Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802016677/dn6038sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802016677/dn6038Isup2.hkl |
CCDC reference: 198964
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.035
- wR factor = 0.085
- Data-to-parameter ratio = 9.1
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level A:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 32.04 From the CIF: _reflns_number_total 4422 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 6672 Completeness (_total/calc) 66.28% Alert A: < 85% complete (theta max?)
Alert Level C:
PLAT_162 Alert C Missing or Zero su (esd) on y-coordinate for . O1A General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 32.04 From the CIF: _reflns_number_total 4422 Count of symmetry unique reflns 6672 Completeness (_total/calc) 66.28% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
1 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
To a solution of quinoline (1.00 mmol) and (4S)-4-benzyl-2-oxo-oxazolidine-3-carbonyl chloride (1.10 mmol) in anhydrous CH2Cl2 (2 ml) was added trimethylsilyl cyanide (2.00 mmol). The reaction mixture was then stirred at room temperature for 16 h. Water (3 ml) was added and the aqueous phase was extracted with CH2Cl2 (3 x 5 ml). The CH2Cl2 extracts were combined, washed with brine (10 ml), dried over anhydrous MgSO4, filtered and concentrated. The crude mixture was flash-chromatographed on silica (eluent: CH2Cl2) to afford (Ia) (175 mg, 49%) along with its diastereomer (Ib) (140 mg, 39%). Single crystals of (Ia) suitable for X-ray analysis were obtained by slow evaporation from CH2Cl2 at room temperature.
Since no atoms heavier than Si are present in the structure, Friedel-pair reflections were merged. All non-H atoms were refined with anisotropic atomic displacement parameters. H atoms were found initially in difference Fourier maps and then fixed at calculated positions. A riding isotropic displacement parameter was used for all hydrogen atoms.
Data collection: Collect (Nonius, 1998); cell refinement: HKL SCALEPACK; data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 1995); program(s) used to refine structure: JANA2000 (Petricek & Dusek, 2000); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: JANA2000.
Fig. 1. Molecular structure (molecule a), showing 50% probability displacement ellipsoids. H are omitted for clarity. |
C21H17N3O3 | F(000) = 752 |
Mr = 359.4 | Dx = 1.294 (1) Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P 2yb | Cell parameters from 70335 reflections |
a = 10.7330 (5) Å | θ = 2.9–32.0° |
b = 12.6853 (5) Å | µ = 0.09 mm−1 |
c = 14.0824 (5) Å | T = 298 K |
β = 105.875 (3)° | Block, colourless |
V = 1844.21 (13) Å3 | 0.46 × 0.26 × 0.23 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 3918 reflections with I > 2σ(I) |
Horizonally mounted graphite crystal monochromator | Rint = 0.054 |
Detector resolution: 9 pixels mm-1 | θmax = 32.0°, θmin = 3.0° |
ϕ and ω scans | h = −16→16 |
68549 measured reflections | k = −18→18 |
4422 independent reflections | l = −20→21 |
Refinement on F2 | Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.001296I2] |
R[F2 > 2σ(F2)] = 0.035 | (Δ/σ)max = 0.001 |
wR(F2) = 0.085 | Δρmax = 0.14 e Å−3 |
S = 1.57 | Δρmin = −0.12 e Å−3 |
4422 reflections | Extinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974) |
487 parameters | Extinction coefficient: 5.5 (5) |
H-atom parameters not refined | Absolute structure: from known (S)-configuration at C14 |
C21H17N3O3 | V = 1844.21 (13) Å3 |
Mr = 359.4 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 10.7330 (5) Å | µ = 0.09 mm−1 |
b = 12.6853 (5) Å | T = 298 K |
c = 14.0824 (5) Å | 0.46 × 0.26 × 0.23 mm |
β = 105.875 (3)° |
Nonius KappaCCD diffractometer | 3918 reflections with I > 2σ(I) |
68549 measured reflections | Rint = 0.054 |
4422 independent reflections |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters not refined |
wR(F2) = 0.085 | Δρmax = 0.14 e Å−3 |
S = 1.57 | Δρmin = −0.12 e Å−3 |
4422 reflections | Absolute structure: from known (S)-configuration at C14 |
487 parameters |
Refinement. Owing to the absence of atom types > Si, the Friedel pairs have been merged prior to refinement. |
x | y | z | Uiso*/Ueq | ||
O1a | 0.01873 (13) | 0.5594 | 0.62059 (9) | 0.0499 (4) | |
O2a | −0.02922 (16) | 0.22199 (14) | 0.57898 (11) | 0.0594 (5) | |
O3a | 0.09094 (13) | 0.27146 (14) | 0.72847 (10) | 0.0555 (5) | |
N1a | 0.20283 (14) | 0.48219 (15) | 0.71307 (11) | 0.0470 (5) | |
N2a | 0.04755 (14) | 0.38557 (14) | 0.59405 (10) | 0.0395 (5) | |
N3a | 0.3976 (2) | 0.6936 (2) | 0.7233 (2) | 0.0890 (10) | |
C1a | 0.22969 (18) | 0.5754 (2) | 0.77777 (14) | 0.0514 (7) | |
C2a | 0.2813 (2) | 0.5404 (2) | 0.88391 (15) | 0.0632 (8) | |
C3a | 0.3500 (2) | 0.4531 (2) | 0.90379 (15) | 0.0656 (8) | |
C4a | 0.4784 (2) | 0.3164 (2) | 0.84249 (17) | 0.0652 (8) | |
C5a | 0.5035 (2) | 0.2605 (2) | 0.7667 (2) | 0.0705 (9) | |
C6a | 0.43115 (19) | 0.2784 (2) | 0.67123 (17) | 0.0630 (8) | |
C7a | 0.33263 (18) | 0.35159 (19) | 0.65101 (14) | 0.0510 (6) | |
C8a | 0.30409 (17) | 0.40628 (17) | 0.72811 (13) | 0.0446 (6) | |
C9a | 0.37837 (18) | 0.3909 (2) | 0.82519 (14) | 0.0525 (6) | |
C10a | 0.3234 (2) | 0.6441 (2) | 0.74737 (17) | 0.0592 (8) | |
C11a | 0.08652 (17) | 0.48104 (17) | 0.64241 (12) | 0.0392 (5) | |
C12a | 0.04270 (17) | 0.29102 (17) | 0.64369 (14) | 0.0433 (6) | |
C13a | −0.0709 (2) | 0.26866 (19) | 0.48166 (16) | 0.0623 (8) | |
C14a | −0.05244 (17) | 0.38641 (17) | 0.49871 (12) | 0.0414 (5) | |
C15a | −0.0108 (2) | 0.4429 (2) | 0.41699 (13) | 0.0537 (7) | |
C16a | −0.11654 (19) | 0.43629 (18) | 0.32056 (13) | 0.0477 (6) | |
C17a | −0.1060 (2) | 0.36601 (19) | 0.24795 (14) | 0.0565 (7) | |
C18a | −0.2043 (3) | 0.3568 (2) | 0.16157 (16) | 0.0810 (11) | |
C19a | −0.3136 (3) | 0.4168 (3) | 0.1473 (2) | 0.0921 (13) | |
C20a | −0.3253 (3) | 0.4867 (3) | 0.2179 (2) | 0.0947 (13) | |
C21a | −0.2263 (3) | 0.4972 (2) | 0.30500 (16) | 0.0697 (9) | |
O1b | 0.82100 (14) | 0.37937 (13) | 0.70072 (10) | 0.0538 (5) | |
O2b | 0.80661 (16) | 0.72104 (15) | 0.67889 (13) | 0.0701 (6) | |
O3b | 0.94559 (14) | 0.65663 (16) | 0.81503 (11) | 0.0615 (5) | |
N1b | 0.85680 (14) | 0.44609 (15) | 0.85528 (10) | 0.0438 (5) | |
N2b | 0.78192 (14) | 0.55415 (15) | 0.71540 (10) | 0.0440 (5) | |
N3b | 0.7892 (2) | 0.20178 (19) | 0.93247 (15) | 0.0700 (8) | |
C1b | 0.93530 (18) | 0.35390 (18) | 0.89668 (14) | 0.0467 (6) | |
C2b | 1.0395 (2) | 0.3836 (2) | 0.98871 (16) | 0.0582 (7) | |
C3b | 1.02673 (19) | 0.4673 (2) | 1.03982 (15) | 0.0600 (7) | |
C4b | 0.8805 (2) | 0.6016 (2) | 1.08060 (15) | 0.0572 (7) | |
C5b | 0.7646 (2) | 0.6559 (2) | 1.05735 (16) | 0.0636 (8) | |
C6b | 0.6750 (2) | 0.6369 (2) | 0.96756 (16) | 0.0597 (8) | |
C7b | 0.70157 (18) | 0.56677 (18) | 0.90029 (14) | 0.0498 (6) | |
C8b | 0.82111 (18) | 0.51663 (17) | 0.92278 (13) | 0.0429 (6) | |
C9b | 0.90993 (18) | 0.53142 (18) | 1.01481 (14) | 0.0475 (6) | |
C10b | 0.85268 (18) | 0.26756 (19) | 0.91676 (14) | 0.0486 (6) | |
C11b | 0.82027 (16) | 0.45367 (17) | 0.75464 (13) | 0.0418 (6) | |
C12b | 0.85477 (19) | 0.64449 (18) | 0.74489 (15) | 0.0501 (7) | |
C13b | 0.6960 (3) | 0.6833 (2) | 0.6055 (2) | 0.0853 (11) | |
C14b | 0.69883 (17) | 0.56450 (19) | 0.61431 (13) | 0.0482 (6) | |
C15b | 0.5670 (2) | 0.5142 (2) | 0.60182 (16) | 0.0626 (8) | |
C16b | 0.48105 (19) | 0.5182 (2) | 0.49839 (16) | 0.0568 (7) | |
C17b | 0.3843 (2) | 0.5920 (3) | 0.47061 (19) | 0.0791 (10) | |
C18b | 0.3031 (3) | 0.5946 (4) | 0.3744 (3) | 0.1064 (15) | |
C19b | 0.3220 (3) | 0.5239 (4) | 0.3078 (2) | 0.1100 (16) | |
C20b | 0.4192 (4) | 0.4485 (3) | 0.3333 (2) | 0.1012 (14) | |
C21b | 0.4981 (3) | 0.4467 (3) | 0.42909 (19) | 0.0770 (10) | |
Hc1a | 0.1511 | 0.6147 | 0.7703 | 0.061* | |
Hc2a | 0.2698 | 0.5753 | 0.9415 | 0.076* | |
Hc3a | 0.378 | 0.4356 | 0.9727 | 0.078* | |
Hc4a | 0.5313 | 0.3031 | 0.9083 | 0.078* | |
Hc5a | 0.5721 | 0.2091 | 0.7808 | 0.085* | |
Hc6a | 0.4495 | 0.239 | 0.6181 | 0.074* | |
Hc7a | 0.2843 | 0.3647 | 0.5836 | 0.061* | |
H1c13a | −0.1602 | 0.2513 | 0.4518 | 0.076* | |
H2c13a | −0.019 | 0.2421 | 0.4413 | 0.076* | |
Hc14a | −0.1291 | 0.4248 | 0.5005 | 0.05* | |
H1c15a | 0.0068 | 0.5158 | 0.4346 | 0.065* | |
H2c15a | 0.0663 | 0.4098 | 0.4088 | 0.065* | |
Hc17a | −0.0293 | 0.3233 | 0.2571 | 0.068* | |
Hc18a | −0.1967 | 0.3081 | 0.1111 | 0.097* | |
Hc19a | −0.3824 | 0.4094 | 0.0878 | 0.11* | |
Hc20a | −0.4022 | 0.5288 | 0.2067 | 0.113* | |
Hc21a | −0.234 | 0.5466 | 0.3549 | 0.084* | |
Hc1b | 0.9756 | 0.3291 | 0.8478 | 0.061* | |
Hc2b | 1.1191 | 0.3463 | 1.0166 | 0.076* | |
Hc3b | 1.1013 | 0.4814 | 1.0943 | 0.078* | |
Hc4b | 0.9421 | 0.6128 | 1.1438 | 0.078* | |
Hc5b | 0.7463 | 0.7064 | 1.1027 | 0.085* | |
Hc6b | 0.5929 | 0.6726 | 0.9517 | 0.074* | |
Hc7b | 0.6378 | 0.5533 | 0.8387 | 0.061* | |
H1c13b | 0.7019 | 0.7052 | 0.5413 | 0.076* | |
H2c13b | 0.6191 | 0.7122 | 0.6172 | 0.076* | |
Hc14b | 0.7303 | 0.5282 | 0.5654 | 0.05* | |
H1c15b | 0.5792 | 0.4413 | 0.6217 | 0.065* | |
H2c15b | 0.5243 | 0.5509 | 0.644 | 0.065* | |
Hc17b | 0.3726 | 0.6418 | 0.5191 | 0.065* | |
Hc18b | 0.2344 | 0.6455 | 0.3541 | 0.097* | |
Hc19b | 0.2655 | 0.5266 | 0.2417 | 0.11* | |
Hc20b | 0.4313 | 0.3982 | 0.2857 | 0.113* | |
Hc21b | 0.566 | 0.395 | 0.4474 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1a | 0.0598 (7) | 0.0356 (7) | 0.0511 (7) | 0.0031 (6) | 0.0096 (6) | −0.0016 (6) |
O2a | 0.0807 (10) | 0.0333 (6) | 0.0604 (8) | −0.0093 (7) | 0.0128 (7) | 0.0021 (6) |
O3a | 0.0579 (8) | 0.0548 (8) | 0.0516 (8) | 0.0053 (7) | 0.0113 (6) | 0.0157 (6) |
N1a | 0.0434 (8) | 0.0457 (8) | 0.0498 (8) | −0.0005 (7) | 0.0092 (7) | −0.0162 (7) |
N2a | 0.0444 (8) | 0.0335 (7) | 0.0385 (7) | −0.0013 (6) | 0.0076 (6) | 0.0000 (6) |
N3a | 0.0919 (15) | 0.0689 (13) | 0.1205 (19) | −0.0177 (12) | 0.0533 (14) | −0.0220 (13) |
C1a | 0.0454 (9) | 0.0533 (11) | 0.0558 (11) | −0.0027 (9) | 0.0145 (8) | −0.0210 (9) |
C2a | 0.0632 (12) | 0.0803 (15) | 0.0471 (11) | −0.0062 (12) | 0.0165 (10) | −0.0210 (11) |
C3a | 0.0656 (13) | 0.0859 (17) | 0.0438 (10) | −0.0049 (13) | 0.0126 (9) | −0.0066 (11) |
C4a | 0.0515 (11) | 0.0691 (14) | 0.0653 (13) | 0.0015 (11) | −0.0004 (10) | 0.0005 (11) |
C5a | 0.0472 (11) | 0.0659 (14) | 0.0922 (17) | 0.0078 (10) | 0.0083 (11) | −0.0127 (13) |
C6a | 0.0487 (11) | 0.0646 (13) | 0.0768 (15) | 0.0013 (10) | 0.0190 (10) | −0.0207 (12) |
C7a | 0.0424 (9) | 0.0561 (11) | 0.0538 (11) | −0.0021 (9) | 0.0121 (8) | −0.0125 (9) |
C8a | 0.0371 (8) | 0.0451 (10) | 0.0516 (10) | −0.0036 (7) | 0.0123 (8) | −0.0072 (8) |
C9a | 0.0454 (10) | 0.0586 (11) | 0.0510 (10) | −0.0056 (9) | 0.0088 (8) | −0.0072 (9) |
C10a | 0.0603 (12) | 0.0497 (11) | 0.0689 (13) | −0.0038 (10) | 0.0200 (11) | −0.0199 (10) |
C11a | 0.0451 (9) | 0.0368 (8) | 0.0370 (8) | −0.0027 (7) | 0.0136 (7) | −0.0015 (7) |
C12a | 0.0462 (9) | 0.0367 (9) | 0.0488 (11) | 0.0013 (7) | 0.0160 (8) | 0.0025 (8) |
C13a | 0.0823 (15) | 0.0418 (10) | 0.0541 (12) | −0.0087 (11) | 0.0042 (11) | −0.0043 (9) |
C14a | 0.0448 (9) | 0.0368 (8) | 0.0397 (8) | −0.0014 (7) | 0.0067 (7) | −0.0022 (7) |
C15a | 0.0653 (12) | 0.0524 (11) | 0.0422 (10) | −0.0065 (10) | 0.0129 (9) | 0.0011 (9) |
C16a | 0.0605 (11) | 0.0458 (10) | 0.0381 (9) | 0.0018 (9) | 0.0157 (8) | 0.0062 (8) |
C17a | 0.0834 (14) | 0.0456 (10) | 0.0437 (10) | 0.0013 (10) | 0.0229 (10) | 0.0026 (8) |
C18a | 0.133 (2) | 0.0686 (15) | 0.0406 (11) | −0.0338 (17) | 0.0218 (14) | −0.0039 (11) |
C19a | 0.090 (2) | 0.116 (3) | 0.0550 (14) | −0.027 (2) | −0.0063 (14) | 0.0226 (16) |
C20a | 0.0679 (16) | 0.122 (3) | 0.0895 (19) | 0.0220 (17) | 0.0135 (15) | 0.046 (2) |
C21a | 0.0799 (15) | 0.0735 (15) | 0.0581 (13) | 0.0204 (13) | 0.0231 (12) | 0.0087 (11) |
O1b | 0.0633 (8) | 0.0488 (7) | 0.0489 (7) | 0.0062 (7) | 0.0148 (6) | −0.0054 (6) |
O2b | 0.0718 (10) | 0.0498 (8) | 0.0802 (10) | −0.0064 (8) | 0.0065 (8) | 0.0184 (8) |
O3b | 0.0606 (8) | 0.0610 (9) | 0.0583 (8) | −0.0171 (7) | 0.0086 (7) | 0.0009 (7) |
N1b | 0.0513 (8) | 0.0406 (8) | 0.0409 (8) | 0.0042 (7) | 0.0148 (7) | 0.0031 (6) |
N2b | 0.0448 (7) | 0.0432 (8) | 0.0429 (8) | −0.0017 (7) | 0.0103 (6) | 0.0047 (7) |
N3b | 0.0702 (12) | 0.0588 (11) | 0.0765 (13) | −0.0039 (10) | 0.0126 (10) | 0.0166 (10) |
C1b | 0.0492 (10) | 0.0448 (10) | 0.0477 (10) | 0.0074 (8) | 0.0159 (8) | 0.0016 (8) |
C2b | 0.0463 (10) | 0.0581 (12) | 0.0641 (12) | 0.0060 (10) | 0.0049 (9) | 0.0047 (11) |
C3b | 0.0515 (11) | 0.0620 (13) | 0.0582 (12) | −0.0051 (10) | 0.0010 (9) | −0.0018 (11) |
C4b | 0.0687 (12) | 0.0516 (11) | 0.0513 (11) | −0.0140 (10) | 0.0165 (10) | −0.0089 (9) |
C5b | 0.0823 (15) | 0.0515 (11) | 0.0641 (13) | −0.0049 (11) | 0.0322 (12) | −0.0128 (10) |
C6b | 0.0635 (12) | 0.0559 (11) | 0.0656 (12) | 0.0051 (10) | 0.0278 (10) | −0.0064 (10) |
C7b | 0.0508 (10) | 0.0499 (11) | 0.0510 (10) | 0.0026 (9) | 0.0178 (8) | 0.0000 (9) |
C8b | 0.0504 (10) | 0.0380 (9) | 0.0442 (10) | −0.0032 (8) | 0.0195 (8) | 0.0001 (7) |
C9b | 0.0509 (10) | 0.0443 (10) | 0.0465 (10) | −0.0094 (8) | 0.0122 (8) | 0.0013 (8) |
C10b | 0.0550 (10) | 0.0436 (10) | 0.0435 (10) | 0.0079 (9) | 0.0073 (8) | 0.0040 (8) |
C11b | 0.0419 (9) | 0.0414 (10) | 0.0430 (9) | −0.0003 (8) | 0.0132 (7) | 0.0008 (8) |
C12b | 0.0533 (10) | 0.0442 (10) | 0.0554 (11) | −0.0037 (9) | 0.0192 (10) | 0.0048 (9) |
C13b | 0.0874 (18) | 0.0645 (15) | 0.0856 (18) | −0.0019 (14) | −0.0073 (15) | 0.0244 (14) |
C14b | 0.0455 (9) | 0.0573 (11) | 0.0426 (9) | 0.0009 (9) | 0.0132 (8) | 0.0087 (9) |
C15b | 0.0480 (11) | 0.0840 (16) | 0.0562 (12) | −0.0035 (11) | 0.0147 (9) | 0.0127 (11) |
C16b | 0.0399 (10) | 0.0727 (13) | 0.0564 (11) | −0.0093 (9) | 0.0109 (9) | 0.0099 (10) |
C17b | 0.0544 (12) | 0.109 (2) | 0.0728 (15) | 0.0105 (14) | 0.0163 (11) | 0.0116 (15) |
C18b | 0.0540 (14) | 0.158 (3) | 0.096 (2) | 0.0110 (19) | 0.0012 (15) | 0.040 (2) |
C19b | 0.0763 (19) | 0.171 (4) | 0.0641 (17) | −0.036 (2) | −0.0125 (15) | 0.013 (2) |
C20b | 0.109 (2) | 0.116 (3) | 0.0711 (17) | −0.039 (2) | 0.0119 (17) | −0.0201 (18) |
C21b | 0.0736 (15) | 0.0763 (17) | 0.0757 (16) | −0.0112 (14) | 0.0111 (13) | −0.0022 (14) |
O1a—C11a | 1.220 (2) | O1b—C11b | 1.212 (3) |
O2a—C12a | 1.345 (2) | O2b—C12b | 1.346 (3) |
O2a—C13a | 1.447 (3) | O2b—C13b | 1.426 (3) |
O3a—C12a | 1.190 (2) | O3b—C12b | 1.193 (2) |
N1a—C1a | 1.472 (3) | N1b—C1b | 1.466 (3) |
N1a—C8a | 1.424 (3) | N1b—C8b | 1.432 (3) |
N1a—C11a | 1.367 (2) | N1b—C11b | 1.367 (2) |
N2a—C11a | 1.396 (3) | N2b—C11b | 1.405 (3) |
N2a—C12a | 1.396 (3) | N2b—C12b | 1.385 (3) |
N2a—C14a | 1.4718 (19) | N2b—C14b | 1.464 (2) |
N3a—C10a | 1.136 (4) | N3b—C10b | 1.137 (3) |
C1a—C2a | 1.512 (3) | C1b—C2b | 1.510 (3) |
C1a—C10a | 1.480 (3) | C1b—C10b | 1.484 (3) |
C1a—Hc1a | 0.961 | C1b—Hc1b | 0.961 |
C2a—C3a | 1.317 (4) | C2b—C3b | 1.311 (4) |
C2a—Hc2a | 0.961 | C2b—Hc2b | 0.961 |
C3a—C9a | 1.457 (3) | C3b—C9b | 1.454 (3) |
C3a—Hc3a | 0.960 | C3b—Hc3b | 0.9619 |
C4a—C5a | 1.368 (4) | C4b—C5b | 1.380 (3) |
C4a—C9a | 1.401 (3) | C4b—C9b | 1.383 (3) |
C4a—Hc4a | 0.960 | C4b—Hc4b | 0.9631 |
C5a—C6a | 1.375 (3) | C5b—C6b | 1.385 (3) |
C5a—Hc5a | 0.963 | C5b—Hc5b | 0.962 |
C6a—C7a | 1.377 (3) | C6b—C7b | 1.385 (3) |
C6a—Hc6a | 0.964 | C6b—Hc6b | 0.961 |
C7a—C8a | 1.391 (3) | C7b—C8b | 1.389 (3) |
C7a—Hc7a | 0.9636 | C7b—Hc7b | 0.9619 |
C8a—C9a | 1.395 (2) | C8b—C9b | 1.396 (2) |
C13a—C14a | 1.517 (3) | C13b—C14b | 1.512 (4) |
C13a—H1c13a | 0.961 | C13b—H1c13b | 0.965 |
C13a—H2c13a | 0.959 | C13b—H2c13b | 0.957 |
C14a—C15a | 1.523 (3) | C14b—C15b | 1.518 (3) |
C14a—Hc14a | 0.962 | C14b—Hc14b | 0.963 |
C15a—C16a | 1.515 (2) | C15b—C16b | 1.497 (3) |
C15a—H1c15a | 0.963 | C15b—H1c15b | 0.965 |
C15a—H2c15a | 0.962 | C15b—H2c15b | 0.963 |
C16a—C17a | 1.384 (3) | C16b—C17b | 1.373 (4) |
C16a—C21a | 1.375 (4) | C16b—C21b | 1.381 (4) |
C17a—C18a | 1.380 (3) | C17b—C18b | 1.397 (4) |
C17a—Hc17a | 0.964 | C17b—Hc17b | 0.964 |
C18a—C19a | 1.366 (5) | C18b—C19b | 1.352 (6) |
C18a—Hc18a | 0.962 | C18b—Hc18b | 0.963 |
C19a—C20a | 1.365 (5) | C19b—C20b | 1.388 (6) |
C19a—Hc19a | 0.958 | C19b—Hc19b | 0.963 |
C20a—C21a | 1.392 (3) | C20b—C21b | 1.383 (4) |
C20a—Hc20a | 0.959 | C20b—Hc20b | 0.960 |
C21a—Hc21a | 0.962 | C21b—Hc21b | 0.961 |
C12a—O2a—C13a | 110.30 (18) | C12b—O2b—C13b | 110.2 (2) |
C1a—N1a—C8a | 116.02 (13) | C1b—N1b—C8b | 117.62 (14) |
C1a—N1a—C11a | 116.38 (17) | C1b—N1b—C11b | 116.06 (17) |
C8a—N1a—C11a | 127.51 (17) | C8b—N1b—C11b | 126.26 (17) |
C11a—N2a—C12a | 123.23 (14) | C11b—N2b—C12b | 123.49 (14) |
C11a—N2a—C14a | 119.02 (16) | C11b—N2b—C14b | 119.90 (17) |
C12a—N2a—C14a | 110.19 (15) | C12b—N2b—C14b | 111.16 (17) |
N1a—C1a—C2a | 109.5 (2) | N1b—C1b—C2b | 110.65 (18) |
N1a—C1a—C10a | 109.12 (18) | N1b—C1b—C10b | 110.87 (16) |
N1a—C1a—Hc1a | 109.38 | N1b—C1b—Hc1b | 107.38 |
C2a—C1a—C10a | 111.39 (16) | C2b—C1b—C10b | 111.19 (17) |
C2a—C1a—Hc1a | 109.5 | C2b—C1b—Hc1b | 108.89 |
C10a—C1a—Hc1a | 107.9 | C10b—C1b—Hc1b | 107.7 |
C1a—C2a—C3a | 119.3 (2) | C1b—C2b—C3b | 120.61 (19) |
C1a—C2a—Hc2a | 127.0 | C1b—C2b—Hc2b | 126.5 |
C3a—C2a—Hc2a | 113.7 | C3b—C2b—Hc2b | 112.89 |
C2a—C3a—C9a | 120.96 (19) | C2b—C3b—C9b | 122.19 (17) |
C2a—C3a—Hc3a | 114.3 | C2b—C3b—Hc3b | 113.5 |
C9a—C3a—Hc3a | 124.8 | C9b—C3b—Hc3b | 124.3 |
C5a—C4a—C9a | 121.3 (2) | C5b—C4b—C9b | 121.25 (18) |
C5a—C4a—Hc4a | 118.1 | C5b—C4b—Hc4b | 119.5 |
C9a—C4a—Hc4a | 120.6 | C9b—C4b—Hc4b | 119.3 |
C4a—C5a—C6a | 119.9 (2) | C4b—C5b—C6b | 119.0 (2) |
C4a—C5a—Hc5a | 119.6 | C4b—C5b—Hc5b | 120.6 |
C6a—C5a—Hc5a | 120.6 | C6b—C5b—Hc5b | 120.3 |
C5a—C6a—C7a | 120.6 (2) | C5b—C6b—C7b | 121.0 (2) |
C5a—C6a—Hc6a | 119.5 | C5b—C6b—Hc6b | 119.6 |
C7a—C6a—Hc6a | 119.8 | C7b—C6b—Hc6b | 119.41 |
C6a—C7a—C8a | 119.69 (18) | C6b—C7b—C8b | 119.24 (16) |
C6a—C7a—Hc7a | 119.7 | C6b—C7b—Hc7b | 120.13 |
C8a—C7a—Hc7a | 120.6 | C8b—C7b—Hc7b | 120.6 |
N1a—C8a—C7a | 122.89 (15) | N1b—C8b—C7b | 122.21 (15) |
N1a—C8a—C9a | 116.65 (18) | N1b—C8b—C9b | 117.49 (17) |
C7a—C8a—C9a | 120.42 (18) | C7b—C8b—C9b | 120.27 (19) |
C3a—C9a—C4a | 122.84 (18) | C3b—C9b—C4b | 122.54 (17) |
C3a—C9a—C8a | 119.12 (19) | C3b—C9b—C8b | 118.31 (19) |
C4a—C9a—C8a | 118.0 (2) | C4b—C9b—C8b | 119.05 (18) |
N3a—C10a—C1a | 177.4 (3) | N3b—C10b—C1b | 179.6 (2) |
O1a—C11a—N1a | 122.50 (18) | O1b—C11b—N1b | 123.09 (19) |
O1a—C11a—N2a | 120.34 (14) | O1b—C11b—N2b | 120.69 (16) |
N1a—C11a—N2a | 117.15 (17) | N1b—C11b—N2b | 116.21 (18) |
O2a—C12a—O3a | 123.8 (2) | O2b—C12b—O3b | 123.5 (2) |
O2a—C12a—N2a | 108.25 (15) | O2b—C12b—N2b | 108.13 (15) |
O3a—C12a—N2a | 128.00 (18) | O3b—C12b—N2b | 128.4 (2) |
O2a—C13a—C14a | 105.05 (16) | O2b—C13b—C14b | 106.3 (2) |
O2a—C13a—H1c13a | 109.5 | O2b—C13b—H1c13b | 109.1 |
O2a—C13a—H2c13a | 109.8 | O2b—C13b—H2c13b | 109.5 |
C14a—C13a—H1c13a | 111.5 | C14b—C13b—H1c13b | 111.0 |
C14a—C13a—H2c13a | 111.6 | C14b—C13b—H2c13b | 111.5 |
H1c13a—C13a—H2c13a | 109.4 | H1c13b—C13b—H2c13b | 109.4 |
N2a—C14a—C13a | 99.69 (15) | N2b—C14b—C13b | 99.32 (18) |
N2a—C14a—C15a | 113.66 (15) | N2b—C14b—C15b | 112.05 (17) |
N2a—C14a—Hc14a | 113.27 | N2b—C14b—Hc14b | 114.39 |
C13a—C14a—C15a | 113.32 (18) | C13b—C14b—C15b | 114.3 (2) |
C13a—C14a—Hc14a | 115.27 | C13b—C14b—Hc14b | 114.9 |
C15a—C14a—Hc14a | 102.22 | C15b—C14b—Hc14b | 102.39 |
C14a—C15a—C16a | 110.41 (17) | C14b—C15b—C16b | 113.9 (2) |
C14a—C15a—H1c15a | 109.54 | C14b—C15b—H1c15b | 108.71 |
C14a—C15a—H2c15a | 109.00 | C14b—C15b—H2c15b | 108.1 |
C16a—C15a—H1c15a | 109.24 | C16b—C15b—H1c15b | 108.3 |
C16a—C15a—H2c15a | 109.06 | C16b—C15b—H2c15b | 108.26 |
H1c15a—C15a—H2c15a | 109.6 | H1c15b—C15b—H2c15b | 109.5 |
C15a—C16a—C17a | 120.31 (19) | C15b—C16b—C17b | 121.2 (2) |
C15a—C16a—C21a | 120.73 (19) | C15b—C16b—C21b | 120.0 (2) |
C17a—C16a—C21a | 118.92 (17) | C17b—C16b—C21b | 118.9 (2) |
C16a—C17a—C18a | 120.6 (2) | C16b—C17b—C18b | 121.0 (3) |
C16a—C17a—Hc17a | 120.17 | C16b—C17b—Hc17b | 118.7 |
C18a—C17a—Hc17a | 119.3 | C18b—C17b—Hc17b | 120.3 |
C17a—C18a—C19a | 120.1 (3) | C17b—C18b—C19b | 119.0 (3) |
C17a—C18a—Hc18a | 120.5 | C17b—C18b—Hc18b | 121.8 |
C19a—C18a—Hc18a | 119.4 | C19b—C18b—Hc18b | 119.1 |
C18a—C19a—C20a | 120.1 (2) | C18b—C19b—C20b | 121.5 (3) |
C18a—C19a—Hc19a | 120.0 | C18b—C19b—Hc19b | 118.2 |
C20a—C19a—Hc19a | 119.9 | C20b—C19b—Hc19b | 120.3 |
C19a—C20a—C21a | 120.2 (3) | C19b—C20b—C21b | 118.7 (3) |
C19a—C20a—Hc20a | 119.2 | C19b—C20b—Hc20b | 120.9 |
C21a—C20a—Hc20a | 120.5 | C21b—C20b—Hc20b | 120.4 |
C16a—C21a—C20a | 120.1 (3) | C16b—C21b—C20b | 120.9 (3) |
C16a—C21a—Hc21a | 119.4 | C16b—C21b—Hc21b | 119.7 |
C20a—C21a—Hc21a | 120.5 | C20b—C21b—Hc21b | 119.3 |
N1a—C11a—N2a—C12a | 52.5 (3) | C11b—N2b—C12b—O3b | −13.1 (4) |
N1b—C11b—N2b—C12b | 50.6 (3) | C1a—N1a—C11a—O1a | 13.5 (3) |
C11a—N2a—C12a—O3a | −15.3 (3) | C1b—N1b—C11b—O1b | 18.8 (3) |
Experimental details
Crystal data | |
Chemical formula | C21H17N3O3 |
Mr | 359.4 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 298 |
a, b, c (Å) | 10.7330 (5), 12.6853 (5), 14.0824 (5) |
β (°) | 105.875 (3) |
V (Å3) | 1844.21 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.46 × 0.26 × 0.23 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 68549, 4422, 3918 |
Rint | 0.054 |
(sin θ/λ)max (Å−1) | 0.746 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.085, 1.57 |
No. of reflections | 4422 |
No. of parameters | 487 |
No. of restraints | ? |
H-atom treatment | H-atom parameters not refined |
Δρmax, Δρmin (e Å−3) | 0.14, −0.12 |
Absolute structure | From known (S)-configuration at C14 |
Computer programs: Collect (Nonius, 1998), HKL SCALEPACK, HKL DENZO and SCALEPACK (Otwinowski & Minor 1997), SHELXTL (Sheldrick, 1995), JANA2000 (Petricek & Dusek, 2000), DIAMOND (Brandenburg & Berndt, 1999), JANA2000.
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The Reissert reaction (Reissert, 1905) consists of the 1,2-addition reaction of a cyano group to an N-acyl quinolinium salt (Duarte et al., 1991; Akiba et al., 1979; Abushanab et al., 1975). Recently, the first enantioselective Reissert reaction has been described by Takamura (2001) and applied to a synthesis of the potent NMDA receptor antagonist (-)-L-689,560 implicated in several neurodegenerative disorders (Leeson et al., 1992; Carling et al., 1993).
In the course of an ongoing project directed towards the asymmetric synthesis of alkaloids of biological interest, we have developed a new diastereoselective Reissert reaction using chiral oxazolidinones as chiral auxiliaries. Herein, we report the structure of a Reissert adduct, (I), isolated after reaction of trimethylsilyl cyanide with the in situ generated (4S)-1-(4-benzyl-2-oxo-oxazolidine-3-carbonyl)-quinolinium chloride. The absolute configuration of the newly created stereogenic carbon C1 could be deduced from the relative configurations of carbons C1 and C14 (see Scheme).
Both molecules are similar, as indicated by the following dihedral angles: 52.5 (3) and 50.6 (3)° for N1—C11—N2—C12, −15.3 (3) and −13.1 (4)° for C11—N2—C12—O3 and 13.5 (3) and 18.8 (3)° for C1—N1—C11—O1 (values for molecules a and b, respectively).