In the asymmetric unit of the title compound, C
16H
14N
4O, there are two crystallographically independent molecules, which are connected to each other by O—H
N hydrogen bonds, forming a molecular chain. The neighboring chains are linked into a layer through π–π stacking interactions.
Supporting information
CCDC reference: 633981
Key indicators
- Single-crystal X-ray study
- T = 250 K
- Mean (C-C) = 0.003 Å
- R factor = 0.059
- wR factor = 0.182
- Data-to-parameter ratio = 20.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for N5 - C29 .. 6.06 su
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: PROCESS-AUTO (Rigaku/MSC, 2004); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2003).
N-[5-(1-Naphthyl)pyrimidin-4-yl]acetamide oxime
top
Crystal data top
C16H14N4O | Z = 4 |
Mr = 278.31 | F(000) = 584.00 |
Triclinic, P1 | Dx = 1.326 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71075 Å |
a = 10.8011 (6) Å | Cell parameters from 14565 reflections |
b = 11.6051 (6) Å | θ = 3.0–30.0° |
c = 12.8489 (8) Å | µ = 0.09 mm−1 |
α = 63.3951 (16)° | T = 250 K |
β = 76.8282 (16)° | Plate, colorless |
γ = 89.5278 (19)° | 0.38 × 0.30 × 0.10 mm |
V = 1394.00 (14) Å3 | |
Data collection top
Rigaku R-AXIS RAPID-II diffractometer | Rint = 0.065 |
Detector resolution: 10.00 pixels mm-1 | θmax = 30.0° |
ω scans | h = −15→15 |
24844 measured reflections | k = −16→14 |
8057 independent reflections | l = −18→18 |
4461 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.059 | w = 1/[σ2(Fo2) + (0.0969P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.182 | (Δ/σ)max < 0.001 |
S = 0.98 | Δρmax = 0.19 e Å−3 |
8057 reflections | Δρmin = −0.29 e Å−3 |
396 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | −0.04449 (11) | 0.72598 (12) | −0.02991 (10) | 0.0559 (3) | |
O2 | 0.47007 (12) | 0.21978 (13) | 0.44912 (11) | 0.0614 (4) | |
N1 | 0.33828 (15) | 0.35923 (14) | 0.27913 (13) | 0.0567 (4) | |
N2 | 0.30864 (12) | 0.49534 (13) | 0.08461 (12) | 0.0476 (3) | |
N3 | 0.11721 (12) | 0.58780 (12) | 0.06085 (10) | 0.0402 (3) | |
N4 | 0.04303 (12) | 0.69267 (13) | −0.11028 (10) | 0.0463 (3) | |
N5 | 0.78779 (15) | −0.16030 (14) | 0.83121 (14) | 0.0587 (4) | |
N6 | 0.78593 (12) | −0.03469 (14) | 0.62523 (13) | 0.0518 (3) | |
N7 | 0.61025 (13) | 0.07402 (13) | 0.57141 (11) | 0.0427 (3) | |
N8 | 0.57076 (13) | 0.18216 (13) | 0.38248 (11) | 0.0513 (3) | |
C1 | 0.01803 (16) | 0.48307 (15) | 0.31973 (12) | 0.0462 (4) | |
C2 | −0.07889 (19) | 0.38326 (17) | 0.38622 (14) | 0.0599 (5) | |
H2 | −0.0644 | 0.3007 | 0.3950 | 0.072* | |
C3 | −0.1996 (2) | 0.4038 (2) | 0.44119 (17) | 0.0710 (6) | |
H3 | −0.2637 | 0.3349 | 0.4860 | 0.085* | |
C4 | −0.22295 (18) | 0.5247 (2) | 0.42895 (15) | 0.0645 (5) | |
H4 | −0.3038 | 0.5378 | 0.4634 | 0.077* | |
C5 | −0.14543 (18) | 0.75530 (18) | 0.35143 (15) | 0.0574 (4) | |
H5 | −0.2259 | 0.7706 | 0.3846 | 0.069* | |
C6 | −0.04983 (19) | 0.85490 (18) | 0.29153 (16) | 0.0616 (5) | |
H6 | −0.0650 | 0.9366 | 0.2849 | 0.074* | |
C7 | 0.07051 (18) | 0.83380 (17) | 0.24039 (16) | 0.0573 (4) | |
H7 | 0.1359 | 0.9017 | 0.2003 | 0.069* | |
C8 | 0.09417 (15) | 0.71536 (15) | 0.24816 (14) | 0.0475 (4) | |
H8 | 0.1752 | 0.7039 | 0.2124 | 0.057* | |
C9 | −0.00263 (15) | 0.60869 (15) | 0.30991 (12) | 0.0430 (3) | |
C10 | −0.12578 (15) | 0.62982 (16) | 0.36463 (13) | 0.0490 (4) | |
C11 | 0.14374 (15) | 0.45955 (14) | 0.26067 (13) | 0.0423 (3) | |
C12 | 0.22162 (17) | 0.38127 (15) | 0.32642 (14) | 0.0526 (4) | |
H12 | 0.1918 | 0.3404 | 0.4097 | 0.063* | |
C13 | 0.37459 (17) | 0.41987 (16) | 0.16029 (16) | 0.0535 (4) | |
H13 | 0.4561 | 0.4082 | 0.1256 | 0.064* | |
C14 | 0.19194 (14) | 0.51403 (14) | 0.13353 (12) | 0.0387 (3) | |
C15 | 0.12498 (14) | 0.62361 (13) | −0.05942 (12) | 0.0385 (3) | |
C16 | 0.22325 (16) | 0.58013 (17) | −0.13202 (14) | 0.0531 (4) | |
H16A | 0.2232 | 0.4878 | −0.0894 | 0.080* | |
H16B | 0.3060 | 0.6217 | −0.1457 | 0.080* | |
H16C | 0.2040 | 0.6028 | −0.2078 | 0.080* | |
C17 | 0.47810 (15) | −0.01293 (14) | 0.82413 (12) | 0.0416 (3) | |
C18 | 0.37447 (17) | −0.10496 (16) | 0.88365 (14) | 0.0524 (4) | |
H18 | 0.3844 | −0.1894 | 0.8958 | 0.063* | |
C19 | 0.25289 (18) | −0.07460 (18) | 0.92704 (16) | 0.0603 (5) | |
H19 | 0.1841 | −0.1389 | 0.9678 | 0.072* | |
C20 | 0.23632 (16) | 0.04897 (17) | 0.90920 (14) | 0.0543 (4) | |
H20 | 0.1557 | 0.0686 | 0.9369 | 0.065* | |
C21 | 0.32672 (16) | 0.27622 (16) | 0.82942 (14) | 0.0522 (4) | |
H21 | 0.2463 | 0.2979 | 0.8547 | 0.063* | |
C22 | 0.42834 (17) | 0.36959 (17) | 0.77440 (16) | 0.0576 (4) | |
H22 | 0.4170 | 0.4537 | 0.7626 | 0.069* | |
C23 | 0.54950 (17) | 0.33825 (16) | 0.73590 (16) | 0.0557 (4) | |
H23 | 0.6188 | 0.4019 | 0.6994 | 0.067* | |
C24 | 0.56796 (15) | 0.21627 (15) | 0.75083 (14) | 0.0465 (4) | |
H24 | 0.6495 | 0.1979 | 0.7241 | 0.056* | |
C25 | 0.46377 (13) | 0.11615 (14) | 0.80699 (12) | 0.0392 (3) | |
C26 | 0.34032 (14) | 0.14759 (15) | 0.84902 (12) | 0.0424 (3) | |
C27 | 0.60582 (14) | −0.04808 (14) | 0.78141 (13) | 0.0417 (3) | |
C28 | 0.67047 (17) | −0.12698 (16) | 0.86208 (15) | 0.0526 (4) | |
H28 | 0.6309 | −0.1597 | 0.9435 | 0.063* | |
C29 | 0.83767 (17) | −0.11026 (17) | 0.71363 (18) | 0.0591 (5) | |
H29 | 0.9193 | −0.1308 | 0.6901 | 0.071* | |
C30 | 0.66898 (14) | −0.00305 (14) | 0.65795 (13) | 0.0410 (3) | |
C31 | 0.63956 (15) | 0.10959 (14) | 0.44876 (12) | 0.0428 (3) | |
C32 | 0.74810 (18) | 0.06245 (19) | 0.38940 (15) | 0.0640 (5) | |
H32A | 0.7396 | −0.0306 | 0.4296 | 0.096* | |
H32B | 0.8272 | 0.0952 | 0.3936 | 0.096* | |
H32C | 0.7475 | 0.0923 | 0.3067 | 0.096* | |
H1O | −0.099 (2) | 0.757 (2) | −0.072 (2) | 0.090 (8)* | |
H3N | 0.0453 (18) | 0.6067 (18) | 0.0991 (17) | 0.065 (5)* | |
H2O | 0.434 (2) | 0.265 (2) | 0.390 (2) | 0.080 (7)* | |
H7N | 0.5380 (17) | 0.0975 (18) | 0.5978 (17) | 0.059 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0496 (7) | 0.0734 (8) | 0.0426 (6) | 0.0288 (6) | −0.0196 (5) | −0.0214 (6) |
O2 | 0.0621 (8) | 0.0756 (8) | 0.0403 (6) | 0.0309 (6) | −0.0227 (6) | −0.0170 (6) |
N1 | 0.0686 (10) | 0.0544 (8) | 0.0583 (9) | 0.0242 (7) | −0.0375 (8) | −0.0256 (7) |
N2 | 0.0462 (7) | 0.0566 (8) | 0.0445 (7) | 0.0185 (6) | −0.0179 (6) | −0.0242 (6) |
N3 | 0.0439 (7) | 0.0478 (7) | 0.0302 (6) | 0.0166 (6) | −0.0139 (5) | −0.0170 (5) |
N4 | 0.0466 (7) | 0.0557 (8) | 0.0317 (6) | 0.0137 (6) | −0.0144 (5) | −0.0139 (6) |
N5 | 0.0649 (9) | 0.0603 (9) | 0.0686 (10) | 0.0302 (7) | −0.0412 (8) | −0.0338 (8) |
N6 | 0.0459 (8) | 0.0641 (9) | 0.0583 (8) | 0.0224 (7) | −0.0207 (6) | −0.0358 (7) |
N7 | 0.0428 (7) | 0.0523 (7) | 0.0344 (6) | 0.0168 (6) | −0.0131 (5) | −0.0195 (5) |
N8 | 0.0539 (8) | 0.0579 (8) | 0.0336 (6) | 0.0097 (6) | −0.0118 (6) | −0.0135 (6) |
C1 | 0.0574 (10) | 0.0505 (9) | 0.0290 (7) | 0.0049 (7) | −0.0132 (6) | −0.0157 (6) |
C2 | 0.0774 (13) | 0.0539 (10) | 0.0398 (8) | −0.0077 (9) | −0.0039 (8) | −0.0187 (7) |
C3 | 0.0714 (13) | 0.0800 (13) | 0.0474 (10) | −0.0202 (10) | 0.0060 (9) | −0.0264 (9) |
C4 | 0.0577 (11) | 0.0882 (14) | 0.0420 (9) | −0.0019 (10) | −0.0014 (8) | −0.0300 (9) |
C5 | 0.0586 (11) | 0.0758 (12) | 0.0428 (9) | 0.0229 (9) | −0.0138 (8) | −0.0313 (9) |
C6 | 0.0727 (12) | 0.0602 (11) | 0.0580 (10) | 0.0222 (9) | −0.0179 (9) | −0.0318 (9) |
C7 | 0.0621 (11) | 0.0530 (10) | 0.0576 (10) | 0.0100 (8) | −0.0113 (8) | −0.0277 (8) |
C8 | 0.0475 (9) | 0.0520 (9) | 0.0447 (8) | 0.0085 (7) | −0.0095 (7) | −0.0247 (7) |
C9 | 0.0484 (9) | 0.0522 (9) | 0.0309 (7) | 0.0104 (7) | −0.0133 (6) | −0.0196 (6) |
C10 | 0.0487 (9) | 0.0669 (10) | 0.0311 (7) | 0.0081 (8) | −0.0080 (7) | −0.0231 (7) |
C11 | 0.0546 (9) | 0.0406 (8) | 0.0346 (7) | 0.0096 (6) | −0.0183 (6) | −0.0164 (6) |
C12 | 0.0725 (12) | 0.0487 (9) | 0.0383 (8) | 0.0128 (8) | −0.0265 (8) | −0.0157 (7) |
C13 | 0.0562 (10) | 0.0599 (10) | 0.0566 (10) | 0.0244 (8) | −0.0281 (8) | −0.0311 (8) |
C14 | 0.0435 (8) | 0.0413 (7) | 0.0349 (7) | 0.0126 (6) | −0.0168 (6) | −0.0174 (6) |
C15 | 0.0393 (8) | 0.0425 (7) | 0.0289 (6) | 0.0062 (6) | −0.0103 (6) | −0.0115 (6) |
C16 | 0.0556 (10) | 0.0680 (10) | 0.0363 (8) | 0.0152 (8) | −0.0105 (7) | −0.0251 (7) |
C17 | 0.0477 (8) | 0.0469 (8) | 0.0300 (6) | 0.0094 (7) | −0.0145 (6) | −0.0153 (6) |
C18 | 0.0603 (10) | 0.0480 (9) | 0.0426 (8) | 0.0016 (8) | −0.0081 (7) | −0.0176 (7) |
C19 | 0.0535 (11) | 0.0667 (11) | 0.0480 (9) | −0.0119 (9) | 0.0032 (8) | −0.0225 (8) |
C20 | 0.0447 (9) | 0.0713 (11) | 0.0428 (8) | 0.0032 (8) | −0.0029 (7) | −0.0263 (8) |
C21 | 0.0506 (9) | 0.0625 (10) | 0.0470 (9) | 0.0176 (8) | −0.0110 (7) | −0.0289 (8) |
C22 | 0.0625 (11) | 0.0501 (9) | 0.0635 (11) | 0.0153 (8) | −0.0135 (9) | −0.0301 (8) |
C23 | 0.0548 (10) | 0.0490 (9) | 0.0610 (10) | 0.0049 (8) | −0.0072 (8) | −0.0268 (8) |
C24 | 0.0405 (8) | 0.0517 (9) | 0.0494 (9) | 0.0092 (7) | −0.0091 (7) | −0.0261 (7) |
C25 | 0.0416 (8) | 0.0472 (8) | 0.0308 (6) | 0.0112 (6) | −0.0121 (6) | −0.0182 (6) |
C26 | 0.0405 (8) | 0.0538 (9) | 0.0319 (7) | 0.0090 (7) | −0.0074 (6) | −0.0196 (6) |
C27 | 0.0488 (9) | 0.0426 (8) | 0.0393 (7) | 0.0135 (6) | −0.0196 (6) | −0.0197 (6) |
C28 | 0.0655 (11) | 0.0530 (9) | 0.0471 (9) | 0.0187 (8) | −0.0292 (8) | −0.0228 (7) |
C29 | 0.0536 (10) | 0.0642 (11) | 0.0824 (13) | 0.0292 (8) | −0.0340 (9) | −0.0457 (10) |
C30 | 0.0411 (8) | 0.0455 (8) | 0.0430 (8) | 0.0134 (6) | −0.0175 (6) | −0.0227 (6) |
C31 | 0.0447 (8) | 0.0475 (8) | 0.0320 (7) | 0.0042 (7) | −0.0071 (6) | −0.0158 (6) |
C32 | 0.0649 (12) | 0.0790 (13) | 0.0440 (9) | 0.0191 (9) | −0.0055 (8) | −0.0286 (9) |
Geometric parameters (Å, º) top
O1—N4 | 1.4199 (16) | C8—H8 | 0.9300 |
O1—H1O | 0.86 (2) | C9—C10 | 1.431 (2) |
O2—N8 | 1.4175 (17) | C11—C12 | 1.368 (2) |
O2—H2O | 0.88 (2) | C11—C14 | 1.4256 (19) |
N1—C13 | 1.323 (2) | C12—H12 | 0.9300 |
N1—C12 | 1.344 (2) | C13—H13 | 0.9300 |
N2—C13 | 1.3277 (19) | C15—C16 | 1.488 (2) |
N2—C14 | 1.3369 (18) | C16—H16A | 0.9600 |
N3—C14 | 1.3684 (18) | C16—H16B | 0.9600 |
N3—C15 | 1.3907 (17) | C16—H16C | 0.9600 |
N3—H3N | 0.901 (18) | C17—C18 | 1.370 (2) |
N4—C15 | 1.2790 (18) | C17—C25 | 1.426 (2) |
N5—C29 | 1.326 (2) | C17—C27 | 1.489 (2) |
N5—C28 | 1.346 (2) | C18—C19 | 1.412 (2) |
N6—C29 | 1.327 (2) | C18—H18 | 0.9300 |
N6—C30 | 1.3401 (18) | C19—C20 | 1.364 (2) |
N7—C30 | 1.3638 (18) | C19—H19 | 0.9300 |
N7—C31 | 1.3951 (18) | C20—C26 | 1.415 (2) |
N7—H7N | 0.870 (18) | C20—H20 | 0.9300 |
N8—C31 | 1.274 (2) | C21—C22 | 1.363 (2) |
C1—C2 | 1.376 (2) | C21—C26 | 1.411 (2) |
C1—C9 | 1.426 (2) | C21—H21 | 0.9300 |
C1—C11 | 1.485 (2) | C22—C23 | 1.396 (2) |
C2—C3 | 1.407 (3) | C22—H22 | 0.9300 |
C2—H2 | 0.9300 | C23—C24 | 1.360 (2) |
C3—C4 | 1.368 (3) | C23—H23 | 0.9300 |
C3—H3 | 0.9300 | C24—C25 | 1.427 (2) |
C4—C10 | 1.413 (2) | C24—H24 | 0.9300 |
C4—H4 | 0.9300 | C25—C26 | 1.4294 (19) |
C5—C6 | 1.362 (3) | C27—C28 | 1.367 (2) |
C5—C10 | 1.409 (2) | C27—C30 | 1.423 (2) |
C5—H5 | 0.9300 | C28—H28 | 0.9300 |
C6—C7 | 1.390 (2) | C29—H29 | 0.9300 |
C6—H6 | 0.9300 | C31—C32 | 1.487 (2) |
C7—C8 | 1.359 (2) | C32—H32A | 0.9600 |
C7—H7 | 0.9300 | C32—H32B | 0.9600 |
C8—C9 | 1.421 (2) | C32—H32C | 0.9600 |
| | | |
N4—O1—H1O | 98.9 (15) | N3—C15—C16 | 122.39 (13) |
N8—O2—H2O | 97.5 (14) | C15—C16—H16A | 109.5 |
C13—N1—C12 | 114.56 (14) | C15—C16—H16B | 109.5 |
C13—N2—C14 | 116.63 (13) | H16A—C16—H16B | 109.5 |
C14—N3—C15 | 130.23 (13) | C15—C16—H16C | 109.5 |
C14—N3—H3N | 115.0 (13) | H16A—C16—H16C | 109.5 |
C15—N3—H3N | 114.2 (13) | H16B—C16—H16C | 109.5 |
C15—N4—O1 | 111.06 (12) | C18—C17—C25 | 119.44 (14) |
C29—N5—C28 | 114.32 (14) | C18—C17—C27 | 120.44 (14) |
C29—N6—C30 | 116.43 (14) | C25—C17—C27 | 120.08 (13) |
C30—N7—C31 | 130.34 (13) | C17—C18—C19 | 121.52 (16) |
C30—N7—H7N | 115.1 (12) | C17—C18—H18 | 119.2 |
C31—N7—H7N | 114.1 (13) | C19—C18—H18 | 119.2 |
C31—N8—O2 | 111.40 (12) | C20—C19—C18 | 120.04 (15) |
C2—C1—C9 | 119.40 (15) | C20—C19—H19 | 120.0 |
C2—C1—C11 | 120.27 (15) | C18—C19—H19 | 120.0 |
C9—C1—C11 | 120.32 (13) | C19—C20—C26 | 120.78 (15) |
C1—C2—C3 | 121.27 (17) | C19—C20—H20 | 119.6 |
C1—C2—H2 | 119.4 | C26—C20—H20 | 119.6 |
C3—C2—H2 | 119.4 | C22—C21—C26 | 121.77 (15) |
C4—C3—C2 | 120.23 (17) | C22—C21—H21 | 119.1 |
C4—C3—H3 | 119.9 | C26—C21—H21 | 119.1 |
C2—C3—H3 | 119.9 | C21—C22—C23 | 119.64 (15) |
C3—C4—C10 | 120.85 (17) | C21—C22—H22 | 120.2 |
C3—C4—H4 | 119.6 | C23—C22—H22 | 120.2 |
C10—C4—H4 | 119.6 | C24—C23—C22 | 121.15 (16) |
C6—C5—C10 | 121.85 (16) | C24—C23—H23 | 119.4 |
C6—C5—H5 | 119.1 | C22—C23—H23 | 119.4 |
C10—C5—H5 | 119.1 | C23—C24—C25 | 120.88 (14) |
C5—C6—C7 | 119.67 (17) | C23—C24—H24 | 119.6 |
C5—C6—H6 | 120.2 | C25—C24—H24 | 119.6 |
C7—C6—H6 | 120.2 | C17—C25—C24 | 122.98 (13) |
C8—C7—C6 | 120.99 (17) | C17—C25—C26 | 119.11 (13) |
C8—C7—H7 | 119.5 | C24—C25—C26 | 117.90 (13) |
C6—C7—H7 | 119.5 | C21—C26—C20 | 122.28 (14) |
C7—C8—C9 | 121.24 (15) | C21—C26—C25 | 118.62 (13) |
C7—C8—H8 | 119.4 | C20—C26—C25 | 119.10 (14) |
C9—C8—H8 | 119.4 | C28—C27—C30 | 115.80 (14) |
C8—C9—C1 | 123.02 (14) | C28—C27—C17 | 120.37 (14) |
C8—C9—C10 | 117.73 (14) | C30—C27—C17 | 123.83 (13) |
C1—C9—C10 | 119.25 (14) | N5—C28—C27 | 124.22 (16) |
C5—C10—C4 | 122.60 (16) | N5—C28—H28 | 117.9 |
C5—C10—C9 | 118.49 (15) | C27—C28—H28 | 117.9 |
C4—C10—C9 | 118.91 (16) | N5—C29—N6 | 128.26 (15) |
C12—C11—C14 | 115.04 (14) | N5—C29—H29 | 115.9 |
C12—C11—C1 | 121.42 (14) | N6—C29—H29 | 115.9 |
C14—C11—C1 | 123.54 (13) | N6—C30—N7 | 119.35 (13) |
N1—C12—C11 | 124.61 (15) | N6—C30—C27 | 120.95 (14) |
N1—C12—H12 | 117.7 | N7—C30—C27 | 119.70 (13) |
C11—C12—H12 | 117.7 | N8—C31—N7 | 120.72 (14) |
N1—C13—N2 | 127.78 (16) | N8—C31—C32 | 116.61 (14) |
N1—C13—H13 | 116.1 | N7—C31—C32 | 122.64 (14) |
N2—C13—H13 | 116.1 | C31—C32—H32A | 109.5 |
N2—C14—N3 | 119.78 (12) | C31—C32—H32B | 109.5 |
N2—C14—C11 | 121.24 (13) | H32A—C32—H32B | 109.5 |
N3—C14—C11 | 118.97 (13) | C31—C32—H32C | 109.5 |
N4—C15—N3 | 120.00 (13) | H32A—C32—H32C | 109.5 |
N4—C15—C16 | 117.57 (13) | H32B—C32—H32C | 109.5 |
| | | |
C9—C1—C2—C3 | 2.3 (3) | C25—C17—C18—C19 | 1.0 (2) |
C11—C1—C2—C3 | −178.83 (16) | C27—C17—C18—C19 | 178.78 (15) |
C1—C2—C3—C4 | 0.2 (3) | C17—C18—C19—C20 | 0.5 (3) |
C2—C3—C4—C10 | −2.1 (3) | C18—C19—C20—C26 | −1.0 (3) |
C10—C5—C6—C7 | 0.7 (3) | C26—C21—C22—C23 | 0.1 (3) |
C5—C6—C7—C8 | 0.7 (3) | C21—C22—C23—C24 | 0.9 (3) |
C6—C7—C8—C9 | −0.8 (3) | C22—C23—C24—C25 | −0.3 (3) |
C7—C8—C9—C1 | 179.74 (15) | C18—C17—C25—C24 | 177.09 (14) |
C7—C8—C9—C10 | −0.5 (2) | C27—C17—C25—C24 | −0.7 (2) |
C2—C1—C9—C8 | 176.77 (15) | C18—C17—C25—C26 | −2.0 (2) |
C11—C1—C9—C8 | −2.1 (2) | C27—C17—C25—C26 | −179.83 (12) |
C2—C1—C9—C10 | −3.0 (2) | C23—C24—C25—C17 | 179.67 (15) |
C11—C1—C9—C10 | 178.15 (13) | C23—C24—C25—C26 | −1.2 (2) |
C6—C5—C10—C4 | 178.42 (16) | C22—C21—C26—C20 | 178.07 (16) |
C6—C5—C10—C9 | −2.0 (2) | C22—C21—C26—C25 | −1.6 (2) |
C3—C4—C10—C5 | −179.07 (17) | C19—C20—C26—C21 | −179.77 (16) |
C3—C4—C10—C9 | 1.3 (3) | C19—C20—C26—C25 | −0.1 (2) |
C8—C9—C10—C5 | 1.8 (2) | C17—C25—C26—C21 | −178.73 (13) |
C1—C9—C10—C5 | −178.41 (14) | C24—C25—C26—C21 | 2.1 (2) |
C8—C9—C10—C4 | −178.57 (15) | C17—C25—C26—C20 | 1.6 (2) |
C1—C9—C10—C4 | 1.2 (2) | C24—C25—C26—C20 | −177.57 (14) |
C2—C1—C11—C12 | −66.0 (2) | C18—C17—C27—C28 | −68.1 (2) |
C9—C1—C11—C12 | 112.85 (17) | C25—C17—C27—C28 | 109.68 (17) |
C2—C1—C11—C14 | 113.21 (18) | C18—C17—C27—C30 | 112.52 (18) |
C9—C1—C11—C14 | −67.9 (2) | C25—C17—C27—C30 | −69.7 (2) |
C13—N1—C12—C11 | −0.3 (2) | C29—N5—C28—C27 | −0.3 (3) |
C14—C11—C12—N1 | 3.1 (2) | C30—C27—C28—N5 | 1.5 (2) |
C1—C11—C12—N1 | −177.60 (14) | C17—C27—C28—N5 | −177.89 (14) |
C12—N1—C13—N2 | −1.9 (3) | C28—N5—C29—N6 | −1.1 (3) |
C14—N2—C13—N1 | 0.8 (3) | C30—N6—C29—N5 | 0.9 (3) |
C13—N2—C14—N3 | −178.20 (14) | C29—N6—C30—N7 | −179.77 (14) |
C13—N2—C14—C11 | 2.5 (2) | C29—N6—C30—C27 | 0.6 (2) |
C15—N3—C14—N2 | 19.0 (2) | C31—N7—C30—N6 | 14.0 (3) |
C15—N3—C14—C11 | −161.64 (14) | C31—N7—C30—C27 | −166.31 (15) |
C12—C11—C14—N2 | −4.2 (2) | C28—C27—C30—N6 | −1.7 (2) |
C1—C11—C14—N2 | 176.50 (14) | C17—C27—C30—N6 | 177.71 (14) |
C12—C11—C14—N3 | 176.43 (14) | C28—C27—C30—N7 | 178.68 (14) |
C1—C11—C14—N3 | −2.8 (2) | C17—C27—C30—N7 | −1.9 (2) |
O1—N4—C15—N3 | 2.1 (2) | O2—N8—C31—N7 | 1.4 (2) |
O1—N4—C15—C16 | 179.69 (13) | O2—N8—C31—C32 | 179.46 (14) |
C14—N3—C15—N4 | 179.04 (15) | C30—N7—C31—N8 | 179.00 (15) |
C14—N3—C15—C16 | 1.5 (2) | C30—N7—C31—C32 | 1.1 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···N5i | 0.86 (2) | 1.89 (2) | 2.744 (2) | 175.4 (19) |
O2—H2O···N1 | 0.88 (2) | 1.89 (2) | 2.762 (2) | 172.7 (18) |
N3—H3N···O1 | 0.90 (2) | 2.064 (19) | 2.4878 (17) | 107.5 (15) |
N7—H7N···O2 | 0.870 (19) | 2.097 (18) | 2.5068 (18) | 108.0 (14) |
Symmetry code: (i) x−1, y+1, z−1. |