The crystal structures of three mackinazolinone derivatives (2-amino-6,7,8,9-tetrahydro-11
H-pyrido[2,1-
b]quinazolin-11-one at room temperature, and 2-nitro-6,7,8,9-tetrahydro-11
H-pyrido[2,1-
b]quinazolin-11-one and
N-(11-oxo-6,8,9,11-tetrahydro-7
H-pyrido[2,1-
b]quinazolin-2-yl)benzamide at 100 K) are explored using X-ray crystallography. To delineate the different intermolecular interactions and the respective interaction energies in the crystal architectures, energy framework analyses were carried out using the CE-B3LYP/6-31G(d,p) method implemented in the
CrystalExplorer software. In the structures the different molecules are linked by C—H
O, C—H
N and N—H
O hydrogen bonds. Together with these hydrogen bonds, C—H
π and C—O
π interactions are involved in the formation of a three-dimensional crystal network. A Hirshfeld surface analysis allows the visualization of the two-dimensional fingerprint plots and the quantification of the contributions of H
H, H
C/C
H and H
O/O
H contacts throughout the different crystal structures. To obtain additional information on the intrinsic properties of our targets and to compare the experimental crystal structures with their respective conformations in the gas phase, quantum chemical calculations at the B3LYP-D3BJ/6-311++G(d,p) level of theory, including Grimme's D3 correction term and BJ damping functions, were carried out to account for intramolecular dispersion interactions. The identified energy gaps between the highest occupied and the lowest unoccupied molecular orbitals (HOMO–LUMO gap) of our targets in the gas phase and in two implicit solvents (methanol and dimethyl sulfoxide) allow us to quantify the impact of different substituents on the reactivity of mackinazolinone derivatives.
Supporting information
CCDC references: 2074781; 2074782; 2074783
For all structures, data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2018). Molecular graphics: PLATON (Spek, 2020) for (2), (4); PLATON (Spek, 2009) for (3). Software used to prepare material for publication: publCIF (Westrip, 2010) for (2), (4).
Crystal data top
C12H13N3O | F(000) = 456 |
Mr = 215.25 | Dx = 1.361 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
a = 9.6282 (3) Å | Cell parameters from 1630 reflections |
b = 9.5416 (4) Å | θ = 3.9–75.5° |
c = 11.6064 (4) Å | µ = 0.73 mm−1 |
β = 99.863 (3)° | T = 298 K |
V = 1050.50 (7) Å3 | Rod, colourless |
Z = 4 | 0.20 × 0.20 × 0.20 mm |
Data collection top
Xcalibur, Ruby diffractometer | 2124 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 1439 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
Detector resolution: 10.2576 pixels mm-1 | θmax = 75.6°, θmin = 5.5° |
ω scans | h = −11→9 |
Absorption correction: multi-scan CrysAlisPro, Oxford Diffraction, 2009 | k = −11→10 |
Tmin = 0.881, Tmax = 1.000 | l = −13→14 |
4385 measured reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.173 | w = 1/[σ2(Fo2) + (0.0917P)2 + 0.143P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
2124 reflections | Δρmax = 0.38 e Å−3 |
152 parameters | Δρmin = −0.20 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O | 0.56471 (18) | 0.1894 (2) | 0.45187 (15) | 0.0694 (6) | |
N' | 0.0906 (2) | 0.3549 (3) | 0.5509 (2) | 0.0620 (6) | |
H1A' | 0.037 (3) | 0.403 (3) | 0.597 (3) | 0.077 (9)* | |
H1B' | 0.097 (4) | 0.393 (4) | 0.471 (4) | 0.115* | |
C1 | 0.3202 (2) | 0.2522 (2) | 0.54959 (17) | 0.0475 (5) | |
H1 | 0.315603 | 0.276579 | 0.471443 | 0.057* | |
C2 | 0.2111 (2) | 0.2883 (2) | 0.60774 (19) | 0.0475 (5) | |
C3 | 0.2217 (2) | 0.2515 (3) | 0.72608 (19) | 0.0522 (6) | |
H3 | 0.150765 | 0.277993 | 0.766783 | 0.063* | |
C4 | 0.3342 (2) | 0.1776 (3) | 0.78212 (19) | 0.0525 (6) | |
H4 | 0.337699 | 0.152424 | 0.859966 | 0.063* | |
C4A | 0.4454 (2) | 0.1388 (2) | 0.72413 (18) | 0.0446 (5) | |
N5 | 0.55998 (17) | 0.0647 (2) | 0.78495 (16) | 0.0495 (5) | |
C5A | 0.6664 (2) | 0.0421 (2) | 0.7317 (2) | 0.0469 (5) | |
C6 | 0.7900 (2) | −0.0381 (3) | 0.7958 (2) | 0.0596 (6) | |
H6A | 0.778191 | −0.136667 | 0.776212 | 0.071* | |
H6B | 0.792178 | −0.028570 | 0.879309 | 0.071* | |
C7 | 0.9294 (2) | 0.0125 (3) | 0.7662 (2) | 0.0619 (7) | |
H7A | 0.945205 | 0.109713 | 0.789179 | 0.074* | |
H7B | 1.006434 | −0.043182 | 0.807489 | 0.074* | |
C8 | 0.9218 (2) | −0.0025 (3) | 0.6360 (3) | 0.0674 (7) | |
H8A | 1.010449 | 0.027690 | 0.615188 | 0.081* | |
H8B | 0.908424 | −0.100502 | 0.614754 | 0.081* | |
C9 | 0.8036 (2) | 0.0821 (3) | 0.5678 (2) | 0.0582 (6) | |
H9A | 0.836517 | 0.177325 | 0.560826 | 0.070* | |
H9B | 0.780856 | 0.043574 | 0.489540 | 0.070* | |
N10 | 0.67213 (17) | 0.08683 (19) | 0.61957 (16) | 0.0472 (5) | |
C11 | 0.5587 (2) | 0.1536 (2) | 0.55063 (19) | 0.0481 (5) | |
C11A | 0.4374 (2) | 0.1791 (2) | 0.60824 (17) | 0.0429 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O | 0.0717 (11) | 0.0925 (14) | 0.0493 (9) | 0.0214 (10) | 0.0251 (8) | 0.0157 (9) |
N' | 0.0526 (11) | 0.0819 (16) | 0.0495 (11) | 0.0195 (11) | 0.0031 (9) | −0.0031 (11) |
C1 | 0.0518 (12) | 0.0556 (13) | 0.0338 (10) | 0.0024 (11) | 0.0035 (8) | −0.0003 (9) |
C2 | 0.0415 (10) | 0.0528 (13) | 0.0464 (11) | 0.0000 (10) | 0.0028 (9) | −0.0083 (10) |
C3 | 0.0430 (11) | 0.0683 (16) | 0.0461 (12) | 0.0027 (11) | 0.0101 (9) | −0.0045 (11) |
C4 | 0.0480 (11) | 0.0713 (16) | 0.0388 (11) | −0.0001 (11) | 0.0090 (9) | 0.0037 (11) |
C4A | 0.0421 (10) | 0.0501 (12) | 0.0406 (11) | −0.0016 (9) | 0.0042 (8) | 0.0022 (9) |
N5 | 0.0407 (9) | 0.0599 (12) | 0.0469 (10) | 0.0006 (8) | 0.0046 (8) | 0.0063 (9) |
C5A | 0.0450 (11) | 0.0452 (12) | 0.0483 (12) | −0.0007 (10) | 0.0015 (9) | 0.0026 (10) |
C6 | 0.0522 (13) | 0.0580 (15) | 0.0658 (16) | 0.0084 (11) | 0.0024 (11) | 0.0081 (12) |
C7 | 0.0465 (12) | 0.0640 (15) | 0.0720 (17) | 0.0043 (12) | 0.0006 (11) | 0.0000 (13) |
C8 | 0.0482 (13) | 0.0771 (18) | 0.0766 (18) | 0.0041 (13) | 0.0099 (12) | −0.0082 (15) |
C9 | 0.0510 (12) | 0.0662 (15) | 0.0608 (15) | 0.0033 (12) | 0.0196 (11) | 0.0003 (12) |
N10 | 0.0422 (9) | 0.0493 (10) | 0.0509 (10) | 0.0041 (8) | 0.0099 (8) | 0.0000 (8) |
C11 | 0.0530 (12) | 0.0523 (13) | 0.0389 (11) | 0.0020 (10) | 0.0077 (9) | 0.0018 (9) |
C11A | 0.0427 (10) | 0.0452 (11) | 0.0401 (11) | −0.0015 (9) | 0.0052 (8) | −0.0033 (9) |
Geometric parameters (Å, º) top
O—C11 | 1.207 (3) | N5—C5A | 1.302 (3) |
N'—C2 | 1.387 (3) | C5A—N10 | 1.380 (3) |
C1—C2 | 1.386 (3) | C5A—C6 | 1.500 (3) |
C1—C11A | 1.399 (3) | C6—C7 | 1.520 (3) |
C2—C3 | 1.404 (3) | C7—C8 | 1.507 (4) |
C3—C4 | 1.360 (3) | C8—C9 | 1.505 (4) |
C4—C4A | 1.408 (3) | C9—N10 | 1.491 (3) |
C4A—C11A | 1.388 (3) | N10—C11 | 1.392 (3) |
C4A—N5 | 1.396 (3) | C11—C11A | 1.463 (3) |
| | | |
C2—C1—C11A | 120.12 (19) | C5A—C6—C7 | 112.4 (2) |
C1—C2—N' | 121.7 (2) | C8—C7—C6 | 107.7 (2) |
C1—C2—C3 | 118.68 (19) | C9—C8—C7 | 112.2 (2) |
N'—C2—C3 | 119.6 (2) | N10—C9—C8 | 114.9 (2) |
C4—C3—C2 | 121.1 (2) | C5A—N10—C11 | 121.96 (18) |
C3—C4—C4A | 121.0 (2) | C5A—N10—C9 | 122.97 (18) |
C11A—C4A—N5 | 122.55 (19) | C11—N10—C9 | 114.74 (18) |
C11A—C4A—C4 | 118.00 (19) | O—C11—N10 | 121.0 (2) |
N5—C4A—C4 | 119.44 (19) | O—C11—C11A | 124.0 (2) |
C5A—N5—C4A | 117.51 (18) | N10—C11—C11A | 115.02 (18) |
N5—C5A—N10 | 123.95 (19) | C4A—C11A—C1 | 121.04 (19) |
N5—C5A—C6 | 118.1 (2) | C4A—C11A—C11 | 118.73 (19) |
N10—C5A—C6 | 118.0 (2) | C1—C11A—C11 | 120.07 (19) |
| | | |
C11A—C1—C2—N' | −177.0 (2) | N5—C5A—N10—C9 | 169.0 (2) |
C11A—C1—C2—C3 | 0.7 (3) | C6—C5A—N10—C9 | −11.4 (3) |
C1—C2—C3—C4 | −2.3 (4) | C8—C9—N10—C5A | 12.5 (3) |
N'—C2—C3—C4 | 175.5 (2) | C8—C9—N10—C11 | −174.0 (2) |
C2—C3—C4—C4A | 1.6 (4) | C5A—N10—C11—O | −178.5 (2) |
C3—C4—C4A—C11A | 0.5 (3) | C9—N10—C11—O | 7.9 (3) |
C3—C4—C4A—N5 | 179.1 (2) | C5A—N10—C11—C11A | 3.2 (3) |
C11A—C4A—N5—C5A | 4.8 (3) | C9—N10—C11—C11A | −170.37 (19) |
C4—C4A—N5—C5A | −173.7 (2) | N5—C4A—C11A—C1 | 179.4 (2) |
C4A—N5—C5A—N10 | −0.1 (3) | C4—C4A—C11A—C1 | −2.1 (3) |
C4A—N5—C5A—C6 | −179.7 (2) | N5—C4A—C11A—C11 | −5.3 (3) |
N5—C5A—C6—C7 | −145.6 (2) | C4—C4A—C11A—C11 | 173.2 (2) |
N10—C5A—C6—C7 | 34.8 (3) | C2—C1—C11A—C4A | 1.4 (3) |
C5A—C6—C7—C8 | −58.3 (3) | C2—C1—C11A—C11 | −173.8 (2) |
C6—C7—C8—C9 | 59.8 (3) | O—C11—C11A—C4A | −177.0 (2) |
C7—C8—C9—N10 | −37.3 (3) | N10—C11—C11A—C4A | 1.2 (3) |
N5—C5A—N10—C11 | −4.0 (3) | O—C11—C11A—C1 | −1.7 (4) |
C6—C5A—N10—C11 | 175.6 (2) | N10—C11—C11A—C1 | 176.57 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N′—H1A′···N5i | 0.93 (3) | 2.36 (3) | 3.268 (3) | 167 (3) |
N′—H1B′···N5ii | 1.00 (4) | 2.17 (4) | 3.146 (3) | 164 (3) |
C3—H3···Oiii | 0.93 | 2.45 | 3.291 (3) | 150 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+3/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) x−1/2, −y+1/2, z+1/2. |
Crystal data top
C12H11N3O3 | F(000) = 512 |
Mr = 245.24 | Dx = 1.494 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
a = 13.0177 (3) Å | Cell parameters from 2233 reflections |
b = 5.6433 (14) Å | θ = 3.5–75.5° |
c = 15.4366 (4) Å | µ = 0.92 mm−1 |
β = 105.949 (3)° | T = 100 K |
V = 1090.4 (3) Å3 | Plate, colourless |
Z = 4 | 0.50 × 0.40 × 0.15 mm |
Data collection top
Xcalibur, Ruby diffractometer | 2226 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 1777 reflections with I > 2σ(I) |
Detector resolution: 10.2576 pixels mm-1 | Rint = 0.023 |
ω scans | θmax = 75.7°, θmin = 4.0° |
Absorption correction: multi-scan CrysAlisPro, Oxford Diffraction, 2009 | h = −12→16 |
Tmin = 0.710, Tmax = 1.000 | k = −4→6 |
4411 measured reflections | l = −19→15 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.0746P)2 + 0.0703P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2226 reflections | Δρmax = 0.29 e Å−3 |
163 parameters | Δρmin = −0.24 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O | 0.33031 (8) | −0.32586 (19) | 0.26740 (7) | 0.0253 (3) | |
O'1 | 0.61695 (9) | −0.0346 (3) | 0.13807 (8) | 0.0403 (3) | |
O'2 | 0.71362 (9) | 0.2653 (2) | 0.19815 (8) | 0.0344 (3) | |
N' | 0.64191 (10) | 0.1218 (3) | 0.19517 (8) | 0.0270 (3) | |
C1 | 0.50654 (11) | −0.0287 (3) | 0.26350 (9) | 0.0211 (3) | |
H1 | 0.495910 | −0.160067 | 0.223516 | 0.025* | |
C2 | 0.58166 (10) | 0.1408 (3) | 0.26255 (9) | 0.0210 (3) | |
C3 | 0.60190 (11) | 0.3344 (3) | 0.32164 (10) | 0.0220 (3) | |
H3 | 0.655000 | 0.447849 | 0.319370 | 0.026* | |
C4 | 0.54309 (11) | 0.3569 (3) | 0.38326 (9) | 0.0207 (3) | |
H4 | 0.556516 | 0.485256 | 0.424665 | 0.025* | |
C4A | 0.46322 (10) | 0.1898 (2) | 0.38484 (9) | 0.0178 (3) | |
N5 | 0.40190 (9) | 0.2257 (2) | 0.44384 (8) | 0.0191 (3) | |
C5A | 0.32489 (10) | 0.0765 (2) | 0.44146 (9) | 0.0181 (3) | |
C6 | 0.25885 (11) | 0.1215 (3) | 0.50637 (9) | 0.0210 (3) | |
H6A | 0.253274 | 0.294703 | 0.514151 | 0.025* | |
H6B | 0.296691 | 0.053883 | 0.565747 | 0.025* | |
C7 | 0.14660 (11) | 0.0174 (3) | 0.47687 (10) | 0.0256 (3) | |
H7A | 0.111516 | 0.032355 | 0.525966 | 0.031* | |
H7B | 0.102938 | 0.103073 | 0.423405 | 0.031* | |
C8 | 0.15657 (12) | −0.2414 (3) | 0.45431 (10) | 0.0257 (3) | |
H8A | 0.085130 | −0.316611 | 0.438814 | 0.031* | |
H8B | 0.202489 | −0.324203 | 0.507484 | 0.031* | |
C9 | 0.20458 (11) | −0.2650 (3) | 0.37553 (10) | 0.0228 (3) | |
H9A | 0.223240 | −0.433154 | 0.369520 | 0.027* | |
H9B | 0.150309 | −0.218812 | 0.319467 | 0.027* | |
N10 | 0.30152 (9) | −0.1171 (2) | 0.38558 (8) | 0.0183 (3) | |
C11 | 0.35736 (11) | −0.1648 (3) | 0.32178 (9) | 0.0196 (3) | |
C11A | 0.44587 (10) | −0.0026 (2) | 0.32518 (9) | 0.0180 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O | 0.0293 (5) | 0.0234 (5) | 0.0239 (5) | −0.0033 (4) | 0.0087 (4) | −0.0074 (4) |
O'1 | 0.0335 (6) | 0.0644 (9) | 0.0275 (6) | −0.0036 (6) | 0.0162 (5) | −0.0176 (6) |
O'2 | 0.0334 (6) | 0.0417 (7) | 0.0361 (7) | −0.0019 (5) | 0.0227 (5) | 0.0018 (5) |
N' | 0.0225 (6) | 0.0400 (8) | 0.0202 (6) | 0.0056 (5) | 0.0087 (5) | 0.0003 (6) |
C1 | 0.0210 (6) | 0.0254 (7) | 0.0158 (6) | 0.0055 (6) | 0.0035 (5) | −0.0024 (6) |
C2 | 0.0184 (6) | 0.0299 (8) | 0.0162 (6) | 0.0068 (6) | 0.0074 (5) | 0.0020 (6) |
C3 | 0.0182 (6) | 0.0261 (7) | 0.0228 (7) | 0.0004 (6) | 0.0073 (5) | 0.0024 (6) |
C4 | 0.0211 (6) | 0.0212 (7) | 0.0210 (7) | 0.0004 (5) | 0.0076 (5) | −0.0029 (5) |
C4A | 0.0181 (6) | 0.0195 (7) | 0.0159 (6) | 0.0026 (5) | 0.0048 (5) | −0.0001 (5) |
N5 | 0.0205 (6) | 0.0202 (6) | 0.0180 (6) | 0.0003 (5) | 0.0080 (4) | −0.0019 (5) |
C5A | 0.0197 (6) | 0.0188 (7) | 0.0161 (6) | 0.0026 (5) | 0.0056 (5) | 0.0011 (5) |
C6 | 0.0229 (7) | 0.0218 (7) | 0.0209 (7) | −0.0001 (5) | 0.0105 (5) | −0.0018 (6) |
C7 | 0.0212 (7) | 0.0325 (8) | 0.0259 (7) | 0.0006 (6) | 0.0110 (6) | 0.0001 (6) |
C8 | 0.0256 (7) | 0.0292 (8) | 0.0239 (7) | −0.0073 (6) | 0.0094 (6) | −0.0002 (6) |
C9 | 0.0251 (7) | 0.0223 (7) | 0.0218 (7) | −0.0063 (6) | 0.0079 (5) | −0.0005 (6) |
N10 | 0.0194 (5) | 0.0186 (6) | 0.0171 (5) | −0.0014 (5) | 0.0055 (4) | 0.0009 (5) |
C11 | 0.0213 (6) | 0.0196 (7) | 0.0172 (6) | 0.0025 (5) | 0.0043 (5) | −0.0001 (5) |
C11A | 0.0180 (6) | 0.0199 (7) | 0.0160 (6) | 0.0037 (5) | 0.0042 (5) | 0.0005 (5) |
Geometric parameters (Å, º) top
O—C11 | 1.2218 (17) | C4A—C11A | 1.4013 (19) |
O'1—N' | 1.2264 (18) | N5—C5A | 1.3018 (18) |
O'2—N' | 1.2272 (17) | C5A—N10 | 1.3737 (18) |
N'—C2 | 1.4687 (16) | C5A—C6 | 1.5102 (17) |
C1—C2 | 1.371 (2) | C6—C7 | 1.5238 (19) |
C1—C11A | 1.4020 (18) | C7—C8 | 1.515 (2) |
C2—C3 | 1.401 (2) | C8—C9 | 1.5182 (19) |
C3—C4 | 1.3811 (18) | C9—N10 | 1.4851 (17) |
C4—C4A | 1.4088 (19) | N10—C11 | 1.4015 (16) |
C4A—N5 | 1.3812 (16) | C11—C11A | 1.4608 (19) |
| | | |
O'1—N'—O'2 | 123.41 (12) | N10—C5A—C6 | 118.82 (12) |
O'1—N'—C2 | 118.29 (13) | C5A—C6—C7 | 114.27 (12) |
O'2—N'—C2 | 118.29 (13) | C8—C7—C6 | 107.72 (12) |
C2—C1—C11A | 118.07 (13) | C7—C8—C9 | 110.43 (12) |
C1—C2—C3 | 122.97 (12) | N10—C9—C8 | 113.07 (11) |
C1—C2—N' | 118.55 (13) | C5A—N10—C11 | 121.71 (12) |
C3—C2—N' | 118.47 (13) | C5A—N10—C9 | 123.23 (11) |
C4—C3—C2 | 118.66 (13) | C11—N10—C9 | 114.13 (11) |
C3—C4—C4A | 120.11 (13) | O—C11—N10 | 121.21 (13) |
N5—C4A—C11A | 121.95 (12) | O—C11—C11A | 124.50 (13) |
N5—C4A—C4 | 118.43 (12) | N10—C11—C11A | 114.26 (12) |
C11A—C4A—C4 | 119.59 (12) | C4A—C11A—C1 | 120.56 (13) |
C5A—N5—C4A | 117.81 (12) | C4A—C11A—C11 | 119.48 (12) |
N5—C5A—N10 | 124.63 (12) | C1—C11A—C11 | 119.72 (13) |
N5—C5A—C6 | 116.55 (12) | | |
| | | |
C11A—C1—C2—C3 | 1.6 (2) | N5—C5A—N10—C11 | −3.1 (2) |
C11A—C1—C2—N' | −176.95 (12) | C6—C5A—N10—C11 | 177.88 (12) |
O'1—N'—C2—C1 | 5.5 (2) | N5—C5A—N10—C9 | −171.42 (12) |
O'2—N'—C2—C1 | −175.52 (13) | C6—C5A—N10—C9 | 9.57 (19) |
O'1—N'—C2—C3 | −173.09 (13) | C8—C9—N10—C5A | −20.92 (19) |
O'2—N'—C2—C3 | 5.9 (2) | C8—C9—N10—C11 | 169.96 (12) |
C1—C2—C3—C4 | −0.5 (2) | C5A—N10—C11—O | −173.86 (13) |
N'—C2—C3—C4 | 178.02 (12) | C9—N10—C11—O | −4.55 (19) |
C2—C3—C4—C4A | −1.2 (2) | C5A—N10—C11—C11A | 4.33 (18) |
C3—C4—C4A—N5 | −176.29 (12) | C9—N10—C11—C11A | 173.64 (11) |
C3—C4—C4A—C11A | 1.7 (2) | N5—C4A—C11A—C1 | 177.31 (12) |
C11A—C4A—N5—C5A | −1.33 (19) | C4—C4A—C11A—C1 | −0.6 (2) |
C4—C4A—N5—C5A | 176.63 (12) | N5—C4A—C11A—C11 | 2.94 (19) |
C4A—N5—C5A—N10 | 1.3 (2) | C4—C4A—C11A—C11 | −175.00 (12) |
C4A—N5—C5A—C6 | −179.62 (11) | C2—C1—C11A—C4A | −1.0 (2) |
N5—C5A—C6—C7 | 155.44 (13) | C2—C1—C11A—C11 | 173.38 (12) |
N10—C5A—C6—C7 | −25.47 (18) | O—C11—C11A—C4A | 173.87 (13) |
C5A—C6—C7—C8 | 51.56 (16) | N10—C11—C11A—C4A | −4.26 (18) |
C6—C7—C8—C9 | −63.01 (16) | O—C11—C11A—C1 | −0.5 (2) |
C7—C8—C9—N10 | 47.86 (17) | N10—C11—C11A—C1 | −178.67 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O′2i | 0.95 | 2.54 | 3.4899 (19) | 175 |
C4—H4···N5ii | 0.95 | 2.54 | 3.4834 (19) | 170 |
C9—H9B···Oiii | 0.99 | 2.64 | 3.2659 (18) | 121 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) −x+1/2, y+1/2, −z+1/2. |
Crystal data top
C19H17N3O2 | F(000) = 1344 |
Mr = 319.35 | Dx = 1.376 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54184 Å |
a = 10.6548 (3) Å | Cell parameters from 4480 reflections |
b = 12.6232 (3) Å | θ = 3.5–75.7° |
c = 22.9326 (6) Å | µ = 0.74 mm−1 |
β = 91.457 (3)° | T = 100 K |
V = 3083.38 (14) Å3 | Prismatic, colourless |
Z = 8 | 0.30 × 0.20 × 0.20 mm |
Data collection top
Xcalibur, Ruby diffractometer | 6257 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 4394 reflections with I > 2σ(I) |
Detector resolution: 10.2576 pixels mm-1 | Rint = 0.037 |
ω scans | θmax = 75.8°, θmin = 3.9° |
Absorption correction: multi-scan CrysAlisPro, Oxford Diffraction, 2009 | h = −13→9 |
Tmin = 0.798, Tmax = 1.000 | k = −9→15 |
13441 measured reflections | l = −28→28 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.0697P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max < 0.001 |
6257 reflections | Δρmax = 0.23 e Å−3 |
440 parameters | Δρmin = −0.27 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N' | 0.20635 (14) | −0.06986 (11) | −0.01815 (7) | 0.0177 (3) | |
H1A' | 0.243 (2) | −0.1357 (17) | −0.0176 (9) | 0.031 (6)* | |
O' | 0.20915 (12) | 0.10014 (9) | 0.01560 (5) | 0.0216 (3) | |
C1 | 0.04761 (16) | 0.03155 (13) | −0.07541 (7) | 0.0169 (3) | |
H1 | 0.070309 | 0.096016 | −0.056555 | 0.020* | |
C1' | 0.37132 (16) | −0.01400 (13) | 0.05138 (7) | 0.0173 (4) | |
O1 | −0.08754 (12) | 0.21519 (9) | −0.11290 (5) | 0.0218 (3) | |
C2 | 0.10840 (16) | −0.06185 (13) | −0.06059 (7) | 0.0165 (3) | |
C2' | 0.43847 (17) | −0.10833 (14) | 0.04804 (8) | 0.0203 (4) | |
H2' | 0.406911 | −0.164921 | 0.024618 | 0.024* | |
C3 | 0.07318 (17) | −0.15684 (13) | −0.08966 (7) | 0.0185 (4) | |
H3 | 0.115032 | −0.221074 | −0.079785 | 0.022* | |
C3' | 0.55187 (18) | −0.11987 (14) | 0.07898 (8) | 0.0225 (4) | |
H3' | 0.597616 | −0.184257 | 0.076574 | 0.027* | |
C4 | −0.02049 (17) | −0.15734 (13) | −0.13186 (7) | 0.0189 (4) | |
H4 | −0.042669 | −0.221818 | −0.150840 | 0.023* | |
C4' | 0.59791 (18) | −0.03771 (14) | 0.11319 (8) | 0.0240 (4) | |
H4' | 0.676061 | −0.045246 | 0.133642 | 0.029* | |
C4A | −0.08388 (17) | −0.06353 (13) | −0.14727 (7) | 0.0175 (4) | |
N5 | −0.17937 (14) | −0.06669 (11) | −0.18972 (6) | 0.0182 (3) | |
C5' | 0.53021 (19) | 0.05577 (15) | 0.11772 (8) | 0.0250 (4) | |
H5' | 0.561161 | 0.111505 | 0.141919 | 0.030* | |
C5A | −0.23902 (17) | 0.02073 (13) | −0.20157 (7) | 0.0176 (4) | |
C6 | −0.34776 (17) | 0.01584 (13) | −0.24478 (8) | 0.0209 (4) | |
H6A | −0.421815 | −0.012891 | −0.224901 | 0.025* | |
H6B | −0.326548 | −0.034087 | −0.276329 | 0.025* | |
C6' | 0.41745 (18) | 0.06779 (14) | 0.08693 (8) | 0.0223 (4) | |
H6' | 0.371369 | 0.131894 | 0.090014 | 0.027* | |
C7 | −0.38289 (18) | 0.12224 (14) | −0.27193 (8) | 0.0219 (4) | |
H7A | −0.316206 | 0.145906 | −0.298248 | 0.026* | |
H7B | −0.462260 | 0.115665 | −0.295041 | 0.026* | |
C8 | −0.39839 (18) | 0.20187 (14) | −0.22323 (8) | 0.0224 (4) | |
H8A | −0.428443 | 0.270087 | −0.239665 | 0.027* | |
H8B | −0.461693 | 0.175808 | −0.195805 | 0.027* | |
C9 | −0.27460 (17) | 0.21828 (13) | −0.19110 (8) | 0.0218 (4) | |
H9A | −0.218914 | 0.260947 | −0.215806 | 0.026* | |
H9B | −0.289290 | 0.259078 | −0.155042 | 0.026* | |
N10 | −0.21016 (14) | 0.11761 (11) | −0.17538 (6) | 0.0176 (3) | |
C11 | −0.11300 (16) | 0.12743 (13) | −0.13402 (7) | 0.0168 (3) | |
C11A | −0.04797 (16) | 0.02991 (13) | −0.11862 (7) | 0.0161 (3) | |
C12 | 0.25443 (17) | 0.01106 (13) | 0.01536 (7) | 0.0174 (4) | |
O'A | 1.12370 (12) | 0.57114 (9) | −0.13152 (5) | 0.0214 (3) | |
N'A | 0.99853 (14) | 0.43176 (11) | −0.10650 (7) | 0.0187 (3) | |
H'A | 0.9816 (19) | 0.3648 (16) | −0.1111 (8) | 0.022* | |
C1A | 0.84051 (16) | 0.41220 (13) | −0.03504 (7) | 0.0167 (3) | |
H1A | 0.850020 | 0.337626 | −0.038318 | 0.020* | |
O1A | 0.68461 (12) | 0.28595 (9) | 0.03716 (5) | 0.0214 (3) | |
C1'A | 1.15860 (16) | 0.40492 (14) | −0.17763 (7) | 0.0190 (4) | |
C2A | 0.91416 (16) | 0.47886 (13) | −0.06757 (7) | 0.0171 (4) | |
C2'A | 1.16697 (18) | 0.29544 (15) | −0.17028 (8) | 0.0251 (4) | |
H2'A | 1.133319 | 0.262817 | −0.136777 | 0.030* | |
C3A | 0.89915 (17) | 0.58995 (13) | −0.06187 (7) | 0.0182 (4) | |
H3A | 0.950511 | 0.636426 | −0.083460 | 0.022* | |
C3'A | 1.2246 (2) | 0.23461 (15) | −0.21209 (9) | 0.0307 (5) | |
H3'A | 1.229283 | 0.159977 | −0.207151 | 0.037* | |
C4AA | 0.81077 (18) | 0.63121 (13) | −0.02532 (8) | 0.0203 (4) | |
H4AA | 0.800740 | 0.705801 | −0.022521 | 0.024* | |
C4AB | 0.73542 (17) | 0.56399 (13) | 0.00782 (7) | 0.0175 (4) | |
C4'A | 1.27577 (18) | 0.28063 (16) | −0.26117 (8) | 0.0270 (4) | |
H4'A | 1.314302 | 0.237964 | −0.289770 | 0.032* | |
N5A | 0.64844 (14) | 0.60700 (11) | 0.04506 (6) | 0.0205 (3) | |
C5AB | 0.58566 (16) | 0.54345 (13) | 0.07766 (7) | 0.0180 (4) | |
C5'A | 1.26976 (19) | 0.38956 (16) | −0.26775 (8) | 0.0270 (4) | |
H5'A | 1.305514 | 0.422234 | −0.300743 | 0.032* | |
C6'A | 1.21170 (18) | 0.45089 (15) | −0.22629 (8) | 0.0241 (4) | |
H6'A | 1.208054 | 0.525575 | −0.231157 | 0.029* | |
C6A | 0.49754 (18) | 0.59253 (14) | 0.12060 (8) | 0.0236 (4) | |
H6AA | 0.447364 | 0.647632 | 0.099999 | 0.028* | |
H6AB | 0.548543 | 0.628416 | 0.151412 | 0.028* | |
C7A | 0.40798 (18) | 0.51692 (14) | 0.14971 (8) | 0.0251 (4) | |
H7AA | 0.371563 | 0.551288 | 0.184206 | 0.030* | |
H7AB | 0.338510 | 0.497992 | 0.122168 | 0.030* | |
C8A | 0.47884 (19) | 0.41812 (15) | 0.16823 (8) | 0.0275 (4) | |
H8AA | 0.549752 | 0.437558 | 0.194847 | 0.033* | |
H8AB | 0.422367 | 0.370224 | 0.189482 | 0.033* | |
C9A | 0.52811 (19) | 0.36190 (14) | 0.11529 (9) | 0.0259 (4) | |
H9AA | 0.584158 | 0.303483 | 0.128277 | 0.031* | |
H9AB | 0.456728 | 0.330385 | 0.092909 | 0.031* | |
N10A | 0.59807 (14) | 0.43378 (11) | 0.07662 (6) | 0.0185 (3) | |
C11C | 0.67862 (16) | 0.38367 (13) | 0.03843 (7) | 0.0171 (4) | |
C11B | 0.75229 (16) | 0.45387 (13) | 0.00259 (7) | 0.0166 (4) | |
C12A | 1.09334 (16) | 0.47725 (13) | −0.13591 (7) | 0.0187 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N' | 0.0183 (7) | 0.0102 (7) | 0.0246 (7) | 0.0015 (6) | −0.0028 (6) | −0.0005 (6) |
O' | 0.0247 (7) | 0.0123 (6) | 0.0278 (6) | 0.0012 (5) | −0.0027 (6) | −0.0029 (5) |
C1 | 0.0197 (9) | 0.0102 (8) | 0.0210 (8) | −0.0006 (7) | 0.0013 (7) | −0.0015 (7) |
C1' | 0.0176 (8) | 0.0149 (8) | 0.0194 (8) | −0.0028 (7) | 0.0022 (7) | 0.0020 (7) |
O1 | 0.0256 (7) | 0.0102 (6) | 0.0295 (7) | 0.0011 (5) | −0.0036 (5) | −0.0025 (5) |
C2 | 0.0167 (8) | 0.0123 (8) | 0.0206 (8) | −0.0010 (7) | 0.0016 (7) | −0.0001 (7) |
C2' | 0.0229 (9) | 0.0150 (8) | 0.0229 (8) | −0.0019 (7) | −0.0013 (7) | −0.0015 (7) |
C3 | 0.0226 (9) | 0.0099 (8) | 0.0229 (8) | 0.0018 (7) | 0.0016 (7) | −0.0001 (7) |
C3' | 0.0235 (9) | 0.0171 (8) | 0.0271 (9) | 0.0005 (7) | 0.0016 (8) | 0.0045 (8) |
C4 | 0.0259 (9) | 0.0102 (8) | 0.0208 (8) | −0.0014 (7) | 0.0020 (7) | −0.0028 (7) |
C4' | 0.0241 (10) | 0.0232 (9) | 0.0245 (9) | −0.0038 (8) | −0.0042 (8) | 0.0047 (8) |
C4A | 0.0197 (9) | 0.0129 (8) | 0.0200 (8) | −0.0012 (7) | 0.0014 (7) | −0.0001 (7) |
N5 | 0.0208 (8) | 0.0122 (7) | 0.0214 (7) | 0.0000 (6) | −0.0016 (6) | −0.0004 (6) |
C5' | 0.0299 (10) | 0.0182 (9) | 0.0267 (9) | −0.0049 (8) | −0.0058 (8) | −0.0006 (8) |
C5A | 0.0213 (9) | 0.0124 (8) | 0.0193 (8) | −0.0001 (7) | 0.0018 (7) | 0.0001 (7) |
C6 | 0.0224 (9) | 0.0142 (8) | 0.0259 (9) | 0.0007 (7) | −0.0025 (8) | −0.0016 (7) |
C6' | 0.0254 (10) | 0.0158 (8) | 0.0256 (9) | −0.0006 (7) | −0.0015 (8) | −0.0004 (7) |
C7 | 0.0236 (9) | 0.0183 (9) | 0.0235 (9) | 0.0014 (7) | −0.0034 (7) | −0.0001 (8) |
C8 | 0.0239 (9) | 0.0165 (8) | 0.0267 (9) | 0.0040 (7) | −0.0024 (8) | 0.0001 (8) |
C9 | 0.0270 (10) | 0.0102 (8) | 0.0279 (9) | 0.0049 (7) | −0.0053 (8) | 0.0000 (7) |
N10 | 0.0211 (8) | 0.0099 (7) | 0.0218 (7) | 0.0020 (6) | 0.0003 (6) | −0.0005 (6) |
C11 | 0.0195 (8) | 0.0105 (8) | 0.0206 (8) | −0.0006 (7) | 0.0020 (7) | −0.0003 (7) |
C11A | 0.0180 (8) | 0.0093 (8) | 0.0211 (8) | 0.0011 (7) | 0.0030 (7) | 0.0002 (7) |
C12 | 0.0198 (9) | 0.0131 (8) | 0.0193 (8) | −0.0009 (7) | 0.0012 (7) | 0.0001 (7) |
O'A | 0.0234 (7) | 0.0157 (6) | 0.0252 (6) | −0.0033 (5) | 0.0004 (5) | −0.0009 (5) |
N'A | 0.0208 (8) | 0.0113 (7) | 0.0241 (7) | −0.0013 (6) | 0.0023 (6) | −0.0022 (6) |
C1A | 0.0194 (8) | 0.0092 (7) | 0.0214 (8) | 0.0007 (7) | −0.0038 (7) | −0.0014 (7) |
O1A | 0.0231 (7) | 0.0103 (6) | 0.0310 (7) | 0.0011 (5) | 0.0018 (6) | 0.0001 (5) |
C1'A | 0.0170 (8) | 0.0179 (8) | 0.0218 (8) | 0.0014 (7) | −0.0027 (7) | 0.0007 (7) |
C2A | 0.0178 (8) | 0.0136 (8) | 0.0196 (8) | 0.0023 (7) | −0.0016 (7) | −0.0022 (7) |
C2'A | 0.0271 (10) | 0.0204 (9) | 0.0282 (9) | 0.0049 (8) | 0.0068 (8) | 0.0024 (8) |
C3A | 0.0218 (9) | 0.0126 (8) | 0.0204 (8) | −0.0009 (7) | 0.0021 (7) | 0.0012 (7) |
C3'A | 0.0345 (11) | 0.0193 (9) | 0.0386 (11) | 0.0070 (9) | 0.0078 (9) | −0.0008 (9) |
C4AA | 0.0277 (10) | 0.0095 (8) | 0.0237 (9) | 0.0027 (7) | −0.0013 (8) | −0.0010 (7) |
C4AB | 0.0201 (9) | 0.0110 (8) | 0.0214 (8) | 0.0019 (7) | −0.0023 (7) | −0.0017 (7) |
C4'A | 0.0258 (10) | 0.0294 (10) | 0.0258 (9) | 0.0085 (8) | 0.0020 (8) | −0.0018 (8) |
N5A | 0.0252 (8) | 0.0120 (7) | 0.0243 (7) | 0.0021 (6) | 0.0009 (7) | −0.0024 (6) |
C5AB | 0.0197 (9) | 0.0116 (8) | 0.0226 (8) | 0.0020 (7) | −0.0017 (7) | −0.0018 (7) |
C5'A | 0.0259 (10) | 0.0303 (10) | 0.0249 (9) | 0.0062 (8) | 0.0028 (8) | 0.0062 (8) |
C6'A | 0.0230 (9) | 0.0204 (9) | 0.0288 (9) | 0.0027 (8) | −0.0004 (8) | 0.0035 (8) |
C6A | 0.0258 (10) | 0.0166 (9) | 0.0287 (9) | 0.0042 (8) | 0.0043 (8) | −0.0029 (8) |
C7A | 0.0258 (10) | 0.0206 (9) | 0.0293 (10) | 0.0046 (8) | 0.0056 (8) | −0.0002 (8) |
C8A | 0.0278 (10) | 0.0253 (10) | 0.0297 (10) | 0.0011 (8) | 0.0062 (8) | 0.0037 (8) |
C9A | 0.0282 (10) | 0.0148 (8) | 0.0351 (10) | −0.0001 (8) | 0.0101 (9) | 0.0033 (8) |
N10A | 0.0187 (7) | 0.0116 (7) | 0.0254 (7) | 0.0000 (6) | 0.0025 (6) | 0.0001 (6) |
C11C | 0.0174 (8) | 0.0104 (8) | 0.0232 (8) | 0.0016 (7) | −0.0045 (7) | −0.0022 (7) |
C11B | 0.0189 (8) | 0.0105 (8) | 0.0201 (8) | 0.0006 (7) | −0.0039 (7) | −0.0019 (7) |
C12A | 0.0184 (8) | 0.0156 (8) | 0.0220 (8) | 0.0004 (7) | −0.0042 (7) | 0.0021 (7) |
Geometric parameters (Å, º) top
N'—C12 | 1.370 (2) | O'A—C12A | 1.232 (2) |
N'—C2 | 1.412 (2) | N'A—C12A | 1.356 (2) |
O'—C12 | 1.224 (2) | N'A—C2A | 1.414 (2) |
C1—C2 | 1.383 (2) | C1A—C2A | 1.382 (2) |
C1—C11A | 1.403 (2) | C1A—C11B | 1.395 (2) |
C1'—C2' | 1.392 (2) | O1A—C11C | 1.235 (2) |
C1'—C6' | 1.397 (2) | C1'A—C6'A | 1.391 (2) |
C1'—C12 | 1.510 (2) | C1'A—C2'A | 1.395 (2) |
O1—C11 | 1.236 (2) | C1'A—C12A | 1.505 (2) |
C2—C3 | 1.418 (2) | C2A—C3A | 1.418 (2) |
C2'—C3' | 1.393 (2) | C2'A—C3'A | 1.384 (3) |
C3—C4 | 1.372 (2) | C3A—C4AA | 1.379 (2) |
C3'—C4' | 1.383 (2) | C3'A—C4'A | 1.390 (3) |
C4—C4A | 1.404 (2) | C4AA—C4AB | 1.405 (2) |
C4'—C5' | 1.388 (3) | C4AB—N5A | 1.387 (2) |
C4A—N5 | 1.391 (2) | C4AB—C11B | 1.407 (2) |
C4A—C11A | 1.399 (2) | C4'A—C5'A | 1.385 (3) |
N5—C5A | 1.299 (2) | N5A—C5AB | 1.294 (2) |
C5'—C6' | 1.386 (3) | C5AB—N10A | 1.391 (2) |
C5A—N10 | 1.393 (2) | C5AB—C6A | 1.511 (2) |
C5A—C6 | 1.507 (2) | C5'A—C6'A | 1.384 (3) |
C6—C7 | 1.523 (2) | C6A—C7A | 1.516 (2) |
C7—C8 | 1.515 (2) | C7A—C8A | 1.513 (2) |
C8—C9 | 1.509 (2) | C8A—C9A | 1.512 (2) |
C9—N10 | 1.484 (2) | C9A—N10A | 1.483 (2) |
N10—C11 | 1.392 (2) | N10A—C11C | 1.393 (2) |
C11—C11A | 1.452 (2) | C11C—C11B | 1.452 (2) |
| | | |
C12—N'—C2 | 126.32 (15) | C12A—N'A—C2A | 129.01 (15) |
C2—C1—C11A | 119.21 (16) | C2A—C1A—C11B | 120.34 (16) |
C2'—C1'—C6' | 119.38 (17) | C6'A—C1'A—C2'A | 118.97 (17) |
C2'—C1'—C12 | 124.52 (15) | C6'A—C1'A—C12A | 117.44 (16) |
C6'—C1'—C12 | 115.93 (16) | C2'A—C1'A—C12A | 123.59 (16) |
C1—C2—N' | 124.30 (15) | C1A—C2A—N'A | 117.62 (15) |
C1—C2—C3 | 119.24 (16) | C1A—C2A—C3A | 119.04 (16) |
N'—C2—C3 | 116.46 (15) | N'A—C2A—C3A | 123.30 (16) |
C1'—C2'—C3' | 120.10 (16) | C3'A—C2'A—C1'A | 119.61 (18) |
C4—C3—C2 | 120.96 (16) | C4AA—C3A—C2A | 120.67 (16) |
C4'—C3'—C2' | 120.07 (17) | C2'A—C3'A—C4'A | 121.26 (18) |
C3—C4—C4A | 120.67 (16) | C3A—C4AA—C4AB | 120.62 (16) |
C3'—C4'—C5' | 120.16 (18) | N5A—C4AB—C4AA | 119.79 (15) |
N5—C4A—C11A | 122.64 (16) | N5A—C4AB—C11B | 121.87 (16) |
N5—C4A—C4 | 119.38 (15) | C4AA—C4AB—C11B | 118.34 (16) |
C11A—C4A—C4 | 117.97 (16) | C5'A—C4'A—C3'A | 119.03 (18) |
C5A—N5—C4A | 117.87 (15) | C5AB—N5A—C4AB | 118.44 (15) |
C6'—C5'—C4' | 120.01 (17) | N5A—C5AB—N10A | 123.80 (16) |
N5—C5A—N10 | 123.65 (16) | N5A—C5AB—C6A | 117.46 (15) |
N5—C5A—C6 | 117.83 (15) | N10A—C5AB—C6A | 118.70 (15) |
N10—C5A—C6 | 118.49 (15) | C6'A—C5'A—C4'A | 120.06 (18) |
C5A—C6—C7 | 114.18 (15) | C5'A—C6'A—C1'A | 121.05 (18) |
C5'—C6'—C1' | 120.24 (17) | C5AB—C6A—C7A | 115.93 (15) |
C8—C7—C6 | 108.30 (14) | C8A—C7A—C6A | 109.10 (15) |
C9—C8—C7 | 109.93 (15) | C9A—C8A—C7A | 110.03 (16) |
N10—C9—C8 | 113.22 (14) | N10A—C9A—C8A | 112.52 (15) |
C11—N10—C5A | 121.60 (14) | C5AB—N10A—C11C | 121.52 (15) |
C11—N10—C9 | 114.88 (14) | C5AB—N10A—C9A | 123.32 (15) |
C5A—N10—C9 | 123.45 (14) | C11C—N10A—C9A | 115.16 (14) |
O1—C11—N10 | 119.92 (15) | O1A—C11C—N10A | 120.07 (16) |
O1—C11—C11A | 124.46 (16) | O1A—C11C—C11B | 124.52 (16) |
N10—C11—C11A | 115.62 (14) | N10A—C11C—C11B | 115.41 (15) |
C4A—C11A—C1 | 121.94 (16) | C1A—C11B—C4AB | 120.97 (16) |
C4A—C11A—C11 | 118.53 (16) | C1A—C11B—C11C | 120.16 (15) |
C1—C11A—C11 | 119.52 (15) | C4AB—C11B—C11C | 118.84 (16) |
O'—C12—N' | 123.10 (16) | O'A—C12A—N'A | 124.33 (17) |
O'—C12—C1' | 120.64 (16) | O'A—C12A—C1'A | 120.72 (16) |
N'—C12—C1' | 116.23 (15) | N'A—C12A—C1'A | 114.91 (15) |
| | | |
C11A—C1—C2—N' | 179.56 (15) | C11B—C1A—C2A—N'A | −177.71 (15) |
C11A—C1—C2—C3 | 0.4 (2) | C11B—C1A—C2A—C3A | 0.3 (2) |
C12—N'—C2—C1 | 1.4 (3) | C12A—N'A—C2A—C1A | −168.46 (17) |
C12—N'—C2—C3 | −179.40 (16) | C12A—N'A—C2A—C3A | 13.6 (3) |
C6'—C1'—C2'—C3' | −1.3 (3) | C6'A—C1'A—C2'A—C3'A | −1.7 (3) |
C12—C1'—C2'—C3' | 173.78 (16) | C12A—C1'A—C2'A—C3'A | 177.48 (17) |
C1—C2—C3—C4 | −0.4 (3) | C1A—C2A—C3A—C4AA | −1.3 (3) |
N'—C2—C3—C4 | −179.63 (16) | N'A—C2A—C3A—C4AA | 176.67 (16) |
C1'—C2'—C3'—C4' | 0.1 (3) | C1'A—C2'A—C3'A—C4'A | 0.7 (3) |
C2—C3—C4—C4A | 0.0 (3) | C2A—C3A—C4AA—C4AB | 1.2 (3) |
C2'—C3'—C4'—C5' | 1.2 (3) | C3A—C4AA—C4AB—N5A | 178.95 (16) |
C3—C4—C4A—N5 | −179.27 (16) | C3A—C4AA—C4AB—C11B | −0.2 (3) |
C3—C4—C4A—C11A | 0.4 (3) | C2'A—C3'A—C4'A—C5'A | 0.7 (3) |
C11A—C4A—N5—C5A | −2.0 (3) | C4AA—C4AB—N5A—C5AB | −175.89 (16) |
C4—C4A—N5—C5A | 177.71 (16) | C11B—C4AB—N5A—C5AB | 3.2 (2) |
C3'—C4'—C5'—C6' | −1.4 (3) | C4AB—N5A—C5AB—N10A | −1.6 (3) |
C4A—N5—C5A—N10 | 1.9 (3) | C4AB—N5A—C5AB—C6A | 176.18 (15) |
C4A—N5—C5A—C6 | −176.21 (15) | C3'A—C4'A—C5'A—C6'A | −1.0 (3) |
N5—C5A—C6—C7 | −159.86 (16) | C4'A—C5'A—C6'A—C1'A | 0.0 (3) |
N10—C5A—C6—C7 | 21.9 (2) | C2'A—C1'A—C6'A—C5'A | 1.4 (3) |
C4'—C5'—C6'—C1' | 0.2 (3) | C12A—C1'A—C6'A—C5'A | −177.85 (17) |
C2'—C1'—C6'—C5' | 1.2 (3) | N5A—C5AB—C6A—C7A | 168.85 (16) |
C12—C1'—C6'—C5' | −174.33 (16) | N10A—C5AB—C6A—C7A | −13.3 (2) |
C5A—C6—C7—C8 | −51.1 (2) | C5AB—C6A—C7A—C8A | 43.9 (2) |
C6—C7—C8—C9 | 64.22 (19) | C6A—C7A—C8A—C9A | −62.8 (2) |
C7—C8—C9—N10 | −47.7 (2) | C7A—C8A—C9A—N10A | 50.8 (2) |
N5—C5A—N10—C11 | 0.2 (3) | N5A—C5AB—N10A—C11C | −1.7 (3) |
C6—C5A—N10—C11 | 178.39 (16) | C6A—C5AB—N10A—C11C | −179.40 (15) |
N5—C5A—N10—C9 | 176.99 (17) | N5A—C5AB—N10A—C9A | 178.32 (17) |
C6—C5A—N10—C9 | −4.9 (2) | C6A—C5AB—N10A—C9A | 0.6 (3) |
C8—C9—N10—C11 | −164.95 (15) | C8A—C9A—N10A—C5AB | −19.7 (3) |
C8—C9—N10—C5A | 18.1 (2) | C8A—C9A—N10A—C11C | 160.24 (16) |
C5A—N10—C11—O1 | 177.88 (16) | C5AB—N10A—C11C—O1A | −177.62 (16) |
C9—N10—C11—O1 | 0.9 (2) | C9A—N10A—C11C—O1A | 2.4 (2) |
C5A—N10—C11—C11A | −2.3 (2) | C5AB—N10A—C11C—C11B | 3.1 (2) |
C9—N10—C11—C11A | −179.31 (14) | C9A—N10A—C11C—C11B | −176.91 (15) |
N5—C4A—C11A—C1 | 179.25 (15) | C2A—C1A—C11B—C4AB | 0.7 (2) |
C4—C4A—C11A—C1 | −0.4 (3) | C2A—C1A—C11B—C11C | −177.54 (15) |
N5—C4A—C11A—C11 | −0.1 (3) | N5A—C4AB—C11B—C1A | −179.85 (15) |
C4—C4A—C11A—C11 | −179.82 (15) | C4AA—C4AB—C11B—C1A | −0.8 (2) |
C2—C1—C11A—C4A | 0.0 (3) | N5A—C4AB—C11B—C11C | −1.6 (2) |
C2—C1—C11A—C11 | 179.41 (15) | C4AA—C4AB—C11B—C11C | 177.47 (15) |
O1—C11—C11A—C4A | −178.01 (17) | O1A—C11C—C11B—C1A | −2.5 (3) |
N10—C11—C11A—C4A | 2.2 (2) | N10A—C11C—C11B—C1A | 176.78 (15) |
O1—C11—C11A—C1 | 2.6 (3) | O1A—C11C—C11B—C4AB | 179.27 (17) |
N10—C11—C11A—C1 | −177.22 (15) | N10A—C11C—C11B—C4AB | −1.5 (2) |
C2—N'—C12—O' | 6.6 (3) | C2A—N'A—C12A—O'A | 2.2 (3) |
C2—N'—C12—C1' | −171.41 (15) | C2A—N'A—C12A—C1'A | −175.40 (16) |
C2'—C1'—C12—O' | −171.22 (17) | C6'A—C1'A—C12A—O'A | −26.6 (2) |
C6'—C1'—C12—O' | 4.0 (2) | C2'A—C1'A—C12A—O'A | 154.22 (18) |
C2'—C1'—C12—N' | 6.8 (3) | C6'A—C1'A—C12A—N'A | 151.12 (16) |
C6'—C1'—C12—N' | −177.94 (15) | C2'A—C1'A—C12A—N'A | −28.1 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N′—H1A′···O1Ai | 0.92 (2) | 2.10 (2) | 3.0011 (18) | 166.6 (19) |
C1—H1···O′ | 0.95 | 2.19 | 2.808 (2) | 122 |
C3—H3···O1Ai | 0.95 | 2.47 | 3.257 (2) | 141 |
N′A—H′A···O1ii | 0.87 (2) | 2.03 (2) | 2.8861 (18) | 169.0 (19) |
C1A—H1A···O1ii | 0.95 | 2.41 | 3.167 (2) | 136 |
C3A—H3A···O′A | 0.95 | 2.32 | 2.920 (2) | 120 |
C4AA—H4AA···O′iii | 0.95 | 2.46 | 3.405 (2) | 176 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x+1, y, z; (iii) −x+1, −y+1, −z. |