8—N1—N2 | 110.29 (17) |
H7A—C7—H7B | 109.5 | C8—N1—C1 | 130.74 (18) |
C4—C7—H7C | 109.5 | N2—N1—C1 | 118.90 (17) |
H7A—C7—H7C | 109.5 | N3—N2—N1 | 107.06 (17) |
H7B—C7—H7C | 109.5 | N2—N3—C9 | 108.89 (17) |
N1—C8—C9 | 105.08 (18) | C14—N4—C10 | 116.5 (2) |
N1—C8—H8 | 127.5 |
C14H9F3N4 | Z = 2 |
Mr = 290.25 | F(000) = 296 |
Triclinic, P1 | Dx = 1.585 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.7460 (1) Å | Cell parameters from 9548 reflections |
b = 7.2076 (2) Å | θ = 2.9–27.5° |
c = 15.2997 (4) Å | µ = 0.13 mm−1 |
α = 103.045 (2)° | T = 120 K |
β = 98.768 (2)° | Block, colourless |
γ = 92.290 (2)° | 0.60 × 0.20 × 0.18 mm |
V = 608.25 (3) Å3 |
Bruker-Nonius CCD camera on κ-goniostat diffractometer | 2785 independent reflections |
Radiation source: Bruker Nonius FR591 Rotating Anode | 2436 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 2.9° |
ϕ & ω scans to fill the asymmetric unit | h = −7→7 |
Absorption correction: multi-scan SADABS 2007/2 (Sheldrick, G.M., 2007) | k = −9→9 |
Tmin = 0.925, Tmax = 0.977 | l = −19→19 |
14232 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.109 | w = 1/[σ2(Fo2) + (0.0577P)2 + 0.2868P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
2785 reflections | Δρmax = 0.37 e Å−3 |
191 parameters | Δρmin = −0.30 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: 0.040 (9) |
C14H9F3N4 | γ = 92.290 (2)° |
Mr = 290.25 | V = 608.25 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.7460 (1) Å | Mo Kα radiation |
b = 7.2076 (2) Å | µ = 0.13 mm−1 |
c = 15.2997 (4) Å | T = 120 K |
α = 103.045 (2)° | 0.60 × 0.20 × 0.18 mm |
β = 98.768 (2)° |
Bruker-Nonius CCD camera on κ-goniostat diffractometer | 2785 independent reflections |
Absorption correction: multi-scan SADABS 2007/2 (Sheldrick, G.M., 2007) | 2436 reflections with I > 2σ(I) |
Tmin = 0.925, Tmax = 0.977 | Rint = 0.035 |
14232 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.109 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.37 e Å−3 |
2785 reflections | Δρmin = −0.30 e Å−3 |
191 parameters |
Experimental. SADABS was used to perform the Absorption correction Estimated minimum and maximum transmission: 0.6704 0.7456 The given Tmin and Tmax were generated using the SHELX SIZE command |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | ||
F1 | 0.3128 (2) | 0.43341 (14) | 0.05724 (6) | 0.0375 (3) | |
F2 | 0.52678 (16) | 0.21283 (14) | 0.00329 (6) | 0.0297 (2) | |
F3 | 0.19398 (17) | 0.13851 (15) | 0.03806 (6) | 0.0353 (3) | |
N4 | 0.7027 (2) | 0.16644 (16) | 0.68200 (8) | 0.0179 (3) | |
N2 | 1.04755 (19) | 0.27825 (17) | 0.44702 (8) | 0.0188 (3) | |
N1 | 0.80777 (19) | 0.25217 (16) | 0.42478 (7) | 0.0155 (2) | |
N3 | 1.1018 (2) | 0.27229 (17) | 0.53222 (8) | 0.0189 (3) | |
C14 | 0.7054 (2) | 0.16196 (19) | 0.76930 (9) | 0.0187 (3) | |
H16 | 0.5652 | 0.1146 | 0.7854 | 0.022* | |
C5 | 0.3835 (2) | 0.33679 (18) | 0.23248 (9) | 0.0170 (3) | |
H5 | 0.2352 | 0.3883 | 0.2213 | 0.020* | |
C6 | 0.4823 (2) | 0.33276 (18) | 0.32066 (9) | 0.0169 (3) | |
H6 | 0.4027 | 0.3808 | 0.3702 | 0.020* | |
C1 | 0.6999 (2) | 0.25706 (18) | 0.33522 (8) | 0.0152 (3) | |
C4 | 0.5016 (2) | 0.26543 (18) | 0.16024 (9) | 0.0160 (3) | |
C9 | 0.8988 (2) | 0.24162 (18) | 0.56547 (9) | 0.0159 (3) | |
C10 | 0.9042 (2) | 0.23227 (18) | 0.66061 (9) | 0.0153 (3) | |
C11 | 1.1095 (2) | 0.29355 (19) | 0.72447 (9) | 0.0180 (3) | |
H13 | 1.2491 | 0.3372 | 0.7066 | 0.022* | |
C8 | 0.7093 (2) | 0.22909 (18) | 0.49709 (9) | 0.0163 (3) | |
H8 | 0.5465 | 0.2089 | 0.4999 | 0.020* | |
C13 | 0.8992 (2) | 0.22189 (19) | 0.83764 (9) | 0.0191 (3) | |
H15 | 0.8911 | 0.2169 | 0.8986 | 0.023* | |
C12 | 1.1058 (2) | 0.28946 (19) | 0.81446 (9) | 0.0195 (3) | |
H14 | 1.2420 | 0.3321 | 0.8595 | 0.023* | |
C7 | 0.3857 (2) | 0.26374 (19) | 0.06569 (9) | 0.0192 (3) | |
C2 | 0.8201 (2) | 0.18751 (18) | 0.26371 (9) | 0.0165 (3) | |
H2 | 0.9694 | 0.1376 | 0.2750 | 0.020* | |
C3 | 0.7204 (2) | 0.19164 (18) | 0.17579 (9) | 0.0171 (3) | |
H3 | 0.8008 | 0.1444 | 0.1265 | 0.021* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0611 (7) | 0.0297 (5) | 0.0225 (5) | 0.0215 (5) | 0.0019 (4) | 0.0080 (4) |
F2 | 0.0324 (5) | 0.0430 (5) | 0.0163 (4) | 0.0086 (4) | 0.0083 (4) | 0.0087 (4) |
F3 | 0.0303 (5) | 0.0483 (6) | 0.0226 (5) | −0.0140 (4) | −0.0059 (4) | 0.0087 (4) |
N4 | 0.0164 (5) | 0.0201 (5) | 0.0182 (6) | 0.0016 (4) | 0.0032 (4) | 0.0063 (4) |
N2 | 0.0147 (5) | 0.0254 (6) | 0.0161 (5) | 0.0011 (4) | 0.0018 (4) | 0.0053 (4) |
N1 | 0.0135 (5) | 0.0188 (5) | 0.0144 (5) | 0.0003 (4) | 0.0024 (4) | 0.0043 (4) |
N3 | 0.0163 (5) | 0.0249 (6) | 0.0164 (6) | 0.0023 (4) | 0.0031 (4) | 0.0063 (4) |
C14 | 0.0176 (6) | 0.0206 (6) | 0.0201 (7) | 0.0033 (5) | 0.0058 (5) | 0.0074 (5) |
C5 | 0.0149 (6) | 0.0179 (6) | 0.0186 (6) | 0.0015 (5) | 0.0022 (5) | 0.0057 (5) |
C6 | 0.0171 (6) | 0.0179 (6) | 0.0161 (6) | 0.0005 (5) | 0.0056 (5) | 0.0035 (5) |
C1 | 0.0156 (6) | 0.0158 (6) | 0.0142 (6) | −0.0019 (5) | 0.0020 (5) | 0.0045 (5) |
C4 | 0.0183 (6) | 0.0143 (6) | 0.0149 (6) | −0.0019 (5) | 0.0020 (5) | 0.0036 (5) |
C9 | 0.0155 (6) | 0.0157 (6) | 0.0167 (6) | 0.0012 (5) | 0.0036 (5) | 0.0034 (5) |
C10 | 0.0159 (6) | 0.0148 (6) | 0.0157 (6) | 0.0027 (5) | 0.0031 (5) | 0.0041 (5) |
C11 | 0.0163 (6) | 0.0191 (6) | 0.0193 (7) | −0.0001 (5) | 0.0022 (5) | 0.0066 (5) |
C8 | 0.0156 (6) | 0.0193 (6) | 0.0153 (6) | 0.0001 (5) | 0.0040 (5) | 0.0058 (5) |
C13 | 0.0237 (7) | 0.0191 (6) | 0.0160 (6) | 0.0052 (5) | 0.0044 (5) | 0.0057 (5) |
C12 | 0.0210 (7) | 0.0191 (6) | 0.0168 (6) | 0.0015 (5) | −0.0012 (5) | 0.0034 (5) |
C7 | 0.0229 (7) | 0.0185 (6) | 0.0163 (6) | 0.0019 (5) | 0.0031 (5) | 0.0044 (5) |
C2 | 0.0154 (6) | 0.0170 (6) | 0.0176 (6) | 0.0011 (5) | 0.0039 (5) | 0.0042 (5) |
C3 | 0.0186 (6) | 0.0169 (6) | 0.0157 (6) | 0.0001 (5) | 0.0051 (5) | 0.0022 (5) |
F1—C7 | 1.3355 (16) | C6—H6 | 0.9500 |
F2—C7 | 1.3434 (16) | C1—C2 | 1.3914 (18) |
F3—C7 | 1.3466 (16) | C4—C3 | 1.3925 (19) |
N4—C14 | 1.3410 (17) | C4—C7 | 1.4947 (18) |
N4—C10 | 1.3471 (17) | C9—C8 | 1.3749 (18) |
N2—N3 | 1.3042 (16) | C9—C10 | 1.4679 (18) |
N2—N1 | 1.3627 (15) | C10—C11 | 1.3977 (18) |
N1—C8 | 1.3556 (16) | C11—C12 | 1.3871 (19) |
N1—C1 | 1.4240 (16) | C11—H13 | 0.9500 |
N3—C9 | 1.3707 (17) | C8—H8 | 0.9500 |
C14—C13 | 1.387 (2) | C13—C12 | 1.390 (2) |
C14—H16 | 0.9500 | C13—H15 | 0.9500 |
C5—C6 | 1.3889 (18) | C12—H14 | 0.9500 |
C5—C4 | 1.3950 (18) | C2—C3 | 1.3869 (18) |
C5—H5 | 0.9500 | C2—H2 | 0.9500 |
C6—C1 | 1.3909 (18) | C3—H3 | 0.9500 |
C14—N4—C10 | 116.77 (12) | C11—C10—C9 | 120.30 (12) |
N3—N2—N1 | 107.11 (10) | C12—C11—C10 | 118.78 (12) |
C8—N1—N2 | 110.86 (11) | C12—C11—H13 | 120.6 |
C8—N1—C1 | 130.30 (11) | C10—C11—H13 | 120.6 |
N2—N1—C1 | 118.82 (10) | N1—C8—C9 | 104.27 (11) |
N2—N3—C9 | 109.18 (11) | N1—C8—H8 | 127.9 |
N4—C14—C13 | 124.35 (13) | C9—C8—H8 | 127.9 |
N4—C14—H16 | 117.8 | C14—C13—C12 | 118.17 (12) |
C13—C14—H16 | 117.8 | C14—C13—H15 | 120.9 |
C6—C5—C4 | 120.15 (12) | C12—C13—H15 | 120.9 |
C6—C5—H5 | 119.9 | C11—C12—C13 | 118.86 (12) |
C4—C5—H5 | 119.9 | C11—C12—H14 | 120.6 |
C5—C6—C1 | 118.82 (12) | C13—C12—H14 | 120.6 |
C5—C6—H6 | 120.6 | F1—C7—F2 | 106.28 (11) |
C1—C6—H6 | 120.6 | F1—C7—F3 | 106.38 (12) |
C6—C1—C2 | 121.43 (12) | F2—C7—F3 | 105.48 (11) |
C6—C1—N1 | 120.42 (11) | F1—C7—C4 | 112.90 (11) |
C2—C1—N1 | 118.14 (11) | F2—C7—C4 | 113.35 (11) |
C3—C4—C5 | 120.49 (12) | F3—C7—C4 | 111.87 (11) |
C3—C4—C7 | 120.62 (12) | C3—C2—C1 | 119.48 (12) |
C5—C4—C7 | 118.86 (12) | C3—C2—H2 | 120.3 |
N3—C9—C8 | 108.57 (11) | C1—C2—H2 | 120.3 |
N3—C9—C10 | 121.56 (12) | C2—C3—C4 | 119.63 (12) |
C8—C9—C10 | 129.85 (12) | C2—C3—H3 | 120.2 |
N4—C10—C11 | 123.07 (12) | C4—C3—H3 | 120.2 |
N4—C10—C9 | 116.62 (11) |
C14H9N5 | F(000) = 1024 |
Mr = 247.26 | Dx = 1.426 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71075 Å |
a = 16.0427 (19) Å | Cell parameters from 7318 reflections |
b = 5.8677 (6) Å | θ = 3.1–27.5° |
c = 24.487 (3) Å | µ = 0.09 mm−1 |
β = 92.354 (8)° | T = 100 K |
V = 2303.1 (5) Å3 | Needle, colourless |
Z = 8 | 0.22 × 0.14 × 0.04 mm |
Rigaku AFC12 (Right) diffractometer | 2638 independent reflections |
Radiation source: Rotating Anode | 2154 reflections with I > 2σ(I) |
Detector resolution: 28.5714 pixels mm-1 | Rint = 0.061 |
profile data from ω–scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) | h = −20→20 |
Tmin = 0.677, Tmax = 1.000 | k = −7→6 |
9891 measured reflections | l = −31→27 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0528P)2 + 1.8279P] where P = (Fo2 + 2Fc2)/3 |
2638 reflections | (Δ/σ)max = 0.002 |
172 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C14H9N5 | V = 2303.1 (5) Å3 |
Mr = 247.26 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 16.0427 (19) Å | µ = 0.09 mm−1 |
b = 5.8677 (6) Å | T = 100 K |
c = 24.487 (3) Å | 0.22 × 0.14 × 0.04 mm |
β = 92.354 (8)° |
Rigaku AFC12 (Right) diffractometer | 2638 independent reflections |
Absorption correction: multi-scan CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) | 2154 reflections with I > 2σ(I) |
Tmin = 0.677, Tmax = 1.000 | Rint = 0.061 |
9891 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.29 e Å−3 |
2638 reflections | Δρmin = −0.25 e Å−3 |
172 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 | ||
N1 | 0.35743 (7) | 0.2188 (2) | 0.47731 (5) | 0.0177 (3) | |
N3 | 0.32562 (8) | 0.5052 (2) | 0.42604 (5) | 0.0220 (3) | |
C3 | 0.46589 (9) | 0.2117 (2) | 0.54970 (6) | 0.0202 (3) | |
H3 | 0.4851 | 0.3560 | 0.5379 | 0.024* | |
N4 | 0.55444 (9) | −0.3310 (3) | 0.68852 (6) | 0.0344 (4) | |
C5 | 0.47687 (9) | −0.1099 (2) | 0.61043 (6) | 0.0195 (3) | |
C6 | 0.39778 (9) | 0.1079 (2) | 0.52296 (6) | 0.0172 (3) | |
C7 | 0.50536 (9) | 0.1029 (2) | 0.59359 (6) | 0.0209 (3) | |
H7 | 0.5518 | 0.1725 | 0.6123 | 0.025* | |
N5 | 0.18609 (8) | 0.1422 (2) | 0.34327 (5) | 0.0222 (3) | |
C9 | 0.23253 (9) | 0.3287 (2) | 0.35441 (6) | 0.0186 (3) | |
C10 | 0.40805 (9) | −0.2120 (2) | 0.58360 (6) | 0.0209 (3) | |
H10 | 0.3885 | −0.3560 | 0.5954 | 0.025* | |
C11 | 0.36849 (9) | −0.1020 (2) | 0.53979 (6) | 0.0191 (3) | |
H11 | 0.3215 | −0.1698 | 0.5213 | 0.023* | |
C12 | 0.52014 (9) | −0.2301 (3) | 0.65463 (6) | 0.0235 (3) | |
N2 | 0.36875 (8) | 0.4461 (2) | 0.47029 (5) | 0.0215 (3) | |
C14 | 0.13583 (10) | 0.1492 (3) | 0.29828 (6) | 0.0250 (3) | |
H14 | 0.1026 | 0.0189 | 0.2897 | 0.030* | |
C15 | 0.23084 (10) | 0.5219 (3) | 0.32145 (6) | 0.0223 (3) | |
H15 | 0.2652 | 0.6493 | 0.3306 | 0.027* | |
C16 | 0.30640 (9) | 0.1329 (2) | 0.43690 (6) | 0.0184 (3) | |
H16 | 0.2885 | −0.0204 | 0.4322 | 0.022* | |
C17 | 0.28639 (9) | 0.3169 (2) | 0.40433 (6) | 0.0183 (3) | |
C18 | 0.17840 (10) | 0.5253 (3) | 0.27525 (6) | 0.0249 (3) | |
H18 | 0.1760 | 0.6551 | 0.2520 | 0.030* | |
C19 | 0.12936 (10) | 0.3355 (3) | 0.26343 (6) | 0.0250 (3) | |
H19 | 0.0922 | 0.3331 | 0.2322 | 0.030* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0184 (6) | 0.0143 (5) | 0.0202 (6) | −0.0022 (5) | −0.0014 (5) | −0.0016 (4) |
N3 | 0.0236 (7) | 0.0181 (6) | 0.0239 (6) | −0.0020 (5) | −0.0044 (5) | −0.0005 (5) |
C3 | 0.0209 (7) | 0.0173 (6) | 0.0224 (7) | −0.0034 (6) | −0.0004 (5) | −0.0020 (5) |
N4 | 0.0316 (8) | 0.0385 (8) | 0.0325 (8) | −0.0031 (6) | −0.0070 (6) | 0.0057 (6) |
C5 | 0.0186 (7) | 0.0214 (7) | 0.0185 (7) | 0.0011 (6) | −0.0006 (5) | −0.0018 (5) |
C6 | 0.0175 (7) | 0.0170 (6) | 0.0171 (6) | 0.0015 (5) | −0.0008 (5) | −0.0022 (5) |
C7 | 0.0171 (7) | 0.0226 (7) | 0.0229 (7) | −0.0031 (6) | −0.0025 (5) | −0.0041 (6) |
N5 | 0.0235 (7) | 0.0205 (6) | 0.0224 (6) | −0.0028 (5) | −0.0022 (5) | −0.0010 (5) |
C9 | 0.0182 (7) | 0.0187 (7) | 0.0189 (7) | −0.0001 (5) | 0.0000 (5) | −0.0009 (5) |
C10 | 0.0215 (7) | 0.0185 (7) | 0.0224 (7) | −0.0013 (6) | −0.0003 (6) | −0.0011 (5) |
C11 | 0.0175 (7) | 0.0177 (7) | 0.0220 (7) | −0.0018 (5) | −0.0018 (5) | −0.0035 (5) |
C12 | 0.0206 (7) | 0.0252 (7) | 0.0246 (8) | −0.0022 (6) | −0.0016 (6) | −0.0001 (6) |
N2 | 0.0250 (7) | 0.0137 (6) | 0.0255 (7) | −0.0018 (5) | −0.0045 (5) | −0.0001 (5) |
C14 | 0.0254 (8) | 0.0257 (8) | 0.0235 (7) | −0.0060 (6) | −0.0042 (6) | −0.0023 (6) |
C15 | 0.0239 (8) | 0.0190 (7) | 0.0240 (7) | −0.0020 (6) | −0.0012 (6) | 0.0002 (5) |
C16 | 0.0175 (7) | 0.0180 (7) | 0.0195 (7) | −0.0028 (5) | −0.0016 (5) | −0.0024 (5) |
C17 | 0.0171 (7) | 0.0175 (7) | 0.0204 (7) | −0.0014 (5) | 0.0004 (5) | −0.0021 (5) |
C18 | 0.0282 (8) | 0.0233 (8) | 0.0231 (7) | 0.0027 (6) | 0.0000 (6) | 0.0034 (6) |
C19 | 0.0243 (8) | 0.0302 (8) | 0.0201 (7) | 0.0019 (6) | −0.0044 (6) | −0.0009 (6) |
N1—C6 | 1.4256 (18) | N5—C14 | 1.3389 (19) |
N1—N2 | 1.3578 (17) | C9—C15 | 1.391 (2) |
N1—C16 | 1.3551 (17) | C9—C17 | 1.4694 (19) |
N3—N2 | 1.3083 (17) | C10—H10 | 0.9500 |
N3—C17 | 1.3680 (18) | C10—C11 | 1.384 (2) |
C3—H3 | 0.9500 | C11—H11 | 0.9500 |
C3—C6 | 1.391 (2) | C14—H14 | 0.9500 |
C3—C7 | 1.381 (2) | C14—C19 | 1.388 (2) |
N4—C12 | 1.142 (2) | C15—H15 | 0.9500 |
C5—C7 | 1.398 (2) | C15—C18 | 1.382 (2) |
C5—C10 | 1.396 (2) | C16—H16 | 0.9500 |
C5—C12 | 1.445 (2) | C16—C17 | 1.373 (2) |
C6—C11 | 1.387 (2) | C18—H18 | 0.9500 |
C7—H7 | 0.9500 | C18—C19 | 1.387 (2) |
N5—C9 | 1.3456 (18) | C19—H19 | 0.9500 |
N2—N1—C6 | 119.25 (11) | C6—C11—H11 | 120.2 |
C16—N1—C6 | 130.10 (12) | C10—C11—C6 | 119.64 (13) |
C16—N1—N2 | 110.64 (11) | C10—C11—H11 | 120.2 |
N2—N3—C17 | 109.09 (12) | N4—C12—C5 | 177.84 (17) |
C6—C3—H3 | 120.3 | N3—N2—N1 | 107.24 (11) |
C7—C3—H3 | 120.3 | N5—C14—H14 | 118.1 |
C7—C3—C6 | 119.33 (13) | N5—C14—C19 | 123.86 (14) |
C7—C5—C12 | 120.27 (13) | C19—C14—H14 | 118.1 |
C10—C5—C7 | 120.40 (13) | C9—C15—H15 | 120.5 |
C10—C5—C12 | 119.29 (14) | C18—C15—C9 | 118.93 (14) |
C3—C6—N1 | 119.46 (13) | C18—C15—H15 | 120.5 |
C11—C6—N1 | 119.33 (13) | N1—C16—H16 | 127.7 |
C11—C6—C3 | 121.21 (13) | N1—C16—C17 | 104.58 (12) |
C3—C7—C5 | 119.84 (13) | C17—C16—H16 | 127.7 |
C3—C7—H7 | 120.1 | N3—C17—C9 | 122.05 (12) |
C5—C7—H7 | 120.1 | N3—C17—C16 | 108.45 (12) |
C14—N5—C9 | 116.85 (13) | C16—C17—C9 | 129.50 (13) |
N5—C9—C15 | 123.21 (14) | C15—C18—H18 | 120.7 |
N5—C9—C17 | 115.59 (12) | C15—C18—C19 | 118.68 (14) |
C15—C9—C17 | 121.20 (13) | C19—C18—H18 | 120.7 |
C5—C10—H10 | 120.2 | C14—C19—H19 | 120.8 |
C11—C10—C5 | 119.57 (14) | C18—C19—C14 | 118.47 (14) |
C11—C10—H10 | 120.2 | C18—C19—H19 | 120.8 |
N1—C6—C11—C10 | 179.13 (12) | C10—C5—C12—N4 | 50 (5) |
N1—C16—C17—N3 | −0.02 (16) | C12—C5—C7—C3 | 177.05 (14) |
N1—C16—C17—C9 | −179.56 (14) | C12—C5—C10—C11 | −177.32 (13) |
C3—C6—C11—C10 | −0.7 (2) | N2—N1—C6—C3 | −19.19 (19) |
C5—C10—C11—C6 | 0.2 (2) | N2—N1—C6—C11 | 161.01 (13) |
C6—N1—N2—N3 | 179.99 (11) | N2—N1—C16—C17 | 0.00 (15) |
C6—N1—C16—C17 | −179.97 (13) | N2—N3—C17—C9 | 179.61 (12) |
C6—C3—C7—C5 | 0.3 (2) | N2—N3—C17—C16 | 0.04 (17) |
C7—C3—C6—N1 | −179.38 (12) | C14—N5—C9—C15 | −0.7 (2) |
C7—C3—C6—C11 | 0.4 (2) | C14—N5—C9—C17 | 179.39 (13) |
C7—C5—C10—C11 | 0.6 (2) | C15—C9—C17—N3 | 11.9 (2) |
C7—C5—C12—N4 | −128 (4) | C15—C9—C17—C16 | −168.67 (15) |
N5—C9—C15—C18 | 0.8 (2) | C15—C18—C19—C14 | −0.7 (2) |
N5—C9—C17—N3 | −168.23 (13) | C16—N1—C6—C3 | 160.78 (14) |
N5—C9—C17—C16 | 11.3 (2) | C16—N1—C6—C11 | −19.0 (2) |
N5—C14—C19—C18 | 0.8 (2) | C16—N1—N2—N3 | 0.02 (15) |
C9—N5—C14—C19 | −0.1 (2) | C17—N3—N2—N1 | −0.03 (16) |
C9—C15—C18—C19 | −0.1 (2) | C17—C9—C15—C18 | −179.30 (13) |
C10—C5—C7—C3 | −0.9 (2) |
C14H12N4O | Z = 2 |
Mr = 252.28 | F(000) = 264 |
Triclinic, P1 | Dx = 1.435 Mg m−3 |
a = 3.7837 (4) Å | Mo Kα radiation, λ = 0.71075 Å |
b = 10.8502 (16) Å | Cell parameters from 5805 reflections |
c = 15.2200 (17) Å | θ = 3.4–27.5° |
α = 109.226 (11)° | µ = 0.10 mm−1 |
β = 97.056 (6)° | T = 100 K |
γ = 91.514 (9)° | Lath, colourless |
V = 584.03 (12) Å3 | 0.16 × 0.04 × 0.01 mm |
Rigaku AFC12 (Right) diffractometer | 2617 independent reflections |
Radiation source: Rotating Anode, Rotating Anode | 2049 reflections with > 2˘I) |
Detector resolution: 28.5714 pixels mm-1 | Rint = 0.062 |
profile data from ω–scans | θmax = 27.5°, θmin = 3.8° |
Absorption correction: multi-scan CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) | h = −4→4 |
Tmin = 0.624, Tmax = 1.000 | k = −11→14 |
6395 measured reflections | l = −19→19 |
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: inferred from neighbouring sites |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0483P)2 + 0.0584P] where P = (Fo2 + 2Fc2)/3 |
2617 reflections | (Δ/σ)max < 0.001 |
345 parameters | Δρmax = 0.25 e Å−3 |
3 restraints | Δρmin = −0.29 e Å−3 |
C14H12N4O | γ = 91.514 (9)° |
Mr = 252.28 | V = 584.03 (12) Å3 |
Triclinic, P1 | Z = 2 |
a = 3.7837 (4) Å | Mo Kα radiation |
b = 10.8502 (16) Å | µ = 0.10 mm−1 |
c = 15.2200 (17) Å | T = 100 K |
α = 109.226 (11)° | 0.16 × 0.04 × 0.01 mm |
β = 97.056 (6)° |
Rigaku AFC12 (Right) diffractometer | 2617 independent reflections |
Absorption correction: multi-scan CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) | 2049 reflections with > 2˘I) |
Tmin = 0.624, Tmax = 1.000 | Rint = 0.062 |
6395 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 3 restraints |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.25 e Å−3 |
2617 reflections | Δρmin = −0.29 e Å−3 |
345 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 | ||
O18 | 0.7712 (8) | 0.3650 (2) | 0.32489 (18) | 0.0244 (7) | |
N1 | 0.9147 (10) | 1.0178 (3) | 0.9030 (2) | 0.0239 (8) | |
N8 | 1.1451 (9) | 0.6801 (3) | 0.8522 (2) | 0.0222 (8) | |
N9 | 1.1139 (9) | 0.5903 (3) | 0.7696 (2) | 0.0226 (8) | |
N10 | 0.9831 (9) | 0.6468 (3) | 0.7063 (2) | 0.0182 (7) | |
C2 | 0.9018 (12) | 1.1276 (4) | 0.9753 (3) | 0.0256 (10) | |
H2 | 0.8249 | 1.2029 | 0.9619 | 0.031* | |
C3 | 0.9930 (11) | 1.1380 (4) | 1.0678 (3) | 0.0234 (9) | |
H3 | 0.9800 | 1.2186 | 1.1166 | 0.028* | |
C4 | 1.1033 (11) | 1.0296 (4) | 1.0884 (3) | 0.0244 (9) | |
H4 | 1.1659 | 1.0332 | 1.1516 | 0.029* | |
C5 | 1.1206 (11) | 0.9150 (4) | 1.0145 (3) | 0.0220 (9) | |
H5 | 1.1983 | 0.8386 | 1.0262 | 0.026* | |
C6 | 1.0232 (11) | 0.9132 (4) | 0.9233 (3) | 0.0181 (8) | |
C7 | 1.0307 (11) | 0.7940 (4) | 0.8429 (3) | 0.0192 (9) | |
C11 | 0.9277 (10) | 0.7735 (4) | 0.7499 (3) | 0.0180 (8) | |
H11 | 0.8370 | 0.8348 | 0.7220 | 0.022* | |
C12 | 0.9172 (11) | 0.5738 (4) | 0.6086 (3) | 0.0180 (9) | |
C13 | 0.7608 (11) | 0.4482 (4) | 0.5792 (3) | 0.0199 (9) | |
H13 | 0.6907 | 0.4121 | 0.6239 | 0.024* | |
C14 | 0.7054 (10) | 0.3739 (4) | 0.4838 (3) | 0.0188 (9) | |
H14 | 0.6002 | 0.2869 | 0.4633 | 0.023* | |
C15 | 0.8051 (11) | 0.4283 (4) | 0.4196 (3) | 0.0192 (9) | |
C16 | 0.9558 (11) | 0.5565 (4) | 0.4498 (3) | 0.0195 (9) | |
H16 | 1.0179 | 0.5938 | 0.4050 | 0.023* | |
C17 | 1.0157 (11) | 0.6294 (4) | 0.5437 (3) | 0.0198 (9) | |
H17 | 1.1223 | 0.7161 | 0.5642 | 0.024* | |
C19 | 0.6221 (12) | 0.2336 (4) | 0.2930 (3) | 0.0277 (10) | |
H19D | 0.6098 | 0.1969 | 0.2245 | 0.042* | |
H19E | 0.3814 | 0.2317 | 0.3102 | 0.042* | |
H19F | 0.7725 | 0.1816 | 0.3222 | 0.042* | |
O18A | 0.6591 (7) | 0.4355 (2) | 0.00749 (18) | 0.0212 (6) | |
N1A | 0.3987 (9) | 0.9687 (3) | 0.6207 (2) | 0.0191 (7) | |
N8A | 0.2712 (9) | 1.0350 (3) | 0.3989 (2) | 0.0209 (8) | |
N9A | 0.3208 (9) | 0.9575 (3) | 0.3158 (2) | 0.0208 (8) | |
N10A | 0.4419 (9) | 0.8457 (3) | 0.3268 (2) | 0.0183 (7) | |
C2A | 0.3704 (11) | 1.0283 (4) | 0.7117 (3) | 0.0217 (9) | |
H2A | 0.4200 | 0.9803 | 0.7534 | 0.026* | |
C3A | 0.2740 (10) | 1.1546 (4) | 0.7484 (3) | 0.0213 (9) | |
H3A | 0.2588 | 1.1923 | 0.8136 | 0.026* | |
C4A | 0.1998 (11) | 1.2252 (4) | 0.6884 (3) | 0.0215 (9) | |
H4A | 0.1347 | 1.3129 | 0.7116 | 0.026* | |
C5A | 0.2220 (11) | 1.1661 (4) | 0.5944 (3) | 0.0199 (9) | |
H5A | 0.1690 | 1.2121 | 0.5515 | 0.024* | |
C6A | 0.3230 (10) | 1.0383 (4) | 0.5629 (3) | 0.0148 (8) | |
C7A | 0.3536 (11) | 0.9742 (4) | 0.4636 (3) | 0.0180 (8) | |
C11A | 0.4646 (10) | 0.8534 (4) | 0.4172 (3) | 0.0173 (8) | |
H11A | 0.5413 | 0.7889 | 0.4436 | 0.021* | |
C12A | 0.5123 (10) | 0.7413 (4) | 0.2458 (3) | 0.0168 (8) | |
C13A | 0.4643 (10) | 0.6128 (3) | 0.2417 (3) | 0.0185 (8) | |
H13A | 0.3926 | 0.5932 | 0.2935 | 0.022* | |
C14A | 0.5213 (11) | 0.5125 (4) | 0.1614 (3) | 0.0206 (9) | |
H14A | 0.4946 | 0.4241 | 0.1591 | 0.025* | |
C15A | 0.6172 (10) | 0.5405 (4) | 0.0845 (3) | 0.0170 (8) | |
C16A | 0.6668 (11) | 0.6702 (4) | 0.0895 (3) | 0.0192 (8) | |
H16A | 0.7358 | 0.6901 | 0.0375 | 0.023* | |
C17A | 0.6158 (10) | 0.7701 (4) | 0.1700 (3) | 0.0175 (8) | |
H17A | 0.6516 | 0.8586 | 0.1734 | 0.021* | |
C19A | 0.7692 (11) | 0.4626 (4) | −0.0707 (3) | 0.0241 (9) | |
H19A | 0.8039 | 0.3802 | −0.1195 | 0.036* | |
H19B | 0.9941 | 0.5174 | −0.0507 | 0.036* | |
H19C | 0.5855 | 0.5088 | −0.0959 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O18 | 0.0308 (18) | 0.0212 (15) | 0.0221 (15) | 0.0018 (12) | 0.0060 (13) | 0.0078 (13) |
N1 | 0.031 (2) | 0.0188 (18) | 0.0240 (19) | 0.0067 (15) | 0.0059 (16) | 0.0083 (15) |
N8 | 0.026 (2) | 0.0186 (18) | 0.0204 (19) | 0.0012 (14) | −0.0013 (15) | 0.0063 (15) |
N9 | 0.030 (2) | 0.0170 (17) | 0.0196 (18) | 0.0029 (14) | −0.0008 (15) | 0.0064 (15) |
N10 | 0.0194 (18) | 0.0179 (17) | 0.0207 (17) | 0.0033 (14) | 0.0009 (14) | 0.0116 (14) |
C2 | 0.030 (3) | 0.024 (2) | 0.028 (2) | 0.0084 (18) | 0.0056 (19) | 0.014 (2) |
C3 | 0.028 (2) | 0.020 (2) | 0.020 (2) | 0.0005 (18) | 0.0048 (18) | 0.0016 (17) |
C4 | 0.027 (2) | 0.030 (2) | 0.017 (2) | −0.0034 (18) | 0.0016 (18) | 0.0093 (18) |
C5 | 0.022 (2) | 0.021 (2) | 0.025 (2) | 0.0006 (16) | 0.0018 (18) | 0.0117 (17) |
C6 | 0.017 (2) | 0.018 (2) | 0.0196 (19) | 0.0013 (16) | 0.0038 (16) | 0.0063 (16) |
C7 | 0.014 (2) | 0.021 (2) | 0.027 (2) | 0.0027 (16) | 0.0019 (17) | 0.0145 (18) |
C11 | 0.020 (2) | 0.015 (2) | 0.022 (2) | 0.0035 (16) | 0.0031 (17) | 0.0105 (17) |
C12 | 0.020 (2) | 0.016 (2) | 0.019 (2) | 0.0055 (16) | 0.0006 (17) | 0.0075 (17) |
C13 | 0.020 (2) | 0.019 (2) | 0.024 (2) | 0.0057 (16) | 0.0049 (17) | 0.0107 (17) |
C14 | 0.018 (2) | 0.017 (2) | 0.024 (2) | 0.0040 (16) | 0.0050 (17) | 0.0103 (17) |
C15 | 0.018 (2) | 0.021 (2) | 0.018 (2) | 0.0045 (16) | 0.0035 (16) | 0.0062 (17) |
C16 | 0.019 (2) | 0.021 (2) | 0.021 (2) | 0.0045 (17) | 0.0039 (17) | 0.0103 (17) |
C17 | 0.021 (2) | 0.014 (2) | 0.025 (2) | 0.0029 (16) | 0.0063 (18) | 0.0063 (17) |
C19 | 0.028 (2) | 0.026 (2) | 0.029 (2) | 0.0003 (18) | 0.0091 (19) | 0.0064 (18) |
O18A | 0.0291 (17) | 0.0152 (14) | 0.0175 (14) | 0.0044 (12) | 0.0086 (12) | 0.0010 (11) |
N1A | 0.0177 (18) | 0.0187 (18) | 0.0224 (18) | 0.0004 (14) | 0.0008 (14) | 0.0097 (14) |
N8A | 0.030 (2) | 0.0151 (17) | 0.0190 (18) | 0.0045 (15) | 0.0057 (15) | 0.0058 (14) |
N9A | 0.026 (2) | 0.0139 (17) | 0.0204 (19) | 0.0036 (14) | 0.0013 (15) | 0.0038 (14) |
N10A | 0.0209 (19) | 0.0133 (16) | 0.0210 (18) | 0.0016 (13) | 0.0035 (15) | 0.0061 (14) |
C2A | 0.023 (2) | 0.024 (2) | 0.021 (2) | 0.0009 (17) | 0.0032 (18) | 0.0108 (18) |
C3A | 0.018 (2) | 0.024 (2) | 0.023 (2) | 0.0038 (17) | 0.0045 (18) | 0.0091 (18) |
C4A | 0.021 (2) | 0.016 (2) | 0.031 (2) | 0.0059 (16) | 0.0075 (18) | 0.0112 (18) |
C5A | 0.021 (2) | 0.021 (2) | 0.022 (2) | 0.0052 (17) | 0.0065 (18) | 0.0119 (18) |
C6A | 0.0107 (19) | 0.016 (2) | 0.019 (2) | 0.0010 (15) | 0.0017 (16) | 0.0080 (16) |
C7A | 0.0136 (19) | 0.020 (2) | 0.022 (2) | 0.0009 (15) | 0.0014 (16) | 0.0097 (17) |
C11A | 0.015 (2) | 0.020 (2) | 0.019 (2) | 0.0020 (16) | 0.0040 (16) | 0.0096 (17) |
C12A | 0.012 (2) | 0.018 (2) | 0.019 (2) | 0.0027 (15) | 0.0013 (16) | 0.0061 (16) |
C13A | 0.023 (2) | 0.018 (2) | 0.017 (2) | 0.0016 (16) | 0.0043 (17) | 0.0089 (16) |
C14A | 0.021 (2) | 0.014 (2) | 0.028 (2) | −0.0010 (16) | 0.0041 (17) | 0.0080 (17) |
C15A | 0.016 (2) | 0.017 (2) | 0.0155 (19) | 0.0015 (15) | 0.0022 (15) | 0.0023 (16) |
C16A | 0.023 (2) | 0.016 (2) | 0.019 (2) | 0.0011 (16) | 0.0022 (17) | 0.0062 (16) |
C17A | 0.022 (2) | 0.0127 (19) | 0.0167 (19) | 0.0026 (15) | −0.0008 (17) | 0.0047 (15) |
C19A | 0.026 (2) | 0.026 (2) | 0.025 (2) | 0.0065 (18) | 0.0103 (18) | 0.0108 (18) |
O18—C15 | 1.366 (4) | O18A—C15A | 1.368 (4) |
O18—C19 | 1.422 (5) | O18A—C19A | 1.422 (4) |
N1—C2 | 1.336 (5) | N1A—C2A | 1.340 (5) |
N1—C6 | 1.333 (5) | N1A—C6A | 1.346 (4) |
N8—N9 | 1.302 (4) | N8A—N9A | 1.307 (4) |
N8—C7 | 1.365 (5) | N8A—C7A | 1.366 (5) |
N9—N10 | 1.355 (4) | N9A—N10A | 1.361 (4) |
N10—C11 | 1.350 (5) | N10A—C11A | 1.344 (5) |
N10—C12 | 1.422 (5) | N10A—C12A | 1.431 (5) |
C2—H2 | 0.9500 | C2A—H2A | 0.9500 |
C2—C3 | 1.375 (5) | C2A—C3A | 1.377 (5) |
C3—H3 | 0.9500 | C3A—H3A | 0.9500 |
C3—C4 | 1.376 (6) | C3A—C4A | 1.382 (5) |
C4—H4 | 0.9500 | C4A—H4A | 0.9500 |
C4—C5 | 1.384 (6) | C4A—C5A | 1.375 (5) |
C5—H5 | 0.9500 | C5A—H5A | 0.9500 |
C5—C6 | 1.385 (5) | C5A—C6A | 1.391 (5) |
C6—C7 | 1.463 (5) | C6A—C7A | 1.463 (5) |
C7—C11 | 1.362 (6) | C7A—C11A | 1.372 (6) |
C11—H11 | 0.9500 | C11A—H11A | 0.9500 |
C12—C13 | 1.378 (5) | C12A—C13A | 1.381 (5) |
C12—C17 | 1.395 (5) | C12A—C17A | 1.387 (5) |
C13—H13 | 0.9500 | C13A—H13A | 0.9500 |
C13—C14 | 1.395 (5) | C13A—C14A | 1.387 (5) |
C14—H14 | 0.9500 | C14A—H14A | 0.9500 |
C14—C15 | 1.380 (5) | C14A—C15A | 1.389 (5) |
C15—C16 | 1.394 (5) | C15A—C16A | 1.390 (5) |
C16—H16 | 0.9500 | C16A—H16A | 0.9500 |
C16—C17 | 1.373 (5) | C16A—C17A | 1.381 (5) |
C17—H17 | 0.9500 | C17A—H17A | 0.9500 |
C19—H19D | 0.9800 | C19A—H19A | 0.9800 |
C19—H19E | 0.9800 | C19A—H19B | 0.9800 |
C19—H19F | 0.9800 | C19A—H19C | 0.9800 |
C15—O18—C19 | 115.7 (3) | C15A—O18A—C19A | 117.1 (3) |
C6—N1—C2 | 117.0 (3) | C2A—N1A—C6A | 116.7 (3) |
N9—N8—C7 | 109.2 (3) | N9A—N8A—C7A | 109.6 (3) |
N8—N9—N10 | 107.0 (3) | N8A—N9A—N10A | 107.0 (3) |
N9—N10—C12 | 121.0 (3) | N9A—N10A—C12A | 119.1 (3) |
C11—N10—N9 | 110.6 (3) | C11A—N10A—N9A | 110.3 (3) |
C11—N10—C12 | 128.4 (3) | C11A—N10A—C12A | 130.6 (3) |
N1—C2—H2 | 118.0 | N1A—C2A—H2A | 117.9 |
N1—C2—C3 | 123.9 (4) | N1A—C2A—C3A | 124.1 (4) |
C3—C2—H2 | 118.0 | C3A—C2A—H2A | 117.9 |
C2—C3—H3 | 120.6 | C2A—C3A—H3A | 120.7 |
C2—C3—C4 | 118.8 (4) | C2A—C3A—C4A | 118.5 (4) |
C4—C3—H3 | 120.6 | C4A—C3A—H3A | 120.7 |
C3—C4—H4 | 120.9 | C3A—C4A—H4A | 120.6 |
C3—C4—C5 | 118.2 (4) | C5A—C4A—C3A | 118.7 (3) |
C5—C4—H4 | 120.9 | C5A—C4A—H4A | 120.6 |
C4—C5—H5 | 120.4 | C4A—C5A—H5A | 120.4 |
C4—C5—C6 | 119.1 (4) | C4A—C5A—C6A | 119.2 (3) |
C6—C5—H5 | 120.4 | C6A—C5A—H5A | 120.4 |
N1—C6—C5 | 122.9 (3) | N1A—C6A—C5A | 122.7 (3) |
N1—C6—C7 | 115.9 (3) | N1A—C6A—C7A | 117.1 (3) |
C5—C6—C7 | 121.2 (3) | C5A—C6A—C7A | 120.2 (3) |
N8—C7—C6 | 122.7 (3) | N8A—C7A—C6A | 121.6 (3) |
C11—C7—N8 | 108.4 (4) | N8A—C7A—C11A | 107.6 (3) |
C11—C7—C6 | 128.8 (3) | C11A—C7A—C6A | 130.8 (3) |
N10—C11—C7 | 104.7 (3) | N10A—C11A—C7A | 105.5 (3) |
N10—C11—H11 | 127.6 | N10A—C11A—H11A | 127.2 |
C7—C11—H11 | 127.6 | C7A—C11A—H11A | 127.2 |
C13—C12—N10 | 119.5 (3) | C13A—C12A—N10A | 120.4 (3) |
C13—C12—C17 | 120.7 (3) | C13A—C12A—C17A | 120.2 (3) |
C17—C12—N10 | 119.7 (3) | C17A—C12A—N10A | 119.4 (3) |
C12—C13—H13 | 119.9 | C12A—C13A—H13A | 120.1 |
C12—C13—C14 | 120.1 (3) | C12A—C13A—C14A | 119.7 (3) |
C14—C13—H13 | 119.9 | C14A—C13A—H13A | 120.1 |
C13—C14—H14 | 120.4 | C13A—C14A—H14A | 119.8 |
C15—C14—C13 | 119.2 (4) | C13A—C14A—C15A | 120.4 (3) |
C15—C14—H14 | 120.4 | C15A—C14A—H14A | 119.8 |
O18—C15—C14 | 124.8 (3) | O18A—C15A—C14A | 116.4 (3) |
O18—C15—C16 | 115.0 (3) | O18A—C15A—C16A | 124.1 (3) |
C14—C15—C16 | 120.2 (3) | C14A—C15A—C16A | 119.5 (3) |
C15—C16—H16 | 119.6 | C15A—C16A—H16A | 120.0 |
C17—C16—C15 | 120.8 (3) | C17A—C16A—C15A | 120.1 (3) |
C17—C16—H16 | 119.6 | C17A—C16A—H16A | 120.0 |
C12—C17—H17 | 120.6 | C12A—C17A—H17A | 119.9 |
C16—C17—C12 | 118.9 (4) | C16A—C17A—C12A | 120.1 (3) |
C16—C17—H17 | 120.6 | C16A—C17A—H17A | 119.9 |
O18—C19—H19D | 109.5 | O18A—C19A—H19A | 109.5 |
O18—C19—H19E | 109.5 | O18A—C19A—H19B | 109.5 |
O18—C19—H19F | 109.5 | O18A—C19A—H19C | 109.5 |
H19D—C19—H19E | 109.5 | H19A—C19A—H19B | 109.5 |
H19D—C19—H19F | 109.5 | H19A—C19A—H19C | 109.5 |
H19E—C19—H19F | 109.5 | H19B—C19A—H19C | 109.5 |
O18—C15—C16—C17 | −177.8 (4) | O18A—C15A—C16A—C17A | 179.5 (4) |
N1—C2—C3—C4 | −0.3 (7) | N1A—C2A—C3A—C4A | 0.2 (6) |
N1—C6—C7—N8 | 178.1 (4) | N1A—C6A—C7A—N8A | 177.8 (4) |
N1—C6—C7—C11 | −3.0 (6) | N1A—C6A—C7A—C11A | −3.4 (6) |
N8—N9—N10—C11 | −0.7 (4) | N8A—N9A—N10A—C11A | 0.6 (4) |
N8—N9—N10—C12 | −179.9 (3) | N8A—N9A—N10A—C12A | 178.7 (3) |
N8—C7—C11—N10 | 0.2 (4) | N8A—C7A—C11A—N10A | −0.5 (4) |
N9—N8—C7—C6 | 178.4 (3) | N9A—N8A—C7A—C6A | 180.0 (3) |
N9—N8—C7—C11 | −0.6 (5) | N9A—N8A—C7A—C11A | 0.9 (5) |
N9—N10—C11—C7 | 0.3 (4) | N9A—N10A—C11A—C7A | 0.0 (4) |
N9—N10—C12—C13 | 42.1 (5) | N9A—N10A—C12A—C13A | −148.3 (4) |
N9—N10—C12—C17 | −137.0 (4) | N9A—N10A—C12A—C17A | 29.2 (5) |
N10—C12—C13—C14 | −177.9 (4) | N10A—C12A—C13A—C14A | 177.7 (4) |
N10—C12—C17—C16 | 178.8 (3) | N10A—C12A—C17A—C16A | −176.7 (4) |
C2—N1—C6—C5 | −0.1 (6) | C2A—N1A—C6A—C5A | 0.4 (5) |
C2—N1—C6—C7 | 179.3 (4) | C2A—N1A—C6A—C7A | 179.9 (3) |
C2—C3—C4—C5 | 0.6 (6) | C2A—C3A—C4A—C5A | 0.6 (6) |
C3—C4—C5—C6 | −0.7 (6) | C3A—C4A—C5A—C6A | −0.9 (6) |
C4—C5—C6—N1 | 0.4 (6) | C4A—C5A—C6A—N1A | 0.4 (6) |
C4—C5—C6—C7 | −178.9 (4) | C4A—C5A—C6A—C7A | −179.1 (4) |
C5—C6—C7—N8 | −2.5 (6) | C5A—C6A—C7A—N8A | −2.7 (5) |
C5—C6—C7—C11 | 176.4 (4) | C5A—C6A—C7A—C11A | 176.2 (4) |
C6—N1—C2—C3 | 0.0 (6) | C6A—N1A—C2A—C3A | −0.7 (6) |
C6—C7—C11—N10 | −178.8 (4) | C6A—C7A—C11A—N10A | −179.5 (4) |
C7—N8—N9—N10 | 0.8 (4) | C7A—N8A—N9A—N10A | −0.9 (4) |
C11—N10—C12—C13 | −136.9 (4) | C11A—N10A—C12A—C13A | 29.4 (6) |
C11—N10—C12—C17 | 44.0 (6) | C11A—N10A—C12A—C17A | −153.1 (4) |
C12—N10—C11—C7 | 179.4 (4) | C12A—N10A—C11A—C7A | −177.9 (4) |
C12—C13—C14—C15 | −0.7 (5) | C12A—C13A—C14A—C15A | −1.7 (6) |
C13—C12—C17—C16 | −0.3 (6) | C13A—C12A—C17A—C16A | 0.9 (6) |
C13—C14—C15—O18 | 178.7 (4) | C13A—C14A—C15A—O18A | −178.4 (4) |
C13—C14—C15—C16 | −0.7 (6) | C13A—C14A—C15A—C16A | 2.0 (6) |
C14—C15—C16—C17 | 1.6 (6) | C14A—C15A—C16A—C17A | −0.9 (6) |
C15—C16—C17—C12 | −1.1 (6) | C15A—C16A—C17A—C12A | −0.5 (6) |
C17—C12—C13—C14 | 1.2 (5) | C17A—C12A—C13A—C14A | 0.2 (6) |
C19—O18—C15—C14 | −0.2 (5) | C19A—O18A—C15A—C14A | −177.9 (4) |
C19—O18—C15—C16 | 179.2 (3) | C19A—O18A—C15A—C16A | 1.7 (5) |
C14H10N4O2 | F(000) = 552 |
Mr = 266.26 | Dx = 1.491 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71075 Å |
a = 10.5970 (17) Å | Cell parameters from 3755 reflections |
b = 14.471 (2) Å | θ = 3.4–27.5° |
c = 7.7343 (12) Å | µ = 0.11 mm−1 |
β = 90.121 (6)° | T = 100 K |
V = 1186.0 (3) Å3 | Hexagonal tablet, colourless |
Z = 4 | 0.12 × 0.12 × 0.03 mm |
Rigaku AFC12 (Right) diffractometer | 2705 independent reflections |
Radiation source: Rotating Anode | 1862 reflections with I > 2σ(I) |
Detector resolution: 28.5714 pixels mm-1 | Rint = 0.058 |
profile data from ω–scans | θmax = 27.5°, θmin = 3.4° |
Absorption correction: multi-scan CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) | h = −13→13 |
Tmin = 0.516, Tmax = 1.000 | k = −17→18 |
5844 measured reflections | l = −10→9 |
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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.161 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0647P)2 + 0.6263P] where P = (Fo2 + 2Fc2)/3 |
2705 reflections | (Δ/σ)max < 0.001 |
182 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
C14H10N4O2 | V = 1186.0 (3) Å3 |
Mr = 266.26 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.5970 (17) Å | µ = 0.11 mm−1 |
b = 14.471 (2) Å | T = 100 K |
c = 7.7343 (12) Å | 0.12 × 0.12 × 0.03 mm |
β = 90.121 (6)° |
Rigaku AFC12 (Right) diffractometer | 2705 independent reflections |
Absorption correction: multi-scan CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) | 1862 reflections with I > 2σ(I) |
Tmin = 0.516, Tmax = 1.000 | Rint = 0.058 |
5844 measured reflections |
R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
wR(F2) = 0.161 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.34 e Å−3 |
2705 reflections | Δρmin = −0.29 e Å−3 |
182 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 | ||
O1 | 0.29090 (16) | 0.26161 (12) | 0.0038 (2) | 0.0252 (4) | |
H1 | 0.2269 | 0.2748 | 0.0578 | 0.038* | |
O2 | 0.23870 (16) | 0.11779 (12) | 0.0831 (2) | 0.0257 (4) | |
N1 | 0.90055 (18) | −0.17000 (14) | −0.6767 (2) | 0.0189 (4) | |
N8 | 0.8241 (2) | 0.07445 (15) | −0.6588 (3) | 0.0267 (5) | |
N9 | 0.7414 (2) | 0.11677 (14) | −0.5638 (3) | 0.0254 (5) | |
N10 | 0.69803 (18) | 0.05483 (13) | −0.4468 (2) | 0.0196 (4) | |
C2 | 0.9784 (2) | −0.22820 (18) | −0.7587 (3) | 0.0242 (6) | |
H2 | 0.9651 | −0.2914 | −0.7470 | 0.029* | |
C3 | 1.0777 (2) | −0.19837 (18) | −0.8600 (3) | 0.0257 (6) | |
H3 | 1.1302 | −0.2407 | −0.9147 | 0.031* | |
C4 | 1.0974 (2) | −0.10506 (18) | −0.8783 (3) | 0.0239 (6) | |
H4 | 1.1631 | −0.0833 | −0.9466 | 0.029* | |
C5 | 1.0188 (2) | −0.04411 (17) | −0.7942 (3) | 0.0214 (5) | |
H5 | 1.0311 | 0.0193 | −0.8042 | 0.026* | |
C6 | 0.9201 (2) | −0.07900 (16) | −0.6936 (3) | 0.0179 (5) | |
C7 | 0.8345 (2) | −0.01517 (17) | −0.6054 (3) | 0.0190 (5) | |
C11 | 0.7529 (2) | −0.02822 (16) | −0.4690 (3) | 0.0170 (5) | |
H11 | 0.7389 | −0.0822 | −0.4065 | 0.020* | |
C12 | 0.6029 (2) | 0.08282 (17) | −0.3278 (3) | 0.0184 (5) | |
C13 | 0.5173 (2) | 0.01886 (17) | −0.2646 (3) | 0.0186 (5) | |
H13 | 0.5236 | −0.0430 | −0.2957 | 0.022* | |
C14 | 0.4221 (2) | 0.04811 (17) | −0.1543 (3) | 0.0193 (5) | |
H14 | 0.3648 | 0.0056 | −0.1102 | 0.023* | |
C15 | 0.4124 (2) | 0.14079 (16) | −0.1097 (3) | 0.0194 (5) | |
C16 | 0.5004 (2) | 0.20375 (17) | −0.1718 (3) | 0.0224 (5) | |
H16 | 0.4944 | 0.2657 | −0.1406 | 0.027* | |
C17 | 0.5967 (2) | 0.17520 (17) | −0.2796 (3) | 0.0215 (5) | |
H17 | 0.6565 | 0.2172 | −0.3193 | 0.026* | |
C18 | 0.3052 (2) | 0.17172 (17) | 0.0019 (3) | 0.0186 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0253 (9) | 0.0216 (10) | 0.0286 (10) | 0.0029 (7) | 0.0103 (7) | −0.0023 (7) |
O2 | 0.0269 (9) | 0.0255 (10) | 0.0246 (9) | 0.0007 (8) | 0.0071 (7) | 0.0027 (8) |
N1 | 0.0208 (10) | 0.0183 (10) | 0.0176 (9) | −0.0001 (8) | 0.0009 (8) | 0.0002 (8) |
N8 | 0.0290 (11) | 0.0205 (12) | 0.0307 (11) | 0.0010 (9) | 0.0102 (9) | 0.0002 (9) |
N9 | 0.0293 (11) | 0.0189 (11) | 0.0279 (11) | 0.0022 (9) | 0.0118 (9) | 0.0011 (9) |
N10 | 0.0213 (10) | 0.0180 (11) | 0.0194 (9) | −0.0003 (8) | 0.0037 (8) | 0.0003 (8) |
C2 | 0.0272 (13) | 0.0204 (13) | 0.0250 (12) | 0.0021 (10) | −0.0023 (10) | −0.0017 (10) |
C3 | 0.0246 (12) | 0.0306 (15) | 0.0221 (12) | 0.0098 (11) | 0.0015 (10) | −0.0016 (11) |
C4 | 0.0186 (12) | 0.0343 (15) | 0.0189 (12) | 0.0004 (11) | 0.0049 (9) | 0.0053 (11) |
C5 | 0.0229 (12) | 0.0197 (13) | 0.0217 (11) | −0.0031 (10) | −0.0030 (10) | 0.0022 (10) |
C6 | 0.0175 (11) | 0.0206 (13) | 0.0157 (10) | 0.0027 (10) | −0.0019 (9) | −0.0004 (9) |
C7 | 0.0186 (11) | 0.0190 (13) | 0.0193 (11) | −0.0024 (9) | −0.0002 (9) | −0.0003 (9) |
C11 | 0.0198 (11) | 0.0141 (12) | 0.0172 (10) | −0.0003 (9) | 0.0002 (9) | 0.0023 (9) |
C12 | 0.0171 (11) | 0.0199 (13) | 0.0181 (11) | 0.0032 (9) | 0.0002 (9) | −0.0016 (9) |
C13 | 0.0212 (12) | 0.0176 (12) | 0.0172 (11) | 0.0017 (9) | 0.0008 (9) | −0.0025 (9) |
C14 | 0.0189 (11) | 0.0213 (13) | 0.0176 (11) | −0.0005 (10) | −0.0010 (9) | 0.0014 (9) |
C15 | 0.0195 (11) | 0.0221 (13) | 0.0165 (11) | 0.0034 (10) | −0.0007 (9) | −0.0010 (9) |
C16 | 0.0226 (12) | 0.0186 (13) | 0.0260 (12) | 0.0029 (10) | 0.0019 (10) | −0.0037 (10) |
C17 | 0.0208 (12) | 0.0185 (12) | 0.0253 (12) | −0.0010 (10) | 0.0035 (10) | −0.0012 (10) |
C18 | 0.0188 (11) | 0.0192 (12) | 0.0178 (11) | 0.0014 (10) | −0.0029 (9) | 0.0000 (10) |
O1—H1 | 0.8200 | C5—H5 | 0.9300 |
O1—C18 | 1.310 (3) | C5—C6 | 1.399 (3) |
O2—C18 | 1.226 (3) | C6—C7 | 1.465 (3) |
N1—C2 | 1.340 (3) | C7—C11 | 1.378 (3) |
N1—C6 | 1.339 (3) | C11—H11 | 0.9300 |
N8—N9 | 1.299 (3) | C12—C13 | 1.386 (3) |
N8—C7 | 1.366 (3) | C12—C17 | 1.389 (3) |
N9—N10 | 1.355 (3) | C13—H13 | 0.9300 |
N10—C11 | 1.346 (3) | C13—C14 | 1.388 (3) |
N10—C12 | 1.425 (3) | C14—H14 | 0.9300 |
C2—H2 | 0.9300 | C14—C15 | 1.389 (3) |
C2—C3 | 1.382 (3) | C15—C16 | 1.390 (3) |
C3—H3 | 0.9300 | C15—C18 | 1.497 (3) |
C3—C4 | 1.374 (4) | C16—H16 | 0.9300 |
C4—H4 | 0.9300 | C16—C17 | 1.382 (3) |
C4—C5 | 1.377 (3) | C17—H17 | 0.9300 |
C18—O1—H1 | 109.5 | N10—C11—C7 | 104.3 (2) |
C6—N1—C2 | 118.5 (2) | N10—C11—H11 | 127.8 |
N9—N8—C7 | 109.3 (2) | C7—C11—H11 | 127.8 |
N8—N9—N10 | 107.24 (19) | C13—C12—N10 | 120.2 (2) |
N9—N10—C12 | 118.98 (19) | C13—C12—C17 | 121.1 (2) |
C11—N10—N9 | 111.00 (19) | C17—C12—N10 | 118.7 (2) |
C11—N10—C12 | 130.0 (2) | C12—C13—H13 | 120.3 |
N1—C2—H2 | 118.6 | C12—C13—C14 | 119.3 (2) |
N1—C2—C3 | 122.8 (2) | C14—C13—H13 | 120.3 |
C3—C2—H2 | 118.6 | C13—C14—H14 | 120.0 |
C2—C3—H3 | 120.6 | C13—C14—C15 | 120.1 (2) |
C4—C3—C2 | 118.8 (2) | C15—C14—H14 | 120.0 |
C4—C3—H3 | 120.6 | C14—C15—C16 | 119.8 (2) |
C3—C4—H4 | 120.4 | C14—C15—C18 | 119.2 (2) |
C3—C4—C5 | 119.3 (2) | C16—C15—C18 | 120.9 (2) |
C5—C4—H4 | 120.4 | C15—C16—H16 | 119.7 |
C4—C5—H5 | 120.5 | C17—C16—C15 | 120.6 (2) |
C4—C5—C6 | 119.0 (2) | C17—C16—H16 | 119.7 |
C6—C5—H5 | 120.5 | C12—C17—H17 | 120.5 |
N1—C6—C5 | 121.6 (2) | C16—C17—C12 | 119.0 (2) |
N1—C6—C7 | 118.6 (2) | C16—C17—H17 | 120.5 |
C5—C6—C7 | 119.7 (2) | O1—C18—C15 | 113.0 (2) |
N8—C7—C6 | 120.5 (2) | O2—C18—O1 | 124.1 (2) |
N8—C7—C11 | 108.2 (2) | O2—C18—C15 | 122.9 (2) |
C11—C7—C6 | 131.3 (2) | ||
N1—C2—C3—C4 | −0.3 (4) | C5—C6—C7—C11 | −161.5 (2) |
N1—C6—C7—N8 | −159.3 (2) | C6—N1—C2—C3 | −0.1 (3) |
N1—C6—C7—C11 | 19.2 (4) | C6—C7—C11—N10 | −179.1 (2) |
N8—N9—N10—C11 | −0.7 (3) | C7—N8—N9—N10 | 0.4 (3) |
N8—N9—N10—C12 | −178.44 (19) | C11—N10—C12—C13 | −26.9 (3) |
N8—C7—C11—N10 | −0.4 (2) | C11—N10—C12—C17 | 154.2 (2) |
N9—N8—C7—C6 | 178.8 (2) | C12—N10—C11—C7 | 178.1 (2) |
N9—N8—C7—C11 | 0.0 (3) | C12—C13—C14—C15 | 0.7 (3) |
N9—N10—C11—C7 | 0.7 (2) | C13—C12—C17—C16 | −2.4 (3) |
N9—N10—C12—C13 | 150.4 (2) | C13—C14—C15—C16 | −1.8 (3) |
N9—N10—C12—C17 | −28.5 (3) | C13—C14—C15—C18 | 176.8 (2) |
N10—C12—C13—C14 | −177.40 (19) | C14—C15—C16—C17 | 0.9 (3) |
N10—C12—C17—C16 | 176.4 (2) | C14—C15—C18—O1 | −166.1 (2) |
C2—N1—C6—C5 | 0.2 (3) | C14—C15—C18—O2 | 14.2 (3) |
C2—N1—C6—C7 | 179.45 (19) | C15—C16—C17—C12 | 1.3 (3) |
C2—C3—C4—C5 | 0.6 (3) | C16—C15—C18—O1 | 12.5 (3) |
C3—C4—C5—C6 | −0.6 (3) | C16—C15—C18—O2 | −167.1 (2) |
C4—C5—C6—N1 | 0.2 (3) | C17—C12—C13—C14 | 1.5 (3) |
C4—C5—C6—C7 | −179.1 (2) | C18—C15—C16—C17 | −177.8 (2) |
C5—C6—C7—N8 | 20.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.82 | 1.82 | 2.626 (3) | 167 |
Symmetry code: (i) −x+1, y+1/2, −z−1/2. |
Experimental details
(L1) | (L3) | (L4) | (L5) | |
Crystal data | ||||
Chemical formula | C13H10N4 | C13H9FN4 | C13H9ClN4 | C14H12N4 |
Mr | 222.25 | 240.24 | 256.69 | 236.28 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, C2/c | Monoclinic, P21 |
Temperature (K) | 120 | 120 | 120 | 120 |
a, b, c (Å) | 22.6348 (5), 5.8250 (1), 17.8421 (4) | 12.2031 (3), 7.9798 (2), 11.6329 (3) | 16.0000 (11), 5.9258 (2), 24.3829 (17) | 5.7797 (5), 6.7414 (4), 15.0259 (12) |
α, β, γ (°) | 90, 113.007 (1), 90 | 90, 104.043 (2), 90 | 90, 93.109 (8), 90 | 90, 92.359 (4), 90 |
V (Å3) | 2165.32 (8) | 1098.94 (5) | 2308.4 (2) | 584.96 (8) |
Z | 8 | 4 | 8 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.09 | 0.10 | 0.32 | 0.08 |
Crystal size (mm) | 0.34 × 0.23 × 0.20 | 0.60 × 0.58 × 0.40 | 0.36 × 0.12 × 0.06 | 0.38 × 0.12 × 0.10 |
Data collection | ||||
Diffractometer | Bruker-Nonius CCD camera on κ-goniostat diffractometer | Bruker-Nonius CCD camera on κ-goniostat diffractometer | Rigaku R-AXIS SPIDER IP diffractometer | Bruker-Nonius CCD camera on κ-goniostat diffractometer |
Absorption correction | Multi-scan SADABS 2007/2 (Sheldrick, G.M., 2007) | Multi-scan SADABS 2007/2 (Sheldrick, G.M., 2007) | Multi-scan CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) | Multi-scan SADABS 2007/2 (Sheldrick, G.M., 2007) |
Tmin, Tmax | 0.971, 0.983 | 0.940, 0.960 | 0.608, 1.000 | 0.969, 0.992 |
No. of measured, independent and observed reflections | 35200, 4956, 4405 [I > 2σ(I)] | 13725, 2510, 2228 [I > 2σ(I)] | 11996, 2636, 1654 [I > 2σ(I)] | 9647, 2622, 2042 [I > 2σ(I)] |
Rint | 0.057 | 0.031 | 0.050 | 0.056 |
(sin θ/λ)max (Å−1) | 0.649 | 0.649 | 0.649 | 0.649 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.108, 1.06 | 0.038, 0.092, 1.05 | 0.045, 0.137, 1.05 | 0.048, 0.124, 1.04 |
No. of reflections | 4956 | 2510 | 2636 | 2622 |
No. of parameters | 309 | 163 | 163 | 165 |
No. of restraints | 0 | 0 | 0 | 1 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.35 | 0.26, −0.23 | 0.25, −0.46 | 0.17, −0.18 |
(L6) | (L7) | (L8) | (L11) | |
Crystal data | ||||
Chemical formula | C14H9F3N4 | C14H9N5 | C14H12N4O | C14H10N4O2 |
Mr | 290.25 | 247.26 | 252.28 | 266.26 |
Crystal system, space group | Triclinic, P1 | Monoclinic, C2/c | Triclinic, P1 | Monoclinic, P21/c |
Temperature (K) | 120 | 100 | 100 | 100 |
a, b, c (Å) | 5.7460 (1), 7.2076 (2), 15.2997 (4) | 16.0427 (19), 5.8677 (6), 24.487 (3) | 3.7837 (4), 10.8502 (16), 15.2200 (17) | 10.5970 (17), 14.471 (2), 7.7343 (12) |
α, β, γ (°) | 103.045 (2), 98.768 (2), 92.290 (2) | 90, 92.354 (8), 90 | 109.226 (11), 97.056 (6), 91.514 (9) | 90, 90.121 (6), 90 |
V (Å3) | 608.25 (3) | 2303.1 (5) | 584.03 (12) | 1186.0 (3) |
Z | 2 | 8 | 2 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.13 | 0.09 | 0.10 | 0.11 |
Crystal size (mm) | 0.60 × 0.20 × 0.18 | 0.22 × 0.14 × 0.04 | 0.16 × 0.04 × 0.01 | 0.12 × 0.12 × 0.03 |
Data collection | ||||
Diffractometer | Bruker-Nonius CCD camera on κ-goniostat diffractometer | Rigaku AFC12 (Right) diffractometer | Rigaku AFC12 (Right) diffractometer | Rigaku AFC12 (Right) diffractometer |
Absorption correction | Multi-scan SADABS 2007/2 (Sheldrick, G.M., 2007) | Multi-scan CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) | Multi-scan CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) | Multi-scan CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011) |
Tmin, Tmax | 0.925, 0.977 | 0.677, 1.000 | 0.624, 1.000 | 0.516, 1.000 |
No. of measured, independent and observed reflections | 14232, 2785, 2436 [I > 2σ(I)] | 9891, 2638, 2154 [I > 2σ(I)] | 6395, 2617, 2049 [ > 2˘I)] | 5844, 2705, 1862 [I > 2σ(I)] |
Rint | 0.035 | 0.061 | 0.062 | 0.058 |
(sin θ/λ)max (Å−1) | 0.649 | 0.649 | 0.649 | 0.649 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.109, 1.03 | 0.046, 0.121, 1.06 | 0.053, 0.116, 1.08 | 0.062, 0.161, 1.05 |
No. of reflections | 2785 | 2638 | 2617 | 2705 |
No. of parameters | 191 | 172 | 345 | 182 |
No. of restraints | 0 | 0 | 3 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.37, −0.30 | 0.29, −0.25 | 0.25, −0.29 | 0.34, −0.29 |
Computer programs: , CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011), CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011), DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998), SUPERFLIP (Palatinus & Chapuis, 2007), olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011), SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122, SHELXD, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122, SHELXL97 (Sheldrick, 1997), SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122, SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122, OLEX2 (Dolomanov, Bourhis, Gildea, Howard & Puschmann, 2009), O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341., WinGX (Farrugia, 1998).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1i | 0.82 | 1.82 | 2.626 (3) | 167.2 |
Symmetry code: (i) −x+1, y+1/2, −z−1/2. |
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