The structures of 12 new
N6-substituted 2-amino-4-chloro-5-formylpyrimidines, where the
N6 substituent is of the type NH
R or N
R1R2, have been determined. The intramolecular dimensions provide strong evidence for the development of polarized, charge-separated molecular-electronic structures, with the positive charge delocalized over the two exocyclic amino N atoms and with negative charge on the formyl O atom. This polarization appears to be independent of the significant puckering, in seven of the compounds, of the pyrimidine rings from planarity towards boat, twist-boat or screw-boat conformations. In 11 of the compounds studied here, N—H
N hydrogen bonds link pairs of molecules into centrosymmetric
dimer units, and their overall crystal structures are determined by the patterns of hydrogen bonds by which these units are further linked. Examples are reported in which no further hydrogen bonding occurs; in which the
dimers are linked into chains of rings, or into sheets; and in which sheets are formed by the π-stacking of hydrogen-bonded chains of rings. In the sole structure lacking the
dimer motif, N—H
O and N—H
N hydrogen bonds cooperate to generate a three-dimensional framework structure.
Supporting information
| Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768108019915/bm5057sup1.cif Contains datablocks global, I, II, III, IV, V, VI, VII, VIII, IX, X, XI, XII |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019915/bm5057Isup2.fcf Contains datablock I |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019915/bm5057IIsup3.fcf Contains datablock II |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019915/bm5057IIIsup4.fcf Contains datablock III |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019915/bm5057IVsup5.fcf Contains datablock IV |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019915/bm5057Vsup6.fcf Contains datablock V |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019915/bm5057VIsup7.fcf Contains datablock VI |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019915/bm5057VIIsup8.fcf Contains datablock VII |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019915/bm5057VIIIsup9.fcf Contains datablock VIII |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019915/bm5057IXsup10.fcf Contains datablock IX |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019915/bm5057Xsup11.fcf Contains datablock X |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019915/bm5057XIsup12.fcf Contains datablock XI |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768108019915/bm5057XIIsup13.fcf Contains datablock XII |
CCDC references: 705592; 705593; 705594; 705595; 705596; 705597; 705598; 705599; 705600; 705601; 705602; 705603
For all compounds, data collection: COLLECT (Hooft, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: Sir2004 (Burla et al., 2005). Program(s) used to refine structure: OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997) for (I), (II), (III), (IV), (V), (VII), (VIII), (IX), (X); OSCAIL (McArdle, 2003) & SHELXL97 (Sheldrick, 1997) for (VI), (XI), (XII). For all compounds, molecular graphics: PLATON (Spek, 2003). Software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999) for (I), (II), (III), (IV), (V), (VII), (VIII), (IX), (X); SHELXL97 & PRPKAPPA (Ferguson, 1999) for (VI), (XI), (XII).
Crystal data top
C11H15ClN4O | Z = 2 |
Mr = 254.72 | F(000) = 268 |
Triclinic, P1 | Dx = 1.382 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.907 (2) Å | Cell parameters from 2807 reflections |
b = 10.398 (3) Å | θ = 3.4–27.5° |
c = 10.801 (2) Å | µ = 0.30 mm−1 |
α = 110.86 (3)° | T = 120 K |
β = 94.19 (2)° | Plate, colourless |
γ = 96.00 (3)° | 0.48 × 0.28 × 0.08 mm |
V = 612.2 (3) Å3 | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 2807 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 2278 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
ϕ & ω scans | θmax = 27.5°, θmin = 3.4° |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | h = −7→7 |
Tmin = 0.869, Tmax = 0.976 | k = −13→13 |
16678 measured reflections | l = −13→14 |
Refinement top
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0393P)2 + 0.3635P] where P = (Fo2 + 2Fc2)/3 |
2807 reflections | (Δ/σ)max < 0.001 |
154 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
Crystal data top
C11H15ClN4O | γ = 96.00 (3)° |
Mr = 254.72 | V = 612.2 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.907 (2) Å | Mo Kα radiation |
b = 10.398 (3) Å | µ = 0.30 mm−1 |
c = 10.801 (2) Å | T = 120 K |
α = 110.86 (3)° | 0.48 × 0.28 × 0.08 mm |
β = 94.19 (2)° | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 2807 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 2278 reflections with I > 2σ(I) |
Tmin = 0.869, Tmax = 0.976 | Rint = 0.045 |
16678 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.25 e Å−3 |
2807 reflections | Δρmin = −0.37 e Å−3 |
154 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl4 | 0.56158 (7) | 1.01124 (4) | 0.74715 (4) | 0.02841 (13) | |
O51 | 0.0293 (2) | 0.66373 (13) | 0.56409 (12) | 0.0289 (3) | |
N1 | 0.5886 (2) | 0.70091 (14) | 0.34068 (14) | 0.0226 (3) | |
N2 | 0.9231 (2) | 0.83585 (15) | 0.34262 (14) | 0.0267 (3) | |
N3 | 0.7374 (2) | 0.91037 (14) | 0.52819 (13) | 0.0214 (3) | |
N61 | 0.2491 (2) | 0.57177 (14) | 0.34223 (14) | 0.0232 (3) | |
C2 | 0.7431 (3) | 0.81334 (17) | 0.40417 (16) | 0.0211 (3) | |
C4 | 0.5594 (3) | 0.88767 (16) | 0.58716 (16) | 0.0205 (3) | |
C5 | 0.3806 (3) | 0.77795 (17) | 0.53498 (16) | 0.0209 (3) | |
C6 | 0.4079 (3) | 0.68211 (16) | 0.40452 (16) | 0.0207 (3) | |
C51 | 0.1866 (3) | 0.76130 (18) | 0.60481 (17) | 0.0250 (4) | |
C61 | 0.2650 (3) | 0.46937 (17) | 0.21055 (16) | 0.0218 (3) | |
C62 | 0.4087 (3) | 0.35948 (19) | 0.22014 (18) | 0.0285 (4) | |
C63 | 0.4210 (3) | 0.2515 (2) | 0.0818 (2) | 0.0332 (4) | |
C64 | 0.1811 (3) | 0.18498 (19) | 0.01160 (19) | 0.0334 (4) | |
C65 | 0.0392 (3) | 0.2959 (2) | 0.00314 (18) | 0.0313 (4) | |
C66 | 0.0247 (3) | 0.40317 (18) | 0.14136 (17) | 0.0249 (4) | |
H2A | 0.9351 | 0.7766 | 0.2648 | 0.032* | |
H2B | 1.0214 | 0.9093 | 0.3812 | 0.032* | |
H61 | 0.1440 | 0.5598 | 0.3897 | 0.028* | |
H51 | 0.1801 | 0.8316 | 0.6892 | 0.030* | |
H61A | 0.3402 | 0.5183 | 0.1565 | 0.026* | |
H62A | 0.3405 | 0.3129 | 0.2769 | 0.034* | |
H62B | 0.5654 | 0.4044 | 0.2624 | 0.034* | |
H63A | 0.5018 | 0.2966 | 0.0276 | 0.040* | |
H63B | 0.5093 | 0.1787 | 0.0906 | 0.040* | |
H64A | 0.1921 | 0.1188 | −0.0794 | 0.040* | |
H64B | 0.1053 | 0.1326 | 0.0614 | 0.040* | |
H65A | −0.1173 | 0.2516 | −0.0402 | 0.038* | |
H65B | 0.1091 | 0.3432 | −0.0527 | 0.038* | |
H66A | −0.0641 | 0.4758 | 0.1328 | 0.030* | |
H66B | −0.0553 | 0.3576 | 0.1954 | 0.030* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl4 | 0.0280 (2) | 0.0250 (2) | 0.0229 (2) | −0.00440 (16) | 0.00387 (15) | −0.00040 (16) |
O51 | 0.0227 (6) | 0.0290 (7) | 0.0308 (7) | −0.0057 (5) | 0.0045 (5) | 0.0084 (5) |
N1 | 0.0187 (7) | 0.0217 (7) | 0.0230 (7) | −0.0046 (5) | 0.0006 (5) | 0.0053 (6) |
N2 | 0.0224 (7) | 0.0263 (7) | 0.0226 (7) | −0.0085 (6) | 0.0031 (5) | 0.0018 (6) |
N3 | 0.0197 (7) | 0.0201 (7) | 0.0210 (7) | −0.0031 (5) | −0.0005 (5) | 0.0057 (5) |
N61 | 0.0190 (7) | 0.0221 (7) | 0.0224 (7) | −0.0052 (5) | 0.0027 (5) | 0.0030 (6) |
C2 | 0.0184 (8) | 0.0217 (8) | 0.0216 (8) | −0.0017 (6) | 0.0001 (6) | 0.0078 (6) |
C4 | 0.0211 (8) | 0.0191 (7) | 0.0190 (7) | 0.0010 (6) | −0.0005 (6) | 0.0051 (6) |
C5 | 0.0188 (8) | 0.0208 (8) | 0.0209 (8) | −0.0017 (6) | 0.0004 (6) | 0.0064 (6) |
C6 | 0.0189 (8) | 0.0197 (8) | 0.0226 (8) | −0.0002 (6) | −0.0003 (6) | 0.0079 (6) |
C51 | 0.0235 (8) | 0.0236 (8) | 0.0248 (8) | 0.0001 (7) | 0.0034 (7) | 0.0058 (7) |
C61 | 0.0195 (8) | 0.0209 (8) | 0.0205 (8) | −0.0040 (6) | 0.0018 (6) | 0.0039 (6) |
C62 | 0.0194 (8) | 0.0324 (9) | 0.0297 (9) | 0.0021 (7) | 0.0013 (7) | 0.0072 (8) |
C63 | 0.0289 (10) | 0.0305 (10) | 0.0365 (10) | 0.0064 (8) | 0.0099 (8) | 0.0060 (8) |
C64 | 0.0362 (10) | 0.0242 (9) | 0.0307 (10) | −0.0028 (8) | 0.0092 (8) | 0.0002 (7) |
C65 | 0.0269 (9) | 0.0332 (10) | 0.0241 (9) | −0.0046 (7) | −0.0008 (7) | 0.0020 (7) |
C66 | 0.0196 (8) | 0.0244 (8) | 0.0239 (8) | −0.0008 (6) | −0.0020 (6) | 0.0027 (7) |
Geometric parameters (Å, º) top
Cl4—C4 | 1.7461 (17) | C61—C66 | 1.523 (2) |
O51—C51 | 1.229 (2) | C61—H61A | 1.00 |
N1—C2 | 1.336 (2) | C62—C63 | 1.529 (3) |
N1—C6 | 1.346 (2) | C62—H62A | 0.99 |
N2—C2 | 1.338 (2) | C62—H62B | 0.99 |
N2—H2A | 0.86 | C63—C64 | 1.525 (3) |
N2—H2B | 0.86 | C63—H63A | 0.99 |
N3—C4 | 1.311 (2) | C63—H63B | 0.99 |
N3—C2 | 1.366 (2) | C64—C65 | 1.519 (3) |
N61—C6 | 1.335 (2) | C64—H64A | 0.99 |
N61—C61 | 1.459 (2) | C64—H64B | 0.99 |
N61—H61 | 0.8597 | C65—C66 | 1.527 (2) |
C4—C5 | 1.392 (2) | C65—H65A | 0.99 |
C5—C6 | 1.439 (2) | C65—H65B | 0.99 |
C5—C51 | 1.446 (2) | C66—H66A | 0.99 |
C51—H51 | 0.95 | C66—H66B | 0.99 |
C61—C62 | 1.520 (2) | | |
| | | |
C2—N1—C6 | 116.86 (14) | C61—C62—H62A | 109.5 |
C2—N2—H2A | 118.5 | C63—C62—H62A | 109.5 |
C2—N2—H2B | 119.2 | C61—C62—H62B | 109.5 |
H2A—N2—H2B | 122.2 | C63—C62—H62B | 109.5 |
C4—N3—C2 | 114.73 (14) | H62A—C62—H62B | 108.1 |
C6—N61—C61 | 123.28 (14) | C64—C63—C62 | 110.69 (15) |
C6—N61—H61 | 114.6 | C64—C63—H63A | 109.5 |
C61—N61—H61 | 121.7 | C62—C63—H63A | 109.5 |
N1—C2—N2 | 118.27 (15) | C64—C63—H63B | 109.5 |
N1—C2—N3 | 126.44 (15) | C62—C63—H63B | 109.5 |
N2—C2—N3 | 115.29 (14) | H63A—C63—H63B | 108.1 |
N3—C4—C5 | 126.53 (15) | C65—C64—C63 | 110.28 (15) |
N3—C4—Cl4 | 113.45 (12) | C65—C64—H64A | 109.6 |
C5—C4—Cl4 | 120.02 (13) | C63—C64—H64A | 109.6 |
C4—C5—C6 | 113.37 (15) | C65—C64—H64B | 109.6 |
C4—C5—C51 | 123.47 (15) | C63—C64—H64B | 109.6 |
C6—C5—C51 | 123.16 (14) | H64A—C64—H64B | 108.1 |
N61—C6—N1 | 118.02 (15) | C64—C65—C66 | 111.32 (15) |
N61—C6—C5 | 119.91 (14) | C64—C65—H65A | 109.4 |
N1—C6—C5 | 122.06 (14) | C66—C65—H65A | 109.4 |
O51—C51—C5 | 125.42 (16) | C64—C65—H65B | 109.4 |
O51—C51—H51 | 117.3 | C66—C65—H65B | 109.4 |
C5—C51—H51 | 117.3 | H65A—C65—H65B | 108.0 |
N61—C61—C62 | 111.22 (14) | C61—C66—C65 | 109.85 (14) |
N61—C61—C66 | 109.38 (13) | C61—C66—H66A | 109.7 |
C62—C61—C66 | 110.89 (14) | C65—C66—H66A | 109.7 |
N61—C61—H61A | 108.4 | C61—C66—H66B | 109.7 |
C62—C61—H61A | 108.4 | C65—C66—H66B | 109.7 |
C66—C61—H61A | 108.4 | H66A—C66—H66B | 108.2 |
C61—C62—C63 | 110.78 (15) | | |
| | | |
C6—N1—C2—N2 | −179.16 (15) | C51—C5—C6—N61 | 0.2 (2) |
C6—N1—C2—N3 | 0.8 (2) | C4—C5—C6—N1 | −1.1 (2) |
C4—N3—C2—N1 | −0.4 (2) | C51—C5—C6—N1 | 179.05 (15) |
C4—N3—C2—N2 | 179.58 (14) | C4—C5—C51—O51 | −177.51 (17) |
C2—N3—C4—C5 | −1.0 (2) | C6—C5—C51—O51 | 2.3 (3) |
C2—N3—C4—Cl4 | 178.43 (11) | C6—N61—C61—C62 | 84.52 (19) |
N3—C4—C5—C6 | 1.7 (2) | C6—N61—C61—C66 | −152.66 (15) |
Cl4—C4—C5—C6 | −177.69 (11) | N61—C61—C62—C63 | 179.10 (14) |
N3—C4—C5—C51 | −178.52 (16) | C66—C61—C62—C63 | 57.15 (19) |
Cl4—C4—C5—C51 | 2.1 (2) | C61—C62—C63—C64 | −56.6 (2) |
C61—N61—C6—N1 | 1.6 (2) | C62—C63—C64—C65 | 56.5 (2) |
C61—N61—C6—C5 | −179.52 (15) | C63—C64—C65—C66 | −57.3 (2) |
C2—N1—C6—N61 | 178.89 (14) | N61—C61—C66—C65 | 179.87 (14) |
C2—N1—C6—C5 | 0.0 (2) | C62—C61—C66—C65 | −57.11 (19) |
C4—C5—C6—N61 | −179.97 (15) | C64—C65—C66—C61 | 57.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···N3i | 0.86 | 2.11 | 2.966 (2) | 179 |
N61—H61···O51 | 0.86 | 2.02 | 2.725 (2) | 139 |
Symmetry code: (i) −x+2, −y+2, −z+1. |
Crystal data top
C9H13ClN4O | F(000) = 480 |
Mr = 228.68 | Dx = 1.474 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2357 reflections |
a = 11.328 (3) Å | θ = 4.4–27.5° |
b = 8.0810 (4) Å | µ = 0.35 mm−1 |
c = 11.3849 (12) Å | T = 120 K |
β = 98.709 (14)° | Plate, colourless |
V = 1030.2 (3) Å3 | 0.37 × 0.36 × 0.08 mm |
Z = 4 | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 2357 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 1408 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.099 |
ϕ & ω scans | θmax = 27.5°, θmin = 4.4° |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | h = −14→14 |
Tmin = 0.882, Tmax = 0.973 | k = −10→10 |
21126 measured reflections | l = −14→14 |
Refinement top
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0594P)2 + 1.3692P] where P = (Fo2 + 2Fc2)/3 |
2357 reflections | (Δ/σ)max < 0.001 |
138 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
Crystal data top
C9H13ClN4O | V = 1030.2 (3) Å3 |
Mr = 228.68 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.328 (3) Å | µ = 0.35 mm−1 |
b = 8.0810 (4) Å | T = 120 K |
c = 11.3849 (12) Å | 0.37 × 0.36 × 0.08 mm |
β = 98.709 (14)° | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 2357 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 1408 reflections with I > 2σ(I) |
Tmin = 0.882, Tmax = 0.973 | Rint = 0.099 |
21126 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.43 e Å−3 |
2357 reflections | Δρmin = −0.37 e Å−3 |
138 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.4610 (2) | 0.3978 (3) | 0.6130 (2) | 0.0187 (6) | |
C2 | 0.4704 (3) | 0.2420 (4) | 0.5792 (3) | 0.0186 (7) | |
N2 | 0.5733 (2) | 0.1648 (3) | 0.6119 (2) | 0.0227 (7) | |
N3 | 0.3803 (2) | 0.1501 (3) | 0.5177 (2) | 0.0186 (6) | |
C4 | 0.2886 (3) | 0.2376 (4) | 0.4691 (3) | 0.0195 (7) | |
Cl4 | 0.17783 (7) | 0.11931 (10) | 0.38568 (7) | 0.0246 (3) | |
C5 | 0.2745 (3) | 0.4087 (4) | 0.4785 (3) | 0.0182 (7) | |
C51 | 0.1943 (3) | 0.4955 (4) | 0.3876 (3) | 0.0214 (7) | |
O51 | 0.20011 (19) | 0.6406 (3) | 0.3598 (2) | 0.0245 (6) | |
C6 | 0.3614 (3) | 0.4822 (4) | 0.5689 (3) | 0.0189 (7) | |
N61 | 0.3501 (2) | 0.6334 (3) | 0.6160 (2) | 0.0188 (6) | |
C62 | 0.2380 (3) | 0.7273 (4) | 0.6073 (3) | 0.0225 (8) | |
C63 | 0.1350 (3) | 0.6336 (4) | 0.6493 (3) | 0.0281 (8) | |
C64 | 0.4488 (3) | 0.7008 (4) | 0.7017 (3) | 0.0211 (7) | |
C65 | 0.4339 (3) | 0.6638 (4) | 0.8289 (3) | 0.0267 (8) | |
H2A | 0.6355 | 0.2226 | 0.6381 | 0.027* | |
H2B | 0.5826 | 0.0744 | 0.5745 | 0.027* | |
H51 | 0.1306 | 0.4328 | 0.3454 | 0.026* | |
H62A | 0.2134 | 0.7605 | 0.5234 | 0.027* | |
H62B | 0.2530 | 0.8297 | 0.6549 | 0.027* | |
H63A | 0.1105 | 0.5418 | 0.5947 | 0.042* | |
H63B | 0.0674 | 0.7088 | 0.6507 | 0.042* | |
H63C | 0.1610 | 0.5899 | 0.7293 | 0.042* | |
H64A | 0.4528 | 0.8221 | 0.6909 | 0.025* | |
H64B | 0.5251 | 0.6527 | 0.6855 | 0.025* | |
H65A | 0.3589 | 0.7124 | 0.8457 | 0.040* | |
H65B | 0.5009 | 0.7114 | 0.8828 | 0.040* | |
H65C | 0.4321 | 0.5438 | 0.8407 | 0.040* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0210 (14) | 0.0158 (15) | 0.0196 (14) | −0.0007 (11) | 0.0045 (11) | −0.0004 (11) |
C2 | 0.0214 (17) | 0.0174 (17) | 0.0179 (16) | 0.0004 (14) | 0.0061 (13) | 0.0011 (13) |
N2 | 0.0212 (15) | 0.0190 (15) | 0.0269 (16) | 0.0005 (12) | 0.0004 (12) | −0.0056 (12) |
N3 | 0.0200 (14) | 0.0145 (15) | 0.0221 (14) | 0.0009 (11) | 0.0055 (11) | 0.0003 (11) |
C4 | 0.0208 (17) | 0.0205 (18) | 0.0185 (17) | −0.0015 (14) | 0.0075 (13) | −0.0032 (13) |
Cl4 | 0.0231 (4) | 0.0193 (4) | 0.0307 (5) | −0.0024 (4) | 0.0017 (3) | −0.0041 (4) |
C5 | 0.0213 (17) | 0.0146 (18) | 0.0198 (17) | 0.0003 (13) | 0.0066 (13) | −0.0009 (13) |
C51 | 0.0210 (18) | 0.0218 (19) | 0.0217 (17) | 0.0011 (14) | 0.0043 (14) | −0.0037 (14) |
O51 | 0.0247 (13) | 0.0188 (14) | 0.0293 (13) | 0.0025 (10) | 0.0020 (10) | 0.0038 (10) |
C6 | 0.0199 (17) | 0.0153 (17) | 0.0228 (17) | −0.0036 (14) | 0.0074 (13) | 0.0016 (13) |
N61 | 0.0214 (15) | 0.0121 (14) | 0.0228 (15) | 0.0017 (11) | 0.0031 (11) | −0.0018 (11) |
C62 | 0.0237 (18) | 0.0141 (17) | 0.0298 (19) | 0.0060 (13) | 0.0042 (15) | −0.0011 (14) |
C63 | 0.029 (2) | 0.026 (2) | 0.031 (2) | 0.0048 (16) | 0.0087 (15) | −0.0024 (16) |
C64 | 0.0217 (17) | 0.0179 (18) | 0.0239 (18) | −0.0044 (14) | 0.0043 (14) | −0.0054 (14) |
C65 | 0.0272 (19) | 0.024 (2) | 0.0285 (19) | −0.0006 (15) | 0.0039 (15) | −0.0057 (15) |
Geometric parameters (Å, º) top
N1—C2 | 1.326 (4) | N61—C62 | 1.470 (4) |
N1—C6 | 1.349 (4) | N61—C64 | 1.472 (4) |
C2—N2 | 1.325 (4) | C62—C63 | 1.527 (5) |
C2—N3 | 1.367 (4) | C62—H62A | 0.99 |
N2—H2A | 0.86 | C62—H62B | 0.99 |
N2—H2B | 0.86 | C63—H63A | 0.98 |
N3—C4 | 1.308 (4) | C63—H63B | 0.98 |
C4—C5 | 1.398 (4) | C63—H63C | 0.98 |
C4—Cl4 | 1.740 (3) | C64—C65 | 1.513 (5) |
C5—C6 | 1.440 (4) | C64—H64A | 0.99 |
C5—C51 | 1.450 (4) | C64—H64B | 0.99 |
C51—O51 | 1.219 (4) | C65—H65A | 0.98 |
C51—H51 | 0.95 | C65—H65B | 0.98 |
C6—N61 | 1.348 (4) | C65—H65C | 0.98 |
| | | |
C2—N1—C6 | 118.1 (3) | N61—C62—H62A | 108.6 |
N2—C2—N1 | 118.1 (3) | C63—C62—H62A | 108.6 |
N2—C2—N3 | 116.4 (3) | N61—C62—H62B | 108.6 |
N1—C2—N3 | 125.3 (3) | C63—C62—H62B | 108.6 |
C2—N2—H2A | 118.8 | H62A—C62—H62B | 107.6 |
C2—N2—H2B | 115.4 | C62—C63—H63A | 109.5 |
H2A—N2—H2B | 118.6 | C62—C63—H63B | 109.5 |
C4—N3—C2 | 114.0 (3) | H63A—C63—H63B | 109.5 |
N3—C4—C5 | 126.5 (3) | C62—C63—H63C | 109.5 |
N3—C4—Cl4 | 113.2 (2) | H63A—C63—H63C | 109.5 |
C5—C4—Cl4 | 120.2 (2) | H63B—C63—H63C | 109.5 |
C4—C5—C6 | 112.9 (3) | N61—C64—C65 | 112.2 (3) |
C4—C5—C51 | 119.4 (3) | N61—C64—H64A | 109.2 |
C6—C5—C51 | 126.7 (3) | C65—C64—H64A | 109.2 |
O51—C51—C5 | 126.7 (3) | N61—C64—H64B | 109.2 |
O51—C51—H51 | 116.7 | C65—C64—H64B | 109.2 |
C5—C51—H51 | 116.7 | H64A—C64—H64B | 107.9 |
N61—C6—N1 | 115.8 (3) | C64—C65—H65A | 109.5 |
N61—C6—C5 | 124.2 (3) | C64—C65—H65B | 109.5 |
N1—C6—C5 | 120.1 (3) | H65A—C65—H65B | 109.5 |
C6—N61—C62 | 125.1 (3) | C64—C65—H65C | 109.5 |
C6—N61—C64 | 119.4 (3) | H65A—C65—H65C | 109.5 |
C62—N61—C64 | 114.6 (3) | H65B—C65—H65C | 109.5 |
N61—C62—C63 | 114.6 (3) | | |
| | | |
C6—N1—C2—N2 | 172.7 (3) | C2—N1—C6—C5 | −6.2 (4) |
C6—N1—C2—N3 | −10.7 (5) | C4—C5—C6—N61 | −162.6 (3) |
N2—C2—N3—C4 | −168.3 (3) | C51—C5—C6—N61 | 29.6 (5) |
N1—C2—N3—C4 | 15.1 (4) | C4—C5—C6—N1 | 16.4 (4) |
C2—N3—C4—C5 | −2.4 (5) | C51—C5—C6—N1 | −151.4 (3) |
C2—N3—C4—Cl4 | 177.3 (2) | N1—C6—N61—C62 | −162.3 (3) |
N3—C4—C5—C6 | −12.2 (5) | C5—C6—N61—C62 | 16.7 (5) |
Cl4—C4—C5—C6 | 168.1 (2) | N1—C6—N61—C64 | 5.4 (4) |
N3—C4—C5—C51 | 156.6 (3) | C5—C6—N61—C64 | −175.6 (3) |
Cl4—C4—C5—C51 | −23.1 (4) | C6—N61—C62—C63 | 53.7 (4) |
C4—C5—C51—O51 | −153.8 (3) | C64—N61—C62—C63 | −114.5 (3) |
C6—C5—C51—O51 | 13.2 (5) | C6—N61—C64—C65 | −93.4 (3) |
C2—N1—C6—N61 | 172.8 (3) | C62—N61—C64—C65 | 75.5 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O51i | 0.86 | 2.16 | 2.986 (3) | 160 |
N2—H2B···N3ii | 0.86 | 2.17 | 3.026 (3) | 176 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1. |
Crystal data top
C9H11ClN4O2 | F(000) = 504 |
Mr = 242.67 | Dx = 1.545 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2411 reflections |
a = 7.3540 (5) Å | θ = 3.4–27.5° |
b = 8.2910 (13) Å | µ = 0.36 mm−1 |
c = 17.276 (3) Å | T = 120 K |
β = 97.962 (9)° | Block, colourless |
V = 1043.2 (3) Å3 | 0.43 × 0.27 × 0.25 mm |
Z = 4 | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 2411 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 1847 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
ϕ & ω scans | θmax = 27.5°, θmin = 3.4° |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | h = −9→9 |
Tmin = 0.862, Tmax = 0.916 | k = −10→10 |
23197 measured reflections | l = −22→22 |
Refinement top
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) = 0.087 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0287P)2 + 0.8135P] where P = (Fo2 + 2Fc2)/3 |
2411 reflections | (Δ/σ)max < 0.001 |
145 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
Crystal data top
C9H11ClN4O2 | V = 1043.2 (3) Å3 |
Mr = 242.67 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.3540 (5) Å | µ = 0.36 mm−1 |
b = 8.2910 (13) Å | T = 120 K |
c = 17.276 (3) Å | 0.43 × 0.27 × 0.25 mm |
β = 97.962 (9)° | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 2411 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 1847 reflections with I > 2σ(I) |
Tmin = 0.862, Tmax = 0.916 | Rint = 0.057 |
23197 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.087 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.26 e Å−3 |
2411 reflections | Δρmin = −0.30 e Å−3 |
145 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl4 | 0.04078 (6) | 0.11154 (6) | 0.38668 (3) | 0.02457 (14) | |
O51 | 0.04412 (17) | 0.62528 (15) | 0.41908 (8) | 0.0199 (3) | |
O64 | 0.55062 (17) | 0.80546 (16) | 0.24959 (8) | 0.0220 (3) | |
N1 | 0.55786 (19) | 0.39370 (17) | 0.43026 (8) | 0.0141 (3) | |
N2 | 0.6843 (2) | 0.16390 (19) | 0.48805 (9) | 0.0178 (3) | |
N3 | 0.3866 (2) | 0.14625 (18) | 0.42907 (9) | 0.0168 (3) | |
N61 | 0.42737 (19) | 0.61957 (18) | 0.36997 (9) | 0.0154 (3) | |
C2 | 0.5403 (2) | 0.2400 (2) | 0.44905 (10) | 0.0153 (4) | |
C4 | 0.2386 (2) | 0.2298 (2) | 0.40523 (10) | 0.0164 (4) | |
C5 | 0.2268 (2) | 0.3973 (2) | 0.39611 (10) | 0.0150 (4) | |
C6 | 0.4057 (2) | 0.4716 (2) | 0.39821 (10) | 0.0148 (4) | |
C51 | 0.0596 (2) | 0.4806 (2) | 0.40591 (10) | 0.0174 (4) | |
C62 | 0.2953 (2) | 0.6987 (2) | 0.31075 (11) | 0.0184 (4) | |
C63 | 0.3810 (2) | 0.7207 (2) | 0.23665 (11) | 0.0203 (4) | |
C65 | 0.6784 (2) | 0.7207 (2) | 0.30431 (11) | 0.0204 (4) | |
C66 | 0.6050 (2) | 0.7030 (2) | 0.38147 (11) | 0.0171 (4) | |
H2A | 0.7710 | 0.2258 | 0.5093 | 0.021* | |
H2B | 0.6663 | 0.0700 | 0.5067 | 0.021* | |
H51 | −0.0492 | 0.4176 | 0.4018 | 0.021* | |
H62A | 0.2604 | 0.8050 | 0.3303 | 0.022* | |
H62B | 0.1830 | 0.6320 | 0.2998 | 0.022* | |
H63A | 0.4017 | 0.6134 | 0.2143 | 0.024* | |
H63B | 0.2944 | 0.7805 | 0.1980 | 0.024* | |
H65A | 0.7964 | 0.7801 | 0.3125 | 0.024* | |
H65B | 0.7015 | 0.6126 | 0.2833 | 0.024* | |
H66A | 0.6935 | 0.6410 | 0.4184 | 0.021* | |
H66B | 0.5903 | 0.8109 | 0.4043 | 0.021* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl4 | 0.0143 (2) | 0.0211 (2) | 0.0371 (3) | −0.00387 (19) | −0.00087 (18) | 0.0013 (2) |
O51 | 0.0151 (6) | 0.0197 (7) | 0.0248 (7) | 0.0019 (5) | 0.0027 (5) | −0.0005 (6) |
O64 | 0.0183 (7) | 0.0262 (7) | 0.0212 (7) | −0.0034 (6) | 0.0021 (5) | 0.0081 (6) |
N1 | 0.0118 (7) | 0.0165 (7) | 0.0143 (7) | 0.0015 (6) | 0.0026 (6) | 0.0021 (6) |
N2 | 0.0134 (7) | 0.0168 (8) | 0.0231 (8) | −0.0009 (6) | 0.0019 (6) | 0.0032 (6) |
N3 | 0.0133 (7) | 0.0179 (8) | 0.0192 (8) | −0.0002 (6) | 0.0014 (6) | 0.0009 (6) |
N61 | 0.0102 (7) | 0.0190 (8) | 0.0169 (7) | −0.0009 (6) | 0.0017 (6) | 0.0033 (6) |
C2 | 0.0129 (8) | 0.0194 (9) | 0.0143 (9) | 0.0008 (7) | 0.0047 (7) | −0.0006 (7) |
C4 | 0.0133 (8) | 0.0210 (9) | 0.0151 (9) | −0.0026 (7) | 0.0024 (7) | −0.0003 (7) |
C5 | 0.0113 (8) | 0.0185 (9) | 0.0151 (8) | 0.0004 (7) | 0.0019 (7) | 0.0011 (7) |
C6 | 0.0145 (8) | 0.0178 (9) | 0.0124 (8) | 0.0008 (7) | 0.0033 (7) | −0.0022 (7) |
C51 | 0.0115 (8) | 0.0229 (10) | 0.0175 (9) | −0.0003 (7) | 0.0009 (7) | 0.0010 (7) |
C62 | 0.0140 (8) | 0.0201 (9) | 0.0209 (10) | 0.0023 (7) | 0.0014 (7) | 0.0057 (7) |
C63 | 0.0177 (9) | 0.0235 (10) | 0.0189 (9) | −0.0018 (8) | 0.0000 (7) | 0.0042 (8) |
C65 | 0.0146 (9) | 0.0250 (10) | 0.0218 (10) | 0.0000 (8) | 0.0029 (7) | 0.0041 (8) |
C66 | 0.0145 (8) | 0.0180 (9) | 0.0188 (9) | −0.0008 (7) | 0.0018 (7) | 0.0017 (7) |
Geometric parameters (Å, º) top
Cl4—C4 | 1.7466 (18) | C4—C5 | 1.399 (3) |
O51—C51 | 1.229 (2) | C5—C51 | 1.441 (2) |
O64—C63 | 1.422 (2) | C5—C6 | 1.449 (2) |
O64—C65 | 1.423 (2) | C51—H51 | 0.95 |
N1—C2 | 1.326 (2) | C62—C63 | 1.514 (3) |
N1—C6 | 1.344 (2) | C62—H62A | 0.99 |
N2—C2 | 1.333 (2) | C62—H62B | 0.99 |
N2—H2A | 0.8601 | C63—H63A | 0.99 |
N2—H2B | 0.86 | C63—H63B | 0.99 |
N3—C4 | 1.308 (2) | C65—C66 | 1.513 (3) |
N3—C2 | 1.376 (2) | C65—H65A | 0.99 |
N61—C6 | 1.338 (2) | C65—H65B | 0.99 |
N61—C62 | 1.464 (2) | C66—H66A | 0.99 |
N61—C66 | 1.467 (2) | C66—H66B | 0.99 |
| | | |
C63—O64—C65 | 110.16 (14) | N61—C62—C63 | 109.34 (15) |
C2—N1—C6 | 117.34 (15) | N61—C62—H62A | 109.8 |
C2—N2—H2A | 115.1 | C63—C62—H62A | 109.8 |
C2—N2—H2B | 117.7 | N61—C62—H62B | 109.8 |
H2A—N2—H2B | 121.6 | C63—C62—H62B | 109.8 |
C4—N3—C2 | 113.49 (15) | H62A—C62—H62B | 108.3 |
C6—N61—C62 | 124.36 (15) | O64—C63—C62 | 112.66 (15) |
C6—N61—C66 | 122.13 (15) | O64—C63—H63A | 109.1 |
C62—N61—C66 | 112.04 (14) | C62—C63—H63A | 109.1 |
N1—C2—N2 | 118.77 (16) | O64—C63—H63B | 109.1 |
N1—C2—N3 | 125.90 (16) | C62—C63—H63B | 109.1 |
N2—C2—N3 | 115.27 (16) | H63A—C63—H63B | 107.8 |
N3—C4—C5 | 126.66 (16) | O64—C65—C66 | 110.48 (15) |
N3—C4—Cl4 | 113.34 (14) | O64—C65—H65A | 109.6 |
C5—C4—Cl4 | 119.97 (13) | C66—C65—H65A | 109.6 |
C4—C5—C51 | 120.22 (16) | O64—C65—H65B | 109.6 |
C4—C5—C6 | 112.20 (15) | C66—C65—H65B | 109.6 |
C51—C5—C6 | 125.43 (16) | H65A—C65—H65B | 108.1 |
N61—C6—N1 | 117.17 (16) | N61—C66—C65 | 110.25 (15) |
N61—C6—C5 | 122.34 (16) | N61—C66—H66A | 109.6 |
N1—C6—C5 | 120.48 (16) | C65—C66—H66A | 109.6 |
O51—C51—C5 | 126.31 (17) | N61—C66—H66B | 109.6 |
O51—C51—H51 | 116.8 | C65—C66—H66B | 109.6 |
C5—C51—H51 | 116.8 | H66A—C66—H66B | 108.1 |
| | | |
C6—N1—C2—N2 | −173.30 (15) | C2—N1—C6—C5 | 9.5 (2) |
C6—N1—C2—N3 | 9.7 (3) | C4—C5—C6—N61 | 161.18 (16) |
C4—N3—C2—N1 | −15.8 (3) | C51—C5—C6—N61 | −35.6 (3) |
C4—N3—C2—N2 | 167.08 (15) | C4—C5—C6—N1 | −19.8 (2) |
C2—N3—C4—C5 | 2.6 (3) | C51—C5—C6—N1 | 143.43 (18) |
C2—N3—C4—Cl4 | −175.63 (12) | C4—C5—C51—O51 | 160.36 (18) |
N3—C4—C5—C51 | −150.49 (18) | C6—C5—C51—O51 | −1.7 (3) |
Cl4—C4—C5—C51 | 27.6 (2) | C6—N61—C62—C63 | −113.98 (18) |
N3—C4—C5—C6 | 13.7 (3) | C66—N61—C62—C63 | 52.4 (2) |
Cl4—C4—C5—C6 | −168.16 (13) | C65—O64—C63—C62 | 59.5 (2) |
C62—N61—C6—N1 | 157.70 (16) | N61—C62—C63—O64 | −55.1 (2) |
C66—N61—C6—N1 | −7.4 (2) | C63—O64—C65—C66 | −59.81 (19) |
C62—N61—C6—C5 | −23.3 (3) | C6—N61—C66—C65 | 112.30 (18) |
C66—N61—C6—C5 | 171.66 (16) | C62—N61—C66—C65 | −54.43 (19) |
C2—N1—C6—N61 | −171.45 (15) | O64—C65—C66—N61 | 57.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O51i | 0.86 | 2.11 | 2.955 (2) | 169 |
N2—H2B···N3ii | 0.86 | 2.17 | 3.023 (2) | 171 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1. |
Crystal data top
C12H17ClN4O | Z = 2 |
Mr = 268.75 | F(000) = 284 |
Triclinic, P1 | Dx = 1.385 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.5722 (6) Å | Cell parameters from 2950 reflections |
b = 8.7195 (5) Å | θ = 3.1–27.5° |
c = 8.7681 (7) Å | µ = 0.29 mm−1 |
α = 82.598 (6)° | T = 120 K |
β = 82.701 (5)° | Lath, colourless |
γ = 88.645 (5)° | 0.55 × 0.29 × 0.12 mm |
V = 644.63 (8) Å3 | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 2950 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 2650 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
ϕ & ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | h = −11→11 |
Tmin = 0.856, Tmax = 0.966 | k = −11→11 |
18098 measured reflections | l = −11→11 |
Refinement top
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.080 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0351P)2 + 0.3109P] where P = (Fo2 + 2Fc2)/3 |
2950 reflections | (Δ/σ)max < 0.001 |
164 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Crystal data top
C12H17ClN4O | γ = 88.645 (5)° |
Mr = 268.75 | V = 644.63 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.5722 (6) Å | Mo Kα radiation |
b = 8.7195 (5) Å | µ = 0.29 mm−1 |
c = 8.7681 (7) Å | T = 120 K |
α = 82.598 (6)° | 0.55 × 0.29 × 0.12 mm |
β = 82.701 (5)° | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 2950 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 2650 reflections with I > 2σ(I) |
Tmin = 0.856, Tmax = 0.966 | Rint = 0.018 |
18098 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.080 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.34 e Å−3 |
2950 reflections | Δρmin = −0.24 e Å−3 |
164 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl4 | 0.08515 (3) | 0.86418 (3) | 0.14913 (4) | 0.02344 (10) | |
O51 | 0.10958 (10) | 0.37823 (10) | 0.11711 (10) | 0.02188 (19) | |
N1 | 0.53482 (11) | 0.59963 (11) | 0.14624 (11) | 0.0155 (2) | |
N2 | 0.65263 (12) | 0.82596 (11) | 0.03284 (12) | 0.0191 (2) | |
N3 | 0.38672 (12) | 0.83698 (11) | 0.11058 (12) | 0.0171 (2) | |
N61 | 0.41428 (11) | 0.37877 (11) | 0.27134 (11) | 0.0160 (2) | |
C2 | 0.52251 (14) | 0.74955 (13) | 0.09633 (13) | 0.0158 (2) | |
C4 | 0.25849 (14) | 0.75455 (13) | 0.14349 (13) | 0.0165 (2) | |
C5 | 0.25019 (13) | 0.59279 (13) | 0.17197 (13) | 0.0159 (2) | |
C6 | 0.40092 (13) | 0.52129 (13) | 0.19577 (13) | 0.0147 (2) | |
C51 | 0.11337 (14) | 0.51353 (14) | 0.14201 (14) | 0.0196 (2) | |
C61 | 0.57301 (13) | 0.31075 (13) | 0.28449 (13) | 0.0159 (2) | |
C62 | 0.57286 (15) | 0.13447 (13) | 0.29619 (15) | 0.0205 (2) | |
C63 | 0.74075 (16) | 0.07226 (15) | 0.29846 (15) | 0.0253 (3) | |
C64 | 0.81615 (16) | 0.12409 (16) | 0.43179 (16) | 0.0261 (3) | |
C65 | 0.81133 (15) | 0.29982 (15) | 0.42411 (15) | 0.0229 (3) | |
C66 | 0.64347 (14) | 0.36293 (14) | 0.42108 (14) | 0.0187 (2) | |
C67 | 0.28209 (15) | 0.30183 (14) | 0.37147 (15) | 0.0214 (3) | |
H2A | 0.7349 | 0.7723 | 0.0066 | 0.023* | |
H2B | 0.6437 | 0.9209 | −0.0062 | 0.023* | |
H51 | 0.0179 | 0.5710 | 0.1415 | 0.024* | |
H61 | 0.6426 | 0.3502 | 0.1877 | 0.019* | |
H62A | 0.5282 | 0.1024 | 0.2066 | 0.025* | |
H62B | 0.5065 | 0.0911 | 0.3921 | 0.025* | |
H63A | 0.7394 | −0.0421 | 0.3093 | 0.030* | |
H63B | 0.8046 | 0.1096 | 0.1990 | 0.030* | |
H64A | 0.7594 | 0.0774 | 0.5318 | 0.031* | |
H64B | 0.9267 | 0.0876 | 0.4263 | 0.031* | |
H65A | 0.8784 | 0.3458 | 0.3298 | 0.027* | |
H65B | 0.8544 | 0.3303 | 0.5153 | 0.027* | |
H66A | 0.6445 | 0.4773 | 0.4110 | 0.022* | |
H66B | 0.5781 | 0.3247 | 0.5194 | 0.022* | |
H67A | 0.2400 | 0.2225 | 0.3185 | 0.032* | |
H67B | 0.1996 | 0.3781 | 0.3949 | 0.032* | |
H67C | 0.3180 | 0.2532 | 0.4682 | 0.032* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl4 | 0.02018 (16) | 0.02003 (15) | 0.02897 (17) | 0.00824 (11) | −0.00240 (11) | −0.00103 (12) |
O51 | 0.0208 (4) | 0.0190 (4) | 0.0262 (5) | −0.0006 (3) | −0.0041 (3) | −0.0032 (3) |
N1 | 0.0168 (5) | 0.0128 (4) | 0.0165 (5) | 0.0012 (4) | −0.0027 (4) | −0.0002 (4) |
N2 | 0.0189 (5) | 0.0118 (4) | 0.0255 (5) | 0.0010 (4) | −0.0017 (4) | 0.0006 (4) |
N3 | 0.0195 (5) | 0.0131 (4) | 0.0184 (5) | 0.0031 (4) | −0.0026 (4) | −0.0013 (4) |
N61 | 0.0157 (5) | 0.0140 (4) | 0.0172 (5) | 0.0014 (4) | −0.0022 (4) | 0.0019 (4) |
C2 | 0.0188 (6) | 0.0145 (5) | 0.0148 (5) | 0.0020 (4) | −0.0041 (4) | −0.0027 (4) |
C4 | 0.0184 (5) | 0.0171 (5) | 0.0137 (5) | 0.0059 (4) | −0.0032 (4) | −0.0013 (4) |
C5 | 0.0171 (5) | 0.0157 (5) | 0.0147 (5) | 0.0026 (4) | −0.0023 (4) | −0.0007 (4) |
C6 | 0.0180 (5) | 0.0134 (5) | 0.0129 (5) | 0.0023 (4) | −0.0023 (4) | −0.0022 (4) |
C51 | 0.0176 (6) | 0.0205 (6) | 0.0205 (6) | 0.0025 (4) | −0.0036 (4) | −0.0011 (5) |
C61 | 0.0168 (5) | 0.0139 (5) | 0.0161 (5) | 0.0037 (4) | −0.0020 (4) | 0.0005 (4) |
C62 | 0.0269 (6) | 0.0150 (5) | 0.0196 (6) | 0.0031 (5) | −0.0063 (5) | 0.0003 (4) |
C63 | 0.0319 (7) | 0.0200 (6) | 0.0240 (6) | 0.0116 (5) | −0.0061 (5) | −0.0026 (5) |
C64 | 0.0262 (7) | 0.0281 (7) | 0.0239 (6) | 0.0106 (5) | −0.0071 (5) | −0.0003 (5) |
C65 | 0.0179 (6) | 0.0277 (6) | 0.0231 (6) | 0.0037 (5) | −0.0044 (5) | −0.0019 (5) |
C66 | 0.0185 (6) | 0.0191 (5) | 0.0187 (6) | 0.0032 (4) | −0.0028 (4) | −0.0028 (4) |
C67 | 0.0199 (6) | 0.0201 (6) | 0.0220 (6) | −0.0010 (5) | −0.0009 (5) | 0.0040 (5) |
Geometric parameters (Å, º) top
Cl4—C4 | 1.7465 (11) | C61—H61 | 1.00 |
O51—C51 | 1.2290 (15) | C62—C63 | 1.5275 (17) |
N1—C2 | 1.3301 (15) | C62—H62A | 0.99 |
N1—C6 | 1.3441 (15) | C62—H62B | 0.99 |
N2—C2 | 1.3340 (15) | C63—C64 | 1.5266 (19) |
N2—H2A | 0.8603 | C63—H63A | 0.99 |
N2—H2B | 0.86 | C63—H63B | 0.99 |
N3—C4 | 1.3082 (16) | C64—C65 | 1.5249 (19) |
N3—C2 | 1.3775 (15) | C64—H64A | 0.99 |
N61—C6 | 1.3405 (15) | C64—H64B | 0.99 |
N61—C67 | 1.4616 (15) | C65—C66 | 1.5306 (16) |
N61—C61 | 1.4835 (14) | C65—H65A | 0.99 |
C4—C5 | 1.4023 (16) | C65—H65B | 0.99 |
C5—C51 | 1.4441 (17) | C66—H66A | 0.99 |
C5—C6 | 1.4487 (15) | C66—H66B | 0.99 |
C51—H51 | 0.95 | C67—H67A | 0.98 |
C61—C62 | 1.5273 (16) | C67—H67B | 0.98 |
C61—C66 | 1.5308 (16) | C67—H67C | 0.98 |
| | | |
C2—N1—C6 | 117.52 (10) | C63—C62—H62B | 109.7 |
C2—N2—H2A | 117.7 | H62A—C62—H62B | 108.2 |
C2—N2—H2B | 118.4 | C64—C63—C62 | 111.39 (10) |
H2A—N2—H2B | 121.0 | C64—C63—H63A | 109.4 |
C4—N3—C2 | 113.70 (10) | C62—C63—H63A | 109.4 |
C6—N61—C67 | 121.95 (10) | C64—C63—H63B | 109.4 |
C6—N61—C61 | 119.35 (10) | C62—C63—H63B | 109.4 |
C67—N61—C61 | 117.18 (9) | H63A—C63—H63B | 108.0 |
N1—C2—N2 | 118.40 (10) | C65—C64—C63 | 110.76 (10) |
N1—C2—N3 | 125.65 (11) | C65—C64—H64A | 109.5 |
N2—C2—N3 | 115.88 (10) | C63—C64—H64A | 109.5 |
N3—C4—C5 | 126.41 (11) | C65—C64—H64B | 109.5 |
N3—C4—Cl4 | 114.03 (9) | C63—C64—H64B | 109.5 |
C5—C4—Cl4 | 119.56 (9) | H64A—C64—H64B | 108.1 |
C4—C5—C51 | 120.36 (10) | C64—C65—C66 | 111.47 (11) |
C4—C5—C6 | 112.53 (10) | C64—C65—H65A | 109.3 |
C51—C5—C6 | 125.50 (10) | C66—C65—H65A | 109.3 |
N61—C6—N1 | 117.04 (10) | C64—C65—H65B | 109.3 |
N61—C6—C5 | 122.60 (10) | C66—C65—H65B | 109.3 |
N1—C6—C5 | 120.32 (10) | H65A—C65—H65B | 108.0 |
O51—C51—C5 | 125.76 (11) | C65—C66—C61 | 109.85 (10) |
O51—C51—H51 | 117.1 | C65—C66—H66A | 109.7 |
C5—C51—H51 | 117.1 | C61—C66—H66A | 109.7 |
N61—C61—C62 | 112.29 (10) | C65—C66—H66B | 109.7 |
N61—C61—C66 | 111.37 (9) | C61—C66—H66B | 109.7 |
C62—C61—C66 | 110.60 (9) | H66A—C66—H66B | 108.2 |
N61—C61—H61 | 107.4 | N61—C67—H67A | 109.5 |
C62—C61—H61 | 107.4 | N61—C67—H67B | 109.5 |
C66—C61—H61 | 107.4 | H67A—C67—H67B | 109.5 |
C61—C62—C63 | 109.77 (10) | N61—C67—H67C | 109.5 |
C61—C62—H62A | 109.7 | H67A—C67—H67C | 109.5 |
C63—C62—H62A | 109.7 | H67B—C67—H67C | 109.5 |
C61—C62—H62B | 109.7 | | |
| | | |
C6—N1—C2—N2 | −173.62 (10) | C51—C5—C6—N61 | −36.33 (17) |
C6—N1—C2—N3 | 9.61 (17) | C4—C5—C6—N1 | −19.52 (15) |
C4—N3—C2—N1 | −16.20 (17) | C51—C5—C6—N1 | 146.00 (12) |
C4—N3—C2—N2 | 166.96 (10) | C4—C5—C51—O51 | 156.72 (12) |
C2—N3—C4—C5 | 3.51 (17) | C6—C5—C51—O51 | −7.8 (2) |
C2—N3—C4—Cl4 | −175.98 (8) | C6—N61—C61—C62 | −151.21 (10) |
N3—C4—C5—C51 | −153.44 (12) | C67—N61—C61—C62 | 42.58 (14) |
Cl4—C4—C5—C51 | 26.02 (15) | C6—N61—C61—C66 | 84.13 (13) |
N3—C4—C5—C6 | 12.91 (17) | C67—N61—C61—C66 | −82.08 (12) |
Cl4—C4—C5—C6 | −167.63 (8) | N61—C61—C62—C63 | 176.23 (10) |
C67—N61—C6—N1 | 160.41 (11) | C66—C61—C62—C63 | −58.69 (13) |
C61—N61—C6—N1 | −5.12 (15) | C61—C62—C63—C64 | 57.30 (14) |
C67—N61—C6—C5 | −17.34 (17) | C62—C63—C64—C65 | −55.66 (15) |
C61—N61—C6—C5 | 177.13 (10) | C63—C64—C65—C66 | 55.32 (14) |
C2—N1—C6—N61 | −168.26 (10) | C64—C65—C66—C61 | −56.62 (14) |
C2—N1—C6—C5 | 9.54 (16) | N61—C61—C66—C65 | −176.05 (9) |
C4—C5—C6—N61 | 158.15 (11) | C62—C61—C66—C65 | 58.35 (13) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O51i | 0.86 | 2.14 | 2.9672 (14) | 160 |
N2—H2B···N3ii | 0.86 | 2.21 | 3.0727 (14) | 178 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+2, −z. |
Crystal data top
C14H15ClN4O | Z = 2 |
Mr = 290.75 | F(000) = 304 |
Triclinic, P1 | Dx = 1.388 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.9897 (5) Å | Cell parameters from 3191 reflections |
b = 8.0922 (4) Å | θ = 3.1–27.5° |
c = 11.2786 (7) Å | µ = 0.28 mm−1 |
α = 91.602 (4)° | T = 120 K |
β = 107.220 (5)° | Block, colourless |
γ = 91.776 (5)° | 0.29 × 0.28 × 0.21 mm |
V = 695.66 (7) Å3 | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 3191 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 2729 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ϕ & ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | h = −10→10 |
Tmin = 0.929, Tmax = 0.944 | k = −10→10 |
19407 measured reflections | l = −14→14 |
Refinement top
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0295P)2 + 0.4094P] where P = (Fo2 + 2Fc2)/3 |
3191 reflections | (Δ/σ)max < 0.001 |
182 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
Crystal data top
C14H15ClN4O | γ = 91.776 (5)° |
Mr = 290.75 | V = 695.66 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.9897 (5) Å | Mo Kα radiation |
b = 8.0922 (4) Å | µ = 0.28 mm−1 |
c = 11.2786 (7) Å | T = 120 K |
α = 91.602 (4)° | 0.29 × 0.28 × 0.21 mm |
β = 107.220 (5)° | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 3191 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 2729 reflections with I > 2σ(I) |
Tmin = 0.929, Tmax = 0.944 | Rint = 0.026 |
19407 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.082 | H-atom parameters constrained |
S = 1.12 | Δρmax = 0.28 e Å−3 |
3191 reflections | Δρmin = −0.30 e Å−3 |
182 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl4 | 0.16086 (5) | 0.10251 (4) | 0.15234 (4) | 0.02196 (10) | |
O51 | 0.67154 (13) | 0.09713 (12) | 0.11486 (9) | 0.0192 (2) | |
N1 | 0.45541 (15) | 0.56822 (14) | 0.12673 (10) | 0.0140 (2) | |
N2 | 0.18588 (15) | 0.67590 (14) | 0.04287 (11) | 0.0172 (2) | |
N3 | 0.18943 (15) | 0.41157 (14) | 0.11221 (11) | 0.0152 (2) | |
N61 | 0.72480 (15) | 0.46270 (14) | 0.21076 (10) | 0.0139 (2) | |
C2 | 0.28169 (17) | 0.54892 (17) | 0.09391 (12) | 0.0139 (3) | |
C4 | 0.28395 (18) | 0.28129 (17) | 0.14313 (12) | 0.0150 (3) | |
C5 | 0.46476 (17) | 0.27389 (17) | 0.16236 (12) | 0.0141 (3) | |
C6 | 0.54986 (17) | 0.43489 (17) | 0.16665 (12) | 0.0132 (3) | |
C51 | 0.54016 (18) | 0.11612 (17) | 0.14745 (13) | 0.0174 (3) | |
C61 | 0.78125 (18) | 0.30538 (17) | 0.40537 (13) | 0.0164 (3) | |
C62 | 0.7823 (2) | 0.14111 (19) | 0.43793 (14) | 0.0230 (3) | |
C63 | 0.7301 (2) | 0.0948 (2) | 0.54002 (16) | 0.0300 (4) | |
C64 | 0.6779 (2) | 0.2127 (2) | 0.61128 (15) | 0.0292 (4) | |
C65 | 0.6772 (2) | 0.3769 (2) | 0.57982 (14) | 0.0263 (3) | |
C66 | 0.72774 (19) | 0.42296 (19) | 0.47748 (14) | 0.0211 (3) | |
C67 | 0.84363 (17) | 0.35478 (17) | 0.29666 (13) | 0.0162 (3) | |
C68 | 0.80377 (18) | 0.61997 (17) | 0.18582 (13) | 0.0168 (3) | |
C69 | 0.8290 (2) | 0.75189 (18) | 0.28807 (14) | 0.0218 (3) | |
H2A | 0.2378 | 0.7508 | 0.0123 | 0.021* | |
H2B | 0.0767 | 0.6537 | 0.0053 | 0.021* | |
H51 | 0.4823 | 0.0194 | 0.1645 | 0.021* | |
H62 | 0.8191 | 0.0594 | 0.3900 | 0.028* | |
H63 | 0.7303 | −0.0182 | 0.5607 | 0.036* | |
H64 | 0.6429 | 0.1813 | 0.6812 | 0.035* | |
H65 | 0.6419 | 0.4586 | 0.6286 | 0.032* | |
H66 | 0.7258 | 0.5359 | 0.4564 | 0.025* | |
H67A | 0.9602 | 0.4124 | 0.3289 | 0.019* | |
H67B | 0.8580 | 0.2534 | 0.2501 | 0.019* | |
H68A | 0.7280 | 0.6624 | 0.1074 | 0.020* | |
H68B | 0.9191 | 0.5984 | 0.1738 | 0.020* | |
H69A | 0.7154 | 0.7744 | 0.3006 | 0.033* | |
H69B | 0.8791 | 0.8534 | 0.2646 | 0.033* | |
H69C | 0.9087 | 0.7133 | 0.3653 | 0.033* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl4 | 0.01736 (17) | 0.01823 (17) | 0.0303 (2) | −0.00224 (12) | 0.00687 (14) | 0.00692 (14) |
O51 | 0.0185 (5) | 0.0184 (5) | 0.0211 (5) | 0.0030 (4) | 0.0061 (4) | 0.0008 (4) |
N1 | 0.0141 (5) | 0.0149 (5) | 0.0127 (5) | 0.0009 (4) | 0.0033 (4) | 0.0001 (4) |
N2 | 0.0133 (6) | 0.0170 (6) | 0.0209 (6) | 0.0008 (4) | 0.0039 (5) | 0.0039 (5) |
N3 | 0.0137 (5) | 0.0177 (6) | 0.0143 (5) | 0.0006 (4) | 0.0039 (4) | 0.0021 (4) |
N61 | 0.0127 (5) | 0.0151 (6) | 0.0130 (5) | 0.0003 (4) | 0.0025 (4) | 0.0003 (4) |
C2 | 0.0154 (6) | 0.0158 (6) | 0.0104 (6) | 0.0009 (5) | 0.0038 (5) | −0.0009 (5) |
C4 | 0.0160 (6) | 0.0172 (7) | 0.0113 (6) | −0.0021 (5) | 0.0035 (5) | 0.0014 (5) |
C5 | 0.0148 (6) | 0.0153 (6) | 0.0114 (6) | 0.0013 (5) | 0.0026 (5) | 0.0019 (5) |
C6 | 0.0147 (6) | 0.0164 (6) | 0.0091 (6) | 0.0008 (5) | 0.0044 (5) | −0.0013 (5) |
C51 | 0.0175 (7) | 0.0146 (7) | 0.0189 (7) | 0.0003 (5) | 0.0035 (5) | 0.0026 (5) |
C61 | 0.0123 (6) | 0.0193 (7) | 0.0140 (6) | 0.0013 (5) | −0.0016 (5) | 0.0008 (5) |
C62 | 0.0271 (8) | 0.0190 (7) | 0.0189 (7) | 0.0008 (6) | 0.0010 (6) | −0.0008 (6) |
C63 | 0.0358 (9) | 0.0253 (8) | 0.0248 (8) | −0.0044 (7) | 0.0026 (7) | 0.0069 (6) |
C64 | 0.0265 (8) | 0.0407 (10) | 0.0202 (8) | −0.0009 (7) | 0.0063 (6) | 0.0090 (7) |
C65 | 0.0258 (8) | 0.0358 (9) | 0.0184 (7) | 0.0074 (7) | 0.0075 (6) | 0.0015 (6) |
C66 | 0.0222 (7) | 0.0213 (7) | 0.0190 (7) | 0.0048 (6) | 0.0042 (6) | 0.0019 (6) |
C67 | 0.0121 (6) | 0.0186 (7) | 0.0163 (6) | 0.0035 (5) | 0.0017 (5) | 0.0002 (5) |
C68 | 0.0143 (6) | 0.0180 (7) | 0.0184 (7) | −0.0009 (5) | 0.0054 (5) | 0.0013 (5) |
C69 | 0.0237 (7) | 0.0168 (7) | 0.0230 (7) | −0.0028 (6) | 0.0047 (6) | −0.0025 (6) |
Geometric parameters (Å, º) top
Cl4—C4 | 1.7469 (14) | C61—C67 | 1.513 (2) |
O51—C51 | 1.2230 (17) | C62—C63 | 1.393 (2) |
N1—C2 | 1.3292 (17) | C62—H62 | 0.95 |
N1—C6 | 1.3464 (17) | C63—C64 | 1.382 (3) |
N2—C2 | 1.3394 (18) | C63—H63 | 0.95 |
N2—H2A | 0.8599 | C64—C65 | 1.385 (2) |
N2—H2B | 0.8601 | C64—H64 | 0.95 |
N3—C4 | 1.3105 (18) | C65—C66 | 1.387 (2) |
N3—C2 | 1.3687 (17) | C65—H65 | 0.95 |
N61—C6 | 1.3469 (17) | C66—H66 | 0.95 |
N61—C67 | 1.4686 (17) | C67—H67A | 0.99 |
N61—C68 | 1.4738 (17) | C67—H67B | 0.99 |
C4—C5 | 1.3994 (19) | C68—C69 | 1.513 (2) |
C5—C6 | 1.4436 (18) | C68—H68A | 0.99 |
C5—C51 | 1.4549 (19) | C68—H68B | 0.99 |
C51—H51 | 0.95 | C69—H69A | 0.98 |
C61—C62 | 1.389 (2) | C69—H69B | 0.98 |
C61—C66 | 1.392 (2) | C69—H69C | 0.98 |
| | | |
C2—N1—C6 | 117.62 (12) | C64—C63—H63 | 119.9 |
C2—N2—H2A | 116.7 | C62—C63—H63 | 119.9 |
C2—N2—H2B | 116.6 | C63—C64—C65 | 119.41 (15) |
H2A—N2—H2B | 117.1 | C63—C64—H64 | 120.3 |
C4—N3—C2 | 114.22 (12) | C65—C64—H64 | 120.3 |
C6—N61—C67 | 124.10 (11) | C64—C65—C66 | 120.42 (15) |
C6—N61—C68 | 119.46 (11) | C64—C65—H65 | 119.8 |
C67—N61—C68 | 115.99 (11) | C66—C65—H65 | 119.8 |
N1—C2—N2 | 118.27 (12) | C65—C66—C61 | 120.66 (14) |
N1—C2—N3 | 125.73 (12) | C65—C66—H66 | 119.7 |
N2—C2—N3 | 115.95 (12) | C61—C66—H66 | 119.7 |
N3—C4—C5 | 126.38 (13) | N61—C67—C61 | 113.93 (11) |
N3—C4—Cl4 | 113.59 (10) | N61—C67—H67A | 108.8 |
C5—C4—Cl4 | 119.97 (11) | C61—C67—H67A | 108.8 |
C4—C5—C6 | 112.88 (12) | N61—C67—H67B | 108.8 |
C4—C5—C51 | 119.72 (12) | C61—C67—H67B | 108.8 |
C6—C5—C51 | 125.72 (12) | H67A—C67—H67B | 107.7 |
N1—C6—N61 | 115.90 (12) | N61—C68—C69 | 113.83 (12) |
N1—C6—C5 | 120.79 (12) | N61—C68—H68A | 108.8 |
N61—C6—C5 | 123.30 (12) | C69—C68—H68A | 108.8 |
O51—C51—C5 | 125.71 (13) | N61—C68—H68B | 108.8 |
O51—C51—H51 | 117.1 | C69—C68—H68B | 108.8 |
C5—C51—H51 | 117.1 | H68A—C68—H68B | 107.7 |
C62—C61—C66 | 118.52 (14) | C68—C69—H69A | 109.5 |
C62—C61—C67 | 120.24 (13) | C68—C69—H69B | 109.5 |
C66—C61—C67 | 121.20 (13) | H69A—C69—H69B | 109.5 |
C61—C62—C63 | 120.78 (15) | C68—C69—H69C | 109.5 |
C61—C62—H62 | 119.6 | H69A—C69—H69C | 109.5 |
C63—C62—H62 | 119.6 | H69B—C69—H69C | 109.5 |
C64—C63—C62 | 120.21 (15) | | |
| | | |
C6—N1—C2—N2 | −173.70 (12) | C4—C5—C6—N61 | 164.82 (12) |
C6—N1—C2—N3 | 9.2 (2) | C51—C5—C6—N61 | −30.1 (2) |
C4—N3—C2—N1 | −13.34 (19) | C4—C5—C51—O51 | 150.42 (14) |
C4—N3—C2—N2 | 169.51 (12) | C6—C5—C51—O51 | −13.7 (2) |
C2—N3—C4—C5 | 2.4 (2) | C66—C61—C62—C63 | 0.4 (2) |
C2—N3—C4—Cl4 | −174.52 (9) | C67—C61—C62—C63 | 178.11 (14) |
N3—C4—C5—C6 | 10.4 (2) | C61—C62—C63—C64 | −0.7 (2) |
Cl4—C4—C5—C6 | −172.83 (9) | C62—C63—C64—C65 | 0.4 (3) |
N3—C4—C5—C51 | −155.60 (14) | C63—C64—C65—C66 | 0.2 (2) |
Cl4—C4—C5—C51 | 21.12 (17) | C64—C65—C66—C61 | −0.5 (2) |
C2—N1—C6—N61 | −173.59 (12) | C62—C61—C66—C65 | 0.2 (2) |
C2—N1—C6—C5 | 5.82 (18) | C67—C61—C66—C65 | −177.50 (13) |
C67—N61—C6—N1 | 157.43 (12) | C6—N61—C67—C61 | −46.82 (18) |
C68—N61—C6—N1 | −14.55 (18) | C68—N61—C67—C61 | 125.42 (12) |
C67—N61—C6—C5 | −22.0 (2) | C62—C61—C67—N61 | 132.45 (14) |
C68—N61—C6—C5 | 166.05 (12) | C66—C61—C67—N61 | −49.87 (18) |
C4—C5—C6—N1 | −14.54 (18) | C6—N61—C68—C69 | 94.02 (15) |
C51—C5—C6—N1 | 150.51 (13) | C67—N61—C68—C69 | −78.60 (15) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O51i | 0.86 | 2.18 | 3.0148 (16) | 164 |
N2—H2B···N3ii | 0.86 | 2.19 | 3.0407 (17) | 172 |
C65—H65···Cg1iii | 0.95 | 2.86 | 3.7061 (17) | 149 |
C68—H68A···Cg1i | 0.99 | 2.66 | 3.4643 (15) | 138 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y+1, −z; (iii) −x+1, −y+1, −z+1. |
Crystal data top
C13H13ClN4O | Z = 2 |
Mr = 276.72 | F(000) = 288 |
Triclinic, P1 | Dx = 1.446 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.1811 (12) Å | Cell parameters from 2902 reflections |
b = 8.8325 (10) Å | θ = 4.0–27.5° |
c = 9.3356 (6) Å | µ = 0.30 mm−1 |
α = 81.844 (9)° | T = 120 K |
β = 82.015 (10)° | Block, colourless |
γ = 73.041 (7)° | 0.56 × 0.46 × 0.24 mm |
V = 635.38 (12) Å3 | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 2902 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 2269 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
ϕ & ω scans | θmax = 27.5°, θmin = 4.0° |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | h = −10→10 |
Tmin = 0.851, Tmax = 0.932 | k = −11→11 |
15349 measured reflections | l = −12→12 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0368P)2 + 0.5204P] where P = (Fo2 + 2Fc2)/3 |
2902 reflections | (Δ/σ)max < 0.001 |
173 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
Crystal data top
C13H13ClN4O | γ = 73.041 (7)° |
Mr = 276.72 | V = 635.38 (12) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.1811 (12) Å | Mo Kα radiation |
b = 8.8325 (10) Å | µ = 0.30 mm−1 |
c = 9.3356 (6) Å | T = 120 K |
α = 81.844 (9)° | 0.56 × 0.46 × 0.24 mm |
β = 82.015 (10)° | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 2902 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 2269 reflections with I > 2σ(I) |
Tmin = 0.851, Tmax = 0.932 | Rint = 0.035 |
15349 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 1.11 | Δρmax = 0.31 e Å−3 |
2902 reflections | Δρmin = −0.36 e Å−3 |
173 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.37106 (18) | 0.41564 (17) | 0.35666 (16) | 0.0167 (3) | |
C2 | 0.4146 (2) | 0.2600 (2) | 0.40258 (19) | 0.0162 (3) | |
N2 | 0.28800 (19) | 0.19310 (17) | 0.45152 (17) | 0.0200 (3) | |
N3 | 0.57793 (18) | 0.16112 (16) | 0.40022 (16) | 0.0168 (3) | |
C4 | 0.6990 (2) | 0.2342 (2) | 0.36126 (19) | 0.0159 (3) | |
Cl4 | 0.90398 (5) | 0.10358 (5) | 0.35724 (5) | 0.02291 (14) | |
C5 | 0.6751 (2) | 0.3975 (2) | 0.32623 (18) | 0.0158 (3) | |
C51 | 0.8088 (2) | 0.4768 (2) | 0.33055 (19) | 0.0184 (4) | |
O51 | 0.95965 (17) | 0.41303 (16) | 0.34220 (17) | 0.0285 (3) | |
C6 | 0.4980 (2) | 0.4846 (2) | 0.31588 (18) | 0.0154 (3) | |
N61 | 0.44703 (18) | 0.64297 (16) | 0.26808 (16) | 0.0162 (3) | |
C61 | 0.5548 (2) | 0.7204 (2) | 0.16731 (19) | 0.0165 (4) | |
C62 | 0.6392 (2) | 0.6518 (2) | 0.0426 (2) | 0.0193 (4) | |
C63 | 0.7468 (2) | 0.7248 (2) | −0.0521 (2) | 0.0226 (4) | |
C64 | 0.7673 (2) | 0.8674 (2) | −0.0235 (2) | 0.0228 (4) | |
C65 | 0.6793 (2) | 0.9378 (2) | 0.0982 (2) | 0.0215 (4) | |
C66 | 0.5730 (2) | 0.8648 (2) | 0.1942 (2) | 0.0189 (4) | |
C67 | 0.2623 (2) | 0.7297 (2) | 0.2839 (2) | 0.0186 (4) | |
C68 | 0.1674 (2) | 0.7211 (2) | 0.1582 (2) | 0.0240 (4) | |
H2A | 0.1803 | 0.2511 | 0.4528 | 0.024* | |
H2B | 0.3122 | 0.0910 | 0.4825 | 0.024* | |
H51 | 0.7732 | 0.5898 | 0.3235 | 0.022* | |
H62 | 0.6231 | 0.5550 | 0.0222 | 0.023* | |
H63 | 0.8063 | 0.6769 | −0.1364 | 0.027* | |
H64 | 0.8419 | 0.9168 | −0.0877 | 0.027* | |
H65 | 0.6919 | 1.0368 | 0.1163 | 0.026* | |
H66 | 0.5128 | 0.9135 | 0.2779 | 0.023* | |
H67B | 0.2505 | 0.8428 | 0.2929 | 0.022* | |
H67A | 0.2076 | 0.6853 | 0.3751 | 0.022* | |
H68A | 0.2279 | 0.7540 | 0.0664 | 0.036* | |
H68B | 0.0504 | 0.7920 | 0.1691 | 0.036* | |
H68C | 0.1625 | 0.6116 | 0.1580 | 0.036* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0148 (7) | 0.0142 (7) | 0.0199 (8) | −0.0029 (6) | −0.0018 (6) | 0.0003 (6) |
C2 | 0.0168 (8) | 0.0159 (8) | 0.0159 (8) | −0.0039 (7) | −0.0023 (7) | −0.0023 (6) |
N2 | 0.0157 (7) | 0.0141 (7) | 0.0287 (8) | −0.0038 (6) | −0.0023 (6) | 0.0019 (6) |
N3 | 0.0161 (7) | 0.0138 (7) | 0.0196 (7) | −0.0027 (6) | −0.0023 (6) | −0.0011 (6) |
C4 | 0.0143 (8) | 0.0150 (8) | 0.0164 (8) | −0.0006 (6) | −0.0022 (6) | −0.0023 (6) |
Cl4 | 0.0161 (2) | 0.0168 (2) | 0.0316 (3) | 0.00076 (16) | −0.00190 (17) | −0.00073 (17) |
C5 | 0.0144 (8) | 0.0153 (8) | 0.0158 (8) | −0.0024 (6) | −0.0009 (6) | 0.0002 (6) |
C51 | 0.0182 (9) | 0.0168 (8) | 0.0188 (9) | −0.0048 (7) | −0.0006 (7) | 0.0009 (7) |
O51 | 0.0150 (6) | 0.0253 (7) | 0.0440 (9) | −0.0048 (5) | −0.0040 (6) | −0.0006 (6) |
C6 | 0.0160 (8) | 0.0142 (8) | 0.0150 (8) | −0.0023 (6) | −0.0012 (6) | −0.0029 (6) |
N61 | 0.0135 (7) | 0.0131 (7) | 0.0202 (8) | −0.0025 (6) | −0.0001 (6) | 0.0002 (6) |
C61 | 0.0151 (8) | 0.0150 (8) | 0.0180 (9) | −0.0029 (6) | −0.0029 (7) | 0.0009 (6) |
C62 | 0.0195 (9) | 0.0179 (8) | 0.0206 (9) | −0.0046 (7) | −0.0031 (7) | −0.0027 (7) |
C63 | 0.0214 (9) | 0.0254 (10) | 0.0181 (9) | −0.0029 (7) | −0.0009 (7) | −0.0015 (7) |
C64 | 0.0197 (9) | 0.0255 (10) | 0.0224 (9) | −0.0081 (7) | −0.0032 (7) | 0.0049 (7) |
C65 | 0.0236 (9) | 0.0160 (8) | 0.0255 (10) | −0.0062 (7) | −0.0061 (8) | 0.0010 (7) |
C66 | 0.0214 (9) | 0.0153 (8) | 0.0184 (9) | −0.0022 (7) | −0.0035 (7) | −0.0015 (7) |
C67 | 0.0155 (8) | 0.0132 (8) | 0.0239 (9) | 0.0000 (6) | −0.0007 (7) | −0.0016 (7) |
C68 | 0.0192 (9) | 0.0215 (9) | 0.0306 (10) | −0.0031 (7) | −0.0061 (8) | −0.0018 (8) |
Geometric parameters (Å, º) top
N1—C6 | 1.337 (2) | C61—C62 | 1.390 (2) |
N1—C2 | 1.338 (2) | C62—C63 | 1.388 (3) |
C2—N2 | 1.334 (2) | C62—H62 | 0.95 |
C2—N3 | 1.366 (2) | C63—C64 | 1.385 (3) |
N2—H2A | 0.88 | C63—H63 | 0.95 |
N2—H2B | 0.88 | C64—C65 | 1.382 (3) |
N3—C4 | 1.318 (2) | C64—H64 | 0.95 |
C4—C5 | 1.395 (2) | C65—C66 | 1.386 (3) |
C4—Cl4 | 1.7350 (17) | C65—H65 | 0.95 |
C5—C6 | 1.438 (2) | C66—H66 | 0.95 |
C5—C51 | 1.467 (2) | C67—C68 | 1.517 (3) |
C51—O51 | 1.211 (2) | C67—H67B | 0.99 |
C51—H51 | 0.95 | C67—H67A | 0.99 |
C6—N61 | 1.365 (2) | C68—H68A | 0.98 |
N61—C61 | 1.438 (2) | C68—H68B | 0.98 |
N61—C67 | 1.479 (2) | C68—H68C | 0.98 |
C61—C66 | 1.387 (2) | | |
| | | |
C6—N1—C2 | 117.63 (15) | C63—C62—H62 | 120.0 |
N2—C2—N1 | 117.66 (15) | C61—C62—H62 | 120.0 |
N2—C2—N3 | 116.44 (15) | C64—C63—C62 | 119.87 (17) |
N1—C2—N3 | 125.86 (16) | C64—C63—H63 | 120.1 |
C2—N2—H2A | 120.0 | C62—C63—H63 | 120.1 |
C2—N2—H2B | 120.0 | C65—C64—C63 | 120.10 (17) |
H2A—N2—H2B | 120.0 | C65—C64—H64 | 119.9 |
C4—N3—C2 | 114.27 (14) | C63—C64—H64 | 119.9 |
N3—C4—C5 | 126.64 (16) | C64—C65—C66 | 120.37 (17) |
N3—C4—Cl4 | 112.61 (12) | C64—C65—H65 | 119.8 |
C5—C4—Cl4 | 120.75 (13) | C66—C65—H65 | 119.8 |
C4—C5—C6 | 113.00 (15) | C65—C66—C61 | 119.64 (17) |
C4—C5—C51 | 123.44 (15) | C65—C66—H66 | 120.2 |
C6—C5—C51 | 122.32 (15) | C61—C66—H66 | 120.2 |
O51—C51—C5 | 126.75 (17) | N61—C67—C68 | 113.75 (15) |
O51—C51—H51 | 116.6 | N61—C67—H67B | 108.8 |
C5—C51—H51 | 116.6 | C68—C67—H67B | 108.8 |
N1—C6—N61 | 115.38 (15) | N61—C67—H67A | 108.8 |
N1—C6—C5 | 121.71 (15) | C68—C67—H67A | 108.8 |
N61—C6—C5 | 122.89 (16) | H67B—C67—H67A | 107.7 |
C6—N61—C61 | 122.50 (14) | C67—C68—H68A | 109.5 |
C6—N61—C67 | 119.41 (14) | C67—C68—H68B | 109.5 |
C61—N61—C67 | 115.77 (13) | H68A—C68—H68B | 109.5 |
C66—C61—C62 | 120.01 (16) | C67—C68—H68C | 109.5 |
C66—C61—N61 | 119.76 (15) | H68A—C68—H68C | 109.5 |
C62—C61—N61 | 120.22 (15) | H68B—C68—H68C | 109.5 |
C63—C62—C61 | 119.95 (17) | | |
| | | |
C6—N1—C2—N2 | 176.06 (16) | N1—C6—N61—C61 | −153.43 (16) |
C6—N1—C2—N3 | −6.0 (3) | C5—C6—N61—C61 | 28.3 (3) |
N2—C2—N3—C4 | −175.28 (15) | N1—C6—N61—C67 | 8.6 (2) |
N1—C2—N3—C4 | 6.7 (3) | C5—C6—N61—C67 | −169.72 (15) |
C2—N3—C4—C5 | 1.2 (3) | C6—N61—C61—C66 | −133.60 (18) |
C2—N3—C4—Cl4 | −179.11 (12) | C67—N61—C61—C66 | 63.8 (2) |
N3—C4—C5—C6 | −8.4 (3) | C6—N61—C61—C62 | 47.1 (2) |
Cl4—C4—C5—C6 | 171.95 (12) | C67—N61—C61—C62 | −115.51 (18) |
N3—C4—C5—C51 | 159.16 (17) | C66—C61—C62—C63 | 2.5 (3) |
Cl4—C4—C5—C51 | −20.5 (2) | N61—C61—C62—C63 | −178.18 (16) |
C4—C5—C51—O51 | 12.0 (3) | C61—C62—C63—C64 | −1.3 (3) |
C6—C5—C51—O51 | 178.33 (18) | C62—C63—C64—C65 | −0.7 (3) |
C2—N1—C6—N61 | 179.15 (15) | C63—C64—C65—C66 | 1.4 (3) |
C2—N1—C6—C5 | −2.6 (2) | C64—C65—C66—C61 | −0.1 (3) |
C4—C5—C6—N1 | 8.9 (2) | C62—C61—C66—C65 | −1.8 (3) |
C51—C5—C6—N1 | −158.77 (16) | N61—C61—C66—C65 | 178.86 (16) |
C4—C5—C6—N61 | −172.94 (16) | C6—N61—C67—C68 | −86.95 (19) |
C51—C5—C6—N61 | 19.4 (3) | C61—N61—C67—C68 | 76.21 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O51i | 0.88 | 2.23 | 3.031 (2) | 152 |
N2—H2B···N3ii | 0.88 | 2.32 | 3.178 (2) | 165 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y, −z+1. |
Crystal data top
C12H11ClN4O | Z = 2 |
Mr = 262.70 | F(000) = 272 |
Triclinic, P1 | Dx = 1.470 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.0568 (7) Å | Cell parameters from 2729 reflections |
b = 8.211 (2) Å | θ = 3.1–27.5° |
c = 10.565 (3) Å | µ = 0.32 mm−1 |
α = 84.590 (16)° | T = 120 K |
β = 82.363 (14)° | Block, colourless |
γ = 78.687 (14)° | 0.41 × 0.20 × 0.13 mm |
V = 593.5 (2) Å3 | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 2729 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 1754 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.061 |
ϕ & ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | h = −9→9 |
Tmin = 0.882, Tmax = 0.960 | k = −10→10 |
15054 measured reflections | l = −13→13 |
Refinement top
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0602P)2 + 0.5473P] where P = (Fo2 + 2Fc2)/3 |
2729 reflections | (Δ/σ)max < 0.001 |
163 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.59 e Å−3 |
Crystal data top
C12H11ClN4O | γ = 78.687 (14)° |
Mr = 262.70 | V = 593.5 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.0568 (7) Å | Mo Kα radiation |
b = 8.211 (2) Å | µ = 0.32 mm−1 |
c = 10.565 (3) Å | T = 120 K |
α = 84.590 (16)° | 0.41 × 0.20 × 0.13 mm |
β = 82.363 (14)° | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 2729 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 1754 reflections with I > 2σ(I) |
Tmin = 0.882, Tmax = 0.960 | Rint = 0.061 |
15054 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.50 e Å−3 |
2729 reflections | Δρmin = −0.59 e Å−3 |
163 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl4 | 0.63213 (10) | 0.04943 (9) | −0.23227 (6) | 0.0276 (2) | |
O51 | 0.1179 (3) | 0.3852 (3) | −0.09322 (19) | 0.0328 (5) | |
N1 | 0.5938 (3) | 0.2896 (3) | 0.1345 (2) | 0.0214 (5) | |
N2 | 0.9020 (3) | 0.1404 (3) | 0.1475 (2) | 0.0281 (6) | |
N3 | 0.7625 (3) | 0.1070 (3) | −0.0284 (2) | 0.0207 (5) | |
N61 | 0.2808 (3) | 0.4306 (3) | 0.1178 (2) | 0.0223 (5) | |
C2 | 0.7471 (4) | 0.1828 (3) | 0.0836 (2) | 0.0215 (6) | |
C4 | 0.6083 (4) | 0.1468 (3) | −0.0899 (2) | 0.0212 (6) | |
C5 | 0.4359 (4) | 0.2557 (3) | −0.0510 (2) | 0.0211 (6) | |
C6 | 0.4376 (4) | 0.3261 (3) | 0.0686 (2) | 0.0201 (6) | |
C51 | 0.2720 (4) | 0.2909 (4) | −0.1231 (3) | 0.0272 (6) | |
C61 | 0.1972 (4) | 0.3800 (3) | 0.3512 (3) | 0.0236 (6) | |
C62 | −0.0008 (4) | 0.3746 (3) | 0.3802 (3) | 0.0255 (6) | |
C63 | −0.0638 (4) | 0.2696 (4) | 0.4798 (3) | 0.0296 (7) | |
C64 | 0.0675 (5) | 0.1682 (4) | 0.5527 (3) | 0.0317 (7) | |
C65 | 0.2640 (5) | 0.1714 (4) | 0.5244 (3) | 0.0328 (7) | |
C66 | 0.3288 (4) | 0.2768 (4) | 0.4246 (3) | 0.0288 (7) | |
C67 | 0.2650 (4) | 0.4976 (3) | 0.2433 (2) | 0.0230 (6) | |
H2A | 1.0005 | 0.0661 | 0.1163 | 0.034* | |
H2B | 0.9094 | 0.1923 | 0.2154 | 0.034* | |
H61 | 0.1563 | 0.4587 | 0.0722 | 0.027* | |
H51 | 0.2838 | 0.2368 | −0.2002 | 0.033* | |
H62 | −0.0926 | 0.4438 | 0.3310 | 0.031* | |
H63 | −0.1987 | 0.2670 | 0.4984 | 0.036* | |
H64 | 0.0232 | 0.0968 | 0.6216 | 0.038* | |
H65 | 0.3550 | 0.1011 | 0.5737 | 0.039* | |
H66 | 0.4639 | 0.2787 | 0.4063 | 0.035* | |
H67A | 0.1722 | 0.6050 | 0.2442 | 0.028* | |
H67B | 0.3935 | 0.5193 | 0.2574 | 0.028* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl4 | 0.0278 (4) | 0.0324 (4) | 0.0228 (4) | −0.0022 (3) | −0.0036 (3) | −0.0087 (3) |
O51 | 0.0226 (10) | 0.0432 (13) | 0.0301 (11) | 0.0039 (9) | −0.0054 (9) | −0.0079 (9) |
N1 | 0.0179 (11) | 0.0255 (12) | 0.0206 (11) | −0.0030 (9) | −0.0016 (9) | −0.0039 (9) |
N2 | 0.0229 (12) | 0.0349 (14) | 0.0257 (13) | 0.0028 (10) | −0.0074 (10) | −0.0095 (11) |
N3 | 0.0188 (11) | 0.0233 (12) | 0.0198 (12) | −0.0022 (9) | −0.0026 (9) | −0.0031 (9) |
N61 | 0.0205 (11) | 0.0255 (12) | 0.0190 (11) | 0.0002 (9) | −0.0010 (9) | −0.0042 (9) |
C2 | 0.0232 (14) | 0.0223 (14) | 0.0192 (14) | −0.0055 (11) | −0.0024 (11) | 0.0000 (11) |
C4 | 0.0231 (14) | 0.0222 (14) | 0.0182 (13) | −0.0052 (11) | 0.0007 (11) | −0.0027 (11) |
C5 | 0.0223 (13) | 0.0237 (14) | 0.0176 (13) | −0.0060 (11) | −0.0012 (11) | −0.0005 (11) |
C6 | 0.0204 (13) | 0.0201 (14) | 0.0195 (13) | −0.0057 (11) | 0.0006 (11) | 0.0000 (11) |
C51 | 0.0255 (15) | 0.0344 (17) | 0.0214 (14) | −0.0031 (13) | −0.0022 (12) | −0.0066 (12) |
C61 | 0.0276 (15) | 0.0225 (14) | 0.0208 (14) | −0.0010 (11) | −0.0033 (11) | −0.0089 (11) |
C62 | 0.0269 (15) | 0.0271 (15) | 0.0229 (15) | −0.0031 (12) | −0.0050 (12) | −0.0057 (12) |
C63 | 0.0321 (16) | 0.0327 (16) | 0.0259 (15) | −0.0096 (13) | −0.0011 (13) | −0.0074 (13) |
C64 | 0.0450 (19) | 0.0282 (16) | 0.0213 (15) | −0.0099 (14) | 0.0033 (13) | −0.0020 (12) |
C65 | 0.0422 (18) | 0.0324 (17) | 0.0216 (15) | 0.0006 (14) | −0.0057 (13) | −0.0040 (12) |
C66 | 0.0263 (15) | 0.0350 (17) | 0.0237 (15) | 0.0019 (13) | −0.0050 (12) | −0.0085 (13) |
C67 | 0.0242 (14) | 0.0242 (15) | 0.0208 (14) | −0.0038 (11) | −0.0011 (11) | −0.0061 (11) |
Geometric parameters (Å, º) top
Cl4—C4 | 1.743 (3) | C51—H51 | 0.95 |
O51—C51 | 1.227 (3) | C61—C66 | 1.394 (4) |
N1—C2 | 1.338 (3) | C61—C62 | 1.398 (4) |
N1—C6 | 1.351 (3) | C61—C67 | 1.513 (4) |
N2—C2 | 1.332 (3) | C62—C63 | 1.380 (4) |
N2—H2A | 0.88 | C62—H62 | 0.95 |
N2—H2B | 0.88 | C63—C64 | 1.382 (4) |
N3—C4 | 1.312 (3) | C63—H63 | 0.95 |
N3—C2 | 1.370 (3) | C64—C65 | 1.384 (4) |
N61—C6 | 1.338 (3) | C64—H64 | 0.95 |
N61—C67 | 1.466 (3) | C65—C66 | 1.388 (4) |
N61—H61 | 1.0337 | C65—H65 | 0.95 |
C4—C5 | 1.399 (4) | C66—H66 | 0.95 |
C5—C51 | 1.437 (4) | C67—H67A | 0.99 |
C5—C6 | 1.440 (4) | C67—H67B | 0.99 |
| | | |
C2—N1—C6 | 116.5 (2) | C66—C61—C67 | 121.1 (3) |
C2—N2—H2A | 118.4 | C62—C61—C67 | 120.3 (2) |
C2—N2—H2B | 120.4 | C63—C62—C61 | 120.5 (3) |
H2A—N2—H2B | 121.0 | C63—C62—H62 | 119.7 |
C4—N3—C2 | 114.7 (2) | C61—C62—H62 | 119.7 |
C6—N61—C67 | 123.3 (2) | C62—C63—C64 | 120.6 (3) |
C6—N61—H61 | 120.7 | C62—C63—H63 | 119.7 |
C67—N61—H61 | 115.7 | C64—C63—H63 | 119.7 |
N2—C2—N1 | 118.3 (2) | C63—C64—C65 | 119.5 (3) |
N2—C2—N3 | 114.9 (2) | C63—C64—H64 | 120.3 |
N1—C2—N3 | 126.9 (2) | C65—C64—H64 | 120.3 |
N3—C4—C5 | 126.2 (2) | C64—C65—C66 | 120.3 (3) |
N3—C4—Cl4 | 113.71 (19) | C64—C65—H65 | 119.8 |
C5—C4—Cl4 | 120.1 (2) | C66—C65—H65 | 119.8 |
C4—C5—C51 | 122.7 (2) | C65—C66—C61 | 120.5 (3) |
C4—C5—C6 | 113.7 (2) | C65—C66—H66 | 119.8 |
C51—C5—C6 | 123.5 (2) | C61—C66—H66 | 119.8 |
N61—C6—N1 | 118.0 (2) | N61—C67—C61 | 112.3 (2) |
N61—C6—C5 | 119.9 (2) | N61—C67—H67A | 109.2 |
N1—C6—C5 | 122.0 (2) | C61—C67—H67A | 109.2 |
O51—C51—C5 | 125.3 (3) | N61—C67—H67B | 109.2 |
O51—C51—H51 | 117.4 | C61—C67—H67B | 109.2 |
C5—C51—H51 | 117.4 | H67A—C67—H67B | 107.9 |
C66—C61—C62 | 118.6 (3) | | |
| | | |
C6—N1—C2—N2 | −178.3 (2) | C4—C5—C6—N1 | 0.6 (4) |
C6—N1—C2—N3 | 0.2 (4) | C51—C5—C6—N1 | 179.5 (2) |
C4—N3—C2—N2 | 178.8 (2) | C4—C5—C51—O51 | 180.0 (3) |
C4—N3—C2—N1 | 0.3 (4) | C6—C5—C51—O51 | 1.2 (5) |
C2—N3—C4—C5 | −0.3 (4) | C66—C61—C62—C63 | 0.2 (4) |
C2—N3—C4—Cl4 | 179.74 (18) | C67—C61—C62—C63 | −178.9 (2) |
N3—C4—C5—C51 | −179.0 (3) | C61—C62—C63—C64 | 0.1 (4) |
Cl4—C4—C5—C51 | 0.9 (4) | C62—C63—C64—C65 | −0.6 (4) |
N3—C4—C5—C6 | −0.1 (4) | C63—C64—C65—C66 | 0.7 (4) |
Cl4—C4—C5—C6 | 179.83 (19) | C64—C65—C66—C61 | −0.4 (4) |
C67—N61—C6—N1 | −4.5 (4) | C62—C61—C66—C65 | 0.0 (4) |
C67—N61—C6—C5 | 175.2 (2) | C67—C61—C66—C65 | 179.1 (2) |
C2—N1—C6—N61 | 179.0 (2) | C6—N61—C67—C61 | −84.3 (3) |
C2—N1—C6—C5 | −0.6 (4) | C66—C61—C67—N61 | 99.4 (3) |
C4—C5—C6—N61 | −179.1 (2) | C62—C61—C67—N61 | −81.5 (3) |
C51—C5—C6—N61 | −0.1 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N3i | 0.88 | 2.14 | 3.020 (3) | 176 |
N61—H61···O51 | 1.03 | 1.97 | 2.727 (3) | 128 |
N61—H61···O51ii | 1.03 | 2.10 | 2.953 (3) | 138 |
Symmetry codes: (i) −x+2, −y, −z; (ii) −x, −y+1, −z. |
Crystal data top
C12H11ClN4O | Z = 2 |
Mr = 262.70 | F(000) = 272 |
Triclinic, P1 | Dx = 1.490 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.9938 (6) Å | Cell parameters from 2681 reflections |
b = 7.9544 (10) Å | θ = 3.3–27.5° |
c = 10.7507 (14) Å | µ = 0.32 mm−1 |
α = 81.191 (11)° | T = 120 K |
β = 82.469 (12)° | Block, colourless |
γ = 87.333 (10)° | 0.37 × 0.27 × 0.18 mm |
V = 585.71 (12) Å3 | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 2681 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 2305 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ϕ & ω scans | θmax = 27.5°, θmin = 3.3° |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | h = −9→9 |
Tmin = 0.891, Tmax = 0.945 | k = −10→10 |
16227 measured reflections | l = −13→13 |
Refinement top
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.086 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0397P)2 + 0.2942P] where P = (Fo2 + 2Fc2)/3 |
2681 reflections | (Δ/σ)max = 0.001 |
164 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Crystal data top
C12H11ClN4O | γ = 87.333 (10)° |
Mr = 262.70 | V = 585.71 (12) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.9938 (6) Å | Mo Kα radiation |
b = 7.9544 (10) Å | µ = 0.32 mm−1 |
c = 10.7507 (14) Å | T = 120 K |
α = 81.191 (11)° | 0.37 × 0.27 × 0.18 mm |
β = 82.469 (12)° | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 2681 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 2305 reflections with I > 2σ(I) |
Tmin = 0.891, Tmax = 0.945 | Rint = 0.030 |
16227 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.086 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.28 e Å−3 |
2681 reflections | Δρmin = −0.28 e Å−3 |
164 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl4 | 0.72228 (5) | 0.49826 (5) | 0.82657 (3) | 0.02217 (11) | |
O51 | 0.35658 (16) | 0.33220 (16) | 0.93484 (10) | 0.0301 (3) | |
N1 | 0.56599 (16) | 0.28146 (14) | 0.49852 (11) | 0.0154 (2) | |
N3 | 0.78362 (16) | 0.42468 (14) | 0.60044 (11) | 0.0157 (2) | |
N2 | 0.84978 (16) | 0.38898 (15) | 0.39177 (11) | 0.0183 (3) | |
N61 | 0.28786 (16) | 0.16274 (15) | 0.60665 (11) | 0.0163 (2) | |
C2 | 0.72857 (19) | 0.36471 (16) | 0.49935 (13) | 0.0148 (3) | |
C4 | 0.65813 (19) | 0.40239 (17) | 0.70477 (13) | 0.0156 (3) | |
C5 | 0.48512 (19) | 0.31854 (17) | 0.71853 (13) | 0.0158 (3) | |
C6 | 0.44858 (19) | 0.25373 (16) | 0.60730 (13) | 0.0148 (3) | |
C51 | 0.3331 (2) | 0.32071 (18) | 0.82711 (13) | 0.0193 (3) | |
C61 | 0.21544 (19) | 0.04117 (17) | 0.71367 (13) | 0.0162 (3) | |
C62 | 0.0172 (2) | 0.02756 (18) | 0.74752 (14) | 0.0198 (3) | |
C63 | −0.0540 (2) | −0.09574 (19) | 0.84624 (14) | 0.0229 (3) | |
C64 | 0.0714 (2) | −0.20491 (19) | 0.91204 (14) | 0.0236 (3) | |
C65 | 0.2691 (2) | −0.18997 (19) | 0.87914 (14) | 0.0224 (3) | |
C66 | 0.3410 (2) | −0.06811 (18) | 0.77910 (13) | 0.0193 (3) | |
C67 | 0.2366 (2) | 0.13208 (18) | 0.48390 (13) | 0.0184 (3) | |
H2A | 0.8277 | 0.3449 | 0.3270 | 0.022* | |
H2B | 0.9553 | 0.4401 | 0.3924 | 0.022* | |
H51 | 0.2039 | 0.3122 | 0.8108 | 0.023* | |
H62 | −0.0692 | 0.1025 | 0.7032 | 0.024* | |
H63 | −0.1894 | −0.1055 | 0.8689 | 0.027* | |
H64 | 0.0220 | −0.2895 | 0.9793 | 0.028* | |
H65 | 0.3554 | −0.2630 | 0.9250 | 0.027* | |
H66 | 0.4763 | −0.0597 | 0.7555 | 0.023* | |
H67A | 0.2741 | 0.2294 | 0.4190 | 0.028* | |
H67B | 0.0971 | 0.1175 | 0.4907 | 0.028* | |
H67C | 0.3046 | 0.0289 | 0.4602 | 0.028* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl4 | 0.02378 (19) | 0.0263 (2) | 0.01806 (18) | −0.00996 (14) | −0.00248 (13) | −0.00566 (13) |
O51 | 0.0298 (6) | 0.0426 (7) | 0.0190 (5) | −0.0145 (5) | 0.0028 (4) | −0.0090 (5) |
N1 | 0.0152 (5) | 0.0134 (5) | 0.0175 (6) | −0.0016 (4) | −0.0020 (4) | −0.0017 (4) |
N3 | 0.0146 (5) | 0.0158 (5) | 0.0165 (6) | −0.0023 (4) | −0.0019 (4) | −0.0010 (4) |
N2 | 0.0140 (6) | 0.0234 (6) | 0.0177 (6) | −0.0048 (5) | 0.0003 (4) | −0.0042 (5) |
N61 | 0.0154 (6) | 0.0168 (6) | 0.0170 (6) | −0.0047 (4) | −0.0028 (4) | −0.0016 (4) |
C2 | 0.0139 (6) | 0.0121 (6) | 0.0178 (6) | 0.0012 (5) | −0.0028 (5) | −0.0001 (5) |
C4 | 0.0167 (6) | 0.0139 (6) | 0.0166 (6) | −0.0008 (5) | −0.0043 (5) | −0.0021 (5) |
C5 | 0.0160 (6) | 0.0150 (6) | 0.0162 (6) | −0.0017 (5) | −0.0023 (5) | −0.0014 (5) |
C6 | 0.0142 (6) | 0.0118 (6) | 0.0181 (6) | 0.0004 (5) | −0.0034 (5) | −0.0006 (5) |
C51 | 0.0192 (7) | 0.0175 (7) | 0.0214 (7) | −0.0070 (5) | 0.0008 (5) | −0.0040 (5) |
C61 | 0.0175 (7) | 0.0151 (6) | 0.0163 (6) | −0.0048 (5) | −0.0007 (5) | −0.0030 (5) |
C62 | 0.0169 (7) | 0.0205 (7) | 0.0220 (7) | −0.0025 (5) | −0.0028 (5) | −0.0021 (6) |
C63 | 0.0174 (7) | 0.0258 (8) | 0.0253 (7) | −0.0074 (6) | 0.0010 (6) | −0.0045 (6) |
C64 | 0.0265 (8) | 0.0226 (7) | 0.0201 (7) | −0.0089 (6) | 0.0012 (6) | 0.0005 (6) |
C65 | 0.0239 (7) | 0.0220 (7) | 0.0206 (7) | −0.0017 (6) | −0.0034 (6) | 0.0001 (6) |
C66 | 0.0165 (7) | 0.0200 (7) | 0.0212 (7) | −0.0031 (5) | −0.0011 (5) | −0.0031 (5) |
C67 | 0.0189 (7) | 0.0189 (7) | 0.0184 (7) | −0.0034 (5) | −0.0058 (5) | −0.0023 (5) |
Geometric parameters (Å, º) top
Cl4—C4 | 1.7289 (14) | C51—H51 | 0.95 |
O51—C51 | 1.2085 (18) | C61—C66 | 1.387 (2) |
N1—C6 | 1.3330 (18) | C61—C62 | 1.3916 (19) |
N1—C2 | 1.3439 (17) | C62—C63 | 1.387 (2) |
N3—C4 | 1.3249 (18) | C62—H62 | 0.95 |
N3—C2 | 1.3574 (17) | C63—C64 | 1.388 (2) |
N2—C2 | 1.3354 (17) | C63—H63 | 0.95 |
N2—H2A | 0.8604 | C64—C65 | 1.388 (2) |
N2—H2B | 0.8602 | C64—H64 | 0.95 |
N61—C6 | 1.3663 (17) | C65—C66 | 1.391 (2) |
N61—C61 | 1.4379 (17) | C65—H65 | 0.95 |
N61—C67 | 1.4697 (17) | C66—H66 | 0.95 |
C4—C5 | 1.3888 (19) | C67—H67A | 0.98 |
C5—C6 | 1.4290 (19) | C67—H67B | 0.98 |
C5—C51 | 1.4739 (19) | C67—H67C | 0.98 |
| | | |
C6—N1—C2 | 117.05 (12) | C66—C61—N61 | 120.56 (12) |
C4—N3—C2 | 114.92 (11) | C62—C61—N61 | 119.47 (12) |
C2—N2—H2A | 120.3 | C63—C62—C61 | 119.82 (13) |
C2—N2—H2B | 117.8 | C63—C62—H62 | 120.1 |
H2A—N2—H2B | 121.6 | C61—C62—H62 | 120.1 |
C6—N61—C61 | 121.73 (11) | C62—C63—C64 | 120.38 (13) |
C6—N61—C67 | 118.38 (11) | C62—C63—H63 | 119.8 |
C61—N61—C67 | 115.00 (11) | C64—C63—H63 | 119.8 |
N2—C2—N1 | 117.52 (12) | C65—C64—C63 | 119.75 (13) |
N2—C2—N3 | 116.41 (12) | C65—C64—H64 | 120.1 |
N1—C2—N3 | 126.06 (12) | C63—C64—H64 | 120.1 |
N3—C4—C5 | 125.55 (12) | C64—C65—C66 | 120.04 (14) |
N3—C4—Cl4 | 113.56 (10) | C64—C65—H65 | 120.0 |
C5—C4—Cl4 | 120.82 (10) | C66—C65—H65 | 120.0 |
C4—C5—C6 | 114.04 (12) | C61—C66—C65 | 120.11 (13) |
C4—C5—C51 | 124.35 (12) | C61—C66—H66 | 119.9 |
C6—C5—C51 | 120.70 (12) | C65—C66—H66 | 119.9 |
N1—C6—N61 | 116.50 (12) | N61—C67—H67A | 109.5 |
N1—C6—C5 | 122.20 (12) | N61—C67—H67B | 109.5 |
N61—C6—C5 | 121.28 (12) | H67A—C67—H67B | 109.5 |
O51—C51—C5 | 126.42 (13) | N61—C67—H67C | 109.5 |
O51—C51—H51 | 116.8 | H67A—C67—H67C | 109.5 |
C5—C51—H51 | 116.8 | H67B—C67—H67C | 109.5 |
C66—C61—C62 | 119.88 (13) | | |
| | | |
C6—N1—C2—N2 | 178.18 (12) | C51—C5—C6—N1 | 165.70 (12) |
C6—N1—C2—N3 | −0.7 (2) | C4—C5—C6—N61 | 177.63 (12) |
C4—N3—C2—N2 | 178.39 (11) | C51—C5—C6—N61 | −12.8 (2) |
C4—N3—C2—N1 | −2.75 (19) | C4—C5—C51—O51 | −30.8 (2) |
C2—N3—C4—C5 | 2.9 (2) | C6—C5—C51—O51 | 160.78 (14) |
C2—N3—C4—Cl4 | −174.10 (9) | C6—N61—C61—C66 | −41.77 (19) |
N3—C4—C5—C6 | 0.1 (2) | C67—N61—C61—C66 | 113.07 (14) |
Cl4—C4—C5—C6 | 176.94 (10) | C6—N61—C61—C62 | 141.53 (13) |
N3—C4—C5—C51 | −168.97 (13) | C67—N61—C61—C62 | −63.63 (17) |
Cl4—C4—C5—C51 | 7.83 (19) | C66—C61—C62—C63 | −0.3 (2) |
C2—N1—C6—N61 | −177.32 (11) | N61—C61—C62—C63 | 176.46 (13) |
C2—N1—C6—C5 | 4.10 (19) | C61—C62—C63—C64 | 0.4 (2) |
C61—N61—C6—N1 | 142.26 (13) | C62—C63—C64—C65 | 0.3 (2) |
C67—N61—C6—N1 | −11.77 (18) | C63—C64—C65—C66 | −1.2 (2) |
C61—N61—C6—C5 | −39.15 (19) | C62—C61—C66—C65 | −0.6 (2) |
C67—N61—C6—C5 | 166.83 (12) | N61—C61—C66—C65 | −177.32 (13) |
C4—C5—C6—N1 | −3.85 (19) | C64—C65—C66—C61 | 1.4 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···Cg2i | 0.86 | 2.74 | 3.5257 (14) | 152 |
N2—H2B···N3ii | 0.86 | 2.18 | 3.0374 (17) | 178 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+2, −y+1, −z+1. |
Crystal data top
C18H15ClN4O | Z = 2 |
Mr = 338.79 | F(000) = 352 |
Triclinic, P1 | Dx = 1.415 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.5520 (11) Å | Cell parameters from 3642 reflections |
b = 11.1012 (7) Å | θ = 3.2–27.5° |
c = 11.4111 (4) Å | µ = 0.25 mm−1 |
α = 79.958 (5)° | T = 120 K |
β = 84.802 (9)° | Plate, yellow |
γ = 77.009 (9)° | 0.58 × 0.48 × 0.05 mm |
V = 795.21 (15) Å3 | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 3642 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 2645 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ϕ & ω scans | θmax = 27.5°, θmin = 3.2° |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | h = −8→8 |
Tmin = 0.867, Tmax = 0.988 | k = −14→14 |
19326 measured reflections | l = −14→14 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0241P)2 + 0.4915P] where P = (Fo2 + 2Fc2)/3 |
3642 reflections | (Δ/σ)max < 0.001 |
217 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Crystal data top
C18H15ClN4O | γ = 77.009 (9)° |
Mr = 338.79 | V = 795.21 (15) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.5520 (11) Å | Mo Kα radiation |
b = 11.1012 (7) Å | µ = 0.25 mm−1 |
c = 11.4111 (4) Å | T = 120 K |
α = 79.958 (5)° | 0.58 × 0.48 × 0.05 mm |
β = 84.802 (9)° | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 3642 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 2645 reflections with I > 2σ(I) |
Tmin = 0.867, Tmax = 0.988 | Rint = 0.038 |
19326 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.26 e Å−3 |
3642 reflections | Δρmin = −0.28 e Å−3 |
217 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl4 | 0.58889 (7) | 0.71360 (4) | 0.30061 (4) | 0.02553 (12) | |
O51 | 0.2480 (2) | 0.64590 (13) | 0.18932 (14) | 0.0371 (4) | |
N1 | 0.6929 (2) | 0.30293 (13) | 0.42419 (12) | 0.0203 (3) | |
N2 | 0.9672 (3) | 0.32794 (14) | 0.52188 (14) | 0.0278 (4) | |
N3 | 0.7843 (2) | 0.50333 (13) | 0.40947 (12) | 0.0200 (3) | |
N61 | 0.4245 (2) | 0.27529 (13) | 0.32288 (13) | 0.0208 (3) | |
C2 | 0.8083 (3) | 0.37920 (16) | 0.45084 (15) | 0.0198 (4) | |
C4 | 0.6211 (3) | 0.55272 (16) | 0.34335 (15) | 0.0190 (4) | |
C5 | 0.4809 (3) | 0.48764 (16) | 0.31274 (15) | 0.0187 (4) | |
C6 | 0.5339 (3) | 0.35550 (16) | 0.35337 (15) | 0.0186 (4) | |
C51 | 0.2800 (3) | 0.54878 (18) | 0.25838 (17) | 0.0259 (4) | |
C61 | 0.6504 (3) | 0.06368 (16) | 0.31124 (17) | 0.0263 (4) | |
C62 | 0.6169 (4) | 0.02933 (18) | 0.20385 (18) | 0.0356 (5) | |
C63 | 0.7806 (4) | −0.03815 (19) | 0.1407 (2) | 0.0470 (6) | |
C64 | 0.9789 (4) | −0.0739 (2) | 0.1842 (2) | 0.0508 (7) | |
C65 | 1.0133 (4) | −0.04222 (19) | 0.2918 (2) | 0.0446 (6) | |
C66 | 0.8506 (3) | 0.02662 (18) | 0.3544 (2) | 0.0333 (5) | |
C67 | 0.4741 (3) | 0.14145 (17) | 0.37834 (17) | 0.0257 (4) | |
C611 | 0.3194 (3) | 0.30034 (16) | 0.21304 (16) | 0.0207 (4) | |
C612 | 0.4158 (3) | 0.34625 (16) | 0.10680 (16) | 0.0228 (4) | |
C613 | 0.3178 (3) | 0.36222 (18) | 0.00097 (18) | 0.0319 (5) | |
C614 | 0.1264 (3) | 0.3295 (2) | 0.0004 (2) | 0.0383 (5) | |
C615 | 0.0322 (3) | 0.2819 (2) | 0.1062 (2) | 0.0367 (5) | |
C616 | 0.1255 (3) | 0.26871 (18) | 0.21285 (19) | 0.0285 (4) | |
H2B | 1.0390 | 0.3778 | 0.5436 | 0.033* | |
H2A | 0.9802 | 0.2494 | 0.5563 | 0.033* | |
H51 | 0.1657 | 0.5082 | 0.2796 | 0.031* | |
H62 | 0.4806 | 0.0524 | 0.1738 | 0.043* | |
H63 | 0.7564 | −0.0600 | 0.0671 | 0.056* | |
H64 | 1.0910 | −0.1199 | 0.1406 | 0.061* | |
H65 | 1.1488 | −0.0678 | 0.3227 | 0.053* | |
H66 | 0.8759 | 0.0488 | 0.4276 | 0.040* | |
H67A | 0.3469 | 0.1066 | 0.3816 | 0.031* | |
H67B | 0.5136 | 0.1355 | 0.4612 | 0.031* | |
H612 | 0.5491 | 0.3668 | 0.1066 | 0.027* | |
H613 | 0.3823 | 0.3958 | −0.0716 | 0.038* | |
H614 | 0.0601 | 0.3397 | −0.0724 | 0.046* | |
H615 | −0.0981 | 0.2580 | 0.1056 | 0.044* | |
H616 | 0.0578 | 0.2382 | 0.2856 | 0.034* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl4 | 0.0330 (3) | 0.0174 (2) | 0.0280 (2) | −0.00704 (18) | −0.00748 (19) | −0.00352 (18) |
O51 | 0.0343 (8) | 0.0247 (8) | 0.0529 (10) | 0.0012 (6) | −0.0203 (7) | −0.0078 (7) |
N1 | 0.0249 (8) | 0.0203 (8) | 0.0180 (7) | −0.0087 (6) | −0.0023 (6) | −0.0030 (6) |
N2 | 0.0389 (10) | 0.0196 (8) | 0.0282 (9) | −0.0108 (7) | −0.0156 (7) | −0.0001 (7) |
N3 | 0.0253 (8) | 0.0201 (8) | 0.0162 (7) | −0.0079 (6) | −0.0031 (6) | −0.0028 (6) |
N61 | 0.0233 (8) | 0.0199 (8) | 0.0223 (8) | −0.0104 (6) | −0.0011 (6) | −0.0043 (6) |
C2 | 0.0250 (9) | 0.0205 (9) | 0.0160 (9) | −0.0078 (7) | −0.0014 (7) | −0.0046 (7) |
C4 | 0.0226 (9) | 0.0184 (9) | 0.0164 (9) | −0.0048 (7) | 0.0019 (7) | −0.0049 (7) |
C5 | 0.0198 (9) | 0.0182 (9) | 0.0190 (9) | −0.0037 (7) | −0.0001 (7) | −0.0067 (7) |
C6 | 0.0202 (9) | 0.0224 (9) | 0.0154 (9) | −0.0081 (7) | 0.0031 (7) | −0.0068 (7) |
C51 | 0.0219 (10) | 0.0241 (10) | 0.0353 (11) | −0.0036 (8) | −0.0032 (8) | −0.0149 (9) |
C61 | 0.0360 (11) | 0.0150 (9) | 0.0289 (10) | −0.0107 (8) | −0.0008 (8) | 0.0008 (7) |
C62 | 0.0540 (14) | 0.0180 (10) | 0.0347 (12) | −0.0063 (9) | −0.0060 (10) | −0.0042 (9) |
C63 | 0.0762 (19) | 0.0210 (11) | 0.0394 (13) | −0.0018 (11) | 0.0030 (12) | −0.0073 (10) |
C64 | 0.0615 (17) | 0.0175 (10) | 0.0638 (17) | −0.0008 (11) | 0.0233 (14) | −0.0039 (11) |
C65 | 0.0407 (13) | 0.0191 (10) | 0.0692 (17) | −0.0063 (9) | 0.0013 (12) | 0.0034 (11) |
C66 | 0.0377 (12) | 0.0190 (9) | 0.0431 (12) | −0.0097 (9) | −0.0044 (10) | 0.0014 (9) |
C67 | 0.0324 (11) | 0.0237 (10) | 0.0252 (10) | −0.0163 (8) | 0.0004 (8) | −0.0026 (8) |
C611 | 0.0197 (9) | 0.0173 (9) | 0.0268 (10) | −0.0030 (7) | −0.0039 (7) | −0.0078 (7) |
C612 | 0.0211 (9) | 0.0212 (9) | 0.0278 (10) | −0.0034 (7) | −0.0044 (8) | −0.0084 (8) |
C613 | 0.0423 (12) | 0.0272 (11) | 0.0278 (11) | −0.0047 (9) | −0.0093 (9) | −0.0084 (8) |
C614 | 0.0408 (13) | 0.0323 (12) | 0.0450 (13) | 0.0024 (10) | −0.0257 (11) | −0.0160 (10) |
C615 | 0.0202 (10) | 0.0340 (11) | 0.0613 (15) | −0.0008 (9) | −0.0138 (10) | −0.0227 (11) |
C616 | 0.0215 (9) | 0.0266 (10) | 0.0417 (12) | −0.0075 (8) | 0.0016 (8) | −0.0155 (9) |
Geometric parameters (Å, º) top
Cl4—C4 | 1.7370 (18) | C63—C64 | 1.381 (4) |
O51—C51 | 1.208 (2) | C63—H63 | 0.95 |
N1—C6 | 1.339 (2) | C64—C65 | 1.385 (3) |
N1—C2 | 1.342 (2) | C64—H64 | 0.95 |
N2—C2 | 1.338 (2) | C65—C66 | 1.384 (3) |
N2—H2B | 0.88 | C65—H65 | 0.95 |
N2—H2A | 0.88 | C66—H66 | 0.95 |
N3—C4 | 1.323 (2) | C67—H67A | 0.99 |
N3—C2 | 1.355 (2) | C67—H67B | 0.99 |
N61—C6 | 1.367 (2) | C611—C612 | 1.385 (3) |
N61—C611 | 1.439 (2) | C611—C616 | 1.392 (2) |
N61—C67 | 1.485 (2) | C612—C613 | 1.385 (3) |
C4—C5 | 1.390 (2) | C612—H612 | 0.95 |
C5—C6 | 1.432 (2) | C613—C614 | 1.382 (3) |
C5—C51 | 1.476 (2) | C613—H613 | 0.95 |
C51—H51 | 0.95 | C614—C615 | 1.381 (3) |
C61—C66 | 1.391 (3) | C614—H614 | 0.95 |
C61—C62 | 1.395 (3) | C615—C616 | 1.382 (3) |
C61—C67 | 1.513 (3) | C615—H615 | 0.95 |
C62—C63 | 1.385 (3) | C616—H616 | 0.95 |
C62—H62 | 0.95 | | |
| | | |
C6—N1—C2 | 116.83 (15) | C63—C64—H64 | 120.2 |
C2—N2—H2B | 118.2 | C65—C64—H64 | 120.2 |
C2—N2—H2A | 118.9 | C66—C65—C64 | 120.2 (2) |
H2B—N2—H2A | 121.8 | C66—C65—H65 | 119.9 |
C4—N3—C2 | 115.06 (14) | C64—C65—H65 | 119.9 |
C6—N61—C611 | 122.46 (15) | C65—C66—C61 | 120.8 (2) |
C6—N61—C67 | 119.02 (15) | C65—C66—H66 | 119.6 |
C611—N61—C67 | 114.93 (13) | C61—C66—H66 | 119.6 |
N2—C2—N1 | 117.43 (16) | N61—C67—C61 | 112.83 (14) |
N2—C2—N3 | 116.26 (15) | N61—C67—H67A | 109.0 |
N1—C2—N3 | 126.26 (16) | C61—C67—H67A | 109.0 |
N3—C4—C5 | 125.49 (16) | N61—C67—H67B | 109.0 |
N3—C4—Cl4 | 113.00 (13) | C61—C67—H67B | 109.0 |
C5—C4—Cl4 | 121.46 (13) | H67A—C67—H67B | 107.8 |
C4—C5—C6 | 113.92 (15) | C612—C611—C616 | 119.88 (17) |
C4—C5—C51 | 123.74 (16) | C612—C611—N61 | 120.80 (15) |
C6—C5—C51 | 121.82 (15) | C616—C611—N61 | 119.13 (17) |
N1—C6—N61 | 115.85 (15) | C613—C612—C611 | 119.92 (17) |
N1—C6—C5 | 122.07 (15) | C613—C612—H612 | 120.0 |
N61—C6—C5 | 122.07 (16) | C611—C612—H612 | 120.0 |
O51—C51—C5 | 125.74 (18) | C614—C613—C612 | 120.3 (2) |
O51—C51—H51 | 117.1 | C614—C613—H613 | 119.9 |
C5—C51—H51 | 117.1 | C612—C613—H613 | 119.9 |
C66—C61—C62 | 118.55 (19) | C615—C614—C613 | 119.67 (19) |
C66—C61—C67 | 120.67 (18) | C615—C614—H614 | 120.2 |
C62—C61—C67 | 120.77 (18) | C613—C614—H614 | 120.2 |
C63—C62—C61 | 120.5 (2) | C614—C615—C616 | 120.66 (19) |
C63—C62—H62 | 119.7 | C614—C615—H615 | 119.7 |
C61—C62—H62 | 119.7 | C616—C615—H615 | 119.7 |
C64—C63—C62 | 120.4 (2) | C615—C616—C611 | 119.56 (19) |
C64—C63—H63 | 119.8 | C615—C616—H616 | 120.2 |
C62—C63—H63 | 119.8 | C611—C616—H616 | 120.2 |
C63—C64—C65 | 119.6 (2) | | |
| | | |
C6—N1—C2—N2 | 179.77 (16) | C67—C61—C62—C63 | 177.74 (18) |
C6—N1—C2—N3 | −2.6 (3) | C61—C62—C63—C64 | 0.9 (3) |
C4—N3—C2—N2 | −177.43 (16) | C62—C63—C64—C65 | 0.2 (3) |
C4—N3—C2—N1 | 4.9 (3) | C63—C64—C65—C66 | −1.1 (3) |
C2—N3—C4—C5 | −1.4 (2) | C64—C65—C66—C61 | 0.8 (3) |
C2—N3—C4—Cl4 | 176.24 (12) | C62—C61—C66—C65 | 0.4 (3) |
N3—C4—C5—C6 | −3.7 (3) | C67—C61—C66—C65 | −178.58 (17) |
Cl4—C4—C5—C6 | 178.86 (12) | C6—N61—C67—C61 | −86.92 (19) |
N3—C4—C5—C51 | 168.10 (17) | C611—N61—C67—C61 | 72.27 (19) |
Cl4—C4—C5—C51 | −9.3 (2) | C66—C61—C67—N61 | 103.74 (19) |
C2—N1—C6—N61 | 177.08 (15) | C62—C61—C67—N61 | −75.2 (2) |
C2—N1—C6—C5 | −3.3 (2) | C6—N61—C611—C612 | 43.4 (2) |
C611—N61—C6—N1 | −151.63 (15) | C67—N61—C611—C612 | −115.03 (18) |
C67—N61—C6—N1 | 5.9 (2) | C6—N61—C611—C616 | −141.62 (17) |
C611—N61—C6—C5 | 28.7 (2) | C67—N61—C611—C616 | 60.0 (2) |
C67—N61—C6—C5 | −173.71 (15) | C616—C611—C612—C613 | 0.9 (3) |
C4—C5—C6—N1 | 6.2 (2) | N61—C611—C612—C613 | 175.89 (16) |
C51—C5—C6—N1 | −165.86 (16) | C611—C612—C613—C614 | −1.7 (3) |
C4—C5—C6—N61 | −174.25 (15) | C612—C613—C614—C615 | 0.6 (3) |
C51—C5—C6—N61 | 13.7 (3) | C613—C614—C615—C616 | 1.1 (3) |
C4—C5—C51—O51 | 34.1 (3) | C614—C615—C616—C611 | −1.9 (3) |
C6—C5—C51—O51 | −154.70 (18) | C612—C611—C616—C615 | 0.8 (3) |
C66—C61—C62—C63 | −1.2 (3) | N61—C611—C616—C615 | −174.22 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2B···N3i | 0.88 | 2.10 | 2.981 (2) | 178 |
C614—H614···O51ii | 0.95 | 2.48 | 3.352 (3) | 153 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x, −y+1, −z. |
Crystal data top
C15H12ClN5O | F(000) = 648 |
Mr = 313.75 | Dx = 1.514 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3149 reflections |
a = 7.5716 (7) Å | θ = 3.1–27.5° |
b = 16.6432 (18) Å | µ = 0.29 mm−1 |
c = 10.9450 (7) Å | T = 120 K |
β = 93.549 (6)° | Lath, colourless |
V = 1376.6 (2) Å3 | 0.51 × 0.25 × 0.10 mm |
Z = 4 | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 3149 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 2236 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
ϕ & ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | h = −9→9 |
Tmin = 0.867, Tmax = 0.972 | k = −21→21 |
32885 measured reflections | l = −14→14 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0507P)2 + 1.2389P] where P = (Fo2 + 2Fc2)/3 |
3149 reflections | (Δ/σ)max < 0.001 |
199 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.48 e Å−3 |
Crystal data top
C15H12ClN5O | V = 1376.6 (2) Å3 |
Mr = 313.75 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.5716 (7) Å | µ = 0.29 mm−1 |
b = 16.6432 (18) Å | T = 120 K |
c = 10.9450 (7) Å | 0.51 × 0.25 × 0.10 mm |
β = 93.549 (6)° | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 3149 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 2236 reflections with I > 2σ(I) |
Tmin = 0.867, Tmax = 0.972 | Rint = 0.057 |
32885 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.11 | Δρmax = 0.36 e Å−3 |
3149 reflections | Δρmin = −0.48 e Å−3 |
199 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl4 | 0.28800 (8) | 0.36592 (3) | 0.23753 (5) | 0.02223 (16) | |
O51 | 0.1645 (2) | 0.13615 (9) | 0.38717 (14) | 0.0212 (4) | |
N1 | 0.3950 (2) | 0.31159 (10) | 0.63242 (16) | 0.0174 (4) | |
N2 | 0.5171 (3) | 0.43677 (11) | 0.64767 (16) | 0.0210 (4) | |
N3 | 0.3967 (2) | 0.40048 (10) | 0.45792 (16) | 0.0171 (4) | |
N61 | 0.2690 (2) | 0.18541 (10) | 0.61607 (16) | 0.0182 (4) | |
N62 | 0.3305 (2) | 0.02393 (11) | 0.68429 (16) | 0.0186 (4) | |
C2 | 0.4343 (3) | 0.38122 (13) | 0.57843 (19) | 0.0170 (4) | |
C4 | 0.3260 (3) | 0.34162 (13) | 0.39188 (19) | 0.0170 (4) | |
C5 | 0.2806 (3) | 0.26535 (13) | 0.43352 (19) | 0.0166 (4) | |
C6 | 0.3158 (3) | 0.25521 (12) | 0.56319 (19) | 0.0162 (4) | |
C51 | 0.2037 (3) | 0.20430 (13) | 0.3539 (2) | 0.0195 (5) | |
C61 | 0.2949 (3) | 0.16556 (13) | 0.74230 (19) | 0.0166 (4) | |
C62 | 0.3306 (3) | 0.08584 (13) | 0.7749 (2) | 0.0175 (4) | |
C63 | 0.3638 (3) | 0.06497 (14) | 0.8970 (2) | 0.0211 (5) | |
C64 | 0.3618 (3) | 0.12309 (14) | 0.9881 (2) | 0.0230 (5) | |
C65 | 0.3172 (3) | 0.20096 (14) | 0.9559 (2) | 0.0227 (5) | |
C66 | 0.2827 (3) | 0.22276 (13) | 0.8345 (2) | 0.0210 (5) | |
C622 | 0.1825 (3) | −0.00186 (13) | 0.6163 (2) | 0.0196 (5) | |
C623 | 0.2245 (3) | −0.07029 (13) | 0.5560 (2) | 0.0211 (5) | |
C624 | 0.4045 (3) | −0.08700 (13) | 0.5875 (2) | 0.0228 (5) | |
C625 | 0.4664 (3) | −0.02910 (13) | 0.6674 (2) | 0.0222 (5) | |
H2A | 0.5392 | 0.4259 | 0.7239 | 0.025* | |
H2B | 0.5399 | 0.4828 | 0.6166 | 0.025* | |
H61 | 0.2321 | 0.1495 | 0.5641 | 0.022* | |
H51 | 0.1817 | 0.2174 | 0.2699 | 0.023* | |
H63 | 0.3881 | 0.0106 | 0.9184 | 0.025* | |
H64 | 0.3907 | 0.1094 | 1.0712 | 0.028* | |
H65 | 0.3101 | 0.2404 | 1.0181 | 0.027* | |
H66 | 0.2507 | 0.2765 | 0.8142 | 0.025* | |
H622 | 0.0700 | 0.0237 | 0.6120 | 0.024* | |
H623 | 0.1472 | −0.1010 | 0.5027 | 0.025* | |
H624 | 0.4706 | −0.1307 | 0.5584 | 0.027* | |
H625 | 0.5828 | −0.0259 | 0.7049 | 0.027* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl4 | 0.0292 (3) | 0.0221 (3) | 0.0151 (3) | −0.0020 (2) | −0.0017 (2) | 0.0040 (2) |
O51 | 0.0244 (9) | 0.0175 (8) | 0.0210 (8) | −0.0033 (6) | −0.0031 (6) | −0.0002 (6) |
N1 | 0.0217 (10) | 0.0137 (9) | 0.0168 (9) | −0.0006 (7) | 0.0003 (7) | −0.0001 (7) |
N2 | 0.0321 (11) | 0.0165 (9) | 0.0143 (9) | −0.0030 (8) | −0.0006 (8) | 0.0016 (7) |
N3 | 0.0215 (10) | 0.0150 (9) | 0.0147 (9) | −0.0006 (7) | 0.0003 (7) | 0.0017 (7) |
N61 | 0.0259 (11) | 0.0130 (9) | 0.0155 (9) | −0.0008 (7) | −0.0001 (7) | 0.0010 (7) |
N62 | 0.0201 (10) | 0.0159 (9) | 0.0196 (9) | 0.0006 (7) | 0.0011 (7) | 0.0020 (7) |
C2 | 0.0181 (11) | 0.0164 (10) | 0.0166 (10) | 0.0029 (8) | 0.0023 (8) | −0.0004 (8) |
C4 | 0.0164 (11) | 0.0192 (11) | 0.0154 (10) | 0.0020 (8) | −0.0005 (8) | 0.0016 (8) |
C5 | 0.0176 (11) | 0.0175 (11) | 0.0147 (10) | 0.0001 (8) | −0.0001 (8) | 0.0004 (8) |
C6 | 0.0161 (11) | 0.0159 (10) | 0.0165 (11) | 0.0019 (8) | 0.0011 (8) | 0.0011 (8) |
C51 | 0.0195 (12) | 0.0211 (12) | 0.0175 (11) | −0.0001 (9) | −0.0010 (9) | 0.0019 (9) |
C61 | 0.0162 (11) | 0.0169 (10) | 0.0167 (10) | −0.0015 (8) | 0.0015 (8) | 0.0029 (8) |
C62 | 0.0175 (11) | 0.0165 (10) | 0.0184 (10) | −0.0020 (9) | 0.0008 (8) | −0.0023 (8) |
C63 | 0.0212 (12) | 0.0176 (11) | 0.0243 (12) | 0.0022 (9) | −0.0010 (9) | 0.0054 (9) |
C64 | 0.0254 (13) | 0.0288 (12) | 0.0145 (10) | −0.0031 (10) | −0.0008 (9) | 0.0022 (9) |
C65 | 0.0275 (13) | 0.0229 (12) | 0.0180 (11) | −0.0052 (10) | 0.0041 (9) | −0.0026 (9) |
C66 | 0.0272 (13) | 0.0153 (11) | 0.0211 (11) | −0.0002 (9) | 0.0056 (9) | 0.0014 (9) |
C622 | 0.0201 (11) | 0.0190 (11) | 0.0194 (11) | −0.0010 (9) | −0.0007 (9) | 0.0017 (9) |
C623 | 0.0278 (13) | 0.0185 (11) | 0.0170 (11) | −0.0020 (9) | 0.0009 (9) | 0.0001 (9) |
C624 | 0.0249 (13) | 0.0175 (11) | 0.0269 (12) | 0.0018 (9) | 0.0081 (10) | −0.0012 (9) |
C625 | 0.0209 (12) | 0.0199 (11) | 0.0256 (12) | 0.0037 (9) | 0.0010 (9) | 0.0016 (9) |
Geometric parameters (Å, º) top
Cl4—C4 | 1.744 (2) | C51—H51 | 0.95 |
O51—C51 | 1.233 (3) | C61—C66 | 1.395 (3) |
N1—C6 | 1.326 (3) | C61—C62 | 1.396 (3) |
N1—C2 | 1.343 (3) | C62—C63 | 1.389 (3) |
N2—C2 | 1.328 (3) | C63—C64 | 1.390 (3) |
N2—H2A | 0.8599 | C63—H63 | 0.95 |
N2—H2B | 0.8599 | C64—C65 | 1.379 (3) |
N3—C4 | 1.312 (3) | C64—H64 | 0.95 |
N3—C2 | 1.370 (3) | C65—C66 | 1.386 (3) |
N61—C6 | 1.355 (3) | C65—H65 | 0.95 |
N61—C61 | 1.422 (3) | C66—H66 | 0.95 |
N61—H61 | 0.86 | C622—C623 | 1.364 (3) |
N62—C622 | 1.375 (3) | C622—H622 | 0.95 |
N62—C625 | 1.377 (3) | C623—C624 | 1.413 (3) |
N62—C62 | 1.430 (3) | C623—H623 | 0.95 |
C4—C5 | 1.399 (3) | C624—C625 | 1.365 (3) |
C5—C6 | 1.438 (3) | C624—H624 | 0.95 |
C5—C51 | 1.438 (3) | C625—H625 | 0.95 |
| | | |
C6—N1—C2 | 117.65 (18) | C62—C61—N61 | 118.80 (19) |
C2—N2—H2A | 117.7 | C63—C62—C61 | 120.3 (2) |
C2—N2—H2B | 119.6 | C63—C62—N62 | 118.65 (19) |
H2A—N2—H2B | 122.6 | C61—C62—N62 | 121.07 (19) |
C4—N3—C2 | 114.16 (18) | C62—C63—C64 | 120.5 (2) |
C6—N61—C61 | 126.15 (18) | C62—C63—H63 | 119.8 |
C6—N61—H61 | 113.4 | C64—C63—H63 | 119.8 |
C61—N61—H61 | 120.1 | C65—C64—C63 | 118.9 (2) |
C622—N62—C625 | 108.57 (18) | C65—C64—H64 | 120.5 |
C622—N62—C62 | 124.45 (18) | C63—C64—H64 | 120.5 |
C625—N62—C62 | 125.90 (19) | C64—C65—C66 | 121.3 (2) |
N2—C2—N1 | 117.34 (19) | C64—C65—H65 | 119.4 |
N2—C2—N3 | 116.70 (19) | C66—C65—H65 | 119.4 |
N1—C2—N3 | 125.96 (19) | C65—C66—C61 | 119.9 (2) |
N3—C4—C5 | 126.74 (19) | C65—C66—H66 | 120.1 |
N3—C4—Cl4 | 113.45 (16) | C61—C66—H66 | 120.1 |
C5—C4—Cl4 | 119.81 (16) | C623—C622—N62 | 108.4 (2) |
C4—C5—C6 | 113.21 (18) | C623—C622—H622 | 125.8 |
C4—C5—C51 | 122.83 (19) | N62—C622—H622 | 125.8 |
C6—C5—C51 | 123.96 (19) | C622—C623—C624 | 107.3 (2) |
N1—C6—N61 | 118.93 (18) | C622—C623—H623 | 126.4 |
N1—C6—C5 | 122.05 (19) | C624—C623—H623 | 126.4 |
N61—C6—C5 | 119.01 (19) | C625—C624—C623 | 107.8 (2) |
O51—C51—C5 | 124.5 (2) | C625—C624—H624 | 126.1 |
O51—C51—H51 | 117.7 | C623—C624—H624 | 126.1 |
C5—C51—H51 | 117.7 | C624—C625—N62 | 108.0 (2) |
C66—C61—C62 | 118.97 (19) | C624—C625—H625 | 126.0 |
C66—C61—N61 | 122.21 (19) | N62—C625—H625 | 126.0 |
| | | |
C6—N1—C2—N2 | −178.58 (19) | C66—C61—C62—C63 | −3.9 (3) |
C6—N1—C2—N3 | 1.5 (3) | N61—C61—C62—C63 | 177.3 (2) |
C4—N3—C2—N2 | 175.57 (19) | C66—C61—C62—N62 | 175.0 (2) |
C4—N3—C2—N1 | −4.5 (3) | N61—C61—C62—N62 | −3.8 (3) |
C2—N3—C4—C5 | 2.9 (3) | C622—N62—C62—C63 | 111.5 (2) |
C2—N3—C4—Cl4 | −177.37 (15) | C625—N62—C62—C63 | −55.3 (3) |
N3—C4—C5—C6 | 1.2 (3) | C622—N62—C62—C61 | −67.4 (3) |
Cl4—C4—C5—C6 | −178.50 (16) | C625—N62—C62—C61 | 125.9 (2) |
N3—C4—C5—C51 | −179.8 (2) | C61—C62—C63—C64 | 0.1 (3) |
Cl4—C4—C5—C51 | 0.5 (3) | N62—C62—C63—C64 | −178.8 (2) |
C2—N1—C6—N61 | −177.72 (19) | C62—C63—C64—C65 | 3.3 (3) |
C2—N1—C6—C5 | 3.3 (3) | C63—C64—C65—C66 | −3.0 (4) |
C61—N61—C6—N1 | 0.6 (3) | C64—C65—C66—C61 | −0.8 (4) |
C61—N61—C6—C5 | 179.6 (2) | C62—C61—C66—C65 | 4.2 (3) |
C4—C5—C6—N1 | −4.5 (3) | N61—C61—C66—C65 | −177.0 (2) |
C51—C5—C6—N1 | 176.5 (2) | C625—N62—C622—C623 | −0.5 (2) |
C4—C5—C6—N61 | 176.52 (19) | C62—N62—C622—C623 | −169.19 (19) |
C51—C5—C6—N61 | −2.4 (3) | N62—C622—C623—C624 | −0.2 (2) |
C4—C5—C51—O51 | 178.9 (2) | C622—C623—C624—C625 | 0.9 (3) |
C6—C5—C51—O51 | −2.2 (4) | C623—C624—C625—N62 | −1.2 (3) |
C6—N61—C61—C66 | 35.0 (3) | C622—N62—C625—C624 | 1.1 (2) |
C6—N61—C61—C62 | −146.3 (2) | C62—N62—C625—C624 | 169.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O51i | 0.86 | 2.22 | 3.038 (2) | 158 |
N2—H2B···N3ii | 0.86 | 2.17 | 3.032 (3) | 178 |
N61—H61···O51 | 0.86 | 1.98 | 2.707 (2) | 141 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z+1. |
Crystal data top
C11H16ClN5O2 | Z = 2 |
Mr = 285.74 | F(000) = 300 |
Triclinic, P1 | Dx = 1.480 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.2147 (6) Å | Cell parameters from 2936 reflections |
b = 8.8563 (10) Å | θ = 4.0–27.5° |
c = 10.2855 (12) Å | µ = 0.31 mm−1 |
α = 84.856 (10)° | T = 120 K |
β = 85.296 (10)° | Block, colourless |
γ = 79.092 (7)° | 0.58 × 0.29 × 0.22 mm |
V = 641.28 (12) Å3 | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 2936 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 2402 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ϕ & ω scans | θmax = 27.5°, θmin = 4.0° |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | h = −9→9 |
Tmin = 0.843, Tmax = 0.936 | k = −11→11 |
15336 measured reflections | l = −13→13 |
Refinement top
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) = 0.102 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0442P)2 + 0.4199P] where P = (Fo2 + 2Fc2)/3 |
2936 reflections | (Δ/σ)max = 0.001 |
173 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Crystal data top
C11H16ClN5O2 | γ = 79.092 (7)° |
Mr = 285.74 | V = 641.28 (12) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.2147 (6) Å | Mo Kα radiation |
b = 8.8563 (10) Å | µ = 0.31 mm−1 |
c = 10.2855 (12) Å | T = 120 K |
α = 84.856 (10)° | 0.58 × 0.29 × 0.22 mm |
β = 85.296 (10)° | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 2936 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 2402 reflections with I > 2σ(I) |
Tmin = 0.843, Tmax = 0.936 | Rint = 0.024 |
15336 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 1.13 | Δρmax = 0.31 e Å−3 |
2936 reflections | Δρmin = −0.27 e Å−3 |
173 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 1.03833 (19) | 0.19931 (16) | 0.42088 (13) | 0.0173 (3) | |
C2 | 1.2103 (2) | 0.12399 (18) | 0.45074 (15) | 0.0171 (3) | |
N2 | 1.27779 (19) | 0.14946 (17) | 0.56113 (13) | 0.0209 (3) | |
N3 | 1.32379 (18) | 0.01454 (15) | 0.37787 (13) | 0.0161 (3) | |
C4 | 1.2683 (2) | 0.00979 (18) | 0.26145 (16) | 0.0161 (3) | |
Cl4 | 1.42263 (5) | −0.12121 (5) | 0.16646 (4) | 0.02160 (13) | |
C5 | 1.1057 (2) | 0.09739 (18) | 0.20756 (15) | 0.0152 (3) | |
C51 | 1.1005 (2) | 0.12611 (19) | 0.06761 (16) | 0.0186 (3) | |
O51 | 0.98395 (17) | 0.21939 (15) | 0.00677 (12) | 0.0249 (3) | |
C6 | 0.9799 (2) | 0.18337 (18) | 0.30393 (15) | 0.0151 (3) | |
N61 | 0.80235 (18) | 0.25359 (15) | 0.27918 (13) | 0.0156 (3) | |
C62 | 0.6818 (2) | 0.18210 (19) | 0.20446 (16) | 0.0181 (3) | |
C65 | 0.5348 (2) | 0.46549 (19) | 0.31328 (16) | 0.0191 (3) | |
C63 | 0.5254 (2) | 0.30174 (19) | 0.14700 (16) | 0.0174 (3) | |
N64 | 0.41036 (18) | 0.38617 (15) | 0.25008 (13) | 0.0158 (3) | |
C641 | 0.2497 (2) | 0.49297 (19) | 0.19543 (15) | 0.0174 (3) | |
C642 | 0.1194 (2) | 0.57779 (19) | 0.29963 (16) | 0.0182 (3) | |
O64 | −0.05701 (16) | 0.65227 (15) | 0.24939 (12) | 0.0221 (3) | |
C66 | 0.6914 (2) | 0.3512 (2) | 0.37695 (16) | 0.0193 (3) | |
H2A | 1.2098 | 0.2151 | 0.6136 | 0.025* | |
H2B | 1.3906 | 0.1008 | 0.5820 | 0.025* | |
H51 | 1.1983 | 0.0662 | 0.0166 | 0.022* | |
H62A | 0.6257 | 0.1049 | 0.2626 | 0.022* | |
H62B | 0.7598 | 0.1279 | 0.1330 | 0.022* | |
H65A | 0.4598 | 0.5291 | 0.3805 | 0.023* | |
H65B | 0.5910 | 0.5352 | 0.2474 | 0.023* | |
H63A | 0.5812 | 0.3748 | 0.0841 | 0.021* | |
H63B | 0.4444 | 0.2504 | 0.0990 | 0.021* | |
H64A | 0.1764 | 0.4345 | 0.1477 | 0.021* | |
H64B | 0.2981 | 0.5693 | 0.1317 | 0.021* | |
H64C | 0.0954 | 0.5037 | 0.3742 | 0.022* | |
H64D | 0.1821 | 0.6559 | 0.3323 | 0.022* | |
H64 | −0.0367 | 0.6977 | 0.1758 | 0.026* | |
H66A | 0.7752 | 0.4075 | 0.4174 | 0.023* | |
H66B | 0.6358 | 0.2857 | 0.4468 | 0.023* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0137 (6) | 0.0198 (7) | 0.0167 (7) | 0.0008 (5) | −0.0012 (5) | −0.0006 (5) |
C2 | 0.0144 (7) | 0.0186 (8) | 0.0164 (8) | 0.0004 (6) | −0.0003 (6) | 0.0007 (6) |
N2 | 0.0159 (7) | 0.0259 (8) | 0.0175 (7) | 0.0063 (6) | −0.0031 (5) | −0.0035 (6) |
N3 | 0.0135 (6) | 0.0162 (7) | 0.0170 (7) | 0.0003 (5) | −0.0006 (5) | 0.0003 (5) |
C4 | 0.0129 (7) | 0.0150 (7) | 0.0202 (8) | −0.0025 (6) | 0.0014 (6) | −0.0025 (6) |
Cl4 | 0.0182 (2) | 0.0203 (2) | 0.0248 (2) | 0.00261 (15) | −0.00083 (15) | −0.00750 (16) |
C5 | 0.0127 (7) | 0.0153 (7) | 0.0179 (8) | −0.0024 (6) | −0.0006 (6) | −0.0035 (6) |
C51 | 0.0162 (7) | 0.0207 (8) | 0.0193 (8) | −0.0026 (6) | −0.0012 (6) | −0.0060 (6) |
O51 | 0.0227 (6) | 0.0308 (7) | 0.0187 (6) | 0.0012 (5) | −0.0037 (5) | −0.0002 (5) |
C6 | 0.0134 (7) | 0.0133 (7) | 0.0179 (8) | −0.0018 (6) | −0.0004 (6) | −0.0003 (6) |
N61 | 0.0113 (6) | 0.0175 (7) | 0.0174 (7) | 0.0007 (5) | −0.0021 (5) | −0.0052 (5) |
C62 | 0.0140 (7) | 0.0192 (8) | 0.0211 (8) | −0.0013 (6) | −0.0024 (6) | −0.0041 (6) |
C65 | 0.0151 (7) | 0.0208 (8) | 0.0202 (8) | 0.0031 (6) | −0.0032 (6) | −0.0070 (6) |
C63 | 0.0153 (7) | 0.0211 (8) | 0.0159 (8) | −0.0026 (6) | −0.0006 (6) | −0.0040 (6) |
N64 | 0.0115 (6) | 0.0189 (7) | 0.0160 (6) | 0.0016 (5) | −0.0015 (5) | −0.0036 (5) |
C641 | 0.0155 (7) | 0.0200 (8) | 0.0157 (7) | 0.0002 (6) | −0.0023 (6) | −0.0017 (6) |
C642 | 0.0151 (7) | 0.0213 (8) | 0.0159 (8) | 0.0026 (6) | −0.0012 (6) | −0.0015 (6) |
O64 | 0.0154 (6) | 0.0283 (7) | 0.0189 (6) | 0.0057 (5) | −0.0023 (4) | −0.0012 (5) |
C66 | 0.0149 (7) | 0.0238 (8) | 0.0176 (8) | 0.0039 (6) | −0.0024 (6) | −0.0072 (6) |
Geometric parameters (Å, º) top
N1—C6 | 1.334 (2) | C62—H62B | 0.99 |
N1—C2 | 1.338 (2) | C65—N64 | 1.462 (2) |
C2—N2 | 1.325 (2) | C65—C66 | 1.517 (2) |
C2—N3 | 1.379 (2) | C65—H65A | 0.99 |
N2—H2A | 0.88 | C65—H65B | 0.99 |
N2—H2B | 0.88 | C63—N64 | 1.461 (2) |
N3—C4 | 1.300 (2) | C63—H63A | 0.99 |
C4—C5 | 1.404 (2) | C63—H63B | 0.99 |
C4—Cl4 | 1.7537 (16) | N64—C641 | 1.4663 (19) |
C5—C51 | 1.441 (2) | C641—C642 | 1.520 (2) |
C5—C6 | 1.453 (2) | C641—H64A | 0.99 |
C51—O51 | 1.230 (2) | C641—H64B | 0.99 |
C51—H51 | 0.95 | C642—O64 | 1.4322 (19) |
C6—N61 | 1.348 (2) | C642—H64C | 0.99 |
N61—C62 | 1.467 (2) | C642—H64D | 0.99 |
N61—C66 | 1.470 (2) | O64—H64 | 0.84 |
C62—C63 | 1.513 (2) | C66—H66A | 0.99 |
C62—H62A | 0.99 | C66—H66B | 0.99 |
| | | |
C6—N1—C2 | 118.17 (14) | N64—C65—H65B | 109.4 |
N2—C2—N1 | 119.01 (14) | C66—C65—H65B | 109.4 |
N2—C2—N3 | 115.72 (14) | H65A—C65—H65B | 108.0 |
N1—C2—N3 | 125.21 (15) | N64—C63—C62 | 110.64 (13) |
C2—N2—H2A | 120.0 | N64—C63—H63A | 109.5 |
C2—N2—H2B | 120.0 | C62—C63—H63A | 109.5 |
H2A—N2—H2B | 120.0 | N64—C63—H63B | 109.5 |
C4—N3—C2 | 113.99 (13) | C62—C63—H63B | 109.5 |
N3—C4—C5 | 127.20 (15) | H63A—C63—H63B | 108.1 |
N3—C4—Cl4 | 113.34 (12) | C63—N64—C65 | 107.16 (12) |
C5—C4—Cl4 | 119.45 (12) | C63—N64—C641 | 110.50 (12) |
C4—C5—C51 | 119.74 (14) | C65—N64—C641 | 112.43 (13) |
C4—C5—C6 | 112.50 (14) | N64—C641—C642 | 112.68 (13) |
C51—C5—C6 | 125.62 (14) | N64—C641—H64A | 109.1 |
O51—C51—C5 | 127.38 (15) | C642—C641—H64A | 109.1 |
O51—C51—H51 | 116.3 | N64—C641—H64B | 109.1 |
C5—C51—H51 | 116.3 | C642—C641—H64B | 109.1 |
N1—C6—N61 | 116.93 (14) | H64A—C641—H64B | 107.8 |
N1—C6—C5 | 120.81 (14) | O64—C642—C641 | 111.48 (13) |
N61—C6—C5 | 122.24 (14) | O64—C642—H64C | 109.3 |
C6—N61—C62 | 121.65 (13) | C641—C642—H64C | 109.3 |
C6—N61—C66 | 118.69 (13) | O64—C642—H64D | 109.3 |
C62—N61—C66 | 111.99 (12) | C641—C642—H64D | 109.3 |
N61—C62—C63 | 111.10 (13) | H64C—C642—H64D | 108.0 |
N61—C62—H62A | 109.4 | C642—O64—H64 | 109.5 |
C63—C62—H62A | 109.4 | N61—C66—C65 | 110.30 (13) |
N61—C62—H62B | 109.4 | N61—C66—H66A | 109.6 |
C63—C62—H62B | 109.4 | C65—C66—H66A | 109.6 |
H62A—C62—H62B | 108.0 | N61—C66—H66B | 109.6 |
N64—C65—C66 | 111.08 (13) | C65—C66—H66B | 109.6 |
N64—C65—H65A | 109.4 | H66A—C66—H66B | 108.1 |
C66—C65—H65A | 109.4 | | |
| | | |
C6—N1—C2—N2 | 173.82 (15) | N1—C6—N61—C62 | −142.52 (15) |
C6—N1—C2—N3 | −9.1 (2) | C5—C6—N61—C62 | 39.2 (2) |
N2—C2—N3—C4 | −169.67 (14) | N1—C6—N61—C66 | 4.5 (2) |
N1—C2—N3—C4 | 13.1 (2) | C5—C6—N61—C66 | −173.85 (14) |
C2—N3—C4—C5 | −3.0 (2) | C6—N61—C62—C63 | −158.67 (14) |
C2—N3—C4—Cl4 | 176.10 (11) | C66—N61—C62—C63 | 52.35 (17) |
N3—C4—C5—C51 | 155.15 (16) | N61—C62—C63—N64 | −57.80 (17) |
Cl4—C4—C5—C51 | −23.9 (2) | C62—C63—N64—C65 | 61.88 (16) |
N3—C4—C5—C6 | −9.2 (2) | C62—C63—N64—C641 | −175.31 (13) |
Cl4—C4—C5—C6 | 171.78 (11) | C66—C65—N64—C63 | −62.39 (17) |
C4—C5—C51—O51 | −167.22 (16) | C66—C65—N64—C641 | 176.01 (13) |
C6—C5—C51—O51 | −5.1 (3) | C63—N64—C641—C642 | 176.97 (13) |
C2—N1—C6—N61 | 176.47 (14) | C65—N64—C641—C642 | −63.35 (17) |
C2—N1—C6—C5 | −5.2 (2) | N64—C641—C642—O64 | −166.20 (13) |
C4—C5—C6—N1 | 13.3 (2) | C6—N61—C66—C65 | 157.87 (14) |
C51—C5—C6—N1 | −149.95 (16) | C62—N61—C66—C65 | −52.14 (18) |
C4—C5—C6—N61 | −168.45 (14) | N64—C65—C66—N61 | 58.05 (18) |
C51—C5—C6—N61 | 28.3 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O64i | 0.88 | 2.03 | 2.909 (2) | 174 |
N2—H2B···N3ii | 0.88 | 2.17 | 3.053 (2) | 177 |
O64—H64···O51iii | 0.84 | 1.99 | 2.824 (2) | 173 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3, −y, −z+1; (iii) −x+1, −y+1, −z. |
Crystal data top
C10H13ClN4O | F(000) = 504 |
Mr = 240.69 | Dx = 1.488 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 2460 reflections |
a = 14.4681 (17) Å | θ = 4.4–27.5° |
b = 11.1378 (17) Å | µ = 0.34 mm−1 |
c = 7.4534 (7) Å | T = 120 K |
β = 116.535 (7)° | Block, colourless |
V = 1074.5 (2) Å3 | 0.30 × 0.26 × 0.15 mm |
Z = 4 | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 2460 independent reflections |
Radiation source: Bruker-Nonius FR591 rotating anode | 1972 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
ϕ & ω scans | θmax = 27.5°, θmin = 4.4° |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | h = −18→18 |
Tmin = 0.896, Tmax = 0.951 | k = −14→14 |
12891 measured reflections | l = −9→9 |
Refinement top
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)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.0345P)2 + 0.8328P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max < 0.001 |
2460 reflections | Δρmax = 0.33 e Å−3 |
145 parameters | Δρmin = −0.28 e Å−3 |
2 restraints | Absolute structure: Flack (1983), 1219 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.07 (7) |
Crystal data top
C10H13ClN4O | V = 1074.5 (2) Å3 |
Mr = 240.69 | Z = 4 |
Monoclinic, Cc | Mo Kα radiation |
a = 14.4681 (17) Å | µ = 0.34 mm−1 |
b = 11.1378 (17) Å | T = 120 K |
c = 7.4534 (7) Å | 0.30 × 0.26 × 0.15 mm |
β = 116.535 (7)° | |
Data collection top
Bruker-Nonius KappaCCD diffractometer | 2460 independent reflections |
Absorption correction: multi-scan SADABS 2.10 (Sheldrick, 2003) | 1972 reflections with I > 2σ(I) |
Tmin = 0.896, Tmax = 0.951 | Rint = 0.050 |
12891 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.087 | Δρmax = 0.33 e Å−3 |
S = 1.11 | Δρmin = −0.28 e Å−3 |
2460 reflections | Absolute structure: Flack (1983), 1219 Friedel pairs |
145 parameters | Absolute structure parameter: 0.07 (7) |
2 restraints | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.59294 (17) | 0.3488 (2) | 0.4572 (3) | 0.0161 (5) | |
N2 | 0.51703 (17) | 0.4914 (2) | 0.5696 (3) | 0.0219 (5) | |
C2 | 0.6028 (2) | 0.4360 (2) | 0.5881 (4) | 0.0173 (5) | |
N3 | 0.69313 (17) | 0.47822 (19) | 0.7374 (3) | 0.0188 (5) | |
C4 | 0.77235 (19) | 0.4102 (2) | 0.7720 (4) | 0.0168 (5) | |
Cl4 | 0.88693 (5) | 0.45866 (5) | 0.97132 (8) | 0.02421 (16) | |
C5 | 0.7727 (2) | 0.3043 (2) | 0.6698 (4) | 0.0175 (6) | |
C51 | 0.8463 (2) | 0.2113 (2) | 0.7736 (4) | 0.0181 (5) | |
O51 | 0.83796 (14) | 0.10397 (15) | 0.7284 (3) | 0.0214 (4) | |
C6 | 0.67916 (19) | 0.2882 (2) | 0.4875 (4) | 0.0159 (6) | |
N61 | 0.67345 (16) | 0.21224 (18) | 0.3428 (3) | 0.0168 (5) | |
C62 | 0.7639 (2) | 0.1678 (2) | 0.3234 (4) | 0.0196 (6) | |
C63 | 0.7551 (2) | 0.1935 (3) | 0.1173 (4) | 0.0247 (6) | |
C64 | 0.6546 (2) | 0.1463 (3) | −0.0465 (4) | 0.0271 (7) | |
C65 | 0.5642 (2) | 0.2008 (3) | −0.0246 (4) | 0.0249 (6) | |
C66 | 0.5741 (2) | 0.1725 (2) | 0.1831 (4) | 0.0200 (6) | |
H2A | 0.4565 | 0.4702 | 0.4736 | 0.026* | |
H2B | 0.5211 | 0.5491 | 0.6534 | 0.026* | |
H51 | 0.9072 | 0.2348 | 0.8881 | 0.022* | |
H62A | 0.7706 | 0.0802 | 0.3480 | 0.023* | |
H62B | 0.8270 | 0.2068 | 0.4258 | 0.023* | |
H63A | 0.8138 | 0.1557 | 0.1045 | 0.030* | |
H63B | 0.7590 | 0.2813 | 0.1008 | 0.030* | |
H64A | 0.6499 | 0.1671 | −0.1795 | 0.033* | |
H64B | 0.6525 | 0.0578 | −0.0372 | 0.033* | |
H65A | 0.4986 | 0.1677 | −0.1284 | 0.030* | |
H65B | 0.5634 | 0.2889 | −0.0433 | 0.030* | |
H66A | 0.5173 | 0.2125 | 0.1999 | 0.024* | |
H66B | 0.5670 | 0.0848 | 0.1949 | 0.024* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0175 (11) | 0.0152 (11) | 0.0167 (11) | 0.0006 (9) | 0.0086 (9) | 0.0000 (9) |
N2 | 0.0183 (12) | 0.0219 (11) | 0.0214 (11) | 0.0022 (9) | 0.0051 (9) | −0.0075 (9) |
C2 | 0.0164 (13) | 0.0184 (14) | 0.0162 (12) | −0.0011 (10) | 0.0065 (11) | 0.0013 (10) |
N3 | 0.0162 (11) | 0.0205 (12) | 0.0165 (11) | −0.0013 (9) | 0.0043 (9) | −0.0032 (9) |
C4 | 0.0144 (13) | 0.0178 (13) | 0.0153 (12) | −0.0042 (10) | 0.0039 (10) | 0.0023 (10) |
Cl4 | 0.0198 (3) | 0.0256 (3) | 0.0210 (3) | −0.0033 (3) | 0.0036 (2) | −0.0050 (3) |
C5 | 0.0170 (13) | 0.0201 (13) | 0.0172 (13) | 0.0011 (11) | 0.0094 (11) | 0.0014 (11) |
C51 | 0.0173 (13) | 0.0206 (13) | 0.0168 (13) | −0.0017 (11) | 0.0080 (11) | −0.0002 (11) |
O51 | 0.0209 (10) | 0.0188 (10) | 0.0215 (10) | 0.0016 (8) | 0.0067 (8) | 0.0025 (8) |
C6 | 0.0153 (13) | 0.0200 (14) | 0.0114 (13) | −0.0003 (11) | 0.0050 (11) | 0.0016 (10) |
N61 | 0.0164 (11) | 0.0177 (11) | 0.0163 (10) | 0.0000 (9) | 0.0073 (9) | −0.0027 (9) |
C62 | 0.0189 (14) | 0.0214 (14) | 0.0188 (14) | 0.0017 (10) | 0.0088 (12) | −0.0014 (11) |
C63 | 0.0259 (15) | 0.0292 (15) | 0.0230 (15) | −0.0007 (12) | 0.0144 (13) | −0.0001 (12) |
C64 | 0.0355 (17) | 0.0314 (17) | 0.0173 (15) | −0.0027 (14) | 0.0144 (14) | −0.0005 (13) |
C65 | 0.0287 (16) | 0.0225 (14) | 0.0165 (14) | −0.0007 (13) | 0.0037 (12) | −0.0004 (11) |
C66 | 0.0178 (14) | 0.0199 (13) | 0.0196 (14) | −0.0014 (11) | 0.0060 (11) | −0.0044 (11) |
Geometric parameters (Å, º) top
N1—C2 | 1.338 (3) | N61—C66 | 1.467 (3) |
N1—C6 | 1.345 (3) | C62—C63 | 1.510 (4) |
N2—C2 | 1.337 (3) | C62—H62A | 0.99 |
N2—H2A | 0.88 | C62—H62B | 0.99 |
N2—H2B | 0.88 | C63—C64 | 1.515 (4) |
C2—N3 | 1.367 (3) | C63—H63A | 0.99 |
N3—C4 | 1.300 (3) | C63—H63B | 0.99 |
C4—C5 | 1.405 (4) | C64—C65 | 1.515 (4) |
C4—Cl4 | 1.745 (3) | C64—H64A | 0.99 |
C5—C6 | 1.438 (3) | C64—H64B | 0.99 |
C5—C51 | 1.439 (4) | C65—C66 | 1.523 (4) |
C51—O51 | 1.233 (3) | C65—H65A | 0.99 |
C51—H51 | 0.95 | C65—H65B | 0.99 |
C6—N61 | 1.344 (3) | C66—H66A | 0.99 |
N61—C62 | 1.466 (3) | C66—H66B | 0.99 |
| | | |
C2—N1—C6 | 116.9 (2) | C63—C62—H62B | 109.4 |
C2—N2—H2A | 120.0 | H62A—C62—H62B | 108.0 |
C2—N2—H2B | 120.0 | C62—C63—C64 | 111.6 (2) |
H2A—N2—H2B | 120.0 | C62—C63—H63A | 109.3 |
N2—C2—N1 | 117.9 (2) | C64—C63—H63A | 109.3 |
N2—C2—N3 | 115.5 (2) | C62—C63—H63B | 109.3 |
N1—C2—N3 | 126.5 (2) | C64—C63—H63B | 109.3 |
C4—N3—C2 | 113.5 (2) | H63A—C63—H63B | 108.0 |
N3—C4—C5 | 126.7 (2) | C65—C64—C63 | 109.7 (2) |
N3—C4—Cl4 | 113.96 (19) | C65—C64—H64A | 109.7 |
C5—C4—Cl4 | 119.28 (19) | C63—C64—H64A | 109.7 |
C4—C5—C6 | 112.8 (2) | C65—C64—H64B | 109.7 |
C4—C5—C51 | 119.6 (2) | C63—C64—H64B | 109.7 |
C6—C5—C51 | 125.2 (2) | H64A—C64—H64B | 108.2 |
O51—C51—C5 | 126.4 (2) | C64—C65—C66 | 109.4 (2) |
O51—C51—H51 | 116.8 | C64—C65—H65A | 109.8 |
C5—C51—H51 | 116.8 | C66—C65—H65A | 109.8 |
N61—C6—N1 | 117.4 (2) | C64—C65—H65B | 109.8 |
N61—C6—C5 | 122.1 (2) | C66—C65—H65B | 109.8 |
N1—C6—C5 | 120.5 (2) | H65A—C65—H65B | 108.2 |
C6—N61—C62 | 123.6 (2) | N61—C66—C65 | 112.0 (2) |
C6—N61—C66 | 121.9 (2) | N61—C66—H66A | 109.2 |
C62—N61—C66 | 114.4 (2) | C65—C66—H66A | 109.2 |
N61—C62—C63 | 111.2 (2) | N61—C66—H66B | 109.2 |
N61—C62—H62A | 109.4 | C65—C66—H66B | 109.2 |
C63—C62—H62A | 109.4 | H66A—C66—H66B | 107.9 |
N61—C62—H62B | 109.4 | | |
| | | |
C6—N1—C2—N2 | −175.2 (2) | C51—C5—C6—N61 | −35.6 (4) |
C6—N1—C2—N3 | 7.2 (4) | C4—C5—C6—N1 | −18.5 (3) |
N2—C2—N3—C4 | 169.3 (2) | C51—C5—C6—N1 | 143.6 (3) |
N1—C2—N3—C4 | −13.0 (4) | N1—C6—N61—C62 | 161.2 (2) |
C2—N3—C4—C5 | 1.7 (4) | C5—C6—N61—C62 | −19.6 (4) |
C2—N3—C4—Cl4 | −176.73 (18) | N1—C6—N61—C66 | −15.2 (3) |
N3—C4—C5—C6 | 12.8 (4) | C5—C6—N61—C66 | 164.1 (2) |
Cl4—C4—C5—C6 | −168.76 (18) | C6—N61—C62—C63 | −124.8 (3) |
N3—C4—C5—C51 | −150.4 (3) | C66—N61—C62—C63 | 51.8 (3) |
Cl4—C4—C5—C51 | 28.0 (3) | N61—C62—C63—C64 | −53.5 (3) |
C4—C5—C51—O51 | 157.1 (3) | C62—C63—C64—C65 | 57.3 (3) |
C6—C5—C51—O51 | −3.9 (4) | C63—C64—C65—C66 | −57.3 (3) |
C2—N1—C6—N61 | −171.0 (2) | C6—N61—C66—C65 | 123.2 (3) |
C2—N1—C6—C5 | 9.8 (4) | C62—N61—C66—C65 | −53.4 (3) |
C4—C5—C6—N61 | 162.2 (2) | C64—C65—C66—N61 | 55.4 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O51i | 0.88 | 2.04 | 2.902 (3) | 166 |
N2—H2B···N1ii | 0.88 | 2.32 | 3.144 (3) | 155 |
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x, −y+1, z+1/2. |
Experimental details
| (I) | (II) | (III) | (IV) |
Crystal data |
Chemical formula | C11H15ClN4O | C9H13ClN4O | C9H11ClN4O2 | C12H17ClN4O |
Mr | 254.72 | 228.68 | 242.67 | 268.75 |
Crystal system, space group | Triclinic, P1 | Monoclinic, P21/n | Monoclinic, P21/c | Triclinic, P1 |
Temperature (K) | 120 | 120 | 120 | 120 |
a, b, c (Å) | 5.907 (2), 10.398 (3), 10.801 (2) | 11.328 (3), 8.0810 (4), 11.3849 (12) | 7.3540 (5), 8.2910 (13), 17.276 (3) | 8.5722 (6), 8.7195 (5), 8.7681 (7) |
α, β, γ (°) | 110.86 (3), 94.19 (2), 96.00 (3) | 90, 98.709 (14), 90 | 90, 97.962 (9), 90 | 82.598 (6), 82.701 (5), 88.645 (5) |
V (Å3) | 612.2 (3) | 1030.2 (3) | 1043.2 (3) | 644.63 (8) |
Z | 2 | 4 | 4 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.30 | 0.35 | 0.36 | 0.29 |
Crystal size (mm) | 0.48 × 0.28 × 0.08 | 0.37 × 0.36 × 0.08 | 0.43 × 0.27 × 0.25 | 0.55 × 0.29 × 0.12 |
|
Data collection |
Diffractometer | Bruker-Nonius KappaCCD diffractometer | Bruker-Nonius KappaCCD diffractometer | Bruker-Nonius KappaCCD diffractometer | Bruker-Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan SADABS 2.10 (Sheldrick, 2003) | Multi-scan SADABS 2.10 (Sheldrick, 2003) | Multi-scan SADABS 2.10 (Sheldrick, 2003) | Multi-scan SADABS 2.10 (Sheldrick, 2003) |
Tmin, Tmax | 0.869, 0.976 | 0.882, 0.973 | 0.862, 0.916 | 0.856, 0.966 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16678, 2807, 2278 | 21126, 2357, 1408 | 23197, 2411, 1847 | 18098, 2950, 2650 |
Rint | 0.045 | 0.099 | 0.057 | 0.018 |
(sin θ/λ)max (Å−1) | 0.650 | 0.650 | 0.650 | 0.650 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.099, 1.08 | 0.058, 0.155, 1.08 | 0.038, 0.087, 1.08 | 0.031, 0.080, 1.08 |
No. of reflections | 2807 | 2357 | 2411 | 2950 |
No. of parameters | 154 | 138 | 145 | 164 |
No. of restraints | 0 | 0 | 0 | 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) | 0.25, −0.37 | 0.43, −0.37 | 0.26, −0.30 | 0.34, −0.24 |
Absolute structure | ? | ? | ? | ? |
Absolute structure parameter | ? | ? | ? | ? |
| (V) | (VI) | (VII) | (VIII) |
Crystal data |
Chemical formula | C14H15ClN4O | C13H13ClN4O | C12H11ClN4O | C12H11ClN4O |
Mr | 290.75 | 276.72 | 262.70 | 262.70 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 120 | 120 | 120 | 120 |
a, b, c (Å) | 7.9897 (5), 8.0922 (4), 11.2786 (7) | 8.1811 (12), 8.8325 (10), 9.3356 (6) | 7.0568 (7), 8.211 (2), 10.565 (3) | 6.9938 (6), 7.9544 (10), 10.7507 (14) |
α, β, γ (°) | 91.602 (4), 107.220 (5), 91.776 (5) | 81.844 (9), 82.015 (10), 73.041 (7) | 84.590 (16), 82.363 (14), 78.687 (14) | 81.191 (11), 82.469 (12), 87.333 (10) |
V (Å3) | 695.66 (7) | 635.38 (12) | 593.5 (2) | 585.71 (12) |
Z | 2 | 2 | 2 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.28 | 0.30 | 0.32 | 0.32 |
Crystal size (mm) | 0.29 × 0.28 × 0.21 | 0.56 × 0.46 × 0.24 | 0.41 × 0.20 × 0.13 | 0.37 × 0.27 × 0.18 |
|
Data collection |
Diffractometer | Bruker-Nonius KappaCCD diffractometer | Bruker-Nonius KappaCCD diffractometer | Bruker-Nonius KappaCCD diffractometer | Bruker-Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan SADABS 2.10 (Sheldrick, 2003) | Multi-scan SADABS 2.10 (Sheldrick, 2003) | Multi-scan SADABS 2.10 (Sheldrick, 2003) | Multi-scan SADABS 2.10 (Sheldrick, 2003) |
Tmin, Tmax | 0.929, 0.944 | 0.851, 0.932 | 0.882, 0.960 | 0.891, 0.945 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19407, 3191, 2729 | 15349, 2902, 2269 | 15054, 2729, 1754 | 16227, 2681, 2305 |
Rint | 0.026 | 0.035 | 0.061 | 0.030 |
(sin θ/λ)max (Å−1) | 0.650 | 0.650 | 0.649 | 0.649 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.082, 1.12 | 0.040, 0.102, 1.11 | 0.052, 0.144, 1.06 | 0.033, 0.086, 1.09 |
No. of reflections | 3191 | 2902 | 2729 | 2681 |
No. of parameters | 182 | 173 | 163 | 164 |
No. of restraints | 0 | 0 | 0 | 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) | 0.28, −0.30 | 0.31, −0.36 | 0.50, −0.59 | 0.28, −0.28 |
Absolute structure | ? | ? | ? | ? |
Absolute structure parameter | ? | ? | ? | ? |
| (IX) | (X) | (XI) | (XII) |
Crystal data |
Chemical formula | C18H15ClN4O | C15H12ClN5O | C11H16ClN5O2 | C10H13ClN4O |
Mr | 338.79 | 313.75 | 285.74 | 240.69 |
Crystal system, space group | Triclinic, P1 | Monoclinic, P21/n | Triclinic, P1 | Monoclinic, Cc |
Temperature (K) | 120 | 120 | 120 | 120 |
a, b, c (Å) | 6.5520 (11), 11.1012 (7), 11.4111 (4) | 7.5716 (7), 16.6432 (18), 10.9450 (7) | 7.2147 (6), 8.8563 (10), 10.2855 (12) | 14.4681 (17), 11.1378 (17), 7.4534 (7) |
α, β, γ (°) | 79.958 (5), 84.802 (9), 77.009 (9) | 90, 93.549 (6), 90 | 84.856 (10), 85.296 (10), 79.092 (7) | 90, 116.535 (7), 90 |
V (Å3) | 795.21 (15) | 1376.6 (2) | 641.28 (12) | 1074.5 (2) |
Z | 2 | 4 | 2 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.25 | 0.29 | 0.31 | 0.34 |
Crystal size (mm) | 0.58 × 0.48 × 0.05 | 0.51 × 0.25 × 0.10 | 0.58 × 0.29 × 0.22 | 0.30 × 0.26 × 0.15 |
|
Data collection |
Diffractometer | Bruker-Nonius KappaCCD diffractometer | Bruker-Nonius KappaCCD diffractometer | Bruker-Nonius KappaCCD diffractometer | Bruker-Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan SADABS 2.10 (Sheldrick, 2003) | Multi-scan SADABS 2.10 (Sheldrick, 2003) | Multi-scan SADABS 2.10 (Sheldrick, 2003) | Multi-scan SADABS 2.10 (Sheldrick, 2003) |
Tmin, Tmax | 0.867, 0.988 | 0.867, 0.972 | 0.843, 0.936 | 0.896, 0.951 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19326, 3642, 2645 | 32885, 3149, 2236 | 15336, 2936, 2402 | 12891, 2460, 1972 |
Rint | 0.038 | 0.057 | 0.024 | 0.050 |
(sin θ/λ)max (Å−1) | 0.649 | 0.650 | 0.650 | 0.650 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.089, 1.09 | 0.045, 0.121, 1.11 | 0.038, 0.102, 1.13 | 0.038, 0.087, 1.11 |
No. of reflections | 3642 | 3149 | 2936 | 2460 |
No. of parameters | 217 | 199 | 173 | 145 |
No. of restraints | 0 | 0 | 0 | 2 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.28 | 0.36, −0.48 | 0.31, −0.27 | 0.33, −0.28 |
Absolute structure | ? | ? | ? | Flack (1983), 1219 Friedel pairs |
Absolute structure parameter | ? | ? | ? | 0.07 (7) |
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