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The title compound, C18H19N3O3S, was identified as one of two possible isomers. Key bond lengths are N—N 1.402 (2) Å and N—S 1.6894 (18) Å. Classical hydrogen bonds N—H...O connect the mol­ecules to form inversion-symmetric dimers, which are further linked by a weak C—H...O hydrogen bond, forming ribbons.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802019177/bt6207sup1.cif
Contains datablocks 5, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802019177/bt62075sup2.hkl
Contains datablock 5

CCDC reference: 178312

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.037
  • wR factor = 0.097
  • Data-to-parameter ratio = 13.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C3 - C10 = 1.44 Ang. PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 34 C4 -C3 -C10 -N3 13.00 8.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 35 C2 -C3 -C10 -N3 -167.00 8.00 1.555 1.555 1.555 1.555
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check

Computing details top

Data collection: XSCANS (Fait, 1991); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

N-(3-Cyano-2-oxo-2,5,6,7,8,9-hexahydro-1H-cyclohepta[b]pyridin-1- yl)-4-methylbenzenesulfonamide top
Crystal data top
C18H19N3O3SF(000) = 752
Mr = 357.42Dx = 1.388 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.7423 (16) ÅCell parameters from 72 reflections
b = 11.9050 (14) Åθ = 4–12.5°
c = 12.2458 (14) ŵ = 0.21 mm1
β = 91.816 (12)°T = 173 K
V = 1711.0 (4) Å3Irregular prism, colourless
Z = 40.7 × 0.4 × 0.2 mm
Data collection top
Siemens P4
diffractometer
Rint = 0.013
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 3.3°
Graphite monochromatorh = 1313
ω scansk = 142
3649 measured reflectionsl = 140
2995 independent reflections3 standard reflections every 247 reflections
2241 reflections with I > 2σ(I) intensity decay: none
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0551P)2]
where P = (Fo2 + 2Fc2)/3
2995 reflections(Δ/σ)max = 0.001
231 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.29 e Å3
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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 1.9733 (0.0082) x - 0.5492 (0.0094) y + 12.1176 (0.0028) z = 4.0391 (0.0066)

* -0.0018 (0.0012) N1 * -0.0123 (0.0012) C2 * 0.0162 (0.0013) C3 * -0.0055 (0.0013) C4 * -0.0095 (0.0014) C4A * 0.0128 (0.0013) C9A

Rms deviation of fitted atoms = 0.0108

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S0.70179 (4)0.54246 (5)0.33855 (5)0.03474 (17)
O10.47535 (10)0.38556 (11)0.42468 (10)0.0294 (3)
O20.69531 (13)0.45370 (14)0.25925 (12)0.0487 (4)
O30.80514 (12)0.60340 (15)0.35186 (17)0.0668 (6)
N10.66690 (12)0.36537 (13)0.45834 (12)0.0249 (4)
N20.67733 (14)0.48269 (14)0.46071 (14)0.0267 (4)
H00.6262 (17)0.5112 (18)0.4915 (16)0.030 (6)*
N30.35661 (17)0.10818 (18)0.40522 (17)0.0535 (6)
C20.55744 (15)0.32181 (16)0.43767 (14)0.0246 (4)
C30.55336 (16)0.20144 (17)0.43390 (15)0.0285 (4)
C40.65034 (17)0.13860 (17)0.44506 (16)0.0333 (5)
H40.64470.05920.43950.040*
C4A0.75741 (17)0.18679 (17)0.46435 (15)0.0298 (5)
C50.86201 (17)0.11303 (18)0.47684 (17)0.0371 (5)
H5A0.91860.13810.42370.045*
H5B0.84020.03490.45780.045*
C60.91849 (18)0.1131 (2)0.59048 (18)0.0422 (6)
H6A0.85850.10670.64520.051*
H6B0.96780.04600.59790.051*
C70.98973 (19)0.2166 (2)0.61649 (18)0.0454 (6)
H7A1.05190.22060.56390.055*
H7B1.02530.20740.69030.055*
C80.92586 (18)0.3275 (2)0.61316 (17)0.0410 (6)
H8A0.97840.38770.63870.049*
H8B0.86300.32350.66500.049*
C90.87584 (15)0.36006 (18)0.49995 (17)0.0335 (5)
H9A0.86360.44230.49770.040*
H9B0.93150.34100.44380.040*
C9A0.76544 (15)0.30201 (17)0.47271 (14)0.0277 (4)
C100.44313 (18)0.15085 (18)0.41754 (17)0.0340 (5)
C110.59164 (15)0.64010 (17)0.31379 (15)0.0270 (4)
C120.61699 (17)0.75385 (17)0.31218 (16)0.0331 (5)
H120.69090.77990.33360.040*
C130.53298 (18)0.82865 (18)0.27887 (16)0.0356 (5)
H130.54980.90670.27820.043*
C140.42434 (16)0.79277 (18)0.24630 (16)0.0325 (5)
C150.40096 (16)0.67852 (18)0.25147 (16)0.0320 (5)
H150.32670.65260.23140.038*
C160.48278 (15)0.60198 (17)0.28506 (15)0.0277 (4)
H160.46510.52420.28860.033*
C170.33655 (19)0.8742 (2)0.2015 (2)0.0509 (6)
H17A0.33470.94070.24860.061*
H17B0.26150.83820.19930.061*
H17C0.35630.89670.12750.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0231 (3)0.0340 (3)0.0473 (3)0.0038 (2)0.0036 (2)0.0119 (3)
O10.0246 (7)0.0304 (8)0.0328 (7)0.0049 (6)0.0029 (6)0.0009 (6)
O20.0658 (11)0.0429 (9)0.0382 (9)0.0257 (8)0.0168 (7)0.0040 (8)
O30.0241 (8)0.0609 (12)0.1148 (16)0.0074 (8)0.0057 (9)0.0427 (11)
N10.0249 (8)0.0222 (9)0.0275 (8)0.0032 (7)0.0023 (6)0.0012 (7)
N20.0246 (9)0.0230 (9)0.0323 (9)0.0036 (7)0.0021 (7)0.0027 (8)
N30.0485 (12)0.0504 (13)0.0608 (14)0.0122 (11)0.0120 (10)0.0081 (11)
C20.0249 (10)0.0284 (11)0.0204 (9)0.0009 (9)0.0012 (7)0.0005 (8)
C30.0323 (10)0.0267 (10)0.0264 (10)0.0008 (9)0.0015 (8)0.0038 (9)
C40.0441 (12)0.0241 (11)0.0314 (11)0.0038 (10)0.0020 (9)0.0016 (9)
C4A0.0324 (11)0.0291 (11)0.0277 (11)0.0091 (9)0.0001 (8)0.0038 (9)
C50.0399 (12)0.0325 (12)0.0390 (12)0.0132 (10)0.0004 (9)0.0004 (10)
C60.0406 (12)0.0468 (14)0.0392 (13)0.0234 (11)0.0023 (10)0.0091 (11)
C70.0386 (12)0.0594 (16)0.0377 (13)0.0159 (12)0.0094 (10)0.0026 (12)
C80.0330 (11)0.0509 (14)0.0384 (12)0.0077 (11)0.0095 (9)0.0039 (11)
C90.0251 (10)0.0361 (12)0.0392 (12)0.0059 (9)0.0025 (8)0.0011 (10)
C9A0.0276 (10)0.0338 (11)0.0216 (10)0.0075 (9)0.0008 (8)0.0011 (9)
C100.0394 (12)0.0274 (11)0.0347 (12)0.0003 (10)0.0063 (9)0.0043 (10)
C110.0278 (10)0.0271 (11)0.0261 (10)0.0019 (8)0.0009 (8)0.0028 (9)
C120.0336 (11)0.0293 (12)0.0360 (12)0.0035 (9)0.0041 (9)0.0020 (9)
C130.0472 (13)0.0236 (11)0.0359 (12)0.0004 (10)0.0012 (9)0.0036 (9)
C140.0342 (11)0.0352 (12)0.0284 (11)0.0079 (9)0.0042 (8)0.0079 (9)
C150.0247 (10)0.0394 (13)0.0320 (11)0.0012 (9)0.0001 (8)0.0064 (10)
C160.0280 (10)0.0252 (10)0.0297 (10)0.0018 (8)0.0004 (8)0.0039 (9)
C170.0430 (13)0.0484 (15)0.0614 (16)0.0162 (12)0.0062 (11)0.0166 (13)
Geometric parameters (Å, º) top
S—O31.4189 (16)C7—C81.518 (3)
S—O21.4355 (17)C7—H7A0.9900
S—N21.6894 (18)C7—H7B0.9900
S—C111.7583 (19)C8—C91.538 (3)
O1—C21.233 (2)C8—H8A0.9900
N1—C9A1.388 (2)C8—H8B0.9900
N1—C21.402 (2)C9—C9A1.497 (3)
N1—N21.402 (2)C9—H9A0.9900
N2—H00.79 (2)C9—H9B0.9900
N3—C101.142 (3)C11—C121.387 (3)
C2—C31.435 (3)C11—C161.391 (3)
C3—C41.366 (3)C12—C131.381 (3)
C3—C101.436 (3)C12—H120.9500
C4—C4A1.395 (3)C13—C141.392 (3)
C4—H40.9500C13—H130.9500
C4A—C9A1.379 (3)C14—C151.389 (3)
C4A—C51.514 (3)C14—C171.506 (3)
C5—C61.523 (3)C15—C161.377 (3)
C5—H5A0.9900C15—H150.9500
C5—H5B0.9900C16—H160.9500
C6—C71.517 (3)C17—H17A0.9800
C6—H6A0.9900C17—H17B0.9800
C6—H6B0.9900C17—H17C0.9800
O3—S—O2118.75 (11)H7A—C7—H7B107.4
O3—S—N2106.41 (10)C7—C8—C9114.70 (18)
O2—S—N2106.39 (9)C7—C8—H8A108.6
O3—S—C11107.67 (10)C9—C8—H8A108.6
O2—S—C11110.31 (9)C7—C8—H8B108.6
N2—S—C11106.64 (9)C9—C8—H8B108.6
C9A—N1—C2125.31 (16)H8A—C8—H8B107.6
C9A—N1—N2117.83 (15)C9A—C9—C8112.80 (17)
C2—N1—N2116.82 (15)C9A—C9—H9A109.0
N1—N2—S114.73 (13)C8—C9—H9A109.0
N1—N2—H0111.6 (16)C9A—C9—H9B109.0
S—N2—H0113.1 (15)C8—C9—H9B109.0
O1—C2—N1120.28 (17)H9A—C9—H9B107.8
O1—C2—C3125.84 (18)C4A—C9A—N1118.47 (18)
N1—C2—C3113.88 (16)C4A—C9A—C9122.17 (18)
C4—C3—C2121.14 (18)N1—C9A—C9119.34 (17)
C4—C3—C10121.96 (18)N3—C10—C3178.3 (2)
C2—C3—C10116.90 (17)C12—C11—C16120.73 (18)
C3—C4—C4A122.39 (19)C12—C11—S119.40 (15)
C3—C4—H4118.8C16—C11—S119.54 (15)
C4A—C4—H4118.8C13—C12—C11118.83 (18)
C9A—C4A—C4118.74 (18)C13—C12—H12120.6
C9A—C4A—C5121.09 (19)C11—C12—H12120.6
C4—C4A—C5120.16 (18)C12—C13—C14121.77 (19)
C4A—C5—C6114.86 (17)C12—C13—H13119.1
C4A—C5—H5A108.6C14—C13—H13119.1
C6—C5—H5A108.6C15—C14—C13117.91 (18)
C4A—C5—H5B108.6C15—C14—C17120.86 (19)
C6—C5—H5B108.6C13—C14—C17121.2 (2)
H5A—C5—H5B107.5C16—C15—C14121.62 (19)
C7—C6—C5114.45 (19)C16—C15—H15119.2
C7—C6—H6A108.6C14—C15—H15119.2
C5—C6—H6A108.6C15—C16—C11119.10 (19)
C7—C6—H6B108.6C15—C16—H16120.5
C5—C6—H6B108.6C11—C16—H16120.5
H6A—C6—H6B107.6C14—C17—H17A109.5
C6—C7—C8115.57 (17)C14—C17—H17B109.5
C6—C7—H7A108.4H17A—C17—H17B109.5
C8—C7—H7A108.4C14—C17—H17C109.5
C6—C7—H7B108.4H17A—C17—H17C109.5
C8—C7—H7B108.4H17B—C17—H17C109.5
C9A—N1—N2—S88.68 (17)C5—C4A—C9A—C93.1 (3)
C2—N1—N2—S89.15 (17)C2—N1—C9A—C4A1.3 (3)
O3—S—N2—N1122.44 (14)N2—N1—C9A—C4A176.34 (17)
O2—S—N2—N15.10 (15)C2—N1—C9A—C9176.91 (16)
C11—S—N2—N1122.84 (14)N2—N1—C9A—C95.5 (2)
C9A—N1—C2—O1179.05 (16)C8—C9—C9A—C4A61.9 (3)
N2—N1—C2—O11.4 (2)C8—C9—C9A—N1116.18 (19)
C9A—N1—C2—C31.0 (3)C4—C3—C10—N313 (8)
N2—N1—C2—C3178.64 (16)C2—C3—C10—N3167 (8)
O1—C2—C3—C4177.33 (18)O3—S—C11—C120.9 (2)
N1—C2—C3—C42.7 (3)O2—S—C11—C12131.89 (16)
O1—C2—C3—C102.5 (3)N2—S—C11—C12112.99 (17)
N1—C2—C3—C10177.50 (16)O3—S—C11—C16172.53 (16)
C2—C3—C4—C4A2.3 (3)O2—S—C11—C1641.52 (18)
C10—C3—C4—C4A177.97 (18)N2—S—C11—C1673.61 (16)
C3—C4—C4A—C9A0.2 (3)C16—C11—C12—C131.6 (3)
C3—C4—C4A—C5179.57 (18)S—C11—C12—C13171.72 (15)
C9A—C4A—C5—C666.3 (3)C11—C12—C13—C140.5 (3)
C4—C4A—C5—C6113.1 (2)C12—C13—C14—C152.0 (3)
C4A—C5—C6—C777.2 (2)C12—C13—C14—C17174.9 (2)
C5—C6—C7—C860.6 (3)C13—C14—C15—C161.6 (3)
C6—C7—C8—C964.2 (3)C17—C14—C15—C16175.42 (19)
C7—C8—C9—C9A80.8 (2)C14—C15—C16—C110.4 (3)
C4—C4A—C9A—N11.9 (3)C12—C11—C16—C152.1 (3)
C5—C4A—C9A—N1178.73 (16)S—C11—C16—C15171.27 (15)
C4—C4A—C9A—C9176.25 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H0···O1i0.79 (2)2.02 (2)2.793 (2)166 (2)
C8—H8A···O3ii0.992.543.279 (3)131
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y+1, z+1.
 

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