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The title compound, (2S)-1-{[(4S)-4-benzyl-2-oxo-1,3-oxa­zolidin-3-yl]carbonyl}-1,2-di­hydro­quinoline-2-carbo­nitrile, C21H17N3O3, is the result of a diastereoselective Reissert-type reaction performed on a quinoline ring bearing a 4-benzyl oxazolidinone ring as chiral auxiliary. By means of X-ray analysis and according to the known S configuration at the C atom to which the benzyl group is attached, the S configuration at the C atom to which the nitrile group is attached was determined.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802016677/dn6038sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802016677/dn6038Isup2.hkl
Contains datablock I

CCDC reference: 198964

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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


Red Alert 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?)
Yellow Alert 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

Comment top

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).

Experimental top

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.

Refinement top

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.

Computing details top

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.

Figures top
[Figure 1] Fig. 1. Molecular structure (molecule a), showing 50% probability displacement ellipsoids. H are omitted for clarity.
(I) top
Crystal data top
C21H17N3O3F(000) = 752
Mr = 359.4Dx = 1.294 (1) Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ybCell parameters from 70335 reflections
a = 10.7330 (5) Åθ = 2.9–32.0°
b = 12.6853 (5) ŵ = 0.09 mm1
c = 14.0824 (5) ÅT = 298 K
β = 105.875 (3)°Block, colourless
V = 1844.21 (13) Å30.46 × 0.26 × 0.23 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
3918 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromatorRint = 0.054
Detector resolution: 9 pixels mm-1θmax = 32.0°, θmin = 3.0°
ϕ and ω scansh = 1616
68549 measured reflectionsk = 1818
4422 independent reflectionsl = 2021
Refinement top
Refinement on F2Weighting 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) = 0.085Δρmax = 0.14 e Å3
S = 1.57Δρmin = 0.12 e Å3
4422 reflectionsExtinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
487 parametersExtinction coefficient: 5.5 (5)
H-atom parameters not refinedAbsolute structure: from known (S)-configuration at C14
Crystal data top
C21H17N3O3V = 1844.21 (13) Å3
Mr = 359.4Z = 4
Monoclinic, P21Mo Kα radiation
a = 10.7330 (5) ŵ = 0.09 mm1
b = 12.6853 (5) ÅT = 298 K
c = 14.0824 (5) Å0.46 × 0.26 × 0.23 mm
β = 105.875 (3)°
Data collection top
Nonius KappaCCD
diffractometer
3918 reflections with I > 2σ(I)
68549 measured reflectionsRint = 0.054
4422 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.035H-atom parameters not refined
wR(F2) = 0.085Δρmax = 0.14 e Å3
S = 1.57Δρmin = 0.12 e Å3
4422 reflectionsAbsolute structure: from known (S)-configuration at C14
487 parameters
Special details top

Refinement. Owing to the absence of atom types > Si, the Friedel pairs have been merged prior to refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1a0.01873 (13)0.55940.62059 (9)0.0499 (4)
O2a0.02922 (16)0.22199 (14)0.57898 (11)0.0594 (5)
O3a0.09094 (13)0.27146 (14)0.72847 (10)0.0555 (5)
N1a0.20283 (14)0.48219 (15)0.71307 (11)0.0470 (5)
N2a0.04755 (14)0.38557 (14)0.59405 (10)0.0395 (5)
N3a0.3976 (2)0.6936 (2)0.7233 (2)0.0890 (10)
C1a0.22969 (18)0.5754 (2)0.77777 (14)0.0514 (7)
C2a0.2813 (2)0.5404 (2)0.88391 (15)0.0632 (8)
C3a0.3500 (2)0.4531 (2)0.90379 (15)0.0656 (8)
C4a0.4784 (2)0.3164 (2)0.84249 (17)0.0652 (8)
C5a0.5035 (2)0.2605 (2)0.7667 (2)0.0705 (9)
C6a0.43115 (19)0.2784 (2)0.67123 (17)0.0630 (8)
C7a0.33263 (18)0.35159 (19)0.65101 (14)0.0510 (6)
C8a0.30409 (17)0.40628 (17)0.72811 (13)0.0446 (6)
C9a0.37837 (18)0.3909 (2)0.82519 (14)0.0525 (6)
C10a0.3234 (2)0.6441 (2)0.74737 (17)0.0592 (8)
C11a0.08652 (17)0.48104 (17)0.64241 (12)0.0392 (5)
C12a0.04270 (17)0.29102 (17)0.64369 (14)0.0433 (6)
C13a0.0709 (2)0.26866 (19)0.48166 (16)0.0623 (8)
C14a0.05244 (17)0.38641 (17)0.49871 (12)0.0414 (5)
C15a0.0108 (2)0.4429 (2)0.41699 (13)0.0537 (7)
C16a0.11654 (19)0.43629 (18)0.32056 (13)0.0477 (6)
C17a0.1060 (2)0.36601 (19)0.24795 (14)0.0565 (7)
C18a0.2043 (3)0.3568 (2)0.16157 (16)0.0810 (11)
C19a0.3136 (3)0.4168 (3)0.1473 (2)0.0921 (13)
C20a0.3253 (3)0.4867 (3)0.2179 (2)0.0947 (13)
C21a0.2263 (3)0.4972 (2)0.30500 (16)0.0697 (9)
O1b0.82100 (14)0.37937 (13)0.70072 (10)0.0538 (5)
O2b0.80661 (16)0.72104 (15)0.67889 (13)0.0701 (6)
O3b0.94559 (14)0.65663 (16)0.81503 (11)0.0615 (5)
N1b0.85680 (14)0.44609 (15)0.85528 (10)0.0438 (5)
N2b0.78192 (14)0.55415 (15)0.71540 (10)0.0440 (5)
N3b0.7892 (2)0.20178 (19)0.93247 (15)0.0700 (8)
C1b0.93530 (18)0.35390 (18)0.89668 (14)0.0467 (6)
C2b1.0395 (2)0.3836 (2)0.98871 (16)0.0582 (7)
C3b1.02673 (19)0.4673 (2)1.03982 (15)0.0600 (7)
C4b0.8805 (2)0.6016 (2)1.08060 (15)0.0572 (7)
C5b0.7646 (2)0.6559 (2)1.05735 (16)0.0636 (8)
C6b0.6750 (2)0.6369 (2)0.96756 (16)0.0597 (8)
C7b0.70157 (18)0.56677 (18)0.90029 (14)0.0498 (6)
C8b0.82111 (18)0.51663 (17)0.92278 (13)0.0429 (6)
C9b0.90993 (18)0.53142 (18)1.01481 (14)0.0475 (6)
C10b0.85268 (18)0.26756 (19)0.91676 (14)0.0486 (6)
C11b0.82027 (16)0.45367 (17)0.75464 (13)0.0418 (6)
C12b0.85477 (19)0.64449 (18)0.74489 (15)0.0501 (7)
C13b0.6960 (3)0.6833 (2)0.6055 (2)0.0853 (11)
C14b0.69883 (17)0.56450 (19)0.61431 (13)0.0482 (6)
C15b0.5670 (2)0.5142 (2)0.60182 (16)0.0626 (8)
C16b0.48105 (19)0.5182 (2)0.49839 (16)0.0568 (7)
C17b0.3843 (2)0.5920 (3)0.47061 (19)0.0791 (10)
C18b0.3031 (3)0.5946 (4)0.3744 (3)0.1064 (15)
C19b0.3220 (3)0.5239 (4)0.3078 (2)0.1100 (16)
C20b0.4192 (4)0.4485 (3)0.3333 (2)0.1012 (14)
C21b0.4981 (3)0.4467 (3)0.42909 (19)0.0770 (10)
Hc1a0.15110.61470.77030.061*
Hc2a0.26980.57530.94150.076*
Hc3a0.3780.43560.97270.078*
Hc4a0.53130.30310.90830.078*
Hc5a0.57210.20910.78080.085*
Hc6a0.44950.2390.61810.074*
Hc7a0.28430.36470.58360.061*
H1c13a0.16020.25130.45180.076*
H2c13a0.0190.24210.44130.076*
Hc14a0.12910.42480.50050.05*
H1c15a0.00680.51580.43460.065*
H2c15a0.06630.40980.40880.065*
Hc17a0.02930.32330.25710.068*
Hc18a0.19670.30810.11110.097*
Hc19a0.38240.40940.08780.11*
Hc20a0.40220.52880.20670.113*
Hc21a0.2340.54660.35490.084*
Hc1b0.97560.32910.84780.061*
Hc2b1.11910.34631.01660.076*
Hc3b1.10130.48141.09430.078*
Hc4b0.94210.61281.14380.078*
Hc5b0.74630.70641.10270.085*
Hc6b0.59290.67260.95170.074*
Hc7b0.63780.55330.83870.061*
H1c13b0.70190.70520.54130.076*
H2c13b0.61910.71220.61720.076*
Hc14b0.73030.52820.56540.05*
H1c15b0.57920.44130.62170.065*
H2c15b0.52430.55090.6440.065*
Hc17b0.37260.64180.51910.065*
Hc18b0.23440.64550.35410.097*
Hc19b0.26550.52660.24170.11*
Hc20b0.43130.39820.28570.113*
Hc21b0.5660.3950.44740.084*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1a0.0598 (7)0.0356 (7)0.0511 (7)0.0031 (6)0.0096 (6)0.0016 (6)
O2a0.0807 (10)0.0333 (6)0.0604 (8)0.0093 (7)0.0128 (7)0.0021 (6)
O3a0.0579 (8)0.0548 (8)0.0516 (8)0.0053 (7)0.0113 (6)0.0157 (6)
N1a0.0434 (8)0.0457 (8)0.0498 (8)0.0005 (7)0.0092 (7)0.0162 (7)
N2a0.0444 (8)0.0335 (7)0.0385 (7)0.0013 (6)0.0076 (6)0.0000 (6)
N3a0.0919 (15)0.0689 (13)0.1205 (19)0.0177 (12)0.0533 (14)0.0220 (13)
C1a0.0454 (9)0.0533 (11)0.0558 (11)0.0027 (9)0.0145 (8)0.0210 (9)
C2a0.0632 (12)0.0803 (15)0.0471 (11)0.0062 (12)0.0165 (10)0.0210 (11)
C3a0.0656 (13)0.0859 (17)0.0438 (10)0.0049 (13)0.0126 (9)0.0066 (11)
C4a0.0515 (11)0.0691 (14)0.0653 (13)0.0015 (11)0.0004 (10)0.0005 (11)
C5a0.0472 (11)0.0659 (14)0.0922 (17)0.0078 (10)0.0083 (11)0.0127 (13)
C6a0.0487 (11)0.0646 (13)0.0768 (15)0.0013 (10)0.0190 (10)0.0207 (12)
C7a0.0424 (9)0.0561 (11)0.0538 (11)0.0021 (9)0.0121 (8)0.0125 (9)
C8a0.0371 (8)0.0451 (10)0.0516 (10)0.0036 (7)0.0123 (8)0.0072 (8)
C9a0.0454 (10)0.0586 (11)0.0510 (10)0.0056 (9)0.0088 (8)0.0072 (9)
C10a0.0603 (12)0.0497 (11)0.0689 (13)0.0038 (10)0.0200 (11)0.0199 (10)
C11a0.0451 (9)0.0368 (8)0.0370 (8)0.0027 (7)0.0136 (7)0.0015 (7)
C12a0.0462 (9)0.0367 (9)0.0488 (11)0.0013 (7)0.0160 (8)0.0025 (8)
C13a0.0823 (15)0.0418 (10)0.0541 (12)0.0087 (11)0.0042 (11)0.0043 (9)
C14a0.0448 (9)0.0368 (8)0.0397 (8)0.0014 (7)0.0067 (7)0.0022 (7)
C15a0.0653 (12)0.0524 (11)0.0422 (10)0.0065 (10)0.0129 (9)0.0011 (9)
C16a0.0605 (11)0.0458 (10)0.0381 (9)0.0018 (9)0.0157 (8)0.0062 (8)
C17a0.0834 (14)0.0456 (10)0.0437 (10)0.0013 (10)0.0229 (10)0.0026 (8)
C18a0.133 (2)0.0686 (15)0.0406 (11)0.0338 (17)0.0218 (14)0.0039 (11)
C19a0.090 (2)0.116 (3)0.0550 (14)0.027 (2)0.0063 (14)0.0226 (16)
C20a0.0679 (16)0.122 (3)0.0895 (19)0.0220 (17)0.0135 (15)0.046 (2)
C21a0.0799 (15)0.0735 (15)0.0581 (13)0.0204 (13)0.0231 (12)0.0087 (11)
O1b0.0633 (8)0.0488 (7)0.0489 (7)0.0062 (7)0.0148 (6)0.0054 (6)
O2b0.0718 (10)0.0498 (8)0.0802 (10)0.0064 (8)0.0065 (8)0.0184 (8)
O3b0.0606 (8)0.0610 (9)0.0583 (8)0.0171 (7)0.0086 (7)0.0009 (7)
N1b0.0513 (8)0.0406 (8)0.0409 (8)0.0042 (7)0.0148 (7)0.0031 (6)
N2b0.0448 (7)0.0432 (8)0.0429 (8)0.0017 (7)0.0103 (6)0.0047 (7)
N3b0.0702 (12)0.0588 (11)0.0765 (13)0.0039 (10)0.0126 (10)0.0166 (10)
C1b0.0492 (10)0.0448 (10)0.0477 (10)0.0074 (8)0.0159 (8)0.0016 (8)
C2b0.0463 (10)0.0581 (12)0.0641 (12)0.0060 (10)0.0049 (9)0.0047 (11)
C3b0.0515 (11)0.0620 (13)0.0582 (12)0.0051 (10)0.0010 (9)0.0018 (11)
C4b0.0687 (12)0.0516 (11)0.0513 (11)0.0140 (10)0.0165 (10)0.0089 (9)
C5b0.0823 (15)0.0515 (11)0.0641 (13)0.0049 (11)0.0322 (12)0.0128 (10)
C6b0.0635 (12)0.0559 (11)0.0656 (12)0.0051 (10)0.0278 (10)0.0064 (10)
C7b0.0508 (10)0.0499 (11)0.0510 (10)0.0026 (9)0.0178 (8)0.0000 (9)
C8b0.0504 (10)0.0380 (9)0.0442 (10)0.0032 (8)0.0195 (8)0.0001 (7)
C9b0.0509 (10)0.0443 (10)0.0465 (10)0.0094 (8)0.0122 (8)0.0013 (8)
C10b0.0550 (10)0.0436 (10)0.0435 (10)0.0079 (9)0.0073 (8)0.0040 (8)
C11b0.0419 (9)0.0414 (10)0.0430 (9)0.0003 (8)0.0132 (7)0.0008 (8)
C12b0.0533 (10)0.0442 (10)0.0554 (11)0.0037 (9)0.0192 (10)0.0048 (9)
C13b0.0874 (18)0.0645 (15)0.0856 (18)0.0019 (14)0.0073 (15)0.0244 (14)
C14b0.0455 (9)0.0573 (11)0.0426 (9)0.0009 (9)0.0132 (8)0.0087 (9)
C15b0.0480 (11)0.0840 (16)0.0562 (12)0.0035 (11)0.0147 (9)0.0127 (11)
C16b0.0399 (10)0.0727 (13)0.0564 (11)0.0093 (9)0.0109 (9)0.0099 (10)
C17b0.0544 (12)0.109 (2)0.0728 (15)0.0105 (14)0.0163 (11)0.0116 (15)
C18b0.0540 (14)0.158 (3)0.096 (2)0.0110 (19)0.0012 (15)0.040 (2)
C19b0.0763 (19)0.171 (4)0.0641 (17)0.036 (2)0.0125 (15)0.013 (2)
C20b0.109 (2)0.116 (3)0.0711 (17)0.039 (2)0.0119 (17)0.0201 (18)
C21b0.0736 (15)0.0763 (17)0.0757 (16)0.0112 (14)0.0111 (13)0.0022 (14)
Geometric parameters (Å, º) top
O1a—C11a1.220 (2)O1b—C11b1.212 (3)
O2a—C12a1.345 (2)O2b—C12b1.346 (3)
O2a—C13a1.447 (3)O2b—C13b1.426 (3)
O3a—C12a1.190 (2)O3b—C12b1.193 (2)
N1a—C1a1.472 (3)N1b—C1b1.466 (3)
N1a—C8a1.424 (3)N1b—C8b1.432 (3)
N1a—C11a1.367 (2)N1b—C11b1.367 (2)
N2a—C11a1.396 (3)N2b—C11b1.405 (3)
N2a—C12a1.396 (3)N2b—C12b1.385 (3)
N2a—C14a1.4718 (19)N2b—C14b1.464 (2)
N3a—C10a1.136 (4)N3b—C10b1.137 (3)
C1a—C2a1.512 (3)C1b—C2b1.510 (3)
C1a—C10a1.480 (3)C1b—C10b1.484 (3)
C1a—Hc1a0.961C1b—Hc1b0.961
C2a—C3a1.317 (4)C2b—C3b1.311 (4)
C2a—Hc2a0.961C2b—Hc2b0.961
C3a—C9a1.457 (3)C3b—C9b1.454 (3)
C3a—Hc3a0.960C3b—Hc3b0.9619
C4a—C5a1.368 (4)C4b—C5b1.380 (3)
C4a—C9a1.401 (3)C4b—C9b1.383 (3)
C4a—Hc4a0.960C4b—Hc4b0.9631
C5a—C6a1.375 (3)C5b—C6b1.385 (3)
C5a—Hc5a0.963C5b—Hc5b0.962
C6a—C7a1.377 (3)C6b—C7b1.385 (3)
C6a—Hc6a0.964C6b—Hc6b0.961
C7a—C8a1.391 (3)C7b—C8b1.389 (3)
C7a—Hc7a0.9636C7b—Hc7b0.9619
C8a—C9a1.395 (2)C8b—C9b1.396 (2)
C13a—C14a1.517 (3)C13b—C14b1.512 (4)
C13a—H1c13a0.961C13b—H1c13b0.965
C13a—H2c13a0.959C13b—H2c13b0.957
C14a—C15a1.523 (3)C14b—C15b1.518 (3)
C14a—Hc14a0.962C14b—Hc14b0.963
C15a—C16a1.515 (2)C15b—C16b1.497 (3)
C15a—H1c15a0.963C15b—H1c15b0.965
C15a—H2c15a0.962C15b—H2c15b0.963
C16a—C17a1.384 (3)C16b—C17b1.373 (4)
C16a—C21a1.375 (4)C16b—C21b1.381 (4)
C17a—C18a1.380 (3)C17b—C18b1.397 (4)
C17a—Hc17a0.964C17b—Hc17b0.964
C18a—C19a1.366 (5)C18b—C19b1.352 (6)
C18a—Hc18a0.962C18b—Hc18b0.963
C19a—C20a1.365 (5)C19b—C20b1.388 (6)
C19a—Hc19a0.958C19b—Hc19b0.963
C20a—C21a1.392 (3)C20b—C21b1.383 (4)
C20a—Hc20a0.959C20b—Hc20b0.960
C21a—Hc21a0.962C21b—Hc21b0.961
C12a—O2a—C13a110.30 (18)C12b—O2b—C13b110.2 (2)
C1a—N1a—C8a116.02 (13)C1b—N1b—C8b117.62 (14)
C1a—N1a—C11a116.38 (17)C1b—N1b—C11b116.06 (17)
C8a—N1a—C11a127.51 (17)C8b—N1b—C11b126.26 (17)
C11a—N2a—C12a123.23 (14)C11b—N2b—C12b123.49 (14)
C11a—N2a—C14a119.02 (16)C11b—N2b—C14b119.90 (17)
C12a—N2a—C14a110.19 (15)C12b—N2b—C14b111.16 (17)
N1a—C1a—C2a109.5 (2)N1b—C1b—C2b110.65 (18)
N1a—C1a—C10a109.12 (18)N1b—C1b—C10b110.87 (16)
N1a—C1a—Hc1a109.38N1b—C1b—Hc1b107.38
C2a—C1a—C10a111.39 (16)C2b—C1b—C10b111.19 (17)
C2a—C1a—Hc1a109.5C2b—C1b—Hc1b108.89
C10a—C1a—Hc1a107.9C10b—C1b—Hc1b107.7
C1a—C2a—C3a119.3 (2)C1b—C2b—C3b120.61 (19)
C1a—C2a—Hc2a127.0C1b—C2b—Hc2b126.5
C3a—C2a—Hc2a113.7C3b—C2b—Hc2b112.89
C2a—C3a—C9a120.96 (19)C2b—C3b—C9b122.19 (17)
C2a—C3a—Hc3a114.3C2b—C3b—Hc3b113.5
C9a—C3a—Hc3a124.8C9b—C3b—Hc3b124.3
C5a—C4a—C9a121.3 (2)C5b—C4b—C9b121.25 (18)
C5a—C4a—Hc4a118.1C5b—C4b—Hc4b119.5
C9a—C4a—Hc4a120.6C9b—C4b—Hc4b119.3
C4a—C5a—C6a119.9 (2)C4b—C5b—C6b119.0 (2)
C4a—C5a—Hc5a119.6C4b—C5b—Hc5b120.6
C6a—C5a—Hc5a120.6C6b—C5b—Hc5b120.3
C5a—C6a—C7a120.6 (2)C5b—C6b—C7b121.0 (2)
C5a—C6a—Hc6a119.5C5b—C6b—Hc6b119.6
C7a—C6a—Hc6a119.8C7b—C6b—Hc6b119.41
C6a—C7a—C8a119.69 (18)C6b—C7b—C8b119.24 (16)
C6a—C7a—Hc7a119.7C6b—C7b—Hc7b120.13
C8a—C7a—Hc7a120.6C8b—C7b—Hc7b120.6
N1a—C8a—C7a122.89 (15)N1b—C8b—C7b122.21 (15)
N1a—C8a—C9a116.65 (18)N1b—C8b—C9b117.49 (17)
C7a—C8a—C9a120.42 (18)C7b—C8b—C9b120.27 (19)
C3a—C9a—C4a122.84 (18)C3b—C9b—C4b122.54 (17)
C3a—C9a—C8a119.12 (19)C3b—C9b—C8b118.31 (19)
C4a—C9a—C8a118.0 (2)C4b—C9b—C8b119.05 (18)
N3a—C10a—C1a177.4 (3)N3b—C10b—C1b179.6 (2)
O1a—C11a—N1a122.50 (18)O1b—C11b—N1b123.09 (19)
O1a—C11a—N2a120.34 (14)O1b—C11b—N2b120.69 (16)
N1a—C11a—N2a117.15 (17)N1b—C11b—N2b116.21 (18)
O2a—C12a—O3a123.8 (2)O2b—C12b—O3b123.5 (2)
O2a—C12a—N2a108.25 (15)O2b—C12b—N2b108.13 (15)
O3a—C12a—N2a128.00 (18)O3b—C12b—N2b128.4 (2)
O2a—C13a—C14a105.05 (16)O2b—C13b—C14b106.3 (2)
O2a—C13a—H1c13a109.5O2b—C13b—H1c13b109.1
O2a—C13a—H2c13a109.8O2b—C13b—H2c13b109.5
C14a—C13a—H1c13a111.5C14b—C13b—H1c13b111.0
C14a—C13a—H2c13a111.6C14b—C13b—H2c13b111.5
H1c13a—C13a—H2c13a109.4H1c13b—C13b—H2c13b109.4
N2a—C14a—C13a99.69 (15)N2b—C14b—C13b99.32 (18)
N2a—C14a—C15a113.66 (15)N2b—C14b—C15b112.05 (17)
N2a—C14a—Hc14a113.27N2b—C14b—Hc14b114.39
C13a—C14a—C15a113.32 (18)C13b—C14b—C15b114.3 (2)
C13a—C14a—Hc14a115.27C13b—C14b—Hc14b114.9
C15a—C14a—Hc14a102.22C15b—C14b—Hc14b102.39
C14a—C15a—C16a110.41 (17)C14b—C15b—C16b113.9 (2)
C14a—C15a—H1c15a109.54C14b—C15b—H1c15b108.71
C14a—C15a—H2c15a109.00C14b—C15b—H2c15b108.1
C16a—C15a—H1c15a109.24C16b—C15b—H1c15b108.3
C16a—C15a—H2c15a109.06C16b—C15b—H2c15b108.26
H1c15a—C15a—H2c15a109.6H1c15b—C15b—H2c15b109.5
C15a—C16a—C17a120.31 (19)C15b—C16b—C17b121.2 (2)
C15a—C16a—C21a120.73 (19)C15b—C16b—C21b120.0 (2)
C17a—C16a—C21a118.92 (17)C17b—C16b—C21b118.9 (2)
C16a—C17a—C18a120.6 (2)C16b—C17b—C18b121.0 (3)
C16a—C17a—Hc17a120.17C16b—C17b—Hc17b118.7
C18a—C17a—Hc17a119.3C18b—C17b—Hc17b120.3
C17a—C18a—C19a120.1 (3)C17b—C18b—C19b119.0 (3)
C17a—C18a—Hc18a120.5C17b—C18b—Hc18b121.8
C19a—C18a—Hc18a119.4C19b—C18b—Hc18b119.1
C18a—C19a—C20a120.1 (2)C18b—C19b—C20b121.5 (3)
C18a—C19a—Hc19a120.0C18b—C19b—Hc19b118.2
C20a—C19a—Hc19a119.9C20b—C19b—Hc19b120.3
C19a—C20a—C21a120.2 (3)C19b—C20b—C21b118.7 (3)
C19a—C20a—Hc20a119.2C19b—C20b—Hc20b120.9
C21a—C20a—Hc20a120.5C21b—C20b—Hc20b120.4
C16a—C21a—C20a120.1 (3)C16b—C21b—C20b120.9 (3)
C16a—C21a—Hc21a119.4C16b—C21b—Hc21b119.7
C20a—C21a—Hc21a120.5C20b—C21b—Hc21b119.3
N1a—C11a—N2a—C12a52.5 (3)C11b—N2b—C12b—O3b13.1 (4)
N1b—C11b—N2b—C12b50.6 (3)C1a—N1a—C11a—O1a13.5 (3)
C11a—N2a—C12a—O3a15.3 (3)C1b—N1b—C11b—O1b18.8 (3)

Experimental details

Crystal data
Chemical formulaC21H17N3O3
Mr359.4
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)10.7330 (5), 12.6853 (5), 14.0824 (5)
β (°) 105.875 (3)
V3)1844.21 (13)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.46 × 0.26 × 0.23
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
68549, 4422, 3918
Rint0.054
(sin θ/λ)max1)0.746
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.085, 1.57
No. of reflections4422
No. of parameters487
No. of restraints?
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å3)0.14, 0.12
Absolute structureFrom 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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