organic compounds
In the title compound, C28H38N4O6, the 4-aryl substituent occupies a pseudo-axial position approximately orthogonal to the plane of the dihydropyridine ring [88.1 (3)°]. The dihydropyridine ring adopts a flattened boat conformation. The H atom on the pyridine N atom is involved in a bifurcated intramolecular hydrogen bond, the acceptors being the N atoms of the two piperidylmethyl groups [NN 2.629 (4) and 2.695 (4) Å].
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100010416/fr1242sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100010416/fr1242Isup2.hkl |
CCDC reference: 153891
Computing details top
Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: PARST (Nardelli, 1983, 1995) and PARSTCIF (Nardelli, 1991).
Ethyl methyl 1,4-dihydro-4-(3-nitrophenyl)-2,6-bis(1-piperidylmethyl)pyridine
-3,5-dicarboxylate top
Crystal data top
C28H38N4O6 | F(000) = 1128.0 |
Mr = 526.62 | Dx = 1.256 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 8.9714 (6) Å | Cell parameters from 38 reflections |
b = 11.7112 (11) Å | θ = 21.5–53.8° |
c = 26.718 (2) Å | µ = 0.73 mm−1 |
β = 97.271 (5)° | T = 296 K |
V = 2784.6 (4) Å3 | Prismatic, light yellow |
Z = 4 | 0.28 × 0.24 × 0.20 mm |
Data collection top
Siemens P4 four-circle diffractometer | 2435 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.041 |
Graphite monochromator | θmax = 69.1°, θmin = 4.5° |
2θ/ω scans | h = −1→10 |
Absorption correction: ψ-scan (North et al., 1968) | k = −1→14 |
Tmin = 0.725, Tmax = 0.864 | l = −32→32 |
6839 measured reflections | 3 standard reflections every 100 reflections |
4939 independent reflections | intensity decay: <1.7% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.054 | H-atom parameters constrained |
wR(F2) = 0.270 | w = 1/[σ2(Fo2) + (0.1088P)2 + 2.85P] where P = [max(Fo2,0) + 2Fc2]/3 |
S = 1.21 | (Δ/σ)max < 0.001 |
4939 reflections | Δρmax = 0.32 e Å−3 |
346 parameters | Δρmin = −0.28 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: none |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O4 | 0.9166 (5) | 0.4428 (3) | 0.2188 (2) | 0.1154 (19) | |
O3 | 1.0384 (4) | 0.3111 (3) | 0.2601 (2) | 0.1006 (17) | |
O2 | 0.7231 (4) | 0.2964 (3) | −0.0250 (1) | 0.0768 (13) | |
O5 | 0.1730 (3) | 0.3352 (3) | 0.1384 (1) | 0.0750 (13) | |
O1 | 0.6325 (4) | 0.1440 (3) | 0.0117 (1) | 0.0701 (13) | |
O6 | 0.2721 (3) | 0.1710 (2) | 0.1158 (1) | 0.0615 (11) | |
N1 | 0.5616 (3) | 0.4921 (3) | 0.0910 (1) | 0.0419 (10) | |
N2 | 0.9385 (5) | 0.3424 (4) | 0.2288 (2) | 0.0688 (16) | |
N3 | 0.7760 (4) | 0.6109 (3) | 0.0569 (1) | 0.0464 (12) | |
N4 | 0.4550 (4) | 0.6247 (3) | 0.1608 (1) | 0.0463 (12) | |
C4 | 0.5315 (4) | 0.2575 (3) | 0.0900 (1) | 0.0387 (12) | |
C6 | 0.6317 (4) | 0.4345 (3) | 0.0558 (1) | 0.0401 (13) | |
C1' | 0.6453 (4) | 0.2166 (3) | 0.1336 (1) | 0.0400 (13) | |
C3 | 0.4141 (4) | 0.3348 (3) | 0.1083 (1) | 0.0385 (12) | |
C13 | 0.3529 (4) | 0.5402 (3) | 0.1344 (2) | 0.0480 (14) | |
C5 | 0.6092 (4) | 0.3200 (3) | 0.0505 (1) | 0.0403 (12) | |
C2 | 0.4411 (4) | 0.4490 (3) | 0.1117 (1) | 0.0396 (13) | |
C2' | 0.7389 (4) | 0.2940 (3) | 0.1614 (2) | 0.0462 (13) | |
C3' | 0.8435 (4) | 0.2566 (4) | 0.2002 (2) | 0.0465 (13) | |
C19 | 0.2741 (5) | 0.2858 (4) | 0.1226 (2) | 0.0469 (14) | |
C18 | 0.5228 (5) | 0.5800 (4) | 0.2093 (2) | 0.0609 (15) | |
C6' | 0.6622 (5) | 0.1013 (4) | 0.1466 (2) | 0.0561 (17) | |
C4' | 0.8609 (5) | 0.1432 (4) | 0.2132 (2) | 0.0553 (16) | |
C7 | 0.7265 (5) | 0.5111 (4) | 0.0263 (2) | 0.0496 (14) | |
C12 | 0.9083 (5) | 0.5834 (4) | 0.0928 (2) | 0.0592 (16) | |
C5A | 0.6624 (5) | 0.2579 (4) | 0.0091 (2) | 0.0495 (15) | |
C5' | 0.7683 (5) | 0.0664 (4) | 0.1857 (2) | 0.0635 (18) | |
C11 | 0.9456 (6) | 0.6808 (4) | 0.1293 (2) | 0.076 (2) | |
C14 | 0.3773 (5) | 0.7318 (4) | 0.1679 (2) | 0.0599 (16) | |
C16 | 0.5644 (6) | 0.7770 (4) | 0.2426 (2) | 0.074 (2) | |
C17 | 0.6352 (5) | 0.6625 (4) | 0.2364 (2) | 0.0711 (19) | |
C8 | 0.8071 (6) | 0.7090 (4) | 0.0267 (2) | 0.0724 (19) | |
C15 | 0.4870 (6) | 0.8199 (4) | 0.1926 (2) | 0.076 (2) | |
C20 | 0.1367 (5) | 0.1139 (4) | 0.1257 (2) | 0.075 (2) | |
C10 | 0.9734 (7) | 0.7875 (5) | 0.1012 (2) | 0.086 (2) | |
C22 | 0.6684 (8) | 0.0755 (4) | −0.0309 (2) | 0.112 (3) | |
C9 | 0.8426 (7) | 0.8115 (4) | 0.0606 (3) | 0.097 (3) | |
C21 | 0.0183 (8) | 0.1248 (6) | 0.0830 (3) | 0.121 (3) | |
H1 | 0.59483 | 0.55855 | 0.10045 | 0.0545* | |
H4 | 0.48034 | 0.19042 | 0.07398 | 0.0504* | |
H13A | 0.28614 | 0.57763 | 0.10802 | 0.0625* | |
H13B | 0.29201 | 0.50598 | 0.15794 | 0.0625* | |
H2' | 0.73111 | 0.37147 | 0.15385 | 0.0601* | |
H18A | 0.57280 | 0.50838 | 0.20403 | 0.0792* | |
H18B | 0.44439 | 0.56467 | 0.23033 | 0.0792* | |
H6' | 0.60118 | 0.04715 | 0.12864 | 0.0729* | |
H4' | 0.93240 | 0.11967 | 0.23941 | 0.0719* | |
H7A | 0.81312 | 0.46913 | 0.01790 | 0.0645* | |
H7B | 0.66774 | 0.53533 | −0.00483 | 0.0645* | |
H12A | 0.99336 | 0.56856 | 0.07469 | 0.0769* | |
H12B | 0.88896 | 0.51498 | 0.11141 | 0.0769* | |
H5' | 0.77696 | −0.01083 | 0.19366 | 0.0826* | |
H11A | 0.86293 | 0.69285 | 0.14881 | 0.0987* | |
H11B | 1.03430 | 0.66184 | 0.15242 | 0.0987* | |
H14A | 0.29850 | 0.71880 | 0.18901 | 0.0779* | |
H14B | 0.33101 | 0.76013 | 0.13552 | 0.0779* | |
H16A | 0.64111 | 0.83111 | 0.25602 | 0.0960* | |
H16B | 0.49175 | 0.77085 | 0.26646 | 0.0960* | |
H17A | 0.67277 | 0.63192 | 0.26938 | 0.0924* | |
H17B | 0.71958 | 0.67113 | 0.21739 | 0.0924* | |
H8A | 0.72040 | 0.72528 | 0.00218 | 0.0942* | |
H8B | 0.89163 | 0.69249 | 0.00855 | 0.0942* | |
H15A | 0.56175 | 0.83671 | 0.17034 | 0.0992* | |
H15B | 0.43360 | 0.89005 | 0.19782 | 0.0992* | |
H20A | 0.10231 | 0.14664 | 0.15556 | 0.0972* | |
H20B | 0.15797 | 0.03375 | 0.13226 | 0.0972* | |
H10A | 1.06510 | 0.77932 | 0.08582 | 0.1123* | |
H10B | 0.98619 | 0.85119 | 0.12456 | 0.1123* | |
H22A | 0.60179 | 0.09566 | −0.06060 | 0.1452* | |
H22B | 0.65663 | −0.00396 | −0.02360 | 0.1452* | |
H22C | 0.77030 | 0.08994 | −0.03652 | 0.1452* | |
H9A | 0.75462 | 0.83162 | 0.07636 | 0.1259* | |
H9B | 0.86733 | 0.87602 | 0.04039 | 0.1259* | |
H21A | −0.00631 | 0.20392 | 0.07756 | 0.1567* | |
H21B | −0.06925 | 0.08390 | 0.09023 | 0.1567* | |
H21C | 0.05283 | 0.09356 | 0.05333 | 0.1567* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O4 | 0.127 (3) | 0.062 (3) | 0.134 (4) | 0.003 (2) | −0.072 (3) | −0.015 (2) |
O3 | 0.092 (3) | 0.101 (3) | 0.093 (3) | −0.002 (2) | −0.049 (2) | 0.014 (2) |
O2 | 0.111 (3) | 0.065 (2) | 0.062 (2) | −0.014 (2) | 0.042 (2) | −0.0048 (17) |
O5 | 0.0502 (18) | 0.064 (2) | 0.116 (3) | −0.0087 (16) | 0.0343 (19) | −0.0229 (19) |
O1 | 0.104 (3) | 0.0476 (19) | 0.066 (2) | 0.0000 (18) | 0.0393 (19) | −0.0091 (15) |
O6 | 0.0507 (17) | 0.0490 (18) | 0.089 (2) | −0.0187 (14) | 0.0255 (16) | −0.0022 (16) |
N1 | 0.0419 (17) | 0.0378 (18) | 0.0461 (18) | −0.0102 (15) | 0.0057 (15) | −0.0057 (15) |
N2 | 0.070 (3) | 0.069 (3) | 0.060 (3) | 0.003 (2) | −0.021 (2) | 0.001 (2) |
N3 | 0.0448 (18) | 0.0469 (19) | 0.0457 (19) | −0.0123 (16) | −0.0014 (16) | 0.0057 (16) |
N4 | 0.057 (2) | 0.037 (2) | 0.0438 (18) | −0.0007 (16) | 0.0032 (16) | −0.0033 (15) |
C4 | 0.038 (2) | 0.038 (2) | 0.039 (2) | −0.0082 (18) | 0.0023 (17) | −0.0034 (17) |
C6 | 0.034 (2) | 0.048 (2) | 0.036 (2) | −0.0053 (18) | −0.0031 (17) | 0.0028 (18) |
C1' | 0.040 (2) | 0.039 (2) | 0.042 (2) | −0.0021 (18) | 0.0127 (18) | 0.0005 (18) |
C3 | 0.037 (2) | 0.039 (2) | 0.038 (2) | −0.0052 (18) | 0.0041 (17) | −0.0010 (18) |
C13 | 0.046 (2) | 0.045 (2) | 0.053 (2) | −0.001 (2) | 0.0038 (19) | −0.008 (2) |
C5 | 0.037 (2) | 0.044 (2) | 0.040 (2) | −0.0039 (18) | 0.0044 (17) | −0.0006 (18) |
C2 | 0.037 (2) | 0.043 (2) | 0.037 (2) | −0.0035 (18) | −0.0004 (17) | −0.0010 (18) |
C2' | 0.047 (2) | 0.039 (2) | 0.051 (2) | 0.005 (2) | −0.001 (2) | 0.004 (2) |
C3' | 0.046 (2) | 0.047 (2) | 0.046 (2) | 0.003 (2) | 0.002 (2) | 0.004 (2) |
C19 | 0.042 (2) | 0.044 (2) | 0.055 (3) | −0.009 (2) | 0.007 (2) | −0.004 (2) |
C18 | 0.067 (3) | 0.063 (3) | 0.051 (3) | 0.006 (2) | 0.002 (2) | 0.005 (2) |
C6' | 0.060 (3) | 0.041 (2) | 0.067 (3) | −0.005 (2) | 0.011 (2) | 0.005 (2) |
C4' | 0.054 (3) | 0.059 (3) | 0.053 (2) | 0.010 (2) | 0.011 (2) | 0.016 (2) |
C7 | 0.053 (2) | 0.053 (3) | 0.042 (2) | −0.012 (2) | 0.005 (2) | 0.005 (2) |
C12 | 0.050 (2) | 0.066 (3) | 0.058 (3) | −0.011 (2) | −0.004 (2) | 0.004 (2) |
C5A | 0.054 (3) | 0.048 (3) | 0.048 (2) | 0.002 (2) | 0.008 (2) | −0.001 (2) |
C5' | 0.067 (3) | 0.045 (3) | 0.079 (3) | 0.007 (3) | 0.013 (3) | 0.022 (3) |
C11 | 0.074 (3) | 0.093 (4) | 0.059 (3) | −0.035 (3) | 0.005 (3) | −0.005 (3) |
C14 | 0.074 (3) | 0.044 (3) | 0.062 (3) | 0.006 (3) | 0.007 (2) | −0.008 (2) |
C16 | 0.076 (3) | 0.074 (4) | 0.072 (3) | −0.011 (3) | 0.008 (3) | −0.023 (3) |
C17 | 0.065 (3) | 0.086 (4) | 0.059 (3) | −0.003 (3) | −0.006 (2) | −0.018 (3) |
C8 | 0.082 (3) | 0.058 (3) | 0.073 (3) | −0.025 (3) | −0.010 (3) | 0.019 (3) |
C15 | 0.095 (4) | 0.043 (3) | 0.091 (4) | −0.007 (3) | 0.009 (3) | −0.015 (3) |
C20 | 0.069 (3) | 0.066 (3) | 0.101 (4) | −0.027 (3) | 0.020 (3) | −0.007 (3) |
C10 | 0.093 (4) | 0.083 (4) | 0.083 (4) | −0.040 (3) | 0.009 (3) | −0.015 (3) |
C22 | 0.185 (7) | 0.050 (3) | 0.122 (5) | −0.004 (4) | 0.103 (5) | −0.020 (3) |
C9 | 0.116 (5) | 0.053 (3) | 0.118 (3) | −0.022 (3) | 0.002 (4) | 0.011 (3) |
C21 | 0.101 (5) | 0.127 (6) | 0.138 (6) | −0.036 (4) | 0.034 (5) | −0.021 (5) |
Geometric parameters (Å, º) top
O4—N2 | 1.216 (6) | C4'—C5' | 1.372 (6) |
O3—N2 | 1.203 (5) | C4'—H4' | 0.930 |
O2—C5A | 1.207 (6) | C7—H7A | 0.970 |
O5—C19 | 1.197 (5) | C7—H7B | 0.970 |
O1—C5A | 1.364 (5) | C12—C11 | 1.508 (7) |
O1—C22 | 1.460 (7) | C12—H12A | 0.970 |
O6—C19 | 1.356 (5) | C12—H12B | 0.970 |
O6—C20 | 1.440 (6) | C5'—H5' | 0.930 |
N1—C6 | 1.371 (5) | C11—C10 | 1.494 (8) |
N1—C2 | 1.372 (5) | C11—H11A | 0.970 |
N1—H1 | 0.860 | C11—H11B | 0.970 |
N2—C3' | 1.469 (6) | C14—C15 | 1.518 (7) |
N3—C7 | 1.462 (5) | C14—H14A | 0.970 |
N3—C12 | 1.466 (5) | C14—H14B | 0.970 |
N3—C8 | 1.450 (6) | C16—C17 | 1.502 (7) |
N4—C13 | 1.467 (5) | C16—C15 | 1.513 (7) |
N4—C18 | 1.457 (5) | C16—H16A | 0.970 |
N4—C14 | 1.459 (5) | C16—H16B | 0.970 |
C4—C1' | 1.525 (5) | C17—H17A | 0.970 |
C4—C3 | 1.516 (5) | C17—H17B | 0.970 |
C4—C5 | 1.524 (5) | C8—C9 | 1.513 (7) |
C4—H4 | 0.980 | C8—H8A | 0.970 |
C6—C5 | 1.360 (5) | C8—H8B | 0.970 |
C6—C7 | 1.522 (6) | C15—H15A | 0.970 |
C1'—C2' | 1.387 (5) | C15—H15B | 0.970 |
C1'—C6' | 1.398 (6) | C20—C21 | 1.461 (8) |
C3—C2 | 1.360 (5) | C20—H20A | 0.970 |
C3—C19 | 1.475 (6) | C20—H20B | 0.970 |
C13—C2 | 1.502 (6) | C10—C9 | 1.521 (8) |
C13—H13A | 0.970 | C10—H10A | 0.970 |
C13—H13B | 0.970 | C10—H10B | 0.970 |
C5—C5A | 1.454 (6) | C22—H22A | 0.960 |
C2'—C3' | 1.378 (5) | C22—H22B | 0.960 |
C2'—H2' | 0.930 | C22—H22C | 0.960 |
C3'—C4' | 1.377 (6) | C9—H9A | 0.970 |
C18—C17 | 1.513 (6) | C9—H9B | 0.970 |
C18—H18A | 0.970 | C21—H21A | 0.960 |
C18—H18B | 0.970 | C21—H21B | 0.960 |
C6'—C5' | 1.384 (6) | C21—H21C | 0.960 |
C6'—H6' | 0.930 | ||
O4···O3 | 2.118 (6) | C12···C8 | 2.388 (6) |
O4···C2' | 2.703 (6) | C12···C10 | 2.463 (7) |
O4···C3' | 2.313 (6) | C12···C9 | 2.846 (7) |
O4···H2' | 2.397 | C12···H1 | 2.860 |
O4···H12B | 2.970 | C12···H7A | 2.470 |
O3···C3' | 2.307 (5) | C12···H11A | 2.049 |
O3···C4' | 2.733 (6) | C12···H11B | 2.049 |
O3···H4' | 2.470 | C12···H8B | 2.577 |
O2···O1 | 2.238 (5) | C12···H10A | 2.710 |
O2···C6 | 2.899 (5) | C5A···C22 | 2.392 (7) |
O2···C5 | 2.391 (5) | C5A···H4 | 2.649 |
O2···C7 | 2.862 (5) | C5A···H7A | 2.815 |
O2···C22 | 2.634 (6) | C5A···H22A | 2.668 |
O2···H7A | 2.413 | C5A···H22C | 2.567 |
O2···H7B | 2.904 | C5'···H6' | 2.012 |
O2···H22A | 2.712 | C5'···H4' | 2.019 |
O2···H22C | 2.481 | C11···C8 | 2.881 (7) |
O5···O6 | 2.233 (4) | C11···C9 | 2.477 (8) |
O5···C3 | 2.401 (5) | C11···H12A | 2.048 |
O5···C13 | 2.903 (5) | C11···H12B | 2.048 |
O5···C2 | 2.916 (5) | C11···H10A | 2.036 |
O5···C20 | 2.628 (6) | C11···H10B | 2.036 |
O5···H13B | 2.296 | C11···H9A | 2.728 |
O5···H20A | 2.358 | C14···C16 | 2.497 (7) |
O5···H21A | 2.633 | C14···C17 | 2.879 (6) |
O1···C4 | 2.729 (5) | C14···H13A | 2.482 |
O1···C5 | 2.329 (5) | C14···H13B | 2.757 |
O1···H4 | 2.347 | C14···H18B | 2.592 |
O1···H22A | 1.997 | C14···H16B | 2.740 |
O1···H22B | 1.997 | C14···H15A | 2.056 |
O1···H22C | 1.997 | C14···H15B | 2.055 |
O6···C4 | 2.706 (5) | C16···H18B | 2.713 |
O6···C3 | 2.325 (5) | C16···H14A | 2.710 |
O6···C21 | 2.395 (7) | C16···H17A | 2.042 |
O6···H4 | 2.306 | C16···H17B | 2.042 |
O6···H20A | 1.985 | C16···H15A | 2.051 |
O6···H20B | 1.985 | C16···H15B | 2.051 |
O6···H21A | 2.605 | C17···C15 | 2.479 (7) |
O6···H21C | 2.578 | C17···H18A | 2.049 |
N1···N3 | 2.629 (5) | C17···H18B | 2.049 |
N1···N4 | 2.695 (5) | C17···H16A | 2.042 |
N1···C4 | 2.761 (5) | C17···H16B | 2.042 |
N1···C3 | 2.349 (5) | C17···H15A | 2.724 |
N1···C13 | 2.392 (5) | C8···C10 | 2.507 (7) |
N1···C5 | 2.351 (5) | C8···H7A | 2.820 |
N1···C7 | 2.422 (5) | C8···H7B | 2.478 |
N1···H13A | 2.757 | C8···H12A | 2.569 |
N1···H2' | 2.547 | C8···H10A | 2.758 |
N1···H7B | 2.886 | C8···H9A | 2.050 |
N1···H12B | 2.931 | C8···H9B | 2.050 |
N2···C2' | 2.441 (5) | C15···H14A | 2.057 |
N2···C4' | 2.455 (6) | C15···H14B | 2.057 |
N2···H2' | 2.578 | C15···H16A | 2.052 |
N2···H4' | 2.625 | C15···H16B | 2.052 |
N3···C6 | 2.437 (5) | C15···H17B | 2.735 |
N3···C11 | 2.445 (6) | C20···H21A | 1.998 |
N3···C10 | 2.878 (6) | C20···H21B | 1.998 |
N3···C9 | 2.423 (6) | C20···H21C | 1.998 |
N3···H1 | 2.203 | C10···H12A | 2.672 |
N3···H7A | 2.010 | C10···H11A | 2.036 |
N3···H7B | 2.010 | C10···H11B | 2.036 |
N3···H12A | 2.010 | C10···H8B | 2.729 |
N3···H12B | 2.010 | C10···H9A | 2.057 |
N3···H11A | 2.661 | C10···H9B | 2.057 |
N3···H8A | 1.998 | C9···H11A | 2.723 |
N3···H8B | 1.998 | C9···H8A | 2.055 |
N3···H9A | 2.648 | C9···H8B | 2.055 |
N4···C2 | 2.435 (5) | C9···H10A | 2.059 |
N4···C16 | 2.894 (6) | C9···H10B | 2.059 |
N4···C17 | 2.462 (5) | C21···H20A | 2.004 |
N4···C15 | 2.443 (6) | C21···H20B | 2.004 |
N4···H1 | 2.300 | H1···H13A | 2.811 |
N4···H13A | 2.013 | H1···H2' | 2.809 |
N4···H13B | 2.013 | H1···H18A | 2.860 |
N4···H18A | 1.999 | H1···H7B | 2.980 |
N4···H18B | 1.999 | H1···H12B | 2.667 |
N4···H14A | 2.005 | H4···H6' | 2.392 |
N4···H14B | 2.005 | H13A···H13B | 1.571 |
N4···H17B | 2.703 | H13A···H14A | 2.714 |
N4···H15A | 2.661 | H13A···H14B | 2.279 |
C4···C6 | 2.479 (5) | H13B···H18A | 2.660 |
C4···C2 | 2.479 (5) | H13B···H18B | 2.327 |
C4···C2' | 2.527 (5) | H13B···H14A | 2.625 |
C4···C19 | 2.591 (6) | H2'···H18A | 2.621 |
C4···C6' | 2.561 (6) | H2'···H12B | 2.554 |
C4···C5A | 2.587 (6) | H18A···H18B | 1.569 |
C4···H2' | 2.670 | H18A···H17A | 2.356 |
C4···H6' | 2.713 | H18A···H17B | 2.319 |
C6···C3 | 2.799 (5) | H18B···H14A | 2.413 |
C6···C2 | 2.415 (6) | H18B···H16B | 2.615 |
C6···C5A | 2.450 (6) | H18B···H17A | 2.316 |
C6···H1 | 1.934 | H18B···H17B | 2.826 |
C6···H2' | 2.758 | H6'···H5' | 2.296 |
C6···H7A | 2.064 | H4'···H5' | 2.312 |
C6···H7B | 2.064 | H7A···H7B | 1.572 |
C6···H12B | 2.748 | H7A···H12A | 2.377 |
C1'···C3 | 2.514 (5) | H7A···H12B | 2.562 |
C1'···C5 | 2.513 (5) | H7A···H8B | 2.729 |
C1'···C3' | 2.397 (5) | H7B···H8A | 2.277 |
C1'···C4' | 2.822 (6) | H7B···H8B | 2.714 |
C1'···C5' | 2.422 (6) | H12A···H12B | 1.570 |
C1'···H4 | 2.054 | H12A···H11A | 2.828 |
C1'···H2' | 2.018 | H12A···H11B | 2.334 |
C1'···H6' | 2.024 | H12A···H8B | 2.378 |
C3···C13 | 2.584 (5) | H12A···H10A | 2.559 |
C3···C5 | 2.482 (6) | H12B···H11A | 2.335 |
C3···H4 | 2.047 | H12B···H11B | 2.345 |
C3···H13B | 2.710 | H11A···H11B | 1.571 |
C3···H2' | 2.980 | H11A···H17B | 2.382 |
C13···C18 | 2.403 (6) | H11A···H10A | 2.814 |
C13···C14 | 2.415 (6) | H11A···H10B | 2.294 |
C13···H1 | 2.466 | H11A···H9A | 2.618 |
C13···H18A | 2.562 | H11B···H10A | 2.293 |
C13···H18B | 2.606 | H11B···H10B | 2.361 |
C13···H14A | 2.630 | H14A···H14B | 1.571 |
C13···H14B | 2.583 | H14A···H16B | 2.598 |
C5···C2 | 2.803 (6) | H14A···H15A | 2.834 |
C5···C7 | 2.589 (6) | H14A···H15B | 2.340 |
C5···H4 | 2.054 | H14B···H15A | 2.338 |
C5···H2' | 2.902 | H14B···H15B | 2.355 |
C5···H7A | 2.749 | H16A···H16B | 1.570 |
C2···C19 | 2.469 (6) | H16A···H17A | 2.372 |
C2···H1 | 1.935 | H16A···H17B | 2.292 |
C2···H13A | 2.043 | H16A···H15A | 2.311 |
C2···H13B | 2.043 | H16A···H15B | 2.372 |
C2···H2' | 2.850 | H16B···H17A | 2.293 |
C2···H18A | 2.688 | H16B···H17B | 2.818 |
C2'···C6' | 2.378 (6) | H16B···H15A | 2.827 |
C2'···C4' | 2.418 (6) | H16B···H15B | 2.311 |
C2'···C5' | 2.749 (6) | H17A···H17B | 1.570 |
C3'···C6' | 2.723 (6) | H17B···H15A | 2.626 |
C3'···C5' | 2.345 (6) | H8A···H8B | 1.572 |
C3'···H2' | 2.010 | H8A···H9A | 2.328 |
C3'···H4' | 2.024 | H8A···H9B | 2.357 |
C19···C20 | 2.366 (7) | H8B···H10A | 2.628 |
C19···H4 | 2.639 | H8B···H9A | 2.830 |
C19···H13B | 2.744 | H8B···H9B | 2.332 |
C19···H20A | 2.480 | H15A···H15B | 1.570 |
C19···H21A | 2.816 | H20A···H20B | 1.569 |
C18···C14 | 2.393 (6) | H20A···H21A | 2.287 |
C18···C16 | 2.484 (7) | H20A···H21B | 2.297 |
C18···C15 | 2.857 (7) | H20A···H21C | 2.782 |
C18···H13B | 2.491 | H20B···H21A | 2.781 |
C18···H14A | 2.590 | H20B···H21B | 2.276 |
C18···H16B | 2.741 | H20B···H21C | 2.307 |
C18···H17A | 2.051 | H10A···H10B | 1.571 |
C18···H17B | 2.051 | H10A···H9A | 2.832 |
C6'···C4' | 2.405 (6) | H10A···H9B | 2.315 |
C6'···H4 | 2.591 | H10B···H9A | 2.313 |
C6'···H5' | 2.010 | H10B···H9B | 2.382 |
C4'···H5' | 1.998 | H22A···H22B | 1.568 |
C7···C12 | 2.409 (6) | H22A···H22C | 1.568 |
C7···C8 | 2.427 (6) | H22B···H22C | 1.568 |
C7···H1 | 2.493 | H9A···H9B | 1.569 |
C7···H12A | 2.659 | H21A···H21B | 1.568 |
C7···H12B | 2.541 | H21A···H21C | 1.568 |
C7···H8A | 2.589 | H21B···H21C | 1.568 |
C7···H8B | 2.667 | ||
C5A—O1—C22 | 115.7 (3) | H12A—C12—H12B | 108.1 |
C19—O6—C20 | 115.6 (3) | O2—C5A—O1 | 120.9 (4) |
C6—N1—C2 | 123.3 (3) | O2—C5A—C5 | 127.6 (4) |
C6—N1—H1 | 118.4 | O1—C5A—C5 | 111.4 (3) |
C2—N1—H1 | 118.4 | C6'—C5'—C4' | 121.5 (4) |
O4—N2—O3 | 122.2 (4) | C6'—C5'—H5' | 119.2 |
O4—N2—C3' | 118.6 (4) | C4'—C5'—H5' | 119.2 |
O3—N2—C3' | 119.1 (4) | C12—C11—C10 | 110.2 (4) |
C7—N3—C12 | 110.7 (3) | C12—C11—H11A | 109.6 |
C7—N3—C8 | 112.9 (3) | C12—C11—H11B | 109.6 |
C12—N3—C8 | 110.0 (3) | C10—C11—H11A | 109.6 |
C13—N4—C18 | 110.5 (3) | C10—C11—H11B | 109.6 |
C13—N4—C14 | 111.2 (3) | H11A—C11—H11B | 108.1 |
C18—N4—C14 | 110.2 (3) | N4—C14—C15 | 110.3 (3) |
C1'—C4—C3 | 111.5 (3) | N4—C14—H14A | 109.6 |
C1'—C4—C5 | 111.1 (3) | N4—C14—H14B | 109.6 |
C1'—C4—H4 | 108.2 | C15—C14—H14A | 109.6 |
C3—C4—C5 | 109.5 (3) | C15—C14—H14B | 109.6 |
C3—C4—H4 | 108.2 | H14A—C14—H14B | 108.1 |
C5—C4—H4 | 108.2 | C17—C16—C15 | 110.7 (4) |
N1—C6—C5 | 118.8 (3) | C17—C16—H16A | 109.5 |
N1—C6—C7 | 113.5 (3) | C17—C16—H16B | 109.5 |
C5—C6—C7 | 127.7 (3) | C15—C16—H16A | 109.5 |
C4—C1'—C2' | 120.4 (3) | C15—C16—H16B | 109.5 |
C4—C1'—C6' | 122.3 (3) | H16A—C16—H16B | 108.1 |
C2'—C1'—C6' | 117.3 (3) | C18—C17—C16 | 110.9 (4) |
C4—C3—C2 | 118.9 (3) | C18—C17—H17A | 109.4 |
C4—C3—C19 | 120.0 (3) | C18—C17—H17B | 109.5 |
C2—C3—C19 | 121.0 (3) | C16—C17—H17A | 109.4 |
N4—C13—C2 | 110.2 (3) | C16—C17—H17B | 109.5 |
N4—C13—H13A | 109.6 | H17A—C17—H17B | 108.0 |
N4—C13—H13B | 109.6 | N3—C8—C9 | 109.7 (4) |
C2—C13—H13A | 109.6 | N3—C8—H8A | 109.7 |
C2—C13—H13B | 109.6 | N3—C8—H8B | 109.7 |
H13A—C13—H13B | 108.1 | C9—C8—H8A | 109.7 |
C4—C5—C6 | 118.4 (3) | C9—C8—H8B | 109.7 |
C4—C5—C5A | 120.6 (3) | H8A—C8—H8B | 108.2 |
C6—C5—C5A | 120.9 (3) | C14—C15—C16 | 110.9 (4) |
N1—C2—C3 | 118.5 (3) | C14—C15—H15A | 109.4 |
N1—C2—C13 | 112.6 (3) | C14—C15—H15B | 109.4 |
C3—C2—C13 | 128.9 (3) | C16—C15—H15A | 109.5 |
C1'—C2'—C3' | 120.2 (4) | C16—C15—H15B | 109.5 |
C1'—C2'—H2' | 119.9 | H15A—C15—H15B | 108.0 |
C3'—C2'—H2' | 119.9 | O6—C20—C21 | 111.3 (4) |
N2—C3'—C2' | 118.0 (4) | O6—C20—H20A | 109.4 |
N2—C3'—C4' | 119.2 (4) | O6—C20—H20B | 109.4 |
C2'—C3'—C4' | 122.8 (4) | C21—C20—H20A | 109.4 |
O5—C19—O6 | 121.9 (4) | C21—C20—H20B | 109.4 |
O5—C19—C3 | 127.7 (4) | H20A—C20—H20B | 108.0 |
O6—C19—C3 | 110.4 (3) | C11—C10—C9 | 110.5 (4) |
N4—C18—C17 | 111.9 (4) | C11—C10—H10A | 109.6 |
N4—C18—H18A | 109.2 | C11—C10—H10B | 109.5 |
N4—C18—H18B | 109.2 | C9—C10—H10A | 109.6 |
C17—C18—H18A | 109.2 | C9—C10—H10B | 109.6 |
C17—C18—H18B | 109.2 | H10A—C10—H10B | 108.1 |
H18A—C18—H18B | 107.9 | O1—C22—H22A | 109.5 |
C1'—C6'—C5' | 121.1 (4) | O1—C22—H22B | 109.5 |
C1'—C6'—H6' | 119.5 | O1—C22—H22C | 109.5 |
C5'—C6'—H6' | 119.5 | H22A—C22—H22B | 109.5 |
C3'—C4'—C5' | 117.1 (4) | H22A—C22—H22C | 109.5 |
C3'—C4'—H4' | 121.4 | H22B—C22—H22C | 109.5 |
C5'—C4'—H4' | 121.4 | C8—C9—C10 | 111.4 (5) |
N3—C7—C6 | 109.4 (3) | C8—C9—H9A | 109.3 |
N3—C7—H7A | 109.8 | C8—C9—H9B | 109.3 |
N3—C7—H7B | 109.8 | C10—C9—H9A | 109.3 |
C6—C7—H7A | 109.8 | C10—C9—H9B | 109.3 |
C6—C7—H7B | 109.8 | H9A—C9—H9B | 108.0 |
H7A—C7—H7B | 108.2 | C20—C21—H21A | 109.5 |
N3—C12—C11 | 110.6 (3) | C20—C21—H21B | 109.5 |
N3—C12—H12A | 109.5 | C20—C21—H21C | 109.5 |
N3—C12—H12B | 109.5 | H21A—C21—H21B | 109.5 |
C11—C12—H12A | 109.5 | H21A—C21—H21C | 109.5 |
C11—C12—H12B | 109.5 | H21B—C21—H21C | 109.5 |
C22—O1—C5A—O2 | −4.4 (6) | H13A—C13—C2—C3 | −97.5 |
C22—O1—C5A—C5 | 174.3 (4) | H13B—C13—C2—N1 | −160.9 |
C5A—O1—C22—H22A | −67.8 | H13B—C13—C2—C3 | 21.1 |
C5A—O1—C22—H22B | 172.2 | C4—C5—C5A—O2 | 178.7 (4) |
C5A—O1—C22—H22C | 52.2 | C4—C5—C5A—O1 | 0.2 (5) |
C20—O6—C19—O5 | 3.8 (6) | C6—C5—C5A—O2 | −3.4 (7) |
C20—O6—C19—C3 | −176.5 (3) | C6—C5—C5A—O1 | 178.1 (3) |
C19—O6—C20—C21 | 80.3 (5) | C1'—C2'—C3'—N2 | −179.3 (4) |
C19—O6—C20—H20A | −40.7 | C1'—C2'—C3'—C4' | 0.1 (6) |
C19—O6—C20—H20B | −158.8 | H2'—C2'—C3'—N2 | 0.7 |
C2—N1—C6—C5 | −17.6 (5) | H2'—C2'—C3'—C4' | −179.9 |
C2—N1—C6—C7 | 161.6 (3) | N2—C3'—C4'—C5' | 179.2 (4) |
H1—N1—C6—C5 | 162.4 | N2—C3'—C4'—H4' | −0.8 |
H1—N1—C6—C7 | −18.5 | C2'—C3'—C4'—C5' | −0.2 (6) |
C6—N1—C2—C3 | 18.1 (5) | C2'—C3'—C4'—H4' | 179.8 |
C6—N1—C2—C13 | −160.1 (3) | N4—C18—C17—C16 | 55.4 (5) |
H1—N1—C2—C3 | −161.9 | N4—C18—C17—H17A | 176.3 |
H1—N1—C2—C13 | 19.9 | N4—C18—C17—H17B | −65.5 |
O4—N2—C3'—C2' | 3.4 (6) | H18A—C18—C17—C16 | 176.5 |
O4—N2—C3'—C4' | −176.1 (4) | H18A—C18—C17—H17A | −62.6 |
O3—N2—C3'—C2' | −174.2 (4) | H18A—C18—C17—H17B | 55.6 |
O3—N2—C3'—C4' | 6.4 (6) | H18B—C18—C17—C16 | −65.7 |
C12—N3—C7—C6 | 81.7 (4) | H18B—C18—C17—H17A | 55.2 |
C12—N3—C7—H7A | −38.9 | H18B—C18—C17—H17B | 173.4 |
C12—N3—C7—H7B | −157.8 | C1'—C6'—C5'—C4' | −0.1 (7) |
C8—N3—C7—C6 | −154.5 (3) | C1'—C6'—C5'—H5' | 179.9 |
C8—N3—C7—H7A | 85.0 | H6'—C6'—C5'—C4' | 179.9 |
C8—N3—C7—H7B | −33.9 | H6'—C6'—C5'—H5' | −0.2 |
C7—N3—C12—C11 | −171.7 (3) | C3'—C4'—C5'—C6' | 0.2 (7) |
C7—N3—C12—H12A | 67.5 | C3'—C4'—C5'—H5' | −179.8 |
C7—N3—C12—H12B | −50.9 | H4'—C4'—C5'—C6' | −179.8 |
C8—N3—C12—C11 | 62.7 (4) | H4'—C4'—C5'—H5' | 0.2 |
C8—N3—C12—H12A | −58.1 | N3—C12—C11—C10 | −58.3 (5) |
C8—N3—C12—H12B | −176.4 | N3—C12—C11—H11A | 62.5 |
C7—N3—C8—C9 | 174.4 (4) | N3—C12—C11—H11B | −179.0 |
C7—N3—C8—H8A | 53.8 | H12A—C12—C11—C10 | 62.5 |
C7—N3—C8—H8B | −64.9 | H12A—C12—C11—H11A | −176.7 |
C12—N3—C8—C9 | −61.3 (5) | H12A—C12—C11—H11B | −58.2 |
C12—N3—C8—H8A | 178.1 | H12B—C12—C11—C10 | −179.1 |
C12—N3—C8—H8B | 59.3 | H12B—C12—C11—H11A | −58.4 |
C18—N4—C13—C2 | −76.9 (4) | H12B—C12—C11—H11B | 60.2 |
C18—N4—C13—H13A | 162.4 | C12—C11—C10—C9 | 52.9 (6) |
C18—N4—C13—H13B | 43.8 | C12—C11—C10—H10A | −67.9 |
C14—N4—C13—C2 | 160.3 (3) | C12—C11—C10—H10B | 173.7 |
C14—N4—C13—H13A | 39.6 | H11A—C11—C10—C9 | −67.8 |
C14—N4—C13—H13B | −79.0 | H11A—C11—C10—H10A | 171.4 |
C13—N4—C18—C17 | 177.0 (3) | H11A—C11—C10—H10B | 53.0 |
C13—N4—C18—H18A | 55.9 | H11B—C11—C10—C9 | 173.7 |
C13—N4—C18—H18B | −62.0 | H11B—C11—C10—H10A | 52.9 |
C14—N4—C18—C17 | −59.7 (4) | H11B—C11—C10—H10B | −65.6 |
C14—N4—C18—H18A | 179.2 | N4—C14—C15—C16 | −57.7 (5) |
C14—N4—C18—H18B | 61.4 | N4—C14—C15—H15A | 63.2 |
C13—N4—C14—C15 | −176.7 (3) | N4—C14—C15—H15B | −178.6 |
C13—N4—C14—H14A | 62.5 | H14A—C14—C15—C16 | 63.0 |
C13—N4—C14—H14B | −56.0 | H14A—C14—C15—H15A | −176.1 |
C18—N4—C14—C15 | 60.3 (4) | H14A—C14—C15—H15B | −57.8 |
C18—N4—C14—H14A | −60.4 | H14B—C14—C15—C16 | −178.4 |
C18—N4—C14—H14B | −178.9 | H14B—C14—C15—H15A | −57.6 |
C3—C4—C1'—C2' | −64.1 (4) | H14B—C14—C15—H15B | 60.7 |
C3—C4—C1'—C6' | 117.1 (4) | C15—C16—C17—C18 | −51.8 (5) |
C5—C4—C1'—C2' | 58.2 (4) | C15—C16—C17—H17A | −172.7 |
C5—C4—C1'—C6' | −120.5 (4) | C15—C16—C17—H17B | 69.1 |
H4—C4—C1'—C2' | 176.9 | H16A—C16—C17—C18 | −172.6 |
H4—C4—C1'—C6' | −1.8 | H16A—C16—C17—H17A | 66.5 |
C1'—C4—C3—C2 | 88.8 (4) | H16A—C16—C17—H17B | −51.7 |
C1'—C4—C3—C19 | −90.4 (4) | H16B—C16—C17—C18 | 69.0 |
C5—C4—C3—C2 | −34.5 (5) | H16B—C16—C17—H17A | −51.9 |
C5—C4—C3—C19 | 146.3 (3) | H16B—C16—C17—H17B | −170.1 |
H4—C4—C3—C2 | −152.2 | C17—C16—C15—C14 | 53.4 (6) |
H4—C4—C3—C19 | 28.5 | C17—C16—C15—H15A | −67.5 |
C1'—C4—C5—C6 | −88.7 (4) | C17—C16—C15—H15B | 174.3 |
C1'—C4—C5—C5A | 89.2 (4) | H16A—C16—C15—C14 | 174.2 |
C3—C4—C5—C6 | 34.8 (4) | H16A—C16—C15—H15A | 53.3 |
C3—C4—C5—C5A | −147.3 (3) | H16A—C16—C15—H15B | −64.9 |
H4—C4—C5—C6 | 152.6 | H16B—C16—C15—C14 | −67.4 |
H4—C4—C5—C5A | −29.5 | H16B—C16—C15—H15A | 171.7 |
N1—C6—C5—C4 | −11.2 (5) | H16B—C16—C15—H15B | 53.5 |
N1—C6—C5—C5A | 170.9 (3) | N3—C8—C9—C10 | 56.7 (6) |
C7—C6—C5—C4 | 169.8 (3) | N3—C8—C9—H9A | −64.3 |
C7—C6—C5—C5A | −8.1 (6) | N3—C8—C9—H9B | 177.7 |
N1—C6—C7—N3 | 26.4 (4) | H8A—C8—C9—C10 | 177.3 |
N1—C6—C7—H7A | 147.0 | H8A—C8—C9—H9A | 56.3 |
N1—C6—C7—H7B | −94.1 | H8A—C8—C9—H9B | −61.7 |
C5—C6—C7—N3 | −154.5 (4) | H8B—C8—C9—C10 | −63.9 |
C5—C6—C7—H7A | −34.0 | H8B—C8—C9—H9A | 175.1 |
C5—C6—C7—H7B | 84.9 | H8B—C8—C9—H9B | 57.0 |
C4—C1'—C2'—C3' | −178.8 (3) | O6—C20—C21—H21A | −61.9 |
C4—C1'—C2'—H2' | 1.2 | O6—C20—C21—H21B | 178.1 |
C6'—C1'—C2'—C3' | 0.0 (6) | O6—C20—C21—H21C | 58.1 |
C6'—C1'—C2'—H2' | 180.0 | H20A—C20—C21—H21A | 59.1 |
C4—C1'—C6'—C5' | 178.8 (4) | H20A—C20—C21—H21B | −60.9 |
C4—C1'—C6'—H6' | −1.2 | H20A—C20—C21—H21C | 179.1 |
C2'—C1'—C6'—C5' | 0.0 (6) | H20B—C20—C21—H21A | 177.2 |
C2'—C1'—C6'—H6' | −179.9 | H20B—C20—C21—H21B | 57.2 |
C4—C3—C2—N1 | 10.4 (5) | H20B—C20—C21—H21C | −62.8 |
C4—C3—C2—C13 | −171.7 (4) | C11—C10—C9—C8 | −52.8 (6) |
C19—C3—C2—N1 | −170.4 (3) | C11—C10—C9—H9A | 68.2 |
C19—C3—C2—C13 | 7.5 (6) | C11—C10—C9—H9B | −173.7 |
C4—C3—C19—O5 | 178.6 (4) | H10A—C10—C9—C8 | 68.0 |
C4—C3—C19—O6 | −1.1 (5) | H10A—C10—C9—H9A | −171.0 |
C2—C3—C19—O5 | −0.6 (7) | H10A—C10—C9—H9B | −53.0 |
C2—C3—C19—O6 | 179.7 (3) | H10B—C10—C9—C8 | −173.5 |
N4—C13—C2—N1 | −40.2 (4) | H10B—C10—C9—H9A | −52.6 |
N4—C13—C2—C3 | 141.8 (4) | H10B—C10—C9—H9B | 65.5 |
H13A—C13—C2—N1 | 80.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N3 | 0.86 | 2.20 | 2.629 (4) | 110 |
N1—H1···N4 | 0.86 | 2.30 | 2.695 (4) | 108 |