Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The mol­ecular packing of the title compound, C24H30N2O3S, is stabilized by a hydrogen-bonded network. Both sulfonyl O atoms are involved in inter­molecular hydrogen bonds of types N—H...O and C—H...O. An inter­molecular N—H...N hydrogen bond is also observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806045843/om2064sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806045843/om2064Isup2.hkl
Contains datablock I

CCDC reference: 630208

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.057
  • wR factor = 0.152
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C19
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT057_ALERT_3_C Correction for Absorption Required RT(exp) ... 1.12 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.89 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C22 PLAT301_ALERT_3_C Main Residue Disorder ......................... 3.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 27.70 Deg. C20B -C19 -C20A 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4-PC (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: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

2-Aminoquinolin-4-yl 2,4,6-triisopropylbenzenesulfonate top
Crystal data top
C24H30N2O3SZ = 2
Mr = 426.56F(000) = 456
Triclinic, P1Dx = 1.219 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54180 Å
a = 9.431 (1) ÅCell parameters from 25 reflections
b = 11.015 (2) Åθ = 4.4–24.6°
c = 12.312 (2) ŵ = 1.45 mm1
α = 77.61 (1)°T = 299 K
β = 80.79 (1)°Prism, yellow
γ = 69.11 (1)°0.28 × 0.13 × 0.08 mm
V = 1162.2 (3) Å3
Data collection top
Nonius CAD-4
diffractometer
Rint = 0.027
Radiation source: fine-focus sealed tubeθmax = 66.9°, θmin = 3.7°
Graphite monochromatorh = 111
w/2θ scansk = 1312
4540 measured reflectionsl = 1414
3997 independent reflections3 standard reflections every 120 min
2461 reflections with I > 2σ(I) intensity decay: 2.5%
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)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0729P)2]
where P = (Fo2 + 2Fc2)/3
3997 reflections(Δ/σ)max = 0.012
287 parametersΔρmax = 0.23 e Å3
1 restraintΔρmin = 0.33 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*/UeqOcc. (<1)
C10.0027 (4)0.7925 (3)0.4403 (2)0.0460 (8)
C20.0206 (4)0.9240 (3)0.3868 (2)0.0458 (8)
C30.0965 (4)0.9681 (4)0.3267 (3)0.0578 (9)
H30.19500.90850.31970.069*
C40.0685 (5)1.0965 (4)0.2785 (3)0.0697 (11)
H40.14681.12440.23820.084*
C50.0790 (5)1.1863 (4)0.2901 (3)0.0718 (11)
H50.09781.27430.25790.086*
C60.1966 (4)1.1473 (4)0.3481 (3)0.0628 (10)
H60.29411.20880.35410.075*
C70.1706 (4)1.0152 (3)0.3982 (3)0.0467 (8)
C80.2653 (4)0.8568 (3)0.5061 (2)0.0487 (8)
C90.1186 (4)0.7584 (3)0.4996 (3)0.0519 (9)
H90.10370.67210.53580.062*
C100.2551 (4)0.6691 (3)0.2261 (2)0.0425 (8)
C110.4038 (4)0.6759 (3)0.2159 (2)0.0437 (8)
C120.4659 (4)0.7119 (3)0.1090 (3)0.0490 (8)
H120.56470.71440.10040.059*
C130.3887 (4)0.7443 (3)0.0145 (3)0.0500 (8)
C140.2395 (4)0.7478 (3)0.0303 (3)0.0558 (9)
H140.18430.77410.03180.067*
C150.1669 (4)0.7140 (3)0.1338 (3)0.0481 (8)
C160.5023 (4)0.6478 (4)0.3113 (3)0.0598 (10)
H160.43880.63890.38170.072*
C170.6328 (5)0.5173 (4)0.3081 (4)0.0890 (14)
H17A0.69510.52260.23870.107*
H17B0.59200.44750.31460.107*
H17C0.69340.49980.36890.107*
C180.5615 (5)0.7596 (5)0.3085 (4)0.0880 (14)
H18A0.47700.83950.31410.106*
H18B0.62310.77110.23970.106*
H18C0.62170.73910.37010.106*
C190.4656 (4)0.7703 (4)0.1008 (3)0.0643 (10)
H150.39420.78870.15670.077*
C20A0.6053 (19)0.6531 (15)0.1218 (14)0.104 (5)0.65
H20A0.57590.57650.11440.125*0.65
H20B0.67640.63750.06850.125*0.65
H20C0.65200.67090.19590.125*0.65
C20B0.545 (4)0.647 (2)0.148 (3)0.122 (13)0.35
H20D0.47340.60470.15070.147*0.35
H20E0.62320.58900.10100.147*0.35
H20F0.59090.66820.22160.147*0.35
C210.5289 (6)0.8799 (5)0.1172 (4)0.1096 (18)
H21A0.60560.85770.06680.131*
H21B0.44860.95930.10280.131*
H21C0.57330.89320.19270.131*
C220.0017 (4)0.7308 (4)0.1370 (3)0.0658 (10)
H220.04180.71830.21550.079*
C230.0209 (6)0.6269 (6)0.0841 (5)0.1105 (18)
H23A0.03300.54100.12280.133*
H23B0.01930.63580.00720.133*
H23C0.12720.63780.08860.133*
C240.0917 (5)0.8694 (5)0.0829 (5)0.1127 (19)
H24A0.05260.88550.00620.135*
H24B0.08210.93250.12180.135*
H24C0.19710.87780.08650.135*
N10.2910 (3)0.9808 (3)0.4562 (2)0.0514 (7)
N20.3833 (4)0.8242 (3)0.5675 (3)0.0612 (9)
H21N0.369 (4)0.743 (4)0.587 (3)0.073*
H22N0.471 (5)0.882 (4)0.561 (3)0.073*
O10.1448 (2)0.6977 (2)0.43644 (17)0.0528 (6)
O20.0565 (3)0.5618 (2)0.3458 (2)0.0663 (7)
O30.3139 (3)0.4865 (2)0.4031 (2)0.0685 (8)
S10.18909 (11)0.59108 (8)0.35524 (7)0.0531 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0408 (19)0.0531 (18)0.0394 (16)0.0086 (15)0.0004 (14)0.0124 (14)
C20.0434 (19)0.0557 (19)0.0375 (16)0.0142 (15)0.0008 (14)0.0139 (14)
C30.048 (2)0.062 (2)0.065 (2)0.0209 (17)0.0093 (17)0.0205 (17)
C40.068 (3)0.067 (2)0.079 (3)0.034 (2)0.012 (2)0.015 (2)
C50.070 (3)0.058 (2)0.084 (3)0.027 (2)0.002 (2)0.002 (2)
C60.055 (2)0.056 (2)0.072 (2)0.0147 (18)0.0065 (19)0.0053 (18)
C70.043 (2)0.0547 (19)0.0440 (17)0.0176 (16)0.0018 (15)0.0116 (14)
C80.042 (2)0.060 (2)0.0404 (17)0.0143 (16)0.0006 (14)0.0094 (15)
C90.051 (2)0.0529 (19)0.0425 (17)0.0120 (16)0.0060 (15)0.0049 (14)
C100.0393 (19)0.0406 (16)0.0427 (16)0.0116 (14)0.0036 (14)0.0053 (13)
C110.0419 (19)0.0472 (18)0.0407 (16)0.0146 (15)0.0030 (14)0.0055 (14)
C120.0374 (19)0.059 (2)0.0519 (19)0.0218 (16)0.0004 (15)0.0061 (15)
C130.046 (2)0.064 (2)0.0403 (17)0.0233 (17)0.0009 (15)0.0034 (15)
C140.051 (2)0.068 (2)0.0491 (19)0.0221 (18)0.0129 (16)0.0008 (16)
C150.0371 (19)0.0505 (18)0.056 (2)0.0149 (15)0.0038 (15)0.0078 (15)
C160.052 (2)0.077 (2)0.050 (2)0.022 (2)0.0083 (17)0.0068 (17)
C170.061 (3)0.103 (3)0.080 (3)0.003 (2)0.020 (2)0.001 (2)
C180.087 (3)0.124 (4)0.072 (3)0.050 (3)0.017 (2)0.025 (3)
C190.060 (3)0.087 (3)0.046 (2)0.034 (2)0.0014 (17)0.0018 (18)
C20A0.164 (12)0.095 (7)0.045 (7)0.033 (8)0.021 (6)0.031 (4)
C20B0.24 (4)0.072 (10)0.051 (15)0.050 (16)0.029 (16)0.035 (9)
C210.131 (5)0.102 (4)0.089 (3)0.057 (3)0.042 (3)0.008 (3)
C220.042 (2)0.079 (3)0.075 (3)0.0243 (19)0.0066 (18)0.003 (2)
C230.075 (3)0.155 (5)0.133 (5)0.070 (4)0.002 (3)0.042 (4)
C240.050 (3)0.116 (4)0.141 (5)0.012 (3)0.021 (3)0.022 (3)
N10.0391 (16)0.0611 (17)0.0502 (16)0.0148 (13)0.0007 (13)0.0074 (13)
N20.0460 (19)0.0629 (19)0.0633 (19)0.0161 (16)0.0112 (16)0.0025 (16)
O10.0415 (13)0.0592 (13)0.0490 (12)0.0070 (11)0.0021 (10)0.0130 (10)
O20.0711 (18)0.0702 (16)0.0677 (16)0.0434 (14)0.0121 (13)0.0117 (12)
O30.0678 (17)0.0475 (13)0.0646 (15)0.0032 (12)0.0071 (13)0.0062 (11)
S10.0552 (6)0.0464 (4)0.0501 (5)0.0159 (4)0.0110 (4)0.0058 (3)
Geometric parameters (Å, º) top
C1—C91.338 (4)C17—H17A0.9600
C1—O11.412 (3)C17—H17B0.9600
C1—C21.418 (4)C17—H17C0.9600
C2—C31.404 (4)C18—H18A0.9600
C2—C71.419 (4)C18—H18B0.9600
C3—C41.358 (5)C18—H18C0.9600
C3—H30.9300C19—C20B1.486 (14)
C4—C51.396 (5)C19—C211.492 (6)
C4—H40.9300C19—C20A1.513 (11)
C5—C61.370 (5)C19—H150.9800
C5—H50.9300C20A—H20A0.9600
C6—C71.403 (4)C20A—H20B0.9600
C6—H60.9300C20A—H20C0.9600
C7—N11.370 (4)C20B—H20D0.9600
C8—N11.324 (4)C20B—H20E0.9600
C8—N21.355 (4)C20B—H20F0.9600
C8—C91.424 (4)C21—H21A0.9600
C9—H90.9300C21—H21B0.9600
C10—C151.413 (4)C21—H21C0.9600
C10—C111.415 (4)C22—C231.506 (6)
C10—S11.770 (3)C22—C241.522 (5)
C11—C121.389 (4)C22—H220.9800
C11—C161.525 (5)C23—H23A0.9600
C12—C131.386 (4)C23—H23B0.9600
C12—H120.9300C23—H23C0.9600
C13—C141.378 (5)C24—H24A0.9600
C13—C191.505 (4)C24—H24B0.9600
C14—C151.390 (4)C24—H24C0.9600
C14—H140.9300N2—H21N0.84 (4)
C15—C221.529 (5)N2—H22N0.85 (4)
C16—C181.515 (5)O1—S11.605 (2)
C16—C171.526 (5)O2—S11.425 (3)
C16—H160.9800O3—S11.423 (2)
C9—C1—O1119.6 (3)C16—C18—H18C109.5
C9—C1—C2122.1 (3)H18A—C18—H18C109.5
O1—C1—C2118.2 (3)H18B—C18—H18C109.5
C3—C2—C7119.4 (3)C20B—C19—C21123.0 (18)
C3—C2—C1125.3 (3)C20B—C19—C13112.1 (16)
C7—C2—C1115.3 (3)C21—C19—C13113.6 (3)
C4—C3—C2121.1 (3)C20B—C19—C20A27.7 (16)
C4—C3—H3119.4C21—C19—C20A103.0 (9)
C2—C3—H3119.4C13—C19—C20A110.6 (8)
C3—C4—C5119.4 (4)C20B—C19—H1584.0
C3—C4—H4120.3C21—C19—H15109.8
C5—C4—H4120.3C13—C19—H15109.8
C6—C5—C4121.4 (4)C20A—C19—H15109.8
C6—C5—H5119.3C19—C20A—H20A109.5
C4—C5—H5119.3C19—C20A—H20B109.5
C5—C6—C7120.3 (3)H20A—C20A—H20B109.5
C5—C6—H6119.9C19—C20A—H20C109.5
C7—C6—H6119.9H20A—C20A—H20C109.5
N1—C7—C6118.4 (3)H20B—C20A—H20C109.5
N1—C7—C2123.2 (3)C19—C20B—H20D109.5
C6—C7—C2118.4 (3)C19—C20B—H20E109.5
N1—C8—N2118.1 (3)H20D—C20B—H20E109.5
N1—C8—C9122.5 (3)C19—C20B—H20F109.5
N2—C8—C9119.4 (3)H20D—C20B—H20F109.5
C1—C9—C8118.7 (3)H20E—C20B—H20F109.5
C1—C9—H9120.7C19—C21—H21A109.5
C8—C9—H9120.7C19—C21—H21B109.5
C15—C10—C11121.1 (3)H21A—C21—H21B109.5
C15—C10—S1121.0 (2)C19—C21—H21C109.5
C11—C10—S1117.7 (2)H21A—C21—H21C109.5
C12—C11—C10117.0 (3)H21B—C21—H21C109.5
C12—C11—C16116.8 (3)C23—C22—C24111.9 (4)
C10—C11—C16126.2 (3)C23—C22—C15110.8 (3)
C13—C12—C11123.5 (3)C24—C22—C15111.0 (3)
C13—C12—H12118.2C23—C22—H22107.7
C11—C12—H12118.2C24—C22—H22107.7
C14—C13—C12117.0 (3)C15—C22—H22107.7
C14—C13—C19121.3 (3)C22—C23—H23A109.5
C12—C13—C19121.6 (3)C22—C23—H23B109.5
C13—C14—C15123.7 (3)H23A—C23—H23B109.5
C13—C14—H14118.2C22—C23—H23C109.5
C15—C14—H14118.2H23A—C23—H23C109.5
C14—C15—C10117.0 (3)H23B—C23—H23C109.5
C14—C15—C22116.7 (3)C22—C24—H24A109.5
C10—C15—C22126.3 (3)C22—C24—H24B109.5
C18—C16—C11111.8 (3)H24A—C24—H24B109.5
C18—C16—C17111.3 (3)C22—C24—H24C109.5
C11—C16—C17110.0 (3)H24A—C24—H24C109.5
C18—C16—H16107.9H24B—C24—H24C109.5
C11—C16—H16107.9C8—N1—C7118.3 (3)
C17—C16—H16107.9C8—N2—H21N116 (3)
C16—C17—H17A109.5C8—N2—H22N116 (3)
C16—C17—H17B109.5H21N—N2—H22N123 (4)
H17A—C17—H17B109.5C1—O1—S1119.8 (2)
C16—C17—H17C109.5O3—S1—O2117.72 (16)
H17A—C17—H17C109.5O3—S1—O1103.69 (14)
H17B—C17—H17C109.5O2—S1—O1108.86 (14)
C16—C18—H18A109.5O3—S1—C10109.19 (15)
C16—C18—H18B109.5O2—S1—C10111.67 (16)
H18A—C18—H18B109.5O1—S1—C10104.61 (13)
C9—C1—C2—C3177.6 (3)S1—C10—C15—C14166.5 (2)
O1—C1—C2—C31.9 (5)C11—C10—C15—C22170.6 (3)
C9—C1—C2—C71.6 (5)S1—C10—C15—C2214.3 (5)
O1—C1—C2—C7177.3 (3)C12—C11—C16—C1851.9 (4)
C7—C2—C3—C40.5 (5)C10—C11—C16—C18127.9 (4)
C1—C2—C3—C4179.7 (3)C12—C11—C16—C1772.2 (4)
C2—C3—C4—C50.7 (6)C10—C11—C16—C17108.0 (4)
C3—C4—C5—C60.8 (6)C14—C13—C19—C20B91.3 (14)
C4—C5—C6—C70.6 (6)C12—C13—C19—C20B86.6 (14)
C5—C6—C7—N1179.4 (3)C14—C13—C19—C21123.6 (4)
C5—C6—C7—C20.3 (5)C12—C13—C19—C2158.4 (5)
C3—C2—C7—N1179.4 (3)C14—C13—C19—C20A121.1 (8)
C1—C2—C7—N10.1 (5)C12—C13—C19—C20A56.8 (8)
C3—C2—C7—C60.3 (5)C14—C15—C22—C2372.1 (4)
C1—C2—C7—C6179.6 (3)C10—C15—C22—C23108.7 (4)
O1—C1—C9—C8177.5 (3)C14—C15—C22—C2452.8 (5)
C2—C1—C9—C81.9 (5)C10—C15—C22—C24126.3 (4)
N1—C8—C9—C10.3 (5)N2—C8—N1—C7177.2 (3)
N2—C8—C9—C1178.8 (3)C9—C8—N1—C71.4 (5)
C15—C10—C11—C128.2 (4)C6—C7—N1—C8178.1 (3)
S1—C10—C11—C12167.0 (2)C2—C7—N1—C81.6 (5)
C15—C10—C11—C16171.6 (3)C9—C1—O1—S179.1 (3)
S1—C10—C11—C1613.2 (4)C2—C1—O1—S1105.1 (3)
C10—C11—C12—C131.9 (5)C1—O1—S1—O3157.9 (2)
C16—C11—C12—C13178.0 (3)C1—O1—S1—O231.8 (3)
C11—C12—C13—C143.9 (5)C1—O1—S1—C1087.7 (2)
C11—C12—C13—C19174.1 (3)C15—C10—S1—O3141.8 (3)
C12—C13—C14—C153.5 (5)C11—C10—S1—O333.5 (3)
C19—C13—C14—C15174.5 (3)C15—C10—S1—O29.8 (3)
C13—C14—C15—C102.5 (5)C11—C10—S1—O2165.4 (2)
C13—C14—C15—C22176.7 (3)C15—C10—S1—O1107.8 (3)
C11—C10—C15—C148.6 (5)C11—C10—S1—O177.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21N···O3i0.84 (4)2.37 (4)3.197 (4)167 (4)
N2—H22N···N1ii0.85 (4)2.22 (4)3.073 (4)175 (4)
C9—H9···O2i0.932.603.522 (4)174
Symmetry codes: (i) x, y+1, z+1; (ii) x1, y+2, z+1.
 

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