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The crystal structures of a new polymorph and seven new derivatives of 2-(1-phenyl-1H-1,2,3-triazol-4-yl)pyridine have been characterized and examined along with three structures from the literature to identify trends in their intermolecular contact patterns and packing arrangements in order to develop an insight into the crystallization behaviour of this class of compound. Seven unique C—H...X contacts were identified in the structures and three of these are present in four or more structures, indicating that these are reliable supramolecular synthons. Analysis of the packing arrangements of the molecules using XPac identified two closely related supramolecular constructs that are present in eight of the 11 structures; in all cases, the structures feature at least one of the three most common intermolecular contacts, suggesting a clear relationship between the intermolecular contacts and the packing arrangements of the structures. Both the intermolecular contacts and packing arrangements appear to be remarkably consistent between structures featuring different functional groups, with the expected exception of the carboxylic acid derivative 4-(4-(pyridin-2-yl)-1H-1,2,3-triazol-1-yl) benzoic acid (L11), where the introduction of a strong hydrogen-bonding group results in a markedly different supramolecular structure being adopted. The occurrence of these structural features has been compared with the packing efficiency of the structures and their melting points in order to assess the relative favourability of the supramolecular structural features in stabilizing the crystal structures.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520614001152/eb5029sup1.cif
Contains datablocks L1, L3, L4, L5, L6, L7, L8, L11

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L1sup2.hkl
Contains datablock L1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L3sup3.hkl
Contains datablock L3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L4sup4.hkl
Contains datablock L4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L5sup5.hkl
Contains datablock L5

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L6sup6.hkl
Contains datablock L6

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L7sup7.hkl
Contains datablock L7

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L8sup8.hkl
Contains datablock L8

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L11sup9.hkl
Contains datablock L11

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L1unmergedsup10.hkl
Unmerged hkl file for L1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L3unmergedsup11.hkl
Unmerged hkl file for L3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L4unmergedsup12.hkl
Unmerged hkl file for L4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L5unmergedsup13.hkl
Unmerged hkl file for L5

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L6unmergedsup14.hkl
Unmerged hkl file for L6

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L7unmergedsup15.hkl
Unmerged hkl file for L7

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L8unmergedsup16.hkl
Unmerged hkl file for L8

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614001152/eb5029L11unmergedsup17.hkl
Unmerged hkl file for L11

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520614001152/eb5029sup18.pdf
Mass, 1H and 13C NMR spectra of the novel ligands synthesised in this work.

Experimental top

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1.

Results and discussion top

Computing details top

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.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
[Figure 11]
[Figure 12]
[Figure 13]
[Figure 14]
(L1) top
Crystal data top
C13H10N4F(000) = 928
Mr = 222.25Dx = 1.364 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 39537 reflections
a = 22.6348 (5) Åθ = 2.9–27.5°
b = 5.8250 (1) ŵ = 0.09 mm1
c = 17.8421 (4) ÅT = 120 K
β = 113.007 (1)°Block, colourless
V = 2165.32 (8) Å30.34 × 0.23 × 0.20 mm
Z = 8
Data collection top
Bruker-Nonius CCD camera on κ-goniostat
diffractometer
4956 independent reflections
Radiation source: Bruker Nonius FR591 Rotating Anode4405 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.9°
ϕ & ω scans to fill the asymmetric unith = 2929
Absorption correction: multi-scan
SADABS 2007/2 (Sheldrick, G.M., 2007)
k = 76
Tmin = 0.971, Tmax = 0.983l = 2320
35200 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-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 reflectionsΔρmax = 0.27 e Å3
309 parametersΔρmin = 0.35 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.033 (2)
Crystal data top
C13H10N4V = 2165.32 (8) Å3
Mr = 222.25Z = 8
Monoclinic, P21/cMo Kα radiation
a = 22.6348 (5) ŵ = 0.09 mm1
b = 5.8250 (1) ÅT = 120 K
c = 17.8421 (4) Å0.34 × 0.23 × 0.20 mm
β = 113.007 (1)°
Data collection top
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 = 0.983Rint = 0.057
35200 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.108H-atom parameters constrained
S = 1.06Δρmax = 0.27 e Å3
4956 reflectionsΔρmin = 0.35 e Å3
309 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.07886 (7)0.2174 (3)0.01624 (10)0.0207 (3)
H10.08470.05560.01360.025*
C20.11370 (8)0.3780 (3)0.03988 (10)0.0207 (3)
C30.16646 (8)0.3450 (3)0.11954 (10)0.0211 (3)
C40.18296 (8)0.5191 (3)0.17764 (11)0.0242 (4)
H40.16260.66480.16520.029*
C50.23002 (8)0.4744 (3)0.25434 (11)0.0276 (4)
H50.24200.58890.29550.033*
C60.25929 (8)0.2604 (3)0.26986 (11)0.0263 (4)
H60.29120.22450.32190.032*
C70.24073 (8)0.1002 (3)0.20739 (11)0.0257 (4)
H70.26170.04470.21780.031*
C80.01622 (7)0.2653 (3)0.14985 (9)0.0198 (3)
C90.03706 (8)0.4117 (3)0.21675 (10)0.0225 (3)
H90.01800.55860.21370.027*
C100.08616 (8)0.3396 (3)0.28803 (11)0.0261 (4)
H100.10110.43800.33410.031*
C110.11352 (8)0.1245 (3)0.29233 (11)0.0277 (4)
H110.14700.07560.34140.033*
C120.09199 (8)0.0197 (3)0.22483 (11)0.0249 (4)
H120.11070.16720.22810.030*
C130.04348 (8)0.0499 (3)0.15298 (10)0.0214 (3)
H130.02910.04770.10660.026*
N10.08924 (7)0.5912 (2)0.01212 (9)0.0240 (3)
N20.04099 (7)0.5688 (2)0.05851 (9)0.0233 (3)
N30.03426 (6)0.3409 (2)0.07632 (8)0.0199 (3)
N40.19505 (7)0.1371 (2)0.13310 (9)0.0241 (3)
C210.57059 (7)0.2865 (3)0.09585 (9)0.0207 (3)
H210.57730.44780.09860.025*
C220.60466 (8)0.1210 (3)0.07479 (10)0.0209 (3)
C230.65878 (7)0.1470 (3)0.04927 (10)0.0205 (3)
C240.67754 (8)0.0357 (3)0.01264 (10)0.0234 (4)
H240.65660.18020.00540.028*
C250.72751 (8)0.0009 (3)0.01287 (11)0.0271 (4)
H250.74110.12150.03830.032*
C260.75731 (8)0.2115 (3)0.00089 (11)0.0275 (4)
H260.79150.23990.01790.033*
C270.73577 (8)0.3812 (3)0.03657 (11)0.0261 (4)
H270.75640.52640.04490.031*
C280.47567 (7)0.2492 (3)0.13615 (9)0.0198 (3)
C290.44870 (8)0.4638 (3)0.11137 (10)0.0217 (3)
H290.46280.55830.07820.026*
C300.40055 (8)0.5388 (3)0.13592 (10)0.0237 (4)
H300.38200.68620.11980.028*
C310.37951 (8)0.3996 (3)0.18367 (11)0.0263 (4)
H310.34640.45100.19970.032*
C320.40712 (8)0.1847 (3)0.20791 (10)0.0254 (4)
H320.39260.08950.24050.030*
C330.45560 (8)0.1081 (3)0.18493 (10)0.0225 (3)
H330.47480.03790.20210.027*
N210.57889 (7)0.0893 (2)0.07871 (9)0.0236 (3)
N220.53075 (7)0.0610 (2)0.10136 (9)0.0234 (3)
N230.52527 (6)0.1679 (2)0.11189 (8)0.0198 (3)
N240.68751 (7)0.3542 (2)0.06206 (9)0.0234 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0231 (8)0.0175 (8)0.0222 (8)0.0020 (6)0.0096 (7)0.0011 (6)
C20.0227 (8)0.0194 (8)0.0217 (8)0.0001 (6)0.0107 (7)0.0009 (6)
C30.0202 (7)0.0219 (8)0.0225 (8)0.0021 (6)0.0098 (7)0.0001 (6)
C40.0252 (8)0.0207 (8)0.0264 (9)0.0004 (6)0.0095 (7)0.0020 (7)
C50.0272 (9)0.0280 (9)0.0251 (9)0.0042 (7)0.0075 (7)0.0062 (7)
C60.0215 (8)0.0304 (9)0.0241 (9)0.0021 (7)0.0058 (7)0.0008 (7)
C70.0220 (8)0.0220 (8)0.0312 (10)0.0004 (6)0.0084 (7)0.0023 (7)
C80.0199 (7)0.0202 (8)0.0211 (8)0.0003 (6)0.0098 (7)0.0020 (6)
C90.0238 (8)0.0198 (8)0.0247 (9)0.0011 (6)0.0103 (7)0.0022 (6)
C100.0251 (8)0.0293 (9)0.0224 (8)0.0039 (7)0.0076 (7)0.0038 (7)
C110.0215 (8)0.0326 (10)0.0250 (9)0.0006 (7)0.0046 (7)0.0044 (7)
C120.0231 (8)0.0210 (8)0.0319 (9)0.0015 (6)0.0121 (7)0.0035 (7)
C130.0221 (8)0.0194 (8)0.0231 (8)0.0019 (6)0.0092 (7)0.0020 (6)
N10.0259 (7)0.0204 (7)0.0254 (8)0.0016 (6)0.0096 (6)0.0003 (5)
N20.0277 (7)0.0155 (7)0.0257 (8)0.0014 (5)0.0094 (6)0.0009 (5)
N30.0227 (7)0.0169 (6)0.0201 (7)0.0009 (5)0.0082 (6)0.0007 (5)
N40.0234 (7)0.0237 (7)0.0254 (8)0.0004 (6)0.0097 (6)0.0013 (6)
C210.0227 (8)0.0182 (8)0.0189 (8)0.0030 (6)0.0056 (7)0.0001 (6)
C220.0229 (8)0.0191 (8)0.0180 (8)0.0004 (6)0.0049 (7)0.0006 (6)
C230.0200 (7)0.0203 (8)0.0181 (8)0.0013 (6)0.0040 (6)0.0022 (6)
C240.0250 (8)0.0197 (8)0.0237 (8)0.0008 (6)0.0074 (7)0.0004 (6)
C250.0258 (8)0.0277 (9)0.0281 (9)0.0041 (7)0.0111 (8)0.0015 (7)
C260.0204 (8)0.0308 (9)0.0297 (9)0.0024 (7)0.0082 (7)0.0074 (7)
C270.0201 (8)0.0229 (8)0.0295 (9)0.0022 (6)0.0033 (7)0.0039 (7)
C280.0192 (7)0.0199 (7)0.0184 (8)0.0030 (6)0.0054 (6)0.0023 (6)
C290.0231 (7)0.0201 (8)0.0187 (8)0.0039 (6)0.0049 (7)0.0003 (6)
C300.0221 (8)0.0180 (8)0.0261 (9)0.0004 (6)0.0039 (7)0.0014 (6)
C310.0220 (8)0.0295 (9)0.0273 (9)0.0009 (7)0.0094 (7)0.0025 (7)
C320.0247 (8)0.0281 (9)0.0229 (9)0.0034 (7)0.0088 (7)0.0041 (7)
C330.0244 (8)0.0203 (8)0.0203 (8)0.0020 (6)0.0061 (7)0.0012 (6)
N210.0271 (7)0.0196 (7)0.0233 (8)0.0005 (6)0.0092 (6)0.0010 (5)
N220.0275 (7)0.0169 (7)0.0252 (8)0.0006 (5)0.0097 (6)0.0001 (5)
N230.0233 (7)0.0152 (6)0.0200 (7)0.0017 (5)0.0074 (6)0.0001 (5)
N240.0213 (7)0.0200 (7)0.0239 (7)0.0008 (5)0.0036 (6)0.0007 (5)
Geometric parameters (Å, º) top
C1—N31.357 (2)C21—N231.357 (2)
C1—C21.372 (2)C21—C221.375 (2)
C1—H10.9500C21—H210.9500
C2—N11.371 (2)C22—N211.371 (2)
C2—C31.469 (2)C22—C231.472 (2)
C3—N41.350 (2)C23—N241.348 (2)
C3—C41.393 (2)C23—C241.399 (2)
C4—C51.391 (2)C24—C251.389 (2)
C4—H40.9500C24—H240.9500
C5—C61.388 (3)C25—C261.385 (3)
C5—H50.9500C25—H250.9500
C6—C71.387 (2)C26—C271.384 (3)
C6—H60.9500C26—H260.9500
C7—N41.342 (2)C27—N241.347 (2)
C7—H70.9500C27—H270.9500
C8—C131.389 (2)C28—C291.386 (2)
C8—C91.391 (2)C28—C331.396 (2)
C8—N31.431 (2)C28—N231.433 (2)
C9—C101.387 (2)C29—C301.394 (2)
C9—H90.9500C29—H290.9500
C10—C111.386 (2)C30—C311.388 (2)
C10—H100.9500C30—H300.9500
C11—C121.391 (3)C31—C321.390 (2)
C11—H110.9500C31—H310.9500
C12—C131.383 (2)C32—C331.387 (2)
C12—H120.9500C32—H320.9500
C13—H130.9500C33—H330.9500
N1—N21.312 (2)N21—N221.3123 (19)
N2—N31.3601 (18)N22—N231.3585 (18)
N3—C1—C2104.64 (14)N23—C21—C22104.57 (14)
N3—C1—H1127.7N23—C21—H21127.7
C2—C1—H1127.7C22—C21—H21127.7
N1—C2—C1108.56 (14)N21—C22—C21108.49 (14)
N1—C2—C3121.96 (14)N21—C22—C23122.00 (14)
C1—C2—C3129.41 (15)C21—C22—C23129.49 (15)
N4—C3—C4123.34 (16)N24—C23—C24123.09 (15)
N4—C3—C2116.28 (14)N24—C23—C22116.38 (14)
C4—C3—C2120.33 (15)C24—C23—C22120.52 (14)
C5—C4—C3118.40 (16)C25—C24—C23118.47 (16)
C5—C4—H4120.8C25—C24—H24120.8
C3—C4—H4120.8C23—C24—H24120.8
C6—C5—C4119.10 (16)C26—C25—C24119.30 (16)
C6—C5—H5120.5C26—C25—H25120.3
C4—C5—H5120.5C24—C25—H25120.3
C7—C6—C5118.23 (16)C27—C26—C25118.04 (16)
C7—C6—H6120.9C27—C26—H26121.0
C5—C6—H6120.9C25—C26—H26121.0
N4—C7—C6124.08 (16)N24—C27—C26124.41 (16)
N4—C7—H7118.0N24—C27—H27117.8
C6—C7—H7118.0C26—C27—H27117.8
C13—C8—C9121.53 (15)C29—C28—C33121.33 (15)
C13—C8—N3119.84 (14)C29—C28—N23120.10 (14)
C9—C8—N3118.63 (14)C33—C28—N23118.57 (14)
C10—C9—C8118.84 (16)C28—C29—C30118.90 (15)
C10—C9—H9120.6C28—C29—H29120.5
C8—C9—H9120.6C30—C29—H29120.5
C11—C10—C9120.33 (16)C31—C30—C29120.52 (15)
C11—C10—H10119.8C31—C30—H30119.7
C9—C10—H10119.8C29—C30—H30119.7
C10—C11—C12120.00 (16)C30—C31—C32119.76 (16)
C10—C11—H11120.0C30—C31—H31120.1
C12—C11—H11120.0C32—C31—H31120.1
C13—C12—C11120.54 (16)C33—C32—C31120.60 (16)
C13—C12—H12119.7C33—C32—H32119.7
C11—C12—H12119.7C31—C32—H32119.7
C12—C13—C8118.76 (15)C32—C33—C28118.88 (15)
C12—C13—H13120.6C32—C33—H33120.6
C8—C13—H13120.6C28—C33—H33120.6
N2—N1—C2108.92 (13)N22—N21—C22108.94 (13)
N1—N2—N3107.24 (12)N21—N22—N23107.32 (13)
C1—N3—N2110.63 (13)C21—N23—N22110.68 (13)
C1—N3—C8129.94 (14)C21—N23—C28129.91 (14)
N2—N3—C8119.41 (13)N22—N23—C28119.41 (13)
C7—N4—C3116.82 (15)C27—N24—C23116.67 (14)
N3—C1—C2—N10.01 (17)N23—C21—C22—N210.09 (17)
N3—C1—C2—C3176.83 (15)N23—C21—C22—C23178.42 (16)
N1—C2—C3—N4166.85 (15)N21—C22—C23—N24168.14 (14)
C1—C2—C3—N416.7 (3)C21—C22—C23—N2413.7 (3)
N1—C2—C3—C415.7 (2)N21—C22—C23—C2412.9 (2)
C1—C2—C3—C4160.72 (17)C21—C22—C23—C24165.23 (17)
N4—C3—C4—C51.9 (3)N24—C23—C24—C251.0 (2)
C2—C3—C4—C5175.32 (15)C22—C23—C24—C25177.90 (15)
C3—C4—C5—C60.8 (3)C23—C24—C25—C260.4 (2)
C4—C5—C6—C70.8 (3)C24—C25—C26—C270.2 (3)
C5—C6—C7—N41.6 (3)C25—C26—C27—N240.2 (3)
C13—C8—C9—C100.1 (2)C33—C28—C29—C300.0 (2)
N3—C8—C9—C10179.73 (14)N23—C28—C29—C30179.95 (14)
C8—C9—C10—C110.4 (2)C28—C29—C30—C310.7 (2)
C9—C10—C11—C120.3 (3)C29—C30—C31—C320.7 (3)
C10—C11—C12—C130.3 (3)C30—C31—C32—C330.1 (3)
C11—C12—C13—C80.7 (2)C31—C32—C33—C280.8 (2)
C9—C8—C13—C120.7 (2)C29—C28—C33—C320.8 (2)
N3—C8—C13—C12179.70 (14)N23—C28—C33—C32179.30 (14)
C1—C2—N1—N20.03 (18)C21—C22—N21—N220.16 (18)
C3—C2—N1—N2177.15 (14)C23—C22—N21—N22178.63 (14)
C2—N1—N2—N30.06 (17)C22—N21—N22—N230.15 (17)
C2—C1—N3—N20.05 (17)C22—C21—N23—N220.00 (17)
C2—C1—N3—C8178.43 (15)C22—C21—N23—C28179.46 (15)
N1—N2—N3—C10.07 (17)N21—N22—N23—C210.10 (17)
N1—N2—N3—C8178.59 (13)N21—N22—N23—C28179.42 (13)
C13—C8—N3—C128.4 (2)C29—C28—N23—C2130.2 (2)
C9—C8—N3—C1151.93 (16)C33—C28—N23—C21149.71 (16)
C13—C8—N3—N2149.95 (15)C29—C28—N23—N22149.22 (15)
C9—C8—N3—N229.7 (2)C33—C28—N23—N2230.9 (2)
C6—C7—N4—C30.6 (2)C26—C27—N24—C230.3 (2)
C4—C3—N4—C71.2 (2)C24—C23—N24—C270.9 (2)
C2—C3—N4—C7176.13 (14)C22—C23—N24—C27178.02 (14)
(L3) top
Crystal data top
C13H9FN4F(000) = 496
Mr = 240.24Dx = 1.452 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 12628 reflections
a = 12.2031 (3) Åθ = 2.9–27.5°
b = 7.9798 (2) ŵ = 0.10 mm1
c = 11.6329 (3) ÅT = 120 K
β = 104.043 (2)°Block, colourless
V = 1098.94 (5) Å30.60 × 0.58 × 0.40 mm
Z = 4
Data collection top
Bruker-Nonius CCD camera on κ-goniostat
diffractometer
2510 independent reflections
Radiation source: Bruker Nonius FR591 Rotating Anode2228 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.1°
ϕ & ω scans to fill the asymmetric unith = 1515
Absorption correction: multi-scan
SADABS 2007/2 (Sheldrick, G.M., 2007)
k = 1010
Tmin = 0.940, Tmax = 0.960l = 1415
13725 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-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 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C13H9FN4V = 1098.94 (5) Å3
Mr = 240.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.2031 (3) ŵ = 0.10 mm1
b = 7.9798 (2) ÅT = 120 K
c = 11.6329 (3) Å0.60 × 0.58 × 0.40 mm
β = 104.043 (2)°
Data collection top
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 = 0.960Rint = 0.031
13725 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.092H-atom parameters constrained
S = 1.05Δρmax = 0.26 e Å3
2510 reflectionsΔρmin = 0.23 e Å3
163 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.07126 (9)0.68437 (14)0.02975 (10)0.0172 (2)
C20.09543 (10)0.64013 (15)0.07707 (10)0.0195 (2)
H20.04710.67520.14990.023*
C30.19055 (10)0.54448 (16)0.07679 (10)0.0216 (3)
H30.20830.51290.14890.026*
C40.25856 (10)0.49649 (15)0.03077 (11)0.0211 (3)
C50.23515 (10)0.53617 (16)0.13772 (10)0.0231 (3)
H50.28320.49900.21020.028*
C60.14010 (10)0.63142 (15)0.13718 (10)0.0213 (3)
H60.12210.66040.20960.026*
C70.10673 (9)0.84006 (14)0.06520 (10)0.0187 (2)
H70.10940.82580.14690.022*
C80.18276 (10)0.92393 (14)0.01644 (10)0.0188 (2)
C90.28701 (10)1.01073 (14)0.07681 (10)0.0193 (2)
C100.35449 (10)1.09363 (16)0.01403 (11)0.0247 (3)
H100.33421.09580.07010.030*
C110.45169 (11)1.17277 (17)0.07651 (13)0.0287 (3)
H110.49921.23000.03580.034*
C120.47890 (10)1.16740 (16)0.19944 (12)0.0278 (3)
H120.54501.22080.24460.033*
C130.40682 (11)1.08175 (17)0.25425 (12)0.0269 (3)
H130.42551.07810.33840.032*
N10.02727 (8)0.78225 (12)0.02857 (8)0.0175 (2)
N20.05257 (9)0.82826 (14)0.13177 (9)0.0233 (2)
N30.14679 (9)0.91435 (14)0.10410 (9)0.0239 (2)
N40.31256 (9)1.00390 (13)0.19595 (9)0.0230 (2)
F10.35306 (6)0.40439 (10)0.03134 (7)0.0304 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0174 (5)0.0178 (5)0.0160 (5)0.0038 (4)0.0033 (4)0.0004 (4)
C20.0205 (6)0.0235 (6)0.0136 (5)0.0049 (5)0.0027 (4)0.0004 (4)
C30.0222 (6)0.0254 (6)0.0183 (5)0.0047 (5)0.0070 (4)0.0024 (5)
C40.0182 (5)0.0213 (6)0.0238 (6)0.0004 (5)0.0047 (4)0.0014 (5)
C50.0248 (6)0.0249 (6)0.0172 (6)0.0008 (5)0.0005 (5)0.0008 (5)
C60.0255 (6)0.0238 (6)0.0139 (5)0.0009 (5)0.0036 (4)0.0014 (4)
C70.0205 (6)0.0208 (5)0.0142 (5)0.0028 (5)0.0029 (4)0.0011 (4)
C80.0214 (6)0.0178 (5)0.0168 (5)0.0044 (4)0.0041 (4)0.0002 (4)
C90.0197 (5)0.0179 (5)0.0201 (6)0.0050 (4)0.0044 (4)0.0004 (4)
C100.0257 (6)0.0257 (6)0.0241 (6)0.0019 (5)0.0086 (5)0.0016 (5)
C110.0232 (6)0.0267 (6)0.0377 (7)0.0002 (5)0.0105 (5)0.0049 (6)
C120.0204 (6)0.0231 (6)0.0362 (7)0.0007 (5)0.0001 (5)0.0009 (5)
C130.0253 (6)0.0277 (6)0.0243 (6)0.0000 (5)0.0005 (5)0.0005 (5)
N10.0208 (5)0.0193 (5)0.0122 (4)0.0026 (4)0.0033 (3)0.0003 (4)
N20.0268 (5)0.0290 (5)0.0140 (5)0.0030 (4)0.0046 (4)0.0024 (4)
N30.0270 (5)0.0271 (5)0.0169 (5)0.0023 (4)0.0039 (4)0.0011 (4)
N40.0231 (5)0.0259 (5)0.0185 (5)0.0004 (4)0.0023 (4)0.0001 (4)
F10.0241 (4)0.0372 (4)0.0296 (4)0.0076 (3)0.0056 (3)0.0022 (3)
Geometric parameters (Å, º) top
C1—C21.3906 (15)C8—C91.4689 (16)
C1—C61.3916 (16)C8—N31.3660 (15)
C1—N11.4310 (15)C9—C101.3932 (17)
C2—H20.9500C9—N41.3458 (15)
C2—C31.3886 (17)C10—H100.9500
C3—H30.9500C10—C111.3841 (18)
C3—C41.3773 (17)C11—H110.9500
C4—C51.3792 (17)C11—C121.388 (2)
C4—F11.3662 (14)C12—H120.9500
C5—H50.9500C12—C131.3854 (19)
C5—C61.3854 (17)C13—H130.9500
C6—H60.9500C13—N41.3381 (16)
C7—H70.9500N1—N21.3605 (13)
C7—C81.3733 (17)N2—N31.3107 (15)
C7—N11.3527 (14)
C2—C1—C6120.84 (11)N3—C8—C9122.85 (11)
C2—C1—N1119.34 (10)C10—C9—C8121.78 (11)
C6—C1—N1119.81 (10)N4—C9—C8115.51 (10)
C1—C2—H2120.1N4—C9—C10122.71 (11)
C3—C2—C1119.73 (11)C9—C10—H10120.6
C3—C2—H2120.1C11—C10—C9118.79 (12)
C2—C3—H3120.9C11—C10—H10120.6
C4—C3—C2118.29 (11)C10—C11—H11120.4
C4—C3—H3120.9C10—C11—C12119.15 (12)
C3—C4—C5123.00 (11)C12—C11—H11120.4
F1—C4—C3118.41 (11)C11—C12—H12121.0
F1—C4—C5118.59 (10)C13—C12—C11118.00 (12)
C4—C5—H5120.7C13—C12—H12121.0
C4—C5—C6118.57 (11)C12—C13—H13118.0
C6—C5—H5120.7N4—C13—C12124.02 (12)
C1—C6—H6120.2N4—C13—H13118.0
C5—C6—C1119.54 (11)C7—N1—C1129.06 (10)
C5—C6—H6120.2C7—N1—N2110.35 (10)
C8—C7—H7127.6N2—N1—C1120.59 (9)
N1—C7—H7127.6N3—N2—N1107.35 (9)
N1—C7—C8104.89 (10)N2—N3—C8109.01 (10)
C7—C8—C9128.74 (11)C13—N4—C9117.32 (11)
N3—C8—C7108.40 (10)
(L4) top
Crystal data top
C13H9ClN4F(000) = 1056
Mr = 256.69Dx = 1.477 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 16.0000 (11) ÅCell parameters from 7275 reflections
b = 5.9258 (2) Åθ = 3.1–27.5°
c = 24.3829 (17) ŵ = 0.32 mm1
β = 93.109 (8)°T = 120 K
V = 2308.4 (2) Å3Block, colourless
Z = 80.36 × 0.12 × 0.06 mm
Data collection top
Rigaku R-AXIS SPIDER IP
diffractometer
2636 independent reflections
Radiation source: Sealed X-Ray tube1654 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
Detector resolution: 10 pixels mm-1θmax = 27.5°, θmin = 3.1°
profile data from oscillation ω–scansh = 2020
Absorption correction: multi-scan
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
k = 76
Tmin = 0.608, Tmax = 1.000l = 3131
11996 measured reflections
Refinement top
Refinement on F2Primary atom site location: iterative
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-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 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.46 e Å3
Crystal data top
C13H9ClN4V = 2308.4 (2) Å3
Mr = 256.69Z = 8
Monoclinic, C2/cMo Kα radiation
a = 16.0000 (11) ŵ = 0.32 mm1
b = 5.9258 (2) ÅT = 120 K
c = 24.3829 (17) Å0.36 × 0.12 × 0.06 mm
β = 93.109 (8)°
Data collection top
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 = 1.000Rint = 0.050
11996 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.137H-atom parameters constrained
S = 1.05Δρmax = 0.25 e Å3
2636 reflectionsΔρmin = 0.46 e Å3
163 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.46583 (4)0.73367 (10)0.32948 (2)0.0400 (2)
N10.81166 (11)0.3764 (3)0.65649 (7)0.0331 (4)
N80.67605 (12)0.0050 (3)0.57198 (8)0.0334 (4)
N90.63176 (12)0.0605 (3)0.52701 (8)0.0336 (5)
N100.64080 (11)0.2865 (3)0.51988 (7)0.0269 (4)
C20.86138 (15)0.3720 (4)0.70229 (9)0.0368 (5)
H20.89300.50010.71090.044*
C30.86908 (15)0.1908 (4)0.73758 (9)0.0362 (5)
H30.90490.19670.76890.043*
C40.82221 (14)0.0005 (4)0.72520 (9)0.0358 (5)
H40.82510.12410.74840.043*
C50.77106 (14)0.0028 (4)0.67803 (9)0.0344 (5)
H50.73950.13020.66870.041*
C60.76725 (14)0.1877 (3)0.64441 (9)0.0290 (5)
C70.71381 (13)0.1947 (3)0.59369 (9)0.0274 (5)
C110.69147 (13)0.3742 (3)0.56060 (8)0.0278 (5)
H110.70770.52400.56520.033*
C120.59896 (12)0.3934 (3)0.47387 (8)0.0267 (5)
C130.62574 (13)0.6034 (3)0.45686 (8)0.0288 (5)
H130.67100.67340.47540.035*
C140.58504 (14)0.7085 (3)0.41235 (9)0.0301 (5)
H140.60270.84920.40060.036*
C150.51758 (13)0.6012 (4)0.38542 (8)0.0303 (5)
C160.49039 (14)0.3917 (4)0.40234 (9)0.0320 (5)
H160.44520.32170.38370.038*
C170.53063 (13)0.2880 (3)0.44687 (9)0.0297 (5)
H170.51230.14840.45890.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0384 (4)0.0445 (4)0.0364 (4)0.0038 (3)0.0039 (2)0.0032 (2)
N10.0349 (11)0.0312 (10)0.0330 (11)0.0047 (8)0.0006 (8)0.0007 (8)
N80.0359 (11)0.0268 (9)0.0370 (11)0.0022 (8)0.0010 (8)0.0006 (8)
N90.0369 (11)0.0226 (9)0.0411 (11)0.0038 (8)0.0005 (9)0.0004 (8)
N100.0296 (10)0.0219 (9)0.0296 (10)0.0028 (7)0.0048 (7)0.0027 (7)
C20.0371 (13)0.0328 (12)0.0401 (13)0.0074 (10)0.0001 (10)0.0019 (10)
C30.0360 (13)0.0410 (13)0.0314 (13)0.0025 (11)0.0010 (10)0.0011 (10)
C40.0429 (14)0.0315 (12)0.0331 (12)0.0027 (10)0.0037 (10)0.0053 (10)
C50.0383 (13)0.0282 (12)0.0370 (13)0.0019 (10)0.0052 (10)0.0013 (9)
C60.0302 (12)0.0277 (12)0.0297 (12)0.0004 (9)0.0061 (9)0.0018 (9)
C70.0263 (11)0.0258 (11)0.0306 (11)0.0037 (9)0.0046 (9)0.0013 (9)
C110.0301 (12)0.0240 (11)0.0295 (11)0.0060 (9)0.0032 (9)0.0023 (9)
C120.0261 (11)0.0247 (11)0.0298 (12)0.0005 (9)0.0050 (9)0.0050 (9)
C130.0292 (12)0.0250 (11)0.0325 (12)0.0029 (9)0.0032 (9)0.0048 (9)
C140.0321 (12)0.0261 (11)0.0324 (12)0.0041 (9)0.0057 (9)0.0013 (9)
C150.0301 (12)0.0321 (12)0.0290 (11)0.0003 (9)0.0043 (9)0.0043 (9)
C160.0288 (12)0.0315 (12)0.0357 (12)0.0074 (9)0.0023 (9)0.0075 (10)
C170.0277 (12)0.0266 (11)0.0353 (13)0.0037 (9)0.0045 (9)0.0027 (9)
Geometric parameters (Å, º) top
Cl1—C151.743 (2)C5—C61.395 (3)
N1—C21.336 (3)C6—C71.465 (3)
N1—C61.349 (3)C7—C111.371 (3)
N8—N91.315 (3)C11—H110.9300
N8—C71.369 (3)C12—C131.387 (3)
N9—N101.359 (2)C12—C171.393 (3)
N10—C111.351 (3)C13—H130.9300
N10—C121.423 (3)C13—C141.383 (3)
C2—H20.9300C14—H140.9300
C2—C31.377 (3)C14—C151.387 (3)
C3—H30.9300C15—C161.385 (3)
C3—C41.379 (3)C16—H160.9300
C4—H40.9300C16—C171.377 (3)
C4—C51.375 (3)C17—H170.9300
C5—H50.9300
C2—N1—C6116.68 (19)C11—C7—C6129.8 (2)
N9—N8—C7108.87 (17)N10—C11—C7105.12 (18)
N8—N9—N10107.28 (17)N10—C11—H11127.4
N9—N10—C12119.36 (17)C7—C11—H11127.4
C11—N10—N9110.41 (17)C13—C12—N10119.68 (18)
C11—N10—C12130.23 (17)C13—C12—C17120.54 (19)
N1—C2—H2117.7C17—C12—N10119.77 (19)
N1—C2—C3124.5 (2)C12—C13—H13120.0
C3—C2—H2117.7C14—C13—C12119.92 (19)
C2—C3—H3120.9C14—C13—H13120.0
C2—C3—C4118.1 (2)C13—C14—H14120.5
C4—C3—H3120.9C13—C14—C15119.09 (19)
C3—C4—H4120.4C15—C14—H14120.5
C5—C4—C3119.1 (2)C14—C15—Cl1119.23 (17)
C5—C4—H4120.4C16—C15—Cl1119.53 (17)
C4—C5—H5120.5C16—C15—C14121.2 (2)
C4—C5—C6119.0 (2)C15—C16—H16120.2
C6—C5—H5120.5C17—C16—C15119.6 (2)
N1—C6—C5122.5 (2)C17—C16—H16120.2
N1—C6—C7115.94 (19)C12—C17—H17120.2
C5—C6—C7121.6 (2)C16—C17—C12119.60 (19)
N8—C7—C6121.89 (19)C16—C17—H17120.2
N8—C7—C11108.32 (19)
Cl1—C15—C16—C17179.30 (16)C4—C5—C6—N10.3 (3)
N1—C2—C3—C40.3 (4)C4—C5—C6—C7179.9 (2)
N1—C6—C7—N8169.32 (19)C5—C6—C7—N811.1 (3)
N1—C6—C7—C1111.4 (3)C5—C6—C7—C11168.2 (2)
N8—N9—N10—C110.2 (2)C6—N1—C2—C30.8 (3)
N8—N9—N10—C12179.86 (16)C6—C7—C11—N10179.4 (2)
N8—C7—C11—N100.0 (2)C7—N8—N9—N100.2 (2)
N9—N8—C7—C6179.56 (18)C11—N10—C12—C1318.8 (3)
N9—N8—C7—C110.1 (2)C11—N10—C12—C17160.1 (2)
N9—N10—C11—C70.1 (2)C12—N10—C11—C7179.96 (19)
N9—N10—C12—C13161.09 (19)C12—C13—C14—C150.1 (3)
N9—N10—C12—C1720.0 (3)C13—C12—C17—C161.2 (3)
N10—C12—C13—C14179.67 (18)C13—C14—C15—Cl1179.72 (14)
N10—C12—C17—C16179.92 (18)C13—C14—C15—C160.1 (3)
C2—N1—C6—C51.1 (3)C14—C15—C16—C170.3 (3)
C2—N1—C6—C7179.30 (18)C15—C16—C17—C120.9 (3)
C2—C3—C4—C51.1 (3)C17—C12—C13—C140.7 (3)
C3—C4—C5—C60.8 (3)
(L5) top
Crystal data top
C14H12N4F(000) = 248
Mr = 236.28Dx = 1.341 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 17303 reflections
a = 5.7797 (5) Åθ = 2.9–27.5°
b = 6.7414 (4) ŵ = 0.08 mm1
c = 15.0259 (12) ÅT = 120 K
β = 92.359 (4)°Block, colourless
V = 584.96 (8) Å30.38 × 0.12 × 0.10 mm
Z = 2
Data collection top
Bruker-Nonius CCD camera on κ-goniostat
diffractometer
2622 independent reflections
Radiation source: Bruker Nonius FR591 Rotating Anode2042 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.3°
ϕ & ω scans to fill the asymmetric unith = 77
Absorption correction: multi-scan
SADABS 2007/2 (Sheldrick, G.M., 2007)
k = 88
Tmin = 0.969, Tmax = 0.992l = 1919
9647 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-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 reflectionsΔρmax = 0.17 e Å3
165 parametersΔρmin = 0.18 e Å3
1 restraintExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.047 (8)
Crystal data top
C14H12N4V = 584.96 (8) Å3
Mr = 236.28Z = 2
Monoclinic, P21Mo Kα radiation
a = 5.7797 (5) ŵ = 0.08 mm1
b = 6.7414 (4) ÅT = 120 K
c = 15.0259 (12) Å0.38 × 0.12 × 0.10 mm
β = 92.359 (4)°
Data collection top
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 = 0.992Rint = 0.056
9647 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0481 restraint
wR(F2) = 0.124H-atom parameters constrained
S = 1.04Δρmax = 0.17 e Å3
2622 reflectionsΔρmin = 0.18 e Å3
165 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.7152 (4)0.7358 (3)0.18589 (13)0.0263 (5)
C20.9309 (4)0.6565 (3)0.20725 (14)0.0295 (5)
H21.03400.72180.24850.035*
C30.9947 (4)0.4795 (3)0.16742 (14)0.0307 (5)
H31.14240.42430.18240.037*
C40.8491 (4)0.3815 (3)0.10649 (13)0.0285 (5)
C50.6324 (4)0.4656 (3)0.08594 (14)0.0331 (5)
H50.52900.40100.04460.040*
C60.5658 (4)0.6421 (3)0.12498 (14)0.0320 (5)
H60.41860.69830.11000.038*
C70.9249 (4)0.1921 (3)0.06262 (14)0.0360 (6)
H7A0.98630.22280.00440.054*
H7B0.79200.10260.05470.054*
H7C1.04550.12790.10030.054*
C80.7622 (4)1.0476 (3)0.27842 (13)0.0270 (5)
H80.92421.04910.29200.032*
C90.6011 (4)1.1810 (3)0.30500 (13)0.0277 (5)
C100.6295 (4)1.3623 (3)0.35857 (14)0.0282 (5)
C110.4514 (4)1.5010 (3)0.36158 (15)0.0331 (5)
H110.30851.47890.32960.040*
C120.4854 (4)1.6720 (4)0.41189 (15)0.0395 (6)
H120.36771.76990.41440.047*
C130.6950 (4)1.6958 (4)0.45822 (15)0.0422 (6)
H130.72411.81070.49350.051*
C140.8611 (4)1.5505 (4)0.45245 (15)0.0412 (6)
H141.00371.56900.48510.049*
N10.6415 (3)0.9134 (3)0.22877 (11)0.0268 (4)
N20.4112 (3)0.9609 (3)0.22484 (13)0.0349 (5)
N30.3881 (3)1.1240 (3)0.27119 (12)0.0356 (5)
N40.8353 (3)1.3853 (3)0.40398 (11)0.0345 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0255 (11)0.0259 (11)0.0276 (10)0.0023 (9)0.0029 (9)0.0025 (9)
C20.0248 (11)0.0292 (12)0.0342 (11)0.0000 (9)0.0020 (9)0.0041 (9)
C30.0267 (11)0.0326 (12)0.0328 (11)0.0002 (10)0.0011 (9)0.0029 (9)
C40.0310 (12)0.0281 (12)0.0266 (10)0.0018 (10)0.0047 (9)0.0025 (9)
C50.0313 (12)0.0378 (13)0.0299 (12)0.0038 (10)0.0017 (9)0.0070 (9)
C60.0266 (11)0.0383 (13)0.0309 (11)0.0001 (10)0.0022 (9)0.0001 (10)
C70.0405 (14)0.0345 (13)0.0328 (12)0.0012 (11)0.0009 (10)0.0035 (9)
C80.0244 (11)0.0292 (12)0.0274 (11)0.0008 (9)0.0006 (8)0.0026 (9)
C90.0261 (11)0.0275 (11)0.0295 (11)0.0003 (9)0.0021 (8)0.0025 (9)
C100.0288 (11)0.0295 (12)0.0269 (10)0.0002 (9)0.0080 (8)0.0026 (9)
C110.0338 (12)0.0352 (14)0.0309 (11)0.0052 (11)0.0059 (9)0.0045 (10)
C120.0455 (15)0.0337 (13)0.0404 (13)0.0039 (11)0.0152 (11)0.0005 (10)
C130.0444 (15)0.0403 (14)0.0427 (14)0.0046 (12)0.0117 (12)0.0088 (11)
C140.0415 (14)0.0439 (15)0.0385 (13)0.0035 (12)0.0064 (10)0.0102 (11)
N10.0211 (9)0.0281 (10)0.0312 (9)0.0007 (7)0.0001 (7)0.0002 (8)
N20.0228 (10)0.0367 (11)0.0450 (11)0.0043 (8)0.0017 (8)0.0039 (8)
N30.0274 (10)0.0362 (11)0.0432 (11)0.0025 (8)0.0006 (8)0.0053 (9)
N40.0334 (11)0.0366 (11)0.0337 (10)0.0011 (9)0.0032 (8)0.0034 (8)
Geometric parameters (Å, º) top
C1—C21.382 (3)C8—C91.366 (3)
C1—C61.385 (3)C8—H80.9500
C1—N11.433 (3)C9—N31.367 (3)
C2—C31.391 (3)C9—C101.469 (3)
C2—H20.9500C10—N41.356 (3)
C3—C41.386 (3)C10—C111.393 (3)
C3—H30.9500C11—C121.388 (3)
C4—C51.398 (3)C11—H110.9500
C4—C71.510 (3)C12—C131.382 (4)
C5—C61.388 (3)C12—H120.9500
C5—H50.9500C13—C141.377 (3)
C6—H60.9500C13—H130.9500
C7—H7A0.9800C14—N41.336 (3)
C7—H7B0.9800C14—H140.9500
C7—H7C0.9800N1—N21.368 (2)
C8—N11.349 (3)N2—N31.311 (3)
C2—C1—C6120.6 (2)C9—C8—H8127.5
C2—C1—N1120.08 (19)C8—C9—N3108.68 (19)
C6—C1—N1119.30 (19)C8—C9—C10130.2 (2)
C1—C2—C3119.0 (2)N3—C9—C10121.09 (19)
C1—C2—H2120.5N4—C10—C11122.8 (2)
C3—C2—H2120.5N4—C10—C9116.55 (18)
C4—C3—C2121.9 (2)C11—C10—C9120.7 (2)
C4—C3—H3119.0C12—C11—C10119.2 (2)
C2—C3—H3119.0C12—C11—H11120.4
C3—C4—C5117.82 (19)C10—C11—H11120.4
C3—C4—C7120.8 (2)C13—C12—C11118.2 (2)
C5—C4—C7121.3 (2)C13—C12—H12120.9
C6—C5—C4121.1 (2)C11—C12—H12120.9
C6—C5—H5119.5C14—C13—C12119.0 (2)
C4—C5—H5119.5C14—C13—H13120.5
C1—C6—C5119.6 (2)C12—C13—H13120.5
C1—C6—H6120.2N4—C14—C13124.4 (2)
C5—C6—H6120.2N4—C14—H14117.8
C4—C7—H7A109.5C13—C14—H14117.8
C4—C7—H7B109.5C8—N1—N2110.29 (17)
H7A—C7—H7B109.5C8—N1—C1130.74 (18)
C4—C7—H7C109.5N2—N1—C1118.90 (17)
H7A—C7—H7C109.5N3—N2—N1107.06 (17)
H7B—C7—H7C109.5N2—N3—C9108.89 (17)
N1—C8—C9105.08 (18)C14—N4—C10116.5 (2)
N1—C8—H8127.5
(L6) top
Crystal data top
C14H9F3N4Z = 2
Mr = 290.25F(000) = 296
Triclinic, P1Dx = 1.585 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.7460 (1) ÅCell parameters from 9548 reflections
b = 7.2076 (2) Åθ = 2.9–27.5°
c = 15.2997 (4) ŵ = 0.13 mm1
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
Data collection top
Bruker-Nonius CCD camera on κ-goniostat
diffractometer
2785 independent reflections
Radiation source: Bruker Nonius FR591 Rotating Anode2436 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.9°
ϕ & ω scans to fill the asymmetric unith = 77
Absorption correction: multi-scan
SADABS 2007/2 (Sheldrick, G.M., 2007)
k = 99
Tmin = 0.925, Tmax = 0.977l = 1919
14232 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-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 reflectionsΔρmax = 0.37 e Å3
191 parametersΔρmin = 0.30 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.040 (9)
Crystal data top
C14H9F3N4γ = 92.290 (2)°
Mr = 290.25V = 608.25 (3) Å3
Triclinic, P1Z = 2
a = 5.7460 (1) ÅMo Kα radiation
b = 7.2076 (2) ŵ = 0.13 mm1
c = 15.2997 (4) ÅT = 120 K
α = 103.045 (2)°0.60 × 0.20 × 0.18 mm
β = 98.768 (2)°
Data collection top
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 = 0.977Rint = 0.035
14232 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.109H-atom parameters constrained
S = 1.03Δρmax = 0.37 e Å3
2785 reflectionsΔρmin = 0.30 e Å3
191 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.3128 (2)0.43341 (14)0.05724 (6)0.0375 (3)
F20.52678 (16)0.21283 (14)0.00329 (6)0.0297 (2)
F30.19398 (17)0.13851 (15)0.03806 (6)0.0353 (3)
N40.7027 (2)0.16644 (16)0.68200 (8)0.0179 (3)
N21.04755 (19)0.27825 (17)0.44702 (8)0.0188 (3)
N10.80777 (19)0.25217 (16)0.42478 (7)0.0155 (2)
N31.1018 (2)0.27229 (17)0.53222 (8)0.0189 (3)
C140.7054 (2)0.16196 (19)0.76930 (9)0.0187 (3)
H160.56520.11460.78540.022*
C50.3835 (2)0.33679 (18)0.23248 (9)0.0170 (3)
H50.23520.38830.22130.020*
C60.4823 (2)0.33276 (18)0.32066 (9)0.0169 (3)
H60.40270.38080.37020.020*
C10.6999 (2)0.25706 (18)0.33522 (8)0.0152 (3)
C40.5016 (2)0.26543 (18)0.16024 (9)0.0160 (3)
C90.8988 (2)0.24162 (18)0.56547 (9)0.0159 (3)
C100.9042 (2)0.23227 (18)0.66061 (9)0.0153 (3)
C111.1095 (2)0.29355 (19)0.72447 (9)0.0180 (3)
H131.24910.33720.70660.022*
C80.7093 (2)0.22909 (18)0.49709 (9)0.0163 (3)
H80.54650.20890.49990.020*
C130.8992 (2)0.22189 (19)0.83764 (9)0.0191 (3)
H150.89110.21690.89860.023*
C121.1058 (2)0.28946 (19)0.81446 (9)0.0195 (3)
H141.24200.33210.85950.023*
C70.3857 (2)0.26374 (19)0.06569 (9)0.0192 (3)
C20.8201 (2)0.18751 (18)0.26371 (9)0.0165 (3)
H20.96940.13760.27500.020*
C30.7204 (2)0.19164 (18)0.17579 (9)0.0171 (3)
H30.80080.14440.12650.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0611 (7)0.0297 (5)0.0225 (5)0.0215 (5)0.0019 (4)0.0080 (4)
F20.0324 (5)0.0430 (5)0.0163 (4)0.0086 (4)0.0083 (4)0.0087 (4)
F30.0303 (5)0.0483 (6)0.0226 (5)0.0140 (4)0.0059 (4)0.0087 (4)
N40.0164 (5)0.0201 (5)0.0182 (6)0.0016 (4)0.0032 (4)0.0063 (4)
N20.0147 (5)0.0254 (6)0.0161 (5)0.0011 (4)0.0018 (4)0.0053 (4)
N10.0135 (5)0.0188 (5)0.0144 (5)0.0003 (4)0.0024 (4)0.0043 (4)
N30.0163 (5)0.0249 (6)0.0164 (6)0.0023 (4)0.0031 (4)0.0063 (4)
C140.0176 (6)0.0206 (6)0.0201 (7)0.0033 (5)0.0058 (5)0.0074 (5)
C50.0149 (6)0.0179 (6)0.0186 (6)0.0015 (5)0.0022 (5)0.0057 (5)
C60.0171 (6)0.0179 (6)0.0161 (6)0.0005 (5)0.0056 (5)0.0035 (5)
C10.0156 (6)0.0158 (6)0.0142 (6)0.0019 (5)0.0020 (5)0.0045 (5)
C40.0183 (6)0.0143 (6)0.0149 (6)0.0019 (5)0.0020 (5)0.0036 (5)
C90.0155 (6)0.0157 (6)0.0167 (6)0.0012 (5)0.0036 (5)0.0034 (5)
C100.0159 (6)0.0148 (6)0.0157 (6)0.0027 (5)0.0031 (5)0.0041 (5)
C110.0163 (6)0.0191 (6)0.0193 (7)0.0001 (5)0.0022 (5)0.0066 (5)
C80.0156 (6)0.0193 (6)0.0153 (6)0.0001 (5)0.0040 (5)0.0058 (5)
C130.0237 (7)0.0191 (6)0.0160 (6)0.0052 (5)0.0044 (5)0.0057 (5)
C120.0210 (7)0.0191 (6)0.0168 (6)0.0015 (5)0.0012 (5)0.0034 (5)
C70.0229 (7)0.0185 (6)0.0163 (6)0.0019 (5)0.0031 (5)0.0044 (5)
C20.0154 (6)0.0170 (6)0.0176 (6)0.0011 (5)0.0039 (5)0.0042 (5)
C30.0186 (6)0.0169 (6)0.0157 (6)0.0001 (5)0.0051 (5)0.0022 (5)
Geometric parameters (Å, º) top
F1—C71.3355 (16)C6—H60.9500
F2—C71.3434 (16)C1—C21.3914 (18)
F3—C71.3466 (16)C4—C31.3925 (19)
N4—C141.3410 (17)C4—C71.4947 (18)
N4—C101.3471 (17)C9—C81.3749 (18)
N2—N31.3042 (16)C9—C101.4679 (18)
N2—N11.3627 (15)C10—C111.3977 (18)
N1—C81.3556 (16)C11—C121.3871 (19)
N1—C11.4240 (16)C11—H130.9500
N3—C91.3707 (17)C8—H80.9500
C14—C131.387 (2)C13—C121.390 (2)
C14—H160.9500C13—H150.9500
C5—C61.3889 (18)C12—H140.9500
C5—C41.3950 (18)C2—C31.3869 (18)
C5—H50.9500C2—H20.9500
C6—C11.3909 (18)C3—H30.9500
C14—N4—C10116.77 (12)C11—C10—C9120.30 (12)
N3—N2—N1107.11 (10)C12—C11—C10118.78 (12)
C8—N1—N2110.86 (11)C12—C11—H13120.6
C8—N1—C1130.30 (11)C10—C11—H13120.6
N2—N1—C1118.82 (10)N1—C8—C9104.27 (11)
N2—N3—C9109.18 (11)N1—C8—H8127.9
N4—C14—C13124.35 (13)C9—C8—H8127.9
N4—C14—H16117.8C14—C13—C12118.17 (12)
C13—C14—H16117.8C14—C13—H15120.9
C6—C5—C4120.15 (12)C12—C13—H15120.9
C6—C5—H5119.9C11—C12—C13118.86 (12)
C4—C5—H5119.9C11—C12—H14120.6
C5—C6—C1118.82 (12)C13—C12—H14120.6
C5—C6—H6120.6F1—C7—F2106.28 (11)
C1—C6—H6120.6F1—C7—F3106.38 (12)
C6—C1—C2121.43 (12)F2—C7—F3105.48 (11)
C6—C1—N1120.42 (11)F1—C7—C4112.90 (11)
C2—C1—N1118.14 (11)F2—C7—C4113.35 (11)
C3—C4—C5120.49 (12)F3—C7—C4111.87 (11)
C3—C4—C7120.62 (12)C3—C2—C1119.48 (12)
C5—C4—C7118.86 (12)C3—C2—H2120.3
N3—C9—C8108.57 (11)C1—C2—H2120.3
N3—C9—C10121.56 (12)C2—C3—C4119.63 (12)
C8—C9—C10129.85 (12)C2—C3—H3120.2
N4—C10—C11123.07 (12)C4—C3—H3120.2
N4—C10—C9116.62 (11)
(L7) top
Crystal data top
C14H9N5F(000) = 1024
Mr = 247.26Dx = 1.426 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71075 Å
a = 16.0427 (19) ÅCell parameters from 7318 reflections
b = 5.8677 (6) Åθ = 3.1–27.5°
c = 24.487 (3) ŵ = 0.09 mm1
β = 92.354 (8)°T = 100 K
V = 2303.1 (5) Å3Needle, colourless
Z = 80.22 × 0.14 × 0.04 mm
Data collection top
Rigaku AFC12 (Right)
diffractometer
2638 independent reflections
Radiation source: Rotating Anode2154 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm-1Rint = 0.061
profile data from ω–scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
h = 2020
Tmin = 0.677, Tmax = 1.000k = 76
9891 measured reflectionsl = 3127
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-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 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C14H9N5V = 2303.1 (5) Å3
Mr = 247.26Z = 8
Monoclinic, C2/cMo Kα radiation
a = 16.0427 (19) ŵ = 0.09 mm1
b = 5.8677 (6) ÅT = 100 K
c = 24.487 (3) Å0.22 × 0.14 × 0.04 mm
β = 92.354 (8)°
Data collection top
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 = 1.000Rint = 0.061
9891 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.121H-atom parameters constrained
S = 1.06Δρmax = 0.29 e Å3
2638 reflectionsΔρmin = 0.25 e Å3
172 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.35743 (7)0.2188 (2)0.47731 (5)0.0177 (3)
N30.32562 (8)0.5052 (2)0.42604 (5)0.0220 (3)
C30.46589 (9)0.2117 (2)0.54970 (6)0.0202 (3)
H30.48510.35600.53790.024*
N40.55444 (9)0.3310 (3)0.68852 (6)0.0344 (4)
C50.47687 (9)0.1099 (2)0.61043 (6)0.0195 (3)
C60.39778 (9)0.1079 (2)0.52296 (6)0.0172 (3)
C70.50536 (9)0.1029 (2)0.59359 (6)0.0209 (3)
H70.55180.17250.61230.025*
N50.18609 (8)0.1422 (2)0.34327 (5)0.0222 (3)
C90.23253 (9)0.3287 (2)0.35441 (6)0.0186 (3)
C100.40805 (9)0.2120 (2)0.58360 (6)0.0209 (3)
H100.38850.35600.59540.025*
C110.36849 (9)0.1020 (2)0.53979 (6)0.0191 (3)
H110.32150.16980.52130.023*
C120.52014 (9)0.2301 (3)0.65463 (6)0.0235 (3)
N20.36875 (8)0.4461 (2)0.47029 (5)0.0215 (3)
C140.13583 (10)0.1492 (3)0.29828 (6)0.0250 (3)
H140.10260.01890.28970.030*
C150.23084 (10)0.5219 (3)0.32145 (6)0.0223 (3)
H150.26520.64930.33060.027*
C160.30640 (9)0.1329 (2)0.43690 (6)0.0184 (3)
H160.28850.02040.43220.022*
C170.28639 (9)0.3169 (2)0.40433 (6)0.0183 (3)
C180.17840 (10)0.5253 (3)0.27525 (6)0.0249 (3)
H180.17600.65510.25200.030*
C190.12936 (10)0.3355 (3)0.26343 (6)0.0250 (3)
H190.09220.33310.23220.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0184 (6)0.0143 (5)0.0202 (6)0.0022 (5)0.0014 (5)0.0016 (4)
N30.0236 (7)0.0181 (6)0.0239 (6)0.0020 (5)0.0044 (5)0.0005 (5)
C30.0209 (7)0.0173 (6)0.0224 (7)0.0034 (6)0.0004 (5)0.0020 (5)
N40.0316 (8)0.0385 (8)0.0325 (8)0.0031 (6)0.0070 (6)0.0057 (6)
C50.0186 (7)0.0214 (7)0.0185 (7)0.0011 (6)0.0006 (5)0.0018 (5)
C60.0175 (7)0.0170 (6)0.0171 (6)0.0015 (5)0.0008 (5)0.0022 (5)
C70.0171 (7)0.0226 (7)0.0229 (7)0.0031 (6)0.0025 (5)0.0041 (6)
N50.0235 (7)0.0205 (6)0.0224 (6)0.0028 (5)0.0022 (5)0.0010 (5)
C90.0182 (7)0.0187 (7)0.0189 (7)0.0001 (5)0.0000 (5)0.0009 (5)
C100.0215 (7)0.0185 (7)0.0224 (7)0.0013 (6)0.0003 (6)0.0011 (5)
C110.0175 (7)0.0177 (7)0.0220 (7)0.0018 (5)0.0018 (5)0.0035 (5)
C120.0206 (7)0.0252 (7)0.0246 (8)0.0022 (6)0.0016 (6)0.0001 (6)
N20.0250 (7)0.0137 (6)0.0255 (7)0.0018 (5)0.0045 (5)0.0001 (5)
C140.0254 (8)0.0257 (8)0.0235 (7)0.0060 (6)0.0042 (6)0.0023 (6)
C150.0239 (8)0.0190 (7)0.0240 (7)0.0020 (6)0.0012 (6)0.0002 (5)
C160.0175 (7)0.0180 (7)0.0195 (7)0.0028 (5)0.0016 (5)0.0024 (5)
C170.0171 (7)0.0175 (7)0.0204 (7)0.0014 (5)0.0004 (5)0.0021 (5)
C180.0282 (8)0.0233 (8)0.0231 (7)0.0027 (6)0.0000 (6)0.0034 (6)
C190.0243 (8)0.0302 (8)0.0201 (7)0.0019 (6)0.0044 (6)0.0009 (6)
Geometric parameters (Å, º) top
N1—C61.4256 (18)N5—C141.3389 (19)
N1—N21.3578 (17)C9—C151.391 (2)
N1—C161.3551 (17)C9—C171.4694 (19)
N3—N21.3083 (17)C10—H100.9500
N3—C171.3680 (18)C10—C111.384 (2)
C3—H30.9500C11—H110.9500
C3—C61.391 (2)C14—H140.9500
C3—C71.381 (2)C14—C191.388 (2)
N4—C121.142 (2)C15—H150.9500
C5—C71.398 (2)C15—C181.382 (2)
C5—C101.396 (2)C16—H160.9500
C5—C121.445 (2)C16—C171.373 (2)
C6—C111.387 (2)C18—H180.9500
C7—H70.9500C18—C191.387 (2)
N5—C91.3456 (18)C19—H190.9500
N2—N1—C6119.25 (11)C6—C11—H11120.2
C16—N1—C6130.10 (12)C10—C11—C6119.64 (13)
C16—N1—N2110.64 (11)C10—C11—H11120.2
N2—N3—C17109.09 (12)N4—C12—C5177.84 (17)
C6—C3—H3120.3N3—N2—N1107.24 (11)
C7—C3—H3120.3N5—C14—H14118.1
C7—C3—C6119.33 (13)N5—C14—C19123.86 (14)
C7—C5—C12120.27 (13)C19—C14—H14118.1
C10—C5—C7120.40 (13)C9—C15—H15120.5
C10—C5—C12119.29 (14)C18—C15—C9118.93 (14)
C3—C6—N1119.46 (13)C18—C15—H15120.5
C11—C6—N1119.33 (13)N1—C16—H16127.7
C11—C6—C3121.21 (13)N1—C16—C17104.58 (12)
C3—C7—C5119.84 (13)C17—C16—H16127.7
C3—C7—H7120.1N3—C17—C9122.05 (12)
C5—C7—H7120.1N3—C17—C16108.45 (12)
C14—N5—C9116.85 (13)C16—C17—C9129.50 (13)
N5—C9—C15123.21 (14)C15—C18—H18120.7
N5—C9—C17115.59 (12)C15—C18—C19118.68 (14)
C15—C9—C17121.20 (13)C19—C18—H18120.7
C5—C10—H10120.2C14—C19—H19120.8
C11—C10—C5119.57 (14)C18—C19—C14118.47 (14)
C11—C10—H10120.2C18—C19—H19120.8
N1—C6—C11—C10179.13 (12)C10—C5—C12—N450 (5)
N1—C16—C17—N30.02 (16)C12—C5—C7—C3177.05 (14)
N1—C16—C17—C9179.56 (14)C12—C5—C10—C11177.32 (13)
C3—C6—C11—C100.7 (2)N2—N1—C6—C319.19 (19)
C5—C10—C11—C60.2 (2)N2—N1—C6—C11161.01 (13)
C6—N1—N2—N3179.99 (11)N2—N1—C16—C170.00 (15)
C6—N1—C16—C17179.97 (13)N2—N3—C17—C9179.61 (12)
C6—C3—C7—C50.3 (2)N2—N3—C17—C160.04 (17)
C7—C3—C6—N1179.38 (12)C14—N5—C9—C150.7 (2)
C7—C3—C6—C110.4 (2)C14—N5—C9—C17179.39 (13)
C7—C5—C10—C110.6 (2)C15—C9—C17—N311.9 (2)
C7—C5—C12—N4128 (4)C15—C9—C17—C16168.67 (15)
N5—C9—C15—C180.8 (2)C15—C18—C19—C140.7 (2)
N5—C9—C17—N3168.23 (13)C16—N1—C6—C3160.78 (14)
N5—C9—C17—C1611.3 (2)C16—N1—C6—C1119.0 (2)
N5—C14—C19—C180.8 (2)C16—N1—N2—N30.02 (15)
C9—N5—C14—C190.1 (2)C17—N3—N2—N10.03 (16)
C9—C15—C18—C190.1 (2)C17—C9—C15—C18179.30 (13)
C10—C5—C7—C30.9 (2)
(L8) top
Crystal data top
C14H12N4OZ = 2
Mr = 252.28F(000) = 264
Triclinic, P1Dx = 1.435 Mg m3
a = 3.7837 (4) ÅMo Kα radiation, λ = 0.71075 Å
b = 10.8502 (16) ÅCell parameters from 5805 reflections
c = 15.2200 (17) Åθ = 3.4–27.5°
α = 109.226 (11)°µ = 0.10 mm1
β = 97.056 (6)°T = 100 K
γ = 91.514 (9)°Lath, colourless
V = 584.03 (12) Å30.16 × 0.04 × 0.01 mm
Data collection top
Rigaku AFC12 (Right)
diffractometer
2617 independent reflections
Radiation source: Rotating Anode, Rotating Anode2049 reflections with > 2˘I)
Detector resolution: 28.5714 pixels mm-1Rint = 0.062
profile data from ω–scansθmax = 27.5°, θmin = 3.8°
Absorption correction: multi-scan
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
h = 44
Tmin = 0.624, Tmax = 1.000k = 1114
6395 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-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 parametersΔρmax = 0.25 e Å3
3 restraintsΔρmin = 0.29 e Å3
Crystal data top
C14H12N4Oγ = 91.514 (9)°
Mr = 252.28V = 584.03 (12) Å3
Triclinic, P1Z = 2
a = 3.7837 (4) ÅMo Kα radiation
b = 10.8502 (16) ŵ = 0.10 mm1
c = 15.2200 (17) ÅT = 100 K
α = 109.226 (11)°0.16 × 0.04 × 0.01 mm
β = 97.056 (6)°
Data collection top
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 = 1.000Rint = 0.062
6395 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0533 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 1.08Δρmax = 0.25 e Å3
2617 reflectionsΔρmin = 0.29 e Å3
345 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O180.7712 (8)0.3650 (2)0.32489 (18)0.0244 (7)
N10.9147 (10)1.0178 (3)0.9030 (2)0.0239 (8)
N81.1451 (9)0.6801 (3)0.8522 (2)0.0222 (8)
N91.1139 (9)0.5903 (3)0.7696 (2)0.0226 (8)
N100.9831 (9)0.6468 (3)0.7063 (2)0.0182 (7)
C20.9018 (12)1.1276 (4)0.9753 (3)0.0256 (10)
H20.82491.20290.96190.031*
C30.9930 (11)1.1380 (4)1.0678 (3)0.0234 (9)
H30.98001.21861.11660.028*
C41.1033 (11)1.0296 (4)1.0884 (3)0.0244 (9)
H41.16591.03321.15160.029*
C51.1206 (11)0.9150 (4)1.0145 (3)0.0220 (9)
H51.19830.83861.02620.026*
C61.0232 (11)0.9132 (4)0.9233 (3)0.0181 (8)
C71.0307 (11)0.7940 (4)0.8429 (3)0.0192 (9)
C110.9277 (10)0.7735 (4)0.7499 (3)0.0180 (8)
H110.83700.83480.72200.022*
C120.9172 (11)0.5738 (4)0.6086 (3)0.0180 (9)
C130.7608 (11)0.4482 (4)0.5792 (3)0.0199 (9)
H130.69070.41210.62390.024*
C140.7054 (10)0.3739 (4)0.4838 (3)0.0188 (9)
H140.60020.28690.46330.023*
C150.8051 (11)0.4283 (4)0.4196 (3)0.0192 (9)
C160.9558 (11)0.5565 (4)0.4498 (3)0.0195 (9)
H161.01790.59380.40500.023*
C171.0157 (11)0.6294 (4)0.5437 (3)0.0198 (9)
H171.12230.71610.56420.024*
C190.6221 (12)0.2336 (4)0.2930 (3)0.0277 (10)
H19D0.60980.19690.22450.042*
H19E0.38140.23170.31020.042*
H19F0.77250.18160.32220.042*
O18A0.6591 (7)0.4355 (2)0.00749 (18)0.0212 (6)
N1A0.3987 (9)0.9687 (3)0.6207 (2)0.0191 (7)
N8A0.2712 (9)1.0350 (3)0.3989 (2)0.0209 (8)
N9A0.3208 (9)0.9575 (3)0.3158 (2)0.0208 (8)
N10A0.4419 (9)0.8457 (3)0.3268 (2)0.0183 (7)
C2A0.3704 (11)1.0283 (4)0.7117 (3)0.0217 (9)
H2A0.42000.98030.75340.026*
C3A0.2740 (10)1.1546 (4)0.7484 (3)0.0213 (9)
H3A0.25881.19230.81360.026*
C4A0.1998 (11)1.2252 (4)0.6884 (3)0.0215 (9)
H4A0.13471.31290.71160.026*
C5A0.2220 (11)1.1661 (4)0.5944 (3)0.0199 (9)
H5A0.16901.21210.55150.024*
C6A0.3230 (10)1.0383 (4)0.5629 (3)0.0148 (8)
C7A0.3536 (11)0.9742 (4)0.4636 (3)0.0180 (8)
C11A0.4646 (10)0.8534 (4)0.4172 (3)0.0173 (8)
H11A0.54130.78890.44360.021*
C12A0.5123 (10)0.7413 (4)0.2458 (3)0.0168 (8)
C13A0.4643 (10)0.6128 (3)0.2417 (3)0.0185 (8)
H13A0.39260.59320.29350.022*
C14A0.5213 (11)0.5125 (4)0.1614 (3)0.0206 (9)
H14A0.49460.42410.15910.025*
C15A0.6172 (10)0.5405 (4)0.0845 (3)0.0170 (8)
C16A0.6668 (11)0.6702 (4)0.0895 (3)0.0192 (8)
H16A0.73580.69010.03750.023*
C17A0.6158 (10)0.7701 (4)0.1700 (3)0.0175 (8)
H17A0.65160.85860.17340.021*
C19A0.7692 (11)0.4626 (4)0.0707 (3)0.0241 (9)
H19A0.80390.38020.11950.036*
H19B0.99410.51740.05070.036*
H19C0.58550.50880.09590.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O180.0308 (18)0.0212 (15)0.0221 (15)0.0018 (12)0.0060 (13)0.0078 (13)
N10.031 (2)0.0188 (18)0.0240 (19)0.0067 (15)0.0059 (16)0.0083 (15)
N80.026 (2)0.0186 (18)0.0204 (19)0.0012 (14)0.0013 (15)0.0063 (15)
N90.030 (2)0.0170 (17)0.0196 (18)0.0029 (14)0.0008 (15)0.0064 (15)
N100.0194 (18)0.0179 (17)0.0207 (17)0.0033 (14)0.0009 (14)0.0116 (14)
C20.030 (3)0.024 (2)0.028 (2)0.0084 (18)0.0056 (19)0.014 (2)
C30.028 (2)0.020 (2)0.020 (2)0.0005 (18)0.0048 (18)0.0016 (17)
C40.027 (2)0.030 (2)0.017 (2)0.0034 (18)0.0016 (18)0.0093 (18)
C50.022 (2)0.021 (2)0.025 (2)0.0006 (16)0.0018 (18)0.0117 (17)
C60.017 (2)0.018 (2)0.0196 (19)0.0013 (16)0.0038 (16)0.0063 (16)
C70.014 (2)0.021 (2)0.027 (2)0.0027 (16)0.0019 (17)0.0145 (18)
C110.020 (2)0.015 (2)0.022 (2)0.0035 (16)0.0031 (17)0.0105 (17)
C120.020 (2)0.016 (2)0.019 (2)0.0055 (16)0.0006 (17)0.0075 (17)
C130.020 (2)0.019 (2)0.024 (2)0.0057 (16)0.0049 (17)0.0107 (17)
C140.018 (2)0.017 (2)0.024 (2)0.0040 (16)0.0050 (17)0.0103 (17)
C150.018 (2)0.021 (2)0.018 (2)0.0045 (16)0.0035 (16)0.0062 (17)
C160.019 (2)0.021 (2)0.021 (2)0.0045 (17)0.0039 (17)0.0103 (17)
C170.021 (2)0.014 (2)0.025 (2)0.0029 (16)0.0063 (18)0.0063 (17)
C190.028 (2)0.026 (2)0.029 (2)0.0003 (18)0.0091 (19)0.0064 (18)
O18A0.0291 (17)0.0152 (14)0.0175 (14)0.0044 (12)0.0086 (12)0.0010 (11)
N1A0.0177 (18)0.0187 (18)0.0224 (18)0.0004 (14)0.0008 (14)0.0097 (14)
N8A0.030 (2)0.0151 (17)0.0190 (18)0.0045 (15)0.0057 (15)0.0058 (14)
N9A0.026 (2)0.0139 (17)0.0204 (19)0.0036 (14)0.0013 (15)0.0038 (14)
N10A0.0209 (19)0.0133 (16)0.0210 (18)0.0016 (13)0.0035 (15)0.0061 (14)
C2A0.023 (2)0.024 (2)0.021 (2)0.0009 (17)0.0032 (18)0.0108 (18)
C3A0.018 (2)0.024 (2)0.023 (2)0.0038 (17)0.0045 (18)0.0091 (18)
C4A0.021 (2)0.016 (2)0.031 (2)0.0059 (16)0.0075 (18)0.0112 (18)
C5A0.021 (2)0.021 (2)0.022 (2)0.0052 (17)0.0065 (18)0.0119 (18)
C6A0.0107 (19)0.016 (2)0.019 (2)0.0010 (15)0.0017 (16)0.0080 (16)
C7A0.0136 (19)0.020 (2)0.022 (2)0.0009 (15)0.0014 (16)0.0097 (17)
C11A0.015 (2)0.020 (2)0.019 (2)0.0020 (16)0.0040 (16)0.0096 (17)
C12A0.012 (2)0.018 (2)0.019 (2)0.0027 (15)0.0013 (16)0.0061 (16)
C13A0.023 (2)0.018 (2)0.017 (2)0.0016 (16)0.0043 (17)0.0089 (16)
C14A0.021 (2)0.014 (2)0.028 (2)0.0010 (16)0.0041 (17)0.0080 (17)
C15A0.016 (2)0.017 (2)0.0155 (19)0.0015 (15)0.0022 (15)0.0023 (16)
C16A0.023 (2)0.016 (2)0.019 (2)0.0011 (16)0.0022 (17)0.0062 (16)
C17A0.022 (2)0.0127 (19)0.0167 (19)0.0026 (15)0.0008 (17)0.0047 (15)
C19A0.026 (2)0.026 (2)0.025 (2)0.0065 (18)0.0103 (18)0.0108 (18)
Geometric parameters (Å, º) top
O18—C151.366 (4)O18A—C15A1.368 (4)
O18—C191.422 (5)O18A—C19A1.422 (4)
N1—C21.336 (5)N1A—C2A1.340 (5)
N1—C61.333 (5)N1A—C6A1.346 (4)
N8—N91.302 (4)N8A—N9A1.307 (4)
N8—C71.365 (5)N8A—C7A1.366 (5)
N9—N101.355 (4)N9A—N10A1.361 (4)
N10—C111.350 (5)N10A—C11A1.344 (5)
N10—C121.422 (5)N10A—C12A1.431 (5)
C2—H20.9500C2A—H2A0.9500
C2—C31.375 (5)C2A—C3A1.377 (5)
C3—H30.9500C3A—H3A0.9500
C3—C41.376 (6)C3A—C4A1.382 (5)
C4—H40.9500C4A—H4A0.9500
C4—C51.384 (6)C4A—C5A1.375 (5)
C5—H50.9500C5A—H5A0.9500
C5—C61.385 (5)C5A—C6A1.391 (5)
C6—C71.463 (5)C6A—C7A1.463 (5)
C7—C111.362 (6)C7A—C11A1.372 (6)
C11—H110.9500C11A—H11A0.9500
C12—C131.378 (5)C12A—C13A1.381 (5)
C12—C171.395 (5)C12A—C17A1.387 (5)
C13—H130.9500C13A—H13A0.9500
C13—C141.395 (5)C13A—C14A1.387 (5)
C14—H140.9500C14A—H14A0.9500
C14—C151.380 (5)C14A—C15A1.389 (5)
C15—C161.394 (5)C15A—C16A1.390 (5)
C16—H160.9500C16A—H16A0.9500
C16—C171.373 (5)C16A—C17A1.381 (5)
C17—H170.9500C17A—H17A0.9500
C19—H19D0.9800C19A—H19A0.9800
C19—H19E0.9800C19A—H19B0.9800
C19—H19F0.9800C19A—H19C0.9800
C15—O18—C19115.7 (3)C15A—O18A—C19A117.1 (3)
C6—N1—C2117.0 (3)C2A—N1A—C6A116.7 (3)
N9—N8—C7109.2 (3)N9A—N8A—C7A109.6 (3)
N8—N9—N10107.0 (3)N8A—N9A—N10A107.0 (3)
N9—N10—C12121.0 (3)N9A—N10A—C12A119.1 (3)
C11—N10—N9110.6 (3)C11A—N10A—N9A110.3 (3)
C11—N10—C12128.4 (3)C11A—N10A—C12A130.6 (3)
N1—C2—H2118.0N1A—C2A—H2A117.9
N1—C2—C3123.9 (4)N1A—C2A—C3A124.1 (4)
C3—C2—H2118.0C3A—C2A—H2A117.9
C2—C3—H3120.6C2A—C3A—H3A120.7
C2—C3—C4118.8 (4)C2A—C3A—C4A118.5 (4)
C4—C3—H3120.6C4A—C3A—H3A120.7
C3—C4—H4120.9C3A—C4A—H4A120.6
C3—C4—C5118.2 (4)C5A—C4A—C3A118.7 (3)
C5—C4—H4120.9C5A—C4A—H4A120.6
C4—C5—H5120.4C4A—C5A—H5A120.4
C4—C5—C6119.1 (4)C4A—C5A—C6A119.2 (3)
C6—C5—H5120.4C6A—C5A—H5A120.4
N1—C6—C5122.9 (3)N1A—C6A—C5A122.7 (3)
N1—C6—C7115.9 (3)N1A—C6A—C7A117.1 (3)
C5—C6—C7121.2 (3)C5A—C6A—C7A120.2 (3)
N8—C7—C6122.7 (3)N8A—C7A—C6A121.6 (3)
C11—C7—N8108.4 (4)N8A—C7A—C11A107.6 (3)
C11—C7—C6128.8 (3)C11A—C7A—C6A130.8 (3)
N10—C11—C7104.7 (3)N10A—C11A—C7A105.5 (3)
N10—C11—H11127.6N10A—C11A—H11A127.2
C7—C11—H11127.6C7A—C11A—H11A127.2
C13—C12—N10119.5 (3)C13A—C12A—N10A120.4 (3)
C13—C12—C17120.7 (3)C13A—C12A—C17A120.2 (3)
C17—C12—N10119.7 (3)C17A—C12A—N10A119.4 (3)
C12—C13—H13119.9C12A—C13A—H13A120.1
C12—C13—C14120.1 (3)C12A—C13A—C14A119.7 (3)
C14—C13—H13119.9C14A—C13A—H13A120.1
C13—C14—H14120.4C13A—C14A—H14A119.8
C15—C14—C13119.2 (4)C13A—C14A—C15A120.4 (3)
C15—C14—H14120.4C15A—C14A—H14A119.8
O18—C15—C14124.8 (3)O18A—C15A—C14A116.4 (3)
O18—C15—C16115.0 (3)O18A—C15A—C16A124.1 (3)
C14—C15—C16120.2 (3)C14A—C15A—C16A119.5 (3)
C15—C16—H16119.6C15A—C16A—H16A120.0
C17—C16—C15120.8 (3)C17A—C16A—C15A120.1 (3)
C17—C16—H16119.6C17A—C16A—H16A120.0
C12—C17—H17120.6C12A—C17A—H17A119.9
C16—C17—C12118.9 (4)C16A—C17A—C12A120.1 (3)
C16—C17—H17120.6C16A—C17A—H17A119.9
O18—C19—H19D109.5O18A—C19A—H19A109.5
O18—C19—H19E109.5O18A—C19A—H19B109.5
O18—C19—H19F109.5O18A—C19A—H19C109.5
H19D—C19—H19E109.5H19A—C19A—H19B109.5
H19D—C19—H19F109.5H19A—C19A—H19C109.5
H19E—C19—H19F109.5H19B—C19A—H19C109.5
O18—C15—C16—C17177.8 (4)O18A—C15A—C16A—C17A179.5 (4)
N1—C2—C3—C40.3 (7)N1A—C2A—C3A—C4A0.2 (6)
N1—C6—C7—N8178.1 (4)N1A—C6A—C7A—N8A177.8 (4)
N1—C6—C7—C113.0 (6)N1A—C6A—C7A—C11A3.4 (6)
N8—N9—N10—C110.7 (4)N8A—N9A—N10A—C11A0.6 (4)
N8—N9—N10—C12179.9 (3)N8A—N9A—N10A—C12A178.7 (3)
N8—C7—C11—N100.2 (4)N8A—C7A—C11A—N10A0.5 (4)
N9—N8—C7—C6178.4 (3)N9A—N8A—C7A—C6A180.0 (3)
N9—N8—C7—C110.6 (5)N9A—N8A—C7A—C11A0.9 (5)
N9—N10—C11—C70.3 (4)N9A—N10A—C11A—C7A0.0 (4)
N9—N10—C12—C1342.1 (5)N9A—N10A—C12A—C13A148.3 (4)
N9—N10—C12—C17137.0 (4)N9A—N10A—C12A—C17A29.2 (5)
N10—C12—C13—C14177.9 (4)N10A—C12A—C13A—C14A177.7 (4)
N10—C12—C17—C16178.8 (3)N10A—C12A—C17A—C16A176.7 (4)
C2—N1—C6—C50.1 (6)C2A—N1A—C6A—C5A0.4 (5)
C2—N1—C6—C7179.3 (4)C2A—N1A—C6A—C7A179.9 (3)
C2—C3—C4—C50.6 (6)C2A—C3A—C4A—C5A0.6 (6)
C3—C4—C5—C60.7 (6)C3A—C4A—C5A—C6A0.9 (6)
C4—C5—C6—N10.4 (6)C4A—C5A—C6A—N1A0.4 (6)
C4—C5—C6—C7178.9 (4)C4A—C5A—C6A—C7A179.1 (4)
C5—C6—C7—N82.5 (6)C5A—C6A—C7A—N8A2.7 (5)
C5—C6—C7—C11176.4 (4)C5A—C6A—C7A—C11A176.2 (4)
C6—N1—C2—C30.0 (6)C6A—N1A—C2A—C3A0.7 (6)
C6—C7—C11—N10178.8 (4)C6A—C7A—C11A—N10A179.5 (4)
C7—N8—N9—N100.8 (4)C7A—N8A—N9A—N10A0.9 (4)
C11—N10—C12—C13136.9 (4)C11A—N10A—C12A—C13A29.4 (6)
C11—N10—C12—C1744.0 (6)C11A—N10A—C12A—C17A153.1 (4)
C12—N10—C11—C7179.4 (4)C12A—N10A—C11A—C7A177.9 (4)
C12—C13—C14—C150.7 (5)C12A—C13A—C14A—C15A1.7 (6)
C13—C12—C17—C160.3 (6)C13A—C12A—C17A—C16A0.9 (6)
C13—C14—C15—O18178.7 (4)C13A—C14A—C15A—O18A178.4 (4)
C13—C14—C15—C160.7 (6)C13A—C14A—C15A—C16A2.0 (6)
C14—C15—C16—C171.6 (6)C14A—C15A—C16A—C17A0.9 (6)
C15—C16—C17—C121.1 (6)C15A—C16A—C17A—C12A0.5 (6)
C17—C12—C13—C141.2 (5)C17A—C12A—C13A—C14A0.2 (6)
C19—O18—C15—C140.2 (5)C19A—O18A—C15A—C14A177.9 (4)
C19—O18—C15—C16179.2 (3)C19A—O18A—C15A—C16A1.7 (5)
(L11) top
Crystal data top
C14H10N4O2F(000) = 552
Mr = 266.26Dx = 1.491 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71075 Å
a = 10.5970 (17) ÅCell parameters from 3755 reflections
b = 14.471 (2) Åθ = 3.4–27.5°
c = 7.7343 (12) ŵ = 0.11 mm1
β = 90.121 (6)°T = 100 K
V = 1186.0 (3) Å3Hexagonal tablet, colourless
Z = 40.12 × 0.12 × 0.03 mm
Data collection top
Rigaku AFC12 (Right)
diffractometer
2705 independent reflections
Radiation source: Rotating Anode1862 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm-1Rint = 0.058
profile data from ω–scansθmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
h = 1313
Tmin = 0.516, Tmax = 1.000k = 1718
5844 measured reflectionsl = 109
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161H-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 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
C14H10N4O2V = 1186.0 (3) Å3
Mr = 266.26Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.5970 (17) ŵ = 0.11 mm1
b = 14.471 (2) ÅT = 100 K
c = 7.7343 (12) Å0.12 × 0.12 × 0.03 mm
β = 90.121 (6)°
Data collection top
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 = 1.000Rint = 0.058
5844 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0620 restraints
wR(F2) = 0.161H-atom parameters constrained
S = 1.05Δρmax = 0.34 e Å3
2705 reflectionsΔρmin = 0.29 e Å3
182 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.29090 (16)0.26161 (12)0.0038 (2)0.0252 (4)
H10.22690.27480.05780.038*
O20.23870 (16)0.11779 (12)0.0831 (2)0.0257 (4)
N10.90055 (18)0.17000 (14)0.6767 (2)0.0189 (4)
N80.8241 (2)0.07445 (15)0.6588 (3)0.0267 (5)
N90.7414 (2)0.11677 (14)0.5638 (3)0.0254 (5)
N100.69803 (18)0.05483 (13)0.4468 (2)0.0196 (4)
C20.9784 (2)0.22820 (18)0.7587 (3)0.0242 (6)
H20.96510.29140.74700.029*
C31.0777 (2)0.19837 (18)0.8600 (3)0.0257 (6)
H31.13020.24070.91470.031*
C41.0974 (2)0.10506 (18)0.8783 (3)0.0239 (6)
H41.16310.08330.94660.029*
C51.0188 (2)0.04411 (17)0.7942 (3)0.0214 (5)
H51.03110.01930.80420.026*
C60.9201 (2)0.07900 (16)0.6936 (3)0.0179 (5)
C70.8345 (2)0.01517 (17)0.6054 (3)0.0190 (5)
C110.7529 (2)0.02822 (16)0.4690 (3)0.0170 (5)
H110.73890.08220.40650.020*
C120.6029 (2)0.08282 (17)0.3278 (3)0.0184 (5)
C130.5173 (2)0.01886 (17)0.2646 (3)0.0186 (5)
H130.52360.04300.29570.022*
C140.4221 (2)0.04811 (17)0.1543 (3)0.0193 (5)
H140.36480.00560.11020.023*
C150.4124 (2)0.14079 (16)0.1097 (3)0.0194 (5)
C160.5004 (2)0.20375 (17)0.1718 (3)0.0224 (5)
H160.49440.26570.14060.027*
C170.5967 (2)0.17520 (17)0.2796 (3)0.0215 (5)
H170.65650.21720.31930.026*
C180.3052 (2)0.17172 (17)0.0019 (3)0.0186 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0253 (9)0.0216 (10)0.0286 (10)0.0029 (7)0.0103 (7)0.0023 (7)
O20.0269 (9)0.0255 (10)0.0246 (9)0.0007 (8)0.0071 (7)0.0027 (8)
N10.0208 (10)0.0183 (10)0.0176 (9)0.0001 (8)0.0009 (8)0.0002 (8)
N80.0290 (11)0.0205 (12)0.0307 (11)0.0010 (9)0.0102 (9)0.0002 (9)
N90.0293 (11)0.0189 (11)0.0279 (11)0.0022 (9)0.0118 (9)0.0011 (9)
N100.0213 (10)0.0180 (11)0.0194 (9)0.0003 (8)0.0037 (8)0.0003 (8)
C20.0272 (13)0.0204 (13)0.0250 (12)0.0021 (10)0.0023 (10)0.0017 (10)
C30.0246 (12)0.0306 (15)0.0221 (12)0.0098 (11)0.0015 (10)0.0016 (11)
C40.0186 (12)0.0343 (15)0.0189 (12)0.0004 (11)0.0049 (9)0.0053 (11)
C50.0229 (12)0.0197 (13)0.0217 (11)0.0031 (10)0.0030 (10)0.0022 (10)
C60.0175 (11)0.0206 (13)0.0157 (10)0.0027 (10)0.0019 (9)0.0004 (9)
C70.0186 (11)0.0190 (13)0.0193 (11)0.0024 (9)0.0002 (9)0.0003 (9)
C110.0198 (11)0.0141 (12)0.0172 (10)0.0003 (9)0.0002 (9)0.0023 (9)
C120.0171 (11)0.0199 (13)0.0181 (11)0.0032 (9)0.0002 (9)0.0016 (9)
C130.0212 (12)0.0176 (12)0.0172 (11)0.0017 (9)0.0008 (9)0.0025 (9)
C140.0189 (11)0.0213 (13)0.0176 (11)0.0005 (10)0.0010 (9)0.0014 (9)
C150.0195 (11)0.0221 (13)0.0165 (11)0.0034 (10)0.0007 (9)0.0010 (9)
C160.0226 (12)0.0186 (13)0.0260 (12)0.0029 (10)0.0019 (10)0.0037 (10)
C170.0208 (12)0.0185 (12)0.0253 (12)0.0010 (10)0.0035 (10)0.0012 (10)
C180.0188 (11)0.0192 (12)0.0178 (11)0.0014 (10)0.0029 (9)0.0000 (10)
Geometric parameters (Å, º) top
O1—H10.8200C5—H50.9300
O1—C181.310 (3)C5—C61.399 (3)
O2—C181.226 (3)C6—C71.465 (3)
N1—C21.340 (3)C7—C111.378 (3)
N1—C61.339 (3)C11—H110.9300
N8—N91.299 (3)C12—C131.386 (3)
N8—C71.366 (3)C12—C171.389 (3)
N9—N101.355 (3)C13—H130.9300
N10—C111.346 (3)C13—C141.388 (3)
N10—C121.425 (3)C14—H140.9300
C2—H20.9300C14—C151.389 (3)
C2—C31.382 (3)C15—C161.390 (3)
C3—H30.9300C15—C181.497 (3)
C3—C41.374 (4)C16—H160.9300
C4—H40.9300C16—C171.382 (3)
C4—C51.377 (3)C17—H170.9300
C18—O1—H1109.5N10—C11—C7104.3 (2)
C6—N1—C2118.5 (2)N10—C11—H11127.8
N9—N8—C7109.3 (2)C7—C11—H11127.8
N8—N9—N10107.24 (19)C13—C12—N10120.2 (2)
N9—N10—C12118.98 (19)C13—C12—C17121.1 (2)
C11—N10—N9111.00 (19)C17—C12—N10118.7 (2)
C11—N10—C12130.0 (2)C12—C13—H13120.3
N1—C2—H2118.6C12—C13—C14119.3 (2)
N1—C2—C3122.8 (2)C14—C13—H13120.3
C3—C2—H2118.6C13—C14—H14120.0
C2—C3—H3120.6C13—C14—C15120.1 (2)
C4—C3—C2118.8 (2)C15—C14—H14120.0
C4—C3—H3120.6C14—C15—C16119.8 (2)
C3—C4—H4120.4C14—C15—C18119.2 (2)
C3—C4—C5119.3 (2)C16—C15—C18120.9 (2)
C5—C4—H4120.4C15—C16—H16119.7
C4—C5—H5120.5C17—C16—C15120.6 (2)
C4—C5—C6119.0 (2)C17—C16—H16119.7
C6—C5—H5120.5C12—C17—H17120.5
N1—C6—C5121.6 (2)C16—C17—C12119.0 (2)
N1—C6—C7118.6 (2)C16—C17—H17120.5
C5—C6—C7119.7 (2)O1—C18—C15113.0 (2)
N8—C7—C6120.5 (2)O2—C18—O1124.1 (2)
N8—C7—C11108.2 (2)O2—C18—C15122.9 (2)
C11—C7—C6131.3 (2)
N1—C2—C3—C40.3 (4)C5—C6—C7—C11161.5 (2)
N1—C6—C7—N8159.3 (2)C6—N1—C2—C30.1 (3)
N1—C6—C7—C1119.2 (4)C6—C7—C11—N10179.1 (2)
N8—N9—N10—C110.7 (3)C7—N8—N9—N100.4 (3)
N8—N9—N10—C12178.44 (19)C11—N10—C12—C1326.9 (3)
N8—C7—C11—N100.4 (2)C11—N10—C12—C17154.2 (2)
N9—N8—C7—C6178.8 (2)C12—N10—C11—C7178.1 (2)
N9—N8—C7—C110.0 (3)C12—C13—C14—C150.7 (3)
N9—N10—C11—C70.7 (2)C13—C12—C17—C162.4 (3)
N9—N10—C12—C13150.4 (2)C13—C14—C15—C161.8 (3)
N9—N10—C12—C1728.5 (3)C13—C14—C15—C18176.8 (2)
N10—C12—C13—C14177.40 (19)C14—C15—C16—C170.9 (3)
N10—C12—C17—C16176.4 (2)C14—C15—C18—O1166.1 (2)
C2—N1—C6—C50.2 (3)C14—C15—C18—O214.2 (3)
C2—N1—C6—C7179.45 (19)C15—C16—C17—C121.3 (3)
C2—C3—C4—C50.6 (3)C16—C15—C18—O112.5 (3)
C3—C4—C5—C60.6 (3)C16—C15—C18—O2167.1 (2)
C4—C5—C6—N10.2 (3)C17—C12—C13—C141.5 (3)
C4—C5—C6—C7179.1 (2)C18—C15—C16—C17177.8 (2)
C5—C6—C7—N820.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.821.822.626 (3)167
Symmetry code: (i) x+1, y+1/2, z1/2.

Experimental details

(L1)(L3)(L4)(L5)
Crystal data
Chemical formulaC13H10N4C13H9FN4C13H9ClN4C14H12N4
Mr222.25240.24256.69236.28
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/cMonoclinic, C2/cMonoclinic, P21
Temperature (K)120120120120
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), 9090, 104.043 (2), 9090, 93.109 (8), 9090, 92.359 (4), 90
V3)2165.32 (8)1098.94 (5)2308.4 (2)584.96 (8)
Z8482
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.090.100.320.08
Crystal size (mm)0.34 × 0.23 × 0.200.60 × 0.58 × 0.400.36 × 0.12 × 0.060.38 × 0.12 × 0.10
Data collection
DiffractometerBruker-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 correctionMulti-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, Tmax0.971, 0.9830.940, 0.9600.608, 1.0000.969, 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)]
Rint0.0570.0310.0500.056
(sin θ/λ)max1)0.6490.6490.6490.649
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 reflections4956251026362622
No. of parameters309163163165
No. of restraints0001
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.27, 0.350.26, 0.230.25, 0.460.17, 0.18


(L6)(L7)(L8)(L11)
Crystal data
Chemical formulaC14H9F3N4C14H9N5C14H12N4OC14H10N4O2
Mr290.25247.26252.28266.26
Crystal system, space groupTriclinic, P1Monoclinic, C2/cTriclinic, P1Monoclinic, P21/c
Temperature (K)120100100100
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), 90109.226 (11), 97.056 (6), 91.514 (9)90, 90.121 (6), 90
V3)608.25 (3)2303.1 (5)584.03 (12)1186.0 (3)
Z2824
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.130.090.100.11
Crystal size (mm)0.60 × 0.20 × 0.180.22 × 0.14 × 0.040.16 × 0.04 × 0.010.12 × 0.12 × 0.03
Data collection
DiffractometerBruker-Nonius CCD camera on κ-goniostat
diffractometer
Rigaku AFC12 (Right)
diffractometer
Rigaku AFC12 (Right)
diffractometer
Rigaku AFC12 (Right)
diffractometer
Absorption correctionMulti-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, Tmax0.925, 0.9770.677, 1.0000.624, 1.0000.516, 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)]
Rint0.0350.0610.0620.058
(sin θ/λ)max1)0.6490.6490.6490.649
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 reflections2785263826172705
No. of parameters191172345182
No. of restraints0030
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.300.29, 0.250.25, 0.290.34, 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).

Hydrogen-bond geometry (Å, º) for (L11) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.821.822.626 (3)167.2
Symmetry code: (i) x+1, y+1/2, z1/2.
 

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