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There are two mol­ecules, A and B, in the asymmetric unit of the title compound, C34H34N6O12. In both mol­ecules, the eight-membered ring has a conformation which is close to a boat-boat conformation and the cyclo­hexene ring is characterized by a sofa conformation. The nitro groups in each mol­ecule are situated in equatorial positions. Both nitro groups of mol­ecule A are considerably rotated with respect to the flattened fragment of the cyclo­hexene ring. The same is true for one of the nitro groups of mol­ecule B, whereas the other such group in mol­ecule B is almost coplanar with the corresponding fragment.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680202041X/ob6188sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680202041X/ob6188Isup2.hkl
Contains datablock I

CCDC reference: 202327

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.061
  • wR factor = 0.169
  • Data-to-parameter ratio = 12.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

The conformational properties of substituted bicyclo[3.3.1]nonanes and hetero-analogs have been extensively studied by different experimental and computational methods because of the relationship of these compounds to numerous natural compounds possessing biological activity (Jeyaraman & Avila, 1981; Zefirov & Palyulin, 1991). The critical influence of the stereochemical and conformational characteristics on the activity is well known. In order to gather more information about this conformationally restricted bicyclic system, the crystal structure of the title compound, (I), was studied by X-ray methods.

There are two molecules, A and B, in the asymmetric unit of (I). The piperidine ring adopts a chair conformation. Atoms N3 and C9 deviate from the plane of the remaining atoms of this ring by 0.689 (3) and −0.794 (3) Å, and by −0.688 (3) and 0.781 (3) Å in molecules A and B, respectively. The cyclohexene ring (C1/C8/C7/C6/C5/C9) has a sofa conformation, with atom C9 deviating by −0.783 (3)and −0.776 (3) Å from the mean plane of the remaining atoms in molecules A and B, respectively. The conformation of the eight-membered ring is close to a boat–boat conformation and can be characterized by Zefirov–Palyulin's puckering parameters (Zefirov et al., 1990) as follows (values are quoted for molecules A and B, respectively): S2 = 1.208 and 1.207, S3 = 0.580 and 0.580, S4 = 0.514 and −0.509, ϕ2 = 176.72 and 357.55, and ϕ3 = 181.65 and 2.07. The nitro groups in both molecules are in equatorial positions (Table 1). Moreover, the nitro groups of molecule A and the group at atom C5B of molecule B are considerably rotated with respect to the flattened fragment of the cyclohexene ring (Table 1). In contrast, the other nitro group in the molecule B is almost coplanar with the mentioned fragment. Overall, the most important distinction between molecules A and B is the different orientations of the nitro groups. Atom N3 is displaced from the plane of its three neighboring C atoms by 0.439 (3) and −0.432 (2) Å in molecules A and B, respectively, reflecting the trigonal–pyramidal configuration of this fragment. The phenacyl group is an axial position in the cyclohexene ring, whereas it has an equatorial orientation with respect to the piperidine ring (the relevant torsion angles are listed in Table 1).

Experimental top

Compound (I) was obtained according to the procedure of Leonova et al. (2001). Crystals of (I) were grown by slow evaporation of a toluene solution.

Refinement top

Zefirov–Palyulin's puckering parameters were calculated with RICON (Zotov et al., 1997). All H atoms were located from difference Fourier syntheses. Methyl H atoms were refined as part of rigid groups, which was allowed to rotate but not tip or distort, and with Uiso(H) = 1.5Ueq(C). Other H atoms were refined using a riding model, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: P3 (Siemens, 1989); cell refinement: P3 (Siemens, 1989); data reduction: XDISK (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A view of molecule A of (I). The non-H atoms are shown with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. A view of molecule B of (I). The non-H atoms are shown with displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarity.
3-Methyl-1,5-dinitro-9-phenacyl-3-azabicyclo[3.3.1]non-7-en-6-one top
Crystal data top
C17H17N3O6Z = 4
Mr = 359.34F(000) = 752
Triclinic, P1Dx = 1.402 Mg m3
a = 11.374 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.669 (5) ÅCell parameters from 24 reflections
c = 13.715 (6) Åθ = 10–11°
α = 84.56 (4)°µ = 0.11 mm1
β = 75.64 (4)°T = 293 K
γ = 75.07 (4)°Square prism, yellow
V = 1702.9 (14) Å30.50 × 0.30 × 0.30 mm
Data collection top
Siemens P3
diffractometer
Rint = 0.038
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 1.9°
Graphite monochromatorh = 013
ω scansk = 1313
6198 measured reflectionsl = 1516
5875 independent reflections2 standard reflections every 98 reflections
4198 reflections with I > 2σ(I) intensity decay: 3.4%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: difference Fourier map
wR(F2) = 0.169H-atom parameters constrained
S = 0.95 w = 1/[σ2(Fo2) + (0.1289P)2]
where P = (Fo2 + 2Fc2)/3
5875 reflections(Δ/σ)max = 0.001
469 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C17H17N3O6γ = 75.07 (4)°
Mr = 359.34V = 1702.9 (14) Å3
Triclinic, P1Z = 4
a = 11.374 (6) ÅMo Kα radiation
b = 11.669 (5) ŵ = 0.11 mm1
c = 13.715 (6) ÅT = 293 K
α = 84.56 (4)°0.50 × 0.30 × 0.30 mm
β = 75.64 (4)°
Data collection top
Siemens P3
diffractometer
Rint = 0.038
6198 measured reflections2 standard reflections every 98 reflections
5875 independent reflections intensity decay: 3.4%
4198 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.169H-atom parameters constrained
S = 0.95Δρmax = 0.30 e Å3
5875 reflectionsΔρmin = 0.27 e Å3
469 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
xyzUiso*/Ueq
N1A1.18163 (17)0.70037 (17)0.06086 (13)0.0534 (5)
N2A0.77553 (17)0.96661 (16)0.22244 (15)0.0563 (5)
N3A0.85363 (18)0.70890 (15)0.05651 (14)0.0548 (5)
O1A1.25348 (18)0.60621 (18)0.06737 (16)0.0864 (6)
O2A1.21318 (16)0.78658 (16)0.01460 (14)0.0698 (5)
O3A0.71615 (18)1.03869 (15)0.17316 (15)0.0781 (6)
O4A0.78503 (18)0.98328 (17)0.30666 (14)0.0806 (6)
O5A0.71335 (17)0.76351 (19)0.31564 (16)0.0866 (6)
O6A1.0094 (2)1.07040 (14)0.15322 (15)0.0824 (6)
C1A1.04280 (18)0.71456 (16)0.10841 (14)0.0435 (5)
C2A0.9873 (2)0.69200 (19)0.02134 (17)0.0535 (5)
H2AA1.00580.74650.03500.064*
H2AB1.02470.61170.00140.064*
C4A0.7943 (2)0.82986 (18)0.08911 (17)0.0521 (5)
H4AA0.70420.84160.10890.063*
H4AB0.81430.88640.03490.063*
C5A0.84501 (19)0.84670 (16)0.17842 (15)0.0445 (5)
C6A0.8174 (2)0.7511 (2)0.26045 (17)0.0546 (5)
C7A0.9180 (2)0.64498 (19)0.26346 (17)0.0544 (5)
H7AA0.90750.58900.31580.065*
C8A1.0243 (2)0.62643 (17)0.19309 (16)0.0477 (5)
H8AA1.08730.55830.19680.057*
C9A0.98580 (18)0.84213 (16)0.14396 (14)0.0402 (4)
H9AA0.99830.89650.08540.048*
C10A0.7994 (3)0.6772 (2)0.0197 (2)0.0809 (9)
H10A0.84020.59710.03930.121*
H10B0.81050.73010.07740.121*
H10C0.71170.68340.00730.121*
C11A1.04558 (19)0.87405 (17)0.22265 (15)0.0444 (5)
H11A1.00390.84920.28890.053*
H11B1.13270.83070.21000.053*
C12A1.0383 (2)1.00546 (19)0.22223 (17)0.0524 (5)
C13A1.0678 (2)1.0517 (2)0.30912 (18)0.0558 (6)
C14A1.0366 (3)1.1733 (2)0.3208 (2)0.0805 (8)
H14A0.99931.22440.27490.097*
C15A1.0617 (4)1.2184 (3)0.4019 (3)0.1073 (13)
H15A1.03871.29980.41130.129*
C16A1.1202 (3)1.1430 (4)0.4680 (3)0.0949 (11)
H16A1.13761.17380.52150.114*
C17A1.1529 (3)1.0246 (3)0.4561 (2)0.0811 (8)
H17A1.19320.97440.50090.097*
C18A1.1262 (2)0.9773 (2)0.37659 (18)0.0621 (6)
H18A1.14780.89560.36910.075*
N1B0.7221 (2)0.40555 (18)0.2665 (2)0.0720 (6)
N2B0.2580 (2)0.54668 (18)0.37025 (19)0.0677 (6)
N3B0.47394 (16)0.24604 (13)0.38160 (12)0.0460 (4)
O1B0.7967 (2)0.3901 (3)0.1868 (2)0.1262 (10)
O2B0.7429 (2)0.4435 (2)0.3386 (2)0.1098 (8)
O3B0.1942 (3)0.5432 (3)0.4536 (2)0.1378 (12)
O4B0.23782 (18)0.62839 (15)0.31084 (18)0.0817 (6)
O5B0.2519 (2)0.39300 (15)0.23680 (17)0.0842 (6)
O6B0.42995 (18)0.71600 (12)0.38920 (11)0.0624 (4)
C1B0.5958 (2)0.37680 (17)0.28111 (16)0.0481 (5)
C2B0.5938 (2)0.27512 (17)0.36162 (16)0.0494 (5)
H2BA0.66020.20610.33770.059*
H2BB0.60700.29960.42290.059*
C4B0.3724 (2)0.34702 (17)0.42057 (16)0.0502 (5)
H4BA0.38500.37410.48110.060*
H4BB0.29300.32480.43700.060*
C5B0.3722 (2)0.44563 (16)0.33838 (15)0.0462 (5)
C6B0.3552 (3)0.39547 (18)0.24300 (18)0.0583 (6)
C7B0.4684 (3)0.3486 (2)0.16948 (18)0.0689 (7)
H7BA0.46190.32410.10880.083*
C8B0.5807 (3)0.33867 (19)0.18421 (17)0.0647 (7)
H8BA0.65110.30790.13430.078*
C9B0.4931 (2)0.48808 (16)0.31869 (14)0.0435 (5)
H9BA0.50360.50780.38340.052*
C10B0.4716 (2)0.14129 (18)0.44766 (18)0.0586 (6)
H10D0.53990.07700.41950.088*
H10E0.39400.11960.45450.088*
H10F0.47940.15800.51270.088*
C11B0.5015 (2)0.59467 (17)0.24648 (16)0.0548 (6)
H11C0.58830.58800.21180.066*
H11D0.45500.59360.19620.066*
C12B0.45111 (19)0.71214 (16)0.29848 (15)0.0443 (5)
C13B0.43256 (18)0.82283 (16)0.23475 (15)0.0437 (5)
C14B0.4355 (2)0.92789 (17)0.27364 (18)0.0533 (5)
H14B0.45150.92640.33710.064*
C15B0.4152 (2)1.03251 (19)0.2203 (2)0.0624 (6)
H15B0.41921.10170.24650.075*
C16B0.3888 (3)1.0358 (2)0.1274 (2)0.0703 (7)
H16B0.37381.10760.09130.084*
C17B0.3846 (3)0.9333 (2)0.0872 (2)0.0692 (7)
H17B0.36600.93610.02450.083*
C18B0.4077 (2)0.82704 (19)0.13995 (17)0.0526 (5)
H18B0.40680.75770.11220.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0509 (11)0.0610 (11)0.0442 (10)0.0076 (9)0.0039 (8)0.0173 (8)
N2A0.0481 (11)0.0511 (10)0.0637 (12)0.0008 (8)0.0081 (9)0.0172 (9)
N3A0.0610 (12)0.0476 (10)0.0643 (12)0.0091 (8)0.0304 (10)0.0131 (8)
O1A0.0578 (11)0.0803 (13)0.0944 (14)0.0144 (10)0.0007 (10)0.0046 (10)
O2A0.0630 (11)0.0753 (11)0.0651 (11)0.0241 (9)0.0085 (8)0.0144 (9)
O3A0.0777 (13)0.0526 (10)0.0955 (14)0.0104 (9)0.0280 (11)0.0126 (9)
O4A0.0776 (12)0.0870 (12)0.0674 (12)0.0070 (10)0.0133 (10)0.0404 (10)
O5A0.0533 (11)0.1036 (14)0.0840 (14)0.0141 (10)0.0069 (10)0.0143 (11)
O6A0.1327 (17)0.0490 (9)0.0842 (13)0.0350 (10)0.0497 (12)0.0072 (8)
C1A0.0437 (11)0.0433 (10)0.0422 (10)0.0071 (8)0.0080 (8)0.0097 (8)
C2A0.0678 (15)0.0461 (11)0.0480 (12)0.0058 (10)0.0194 (10)0.0150 (9)
C4A0.0519 (13)0.0509 (11)0.0559 (13)0.0076 (9)0.0203 (10)0.0064 (9)
C5A0.0441 (11)0.0422 (10)0.0468 (11)0.0063 (8)0.0110 (9)0.0096 (8)
C6A0.0465 (13)0.0662 (14)0.0514 (12)0.0184 (10)0.0070 (10)0.0024 (10)
C7A0.0598 (14)0.0523 (12)0.0554 (13)0.0207 (10)0.0180 (11)0.0099 (9)
C8A0.0499 (12)0.0392 (10)0.0564 (12)0.0081 (9)0.0181 (10)0.0059 (8)
C9A0.0437 (11)0.0384 (9)0.0389 (10)0.0100 (8)0.0088 (8)0.0055 (7)
C10A0.091 (2)0.0697 (16)0.100 (2)0.0100 (14)0.0567 (18)0.0256 (14)
C11A0.0465 (11)0.0456 (10)0.0427 (11)0.0122 (8)0.0095 (9)0.0091 (8)
C12A0.0549 (13)0.0478 (11)0.0577 (13)0.0173 (9)0.0112 (10)0.0086 (10)
C13A0.0515 (13)0.0618 (13)0.0578 (13)0.0263 (10)0.0007 (10)0.0171 (10)
C14A0.093 (2)0.0708 (16)0.086 (2)0.0361 (14)0.0096 (16)0.0276 (14)
C15A0.124 (3)0.097 (2)0.111 (3)0.062 (2)0.013 (2)0.058 (2)
C16A0.101 (2)0.137 (3)0.0659 (19)0.072 (2)0.0050 (17)0.0411 (19)
C17A0.0693 (17)0.130 (3)0.0585 (15)0.0519 (17)0.0060 (13)0.0235 (16)
C18A0.0513 (13)0.0833 (16)0.0563 (14)0.0269 (12)0.0035 (11)0.0196 (12)
N1B0.0654 (14)0.0550 (12)0.0895 (17)0.0195 (10)0.0010 (13)0.0035 (11)
N2B0.0602 (13)0.0558 (12)0.0849 (16)0.0017 (10)0.0214 (12)0.0146 (11)
N3B0.0560 (11)0.0382 (8)0.0440 (9)0.0145 (7)0.0088 (8)0.0016 (7)
O1B0.0810 (16)0.150 (2)0.126 (2)0.0434 (15)0.0406 (15)0.0318 (17)
O2B0.0883 (16)0.132 (2)0.130 (2)0.0665 (14)0.0209 (15)0.0112 (16)
O3B0.110 (2)0.128 (2)0.106 (2)0.0418 (17)0.0285 (16)0.0025 (16)
O4B0.0773 (13)0.0476 (9)0.1274 (17)0.0034 (8)0.0506 (12)0.0009 (10)
O5B0.0997 (15)0.0641 (11)0.1138 (16)0.0280 (10)0.0627 (13)0.0009 (10)
O6B0.1005 (13)0.0454 (8)0.0441 (9)0.0246 (8)0.0128 (8)0.0063 (6)
C1B0.0517 (12)0.0391 (10)0.0491 (11)0.0128 (9)0.0003 (9)0.0060 (8)
C2B0.0541 (13)0.0386 (10)0.0522 (12)0.0071 (9)0.0094 (10)0.0046 (8)
C4B0.0529 (12)0.0475 (11)0.0492 (12)0.0154 (9)0.0057 (10)0.0043 (9)
C5B0.0516 (12)0.0384 (10)0.0482 (11)0.0074 (8)0.0124 (9)0.0072 (8)
C6B0.0846 (18)0.0409 (11)0.0609 (14)0.0189 (11)0.0347 (13)0.0006 (9)
C7B0.116 (2)0.0532 (13)0.0435 (13)0.0252 (14)0.0212 (14)0.0118 (10)
C8B0.097 (2)0.0445 (12)0.0404 (12)0.0157 (12)0.0097 (12)0.0111 (9)
C9B0.0573 (12)0.0365 (9)0.0364 (10)0.0124 (8)0.0072 (9)0.0070 (7)
C10B0.0778 (16)0.0440 (11)0.0581 (14)0.0224 (11)0.0168 (12)0.0023 (9)
C11B0.0781 (16)0.0378 (10)0.0435 (11)0.0120 (10)0.0056 (10)0.0046 (8)
C12B0.0500 (12)0.0395 (10)0.0460 (12)0.0166 (8)0.0085 (9)0.0054 (8)
C13B0.0403 (11)0.0383 (10)0.0519 (12)0.0121 (8)0.0062 (9)0.0030 (8)
C14B0.0589 (14)0.0402 (11)0.0623 (14)0.0128 (9)0.0149 (11)0.0051 (9)
C15B0.0686 (15)0.0397 (11)0.0792 (17)0.0165 (10)0.0149 (13)0.0005 (10)
C16B0.0751 (17)0.0470 (13)0.089 (2)0.0182 (11)0.0248 (14)0.0198 (12)
C17B0.0780 (17)0.0670 (15)0.0689 (16)0.0231 (13)0.0286 (14)0.0139 (12)
C18B0.0571 (13)0.0490 (11)0.0561 (13)0.0188 (10)0.0161 (10)0.0003 (9)
Geometric parameters (Å, º) top
N1A—O1A1.199 (2)N1B—O1B1.203 (3)
N1A—O2A1.223 (3)N1B—O2B1.218 (3)
N1A—C1A1.523 (3)N1B—C1B1.520 (3)
N2A—O3A1.203 (2)N2B—O3B1.196 (3)
N2A—O4A1.224 (2)N2B—O4B1.208 (3)
N2A—C5A1.517 (3)N2B—C5B1.515 (3)
N3A—C2A1.443 (3)N3B—C2B1.444 (3)
N3A—C10A1.457 (3)N3B—C10B1.453 (3)
N3A—C4A1.458 (3)N3B—C4B1.456 (3)
O5A—C6A1.217 (3)O5B—C6B1.207 (3)
O6A—C12A1.212 (3)O6B—C12B1.210 (2)
C1A—C8A1.488 (3)C1B—C8B1.503 (3)
C1A—C9A1.535 (3)C1B—C9B1.537 (3)
C1A—C2A1.554 (3)C1B—C2B1.543 (3)
C2A—H2AA0.9700C2B—H2BA0.9700
C2A—H2AB0.9700C2B—H2BB0.9700
C4A—C5A1.525 (3)C4B—C5B1.533 (3)
C4A—H4AA0.9700C4B—H4BA0.9700
C4A—H4AB0.9700C4B—H4BB0.9700
C5A—C9A1.541 (3)C5B—C9B1.534 (3)
C5A—C6A1.541 (3)C5B—C6B1.555 (3)
C6A—C7A1.459 (3)C6B—C7B1.439 (4)
C7A—C8A1.329 (3)C7B—C8B1.317 (4)
C7A—H7AA0.9300C7B—H7BA0.9300
C8A—H8AA0.9300C8B—H8BA0.9300
C9A—C11A1.529 (3)C9B—C11B1.522 (3)
C9A—H9AA0.9800C9B—H9BA0.9800
C10A—H10A0.9600C10B—H10D0.9600
C10A—H10B0.9600C10B—H10E0.9600
C10A—H10C0.9600C10B—H10F0.9600
C11A—C12A1.514 (3)C11B—C12B1.515 (3)
C11A—H11A0.9700C11B—H11C0.9700
C11A—H11B0.9700C11B—H11D0.9700
C12A—C13A1.496 (3)C12B—C13B1.488 (3)
C13A—C18A1.381 (4)C13B—C18B1.391 (3)
C13A—C14A1.386 (4)C13B—C14B1.394 (3)
C14A—C15A1.393 (5)C14B—C15B1.360 (3)
C14A—H14A0.9300C14B—H14B0.9300
C15A—C16A1.373 (5)C15B—C16B1.374 (4)
C15A—H15A0.9300C15B—H15B0.9300
C16A—C17A1.349 (5)C16B—C17B1.380 (4)
C16A—H16A0.9300C16B—H16B0.9300
C17A—C18A1.396 (3)C17B—C18B1.373 (3)
C17A—H17A0.9300C17B—H17B0.9300
C18A—H18A0.9300C18B—H18B0.9300
O1A—N1A—O2A123.3 (2)O1B—N1B—O2B122.8 (3)
O1A—N1A—C1A119.6 (2)O1B—N1B—C1B120.3 (3)
O2A—N1A—C1A117.11 (18)O2B—N1B—C1B116.9 (2)
O3A—N2A—O4A124.42 (18)O3B—N2B—O4B123.2 (2)
O3A—N2A—C5A118.76 (18)O3B—N2B—C5B118.6 (2)
O4A—N2A—C5A116.81 (18)O4B—N2B—C5B118.2 (2)
C2A—N3A—C10A111.1 (2)C2B—N3B—C10B111.29 (17)
C2A—N3A—C4A111.05 (18)C2B—N3B—C4B111.28 (16)
C10A—N3A—C4A111.63 (17)C10B—N3B—C4B112.03 (18)
C8A—C1A—N1A110.50 (17)C8B—C1B—N1B110.7 (2)
C8A—C1A—C9A111.38 (17)C8B—C1B—C9B110.48 (19)
N1A—C1A—C9A108.93 (16)N1B—C1B—C9B108.28 (16)
C8A—C1A—C2A111.15 (17)C8B—C1B—C2B110.64 (17)
N1A—C1A—C2A104.33 (16)N1B—C1B—C2B105.86 (18)
C9A—C1A—C2A110.31 (16)C9B—C1B—C2B110.75 (17)
N3A—C2A—C1A109.37 (17)N3B—C2B—C1B108.68 (17)
N3A—C2A—H2AA109.8N3B—C2B—H2BA110.0
C1A—C2A—H2AA109.8C1B—C2B—H2BA110.0
N3A—C2A—H2AB109.8N3B—C2B—H2BB110.0
C1A—C2A—H2AB109.8C1B—C2B—H2BB110.0
H2AA—C2A—H2AB108.2H2BA—C2B—H2BB108.3
N3A—C4A—C5A106.80 (16)N3B—C4B—C5B107.41 (17)
N3A—C4A—H4AA110.4N3B—C4B—H4BA110.2
C5A—C4A—H4AA110.4C5B—C4B—H4BA110.2
N3A—C4A—H4AB110.4N3B—C4B—H4BB110.2
C5A—C4A—H4AB110.4C5B—C4B—H4BB110.2
H4AA—C4A—H4AB108.6H4BA—C4B—H4BB108.5
N2A—C5A—C4A108.83 (16)N2B—C5B—C4B109.25 (19)
N2A—C5A—C9A109.24 (16)N2B—C5B—C9B111.23 (16)
C4A—C5A—C9A110.18 (17)C4B—C5B—C9B110.22 (17)
N2A—C5A—C6A107.47 (18)N2B—C5B—C6B105.88 (18)
C4A—C5A—C6A108.68 (18)C4B—C5B—C6B107.56 (16)
C9A—C5A—C6A112.35 (16)C9B—C5B—C6B112.52 (18)
O5A—C6A—C7A123.0 (2)O5B—C6B—C7B124.4 (2)
O5A—C6A—C5A119.9 (2)O5B—C6B—C5B119.6 (2)
C7A—C6A—C5A116.95 (19)C7B—C6B—C5B116.0 (2)
C8A—C7A—C6A121.5 (2)C8B—C7B—C6B122.9 (2)
C8A—C7A—H7AA119.2C8B—C7B—H7BA118.5
C6A—C7A—H7AA119.2C6B—C7B—H7BA118.5
C7A—C8A—C1A120.10 (18)C7B—C8B—C1B120.4 (2)
C7A—C8A—H8AA119.9C7B—C8B—H8BA119.8
C1A—C8A—H8AA119.9C1B—C8B—H8BA119.8
C11A—C9A—C1A112.99 (15)C11B—C9B—C5B116.60 (18)
C11A—C9A—C5A115.92 (16)C11B—C9B—C1B112.32 (18)
C1A—C9A—C5A102.80 (15)C5B—C9B—C1B103.40 (15)
C11A—C9A—H9AA108.3C11B—C9B—H9BA108.1
C1A—C9A—H9AA108.3C5B—C9B—H9BA108.1
C5A—C9A—H9AA108.3C1B—C9B—H9BA108.1
N3A—C10A—H10A109.5N3B—C10B—H10D109.5
N3A—C10A—H10B109.5N3B—C10B—H10E109.5
H10A—C10A—H10B109.5H10D—C10B—H10E109.5
N3A—C10A—H10C109.5N3B—C10B—H10F109.5
H10A—C10A—H10C109.5H10D—C10B—H10F109.5
H10B—C10A—H10C109.5H10E—C10B—H10F109.5
C12A—C11A—C9A112.96 (17)C12B—C11B—C9B113.16 (18)
C12A—C11A—H11A109.0C12B—C11B—H11C108.9
C9A—C11A—H11A109.0C9B—C11B—H11C108.9
C12A—C11A—H11B109.0C12B—C11B—H11D108.9
C9A—C11A—H11B109.0C9B—C11B—H11D108.9
H11A—C11A—H11B107.8H11C—C11B—H11D107.8
O6A—C12A—C13A121.6 (2)O6B—C12B—C13B120.93 (17)
O6A—C12A—C11A120.49 (19)O6B—C12B—C11B120.88 (18)
C13A—C12A—C11A117.94 (19)C13B—C12B—C11B118.16 (17)
C18A—C13A—C14A119.4 (2)C18B—C13B—C14B118.60 (19)
C18A—C13A—C12A122.1 (2)C18B—C13B—C12B123.05 (17)
C14A—C13A—C12A118.5 (2)C14B—C13B—C12B118.30 (19)
C13A—C14A—C15A119.5 (3)C15B—C14B—C13B121.0 (2)
C13A—C14A—H14A120.2C15B—C14B—H14B119.5
C15A—C14A—H14A120.2C13B—C14B—H14B119.5
C16A—C15A—C14A120.1 (3)C14B—C15B—C16B119.8 (2)
C16A—C15A—H15A119.9C14B—C15B—H15B120.1
C14A—C15A—H15A119.9C16B—C15B—H15B120.1
C17A—C16A—C15A120.7 (3)C15B—C16B—C17B120.5 (2)
C17A—C16A—H16A119.7C15B—C16B—H16B119.8
C15A—C16A—H16A119.7C17B—C16B—H16B119.8
C16A—C17A—C18A120.1 (3)C18B—C17B—C16B119.9 (2)
C16A—C17A—H17A119.9C18B—C17B—H17B120.1
C18A—C17A—H17A119.9C16B—C17B—H17B120.1
C13A—C18A—C17A120.1 (3)C17B—C18B—C13B120.2 (2)
C13A—C18A—H18A120.0C17B—C18B—H18B119.9
C17A—C18A—H18A120.0C13B—C18B—H18B119.9
N1A—C1A—C9A—C5A173.81 (15)N1B—C1B—C9B—C5B175.72 (17)
N2A—C5A—C9A—C1A176.45 (15)N2B—C5B—C9B—C1B176.40 (17)
O1A—N1A—C1A—C8A25.3 (2)O1B—N1B—C1B—C8B4.1 (3)
O4A—N2A—C5A—C6A47.0 (3)O4B—N2B—C5B—C6B58.9 (3)
C4A—C5A—C9A—C11A172.19 (16)C4B—C5B—C9B—C11B173.97 (16)
C6A—C5A—C9A—C11A66.5 (2)C6B—C5B—C9B—C11B66.0 (2)
O2A—N1A—C1A—C8A157.03 (18)O2B—N1B—C1B—C8B176.3 (2)
O1A—N1A—C1A—C9A147.94 (19)O1B—N1B—C1B—C9B125.3 (3)
O2A—N1A—C1A—C9A34.4 (2)O2B—N1B—C1B—C9B55.1 (3)
O1A—N1A—C1A—C2A94.3 (2)O1B—N1B—C1B—C2B115.9 (3)
O2A—N1A—C1A—C2A83.4 (2)O2B—N1B—C1B—C2B63.8 (3)
C10A—N3A—C2A—C1A174.33 (18)C10B—N3B—C2B—C1B172.99 (16)
C4A—N3A—C2A—C1A60.8 (2)C4B—N3B—C2B—C1B61.3 (2)
C8A—C1A—C2A—N3A63.7 (2)C8B—C1B—C2B—N3B61.9 (2)
N1A—C1A—C2A—N3A177.21 (16)N1B—C1B—C2B—N3B178.11 (16)
C9A—C1A—C2A—N3A60.4 (2)C9B—C1B—C2B—N3B61.0 (2)
C2A—N3A—C4A—C5A63.3 (2)C2B—N3B—C4B—C5B63.0 (2)
C10A—N3A—C4A—C5A172.1 (2)C10B—N3B—C4B—C5B171.71 (17)
O3A—N2A—C5A—C4A16.0 (3)O3B—N2B—C5B—C4B7.4 (3)
O4A—N2A—C5A—C4A164.5 (2)O4B—N2B—C5B—C4B174.49 (19)
O3A—N2A—C5A—C9A104.4 (2)O3B—N2B—C5B—C9B114.5 (3)
O4A—N2A—C5A—C9A75.1 (2)O4B—N2B—C5B—C9B63.6 (3)
O3A—N2A—C5A—C6A133.5 (2)O3B—N2B—C5B—C6B123.0 (3)
N3A—C4A—C5A—N2A173.82 (18)N3B—C4B—C5B—N2B172.83 (16)
N3A—C4A—C5A—C9A66.4 (2)N3B—C4B—C5B—C9B64.7 (2)
N3A—C4A—C5A—C6A57.1 (2)N3B—C4B—C5B—C6B58.3 (2)
N2A—C5A—C6A—O5A38.3 (3)N2B—C5B—C6B—O5B35.6 (3)
C4A—C5A—C6A—O5A79.3 (3)C4B—C5B—C6B—O5B81.1 (2)
C9A—C5A—C6A—O5A158.5 (2)C9B—C5B—C6B—O5B157.29 (19)
N2A—C5A—C6A—C7A145.39 (19)N2B—C5B—C6B—C7B147.7 (2)
C4A—C5A—C6A—C7A97.0 (2)C4B—C5B—C6B—C7B95.6 (2)
C9A—C5A—C6A—C7A25.2 (3)C9B—C5B—C6B—C7B26.0 (2)
O5A—C6A—C7A—C8A170.1 (2)O5B—C6B—C7B—C8B171.0 (2)
C5A—C6A—C7A—C8A6.1 (3)C5B—C6B—C7B—C8B5.5 (3)
C6A—C7A—C8A—C1A0.3 (3)C6B—C7B—C8B—C1B0.1 (4)
N1A—C1A—C8A—C7A159.26 (19)N1B—C1B—C8B—C7B156.7 (2)
C9A—C1A—C8A—C7A38.0 (3)C9B—C1B—C8B—C7B36.8 (3)
C2A—C1A—C8A—C7A85.4 (2)C2B—C1B—C8B—C7B86.3 (3)
C8A—C1A—C9A—C11A61.6 (2)N2B—C5B—C9B—C11B52.6 (2)
N1A—C1A—C9A—C11A60.5 (2)C4B—C5B—C9B—C1B62.3 (2)
C2A—C1A—C9A—C11A174.45 (18)C6B—C5B—C9B—C1B57.8 (2)
C8A—C1A—C9A—C5A64.06 (19)C8B—C1B—C9B—C11B63.6 (2)
C2A—C1A—C9A—C5A59.9 (2)N1B—C1B—C9B—C11B57.7 (2)
N2A—C5A—C9A—C11A52.7 (2)C2B—C1B—C9B—C11B173.40 (18)
C4A—C5A—C9A—C1A64.05 (19)C8B—C1B—C9B—C5B62.9 (2)
C6A—C5A—C9A—C1A57.3 (2)C2B—C1B—C9B—C5B60.1 (2)
C1A—C9A—C11A—C12A152.83 (18)C5B—C9B—C11B—C12B89.4 (2)
C5A—C9A—C11A—C12A88.9 (2)C1B—C9B—C11B—C12B151.50 (19)
C9A—C11A—C12A—O6A13.0 (3)C9B—C11B—C12B—O6B13.1 (3)
C9A—C11A—C12A—C13A167.00 (18)C9B—C11B—C12B—C13B169.02 (18)
O6A—C12A—C13A—C18A165.7 (2)O6B—C12B—C13B—C18B154.3 (2)
C11A—C12A—C13A—C18A14.2 (3)C11B—C12B—C13B—C18B27.8 (3)
O6A—C12A—C13A—C14A13.4 (4)O6B—C12B—C13B—C14B23.1 (3)
C11A—C12A—C13A—C14A166.7 (2)C11B—C12B—C13B—C14B154.8 (2)
C18A—C13A—C14A—C15A1.7 (4)C18B—C13B—C14B—C15B0.3 (3)
C12A—C13A—C14A—C15A179.2 (3)C12B—C13B—C14B—C15B177.9 (2)
C13A—C14A—C15A—C16A1.9 (5)C13B—C14B—C15B—C16B1.4 (4)
C14A—C15A—C16A—C17A0.8 (5)C14B—C15B—C16B—C17B0.9 (4)
C15A—C16A—C17A—C18A0.6 (5)C15B—C16B—C17B—C18B0.5 (4)
C14A—C13A—C18A—C17A0.3 (4)C16B—C17B—C18B—C13B1.5 (4)
C12A—C13A—C18A—C17A179.4 (2)C14B—C13B—C18B—C17B1.1 (3)
C16A—C17A—C18A—C13A0.8 (4)C12B—C13B—C18B—C17B176.3 (2)

Experimental details

Crystal data
Chemical formulaC17H17N3O6
Mr359.34
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)11.374 (6), 11.669 (5), 13.715 (6)
α, β, γ (°)84.56 (4), 75.64 (4), 75.07 (4)
V3)1702.9 (14)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.50 × 0.30 × 0.30
Data collection
DiffractometerSiemens P3
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6198, 5875, 4198
Rint0.038
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.169, 0.95
No. of reflections5875
No. of parameters469
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.27

Computer programs: P3 (Siemens, 1989), XDISK (Siemens, 1991), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.

Selected torsion angles (º) top
N1A—C1A—C9A—C5A173.81 (15)N1B—C1B—C9B—C5B175.72 (17)
N2A—C5A—C9A—C1A176.45 (15)N2B—C5B—C9B—C1B176.40 (17)
O1A—N1A—C1A—C8A25.3 (2)O1B—N1B—C1B—C8B4.1 (3)
O4A—N2A—C5A—C6A47.0 (3)O4B—N2B—C5B—C6B58.9 (3)
C4A—C5A—C9A—C11A172.19 (16)C4B—C5B—C9B—C11B173.97 (16)
C6A—C5A—C9A—C11A66.5 (2)C6B—C5B—C9B—C11B66.0 (2)
 

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