Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680202041X/ob6188sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680202041X/ob6188Isup2.hkl |
CCDC reference: 202327
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.
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).
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.
C17H17N3O6 | Z = 4 |
Mr = 359.34 | F(000) = 752 |
Triclinic, P1 | Dx = 1.402 Mg m−3 |
a = 11.374 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.669 (5) Å | Cell parameters from 24 reflections |
c = 13.715 (6) Å | θ = 10–11° |
α = 84.56 (4)° | µ = 0.11 mm−1 |
β = 75.64 (4)° | T = 293 K |
γ = 75.07 (4)° | Square prism, yellow |
V = 1702.9 (14) Å3 | 0.50 × 0.30 × 0.30 mm |
Siemens P3 diffractometer | Rint = 0.038 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 1.9° |
Graphite monochromator | h = 0→13 |
ω scans | k = −13→13 |
6198 measured reflections | l = −15→16 |
5875 independent reflections | 2 standard reflections every 98 reflections |
4198 reflections with I > 2σ(I) | intensity decay: 3.4% |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.061 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.169 | H-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 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C17H17N3O6 | γ = 75.07 (4)° |
Mr = 359.34 | V = 1702.9 (14) Å3 |
Triclinic, P1 | Z = 4 |
a = 11.374 (6) Å | Mo Kα radiation |
b = 11.669 (5) Å | µ = 0.11 mm−1 |
c = 13.715 (6) Å | T = 293 K |
α = 84.56 (4)° | 0.50 × 0.30 × 0.30 mm |
β = 75.64 (4)° |
Siemens P3 diffractometer | Rint = 0.038 |
6198 measured reflections | 2 standard reflections every 98 reflections |
5875 independent reflections | intensity decay: 3.4% |
4198 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
wR(F2) = 0.169 | H-atom parameters constrained |
S = 0.95 | Δρmax = 0.30 e Å−3 |
5875 reflections | Δρmin = −0.27 e Å−3 |
469 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1A | 1.18163 (17) | 0.70037 (17) | 0.06086 (13) | 0.0534 (5) | |
N2A | 0.77553 (17) | 0.96661 (16) | 0.22244 (15) | 0.0563 (5) | |
N3A | 0.85363 (18) | 0.70890 (15) | 0.05651 (14) | 0.0548 (5) | |
O1A | 1.25348 (18) | 0.60621 (18) | 0.06737 (16) | 0.0864 (6) | |
O2A | 1.21318 (16) | 0.78658 (16) | 0.01460 (14) | 0.0698 (5) | |
O3A | 0.71615 (18) | 1.03869 (15) | 0.17316 (15) | 0.0781 (6) | |
O4A | 0.78503 (18) | 0.98328 (17) | 0.30666 (14) | 0.0806 (6) | |
O5A | 0.71335 (17) | 0.76351 (19) | 0.31564 (16) | 0.0866 (6) | |
O6A | 1.0094 (2) | 1.07040 (14) | 0.15322 (15) | 0.0824 (6) | |
C1A | 1.04280 (18) | 0.71456 (16) | 0.10841 (14) | 0.0435 (5) | |
C2A | 0.9873 (2) | 0.69200 (19) | 0.02134 (17) | 0.0535 (5) | |
H2AA | 1.0058 | 0.7465 | −0.0350 | 0.064* | |
H2AB | 1.0247 | 0.6117 | −0.0014 | 0.064* | |
C4A | 0.7943 (2) | 0.82986 (18) | 0.08911 (17) | 0.0521 (5) | |
H4AA | 0.7042 | 0.8416 | 0.1089 | 0.063* | |
H4AB | 0.8143 | 0.8864 | 0.0349 | 0.063* | |
C5A | 0.84501 (19) | 0.84670 (16) | 0.17842 (15) | 0.0445 (5) | |
C6A | 0.8174 (2) | 0.7511 (2) | 0.26045 (17) | 0.0546 (5) | |
C7A | 0.9180 (2) | 0.64498 (19) | 0.26346 (17) | 0.0544 (5) | |
H7AA | 0.9075 | 0.5890 | 0.3158 | 0.065* | |
C8A | 1.0243 (2) | 0.62643 (17) | 0.19309 (16) | 0.0477 (5) | |
H8AA | 1.0873 | 0.5583 | 0.1968 | 0.057* | |
C9A | 0.98580 (18) | 0.84213 (16) | 0.14396 (14) | 0.0402 (4) | |
H9AA | 0.9983 | 0.8965 | 0.0854 | 0.048* | |
C10A | 0.7994 (3) | 0.6772 (2) | −0.0197 (2) | 0.0809 (9) | |
H10A | 0.8402 | 0.5971 | −0.0393 | 0.121* | |
H10B | 0.8105 | 0.7301 | −0.0774 | 0.121* | |
H10C | 0.7117 | 0.6834 | 0.0073 | 0.121* | |
C11A | 1.04558 (19) | 0.87405 (17) | 0.22265 (15) | 0.0444 (5) | |
H11A | 1.0039 | 0.8492 | 0.2889 | 0.053* | |
H11B | 1.1327 | 0.8307 | 0.2100 | 0.053* | |
C12A | 1.0383 (2) | 1.00546 (19) | 0.22223 (17) | 0.0524 (5) | |
C13A | 1.0678 (2) | 1.0517 (2) | 0.30912 (18) | 0.0558 (6) | |
C14A | 1.0366 (3) | 1.1733 (2) | 0.3208 (2) | 0.0805 (8) | |
H14A | 0.9993 | 1.2244 | 0.2749 | 0.097* | |
C15A | 1.0617 (4) | 1.2184 (3) | 0.4019 (3) | 0.1073 (13) | |
H15A | 1.0387 | 1.2998 | 0.4113 | 0.129* | |
C16A | 1.1202 (3) | 1.1430 (4) | 0.4680 (3) | 0.0949 (11) | |
H16A | 1.1376 | 1.1738 | 0.5215 | 0.114* | |
C17A | 1.1529 (3) | 1.0246 (3) | 0.4561 (2) | 0.0811 (8) | |
H17A | 1.1932 | 0.9744 | 0.5009 | 0.097* | |
C18A | 1.1262 (2) | 0.9773 (2) | 0.37659 (18) | 0.0621 (6) | |
H18A | 1.1478 | 0.8956 | 0.3691 | 0.075* | |
N1B | 0.7221 (2) | 0.40555 (18) | 0.2665 (2) | 0.0720 (6) | |
N2B | 0.2580 (2) | 0.54668 (18) | 0.37025 (19) | 0.0677 (6) | |
N3B | 0.47394 (16) | 0.24604 (13) | 0.38160 (12) | 0.0460 (4) | |
O1B | 0.7967 (2) | 0.3901 (3) | 0.1868 (2) | 0.1262 (10) | |
O2B | 0.7429 (2) | 0.4435 (2) | 0.3386 (2) | 0.1098 (8) | |
O3B | 0.1942 (3) | 0.5432 (3) | 0.4536 (2) | 0.1378 (12) | |
O4B | 0.23782 (18) | 0.62839 (15) | 0.31084 (18) | 0.0817 (6) | |
O5B | 0.2519 (2) | 0.39300 (15) | 0.23680 (17) | 0.0842 (6) | |
O6B | 0.42995 (18) | 0.71600 (12) | 0.38920 (11) | 0.0624 (4) | |
C1B | 0.5958 (2) | 0.37680 (17) | 0.28111 (16) | 0.0481 (5) | |
C2B | 0.5938 (2) | 0.27512 (17) | 0.36162 (16) | 0.0494 (5) | |
H2BA | 0.6602 | 0.2061 | 0.3377 | 0.059* | |
H2BB | 0.6070 | 0.2996 | 0.4229 | 0.059* | |
C4B | 0.3724 (2) | 0.34702 (17) | 0.42057 (16) | 0.0502 (5) | |
H4BA | 0.3850 | 0.3741 | 0.4811 | 0.060* | |
H4BB | 0.2930 | 0.3248 | 0.4370 | 0.060* | |
C5B | 0.3722 (2) | 0.44563 (16) | 0.33838 (15) | 0.0462 (5) | |
C6B | 0.3552 (3) | 0.39547 (18) | 0.24300 (18) | 0.0583 (6) | |
C7B | 0.4684 (3) | 0.3486 (2) | 0.16948 (18) | 0.0689 (7) | |
H7BA | 0.4619 | 0.3241 | 0.1088 | 0.083* | |
C8B | 0.5807 (3) | 0.33867 (19) | 0.18421 (17) | 0.0647 (7) | |
H8BA | 0.6511 | 0.3079 | 0.1343 | 0.078* | |
C9B | 0.4931 (2) | 0.48808 (16) | 0.31869 (14) | 0.0435 (5) | |
H9BA | 0.5036 | 0.5078 | 0.3834 | 0.052* | |
C10B | 0.4716 (2) | 0.14129 (18) | 0.44766 (18) | 0.0586 (6) | |
H10D | 0.5399 | 0.0770 | 0.4195 | 0.088* | |
H10E | 0.3940 | 0.1196 | 0.4545 | 0.088* | |
H10F | 0.4794 | 0.1580 | 0.5127 | 0.088* | |
C11B | 0.5015 (2) | 0.59467 (17) | 0.24648 (16) | 0.0548 (6) | |
H11C | 0.5883 | 0.5880 | 0.2118 | 0.066* | |
H11D | 0.4550 | 0.5936 | 0.1962 | 0.066* | |
C12B | 0.45111 (19) | 0.71214 (16) | 0.29848 (15) | 0.0443 (5) | |
C13B | 0.43256 (18) | 0.82283 (16) | 0.23475 (15) | 0.0437 (5) | |
C14B | 0.4355 (2) | 0.92789 (17) | 0.27364 (18) | 0.0533 (5) | |
H14B | 0.4515 | 0.9264 | 0.3371 | 0.064* | |
C15B | 0.4152 (2) | 1.03251 (19) | 0.2203 (2) | 0.0624 (6) | |
H15B | 0.4192 | 1.1017 | 0.2465 | 0.075* | |
C16B | 0.3888 (3) | 1.0358 (2) | 0.1274 (2) | 0.0703 (7) | |
H16B | 0.3738 | 1.1076 | 0.0913 | 0.084* | |
C17B | 0.3846 (3) | 0.9333 (2) | 0.0872 (2) | 0.0692 (7) | |
H17B | 0.3660 | 0.9361 | 0.0245 | 0.083* | |
C18B | 0.4077 (2) | 0.82704 (19) | 0.13995 (17) | 0.0526 (5) | |
H18B | 0.4068 | 0.7577 | 0.1122 | 0.063* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0509 (11) | 0.0610 (11) | 0.0442 (10) | −0.0076 (9) | −0.0039 (8) | −0.0173 (8) |
N2A | 0.0481 (11) | 0.0511 (10) | 0.0637 (12) | −0.0008 (8) | −0.0081 (9) | −0.0172 (9) |
N3A | 0.0610 (12) | 0.0476 (10) | 0.0643 (12) | −0.0091 (8) | −0.0304 (10) | −0.0131 (8) |
O1A | 0.0578 (11) | 0.0803 (13) | 0.0944 (14) | 0.0144 (10) | −0.0007 (10) | −0.0046 (10) |
O2A | 0.0630 (11) | 0.0753 (11) | 0.0651 (11) | −0.0241 (9) | 0.0085 (8) | −0.0144 (9) |
O3A | 0.0777 (13) | 0.0526 (10) | 0.0955 (14) | 0.0104 (9) | −0.0280 (11) | −0.0126 (9) |
O4A | 0.0776 (12) | 0.0870 (12) | 0.0674 (12) | 0.0070 (10) | −0.0133 (10) | −0.0404 (10) |
O5A | 0.0533 (11) | 0.1036 (14) | 0.0840 (14) | −0.0141 (10) | 0.0069 (10) | 0.0143 (11) |
O6A | 0.1327 (17) | 0.0490 (9) | 0.0842 (13) | −0.0350 (10) | −0.0497 (12) | 0.0072 (8) |
C1A | 0.0437 (11) | 0.0433 (10) | 0.0422 (10) | −0.0071 (8) | −0.0080 (8) | −0.0097 (8) |
C2A | 0.0678 (15) | 0.0461 (11) | 0.0480 (12) | −0.0058 (10) | −0.0194 (10) | −0.0150 (9) |
C4A | 0.0519 (13) | 0.0509 (11) | 0.0559 (13) | −0.0076 (9) | −0.0203 (10) | −0.0064 (9) |
C5A | 0.0441 (11) | 0.0422 (10) | 0.0468 (11) | −0.0063 (8) | −0.0110 (9) | −0.0096 (8) |
C6A | 0.0465 (13) | 0.0662 (14) | 0.0514 (12) | −0.0184 (10) | −0.0070 (10) | −0.0024 (10) |
C7A | 0.0598 (14) | 0.0523 (12) | 0.0554 (13) | −0.0207 (10) | −0.0180 (11) | 0.0099 (9) |
C8A | 0.0499 (12) | 0.0392 (10) | 0.0564 (12) | −0.0081 (9) | −0.0181 (10) | −0.0059 (8) |
C9A | 0.0437 (11) | 0.0384 (9) | 0.0389 (10) | −0.0100 (8) | −0.0088 (8) | −0.0055 (7) |
C10A | 0.091 (2) | 0.0697 (16) | 0.100 (2) | −0.0100 (14) | −0.0567 (18) | −0.0256 (14) |
C11A | 0.0465 (11) | 0.0456 (10) | 0.0427 (11) | −0.0122 (8) | −0.0095 (9) | −0.0091 (8) |
C12A | 0.0549 (13) | 0.0478 (11) | 0.0577 (13) | −0.0173 (9) | −0.0112 (10) | −0.0086 (10) |
C13A | 0.0515 (13) | 0.0618 (13) | 0.0578 (13) | −0.0263 (10) | −0.0007 (10) | −0.0171 (10) |
C14A | 0.093 (2) | 0.0708 (16) | 0.086 (2) | −0.0361 (14) | −0.0096 (16) | −0.0276 (14) |
C15A | 0.124 (3) | 0.097 (2) | 0.111 (3) | −0.062 (2) | 0.013 (2) | −0.058 (2) |
C16A | 0.101 (2) | 0.137 (3) | 0.0659 (19) | −0.072 (2) | 0.0050 (17) | −0.0411 (19) |
C17A | 0.0693 (17) | 0.130 (3) | 0.0585 (15) | −0.0519 (17) | −0.0060 (13) | −0.0235 (16) |
C18A | 0.0513 (13) | 0.0833 (16) | 0.0563 (14) | −0.0269 (12) | −0.0035 (11) | −0.0196 (12) |
N1B | 0.0654 (14) | 0.0550 (12) | 0.0895 (17) | −0.0195 (10) | −0.0010 (13) | −0.0035 (11) |
N2B | 0.0602 (13) | 0.0558 (12) | 0.0849 (16) | −0.0017 (10) | −0.0214 (12) | −0.0146 (11) |
N3B | 0.0560 (11) | 0.0382 (8) | 0.0440 (9) | −0.0145 (7) | −0.0088 (8) | −0.0016 (7) |
O1B | 0.0810 (16) | 0.150 (2) | 0.126 (2) | −0.0434 (15) | 0.0406 (15) | −0.0318 (17) |
O2B | 0.0883 (16) | 0.132 (2) | 0.130 (2) | −0.0665 (14) | −0.0209 (15) | −0.0112 (16) |
O3B | 0.110 (2) | 0.128 (2) | 0.106 (2) | 0.0418 (17) | 0.0285 (16) | −0.0025 (16) |
O4B | 0.0773 (13) | 0.0476 (9) | 0.1274 (17) | −0.0034 (8) | −0.0506 (12) | 0.0009 (10) |
O5B | 0.0997 (15) | 0.0641 (11) | 0.1138 (16) | −0.0280 (10) | −0.0627 (13) | −0.0009 (10) |
O6B | 0.1005 (13) | 0.0454 (8) | 0.0441 (9) | −0.0246 (8) | −0.0128 (8) | −0.0063 (6) |
C1B | 0.0517 (12) | 0.0391 (10) | 0.0491 (11) | −0.0128 (9) | −0.0003 (9) | −0.0060 (8) |
C2B | 0.0541 (13) | 0.0386 (10) | 0.0522 (12) | −0.0071 (9) | −0.0094 (10) | −0.0046 (8) |
C4B | 0.0529 (12) | 0.0475 (11) | 0.0492 (12) | −0.0154 (9) | −0.0057 (10) | −0.0043 (9) |
C5B | 0.0516 (12) | 0.0384 (10) | 0.0482 (11) | −0.0074 (8) | −0.0124 (9) | −0.0072 (8) |
C6B | 0.0846 (18) | 0.0409 (11) | 0.0609 (14) | −0.0189 (11) | −0.0347 (13) | 0.0006 (9) |
C7B | 0.116 (2) | 0.0532 (13) | 0.0435 (13) | −0.0252 (14) | −0.0212 (14) | −0.0118 (10) |
C8B | 0.097 (2) | 0.0445 (12) | 0.0404 (12) | −0.0157 (12) | 0.0097 (12) | −0.0111 (9) |
C9B | 0.0573 (12) | 0.0365 (9) | 0.0364 (10) | −0.0124 (8) | −0.0072 (9) | −0.0070 (7) |
C10B | 0.0778 (16) | 0.0440 (11) | 0.0581 (14) | −0.0224 (11) | −0.0168 (12) | 0.0023 (9) |
C11B | 0.0781 (16) | 0.0378 (10) | 0.0435 (11) | −0.0120 (10) | −0.0056 (10) | −0.0046 (8) |
C12B | 0.0500 (12) | 0.0395 (10) | 0.0460 (12) | −0.0166 (8) | −0.0085 (9) | −0.0054 (8) |
C13B | 0.0403 (11) | 0.0383 (10) | 0.0519 (12) | −0.0121 (8) | −0.0062 (9) | −0.0030 (8) |
C14B | 0.0589 (14) | 0.0402 (11) | 0.0623 (14) | −0.0128 (9) | −0.0149 (11) | −0.0051 (9) |
C15B | 0.0686 (15) | 0.0397 (11) | 0.0792 (17) | −0.0165 (10) | −0.0149 (13) | −0.0005 (10) |
C16B | 0.0751 (17) | 0.0470 (13) | 0.089 (2) | −0.0182 (11) | −0.0248 (14) | 0.0198 (12) |
C17B | 0.0780 (17) | 0.0670 (15) | 0.0689 (16) | −0.0231 (13) | −0.0286 (14) | 0.0139 (12) |
C18B | 0.0571 (13) | 0.0490 (11) | 0.0561 (13) | −0.0188 (10) | −0.0161 (10) | 0.0003 (9) |
N1A—O1A | 1.199 (2) | N1B—O1B | 1.203 (3) |
N1A—O2A | 1.223 (3) | N1B—O2B | 1.218 (3) |
N1A—C1A | 1.523 (3) | N1B—C1B | 1.520 (3) |
N2A—O3A | 1.203 (2) | N2B—O3B | 1.196 (3) |
N2A—O4A | 1.224 (2) | N2B—O4B | 1.208 (3) |
N2A—C5A | 1.517 (3) | N2B—C5B | 1.515 (3) |
N3A—C2A | 1.443 (3) | N3B—C2B | 1.444 (3) |
N3A—C10A | 1.457 (3) | N3B—C10B | 1.453 (3) |
N3A—C4A | 1.458 (3) | N3B—C4B | 1.456 (3) |
O5A—C6A | 1.217 (3) | O5B—C6B | 1.207 (3) |
O6A—C12A | 1.212 (3) | O6B—C12B | 1.210 (2) |
C1A—C8A | 1.488 (3) | C1B—C8B | 1.503 (3) |
C1A—C9A | 1.535 (3) | C1B—C9B | 1.537 (3) |
C1A—C2A | 1.554 (3) | C1B—C2B | 1.543 (3) |
C2A—H2AA | 0.9700 | C2B—H2BA | 0.9700 |
C2A—H2AB | 0.9700 | C2B—H2BB | 0.9700 |
C4A—C5A | 1.525 (3) | C4B—C5B | 1.533 (3) |
C4A—H4AA | 0.9700 | C4B—H4BA | 0.9700 |
C4A—H4AB | 0.9700 | C4B—H4BB | 0.9700 |
C5A—C9A | 1.541 (3) | C5B—C9B | 1.534 (3) |
C5A—C6A | 1.541 (3) | C5B—C6B | 1.555 (3) |
C6A—C7A | 1.459 (3) | C6B—C7B | 1.439 (4) |
C7A—C8A | 1.329 (3) | C7B—C8B | 1.317 (4) |
C7A—H7AA | 0.9300 | C7B—H7BA | 0.9300 |
C8A—H8AA | 0.9300 | C8B—H8BA | 0.9300 |
C9A—C11A | 1.529 (3) | C9B—C11B | 1.522 (3) |
C9A—H9AA | 0.9800 | C9B—H9BA | 0.9800 |
C10A—H10A | 0.9600 | C10B—H10D | 0.9600 |
C10A—H10B | 0.9600 | C10B—H10E | 0.9600 |
C10A—H10C | 0.9600 | C10B—H10F | 0.9600 |
C11A—C12A | 1.514 (3) | C11B—C12B | 1.515 (3) |
C11A—H11A | 0.9700 | C11B—H11C | 0.9700 |
C11A—H11B | 0.9700 | C11B—H11D | 0.9700 |
C12A—C13A | 1.496 (3) | C12B—C13B | 1.488 (3) |
C13A—C18A | 1.381 (4) | C13B—C18B | 1.391 (3) |
C13A—C14A | 1.386 (4) | C13B—C14B | 1.394 (3) |
C14A—C15A | 1.393 (5) | C14B—C15B | 1.360 (3) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C15A—C16A | 1.373 (5) | C15B—C16B | 1.374 (4) |
C15A—H15A | 0.9300 | C15B—H15B | 0.9300 |
C16A—C17A | 1.349 (5) | C16B—C17B | 1.380 (4) |
C16A—H16A | 0.9300 | C16B—H16B | 0.9300 |
C17A—C18A | 1.396 (3) | C17B—C18B | 1.373 (3) |
C17A—H17A | 0.9300 | C17B—H17B | 0.9300 |
C18A—H18A | 0.9300 | C18B—H18B | 0.9300 |
O1A—N1A—O2A | 123.3 (2) | O1B—N1B—O2B | 122.8 (3) |
O1A—N1A—C1A | 119.6 (2) | O1B—N1B—C1B | 120.3 (3) |
O2A—N1A—C1A | 117.11 (18) | O2B—N1B—C1B | 116.9 (2) |
O3A—N2A—O4A | 124.42 (18) | O3B—N2B—O4B | 123.2 (2) |
O3A—N2A—C5A | 118.76 (18) | O3B—N2B—C5B | 118.6 (2) |
O4A—N2A—C5A | 116.81 (18) | O4B—N2B—C5B | 118.2 (2) |
C2A—N3A—C10A | 111.1 (2) | C2B—N3B—C10B | 111.29 (17) |
C2A—N3A—C4A | 111.05 (18) | C2B—N3B—C4B | 111.28 (16) |
C10A—N3A—C4A | 111.63 (17) | C10B—N3B—C4B | 112.03 (18) |
C8A—C1A—N1A | 110.50 (17) | C8B—C1B—N1B | 110.7 (2) |
C8A—C1A—C9A | 111.38 (17) | C8B—C1B—C9B | 110.48 (19) |
N1A—C1A—C9A | 108.93 (16) | N1B—C1B—C9B | 108.28 (16) |
C8A—C1A—C2A | 111.15 (17) | C8B—C1B—C2B | 110.64 (17) |
N1A—C1A—C2A | 104.33 (16) | N1B—C1B—C2B | 105.86 (18) |
C9A—C1A—C2A | 110.31 (16) | C9B—C1B—C2B | 110.75 (17) |
N3A—C2A—C1A | 109.37 (17) | N3B—C2B—C1B | 108.68 (17) |
N3A—C2A—H2AA | 109.8 | N3B—C2B—H2BA | 110.0 |
C1A—C2A—H2AA | 109.8 | C1B—C2B—H2BA | 110.0 |
N3A—C2A—H2AB | 109.8 | N3B—C2B—H2BB | 110.0 |
C1A—C2A—H2AB | 109.8 | C1B—C2B—H2BB | 110.0 |
H2AA—C2A—H2AB | 108.2 | H2BA—C2B—H2BB | 108.3 |
N3A—C4A—C5A | 106.80 (16) | N3B—C4B—C5B | 107.41 (17) |
N3A—C4A—H4AA | 110.4 | N3B—C4B—H4BA | 110.2 |
C5A—C4A—H4AA | 110.4 | C5B—C4B—H4BA | 110.2 |
N3A—C4A—H4AB | 110.4 | N3B—C4B—H4BB | 110.2 |
C5A—C4A—H4AB | 110.4 | C5B—C4B—H4BB | 110.2 |
H4AA—C4A—H4AB | 108.6 | H4BA—C4B—H4BB | 108.5 |
N2A—C5A—C4A | 108.83 (16) | N2B—C5B—C4B | 109.25 (19) |
N2A—C5A—C9A | 109.24 (16) | N2B—C5B—C9B | 111.23 (16) |
C4A—C5A—C9A | 110.18 (17) | C4B—C5B—C9B | 110.22 (17) |
N2A—C5A—C6A | 107.47 (18) | N2B—C5B—C6B | 105.88 (18) |
C4A—C5A—C6A | 108.68 (18) | C4B—C5B—C6B | 107.56 (16) |
C9A—C5A—C6A | 112.35 (16) | C9B—C5B—C6B | 112.52 (18) |
O5A—C6A—C7A | 123.0 (2) | O5B—C6B—C7B | 124.4 (2) |
O5A—C6A—C5A | 119.9 (2) | O5B—C6B—C5B | 119.6 (2) |
C7A—C6A—C5A | 116.95 (19) | C7B—C6B—C5B | 116.0 (2) |
C8A—C7A—C6A | 121.5 (2) | C8B—C7B—C6B | 122.9 (2) |
C8A—C7A—H7AA | 119.2 | C8B—C7B—H7BA | 118.5 |
C6A—C7A—H7AA | 119.2 | C6B—C7B—H7BA | 118.5 |
C7A—C8A—C1A | 120.10 (18) | C7B—C8B—C1B | 120.4 (2) |
C7A—C8A—H8AA | 119.9 | C7B—C8B—H8BA | 119.8 |
C1A—C8A—H8AA | 119.9 | C1B—C8B—H8BA | 119.8 |
C11A—C9A—C1A | 112.99 (15) | C11B—C9B—C5B | 116.60 (18) |
C11A—C9A—C5A | 115.92 (16) | C11B—C9B—C1B | 112.32 (18) |
C1A—C9A—C5A | 102.80 (15) | C5B—C9B—C1B | 103.40 (15) |
C11A—C9A—H9AA | 108.3 | C11B—C9B—H9BA | 108.1 |
C1A—C9A—H9AA | 108.3 | C5B—C9B—H9BA | 108.1 |
C5A—C9A—H9AA | 108.3 | C1B—C9B—H9BA | 108.1 |
N3A—C10A—H10A | 109.5 | N3B—C10B—H10D | 109.5 |
N3A—C10A—H10B | 109.5 | N3B—C10B—H10E | 109.5 |
H10A—C10A—H10B | 109.5 | H10D—C10B—H10E | 109.5 |
N3A—C10A—H10C | 109.5 | N3B—C10B—H10F | 109.5 |
H10A—C10A—H10C | 109.5 | H10D—C10B—H10F | 109.5 |
H10B—C10A—H10C | 109.5 | H10E—C10B—H10F | 109.5 |
C12A—C11A—C9A | 112.96 (17) | C12B—C11B—C9B | 113.16 (18) |
C12A—C11A—H11A | 109.0 | C12B—C11B—H11C | 108.9 |
C9A—C11A—H11A | 109.0 | C9B—C11B—H11C | 108.9 |
C12A—C11A—H11B | 109.0 | C12B—C11B—H11D | 108.9 |
C9A—C11A—H11B | 109.0 | C9B—C11B—H11D | 108.9 |
H11A—C11A—H11B | 107.8 | H11C—C11B—H11D | 107.8 |
O6A—C12A—C13A | 121.6 (2) | O6B—C12B—C13B | 120.93 (17) |
O6A—C12A—C11A | 120.49 (19) | O6B—C12B—C11B | 120.88 (18) |
C13A—C12A—C11A | 117.94 (19) | C13B—C12B—C11B | 118.16 (17) |
C18A—C13A—C14A | 119.4 (2) | C18B—C13B—C14B | 118.60 (19) |
C18A—C13A—C12A | 122.1 (2) | C18B—C13B—C12B | 123.05 (17) |
C14A—C13A—C12A | 118.5 (2) | C14B—C13B—C12B | 118.30 (19) |
C13A—C14A—C15A | 119.5 (3) | C15B—C14B—C13B | 121.0 (2) |
C13A—C14A—H14A | 120.2 | C15B—C14B—H14B | 119.5 |
C15A—C14A—H14A | 120.2 | C13B—C14B—H14B | 119.5 |
C16A—C15A—C14A | 120.1 (3) | C14B—C15B—C16B | 119.8 (2) |
C16A—C15A—H15A | 119.9 | C14B—C15B—H15B | 120.1 |
C14A—C15A—H15A | 119.9 | C16B—C15B—H15B | 120.1 |
C17A—C16A—C15A | 120.7 (3) | C15B—C16B—C17B | 120.5 (2) |
C17A—C16A—H16A | 119.7 | C15B—C16B—H16B | 119.8 |
C15A—C16A—H16A | 119.7 | C17B—C16B—H16B | 119.8 |
C16A—C17A—C18A | 120.1 (3) | C18B—C17B—C16B | 119.9 (2) |
C16A—C17A—H17A | 119.9 | C18B—C17B—H17B | 120.1 |
C18A—C17A—H17A | 119.9 | C16B—C17B—H17B | 120.1 |
C13A—C18A—C17A | 120.1 (3) | C17B—C18B—C13B | 120.2 (2) |
C13A—C18A—H18A | 120.0 | C17B—C18B—H18B | 119.9 |
C17A—C18A—H18A | 120.0 | C13B—C18B—H18B | 119.9 |
N1A—C1A—C9A—C5A | 173.81 (15) | N1B—C1B—C9B—C5B | −175.72 (17) |
N2A—C5A—C9A—C1A | 176.45 (15) | N2B—C5B—C9B—C1B | −176.40 (17) |
O1A—N1A—C1A—C8A | 25.3 (2) | O1B—N1B—C1B—C8B | −4.1 (3) |
O4A—N2A—C5A—C6A | 47.0 (3) | O4B—N2B—C5B—C6B | −58.9 (3) |
C4A—C5A—C9A—C11A | 172.19 (16) | C4B—C5B—C9B—C11B | −173.97 (16) |
C6A—C5A—C9A—C11A | −66.5 (2) | C6B—C5B—C9B—C11B | 66.0 (2) |
O2A—N1A—C1A—C8A | −157.03 (18) | O2B—N1B—C1B—C8B | 176.3 (2) |
O1A—N1A—C1A—C9A | 147.94 (19) | O1B—N1B—C1B—C9B | −125.3 (3) |
O2A—N1A—C1A—C9A | −34.4 (2) | O2B—N1B—C1B—C9B | 55.1 (3) |
O1A—N1A—C1A—C2A | −94.3 (2) | O1B—N1B—C1B—C2B | 115.9 (3) |
O2A—N1A—C1A—C2A | 83.4 (2) | O2B—N1B—C1B—C2B | −63.8 (3) |
C10A—N3A—C2A—C1A | −174.33 (18) | C10B—N3B—C2B—C1B | 172.99 (16) |
C4A—N3A—C2A—C1A | 60.8 (2) | C4B—N3B—C2B—C1B | −61.3 (2) |
C8A—C1A—C2A—N3A | 63.7 (2) | C8B—C1B—C2B—N3B | −61.9 (2) |
N1A—C1A—C2A—N3A | −177.21 (16) | N1B—C1B—C2B—N3B | 178.11 (16) |
C9A—C1A—C2A—N3A | −60.4 (2) | C9B—C1B—C2B—N3B | 61.0 (2) |
C2A—N3A—C4A—C5A | −63.3 (2) | C2B—N3B—C4B—C5B | 63.0 (2) |
C10A—N3A—C4A—C5A | 172.1 (2) | C10B—N3B—C4B—C5B | −171.71 (17) |
O3A—N2A—C5A—C4A | −16.0 (3) | O3B—N2B—C5B—C4B | 7.4 (3) |
O4A—N2A—C5A—C4A | 164.5 (2) | O4B—N2B—C5B—C4B | −174.49 (19) |
O3A—N2A—C5A—C9A | 104.4 (2) | O3B—N2B—C5B—C9B | −114.5 (3) |
O4A—N2A—C5A—C9A | −75.1 (2) | O4B—N2B—C5B—C9B | 63.6 (3) |
O3A—N2A—C5A—C6A | −133.5 (2) | O3B—N2B—C5B—C6B | 123.0 (3) |
N3A—C4A—C5A—N2A | −173.82 (18) | N3B—C4B—C5B—N2B | 172.83 (16) |
N3A—C4A—C5A—C9A | 66.4 (2) | N3B—C4B—C5B—C9B | −64.7 (2) |
N3A—C4A—C5A—C6A | −57.1 (2) | N3B—C4B—C5B—C6B | 58.3 (2) |
N2A—C5A—C6A—O5A | 38.3 (3) | N2B—C5B—C6B—O5B | −35.6 (3) |
C4A—C5A—C6A—O5A | −79.3 (3) | C4B—C5B—C6B—O5B | 81.1 (2) |
C9A—C5A—C6A—O5A | 158.5 (2) | C9B—C5B—C6B—O5B | −157.29 (19) |
N2A—C5A—C6A—C7A | −145.39 (19) | N2B—C5B—C6B—C7B | 147.7 (2) |
C4A—C5A—C6A—C7A | 97.0 (2) | C4B—C5B—C6B—C7B | −95.6 (2) |
C9A—C5A—C6A—C7A | −25.2 (3) | C9B—C5B—C6B—C7B | 26.0 (2) |
O5A—C6A—C7A—C8A | 170.1 (2) | O5B—C6B—C7B—C8B | −171.0 (2) |
C5A—C6A—C7A—C8A | −6.1 (3) | C5B—C6B—C7B—C8B | 5.5 (3) |
C6A—C7A—C8A—C1A | −0.3 (3) | C6B—C7B—C8B—C1B | 0.1 (4) |
N1A—C1A—C8A—C7A | 159.26 (19) | N1B—C1B—C8B—C7B | −156.7 (2) |
C9A—C1A—C8A—C7A | 38.0 (3) | C9B—C1B—C8B—C7B | −36.8 (3) |
C2A—C1A—C8A—C7A | −85.4 (2) | C2B—C1B—C8B—C7B | 86.3 (3) |
C8A—C1A—C9A—C11A | 61.6 (2) | N2B—C5B—C9B—C11B | −52.6 (2) |
N1A—C1A—C9A—C11A | −60.5 (2) | C4B—C5B—C9B—C1B | 62.3 (2) |
C2A—C1A—C9A—C11A | −174.45 (18) | C6B—C5B—C9B—C1B | −57.8 (2) |
C8A—C1A—C9A—C5A | −64.06 (19) | C8B—C1B—C9B—C11B | −63.6 (2) |
C2A—C1A—C9A—C5A | 59.9 (2) | N1B—C1B—C9B—C11B | 57.7 (2) |
N2A—C5A—C9A—C11A | 52.7 (2) | C2B—C1B—C9B—C11B | 173.40 (18) |
C4A—C5A—C9A—C1A | −64.05 (19) | C8B—C1B—C9B—C5B | 62.9 (2) |
C6A—C5A—C9A—C1A | 57.3 (2) | C2B—C1B—C9B—C5B | −60.1 (2) |
C1A—C9A—C11A—C12A | 152.83 (18) | C5B—C9B—C11B—C12B | 89.4 (2) |
C5A—C9A—C11A—C12A | −88.9 (2) | C1B—C9B—C11B—C12B | −151.50 (19) |
C9A—C11A—C12A—O6A | −13.0 (3) | C9B—C11B—C12B—O6B | 13.1 (3) |
C9A—C11A—C12A—C13A | 167.00 (18) | C9B—C11B—C12B—C13B | −169.02 (18) |
O6A—C12A—C13A—C18A | −165.7 (2) | O6B—C12B—C13B—C18B | −154.3 (2) |
C11A—C12A—C13A—C18A | 14.2 (3) | C11B—C12B—C13B—C18B | 27.8 (3) |
O6A—C12A—C13A—C14A | 13.4 (4) | O6B—C12B—C13B—C14B | 23.1 (3) |
C11A—C12A—C13A—C14A | −166.7 (2) | C11B—C12B—C13B—C14B | −154.8 (2) |
C18A—C13A—C14A—C15A | −1.7 (4) | C18B—C13B—C14B—C15B | −0.3 (3) |
C12A—C13A—C14A—C15A | 179.2 (3) | C12B—C13B—C14B—C15B | −177.9 (2) |
C13A—C14A—C15A—C16A | 1.9 (5) | C13B—C14B—C15B—C16B | 1.4 (4) |
C14A—C15A—C16A—C17A | −0.8 (5) | C14B—C15B—C16B—C17B | −0.9 (4) |
C15A—C16A—C17A—C18A | −0.6 (5) | C15B—C16B—C17B—C18B | −0.5 (4) |
C14A—C13A—C18A—C17A | 0.3 (4) | C16B—C17B—C18B—C13B | 1.5 (4) |
C12A—C13A—C18A—C17A | 179.4 (2) | C14B—C13B—C18B—C17B | −1.1 (3) |
C16A—C17A—C18A—C13A | 0.8 (4) | C12B—C13B—C18B—C17B | 176.3 (2) |
Experimental details
Crystal data | |
Chemical formula | C17H17N3O6 |
Mr | 359.34 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 1702.9 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.50 × 0.30 × 0.30 |
Data collection | |
Diffractometer | Siemens P3 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6198, 5875, 4198 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.169, 0.95 |
No. of reflections | 5875 |
No. of parameters | 469 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.27 |
Computer programs: P3 (Siemens, 1989), XDISK (Siemens, 1991), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL97.
N1A—C1A—C9A—C5A | 173.81 (15) | N1B—C1B—C9B—C5B | −175.72 (17) |
N2A—C5A—C9A—C1A | 176.45 (15) | N2B—C5B—C9B—C1B | −176.40 (17) |
O1A—N1A—C1A—C8A | 25.3 (2) | O1B—N1B—C1B—C8B | −4.1 (3) |
O4A—N2A—C5A—C6A | 47.0 (3) | O4B—N2B—C5B—C6B | −58.9 (3) |
C4A—C5A—C9A—C11A | 172.19 (16) | C4B—C5B—C9B—C11B | −173.97 (16) |
C6A—C5A—C9A—C11A | −66.5 (2) | C6B—C5B—C9B—C11B | 66.0 (2) |
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).