6-(2-Hydroxy­phen­yl)-5,6-dihydro­benzimidazolo[1,2-c]quinazolin-12-ium bromide ethanol solvate

Booysen, I.; Gerber, T.I.A.; Hosten, E.; Mayer, P.

doi:10.1107/S1600536809032899

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2216

doi:10.1107/S1600536809032899

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6-(2-Hydroxyphenyl)-5,6-dihydrobenzimidazolo[1,2-c]quinazolin-12-ium bromide ethanol solvate

Irvin Booysen,^a Thomas I. A. Gerber,^a ^* Eric Hosten ^a and Peter Mayer ^b

^aDepartment of Chemistry, Nelson Mandela Metropolitan University, 6031 Port Elizabeth, South Africa, and ^bDepartment of Chemistry, Ludiwig-Maximilians University, D-81377 München, Germany
^*Correspondence e-mail: thomas.gerber@nmmu.ac.za

(Received 18 August 2009; accepted 18 August 2009; online 22 August 2009)

In the title compound, C₂₀H₁₆N₃O⁺·Br⁻·C₂H₆O, the phenol ring forms dihedral angles of 84.5 (1) and 89.3 (1)° with the benzimidazole system and the quinazoline benzene ring, respectively. The two N—H groups act as donors in hydrogen bonds with the bromide ion as acceptor, leading to infinite eight-membered chains along [100]. According to graph-set theory the descriptor on the binary level is C₂¹(8). O—H⋯O and O—H⋯Br hydrogen bonds also occur.

Related literature

For the synthesis of quinazolines, see: Kubicova et al. (2003 ); Niementowski (1895 ). For related literature, see: Cuny et al. (1980 ); Williamson (1957 ). For graph-set analysis, see: Bernstein et al. (1995 ); Etter et al. (1990 ).

Experimental

Crystal data

C₂₀H₁₆N₃O⁺·Br⁻·C₂H₆O
M_r = 440.33
Triclinic, $[P \overline 1]$
a = 9.3438 (5) Å
b = 10.0736 (5) Å
c = 10.8452 (5) Å
α = 86.832 (4)°
β = 77.203 (4)°
γ = 84.674 (4)°
V = 990.53 (9) Å³
Z = 2
Mo Kα radiation
μ = 2.10 mm⁻¹
T = 200 K
0.28 × 0.24 × 0.05 mm

Data collection

Oxford XCalibur diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.783, T_max = 1.000 (expected range = 0.705–0.900)
7695 measured reflections
4004 independent reflections
2664 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.057
S = 0.84
4004 reflections
256 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.84	1.82	2.657 (2)	175
N1—H71⋯Br1ⁱⁱ	0.88	2.61	3.3501 (17)	142
N3—H73⋯Br1ⁱⁱⁱ	0.88	2.45	3.1956 (18)	143
O2—H2⋯Br1	0.84	2.41	3.2378 (17)	168
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y+1, z; (iii) x, y+1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: PARST (Nardelli, 1995 ) and publCIF (Westrip, 20091).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809032899/ng2630sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809032899/ng2630Isup2.hkl

checkCIF report

Comment top

In the present work the structure of 2-(tetrahydrobenzimidazolium[1,2-c]quinazolin-5-yl)phenol bromide has been determined to explore its suitability as a bidentate ligand for various metal ions. In the structure the quinazoline ring adopts a chair conformation: atoms C8, C13, C14, N1 and N2 are coplanar, with atom C7 from the plane by 0.178 Å (Figure 1). The orientation of the phenol ring is determined by a hydrogen-bond between the phenolic oxygen atom and the ethanolic oxygen atom. This ring makes dihedral angles of 84.5° and 89.3° with the benzimidazole and phenyl rings respectively. The ligand bond distances and angles show that N3–C14 is a localized double bond [1.337 (3) Å], with N2–C15 a single bond at 1.398 (3) Å. N3 is protonated, with the C14–N3–C16 bond angle equal to 109.30 (17)°. The N1–C7 bond length is 1.452 (3) Å, and the N1–C7–N2 bond angle [107.71 (16)°] illustrates the sp3 hybridization of C7.

The molecular packing of the title compound is shown in Figure 2. A feature of the structure is parallel stacking of the 5-membered ring N2—C14—N3—C16—C15 and the 6-membered ring C15—C16—C17—C18—C19—C20. These planes have an interplanar angle of 0.45 (11)° and an interplanar distance of 3.4118 (8) Å.

The two O–H groups and the two N–H groups act as donors in four different hydrogen bonds, three of them with bromide as acceptor and one of them with the ethanolic oxygen atom as acceptor. In terms of graph set analysis (Etter et al., 1990; Bernstein et al., 1995), three extended hydrogen bond patterns may be selected and characterized by graph set descriptors. 8-membered chains along [100] are formed by the two hydrogen bonds of the type N–H···Br (graph set descriptor C¹₂(8) on the binary level, Figure 3). A 20-membered ring and a 24-membered ring are formed by six hydrogen bonds within two formula units (Figures 4 and 5). The graph set descriptors R⁴₆(20) and R⁴₆(24), respectively, can be assigned on the ternary level.

Related literature top

For the synthesis of quinazolines, see: Kubicova et al. (2003); Niementowski (1895). For related literature, see: Cuny et al. (1980); Williamson (1957). For graph-set analysis, see: Bernstein et al. (1995); Etter et al. (1990).

Experimental top

All chemicals used (reagent grade) were commercially available. A mass of 0.0244 g (200 µmol) of 2-aminobenzaldehyde was dissolved in methanol (10 cm³), and 0.0418 g (200 µmol) of 2-(2-aminophenyl)-1-benzimidazole was added with stirring. After the mixture was heated under reflux for 30 min, a mass of 0.096 g (100 µmol) of trans-[ReOBr₃(PPh₃)₂] was added, and heating was continued for a further 30 min. After cooling to room temperature, the solution was filtered and left to evaporate slowly at room temperature. After 2 days 0.063 g (72%) of colourless crystals, with the formulation [C₂₀H₁₆N₃O]Br.C₂H₆O and suitable for X-ray analysis, were collected. M.p. 211°C. ¹H NMR (300 MHz, d6-DMSO): 14.71 (1H, br s), 8.62 (1H,d), 8.58 (1H, d), 8.18 (1H, s), 8.04–8.09 (2H, m), 7.72–7.82 (3H, m), 7.68 (1H, dd), 7.42–7.48 (2H, m), 7.28 (1^H, t), 7.19 (1^H, t), 7.06 (1H, d), 3.42 (2H, q), 1.23 (3H, t). IR (KBr, cm^-1): ν(OH) 3460w, ν(NH) 3275, ν(C=N) 1603 s.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PARST (Nardelli, 1995) and publCIF (Westrip, 20091).

Figures top

	Fig. 1. The molecular structure of the title compound (anisotropic displacement ellipsoids drawn at the 50% probablility level).
	Fig. 2. The packing of the title compound, viewed along [-100].
	Fig. 3. The hydrogen bonds leading to infinite 8-membered chains along [100]. b: N1–H71···Br1, c: N3–H73···Br1.
	Fig. 4. The hydrogen bonds leading to 20-membered rings. a: O1–H1···O2, b: N1–H71···Br1, d: O2–H2···Br1.
	Fig. 5. The hydrogen bonds leading to 24-membered rings. a: O1–H1···O2, c: N3–H73···Br1, d: O2–H2···Br1.

6-(2-Hydroxyphenyl)-5,6-dihydrobenzimidazolo[1,2-c]quinazolin-12-ium bromide ethanol solvate top

Crystal data top

C₂₀H₁₆N₃O⁺·Br⁻·C₂H₆O	F(000) = 452
M_r = 440.33	D_x = 1.476 (1) Mg m⁻³
Triclinic, P1	Melting point: 484 K
a = 9.3438 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0736 (5) Å	Cell parameters from 3249 reflections
c = 10.8452 (5) Å	θ = 3.9–26.3°
α = 86.832 (4)°	µ = 2.10 mm⁻¹
β = 77.203 (4)°	T = 200 K
γ = 84.674 (4)°	Platelet, yellow
V = 990.53 (9) Å³	0.28 × 0.24 × 0.05 mm
Z = 2

Data collection top

Oxford XCalibur diffractometer	4004 independent reflections
Radiation source: fine-focus sealed tube	2664 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 15.9809 pixels mm^-1	θ_max = 26.3°, θ_min = 3.9°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −12→12
T_min = 0.783, T_max = 1.000	l = −13→12
7695 measured reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.057	H-atom parameters constrained
S = 0.84	w = 1/[σ²(F_o²) + (0.0232P)²] where P = (F_o² + 2F_c²)/3
4004 reflections	(Δ/σ)_max = 0.001
256 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₀H₁₆N₃O⁺·Br⁻·C₂H₆O	γ = 84.674 (4)°
M_r = 440.33	V = 990.53 (9) Å³
Triclinic, P1	Z = 2
a = 9.3438 (5) Å	Mo Kα radiation
b = 10.0736 (5) Å	µ = 2.10 mm⁻¹
c = 10.8452 (5) Å	T = 200 K
α = 86.832 (4)°	0.28 × 0.24 × 0.05 mm
β = 77.203 (4)°

Data collection top

Oxford XCalibur diffractometer	4004 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	2664 reflections with I > 2σ(I)
T_min = 0.783, T_max = 1.000	R_int = 0.030
7695 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.057	H-atom parameters constrained
S = 0.84	Δρ_max = 0.60 e Å⁻³
4004 reflections	Δρ_min = −0.35 e Å⁻³
256 parameters

Special details top

Experimental. CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.29606 (17)	0.74651 (15)	0.40530 (15)	0.0371 (4)
H1	0.2997	0.7026	0.4728	0.056*
N1	0.14604 (19)	0.98882 (17)	0.28625 (17)	0.0320 (5)
H71	0.0504	1.0043	0.2930	0.038*
N2	0.38107 (18)	0.90626 (17)	0.17422 (16)	0.0253 (4)
N3	0.59036 (18)	0.96092 (17)	0.20465 (17)	0.0281 (5)
H73	0.6551	0.9964	0.2378	0.034*
C1	0.2175 (2)	0.6833 (2)	0.3382 (2)	0.0261 (5)
C2	0.1706 (2)	0.5575 (2)	0.3723 (2)	0.0314 (6)
H2A	0.1938	0.5116	0.4452	0.038*
C3	0.0906 (2)	0.4986 (2)	0.3012 (2)	0.0388 (6)
H3	0.0573	0.4129	0.3264	0.047*
C4	0.0583 (3)	0.5626 (2)	0.1941 (2)	0.0394 (6)
H4	0.0040	0.5211	0.1447	0.047*
C5	0.1056 (2)	0.6874 (2)	0.1593 (2)	0.0324 (6)
H5	0.0842	0.7313	0.0848	0.039*
C6	0.1839 (2)	0.7507 (2)	0.2306 (2)	0.0243 (5)
C7	0.2219 (2)	0.8922 (2)	0.1944 (2)	0.0248 (5)
H7	0.1918	0.9171	0.1127	0.030*
C8	0.2073 (2)	1.0582 (2)	0.3632 (2)	0.0268 (5)
C9	0.1194 (2)	1.1389 (2)	0.4568 (2)	0.0339 (6)
H9	0.0153	1.1454	0.4678	0.041*
C10	0.1830 (3)	1.2084 (2)	0.5323 (2)	0.0393 (6)
H10	0.1218	1.2622	0.5957	0.047*
C11	0.3347 (3)	1.2023 (2)	0.5187 (2)	0.0369 (6)
H11	0.3769	1.2511	0.5721	0.044*
C12	0.4231 (3)	1.1247 (2)	0.4269 (2)	0.0329 (6)
H12	0.5270	1.1201	0.4163	0.039*
C13	0.3605 (2)	1.0524 (2)	0.3490 (2)	0.0251 (5)
C14	0.4443 (2)	0.9756 (2)	0.2468 (2)	0.0249 (5)
C15	0.4906 (2)	0.8449 (2)	0.0805 (2)	0.0234 (5)
C16	0.6239 (2)	0.8808 (2)	0.1001 (2)	0.0248 (5)
C17	0.7569 (2)	0.8389 (2)	0.0233 (2)	0.0300 (6)
H17	0.8475	0.8646	0.0364	0.036*
C18	0.7518 (2)	0.7580 (2)	−0.0733 (2)	0.0337 (6)
H18	0.8411	0.7264	−0.1280	0.040*
C19	0.6187 (3)	0.7212 (2)	−0.0929 (2)	0.0337 (6)
H19	0.6199	0.6650	−0.1607	0.040*
C20	0.4854 (2)	0.7640 (2)	−0.0169 (2)	0.0315 (6)
H20	0.3948	0.7391	−0.0307	0.038*
O2	0.7042 (2)	0.38247 (17)	0.37419 (15)	0.0512 (5)
H2	0.7545	0.3286	0.3219	0.077*
C21	0.5862 (3)	0.4457 (3)	0.3245 (3)	0.0556 (8)
H21A	0.5252	0.5062	0.3880	0.067*
H21B	0.5236	0.3771	0.3092	0.067*
C22	0.6360 (3)	0.5233 (3)	0.2049 (3)	0.0656 (9)
H22A	0.7003	0.5901	0.2188	0.098*
H22B	0.5503	0.5683	0.1774	0.098*
H22C	0.6905	0.4630	0.1396	0.098*
Br1	0.85598 (3)	0.14400 (3)	0.18829 (3)	0.04163 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0462 (10)	0.0364 (10)	0.0337 (11)	−0.0104 (8)	−0.0197 (9)	0.0112 (8)
N1	0.0167 (10)	0.0352 (12)	0.0412 (13)	0.0017 (9)	−0.0023 (9)	0.0008 (10)
N2	0.0197 (10)	0.0283 (11)	0.0270 (12)	−0.0017 (8)	−0.0045 (9)	0.0048 (9)
N3	0.0191 (10)	0.0346 (12)	0.0317 (13)	−0.0045 (8)	−0.0079 (9)	0.0041 (9)
C1	0.0221 (12)	0.0280 (14)	0.0274 (15)	−0.0020 (10)	−0.0036 (11)	−0.0022 (11)
C2	0.0353 (14)	0.0265 (14)	0.0296 (16)	0.0007 (11)	−0.0032 (12)	0.0029 (11)
C3	0.0381 (15)	0.0302 (15)	0.0441 (18)	−0.0069 (12)	0.0013 (13)	−0.0007 (13)
C4	0.0369 (15)	0.0384 (16)	0.0452 (19)	−0.0079 (12)	−0.0097 (13)	−0.0103 (13)
C5	0.0271 (13)	0.0407 (16)	0.0291 (15)	−0.0014 (12)	−0.0064 (11)	0.0007 (12)
C6	0.0170 (12)	0.0280 (13)	0.0257 (15)	−0.0013 (10)	−0.0007 (10)	0.0020 (11)
C7	0.0168 (12)	0.0326 (14)	0.0238 (14)	−0.0003 (10)	−0.0044 (10)	0.0065 (11)
C8	0.0299 (14)	0.0212 (13)	0.0265 (15)	−0.0022 (11)	−0.0027 (11)	0.0084 (11)
C9	0.0248 (13)	0.0294 (14)	0.0409 (17)	0.0003 (11)	0.0037 (12)	0.0067 (12)
C10	0.0484 (17)	0.0286 (15)	0.0329 (16)	0.0009 (12)	0.0072 (13)	−0.0028 (12)
C11	0.0421 (16)	0.0345 (15)	0.0332 (17)	−0.0057 (12)	−0.0056 (13)	−0.0005 (12)
C12	0.0300 (14)	0.0313 (15)	0.0363 (16)	−0.0045 (11)	−0.0060 (12)	0.0068 (12)
C13	0.0253 (13)	0.0246 (13)	0.0221 (14)	−0.0006 (10)	−0.0002 (10)	0.0052 (11)
C14	0.0201 (13)	0.0257 (13)	0.0269 (15)	−0.0018 (10)	−0.0034 (11)	0.0093 (11)
C15	0.0214 (12)	0.0229 (13)	0.0226 (14)	0.0005 (10)	0.0000 (10)	0.0055 (10)
C16	0.0268 (13)	0.0240 (13)	0.0224 (15)	−0.0012 (10)	−0.0044 (11)	0.0052 (11)
C17	0.0221 (13)	0.0276 (14)	0.0382 (16)	0.0000 (10)	−0.0044 (11)	0.0055 (12)
C18	0.0287 (14)	0.0324 (15)	0.0333 (16)	0.0033 (11)	0.0041 (11)	0.0043 (12)
C19	0.0407 (16)	0.0338 (15)	0.0255 (15)	−0.0018 (12)	−0.0043 (12)	−0.0042 (11)
C20	0.0258 (14)	0.0369 (15)	0.0329 (16)	−0.0051 (11)	−0.0096 (12)	0.0059 (12)
O2	0.0656 (13)	0.0575 (13)	0.0339 (12)	−0.0002 (10)	−0.0217 (10)	0.0040 (9)
C21	0.064 (2)	0.0533 (19)	0.050 (2)	−0.0028 (15)	−0.0179 (16)	0.0123 (16)
C22	0.086 (2)	0.0533 (19)	0.060 (2)	−0.0077 (17)	−0.0255 (18)	0.0227 (17)
Br1	0.02457 (14)	0.04927 (18)	0.0522 (2)	−0.00537 (11)	−0.01119 (12)	0.00401 (13)

Geometric parameters (Å, º) top

O1—C1	1.360 (2)	C9—H9	0.9500
O1—H1	0.8400	C10—C11	1.388 (3)
N1—C8	1.365 (3)	C10—H10	0.9500
N1—C7	1.452 (3)	C11—C12	1.373 (3)
N1—H71	0.8800	C11—H11	0.9500
N2—C14	1.342 (3)	C12—C13	1.397 (3)
N2—C15	1.398 (3)	C12—H12	0.9500
N2—C7	1.474 (2)	C13—C14	1.427 (3)
N3—C14	1.336 (2)	C15—C20	1.381 (3)
N3—C16	1.390 (3)	C15—C16	1.392 (3)
N3—H73	0.8800	C16—C17	1.379 (3)
C1—C2	1.383 (3)	C17—C18	1.373 (3)
C1—C6	1.398 (3)	C17—H17	0.9500
C2—C3	1.376 (3)	C18—C19	1.393 (3)
C2—H2A	0.9500	C18—H18	0.9500
C3—C4	1.376 (3)	C19—C20	1.380 (3)
C3—H3	0.9500	C19—H19	0.9500
C4—C5	1.377 (3)	C20—H20	0.9500
C4—H4	0.9500	O2—C21	1.416 (3)
C5—C6	1.390 (3)	O2—H2	0.8400
C5—H5	0.9500	C21—C22	1.482 (3)
C6—C7	1.511 (3)	C21—H21A	0.9900
C7—H7	1.0000	C21—H21B	0.9900
C8—C9	1.401 (3)	C22—H22A	0.9800
C8—C13	1.402 (3)	C22—H22B	0.9800
C9—C10	1.367 (3)	C22—H22C	0.9800

C1—O1—H1	109.5	C12—C11—C10	119.2 (2)
C8—N1—C7	126.93 (17)	C12—C11—H11	120.4
C8—N1—H71	116.5	C10—C11—H11	120.4
C7—N1—H71	116.5	C11—C12—C13	120.2 (2)
C14—N2—C15	109.14 (17)	C11—C12—H12	119.9
C14—N2—C7	125.15 (18)	C13—C12—H12	119.9
C15—N2—C7	125.64 (18)	C12—C13—C8	120.6 (2)
C14—N3—C16	109.31 (18)	C12—C13—C14	123.8 (2)
C14—N3—H73	125.3	C8—C13—C14	115.6 (2)
C16—N3—H73	125.3	N3—C14—N2	108.79 (19)
O1—C1—C2	122.8 (2)	N3—C14—C13	128.8 (2)
O1—C1—C6	117.34 (19)	N2—C14—C13	122.39 (19)
C2—C1—C6	119.9 (2)	C20—C15—C16	121.4 (2)
C3—C2—C1	120.3 (2)	C20—C15—N2	132.57 (19)
C3—C2—H2A	119.8	C16—C15—N2	106.04 (19)
C1—C2—H2A	119.8	C17—C16—N3	131.3 (2)
C2—C3—C4	120.7 (2)	C17—C16—C15	122.0 (2)
C2—C3—H3	119.7	N3—C16—C15	106.71 (19)
C4—C3—H3	119.7	C18—C17—C16	116.6 (2)
C3—C4—C5	119.2 (2)	C18—C17—H17	121.7
C3—C4—H4	120.4	C16—C17—H17	121.7
C5—C4—H4	120.4	C17—C18—C19	121.6 (2)
C4—C5—C6	121.5 (2)	C17—C18—H18	119.2
C4—C5—H5	119.3	C19—C18—H18	119.2
C6—C5—H5	119.3	C20—C19—C18	121.9 (2)
C5—C6—C1	118.4 (2)	C20—C19—H19	119.0
C5—C6—C7	119.27 (19)	C18—C19—H19	119.0
C1—C6—C7	122.17 (19)	C19—C20—C15	116.5 (2)
N1—C7—N2	107.70 (17)	C19—C20—H20	121.8
N1—C7—C6	113.67 (17)	C15—C20—H20	121.8
N2—C7—C6	112.43 (15)	C21—O2—H2	109.5
N1—C7—H7	107.6	O2—C21—C22	113.1 (2)
N2—C7—H7	107.6	O2—C21—H21A	109.0
C6—C7—H7	107.6	C22—C21—H21A	109.0
N1—C8—C9	121.2 (2)	O2—C21—H21B	109.0
N1—C8—C13	120.7 (2)	C22—C21—H21B	109.0
C9—C8—C13	118.2 (2)	H21A—C21—H21B	107.8
C10—C9—C8	120.3 (2)	C21—C22—H22A	109.5
C10—C9—H9	119.9	C21—C22—H22B	109.5
C8—C9—H9	119.9	H22A—C22—H22B	109.5
C9—C10—C11	121.6 (2)	C21—C22—H22C	109.5
C9—C10—H10	119.2	H22A—C22—H22C	109.5
C11—C10—H10	119.2	H22B—C22—H22C	109.5

O1—C1—C2—C3	179.6 (2)	C9—C8—C13—C12	0.4 (3)
C6—C1—C2—C3	−0.3 (3)	N1—C8—C13—C14	2.8 (3)
C1—C2—C3—C4	1.2 (3)	C9—C8—C13—C14	−176.06 (19)
C2—C3—C4—C5	−0.8 (3)	C16—N3—C14—N2	0.7 (2)
C3—C4—C5—C6	−0.6 (3)	C16—N3—C14—C13	−177.9 (2)
C4—C5—C6—C1	1.5 (3)	C15—N2—C14—N3	−0.4 (2)
C4—C5—C6—C7	−174.82 (19)	C7—N2—C14—N3	176.86 (17)
O1—C1—C6—C5	179.06 (19)	C15—N2—C14—C13	178.27 (18)
C2—C1—C6—C5	−1.0 (3)	C7—N2—C14—C13	−4.4 (3)
O1—C1—C6—C7	−4.7 (3)	C12—C13—C14—N3	−2.1 (3)
C2—C1—C6—C7	175.17 (19)	C8—C13—C14—N3	174.23 (19)
C8—N1—C7—N2	−14.3 (3)	C12—C13—C14—N2	179.4 (2)
C8—N1—C7—C6	110.9 (2)	C8—C13—C14—N2	−4.2 (3)
C14—N2—C7—N1	12.6 (3)	C14—N2—C15—C20	−179.8 (2)
C15—N2—C7—N1	−170.59 (17)	C7—N2—C15—C20	2.9 (4)
C14—N2—C7—C6	−113.4 (2)	C14—N2—C15—C16	−0.1 (2)
C15—N2—C7—C6	63.4 (2)	C7—N2—C15—C16	−177.31 (17)
C5—C6—C7—N1	112.5 (2)	C14—N3—C16—C17	178.9 (2)
C1—C6—C7—N1	−63.7 (2)	C14—N3—C16—C15	−0.8 (2)
C5—C6—C7—N2	−124.8 (2)	C20—C15—C16—C17	0.6 (3)
C1—C6—C7—N2	59.0 (3)	N2—C15—C16—C17	−179.22 (19)
C7—N1—C8—C9	−173.6 (2)	C20—C15—C16—N3	−179.71 (19)
C7—N1—C8—C13	7.6 (3)	N2—C15—C16—N3	0.5 (2)
N1—C8—C9—C10	−179.5 (2)	N3—C16—C17—C18	179.6 (2)
C13—C8—C9—C10	−0.7 (3)	C15—C16—C17—C18	−0.8 (3)
C8—C9—C10—C11	0.4 (3)	C16—C17—C18—C19	0.5 (3)
C9—C10—C11—C12	0.1 (3)	C17—C18—C19—C20	0.1 (3)
C10—C11—C12—C13	−0.4 (3)	C18—C19—C20—C15	−0.3 (3)
C11—C12—C13—C8	0.1 (3)	C16—C15—C20—C19	0.0 (3)
C11—C12—C13—C14	176.3 (2)	N2—C15—C20—C19	179.8 (2)
N1—C8—C13—C12	179.27 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.84	1.82	2.657 (2)	175
N1—H71···Br1ⁱⁱ	0.88	2.61	3.3501 (17)	142
N3—H73···Br1ⁱⁱⁱ	0.88	2.45	3.1956 (18)	143
O2—H2···Br1	0.84	2.41	3.2378 (17)	168

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆N₃O⁺·Br⁻·C₂H₆O
M_r	440.33
Crystal system, space group	Triclinic, P1
Temperature (K)	200
a, b, c (Å)	9.3438 (5), 10.0736 (5), 10.8452 (5)
α, β, γ (°)	86.832 (4), 77.203 (4), 84.674 (4)
V (Å³)	990.53 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.10
Crystal size (mm)	0.28 × 0.24 × 0.05

Data collection
Diffractometer	Oxford XCalibur diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.783, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7695, 4004, 2664
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.057, 0.84
No. of reflections	4004
No. of parameters	256
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.35

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), PARST (Nardelli, 1995) and publCIF (Westrip, 20091).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.84	1.82	2.657 (2)	175.2
N1—H71···Br1ⁱⁱ	0.88	2.61	3.3501 (17)	141.8
N3—H73···Br1ⁱⁱⁱ	0.88	2.45	3.1956 (18)	142.7
O2—H2···Br1	0.84	2.41	3.2378 (17)	167.6

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

Acknowledgements

The authors thank Professor P. Klüfers for generous allocation of diffractometer time.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Cuny, E., Lichtenthaler, F. W. & Moser, A. (1980). Tetrahedron Lett. 21, 3029–3032. CrossRef CAS Web of Science Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Kubicova, L., Sustr, M., Kralova, K., Chobnot, V., Vytlacilova, J., Jahodar, L., Vuorela, P., Machacek, M. & Kaustova, J. (2003). Molecules, 8, 756–769. Web of Science CrossRef CAS Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Niementowski, S. (1895). J. Prakt. Chem. 51, 546—566. Google Scholar
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar
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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

6-(2-Hy­droxy­phen­yl)-5,6-di­hydro­benzimidazolo[1,2-c]quinazolin-12-ium bromide ethanol solvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

6-(2-Hydroxyphenyl)-5,6-dihydrobenzimidazolo[1,2-c]quinazolin-12-ium bromide ethanol solvate