1-(2-Hydro­xy­ethyl)-4-{4,5,6,7-tetra­hydro-1-[1-(2-hydroxy­ethyl)-pyridin-4(1H)-yl­idene]-1H-inden-3-yl}pyridinium iodide

Gainsford, G.J.; Kay, A.J.; Woolhouse, A.D.

doi:10.1107/S160053680300686X

Buy article online - an online subscription or single-article purchase is required to access this article.

1-(2-Hydroxyethyl)-4-{4,5,6,7-tetrahydro-1-[1-(2-hydroxyethyl)-pyridin-4(1H)-ylidene]-1H-inden-3-yl}pyridinium iodide

G. J. Gainsford, A. J. Kay and A. D. Woolhouse

The structure of the title compound, C₂₃H₂₇N₂O₂⁺·I⁻, was determined from a 0.14 × 0.10 × 0.003 mm crystal using synchrotron X-radiation. The cation charge is delocalized and there is strong O—H

I⁻ intermolecular hydrogen bonding.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680300686X/cf6250sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680300686X/cf6250Isup2.hkl Contains datablock I

CCDC reference: 209997

checkCIF report

Key indicators

Single-crystal synchrotron study
T = 100 K
Mean (C-C) = 0.004 Å
R factor = 0.025
wR factor = 0.071
Data-to-parameter ratio = 8.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



ABSTM_02  Alert A The ratio of Tmax/Tmin expected RT(exp) is > 1.30
          An absorption correction should be applied.
          Tmin and Tmax expected:      0.695     0.991
          RT(exp) =      1.426

THETM_01  Alert A The value of sine(theta_max)/wavelength is less than 0.550
          Calculated sin(theta_max)/wavelength =    0.5264

Author response: The CCD plate was placed as close to the crystal as was practicable (60 mm); the incomplete shell corresponds to all the available data using the highest wavelength possible on the X9B beamline.


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           28.98
         From the CIF: _reflns_number_total               2300
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         2525
         Completeness (_total/calc)             91.09%
          Alert C: < 95% complete

REFNR_01  Alert C Ratio of reflections to parameters is < 10 for a
          centrosymmetric structure
          sine(theta)/lambda                0.5264
          Proportion of unique data used    1.0000
          Ratio reflections to parameters   8.7786

General Notes



ABSMU_01  Radiation type not identified. Calculation of
          _exptl_absorpt_correction_mu not performed.


 2 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

Comment top

The title compound, (I), was prepared as part of a study into the use of zwitterionic merocyanines as potential non-linear optical (NLO) chromophores (Kay et al., 2001). Initial single-crystal and powder diffraction studies using conventional X-ray sources showed that the larger crystals suffered from both twinning and different hydration states. Access to the X9B beamline at the National Synchrotron Light Source gave sufficient data with a crystallite 0.14 × 0.10 × 0.003 mm, leading to the ordered structure reported here. The crystal contained independent C₂₃H₂₇N₂O₂⁺ cations (Fig. 1) linked in pairs about inversion centres by hydrogen bonds (O—H···I⁻, Table 2). Similar hydroxyethyl O—H···I⁻ interactions have been found in the Cambridge Structural Database (Allen, 2002) by use of Conquest (Bruno et al., 2002), in entries QIGHET, a zwitterionic cyanine dye (Lacroix et al., 2001), NUYDOA (Grobosch et al., 1998) and ABILIG (Wang et al., 2001). The pairs form a `herring-bone' pattern along the b axis, with the normals to the cation molecular planes approximately in the [101] and [101] directions.

The bond distances illustrate both self-consistency (e.g. C8—C16 and C10—C21 in Table 1) and the molecule delocalization, spreading the overall positive charge, e.g. C8—C9 = 1.412 (5) Å and C9—C13 = 1.403 (5) Å. The main molecular fragment excluding the hydoxyethyl and atoms C1/C2/C17/C18/C19 is approximately planar, with an r.m.s. displacement of 0.023 (3) Å. The two pyridine rings are subtly different, with their mean planes inclined at 5.6 (2) and 1.5 (2)° (for the C3 and C13 rings, respectively) to the planar central five-membered ring (atoms C8/C9/C10/C21/C16). Likewise, there is a small difference in the dihedral angles within the hydroxyethyl groups, with N—C—C—O(H) values of 70.7 (4) and −59.1 (4)°. Such deviations are consistent with the observed intermoleculer hydrogen bonding.

Experimental top

The compound was prepared as previously described [compound29a in Kay et al. (2001)].

Computing details top

Data collection: DENZO (Otinowski & Minor, 1997); cell refinement: DENZO; data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. The asymmetric unit of (I) (Farrugia, 1997). Displacement ellipsoids are shown at the 50% probability level and H atoms are of arbitrary radii.

1-(2-Hydroxyethyl)-4-{4,5,6,7-tetrahydro-1-[1-(2-hydroxyethyl)- pyridin-4(1H)-ylidene]-1H-inden-3-yl}pyridinium iodide top

Crystal data top

C₂₃H₂₇N₂O₂⁺·I⁻	F(000) = 992
M_r = 490.37	D_x = 1.573 Mg m⁻³
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.9204 Å
a = 9.0520 (18) Å	Cell parameters from 340 reflections
b = 24.134 (5) Å	θ = 3.8–22.5°
c = 9.5330 (19) Å	µ = 3.03 mm⁻¹
β = 96.22 (3)°	T = 100 K
V = 2070.3 (7) Å³	Plate, black
Z = 4	0.14 × 0.10 × 0.003 mm

Data collection top

Quantum4 CCD detector diffractometer	2191 reflections with I > 2σ(I)
None monochromator	R_int = 0.000
Detector resolution: 4000 pixels mm^-1	θ_max = 29.0°, θ_min = 3.0°
ϕ scans	h = 0→9
2300 measured reflections	k = 0→25
2300 independent reflections	l = −10→9

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.071	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.025P)² + 2.8457P] where P = (F_o² + 2F_c²)/3
2300 reflections	(Δ/σ)_max = 0.002
262 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

C₂₃H₂₇N₂O₂⁺·I⁻	V = 2070.3 (7) Å³
M_r = 490.37	Z = 4
Monoclinic, P2₁/c	Synchrotron radiation, λ = 0.9204 Å
a = 9.0520 (18) Å	µ = 3.03 mm⁻¹
b = 24.134 (5) Å	T = 100 K
c = 9.5330 (19) Å	0.14 × 0.10 × 0.003 mm
β = 96.22 (3)°

Data collection top

Quantum4 CCD detector diffractometer	2191 reflections with I > 2σ(I)
2300 measured reflections	R_int = 0.000
2300 independent reflections	θ_max = 29.0°

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.071	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.51 e Å⁻³
2300 reflections	Δρ_min = −0.58 e Å⁻³
262 parameters

Special details top

Experimental. Crystal decay was monitored and corrected by the inter-frame analysis (DENZO: Otwinowski & Minor, 1997).

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

	x	y	z	U_iso*/U_eq
I1	0.69464 (2)	0.845714 (9)	0.61325 (2)	0.02629 (16)
O1	−0.0167 (3)	0.74846 (10)	1.2136 (3)	0.0338 (7)
H1O	−0.076 (5)	0.7281 (18)	1.185 (5)	0.041*
O2	0.5846 (3)	1.27037 (10)	1.0761 (3)	0.0377 (7)
H2O	0.507 (5)	1.2868 (18)	1.053 (5)	0.045*
N1	−0.1179 (3)	0.86075 (10)	1.1480 (3)	0.0170 (6)
N2	0.6417 (3)	1.15909 (9)	0.9625 (3)	0.0170 (7)
C1	−0.1224 (4)	0.85604 (12)	1.0073 (4)	0.0165 (8)
H1	−0.1878	0.8298	0.9592	0.020*
C2	−0.0353 (3)	0.88799 (12)	0.9317 (3)	0.0165 (7)
H2	−0.0429	0.8839	0.8321	0.020*
C3	0.0664 (3)	0.92725 (11)	0.9976 (3)	0.0145 (7)
C4	0.0594 (4)	0.93277 (12)	1.1460 (3)	0.0171 (7)
H4	0.1200	0.9597	1.1971	0.020*
C5	−0.0312 (4)	0.90080 (12)	1.2159 (4)	0.0186 (7)
H5	−0.0344	0.9063	1.3142	0.022*
C6	−0.2003 (4)	0.82163 (13)	1.2311 (4)	0.0231 (8)
H6A	−0.2767	0.8020	1.1675	0.028*
H6B	−0.2513	0.8425	1.3013	0.028*
C7	−0.0947 (4)	0.77996 (14)	1.3062 (4)	0.0300 (9)
H7A	−0.0222	0.7999	1.3734	0.036*
H7B	−0.1518	0.7545	1.3614	0.036*
C8	0.1659 (3)	0.95914 (11)	0.9251 (3)	0.0140 (7)
C9	0.2564 (4)	1.00253 (12)	0.9852 (3)	0.0148 (7)
H9	0.255 (4)	1.0142 (13)	1.079 (4)	0.018*
C10	0.3347 (4)	1.02670 (12)	0.8816 (3)	0.0151 (7)
C11	0.5656 (4)	1.13870 (13)	1.0664 (3)	0.0180 (8)
H11	0.5817	1.1543	1.1583	0.022*
C12	0.4667 (4)	1.09638 (11)	1.0416 (3)	0.0157 (7)
H12	0.4151	1.0833	1.1167	0.019*
C13	0.4385 (3)	1.07131 (12)	0.9067 (3)	0.0149 (7)
C14	0.5184 (4)	1.09497 (12)	0.8020 (3)	0.0177 (7)
H14	0.5036	1.0808	0.7086	0.021*
C15	0.6160 (4)	1.13758 (13)	0.8313 (3)	0.0179 (7)
H15	0.6670	1.1524	0.7578	0.022*
C16	0.1935 (3)	0.95565 (12)	0.7769 (3)	0.0145 (7)
C17	0.1388 (4)	0.91208 (13)	0.6690 (3)	0.0188 (8)
H17A	0.0333	0.9193	0.6347	0.023*
H17B	0.1452	0.8750	0.7137	0.023*
C18	0.2322 (4)	0.91294 (13)	0.5443 (3)	0.0215 (8)
H18A	0.3314	0.8969	0.5736	0.026*
H18B	0.1834	0.8901	0.4664	0.026*
C19	0.2495 (4)	0.97176 (13)	0.4936 (4)	0.0227 (8)
H19A	0.1503	0.9889	0.4720	0.027*
H19B	0.2991	0.9715	0.4060	0.027*
C20	0.3416 (4)	1.00582 (13)	0.6064 (3)	0.0204 (8)
H20A	0.4476	0.9954	0.6086	0.024*
H20B	0.3324	1.0456	0.5822	0.024*
C21	0.2910 (3)	0.99639 (12)	0.7499 (3)	0.0146 (7)
C23	0.6751 (4)	1.26098 (13)	0.9666 (4)	0.0272 (9)
H23A	0.7512	1.2905	0.9670	0.033*
H23B	0.6138	1.2616	0.8741	0.033*
C22	0.7489 (4)	1.20558 (12)	0.9896 (4)	0.0222 (8)
H22A	0.8280	1.2020	0.9262	0.027*
H22B	0.7962	1.2033	1.0881	0.027*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0229 (2)	0.0389 (2)	0.0163 (2)	−0.00270 (9)	−0.00135 (14)	−0.00171 (8)
O1	0.0292 (16)	0.0273 (14)	0.0458 (17)	0.0000 (11)	0.0083 (14)	0.0059 (12)
O2	0.0477 (18)	0.0355 (15)	0.0289 (15)	0.0186 (13)	−0.0008 (15)	−0.0034 (11)
N1	0.0173 (16)	0.0170 (13)	0.0172 (17)	0.0009 (12)	0.0041 (14)	0.0023 (12)
N2	0.0146 (16)	0.0153 (14)	0.0211 (17)	0.0010 (10)	0.0010 (14)	0.0005 (11)
C1	0.017 (2)	0.0126 (15)	0.019 (2)	0.0015 (13)	−0.0012 (16)	−0.0033 (13)
C2	0.0170 (18)	0.0182 (16)	0.0133 (17)	0.0023 (14)	−0.0027 (15)	−0.0024 (13)
C3	0.0153 (18)	0.0123 (15)	0.0150 (18)	0.0053 (13)	−0.0023 (15)	0.0008 (12)
C4	0.0158 (18)	0.0196 (17)	0.0149 (18)	0.0011 (13)	−0.0026 (15)	−0.0024 (13)
C5	0.0173 (17)	0.0243 (18)	0.0137 (16)	0.0038 (14)	−0.0006 (16)	0.0016 (14)
C6	0.023 (2)	0.0242 (18)	0.0242 (19)	−0.0021 (15)	0.0093 (17)	0.0047 (14)
C7	0.036 (2)	0.0253 (19)	0.029 (2)	−0.0008 (16)	0.0070 (19)	0.0096 (15)
C8	0.0118 (18)	0.0143 (16)	0.0151 (18)	0.0053 (13)	−0.0025 (15)	0.0016 (12)
C9	0.0155 (18)	0.0163 (16)	0.0117 (18)	0.0057 (13)	−0.0022 (15)	−0.0010 (13)
C10	0.0153 (17)	0.0154 (16)	0.0140 (18)	0.0030 (13)	−0.0007 (15)	0.0004 (12)
C11	0.0178 (19)	0.0199 (16)	0.0155 (18)	0.0028 (15)	−0.0012 (16)	−0.0026 (14)
C12	0.0140 (18)	0.0178 (17)	0.0153 (17)	0.0019 (14)	0.0019 (15)	0.0007 (13)
C13	0.0127 (17)	0.0147 (16)	0.0173 (18)	0.0054 (13)	0.0010 (15)	0.0024 (13)
C14	0.0191 (19)	0.0198 (17)	0.0141 (18)	0.0012 (14)	0.0004 (15)	−0.0017 (13)
C15	0.0182 (19)	0.0211 (17)	0.0144 (18)	0.0023 (15)	0.0014 (16)	0.0047 (14)
C16	0.0124 (18)	0.0174 (16)	0.0131 (17)	0.0049 (13)	−0.0012 (15)	−0.0011 (13)
C17	0.0176 (19)	0.0201 (17)	0.0180 (18)	0.0002 (13)	−0.0008 (16)	−0.0022 (14)
C18	0.022 (2)	0.0291 (18)	0.0129 (18)	0.0001 (15)	−0.0020 (16)	−0.0058 (14)
C19	0.024 (2)	0.0307 (19)	0.0133 (18)	−0.0020 (15)	0.0025 (16)	−0.0028 (14)
C20	0.0208 (19)	0.0256 (18)	0.0147 (18)	−0.0034 (14)	0.0014 (15)	−0.0010 (14)
C21	0.0123 (18)	0.0179 (16)	0.0132 (17)	0.0052 (13)	−0.0007 (15)	−0.0020 (13)
C23	0.031 (2)	0.0209 (18)	0.029 (2)	−0.0004 (15)	−0.0011 (19)	−0.0002 (15)
C22	0.0176 (19)	0.0188 (18)	0.029 (2)	−0.0055 (14)	−0.0009 (17)	−0.0001 (14)

Geometric parameters (Å, º) top

O1—C7	1.412 (5)	C23—C22	1.500 (5)
O2—C23	1.413 (5)	O1—H1O	0.75 (4)
N1—C1	1.342 (4)	O2—H2O	0.82 (5)
N1—C5	1.364 (4)	C1—H1	0.950
N1—C6	1.484 (4)	C2—H2	0.950
N2—C15	1.351 (4)	C4—H4	0.950
N2—C11	1.358 (4)	C5—H5	0.950
N2—C22	1.488 (4)	C6—H6A	0.990
C1—C2	1.363 (5)	C6—H6B	0.990
C2—C3	1.420 (4)	C7—H7A	0.990
C3—C8	1.420 (4)	C7—H7B	0.990
C3—C4	1.429 (5)	C9—H9	0.94 (4)
C4—C5	1.352 (5)	C11—H11	0.950
C6—C7	1.513 (5)	C12—H12	0.950
C8—C9	1.412 (5)	C14—H14	0.950
C8—C16	1.464 (4)	C15—H15	0.950
C9—C10	1.403 (5)	C17—H17A	0.990
C10—C13	1.432 (5)	C17—H17B	0.990
C10—C21	1.470 (4)	C18—H18A	0.990
C11—C12	1.362 (5)	C18—H18B	0.990
C12—C13	1.419 (5)	C19—H19A	0.990
C13—C14	1.415 (5)	C19—H19B	0.990
C14—C15	1.365 (5)	C20—H20A	0.990
C16—C21	1.364 (5)	C20—H20B	0.990
C16—C17	1.516 (4)	C23—H23A	0.990
C17—C18	1.532 (5)	C23—H23B	0.990
C18—C19	1.513 (5)	C22—H22A	0.990
C19—C20	1.528 (5)	C22—H22B	0.990
C20—C21	1.506 (5)

C1—N1—C5	119.2 (3)	N1—C6—H6A	109.6
C1—N1—C6	121.1 (3)	C7—C6—H6A	109.6
C5—N1—C6	119.6 (3)	N1—C6—H6B	109.6
C15—N2—C11	119.1 (3)	C7—C6—H6B	109.6
C15—N2—C22	119.6 (3)	H6A—C6—H6B	108.1
C11—N2—C22	121.3 (3)	O1—C7—H7A	108.9
N1—C1—C2	121.6 (3)	C6—C7—H7A	108.9
C1—C2—C3	121.9 (3)	O1—C7—H7B	108.9
C8—C3—C2	124.2 (3)	C6—C7—H7B	108.9
C8—C3—C4	122.0 (3)	H7A—C7—H7B	107.7
C2—C3—C4	113.8 (3)	C10—C9—H9	127 (2)
C5—C4—C3	121.9 (3)	C8—C9—H9	123 (2)
C4—C5—N1	121.3 (3)	N2—C11—H11	119.3
N1—C6—C7	110.3 (3)	C12—C11—H11	119.3
O1—C7—C6	113.3 (3)	C11—C12—H12	119.1
C9—C8—C3	125.1 (3)	C13—C12—H12	119.1
C9—C8—C16	106.4 (3)	C15—C14—H14	119.0
C3—C8—C16	128.5 (3)	C13—C14—H14	119.0
C10—C9—C8	109.7 (3)	N2—C15—H15	119.3
C9—C10—C13	124.6 (3)	C14—C15—H15	119.3
C9—C10—C21	106.6 (3)	C16—C17—H17A	109.6
C13—C10—C21	128.9 (3)	C18—C17—H17A	109.6
N2—C11—C12	121.4 (3)	C16—C17—H17B	109.6
C11—C12—C13	121.8 (3)	C18—C17—H17B	109.6
C14—C13—C12	114.3 (3)	H17A—C17—H17B	108.1
C14—C13—C10	124.2 (3)	C19—C18—H18A	109.6
C12—C13—C10	121.5 (3)	C17—C18—H18A	109.6
C15—C14—C13	121.9 (3)	C19—C18—H18B	109.6
N2—C15—C14	121.4 (3)	C17—C18—H18B	109.6
C21—C16—C8	108.8 (3)	H18A—C18—H18B	108.1
C21—C16—C17	122.8 (3)	C18—C19—H19A	109.6
C8—C16—C17	128.1 (3)	C20—C19—H19A	109.6
C16—C17—C18	110.5 (3)	C18—C19—H19B	109.6
C19—C18—C17	110.2 (3)	C20—C19—H19B	109.6
C18—C19—C20	110.3 (3)	H19A—C19—H19B	108.1
C21—C20—C19	111.2 (3)	C21—C20—H20A	109.4
C16—C21—C10	108.5 (3)	C19—C20—H20A	109.4
C16—C21—C20	123.2 (3)	C21—C20—H20B	109.4
C10—C21—C20	128.3 (3)	C19—C20—H20B	109.4
O2—C23—C22	108.7 (3)	H20A—C20—H20B	108.0
N2—C22—C23	112.0 (3)	O2—C23—H23A	110.0
C7—O1—H1O	101 (3)	C22—C23—H23A	110.0
C23—O2—H2O	116 (3)	O2—C23—H23B	110.0
N1—C1—H1	119.2	C22—C23—H23B	110.0
C2—C1—H1	119.2	H23A—C23—H23B	108.3
C1—C2—H2	119.1	N2—C22—H22A	109.2
C3—C2—H2	119.1	C23—C22—H22A	109.2
C5—C4—H4	119.0	N2—C22—H22B	109.2
C3—C4—H4	119.0	C23—C22—H22B	109.2
C4—C5—H5	119.4	H22A—C22—H22B	107.9
N1—C5—H5	119.4

C5—N1—C1—C2	4.2 (4)	C21—C10—C13—C12	179.4 (3)
C6—N1—C1—C2	−173.1 (3)	C12—C13—C14—C15	1.2 (4)
N1—C1—C2—C3	1.1 (5)	C10—C13—C14—C15	179.9 (3)
C1—C2—C3—C8	176.1 (3)	C11—N2—C15—C14	−1.8 (5)
C1—C2—C3—C4	−4.7 (4)	C22—N2—C15—C14	−179.9 (3)
C8—C3—C4—C5	−177.3 (3)	C13—C14—C15—N2	0.4 (5)
C2—C3—C4—C5	3.4 (4)	C9—C8—C16—C21	−2.2 (3)
C3—C4—C5—N1	1.5 (5)	C3—C8—C16—C21	176.2 (3)
C1—N1—C5—C4	−5.5 (4)	C9—C8—C16—C17	172.3 (3)
C6—N1—C5—C4	171.8 (3)	C3—C8—C16—C17	−9.2 (5)
C1—N1—C6—C7	103.4 (4)	C21—C16—C17—C18	12.4 (4)
C5—N1—C6—C7	−73.9 (4)	C8—C16—C17—C18	−161.4 (3)
N1—C6—C7—O1	−59.0 (4)	C16—C17—C18—C19	−47.6 (4)
C2—C3—C8—C9	172.8 (3)	C17—C18—C19—C20	66.3 (4)
C4—C3—C8—C9	−6.4 (5)	C18—C19—C20—C21	−45.8 (4)
C2—C3—C8—C16	−5.4 (5)	C8—C16—C21—C10	2.0 (3)
C4—C3—C8—C16	175.4 (3)	C17—C16—C21—C10	−172.8 (3)
C3—C8—C9—C10	−177.0 (3)	C8—C16—C21—C20	−178.6 (3)
C16—C8—C9—C10	1.5 (3)	C17—C16—C21—C20	6.5 (5)
C8—C9—C10—C13	−178.9 (3)	C9—C10—C21—C16	−1.1 (3)
C8—C9—C10—C21	−0.3 (3)	C13—C10—C21—C16	177.4 (3)
C15—N2—C11—C12	1.4 (4)	C9—C10—C21—C20	179.6 (3)
C22—N2—C11—C12	179.6 (3)	C13—C10—C21—C20	−1.9 (5)
N2—C11—C12—C13	0.3 (5)	C19—C20—C21—C16	10.4 (4)
C11—C12—C13—C14	−1.5 (4)	C19—C20—C21—C10	−170.3 (3)
C11—C12—C13—C10	179.8 (3)	C15—N2—C22—C23	89.5 (4)
C9—C10—C13—C14	179.2 (3)	C11—N2—C22—C23	−88.7 (4)
C21—C10—C13—C14	0.9 (5)	O2—C23—C22—N2	70.7 (4)
C9—C10—C13—C12	−2.3 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···I1ⁱ	0.82 (4)	2.69 (5)	3.459 (3)	158 (2)
O1—H1O···I1ⁱⁱ	0.76 (4)	2.76 (5)	3.517 (3)	173 (5)

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

Experimental details

Crystal data
Chemical formula	C₂₃H₂₇N₂O₂⁺·I⁻
M_r	490.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.0520 (18), 24.134 (5), 9.5330 (19)
β (°)	96.22 (3)
V (Å³)	2070.3 (7)
Z	4
Radiation type	Synchrotron, λ = 0.9204 Å
µ (mm⁻¹)	3.03
Crystal size (mm)	0.14 × 0.10 × 0.003

Data collection
Diffractometer	Quantum4 CCD detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2300, 2300, 2191
R_int	0.000
θ_max (°)	29.0
(sin θ/λ)_max (Å⁻¹)	0.526

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.071, 1.06
No. of reflections	2300
No. of parameters	262
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.58

Computer programs: DENZO (Otinowski & Minor, 1997), DENZO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.

Selected geometric parameters (Å, º) top

O1—C7	1.412 (5)	C8—C9	1.412 (5)
N1—C1	1.342 (4)	C8—C16	1.464 (4)
N1—C6	1.484 (4)	C9—C10	1.403 (5)
C1—C2	1.363 (5)	C10—C21	1.470 (4)
C2—C3	1.420 (4)	C16—C21	1.364 (5)
C3—C8	1.420 (4)	C17—C18	1.532 (5)

C10—C9—C8	109.7 (3)	C10—C21—C20	128.3 (3)

C4—C3—C8—C9	−6.4 (5)	C3—C8—C16—C17	−9.2 (5)
C21—C10—C13—C14	0.9 (5)	C17—C16—C21—C20	6.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···I1ⁱ	0.82 (4)	2.69 (5)	3.459 (3)	158 (2)
O1—H1O···I1ⁱⁱ	0.76 (4)	2.76 (5)	3.517 (3)	173 (5)

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

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.

E-mail address*
Repeat e-mail address* (for error checking)

Format*	PDF (US $40)
	HTML (US $40)
	PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number (non-UK EC countries only)
Country*

Terms and conditions of use
Contact us

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page