Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the title compound, C16H14N2O2S, the C—N—S—C torsion angle is −63.1 (4)°. One intra­molecular N—H...N hydrogen bond is observed in the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806029734/xu2103sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806029734/xu2103Isup2.hkl
Contains datablock I

CCDC reference: 621553

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.078
  • wR factor = 0.236
  • Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.532 0.611 Tmin and Tmax expected: 0.418 0.540 RR = 1.127 Please check that your absorption correction is appropriate. PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.88 PLAT230_ALERT_2_C Hirshfeld Test Diff for C3 - C4 .. 5.23 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C10 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.884 Tmax scaled 0.540 Tmin scaled 0.470
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

N-Benzylquinoline-8-sulfonamide top
Crystal data top
C16H14N2O2SF(000) = 624
Mr = 298.35Dx = 1.379 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 10.142 (2) Åθ = 5.4–22.2°
b = 9.980 (2) ŵ = 2.05 mm1
c = 14.428 (2) ÅT = 299 K
β = 100.25 (2)°Block, yellow
V = 1437.1 (5) Å30.55 × 0.40 × 0.30 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
2203 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.066
Graphite monochromatorθmax = 66.8°, θmin = 4.9°
ω/2θ scansh = 1211
Absorption correction: ψ scan
(North et al., 1968)
k = 110
Tmin = 0.532, Tmax = 0.611l = 017
2649 measured reflections3 standard reflections every 120 min
2546 independent reflections intensity decay: 1.3%
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)] = 0.078Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.236H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.1508P)2 + 0.7674P]
where P = (Fo2 + 2Fc2)/3
2546 reflections(Δ/σ)max = 0.002
193 parametersΔρmax = 0.80 e Å3
0 restraintsΔρmin = 0.40 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.7359 (4)0.0943 (3)0.4400 (2)0.0559 (8)
C20.7112 (5)0.0004 (4)0.5040 (3)0.0700 (10)
H20.63370.05110.49180.084*
C30.8019 (5)0.0178 (5)0.5873 (3)0.0797 (13)
H30.78410.08100.63080.096*
C40.9159 (6)0.0553 (5)0.6057 (3)0.0823 (14)
H40.97680.03920.66080.099*
C50.9448 (4)0.1569 (4)0.5422 (2)0.0664 (10)
C61.0577 (5)0.2403 (6)0.5588 (3)0.0839 (14)
H61.12070.23090.61370.101*
C71.0749 (5)0.3349 (6)0.4942 (4)0.0879 (14)
H71.14950.39080.50410.105*
C80.9793 (5)0.3463 (5)0.4135 (3)0.0804 (12)
H80.99260.41110.36980.096*
C90.8533 (4)0.1767 (3)0.4580 (2)0.0566 (8)
C100.5138 (5)0.3271 (4)0.3940 (3)0.0794 (12)
H10A0.57460.32860.45400.095*
H10B0.43790.27110.40070.095*
C110.4656 (4)0.4672 (4)0.3686 (2)0.0565 (8)
C120.5526 (5)0.5681 (5)0.3579 (3)0.0755 (11)
H120.64360.54890.36560.091*
C130.5106 (7)0.6958 (5)0.3365 (4)0.0933 (15)
H130.57240.76200.32900.112*
C140.3815 (8)0.7259 (5)0.3263 (3)0.0956 (17)
H140.35400.81380.31350.115*
C150.2872 (5)0.6289 (7)0.3345 (4)0.0983 (18)
H150.19660.65060.32580.118*
C160.3306 (4)0.4954 (5)0.3563 (3)0.0763 (11)
H160.26910.42830.36230.092*
N10.5828 (4)0.2695 (3)0.3216 (2)0.0637 (8)
H1N0.654 (5)0.310 (5)0.317 (3)0.076*
N20.8715 (3)0.2724 (3)0.3943 (2)0.0646 (8)
O10.6874 (3)0.0770 (3)0.25737 (19)0.0775 (8)
O20.5023 (3)0.0407 (3)0.3441 (2)0.0841 (9)
S10.62121 (9)0.11202 (9)0.33302 (6)0.0610 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.073 (2)0.0496 (17)0.0483 (17)0.0134 (15)0.0197 (15)0.0034 (13)
C20.093 (3)0.057 (2)0.067 (2)0.0154 (19)0.032 (2)0.0097 (17)
C30.111 (3)0.075 (3)0.059 (2)0.028 (3)0.030 (2)0.0183 (19)
C40.110 (3)0.095 (3)0.0412 (18)0.046 (3)0.0137 (19)0.0041 (19)
C50.079 (2)0.075 (2)0.0463 (18)0.0205 (19)0.0154 (16)0.0105 (16)
C60.079 (3)0.104 (3)0.065 (2)0.017 (2)0.001 (2)0.029 (2)
C70.086 (3)0.097 (3)0.081 (3)0.015 (3)0.016 (2)0.024 (3)
C80.097 (3)0.070 (2)0.077 (3)0.009 (2)0.023 (2)0.007 (2)
C90.073 (2)0.0531 (18)0.0462 (17)0.0116 (16)0.0173 (15)0.0050 (13)
C100.112 (3)0.071 (3)0.064 (2)0.022 (2)0.038 (2)0.0109 (19)
C110.067 (2)0.0572 (19)0.0468 (16)0.0060 (16)0.0148 (14)0.0011 (14)
C120.080 (3)0.078 (3)0.072 (2)0.004 (2)0.020 (2)0.001 (2)
C130.131 (4)0.065 (3)0.089 (3)0.004 (3)0.034 (3)0.002 (2)
C140.154 (5)0.067 (3)0.065 (3)0.029 (3)0.016 (3)0.001 (2)
C150.083 (3)0.126 (5)0.081 (3)0.043 (3)0.000 (2)0.032 (3)
C160.068 (2)0.085 (3)0.078 (3)0.003 (2)0.0210 (19)0.022 (2)
N10.082 (2)0.0590 (18)0.0520 (16)0.0139 (15)0.0157 (15)0.0048 (13)
N20.078 (2)0.0568 (17)0.0590 (17)0.0003 (15)0.0137 (15)0.0024 (13)
O10.098 (2)0.0792 (18)0.0562 (15)0.0172 (15)0.0151 (13)0.0150 (13)
O20.0794 (18)0.0750 (19)0.097 (2)0.0073 (15)0.0136 (16)0.0046 (16)
S10.0727 (6)0.0571 (6)0.0530 (6)0.0061 (4)0.0103 (4)0.0033 (3)
Geometric parameters (Å, º) top
C1—C21.369 (5)C10—C111.504 (5)
C1—C91.433 (5)C10—H10A0.9700
C1—S11.769 (4)C10—H10B0.9700
C2—C31.388 (6)C11—C121.365 (6)
C2—H20.9300C11—C161.378 (6)
C3—C41.354 (7)C12—C131.363 (7)
C3—H30.9300C12—H120.9300
C4—C51.431 (7)C13—C141.326 (9)
C4—H40.9300C13—H130.9300
C5—C61.401 (7)C14—C151.380 (8)
C5—C91.406 (5)C14—H140.9300
C6—C71.360 (8)C15—C161.421 (7)
C6—H60.9300C15—H150.9300
C7—C81.380 (7)C16—H160.9300
C7—H70.9300N1—S11.621 (3)
C8—N21.307 (6)N1—H1N0.84 (5)
C8—H80.9300O1—S11.423 (3)
C9—N21.360 (5)O2—S11.434 (3)
C10—N11.473 (5)
C2—C1—C9121.1 (4)C11—C10—H10B109.4
C2—C1—S1119.1 (3)H10A—C10—H10B108.0
C9—C1—S1119.8 (2)C12—C11—C16118.8 (4)
C1—C2—C3120.1 (4)C12—C11—C10121.6 (4)
C1—C2—H2120.0C16—C11—C10119.6 (4)
C3—C2—H2120.0C13—C12—C11122.2 (5)
C4—C3—C2120.7 (4)C13—C12—H12118.9
C4—C3—H3119.7C11—C12—H12118.9
C2—C3—H3119.7C14—C13—C12120.0 (5)
C3—C4—C5121.5 (4)C14—C13—H13120.0
C3—C4—H4119.3C12—C13—H13120.0
C5—C4—H4119.3C13—C14—C15121.2 (5)
C6—C5—C9117.2 (4)C13—C14—H14119.4
C6—C5—C4124.5 (4)C15—C14—H14119.4
C9—C5—C4118.3 (4)C14—C15—C16118.9 (4)
C7—C6—C5119.8 (4)C14—C15—H15120.5
C7—C6—H6120.1C16—C15—H15120.5
C5—C6—H6120.1C11—C16—C15118.8 (4)
C6—C7—C8118.6 (5)C11—C16—H16120.6
C6—C7—H7120.7C15—C16—H16120.6
C8—C7—H7120.7C10—N1—S1116.3 (3)
N2—C8—C7124.6 (5)C10—N1—H1N113 (3)
N2—C8—H8117.7S1—N1—H1N106 (3)
C7—C8—H8117.7C8—N2—C9117.5 (4)
N2—C9—C5122.3 (4)O1—S1—O2119.0 (2)
N2—C9—C1119.3 (3)O1—S1—N1107.37 (18)
C5—C9—C1118.4 (3)O2—S1—N1107.52 (19)
N1—C10—C11111.4 (3)O1—S1—C1108.56 (17)
N1—C10—H10A109.4O2—S1—C1106.77 (19)
C11—C10—H10A109.4N1—S1—C1107.11 (17)
N1—C10—H10B109.4
C9—C1—C2—C31.1 (5)C10—C11—C12—C13178.9 (4)
S1—C1—C2—C3178.1 (3)C11—C12—C13—C140.8 (7)
C1—C2—C3—C40.8 (6)C12—C13—C14—C151.8 (8)
C2—C3—C4—C52.3 (6)C13—C14—C15—C161.5 (7)
C3—C4—C5—C6177.0 (4)C12—C11—C16—C150.9 (6)
C3—C4—C5—C92.0 (6)C10—C11—C16—C15178.6 (4)
C9—C5—C6—C70.2 (6)C14—C15—C16—C110.1 (7)
C4—C5—C6—C7179.2 (4)C11—C10—N1—S1171.7 (3)
C5—C6—C7—C80.2 (7)C7—C8—N2—C90.8 (7)
C6—C7—C8—N20.4 (8)C5—C9—N2—C80.8 (5)
C6—C5—C9—N20.2 (5)C1—C9—N2—C8179.5 (3)
C4—C5—C9—N2178.8 (3)C10—N1—S1—O1179.5 (3)
C6—C5—C9—C1179.0 (3)C10—N1—S1—O251.4 (4)
C4—C5—C9—C10.1 (5)C10—N1—S1—C163.1 (4)
C2—C1—C9—N2177.4 (3)C2—C1—S1—O1115.9 (3)
S1—C1—C9—N23.4 (4)C9—C1—S1—O163.3 (3)
C2—C1—C9—C51.4 (5)C2—C1—S1—O213.5 (3)
S1—C1—C9—C5177.8 (2)C9—C1—S1—O2167.3 (3)
N1—C10—C11—C1261.3 (5)C2—C1—S1—N1128.5 (3)
N1—C10—C11—C16119.3 (4)C9—C1—S1—N152.3 (3)
C16—C11—C12—C130.6 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···N20.84 (5)2.32 (5)2.929 (5)130 (4)
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds