2-[(E)-2-(3-Hydr­oxy-4-methoxy­phen­yl)ethen­yl]-1-methyl­quinolinium 0.59-chloride 0.41-iodide monohydrate

The title compound, C₁₉H₁₈NO₂⁺.0.59 C l⁻·0.41I⁻·H₂O, exhibits second-order non-linear optical properties. The cations are essentially planar and they are linked with water mol­ecules through O—H...O hydrogen bonds, and the water mol­ecules are linked with Cl⁻ ions by O—H...Cl hydrogen bonds, forming infinite chains of chloride salts along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in solvent or counterion
• R factor = 0.048
• wR factor = 0.125
• Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT094_ALERT_2_B Ratio of Maximum / Minimum Residual Density ....       4.07

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms ..          ?
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      33.00 Perc.
PLAT410_ALERT_2_C Short Intra H...H Contact  H8     ..  H11     ..       1.97 Ang.
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H10    ..  H19A    ..       1.82 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O

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           28.00
           From the CIF: _reflns_number_total               3964
           Count of symmetry unique reflns         2117
           Completeness (_total/calc)            187.25%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1847
           Fraction of Friedel pairs measured     0.872
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

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 0.59-chloride 0.41-iodide monohydrate

Crystal data

C19H18NO2^+·0.59Cl^−·0.41I^−·H2O	Z = 1
Mr = 383.49	F(000) = 197
Triclinic, P1	Dx = 1.449 Mg m^−3
Hall symbol: P 1	Melting point = 478–480 K
a = 6.2645 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.2382 (8) Å	Cell parameters from 3964 reflections
c = 9.1458 (8) Å	θ = 2.4–28.0°
α = 68.743 (2)°	µ = 0.89 mm^−1
β = 88.273 (1)°	T = 153 K
γ = 87.467 (1)°	Needle, colorless
V = 439.41 (7) Å^3	0.52 × 0.11 × 0.10 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	3964 independent reflections
Radiation source: fine-focus sealed tube	3677 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Detector resolution: 8.33 pixels mm^-1	θmax = 28.0°, θmin = 2.4°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→10
Tmin = 0.661, Tmax = 0.920	l = −11→12
6398 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)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0738P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.16	(Δ/σ)max = 0.003
3964 reflections	Δρmax = 1.14 e Å^−3
224 parameters	Δρmin = −0.28 e Å^−3
3 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (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	Occ. (<1)
I1	0.8955 (9)	0.5782 (6)	0.0877 (7)	0.0560 (7)	0.412 (4)
Cl1	0.896 (3)	0.607 (2)	0.088 (3)	0.0560 (7)	0.588 (4)
O1	1.4583 (5)	0.9645 (4)	0.6709 (4)	0.0602 (8)
H1	1.4118	0.9321	0.7613	0.090*
O2	1.5650 (5)	1.0451 (4)	0.3797 (4)	0.0607 (8)
N1	0.3853 (5)	0.4280 (4)	0.5550 (4)	0.0423 (6)
C1	0.2078 (5)	0.3354 (4)	0.6272 (5)	0.0431 (8)
C2	0.0649 (6)	0.2697 (5)	0.5464 (6)	0.0542 (9)
H2	0.0855	0.2911	0.4400	0.065*
C3	−0.1024 (7)	0.1752 (5)	0.6258 (7)	0.0614 (11)
H3	−0.1942	0.1313	0.5723	0.074*
C4	−0.1396 (8)	0.1430 (6)	0.7800 (8)	0.0715 (14)
H4	−0.2546	0.0767	0.8310	0.086*
C5	−0.0081 (8)	0.2078 (7)	0.8613 (7)	0.0676 (12)
H5	−0.0352	0.1863	0.9671	0.081*
C6	0.1677 (6)	0.3067 (5)	0.7856 (5)	0.0511 (9)
C7	0.3063 (7)	0.3765 (6)	0.8645 (5)	0.0551 (9)
H7	0.2815	0.3582	0.9700	0.066*
C8	0.4741 (6)	0.4692 (5)	0.7889 (5)	0.0513 (8)
H8	0.5623	0.5164	0.8421	0.062*
C9	0.5174 (5)	0.4954 (4)	0.6303 (5)	0.0400 (7)
C10	0.6988 (6)	0.5938 (5)	0.5506 (5)	0.0473 (8)
H10	0.7220	0.6100	0.4454	0.057*
C11	0.8350 (6)	0.6628 (5)	0.6189 (5)	0.0466 (8)
H11	0.8082	0.6457	0.7239	0.056*
C12	1.0210 (6)	0.7619 (4)	0.5463 (5)	0.0450 (8)
C13	1.0780 (6)	0.8027 (5)	0.3928 (5)	0.0515 (8)
H13	0.9960	0.7658	0.3284	0.062*
C14	1.2587 (7)	0.8994 (5)	0.3311 (5)	0.0550 (9)
H14	1.2950	0.9283	0.2255	0.066*
C15	1.3839 (6)	0.9524 (4)	0.4265 (5)	0.0461 (8)
C16	1.3304 (6)	0.9097 (4)	0.5823 (5)	0.0448 (8)
C17	1.1497 (6)	0.8165 (5)	0.6407 (5)	0.0457 (8)
H17	1.1123	0.7891	0.7459	0.055*
C18	1.6353 (10)	1.0837 (8)	0.2236 (7)	0.0815 (16)
H18A	1.7634	1.1484	0.2054	0.122*
H18B	1.5264	1.1518	0.1536	0.122*
H18C	1.6640	0.9771	0.2052	0.122*
C19	0.4269 (8)	0.4478 (7)	0.3924 (6)	0.0606 (10)
H19A	0.5730	0.4776	0.3654	0.091*
H19B	0.3341	0.5385	0.3256	0.091*
H19C	0.4009	0.3402	0.3787	0.091*
O1W	1.3953 (7)	0.8212 (6)	−0.0191 (5)	0.0828 (11)
H1W1	1.5036	0.7889	0.0396	0.124*
H2W1	1.2908	0.7615	0.0300	0.124*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0526 (2)	0.077 (2)	0.0433 (2)	−0.0192 (12)	0.00621 (13)	−0.0260 (12)
Cl1	0.0526 (2)	0.077 (2)	0.0433 (2)	−0.0192 (12)	0.00621 (13)	−0.0260 (12)
O1	0.0519 (15)	0.0741 (17)	0.0598 (18)	−0.0290 (13)	0.0040 (13)	−0.0278 (15)
O2	0.0560 (16)	0.0617 (15)	0.0603 (18)	−0.0233 (13)	0.0126 (13)	−0.0159 (13)
N1	0.0360 (13)	0.0441 (13)	0.0502 (17)	−0.0029 (10)	0.0009 (11)	−0.0212 (12)
C1	0.0314 (14)	0.0361 (14)	0.060 (2)	−0.0026 (11)	0.0003 (13)	−0.0150 (14)
C2	0.0445 (18)	0.0504 (18)	0.075 (3)	−0.0045 (15)	−0.0015 (17)	−0.0308 (18)
C3	0.0421 (18)	0.050 (2)	0.095 (4)	−0.0109 (15)	0.000 (2)	−0.029 (2)
C4	0.048 (2)	0.058 (2)	0.100 (4)	−0.0172 (18)	0.007 (2)	−0.018 (2)
C5	0.050 (2)	0.070 (3)	0.068 (3)	−0.0119 (19)	0.010 (2)	−0.008 (2)
C6	0.0408 (17)	0.0499 (18)	0.058 (2)	−0.0018 (14)	0.0006 (15)	−0.0140 (16)
C7	0.0467 (19)	0.070 (2)	0.045 (2)	−0.0044 (17)	0.0012 (15)	−0.0161 (17)
C8	0.0419 (17)	0.059 (2)	0.055 (2)	−0.0052 (15)	−0.0023 (15)	−0.0224 (17)
C9	0.0318 (13)	0.0413 (15)	0.0490 (18)	0.0003 (11)	−0.0053 (12)	−0.0189 (13)
C10	0.0386 (16)	0.0486 (17)	0.054 (2)	−0.0080 (13)	0.0032 (14)	−0.0168 (15)
C11	0.0393 (16)	0.0479 (17)	0.055 (2)	−0.0058 (13)	0.0005 (14)	−0.0214 (15)
C12	0.0372 (15)	0.0406 (16)	0.059 (2)	−0.0023 (12)	−0.0003 (14)	−0.0197 (15)
C13	0.0456 (18)	0.0547 (19)	0.056 (2)	−0.0062 (15)	−0.0065 (16)	−0.0213 (17)
C14	0.053 (2)	0.061 (2)	0.051 (2)	−0.0066 (17)	0.0039 (16)	−0.0191 (18)
C15	0.0409 (16)	0.0380 (15)	0.054 (2)	−0.0044 (12)	0.0027 (14)	−0.0105 (14)
C16	0.0363 (15)	0.0436 (16)	0.056 (2)	−0.0076 (12)	0.0024 (14)	−0.0194 (15)
C17	0.0387 (16)	0.0458 (16)	0.054 (2)	−0.0071 (13)	0.0019 (14)	−0.0186 (14)
C18	0.073 (3)	0.088 (3)	0.062 (3)	−0.026 (3)	0.022 (2)	−0.002 (3)
C19	0.058 (2)	0.080 (3)	0.055 (2)	−0.0190 (19)	0.0082 (18)	−0.037 (2)
O1W	0.076 (2)	0.113 (3)	0.061 (2)	−0.018 (2)	0.0047 (17)	−0.030 (2)

Geometric parameters (Å, º)

O1—C16	1.356 (5)	C9—C10	1.443 (5)
O1—H1	0.8200	C10—C11	1.331 (5)
O2—C15	1.365 (4)	C10—H10	0.9300
O2—C18	1.407 (6)	C11—C12	1.453 (5)
N1—C9	1.349 (4)	C11—H11	0.9300
N1—C1	1.386 (4)	C12—C13	1.360 (6)
N1—C19	1.453 (5)	C12—C17	1.397 (5)
C1—C6	1.397 (6)	C13—C14	1.396 (6)
C1—C2	1.419 (5)	C13—H13	0.9300
C2—C3	1.359 (6)	C14—C15	1.383 (6)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.352 (8)	C15—C16	1.373 (6)
C3—H3	0.9300	C16—C17	1.379 (5)
C4—C5	1.371 (8)	C17—H17	0.9300
C4—H4	0.9300	C18—H18A	0.9600
C5—C6	1.407 (6)	C18—H18B	0.9600
C5—H5	0.9300	C18—H18C	0.9600
C6—C7	1.410 (6)	C19—H19A	0.9600
C7—C8	1.345 (6)	C19—H19B	0.9600
C7—H7	0.9300	C19—H19C	0.9600
C8—C9	1.407 (6)	O1W—H1W1	0.8500
C8—H8	0.9300	O1W—H2W1	0.8500
C16—O1—H1	109.5	C10—C11—C12	126.7 (4)
C15—O2—C18	117.4 (4)	C10—C11—H11	116.6
C9—N1—C1	122.7 (3)	C12—C11—H11	116.6
C9—N1—C19	120.6 (3)	C13—C12—C17	118.4 (3)
C1—N1—C19	116.8 (3)	C13—C12—C11	123.8 (4)
N1—C1—C6	118.5 (3)	C17—C12—C11	117.8 (4)
N1—C1—C2	122.6 (4)	C12—C13—C14	120.5 (4)
C6—C1—C2	118.9 (3)	C12—C13—H13	119.7
C3—C2—C1	119.5 (5)	C14—C13—H13	119.7
C3—C2—H2	120.3	C15—C14—C13	120.2 (4)
C1—C2—H2	120.3	C15—C14—H14	119.9
C4—C3—C2	122.1 (4)	C13—C14—H14	119.9
C4—C3—H3	118.9	O2—C15—C16	114.8 (4)
C2—C3—H3	118.9	O2—C15—C14	125.3 (4)
C3—C4—C5	120.1 (4)	C16—C15—C14	119.9 (3)
C3—C4—H4	119.9	O1—C16—C15	117.7 (3)
C5—C4—H4	119.9	O1—C16—C17	123.2 (4)
C4—C5—C6	120.4 (5)	C15—C16—C17	119.1 (4)
C4—C5—H5	119.8	C16—C17—C12	121.8 (4)
C6—C5—H5	119.8	C16—C17—H17	119.1
C1—C6—C5	119.0 (4)	C12—C17—H17	119.1
C1—C6—C7	118.8 (3)	O2—C18—H18A	109.5
C5—C6—C7	122.2 (4)	O2—C18—H18B	109.5
C8—C7—C6	120.7 (4)	H18A—C18—H18B	109.5
C8—C7—H7	119.6	O2—C18—H18C	109.5
C6—C7—H7	119.6	H18A—C18—H18C	109.5
C7—C8—C9	120.7 (4)	H18B—C18—H18C	109.5
C7—C8—H8	119.7	N1—C19—H19A	109.5
C9—C8—H8	119.7	N1—C19—H19B	109.5
N1—C9—C8	118.6 (3)	H19A—C19—H19B	109.5
N1—C9—C10	121.2 (3)	N1—C19—H19C	109.5
C8—C9—C10	120.2 (3)	H19A—C19—H19C	109.5
C11—C10—C9	123.8 (4)	H19B—C19—H19C	109.5
C11—C10—H10	118.1	H1W1—O1W—H2W1	107.7
C9—C10—H10	118.1
C9—N1—C1—C6	−1.8 (4)	C7—C8—C9—N1	1.0 (5)
C19—N1—C1—C6	177.1 (3)	C7—C8—C9—C10	−179.5 (4)
C9—N1—C1—C2	177.8 (3)	N1—C9—C10—C11	−179.7 (3)
C19—N1—C1—C2	−3.3 (5)	C8—C9—C10—C11	0.8 (5)
N1—C1—C2—C3	178.0 (3)	C9—C10—C11—C12	179.6 (3)
C6—C1—C2—C3	−2.5 (5)	C10—C11—C12—C13	2.1 (6)
C1—C2—C3—C4	0.9 (6)	C10—C11—C12—C17	−177.1 (3)
C2—C3—C4—C5	0.7 (7)	C17—C12—C13—C14	−1.1 (5)
C3—C4—C5—C6	−0.7 (7)	C11—C12—C13—C14	179.7 (3)
N1—C1—C6—C5	−177.9 (3)	C12—C13—C14—C15	1.1 (6)
C2—C1—C6—C5	2.5 (5)	C18—O2—C15—C16	176.3 (4)
N1—C1—C6—C7	1.4 (5)	C18—O2—C15—C14	−2.9 (6)
C2—C1—C6—C7	−178.1 (3)	C13—C14—C15—O2	179.1 (4)
C4—C5—C6—C1	−1.0 (6)	C13—C14—C15—C16	0.0 (6)
C4—C5—C6—C7	179.7 (4)	O2—C15—C16—O1	0.8 (5)
C1—C6—C7—C8	0.1 (6)	C14—C15—C16—O1	179.9 (3)
C5—C6—C7—C8	179.4 (4)	O2—C15—C16—C17	179.8 (3)
C6—C7—C8—C9	−1.3 (6)	C14—C15—C16—C17	−1.0 (5)
C1—N1—C9—C8	0.6 (4)	O1—C16—C17—C12	180.0 (3)
C19—N1—C9—C8	−178.3 (3)	C15—C16—C17—C12	1.0 (5)
C1—N1—C9—C10	−178.9 (3)	C13—C12—C17—C16	0.1 (5)
C19—N1—C9—C10	2.2 (5)	C11—C12—C17—C16	179.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1W^i	0.82	1.88	2.671 (5)	161
O1W—H1W1···Cl1^ii	0.85	2.78	3.51 (2)	145
O1W—H2W1···Cl1	0.85	2.78	3.59 (2)	161
C3—H3···O1^iii	0.93	2.59	3.254 (6)	129
C19—H19C···O2^iv	0.96	2.59	3.433 (7)	146

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