8-(Tolyl-4-sulfon­yloxy)quinolinium toluene-4-sulfonate

In the cation of the title compound, C₁₆H₁₄NO₃S⁺·C₇H₇O₃S^-, the quinolinium ring system makes a dihedral angle of 69.14 (9)° with the benzene ring.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.042
• wR factor = 0.120
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.75 Ratio

Alert level C
PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) .        500 Ang.
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         500 Deg.
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.96 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   O2      ..       5.16 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 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
   1 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

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

8-(Tolyl-4-sulfonyloxy)quinolinium toluene-4-sulfonate

Crystal data

C16H14NO3S^+·C7H7O3S^−	Z = 2
Mr = 471.53	F(000) = 492
Triclinic, P1	Dx = 1.404 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.643 (5) Å	Cell parameters from 3363 reflections
b = 10.852 (5) Å	θ = 2.3–27.6°
c = 11.421 (5) Å	µ = 0.28 mm^−1
α = 105.470 (5)°	T = 292 K
β = 97.976 (5)°	Block, yellow
γ = 99.295 (5)°	0.45 × 0.26 × 0.24 mm
V = 1115.8 (9) Å^3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	4111 independent reflections
Radiation source: fine-focus sealed tube	3208 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.886, Tmax = 0.936	k = −13→13
8405 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0577P)^2 + 0.4629P] where P = (Fo^2 + 2Fc^2)/3
4111 reflections	(Δ/σ)max = 0.001
291 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.65547 (6)	0.77989 (6)	0.53688 (6)	0.05187 (19)
S2	0.27084 (6)	0.49734 (6)	1.15112 (5)	0.04364 (17)
O1	0.53022 (15)	0.65696 (15)	0.52686 (14)	0.0448 (4)
O2	0.6116 (2)	0.8423 (2)	0.44730 (18)	0.0730 (6)
O3	0.77604 (18)	0.7213 (2)	0.52956 (19)	0.0763 (6)
O4	0.32959 (18)	0.44568 (17)	1.24907 (16)	0.0570 (4)
O5	0.3805 (2)	0.58715 (17)	1.12421 (19)	0.0706 (5)
O6	0.14512 (18)	0.54711 (19)	1.17682 (16)	0.0635 (5)
N1	0.39310 (19)	0.56788 (17)	0.69216 (17)	0.0421 (4)
H1	0.4824	0.5683	0.6926	0.051*
C1	0.3891 (2)	0.6729 (2)	0.52928 (19)	0.0379 (5)
C2	0.3146 (2)	0.7218 (2)	0.4488 (2)	0.0499 (6)
H2	0.3583	0.7509	0.3907	0.060*
C3	0.1710 (3)	0.7279 (3)	0.4538 (3)	0.0592 (7)
H3	0.1210	0.7640	0.4004	0.071*
C4	0.1044 (2)	0.6822 (2)	0.5352 (2)	0.0528 (6)
H4	0.0097	0.6882	0.5378	0.063*
C5	0.1769 (2)	0.6259 (2)	0.6158 (2)	0.0417 (5)
C6	0.1124 (2)	0.5685 (2)	0.6976 (2)	0.0525 (6)
H6	0.0168	0.5694	0.7014	0.063*
C7	0.1870 (3)	0.5119 (3)	0.7704 (2)	0.0587 (7)
H7	0.1425	0.4722	0.8221	0.070*
C8	0.3304 (3)	0.5141 (2)	0.7671 (2)	0.0527 (6)
H8	0.3829	0.4773	0.8182	0.063*
C9	0.3229 (2)	0.62297 (19)	0.61380 (19)	0.0357 (5)
C10	0.6670 (2)	0.8842 (2)	0.6845 (2)	0.0459 (5)
C11	0.6079 (3)	0.9935 (3)	0.6988 (3)	0.0637 (7)
H11	0.5604	1.0107	0.6301	0.076*
C12	0.6199 (3)	1.0765 (3)	0.8148 (4)	0.0768 (9)
H12	0.5820	1.1513	0.8242	0.092*
C13	0.6868 (4)	1.0518 (3)	0.9181 (3)	0.0772 (9)
C14	0.7477 (4)	0.9422 (3)	0.9019 (3)	0.0842 (10)
H14	0.7951	0.9252	0.9706	0.101*
C15	0.7389 (3)	0.8583 (2)	0.7857 (3)	0.0663 (8)
H15	0.7806	0.7855	0.7756	0.080*
C16	0.6996 (5)	1.1426 (4)	1.0475 (4)	0.1344 (18)
H16A	0.7984	1.1693	1.0878	0.202*
H16B	0.6462	1.0978	1.0943	0.202*
H16C	0.6623	1.2183	1.0424	0.202*
C17	0.2144 (2)	0.3616 (2)	1.0161 (2)	0.0404 (5)
C18	0.3148 (2)	0.3100 (2)	0.9522 (2)	0.0484 (6)
H18	0.4119	0.3447	0.9821	0.058*
C19	0.2707 (3)	0.2081 (3)	0.8451 (2)	0.0545 (6)
H19	0.3390	0.1757	0.8027	0.065*
C20	0.1265 (3)	0.1521 (3)	0.7982 (2)	0.0557 (6)
C21	0.0282 (3)	0.2048 (3)	0.8629 (2)	0.0582 (7)
H21	−0.0689	0.1694	0.8334	0.070*
C22	0.0700 (2)	0.3080 (2)	0.9698 (2)	0.0499 (6)
H22	0.0015	0.3419	1.0109	0.060*
C23	0.0804 (4)	0.0404 (3)	0.6809 (3)	0.0873 (10)
H23A	0.0942	0.0719	0.6115	0.131*
H23B	−0.0190	0.0024	0.6719	0.131*
H23C	0.1365	−0.0245	0.6843	0.131*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0347 (3)	0.0648 (4)	0.0562 (4)	0.0067 (3)	0.0173 (3)	0.0158 (3)
S2	0.0335 (3)	0.0478 (3)	0.0547 (4)	0.0137 (2)	0.0109 (2)	0.0191 (3)
O1	0.0312 (8)	0.0491 (9)	0.0536 (9)	0.0115 (7)	0.0126 (7)	0.0100 (7)
O2	0.0642 (12)	0.0985 (15)	0.0635 (12)	−0.0009 (11)	0.0160 (9)	0.0444 (11)
O3	0.0351 (9)	0.0932 (14)	0.0926 (15)	0.0171 (9)	0.0254 (9)	0.0051 (12)
O4	0.0515 (10)	0.0610 (10)	0.0569 (10)	0.0175 (8)	−0.0029 (8)	0.0180 (9)
O5	0.0686 (12)	0.0533 (11)	0.0911 (14)	0.0011 (9)	0.0294 (11)	0.0233 (10)
O6	0.0451 (10)	0.0822 (13)	0.0655 (11)	0.0330 (9)	0.0127 (8)	0.0131 (10)
N1	0.0325 (9)	0.0448 (10)	0.0486 (11)	0.0091 (8)	0.0054 (8)	0.0136 (9)
C1	0.0290 (10)	0.0403 (11)	0.0401 (11)	0.0081 (9)	0.0050 (9)	0.0051 (9)
C2	0.0454 (13)	0.0572 (14)	0.0481 (14)	0.0099 (11)	0.0053 (10)	0.0197 (12)
C3	0.0465 (14)	0.0666 (16)	0.0637 (17)	0.0197 (12)	−0.0065 (12)	0.0217 (14)
C4	0.0330 (12)	0.0607 (15)	0.0602 (15)	0.0182 (11)	0.0023 (11)	0.0084 (12)
C5	0.0298 (11)	0.0436 (12)	0.0440 (12)	0.0080 (9)	0.0067 (9)	0.0000 (10)
C6	0.0349 (12)	0.0583 (15)	0.0552 (15)	0.0033 (11)	0.0158 (11)	0.0017 (12)
C7	0.0511 (15)	0.0679 (17)	0.0568 (16)	−0.0009 (13)	0.0153 (12)	0.0232 (14)
C8	0.0515 (14)	0.0544 (14)	0.0535 (15)	0.0060 (11)	0.0063 (11)	0.0229 (12)
C9	0.0291 (10)	0.0359 (11)	0.0377 (11)	0.0087 (8)	0.0036 (8)	0.0034 (9)
C10	0.0379 (12)	0.0437 (12)	0.0570 (14)	0.0054 (10)	0.0112 (10)	0.0171 (11)
C11	0.0430 (14)	0.0567 (16)	0.089 (2)	0.0143 (12)	0.0048 (13)	0.0186 (15)
C12	0.0525 (17)	0.0541 (17)	0.112 (3)	0.0142 (13)	0.0186 (17)	0.0012 (18)
C13	0.082 (2)	0.0523 (17)	0.078 (2)	−0.0128 (15)	0.0331 (18)	−0.0054 (15)
C14	0.133 (3)	0.0545 (18)	0.0564 (18)	−0.0034 (18)	0.0106 (18)	0.0192 (15)
C15	0.094 (2)	0.0423 (14)	0.0627 (18)	0.0154 (14)	0.0085 (15)	0.0189 (13)
C16	0.159 (4)	0.093 (3)	0.109 (3)	−0.017 (3)	0.059 (3)	−0.032 (2)
C17	0.0336 (11)	0.0484 (12)	0.0471 (13)	0.0123 (9)	0.0118 (9)	0.0234 (10)
C18	0.0321 (11)	0.0642 (15)	0.0544 (14)	0.0138 (11)	0.0134 (10)	0.0219 (12)
C19	0.0491 (14)	0.0655 (16)	0.0541 (15)	0.0195 (12)	0.0190 (11)	0.0173 (13)
C20	0.0581 (16)	0.0586 (15)	0.0495 (14)	0.0080 (12)	0.0092 (12)	0.0176 (12)
C21	0.0404 (13)	0.0689 (17)	0.0617 (16)	0.0010 (12)	0.0076 (12)	0.0206 (14)
C22	0.0319 (12)	0.0652 (15)	0.0589 (15)	0.0121 (11)	0.0145 (10)	0.0250 (13)
C23	0.089 (2)	0.084 (2)	0.070 (2)	0.0028 (19)	0.0126 (17)	0.0010 (17)

Geometric parameters (Å, º)

S1—O3	1.4147 (19)	C10—C15	1.382 (4)
S1—O2	1.423 (2)	C11—C12	1.366 (4)
S1—O1	1.6159 (17)	C11—H11	0.9300
S1—C10	1.740 (3)	C12—C13	1.376 (5)
S2—O6	1.4399 (17)	C12—H12	0.9300
S2—O5	1.4423 (19)	C13—C14	1.390 (5)
S2—O4	1.4656 (17)	C13—C16	1.518 (4)
S2—C17	1.772 (2)	C14—C15	1.377 (4)
O1—C1	1.403 (2)	C14—H14	0.9300
N1—C8	1.317 (3)	C15—H15	0.9300
N1—C9	1.365 (3)	C16—H16A	0.9600
N1—H1	0.8600	C16—H16B	0.9600
C1—C2	1.357 (3)	C16—H16C	0.9600
C1—C9	1.404 (3)	C17—C22	1.388 (3)
C2—C3	1.405 (3)	C17—C18	1.391 (3)
C2—H2	0.9300	C18—C19	1.372 (3)
C3—C4	1.354 (4)	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.391 (4)
C4—C5	1.403 (3)	C19—H19	0.9300
C4—H4	0.9300	C20—C21	1.385 (4)
C5—C6	1.412 (3)	C20—C23	1.502 (4)
C5—C9	1.417 (3)	C21—C22	1.376 (4)
C6—C7	1.355 (3)	C21—H21	0.9300
C6—H6	0.9300	C22—H22	0.9300
C7—C8	1.386 (3)	C23—H23A	0.9600
C7—H7	0.9300	C23—H23B	0.9600
C8—H8	0.9300	C23—H23C	0.9600
C10—C11	1.379 (3)
O3—S1—O2	119.98 (13)	C12—C11—C10	119.3 (3)
O3—S1—O1	101.72 (11)	C12—C11—H11	120.3
O2—S1—O1	109.18 (10)	C10—C11—H11	120.3
O3—S1—C10	111.26 (12)	C11—C12—C13	121.5 (3)
O2—S1—C10	109.38 (13)	C11—C12—H12	119.3
O1—S1—C10	103.86 (10)	C13—C12—H12	119.3
O6—S2—O5	114.90 (12)	C12—C13—C14	118.4 (3)
O6—S2—O4	111.47 (11)	C12—C13—C16	121.9 (4)
O5—S2—O4	111.11 (12)	C14—C13—C16	119.7 (4)
O6—S2—C17	106.60 (11)	C15—C14—C13	121.2 (3)
O5—S2—C17	106.29 (11)	C15—C14—H14	119.4
O4—S2—C17	105.81 (11)	C13—C14—H14	119.4
C1—O1—S1	120.44 (13)	C14—C15—C10	118.8 (3)
C8—N1—C9	123.1 (2)	C14—C15—H15	120.6
C8—N1—H1	118.5	C10—C15—H15	120.6
C9—N1—H1	118.5	C13—C16—H16A	109.5
C2—C1—O1	123.4 (2)	C13—C16—H16B	109.5
C2—C1—C9	120.9 (2)	H16A—C16—H16B	109.5
O1—C1—C9	115.37 (18)	C13—C16—H16C	109.5
C1—C2—C3	119.6 (2)	H16A—C16—H16C	109.5
C1—C2—H2	120.2	H16B—C16—H16C	109.5
C3—C2—H2	120.2	C22—C17—C18	118.9 (2)
C4—C3—C2	121.0 (2)	C22—C17—S2	120.89 (18)
C4—C3—H3	119.5	C18—C17—S2	120.18 (17)
C2—C3—H3	119.5	C19—C18—C17	120.1 (2)
C3—C4—C5	120.7 (2)	C19—C18—H18	119.9
C3—C4—H4	119.7	C17—C18—H18	119.9
C5—C4—H4	119.7	C18—C19—C20	121.8 (2)
C4—C5—C6	124.0 (2)	C18—C19—H19	119.1
C4—C5—C9	118.6 (2)	C20—C19—H19	119.1
C6—C5—C9	117.4 (2)	C21—C20—C19	117.3 (2)
C7—C6—C5	121.3 (2)	C21—C20—C23	121.8 (3)
C7—C6—H6	119.4	C19—C20—C23	120.9 (3)
C5—C6—H6	119.4	C22—C21—C20	121.9 (2)
C6—C7—C8	119.2 (2)	C22—C21—H21	119.0
C6—C7—H7	120.4	C20—C21—H21	119.0
C8—C7—H7	120.4	C21—C22—C17	120.0 (2)
N1—C8—C7	120.6 (2)	C21—C22—H22	120.0
N1—C8—H8	119.7	C17—C22—H22	120.0
C7—C8—H8	119.7	C20—C23—H23A	109.5
N1—C9—C1	122.36 (18)	C20—C23—H23B	109.5
N1—C9—C5	118.45 (19)	H23A—C23—H23B	109.5
C1—C9—C5	119.16 (19)	C20—C23—H23C	109.5
C11—C10—C15	120.9 (3)	H23A—C23—H23C	109.5
C11—C10—S1	119.6 (2)	H23B—C23—H23C	109.5
C15—C10—S1	119.50 (19)
O3—S1—O1—C1	−179.43 (16)	O3—S1—C10—C15	−30.0 (2)
O2—S1—O1—C1	−51.66 (18)	O2—S1—C10—C15	−164.9 (2)
C10—S1—O1—C1	64.94 (17)	O1—S1—C10—C15	78.7 (2)
S1—O1—C1—C2	56.4 (3)	C15—C10—C11—C12	−0.5 (4)
S1—O1—C1—C9	−129.58 (17)	S1—C10—C11—C12	−178.7 (2)
O1—C1—C2—C3	176.7 (2)	C10—C11—C12—C13	−1.5 (4)
C9—C1—C2—C3	2.9 (3)	C11—C12—C13—C14	2.5 (5)
C1—C2—C3—C4	−2.0 (4)	C11—C12—C13—C16	−179.4 (3)
C2—C3—C4—C5	−0.8 (4)	C12—C13—C14—C15	−1.4 (5)
C3—C4—C5—C6	−175.7 (2)	C16—C13—C14—C15	−179.6 (3)
C3—C4—C5—C9	2.7 (3)	C13—C14—C15—C10	−0.5 (5)
C4—C5—C6—C7	177.9 (2)	C11—C10—C15—C14	1.5 (4)
C9—C5—C6—C7	−0.5 (3)	S1—C10—C15—C14	179.7 (2)
C5—C6—C7—C8	1.9 (4)	O6—S2—C17—C22	−11.8 (2)
C9—N1—C8—C7	−0.5 (4)	O5—S2—C17—C22	−134.77 (19)
C6—C7—C8—N1	−1.4 (4)	O4—S2—C17—C22	107.02 (19)
C8—N1—C9—C1	−176.1 (2)	O6—S2—C17—C18	165.84 (18)
C8—N1—C9—C5	1.9 (3)	O5—S2—C17—C18	42.8 (2)
C2—C1—C9—N1	177.0 (2)	O4—S2—C17—C18	−75.4 (2)
O1—C1—C9—N1	2.8 (3)	C22—C17—C18—C19	0.1 (3)
C2—C1—C9—C5	−1.0 (3)	S2—C17—C18—C19	−177.51 (18)
O1—C1—C9—C5	−175.24 (17)	C17—C18—C19—C20	−1.0 (4)
C4—C5—C9—N1	−179.88 (19)	C18—C19—C20—C21	1.1 (4)
C6—C5—C9—N1	−1.4 (3)	C18—C19—C20—C23	−179.9 (3)
C4—C5—C9—C1	−1.8 (3)	C19—C20—C21—C22	−0.3 (4)
C6—C5—C9—C1	176.7 (2)	C23—C20—C21—C22	−179.3 (3)
O3—S1—C10—C11	148.1 (2)	C20—C21—C22—C17	−0.6 (4)
O2—S1—C10—C11	13.3 (2)	C18—C17—C22—C21	0.7 (3)
O1—S1—C10—C11	−103.2 (2)	S2—C17—C22—C21	178.27 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4^i	0.86	1.89	2.703 (3)	158
C4—H4···O3^ii	0.93	2.33	3.256 (3)	173
C8—H8···O5^i	0.93	2.54	3.358 (4)	146
C15—H15···O4^i	0.93	2.49	3.162 (3)	130
C18—H18···O5^i	0.93	2.59	3.288 (3)	132

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) x−1, y, z.