Synthesis and crystal structure of 1,3-bis­(4-hy­droxy­phen­yl)-1H-imidazol-3-ium chloride

The title compound, 1,3-bis­(4-hy­droxy­phen­yl)-1H-imidazol-3-ium chloride (IOH·Cl) is a new imidazolium salt with a hy­droxy functionality.

Key indicators

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.049
• wR factor = 0.083
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.435 Check

Alert level G
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          6 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: APEX3 (Bruker, 2016); data reduction: APEX3 (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b) and CIFFIX (Parkin, 2013).

1,3-Bis(4-hydroxyphenyl)-1H-imidazol-3-ium chloride

Crystal data

C15H13N2O2^+·Cl^−	F(000) = 600
Mr = 288.72	Dx = 1.410 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.1752 (6) Å	Cell parameters from 1847 reflections
b = 13.2684 (8) Å	θ = 3.2–25.1°
c = 12.7391 (10) Å	µ = 0.28 mm^−1
β = 100.105 (3)°	T = 90 K
V = 1360.40 (17) Å^3	Needle, pale yellow
Z = 4	0.24 × 0.03 × 0.03 mm

Data collection

Bruker D8 Venture dual source diffractometer	3109 independent reflections
Radiation source: microsource	1869 reflections with I > 2σ(I)
Detector resolution: 7.41 pixels mm^-1	Rint = 0.103
φ and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −10→10
Tmin = 0.821, Tmax = 0.928	k = −12→17
14925 measured reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: mixed
wR(F^2) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + 0.9975P] where P = (Fo^2 + 2Fc^2)/3
3109 reflections	(Δ/σ)max < 0.001
187 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

Experimental. The crystal was mounted using polyisobutene oil on the tip of a fine glass fibre, which was fastened in a copper mounting pin with electrical solder. It was placed directly into the cold gas stream of a liquid-nitrogen based cryostat (Hope, 1994; Parkin & Hope, 1998).

Diffraction data were collected with the crystal at 90K, which is standard practice in this laboratory for the majority of flash-cooled crystals.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement progress was checked using Platon (Spek, 2009) and by an R-tensor (Parkin, 2000). The final model was further checked with the IUCr utility checkCIF.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.02919 (8)	0.26975 (5)	0.32981 (6)	0.02188 (17)
N1	0.1115 (3)	0.61456 (15)	0.38285 (18)	0.0172 (5)
N2	−0.0616 (3)	0.59391 (15)	0.23466 (18)	0.0177 (5)
O1	0.6632 (2)	0.62630 (14)	0.70648 (16)	0.0267 (5)
H1O	0.754 (4)	0.658 (2)	0.685 (2)	0.040*
O2	−0.3960 (2)	0.45255 (13)	−0.15434 (15)	0.0246 (5)
H2O	−0.407 (3)	0.386 (2)	−0.155 (2)	0.037*
C1	0.0899 (3)	0.56926 (18)	0.2872 (2)	0.0196 (6)
H1	0.168035	0.527175	0.261384	0.023*
C2	−0.0294 (3)	0.66978 (18)	0.3909 (2)	0.0201 (6)
H2	−0.047100	0.709198	0.450155	0.024*
C3	−0.1369 (3)	0.65700 (19)	0.2986 (2)	0.0209 (6)
H3	−0.244440	0.685964	0.280713	0.025*
C4	0.2593 (3)	0.61151 (18)	0.4634 (2)	0.0170 (6)
C5	0.4107 (3)	0.64043 (18)	0.4386 (2)	0.0187 (6)
H5	0.420025	0.657846	0.367563	0.022*
C6	0.5480 (3)	0.64350 (17)	0.5191 (2)	0.0187 (6)
H6	0.653195	0.661931	0.503157	0.022*
C7	0.5329 (3)	0.61976 (18)	0.6233 (2)	0.0195 (6)
C8	0.3809 (3)	0.58845 (18)	0.6463 (2)	0.0199 (6)
H8	0.371354	0.570419	0.717145	0.024*
C9	0.2436 (3)	0.58362 (18)	0.5658 (2)	0.0204 (6)
H9	0.139637	0.561368	0.580702	0.024*
C10	−0.1400 (3)	0.55635 (18)	0.1320 (2)	0.0173 (6)
C11	−0.1393 (3)	0.45368 (19)	0.1120 (2)	0.0222 (7)
H11	−0.082486	0.408543	0.163846	0.027*
C12	−0.2225 (3)	0.41836 (19)	0.0158 (2)	0.0231 (7)
H12	−0.221456	0.348340	0.000365	0.028*
C13	−0.3082 (3)	0.48456 (19)	−0.0591 (2)	0.0186 (6)
C14	−0.3043 (3)	0.58696 (19)	−0.0383 (2)	0.0204 (6)
H14	−0.359489	0.632414	−0.090377	0.025*
C15	−0.2207 (3)	0.62337 (19)	0.0576 (2)	0.0201 (6)
H15	−0.218569	0.693606	0.072208	0.024*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0211 (3)	0.0216 (3)	0.0222 (4)	0.0002 (3)	0.0016 (3)	0.0014 (3)
N1	0.0161 (12)	0.0175 (11)	0.0171 (13)	0.0012 (9)	0.0003 (10)	−0.001 (1)
N2	0.0184 (13)	0.0184 (11)	0.0155 (13)	0.0004 (9)	0.0008 (10)	−0.0011 (9)
O1	0.0184 (11)	0.0370 (12)	0.0223 (12)	−0.0078 (9)	−0.0031 (9)	0.0074 (9)
O2	0.0334 (12)	0.0194 (10)	0.0176 (12)	−0.0022 (9)	−0.0044 (10)	−0.0014 (9)
C1	0.0202 (15)	0.0199 (14)	0.0180 (17)	0.0023 (11)	0.0015 (13)	0.0003 (12)
C2	0.0191 (15)	0.0226 (14)	0.0197 (17)	0.0058 (11)	0.0062 (13)	−0.0025 (12)
C3	0.0180 (15)	0.0222 (14)	0.0222 (17)	0.0054 (12)	0.0028 (13)	−0.0001 (12)
C4	0.0156 (14)	0.0183 (13)	0.0160 (16)	−0.0002 (11)	0.0000 (12)	−0.0012 (12)
C5	0.0222 (16)	0.0182 (14)	0.0158 (16)	0.0015 (11)	0.0035 (13)	−0.0006 (11)
C6	0.0182 (15)	0.0181 (14)	0.0198 (16)	−0.0012 (11)	0.0035 (13)	0.0017 (12)
C7	0.0200 (15)	0.0185 (13)	0.0179 (16)	0.0007 (11)	−0.0021 (13)	0.0016 (12)
C8	0.0228 (16)	0.0238 (15)	0.0135 (16)	−0.0018 (12)	0.0041 (13)	0.0053 (12)
C9	0.0189 (15)	0.0188 (14)	0.0229 (18)	−0.0018 (11)	0.0022 (13)	0.0006 (12)
C10	0.0161 (15)	0.0196 (14)	0.0155 (16)	−0.0014 (11)	0.0005 (12)	−0.0026 (12)
C11	0.0227 (16)	0.0187 (14)	0.0233 (17)	0.0040 (12)	−0.0015 (13)	0.0030 (12)
C12	0.0280 (17)	0.0178 (14)	0.0225 (18)	−0.0012 (12)	0.0015 (14)	0.0001 (12)
C13	0.0182 (15)	0.0238 (14)	0.0138 (16)	−0.0031 (11)	0.0026 (12)	−0.0021 (12)
C14	0.0258 (16)	0.0188 (14)	0.0163 (16)	0.0027 (12)	0.0027 (13)	0.0022 (12)
C15	0.0235 (16)	0.0177 (14)	0.0185 (16)	0.0000 (11)	0.0017 (13)	−0.0010 (12)

Geometric parameters (Å, º)

N1—C1	1.342 (3)	C5—H5	0.9500
N1—C2	1.384 (3)	C6—C7	1.391 (4)
N1—C4	1.442 (3)	C6—H6	0.9500
N2—C1	1.341 (3)	C7—C8	1.389 (3)
N2—C3	1.385 (3)	C8—C9	1.382 (3)
N2—C10	1.441 (3)	C8—H8	0.9500
O1—C7	1.366 (3)	C9—H9	0.9500
O1—H1O	0.93 (3)	C10—C15	1.380 (3)
O2—C13	1.364 (3)	C10—C11	1.386 (3)
O2—H2O	0.89 (3)	C11—C12	1.376 (4)
C1—H1	0.9500	C11—H11	0.9500
C2—C3	1.350 (4)	C12—C13	1.393 (4)
C2—H2	0.9500	C12—H12	0.9500
C3—H3	0.9500	C13—C14	1.384 (3)
C4—C9	1.383 (4)	C14—C15	1.378 (4)
C4—C5	1.384 (3)	C14—H14	0.9500
C5—C6	1.381 (4)	C15—H15	0.9500
C1—N1—C2	109.0 (2)	O1—C7—C6	122.6 (2)
C1—N1—C4	126.4 (2)	C8—C7—C6	120.1 (3)
C2—N1—C4	124.5 (2)	C9—C8—C7	119.8 (3)
C1—N2—C3	108.7 (2)	C9—C8—H8	120.1
C1—N2—C10	126.4 (2)	C7—C8—H8	120.1
C3—N2—C10	124.7 (2)	C8—C9—C4	119.3 (3)
C7—O1—H1O	110.7 (19)	C8—C9—H9	120.3
C13—O2—H2O	111.0 (19)	C4—C9—H9	120.3
N2—C1—N1	107.9 (2)	C15—C10—C11	121.6 (3)
N2—C1—H1	126.1	C15—C10—N2	118.9 (2)
N1—C1—H1	126.1	C11—C10—N2	119.4 (2)
C3—C2—N1	107.0 (2)	C12—C11—C10	118.7 (2)
C3—C2—H2	126.5	C12—C11—H11	120.6
N1—C2—H2	126.5	C10—C11—H11	120.6
C2—C3—N2	107.4 (2)	C11—C12—C13	120.4 (2)
C2—C3—H3	126.3	C11—C12—H12	119.8
N2—C3—H3	126.3	C13—C12—H12	119.8
C9—C4—C5	121.6 (3)	O2—C13—C14	117.9 (2)
C9—C4—N1	118.3 (2)	O2—C13—C12	122.4 (2)
C5—C4—N1	120.1 (2)	C14—C13—C12	119.7 (3)
C6—C5—C4	118.8 (3)	C15—C14—C13	120.4 (2)
C6—C5—H5	120.6	C15—C14—H14	119.8
C4—C5—H5	120.6	C13—C14—H14	119.8
C5—C6—C7	120.4 (3)	C14—C15—C10	119.1 (2)
C5—C6—H6	119.8	C14—C15—H15	120.5
C7—C6—H6	119.8	C10—C15—H15	120.5
O1—C7—C8	117.4 (3)
C3—N2—C1—N1	0.4 (3)	C6—C7—C8—C9	−1.8 (4)
C10—N2—C1—N1	−175.5 (2)	C7—C8—C9—C4	−0.9 (4)
C2—N1—C1—N2	−0.3 (3)	C5—C4—C9—C8	2.6 (4)
C4—N1—C1—N2	−177.5 (2)	N1—C4—C9—C8	−174.5 (2)
C1—N1—C2—C3	0.1 (3)	C1—N2—C10—C15	−135.4 (3)
C4—N1—C2—C3	177.3 (2)	C3—N2—C10—C15	49.3 (4)
N1—C2—C3—N2	0.2 (3)	C1—N2—C10—C11	47.6 (4)
C1—N2—C3—C2	−0.4 (3)	C3—N2—C10—C11	−127.8 (3)
C10—N2—C3—C2	175.7 (2)	C15—C10—C11—C12	−0.5 (4)
C1—N1—C4—C9	−127.9 (3)	N2—C10—C11—C12	176.5 (3)
C2—N1—C4—C9	55.3 (3)	C10—C11—C12—C13	−1.2 (4)
C1—N1—C4—C5	55.0 (4)	C11—C12—C13—O2	−178.2 (3)
C2—N1—C4—C5	−121.8 (3)	C11—C12—C13—C14	2.5 (4)
C9—C4—C5—C6	−1.5 (4)	O2—C13—C14—C15	178.5 (3)
N1—C4—C5—C6	175.5 (2)	C12—C13—C14—C15	−2.2 (4)
C4—C5—C6—C7	−1.2 (4)	C13—C14—C15—C10	0.5 (4)
C5—C6—C7—O1	−176.8 (2)	C11—C10—C15—C14	0.9 (4)
C5—C6—C7—C8	2.8 (4)	N2—C10—C15—C14	−176.1 (2)
O1—C7—C8—C9	177.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···Cl1^i	0.93 (3)	2.06 (3)	2.975 (2)	169 (3)
O2—H2O···Cl1^ii	0.89 (3)	2.13 (3)	3.0118 (19)	171 (3)
C1—H1···O1^i	0.95	2.45	3.280 (3)	145
C1—H1···O2^iii	0.95	2.51	3.271 (3)	137
C2—H2···Cl1^iv	0.95	2.80	3.647 (3)	150
C3—H3···Cl1^v	0.95	2.74	3.655 (3)	163

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