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The title mol­ecule, C26H20BrNO3S, contains a ring-fused 2-pyridinone framework substituted with a 4-bromo-phenyl-, a naphthalen-1-yl­methyl and a methoxy­carbonyl substituent. The main goal of this work was to confirm the stereochemistry for the methoxy­carbonyl substituent, which proved to be 3R. Moreover, the 4-bromo­phenyl substituent was shown to be rotated out of the plane of the 2-pyridinone ring, with a torsion angle of 61.2 (5)°. To allow the best packing arrangement, the naphthalen-1-yl­methyl substituent is pos­itioned to mediate an intermolecular π–π interaction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802011480/ob6142sup1.cif
Contains datablocks global, 5

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802011480/ob61425sup2.hkl
Contains datablock 5

CCDC reference: 193731

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.044
  • wR factor = 0.103
  • Data-to-parameter ratio = 14.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.49 From the CIF: _reflns_number_total 4234 Count of symmetry unique reflns 2652 Completeness (_total/calc) 159.65% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1582 Fraction of Friedel pairs measured 0.597 Are heavy atom types Z>Si present yes 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.

Computing details top

Data collection: COLLECT (Nonius, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

(5) top
Crystal data top
C26H20BrNO3SF(000) = 516
Mr = 506.40Dx = 1.553 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 9.5502 (5) ÅCell parameters from 8301 reflections
b = 8.6443 (5) Åθ = 4.5–27.5°
c = 13.1213 (6) ŵ = 2.02 mm1
β = 91.028 (3)°T = 120 K
V = 1083.05 (10) Å3Plate, colourless
Z = 20.25 × 0.13 × 0.03 mm
Data collection top
KappaCCD
diffractometer
3754 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.052
CCD scansθmax = 27.5°, θmin = 4.5°
Absorption correction: numerical
(Herrendorf et al., 1997)
h = 1212
Tmin = 0.566, Tmax = 0.815k = 1111
8301 measured reflectionsl = 1617
4234 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0225P)2 + 1.1354P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
4234 reflectionsΔρmax = 0.76 e Å3
289 parametersΔρmin = 0.52 e Å3
1 restraintAbsolute structure: (Flack, 1983), 1582 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.013 (10)
Special details top

Experimental. Spectroscopic data, Compond (2): IR λ 2773, 1653, 1564, 1381, 791 cm-1; 1H-NMR (CDCl3, 400 MHz) δ 12.77 (bs, 1H), 11.72 (bs, 1H), 7.49 (d, J=8.3 Hz, 2H), 7.33 (d, J=8.3 Hz, 2H), 4.61 (q, J=7.0 Hz, 2H), 4.00 (s, 2H), 1.44 (t, J=7.0 Hz, 3H); 13C NMR (CDCl3, 400 MHz) δ 176.6, 132.3, 131.2, 130.1, 122.6, 71.2, 38.6, 13.5;

Compound (3): [α]D +53° (c 0.91, CHCl3); IR λ 2951, 1739, 1618, 1487, 1435, 1201, 1012 cm-1; 1H NMR (CDCL3, 400 MHz) δ 7.41 (d, J=8.3 Hz, 2H), 7.14 (d, j=8.3 Hz, 2H), 5.07 (m, 1H), 3.86–3.74 (m, 5H), 3.54 (dd, J=11.3, 8.8 Hz, 1H), 3.46 (dd, J=11.2, 9.6 Hz, 1H); 13C NMR (CDCl3, 400 MHz) δ 172.8, 170.9, 134.4, 131.6, 130.6, 121.2, 77.7, 52.6, 39.9, 35.7; HRMS (FAB+) calcd for C12H12BrNO2S 313.9850, found 313.9854.

Compound (5): [α]D -134° (c1.26, CHCl3); IR λ 3039, 2953, 1745, 1649, 1479, 1205, 1007, 777 cm-1; 1H-NMR (CDCl3, 400 MHz) δ 7.83 (d, J=7.7 Hz, 1H), 7.75 (d, J=8.2 Hz, 1H), 7.59 (d, J=8.1 Hz, 1H), 7.52 (d, J=6.6 Hz, 2H), 7.48–7.34 (m, 3H), 7.22–7.14 (m, 3H), 5.86 (s, 1H), 5.61 (dd, J=11.2, 2.1 Hz, 1H), 4.03–3.87 (m, 2H), 3.82 (s, 3H), 3.68 (dd, J=11.8, 8.6 Hz, 1H), 3.47 (dd, J=11.8, 2.2 Hz, 1H); 13C NMR (CDCl3, 400 MHz) δ 168.3, 161.1, 154.0, 146.6, 135.1, 133.8, 133.5, 132.2, 131.9, 131.6, 131.4, 128.7, 127.7, 126.1,125.6, 125.4, 122.7, 115.5, 114.8, 63.5, 53.3, 36.8, 31.7; HRMS (FAB+) calcd. for C26H20BrNO3S 506.0426, found 506.0435.

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. Data for a crystal of the title compound was collected using a Bruker Nonius KappaCCD diffractometer. The data set showed monoclinic symmetry, the systematic absences 0k0: k=2n indicated the possible space groups P21 and P21/m of which the former, non-centrosymmetric one could be confirmed during the structure determination. Due to the shape of the crystal (thin plate) a numerical absorption correction was applied (Herrendorf, 1997). All non-hydrogen atoms could be localized using direct methods (SHELXS97) and were refined using anisotropic thermal parameters.

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
C10.2950 (5)0.5182 (5)0.5694 (3)0.0391 (10)
H1A0.35460.46910.61930.047*
H1B0.22190.57350.60310.047*
C20.3797 (5)0.6291 (6)0.5053 (3)0.0377 (9)
H20.47760.60450.51020.045*
C30.3919 (4)0.6984 (5)0.3219 (3)0.0337 (9)
C40.3528 (4)0.6548 (5)0.2199 (3)0.0320 (8)
H40.38640.71780.16530.038*
C50.2710 (4)0.5290 (5)0.1984 (3)0.0303 (8)
C60.2241 (5)0.4322 (5)0.2790 (3)0.0308 (9)
C70.2612 (4)0.4759 (5)0.3773 (3)0.0334 (8)
C80.1491 (4)0.2821 (5)0.2655 (3)0.0305 (9)
C90.0092 (4)0.2726 (5)0.2300 (3)0.0328 (10)
H90.03900.36430.20770.039*
C100.0597 (4)0.1306 (5)0.2274 (3)0.0352 (9)
H100.15440.12350.20190.042*
C110.0107 (5)0.0001 (5)0.2607 (3)0.0362 (9)
C120.1481 (5)0.0036 (5)0.2939 (3)0.0358 (9)
H120.19800.08780.31490.043*
C130.2160 (5)0.1452 (5)0.2969 (3)0.0318 (9)
H130.31130.14800.32130.038*
C140.2268 (5)0.4887 (5)0.0901 (3)0.0353 (9)
H14A0.12860.50930.08100.042*
H14B0.24440.38090.07830.042*
C150.2995 (4)0.5734 (5)0.0050 (3)0.0318 (8)
C160.3942 (4)0.4934 (5)0.0543 (3)0.0373 (9)
H160.41400.38660.04020.045*
C170.4650 (5)0.5665 (6)0.1351 (3)0.0389 (10)
H170.52990.50870.17510.047*
C180.4411 (4)0.7185 (6)0.1562 (3)0.0387 (10)
H180.48970.76690.21110.046*
C190.3455 (3)0.8050 (7)0.0989 (2)0.0328 (7)
C200.3199 (5)0.9645 (5)0.1194 (3)0.0386 (9)
H200.36861.01500.17350.046*
C210.2280 (5)1.0479 (5)0.0639 (3)0.0425 (10)
H210.21321.15530.07920.051*
C220.1528 (5)0.9754 (6)0.0142 (3)0.0430 (10)
H220.08811.03550.05290.052*
C230.1737 (4)0.8228 (6)0.0364 (3)0.0384 (10)
H230.12110.77600.09000.046*
C240.2718 (4)0.7321 (5)0.0183 (3)0.0325 (8)
C250.3567 (5)0.7897 (7)0.5439 (3)0.0433 (10)
C260.1871 (8)0.9856 (7)0.5625 (5)0.075 (2)
H26A0.09521.01330.53790.090*
H26B0.18580.97310.63520.090*
H26C0.25221.06570.54540.090*
Br10.08413 (5)0.19489 (6)0.25934 (3)0.04549 (14)
O10.4641 (3)0.8122 (5)0.3478 (2)0.0435 (6)
O20.4342 (4)0.8571 (4)0.6017 (3)0.0615 (10)
O30.2293 (4)0.8407 (4)0.5155 (2)0.0503 (9)
N130.3369 (4)0.6049 (4)0.3979 (2)0.0321 (7)
S10.21891 (16)0.37294 (16)0.48723 (9)0.0544 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.057 (3)0.032 (2)0.0281 (19)0.0011 (19)0.0023 (19)0.0002 (17)
C20.042 (2)0.043 (2)0.0286 (19)0.0004 (19)0.0014 (17)0.0020 (18)
C30.038 (2)0.032 (2)0.0311 (19)0.0042 (17)0.0017 (17)0.0022 (17)
C40.038 (2)0.030 (2)0.0283 (18)0.0014 (16)0.0060 (16)0.0047 (16)
C50.032 (2)0.034 (2)0.0252 (18)0.0037 (16)0.0058 (15)0.0030 (15)
C60.037 (2)0.026 (2)0.030 (2)0.0038 (17)0.0047 (17)0.0006 (16)
C70.040 (2)0.031 (2)0.0294 (19)0.0045 (17)0.0049 (16)0.0013 (16)
C80.0366 (18)0.030 (3)0.0247 (15)0.0003 (17)0.0049 (13)0.0031 (16)
C90.0356 (19)0.032 (3)0.0311 (18)0.0044 (15)0.0038 (15)0.0021 (16)
C100.034 (2)0.041 (2)0.0305 (19)0.0026 (18)0.0011 (16)0.0015 (18)
C110.048 (2)0.034 (2)0.0269 (19)0.0032 (18)0.0069 (17)0.0014 (17)
C120.047 (2)0.0282 (19)0.032 (2)0.0044 (18)0.0020 (18)0.0006 (17)
C130.031 (2)0.032 (2)0.032 (2)0.0032 (17)0.0027 (17)0.0010 (18)
C140.044 (2)0.036 (2)0.0260 (19)0.0047 (18)0.0005 (17)0.0025 (17)
C150.035 (2)0.034 (2)0.0271 (18)0.0035 (17)0.0019 (16)0.0027 (16)
C160.042 (2)0.037 (2)0.033 (2)0.0019 (18)0.0005 (17)0.0011 (18)
C170.041 (2)0.042 (2)0.033 (2)0.0067 (19)0.0074 (19)0.0029 (19)
C180.041 (2)0.045 (3)0.0301 (19)0.005 (2)0.0032 (17)0.0044 (18)
C190.0343 (17)0.0367 (18)0.0273 (16)0.002 (2)0.0028 (13)0.001 (2)
C200.046 (2)0.038 (2)0.032 (2)0.0050 (19)0.0048 (18)0.0076 (18)
C210.058 (3)0.035 (2)0.034 (2)0.006 (2)0.011 (2)0.0001 (19)
C220.051 (3)0.043 (3)0.035 (2)0.011 (2)0.0056 (19)0.0053 (19)
C230.045 (2)0.042 (3)0.0282 (16)0.007 (2)0.0017 (15)0.003 (2)
C240.034 (2)0.035 (2)0.0286 (18)0.0017 (17)0.0000 (16)0.0004 (17)
C250.063 (3)0.035 (2)0.0316 (18)0.008 (3)0.0101 (18)0.003 (2)
C260.129 (6)0.040 (3)0.057 (3)0.019 (3)0.037 (4)0.000 (3)
Br10.0605 (3)0.0338 (2)0.0426 (2)0.0115 (2)0.01229 (17)0.0073 (2)
O10.0542 (15)0.0396 (16)0.0368 (13)0.0151 (19)0.0001 (12)0.0011 (17)
O20.091 (3)0.053 (2)0.0403 (17)0.0337 (19)0.0048 (18)0.0033 (15)
O30.074 (2)0.035 (2)0.0421 (16)0.0099 (15)0.0114 (15)0.0008 (13)
N130.0398 (18)0.0306 (17)0.0257 (16)0.0010 (14)0.0013 (14)0.0020 (14)
S10.0842 (9)0.0499 (7)0.0293 (5)0.0254 (6)0.0038 (6)0.0051 (5)
Geometric parameters (Å, º) top
Br1—C111.912 (4)C10—H100.9600
S1—C71.748 (4)C13—C121.386 (7)
S1—C11.799 (5)C13—H130.9600
O1—C31.245 (6)C1—C21.518 (6)
C19—C181.408 (6)C1—H1A0.9600
C19—C201.425 (8)C1—H1B0.9600
C19—C241.427 (5)O3—C261.456 (6)
C8—C131.403 (6)C23—C221.365 (7)
C8—C91.410 (5)C23—C241.426 (6)
C8—C61.491 (6)C23—H230.9601
C6—C71.384 (6)C18—C171.361 (6)
C6—C51.428 (6)C18—H180.9600
O2—C251.201 (6)C12—C111.376 (6)
C5—C41.366 (6)C12—H120.9601
C5—C141.516 (5)C14—H14A0.9600
N13—C71.353 (5)C14—H14B0.9600
N13—C31.394 (5)C20—C211.358 (6)
N13—C21.476 (5)C20—H200.9599
C25—O31.340 (6)C16—C171.415 (6)
C25—C21.495 (7)C16—H160.9600
C15—C161.388 (6)C2—H20.9599
C15—C241.429 (6)C22—C211.408 (7)
C15—C141.514 (5)C22—H220.9601
C9—C101.392 (6)C21—H210.9600
C9—H90.9600C17—H170.9600
C4—C31.433 (6)C26—H26A0.9599
C4—H40.9599C26—H26B0.9600
C10—C111.381 (7)C26—H26C0.9600
C7—S1—C192.4 (2)C23—C24—C15122.7 (4)
C18—C19—C20121.5 (4)C19—C24—C15119.4 (4)
C18—C19—C24119.6 (5)C11—C12—C13118.2 (4)
C20—C19—C24118.8 (4)C11—C12—H12122.5
C13—C8—C9118.1 (4)C13—C12—H12119.3
C13—C8—C6118.9 (3)N13—C7—C6122.5 (4)
C9—C8—C6122.7 (4)N13—C7—S1112.7 (3)
C7—C6—C5116.9 (4)C6—C7—S1124.8 (3)
C7—C6—C8117.6 (4)C15—C14—C5117.1 (3)
C5—C6—C8125.4 (4)C15—C14—H14A106.2
C4—C5—C6120.0 (4)C5—C14—H14A109.2
C4—C5—C14121.7 (3)C15—C14—H14B105.5
C6—C5—C14118.3 (4)C5—C14—H14B109.1
C7—N13—C3122.9 (3)H14A—C14—H14B109.5
C7—N13—C2116.4 (3)C21—C20—C19121.5 (4)
C3—N13—C2120.0 (3)C21—C20—H20118.8
O2—C25—O3124.2 (5)C19—C20—H20119.7
O2—C25—C2124.8 (5)C15—C16—C17121.5 (4)
O3—C25—C2110.4 (4)C15—C16—H16119.9
C16—C15—C24118.5 (4)C17—C16—H16118.6
C16—C15—C14119.0 (4)N13—C2—C25114.5 (4)
C24—C15—C14122.4 (4)N13—C2—C1107.3 (3)
C10—C9—C8120.3 (4)C25—C2—C1108.4 (3)
C10—C9—H9119.8N13—C2—H2106.6
C8—C9—H9119.9C25—C2—H2109.3
C5—C4—C3122.8 (4)C1—C2—H2110.6
C5—C4—H4119.6C23—C22—C21120.8 (4)
C3—C4—H4117.6C23—C22—H22120.1
C11—C10—C9119.1 (4)C21—C22—H22119.1
C11—C10—H10120.5C20—C21—C22119.8 (4)
C9—C10—H10120.4C20—C21—H21119.7
C12—C13—C8121.8 (4)C22—C21—H21120.5
C12—C13—H13118.2C18—C17—C16120.2 (4)
C8—C13—H13120.0C18—C17—H17119.9
C2—C1—S1108.8 (3)C16—C17—H17119.9
C2—C1—H1A110.0O3—C26—H26A109.3
S1—C1—H1A109.2O3—C26—H26B109.4
C2—C1—H1B109.9H26A—C26—H26B109.5
S1—C1—H1B109.5O3—C26—H26C109.7
H1A—C1—H1B109.5H26A—C26—H26C109.5
C25—O3—C26114.9 (5)H26B—C26—H26C109.5
C22—C23—C24121.2 (4)C12—C11—C10122.5 (4)
C22—C23—H23119.2C12—C11—Br1118.2 (3)
C24—C23—H23119.6C10—C11—Br1119.3 (3)
C17—C18—C19120.8 (4)O1—C3—N13118.5 (4)
C17—C18—H18119.5O1—C3—C4126.6 (4)
C19—C18—H18119.8N13—C3—C4114.8 (4)
C23—C24—C19117.9 (4)
 

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