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The title compound, C14H14NO+·C6H4BrSO3, (I), crystallizes in a non-centrosymmetric space group and exhibits non-linear optical properties. The second-harmonic generation (SHG) effect of (I) is about 0.14 times that of urea. The cation is almost planar and exists in an E configuration. The pyridinium and benzene rings of the cation make a dihedral angle of 4.52 (8)°. The dihedral angles between the benzene ring of the anion and the mean planes through the pyridinium and benzene rings of the cation are 67.06 (8) and 71.56 (8)°, respectively. In the crystal structure, the cations and anions are linked by O—H...O hydrogen bonds and weak C—H...O inter­actions into a three-dimensional network. C—H...π inter­actions are also observed in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046137/wn2084sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046137/wn2084Isup2.hkl
Contains datablock I

CCDC reference: 630504

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.024
  • wR factor = 0.058
  • Data-to-parameter ratio = 21.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.91 PLAT354_ALERT_3_C Short O-H Bond (0.82A) O4 - H1O4 ... 0.71 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C14 H14 N O
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.914 Tmax scaled 0.477 Tmin scaled 0.360 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 29.99 From the CIF: _reflns_number_total 5286 Count of symmetry unique reflns 2740 Completeness (_total/calc) 192.92% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2546 Fraction of Friedel pairs measured 0.929 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 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 4 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-(4-Hydroxystyryl)-1-methylpyridinium 4-bromobenzenesulfonate top
Crystal data top
C14H14NO+·C6H4BrO3SF(000) = 456
Mr = 448.32Dx = 1.625 Mg m3
Monoclinic, P21Melting point = 513–516 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 6.2827 (1) ÅCell parameters from 5107 reflections
b = 19.5377 (3) Åθ = 2.1–30.0°
c = 7.5025 (1) ŵ = 2.39 mm1
β = 95.923 (1)°T = 100 K
V = 916.01 (2) Å3Block, purple
Z = 20.48 × 0.39 × 0.31 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
5286 independent reflections
Radiation source: fine-focus sealed tube5107 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 8.33 pixels mm-1θmax = 30.0°, θmin = 2.1°
ω scansh = 88
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 2727
Tmin = 0.394, Tmax = 0.522l = 1010
15947 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)] = 0.024H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.058 w = 1/[σ2(Fo2) + (0.024P)2 + 0.0214P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
5286 reflectionsΔρmax = 0.60 e Å3
249 parametersΔρmin = 0.43 e Å3
1 restraintAbsolute structure: Flack (1983), with 2427 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.013 (4)
Special details top

Experimental. The data were 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
Br10.35458 (2)0.542441 (10)0.88108 (2)0.02165 (5)
S10.21574 (6)0.63716 (2)0.25977 (6)0.01564 (8)
N11.6968 (2)0.80144 (7)0.9335 (2)0.0175 (3)
O10.3676 (2)0.68651 (6)0.34852 (19)0.0234 (3)
O20.3201 (2)0.57579 (7)0.20216 (18)0.0217 (3)
O30.0701 (2)0.66804 (7)0.11896 (19)0.0223 (3)
O40.4342 (2)0.81972 (7)0.28717 (19)0.0209 (3)
H1O40.405 (4)0.7851 (15)0.298 (4)0.029 (7)*
C10.1844 (3)0.56807 (9)0.6963 (2)0.0175 (3)
C20.2764 (3)0.56796 (9)0.5205 (2)0.0184 (3)
H2A0.41710.55360.49260.022*
C30.1547 (3)0.58972 (9)0.3859 (2)0.0166 (3)
H3A0.21410.59030.26710.020*
C40.0568 (3)0.61062 (8)0.4299 (2)0.0154 (3)
C50.1465 (3)0.60958 (9)0.6078 (2)0.0178 (3)
H5A0.28780.62310.63610.021*
C60.0262 (3)0.58846 (9)0.7433 (2)0.0189 (3)
H6A0.08490.58800.86230.023*
C71.8901 (3)0.81452 (10)1.0241 (2)0.0192 (3)
H7A1.96990.77851.07710.023*
C81.9713 (3)0.87979 (10)1.0397 (2)0.0198 (3)
H8A2.10380.88821.10310.024*
C91.8506 (3)0.93288 (9)0.9583 (3)0.0196 (3)
H9A1.90240.97750.96560.024*
C101.6532 (3)0.91912 (9)0.8664 (2)0.0181 (3)
H10A1.57250.95490.81280.022*
C111.5726 (3)0.85258 (9)0.8525 (2)0.0167 (3)
C121.3673 (3)0.83454 (9)0.7565 (3)0.0197 (3)
H121.32360.78920.76100.024*
C131.2360 (3)0.87866 (9)0.6615 (2)0.0183 (3)
H13A1.28000.92410.65800.022*
C141.0309 (3)0.86125 (9)0.5639 (2)0.0164 (3)
C150.9595 (3)0.79371 (9)0.5400 (3)0.0193 (3)
H15A1.04710.75810.58550.023*
C160.7613 (3)0.77873 (9)0.4500 (3)0.0194 (3)
H16A0.71660.73350.43670.023*
C170.6283 (3)0.83165 (9)0.3792 (2)0.0169 (3)
C180.6970 (3)0.89946 (9)0.4000 (2)0.0180 (3)
H18A0.60940.93500.35400.022*
C190.8956 (3)0.91351 (9)0.4894 (2)0.0181 (3)
H19A0.94120.95870.50050.022*
C201.6250 (3)0.72959 (10)0.9224 (3)0.0246 (4)
H20A1.73290.70080.98350.037*
H20B1.60090.71610.79890.037*
H20C1.49440.72510.97750.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.02040 (8)0.02600 (8)0.01847 (8)0.00373 (7)0.00163 (5)0.00159 (8)
S10.01578 (17)0.01394 (16)0.01682 (19)0.00035 (14)0.00011 (14)0.00063 (14)
N10.0167 (6)0.0156 (7)0.0198 (7)0.0013 (5)0.0009 (5)0.0015 (5)
O10.0242 (7)0.0198 (6)0.0254 (7)0.0075 (5)0.0016 (5)0.0013 (5)
O20.0214 (6)0.0205 (6)0.0235 (7)0.0033 (5)0.0042 (5)0.0006 (5)
O30.0220 (6)0.0232 (6)0.0212 (7)0.0032 (5)0.0011 (5)0.0045 (5)
O40.0163 (6)0.0207 (7)0.0244 (7)0.0017 (5)0.0033 (5)0.0015 (5)
C10.0204 (8)0.0148 (7)0.0177 (8)0.0002 (6)0.0033 (6)0.0008 (6)
C20.0147 (7)0.0179 (7)0.0221 (9)0.0012 (6)0.0005 (6)0.0009 (6)
C30.0169 (7)0.0173 (7)0.0147 (8)0.0013 (6)0.0021 (6)0.0000 (6)
C40.0161 (7)0.0130 (6)0.0169 (8)0.0007 (6)0.0010 (6)0.0016 (6)
C50.0149 (8)0.0177 (7)0.0199 (9)0.0017 (6)0.0023 (6)0.0015 (6)
C60.0205 (8)0.0190 (7)0.0164 (8)0.0003 (6)0.0021 (6)0.0011 (6)
C70.0166 (8)0.0238 (8)0.0170 (8)0.0026 (6)0.0007 (6)0.0021 (6)
C80.0170 (8)0.0260 (8)0.0162 (8)0.0004 (6)0.0011 (6)0.0022 (6)
C90.0177 (8)0.0186 (8)0.0220 (9)0.0014 (6)0.0001 (6)0.0013 (6)
C100.0170 (8)0.0168 (7)0.0204 (9)0.0007 (6)0.0014 (6)0.0005 (6)
C110.0141 (7)0.0185 (8)0.0179 (8)0.0025 (6)0.0031 (6)0.0005 (6)
C120.0169 (8)0.0169 (7)0.0247 (9)0.0000 (6)0.0007 (7)0.0003 (7)
C130.0163 (7)0.0166 (7)0.0216 (9)0.0013 (6)0.0006 (6)0.0011 (6)
C140.0139 (7)0.0188 (7)0.0164 (8)0.0001 (6)0.0015 (6)0.0001 (6)
C150.0166 (8)0.0156 (7)0.0255 (10)0.0031 (6)0.0004 (6)0.0006 (7)
C160.0186 (8)0.0146 (7)0.0246 (9)0.0008 (6)0.0003 (7)0.0008 (6)
C170.0157 (8)0.0182 (8)0.0168 (8)0.0009 (6)0.0026 (6)0.0005 (6)
C180.0192 (7)0.0164 (7)0.0181 (8)0.0020 (6)0.0002 (6)0.0013 (6)
C190.0185 (8)0.0147 (7)0.0211 (9)0.0011 (6)0.0015 (6)0.0009 (6)
C200.0228 (9)0.0165 (8)0.0334 (10)0.0003 (7)0.0023 (7)0.0039 (7)
Geometric parameters (Å, º) top
Br1—C11.9034 (17)C8—H8A0.9300
S1—O21.4535 (13)C9—C101.382 (2)
S1—O31.4551 (14)C9—H9A0.9300
S1—O11.4671 (13)C10—C111.395 (2)
S1—C41.7771 (18)C10—H10A0.9300
N1—C71.354 (2)C11—C121.455 (2)
N1—C111.370 (2)C12—C131.345 (2)
N1—C201.474 (2)C12—H120.9300
O4—C171.358 (2)C13—C141.456 (2)
O4—H1O40.71 (3)C13—H13A0.9300
C1—C21.384 (3)C14—C151.399 (2)
C1—C61.392 (3)C14—C191.407 (2)
C2—C31.394 (2)C15—C161.385 (3)
C2—H2A0.9300C15—H15A0.9300
C3—C41.397 (2)C16—C171.399 (2)
C3—H3A0.9300C16—H16A0.9300
C4—C51.394 (2)C17—C181.397 (2)
C5—C61.391 (3)C18—C191.382 (2)
C5—H5A0.9300C18—H18A0.9300
C6—H6A0.9300C19—H19A0.9300
C7—C81.374 (3)C20—H20A0.9600
C7—H7A0.9300C20—H20B0.9600
C8—C91.389 (3)C20—H20C0.9600
O2—S1—O3113.28 (8)C9—C10—C11121.22 (17)
O2—S1—O1112.64 (8)C9—C10—H10A119.4
O3—S1—O1112.81 (8)C11—C10—H10A119.4
O2—S1—C4106.08 (8)N1—C11—C10117.45 (16)
O3—S1—C4106.54 (8)N1—C11—C12118.56 (15)
O1—S1—C4104.66 (8)C10—C11—C12123.98 (16)
C7—N1—C11121.68 (15)C13—C12—C11124.82 (16)
C7—N1—C20117.49 (15)C13—C12—H12117.6
C11—N1—C20120.82 (15)C11—C12—H12117.6
C17—O4—H1O4109 (2)C12—C13—C14125.41 (16)
C2—C1—C6122.33 (16)C12—C13—H13A117.3
C2—C1—Br1118.88 (13)C14—C13—H13A117.3
C6—C1—Br1118.76 (14)C15—C14—C19117.44 (16)
C1—C2—C3118.88 (16)C15—C14—C13122.71 (16)
C1—C2—H2A120.6C19—C14—C13119.85 (15)
C3—C2—H2A120.6C16—C15—C14121.46 (16)
C2—C3—C4119.84 (16)C16—C15—H15A119.3
C2—C3—H3A120.1C14—C15—H15A119.3
C4—C3—H3A120.1C15—C16—C17120.03 (16)
C5—C4—C3120.16 (16)C15—C16—H16A120.0
C5—C4—S1119.37 (13)C17—C16—H16A120.0
C3—C4—S1120.46 (13)O4—C17—C18118.07 (16)
C6—C5—C4120.53 (16)O4—C17—C16122.40 (16)
C6—C5—H5A119.7C18—C17—C16119.53 (16)
C4—C5—H5A119.7C19—C18—C17119.72 (16)
C5—C6—C1118.26 (17)C19—C18—H18A120.1
C5—C6—H6A120.9C17—C18—H18A120.1
C1—C6—H6A120.9C18—C19—C14121.80 (16)
N1—C7—C8121.61 (17)C18—C19—H19A119.1
N1—C7—H7A119.2C14—C19—H19A119.1
C8—C7—H7A119.2N1—C20—H20A109.5
C7—C8—C9118.32 (17)N1—C20—H20B109.5
C7—C8—H8A120.8H20A—C20—H20B109.5
C9—C8—H8A120.8N1—C20—H20C109.5
C10—C9—C8119.71 (17)H20A—C20—H20C109.5
C10—C9—H9A120.1H20B—C20—H20C109.5
C8—C9—H9A120.1
C6—C1—C2—C30.7 (3)C7—N1—C11—C100.1 (3)
Br1—C1—C2—C3177.11 (12)C20—N1—C11—C10178.91 (16)
C1—C2—C3—C40.5 (2)C7—N1—C11—C12179.58 (16)
C2—C3—C4—C50.2 (2)C20—N1—C11—C120.5 (2)
C2—C3—C4—S1178.96 (13)C9—C10—C11—N10.0 (3)
O2—S1—C4—C589.10 (15)C9—C10—C11—C12179.40 (16)
O3—S1—C4—C5149.93 (14)N1—C11—C12—C13175.52 (17)
O1—S1—C4—C530.21 (16)C10—C11—C12—C133.9 (3)
O2—S1—C4—C389.68 (14)C11—C12—C13—C14179.58 (17)
O3—S1—C4—C331.29 (15)C12—C13—C14—C158.3 (3)
O1—S1—C4—C3151.01 (13)C12—C13—C14—C19171.64 (18)
C3—C4—C5—C60.7 (2)C19—C14—C15—C161.5 (3)
S1—C4—C5—C6179.44 (13)C13—C14—C15—C16178.47 (17)
C4—C5—C6—C10.5 (3)C14—C15—C16—C170.6 (3)
C2—C1—C6—C50.2 (3)C15—C16—C17—O4178.80 (16)
Br1—C1—C6—C5177.57 (13)C15—C16—C17—C180.0 (3)
C11—N1—C7—C80.1 (3)O4—C17—C18—C19178.53 (15)
C20—N1—C7—C8179.22 (17)C16—C17—C18—C190.3 (3)
N1—C7—C8—C90.6 (3)C17—C18—C19—C141.3 (3)
C7—C8—C9—C100.7 (3)C15—C14—C19—C181.8 (3)
C8—C9—C10—C110.4 (3)C13—C14—C19—C18178.13 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H1O4···O10.71 (3)1.98 (3)2.6833 (18)171 (3)
C5—H5A···O10.932.582.921 (2)102
C6—H6A···O3i0.932.493.206 (2)134
C7—H7A···O3ii0.932.263.132 (2)156
C10—H10A···O2iii0.932.463.111 (2)127
C16—H16A···O10.932.413.091 (2)130
C20—H20A···O3ii0.962.343.254 (2)158
C16—H16A···Cg1iv0.933.243.9330 (19)133
C19—H19A···Cg1v0.932.723.6245 (19)165
Symmetry codes: (i) x, y, z+1; (ii) x+2, y, z+1; (iii) x+2, y+1/2, z+1; (iv) x+1, y, z; (v) x+1, y+1/2, z+1.
 

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