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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 [N...N 2.629 (4) and 2.695 (4) Å].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100010416/fr1242sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100010416/fr1242Isup2.hkl
Contains datablock I

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
C28H38N4O6F(000) = 1128.0
Mr = 526.62Dx = 1.256 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 8.9714 (6) ÅCell parameters from 38 reflections
b = 11.7112 (11) Åθ = 21.5–53.8°
c = 26.718 (2) ŵ = 0.73 mm1
β = 97.271 (5)°T = 296 K
V = 2784.6 (4) Å3Prismatic, light yellow
Z = 40.28 × 0.24 × 0.20 mm
Data collection top
Siemens P4 four-circle
diffractometer
2435 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.041
Graphite monochromatorθmax = 69.1°, θmin = 4.5°
2θ/ω scansh = 110
Absorption correction: ψ-scan
(North et al., 1968)
k = 114
Tmin = 0.725, Tmax = 0.864l = 3232
6839 measured reflections3 standard reflections every 100 reflections
4939 independent reflections intensity decay: <1.7%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054H-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 reflectionsΔρmax = 0.32 e Å3
346 parametersΔρmin = 0.28 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: none
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O40.9166 (5)0.4428 (3)0.2188 (2)0.1154 (19)
O31.0384 (4)0.3111 (3)0.2601 (2)0.1006 (17)
O20.7231 (4)0.2964 (3)0.0250 (1)0.0768 (13)
O50.1730 (3)0.3352 (3)0.1384 (1)0.0750 (13)
O10.6325 (4)0.1440 (3)0.0117 (1)0.0701 (13)
O60.2721 (3)0.1710 (2)0.1158 (1)0.0615 (11)
N10.5616 (3)0.4921 (3)0.0910 (1)0.0419 (10)
N20.9385 (5)0.3424 (4)0.2288 (2)0.0688 (16)
N30.7760 (4)0.6109 (3)0.0569 (1)0.0464 (12)
N40.4550 (4)0.6247 (3)0.1608 (1)0.0463 (12)
C40.5315 (4)0.2575 (3)0.0900 (1)0.0387 (12)
C60.6317 (4)0.4345 (3)0.0558 (1)0.0401 (13)
C1'0.6453 (4)0.2166 (3)0.1336 (1)0.0400 (13)
C30.4141 (4)0.3348 (3)0.1083 (1)0.0385 (12)
C130.3529 (4)0.5402 (3)0.1344 (2)0.0480 (14)
C50.6092 (4)0.3200 (3)0.0505 (1)0.0403 (12)
C20.4411 (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)
C190.2741 (5)0.2858 (4)0.1226 (2)0.0469 (14)
C180.5228 (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)
C70.7265 (5)0.5111 (4)0.0263 (2)0.0496 (14)
C120.9083 (5)0.5834 (4)0.0928 (2)0.0592 (16)
C5A0.6624 (5)0.2579 (4)0.0091 (2)0.0495 (15)
C5'0.7683 (5)0.0664 (4)0.1857 (2)0.0635 (18)
C110.9456 (6)0.6808 (4)0.1293 (2)0.076 (2)
C140.3773 (5)0.7318 (4)0.1679 (2)0.0599 (16)
C160.5644 (6)0.7770 (4)0.2426 (2)0.074 (2)
C170.6352 (5)0.6625 (4)0.2364 (2)0.0711 (19)
C80.8071 (6)0.7090 (4)0.0267 (2)0.0724 (19)
C150.4870 (6)0.8199 (4)0.1926 (2)0.076 (2)
C200.1367 (5)0.1139 (4)0.1257 (2)0.075 (2)
C100.9734 (7)0.7875 (5)0.1012 (2)0.086 (2)
C220.6684 (8)0.0755 (4)0.0309 (2)0.112 (3)
C90.8426 (7)0.8115 (4)0.0606 (3)0.097 (3)
C210.0183 (8)0.1248 (6)0.0830 (3)0.121 (3)
H10.594830.558550.100450.0545*
H40.480340.190420.073980.0504*
H13A0.286140.577630.108020.0625*
H13B0.292010.505980.157940.0625*
H2'0.731110.371470.153850.0601*
H18A0.572800.508380.204030.0792*
H18B0.444390.564670.230330.0792*
H6'0.601180.047150.128640.0729*
H4'0.932400.119670.239410.0719*
H7A0.813120.469130.017900.0645*
H7B0.667740.535330.004830.0645*
H12A0.993360.568560.074690.0769*
H12B0.888960.514980.111410.0769*
H5'0.776960.010830.193660.0826*
H11A0.862930.692850.148810.0987*
H11B1.034300.661840.152420.0987*
H14A0.298500.718800.189010.0779*
H14B0.331010.760130.135520.0779*
H16A0.641110.831110.256020.0960*
H16B0.491750.770850.266460.0960*
H17A0.672770.631920.269380.0924*
H17B0.719580.671130.217390.0924*
H8A0.720400.725280.002180.0942*
H8B0.891630.692490.008550.0942*
H15A0.561750.836710.170340.0992*
H15B0.433600.890050.197820.0992*
H20A0.102310.146640.155560.0972*
H20B0.157970.033750.132260.0972*
H10A1.065100.779320.085820.1123*
H10B0.986190.851190.124560.1123*
H22A0.601790.095660.060600.1452*
H22B0.656630.003960.023600.1452*
H22C0.770300.089940.036520.1452*
H9A0.754620.831620.076360.1259*
H9B0.867330.876020.040390.1259*
H21A0.006310.203920.077560.1567*
H21B0.069250.083900.090230.1567*
H21C0.052830.093560.053330.1567*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.127 (3)0.062 (3)0.134 (4)0.003 (2)0.072 (3)0.015 (2)
O30.092 (3)0.101 (3)0.093 (3)0.002 (2)0.049 (2)0.014 (2)
O20.111 (3)0.065 (2)0.062 (2)0.014 (2)0.042 (2)0.0048 (17)
O50.0502 (18)0.064 (2)0.116 (3)0.0087 (16)0.0343 (19)0.0229 (19)
O10.104 (3)0.0476 (19)0.066 (2)0.0000 (18)0.0393 (19)0.0091 (15)
O60.0507 (17)0.0490 (18)0.089 (2)0.0187 (14)0.0255 (16)0.0022 (16)
N10.0419 (17)0.0378 (18)0.0461 (18)0.0102 (15)0.0057 (15)0.0057 (15)
N20.070 (3)0.069 (3)0.060 (3)0.003 (2)0.021 (2)0.001 (2)
N30.0448 (18)0.0469 (19)0.0457 (19)0.0123 (16)0.0014 (16)0.0057 (16)
N40.057 (2)0.037 (2)0.0438 (18)0.0007 (16)0.0032 (16)0.0033 (15)
C40.038 (2)0.038 (2)0.039 (2)0.0082 (18)0.0023 (17)0.0034 (17)
C60.034 (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)
C30.037 (2)0.039 (2)0.038 (2)0.0052 (18)0.0041 (17)0.0010 (18)
C130.046 (2)0.045 (2)0.053 (2)0.001 (2)0.0038 (19)0.008 (2)
C50.037 (2)0.044 (2)0.040 (2)0.0039 (18)0.0044 (17)0.0006 (18)
C20.037 (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)
C190.042 (2)0.044 (2)0.055 (3)0.009 (2)0.007 (2)0.004 (2)
C180.067 (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)
C70.053 (2)0.053 (3)0.042 (2)0.012 (2)0.005 (2)0.005 (2)
C120.050 (2)0.066 (3)0.058 (3)0.011 (2)0.004 (2)0.004 (2)
C5A0.054 (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)
C110.074 (3)0.093 (4)0.059 (3)0.035 (3)0.005 (3)0.005 (3)
C140.074 (3)0.044 (3)0.062 (3)0.006 (3)0.007 (2)0.008 (2)
C160.076 (3)0.074 (4)0.072 (3)0.011 (3)0.008 (3)0.023 (3)
C170.065 (3)0.086 (4)0.059 (3)0.003 (3)0.006 (2)0.018 (3)
C80.082 (3)0.058 (3)0.073 (3)0.025 (3)0.010 (3)0.019 (3)
C150.095 (4)0.043 (3)0.091 (4)0.007 (3)0.009 (3)0.015 (3)
C200.069 (3)0.066 (3)0.101 (4)0.027 (3)0.020 (3)0.007 (3)
C100.093 (4)0.083 (4)0.083 (4)0.040 (3)0.009 (3)0.015 (3)
C220.185 (7)0.050 (3)0.122 (5)0.004 (4)0.103 (5)0.020 (3)
C90.116 (5)0.053 (3)0.118 (3)0.022 (3)0.002 (4)0.011 (3)
C210.101 (5)0.127 (6)0.138 (6)0.036 (4)0.034 (5)0.021 (5)
Geometric parameters (Å, º) top
O4—N21.216 (6)C4'—C5'1.372 (6)
O3—N21.203 (5)C4'—H4'0.930
O2—C5A1.207 (6)C7—H7A0.970
O5—C191.197 (5)C7—H7B0.970
O1—C5A1.364 (5)C12—C111.508 (7)
O1—C221.460 (7)C12—H12A0.970
O6—C191.356 (5)C12—H12B0.970
O6—C201.440 (6)C5'—H5'0.930
N1—C61.371 (5)C11—C101.494 (8)
N1—C21.372 (5)C11—H11A0.970
N1—H10.860C11—H11B0.970
N2—C3'1.469 (6)C14—C151.518 (7)
N3—C71.462 (5)C14—H14A0.970
N3—C121.466 (5)C14—H14B0.970
N3—C81.450 (6)C16—C171.502 (7)
N4—C131.467 (5)C16—C151.513 (7)
N4—C181.457 (5)C16—H16A0.970
N4—C141.459 (5)C16—H16B0.970
C4—C1'1.525 (5)C17—H17A0.970
C4—C31.516 (5)C17—H17B0.970
C4—C51.524 (5)C8—C91.513 (7)
C4—H40.980C8—H8A0.970
C6—C51.360 (5)C8—H8B0.970
C6—C71.522 (6)C15—H15A0.970
C1'—C2'1.387 (5)C15—H15B0.970
C1'—C6'1.398 (6)C20—C211.461 (8)
C3—C21.360 (5)C20—H20A0.970
C3—C191.475 (6)C20—H20B0.970
C13—C21.502 (6)C10—C91.521 (8)
C13—H13A0.970C10—H10A0.970
C13—H13B0.970C10—H10B0.970
C5—C5A1.454 (6)C22—H22A0.960
C2'—C3'1.378 (5)C22—H22B0.960
C2'—H2'0.930C22—H22C0.960
C3'—C4'1.377 (6)C9—H9A0.970
C18—C171.513 (6)C9—H9B0.970
C18—H18A0.970C21—H21A0.960
C18—H18B0.970C21—H21B0.960
C6'—C5'1.384 (6)C21—H21C0.960
C6'—H6'0.930
O4···O32.118 (6)C12···C82.388 (6)
O4···C2'2.703 (6)C12···C102.463 (7)
O4···C3'2.313 (6)C12···C92.846 (7)
O4···H2'2.397C12···H12.860
O4···H12B2.970C12···H7A2.470
O3···C3'2.307 (5)C12···H11A2.049
O3···C4'2.733 (6)C12···H11B2.049
O3···H4'2.470C12···H8B2.577
O2···O12.238 (5)C12···H10A2.710
O2···C62.899 (5)C5A···C222.392 (7)
O2···C52.391 (5)C5A···H42.649
O2···C72.862 (5)C5A···H7A2.815
O2···C222.634 (6)C5A···H22A2.668
O2···H7A2.413C5A···H22C2.567
O2···H7B2.904C5'···H6'2.012
O2···H22A2.712C5'···H4'2.019
O2···H22C2.481C11···C82.881 (7)
O5···O62.233 (4)C11···C92.477 (8)
O5···C32.401 (5)C11···H12A2.048
O5···C132.903 (5)C11···H12B2.048
O5···C22.916 (5)C11···H10A2.036
O5···C202.628 (6)C11···H10B2.036
O5···H13B2.296C11···H9A2.728
O5···H20A2.358C14···C162.497 (7)
O5···H21A2.633C14···C172.879 (6)
O1···C42.729 (5)C14···H13A2.482
O1···C52.329 (5)C14···H13B2.757
O1···H42.347C14···H18B2.592
O1···H22A1.997C14···H16B2.740
O1···H22B1.997C14···H15A2.056
O1···H22C1.997C14···H15B2.055
O6···C42.706 (5)C16···H18B2.713
O6···C32.325 (5)C16···H14A2.710
O6···C212.395 (7)C16···H17A2.042
O6···H42.306C16···H17B2.042
O6···H20A1.985C16···H15A2.051
O6···H20B1.985C16···H15B2.051
O6···H21A2.605C17···C152.479 (7)
O6···H21C2.578C17···H18A2.049
N1···N32.629 (5)C17···H18B2.049
N1···N42.695 (5)C17···H16A2.042
N1···C42.761 (5)C17···H16B2.042
N1···C32.349 (5)C17···H15A2.724
N1···C132.392 (5)C8···C102.507 (7)
N1···C52.351 (5)C8···H7A2.820
N1···C72.422 (5)C8···H7B2.478
N1···H13A2.757C8···H12A2.569
N1···H2'2.547C8···H10A2.758
N1···H7B2.886C8···H9A2.050
N1···H12B2.931C8···H9B2.050
N2···C2'2.441 (5)C15···H14A2.057
N2···C4'2.455 (6)C15···H14B2.057
N2···H2'2.578C15···H16A2.052
N2···H4'2.625C15···H16B2.052
N3···C62.437 (5)C15···H17B2.735
N3···C112.445 (6)C20···H21A1.998
N3···C102.878 (6)C20···H21B1.998
N3···C92.423 (6)C20···H21C1.998
N3···H12.203C10···H12A2.672
N3···H7A2.010C10···H11A2.036
N3···H7B2.010C10···H11B2.036
N3···H12A2.010C10···H8B2.729
N3···H12B2.010C10···H9A2.057
N3···H11A2.661C10···H9B2.057
N3···H8A1.998C9···H11A2.723
N3···H8B1.998C9···H8A2.055
N3···H9A2.648C9···H8B2.055
N4···C22.435 (5)C9···H10A2.059
N4···C162.894 (6)C9···H10B2.059
N4···C172.462 (5)C21···H20A2.004
N4···C152.443 (6)C21···H20B2.004
N4···H12.300H1···H13A2.811
N4···H13A2.013H1···H2'2.809
N4···H13B2.013H1···H18A2.860
N4···H18A1.999H1···H7B2.980
N4···H18B1.999H1···H12B2.667
N4···H14A2.005H4···H6'2.392
N4···H14B2.005H13A···H13B1.571
N4···H17B2.703H13A···H14A2.714
N4···H15A2.661H13A···H14B2.279
C4···C62.479 (5)H13B···H18A2.660
C4···C22.479 (5)H13B···H18B2.327
C4···C2'2.527 (5)H13B···H14A2.625
C4···C192.591 (6)H2'···H18A2.621
C4···C6'2.561 (6)H2'···H12B2.554
C4···C5A2.587 (6)H18A···H18B1.569
C4···H2'2.670H18A···H17A2.356
C4···H6'2.713H18A···H17B2.319
C6···C32.799 (5)H18B···H14A2.413
C6···C22.415 (6)H18B···H16B2.615
C6···C5A2.450 (6)H18B···H17A2.316
C6···H11.934H18B···H17B2.826
C6···H2'2.758H6'···H5'2.296
C6···H7A2.064H4'···H5'2.312
C6···H7B2.064H7A···H7B1.572
C6···H12B2.748H7A···H12A2.377
C1'···C32.514 (5)H7A···H12B2.562
C1'···C52.513 (5)H7A···H8B2.729
C1'···C3'2.397 (5)H7B···H8A2.277
C1'···C4'2.822 (6)H7B···H8B2.714
C1'···C5'2.422 (6)H12A···H12B1.570
C1'···H42.054H12A···H11A2.828
C1'···H2'2.018H12A···H11B2.334
C1'···H6'2.024H12A···H8B2.378
C3···C132.584 (5)H12A···H10A2.559
C3···C52.482 (6)H12B···H11A2.335
C3···H42.047H12B···H11B2.345
C3···H13B2.710H11A···H11B1.571
C3···H2'2.980H11A···H17B2.382
C13···C182.403 (6)H11A···H10A2.814
C13···C142.415 (6)H11A···H10B2.294
C13···H12.466H11A···H9A2.618
C13···H18A2.562H11B···H10A2.293
C13···H18B2.606H11B···H10B2.361
C13···H14A2.630H14A···H14B1.571
C13···H14B2.583H14A···H16B2.598
C5···C22.803 (6)H14A···H15A2.834
C5···C72.589 (6)H14A···H15B2.340
C5···H42.054H14B···H15A2.338
C5···H2'2.902H14B···H15B2.355
C5···H7A2.749H16A···H16B1.570
C2···C192.469 (6)H16A···H17A2.372
C2···H11.935H16A···H17B2.292
C2···H13A2.043H16A···H15A2.311
C2···H13B2.043H16A···H15B2.372
C2···H2'2.850H16B···H17A2.293
C2···H18A2.688H16B···H17B2.818
C2'···C6'2.378 (6)H16B···H15A2.827
C2'···C4'2.418 (6)H16B···H15B2.311
C2'···C5'2.749 (6)H17A···H17B1.570
C3'···C6'2.723 (6)H17B···H15A2.626
C3'···C5'2.345 (6)H8A···H8B1.572
C3'···H2'2.010H8A···H9A2.328
C3'···H4'2.024H8A···H9B2.357
C19···C202.366 (7)H8B···H10A2.628
C19···H42.639H8B···H9A2.830
C19···H13B2.744H8B···H9B2.332
C19···H20A2.480H15A···H15B1.570
C19···H21A2.816H20A···H20B1.569
C18···C142.393 (6)H20A···H21A2.287
C18···C162.484 (7)H20A···H21B2.297
C18···C152.857 (7)H20A···H21C2.782
C18···H13B2.491H20B···H21A2.781
C18···H14A2.590H20B···H21B2.276
C18···H16B2.741H20B···H21C2.307
C18···H17A2.051H10A···H10B1.571
C18···H17B2.051H10A···H9A2.832
C6'···C4'2.405 (6)H10A···H9B2.315
C6'···H42.591H10B···H9A2.313
C6'···H5'2.010H10B···H9B2.382
C4'···H5'1.998H22A···H22B1.568
C7···C122.409 (6)H22A···H22C1.568
C7···C82.427 (6)H22B···H22C1.568
C7···H12.493H9A···H9B1.569
C7···H12A2.659H21A···H21B1.568
C7···H12B2.541H21A···H21C1.568
C7···H8A2.589H21B···H21C1.568
C7···H8B2.667
C5A—O1—C22115.7 (3)H12A—C12—H12B108.1
C19—O6—C20115.6 (3)O2—C5A—O1120.9 (4)
C6—N1—C2123.3 (3)O2—C5A—C5127.6 (4)
C6—N1—H1118.4O1—C5A—C5111.4 (3)
C2—N1—H1118.4C6'—C5'—C4'121.5 (4)
O4—N2—O3122.2 (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—C10110.2 (4)
C7—N3—C12110.7 (3)C12—C11—H11A109.6
C7—N3—C8112.9 (3)C12—C11—H11B109.6
C12—N3—C8110.0 (3)C10—C11—H11A109.6
C13—N4—C18110.5 (3)C10—C11—H11B109.6
C13—N4—C14111.2 (3)H11A—C11—H11B108.1
C18—N4—C14110.2 (3)N4—C14—C15110.3 (3)
C1'—C4—C3111.5 (3)N4—C14—H14A109.6
C1'—C4—C5111.1 (3)N4—C14—H14B109.6
C1'—C4—H4108.2C15—C14—H14A109.6
C3—C4—C5109.5 (3)C15—C14—H14B109.6
C3—C4—H4108.2H14A—C14—H14B108.1
C5—C4—H4108.2C17—C16—C15110.7 (4)
N1—C6—C5118.8 (3)C17—C16—H16A109.5
N1—C6—C7113.5 (3)C17—C16—H16B109.5
C5—C6—C7127.7 (3)C15—C16—H16A109.5
C4—C1'—C2'120.4 (3)C15—C16—H16B109.5
C4—C1'—C6'122.3 (3)H16A—C16—H16B108.1
C2'—C1'—C6'117.3 (3)C18—C17—C16110.9 (4)
C4—C3—C2118.9 (3)C18—C17—H17A109.4
C4—C3—C19120.0 (3)C18—C17—H17B109.5
C2—C3—C19121.0 (3)C16—C17—H17A109.4
N4—C13—C2110.2 (3)C16—C17—H17B109.5
N4—C13—H13A109.6H17A—C17—H17B108.0
N4—C13—H13B109.6N3—C8—C9109.7 (4)
C2—C13—H13A109.6N3—C8—H8A109.7
C2—C13—H13B109.6N3—C8—H8B109.7
H13A—C13—H13B108.1C9—C8—H8A109.7
C4—C5—C6118.4 (3)C9—C8—H8B109.7
C4—C5—C5A120.6 (3)H8A—C8—H8B108.2
C6—C5—C5A120.9 (3)C14—C15—C16110.9 (4)
N1—C2—C3118.5 (3)C14—C15—H15A109.4
N1—C2—C13112.6 (3)C14—C15—H15B109.4
C3—C2—C13128.9 (3)C16—C15—H15A109.5
C1'—C2'—C3'120.2 (4)C16—C15—H15B109.5
C1'—C2'—H2'119.9H15A—C15—H15B108.0
C3'—C2'—H2'119.9O6—C20—C21111.3 (4)
N2—C3'—C2'118.0 (4)O6—C20—H20A109.4
N2—C3'—C4'119.2 (4)O6—C20—H20B109.4
C2'—C3'—C4'122.8 (4)C21—C20—H20A109.4
O5—C19—O6121.9 (4)C21—C20—H20B109.4
O5—C19—C3127.7 (4)H20A—C20—H20B108.0
O6—C19—C3110.4 (3)C11—C10—C9110.5 (4)
N4—C18—C17111.9 (4)C11—C10—H10A109.6
N4—C18—H18A109.2C11—C10—H10B109.5
N4—C18—H18B109.2C9—C10—H10A109.6
C17—C18—H18A109.2C9—C10—H10B109.6
C17—C18—H18B109.2H10A—C10—H10B108.1
H18A—C18—H18B107.9O1—C22—H22A109.5
C1'—C6'—C5'121.1 (4)O1—C22—H22B109.5
C1'—C6'—H6'119.5O1—C22—H22C109.5
C5'—C6'—H6'119.5H22A—C22—H22B109.5
C3'—C4'—C5'117.1 (4)H22A—C22—H22C109.5
C3'—C4'—H4'121.4H22B—C22—H22C109.5
C5'—C4'—H4'121.4C8—C9—C10111.4 (5)
N3—C7—C6109.4 (3)C8—C9—H9A109.3
N3—C7—H7A109.8C8—C9—H9B109.3
N3—C7—H7B109.8C10—C9—H9A109.3
C6—C7—H7A109.8C10—C9—H9B109.3
C6—C7—H7B109.8H9A—C9—H9B108.0
H7A—C7—H7B108.2C20—C21—H21A109.5
N3—C12—C11110.6 (3)C20—C21—H21B109.5
N3—C12—H12A109.5C20—C21—H21C109.5
N3—C12—H12B109.5H21A—C21—H21B109.5
C11—C12—H12A109.5H21A—C21—H21C109.5
C11—C12—H12B109.5H21B—C21—H21C109.5
C22—O1—C5A—O24.4 (6)H13A—C13—C2—C397.5
C22—O1—C5A—C5174.3 (4)H13B—C13—C2—N1160.9
C5A—O1—C22—H22A67.8H13B—C13—C2—C321.1
C5A—O1—C22—H22B172.2C4—C5—C5A—O2178.7 (4)
C5A—O1—C22—H22C52.2C4—C5—C5A—O10.2 (5)
C20—O6—C19—O53.8 (6)C6—C5—C5A—O23.4 (7)
C20—O6—C19—C3176.5 (3)C6—C5—C5A—O1178.1 (3)
C19—O6—C20—C2180.3 (5)C1'—C2'—C3'—N2179.3 (4)
C19—O6—C20—H20A40.7C1'—C2'—C3'—C4'0.1 (6)
C19—O6—C20—H20B158.8H2'—C2'—C3'—N20.7
C2—N1—C6—C517.6 (5)H2'—C2'—C3'—C4'179.9
C2—N1—C6—C7161.6 (3)N2—C3'—C4'—C5'179.2 (4)
H1—N1—C6—C5162.4N2—C3'—C4'—H4'0.8
H1—N1—C6—C718.5C2'—C3'—C4'—C5'0.2 (6)
C6—N1—C2—C318.1 (5)C2'—C3'—C4'—H4'179.8
C6—N1—C2—C13160.1 (3)N4—C18—C17—C1655.4 (5)
H1—N1—C2—C3161.9N4—C18—C17—H17A176.3
H1—N1—C2—C1319.9N4—C18—C17—H17B65.5
O4—N2—C3'—C2'3.4 (6)H18A—C18—C17—C16176.5
O4—N2—C3'—C4'176.1 (4)H18A—C18—C17—H17A62.6
O3—N2—C3'—C2'174.2 (4)H18A—C18—C17—H17B55.6
O3—N2—C3'—C4'6.4 (6)H18B—C18—C17—C1665.7
C12—N3—C7—C681.7 (4)H18B—C18—C17—H17A55.2
C12—N3—C7—H7A38.9H18B—C18—C17—H17B173.4
C12—N3—C7—H7B157.8C1'—C6'—C5'—C4'0.1 (7)
C8—N3—C7—C6154.5 (3)C1'—C6'—C5'—H5'179.9
C8—N3—C7—H7A85.0H6'—C6'—C5'—C4'179.9
C8—N3—C7—H7B33.9H6'—C6'—C5'—H5'0.2
C7—N3—C12—C11171.7 (3)C3'—C4'—C5'—C6'0.2 (7)
C7—N3—C12—H12A67.5C3'—C4'—C5'—H5'179.8
C7—N3—C12—H12B50.9H4'—C4'—C5'—C6'179.8
C8—N3—C12—C1162.7 (4)H4'—C4'—C5'—H5'0.2
C8—N3—C12—H12A58.1N3—C12—C11—C1058.3 (5)
C8—N3—C12—H12B176.4N3—C12—C11—H11A62.5
C7—N3—C8—C9174.4 (4)N3—C12—C11—H11B179.0
C7—N3—C8—H8A53.8H12A—C12—C11—C1062.5
C7—N3—C8—H8B64.9H12A—C12—C11—H11A176.7
C12—N3—C8—C961.3 (5)H12A—C12—C11—H11B58.2
C12—N3—C8—H8A178.1H12B—C12—C11—C10179.1
C12—N3—C8—H8B59.3H12B—C12—C11—H11A58.4
C18—N4—C13—C276.9 (4)H12B—C12—C11—H11B60.2
C18—N4—C13—H13A162.4C12—C11—C10—C952.9 (6)
C18—N4—C13—H13B43.8C12—C11—C10—H10A67.9
C14—N4—C13—C2160.3 (3)C12—C11—C10—H10B173.7
C14—N4—C13—H13A39.6H11A—C11—C10—C967.8
C14—N4—C13—H13B79.0H11A—C11—C10—H10A171.4
C13—N4—C18—C17177.0 (3)H11A—C11—C10—H10B53.0
C13—N4—C18—H18A55.9H11B—C11—C10—C9173.7
C13—N4—C18—H18B62.0H11B—C11—C10—H10A52.9
C14—N4—C18—C1759.7 (4)H11B—C11—C10—H10B65.6
C14—N4—C18—H18A179.2N4—C14—C15—C1657.7 (5)
C14—N4—C18—H18B61.4N4—C14—C15—H15A63.2
C13—N4—C14—C15176.7 (3)N4—C14—C15—H15B178.6
C13—N4—C14—H14A62.5H14A—C14—C15—C1663.0
C13—N4—C14—H14B56.0H14A—C14—C15—H15A176.1
C18—N4—C14—C1560.3 (4)H14A—C14—C15—H15B57.8
C18—N4—C14—H14A60.4H14B—C14—C15—C16178.4
C18—N4—C14—H14B178.9H14B—C14—C15—H15A57.6
C3—C4—C1'—C2'64.1 (4)H14B—C14—C15—H15B60.7
C3—C4—C1'—C6'117.1 (4)C15—C16—C17—C1851.8 (5)
C5—C4—C1'—C2'58.2 (4)C15—C16—C17—H17A172.7
C5—C4—C1'—C6'120.5 (4)C15—C16—C17—H17B69.1
H4—C4—C1'—C2'176.9H16A—C16—C17—C18172.6
H4—C4—C1'—C6'1.8H16A—C16—C17—H17A66.5
C1'—C4—C3—C288.8 (4)H16A—C16—C17—H17B51.7
C1'—C4—C3—C1990.4 (4)H16B—C16—C17—C1869.0
C5—C4—C3—C234.5 (5)H16B—C16—C17—H17A51.9
C5—C4—C3—C19146.3 (3)H16B—C16—C17—H17B170.1
H4—C4—C3—C2152.2C17—C16—C15—C1453.4 (6)
H4—C4—C3—C1928.5C17—C16—C15—H15A67.5
C1'—C4—C5—C688.7 (4)C17—C16—C15—H15B174.3
C1'—C4—C5—C5A89.2 (4)H16A—C16—C15—C14174.2
C3—C4—C5—C634.8 (4)H16A—C16—C15—H15A53.3
C3—C4—C5—C5A147.3 (3)H16A—C16—C15—H15B64.9
H4—C4—C5—C6152.6H16B—C16—C15—C1467.4
H4—C4—C5—C5A29.5H16B—C16—C15—H15A171.7
N1—C6—C5—C411.2 (5)H16B—C16—C15—H15B53.5
N1—C6—C5—C5A170.9 (3)N3—C8—C9—C1056.7 (6)
C7—C6—C5—C4169.8 (3)N3—C8—C9—H9A64.3
C7—C6—C5—C5A8.1 (6)N3—C8—C9—H9B177.7
N1—C6—C7—N326.4 (4)H8A—C8—C9—C10177.3
N1—C6—C7—H7A147.0H8A—C8—C9—H9A56.3
N1—C6—C7—H7B94.1H8A—C8—C9—H9B61.7
C5—C6—C7—N3154.5 (4)H8B—C8—C9—C1063.9
C5—C6—C7—H7A34.0H8B—C8—C9—H9A175.1
C5—C6—C7—H7B84.9H8B—C8—C9—H9B57.0
C4—C1'—C2'—C3'178.8 (3)O6—C20—C21—H21A61.9
C4—C1'—C2'—H2'1.2O6—C20—C21—H21B178.1
C6'—C1'—C2'—C3'0.0 (6)O6—C20—C21—H21C58.1
C6'—C1'—C2'—H2'180.0H20A—C20—C21—H21A59.1
C4—C1'—C6'—C5'178.8 (4)H20A—C20—C21—H21B60.9
C4—C1'—C6'—H6'1.2H20A—C20—C21—H21C179.1
C2'—C1'—C6'—C5'0.0 (6)H20B—C20—C21—H21A177.2
C2'—C1'—C6'—H6'179.9H20B—C20—C21—H21B57.2
C4—C3—C2—N110.4 (5)H20B—C20—C21—H21C62.8
C4—C3—C2—C13171.7 (4)C11—C10—C9—C852.8 (6)
C19—C3—C2—N1170.4 (3)C11—C10—C9—H9A68.2
C19—C3—C2—C137.5 (6)C11—C10—C9—H9B173.7
C4—C3—C19—O5178.6 (4)H10A—C10—C9—C868.0
C4—C3—C19—O61.1 (5)H10A—C10—C9—H9A171.0
C2—C3—C19—O50.6 (7)H10A—C10—C9—H9B53.0
C2—C3—C19—O6179.7 (3)H10B—C10—C9—C8173.5
N4—C13—C2—N140.2 (4)H10B—C10—C9—H9A52.6
N4—C13—C2—C3141.8 (4)H10B—C10—C9—H9B65.5
H13A—C13—C2—N180.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N30.862.202.629 (4)110
N1—H1···N40.862.302.695 (4)108
 

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