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

The title compound, C₁₉H₁₈NO₂⁺·I⁻·H₂O, crystallizes in a non-cenrosymmetric space group and exhibits a non-linear optical property. The second-harmonic generation (SHG) efficiency is about 1.95 times that of urea. The cation is essentially planar. The water mol­ecules and anions are linked into a chain along the a axis by O_water—H...I hydrogen bonds, and the cations are linked to it via O—H...O_water hydrogen bonds. In addition, π–π and C—H...O inter­actions are observed.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.015
• wR factor = 0.037
• Data-to-parameter ratio = 31.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.90
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4
PLAT410_ALERT_2_C Short Intra H...H Contact  H8     ..  H11     ..       1.98 Ang.
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H10    ..  H18C    ..       1.86 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

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      0.900
            Tmax scaled      0.472 Tmin scaled      0.390
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           35.00
           From the CIF: _reflns_number_total               7236
           Count of symmetry unique reflns         3873
           Completeness (_total/calc)            186.83%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      3363
           Fraction of Friedel pairs measured     0.868
           Are heavy atom types Z>Si present        yes

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   3 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 iodide monohydrate

Crystal data

C19H18NO2^+·I^−·H2O	Z = 1
Mr = 437.26	F(000) = 218
Triclinic, P1	Dx = 1.647 Mg m^−3
Hall symbol: P 1	Melting point = 478–480 K
a = 6.2412 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.2854 (2) Å	Cell parameters from 7236 reflections
c = 9.1961 (2) Å	θ = 2.4–35.0°
α = 68.134 (1)°	µ = 1.83 mm^−1
β = 89.424 (1)°	T = 100 K
γ = 87.720 (1)°	Block, yellow
V = 440.97 (2) Å^3	0.55 × 0.50 × 0.41 mm

Data collection

Bruker SMART APEX II CCD area-detector diffractometer	7236 independent reflections
Radiation source: fine-focus sealed tube	7233 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Detector resolution: 8.33 pixels mm^-1	θmax = 35.0°, θmin = 2.4°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→13
Tmin = 0.433, Tmax = 0.524	l = −14→14
17774 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)] = 0.015	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.037	w = 1/[σ^2(Fo^2) + (0.0184P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.002
7236 reflections	Δρmax = 1.12 e Å^−3
231 parameters	Δρmin = −0.59 e Å^−3
4 restraints	Absolute structure: Flack (1983), 3382 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.012 (7)

Special details

Experimental. The low-temparture 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 (Ų)

	x	y	z	Uiso*/Ueq
O1W	0.35252 (19)	0.78700 (16)	0.47026 (13)	0.02631 (18)
H2W	0.460 (7)	0.720 (5)	0.502 (5)	0.051 (9)*
H1W	0.238 (8)	0.721 (7)	0.498 (6)	0.075 (13)*
I1	0.858200 (2)	0.547700 (2)	0.575700 (2)	0.01983 (2)
C1	0.17133 (16)	0.29751 (13)	1.11718 (13)	0.01403 (15)
C2	0.02827 (17)	0.23253 (14)	1.03651 (14)	0.01710 (17)
H2	0.0486	0.2535	0.9308	0.021*
C3	−0.14230 (19)	0.13746 (15)	1.11567 (16)	0.01976 (19)
H3	−0.2358	0.0941	1.0623	0.024*
C4	−0.1776 (2)	0.10486 (16)	1.27509 (16)	0.0218 (2)
H4	−0.2915	0.0384	1.3270	0.026*
C5	−0.0426 (2)	0.17188 (16)	1.35372 (15)	0.02073 (19)
H5	−0.0672	0.1525	1.4587	0.025*
C6	0.13306 (17)	0.26995 (14)	1.27623 (13)	0.01602 (16)
C7	0.27382 (18)	0.34142 (15)	1.35391 (13)	0.01743 (17)
H7	0.2501	0.3258	1.4582	0.021*
C8	0.44388 (18)	0.43300 (15)	1.27663 (13)	0.01684 (17)
H8	0.5348	0.4798	1.3289	0.020*
C9	0.48488 (16)	0.45832 (13)	1.11703 (12)	0.01333 (15)
C10	0.66675 (17)	0.55516 (14)	1.03628 (13)	0.01612 (16)
H10	0.6906	0.5676	0.9327	0.019*
C11	0.80316 (17)	0.62814 (14)	1.10441 (13)	0.01603 (16)
H11	0.7749	0.6148	1.2077	0.019*
C12	0.98998 (17)	0.72556 (13)	1.03245 (13)	0.01440 (15)
C13	1.11715 (17)	0.78259 (14)	1.12746 (13)	0.01521 (16)
H13	1.0782	0.7578	1.2312	0.018*
C14	1.29947 (17)	0.87503 (13)	1.06985 (13)	0.01470 (15)
C15	1.35771 (17)	0.91485 (13)	0.91238 (13)	0.01508 (16)
C16	1.23208 (19)	0.85885 (15)	0.81666 (13)	0.01743 (17)
H16	1.2700	0.8849	0.7126	0.021*
C17	1.05019 (18)	0.76419 (15)	0.87629 (13)	0.01706 (17)
H17	0.9683	0.7265	0.8120	0.020*
C18	0.3876 (2)	0.40600 (19)	0.87976 (15)	0.0230 (2)
H18A	0.2952	0.4973	0.8109	0.035*
H18B	0.3578	0.2981	0.8692	0.035*
H18C	0.5345	0.4330	0.8529	0.035*
C19	1.6106 (2)	1.04260 (19)	0.71086 (16)	0.0255 (2)
H19A	1.7450	1.0990	0.6957	0.038*
H19B	1.5064	1.1174	0.6383	0.038*
H19C	1.6289	0.9356	0.6935	0.038*
N1	0.34977 (14)	0.38996 (12)	1.04316 (11)	0.01365 (13)
O1	1.53880 (15)	1.00661 (12)	0.86700 (11)	0.01949 (15)
O2	1.42743 (15)	0.93093 (13)	1.15838 (11)	0.02027 (15)
H1O2	1.379 (6)	0.894 (5)	1.247 (4)	0.045 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1W	0.0228 (4)	0.0352 (5)	0.0214 (4)	−0.0053 (4)	0.0021 (3)	−0.0107 (4)
I1	0.01745 (3)	0.02868 (3)	0.01497 (2)	−0.00551 (2)	0.00179 (2)	−0.00958 (2)
C1	0.0113 (4)	0.0135 (3)	0.0171 (4)	−0.0015 (3)	0.0010 (3)	−0.0054 (3)
C2	0.0135 (4)	0.0177 (4)	0.0222 (5)	−0.0026 (3)	−0.0002 (3)	−0.0096 (4)
C3	0.0144 (4)	0.0179 (4)	0.0274 (5)	−0.0040 (3)	0.0010 (4)	−0.0087 (4)
C4	0.0166 (4)	0.0204 (4)	0.0264 (5)	−0.0059 (4)	0.0033 (4)	−0.0060 (4)
C5	0.0169 (5)	0.0224 (5)	0.0197 (5)	−0.0049 (4)	0.0038 (4)	−0.0038 (4)
C6	0.0135 (4)	0.0163 (4)	0.0169 (4)	−0.0016 (3)	0.0011 (3)	−0.0046 (3)
C7	0.0153 (4)	0.0209 (4)	0.0155 (4)	−0.0021 (3)	0.0013 (3)	−0.0058 (3)
C8	0.0152 (4)	0.0214 (4)	0.0147 (4)	−0.0035 (3)	0.0003 (3)	−0.0073 (3)
C9	0.0112 (4)	0.0142 (3)	0.0150 (4)	−0.0014 (3)	−0.0003 (3)	−0.0059 (3)
C10	0.0141 (4)	0.0181 (4)	0.0165 (4)	−0.0047 (3)	0.0008 (3)	−0.0065 (3)
C11	0.0130 (4)	0.0184 (4)	0.0185 (4)	−0.0036 (3)	0.0017 (3)	−0.0086 (3)
C12	0.0128 (4)	0.0148 (4)	0.0164 (4)	−0.0022 (3)	0.0003 (3)	−0.0065 (3)
C13	0.0133 (4)	0.0165 (4)	0.0167 (4)	−0.0038 (3)	0.0016 (3)	−0.0069 (3)
C14	0.0128 (4)	0.0153 (4)	0.0167 (4)	−0.0031 (3)	0.0007 (3)	−0.0065 (3)
C15	0.0135 (4)	0.0148 (4)	0.0161 (4)	−0.0024 (3)	0.0015 (3)	−0.0047 (3)
C16	0.0174 (4)	0.0202 (4)	0.0145 (4)	−0.0031 (3)	0.0007 (3)	−0.0061 (3)
C17	0.0159 (4)	0.0197 (4)	0.0168 (4)	−0.0036 (3)	0.0002 (3)	−0.0079 (3)
C18	0.0214 (5)	0.0353 (6)	0.0182 (5)	−0.0114 (4)	0.0050 (4)	−0.0160 (4)
C19	0.0227 (5)	0.0303 (6)	0.0196 (5)	−0.0069 (4)	0.0066 (4)	−0.0043 (4)
N1	0.0121 (3)	0.0154 (3)	0.0145 (3)	−0.0026 (3)	0.0007 (3)	−0.0065 (3)
O1	0.0179 (3)	0.0207 (3)	0.0187 (4)	−0.0075 (3)	0.0050 (3)	−0.0054 (3)
O2	0.0182 (4)	0.0267 (4)	0.0183 (4)	−0.0097 (3)	0.0018 (3)	−0.0102 (3)

Geometric parameters (Å, º)

O1W—H2W	0.83 (4)	C11—C12	1.4527 (14)
O1W—H1W	0.89 (6)	C11—H11	0.93
C1—N1	1.3981 (13)	C12—C17	1.4007 (15)
C1—C2	1.4094 (15)	C12—C13	1.4029 (15)
C1—C6	1.4132 (16)	C13—C14	1.3846 (14)
C2—C3	1.3812 (15)	C13—H13	0.93
C2—H2	0.93	C14—O2	1.3559 (14)
C3—C4	1.4051 (19)	C14—C15	1.4075 (15)
C3—H3	0.93	C15—O1	1.3609 (13)
C4—C5	1.3748 (19)	C15—C16	1.3971 (16)
C4—H4	0.93	C16—C17	1.3937 (15)
C5—C6	1.4122 (15)	C16—H16	0.93
C5—H5	0.93	C17—H17	0.93
C6—C7	1.4149 (16)	C18—N1	1.4758 (15)
C7—C8	1.3618 (15)	C18—H18A	0.96
C7—H7	0.93	C18—H18B	0.96
C8—C9	1.4252 (15)	C18—H18C	0.96
C8—H8	0.93	C19—O1	1.4250 (16)
C9—N1	1.3526 (14)	C19—H19A	0.96
C9—C10	1.4476 (14)	C19—H19B	0.96
C10—C11	1.3479 (15)	C19—H19C	0.96
C10—H10	0.93	O2—H1O2	0.81 (4)
H2W—O1W—H1W	107 (4)	C17—C12—C11	124.20 (10)
N1—C1—C2	121.52 (10)	C13—C12—C11	117.06 (9)
N1—C1—C6	119.10 (9)	C14—C13—C12	121.31 (10)
C2—C1—C6	119.38 (9)	C14—C13—H13	119.3
C3—C2—C1	119.50 (11)	C12—C13—H13	119.3
C3—C2—H2	120.3	O2—C14—C13	123.03 (10)
C1—C2—H2	120.3	O2—C14—C15	117.36 (9)
C2—C3—C4	121.45 (11)	C13—C14—C15	119.61 (10)
C2—C3—H3	119.3	O1—C15—C16	125.34 (10)
C4—C3—H3	119.3	O1—C15—C14	115.10 (10)
C5—C4—C3	119.51 (10)	C16—C15—C14	119.55 (9)
C5—C4—H4	120.2	C17—C16—C15	120.38 (10)
C3—C4—H4	120.2	C17—C16—H16	119.8
C4—C5—C6	120.48 (11)	C15—C16—H16	119.8
C4—C5—H5	119.8	C16—C17—C12	120.40 (10)
C6—C5—H5	119.8	C16—C17—H17	119.8
C5—C6—C1	119.62 (11)	C12—C17—H17	119.8
C5—C6—C7	121.71 (10)	N1—C18—H18A	109.5
C1—C6—C7	118.67 (9)	N1—C18—H18B	109.5
C8—C7—C6	120.30 (10)	H18A—C18—H18B	109.5
C8—C7—H7	119.9	N1—C18—H18C	109.5
C6—C7—H7	119.9	H18A—C18—H18C	109.5
C7—C8—C9	121.10 (10)	H18B—C18—H18C	109.5
C7—C8—H8	119.4	O1—C19—H19A	109.5
C9—C8—H8	119.4	O1—C19—H19B	109.5
N1—C9—C8	118.40 (9)	H19A—C19—H19B	109.5
N1—C9—C10	120.97 (9)	O1—C19—H19C	109.5
C8—C9—C10	120.63 (9)	H19A—C19—H19C	109.5
C11—C10—C9	122.96 (10)	H19B—C19—H19C	109.5
C11—C10—H10	118.5	C9—N1—C1	122.41 (9)
C9—C10—H10	118.5	C9—N1—C18	121.09 (9)
C10—C11—C12	126.41 (10)	C1—N1—C18	116.48 (9)
C10—C11—H11	116.8	C15—O1—C19	117.27 (10)
C12—C11—H11	116.8	C14—O2—H1O2	107 (3)
C17—C12—C13	118.74 (9)
N1—C1—C2—C3	178.08 (10)	C11—C12—C13—C14	179.43 (10)
C6—C1—C2—C3	−2.42 (16)	C12—C13—C14—O2	−179.38 (11)
C1—C2—C3—C4	0.46 (18)	C12—C13—C14—C15	0.81 (17)
C2—C3—C4—C5	1.40 (19)	O2—C14—C15—O1	−0.07 (15)
C3—C4—C5—C6	−1.3 (2)	C13—C14—C15—O1	179.75 (10)
C4—C5—C6—C1	−0.71 (18)	O2—C14—C15—C16	179.46 (11)
C4—C5—C6—C7	179.59 (12)	C13—C14—C15—C16	−0.72 (16)
N1—C1—C6—C5	−177.93 (10)	O1—C15—C16—C17	179.48 (11)
C2—C1—C6—C5	2.55 (16)	C14—C15—C16—C17	0.01 (17)
N1—C1—C6—C7	1.78 (16)	C15—C16—C17—C12	0.64 (18)
C2—C1—C6—C7	−177.74 (10)	C13—C12—C17—C16	−0.55 (17)
C5—C6—C7—C8	178.93 (12)	C11—C12—C17—C16	179.88 (11)
C1—C6—C7—C8	−0.78 (17)	C8—C9—N1—C1	0.66 (15)
C6—C7—C8—C9	−0.32 (18)	C10—C9—N1—C1	−179.25 (10)
C7—C8—C9—N1	0.40 (17)	C8—C9—N1—C18	−177.76 (11)
C7—C8—C9—C10	−179.69 (11)	C10—C9—N1—C18	2.34 (16)
N1—C9—C10—C11	178.77 (11)	C2—C1—N1—C9	177.75 (10)
C8—C9—C10—C11	−1.13 (17)	C6—C1—N1—C9	−1.76 (15)
C9—C10—C11—C12	179.35 (11)	C2—C1—N1—C18	−3.76 (15)
C10—C11—C12—C17	2.90 (19)	C6—C1—N1—C18	176.73 (11)
C10—C11—C12—C13	−176.67 (11)	C16—C15—O1—C19	−2.59 (17)
C17—C12—C13—C14	−0.17 (17)	C14—C15—O1—C19	176.91 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1W^i	0.82 (3)	1.92 (3)	2.7086 (15)	163 (4)
O1W—H1W···I1^ii	0.89 (6)	2.77 (5)	3.6584 (12)	174 (5)
O1W—H2W···I1	0.84 (4)	2.78 (4)	3.6005 (12)	170 (4)
C3—H3···O2^iii	0.93	2.51	3.1840 (16)	129

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