Ethyl methyl 1,4-dihydro-4-(3-nitrophenyl)-2,6-bis(1-piperidylmethyl)­pyridine-3,5-dicarboxylate

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].

Computing details

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

Crystal data

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) Å^3	Prismatic, light yellow
Z = 4	0.28 × 0.24 × 0.20 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.054	H-atom parameters constrained
wR(F^2) = 0.270	w = 1/[σ^2(Fo^2) + (0.1088P)^2 + 2.85P] where P = [max(Fo^2,0) + 2Fc^2]/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+0.001xFc^2λ^3/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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