2-[(E)-2-(3-Hydr­oxy-4-methoxy­phen­yl)ethen­yl]-1-methyl­quinolinium 4-chloro­benzene­sulfonate

The title compound, C₁₉H₁₈NO₂⁺·C₆H₄ClO₃S⁻, exhibits non-linear optical properties. The cation is almost planar and the benzene ring of the anion makes dihedral angles of 48.97 (6) and 51.63 (7)° with the mean planes through the quinolinium system and the benzene ring of the cation, respectively. The anions are linked by C—H...O inter­actions, forming a chain along the a axis, while the cations are stacked along the a axis. The anionic chains and the cationic stacks are alternately arranged.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.110
• Data-to-parameter ratio = 21.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         S1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C23
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H10    ..  H19A    ..       1.83 Ang.

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           30.06
           From the CIF: _reflns_number_total               6533
           Count of symmetry unique reflns         3700
           Completeness (_total/calc)            176.57%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2833
           Fraction of Friedel pairs measured     0.766
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

2-[(E)-2-(3-Hydroxy-4-methoxyphenyl)ethenyl]-1-methylquinolinium 4-chlorobenzenesulfonate

Crystal data

C19H18NO2^+·C6H4ClO3S^−	Dx = 1.442 Mg m^−3
Mr = 483.96	Melting point = 535–536 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6533 reflections
a = 6.9503 (1) Å	θ = 1.6–30.1°
b = 15.6916 (2) Å	µ = 0.30 mm^−1
c = 20.4365 (3) Å	T = 297 K
V = 2228.83 (5) Å^3	Block, orange
Z = 4	0.51 × 0.31 × 0.31 mm
F(000) = 1008

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	6533 independent reflections
Radiation source: fine-focus sealed tube	4956 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 8.33 pixels mm^-1	θmax = 30.1°, θmin = 1.6°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −22→20
Tmin = 0.860, Tmax = 0.910	l = −24→28
28163 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.052P)^2 + 0.2404P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
6533 reflections	Δρmax = 0.30 e Å^−3
301 parameters	Δρmin = −0.36 e Å^−3
2 restraints	Absolute structure: Flack (1983), 2836 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (6)

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	0.61162 (7)	0.41640 (3)	0.42277 (3)	0.05324 (13)
Cl1	1.27649 (14)	0.67217 (5)	0.48346 (5)	0.1111 (3)
O3	0.7036 (3)	0.33626 (9)	0.41150 (10)	0.0804 (5)
O4	0.4886 (3)	0.41688 (14)	0.47938 (9)	0.0896 (6)
O5	0.5172 (2)	0.45005 (10)	0.36424 (8)	0.0669 (4)
C20	0.7976 (3)	0.49063 (11)	0.43890 (8)	0.0423 (4)
C21	0.7707 (3)	0.55421 (13)	0.48490 (10)	0.0560 (5)
H21	0.6543	0.5586	0.5071	0.067*
C22	0.9171 (4)	0.61106 (13)	0.49759 (11)	0.0662 (6)
H22	0.9000	0.6544	0.5281	0.079*
C23	1.0879 (3)	0.60318 (13)	0.46486 (11)	0.0607 (5)
C24	1.1167 (3)	0.54143 (14)	0.41854 (11)	0.0602 (5)
H24	1.2331	0.5376	0.3963	0.072*
C25	0.9692 (3)	0.48512 (13)	0.40551 (10)	0.0505 (4)
H25	0.9859	0.4431	0.3739	0.061*
O1	0.2589 (2)	0.38939 (10)	0.28294 (8)	0.0646 (4)
H1	0.3432	0.4068	0.3076	0.097*
O2	0.0440 (2)	0.33297 (10)	0.18874 (7)	0.0656 (4)
N1	1.1385 (2)	0.15322 (10)	0.36158 (7)	0.0469 (4)
C1	1.3107 (3)	0.11038 (12)	0.37596 (10)	0.0492 (4)
C2	1.4388 (3)	0.14081 (15)	0.42325 (11)	0.0606 (5)
H2	1.4107	0.1903	0.4464	0.073*
C3	1.6067 (3)	0.09699 (17)	0.43531 (12)	0.0701 (6)
H3	1.6917	0.1177	0.4667	0.084*
C4	1.6521 (4)	0.02303 (18)	0.40199 (13)	0.0746 (7)
H4	1.7657	−0.0058	0.4112	0.089*
C5	1.5286 (4)	−0.00762 (16)	0.35520 (13)	0.0720 (7)
H5	1.5596	−0.0571	0.3325	0.086*
C6	1.3551 (3)	0.03533 (13)	0.34117 (10)	0.0568 (5)
C7	1.2253 (4)	0.00716 (15)	0.29354 (12)	0.0692 (6)
H7	1.2525	−0.0423	0.2702	0.083*
C8	1.0607 (4)	0.05040 (15)	0.28068 (11)	0.0650 (6)
H8	0.9752	0.0296	0.2495	0.078*
C9	1.0179 (3)	0.12695 (12)	0.31433 (10)	0.0497 (4)
C10	0.8465 (3)	0.17639 (13)	0.29797 (10)	0.0532 (5)
H10	0.8288	0.2281	0.3194	0.064*
C11	0.7142 (3)	0.15312 (13)	0.25482 (10)	0.0535 (5)
H11	0.7345	0.1015	0.2336	0.064*
C12	0.5409 (3)	0.19947 (13)	0.23704 (9)	0.0490 (4)
C13	0.4235 (3)	0.16903 (15)	0.18773 (10)	0.0614 (5)
H13	0.4562	0.1188	0.1663	0.074*
C14	0.2576 (3)	0.21212 (15)	0.16956 (11)	0.0613 (5)
H14	0.1819	0.1912	0.1356	0.074*
C15	0.2044 (3)	0.28578 (13)	0.20156 (10)	0.0516 (4)
C16	0.3208 (3)	0.31718 (12)	0.25236 (9)	0.0474 (4)
C17	0.4871 (3)	0.27512 (12)	0.26917 (9)	0.0485 (4)
H17	0.5649	0.2969	0.3022	0.058*
C18	−0.0787 (4)	0.30374 (18)	0.13781 (11)	0.0705 (6)
H18A	−0.1881	0.3408	0.1344	0.106*
H18B	−0.1212	0.2469	0.1475	0.106*
H18C	−0.0095	0.3038	0.0971	0.106*
C19	1.0938 (4)	0.22948 (14)	0.40144 (11)	0.0659 (6)
H19A	0.9606	0.2441	0.3961	0.099*
H19B	1.1726	0.2763	0.3874	0.099*
H19C	1.1191	0.2175	0.4467	0.099*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0453 (2)	0.0489 (3)	0.0656 (3)	−0.0010 (2)	−0.0045 (2)	−0.0004 (2)
Cl1	0.1121 (6)	0.0810 (5)	0.1403 (7)	−0.0424 (4)	−0.0707 (6)	0.0291 (4)
O3	0.0734 (10)	0.0435 (8)	0.1241 (15)	0.0032 (8)	−0.0184 (11)	−0.0085 (9)
O4	0.0623 (10)	0.1208 (16)	0.0856 (12)	−0.0203 (11)	0.0157 (9)	0.0086 (11)
O5	0.0695 (9)	0.0575 (8)	0.0737 (10)	−0.0025 (7)	−0.0272 (8)	−0.0042 (7)
C20	0.0438 (9)	0.0391 (8)	0.0440 (9)	0.0056 (7)	−0.0028 (7)	−0.0022 (7)
C21	0.0617 (12)	0.0543 (11)	0.0521 (11)	0.0137 (10)	0.0029 (10)	−0.0078 (9)
C22	0.0960 (16)	0.0426 (10)	0.0599 (12)	0.0081 (11)	−0.0178 (12)	−0.0109 (9)
C23	0.0655 (12)	0.0469 (10)	0.0698 (13)	−0.0089 (10)	−0.0300 (11)	0.0119 (10)
C24	0.0443 (10)	0.0617 (12)	0.0745 (14)	−0.0002 (9)	−0.0028 (11)	0.0138 (11)
C25	0.0499 (10)	0.0476 (10)	0.0538 (11)	0.0047 (8)	0.0046 (9)	−0.0044 (8)
O1	0.0601 (9)	0.0646 (9)	0.0690 (10)	0.0115 (7)	−0.0186 (8)	−0.0158 (7)
O2	0.0576 (8)	0.0693 (10)	0.0699 (9)	0.0059 (8)	−0.0189 (7)	−0.0081 (8)
N1	0.0506 (9)	0.0431 (8)	0.0471 (8)	0.0037 (7)	0.0048 (7)	0.0026 (7)
C1	0.0496 (10)	0.0479 (10)	0.0502 (10)	0.0054 (8)	0.0099 (8)	0.0154 (8)
C2	0.0554 (12)	0.0669 (13)	0.0596 (12)	0.0036 (10)	0.0016 (10)	0.0090 (11)
C3	0.0516 (11)	0.0861 (17)	0.0726 (14)	0.0031 (12)	0.0004 (12)	0.0211 (13)
C4	0.0550 (13)	0.0839 (17)	0.0848 (17)	0.0146 (12)	0.0129 (12)	0.0356 (14)
C5	0.0717 (15)	0.0634 (13)	0.0810 (16)	0.0222 (12)	0.0229 (14)	0.0172 (12)
C6	0.0609 (12)	0.0532 (11)	0.0562 (11)	0.0100 (9)	0.0129 (9)	0.0104 (9)
C7	0.0843 (16)	0.0523 (12)	0.0708 (14)	0.0175 (12)	0.0081 (12)	−0.0051 (10)
C8	0.0780 (15)	0.0559 (12)	0.0612 (12)	0.0123 (11)	−0.0056 (12)	−0.0101 (10)
C9	0.0541 (11)	0.0456 (10)	0.0493 (10)	0.0039 (8)	0.0056 (9)	0.0056 (8)
C10	0.0584 (12)	0.0462 (10)	0.0551 (11)	0.0057 (9)	−0.0004 (9)	0.0012 (8)
C11	0.0600 (11)	0.0509 (10)	0.0497 (10)	0.0023 (9)	0.0028 (9)	−0.0019 (8)
C12	0.0524 (10)	0.0503 (10)	0.0442 (9)	−0.0022 (8)	0.0015 (8)	0.0014 (8)
C13	0.0636 (13)	0.0606 (12)	0.0600 (12)	0.0036 (10)	−0.0052 (11)	−0.0125 (10)
C14	0.0616 (12)	0.0678 (13)	0.0545 (12)	−0.0071 (11)	−0.0113 (10)	−0.0104 (10)
C15	0.0502 (10)	0.0560 (11)	0.0487 (10)	−0.0053 (9)	−0.0032 (8)	0.0029 (9)
C16	0.0516 (10)	0.0459 (9)	0.0448 (10)	−0.0035 (8)	−0.0010 (8)	0.0004 (8)
C17	0.0511 (10)	0.0495 (10)	0.0451 (10)	−0.0027 (9)	−0.0020 (8)	−0.0009 (8)
C18	0.0589 (13)	0.0937 (17)	0.0588 (12)	0.0004 (12)	−0.0165 (11)	−0.0025 (12)
C19	0.0664 (13)	0.0586 (13)	0.0727 (14)	0.0159 (11)	−0.0115 (12)	−0.0164 (10)

Geometric parameters (Å, º)

S1—O3	1.4293 (17)	C4—H4	0.93
S1—O4	1.4385 (18)	C5—C6	1.411 (3)
S1—O5	1.4631 (16)	C5—H5	0.93
S1—C20	1.7708 (19)	C6—C7	1.399 (3)
Cl1—C23	1.742 (2)	C7—C8	1.356 (3)
C20—C25	1.377 (3)	C7—H7	0.93
C20—C21	1.383 (3)	C8—C9	1.416 (3)
C21—C22	1.378 (3)	C8—H8	0.93
C21—H21	0.93	C9—C10	1.461 (3)
C22—C23	1.368 (4)	C10—C11	1.325 (3)
C22—H22	0.93	C10—H10	0.93
C23—C24	1.369 (3)	C11—C12	1.453 (3)
C24—C25	1.379 (3)	C11—H11	0.93
C24—H24	0.93	C12—C13	1.382 (3)
C25—H25	0.93	C12—C17	1.407 (3)
O1—C16	1.364 (2)	C13—C14	1.387 (3)
O1—H1	0.82	C13—H13	0.93
O2—C15	1.364 (3)	C14—C15	1.379 (3)
O2—C18	1.421 (3)	C14—H14	0.93
N1—C9	1.343 (3)	C15—C16	1.405 (3)
N1—C1	1.404 (2)	C16—C17	1.374 (3)
N1—C19	1.481 (3)	C17—H17	0.93
C1—C2	1.398 (3)	C18—H18A	0.96
C1—C6	1.410 (3)	C18—H18B	0.96
C2—C3	1.377 (3)	C18—H18C	0.96
C2—H2	0.93	C19—H19A	0.96
C3—C4	1.382 (4)	C19—H19B	0.96
C3—H3	0.93	C19—H19C	0.96
C4—C5	1.372 (4)
O3—S1—O4	113.57 (13)	C1—C6—C5	118.9 (2)
O3—S1—O5	112.73 (11)	C8—C7—C6	121.4 (2)
O4—S1—O5	112.90 (11)	C8—C7—H7	119.3
O3—S1—C20	106.40 (10)	C6—C7—H7	119.3
O4—S1—C20	106.30 (10)	C7—C8—C9	120.5 (2)
O5—S1—C20	104.02 (9)	C7—C8—H8	119.8
C25—C20—C21	119.94 (19)	C9—C8—H8	119.8
C25—C20—S1	119.92 (14)	N1—C9—C8	118.60 (19)
C21—C20—S1	120.14 (16)	N1—C9—C10	120.70 (17)
C22—C21—C20	119.7 (2)	C8—C9—C10	120.7 (2)
C22—C21—H21	120.2	C11—C10—C9	124.89 (19)
C20—C21—H21	120.2	C11—C10—H10	117.6
C23—C22—C21	119.36 (19)	C9—C10—H10	117.6
C23—C22—H22	120.3	C10—C11—C12	127.12 (19)
C21—C22—H22	120.3	C10—C11—H11	116.4
C22—C23—C24	121.9 (2)	C12—C11—H11	116.4
C22—C23—Cl1	119.34 (18)	C13—C12—C17	118.34 (19)
C24—C23—Cl1	118.7 (2)	C13—C12—C11	119.93 (19)
C23—C24—C25	118.6 (2)	C17—C12—C11	121.73 (18)
C23—C24—H24	120.7	C12—C13—C14	121.2 (2)
C25—C24—H24	120.7	C12—C13—H13	119.4
C20—C25—C24	120.52 (18)	C14—C13—H13	119.4
C20—C25—H25	119.7	C15—C14—C13	120.3 (2)
C24—C25—H25	119.7	C15—C14—H14	119.8
C16—O1—H1	109.5	C13—C14—H14	119.8
C15—O2—C18	117.12 (18)	O2—C15—C14	125.69 (19)
C9—N1—C1	122.37 (16)	O2—C15—C16	114.99 (18)
C9—N1—C19	120.82 (16)	C14—C15—C16	119.32 (19)
C1—N1—C19	116.80 (17)	O1—C16—C17	123.34 (18)
C2—C1—N1	121.60 (18)	O1—C16—C15	116.62 (18)
C2—C1—C6	119.65 (19)	C17—C16—C15	120.04 (18)
N1—C1—C6	118.75 (19)	C16—C17—C12	120.79 (18)
C3—C2—C1	119.5 (2)	C16—C17—H17	119.6
C3—C2—H2	120.2	C12—C17—H17	119.6
C1—C2—H2	120.2	O2—C18—H18A	109.5
C2—C3—C4	121.6 (2)	O2—C18—H18B	109.5
C2—C3—H3	119.2	H18A—C18—H18B	109.5
C4—C3—H3	119.2	O2—C18—H18C	109.5
C5—C4—C3	119.7 (2)	H18A—C18—H18C	109.5
C5—C4—H4	120.2	H18B—C18—H18C	109.5
C3—C4—H4	120.2	N1—C19—H19A	109.5
C4—C5—C6	120.6 (2)	N1—C19—H19B	109.5
C4—C5—H5	119.7	H19A—C19—H19B	109.5
C6—C5—H5	119.7	N1—C19—H19C	109.5
C7—C6—C1	118.27 (19)	H19A—C19—H19C	109.5
C7—C6—C5	122.8 (2)	H19B—C19—H19C	109.5
O3—S1—C20—C25	37.08 (18)	C4—C5—C6—C1	0.1 (3)
O4—S1—C20—C25	158.44 (16)	C1—C6—C7—C8	0.1 (3)
O5—S1—C20—C25	−82.17 (17)	C5—C6—C7—C8	−179.2 (2)
O3—S1—C20—C21	−143.01 (17)	C6—C7—C8—C9	1.5 (4)
O4—S1—C20—C21	−21.65 (19)	C1—N1—C9—C8	3.9 (3)
O5—S1—C20—C21	97.75 (17)	C19—N1—C9—C8	−175.7 (2)
C25—C20—C21—C22	−0.8 (3)	C1—N1—C9—C10	−175.97 (17)
S1—C20—C21—C22	179.27 (16)	C19—N1—C9—C10	4.4 (3)
C20—C21—C22—C23	−0.6 (3)	C7—C8—C9—N1	−3.5 (3)
C21—C22—C23—C24	1.5 (3)	C7—C8—C9—C10	176.4 (2)
C21—C22—C23—Cl1	−177.25 (16)	N1—C9—C10—C11	−176.05 (19)
C22—C23—C24—C25	−0.9 (3)	C8—C9—C10—C11	4.0 (3)
Cl1—C23—C24—C25	177.85 (16)	C9—C10—C11—C12	179.61 (18)
C21—C20—C25—C24	1.4 (3)	C10—C11—C12—C13	175.7 (2)
S1—C20—C25—C24	−178.67 (15)	C10—C11—C12—C17	−4.8 (3)
C23—C24—C25—C20	−0.6 (3)	C17—C12—C13—C14	0.7 (3)
C9—N1—C1—C2	177.03 (17)	C11—C12—C13—C14	−179.8 (2)
C19—N1—C1—C2	−3.3 (3)	C12—C13—C14—C15	−1.4 (3)
C9—N1—C1—C6	−2.4 (3)	C18—O2—C15—C14	−0.2 (3)
C19—N1—C1—C6	177.28 (18)	C18—O2—C15—C16	−179.91 (18)
N1—C1—C2—C3	−179.48 (18)	C13—C14—C15—O2	−179.1 (2)
C6—C1—C2—C3	−0.1 (3)	C13—C14—C15—C16	0.6 (3)
C1—C2—C3—C4	−0.3 (3)	O2—C15—C16—O1	0.9 (3)
C2—C3—C4—C5	0.6 (3)	C14—C15—C16—O1	−178.85 (19)
C3—C4—C5—C6	−0.5 (3)	O2—C15—C16—C17	−179.48 (17)
C2—C1—C6—C7	−179.15 (19)	C14—C15—C16—C17	0.8 (3)
N1—C1—C6—C7	0.3 (3)	O1—C16—C17—C12	178.21 (18)
C2—C1—C6—C5	0.2 (3)	C15—C16—C17—C12	−1.4 (3)
N1—C1—C6—C5	179.60 (18)	C13—C12—C17—C16	0.6 (3)
C4—C5—C6—C7	179.4 (2)	C11—C12—C17—C16	−178.85 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5	0.82	1.81	2.625 (2)	176
C3—H3···O4^i	0.93	2.40	3.183 (3)	142
C17—H17···O3	0.93	2.51	3.413 (3)	164
C19—H19A···O3	0.96	2.32	3.194 (3)	151
C21—H21···O4	0.93	2.57	2.916 (3)	103
C24—H24···O5^ii	0.93	2.49	3.322 (3)	149

Symmetry codes: (i) x+3/2, −y+1/2, −z+1; (ii) x+1, y, z.