The molecular and supramolecular structures of eight
N4-substituted 2,4-diamino-6-benzyloxy-5-nitrosopyrimidines are discussed, along with one analogue containing no nitroso substituent. The nitroso derivatives all exhibit polarized molecular-electronic structures leading to extensive charge-assisted hydrogen bonding between the molecules. The intermolecular interactions include hard hydrogen bonds of N—H
O and N—H
N types, together with O—H
O and O—H
N types in the monohydrate of 2-amino-6-benzyloxy-4-piperidino-5-nitrosopyrimidine, soft hydrogen bonds of C—H
O, C—H
π(arene) and N—H
π(arene) types and aromatic π
π stacking interactions. The predominant supramolecular structure types take the form of chains and sheets, but no two of the structures determined here exhibit the same combination of hydrogen-bond types.
Supporting information
CCDC references: 210880; 210881; 210882; 210883; 210884; 210885; 210886; 210887
For all compounds, data collection: Kappa-CCD server software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997b); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: PLATON (Spek, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997a) and PRPKAPPA (Ferguson, 1999).
(1) 2-Amino-6-benzyloxy-4-(
N-methylamino)-5-nitrosopyrimidine
top
Crystal data top
C12H13N5O2 | F(000) = 544 |
Mr = 259.27 | Dx = 1.402 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1649 reflections |
a = 7.1122 (2) Å | θ = 3.0–27.5° |
b = 7.3873 (2) Å | µ = 0.10 mm−1 |
c = 23.3867 (7) Å | T = 120 K |
V = 1228.74 (6) Å3 | Plate, pink |
Z = 4 | 0.30 × 0.14 × 0.07 mm |
Data collection top
Kappa-CCD diffractometer | 1649 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 1323 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.060 |
ϕ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −9→7 |
Tmin = 0.954, Tmax = 0.994 | k = −8→9 |
6981 measured reflections | l = −30→30 |
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) = 0.090 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0467P)2] where P = (Fo2 + 2Fc2)/3 |
1649 reflections | (Δ/σ)max < 0.001 |
173 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Crystal data top
C12H13N5O2 | V = 1228.74 (6) Å3 |
Mr = 259.27 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.1122 (2) Å | µ = 0.10 mm−1 |
b = 7.3873 (2) Å | T = 120 K |
c = 23.3867 (7) Å | 0.30 × 0.14 × 0.07 mm |
Data collection top
Kappa-CCD diffractometer | 1649 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 1323 reflections with I > 2σ(I) |
Tmin = 0.954, Tmax = 0.994 | Rint = 0.060 |
6981 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.090 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.18 e Å−3 |
1649 reflections | Δρmin = −0.24 e Å−3 |
173 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.7669 (3) | 1.1531 (2) | 0.13328 (8) | 0.0226 (4) | |
C2 | 0.8858 (3) | 1.2910 (3) | 0.14977 (10) | 0.0220 (5) | |
N2 | 0.8267 (3) | 1.4559 (3) | 0.13741 (9) | 0.0316 (5) | |
N3 | 1.0523 (2) | 1.2758 (2) | 0.17588 (8) | 0.0226 (4) | |
C4 | 1.1051 (3) | 1.1086 (3) | 0.19092 (9) | 0.0198 (5) | |
N4 | 1.2650 (3) | 1.0868 (2) | 0.21909 (8) | 0.0248 (4) | |
C41 | 1.3894 (3) | 1.2361 (3) | 0.23419 (11) | 0.0303 (6) | |
C5 | 0.9949 (3) | 0.9511 (3) | 0.17556 (9) | 0.0193 (5) | |
N5 | 1.0382 (3) | 0.7757 (2) | 0.18412 (8) | 0.0235 (4) | |
O5 | 1.1890 (2) | 0.7408 (2) | 0.21219 (7) | 0.0271 (4) | |
C6 | 0.8244 (3) | 0.9904 (3) | 0.14496 (9) | 0.0194 (5) | |
C61 | 0.5036 (3) | 0.7082 (3) | 0.06605 (9) | 0.0224 (5) | |
C62 | 0.3886 (3) | 0.5793 (3) | 0.09145 (10) | 0.0256 (5) | |
C63 | 0.3519 (3) | 0.4165 (3) | 0.06323 (11) | 0.0294 (6) | |
C64 | 0.4296 (3) | 0.3826 (3) | 0.01079 (10) | 0.0320 (6) | |
C65 | 0.5449 (3) | 0.5104 (3) | −0.01465 (11) | 0.0311 (6) | |
C66 | 0.5817 (3) | 0.6723 (3) | 0.01291 (10) | 0.0271 (6) | |
C67 | 0.5514 (3) | 0.8825 (3) | 0.09596 (10) | 0.0273 (5) | |
O6 | 0.7229 (2) | 0.84726 (19) | 0.12848 (6) | 0.0239 (4) | |
H2A | 0.8962 | 1.5503 | 0.1464 | 0.038* | |
H2B | 0.7178 | 1.4714 | 0.1202 | 0.038* | |
H4 | 1.2978 | 0.9765 | 0.2292 | 0.030* | |
H41A | 1.4801 | 1.2559 | 0.2033 | 0.045* | |
H41B | 1.4569 | 1.2066 | 0.2695 | 0.045* | |
H41C | 1.3150 | 1.3462 | 0.2400 | 0.045* | |
H62 | 0.3350 | 0.6019 | 0.1280 | 0.031* | |
H63 | 0.2725 | 0.3288 | 0.0805 | 0.035* | |
H64 | 0.4045 | 0.2714 | −0.0082 | 0.038* | |
H65 | 0.5989 | 0.4868 | −0.0511 | 0.037* | |
H66 | 0.6610 | 0.7595 | −0.0047 | 0.033* | |
H67A | 0.5725 | 0.9804 | 0.0678 | 0.033* | |
H67B | 0.4481 | 0.9190 | 0.1219 | 0.033* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0226 (10) | 0.0180 (9) | 0.0272 (10) | 0.0025 (8) | −0.0019 (9) | −0.0012 (8) |
C2 | 0.0255 (11) | 0.0177 (11) | 0.0227 (12) | 0.0016 (9) | 0.0014 (10) | −0.0019 (10) |
N2 | 0.0326 (12) | 0.0164 (10) | 0.0458 (13) | 0.0013 (8) | −0.0126 (10) | −0.0008 (9) |
N3 | 0.0227 (10) | 0.0190 (9) | 0.0262 (10) | −0.0009 (8) | −0.0021 (8) | −0.0010 (8) |
C4 | 0.0190 (11) | 0.0212 (12) | 0.0192 (11) | −0.0002 (9) | 0.0005 (9) | −0.0031 (9) |
N4 | 0.0214 (10) | 0.0229 (10) | 0.0300 (11) | 0.0015 (8) | −0.0030 (9) | −0.0020 (8) |
C41 | 0.0218 (12) | 0.0347 (14) | 0.0342 (14) | −0.0071 (11) | −0.0027 (10) | −0.0063 (11) |
C5 | 0.0201 (11) | 0.0165 (11) | 0.0214 (11) | 0.0010 (9) | −0.0003 (10) | −0.0009 (9) |
N5 | 0.0210 (10) | 0.0255 (10) | 0.0239 (10) | 0.0027 (8) | −0.0020 (8) | 0.0004 (8) |
O5 | 0.0233 (8) | 0.0268 (9) | 0.0311 (9) | 0.0058 (7) | −0.0063 (7) | 0.0002 (7) |
C6 | 0.0201 (11) | 0.0174 (11) | 0.0208 (11) | 0.0006 (9) | −0.0005 (9) | −0.0026 (9) |
C61 | 0.0189 (11) | 0.0210 (12) | 0.0273 (13) | 0.0026 (9) | −0.0079 (10) | −0.0004 (9) |
C62 | 0.0247 (13) | 0.0278 (12) | 0.0245 (12) | 0.0016 (10) | −0.0005 (10) | 0.0005 (10) |
C63 | 0.0289 (13) | 0.0264 (13) | 0.0329 (14) | −0.0079 (10) | −0.0030 (12) | 0.0048 (11) |
C64 | 0.0381 (15) | 0.0242 (13) | 0.0338 (14) | −0.0017 (11) | −0.0063 (12) | −0.0060 (11) |
C65 | 0.0308 (14) | 0.0378 (14) | 0.0245 (12) | 0.0026 (11) | 0.0011 (11) | −0.0044 (11) |
C66 | 0.0221 (12) | 0.0302 (14) | 0.0290 (13) | −0.0037 (10) | −0.0014 (11) | 0.0039 (10) |
C67 | 0.0228 (13) | 0.0226 (12) | 0.0365 (13) | 0.0034 (9) | −0.0090 (11) | −0.0042 (10) |
O6 | 0.0229 (8) | 0.0173 (8) | 0.0315 (9) | 0.0004 (6) | −0.0101 (7) | −0.0012 (7) |
Geometric parameters (Å, º) top
N1—C6 | 1.299 (3) | C6—O6 | 1.337 (2) |
N1—C2 | 1.379 (3) | C61—C66 | 1.387 (3) |
C2—N2 | 1.320 (3) | C61—C62 | 1.388 (3) |
C2—N3 | 1.337 (3) | C61—C67 | 1.504 (3) |
N2—H2A | 0.88 | C62—C63 | 1.396 (3) |
N2—H2B | 0.88 | C62—H62 | 0.95 |
N3—C4 | 1.338 (3) | C63—C64 | 1.368 (3) |
C4—N4 | 1.324 (3) | C63—H63 | 0.95 |
C4—C5 | 1.448 (3) | C64—C65 | 1.385 (3) |
N4—C41 | 1.457 (3) | C64—H64 | 0.95 |
N4—H4 | 0.88 | C65—C66 | 1.384 (3) |
C41—H41A | 0.98 | C65—H65 | 0.95 |
C41—H41B | 0.98 | C66—H66 | 0.95 |
C41—H41C | 0.98 | C67—O6 | 1.461 (3) |
C5—N5 | 1.347 (3) | C67—H67A | 0.99 |
C5—C6 | 1.438 (3) | C67—H67B | 0.99 |
N5—O5 | 1.283 (2) | | |
| | | |
C6—N1—C2 | 115.56 (18) | O6—C6—C5 | 116.07 (18) |
N2—C2—N3 | 117.4 (2) | C66—C61—C62 | 119.2 (2) |
N2—C2—N1 | 115.1 (2) | C66—C61—C67 | 119.3 (2) |
N3—C2—N1 | 127.51 (18) | C62—C61—C67 | 121.4 (2) |
C2—N2—H2A | 120.0 | C61—C62—C63 | 119.9 (2) |
C2—N2—H2B | 120.0 | C61—C62—H62 | 120.0 |
H2A—N2—H2B | 120.0 | C63—C62—H62 | 120.0 |
C2—N3—C4 | 116.51 (18) | C64—C63—C62 | 120.4 (2) |
N4—C4—N3 | 118.95 (19) | C64—C63—H63 | 119.8 |
N4—C4—C5 | 119.37 (19) | C62—C63—H63 | 119.8 |
N3—C4—C5 | 121.66 (19) | C63—C64—C65 | 119.9 (2) |
C4—N4—C41 | 123.37 (18) | C63—C64—H64 | 120.0 |
C4—N4—H4 | 118.3 | C65—C64—H64 | 120.0 |
C41—N4—H4 | 118.3 | C66—C65—C64 | 120.1 (2) |
N4—C41—H41A | 109.5 | C66—C65—H65 | 120.0 |
N4—C41—H41B | 109.5 | C64—C65—H65 | 120.0 |
H41A—C41—H41B | 109.5 | C65—C66—C61 | 120.5 (2) |
N4—C41—H41C | 109.5 | C65—C66—H66 | 119.8 |
H41A—C41—H41C | 109.5 | C61—C66—H66 | 119.8 |
H41B—C41—H41C | 109.5 | O6—C67—C61 | 106.16 (18) |
N5—C5—C6 | 117.45 (19) | O6—C67—H67A | 110.5 |
N5—C5—C4 | 127.8 (2) | C61—C67—H67A | 110.5 |
C6—C5—C4 | 114.69 (18) | O6—C67—H67B | 110.5 |
O5—N5—C5 | 117.39 (19) | C61—C67—H67B | 110.5 |
N1—C6—O6 | 120.08 (18) | H67A—C67—H67B | 108.7 |
N1—C6—C5 | 123.85 (18) | C6—O6—C67 | 117.40 (16) |
| | | |
C6—N1—C2—N2 | 179.6 (2) | C4—C5—C6—N1 | −2.4 (3) |
C6—N1—C2—N3 | 0.4 (3) | N5—C5—C6—O6 | 0.9 (3) |
N2—C2—N3—C4 | 176.4 (2) | C4—C5—C6—O6 | 177.79 (18) |
N1—C2—N3—C4 | −4.4 (3) | C66—C61—C62—C63 | −0.5 (3) |
C2—N3—C4—N4 | −177.14 (19) | C67—C61—C62—C63 | −178.0 (2) |
C2—N3—C4—C5 | 4.9 (3) | C61—C62—C63—C64 | 0.4 (4) |
N3—C4—N4—C41 | −0.8 (3) | C62—C63—C64—C65 | −0.2 (4) |
C5—C4—N4—C41 | 177.20 (19) | C63—C64—C65—C66 | 0.0 (3) |
N4—C4—C5—N5 | −3.3 (3) | C64—C65—C66—C61 | −0.1 (3) |
N3—C4—C5—N5 | 174.6 (2) | C62—C61—C66—C65 | 0.3 (3) |
N4—C4—C5—C6 | −179.84 (19) | C67—C61—C66—C65 | 177.9 (2) |
N3—C4—C5—C6 | −1.9 (3) | C66—C61—C67—O6 | −87.4 (2) |
C6—C5—N5—O5 | −178.96 (17) | C62—C61—C67—O6 | 90.2 (2) |
C4—C5—N5—O5 | 4.6 (3) | N1—C6—O6—C67 | 1.8 (3) |
C2—N1—C6—O6 | −177.08 (19) | C5—C6—O6—C67 | −178.41 (18) |
C2—N1—C6—C5 | 3.1 (3) | C61—C67—O6—C6 | 160.73 (19) |
N5—C5—C6—N1 | −179.3 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O5 | 0.88 | 1.95 | 2.618 (2) | 132 |
N2—H2A···N5i | 0.88 | 2.14 | 3.006 (3) | 169 |
N2—H2B···Cg1i | 0.88 | 2.68 | 3.516 (2) | 160 |
C62—H62···O5ii | 0.95 | 2.45 | 3.379 (3) | 165 |
C66—H66···Cg1iii | 0.95 | 2.73 | 3.647 (2) | 163 |
Symmetry codes: (i) x, y+1, z; (ii) x−1, y, z; (iii) x+1/2, −y+3/2, −z. |
(2) 2-Amino-6-benzyloxy-4-(
N-butylamino)-5-nitrosopyrimidine
top
Crystal data top
C15H19N5O2 | F(000) = 640 |
Mr = 301.35 | Dx = 1.325 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3424 reflections |
a = 7.6146 (2) Å | θ = 3.0–27.5° |
b = 13.7686 (4) Å | µ = 0.09 mm−1 |
c = 16.1215 (5) Å | T = 120 K |
β = 116.6180 (15)° | Block, blue |
V = 1511.08 (8) Å3 | 0.35 × 0.20 × 0.15 mm |
Z = 4 | |
Data collection top
Kappa-CCD diffractometer | 3424 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2616 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
ϕ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −9→8 |
Tmin = 0.966, Tmax = 0.988 | k = −17→17 |
12361 measured reflections | l = −19→20 |
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) = 0.120 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0624P)2 + 0.2767P] where P = (Fo2 + 2Fc2)/3 |
3424 reflections | (Δ/σ)max < 0.001 |
200 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
Crystal data top
C15H19N5O2 | V = 1511.08 (8) Å3 |
Mr = 301.35 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.6146 (2) Å | µ = 0.09 mm−1 |
b = 13.7686 (4) Å | T = 120 K |
c = 16.1215 (5) Å | 0.35 × 0.20 × 0.15 mm |
β = 116.6180 (15)° | |
Data collection top
Kappa-CCD diffractometer | 3424 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 2616 reflections with I > 2σ(I) |
Tmin = 0.966, Tmax = 0.988 | Rint = 0.074 |
12361 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.22 e Å−3 |
3424 reflections | Δρmin = −0.29 e Å−3 |
200 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.49974 (16) | 0.21875 (8) | 0.22659 (7) | 0.0202 (3) | |
C2 | 0.32244 (19) | 0.17163 (9) | 0.19166 (9) | 0.0190 (3) | |
N2 | 0.33078 (17) | 0.07829 (8) | 0.21439 (8) | 0.0246 (3) | |
N3 | 0.14484 (16) | 0.20783 (8) | 0.13701 (8) | 0.0198 (3) | |
C4 | 0.13639 (18) | 0.30251 (10) | 0.11613 (9) | 0.0180 (3) | |
C41 | −0.22046 (19) | 0.28505 (10) | 0.02664 (10) | 0.0249 (3) | |
C42 | −0.39648 (19) | 0.35122 (10) | −0.00866 (10) | 0.0248 (3) | |
C43 | −0.58963 (19) | 0.29642 (11) | −0.04435 (10) | 0.0257 (3) | |
C44 | −0.7649 (2) | 0.36379 (12) | −0.08310 (11) | 0.0304 (4) | |
N4 | −0.03742 (16) | 0.34023 (8) | 0.06105 (8) | 0.0210 (3) | |
C5 | 0.31037 (18) | 0.36262 (9) | 0.15438 (9) | 0.0177 (3) | |
N5 | 0.32012 (16) | 0.45998 (8) | 0.14812 (8) | 0.0209 (3) | |
O5 | 0.16146 (13) | 0.50492 (7) | 0.09819 (7) | 0.0248 (2) | |
C6 | 0.48887 (19) | 0.31171 (10) | 0.20825 (9) | 0.0184 (3) | |
O6 | 0.65323 (13) | 0.36451 (7) | 0.24058 (7) | 0.0241 (2) | |
C67 | 0.83886 (19) | 0.31352 (10) | 0.29263 (10) | 0.0250 (3) | |
C61 | 0.99304 (18) | 0.39019 (10) | 0.33463 (9) | 0.0208 (3) | |
C62 | 1.0505 (2) | 0.44570 (10) | 0.27876 (10) | 0.0236 (3) | |
C63 | 1.1890 (2) | 0.51865 (11) | 0.31678 (11) | 0.0280 (3) | |
C64 | 1.2730 (2) | 0.53553 (11) | 0.41100 (11) | 0.0304 (4) | |
C65 | 1.2174 (2) | 0.48152 (12) | 0.46718 (10) | 0.0304 (4) | |
C66 | 1.0771 (2) | 0.40920 (11) | 0.42901 (10) | 0.0261 (3) | |
H2B | 0.2225 | 0.0435 | 0.1936 | 0.030* | |
H2A | 0.4446 | 0.0513 | 0.2502 | 0.030* | |
H41A | −0.2198 | 0.2441 | 0.0773 | 0.030* | |
H41B | −0.2298 | 0.2416 | −0.0241 | 0.030* | |
H42A | −0.3966 | 0.3919 | −0.0593 | 0.030* | |
H42B | −0.3855 | 0.3951 | 0.0421 | 0.030* | |
H43A | −0.5987 | 0.2506 | −0.0934 | 0.031* | |
H43B | −0.5923 | 0.2580 | 0.0070 | 0.031* | |
H44A | −0.7526 | 0.4118 | −0.0359 | 0.046* | |
H44B | −0.8855 | 0.3260 | −0.1006 | 0.046* | |
H44C | −0.7704 | 0.3972 | −0.1379 | 0.046* | |
H4 | −0.0428 | 0.4015 | 0.0444 | 0.025* | |
H67A | 0.8687 | 0.2713 | 0.2509 | 0.030* | |
H67B | 0.8322 | 0.2727 | 0.3417 | 0.030* | |
H62 | 0.9942 | 0.4334 | 0.2140 | 0.028* | |
H63 | 1.2260 | 0.5569 | 0.2781 | 0.034* | |
H64 | 1.3698 | 0.5847 | 0.4373 | 0.036* | |
H65 | 1.2751 | 0.4938 | 0.5320 | 0.036* | |
H66 | 1.0383 | 0.3724 | 0.4679 | 0.031* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0155 (5) | 0.0174 (6) | 0.0242 (6) | −0.0004 (5) | 0.0057 (5) | 0.0009 (4) |
C2 | 0.0184 (7) | 0.0172 (6) | 0.0207 (6) | −0.0001 (5) | 0.0082 (5) | −0.0005 (5) |
N2 | 0.0164 (6) | 0.0165 (6) | 0.0347 (7) | −0.0010 (5) | 0.0058 (5) | 0.0030 (5) |
N3 | 0.0156 (5) | 0.0172 (6) | 0.0242 (6) | 0.0000 (5) | 0.0067 (4) | 0.0010 (4) |
C4 | 0.0151 (6) | 0.0193 (7) | 0.0187 (6) | −0.0005 (5) | 0.0068 (5) | −0.0001 (5) |
C41 | 0.0143 (7) | 0.0226 (7) | 0.0326 (8) | −0.0031 (6) | 0.0058 (6) | −0.0032 (6) |
C42 | 0.0154 (7) | 0.0233 (7) | 0.0323 (8) | −0.0013 (6) | 0.0076 (6) | 0.0044 (6) |
C43 | 0.0171 (7) | 0.0245 (7) | 0.0322 (8) | −0.0026 (6) | 0.0082 (6) | −0.0042 (6) |
C44 | 0.0165 (7) | 0.0368 (9) | 0.0334 (8) | −0.0013 (7) | 0.0070 (6) | −0.0002 (7) |
N4 | 0.0138 (6) | 0.0186 (6) | 0.0261 (6) | −0.0008 (5) | 0.0048 (5) | 0.0034 (5) |
C5 | 0.0145 (6) | 0.0171 (6) | 0.0197 (6) | −0.0010 (5) | 0.0061 (5) | 0.0019 (5) |
N5 | 0.0156 (5) | 0.0199 (6) | 0.0249 (6) | 0.0027 (5) | 0.0069 (5) | 0.0047 (5) |
O5 | 0.0169 (5) | 0.0215 (5) | 0.0310 (5) | 0.0033 (4) | 0.0062 (4) | 0.0068 (4) |
C6 | 0.0150 (6) | 0.0186 (6) | 0.0198 (6) | −0.0012 (5) | 0.0062 (5) | 0.0001 (5) |
O6 | 0.0107 (5) | 0.0185 (5) | 0.0344 (6) | −0.0001 (4) | 0.0024 (4) | 0.0040 (4) |
C67 | 0.0126 (6) | 0.0219 (7) | 0.0329 (8) | 0.0035 (6) | 0.0034 (6) | 0.0028 (6) |
C61 | 0.0117 (6) | 0.0194 (6) | 0.0275 (7) | 0.0037 (5) | 0.0054 (5) | 0.0002 (5) |
C62 | 0.0193 (7) | 0.0252 (7) | 0.0259 (7) | 0.0021 (6) | 0.0097 (6) | −0.0011 (6) |
C63 | 0.0208 (7) | 0.0245 (7) | 0.0423 (9) | 0.0017 (6) | 0.0172 (6) | 0.0015 (6) |
C64 | 0.0145 (7) | 0.0244 (7) | 0.0475 (9) | −0.0001 (6) | 0.0098 (6) | −0.0076 (7) |
C65 | 0.0192 (7) | 0.0349 (9) | 0.0285 (8) | 0.0046 (6) | 0.0030 (6) | −0.0068 (6) |
C66 | 0.0182 (7) | 0.0306 (8) | 0.0281 (7) | 0.0052 (6) | 0.0090 (6) | 0.0041 (6) |
Geometric parameters (Å, º) top
N1—C6 | 1.3080 (17) | C44—H44C | 0.9800 |
N1—C2 | 1.3709 (17) | N4—H4 | 0.8800 |
C2—N2 | 1.3301 (17) | C5—N5 | 1.3488 (17) |
C2—N3 | 1.3363 (17) | C5—C6 | 1.4266 (18) |
N2—H2A | 0.8800 | N5—O5 | 1.2724 (14) |
N2—H2B | 0.8800 | C6—O6 | 1.3349 (16) |
N3—C4 | 1.3406 (17) | O6—C67 | 1.4602 (15) |
C4—N4 | 1.3255 (16) | C67—C61 | 1.4964 (19) |
C4—C5 | 1.4451 (18) | C67—H67A | 0.9900 |
C41—N4 | 1.4611 (17) | C67—H67B | 0.9900 |
C41—C42 | 1.5056 (19) | C61—C66 | 1.3858 (19) |
C41—H41A | 0.9900 | C61—C62 | 1.393 (2) |
C41—H41B | 0.9900 | C62—C63 | 1.385 (2) |
C42—C43 | 1.5183 (18) | C62—H62 | 0.9500 |
C42—H42A | 0.9900 | C63—C64 | 1.378 (2) |
C42—H42B | 0.9900 | C63—H63 | 0.9500 |
C43—C44 | 1.512 (2) | C64—C65 | 1.377 (2) |
C43—H43A | 0.9900 | C64—H64 | 0.9500 |
C43—H43B | 0.9900 | C65—C66 | 1.386 (2) |
C44—H44A | 0.9800 | C65—H65 | 0.9500 |
C44—H44B | 0.9800 | C66—H66 | 0.9500 |
| | | |
C6—N1—C2 | 114.79 (11) | C4—N4—C41 | 123.16 (11) |
N2—C2—N3 | 116.83 (12) | C4—N4—H4 | 118.4 |
N2—C2—N1 | 115.30 (12) | C41—N4—H4 | 118.4 |
N3—C2—N1 | 127.87 (12) | N5—C5—C6 | 117.68 (11) |
C2—N2—H2A | 120.0 | N5—C5—C4 | 127.44 (12) |
C2—N2—H2B | 120.0 | C6—C5—C4 | 114.81 (12) |
H2A—N2—H2B | 120.0 | O5—N5—C5 | 117.53 (11) |
C2—N3—C4 | 116.66 (11) | N1—C6—O6 | 119.43 (12) |
N4—C4—N3 | 118.06 (12) | N1—C6—C5 | 124.40 (12) |
N4—C4—C5 | 120.71 (12) | O6—C6—C5 | 116.17 (11) |
N3—C4—C5 | 121.20 (11) | C6—O6—C67 | 117.35 (10) |
N4—C41—C42 | 111.41 (11) | O6—C67—C61 | 106.38 (10) |
N4—C41—H41A | 109.3 | O6—C67—H67A | 110.5 |
C42—C41—H41A | 109.3 | C61—C67—H67A | 110.5 |
N4—C41—H41B | 109.3 | O6—C67—H67B | 110.5 |
C42—C41—H41B | 109.3 | C61—C67—H67B | 110.5 |
H41A—C41—H41B | 108.0 | H67A—C67—H67B | 108.6 |
C41—C42—C43 | 112.93 (12) | C66—C61—C62 | 118.81 (13) |
C41—C42—H42A | 109.0 | C66—C61—C67 | 120.86 (13) |
C43—C42—H42A | 109.0 | C62—C61—C67 | 120.31 (12) |
C41—C42—H42B | 109.0 | C63—C62—C61 | 120.62 (13) |
C43—C42—H42B | 109.0 | C63—C62—H62 | 119.7 |
H42A—C42—H42B | 107.8 | C61—C62—H62 | 119.7 |
C44—C43—C42 | 112.20 (12) | C64—C63—C62 | 119.70 (14) |
C44—C43—H43A | 109.2 | C64—C63—H63 | 120.2 |
C42—C43—H43A | 109.2 | C62—C63—H63 | 120.2 |
C44—C43—H43B | 109.2 | C65—C64—C63 | 120.41 (14) |
C42—C43—H43B | 109.2 | C65—C64—H64 | 119.8 |
H43A—C43—H43B | 107.9 | C63—C64—H64 | 119.8 |
C43—C44—H44A | 109.5 | C64—C65—C66 | 119.91 (14) |
C43—C44—H44B | 109.5 | C64—C65—H65 | 120.0 |
H44A—C44—H44B | 109.5 | C66—C65—H65 | 120.0 |
C43—C44—H44C | 109.5 | C65—C66—C61 | 120.53 (14) |
H44A—C44—H44C | 109.5 | C65—C66—H66 | 119.7 |
H44B—C44—H44C | 109.5 | C61—C66—H66 | 119.7 |
| | | |
C6—N1—C2—N2 | −176.29 (12) | C2—N1—C6—C5 | −1.59 (19) |
C6—N1—C2—N3 | 4.8 (2) | N5—C5—C6—N1 | 174.27 (13) |
N2—C2—N3—C4 | 178.40 (12) | C4—C5—C6—N1 | −2.86 (19) |
N1—C2—N3—C4 | −2.7 (2) | N5—C5—C6—O6 | −6.15 (17) |
C2—N3—C4—N4 | 179.13 (11) | C4—C5—C6—O6 | 176.73 (11) |
C2—N3—C4—C5 | −2.54 (18) | N1—C6—O6—C67 | 2.13 (18) |
N4—C41—C42—C43 | −179.55 (12) | C5—C6—O6—C67 | −177.48 (11) |
C41—C42—C43—C44 | −177.66 (12) | C6—O6—C67—C61 | −170.15 (11) |
N3—C4—N4—C41 | 3.62 (19) | O6—C67—C61—C66 | 107.49 (14) |
C5—C4—N4—C41 | −174.71 (12) | O6—C67—C61—C62 | −70.68 (15) |
C42—C41—N4—C4 | 162.50 (12) | C66—C61—C62—C63 | −0.1 (2) |
N4—C4—C5—N5 | 6.5 (2) | C67—C61—C62—C63 | 178.13 (12) |
N3—C4—C5—N5 | −171.76 (13) | C61—C62—C63—C64 | 1.0 (2) |
N4—C4—C5—C6 | −176.69 (12) | C62—C63—C64—C65 | −1.2 (2) |
N3—C4—C5—C6 | 5.03 (18) | C63—C64—C65—C66 | 0.5 (2) |
C6—C5—N5—O5 | 178.33 (11) | C64—C65—C66—C61 | 0.5 (2) |
C4—C5—N5—O5 | −5.0 (2) | C62—C61—C66—C65 | −0.7 (2) |
C2—N1—C6—O6 | 178.83 (11) | C67—C61—C66—C65 | −178.85 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O5 | 0.88 | 2.00 | 2.642 (2) | 129 |
N2—H2A···N5i | 0.88 | 2.20 | 3.058 (2) | 164 |
N2—H2B···Cg1i | 0.88 | 2.67 | 3.537 (2) | 171 |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |
(3) 2-Amino-6-benzyloxy-4-(
N-dodecylamino)-5-nitrosopyrimidine
top
Crystal data top
C23H35N5O2 | Z = 2 |
Mr = 413.56 | F(000) = 448 |
Triclinic, P1 | Dx = 1.204 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.3567 (4) Å | Cell parameters from 4147 reflections |
b = 7.7784 (4) Å | θ = 3.0–27.5° |
c = 21.4725 (14) Å | µ = 0.08 mm−1 |
α = 92.000 (2)° | T = 120 K |
β = 99.840 (2)° | Plate, purple |
γ = 108.760 (2)° | 0.18 × 0.18 × 0.08 mm |
V = 1141.00 (11) Å3 | |
Data collection top
Kappa-CCD diffractometer | 4147 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2819 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
ϕ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −9→9 |
Tmin = 0.976, Tmax = 0.994 | k = −9→10 |
10984 measured reflections | l = −27→27 |
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) = 0.140 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0752P)2 + 0.1136P] where P = (Fo2 + 2Fc2)/3 |
4147 reflections | (Δ/σ)max < 0.001 |
272 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Crystal data top
C23H35N5O2 | γ = 108.760 (2)° |
Mr = 413.56 | V = 1141.00 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.3567 (4) Å | Mo Kα radiation |
b = 7.7784 (4) Å | µ = 0.08 mm−1 |
c = 21.4725 (14) Å | T = 120 K |
α = 92.000 (2)° | 0.18 × 0.18 × 0.08 mm |
β = 99.840 (2)° | |
Data collection top
Kappa-CCD diffractometer | 4147 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 2819 reflections with I > 2σ(I) |
Tmin = 0.976, Tmax = 0.994 | Rint = 0.048 |
10984 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.22 e Å−3 |
4147 reflections | Δρmin = −0.23 e Å−3 |
272 parameters | |
Special details top
Experimental. bsorpt_correction_T_max 0.9947 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.5363 (2) | 0.19353 (19) | 0.55144 (6) | 0.0231 (4) | |
C2 | 0.3905 (3) | 0.2288 (2) | 0.51088 (8) | 0.0234 (4) | |
N2 | 0.2243 (2) | 0.1990 (2) | 0.53114 (7) | 0.0293 (4) | |
N3 | 0.3984 (2) | 0.29059 (19) | 0.45348 (7) | 0.0236 (4) | |
C4 | 0.5688 (3) | 0.3270 (2) | 0.43450 (8) | 0.0223 (4) | |
C41 | 0.4311 (3) | 0.4504 (3) | 0.34147 (8) | 0.0278 (4) | |
C42 | 0.3255 (3) | 0.3251 (3) | 0.28115 (8) | 0.0273 (4) | |
C43 | 0.1503 (3) | 0.3784 (3) | 0.25104 (8) | 0.0288 (5) | |
C44 | 0.0217 (3) | 0.2609 (3) | 0.19140 (9) | 0.0307 (5) | |
C45 | −0.1591 (3) | 0.3147 (3) | 0.17023 (8) | 0.0284 (4) | |
C46 | −0.2922 (3) | 0.2164 (3) | 0.10839 (9) | 0.0311 (5) | |
C47 | −0.4619 (3) | 0.2879 (3) | 0.08934 (8) | 0.0294 (5) | |
C48 | −0.5937 (3) | 0.2057 (3) | 0.02553 (9) | 0.0311 (5) | |
C49 | −0.7587 (3) | 0.2848 (3) | 0.00868 (8) | 0.0306 (5) | |
C410 | −0.8951 (3) | 0.2067 (3) | −0.05445 (9) | 0.0320 (5) | |
C411 | −1.0583 (3) | 0.2880 (3) | −0.06900 (9) | 0.0359 (5) | |
C412 | −1.1994 (3) | 0.2083 (3) | −0.13125 (10) | 0.0469 (6) | |
N4 | 0.5860 (2) | 0.3970 (2) | 0.37904 (7) | 0.0258 (4) | |
C5 | 0.7347 (3) | 0.2925 (2) | 0.47208 (8) | 0.0205 (4) | |
O5 | 0.94503 (18) | 0.39005 (16) | 0.40582 (6) | 0.0277 (3) | |
N5 | 0.9124 (2) | 0.32132 (19) | 0.45776 (7) | 0.0232 (4) | |
C6 | 0.7010 (3) | 0.2256 (2) | 0.53197 (8) | 0.0214 (4) | |
C61 | 1.0065 (3) | 0.1385 (2) | 0.67025 (8) | 0.0228 (4) | |
C62 | 1.1182 (3) | 0.2673 (2) | 0.72010 (8) | 0.0287 (4) | |
C63 | 1.2871 (3) | 0.2512 (3) | 0.75526 (9) | 0.0337 (5) | |
C64 | 1.3490 (3) | 0.1083 (3) | 0.73945 (9) | 0.0328 (5) | |
C65 | 1.2403 (3) | −0.0204 (3) | 0.68956 (9) | 0.0301 (5) | |
C66 | 1.0671 (3) | −0.0071 (2) | 0.65580 (8) | 0.0273 (4) | |
C67 | 0.8200 (3) | 0.1525 (3) | 0.63341 (8) | 0.0264 (4) | |
O6 | 0.85125 (16) | 0.19713 (15) | 0.56988 (5) | 0.0236 (3) | |
H2A | 0.1251 | 0.2197 | 0.5073 | 0.035* | |
H2B | 0.2127 | 0.1585 | 0.5685 | 0.035* | |
H41A | 0.4887 | 0.5758 | 0.3299 | 0.033* | |
H41B | 0.3342 | 0.4526 | 0.3681 | 0.033* | |
H42A | 0.2807 | 0.1968 | 0.2913 | 0.033* | |
H42B | 0.4158 | 0.3360 | 0.2510 | 0.033* | |
H43A | 0.0676 | 0.3752 | 0.2831 | 0.035* | |
H43B | 0.1992 | 0.5061 | 0.2405 | 0.035* | |
H44A | 0.0976 | 0.2751 | 0.1569 | 0.037* | |
H44B | −0.0189 | 0.1311 | 0.1999 | 0.037* | |
H45A | −0.2369 | 0.2930 | 0.2043 | 0.034* | |
H45B | −0.1160 | 0.4474 | 0.1659 | 0.034* | |
H46A | −0.3447 | 0.0844 | 0.1131 | 0.037* | |
H46B | −0.2149 | 0.2320 | 0.0742 | 0.037* | |
H47A | −0.5428 | 0.2645 | 0.1225 | 0.035* | |
H47B | −0.4080 | 0.4217 | 0.0884 | 0.035* | |
H48A | −0.6510 | 0.0721 | 0.0264 | 0.037* | |
H48B | −0.5138 | 0.2276 | −0.0080 | 0.037* | |
H49A | −0.8368 | 0.2636 | 0.0426 | 0.037* | |
H49B | −0.7003 | 0.4183 | 0.0080 | 0.037* | |
H41C | −0.9538 | 0.0731 | −0.0541 | 0.038* | |
H41D | −0.8182 | 0.2292 | −0.0887 | 0.038* | |
H41E | −1.1326 | 0.2684 | −0.0341 | 0.043* | |
H41F | −0.9993 | 0.4213 | −0.0702 | 0.043* | |
H41G | −1.1273 | 0.2271 | −0.1662 | 0.070* | |
H41H | −1.2981 | 0.2690 | −0.1380 | 0.070* | |
H41I | −1.2639 | 0.0774 | −0.1297 | 0.070* | |
H4 | 0.6945 | 0.4114 | 0.3646 | 0.031* | |
H62 | 1.0784 | 0.3678 | 0.7303 | 0.034* | |
H63 | 1.3604 | 0.3383 | 0.7902 | 0.040* | |
H64 | 1.4664 | 0.0985 | 0.7630 | 0.039* | |
H65 | 1.2837 | −0.1178 | 0.6783 | 0.036* | |
H66 | 0.9897 | −0.0984 | 0.6226 | 0.033* | |
H67A | 0.7123 | 0.0352 | 0.6309 | 0.032* | |
H67B | 0.7843 | 0.2487 | 0.6546 | 0.032* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0173 (9) | 0.0279 (9) | 0.0249 (8) | 0.0107 (7) | 0.0008 (7) | −0.0006 (6) |
C2 | 0.0181 (11) | 0.0246 (10) | 0.0269 (10) | 0.0088 (8) | 0.0004 (8) | −0.0033 (7) |
N2 | 0.0183 (9) | 0.0450 (10) | 0.0273 (9) | 0.0140 (7) | 0.0044 (7) | 0.0051 (7) |
N3 | 0.0173 (9) | 0.0305 (9) | 0.0242 (8) | 0.0106 (7) | 0.0020 (7) | 0.0011 (6) |
C4 | 0.0190 (10) | 0.0222 (10) | 0.0246 (9) | 0.0085 (8) | −0.0009 (8) | −0.0030 (7) |
C41 | 0.0266 (11) | 0.0344 (11) | 0.0255 (10) | 0.0159 (9) | 0.0015 (9) | 0.0057 (8) |
C42 | 0.0259 (11) | 0.0303 (11) | 0.0278 (10) | 0.0130 (8) | 0.0038 (9) | 0.0028 (8) |
C43 | 0.0270 (11) | 0.0322 (11) | 0.0280 (10) | 0.0119 (9) | 0.0033 (9) | 0.0045 (8) |
C44 | 0.0271 (12) | 0.0385 (12) | 0.0265 (10) | 0.0118 (9) | 0.0035 (9) | 0.0010 (8) |
C45 | 0.0272 (12) | 0.0306 (11) | 0.0260 (10) | 0.0097 (9) | 0.0008 (9) | 0.0022 (8) |
C46 | 0.0279 (12) | 0.0351 (11) | 0.0273 (10) | 0.0084 (9) | 0.0018 (9) | 0.0020 (8) |
C47 | 0.0274 (12) | 0.0300 (11) | 0.0278 (10) | 0.0089 (9) | −0.0010 (9) | 0.0008 (8) |
C48 | 0.0282 (12) | 0.0327 (11) | 0.0290 (10) | 0.0085 (9) | 0.0001 (9) | 0.0010 (8) |
C49 | 0.0280 (12) | 0.0326 (11) | 0.0288 (10) | 0.0081 (9) | 0.0023 (9) | 0.0031 (8) |
C410 | 0.0293 (12) | 0.0332 (11) | 0.0292 (10) | 0.0071 (9) | 0.0006 (9) | 0.0038 (8) |
C411 | 0.0300 (12) | 0.0426 (12) | 0.0306 (11) | 0.0084 (9) | 0.0001 (9) | 0.0074 (9) |
C412 | 0.0385 (14) | 0.0486 (14) | 0.0422 (13) | 0.0067 (11) | −0.0088 (11) | 0.0106 (10) |
N4 | 0.0208 (9) | 0.0363 (9) | 0.0240 (8) | 0.0144 (7) | 0.0041 (7) | 0.0035 (6) |
C5 | 0.0162 (10) | 0.0219 (10) | 0.0232 (9) | 0.0076 (8) | 0.0014 (8) | −0.0026 (7) |
O5 | 0.0262 (8) | 0.0324 (7) | 0.0264 (7) | 0.0108 (6) | 0.0079 (6) | 0.0036 (5) |
N5 | 0.0210 (9) | 0.0252 (9) | 0.0232 (8) | 0.0077 (7) | 0.0042 (7) | −0.0004 (6) |
C6 | 0.0173 (11) | 0.0210 (10) | 0.0259 (9) | 0.0091 (8) | 0.0000 (8) | −0.0032 (7) |
C61 | 0.0203 (10) | 0.0293 (10) | 0.0206 (9) | 0.0097 (8) | 0.0050 (8) | 0.0049 (7) |
C62 | 0.0295 (12) | 0.0296 (11) | 0.0285 (10) | 0.0135 (9) | 0.0036 (9) | 0.0004 (8) |
C63 | 0.0307 (12) | 0.0346 (12) | 0.0285 (10) | 0.0068 (9) | −0.0052 (9) | −0.0025 (8) |
C64 | 0.0240 (11) | 0.0398 (12) | 0.0331 (11) | 0.0125 (9) | −0.0029 (9) | 0.0089 (9) |
C65 | 0.0297 (12) | 0.0324 (11) | 0.0334 (11) | 0.0181 (9) | 0.0048 (9) | 0.0044 (8) |
C66 | 0.0249 (11) | 0.0305 (11) | 0.0252 (10) | 0.0101 (8) | 0.0006 (8) | −0.0004 (7) |
C67 | 0.0251 (11) | 0.0347 (11) | 0.0218 (9) | 0.0140 (9) | 0.0030 (8) | 0.0025 (7) |
O6 | 0.0179 (7) | 0.0312 (7) | 0.0235 (6) | 0.0122 (6) | 0.0008 (5) | 0.0032 (5) |
Geometric parameters (Å, º) top
N1—C6 | 1.300 (2) | C48—H48B | 0.99 |
N1—C2 | 1.368 (2) | C49—C410 | 1.516 (2) |
C2—N2 | 1.321 (2) | C49—H49A | 0.99 |
C2—N3 | 1.342 (2) | C49—H49B | 0.99 |
N2—H2A | 0.88 | C410—C411 | 1.520 (3) |
N2—H2B | 0.88 | C410—H41C | 0.99 |
N3—C4 | 1.331 (2) | C410—H41D | 0.99 |
C4—N4 | 1.335 (2) | C411—C412 | 1.517 (3) |
C4—C5 | 1.450 (2) | C411—H41E | 0.99 |
C41—N4 | 1.462 (2) | C411—H41F | 0.99 |
C41—C42 | 1.521 (2) | C412—H41G | 0.98 |
C41—H41A | 0.99 | C412—H41H | 0.98 |
C41—H41B | 0.99 | C412—H41I | 0.98 |
C42—C43 | 1.527 (2) | N4—H4 | 0.88 |
C42—H42A | 0.99 | C5—N5 | 1.344 (2) |
C42—H42B | 0.99 | C5—C6 | 1.435 (2) |
C43—C44 | 1.522 (2) | O5—N5 | 1.2799 (17) |
C43—H43A | 0.99 | C6—O6 | 1.3400 (19) |
C43—H43B | 0.99 | C61—C62 | 1.385 (2) |
C44—C45 | 1.522 (2) | C61—C66 | 1.388 (2) |
C44—H44A | 0.99 | C61—C67 | 1.500 (2) |
C44—H44B | 0.99 | C62—C63 | 1.384 (3) |
C45—C46 | 1.520 (2) | C62—H62 | 0.95 |
C45—H45A | 0.99 | C63—C64 | 1.382 (3) |
C45—H45B | 0.99 | C63—H63 | 0.95 |
C46—C47 | 1.524 (3) | C64—C65 | 1.381 (3) |
C46—H46A | 0.99 | C64—H64 | 0.95 |
C46—H46B | 0.99 | C65—C66 | 1.391 (2) |
C47—C48 | 1.521 (2) | C65—H65 | 0.95 |
C47—H47A | 0.99 | C66—H66 | 0.95 |
C47—H47B | 0.99 | C67—O6 | 1.457 (2) |
C48—C49 | 1.526 (3) | C67—H67A | 0.99 |
C48—H48A | 0.99 | C67—H67B | 0.99 |
| | | |
C6—N1—C2 | 115.76 (15) | C410—C49—C48 | 114.93 (15) |
N2—C2—N3 | 116.97 (15) | C410—C49—H49A | 108.5 |
N2—C2—N1 | 115.71 (16) | C48—C49—H49A | 108.5 |
N3—C2—N1 | 127.31 (17) | C410—C49—H49B | 108.5 |
C2—N2—H2A | 120.0 | C48—C49—H49B | 108.5 |
C2—N2—H2B | 120.0 | H49A—C49—H49B | 107.5 |
H2A—N2—H2B | 120.0 | C49—C410—C411 | 113.15 (16) |
C4—N3—C2 | 116.57 (14) | C49—C410—H41C | 108.9 |
N3—C4—N4 | 118.61 (15) | C411—C410—H41C | 108.9 |
N3—C4—C5 | 121.99 (16) | C49—C410—H41D | 108.9 |
N4—C4—C5 | 119.41 (16) | C411—C410—H41D | 108.9 |
N4—C41—C42 | 113.97 (15) | H41C—C410—H41D | 107.8 |
N4—C41—H41A | 108.8 | C412—C411—C410 | 113.96 (17) |
C42—C41—H41A | 108.8 | C412—C411—H41E | 108.8 |
N4—C41—H41B | 108.8 | C410—C411—H41E | 108.8 |
C42—C41—H41B | 108.8 | C412—C411—H41F | 108.8 |
H41A—C41—H41B | 107.7 | C410—C411—H41F | 108.8 |
C41—C42—C43 | 109.07 (14) | H41E—C411—H41F | 107.7 |
C41—C42—H42A | 109.9 | C411—C412—H41G | 109.5 |
C43—C42—H42A | 109.9 | C411—C412—H41H | 109.5 |
C41—C42—H42B | 109.9 | H41G—C412—H41H | 109.5 |
C43—C42—H42B | 109.9 | C411—C412—H41I | 109.5 |
H42A—C42—H42B | 108.3 | H41G—C412—H41I | 109.5 |
C44—C43—C42 | 116.20 (15) | H41H—C412—H41I | 109.5 |
C44—C43—H43A | 108.2 | C4—N4—C41 | 122.29 (15) |
C42—C43—H43A | 108.2 | C4—N4—H4 | 118.9 |
C44—C43—H43B | 108.2 | C41—N4—H4 | 118.9 |
C42—C43—H43B | 108.2 | N5—C5—C6 | 118.33 (15) |
H43A—C43—H43B | 107.4 | N5—C5—C4 | 127.50 (16) |
C45—C44—C43 | 111.09 (15) | C6—C5—C4 | 114.14 (16) |
C45—C44—H44A | 109.4 | O5—N5—C5 | 118.12 (13) |
C43—C44—H44A | 109.4 | N1—C6—O6 | 118.88 (15) |
C45—C44—H44B | 109.4 | N1—C6—C5 | 124.15 (15) |
C43—C44—H44B | 109.4 | O6—C6—C5 | 116.96 (15) |
H44A—C44—H44B | 108.0 | C62—C61—C66 | 118.90 (16) |
C46—C45—C44 | 116.17 (15) | C62—C61—C67 | 120.89 (16) |
C46—C45—H45A | 108.2 | C66—C61—C67 | 120.19 (16) |
C44—C45—H45A | 108.2 | C63—C62—C61 | 120.82 (17) |
C46—C45—H45B | 108.2 | C63—C62—H62 | 119.6 |
C44—C45—H45B | 108.2 | C61—C62—H62 | 119.6 |
H45A—C45—H45B | 107.4 | C64—C63—C62 | 119.83 (17) |
C45—C46—C47 | 112.09 (15) | C64—C63—H63 | 120.1 |
C45—C46—H46A | 109.2 | C62—C63—H63 | 120.1 |
C47—C46—H46A | 109.2 | C65—C64—C63 | 120.09 (17) |
C45—C46—H46B | 109.2 | C65—C64—H64 | 120.0 |
C47—C46—H46B | 109.2 | C63—C64—H64 | 120.0 |
H46A—C46—H46B | 107.9 | C64—C65—C66 | 119.80 (17) |
C48—C47—C46 | 115.25 (15) | C64—C65—H65 | 120.1 |
C48—C47—H47A | 108.5 | C66—C65—H65 | 120.1 |
C46—C47—H47A | 108.5 | C61—C66—C65 | 120.49 (17) |
C48—C47—H47B | 108.5 | C61—C66—H66 | 119.8 |
C46—C47—H47B | 108.5 | C65—C66—H66 | 119.8 |
H47A—C47—H47B | 107.5 | O6—C67—C61 | 107.91 (14) |
C47—C48—C49 | 112.77 (15) | O6—C67—H67A | 110.1 |
C47—C48—H48A | 109.0 | C61—C67—H67A | 110.1 |
C49—C48—H48A | 109.0 | O6—C67—H67B | 110.1 |
C47—C48—H48B | 109.0 | C61—C67—H67B | 110.1 |
C49—C48—H48B | 109.0 | H67A—C67—H67B | 108.4 |
H48A—C48—H48B | 107.8 | C6—O6—C67 | 115.32 (13) |
| | | |
C6—N1—C2—N2 | −178.94 (14) | N4—C4—C5—C6 | 177.16 (15) |
C6—N1—C2—N3 | 0.7 (3) | C6—C5—N5—O5 | −176.38 (14) |
N2—C2—N3—C4 | 177.46 (14) | C4—C5—N5—O5 | 1.4 (2) |
N1—C2—N3—C4 | −2.2 (3) | C2—N1—C6—O6 | 178.79 (14) |
C2—N3—C4—N4 | −176.84 (15) | C2—N1—C6—C5 | −0.4 (2) |
C2—N3—C4—C5 | 3.3 (2) | N5—C5—C6—N1 | 179.52 (14) |
N4—C41—C42—C43 | 172.21 (15) | C4—C5—C6—N1 | 1.5 (2) |
C41—C42—C43—C44 | −177.34 (16) | N5—C5—C6—O6 | 0.3 (2) |
C42—C43—C44—C45 | 173.80 (16) | C4—C5—C6—O6 | −177.72 (14) |
C43—C44—C45—C46 | 175.76 (16) | C66—C61—C62—C63 | −0.3 (3) |
C44—C45—C46—C47 | −176.54 (16) | C67—C61—C62—C63 | 178.03 (17) |
C45—C46—C47—C48 | 175.84 (16) | C61—C62—C63—C64 | 2.0 (3) |
C46—C47—C48—C49 | −179.09 (16) | C62—C63—C64—C65 | −1.4 (3) |
C47—C48—C49—C410 | −179.74 (16) | C63—C64—C65—C66 | −0.9 (3) |
C48—C49—C410—C411 | 179.44 (17) | C62—C61—C66—C65 | −2.0 (3) |
C49—C410—C411—C412 | −178.59 (17) | C67—C61—C66—C65 | 179.71 (17) |
N3—C4—N4—C41 | 5.8 (2) | C64—C65—C66—C61 | 2.5 (3) |
C5—C4—N4—C41 | −174.38 (15) | C62—C61—C67—O6 | 110.83 (18) |
C42—C41—N4—C4 | −108.68 (19) | C66—C61—C67—O6 | −70.9 (2) |
N3—C4—C5—N5 | 179.17 (15) | N1—C6—O6—C67 | −7.0 (2) |
N4—C4—C5—N5 | −0.7 (3) | C5—C6—O6—C67 | 172.25 (14) |
N3—C4—C5—C6 | −3.0 (2) | C61—C67—O6—C6 | −176.06 (14) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O5 | 0.88 | 1.96 | 2.624 (2) | 131 |
N2—H2A···N5i | 0.88 | 2.12 | 2.987 (2) | 169 |
Symmetry code: (i) x−1, y, z. |
(4) 2-amino-6-benzyloxy-4-(
N-cyclohexylamino)-5-nitrosopyrimidine
top
Crystal data top
C17H21N5O2 | Z = 2 |
Mr = 327.39 | F(000) = 348 |
Triclinic, P1 | Dx = 1.365 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2656 (5) Å | Cell parameters from 3442 reflections |
b = 10.6077 (6) Å | θ = 3.2–27.5° |
c = 10.6743 (7) Å | µ = 0.09 mm−1 |
α = 64.841 (4)° | T = 120 K |
β = 71.021 (3)° | Block, red |
γ = 87.275 (5)° | 0.12 × 0.08 × 0.06 mm |
V = 796.56 (9) Å3 | |
Data collection top
Kappa-CCD diffractometer | 3442 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 1528 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.128 |
ϕ scans, and ω scans with κ offsets | θmax = 27.5°, θmin = 3.2° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −10→10 |
Tmin = 0.974, Tmax = 0.994 | k = −13→13 |
11753 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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0553P)2] where P = (Fo2 + 2Fc2)/3 |
3442 reflections | (Δ/σ)max = 0.001 |
217 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Crystal data top
C17H21N5O2 | γ = 87.275 (5)° |
Mr = 327.39 | V = 796.56 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.2656 (5) Å | Mo Kα radiation |
b = 10.6077 (6) Å | µ = 0.09 mm−1 |
c = 10.6743 (7) Å | T = 120 K |
α = 64.841 (4)° | 0.12 × 0.08 × 0.06 mm |
β = 71.021 (3)° | |
Data collection top
Kappa-CCD diffractometer | 3442 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 1528 reflections with I > 2σ(I) |
Tmin = 0.974, Tmax = 0.994 | Rint = 0.128 |
11753 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.063 | 0 restraints |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 0.95 | Δρmax = 0.39 e Å−3 |
3442 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 | |
N1 | 0.7984 (3) | 0.1635 (3) | 0.5108 (3) | 0.0179 (6) | |
O5 | 0.4348 (2) | 0.1762 (2) | 0.2518 (2) | 0.0205 (5) | |
C2 | 0.9370 (4) | 0.1769 (3) | 0.3892 (3) | 0.0173 (7) | |
N2 | 1.0879 (3) | 0.1751 (3) | 0.4071 (3) | 0.0228 (7) | |
N3 | 0.9343 (3) | 0.1926 (3) | 0.2587 (3) | 0.0188 (6) | |
C4 | 0.7790 (4) | 0.1916 (3) | 0.2447 (3) | 0.0166 (7) | |
C41 | 0.9095 (4) | 0.2424 (3) | −0.0196 (3) | 0.0198 (7) | |
C42 | 0.9246 (4) | 0.3956 (4) | −0.1256 (4) | 0.0270 (8) | |
C43 | 1.0627 (4) | 0.4292 (4) | −0.2743 (3) | 0.0273 (8) | |
C44 | 1.0341 (4) | 0.3353 (4) | −0.3406 (3) | 0.0264 (8) | |
C45 | 1.0200 (4) | 0.1814 (4) | −0.2339 (3) | 0.0255 (8) | |
C46 | 0.8800 (4) | 0.1481 (3) | −0.0860 (3) | 0.0221 (8) | |
N4 | 0.7667 (3) | 0.2110 (3) | 0.1173 (3) | 0.0205 (6) | |
N5 | 0.4587 (3) | 0.1629 (3) | 0.3711 (3) | 0.0187 (6) | |
O6 | 0.5049 (2) | 0.1449 (2) | 0.6097 (2) | 0.0196 (5) | |
C5 | 0.6217 (4) | 0.1701 (3) | 0.3669 (3) | 0.0152 (7) | |
C6 | 0.6473 (4) | 0.1587 (3) | 0.4980 (3) | 0.0162 (7) | |
C61 | 0.4934 (4) | 0.2485 (3) | 0.7763 (3) | 0.0164 (7) | |
C62 | 0.5612 (4) | 0.3820 (3) | 0.6663 (3) | 0.0199 (8) | |
C63 | 0.5404 (4) | 0.4969 (4) | 0.6961 (3) | 0.0238 (8) | |
C64 | 0.4498 (4) | 0.4807 (4) | 0.8378 (3) | 0.0243 (8) | |
C65 | 0.3813 (4) | 0.3493 (3) | 0.9481 (3) | 0.0223 (8) | |
C66 | 0.4022 (4) | 0.2338 (3) | 0.9179 (3) | 0.0217 (8) | |
C67 | 0.5218 (4) | 0.1209 (3) | 0.7491 (3) | 0.0177 (7) | |
H2A | 1.1828 | 0.1842 | 0.3345 | 0.027* | |
H2B | 1.0936 | 0.1650 | 0.4918 | 0.027* | |
H41 | 1.0187 | 0.2225 | 0.0032 | 0.024* | |
H42A | 0.9532 | 0.4544 | −0.0828 | 0.032* | |
H42B | 0.8125 | 0.4187 | −0.1398 | 0.032* | |
H43A | 1.0626 | 0.5280 | −0.3424 | 0.033* | |
H43B | 1.1769 | 0.4182 | −0.2619 | 0.033* | |
H44A | 1.1311 | 0.3553 | −0.4327 | 0.032* | |
H44B | 0.9272 | 0.3550 | −0.3652 | 0.032* | |
H45A | 1.1318 | 0.1591 | −0.2187 | 0.031* | |
H45B | 0.9932 | 0.1220 | −0.2769 | 0.031* | |
H46A | 0.7664 | 0.1602 | −0.0996 | 0.027* | |
H46B | 0.8786 | 0.0491 | −0.0175 | 0.027* | |
H4 | 0.6623 | 0.2044 | 0.1147 | 0.025* | |
H62 | 0.6227 | 0.3940 | 0.5690 | 0.024* | |
H63 | 0.5880 | 0.5874 | 0.6198 | 0.029* | |
H64 | 0.4352 | 0.5600 | 0.8585 | 0.029* | |
H65 | 0.3197 | 0.3379 | 1.0451 | 0.027* | |
H66 | 0.3540 | 0.1435 | 0.9944 | 0.026* | |
H67A | 0.6383 | 0.0942 | 0.7488 | 0.021* | |
H67B | 0.4370 | 0.0423 | 0.8297 | 0.021* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0136 (13) | 0.0226 (16) | 0.0179 (14) | 0.0026 (11) | −0.0041 (12) | −0.0102 (13) |
O5 | 0.0192 (11) | 0.0275 (14) | 0.0182 (12) | 0.0023 (9) | −0.0073 (10) | −0.0122 (11) |
C2 | 0.0184 (17) | 0.0157 (19) | 0.0175 (17) | 0.0030 (13) | −0.0048 (15) | −0.0079 (15) |
N2 | 0.0134 (13) | 0.0380 (19) | 0.0189 (15) | 0.0016 (12) | −0.0057 (12) | −0.0138 (14) |
N3 | 0.0149 (13) | 0.0258 (17) | 0.0184 (14) | 0.0027 (11) | −0.0084 (12) | −0.0100 (13) |
C4 | 0.0186 (16) | 0.0141 (18) | 0.0172 (17) | −0.0008 (13) | −0.0049 (15) | −0.0074 (15) |
C41 | 0.0134 (15) | 0.028 (2) | 0.0157 (17) | 0.0023 (14) | −0.0030 (14) | −0.0089 (16) |
C42 | 0.0264 (18) | 0.028 (2) | 0.0260 (19) | 0.0012 (15) | −0.0028 (16) | −0.0149 (18) |
C43 | 0.0256 (18) | 0.028 (2) | 0.0198 (18) | −0.0025 (15) | −0.0028 (16) | −0.0059 (17) |
C44 | 0.0217 (17) | 0.037 (2) | 0.0170 (18) | 0.0003 (15) | −0.0052 (15) | −0.0091 (17) |
C45 | 0.0241 (18) | 0.031 (2) | 0.0220 (19) | −0.0011 (15) | −0.0042 (16) | −0.0145 (17) |
C46 | 0.0199 (17) | 0.026 (2) | 0.0168 (18) | 0.0036 (15) | −0.0041 (15) | −0.0072 (16) |
N4 | 0.0129 (13) | 0.0361 (18) | 0.0155 (15) | 0.0020 (12) | −0.0047 (12) | −0.0138 (13) |
N5 | 0.0202 (14) | 0.0192 (16) | 0.0229 (15) | 0.0052 (11) | −0.0100 (12) | −0.0128 (13) |
O6 | 0.0157 (11) | 0.0285 (14) | 0.0158 (12) | 0.0021 (9) | −0.0044 (10) | −0.0112 (11) |
C5 | 0.0128 (15) | 0.0174 (18) | 0.0166 (17) | 0.0003 (13) | −0.0046 (13) | −0.0086 (14) |
C6 | 0.0170 (17) | 0.0134 (19) | 0.0146 (17) | 0.0029 (13) | −0.0021 (15) | −0.0053 (15) |
C61 | 0.0135 (15) | 0.0215 (19) | 0.0156 (17) | 0.0046 (13) | −0.0056 (14) | −0.0089 (15) |
C62 | 0.0168 (16) | 0.024 (2) | 0.0134 (17) | −0.0001 (14) | −0.0012 (14) | −0.0058 (16) |
C63 | 0.0223 (17) | 0.019 (2) | 0.024 (2) | 0.0008 (14) | −0.0053 (16) | −0.0060 (16) |
C64 | 0.0288 (18) | 0.022 (2) | 0.025 (2) | 0.0026 (15) | −0.0109 (16) | −0.0121 (18) |
C65 | 0.0262 (18) | 0.029 (2) | 0.0163 (18) | 0.0070 (16) | −0.0091 (15) | −0.0132 (17) |
C66 | 0.0237 (17) | 0.023 (2) | 0.0162 (18) | 0.0020 (15) | −0.0059 (15) | −0.0071 (16) |
C67 | 0.0194 (16) | 0.0196 (19) | 0.0105 (16) | −0.0004 (14) | −0.0033 (14) | −0.0044 (15) |
Geometric parameters (Å, º) top
N1—C6 | 1.305 (4) | C45—H45A | 0.99 |
N1—C2 | 1.382 (4) | C45—H45B | 0.99 |
O5—N5 | 1.301 (3) | C46—H46A | 0.99 |
C2—N2 | 1.320 (4) | C46—H46B | 0.99 |
C2—N3 | 1.338 (4) | N4—H4 | 0.88 |
N2—H2A | 0.88 | N5—C5 | 1.338 (4) |
N2—H2B | 0.88 | O6—C6 | 1.336 (3) |
N3—C4 | 1.341 (4) | O6—C67 | 1.452 (3) |
C4—N4 | 1.323 (4) | C5—C6 | 1.436 (4) |
C4—C5 | 1.454 (4) | C61—C62 | 1.390 (4) |
C41—N4 | 1.463 (4) | C61—C66 | 1.395 (4) |
C41—C42 | 1.517 (4) | C61—C67 | 1.494 (4) |
C41—C46 | 1.517 (4) | C62—C63 | 1.375 (4) |
C41—H41 | 1.00 | C62—H62 | 0.95 |
C42—C43 | 1.526 (4) | C63—C64 | 1.390 (4) |
C42—H42A | 0.99 | C63—H63 | 0.95 |
C42—H42B | 0.99 | C64—C65 | 1.377 (4) |
C43—C44 | 1.510 (4) | C64—H64 | 0.95 |
C43—H43A | 0.99 | C65—C66 | 1.383 (4) |
C43—H43B | 0.99 | C65—H65 | 0.95 |
C44—C45 | 1.526 (5) | C66—H66 | 0.95 |
C44—H44A | 0.99 | C67—H67A | 0.99 |
C44—H44B | 0.99 | C67—H67B | 0.99 |
C45—C46 | 1.528 (4) | | |
| | | |
C6—N1—C2 | 115.5 (2) | C41—C46—C45 | 111.5 (2) |
N2—C2—N3 | 118.0 (3) | C41—C46—H46A | 109.3 |
N2—C2—N1 | 114.3 (2) | C45—C46—H46A | 109.3 |
N3—C2—N1 | 127.6 (3) | C41—C46—H46B | 109.3 |
C2—N2—H2A | 120.0 | C45—C46—H46B | 109.3 |
C2—N2—H2B | 120.0 | H46A—C46—H46B | 108.0 |
H2A—N2—H2B | 120.0 | C4—N4—C41 | 126.5 (2) |
C2—N3—C4 | 116.6 (2) | C4—N4—H4 | 116.7 |
N4—C4—N3 | 119.9 (3) | C41—N4—H4 | 116.7 |
N4—C4—C5 | 118.6 (3) | O5—N5—C5 | 117.0 (2) |
N3—C4—C5 | 121.5 (2) | C6—O6—C67 | 118.4 (2) |
N4—C41—C42 | 110.4 (2) | N5—C5—C6 | 116.7 (3) |
N4—C41—C46 | 108.9 (2) | N5—C5—C4 | 128.4 (2) |
C42—C41—C46 | 111.1 (2) | C6—C5—C4 | 114.9 (2) |
N4—C41—H41 | 108.8 | N1—C6—O6 | 120.2 (2) |
C42—C41—H41 | 108.8 | N1—C6—C5 | 123.8 (3) |
C46—C41—H41 | 108.8 | O6—C6—C5 | 115.9 (2) |
C41—C42—C43 | 111.7 (3) | C62—C61—C66 | 118.4 (3) |
C41—C42—H42A | 109.3 | C62—C61—C67 | 122.2 (3) |
C43—C42—H42A | 109.3 | C66—C61—C67 | 119.4 (3) |
C41—C42—H42B | 109.3 | C63—C62—C61 | 121.0 (3) |
C43—C42—H42B | 109.3 | C63—C62—H62 | 119.5 |
H42A—C42—H42B | 107.9 | C61—C62—H62 | 119.5 |
C44—C43—C42 | 112.0 (3) | C62—C63—C64 | 120.1 (3) |
C44—C43—H43A | 109.2 | C62—C63—H63 | 120.0 |
C42—C43—H43A | 109.2 | C64—C63—H63 | 120.0 |
C44—C43—H43B | 109.2 | C65—C64—C63 | 119.8 (3) |
C42—C43—H43B | 109.2 | C65—C64—H64 | 120.1 |
H43A—C43—H43B | 107.9 | C63—C64—H64 | 120.1 |
C43—C44—C45 | 110.9 (3) | C64—C65—C66 | 120.1 (3) |
C43—C44—H44A | 109.5 | C64—C65—H65 | 120.0 |
C45—C44—H44A | 109.5 | C66—C65—H65 | 120.0 |
C43—C44—H44B | 109.5 | C65—C66—C61 | 120.7 (3) |
C45—C44—H44B | 109.5 | C65—C66—H66 | 119.6 |
H44A—C44—H44B | 108.1 | C61—C66—H66 | 119.6 |
C44—C45—C46 | 111.3 (3) | O6—C67—C61 | 111.4 (2) |
C44—C45—H45A | 109.4 | O6—C67—H67A | 109.4 |
C46—C45—H45A | 109.4 | C61—C67—H67A | 109.4 |
C44—C45—H45B | 109.4 | O6—C67—H67B | 109.4 |
C46—C45—H45B | 109.4 | C61—C67—H67B | 109.4 |
H45A—C45—H45B | 108.0 | H67A—C67—H67B | 108.0 |
| | | |
C6—N1—C2—N2 | −177.1 (3) | N4—C4—C5—C6 | −176.3 (3) |
C6—N1—C2—N3 | 3.7 (4) | N3—C4—C5—C6 | 3.5 (4) |
N2—C2—N3—C4 | 178.9 (3) | C2—N1—C6—O6 | 179.5 (3) |
N1—C2—N3—C4 | −1.9 (5) | C2—N1—C6—C5 | −1.6 (4) |
C2—N3—C4—N4 | 177.9 (3) | C67—O6—C6—N1 | −6.3 (4) |
C2—N3—C4—C5 | −1.9 (4) | C67—O6—C6—C5 | 174.8 (2) |
N4—C41—C42—C43 | −175.3 (2) | N5—C5—C6—N1 | 179.8 (3) |
C46—C41—C42—C43 | −54.4 (3) | C4—C5—C6—N1 | −1.6 (4) |
C41—C42—C43—C44 | 54.7 (4) | N5—C5—C6—O6 | −1.3 (4) |
C42—C43—C44—C45 | −54.6 (4) | C4—C5—C6—O6 | 177.2 (2) |
C43—C44—C45—C46 | 55.1 (3) | C66—C61—C62—C63 | 0.6 (4) |
N4—C41—C46—C45 | 176.9 (2) | C67—C61—C62—C63 | −176.7 (3) |
C42—C41—C46—C45 | 55.1 (3) | C61—C62—C63—C64 | −0.3 (5) |
C44—C45—C46—C41 | −55.7 (3) | C62—C63—C64—C65 | 0.1 (4) |
N3—C4—N4—C41 | −3.7 (5) | C63—C64—C65—C66 | −0.2 (4) |
C5—C4—N4—C41 | 176.1 (3) | C64—C65—C66—C61 | 0.4 (4) |
C42—C41—N4—C4 | −104.6 (3) | C62—C61—C66—C65 | −0.6 (4) |
C46—C41—N4—C4 | 133.2 (3) | C67—C61—C66—C65 | 176.7 (3) |
O5—N5—C5—C6 | 178.6 (2) | C6—O6—C67—C61 | 106.7 (3) |
O5—N5—C5—C4 | 0.3 (4) | C62—C61—C67—O6 | −42.2 (4) |
N4—C4—C5—N5 | 2.0 (5) | C66—C61—C67—O6 | 140.6 (3) |
N3—C4—C5—N5 | −178.2 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O5 | 0.88 | 1.91 | 2.609 (3) | 135 |
N2—H2A···O5i | 0.88 | 1.99 | 2.804 (3) | 153 |
C43—H43B···Cg1ii | 0.99 | 2.73 | 3.717 (4) | 173 |
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z−1. |
(5) 2-Amino-6-benzyloxy-4-(
N-phenylamino)-5-nitrosopyrimidine
top
Crystal data top
C17H15N5O2 | Z = 1 |
Mr = 321.34 | F(000) = 168 |
Triclinic, P1 | Dx = 1.445 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 4.7622 (3) Å | Cell parameters from 2993 reflections |
b = 5.8123 (4) Å | θ = 3.1–27.4° |
c = 13.5635 (11) Å | µ = 0.10 mm−1 |
α = 79.851 (2)° | T = 120 K |
β = 87.346 (2)° | Plate, orange |
γ = 89.692 (5)° | 0.40 × 0.14 × 0.02 mm |
V = 369.16 (5) Å3 | |
Data collection top
Kappa-CCD diffractometer | 2993 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2348 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.071 |
ϕ scans, and ω scans with κ offsets | θmax = 27.4°, θmin = 3.1° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −6→6 |
Tmin = 0.895, Tmax = 0.998 | k = −7→7 |
5085 measured reflections | l = −17→17 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.136 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0712P)2] where P = (Fo2 + 2Fc2)/3 |
2993 reflections | (Δ/σ)max < 0.001 |
217 parameters | Δρmax = 0.24 e Å−3 |
3 restraints | Δρmin = −0.28 e Å−3 |
Crystal data top
C17H15N5O2 | γ = 89.692 (5)° |
Mr = 321.34 | V = 369.16 (5) Å3 |
Triclinic, P1 | Z = 1 |
a = 4.7622 (3) Å | Mo Kα radiation |
b = 5.8123 (4) Å | µ = 0.10 mm−1 |
c = 13.5635 (11) Å | T = 120 K |
α = 79.851 (2)° | 0.40 × 0.14 × 0.02 mm |
β = 87.346 (2)° | |
Data collection top
Kappa-CCD diffractometer | 2993 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 2348 reflections with I > 2σ(I) |
Tmin = 0.895, Tmax = 0.998 | Rint = 0.071 |
5085 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.051 | 3 restraints |
wR(F2) = 0.136 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.24 e Å−3 |
2993 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 | |
O5 | 0.6912 (4) | 0.6660 (4) | 0.42918 (16) | 0.0242 (5) | |
O6 | 0.8705 (4) | 0.9113 (4) | 0.66886 (15) | 0.0220 (5) | |
N1 | 0.5250 (5) | 1.1914 (4) | 0.64857 (18) | 0.0184 (5) | |
N2 | 0.1834 (5) | 1.4673 (4) | 0.62031 (19) | 0.0214 (6) | |
N3 | 0.2449 (5) | 1.2380 (4) | 0.50086 (19) | 0.0190 (6) | |
N4 | 0.3122 (5) | 0.9852 (4) | 0.38606 (18) | 0.0196 (6) | |
N5 | 0.7492 (5) | 0.7482 (4) | 0.50760 (18) | 0.0193 (6) | |
C2 | 0.3201 (6) | 1.2946 (5) | 0.5867 (2) | 0.0168 (6) | |
C4 | 0.3793 (5) | 1.0606 (5) | 0.4697 (2) | 0.0154 (6) | |
C5 | 0.6021 (6) | 0.9377 (5) | 0.5265 (2) | 0.0170 (6) | |
C6 | 0.6623 (5) | 1.0205 (5) | 0.6159 (2) | 0.0172 (6) | |
C41 | 0.1099 (6) | 1.0710 (5) | 0.3147 (2) | 0.0189 (7) | |
C42 | −0.0391 (6) | 1.2776 (5) | 0.3116 (2) | 0.0216 (7) | |
C43 | −0.2282 (6) | 1.3425 (6) | 0.2366 (2) | 0.0252 (7) | |
C44 | −0.2703 (6) | 1.2034 (6) | 0.1654 (2) | 0.0256 (7) | |
C45 | −0.1259 (6) | 0.9967 (6) | 0.1689 (2) | 0.0274 (7) | |
C46 | 0.0648 (6) | 0.9304 (6) | 0.2431 (2) | 0.0252 (7) | |
C61 | 0.6786 (6) | 0.8086 (5) | 0.8404 (2) | 0.0213 (7) | |
C62 | 0.5716 (6) | 0.5998 (6) | 0.8193 (2) | 0.0258 (7) | |
C63 | 0.3680 (7) | 0.4723 (6) | 0.8835 (3) | 0.0364 (9) | |
C64 | 0.2753 (7) | 0.5501 (7) | 0.9694 (3) | 0.0423 (10) | |
C65 | 0.3834 (7) | 0.7516 (7) | 0.9927 (3) | 0.0402 (10) | |
C66 | 0.5845 (7) | 0.8847 (6) | 0.9278 (2) | 0.0295 (8) | |
C67 | 0.8942 (6) | 0.9502 (5) | 0.7712 (2) | 0.0208 (7) | |
H2A | 0.0473 | 1.5407 | 0.5860 | 0.026* | |
H2B | 0.2291 | 1.5083 | 0.6769 | 0.026* | |
H4 | 0.4083 | 0.8633 | 0.3732 | 0.023* | |
H42 | −0.0123 | 1.3738 | 0.3603 | 0.026* | |
H43 | −0.3300 | 1.4843 | 0.2341 | 0.030* | |
H44 | −0.3989 | 1.2507 | 0.1143 | 0.031* | |
H45 | −0.1563 | 0.8999 | 0.1208 | 0.033* | |
H46 | 0.1655 | 0.7882 | 0.2453 | 0.030* | |
H62 | 0.6382 | 0.5442 | 0.7607 | 0.031* | |
H63 | 0.2937 | 0.3324 | 0.8678 | 0.044* | |
H64 | 0.1358 | 0.4640 | 1.0129 | 0.051* | |
H65 | 0.3219 | 0.8016 | 1.0531 | 0.048* | |
H66 | 0.6555 | 1.0257 | 0.9435 | 0.035* | |
H67A | 0.8668 | 1.1182 | 0.7734 | 0.025* | |
H67B | 1.0848 | 0.9060 | 0.7938 | 0.025* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O5 | 0.0259 (11) | 0.0267 (12) | 0.0221 (12) | 0.0076 (9) | −0.0039 (9) | −0.0100 (9) |
O6 | 0.0225 (11) | 0.0290 (12) | 0.0148 (11) | 0.0070 (9) | −0.0034 (8) | −0.0047 (9) |
N1 | 0.0151 (11) | 0.0225 (13) | 0.0186 (13) | 0.0047 (10) | −0.0035 (9) | −0.0061 (10) |
N2 | 0.0200 (13) | 0.0231 (14) | 0.0222 (14) | 0.0066 (10) | −0.0043 (10) | −0.0065 (11) |
N3 | 0.0213 (13) | 0.0171 (13) | 0.0193 (14) | 0.0032 (11) | −0.0011 (10) | −0.0055 (11) |
N4 | 0.0224 (12) | 0.0198 (14) | 0.0176 (14) | 0.0038 (10) | −0.0019 (10) | −0.0062 (11) |
N5 | 0.0215 (13) | 0.0200 (14) | 0.0169 (13) | −0.0008 (11) | 0.0029 (10) | −0.0060 (11) |
C2 | 0.0161 (14) | 0.0188 (16) | 0.0154 (15) | 0.0023 (11) | 0.0004 (11) | −0.0032 (12) |
C4 | 0.0108 (14) | 0.0175 (15) | 0.0173 (16) | 0.0017 (11) | −0.0010 (11) | −0.0011 (12) |
C5 | 0.0159 (15) | 0.0168 (15) | 0.0180 (16) | 0.0005 (11) | −0.0005 (12) | −0.0022 (12) |
C6 | 0.0150 (15) | 0.0185 (15) | 0.0172 (16) | −0.0026 (12) | 0.0011 (11) | −0.0011 (12) |
C41 | 0.0168 (14) | 0.0236 (17) | 0.0167 (16) | −0.0037 (12) | −0.0004 (12) | −0.0042 (13) |
C42 | 0.0196 (15) | 0.0258 (17) | 0.0200 (17) | 0.0048 (12) | −0.0051 (12) | −0.0045 (13) |
C43 | 0.0204 (15) | 0.0264 (18) | 0.0285 (18) | 0.0072 (12) | −0.0056 (12) | −0.0027 (15) |
C44 | 0.0231 (16) | 0.0333 (19) | 0.0200 (17) | 0.0004 (14) | −0.0094 (12) | −0.0018 (14) |
C45 | 0.0329 (18) | 0.0322 (19) | 0.0199 (16) | −0.0051 (14) | −0.0038 (13) | −0.0116 (14) |
C46 | 0.0289 (18) | 0.0286 (18) | 0.0200 (16) | 0.0040 (14) | −0.0006 (13) | −0.0093 (14) |
C61 | 0.0218 (15) | 0.0257 (17) | 0.0162 (15) | 0.0049 (12) | −0.0050 (11) | −0.0027 (13) |
C62 | 0.0268 (16) | 0.0242 (17) | 0.0265 (17) | 0.0049 (13) | −0.0070 (13) | −0.0031 (14) |
C63 | 0.033 (2) | 0.0297 (19) | 0.042 (2) | 0.0003 (15) | −0.0099 (16) | 0.0075 (16) |
C64 | 0.0235 (18) | 0.059 (3) | 0.034 (2) | 0.0045 (18) | 0.0004 (15) | 0.0188 (19) |
C65 | 0.0355 (19) | 0.064 (3) | 0.0191 (18) | 0.0122 (19) | 0.0014 (14) | −0.0023 (18) |
C66 | 0.0321 (18) | 0.034 (2) | 0.0231 (18) | 0.0083 (15) | −0.0030 (13) | −0.0075 (15) |
C67 | 0.0186 (14) | 0.0274 (18) | 0.0177 (15) | 0.0055 (12) | −0.0112 (11) | −0.0049 (13) |
Geometric parameters (Å, º) top
O5—N5 | 1.282 (3) | C43—H43 | 0.9500 |
O6—C6 | 1.342 (3) | C44—C45 | 1.376 (4) |
O6—C67 | 1.455 (3) | C44—H44 | 0.9500 |
N1—C6 | 1.316 (4) | C45—C46 | 1.390 (4) |
N1—C2 | 1.382 (4) | C45—H45 | 0.9500 |
N2—C2 | 1.330 (4) | C46—H46 | 0.9500 |
N2—H2A | 0.8800 | C61—C66 | 1.391 (4) |
N2—H2B | 0.8800 | C61—C62 | 1.399 (4) |
N3—C2 | 1.328 (4) | C61—C67 | 1.503 (4) |
N3—C4 | 1.332 (4) | C62—C63 | 1.396 (5) |
N4—C4 | 1.338 (4) | C62—H62 | 0.9500 |
N4—C41 | 1.423 (4) | C63—C64 | 1.377 (5) |
N4—H4 | 0.8800 | C63—H63 | 0.9500 |
N5—C5 | 1.358 (4) | C64—C65 | 1.375 (6) |
C4—C5 | 1.451 (4) | C64—H64 | 0.9500 |
C5—C6 | 1.423 (4) | C65—C66 | 1.408 (5) |
C41—C42 | 1.387 (4) | C65—H65 | 0.9500 |
C41—C46 | 1.399 (4) | C66—H66 | 0.9500 |
C42—C43 | 1.392 (4) | C67—H67A | 0.9900 |
C42—H42 | 0.9500 | C67—H67B | 0.9900 |
C43—C44 | 1.385 (4) | | |
| | | |
C6—O6—C67 | 117.7 (2) | C45—C44—H44 | 120.0 |
C6—N1—C2 | 114.7 (2) | C43—C44—H44 | 120.0 |
C2—N2—H2A | 120.0 | C44—C45—C46 | 119.6 (3) |
C2—N2—H2B | 120.0 | C44—C45—H45 | 120.2 |
H2A—N2—H2B | 120.0 | C46—C45—H45 | 120.2 |
C2—N3—C4 | 117.3 (2) | C45—C46—C41 | 120.6 (3) |
C4—N4—C41 | 130.2 (3) | C45—C46—H46 | 119.7 |
C4—N4—H4 | 114.9 | C41—C46—H46 | 119.7 |
C41—N4—H4 | 114.9 | C66—C61—C62 | 119.0 (3) |
O5—N5—C5 | 117.4 (2) | C66—C61—C67 | 119.6 (3) |
N3—C2—N2 | 118.2 (3) | C62—C61—C67 | 121.4 (3) |
N3—C2—N1 | 127.7 (2) | C63—C62—C61 | 120.7 (3) |
N2—C2—N1 | 114.1 (3) | C63—C62—H62 | 119.7 |
N3—C4—N4 | 121.8 (2) | C61—C62—H62 | 119.7 |
N3—C4—C5 | 121.0 (2) | C64—C63—C62 | 119.8 (3) |
N4—C4—C5 | 117.2 (2) | C64—C63—H63 | 120.1 |
N5—C5—C6 | 116.5 (2) | C62—C63—H63 | 120.1 |
N5—C5—C4 | 128.2 (3) | C65—C64—C63 | 120.3 (3) |
C6—C5—C4 | 115.2 (2) | C65—C64—H64 | 119.8 |
N1—C6—O6 | 119.8 (2) | C63—C64—H64 | 119.8 |
N1—C6—C5 | 124.0 (2) | C64—C65—C66 | 120.6 (3) |
O6—C6—C5 | 116.2 (2) | C64—C65—H65 | 119.7 |
C42—C41—C46 | 119.5 (3) | C66—C65—H65 | 119.7 |
C42—C41—N4 | 125.3 (3) | C61—C66—C65 | 119.6 (3) |
C46—C41—N4 | 115.2 (3) | C61—C66—H66 | 120.2 |
C41—C42—C43 | 119.3 (3) | C65—C66—H66 | 120.2 |
C41—C42—H42 | 120.4 | O6—C67—C61 | 110.7 (2) |
C43—C42—H42 | 120.4 | O6—C67—H67A | 109.5 |
C44—C43—C42 | 121.0 (3) | C61—C67—H67A | 109.5 |
C44—C43—H43 | 119.5 | O6—C67—H67B | 109.5 |
C42—C43—H43 | 119.5 | C61—C67—H67B | 109.5 |
C45—C44—C43 | 120.0 (3) | H67A—C67—H67B | 108.1 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O5 | 0.88 | 1.86 | 2.593 (3) | 139 |
N2—H2A···N5i | 0.88 | 2.07 | 2.942 (3) | 173 |
C42—H42···O5i | 0.95 | 2.48 | 3.215 (4) | 133 |
Symmetry code: (i) x−1, y+1, z. |
(7) 2-Amino-4-(
N-butylamino)-6-(3-pyridyl)methoxy-5-nitrosopyrimidine
top
Crystal data top
C14H18N6O2 | F(000) = 1280 |
Mr = 302.33 | Dx = 1.348 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 3366 reflections |
a = 28.3925 (6) Å | θ = 3.2–27.5° |
b = 8.1627 (3) Å | µ = 0.10 mm−1 |
c = 15.1540 (5) Å | T = 298 K |
β = 121.9700 (13)° | Block, blue |
V = 2979.39 (17) Å3 | 0.22 × 0.08 × 0.03 mm |
Z = 8 | |
Data collection top
Kappa-CCD diffractometer | 1422 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed X-ray tube | Rint = 0.065 |
Graphite monochromator | θmax = 27.5°, θmin = 3.2° |
ϕ scans, and ω scans with κ offsets | h = −28→36 |
9945 measured reflections | k = −10→10 |
3366 independent reflections | l = −19→16 |
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 0.91 | w = 1/[σ2(Fo2) + (0.0556P)2] where P = (Fo2 + 2Fc2)/3 |
3366 reflections | (Δ/σ)max < 0.001 |
200 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
Crystal data top
C14H18N6O2 | V = 2979.39 (17) Å3 |
Mr = 302.33 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 28.3925 (6) Å | µ = 0.10 mm−1 |
b = 8.1627 (3) Å | T = 298 K |
c = 15.1540 (5) Å | 0.22 × 0.08 × 0.03 mm |
β = 121.9700 (13)° | |
Data collection top
Kappa-CCD diffractometer | 1422 reflections with I > 2σ(I) |
9945 measured reflections | Rint = 0.065 |
3366 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
wR(F2) = 0.145 | H-atom parameters constrained |
S = 0.91 | Δρmax = 0.18 e Å−3 |
3366 reflections | Δρmin = −0.20 e Å−3 |
200 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.09435 (10) | 0.6293 (2) | 0.35945 (17) | 0.0462 (6) | |
C2 | 0.11846 (12) | 0.5643 (3) | 0.4580 (2) | 0.0438 (7) | |
N2 | 0.11195 (10) | 0.6559 (3) | 0.52305 (17) | 0.0593 (7) | |
N3 | 0.14601 (10) | 0.4235 (2) | 0.49342 (16) | 0.0444 (6) | |
N4 | 0.17926 (9) | 0.1942 (3) | 0.45739 (16) | 0.0468 (6) | |
C5 | 0.12872 (11) | 0.3883 (3) | 0.31959 (19) | 0.0387 (7) | |
N5 | 0.13250 (10) | 0.3120 (3) | 0.24433 (17) | 0.0500 (6) | |
O5 | 0.15774 (8) | 0.1743 (2) | 0.26680 (14) | 0.0608 (6) | |
C4 | 0.15148 (11) | 0.3341 (3) | 0.4253 (2) | 0.0395 (7) | |
C41 | 0.20508 (12) | 0.1292 (3) | 0.5627 (2) | 0.0487 (7) | |
C42 | 0.22718 (12) | −0.0406 (3) | 0.5669 (2) | 0.0484 (7) | |
C43 | 0.25527 (14) | −0.1174 (3) | 0.6742 (2) | 0.0557 (8) | |
C44 | 0.27919 (15) | −0.2858 (4) | 0.6761 (3) | 0.0740 (10) | |
C6 | 0.10045 (11) | 0.5410 (3) | 0.29452 (19) | 0.0419 (7) | |
C61 | 0.04640 (12) | 0.8031 (3) | 0.0687 (2) | 0.0446 (7) | |
C62 | 0.07416 (13) | 0.9390 (3) | 0.0682 (2) | 0.0547 (8) | |
N63 | 0.07286 (11) | 0.9978 (3) | −0.01612 (19) | 0.0580 (7) | |
C64 | 0.04292 (13) | 0.9130 (4) | −0.1035 (2) | 0.0573 (8) | |
C65 | 0.01361 (13) | 0.7776 (4) | −0.1114 (2) | 0.0597 (9) | |
C66 | 0.01435 (13) | 0.7223 (3) | −0.0246 (2) | 0.0554 (8) | |
C67 | 0.05078 (14) | 0.7497 (3) | 0.1677 (2) | 0.0596 (9) | |
O6 | 0.07952 (8) | 0.5934 (2) | 0.19662 (13) | 0.0534 (6) | |
H2A | 0.1253 | 0.6239 | 0.5860 | 0.071* | |
H2B | 0.0943 | 0.7474 | 0.5023 | 0.071* | |
H4 | 0.1823 | 0.1375 | 0.4128 | 0.056* | |
H41A | 0.1780 | 0.1252 | 0.5831 | 0.058* | |
H41B | 0.2352 | 0.2005 | 0.6108 | 0.058* | |
H42A | 0.2536 | −0.0352 | 0.5449 | 0.058* | |
H42B | 0.1967 | −0.1103 | 0.5181 | 0.058* | |
H43A | 0.2285 | −0.1282 | 0.6952 | 0.067* | |
H43B | 0.2849 | −0.0462 | 0.7238 | 0.067* | |
H44A | 0.2494 | −0.3605 | 0.6339 | 0.111* | |
H44B | 0.3001 | −0.3255 | 0.7463 | 0.111* | |
H44C | 0.3030 | −0.2772 | 0.6492 | 0.111* | |
H62 | 0.0956 | 0.9951 | 0.1306 | 0.066* | |
H64 | 0.0421 | 0.9488 | −0.1625 | 0.069* | |
H65 | −0.0068 | 0.7223 | −0.1744 | 0.072* | |
H66 | −0.0066 | 0.6314 | −0.0290 | 0.066* | |
H67A | 0.0714 | 0.8300 | 0.2221 | 0.072* | |
H67B | 0.0141 | 0.7382 | 0.1570 | 0.072* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0626 (17) | 0.0455 (13) | 0.0333 (14) | 0.0074 (11) | 0.0274 (13) | 0.0034 (10) |
C2 | 0.056 (2) | 0.0457 (16) | 0.0363 (17) | −0.0018 (14) | 0.0289 (15) | −0.0013 (13) |
N2 | 0.088 (2) | 0.0569 (15) | 0.0408 (15) | 0.0185 (14) | 0.0392 (15) | 0.0061 (11) |
N3 | 0.0541 (16) | 0.0449 (13) | 0.0363 (13) | 0.0065 (11) | 0.0254 (12) | 0.0038 (10) |
N4 | 0.0587 (16) | 0.0461 (13) | 0.0360 (13) | 0.0071 (12) | 0.0254 (12) | 0.0034 (10) |
C5 | 0.0457 (18) | 0.0403 (15) | 0.0324 (15) | −0.0003 (13) | 0.0224 (14) | 0.0003 (11) |
N5 | 0.0584 (17) | 0.0499 (14) | 0.0400 (14) | 0.0014 (12) | 0.0248 (13) | −0.0046 (11) |
O5 | 0.0769 (16) | 0.0540 (12) | 0.0481 (13) | 0.0168 (11) | 0.0306 (12) | −0.0011 (9) |
C4 | 0.0445 (18) | 0.0396 (15) | 0.0375 (17) | −0.0035 (13) | 0.0238 (14) | 0.0014 (12) |
C41 | 0.0515 (19) | 0.0546 (17) | 0.0366 (17) | 0.0033 (14) | 0.0210 (15) | 0.0083 (12) |
C42 | 0.054 (2) | 0.0504 (16) | 0.0403 (17) | 0.0012 (14) | 0.0242 (15) | 0.0059 (13) |
C43 | 0.067 (2) | 0.0563 (18) | 0.0454 (18) | 0.0076 (15) | 0.0312 (17) | 0.0105 (13) |
C44 | 0.095 (3) | 0.067 (2) | 0.064 (2) | 0.024 (2) | 0.044 (2) | 0.0242 (17) |
C6 | 0.0480 (19) | 0.0447 (16) | 0.0308 (16) | −0.0009 (14) | 0.0193 (14) | 0.0040 (12) |
C61 | 0.0573 (19) | 0.0400 (15) | 0.0389 (17) | 0.0105 (15) | 0.0271 (15) | 0.0077 (12) |
C62 | 0.063 (2) | 0.0526 (18) | 0.0397 (18) | 0.0029 (16) | 0.0212 (16) | −0.0025 (13) |
N63 | 0.0644 (18) | 0.0558 (15) | 0.0548 (17) | −0.0018 (13) | 0.0323 (15) | 0.0079 (13) |
C64 | 0.065 (2) | 0.066 (2) | 0.043 (2) | 0.0013 (17) | 0.0301 (18) | 0.0051 (15) |
C65 | 0.075 (2) | 0.0610 (19) | 0.0417 (19) | −0.0074 (17) | 0.0297 (17) | −0.0054 (14) |
C66 | 0.073 (2) | 0.0474 (16) | 0.0500 (19) | −0.0086 (15) | 0.0350 (18) | −0.0005 (14) |
C67 | 0.090 (2) | 0.0510 (17) | 0.0494 (18) | 0.0218 (16) | 0.0443 (19) | 0.0147 (14) |
O6 | 0.0766 (15) | 0.0471 (11) | 0.0367 (12) | 0.0172 (10) | 0.0300 (11) | 0.0099 (8) |
Geometric parameters (Å, º) top
N1—C6 | 1.303 (3) | C43—H43A | 0.97 |
N1—C2 | 1.378 (3) | C43—H43B | 0.97 |
C2—N2 | 1.326 (3) | C44—H44A | 0.96 |
C2—N3 | 1.333 (3) | C44—H44B | 0.96 |
N2—H2A | 0.86 | C44—H44C | 0.96 |
N2—H2B | 0.86 | C6—O6 | 1.343 (3) |
N3—C4 | 1.339 (3) | C61—C62 | 1.363 (4) |
N4—C4 | 1.326 (3) | C61—C66 | 1.378 (4) |
N4—C41 | 1.458 (3) | C61—C67 | 1.503 (4) |
N4—H4 | 0.86 | C62—N63 | 1.347 (3) |
C5—N5 | 1.352 (3) | C62—H62 | 0.93 |
C5—C6 | 1.422 (3) | N63—C64 | 1.328 (3) |
C5—C4 | 1.443 (3) | C64—C65 | 1.350 (4) |
N5—O5 | 1.279 (3) | C64—H64 | 0.93 |
C41—C42 | 1.509 (3) | C65—C66 | 1.380 (4) |
C41—H41A | 0.97 | C65—H65 | 0.93 |
C41—H41B | 0.97 | C66—H66 | 0.93 |
C42—C43 | 1.517 (4) | C67—O6 | 1.452 (3) |
C42—H42A | 0.97 | C67—H67A | 0.97 |
C42—H42B | 0.97 | C67—H67B | 0.97 |
C43—C44 | 1.526 (4) | | |
| | | |
C6—N1—C2 | 114.7 (2) | C44—C43—H43B | 109.3 |
N2—C2—N3 | 118.1 (2) | H43A—C43—H43B | 108.0 |
N2—C2—N1 | 113.8 (2) | C43—C44—H44A | 109.5 |
N3—C2—N1 | 128.1 (2) | C43—C44—H44B | 109.5 |
C2—N2—H2A | 120.0 | H44A—C44—H44B | 109.5 |
C2—N2—H2B | 120.0 | C43—C44—H44C | 109.5 |
H2A—N2—H2B | 120.0 | H44A—C44—H44C | 109.5 |
C2—N3—C4 | 116.3 (2) | H44B—C44—H44C | 109.5 |
C4—N4—C41 | 124.9 (2) | N1—C6—O6 | 120.0 (2) |
C4—N4—H4 | 117.6 | N1—C6—C5 | 124.4 (2) |
C41—N4—H4 | 117.6 | O6—C6—C5 | 115.6 (2) |
N5—C5—C6 | 117.6 (2) | C62—C61—C66 | 117.0 (2) |
N5—C5—C4 | 127.3 (2) | C62—C61—C67 | 119.9 (2) |
C6—C5—C4 | 115.0 (2) | C66—C61—C67 | 123.1 (3) |
O5—N5—C5 | 117.6 (2) | N63—C62—C61 | 124.7 (3) |
N4—C4—N3 | 118.4 (2) | N63—C62—H62 | 117.6 |
N4—C4—C5 | 120.1 (2) | C61—C62—H62 | 117.6 |
N3—C4—C5 | 121.5 (2) | C64—N63—C62 | 116.2 (3) |
N4—C41—C42 | 109.7 (2) | N63—C64—C65 | 123.7 (3) |
N4—C41—H41A | 109.7 | N63—C64—H64 | 118.1 |
C42—C41—H41A | 109.7 | C65—C64—H64 | 118.1 |
N4—C41—H41B | 109.7 | C64—C65—C66 | 119.0 (3) |
C42—C41—H41B | 109.7 | C64—C65—H65 | 120.5 |
H41A—C41—H41B | 108.2 | C66—C65—H65 | 120.5 |
C41—C42—C43 | 113.3 (2) | C61—C66—C65 | 119.3 (3) |
C41—C42—H42A | 108.9 | C61—C66—H66 | 120.3 |
C43—C42—H42A | 108.9 | C65—C66—H66 | 120.3 |
C41—C42—H42B | 108.9 | O6—C67—C61 | 107.0 (2) |
C43—C42—H42B | 108.9 | O6—C67—H67A | 110.3 |
H42A—C42—H42B | 107.7 | C61—C67—H67A | 110.3 |
C42—C43—C44 | 111.6 (2) | O6—C67—H67B | 110.3 |
C42—C43—H43A | 109.3 | C61—C67—H67B | 110.3 |
C44—C43—H43A | 109.3 | H67A—C67—H67B | 108.6 |
C42—C43—H43B | 109.3 | C6—O6—C67 | 117.57 (19) |
| | | |
C6—N1—C2—N2 | 179.9 (2) | C2—N1—C6—C5 | 0.8 (4) |
C6—N1—C2—N3 | −1.0 (4) | N5—C5—C6—N1 | −178.9 (3) |
N2—C2—N3—C4 | 179.7 (2) | C4—C5—C6—N1 | −0.2 (4) |
N1—C2—N3—C4 | 0.6 (4) | N5—C5—C6—O6 | 0.8 (3) |
C6—C5—N5—O5 | −179.7 (2) | C4—C5—C6—O6 | 179.4 (2) |
C4—C5—N5—O5 | 1.9 (4) | C66—C61—C62—N63 | −0.7 (4) |
C41—N4—C4—N3 | −0.4 (4) | C67—C61—C62—N63 | −179.6 (3) |
C41—N4—C4—C5 | 178.5 (2) | C61—C62—N63—C64 | −1.4 (4) |
C2—N3—C4—N4 | 179.0 (2) | C62—N63—C64—C65 | 1.8 (4) |
C2—N3—C4—C5 | 0.1 (4) | N63—C64—C65—C66 | −0.1 (5) |
N5—C5—C4—N4 | −0.7 (4) | C62—C61—C66—C65 | 2.5 (4) |
C6—C5—C4—N4 | −179.2 (2) | C67—C61—C66—C65 | −178.6 (3) |
N5—C5—C4—N3 | 178.2 (3) | C64—C65—C66—C61 | −2.2 (5) |
C6—C5—C4—N3 | −0.2 (4) | C62—C61—C67—O6 | −114.0 (3) |
C4—N4—C41—C42 | 173.6 (2) | C66—C61—C67—O6 | 67.2 (4) |
N4—C41—C42—C43 | 179.6 (2) | N1—C6—O6—C67 | 0.3 (4) |
C41—C42—C43—C44 | −177.5 (3) | C5—C6—O6—C67 | −179.4 (2) |
C2—N1—C6—O6 | −178.9 (2) | C61—C67—O6—C6 | 163.8 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O5 | 0.86 | 1.96 | 2.622 (3) | 133 |
N2—H2A···N5i | 0.86 | 2.36 | 3.095 (3) | 144 |
N2—H2B···N63ii | 0.86 | 2.14 | 2.979 (3) | 164 |
C62—H62···O5iii | 0.93 | 2.38 | 3.289 (3) | 167 |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, −y+2, z+1/2; (iii) x, y+1, z. |
(8) 2-Amino-6-benzyloxy-4-piperidino-5-nitrosopyrimidine monohydrate
top
Crystal data top
C16H19N5O2·H2O | F(000) = 704 |
Mr = 331.38 | Dx = 1.347 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3658 reflections |
a = 7.2557 (4) Å | θ = 2.9–27.4° |
b = 11.4692 (7) Å | µ = 0.10 mm−1 |
c = 20.4417 (15) Å | T = 120 K |
β = 106.113 (3)° | Plate, purple |
V = 1634.27 (18) Å3 | 0.35 × 0.10 × 0.02 mm |
Z = 4 | |
Data collection top
Kappa-CCD diffractometer | 3658 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 1996 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.094 |
ϕ scans, and ω scans with κ offsets | θmax = 27.4°, θmin = 2.9° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −9→9 |
Tmin = 0.956, Tmax = 0.998 | k = −14→13 |
14044 measured reflections | l = −26→26 |
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) = 0.146 | H-atom parameters constrained |
S = 0.96 | w = 1/[σ2(Fo2) + (0.0692P)2] where P = (Fo2 + 2Fc2)/3 |
3658 reflections | (Δ/σ)max < 0.001 |
217 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
Crystal data top
C16H19N5O2·H2O | V = 1634.27 (18) Å3 |
Mr = 331.38 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.2557 (4) Å | µ = 0.10 mm−1 |
b = 11.4692 (7) Å | T = 120 K |
c = 20.4417 (15) Å | 0.35 × 0.10 × 0.02 mm |
β = 106.113 (3)° | |
Data collection top
Kappa-CCD diffractometer | 3658 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 1996 reflections with I > 2σ(I) |
Tmin = 0.956, Tmax = 0.998 | Rint = 0.094 |
14044 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 0.96 | Δρmax = 0.24 e Å−3 |
3658 reflections | Δρmin = −0.32 e Å−3 |
217 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.7546 (3) | 0.11594 (18) | 0.19305 (10) | 0.0218 (5) | |
C2 | 0.6003 (3) | 0.0420 (2) | 0.17565 (11) | 0.0193 (5) | |
N2 | 0.4642 (2) | 0.06307 (18) | 0.20583 (10) | 0.0237 (5) | |
N3 | 0.5709 (2) | −0.04385 (18) | 0.12918 (9) | 0.0210 (5) | |
N4 | 0.6710 (2) | −0.13078 (17) | 0.04380 (9) | 0.0203 (5) | |
C4 | 0.7119 (3) | −0.0656 (2) | 0.09988 (11) | 0.0181 (5) | |
C41 | 0.4782 (3) | −0.1816 (2) | 0.01548 (12) | 0.0253 (6) | |
C42 | 0.4937 (4) | −0.3048 (2) | −0.00936 (14) | 0.0310 (6) | |
C43 | 0.6125 (4) | −0.3086 (2) | −0.06029 (14) | 0.0347 (7) | |
C44 | 0.8075 (4) | −0.2505 (2) | −0.03168 (13) | 0.0305 (6) | |
C45 | 0.7854 (3) | −0.1293 (2) | −0.00578 (12) | 0.0244 (6) | |
C5 | 0.9028 (3) | −0.0174 (2) | 0.13069 (11) | 0.0183 (5) | |
N5 | 1.0750 (3) | −0.06937 (18) | 0.14043 (9) | 0.0211 (5) | |
O5 | 1.0783 (2) | −0.17172 (14) | 0.11555 (8) | 0.0250 (4) | |
C6 | 0.9019 (3) | 0.0838 (2) | 0.17257 (11) | 0.0194 (5) | |
C61 | 1.0098 (3) | 0.3537 (2) | 0.20000 (13) | 0.0284 (6) | |
C62 | 0.8268 (4) | 0.3977 (2) | 0.19198 (13) | 0.0328 (6) | |
C63 | 0.7731 (4) | 0.5022 (3) | 0.15803 (14) | 0.0396 (7) | |
C64 | 0.9025 (5) | 0.5619 (3) | 0.13168 (15) | 0.0449 (8) | |
C65 | 1.0860 (5) | 0.5184 (3) | 0.13951 (15) | 0.0460 (8) | |
C66 | 1.1389 (4) | 0.4145 (3) | 0.17433 (14) | 0.0384 (7) | |
C67 | 1.0713 (3) | 0.2432 (2) | 0.23788 (13) | 0.0281 (6) | |
O6 | 1.0636 (2) | 0.14483 (15) | 0.19078 (8) | 0.0246 (4) | |
O1 | 0.5605 (2) | 0.24413 (16) | 0.31356 (9) | 0.0345 (5) | |
H2A | 0.3582 | 0.0214 | 0.1952 | 0.028* | |
H2B | 0.4797 | 0.1188 | 0.2365 | 0.028* | |
H41A | 0.4041 | −0.1329 | −0.0228 | 0.030* | |
H41B | 0.4090 | −0.1825 | 0.0510 | 0.030* | |
H42A | 0.3636 | −0.3355 | −0.0312 | 0.037* | |
H42B | 0.5540 | −0.3555 | 0.0300 | 0.037* | |
H43A | 0.5419 | −0.2684 | −0.1027 | 0.042* | |
H43B | 0.6315 | −0.3908 | −0.0718 | 0.042* | |
H44A | 0.8868 | −0.2984 | 0.0060 | 0.037* | |
H44B | 0.8745 | −0.2459 | −0.0677 | 0.037* | |
H45A | 0.9138 | −0.0963 | 0.0161 | 0.029* | |
H45B | 0.7217 | −0.0785 | −0.0446 | 0.029* | |
H62 | 0.7382 | 0.3561 | 0.2098 | 0.039* | |
H63 | 0.6482 | 0.5328 | 0.1528 | 0.048* | |
H64 | 0.8653 | 0.6332 | 0.1081 | 0.054* | |
H65 | 1.1742 | 0.5593 | 0.1212 | 0.055* | |
H66 | 1.2649 | 0.3849 | 0.1806 | 0.046* | |
H67A | 1.2039 | 0.2519 | 0.2676 | 0.034* | |
H67B | 0.9865 | 0.2266 | 0.2673 | 0.034* | |
H1A | 0.7023 | 0.2505 | 0.3341 | 0.041* | |
H1B | 0.4960 | 0.3097 | 0.3307 | 0.041* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0150 (9) | 0.0259 (12) | 0.0238 (11) | 0.0002 (8) | 0.0042 (8) | −0.0016 (9) |
C2 | 0.0147 (11) | 0.0229 (14) | 0.0196 (12) | 0.0031 (10) | 0.0034 (9) | 0.0025 (10) |
N2 | 0.0160 (9) | 0.0274 (12) | 0.0293 (11) | −0.0025 (8) | 0.0090 (9) | −0.0075 (9) |
N3 | 0.0170 (9) | 0.0246 (12) | 0.0221 (11) | 0.0002 (8) | 0.0065 (8) | −0.0013 (9) |
N4 | 0.0160 (9) | 0.0247 (12) | 0.0199 (10) | −0.0026 (8) | 0.0047 (8) | −0.0040 (9) |
C4 | 0.0153 (11) | 0.0190 (13) | 0.0197 (12) | 0.0014 (9) | 0.0042 (9) | 0.0036 (10) |
C41 | 0.0178 (12) | 0.0322 (16) | 0.0232 (13) | −0.0019 (10) | 0.0013 (10) | −0.0021 (11) |
C42 | 0.0305 (14) | 0.0302 (16) | 0.0315 (15) | −0.0056 (11) | 0.0074 (11) | −0.0048 (12) |
C43 | 0.0348 (15) | 0.0341 (18) | 0.0348 (16) | −0.0026 (12) | 0.0089 (12) | −0.0117 (13) |
C44 | 0.0319 (13) | 0.0352 (17) | 0.0262 (14) | 0.0003 (12) | 0.0110 (11) | −0.0039 (12) |
C45 | 0.0233 (12) | 0.0306 (15) | 0.0199 (13) | −0.0014 (11) | 0.0070 (10) | 0.0006 (11) |
C5 | 0.0135 (11) | 0.0236 (14) | 0.0177 (12) | 0.0001 (9) | 0.0038 (9) | 0.0027 (10) |
N5 | 0.0195 (10) | 0.0229 (12) | 0.0221 (10) | 0.0003 (8) | 0.0079 (8) | −0.0004 (9) |
O5 | 0.0236 (8) | 0.0215 (10) | 0.0297 (10) | 0.0031 (7) | 0.0071 (7) | −0.0042 (8) |
C6 | 0.0157 (11) | 0.0226 (14) | 0.0193 (12) | −0.0010 (9) | 0.0038 (9) | 0.0036 (10) |
C61 | 0.0299 (13) | 0.0279 (15) | 0.0292 (14) | −0.0073 (11) | 0.0116 (11) | −0.0103 (12) |
C62 | 0.0335 (14) | 0.0313 (16) | 0.0314 (15) | −0.0054 (12) | 0.0055 (12) | −0.0047 (13) |
C63 | 0.0438 (16) | 0.0340 (18) | 0.0365 (16) | 0.0016 (13) | 0.0035 (13) | −0.0031 (14) |
C64 | 0.065 (2) | 0.0322 (18) | 0.0349 (16) | −0.0062 (15) | 0.0086 (15) | −0.0001 (14) |
C65 | 0.063 (2) | 0.040 (2) | 0.0393 (17) | −0.0145 (16) | 0.0210 (15) | −0.0042 (15) |
C66 | 0.0399 (16) | 0.0402 (19) | 0.0389 (16) | −0.0101 (14) | 0.0171 (13) | −0.0107 (14) |
C67 | 0.0218 (12) | 0.0296 (16) | 0.0317 (14) | −0.0019 (11) | 0.0052 (11) | −0.0111 (12) |
O6 | 0.0162 (8) | 0.0248 (10) | 0.0334 (10) | −0.0027 (7) | 0.0080 (7) | −0.0081 (8) |
O1 | 0.0191 (8) | 0.0381 (12) | 0.0453 (11) | −0.0002 (8) | 0.0077 (8) | −0.0184 (9) |
Geometric parameters (Å, º) top
N1—C6 | 1.305 (3) | C45—H45A | 0.99 |
N1—C2 | 1.371 (3) | C45—H45B | 0.99 |
C2—N2 | 1.324 (3) | C5—N5 | 1.348 (3) |
C2—N3 | 1.343 (3) | C5—C6 | 1.443 (3) |
N2—H2A | 0.88 | N5—O5 | 1.282 (2) |
N2—H2B | 0.88 | C6—O6 | 1.328 (3) |
N3—C4 | 1.345 (3) | C61—C66 | 1.383 (4) |
N4—C4 | 1.331 (3) | C61—C62 | 1.387 (4) |
N4—C41 | 1.477 (3) | C61—C67 | 1.488 (4) |
N4—C45 | 1.477 (3) | C62—C63 | 1.386 (4) |
C4—C5 | 1.461 (3) | C62—H62 | 0.95 |
C41—C42 | 1.517 (4) | C63—C64 | 1.386 (4) |
C41—H41A | 0.99 | C63—H63 | 0.95 |
C41—H41B | 0.99 | C64—C65 | 1.389 (4) |
C42—C43 | 1.525 (4) | C64—H64 | 0.95 |
C42—H42A | 0.99 | C65—C66 | 1.386 (4) |
C42—H42B | 0.99 | C65—H65 | 0.95 |
C43—C44 | 1.526 (4) | C66—H66 | 0.95 |
C43—H43A | 0.99 | C67—O6 | 1.474 (3) |
C43—H43B | 0.99 | C67—H67A | 0.99 |
C44—C45 | 1.512 (4) | C67—H67B | 0.99 |
C44—H44A | 0.99 | O1—H1A | 1.00 |
C44—H44B | 0.99 | O1—H1B | 1.00 |
| | | |
C6—N1—C2 | 115.1 (2) | N4—C45—H45A | 109.4 |
N2—C2—N3 | 118.1 (2) | C44—C45—H45A | 109.4 |
N2—C2—N1 | 115.3 (2) | N4—C45—H45B | 109.4 |
N3—C2—N1 | 126.52 (19) | C44—C45—H45B | 109.4 |
C2—N2—H2A | 120.0 | H45A—C45—H45B | 108.0 |
C2—N2—H2B | 120.0 | N5—C5—C6 | 115.10 (19) |
H2A—N2—H2B | 120.0 | N5—C5—C4 | 128.7 (2) |
C2—N3—C4 | 117.38 (19) | C6—C5—C4 | 113.61 (18) |
C4—N4—C41 | 121.30 (18) | O5—N5—C5 | 117.68 (18) |
C4—N4—C45 | 123.44 (18) | N1—C6—O6 | 120.0 (2) |
C41—N4—C45 | 112.75 (18) | N1—C6—C5 | 123.8 (2) |
N4—C4—N3 | 118.19 (19) | O6—C6—C5 | 116.19 (18) |
N4—C4—C5 | 122.81 (19) | C66—C61—C62 | 119.9 (3) |
N3—C4—C5 | 119.0 (2) | C66—C61—C67 | 119.4 (2) |
N4—C41—C42 | 110.41 (19) | C62—C61—C67 | 120.7 (2) |
N4—C41—H41A | 109.6 | C63—C62—C61 | 120.0 (3) |
C42—C41—H41A | 109.6 | C63—C62—H62 | 120.0 |
N4—C41—H41B | 109.6 | C61—C62—H62 | 120.0 |
C42—C41—H41B | 109.6 | C62—C63—C64 | 119.7 (3) |
H41A—C41—H41B | 108.1 | C62—C63—H63 | 120.2 |
C41—C42—C43 | 111.3 (2) | C64—C63—H63 | 120.2 |
C41—C42—H42A | 109.4 | C63—C64—C65 | 120.6 (3) |
C43—C42—H42A | 109.4 | C63—C64—H64 | 119.7 |
C41—C42—H42B | 109.4 | C65—C64—H64 | 119.7 |
C43—C42—H42B | 109.4 | C66—C65—C64 | 119.2 (3) |
H42A—C42—H42B | 108.0 | C66—C65—H65 | 120.4 |
C42—C43—C44 | 111.4 (2) | C64—C65—H65 | 120.4 |
C42—C43—H43A | 109.3 | C61—C66—C65 | 120.5 (3) |
C44—C43—H43A | 109.3 | C61—C66—H66 | 119.7 |
C42—C43—H43B | 109.3 | C65—C66—H66 | 119.7 |
C44—C43—H43B | 109.3 | O6—C67—C61 | 111.1 (2) |
H43A—C43—H43B | 108.0 | O6—C67—H67A | 109.4 |
C45—C44—C43 | 111.0 (2) | C61—C67—H67A | 109.4 |
C45—C44—H44A | 109.4 | O6—C67—H67B | 109.4 |
C43—C44—H44A | 109.4 | C61—C67—H67B | 109.4 |
C45—C44—H44B | 109.4 | H67A—C67—H67B | 108.0 |
C43—C44—H44B | 109.4 | C6—O6—C67 | 117.19 (17) |
H44A—C44—H44B | 108.0 | H1A—O1—H1B | 109.0 |
N4—C45—C44 | 111.3 (2) | | |
| | | |
C6—N1—C2—N2 | 168.9 (2) | C6—C5—N5—O5 | 166.00 (19) |
C6—N1—C2—N3 | −14.8 (3) | C4—C5—N5—O5 | 5.8 (3) |
N2—C2—N3—C4 | −178.8 (2) | C2—N1—C6—O6 | −175.3 (2) |
N1—C2—N3—C4 | 5.1 (3) | C2—N1—C6—C5 | 4.1 (3) |
C41—N4—C4—N3 | −2.1 (3) | N5—C5—C6—N1 | −149.7 (2) |
C45—N4—C4—N3 | 158.6 (2) | C4—C5—C6—N1 | 13.5 (3) |
C41—N4—C4—C5 | 177.8 (2) | N5—C5—C6—O6 | 29.6 (3) |
C45—N4—C4—C5 | −21.5 (3) | C4—C5—C6—O6 | −167.10 (19) |
C2—N3—C4—N4 | −165.3 (2) | C66—C61—C62—C63 | 0.3 (4) |
C2—N3—C4—C5 | 14.8 (3) | C67—C61—C62—C63 | 178.4 (2) |
C4—N4—C41—C42 | −139.7 (2) | C61—C62—C63—C64 | 0.5 (4) |
C45—N4—C41—C42 | 57.7 (3) | C62—C63—C64—C65 | −0.6 (4) |
N4—C41—C42—C43 | −55.0 (3) | C63—C64—C65—C66 | −0.3 (4) |
C41—C42—C43—C44 | 53.1 (3) | C62—C61—C66—C65 | −1.1 (4) |
C42—C43—C44—C45 | −52.3 (3) | C67—C61—C66—C65 | −179.3 (2) |
C4—N4—C45—C44 | 140.2 (2) | C64—C65—C66—C61 | 1.1 (4) |
C41—N4—C45—C44 | −57.6 (3) | C66—C61—C67—O6 | −80.7 (3) |
C43—C44—C45—N4 | 54.1 (3) | C62—C61—C67—O6 | 101.2 (3) |
N4—C4—C5—N5 | −42.6 (3) | N1—C6—O6—C67 | 4.0 (3) |
N3—C4—C5—N5 | 137.3 (2) | C5—C6—O6—C67 | −175.37 (19) |
N4—C4—C5—C6 | 156.9 (2) | C61—C67—O6—C6 | −91.7 (2) |
N3—C4—C5—C6 | −23.2 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N5i | 0.88 | 2.30 | 3.158 (3) | 165 |
N2—H2B···O1 | 0.88 | 2.09 | 2.966 (3) | 171 |
O1—H1A···O5ii | 1.00 | 1.87 | 2.791 (2) | 153 |
O1—H1B···N3iii | 1.00 | 1.99 | 2.968 (3) | 167 |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, y+1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2. |
(9) 2-Amino-6-benzyloxy-4-piperidino-pyrimidine
top
Crystal data top
C16H20N4O | Z = 4 |
Mr = 284.36 | F(000) = 608 |
Triclinic, P1 | Dx = 1.255 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.5025 (2) Å | Cell parameters from 6307 reflections |
b = 11.8006 (4) Å | θ = 3.2–27.4° |
c = 20.7673 (10) Å | µ = 0.08 mm−1 |
α = 76.1950 (14)° | T = 120 K |
β = 82.3623 (14)° | Needle, colourless |
γ = 77.330 (4)° | 0.70 × 0.17 × 0.08 mm |
V = 1504.36 (10) Å3 | |
Data collection top
Kappa-CCD diffractometer | 6307 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 4163 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.054 |
ϕ scans, and ω scans with κ offsets | θmax = 27.4°, θmin = 3.2° |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | h = −7→8 |
Tmin = 0.965, Tmax = 0.994 | k = −15→15 |
17141 measured reflections | l = −26→26 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.161 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0891P)2 + 0.0112P] where P = (Fo2 + 2Fc2)/3 |
6307 reflections | (Δ/σ)max < 0.001 |
379 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
Crystal data top
C16H20N4O | γ = 77.330 (4)° |
Mr = 284.36 | V = 1504.36 (10) Å3 |
Triclinic, P1 | Z = 4 |
a = 6.5025 (2) Å | Mo Kα radiation |
b = 11.8006 (4) Å | µ = 0.08 mm−1 |
c = 20.7673 (10) Å | T = 120 K |
α = 76.1950 (14)° | 0.70 × 0.17 × 0.08 mm |
β = 82.3623 (14)° | |
Data collection top
Kappa-CCD diffractometer | 6307 independent reflections |
Absorption correction: multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | 4163 reflections with I > 2σ(I) |
Tmin = 0.965, Tmax = 0.994 | Rint = 0.054 |
17141 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.161 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.33 e Å−3 |
6307 reflections | Δρmin = −0.37 e Å−3 |
379 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N11 | 0.0110 (2) | 0.75322 (13) | 0.15351 (7) | 0.0218 (4) | |
C12 | 0.1444 (3) | 0.71274 (16) | 0.20260 (9) | 0.0200 (4) | |
N12 | 0.0955 (2) | 0.76122 (14) | 0.25623 (7) | 0.0242 (4) | |
N13 | 0.3227 (2) | 0.63035 (13) | 0.20232 (7) | 0.0210 (4) | |
C14 | 0.3809 (3) | 0.58490 (16) | 0.14718 (9) | 0.0205 (4) | |
C141 | 0.6447 (3) | 0.44842 (19) | 0.09084 (10) | 0.0314 (5) | |
C142 | 0.8839 (3) | 0.41727 (19) | 0.08266 (10) | 0.0309 (5) | |
C143 | 0.9775 (3) | 0.34666 (19) | 0.14661 (10) | 0.0331 (5) | |
C144 | 0.8957 (3) | 0.41368 (18) | 0.20221 (10) | 0.0289 (5) | |
C145 | 0.6577 (3) | 0.43967 (18) | 0.21006 (9) | 0.0272 (4) | |
N14 | 0.5695 (2) | 0.50642 (14) | 0.14686 (7) | 0.0260 (4) | |
C15 | 0.2541 (3) | 0.62060 (16) | 0.09391 (9) | 0.0227 (4) | |
C16 | 0.0735 (3) | 0.70490 (16) | 0.10060 (9) | 0.0216 (4) | |
C161 | −0.3168 (3) | 0.86833 (17) | −0.01596 (9) | 0.0248 (4) | |
C162 | −0.4927 (3) | 0.83524 (18) | −0.03119 (10) | 0.0292 (5) | |
C163 | −0.5641 (3) | 0.87643 (18) | −0.09436 (10) | 0.0327 (5) | |
C164 | −0.4591 (3) | 0.95021 (18) | −0.14270 (10) | 0.0350 (5) | |
C167 | −0.2415 (3) | 0.82596 (19) | 0.05286 (9) | 0.0314 (5) | |
C165 | −0.2834 (3) | 0.98416 (19) | −0.12790 (10) | 0.0357 (5) | |
C166 | −0.2134 (3) | 0.94322 (18) | −0.06497 (10) | 0.0315 (5) | |
O16 | −0.0472 (2) | 0.73968 (12) | 0.04816 (6) | 0.0280 (3) | |
N21 | 0.4331 (2) | 0.75792 (13) | 0.34964 (7) | 0.0214 (4) | |
C22 | 0.5693 (3) | 0.80224 (16) | 0.29988 (9) | 0.0206 (4) | |
N22 | 0.6007 (2) | 0.75660 (14) | 0.24529 (7) | 0.0262 (4) | |
N23 | 0.6787 (2) | 0.88644 (13) | 0.29946 (7) | 0.0211 (4) | |
C24 | 0.6589 (3) | 0.92879 (16) | 0.35557 (9) | 0.0212 (4) | |
C241 | 0.7761 (3) | 1.06592 (18) | 0.41072 (9) | 0.0276 (5) | |
C242 | 0.9988 (3) | 1.07798 (17) | 0.41893 (9) | 0.0256 (4) | |
C243 | 1.1009 (3) | 1.14397 (18) | 0.35516 (10) | 0.0286 (5) | |
C244 | 1.0937 (3) | 1.08613 (18) | 0.29770 (9) | 0.0264 (4) | |
C245 | 0.8687 (3) | 1.07606 (17) | 0.29146 (9) | 0.0258 (4) | |
N24 | 0.7767 (3) | 1.01184 (14) | 0.35427 (7) | 0.0260 (4) | |
C25 | 0.5279 (3) | 0.88589 (16) | 0.41094 (9) | 0.0228 (4) | |
C26 | 0.4195 (3) | 0.80179 (16) | 0.40391 (9) | 0.0208 (4) | |
C261 | 0.0675 (3) | 0.62977 (17) | 0.51869 (9) | 0.0249 (4) | |
C262 | 0.1903 (3) | 0.55205 (18) | 0.56661 (10) | 0.0326 (5) | |
C263 | 0.0977 (4) | 0.50528 (19) | 0.62860 (10) | 0.0361 (5) | |
C264 | −0.1172 (4) | 0.53597 (19) | 0.64308 (10) | 0.0354 (5) | |
C265 | −0.2405 (3) | 0.61248 (19) | 0.59580 (10) | 0.0330 (5) | |
C266 | −0.1483 (3) | 0.65875 (18) | 0.53380 (10) | 0.0293 (5) | |
C267 | 0.1669 (3) | 0.6775 (2) | 0.45064 (10) | 0.0333 (5) | |
O26 | 0.2895 (2) | 0.76187 (12) | 0.45754 (6) | 0.0267 (3) | |
H12A | 0.1791 | 0.7385 | 0.2889 | 0.029* | |
H12B | −0.0200 | 0.8157 | 0.2588 | 0.029* | |
H14A | 0.5921 | 0.5021 | 0.0495 | 0.038* | |
H14B | 0.5869 | 0.3750 | 0.0982 | 0.038* | |
H14C | 0.9404 | 0.4915 | 0.0676 | 0.037* | |
H14D | 0.9281 | 0.3703 | 0.0478 | 0.037* | |
H14E | 1.1338 | 0.3347 | 0.1403 | 0.040* | |
H14F | 0.9374 | 0.2676 | 0.1588 | 0.040* | |
H14G | 0.9506 | 0.3653 | 0.2445 | 0.035* | |
H14H | 0.9480 | 0.4893 | 0.1918 | 0.035* | |
H14I | 0.6059 | 0.3639 | 0.2248 | 0.033* | |
H14J | 0.6082 | 0.4867 | 0.2447 | 0.033* | |
H15 | 0.2904 | 0.5885 | 0.0552 | 0.027* | |
H162 | −0.5654 | 0.7839 | 0.0018 | 0.035* | |
H163 | −0.6858 | 0.8536 | −0.1042 | 0.039* | |
H164 | −0.5071 | 0.9777 | −0.1860 | 0.042* | |
H16A | −0.2160 | 0.8936 | 0.0691 | 0.038* | |
H16B | −0.3491 | 0.7890 | 0.0842 | 0.038* | |
H165 | −0.2110 | 1.0356 | −0.1610 | 0.043* | |
H166 | −0.0925 | 0.9668 | −0.0552 | 0.038* | |
H22A | 0.6891 | 0.7822 | 0.2118 | 0.031* | |
H22B | 0.5329 | 0.7010 | 0.2429 | 0.031* | |
H24A | 0.7200 | 1.0160 | 0.4518 | 0.033* | |
H24B | 0.6825 | 1.1454 | 0.4035 | 0.033* | |
H24C | 0.9932 | 1.1212 | 0.4547 | 0.031* | |
H24D | 1.0867 | 0.9978 | 0.4325 | 0.031* | |
H24E | 1.2498 | 1.1432 | 0.3611 | 0.034* | |
H24F | 1.0255 | 1.2279 | 0.3449 | 0.034* | |
H24G | 1.1490 | 1.1343 | 0.2558 | 0.032* | |
H24H | 1.1849 | 1.0059 | 0.3052 | 0.032* | |
H24I | 0.7812 | 1.1567 | 0.2790 | 0.031* | |
H24J | 0.8684 | 1.0335 | 0.2557 | 0.031* | |
H25 | 0.5142 | 0.9131 | 0.4511 | 0.027* | |
H262 | 0.3388 | 0.5307 | 0.5569 | 0.039* | |
H263 | 0.1828 | 0.4520 | 0.6611 | 0.043* | |
H264 | −0.1803 | 0.5044 | 0.6857 | 0.042* | |
H265 | −0.3890 | 0.6336 | 0.6057 | 0.040* | |
H266 | −0.2346 | 0.7111 | 0.5012 | 0.035* | |
H26A | 0.2596 | 0.6118 | 0.4325 | 0.040* | |
H26B | 0.0560 | 0.7171 | 0.4198 | 0.040* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N11 | 0.0261 (9) | 0.0242 (9) | 0.0153 (8) | −0.0056 (6) | −0.0008 (6) | −0.0046 (7) |
C12 | 0.0210 (10) | 0.0238 (10) | 0.0170 (9) | −0.0097 (7) | 0.0021 (7) | −0.0047 (8) |
N12 | 0.0225 (9) | 0.0331 (10) | 0.0181 (8) | −0.0011 (7) | −0.0017 (6) | −0.0119 (7) |
N13 | 0.0220 (9) | 0.0247 (9) | 0.0158 (8) | −0.0042 (6) | 0.0009 (6) | −0.0051 (7) |
C14 | 0.0269 (10) | 0.0204 (10) | 0.0150 (9) | −0.0077 (8) | 0.0016 (7) | −0.0043 (7) |
C141 | 0.0387 (12) | 0.0340 (12) | 0.0224 (11) | 0.0025 (9) | −0.0064 (8) | −0.0147 (9) |
C142 | 0.0355 (12) | 0.0353 (12) | 0.0205 (10) | 0.0004 (9) | −0.0020 (8) | −0.0099 (9) |
C143 | 0.0321 (12) | 0.0370 (12) | 0.0264 (11) | 0.0030 (9) | −0.0044 (8) | −0.0074 (9) |
C144 | 0.0331 (12) | 0.0309 (11) | 0.0202 (10) | −0.0016 (8) | −0.0072 (8) | −0.0025 (9) |
C145 | 0.0340 (12) | 0.0251 (11) | 0.0199 (10) | −0.0018 (8) | −0.0041 (8) | −0.0025 (8) |
N14 | 0.0305 (9) | 0.0291 (9) | 0.0162 (8) | 0.0040 (7) | −0.0056 (6) | −0.0076 (7) |
C15 | 0.0290 (11) | 0.0247 (10) | 0.0145 (9) | −0.0038 (8) | 0.0002 (7) | −0.0067 (8) |
C16 | 0.0265 (10) | 0.0235 (10) | 0.0149 (9) | −0.0064 (8) | −0.0011 (7) | −0.0030 (8) |
C161 | 0.0283 (11) | 0.0239 (11) | 0.0193 (10) | 0.0006 (8) | −0.0009 (8) | −0.0048 (8) |
C162 | 0.0338 (12) | 0.0252 (11) | 0.0253 (11) | −0.0043 (8) | −0.0007 (8) | −0.0015 (9) |
C163 | 0.0320 (12) | 0.0334 (12) | 0.0340 (12) | −0.0014 (9) | −0.0095 (9) | −0.0105 (10) |
C164 | 0.0478 (14) | 0.0302 (12) | 0.0215 (11) | 0.0062 (10) | −0.0079 (9) | −0.0045 (9) |
C167 | 0.0303 (12) | 0.0378 (12) | 0.0217 (11) | 0.0065 (9) | −0.0051 (8) | −0.0084 (9) |
C165 | 0.0445 (14) | 0.0317 (12) | 0.0253 (11) | −0.0079 (10) | 0.0056 (9) | 0.0005 (9) |
C166 | 0.0320 (12) | 0.0354 (12) | 0.0295 (12) | −0.0083 (9) | −0.0001 (9) | −0.0116 (10) |
O16 | 0.0285 (8) | 0.0347 (8) | 0.0193 (7) | 0.0038 (6) | −0.0069 (5) | −0.0094 (6) |
N21 | 0.0244 (9) | 0.0238 (9) | 0.0156 (8) | −0.0034 (6) | −0.0014 (6) | −0.0050 (6) |
C22 | 0.0212 (10) | 0.0226 (10) | 0.0161 (9) | 0.0008 (7) | −0.0035 (7) | −0.0041 (8) |
N22 | 0.0297 (9) | 0.0350 (10) | 0.0187 (8) | −0.0128 (7) | 0.0038 (6) | −0.0120 (7) |
N23 | 0.0224 (9) | 0.0258 (9) | 0.0156 (8) | −0.0037 (6) | −0.0022 (6) | −0.0060 (7) |
C24 | 0.0225 (10) | 0.0235 (10) | 0.0157 (9) | −0.0009 (8) | −0.0038 (7) | −0.0031 (8) |
C241 | 0.0345 (12) | 0.0317 (12) | 0.0186 (10) | −0.0075 (9) | 0.0009 (8) | −0.0101 (9) |
C242 | 0.0341 (12) | 0.0243 (11) | 0.0199 (10) | −0.0059 (8) | −0.0030 (8) | −0.0070 (8) |
C243 | 0.0344 (12) | 0.0261 (11) | 0.0269 (11) | −0.0100 (9) | −0.0047 (8) | −0.0037 (9) |
C244 | 0.0303 (11) | 0.0264 (11) | 0.0206 (10) | −0.0065 (8) | 0.0006 (8) | −0.0022 (8) |
C245 | 0.0334 (11) | 0.0256 (11) | 0.0178 (10) | −0.0077 (8) | −0.0010 (8) | −0.0019 (8) |
N24 | 0.0340 (10) | 0.0312 (10) | 0.0162 (8) | −0.0131 (7) | 0.0035 (6) | −0.0087 (7) |
C25 | 0.0291 (11) | 0.0234 (10) | 0.0159 (9) | −0.0034 (8) | −0.0015 (7) | −0.0062 (8) |
C26 | 0.0227 (10) | 0.0215 (10) | 0.0146 (9) | −0.0013 (7) | −0.0009 (7) | −0.0002 (8) |
C261 | 0.0338 (12) | 0.0254 (11) | 0.0187 (10) | −0.0134 (8) | −0.0002 (8) | −0.0050 (8) |
C262 | 0.0350 (12) | 0.0354 (12) | 0.0292 (12) | −0.0056 (9) | −0.0055 (9) | −0.0103 (10) |
C263 | 0.0572 (15) | 0.0267 (12) | 0.0236 (11) | −0.0063 (10) | −0.0133 (10) | −0.0006 (9) |
C264 | 0.0546 (15) | 0.0325 (12) | 0.0224 (11) | −0.0213 (10) | 0.0047 (9) | −0.0049 (9) |
C265 | 0.0335 (12) | 0.0344 (12) | 0.0350 (12) | −0.0140 (9) | 0.0046 (9) | −0.0126 (10) |
C266 | 0.0398 (12) | 0.0245 (11) | 0.0252 (11) | −0.0088 (9) | −0.0074 (8) | −0.0035 (9) |
C267 | 0.0464 (13) | 0.0382 (12) | 0.0222 (11) | −0.0238 (10) | 0.0030 (9) | −0.0088 (9) |
O26 | 0.0326 (8) | 0.0318 (8) | 0.0182 (7) | −0.0139 (6) | 0.0052 (5) | −0.0073 (6) |
Geometric parameters (Å, º) top
N11—C16 | 1.333 (2) | N21—C26 | 1.333 (2) |
N11—C12 | 1.357 (2) | N21—C22 | 1.352 (2) |
C12—N13 | 1.341 (2) | C22—N23 | 1.340 (2) |
C12—N12 | 1.341 (2) | C22—N22 | 1.341 (2) |
N12—H12A | 0.88 | N22—H22A | 0.88 |
N12—H12B | 0.88 | N22—H22B | 0.88 |
N13—C14 | 1.353 (2) | N23—C24 | 1.354 (2) |
C14—N14 | 1.365 (2) | C24—N24 | 1.364 (2) |
C14—C15 | 1.396 (3) | C24—C25 | 1.398 (3) |
C141—N14 | 1.464 (2) | C241—N24 | 1.461 (2) |
C141—C142 | 1.514 (3) | C241—C242 | 1.521 (3) |
C141—H14A | 0.99 | C241—H24A | 0.99 |
C141—H14B | 0.99 | C241—H24B | 0.99 |
C142—C143 | 1.514 (3) | C242—C243 | 1.517 (3) |
C142—H14C | 0.99 | C242—H24C | 0.99 |
C142—H14D | 0.99 | C242—H24D | 0.99 |
C143—C144 | 1.526 (3) | C243—C244 | 1.520 (3) |
C143—H14E | 0.99 | C243—H24E | 0.99 |
C143—H14F | 0.99 | C243—H24F | 0.99 |
C144—C145 | 1.505 (3) | C244—C245 | 1.518 (3) |
C144—H14G | 0.99 | C244—H24G | 0.99 |
C144—H14H | 0.99 | C244—H24H | 0.99 |
C145—N14 | 1.477 (2) | C245—N24 | 1.467 (2) |
C145—H14I | 0.99 | C245—H24I | 0.99 |
C145—H14J | 0.99 | C245—H24J | 0.99 |
C15—C16 | 1.378 (3) | C25—C26 | 1.381 (3) |
C15—H15 | 0.95 | C25—H25 | 0.95 |
C16—O16 | 1.357 (2) | C26—O26 | 1.361 (2) |
C161—C162 | 1.383 (3) | C261—C266 | 1.381 (3) |
C161—C166 | 1.385 (3) | C261—C262 | 1.387 (3) |
C161—C167 | 1.507 (3) | C261—C267 | 1.506 (3) |
C162—C163 | 1.390 (3) | C262—C263 | 1.388 (3) |
C162—H162 | 0.95 | C262—H262 | 0.95 |
C163—C164 | 1.376 (3) | C263—C264 | 1.376 (3) |
C163—H163 | 0.95 | C263—H263 | 0.95 |
C164—C165 | 1.383 (3) | C264—C265 | 1.375 (3) |
C164—H164 | 0.95 | C264—H264 | 0.95 |
C167—O16 | 1.447 (2) | C265—C266 | 1.385 (3) |
C167—H16A | 0.99 | C265—H265 | 0.95 |
C167—H16B | 0.99 | C266—H266 | 0.95 |
C165—C166 | 1.382 (3) | C267—O26 | 1.447 (2) |
C165—H165 | 0.95 | C267—H26A | 0.99 |
C166—H166 | 0.95 | C267—H26B | 0.99 |
| | | |
C16—N11—C12 | 113.87 (15) | C26—N21—C22 | 113.65 (15) |
N13—C12—N12 | 116.59 (15) | N23—C22—N22 | 116.24 (15) |
N13—C12—N11 | 126.37 (16) | N23—C22—N21 | 126.91 (16) |
N12—C12—N11 | 117.02 (16) | N22—C22—N21 | 116.84 (16) |
C12—N12—H12A | 120.0 | C22—N22—H22A | 120.0 |
C12—N12—H12B | 120.0 | C22—N22—H22B | 120.0 |
H12A—N12—H12B | 120.0 | H22A—N22—H22B | 120.0 |
C12—N13—C14 | 117.57 (15) | C22—N23—C24 | 117.22 (15) |
N13—C14—N14 | 116.15 (15) | N23—C24—N24 | 115.83 (15) |
N13—C14—C15 | 120.44 (16) | N23—C24—C25 | 120.55 (16) |
N14—C14—C15 | 123.38 (16) | N24—C24—C25 | 123.61 (16) |
N14—C141—C142 | 111.59 (16) | N24—C241—C242 | 110.51 (15) |
N14—C141—H14A | 109.3 | N24—C241—H24A | 109.5 |
C142—C141—H14A | 109.3 | C242—C241—H24A | 109.5 |
N14—C141—H14B | 109.3 | N24—C241—H24B | 109.5 |
C142—C141—H14B | 109.3 | C242—C241—H24B | 109.5 |
H14A—C141—H14B | 108.0 | H24A—C241—H24B | 108.1 |
C141—C142—C143 | 112.36 (17) | C243—C242—C241 | 111.91 (16) |
C141—C142—H14C | 109.1 | C243—C242—H24C | 109.2 |
C143—C142—H14C | 109.1 | C241—C242—H24C | 109.2 |
C141—C142—H14D | 109.1 | C243—C242—H24D | 109.2 |
C143—C142—H14D | 109.1 | C241—C242—H24D | 109.2 |
H14C—C142—H14D | 107.9 | H24C—C242—H24D | 107.9 |
C142—C143—C144 | 109.57 (16) | C242—C243—C244 | 110.49 (16) |
C142—C143—H14E | 109.8 | C242—C243—H24E | 109.6 |
C144—C143—H14E | 109.8 | C244—C243—H24E | 109.6 |
C142—C143—H14F | 109.8 | C242—C243—H24F | 109.6 |
C144—C143—H14F | 109.8 | C244—C243—H24F | 109.6 |
H14E—C143—H14F | 108.2 | H24E—C243—H24F | 108.1 |
C145—C144—C143 | 110.81 (16) | C245—C244—C243 | 110.62 (15) |
C145—C144—H14G | 109.5 | C245—C244—H24G | 109.5 |
C143—C144—H14G | 109.5 | C243—C244—H24G | 109.5 |
C145—C144—H14H | 109.5 | C245—C244—H24H | 109.5 |
C143—C144—H14H | 109.5 | C243—C244—H24H | 109.5 |
H14G—C144—H14H | 108.1 | H24G—C244—H24H | 108.1 |
N14—C145—C144 | 111.14 (16) | N24—C245—C244 | 110.98 (15) |
N14—C145—H14I | 109.4 | N24—C245—H24I | 109.4 |
C144—C145—H14I | 109.4 | C244—C245—H24I | 109.4 |
N14—C145—H14J | 109.4 | N24—C245—H24J | 109.4 |
C144—C145—H14J | 109.4 | C244—C245—H24J | 109.4 |
H14I—C145—H14J | 108.0 | H24I—C245—H24J | 108.0 |
C14—N14—C141 | 120.90 (15) | C24—N24—C241 | 123.04 (15) |
C14—N14—C145 | 120.41 (15) | C24—N24—C245 | 121.54 (15) |
C141—N14—C145 | 113.93 (15) | C241—N24—C245 | 113.58 (15) |
C16—C15—C14 | 116.37 (17) | C26—C25—C24 | 116.20 (17) |
C16—C15—H15 | 121.8 | C26—C25—H25 | 121.9 |
C14—C15—H15 | 121.8 | C24—C25—H25 | 121.9 |
N11—C16—O16 | 118.92 (16) | N21—C26—O26 | 118.65 (16) |
N11—C16—C15 | 125.34 (17) | N21—C26—C25 | 125.39 (16) |
O16—C16—C15 | 115.74 (16) | O26—C26—C25 | 115.96 (16) |
C162—C161—C166 | 118.60 (18) | C266—C261—C262 | 118.68 (18) |
C162—C161—C167 | 120.79 (17) | C266—C261—C267 | 120.79 (18) |
C166—C161—C167 | 120.60 (19) | C262—C261—C267 | 120.48 (19) |
C161—C162—C163 | 120.63 (19) | C261—C262—C263 | 120.5 (2) |
C161—C162—H162 | 119.7 | C261—C262—H262 | 119.8 |
C163—C162—H162 | 119.7 | C263—C262—H262 | 119.8 |
C164—C163—C162 | 120.2 (2) | C264—C263—C262 | 120.13 (19) |
C164—C163—H163 | 119.9 | C264—C263—H263 | 119.9 |
C162—C163—H163 | 119.9 | C262—C263—H263 | 119.9 |
C163—C164—C165 | 119.67 (19) | C265—C264—C263 | 119.88 (19) |
C163—C164—H164 | 120.2 | C265—C264—H264 | 120.1 |
C165—C164—H164 | 120.2 | C263—C264—H264 | 120.1 |
O16—C167—C161 | 107.02 (15) | C264—C265—C266 | 120.0 (2) |
O16—C167—H16A | 110.3 | C264—C265—H265 | 120.0 |
C161—C167—H16A | 110.3 | C266—C265—H265 | 120.0 |
O16—C167—H16B | 110.3 | C261—C266—C265 | 120.84 (19) |
C161—C167—H16B | 110.3 | C261—C266—H266 | 119.6 |
H16A—C167—H16B | 108.6 | C265—C266—H266 | 119.6 |
C166—C165—C164 | 119.94 (19) | O26—C267—C261 | 107.60 (15) |
C166—C165—H165 | 120.0 | O26—C267—H26A | 110.2 |
C164—C165—H165 | 120.0 | C261—C267—H26A | 110.2 |
C165—C166—C161 | 121.0 (2) | O26—C267—H26B | 110.2 |
C165—C166—H166 | 119.5 | C261—C267—H26B | 110.2 |
C161—C166—H166 | 119.5 | H26A—C267—H26B | 108.5 |
C16—O16—C167 | 118.32 (14) | C26—O26—C267 | 117.20 (14) |
| | | |
C16—N11—C12—N13 | −1.3 (3) | C26—N21—C22—N23 | −3.3 (3) |
C16—N11—C12—N12 | 177.36 (16) | C26—N21—C22—N22 | 176.00 (15) |
N12—C12—N13—C14 | −176.54 (15) | N22—C22—N23—C24 | −176.24 (15) |
N11—C12—N13—C14 | 2.2 (3) | N21—C22—N23—C24 | 3.0 (3) |
C12—N13—C14—N14 | 176.31 (16) | C22—N23—C24—N24 | 178.18 (16) |
C12—N13—C14—C15 | −2.1 (2) | C22—N23—C24—C25 | −0.4 (2) |
N14—C141—C142—C143 | 52.5 (2) | N24—C241—C242—C243 | 53.9 (2) |
C141—C142—C143—C144 | −54.2 (2) | C241—C242—C243—C244 | −53.8 (2) |
C142—C143—C144—C145 | 56.0 (2) | C242—C243—C244—C245 | 54.1 (2) |
C143—C144—C145—N14 | −56.2 (2) | C243—C244—C245—N24 | −55.5 (2) |
N13—C14—N14—C141 | 177.79 (17) | N23—C24—N24—C241 | −179.35 (16) |
C15—C14—N14—C141 | −3.8 (3) | C25—C24—N24—C241 | −0.8 (3) |
N13—C14—N14—C145 | 23.7 (2) | N23—C24—N24—C245 | 17.1 (2) |
C15—C14—N14—C145 | −157.90 (18) | C25—C24—N24—C245 | −164.34 (17) |
C142—C141—N14—C14 | 151.72 (17) | C242—C241—N24—C24 | 139.29 (18) |
C142—C141—N14—C145 | −52.7 (2) | C242—C241—N24—C245 | −56.0 (2) |
C144—C145—N14—C14 | −149.19 (17) | C244—C245—N24—C24 | −137.68 (18) |
C144—C145—N14—C141 | 55.1 (2) | C244—C245—N24—C241 | 57.3 (2) |
N13—C14—C15—C16 | 1.4 (3) | N23—C24—C25—C26 | −1.4 (3) |
N14—C14—C15—C16 | −176.88 (17) | N24—C24—C25—C26 | −179.93 (17) |
C12—N11—C16—O16 | −179.43 (15) | C22—N21—C26—O26 | −178.93 (15) |
C12—N11—C16—C15 | 0.5 (3) | C22—N21—C26—C25 | 1.0 (3) |
C14—C15—C16—N11 | −0.6 (3) | C24—C25—C26—N21 | 1.1 (3) |
C14—C15—C16—O16 | 179.34 (16) | C24—C25—C26—O26 | −178.90 (15) |
C166—C161—C162—C163 | −0.1 (3) | C266—C261—C262—C263 | −0.5 (3) |
C167—C161—C162—C163 | 178.70 (18) | C267—C261—C262—C263 | −178.03 (18) |
C161—C162—C163—C164 | 0.5 (3) | C261—C262—C263—C264 | −0.1 (3) |
C162—C163—C164—C165 | −0.7 (3) | C262—C263—C264—C265 | 0.5 (3) |
C162—C161—C167—O16 | 108.5 (2) | C263—C264—C265—C266 | −0.2 (3) |
C166—C161—C167—O16 | −72.7 (2) | C262—C261—C266—C265 | 0.8 (3) |
C163—C164—C165—C166 | 0.5 (3) | C267—C261—C266—C265 | 178.34 (18) |
C164—C165—C166—C161 | −0.1 (3) | C264—C265—C266—C261 | −0.5 (3) |
C162—C161—C166—C165 | −0.1 (3) | C266—C261—C267—O26 | 110.7 (2) |
C167—C161—C166—C165 | −178.89 (19) | C262—C261—C267—O26 | −71.9 (2) |
N11—C16—O16—C167 | −1.4 (2) | N21—C26—O26—C267 | −2.6 (2) |
C15—C16—O16—C167 | 178.57 (16) | C25—C26—O26—C267 | 177.40 (16) |
C161—C167—O16—C16 | 167.65 (16) | C261—C267—O26—C26 | 169.90 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N12—H12A···N21 | 0.88 | 2.29 | 3.105 (2) | 155 |
N12—H12B···N23i | 0.88 | 2.10 | 2.927 (2) | 155 |
N22—H22A···N11ii | 0.88 | 2.27 | 3.064 (2) | 149 |
N22—H22B···N13 | 0.88 | 2.10 | 2.920 (2) | 154 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |
Experimental details
| (1) | (2) | (3) | (4) |
Crystal data |
Chemical formula | C12H13N5O2 | C15H19N5O2 | C23H35N5O2 | C17H21N5O2 |
Mr | 259.27 | 301.35 | 413.56 | 327.39 |
Crystal system, space group | Orthorhombic, P212121 | Monoclinic, P21/c | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 120 | 120 | 120 | 120 |
a, b, c (Å) | 7.1122 (2), 7.3873 (2), 23.3867 (7) | 7.6146 (2), 13.7686 (4), 16.1215 (5) | 7.3567 (4), 7.7784 (4), 21.4725 (14) | 8.2656 (5), 10.6077 (6), 10.6743 (7) |
α, β, γ (°) | 90, 90, 90 | 90, 116.6180 (15), 90 | 92.000 (2), 99.840 (2), 108.760 (2) | 64.841 (4), 71.021 (3), 87.275 (5) |
V (Å3) | 1228.74 (6) | 1511.08 (8) | 1141.00 (11) | 796.56 (9) |
Z | 4 | 4 | 2 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.10 | 0.09 | 0.08 | 0.09 |
Crystal size (mm) | 0.30 × 0.14 × 0.07 | 0.35 × 0.20 × 0.15 | 0.18 × 0.18 × 0.08 | 0.12 × 0.08 × 0.06 |
|
Data collection |
Diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer |
Absorption correction | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.954, 0.994 | 0.966, 0.988 | 0.976, 0.994 | 0.974, 0.994 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6981, 1649, 1323 | 12361, 3424, 2616 | 10984, 4147, 2819 | 11753, 3442, 1528 |
Rint | 0.060 | 0.074 | 0.048 | 0.128 |
(sin θ/λ)max (Å−1) | 0.649 | 0.649 | 0.649 | 0.649 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.090, 1.09 | 0.045, 0.120, 1.04 | 0.052, 0.140, 1.01 | 0.063, 0.146, 0.95 |
No. of reflections | 1649 | 3424 | 4147 | 3442 |
No. of parameters | 173 | 200 | 272 | 217 |
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) | 0.18, −0.24 | 0.22, −0.29 | 0.22, −0.23 | 0.39, −0.28 |
| (5) | (7) | (8) | (9) |
Crystal data |
Chemical formula | C17H15N5O2 | C14H18N6O2 | C16H19N5O2·H2O | C16H20N4O |
Mr | 321.34 | 302.33 | 331.38 | 284.36 |
Crystal system, space group | Triclinic, P1 | Monoclinic, C2/c | Monoclinic, P21/c | Triclinic, P1 |
Temperature (K) | 120 | 298 | 120 | 120 |
a, b, c (Å) | 4.7622 (3), 5.8123 (4), 13.5635 (11) | 28.3925 (6), 8.1627 (3), 15.1540 (5) | 7.2557 (4), 11.4692 (7), 20.4417 (15) | 6.5025 (2), 11.8006 (4), 20.7673 (10) |
α, β, γ (°) | 79.851 (2), 87.346 (2), 89.692 (5) | 90, 121.9700 (13), 90 | 90, 106.113 (3), 90 | 76.1950 (14), 82.3623 (14), 77.330 (4) |
V (Å3) | 369.16 (5) | 2979.39 (17) | 1634.27 (18) | 1504.36 (10) |
Z | 1 | 8 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.10 | 0.10 | 0.10 | 0.08 |
Crystal size (mm) | 0.40 × 0.14 × 0.02 | 0.22 × 0.08 × 0.03 | 0.35 × 0.10 × 0.02 | 0.70 × 0.17 × 0.08 |
|
Data collection |
Diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer | Kappa-CCD diffractometer |
Absorption correction | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | – | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) | Multi-scan DENZO-SMN (Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.895, 0.998 | – | 0.956, 0.998 | 0.965, 0.994 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5085, 2993, 2348 | 9945, 3366, 1422 | 14044, 3658, 1996 | 17141, 6307, 4163 |
Rint | 0.071 | 0.065 | 0.094 | 0.054 |
(sin θ/λ)max (Å−1) | 0.648 | 0.650 | 0.648 | 0.648 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.136, 1.04 | 0.060, 0.145, 0.91 | 0.058, 0.146, 0.96 | 0.056, 0.161, 1.04 |
No. of reflections | 2993 | 3366 | 3658 | 6307 |
No. of parameters | 217 | 200 | 217 | 379 |
No. of restraints | 3 | 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) | 0.24, −0.28 | 0.18, −0.20 | 0.24, −0.32 | 0.33, −0.37 |
Hydrogen-bond geometry (Å, º) for (1) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O5 | 0.88 | 1.95 | 2.618 (2) | 132 |
N2—H2A···N5i | 0.88 | 2.14 | 3.006 (3) | 169 |
N2—H2B···Cg1i | 0.88 | 2.68 | 3.516 (2) | 160 |
C62—H62···O5ii | 0.95 | 2.45 | 3.379 (3) | 165 |
C66—H66···Cg1iii | 0.95 | 2.73 | 3.647 (2) | 163 |
Symmetry codes: (i) x, y+1, z; (ii) x−1, y, z; (iii) x+1/2, −y+3/2, −z. |
Hydrogen-bond geometry (Å, º) for (2) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O5 | 0.88 | 2.00 | 2.642 (2) | 129 |
N2—H2A···N5i | 0.88 | 2.20 | 3.058 (2) | 164 |
N2—H2B···Cg1i | 0.88 | 2.67 | 3.537 (2) | 171 |
Symmetry code: (i) −x+1, y−1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) for (3) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O5 | 0.88 | 1.96 | 2.624 (2) | 131 |
N2—H2A···N5i | 0.88 | 2.12 | 2.987 (2) | 169 |
Symmetry code: (i) x−1, y, z. |
Hydrogen-bond geometry (Å, º) for (4) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O5 | 0.88 | 1.91 | 2.609 (3) | 135 |
N2—H2A···O5i | 0.88 | 1.99 | 2.804 (3) | 153 |
C43—H43B···Cg1ii | 0.99 | 2.73 | 3.717 (4) | 173 |
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z−1. |
Hydrogen-bond geometry (Å, º) for (5) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O5 | 0.88 | 1.86 | 2.593 (3) | 139 |
N2—H2A···N5i | 0.88 | 2.07 | 2.942 (3) | 173 |
C42—H42···O5i | 0.95 | 2.48 | 3.215 (4) | 133 |
Symmetry code: (i) x−1, y+1, z. |
Hydrogen-bond geometry (Å, º) for (7) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O5 | 0.86 | 1.96 | 2.622 (3) | 133 |
N2—H2A···N5i | 0.86 | 2.36 | 3.095 (3) | 144 |
N2—H2B···N63ii | 0.86 | 2.14 | 2.979 (3) | 164 |
C62—H62···O5iii | 0.93 | 2.38 | 3.289 (3) | 167 |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, −y+2, z+1/2; (iii) x, y+1, z. |
Hydrogen-bond geometry (Å, º) for (8) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N5i | 0.88 | 2.30 | 3.158 (3) | 165 |
N2—H2B···O1 | 0.88 | 2.09 | 2.966 (3) | 171 |
O1—H1A···O5ii | 1.00 | 1.87 | 2.791 (2) | 153 |
O1—H1B···N3iii | 1.00 | 1.99 | 2.968 (3) | 167 |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, y+1/2, −z+1/2; (iii) −x+1, y+1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) for (9) top
D—H···A | D—H | H···A | D···A | D—H···A |
N12—H12A···N21 | 0.88 | 2.29 | 3.105 (2) | 155 |
N12—H12B···N23i | 0.88 | 2.10 | 2.927 (2) | 155 |
N22—H22A···N11ii | 0.88 | 2.27 | 3.064 (2) | 149 |
N22—H22B···N13 | 0.88 | 2.10 | 2.920 (2) | 154 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |
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