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The title compound, C19H18NO2+·C6H4BrO3S, crystallizes in a non-centrosymmetric space group and exhibits a non-linear optical property. The second-harmonic generation (SHG) efficiency of the compound is about 0.8 times that of urea. The cation is almost planar. The cations and anions are arranged in alternating layers parallel to the ab plane, and these layers are inter­connected through O—H...O and C—H...O inter­actions, forming a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014213/ci2324sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014213/ci2324Isup2.hkl
Contains datablock I

CCDC reference: 648061

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.037
  • wR factor = 0.090
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.23 PLAT412_ALERT_2_C Short Intra XH3 .. XHn H10A .. H18A .. 1.88 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.01
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 26.99 From the CIF: _reflns_number_total 4133 Count of symmetry unique reflns 2434 Completeness (_total/calc) 169.80% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1699 Fraction of Friedel pairs measured 0.698 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

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-bromobenzenesulfonate top
Crystal data top
C19H18NO2+·C6H4BrO3SF(000) = 540
Mr = 528.41Dx = 1.575 Mg m3
Monoclinic, PcMelting point = 561–562 K
Hall symbol: P -2ycMo Kα radiation, λ = 0.71073 Å
a = 7.942 (3) ÅCell parameters from 4133 reflections
b = 6.751 (2) Åθ = 2.0–27.0°
c = 21.964 (8) ŵ = 1.98 mm1
β = 108.861 (12)°T = 297 K
V = 1114.4 (7) Å3Plate, red-brown
Z = 20.56 × 0.31 × 0.05 mm
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
4133 independent reflections
Radiation source: fine-focus sealed tube3711 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Detector resolution: 8.33 pixels mm-1θmax = 27.0°, θmin = 2.0°
ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 86
Tmin = 0.403, Tmax = 0.899l = 2627
5986 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090 w = 1/[σ2(Fo2)]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.001
4133 reflectionsΔρmax = 0.60 e Å3
304 parametersΔρmin = 0.27 e Å3
5 restraintsAbsolute structure: Flack (1983), 1742 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.000 (7)
Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Br11.18764 (5)0.40372 (6)0.81913 (2)0.05304 (13)
S10.55490 (10)0.22603 (13)0.78533 (4)0.0367 (2)
O10.5514 (4)0.3366 (5)0.72891 (12)0.0579 (8)
O20.6084 (4)0.3494 (4)0.84316 (12)0.0471 (6)
O30.3973 (4)0.1116 (4)0.78004 (15)0.0557 (7)
O40.6341 (4)0.3692 (4)0.46758 (12)0.0470 (7)
H1O40.609 (6)0.357 (6)0.429 (2)0.046 (12)*
O50.7218 (4)0.3246 (4)0.59249 (11)0.0453 (6)
N10.1133 (4)0.7444 (4)0.51810 (12)0.0327 (6)
C10.0568 (6)1.1320 (6)0.6295 (2)0.0497 (9)
H1A0.09731.16070.67330.060*
C20.0557 (6)1.2595 (6)0.5877 (3)0.0582 (11)
H2A0.09291.37430.60300.070*
C30.1148 (6)1.2186 (6)0.5225 (2)0.0556 (11)
H3A0.19331.30590.49450.067*
C40.0604 (5)1.0516 (6)0.49787 (19)0.0465 (9)
H4BA0.09891.02860.45380.056*
C50.0546 (5)0.9157 (5)0.54050 (17)0.0352 (7)
C60.1124 (5)0.9560 (5)0.60676 (17)0.0372 (8)
C70.2238 (5)0.8155 (5)0.64885 (16)0.0385 (7)
H7A0.26030.83690.69300.046*
C80.2776 (5)0.6511 (5)0.62547 (16)0.0351 (7)
H8A0.35030.56040.65380.042*
C90.2248 (4)0.6142 (5)0.55810 (15)0.0313 (7)
C100.2920 (5)0.4465 (5)0.53203 (17)0.0410 (8)
H10A0.26210.43950.48750.049*
C110.3922 (5)0.3023 (5)0.56579 (15)0.0352 (7)
H11A0.42580.31040.61040.042*
C120.4541 (5)0.1306 (5)0.53809 (15)0.0338 (7)
C130.5587 (5)0.0133 (5)0.58002 (14)0.0327 (7)
H13A0.58800.00340.62430.039*
C140.6182 (4)0.1793 (5)0.55609 (14)0.0314 (7)
C150.5713 (5)0.2052 (5)0.48893 (15)0.0344 (7)
C160.4677 (5)0.0644 (6)0.44771 (15)0.0402 (8)
H16A0.43670.08150.40340.048*
C170.4106 (5)0.1010 (5)0.47221 (16)0.0411 (8)
H17A0.34150.19470.44400.049*
C180.0488 (6)0.7038 (7)0.44772 (16)0.0557 (11)
H18A0.05230.56660.43780.067*
H18B0.07510.73860.43330.067*
H18C0.10330.78840.42430.067*
C190.7700 (6)0.3055 (7)0.66054 (16)0.0516 (10)
H19A0.84550.41400.68080.077*
H19B0.66470.30670.67290.077*
H19C0.83250.18290.67380.077*
C200.7286 (5)0.0503 (5)0.79674 (15)0.0352 (8)
C210.8893 (5)0.1110 (6)0.79008 (17)0.0396 (8)
H21A0.90310.24210.77960.048*
C221.0298 (5)0.0209 (6)0.79878 (16)0.0407 (8)
H22A1.13720.02030.79460.049*
C231.0045 (5)0.2169 (6)0.81405 (15)0.0395 (8)
C240.8473 (5)0.2796 (6)0.82149 (17)0.0428 (9)
H24A0.83390.41080.83190.051*
C250.7092 (6)0.1458 (5)0.81330 (19)0.0419 (9)
H25A0.60340.18700.81890.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0519 (2)0.0553 (2)0.04934 (19)0.0075 (2)0.01277 (15)0.00130 (18)
S10.0349 (4)0.0465 (5)0.0287 (4)0.0036 (4)0.0104 (3)0.0016 (3)
O10.0648 (18)0.072 (2)0.0367 (13)0.0163 (16)0.0168 (12)0.0192 (13)
O20.0582 (17)0.0482 (15)0.0386 (13)0.0081 (13)0.0207 (11)0.0012 (11)
O30.0377 (15)0.064 (2)0.0644 (18)0.0107 (13)0.0148 (13)0.0084 (13)
O40.0679 (19)0.0423 (15)0.0305 (13)0.0191 (13)0.0154 (12)0.0023 (11)
O50.0641 (17)0.0383 (14)0.0293 (11)0.0194 (13)0.0092 (11)0.0006 (10)
N10.0321 (15)0.0337 (15)0.0297 (13)0.0039 (12)0.0064 (10)0.0011 (11)
C10.056 (2)0.039 (2)0.062 (2)0.0009 (18)0.031 (2)0.0058 (17)
C20.057 (3)0.032 (2)0.099 (3)0.0074 (18)0.043 (2)0.001 (2)
C30.040 (2)0.035 (2)0.090 (3)0.0098 (17)0.018 (2)0.018 (2)
C40.038 (2)0.040 (2)0.057 (2)0.0096 (16)0.0086 (16)0.0105 (16)
C50.0322 (17)0.0297 (18)0.0440 (18)0.0022 (13)0.0126 (14)0.0059 (13)
C60.0375 (19)0.0313 (18)0.0467 (19)0.0000 (15)0.0191 (15)0.0026 (14)
C70.045 (2)0.0396 (19)0.0319 (16)0.0011 (16)0.0141 (14)0.0016 (14)
C80.0383 (18)0.0340 (17)0.0313 (15)0.0062 (15)0.0089 (13)0.0036 (13)
C90.0318 (17)0.0296 (17)0.0315 (15)0.0034 (13)0.0091 (13)0.0031 (12)
C100.052 (2)0.0361 (19)0.0343 (17)0.0078 (16)0.0128 (15)0.0026 (14)
C110.0384 (18)0.0336 (18)0.0327 (17)0.0032 (14)0.0103 (13)0.0033 (13)
C120.0374 (18)0.0318 (18)0.0334 (16)0.0041 (14)0.0128 (13)0.0012 (12)
C130.0368 (17)0.0337 (17)0.0268 (14)0.0020 (14)0.0092 (12)0.0027 (12)
C140.0336 (17)0.0300 (17)0.0293 (15)0.0015 (13)0.0084 (12)0.0029 (12)
C150.0414 (19)0.0321 (18)0.0321 (16)0.0036 (14)0.0152 (13)0.0005 (13)
C160.045 (2)0.047 (2)0.0267 (16)0.0116 (16)0.0093 (14)0.0008 (13)
C170.049 (2)0.041 (2)0.0316 (16)0.0138 (16)0.0106 (14)0.0066 (14)
C180.063 (3)0.063 (3)0.0319 (18)0.020 (2)0.0024 (16)0.0007 (17)
C190.067 (3)0.055 (2)0.0281 (16)0.021 (2)0.0085 (16)0.0049 (16)
C200.0363 (19)0.044 (2)0.0239 (14)0.0102 (15)0.0079 (13)0.0031 (13)
C210.042 (2)0.042 (2)0.0343 (17)0.0139 (16)0.0118 (15)0.0018 (14)
C220.039 (2)0.048 (2)0.0370 (17)0.0118 (17)0.0148 (14)0.0058 (16)
C230.0377 (19)0.048 (2)0.0303 (17)0.0007 (16)0.0071 (14)0.0051 (14)
C240.046 (2)0.041 (2)0.0403 (19)0.0067 (17)0.0129 (16)0.0038 (15)
C250.040 (2)0.045 (2)0.0399 (18)0.0153 (18)0.0125 (14)0.0028 (17)
Geometric parameters (Å, º) top
Br1—C231.901 (4)C10—H10A0.93
S1—O11.439 (3)C11—C121.466 (5)
S1—O31.443 (3)C11—H11A0.93
S1—O21.462 (3)C12—C171.389 (5)
S1—C201.775 (4)C12—C131.410 (5)
O4—C151.359 (4)C13—C141.384 (5)
O4—H1O40.81 (5)C13—H13A0.93
O5—C141.361 (4)C14—C151.411 (4)
O5—C191.424 (4)C15—C161.385 (5)
N1—C91.351 (4)C16—C171.378 (5)
N1—C51.394 (4)C16—H16A0.93
N1—C181.488 (4)C17—H17A0.93
C1—C21.361 (6)C18—H18A0.95
C1—C61.414 (5)C18—H18B0.96
C1—H1A0.93C18—H18C0.96
C2—C31.384 (7)C19—H19A0.96
C2—H2A0.93C19—H19B0.96
C3—C41.379 (6)C19—H19C0.96
C3—H3A0.93C20—C211.393 (5)
C4—C51.414 (5)C20—C251.394 (5)
C4—H4BA0.93C21—C221.391 (6)
C5—C61.404 (5)C21—H21A0.93
C6—C71.417 (5)C22—C231.396 (6)
C7—C81.349 (5)C22—H22A0.93
C7—H7A0.93C23—C241.377 (6)
C8—C91.423 (5)C24—C251.387 (6)
C8—H8A0.93C24—H24A0.93
C9—C101.447 (5)C25—H25A0.93
C10—C111.323 (5)
O1—S1—O3115.69 (19)C13—C12—C11118.7 (3)
O1—S1—O2111.81 (18)C14—C13—C12120.7 (3)
O3—S1—O2112.09 (18)C14—C13—H13A119.6
O1—S1—C20105.44 (17)C12—C13—H13A119.6
O3—S1—C20105.52 (17)O5—C14—C13125.2 (3)
O2—S1—C20105.29 (16)O5—C14—C15115.5 (3)
C15—O4—H1O4107 (3)C13—C14—C15119.4 (3)
C14—O5—C19117.2 (3)O4—C15—C16122.7 (3)
C9—N1—C5122.2 (3)O4—C15—C14117.4 (3)
C9—N1—C18119.3 (3)C16—C15—C14119.9 (3)
C5—N1—C18118.5 (3)C17—C16—C15120.1 (3)
C2—C1—C6120.3 (4)C17—C16—H16A119.9
C2—C1—H1A119.8C15—C16—H16A119.9
C6—C1—H1A119.8C16—C17—C12121.4 (3)
C1—C2—C3120.1 (4)C16—C17—H17A119.3
C1—C2—H2A120.0C12—C17—H17A119.3
C3—C2—H2A120.0N1—C18—H18A113.0
C4—C3—C2121.7 (4)N1—C18—H18B105.6
C4—C3—H3A119.2H18A—C18—H18B105.3
C2—C3—H3A119.2N1—C18—H18C112.5
C3—C4—C5119.2 (4)H18A—C18—H18C113.8
C3—C4—H4BA120.4H18B—C18—H18C105.6
C5—C4—H4BA120.4O5—C19—H19A109.5
N1—C5—C6119.5 (3)O5—C19—H19B109.5
N1—C5—C4121.5 (3)H19A—C19—H19B109.5
C6—C5—C4119.0 (3)O5—C19—H19C109.5
C5—C6—C1119.6 (3)H19A—C19—H19C109.5
C5—C6—C7118.2 (3)H19B—C19—H19C109.5
C1—C6—C7122.1 (3)C21—C20—C25119.2 (4)
C8—C7—C6120.7 (3)C21—C20—S1119.0 (3)
C8—C7—H7A119.7C25—C20—S1121.7 (3)
C6—C7—H7A119.7C22—C21—C20121.2 (3)
C7—C8—C9121.1 (3)C22—C21—H21A119.4
C7—C8—H8A119.4C20—C21—H21A119.4
C9—C8—H8A119.4C21—C22—C23118.0 (3)
N1—C9—C8118.2 (3)C21—C22—H22A121.0
N1—C9—C10120.0 (3)C23—C22—H22A121.0
C8—C9—C10121.7 (3)C24—C23—C22121.7 (3)
C11—C10—C9125.9 (3)C24—C23—Br1119.7 (3)
C11—C10—H10A117.0C22—C23—Br1118.4 (3)
C9—C10—H10A117.0C23—C24—C25119.6 (3)
C10—C11—C12124.8 (3)C23—C24—H24A120.2
C10—C11—H11A117.6C25—C24—H24A120.2
C12—C11—H11A117.6C24—C25—C20120.2 (4)
C17—C12—C13118.5 (3)C24—C25—H25A119.9
C17—C12—C11122.9 (3)C20—C25—H25A119.9
C6—C1—C2—C30.7 (6)C11—C12—C13—C14179.1 (3)
C1—C2—C3—C41.1 (7)C19—O5—C14—C131.0 (5)
C2—C3—C4—C51.9 (6)C19—O5—C14—C15179.1 (3)
C9—N1—C5—C60.0 (5)C12—C13—C14—O5179.0 (3)
C18—N1—C5—C6179.4 (4)C12—C13—C14—C150.9 (5)
C9—N1—C5—C4179.2 (3)O5—C14—C15—O40.5 (5)
C18—N1—C5—C41.4 (5)C13—C14—C15—O4179.4 (3)
C3—C4—C5—N1179.9 (4)O5—C14—C15—C16179.3 (4)
C3—C4—C5—C60.9 (6)C13—C14—C15—C160.5 (5)
N1—C5—C6—C1178.4 (3)O4—C15—C16—C17178.8 (4)
C4—C5—C6—C10.8 (5)C14—C15—C16—C170.0 (6)
N1—C5—C6—C72.4 (5)C15—C16—C17—C120.2 (6)
C4—C5—C6—C7178.4 (4)C13—C12—C17—C160.1 (6)
C2—C1—C6—C51.6 (6)C11—C12—C17—C16178.5 (4)
C2—C1—C6—C7177.5 (4)O1—S1—C20—C2143.7 (3)
C5—C6—C7—C82.3 (5)O3—S1—C20—C21166.6 (3)
C1—C6—C7—C8178.6 (4)O2—S1—C20—C2174.6 (3)
C6—C7—C8—C90.2 (6)O1—S1—C20—C25137.4 (3)
C5—N1—C9—C82.5 (5)O3—S1—C20—C2514.5 (3)
C18—N1—C9—C8176.9 (3)O2—S1—C20—C25104.2 (3)
C5—N1—C9—C10175.4 (3)C25—C20—C21—C220.9 (5)
C18—N1—C9—C105.2 (5)S1—C20—C21—C22179.7 (3)
C7—C8—C9—N12.6 (5)C20—C21—C22—C230.4 (5)
C7—C8—C9—C10175.2 (4)C21—C22—C23—C241.1 (5)
N1—C9—C10—C11175.4 (4)C21—C22—C23—Br1174.9 (3)
C8—C9—C10—C116.8 (6)C22—C23—C24—C250.4 (5)
C9—C10—C11—C12178.0 (4)Br1—C23—C24—C25175.5 (3)
C10—C11—C12—C170.9 (6)C23—C24—C25—C200.9 (6)
C10—C11—C12—C13179.3 (4)C21—C20—C25—C241.5 (5)
C17—C12—C13—C140.7 (5)S1—C20—C25—C24179.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H1O4···O2i0.81 (4)1.88 (4)2.677 (4)166 (5)
C2—H2A···O5ii0.932.483.337 (5)154
C3—H3A···O4ii0.932.553.409 (5)153
C8—H8A···O10.932.423.347 (5)177
C11—H11A···O10.932.473.400 (4)173
C22—H22A···O3iii0.932.283.204 (5)177
C24—H24A···O2iv0.932.483.269 (5)142
C25—H25A···O30.932.562.919 (6)103
Symmetry codes: (i) x, y, z1/2; (ii) x1, y+2, z; (iii) x+1, y, z; (iv) x, y1, z.
 

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