In the title compound, C
15H
11N
3O
4S, the dihedral angle between the quinoline ring system and the benzene ring is 79.9 (3)°. Intermolecular hydrogen bonds of types N—H
O, C—H
O and C—H
N are observed.
Supporting information
CCDC reference: 289905
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.005 Å
- R factor = 0.055
- wR factor = 0.150
- Data-to-parameter ratio = 10.1
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT482_ALERT_4_A Small D-H..A Angle Rep for C11 .. N2 .. 1.00 Deg.
PLAT728_ALERT_1_A D-H..A Calc 165.00, Rep 1.00 Dev... 164.00 Deg.
C11 -H11 -N2 1.555 1.555 1.455
Alert level C
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 ...... 1.00 Deg.
C11 -H11 -N2 1.555 1.555 1.455
Alert level G
REFLT03_ALERT_4_G 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.
From the CIF: _diffrn_reflns_theta_max 67.90
From the CIF: _reflns_number_total 2109
Count of symmetry unique reflns 1329
Completeness (_total/calc) 158.69%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 780
Fraction of Friedel pairs measured 0.587
Are heavy atom types Z>Si present yes
2 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4-PC Software (Nonius, 1996); cell refinement: CAD-4-PC Software; 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.
4-Nitro-
N-(8-quinolyl)benzenesulfonamide
top
Crystal data top
C15H11N3O4S | F(000) = 340 |
Mr = 329.33 | Dx = 1.538 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: P 2yb | Cell parameters from 25 reflections |
a = 5.0135 (6) Å | θ = 4.3–20.3° |
b = 20.636 (2) Å | µ = 2.27 mm−1 |
c = 6.966 (1) Å | T = 299 K |
β = 99.28 (1)° | Laminar, colourless |
V = 711.26 (15) Å3 | 0.60 × 0.18 × 0.10 mm |
Z = 2 | |
Data collection top
Nonius CAD-4 diffractometer | 2081 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.021 |
Graphite monochromator | θmax = 67.9°, θmin = 4.3° |
ω/2θ scans | h = −6→0 |
Absorption correction: ψ scan (North et al., 1968) | k = −24→11 |
Tmin = 0.282, Tmax = 0.792 | l = −8→8 |
2347 measured reflections | 3 standard reflections every 120 min |
2109 independent reflections | intensity decay: 1.5% |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.055 | w = 1/[σ2(Fo2) + (0.1304P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.150 | (Δ/σ)max < 0.001 |
S = 1.14 | Δρmax = 0.64 e Å−3 |
2109 reflections | Δρmin = −0.35 e Å−3 |
209 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.024 (3) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 778 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.05 (2) |
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 | x | y | z | Uiso*/Ueq | |
C1 | 0.3033 (6) | 0.47779 (18) | 0.1567 (5) | 0.0335 (7) | |
C2 | 0.1150 (7) | 0.5163 (2) | 0.2246 (5) | 0.0445 (9) | |
H2 | 0.0552 | 0.5055 | 0.3401 | 0.053* | |
C3 | 0.0121 (8) | 0.5716 (2) | 0.1217 (6) | 0.0510 (10) | |
H3 | −0.1197 | 0.5961 | 0.1678 | 0.061* | |
C4 | 0.1016 (8) | 0.5900 (2) | −0.0448 (7) | 0.0491 (9) | |
H4 | 0.0362 | 0.6277 | −0.1088 | 0.059* | |
C5 | 0.2947 (7) | 0.5514 (2) | −0.1198 (5) | 0.0431 (8) | |
C6 | 0.3954 (8) | 0.5673 (2) | −0.2909 (6) | 0.0514 (10) | |
H5 | 0.3393 | 0.6049 | −0.3589 | 0.062* | |
C7 | 0.5740 (9) | 0.5273 (2) | −0.3547 (6) | 0.0534 (10) | |
H7 | 0.6419 | 0.5372 | −0.4679 | 0.064* | |
C8 | 0.6576 (8) | 0.4709 (2) | −0.2506 (5) | 0.0463 (9) | |
H8 | 0.7784 | 0.4436 | −0.2996 | 0.056* | |
C9 | 0.3943 (6) | 0.49446 (17) | −0.0198 (5) | 0.0351 (7) | |
C10 | 0.2116 (7) | 0.31181 (19) | 0.1013 (5) | 0.0359 (7) | |
C11 | 0.0071 (7) | 0.32549 (19) | −0.0513 (5) | 0.0388 (8) | |
H11 | −0.1172 | 0.3580 | −0.0383 | 0.047* | |
C12 | −0.0134 (8) | 0.2910 (2) | −0.2229 (5) | 0.0428 (8) | |
H12 | −0.1502 | 0.2998 | −0.3265 | 0.051* | |
C13 | 0.1745 (8) | 0.24313 (19) | −0.2366 (5) | 0.0402 (8) | |
C14 | 0.3839 (8) | 0.2287 (2) | −0.0854 (6) | 0.0486 (9) | |
H14 | 0.5078 | 0.1962 | −0.0989 | 0.058* | |
C15 | 0.4028 (7) | 0.2638 (2) | 0.0842 (6) | 0.0443 (9) | |
H15 | 0.5419 | 0.2555 | 0.1868 | 0.053* | |
N1 | 0.4238 (5) | 0.42424 (16) | 0.2656 (4) | 0.0363 (7) | |
H1N | 0.5944 | 0.4254 | 0.3089 | 0.044* | |
N2 | 0.5751 (6) | 0.45395 (16) | −0.0870 (4) | 0.0394 (7) | |
N3 | 0.1571 (8) | 0.20655 (19) | −0.4186 (5) | 0.0538 (9) | |
O1 | 0.4238 (5) | 0.32587 (15) | 0.4625 (3) | 0.0449 (7) | |
O2 | −0.0106 (5) | 0.38155 (15) | 0.3409 (4) | 0.0461 (7) | |
O3 | −0.0368 (8) | 0.2168 (2) | −0.5470 (5) | 0.0761 (11) | |
O4 | 0.3307 (10) | 0.1676 (2) | −0.4337 (6) | 0.0867 (13) | |
S1 | 0.25229 (12) | 0.36028 (4) | 0.31245 (9) | 0.0337 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0243 (14) | 0.0341 (17) | 0.0403 (15) | 0.0005 (14) | −0.0003 (11) | −0.0043 (14) |
C2 | 0.0360 (17) | 0.049 (2) | 0.0479 (18) | 0.0045 (16) | 0.0057 (14) | −0.0097 (17) |
C3 | 0.0349 (18) | 0.043 (2) | 0.073 (2) | 0.0116 (16) | 0.0022 (16) | −0.0127 (19) |
C4 | 0.0395 (19) | 0.0335 (19) | 0.070 (2) | 0.0030 (16) | −0.0053 (17) | 0.0005 (17) |
C5 | 0.0337 (17) | 0.041 (2) | 0.0501 (18) | −0.0044 (15) | −0.0056 (13) | −0.0016 (17) |
C6 | 0.049 (2) | 0.047 (2) | 0.053 (2) | −0.0072 (18) | −0.0071 (16) | 0.0136 (18) |
C7 | 0.053 (2) | 0.062 (3) | 0.0448 (18) | −0.010 (2) | 0.0070 (16) | 0.0062 (18) |
C8 | 0.0422 (19) | 0.054 (2) | 0.0442 (17) | −0.0007 (17) | 0.0105 (15) | 0.0001 (16) |
C9 | 0.0282 (16) | 0.0371 (19) | 0.0386 (15) | −0.0031 (13) | 0.0007 (12) | −0.0026 (13) |
C10 | 0.0307 (15) | 0.0368 (18) | 0.0406 (15) | 0.0011 (13) | 0.0075 (12) | 0.0041 (13) |
C11 | 0.0307 (16) | 0.043 (2) | 0.0425 (16) | 0.0052 (14) | 0.0066 (13) | 0.0034 (15) |
C12 | 0.0405 (17) | 0.048 (2) | 0.0386 (16) | 0.0031 (16) | 0.0028 (13) | 0.0030 (15) |
C13 | 0.0396 (18) | 0.0373 (19) | 0.0461 (16) | −0.0034 (15) | 0.0136 (14) | 0.0004 (15) |
C14 | 0.040 (2) | 0.0396 (19) | 0.068 (2) | 0.0121 (17) | 0.0146 (17) | 0.0007 (19) |
C15 | 0.0293 (17) | 0.050 (2) | 0.053 (2) | 0.0061 (15) | 0.0040 (15) | 0.0029 (17) |
N1 | 0.0217 (12) | 0.0474 (19) | 0.0394 (13) | 0.0036 (11) | 0.0038 (10) | 0.0033 (12) |
N2 | 0.0368 (14) | 0.0429 (17) | 0.0387 (13) | 0.0032 (13) | 0.0062 (11) | 0.0007 (12) |
N3 | 0.069 (2) | 0.0397 (17) | 0.0567 (18) | −0.0064 (17) | 0.0237 (17) | −0.0041 (16) |
O1 | 0.0324 (12) | 0.0626 (18) | 0.0388 (11) | 0.0068 (11) | 0.0033 (10) | 0.0160 (12) |
O2 | 0.0271 (12) | 0.067 (2) | 0.0461 (12) | 0.0051 (11) | 0.0122 (9) | 0.0014 (11) |
O3 | 0.084 (2) | 0.078 (3) | 0.0618 (18) | −0.009 (2) | −0.0016 (17) | −0.0250 (19) |
O4 | 0.120 (3) | 0.069 (3) | 0.077 (2) | 0.029 (3) | 0.032 (2) | −0.014 (2) |
S1 | 0.0221 (4) | 0.0466 (5) | 0.0331 (4) | 0.0032 (3) | 0.0066 (2) | 0.0060 (3) |
Geometric parameters (Å, º) top
C1—C2 | 1.375 (5) | C10—C11 | 1.382 (5) |
C1—N1 | 1.419 (5) | C10—C15 | 1.398 (5) |
C1—C9 | 1.421 (5) | C10—S1 | 1.763 (4) |
C2—C3 | 1.400 (6) | C11—C12 | 1.381 (5) |
C2—H2 | 0.9300 | C11—H11 | 0.9300 |
C3—C4 | 1.364 (7) | C12—C13 | 1.379 (6) |
C3—H3 | 0.9300 | C12—H12 | 0.9300 |
C4—C5 | 1.417 (6) | C13—C14 | 1.394 (5) |
C4—H4 | 0.9300 | C13—N3 | 1.466 (5) |
C5—C6 | 1.406 (6) | C14—C15 | 1.376 (6) |
C5—C9 | 1.415 (5) | C14—H14 | 0.9300 |
C6—C7 | 1.344 (7) | C15—H15 | 0.9300 |
C6—H5 | 0.9300 | N1—S1 | 1.636 (3) |
C7—C8 | 1.401 (6) | N1—H1N | 0.8600 |
C7—H7 | 0.9300 | N3—O4 | 1.202 (5) |
C8—N2 | 1.321 (5) | N3—O3 | 1.229 (5) |
C8—H8 | 0.9300 | O1—S1 | 1.430 (2) |
C9—N2 | 1.370 (5) | O2—S1 | 1.433 (3) |
| | | |
C2—C1—N1 | 121.5 (3) | C15—C10—S1 | 119.0 (3) |
C2—C1—C9 | 119.5 (3) | C12—C11—C10 | 120.2 (3) |
N1—C1—C9 | 118.9 (3) | C12—C11—H11 | 119.9 |
C1—C2—C3 | 120.8 (4) | C10—C11—H11 | 119.9 |
C1—C2—H2 | 119.6 | C13—C12—C11 | 118.2 (3) |
C3—C2—H2 | 119.6 | C13—C12—H12 | 120.9 |
C4—C3—C2 | 121.2 (4) | C11—C12—H12 | 120.9 |
C4—C3—H3 | 119.4 | C12—C13—C14 | 122.7 (4) |
C2—C3—H3 | 119.4 | C12—C13—N3 | 118.9 (3) |
C3—C4—C5 | 119.7 (4) | C14—C13—N3 | 118.4 (3) |
C3—C4—H4 | 120.2 | C15—C14—C13 | 118.4 (4) |
C5—C4—H4 | 120.2 | C15—C14—H14 | 120.8 |
C6—C5—C9 | 117.7 (4) | C13—C14—H14 | 120.8 |
C6—C5—C4 | 122.8 (4) | C14—C15—C10 | 119.5 (3) |
C9—C5—C4 | 119.5 (4) | C14—C15—H15 | 120.2 |
C7—C6—C5 | 119.1 (4) | C10—C15—H15 | 120.2 |
C7—C6—H5 | 120.4 | C1—N1—S1 | 122.8 (2) |
C5—C6—H5 | 120.4 | C1—N1—H1N | 118.6 |
C6—C7—C8 | 119.9 (4) | S1—N1—H1N | 118.6 |
C6—C7—H7 | 120.1 | C8—N2—C9 | 116.8 (3) |
C8—C7—H7 | 120.1 | O4—N3—O3 | 123.4 (4) |
N2—C8—C7 | 123.9 (4) | O4—N3—C13 | 118.5 (4) |
N2—C8—H8 | 118.1 | O3—N3—C13 | 118.1 (4) |
C7—C8—H8 | 118.1 | O1—S1—O2 | 120.60 (16) |
N2—C9—C5 | 122.6 (3) | O1—S1—N1 | 105.83 (15) |
N2—C9—C1 | 118.1 (3) | O2—S1—N1 | 107.77 (16) |
C5—C9—C1 | 119.3 (3) | O1—S1—C10 | 107.63 (17) |
C11—C10—C15 | 120.9 (3) | O2—S1—C10 | 107.68 (16) |
C11—C10—S1 | 119.8 (3) | N1—S1—C10 | 106.57 (15) |
| | | |
N1—C1—C2—C3 | 175.5 (3) | C12—C13—C14—C15 | 0.1 (6) |
C9—C1—C2—C3 | 0.1 (5) | N3—C13—C14—C15 | 179.0 (4) |
C1—C2—C3—C4 | −2.2 (6) | C13—C14—C15—C10 | 0.8 (6) |
C2—C3—C4—C5 | 2.4 (6) | C11—C10—C15—C14 | −1.3 (6) |
C3—C4—C5—C6 | 179.8 (4) | S1—C10—C15—C14 | −175.4 (3) |
C3—C4—C5—C9 | −0.6 (5) | C2—C1—N1—S1 | 65.4 (4) |
C9—C5—C6—C7 | 1.9 (5) | C9—C1—N1—S1 | −119.1 (3) |
C4—C5—C6—C7 | −178.5 (4) | C7—C8—N2—C9 | 0.9 (6) |
C5—C6—C7—C8 | −0.2 (6) | C5—C9—N2—C8 | 1.0 (5) |
C6—C7—C8—N2 | −1.3 (6) | C1—C9—N2—C8 | −179.6 (3) |
C6—C5—C9—N2 | −2.4 (5) | C12—C13—N3—O4 | 175.6 (4) |
C4—C5—C9—N2 | 178.1 (3) | C14—C13—N3—O4 | −3.3 (6) |
C6—C5—C9—C1 | 178.2 (3) | C12—C13—N3—O3 | −5.3 (6) |
C4—C5—C9—C1 | −1.4 (5) | C14—C13—N3—O3 | 175.8 (4) |
C2—C1—C9—N2 | −177.8 (3) | C1—N1—S1—O1 | −165.7 (3) |
N1—C1—C9—N2 | 6.6 (5) | C1—N1—S1—O2 | −35.4 (3) |
C2—C1—C9—C5 | 1.7 (5) | C1—N1—S1—C10 | 79.9 (3) |
N1—C1—C9—C5 | −173.9 (3) | C11—C10—S1—O1 | 164.5 (3) |
C15—C10—C11—C12 | 0.9 (6) | C15—C10—S1—O1 | −21.3 (3) |
S1—C10—C11—C12 | 175.0 (3) | C11—C10—S1—O2 | 33.1 (3) |
C10—C11—C12—C13 | 0.0 (6) | C15—C10—S1—O2 | −152.7 (3) |
C11—C12—C13—C14 | −0.5 (6) | C11—C10—S1—N1 | −82.3 (3) |
C11—C12—C13—N3 | −179.4 (4) | C15—C10—S1—N1 | 91.9 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.86 | 2.16 | 2.935 (4) | 150 |
C11—H11···N2ii | 0.93 | 2.50 | 3.407 (5) | 1 |
C12—H12···O1iii | 0.93 | 2.45 | 3.360 (4) | 166 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) x−1, y, z−1. |